Caledon Real Estate | Caledon Homes with a Pool for Sale

Set on a half-acre lot (100 x 219 ft) along Mississauga Rd between Mayfield and Old School, this two-storey detached home offers 4,250+ sq ft of total living space, 3,000 of it above grade. The main and upper levels were rebuilt in 2011 (plumbing, electrical and HVAC included) and upgraded steadily since. The heart of the home is a large executive kitchen: premium granite counters, wall-to-wallDon't miss this one.custom cabinetry, ceramic tile backsplash, and a breakfast bar. Stainless appliances include a double fridge (2025), two built-in ovens, built-in microwave, 36" gas cooktop and range hood carpet-free interior pairs hardwood in the living areas and bedrooms with ceramic tile in the foyer, kitchen, baths and basement. Pot lights, a natural oak staircase, upgraded baths with premium vanities, and a large multi-functional basement complete the layout. Outside, a driveway that holds 10+ vehicles, an in-ground saltwater pool, a stamped concrete patio, and a detached garage/workshop with hydro and insulation. Mechanicals are a genuine strength: the home is fully spray-foam insulated and runs on a geothermal furnace and A/C that keeps costs low for its size, plus an owned hot water tank, 200-amp service, drilled well with UV and sediment purification, water softener, and updated pump, pressure tank and sump systems. Space, land and unbeatable quality of life on Caledon's southern edge, minutes from Brampton. Don't miss this one. (id:5764)

12806 Mississauga Road, Caledon

Listing courtesy of RE/MAX REAL ESTATE CENTRE INC..

$1,499,000

4 Beds ⋅ 3 Baths ⋅ W13606962 MLS® #

Set on a half-acre lot (100 x 219 ft) along Mississauga Rd between Mayfield and Old School, this two-storey detached home offers 4,250+ sq ft of total living space, 3,000 of it above grade. The main and upper levels were rebuilt in 2011 (plumbing, electrical and HVAC included) and upgraded steadily since. The heart of the home is a large executive kitchen: premium granite counters, wall-to-wallDon't miss this one.custom cabinetry, ceramic tile backsplash, and a breakfast bar. Stainless appliances include a double fridge (2025), two built-in ovens, built-in microwave, 36" gas cooktop and range hood carpet-free interior pairs hardwood in the living areas and bedrooms with ceramic tile in the foyer, kitchen, baths and basement. Pot lights, a natural oak staircase, upgraded baths with premium vanities, and a large multi-functional basement complete the layout. Outside, a driveway that holds 10+ vehicles, an in-ground saltwater pool, a stamped concrete patio, and a detached garage/workshop with hydro and insulation. Mechanicals are a genuine strength: the home is fully spray-foam insulated and runs on a geothermal furnace and A/C that keeps costs low for its size, plus an owned hot water tank, 200-amp service, drilled well with UV and sediment purification, water softener, and updated pump, pressure tank and sump systems. Space, land and unbeatable quality of life on Caledon's southern edge, minutes from Brampton. Don't miss this one.

12806 Mississauga Road, Caledon

Listing courtesy of RE/MAX REAL ESTATE CENTRE INC..

$5,499,000

4 Beds ⋅ 4 Baths ⋅ W13601824 MLS® #

Extraordinary Caledon estate where privacy, a tranquil setting, natural beauty, and endless opportunity come together on approximately 86 spectacular acres. Tucked away among the rolling hills, this remarkable property offers an exceptional blend of open pasture, productive hay fields, mature hardwood forest, scenic trails, and breathtaking countryside views in every direction. The beautiful home is designed to embrace its surroundings, featuring soaring ceilings, expansive windows that flood the interior with natural light and an open-concept layout. The fully finished walkout lower level seamlessly extends your living space outdoors, leading to a resort-inspired backyard complete with a saltwater inground pool, spacious patios, and multiple areas to relax while taking in the peaceful landscape. For those seeking space to work, create, or operate a business from home, the impressive approximately 3,000 sq. ft. heated workshop offers exceptional flexibility with dedicated office space, generous storage, and room for countless uses. The property also features a traditional barn and fenced pasture with convenient livestock watering access, making it well suited for hobby farming, equestrian pursuits, or a variety of agricultural ventures. Whether you're dreaming of a family estate, multi-generational living, a home-based business, hobby farm, or simply investing in one of Caledon's most desirable rural settings, this property offers outstanding potential both today and for the future. Minutes from the amenities of Caledon and within easy commuting distance to Pearson International Airport and the GTA. Enjoy nearby golf courses, equestrian facilities, skiing, cycling, hiking trails, charming restaurants, boutique shopping, and excellent schools-all while coming home to a setting that feels worlds away. A truly rare offering where lifestyle, land, and limitless possibilities meet. (id:5764)

18250 Duffy's Lane, Caledon

Listing courtesy of COLDWELL BANKER RONAN REALTY.

$5,499,000

4 Beds ⋅ 4 Baths ⋅ W13601824 MLS® #

Extraordinary Caledon estate where privacy, a tranquil setting, natural beauty, and endless opportunity come together on approximately 86 spectacular acres. Tucked away among the rolling hills, this remarkable property offers an exceptional blend of open pasture, productive hay fields, mature hardwood forest, scenic trails, and breathtaking countryside views in every direction. The beautiful home is designed to embrace its surroundings, featuring soaring ceilings, expansive windows that flood the interior with natural light and an open-concept layout. The fully finished walkout lower level seamlessly extends your living space outdoors, leading to a resort-inspired backyard complete with a saltwater inground pool, spacious patios, and multiple areas to relax while taking in the peaceful landscape. For those seeking space to work, create, or operate a business from home, the impressive approximately 3,000 sq. ft. heated workshop offers exceptional flexibility with dedicated office space, generous storage, and room for countless uses. The property also features a traditional barn and fenced pasture with convenient livestock watering access, making it well suited for hobby farming, equestrian pursuits, or a variety of agricultural ventures. Whether you're dreaming of a family estate, multi-generational living, a home-based business, hobby farm, or simply investing in one of Caledon's most desirable rural settings, this property offers outstanding potential both today and for the future. Minutes from the amenities of Caledon and within easy commuting distance to Pearson International Airport and the GTA. Enjoy nearby golf courses, equestrian facilities, skiing, cycling, hiking trails, charming restaurants, boutique shopping, and excellent schools-all while coming home to a setting that feels worlds away. A truly rare offering where lifestyle, land, and limitless possibilities meet.

18250 Duffy's Lane, Caledon

Listing courtesy of COLDWELL BANKER RONAN REALTY.

$1,249,900

4 Beds ⋅ 4 Baths ⋅ W13593018 MLS® #

This bungalow offers over 3,300 sq. ft. of finished living space with a separate entrance, making it ideal for multi-generational living or income potential. Located on a quiet cul-de-sac in a family-friendly neighbourhood, the private backyard overlooks a parkette and features a saltwater pool with slide, spa/hot tub, gazebo, mature trees, and wrought iron gate access on both sides.The open-concept main floor features spacious living and dining areas, a large kitchen, a family room with a three-sided fireplace, and a walkout to an expansive deck overlooking the backyard.The spacious primary suite includes a beautifully updated ensuite with heated floors and a walk-in closet. Two additional bedrooms, a full bath, main-floor laundry, and direct garage access complete the main level.The bright above-grade walkout lower level offers a second kitchen, generous living and dining areas, a private bedroom with ensuite, French doors, a separate entrance, and a laundry rough-in.A rare opportunity to own a spacious home with flexible living space, exceptional outdoor amenities, and a prime location in one of Valleywood's most desirable neighbourhoods.

8 Vista View Court, Caledon

Listing courtesy of KELLER WILLIAMS PORTFOLIO REALTY.

$10,900,000

7 Beds ⋅ 5 Baths ⋅ W13589386 MLS® #

WOODLANDS is an extraordinary 7-bedroom, 5-bathroom estate offering two distinct residences set on approximately 63 private acres of mature forest, scenic trails, and meticulously landscaped gardens. Perfectly positioned at the prestigious corner of Escarpment Sideroad and St. Andrews Road, surrounded by grand country estates and directly across from Paintbrush Golf Club, while just minutes to Devil's Pulpit Golf Association. The main residence is highlighted by a breathtaking 14-foot floor-to-ceiling great room and an elegant open-concept marble and onyx kitchen. A dramatic two-sided floor-to-ceiling fireplace beautifully separates the principal living and dining rooms, while expansive wraparound terraces provide seamless indoor-outdoor living from every principal space. Two luxurious primary suites each feature walk-in closets and spa-inspired 5-piece ensuites. The walk-out lower level is designed for exceptional entertaining, complete with a spacious family room, wine cellar, recreation area, mirrored fitness studio, two above-grade bedrooms, and a custom 10-person wet bar. The contemporary Pool House offers two additional bedrooms, dramatic floor-to-ceiling windows, a spacious 3-piece wet room, and stunning views over the infinity-edge pool and hot tub. Outdoor entertaining is equally impressive with an expansive dining terrace, championship tennis court, beautifully manicured gardens, woodland walking trails, and a tranquil fire pit setting surrounded by towering pines. Offering approximately 6,000 sq. ft. of total living space, WOODLANDS presents a truly exceptional private estate in one of Caledon's most coveted locations. (id:5764)

4780 Escarpment Sideroad, Caledon

Listing courtesy of RE/MAX NOBLECORP REAL ESTATE.

$10,900,000

7 Beds ⋅ 5 Baths ⋅ W13589386 MLS® #

WOODLANDS is an extraordinary 7-bedroom, 5-bathroom estate offering two distinct residences set on approximately 63 private acres of mature forest, scenic trails, and meticulously landscaped gardens. Perfectly positioned at the prestigious corner of Escarpment Sideroad and St. Andrews Road, surrounded by grand country estates and directly across from Paintbrush Golf Club, while just minutes to Devil's Pulpit Golf Association. The main residence is highlighted by a breathtaking 14-foot floor-to-ceiling great room and an elegant open-concept marble and onyx kitchen. A dramatic two-sided floor-to-ceiling fireplace beautifully separates the principal living and dining rooms, while expansive wraparound terraces provide seamless indoor-outdoor living from every principal space. Two luxurious primary suites each feature walk-in closets and spa-inspired 5-piece ensuites. The walk-out lower level is designed for exceptional entertaining, complete with a spacious family room, wine cellar, recreation area, mirrored fitness studio, two above-grade bedrooms, and a custom 10-person wet bar. The contemporary Pool House offers two additional bedrooms, dramatic floor-to-ceiling windows, a spacious 3-piece wet room, and stunning views over the infinity-edge pool and hot tub. Outdoor entertaining is equally impressive with an expansive dining terrace, championship tennis court, beautifully manicured gardens, woodland walking trails, and a tranquil fire pit setting surrounded by towering pines. Offering approximately 6,000 sq. ft. of total living space, WOODLANDS presents a truly exceptional private estate in one of Caledon's most coveted locations.

4780 Escarpment Side Road, Caledon

Listing courtesy of RE/MAX NOBLECORP REAL ESTATE.

$1,465,000

3 Beds ⋅ 4 Baths ⋅ W13584948 MLS® #

Set on an impressive 83.78 x 177.49 ft estate lot in one of Caledon East's most coveted enclaves, this beautifully renovated executive residence offers timeless elegance, exceptional craftsmanship and resort inspired living. With a 3-car garage, refined curb appeal and a thoughtfully designed floor plan, this home seamlessly blends luxury with everyday functionality. Designed for both sophisticated entertaining and comfortable family living, the main level features elegant principal rooms, a private home office and a spectacular custom kitchen that serves as the heart of the home. Appointed with heated floors, a generous centre island, built-in convection ovens with warming drawer and premium finishes, the space is both beautiful and highly functional. The luxurious primary retreat is complemented by a newly renovated spa-inspired experience featuring heated floors, a freestanding soaker tub, double vanity and an oversized glass shower, creating a serene sanctuary. A well-appointed second-floor laundry room with a built-in drying rack and ironing station adds everyday convenience. The private backyard is a true outdoor oasis, designed for effortless entertaining. Surrounded by mature landscaping, enjoy an inground heated pool with a new liner (2023), expansive Trex deck, pergola, charming cabana and a built-in Napoleon BBQ, creating the perfect setting for memorable gatherings and quiet summer evenings. Meticulously maintained and extensively updated, this exceptional home also features an Amber wood front entry door, updated garage doors, roof, fascia, soffits and eavestroughs (2022), furnace and air conditioning (2017), windows (2012), heated floors in the kitchen, main bath and ensuite, and a security monitoring system. A rare offering where thoughtful design, modern comfort and exceptional outdoor living come together in one of Caledon East's most desirable communities.

7 McKee Drive, Caledon

Listing courtesy of SOTHEBY'S INTERNATIONAL REALTY CANADA.

$1,249,900

5 Beds ⋅ 4 Baths ⋅ W13577488 MLS® #

This two-storey, 4-bedroom, 4-bathroom home with a finished walkout basement is a real crowd-pleaser. Situated in the Humber Meadows executive subdivision of detached homes, it features landscaped front stairs and a walkway. Boasting 2,356 sq. ft. plus the finished basement, it offers 9 ft ceilings and hardwood floors on the main and upper levels. The family room has a cozy two-sided fireplace shared with the spacious dining room, perfect for entertaining. The bright living room flows into a stylish kitchen with granite counters, stainless steel appliances, a breakfast bar, and a walkout to a deck with breathtaking views. The primary bedroom fits a king-size bed, includes a lovely sitting area, an updated 5-piece ensuite with a soaker tub, heated floors, glass shower, double sinks, and a walk-in closet. The upper-level main bath is also updated with double sinks and heated floors. The deck overlooks the Humber Valley Heritage Trail and forest. The finished basement includes a bedroom with an egress window, and a 3-piece bath. Located within St. Michaels Catholic Secondary and St. John Paul II school districts, this home also features a heated saltwater above-ground pool. Buyer to verify taxes and measurements.

17 Shangrila Terrace, Caledon

Listing courtesy of CENTURY 21 HERITAGE GROUP LTD..

$7,600,000

9 Beds ⋅ 9 Baths ⋅ W13573998 MLS® #

One of Caledon's Most Spectacular Estates with Breathtaking Views of the Caledon Landscape and Toronto Skyline, this estate is the epitome of luxury living and grand entertaining. Featuring 9 bedrooms and 9 bathrooms, this magnificent home has been meticulously designed to offer the perfect balance of family comfort and sophisticated entertaining spaces. Soaring ceilings and expansive windows throughout create a sense of openness, allowing natural light to flood the home and showcasing the stunning views from every room. The design effortlessly blends luxurious living areas with spaces made for gathering, while walkouts from every level lead to a variety of terraces, patios, and the beautifully landscaped grounds. The gourmet kitchen is a chef's dream, complete with high-end appliances, custom cabinetry, and a large centre island. The formal dining room and great room with a fireplace are perfect for hosting guests, while the cozy English pub in the basement provides a warm, inviting atmosphere for intimate gatherings. The basement also boasts a walkout to a patio, ideal for enjoying the outdoors in style. The estate also includes a nanny suite for added privacy and convenience, as well as a 4-bay garage with loft space above perfect for extra storage or a home office. Indulge in ultimate relaxation with your indoor pool, surrounded by high-end finishes and ample lounging space. Whether you're enjoying the private, serene outdoor spaces or hosting friends and family, this estate is built for both relaxation and entertainment. This one-of-a-kind estate sits is located just moments from Caledon's finest amenities, offering both seclusion and convenience. (id:5764)

2097 Grange Sideroad, Caledon

Listing courtesy of ROYAL LEPAGE MEADOWTOWNE REALTY.

$7,600,000

9 Beds ⋅ 9 Baths ⋅ W13573998 MLS® #

One of Caledon's Most Spectacular Estates with Breathtaking Views of the Caledon Landscape and Toronto Skyline, this estate is the epitome of luxury living and grand entertaining. Featuring 9 bedrooms and 9 bathrooms, this magnificent home has been meticulously designed to offer the perfect balance of family comfort and sophisticated entertaining spaces. Soaring ceilings and expansive windows throughout create a sense of openness, allowing natural light to flood the home and showcasing the stunning views from every room. The design effortlessly blends luxurious living areas with spaces made for gathering, while walkouts from every level lead to a variety of terraces, patios, and the beautifully landscaped grounds. The gourmet kitchen is a chef's dream, complete with high-end appliances, custom cabinetry, and a large centre island. The formal dining room and great room with a fireplace are perfect for hosting guests, while the cozy English pub in the basement provides a warm, inviting atmosphere for intimate gatherings. The basement also boasts a walkout to a patio, ideal for enjoying the outdoors in style. The estate also includes a nanny suite for added privacy and convenience, as well as a 4-bay garage with loft space above perfect for extra storage or a home office. Indulge in ultimate relaxation with your indoor pool, surrounded by high-end finishes and ample lounging space. Whether you're enjoying the private, serene outdoor spaces or hosting friends and family, this estate is built for both relaxation and entertainment. This one-of-a-kind estate sits is located just moments from Caledon's finest amenities, offering both seclusion and convenience.

2097 Grange Side Road, Caledon

Listing courtesy of ROYAL LEPAGE MEADOWTOWNE REALTY.

$1,299,000

4 Beds ⋅ 4 Baths ⋅ W13572646 MLS® #

Welcome to this stunning, fully renovated two-storey family home in the heart of Bolton, where modern luxury meets exceptional functionality. Completely transformed from top to bottom, this impressive four-bedroom residence showcases quality craftsmanship and premium finishes throughout. Step inside to discover a bright, open-concept layout featuring brand-new hardwood flooring throughout, creating a seamless flow between living spaces. The beautifully redesigned kitchen is the heart of the home, boasting elegant quartz countertops and backsplash, a breakfast bar with fluted paneling, abundant workspace for cooking and entertaining, and plenty of cabinet space. Every bathroom has been thoughtfully updated with contemporary finishes. The luxurious primary retreat offers the ultimate spa-like experience with a stunning 5-pc ensuite complete with a free-standing tub, oversized shower with glass enclosure and luxurious rain head, expansive walk-in closet designed to impress. The fully finished basement adds valuable living space and versatility, complete with new waterproof laminate flooring and an additional three-piece bathroom-perfect for a recreation room, home office, gym, or guest accommodations. Outside, enjoy your own private backyard oasis featuring an above-ground pool, spacious patio area, and a large shed for additional storage. Parking is never an issue with a double-car garage, including epoxy floors and a driveway that comfortably accommodates four vehicles. Located in a desirable Bolton neighbourhood close to schools, parks, shopping, and all amenities, this turnkey home offers the perfect blend of style, comfort, and convenience. Simply move in and enjoy everything this beautifully renovated home has to offer.

92 Headwater Road, Caledon

Listing courtesy of RE/MAX PREMIER INC..

$1,399,900

6 Beds ⋅ 4 Baths ⋅ W13570778 MLS® #

Pride of ownership shines throughout this updated, custom-built Grand Brook home offering ~2,400 sq.ft. above grade. Situated on a premium, landscaped oversized pie-shaped lot with an impressive 100-ft frontage, this property features a extra wide driveway with 7 car parking space. Over $100k has been invested in a spectacular private backyard oasis with professional landscaping; a swimming pool ;a custom cabana complete with a TV & wet bar; a large retractable awning-perfect for outdoor entertaining/family gatherings. The interior is recently renovated with quality and tasteful upgrades. The chef's kitchen features quartz countertops, solid hardwood cabinetry, a designer pantry, porcelain flooring, and a spacious eat-in area overlooking the pool through new patio doors. The adjoining family room overlooks the kitchen and offers a cozy fireplace, hardwood flooring, automated power blinds, and an inviting atmosphere. The impressive 17-ft grand foyer welcomes guests with a grand, wainscoted wall staircase, stunning light fixture, extensive pot lighting, and an oversized front hall guest closet. The combined living/dining room features a beautiful new double door entry and gleaming new hardwood floors. The main floor features an upgraded 2-piece powder room and a laundry room with a window, closet, and convenient access to a heated oversized double garage. California shutters throughout add elegance and privacy. The second floor offers 4 generously sized bedrooms with large closets and parquet flooring. The spacious primary bedroom features a walk-in closet and a luxurious, fully updated ensuite complete with a soaker tub and heated floors. The finished basement provides exceptional versatility and can serve as an in-law suite, featuring a full kitchen, full bathroom, 2 additional rooms, and a cantina. This meticulously maintained home combines exceptional craftsmanship, quality upgrades, and outstanding indoor/outdoor living in a highly sought-after neighbourhood.

22 Ashbury Crescent, Caledon

Listing courtesy of WEB MAX REALTY INC..

$3,299,999

7 Beds ⋅ 6 Baths ⋅ W13569080 MLS® #

Introducing a residence of unrivaled grandeur, where architectural brilliance meets timeless sophistication. Set behind a picturesque winding driveway on 10+ pristine acres of professionally landscaped grounds, this extraordinary custom estate offers over 7500 sqft of exquisitely curated living space, masterfully designed for those who appreciate uncompromising luxury. Every room is a showcase of exceptional craftsmanship, from soaring vaulted ceilings and intricate hand-carved architectural details to bespoke finishes that define elegance at every turn. The spectacular formal dining room comfortably hosts 20+ guests beneath a magnificent hand-carved ceiling, while the chef-inspired gourmet kitchen features illuminated back-lit stone countertops, premium appliances, and a stunning fireplace that creates the perfect gathering space. Designed to impress, the home offers Gated Driveway ,5 luxurious bedrooms, an executive office,2 gourmet kitchens, multiple private parking', and a breathtaking hand-carved oak staircase that serves as the architectural centerpiece of the residence. The spectacular resort-inspired solarium provides the ultimate wellness retreat with a sauna and a hot tub, offering year-round relaxation in complete privacy. An exceptional private in-law suite includes 2 additional bedrooms, a full bathroom, kitchen, and spacious living room, making it ideal for extended family, guests, or multi-generational living. Every window captures breathtaking views of rolling lawns, mature trees, and meticulously landscaped gardens, creating a peaceful sanctuary unlike any other. The expansive grounds provide endless possibilities for entertaining, recreation, or simply enjoying the serenity and exclusivity of country estate living. This remarkable multigenerational property seamlessly blends elite craftsmanship, timeless elegance, and resort-style luxury, creating a residence that is as functional as it is a legacy estate. 3 kitchens. (id:5764)

1 Flaherty Lane, Caledon

Listing courtesy of ROYAL LEPAGE FLOWER CITY REALTY.

$6,399,000

6 Beds ⋅ 10 Baths ⋅ W13565682 MLS® #

Welcome to 9 Flaherty Lane, a breathtaking custom estate nestled on over 10.6 acres in one of Caledon's prestigious enclaves and backing onto 50 acres of conservation land. Spanning over 13,500 square feet above grade and over 20,000 square feet total, this residence offers homeowners unmatched luxury, privacy, and scale. Inside, 5 prodigious bedrooms reside, each with its own ensuites, including a mesmerizing Owners' suite with his and her ensuites and a private guest bedroom in the lower level. Soaring ceiling heights are found across all 3 levels and range from 10 ft to 21ft, with 3 open to the above living areas. Both warm and inviting, this home attracts an abundance of natural light via the bespoke solarium and sunroom. As you make your way through this lovely home, signature features are found, including a 2-level mahogany library with an enchanting spiral staircase, a home theatre, a retro 50's inspired diner, a 5-car garage, multiple fireplaces, 9 geothermal heating and cooling systems, and a gourmet kitchen with a 60" Wolf gas cooktop and oven. Winning "North America's Best Pool" award in 1997, the indoor pool is truly a space where loved ones can gather and enjoy all year round. The serene outdoors offers just as much as the inside, with a spring fed 1 acre pond, a gazebo, a large designer patio with custom railing overlooking the water, and ample green space to host large social gatherings. This home is an absolute must see and offers a rare high-capacity well pumping 120 liters of water per minute, as well as an oversized septic tank and a new roof completed in 2024. With 16 interior and exterior cameras operated through Telus, security here is top-tier! Built to the highest standards using custom-made materials, this estate offers a rare blend of elegance and resort-style living. Whether hosting on a grand scale or seeking a private retreat, 9 Flaherty Lane delivers an extraordinary lifestyle! (id:5764)

9 Flaherty Lane, Caledon

Listing courtesy of SAM MCDADI REAL ESTATE INC..

$3,299,999

7 Beds ⋅ 6 Baths ⋅ W13569080 MLS® #

Introducing a residence of unrivaled grandeur, where architectural brilliance meets timeless sophistication. Set behind a picturesque winding driveway on 10+ pristine acres of professionally landscaped grounds, this extraordinary custom estate offers over 7500 sqft of exquisitely curated living space, masterfully designed for those who appreciate uncompromising luxury. Every room is a showcase of exceptional craftsmanship, from soaring vaulted ceilings and intricate hand-carved architectural details to bespoke finishes that define elegance at every turn. The spectacular formal dining room comfortably hosts 20+ guests beneath a magnificent hand-carved ceiling, while the chef-inspired gourmet kitchen features illuminated back-lit stone countertops, premium appliances, and a stunning fireplace that creates the perfect gathering space. Designed to impress, the home offers Gated Driveway ,5 luxurious bedrooms, an executive office,2 gourmet kitchens, multiple private parking', and a breathtaking hand-carved oak staircase that serves as the architectural centerpiece of the residence. The spectacular resort-inspired solarium provides the ultimate wellness retreat with a sauna and a hot tub, offering year-round relaxation in complete privacy. An exceptional private in-law suite includes 2 additional bedrooms, a full bathroom, kitchen, and spacious living room, making it ideal for extended family, guests, or multi-generational living. Every window captures breathtaking views of rolling lawns, mature trees, and meticulously landscaped gardens, creating a peaceful sanctuary unlike any other. The expansive grounds provide endless possibilities for entertaining, recreation, or simply enjoying the serenity and exclusivity of country estate living. This remarkable multigenerational property seamlessly blends elite craftsmanship, timeless elegance, and resort-style luxury, creating a residence that is as functional as it is a legacy estate. 3 kitchens.

1 Flaherty Lane, Caledon

Listing courtesy of ROYAL LEPAGE FLOWER CITY REALTY.

$6,399,000

6 Beds ⋅ 10 Baths ⋅ W13565682 MLS® #

Welcome to 9 Flaherty Lane, a breathtaking custom estate nestled on over 10.6 acres in one of Caledon's prestigious enclaves and backing onto 50 acres of conservation land. Spanning over 13,500 square feet above grade and over 20,000 square feet total, this residence offers homeowners unmatched luxury, privacy, and scale. Inside, 5 prodigious bedrooms reside, each with its own ensuites, including a mesmerizing Owners' suite with his and her ensuites and a private guest bedroom in the lower level. Soaring ceiling heights are found across all 3 levels and range from 10 ft to 21ft, with 3 open to the above living areas. Both warm and inviting, this home attracts an abundance of natural light via the bespoke solarium and sunroom. As you make your way through this lovely home, signature features are found, including a 2-level mahogany library with an enchanting spiral staircase, a home theatre, a retro 50's inspired diner, a 5-car garage, multiple fireplaces, 9 geothermal heating and cooling systems, and a gourmet kitchen with a 60" Wolf gas cooktop and oven. Winning "North America's Best Pool" award in 1997, the indoor pool is truly a space where loved ones can gather and enjoy all year round. The serene outdoors offers just as much as the inside, with a spring fed 1 acre pond, a gazebo, a large designer patio with custom railing overlooking the water, and ample green space to host large social gatherings. This home is an absolute must see and offers a rare high-capacity well pumping 120 liters of water per minute, as well as an oversized septic tank and a new roof completed in 2024. With 16 interior and exterior cameras operated through Telus, security here is top-tier! Built to the highest standards using custom-made materials, this estate offers a rare blend of elegance and resort-style living. Whether hosting on a grand scale or seeking a private retreat, 9 Flaherty Lane delivers an extraordinary lifestyle!

9 Flaherty Lane, Caledon

Listing courtesy of SAM MCDADI REAL ESTATE INC..

$2,199,000

3 Beds ⋅ 4 Baths ⋅ W13549302 MLS® #

Exceptional custom bungalow nestled on nearly 2 acres in one of Caledon's most prestigious executive enclaves. Set back from the road with a long private driveway, this remarkable property offers the perfect blend of luxury, privacy & convenience, just moments from HWY 50. Step outside & discover your own private resort. The beautifully landscaped grounds are designed for exceptional outdoor living, featuring a stunning saltwater inground pool, expansive patio, and an impressive covered outdoor kitchen that creates the ultimate space for entertaining all summer long. Mature trees & lush landscaping provide outstanding privacy, making this property feel like your own retreat. From the moment you enter, you'll be impressed by the cathedral ceilings that create a bright, open atmosphere throughout the grand foyer & elegant living room. The spacious eat-in kitchen, thoughtfully designed with an abundance of cabinetry & generous prep space for everyday living & effortless entertaining. The adjoining solarium is filled with natural light & offers the perfect setting to enjoy meals, unwind with a book, have your morning coffee or take in the peaceful views of the landscaped backyard. The thoughtfully designed main floor features a primary retreat with a walk-in closet & ensuite, along with spacious secondary bedrooms, a main floor laundry rm, and a functional mudroom with access to the backyard. The partially finished basement offers endless possibilities for additional living space, a rec room, home gym, or in-law potential, allowing you to customize it to suit your family's needs. Completing this incredible offering is an oversized three-car garage & ample parking. Rarely does a property combine executive living, resort-style amenities, and such a coveted Caledon location. Experience the tranquility of country living without sacrificing convenience, all tucked away in an exclusive neighbourhood just mins to major commuting routes, amenities, golf & conservation lands.

9 Moraine Place, Caledon

Listing courtesy of COLDWELL BANKER RONAN REALTY.

$1,698,000

4 Beds ⋅ 3 Baths ⋅ W13548102 MLS® #

Rare Caledon East Estate Lot | Nearly 1 Acre | Endless Possibilities Opportunities like this are becoming increasingly rare. Nestled on a spectacular pie shaped lot approaching one acre in one of Caledon East's most established and sought after neighbourhoods, this executive family residence offers the perfect blend of space, privacy and future potential. Surrounded by mature trees and lush landscaping, the property feels like a private country retreat while remaining just minutes from schools, amenities, and commuter routes. The backyard is designed for unforgettable gatherings, featuring a saltwater in-ground pool with attached hot tub, poolside cabana with hydro, expansive stonework, covered sunporch, and multiple outdoor entertaining areas that create a true resort style experience at home. Offering approx. 2600 sqft above grade, the home features spacious principal rooms and versatile layout that can comfortably accommodate growing families, multi-generational living, home offices and extended family under one roof. Whether you're hosting holidays, creating a family compound, or simple looking for room to breathe, this property delivers a lifestyle that is increasingly difficult to find. Beyond the itself lies the true value; the land. Large residential parcels of this size are exceptionally scarce in Caledon East and offers buyers the opportunity to secure a long term family estate in a neighbourhood where properties are tightly held. There may be future severance, redevelopment or estate planning potential , subject to all municipal approvals. For those seeking more than just a house - a place to build memories, create a legacy, and invest in a unique Piece of Caledon East -this is a truly exceptional offering.

19 Jean Street, Caledon

Listing courtesy of PROPERTY.CA INC..

$929,000

3 Beds ⋅ 3 Baths ⋅ W13546214 MLS® #

Located in the desirable South Hill community of Bolton, welcome to 249 Leavens Court. This beautifully updated home features 3 bedrooms, 3 bathrooms, and a finished basement complete with a Cozy rec with rough ins for future kitchen/laundry room.The open-concept main floor offers a fully updated, generously sized kitchen that flows seamlessly into the expansive family room overlooking the backyard-perfect for both everyday living and entertaining.Situated on an oversized 45' x 124' lot with great patio an above ground pool in a quiet, family-friendly court, this property provides plenty of space for children to play and families to enjoy the outdoors. Conveniently located within walking distance to schools, parks, shopping, and other amenities, plus just a four-minute walk to 24-hour public transit, this home offers an exceptional combination of comfort, space, and convenience.

249 Leavens Court, Caledon

Listing courtesy of CENTURY 21 B.J. ROTH REALTY LTD..

$2,399,000

6 Beds ⋅ 6 Baths ⋅ W13537978 MLS® #

This Custom-Built Caledon Estate Sitting On 3.74 Acres Of Manicured Grounds, Offering Unmatched Privacy, Breathtaking Presence, And A Lifestyle Reserved For The Exceptional. Completely Transformed With A Newly Redone Exterior Façade, Fresh Concrete Work, And Extensive Renovations Throughout, This Residence Delivers Modern Luxury Minutes From The City.Inside, A Grand Foyer Opens To A Soaring Family Room Open To Above, Elegant Living And Dining Rooms, A Private Main-Floor Office, And An Eat-In Kitchen Designed For Both Everyday Living And Upscale Entertaining With Outdoor Patio Access. A Spacious Mudroom And 3-Car Garage Complete The Main Level.Upstairs, The Primary Suite Is A True Retreat With A 5-Piece Spa Ensuite Featuring Double Sinks, Glass Shower, Freestanding Tub, Separate Water Closet, And Two Walk-In Closets. A Second Primary Enjoys Its Own 5-Piece Ensuite, While Bedrooms Three And Four Share A Stylish Jack And Jill Bath. A Fifth Bedroom Includes A Full Private Bath, And The Convenience Of An Upper-Level Laundry Room Elevates Daily Living. Hardwood Flooring Throughout Adds Warmth And Sophistication.The Lower Level Is An Entertainer's Dream With A Large Recreation And Bar Lounge, A Full Bedroom With Closet, A Luxurious Bath With Sauna, Ample Storage, And A Dedicated Indoor Basketball Court - A Rare And Extraordinary Feature. Step Outside To Your Personal Resort With An Inground Pool, Expansive Grounds, And Endless Space To Relax, Host, And Enjoy.A One-Of-A-Kind Offering Combining Land, Luxury, And Lifestyle. This Caledon Estate Defines Elevated Living. List Of Upgrades Attached.

6 Country Lane Drive, Caledon

Listing courtesy of RE/MAX REAL ESTATE CENTRE INC..

$1,349,900

4 Beds ⋅ 5 Baths ⋅ W13533608 MLS® #

Enjoy pool days in every season - all from the comfort of home! Set on a beautiful 1-acre lot along a paved country road and surrounded by towering mature trees, this spacious 2-storey home offers comfort, character, and a truly unique resort-style lifestyle.With over 3000 sq. ft. of living space, 4 bedrooms, and 5 bathrooms, this entertainer's dream is designed for everyday comfort and memorable gatherings. The enclosed pool area is a true showstopper, featuring an indoor inground pool, a cozy sitting area with a wood-burning fireplace, three clear roll-up doors, and patio doors leading to a covered outdoor dining space.The bright, open kitchen features ceiling-height cabinetry, a centre island with breakfast bar, modern pot lighting, and a walk-out from the breakfast area directly to the pool. The main level also offers multiple living spaces, including a formal dining room with fireplace, a living room with a second fireplace, and a spacious family room. Premium Jatoba hardwood flooring adds warmth and quality throughout the living, dining, and sitting areas.Upstairs, you'll find four bedrooms and two bathrooms. Major updates include a top-of-the-line geothermal system installed in 2016, central air conditioning with lifetime warranty, triple-pane thermal windows replaced approximately 9 years ago with lifetime warranty, and a 30-year three-tab shingle roof completed in September 2024. The hot water tank is owned, and the propane tank has been recently serviced. Outside, enjoy a detached 2-car garage, with loft and 3pc bathroom. This property boasts peaceful mature-treed surroundings, and plenty of outdoor space with lighting- all just a short drive to town amenities. A rare opportunity to enjoy privacy, space, and year-round poolside living. (id:5764)

19211 Mountainview Road, Caledon

Listing courtesy of CENTURY 21 MILLENNIUM INC..

$1,349,900

4 Beds ⋅ 5 Baths ⋅ W13533608 MLS® #

Enjoy pool days in every season - all from the comfort of home! Set on a beautiful 1-acre lot along a paved country road and surrounded by towering mature trees, this spacious 2-storey home offers comfort, character, and a truly unique resort-style lifestyle.With over 3000 sq. ft. of living space, 4 bedrooms, and 5 bathrooms, this entertainer's dream is designed for everyday comfort and memorable gatherings. The enclosed pool area is a true showstopper, featuring an indoor inground pool, a cozy sitting area with a wood-burning fireplace, three clear roll-up doors, and patio doors leading to a covered outdoor dining space.The bright, open kitchen features ceiling-height cabinetry, a centre island with breakfast bar, modern pot lighting, and a walk-out from the breakfast area directly to the pool. The main level also offers multiple living spaces, including a formal dining room with fireplace, a living room with a second fireplace, and a spacious family room. Premium Jatoba hardwood flooring adds warmth and quality throughout the living, dining, and sitting areas.Upstairs, you'll find four bedrooms and two bathrooms. Major updates include a top-of-the-line geothermal system installed in 2016, central air conditioning with lifetime warranty, triple-pane thermal windows replaced approximately 9 years ago with lifetime warranty, and a 30-year three-tab shingle roof completed in September 2024. The hot water tank is owned, and the propane tank has been recently serviced. Outside, enjoy a detached 2-car garage, with loft and 3pc bathroom. This property boasts peaceful mature-treed surroundings, and plenty of outdoor space with lighting- all just a short drive to town amenities. A rare opportunity to enjoy privacy, space, and year-round poolside living.

19211 Mountainview Road, Caledon

Listing courtesy of CENTURY 21 MILLENNIUM INC..

$1,899,999

5 Beds ⋅ 3 Baths ⋅ W13517430 MLS® #

Set on a spectacular and private 1-acre lot surrounded by rolling hills and mature greenery, this exceptional country property offers the perfect blend of luxury, comfort, and versatility. Featuring 4+1 bedrooms and 3 bathrooms, this beautifully finished home showcases an open-concept design with quality craftsmanship throughout. Bright, expansive living spaces are enhanced by large windows that capture breathtaking countryside views, while a stunning vaulted beam ceiling adds warmth, character, and a true sense of grandeur. The chef-inspired kitchen is designed for both everyday living and entertaining, featuring a centre island with sink, stainless steel appliances, built-in wall ovens, and induction cooktop. The elegant living room boasts bamboo hardwood flooring and a cozy wood-burning fireplace, complemented by a formal dining room and spacious family room. Step outside to a remarkable three-season covered porch overlooking your private backyard oasis, complete with an inground saltwater pool, hot tub, and beautifully landscaped grounds-perfect for relaxing or entertaining family and friends. Adding exceptional value, the fully self-contained in-law suite offers endless possibilities for multi-generational living, extended family, guests, or potential rental income. The main level is completed by two generous bedrooms and a beautifully appointed bathroom. Upstairs, you'll find the luxurious primary suite, an additional bedroom, and a spa-inspired 5-piece bathroom designed as the perfect retreat. Set in a peaceful country setting yet conveniently located within easy reach of nearby amenities, this one-of-a-kind property delivers the privacy, space, and lifestyle you've been searching for. Floor Plans Attached. Please note that some inside pictures have been virtually staged.

4314 Beech Grove Side Road, Caledon

Listing courtesy of ROYAL LEPAGE RCR REALTY.

$1,999,999

5 Beds ⋅ 3 Baths ⋅ W13514846 MLS® #

Beneath the sweeping branches of a magnificent willow tree, where a spring-fed pond glistens with lily pads and a charming bridge leads to its own secluded island, life begins to slow down. Surrounded by some of Caledon's most mature Japanese maples and gardens that bloom through every season, this remarkable 3.4-acre estate is a celebration of nature, privacy, and timeless beauty.Set within the prestigious Forks of the Credit, this executive bungalow offers approximately 3,600 sq. ft. of thoughtfully designed living space, with nearly every principal room overlooking the spectacular grounds.Expansive windows fill the open-concept interior with natural light, while wide-plank hardwood floors, a striking double-sided fireplace, and warm natural finishes create an inviting atmosphere. The custom kitchen features premium stainless steel appliances, quartz countertops, custom cabinetry, a dedicated coffee bar, and generous space for gathering. A separate formal dining room is ideal for entertaining.A private bedroom wing with its own entrance offers flexibility for multi-generational living or guests. Spa-inspired bathrooms, wide doorways, and thoughtfully integrated accessibility features allow the home to evolve with every stage of life.Outside, professionally designed perennial gardens surround a heated saltwater pool with waterfall, while the pool house bunkie with hydro and heat offers endless possibilities as a gym, yoga studio, office, artist's retreat, or private escape.Moments from Devil's Pulpit Golf Course, Belfountain Conservation Area, and some of Caledon's most celebrated scenery, this is a rare opportunity to enjoy country living without sacrificing convenience. Peaceful, private, and within easy reach of the GTA, 2 Cedar Drive offers a lifestyle as extraordinary as its setting. (id:5764)

2 Cedar Drive, Caledon

Listing courtesy of RE/MAX REAL ESTATE CENTRE INC..

$1,999,999

5 Beds ⋅ 3 Baths ⋅ W13514846 MLS® #

Beneath the sweeping branches of a magnificent willow tree, where a spring-fed pond glistens with lily pads and a charming bridge leads to its own secluded island, life begins to slow down. Surrounded by some of Caledon's most mature Japanese maples and gardens that bloom through every season, this remarkable 3.4-acre estate is a celebration of nature, privacy, and timeless beauty.Set within the prestigious Forks of the Credit, this executive bungalow offers approximately 3,600 sq. ft. of thoughtfully designed living space, with nearly every principal room overlooking the spectacular grounds.Expansive windows fill the open-concept interior with natural light, while wide-plank hardwood floors, a striking double-sided fireplace, and warm natural finishes create an inviting atmosphere. The custom kitchen features premium stainless steel appliances, quartz countertops, custom cabinetry, a dedicated coffee bar, and generous space for gathering. A separate formal dining room is ideal for entertaining.A private bedroom wing with its own entrance offers flexibility for multi-generational living or guests. Spa-inspired bathrooms, wide doorways, and thoughtfully integrated accessibility features allow the home to evolve with every stage of life.Outside, professionally designed perennial gardens surround a heated saltwater pool with waterfall, while the pool house bunkie with hydro and heat offers endless possibilities as a gym, yoga studio, office, artist's retreat, or private escape.Moments from Devil's Pulpit Golf Course, Belfountain Conservation Area, and some of Caledon's most celebrated scenery, this is a rare opportunity to enjoy country living without sacrificing convenience. Peaceful, private, and within easy reach of the GTA, 2 Cedar Drive offers a lifestyle as extraordinary as its setting.

2 Cedar Drive, Caledon

Listing courtesy of RE/MAX REAL ESTATE CENTRE INC..

$3,490,000

5 Beds ⋅ 5 Baths ⋅ W13512124 MLS® #

Welcome to 16609 Mount Wolfe Rd a Custom-built Luxury Estate Set on 2.92 Private Acres in Caledon, Offering Over 4700 Sq Ft Above Grade (as Per Mpac). From the Moment You Arrive Through the Automated Wrought Iron Gates, You're Greeted by a Serene Water Feature, Setting the Tone for What Lies Ahead. This 2011 Stone Bungalow Features Timeless Craftsmanship, Top-tier Materials, and Space to Live, Work, and Entertain inComfort. The Main Level Boasts 10-ft Ceilings, Radiant Heated Hickory and Marble Floors, and 8-ft Custom-stained Doors Throughout. The Gourmet Kitchen Includes Cherry Cabinetry, Granite Counters, Dual Islands, Sub-zero and Wolf Appliances. Enjoy a Grand Family Room and Formal Dining Area, With Limestone Fireplaces Both Designed for Gatherings and Day-to-day Elegance. The Executive Office/Cigar Room is Fully Appointed With a Fireplace and Professional-grade Ventilation Built For Productivity, Designed for Prestige. Ideal for Work Hard Play Hard. A True Highlight is the Oversized Main-floor Gym, Complete With Its Own Hot Tub, Perfect for Wellness and Recovery. The Luxurious Primary Suite Offers a Limestone Fireplace, Walk-in Closet, Steam Shower, Jacuzzi Tub, and Radiant Flooring. The Fully Finished Walkout Basement Includes a Soundproof Theatre With Reclining Chairs, a 900-bottle Climate-controlled Wine Cellar, and a Separate 2-bedroom Apartment With Private Kitchen, Laundry, and Its Own Entrances. But What Truly Sets This Estate Apart Are the Two Fully Equipped Workshops, Ideal for Contractors, Car Collectors, or Business Owners. Each Shop Offers 2,400sqft, 400 Amps, Separate Metering, and Heating All Accessed via Their Own Private, Fully Paved Driveway and Parking Area, Completely Separate From the Main Home Entrance. Outdoors, Enjoy a Heated Pool, Pool House With Washroom, Hot Tub, Outdoor Kitchen, Bar Area, and Professional Landscaping With Water Features. This Estate is Built for High-performance Living. SEE ATTACHMENTS

16609 Mount Wolfe Road, Caledon

Listing courtesy of RE/MAX SPECIALISTS TEAM SUKHVINDER.

$1,199,990

4 Beds ⋅ 3 Baths ⋅ W13509378 MLS® #

Welcome to 53 Marilyn Street, an exceptional opportunity to own a beautifully maintained detached home on a premium corner lot in one of Caledon East's most coveted family neighbourhoods. Surrounded by mature trees and prestigious homes, this property offers the perfect blend of privacy, space, and small-town charm. Step into your own backyard retreat featuring a massive entertainment deck, expansive greenspace, mature landscaping, an above-ground pool, storage shed, and a custom treehouse-creating the perfect setting for family fun and summer entertaining. Thoughtfully maintained with valuable updates including a high-efficiency furnace and central air conditioner (2021), hardwired security system with exterior surveillance cameras, and Bell Fibe directly to the home for ultra-fast internet and seamless remote work or streaming. Ideally located just minutes from excellent schools, parks, playgrounds, Caledon East Community Complex, arena, sports fields, scenic walking and cycling trails, conservation areas, restaurants, cafés, shopping and everyday amenities. Enjoy convenient access to Airport Road, Highway 10, Highway 9 and Highway 410, making commuting to Brampton, Vaughan, Pearson Airport and the GTA effortless while enjoying the peaceful lifestyle Caledon East is known for. Opportunities like this in Caledon East are exceptionally rare. A must-see!

53 Marilyn Street, Caledon

Listing courtesy of RE/MAX REALTY SERVICES INC..

$999,900

3 Beds ⋅ 3 Baths ⋅ W13509340 MLS® #

Welcome to 28 Crestridge Drive, a beautifully maintained detached home tucked away on a quiet cul-de-sac in one of Bolton's most sought-after neighbourhoods. The landscaped walkway and double car garage set the tone for the pride of ownership found throughout. Step inside to a warm, inviting atmosphere filled with natural light, thanks to generous windows and excellent sun exposure. The open-concept floor plan flows effortlessly, and two natural gas fireplaces, one in the living room, one in the basement, add warmth and character year-round. The updated kitchen features new cabinetry, stainless steel appliances, and a breakfast bar, opening directly to your backyard oasis. The premium ravine lot offers the ultimate privacy with no rear neighbours, maintenance-free artificial grass, a jacuzzi, and breathtaking views of nature to enjoy all year long. Three spacious bedrooms include a primary retreat with ample storage and a private ensuite, while the fully finished basement is perfect for a rec room, home office, or family entertainment space, complete with a second gas fireplace. Additional highlights include an EV charging hook-up in the garage, parking for up to 6 vehicles, updated furnace and A/C (2018), garage door (2021), and roof (2016). Minutes from grocery stores, parks, schools, and everyday amenities. A rare opportunity in Bolton!

28 Crestridge Drive, Caledon

Listing courtesy of RE/MAX EXPERTS.

$2,500,000

4 Beds ⋅ 6 Baths ⋅ W13505786 MLS® #

Experience the perfect balance of luxury, nature, and convenience. This property will appeal to the discerning buyer seeking something truly special. Inside 6,500 square feet of thoughtfully blends open-concept living with cozy private retreats. Nestled on a unique, secluded 1.88-acre lot, this is not just another estate - it's an exclusive haven waiting to be yours. Bask in natural light in the stunning 2-story great room flowing seamlessly into the well appointed kitchen that offers space for multiple cooks and seamless entertaining. The 2nd story primary suite is a private retreat, complete with a luxurious five-piece ensuite and a massive walk-in closet. Two additional bedrooms on this floor each feature their own ensuite baths and walk-in closets, ensuring comfort and privacy for family or guests. A fourth bedroom, conveniently located on the main floor, offers its own adjacent 3-piece bath. Need more flexibility? Two main-floor offices provide ideal work-from-home setups or creative spaces. The fully finished walk-up basement is a world of possibilities. With a second kitchen, exercise room, media room, 2-piece bath, and ample storage, it's ready to be transformed into the ultimate entertainment space or in-law suite. Outside is your private paradise, where the lush yard and pool are surrounded by mature trees, offering complete tranquility. A sweeping drive and 3-car garage in the front. An outdoor living space tailored for unforgettable gatherings, featuring an inground pool, a cabana with a 2-piece bath, expansive patios, and deck areas for dining, lounging, and family fun in the back. Beyond the property, the Caledon Trailway, Credit River and the quaint village of Cheltenham are nearby, or explore local gems like Terra Cotta and Belfountain. With Pearson Airport only 30 minutes and downtown Toronto an hour's drive, this property offers countryside living without compromise.

57 Kennedy Road, Caledon

Listing courtesy of KELLER WILLIAMS EDGE REALTY.

$1,599,000

4 Beds ⋅ 4 Baths ⋅ W13504738 MLS® #

Welcome to 29 Hayleyvale Rd located in the heart of Caledon Village, set on a private over half-acre lot surrounded by mature trees and landscaped grounds. With plenty of space inside and out, this home is perfect for families who enjoy both comfort and entertaining. The main floor features a renovated kitchen with quartz countertops, custom cabinetry, stainless steel appliances, and a large centre island that opens to the dining area overlooking the backyard. Hardwood floors, crown moulding, and large windows bring in great natural light throughout the home. Upstairs offers spacious bedrooms including a large primary retreat and updated bathrooms with modern finishes. The finished lower level adds even more living space with a cozy lounge, recreation area, games room, and full bathroom. Step outside to your own backyard retreat featuring an in-ground pool, large patio area, covered outdoor lounge with TV, screened-in sunroom, fire pit area, and plenty of yard space to enjoy. Located just minutes from prestigious golf courses, parks, and scenic trails, this property offers an incredible outdoor lifestyle while still being close to schools and commuter routes.

29 Hayleyvale Road, Caledon

Listing courtesy of CAPITAL NORTH REALTY CORPORATION.

$2,500,000

4 Beds ⋅ 7 Baths ⋅ 40844026 MLS® #

Experience the perfect balance of luxury, nature, and convenience. This property will appeal to the discerning buyer seeking something truly special. Inside 6,500 square feet of thoughtfully blends open-concept living with cozy private retreats. Nestled on a unique, secluded 1.88-acre lot, this is not just another estate - it’s an exclusive haven waiting to be yours. Bask in natural light in the stunning 2-story great room flowing seamlessly into the well appointed kitchen that offers space for multiple cooks and seamless entertaining. The 2nd story primary suite is a private retreat, complete with a luxurious five-piece ensuite and a massive walk-in closet. Two additional bedrooms on this floor each feature their own ensuite baths and walk-in closets, ensuring comfort and privacy for family or guests. A fourth bedroom, conveniently located on the main floor, offers its own adjacent 3-piece bath. Need more flexibility? Two main-floor offices provide ideal work-from-home setups or creative spaces. The fully finished walk-up basement is a world of possibilities. With a second kitchen, exercise room, media room, 2-piece bath, and ample storage, it’s ready to be transformed into the ultimate entertainment space or in-law suite. Outside is your private paradise, where the lush yard and pool are surrounded by mature trees, offering complete tranquility. A sweeping drive and 3-car garage in the front. An outdoor living space tailored for unforgettable gatherings, featuring an inground pool, a cabana with a 2-piece bath, expansive patios, and deck areas for dining, lounging, and family fun in the back. Beyond the property, the Caledon Trailway, Credit River and the quaint village of Cheltenham are nearby, or explore local gems like Terra Cotta and Belfountain. With Pearson Airport only 30 minutes and downtown Toronto an hour’s drive, this property offers countryside living without compromise. (id:5764)

57 KENNEDY Road, Caledon

Listing courtesy of Keller Williams Edge Realty.

$2,829,000

8 Beds ⋅ 7 Baths ⋅ W13496264 MLS® #

Your search ends in this very cul de sac! Welcome to 4 Woodlot Court...Multigenerational living at it's finest! This majestic property is nothing short of breathtaking! Situated on a 2 acre lot nestled among gorgeous custom built estate homes! Take in the extensively landscaped yard as you make your way up the long drive to approach a beautifully appointed custom built home featuring over 5,000sf of living space + a finished walk out basement! This property has been lovingly cared for and meticulously maintained inside and out! Pride of ownership is evident the moment you enter this 6 + 2 Bed, 8 bath home boasting soaring 13' vaulted ceilings at the main living space, tastefully upgraded finishes throughout, 3 beds including the Primary bedroom on the main floor + 3 additional beds on the upper level, large windows throughout which offer a sun drenched interior, beautifully finished chic and modern walk out basement featuring 9' ceilings a bar, recreation room, games area, home gym, utility room and plenty of additional storage. Enjoy the versatility of this home whether you occupy it as a bungalow or a 2 storey the possibilities are endless!! Featuring a SELF CONTAINED in law suite that offers a 2 bed, 2 bath floor plan featuring approx. 1,200sf with garage and rear yard access which is PERFECT for aging parents, teenage children or to generate additional rental income!. Host your favourite guests while you soak up the rays of summer in the pool surrounded by gorgeous mature trees in the private oasis of a backyard where you will find a pool house with a kitchenette, washroom, changeroom, outdoor BBQ set up and all that you require to throw the most perfect party! Comfortably store all of your toys, cars, boats or belongings in the massive heated garage which contains 4 doors with the ability to park 5 vehicles! A true rare gem that has so much to offer situated in a highly coveted pocket of beautiful Palgrave..this one must be seen!

4 Woodlot Court, Caledon

Listing courtesy of RE/MAX EXPERTS.

$2,999,000

5 Beds ⋅ 6 Baths ⋅ W13490940 MLS® #

Discover a truly unique and breathtaking country estate where nature, privacy, and exceptional design come together in perfect harmony. Set on a picturesque 2.71 acres and ideally positioned between the Pulpit Club, Caledon Mountain Trout Club, Caledon Ski Club, Brampton Flying Club, and along the Bruce Trail, this magnificent property offers an unmatched lifestyle within close proximity to the city. A resort-like sanctuary awaits, designed for both grand entertaining and quiet, restorative living. An inground saltwater pool, outdoor shower, and cold plunge offer spa-like relaxation, while the wood-fired pizza oven, outdoor bar, and firepit create exceptional gathering spaces. Extensive, thoughtfully constructed walking trails wind throughout the grounds, complemented by aromatic and carefully curated gardens. A charming children's playhouse/bunkie, pool cabana, and 3 decks further enhance this one-of-a-kind outdoor setting. Inside, expansive windows fill the home with natural light and bring the outdoors in. The modern kitchen features marble countertops, stainless steel appliances, and a striking backsplash, flowing into the dining area. The living room is anchored by a stunning brick accent wall and wood-burning fireplace, while a home office with built-in desk and outdoor access provides a serene workspace. The main floor primary suite is a tranquil escape with a luxurious 4-pc ensuite and walk-in shower. Upstairs, 3 spacious bedrooms and 2 well-appointed baths provide comfort for family and guests. The 3rd floor loft serves as a wellness sanctuary with an infrared sauna and custom built-in sauna. Additional highlights include heated marble bathroom floors, new hardwood flooring, and a custom floor-to-ceiling glass wine cellar. Designed for peace of mind, the home features a backup generator, air quality systems, water treatment, and major electrical upgrades. Elegant, modern and immersed in nature - 2814 Forks of the Credit Road leaves nothing to be desired. (id:5764)

2814 Forks Of The Credit Road, Caledon

Listing courtesy of SAM MCDADI REAL ESTATE INC..

$2,999,000

5 Beds ⋅ 6 Baths ⋅ W13490940 MLS® #

Discover a truly unique and breathtaking country estate where nature, privacy, and exceptional design come together in perfect harmony. Set on a picturesque 2.71 acres and ideally positioned between the Pulpit Club, Caledon Mountain Trout Club, Caledon Ski Club, Brampton Flying Club, and along the Bruce Trail, this magnificent property offers an unmatched lifestyle within close proximity to the city. A resort-like sanctuary awaits, designed for both grand entertaining and quiet, restorative living. An inground saltwater pool, outdoor shower, and cold plunge offer spa-like relaxation, while the wood-fired pizza oven, outdoor bar, and firepit create exceptional gathering spaces. Extensive, thoughtfully constructed walking trails wind throughout the grounds, complemented by aromatic and carefully curated gardens. A charming children's playhouse/bunkie, pool cabana, and 3 decks further enhance this one-of-a-kind outdoor setting. Inside, expansive windows fill the home with natural light and bring the outdoors in. The modern kitchen features marble countertops, stainless steel appliances, and a striking backsplash, flowing into the dining area. The living room is anchored by a stunning brick accent wall and wood-burning fireplace, while a home office with built-in desk and outdoor access provides a serene workspace. The main floor primary suite is a tranquil escape with a luxurious 4-pc ensuite and walk-in shower. Upstairs, 3 spacious bedrooms and 2 well-appointed baths provide comfort for family and guests. The 3rd floor loft serves as a wellness sanctuary with an infrared sauna and custom built-in sauna. Additional highlights include heated marble bathroom floors, new hardwood flooring, and a custom floor-to-ceiling glass wine cellar. Designed for peace of mind, the home features a backup generator, air quality systems, water treatment, and major electrical upgrades. Elegant, modern and immersed in nature - 2814 Forks of the Credit Road leaves nothing to be desired.

2814 Forks Of The Credit Road, Caledon

Listing courtesy of SAM MCDADI REAL ESTATE INC..

$959,999

5 Beds ⋅ 3 Baths ⋅ W13489596 MLS® #

Beautiful 3+2 Bedroom Bungalow with a WALK OUT BASEMENT!! Welcome to this stunning fully renovated bungalow nestled in the heart of Alton. This home features 3 spacious bedrooms on the main floor plus 2 full washrooms and a beautifully finished basement with 2 additional bedrooms and a 4 pc bathroom perfect for extended family or guests. Enjoy your private backyard oasis with an in-ground pool, relaxing hot tub, and plenty of space for entertaining on this expansive lot. A true blend of comfort, style, and outdoor luxury, this home has it all! Close to all major amenities.

32 Caledon Street, Caledon

Listing courtesy of RE/MAX REALTY SERVICES INC..

$1,299,000

4 Beds ⋅ 4 Baths ⋅ W13489488 MLS® #

Welcome to 23 Deer Valley Drive, a beautifully maintained all brick family home set on a premium 142 foot deep lot in one of Bolton's most established family neighbourhoods. Lovingly cared for by its original owners, this home has been the backdrop for years of family memories and is ready to welcome its next chapter. Pride of ownership is evident throughout, thoughtfully updated over the years. The main floor offers a functional layout with a spacious formal living room, separate dining room, and a warm family room with a wood burning fireplace overlooking the backyard. The bright eat in kitchen features a breakfast area with a walkout to the patio. Direct access from the garage into the laundry and mudroom adds everyday convenience. Upstairs you will find four generous bedrooms, including a spacious primary retreat with a large walk in closet, private ensuite, and peaceful views overlooking the backyard and Foundry Park. Two full bathrooms on the upper level provide plenty of space for a growing family. The finished basement offers incredible flexibility with a large recreation room, bar area, additional sitting room with a bio flame fireplace, a bathroom, workshop, cold room, and plenty of storage. The backyard is designed for making memories, complete with a solar heated saltwater in-ground pool, stamped concrete patio, mature landscaping, and open views of the park behind. Whether you are hosting family and friends or enjoying a quiet evening at home, this is a space you will appreciate all summer long. This home has been meticulously maintained and thoughtfully improved over the years. Located close to excellent schools, parks, trails, recreation, shopping, restaurants, and all the amenities that make Bolton such a wonderful place to call home, this is a rare opportunity to own a home that has been truly loved and exceptionally cared for.

23 Deer Valley Drive, Caledon

Listing courtesy of RE/MAX REAL ESTATE CENTRE INC..

$1,389,000

5 Beds ⋅ 2 Baths ⋅ W13489022 MLS® #

Welcome to this charming fully renovated bungalow located in the desirable and family-friendly community of Caledon Village. This carpet-free home features a bright and spacious living room with a custom built-in media wall and LED lighting, along with cozy fireplaces in both the living and family rooms. The updated kitchen offers quartz countertops and porcelain tile flooring. Spacious family room with separate access from the front yard and walk-out access to the backyard, offering added convenience and functionality. Basement has a wet bar. Situated on a fully fenced lot with a beautiful inground saltwater pool, perfect for summer entertaining. Enjoy the front porch deck with modern glass railings. Finished basement with 2 bedrooms provides additional living space ideal for extended family or guests. Conveniently located close to parks, schools, amenities, and within walking distance to Hwy 10.

6 Maple Grove Road, Caledon

Listing courtesy of RE/MAX REAL ESTATE CENTRE INC..

$1,349,000

3 Beds ⋅ 3 Baths ⋅ W13478666 MLS® #

Welcome to this beautifully renovated country retreat situated on a spectacular 108' x 235' lot in Caledon Village. Surrounded by conservation land at both the front and rear, this exceptional property offers a rare combination of privacy, nature, and neighbourhood living.Extensively updated throughout, this move-in-ready home features over 2,000 sq. ft. of finished living space, modern finishes, spacious principal rooms, and a thoughtfully redesigned layout ideal for family living and entertaining. The stunning kitchen showcases contemporary cabinetry, a large centre island, ample storage, and overlooks the backyard oasis.Step outside and experience your own private resort. The fully fenced in-ground saltwater pool is complemented by an expansive custom two-level deck, covered outdoor living area, and a 14' x 12' gazebo, creating the perfect setting for summer entertaining, family gatherings, or quiet evenings surrounded by nature.The beautifully landscaped property includes fruit-bearing apple, pear, and cherry trees, and a custom-built chicken coop offering the opportunity for a hobby-farm lifestyle. The expansive backyard provides exceptional space for recreation while enjoying protected conservation views and no rear neighbours.The finished lower level offers a spacious family room with fireplace, dedicated recreation space, and an upgraded laundry room featuring a modern 3-piece bathroom. Additional highlights include an oversized garage with extended storage space, metal roof, updated finishes throughout, and ample parking.Located in a desirable family-friendly enclave of Caledon Village, this rare offering combines modern comfort, outdoor living, and the tranquility of nature while remaining conveniently close to major commuter routes, schools, parks, and amenities. A truly exceptional property where every season can be enjoyed from the comfort of your own private retreat. (id:5764)

24 Mcgregor Drive, Caledon

Listing courtesy of HOMELIFE SUPERSTARS REAL ESTATE LIMITED.

$1,349,000

3 Beds ⋅ 3 Baths ⋅ W13478666 MLS® #

Welcome to this beautifully renovated country retreat situated on a spectacular 108' x 235' lot in Caledon Village. Surrounded by conservation land at both the front and rear, this exceptional property offers a rare combination of privacy, nature, and neighbourhood living.Extensively updated throughout, this move-in-ready home features over 2,000 sq. ft. of finished living space, modern finishes, spacious principal rooms, and a thoughtfully redesigned layout ideal for family living and entertaining. The stunning kitchen showcases contemporary cabinetry, a large centre island, ample storage, and overlooks the backyard oasis.Step outside and experience your own private resort. The fully fenced in-ground saltwater pool is complemented by an expansive custom two-level deck, covered outdoor living area, and a 14' x 12' gazebo, creating the perfect setting for summer entertaining, family gatherings, or quiet evenings surrounded by nature.The beautifully landscaped property includes fruit-bearing apple, pear, and cherry trees, and a custom-built chicken coop offering the opportunity for a hobby-farm lifestyle. The expansive backyard provides exceptional space for recreation while enjoying protected conservation views and no rear neighbours.The finished lower level offers a spacious family room with fireplace, dedicated recreation space, and an upgraded laundry room featuring a modern 3-piece bathroom. Additional highlights include an oversized garage with extended storage space, metal roof, updated finishes throughout, and ample parking.Located in a desirable family-friendly enclave of Caledon Village, this rare offering combines modern comfort, outdoor living, and the tranquility of nature while remaining conveniently close to major commuter routes, schools, parks, and amenities. A truly exceptional property where every season can be enjoyed from the comfort of your own private retreat.

24 Mcgregor Drive, Caledon

Listing courtesy of HOMELIFE SUPERSTARS REAL ESTATE LIMITED.

$1,399,995

4 Beds ⋅ 4 Baths ⋅ W13478224 MLS® #

OPEN HOUSE - SUNDAY JULY 26TH 2PM TO 4PM * The perfect home for summer, this executive residence is ideally located in the heart of Caledon East. Offering four spacious bedrooms and three bathrooms, the home welcomes you with a large foyer and an impressive double staircase, reflecting the care and thoughtful updates it has received over time. Hardwood flooring extends throughout most principal rooms, while the kitchen features stainless steel appliances and a generous breakfast area with a walkout to the pool. The kitchen overlooks the sunken family room, which offers an additional walkout and creates a comfortable, connected living space. The backyard is a beautifully designed private oasis, complete with a stunning 20x40 saltwater pool with two stairways, a separate change house with a two-piece bathroom, and an outdoor shower. Expansive stone patios and walkways include integrated conversation areas, complemented by a fully equipped cabana/bar with hot and cold running water and granite countertops. Recent pool updates include a brand-new liner in 2026, a new high-output Natural Gas heater in 2024, and a new pump motor in 2024. Additional exterior highlights include extensive new fencing completed last year and a full underground sprinkler system. The unfinished basement offers exceptional potential, featuring 1200+ sqft with high ceilings and a completely separate entrance from the garage.

13 Mckee Drive, Caledon

Listing courtesy of ROYAL LEPAGE MEADOWTOWNE REALTY.

$1,299,000

3 Beds ⋅ 2 Baths ⋅ W13475252 MLS® #

This is the opportunity you've been waiting for! Located in a family-friendly neighbourhood surrounded by multi-million-dollar homes, this property offers exceptional potential and outstanding value. Welcome to 44 Pineridge Drive, a charming bungalow nestled in the sought-after Gibson Lake community. Featuring a spacious open-concept layout, this home offers a large kitchen with plenty of storage, a generous dining room with a walkout to the patio, and an inground concretepool-perfect for entertaining family and friends. The finished basement provides additional living space, complete with a cozy fireplace, above-grade windows, and a separate side entrance, offering excellent flexibility for extended family living or future possibilities. Conveniently located close to schools, parks, and golf courses, this home combines comfort, convenience, and incredible potential. Don't miss this fantastic opportunity to own in a highly desirable location!

44 Pineridge Drive, Caledon

Listing courtesy of REMAX YOUR COMMUNITY REALTY.

$1,199,000

4 Beds ⋅ 2 Baths ⋅ W13468334 MLS® #

Welcome to Hilltop Drive. One of Caledon East's most desirable communities. This beautifully updated 4-level side-split offers the ideal blend of modern style, space, and functionality. Featuring four bedrooms and four distinct living levels, this home has been thoughtfully designed to accommodate every stage of family life. At the heart of the home is the stunning renovated kitchen, showcasing an impressive 5' x 9' island, modern cabinetry, stainless appliances, a temperature-controlled wine fridge, abundant storage, and stylish finishes throughout. The adjoining family room is bright and inviting, complete with a walk-out to the patio that seamlessly blends indoor and outdoor living. The upper-level features three spacious bedrooms and a beautifully renovated 4-piece bathroom. On the lower level, you'll find an additional family room with a second walk-out to the yard, a renovated 3-piece bathroom, a fourth bedroom, and a generous laundry room, offering the perfect setup for growing families, multi-generational living, or welcoming overnight guests. The finished fourth lower level provides even more versatile space, with another cozy family room, a beautiful wet bar and seating area, and an abundance of storage space. Summers just got better as you enjoy your own private backyard oasis, surrounded by mature trees, extensive stonework, large garden shed, exceptional privacy, and a beautiful saltwater above-ground pool - the perfect setting for entertaining family and friends. Don't miss this incredible opportunity to call this exceptional Caledon East property your forever home!

25 Hilltop Drive, Caledon

Listing courtesy of ONE PERCENT REALTY LTD..

$3,588,000

4 Beds ⋅ 5 Baths ⋅ W13466736 MLS® #

Welcome To 258 Amos Drive-Luxury Estate On a Conservation-Backed Lot. Welcome To This Stunning 4-Bedroom , 5-Bathroom estate nestled on a Premium 183 X 758 Ft Lot with breathtaking , unobstructed views . Perfect for relaxation or entertaining, The backyard is private oasis featuring : Salt Water Pool 18 Feet X 36 Feet ,All-Season Cedar Sauna, All-Season Pool House With Washroom & Steam Shower, professionally landscaped grounds with sprinkler system front and back. Natural stone entrance porch and interlocking pathway .Inside, enjoy over 4800 sq.ft. of refined luxury with 8" Vintage Hardwood Floors Throughout, Pot Lights, and thoughtful, smart design. The gourmet kitchen is a chef's dream, featuring custom cabinetry with soft-close doors, walk-in pantry, Oversized Centre Island , Built-In Thermador appliances And A Breakfast Area With Walkout To A 21' X 24' Deck Overlooking The Backyard .The Family Room Features A Custom Wall TV Unit, Perfect For Cosy Movie Nights Or Entertaining Guests. The Primary Bedroom Serves As A Private Retreat With Sitting Area ,Two Walk-in Closets And A 5-piece Ensuite. All Closets in the Home Feature Professionally Installed Organizers. Additional Bedrooms Offer Ensuite Access And Walk-in Closets.The Home Also Offers 4 Car Garages With 2 Electrical Outlets For EV'S And A Heater In The Main Garage Area, Combining Convenience And Functionality. Whether Enjoying A Sunrise Coffee, Hosting Friends, Or Simply Relaxing In Style, This Property Offers Unparalleled Comfort , Luxury And Lifestyle - Truly-One-Of-A-Kind!

258 Amos Drive, Caledon

Listing courtesy of TFN REALTY INC..

$8,000,000

5 Beds ⋅ 5 Baths ⋅ W13462682 MLS® #

Exceptional 10-acre country estate offering privacy, versatility, and outstanding lifestyle amenities. This spacious 2-storey brick home features a renovated kitchen (2022) with large island, farmhouse sink, pot fillers, stainless steel appliances, and abundant cabinetry. Enjoy oversized principal rooms, a cozy family room with fireplace and walkout to a deck and interlocking patio, plus 4 bedrooms including a primary suite with spa-inspired ensuite. The finished basement with separate entrance includes a second kitchen, rec room, 5-pc bath, laundry, and ample storage. A bright self-contained studio apartment with separate entrance, kitchen, bedroom, bath, and laundry provides ideal space for extended family or rental income. Outside, discover an above ground heated saltwater pool, pond, greenhouse with hydro, detached workshop with hydro, water, 2 bays and room for 5 vehicles, 2 woodsheds, and a heated 4-car attached garage. Updates include septic and furnace (2022), exterior doors (2022), and roof, soffits & eaves (2016).Located outside of the Greenbelt, close to the proposed HWY 413, this exceptional property offers the perfect blend of immediate multi generational enjoyment and long-term potential, positioned within an evolving and transitioning area poised for future growth. PROPERTY (INTERIOR -OR- EXTERIOR) TO BE VIEWED BY APPOINTMENT ONLY - PLEASE DO NOT APPROACH THE LOT UNLESS A REALTOR IS ACCOMPANYING YOU FOR YOUR SCHEDULED APPOINTMENT - THANKS FOR BEING RESPECTFUL TO THE SELLER(S). (id:5764)

13289 Innis Lake Road, Caledon

Listing courtesy of RE/MAX PROFESSIONALS INC..

$1,699,000

6 Beds ⋅ 3 Baths ⋅ W13462988 MLS® #

Welcome to the country escape everyone talks about but rarely finds. Tucked away on a private, quiet court in rural Caledon, this beautifully renovated home sits on 2.72 acres of pure tranquility, offering the perfect blend of modern comfort and peaceful country living, just a short drive from Caledon East, Caledon Village, and Orangeville. Step outside and experience your own backyard haven: a heated inground saltwater pool, a cozy fire pit for unforgettable evenings under the stars, ample space for kids to run and play freely, concrete pad for basketball court or ice rink in the Winter, garden beds and a walking trail, all framed by mature trees for the ultimate privacy. With a driveway that accommodates 10 vehicles, this property is designed for both relaxation and gathering. Inside, over $300K in upgrades have transformed this home into a turnkey retreat. Stunning wide-plank luxury vinyl flooring, fresh paint and pot lights throughout. The thoughtful main floor layout includes a formal living room with bay window, and a beautiful kitchen open to the dining area with extended cabinetry, additional sink and walkout to the patio. A spacious mudroom/laundry room offers direct garage access and sliding doors to a fenced dog pen. The two-car garage includes a convenient mezzanine for extra storage. With two bedrooms and a full 3-piece bath on the main level, plus a second-floor primary retreat, additional bedroom, charming playroom with reading nook, and a spa-inspired 5-piece bath, there's space for the whole family. The newly renovated basement adds even more versatility with two bedrooms, a full 3-piece bath, and a large, bright recreation space complete with an electric fireplace, perfect for movie nights, games, or a home gym. Professionally landscaped and meticulously maintained, this is your opportunity to leave behind the city grind and subdivision life and finally own the space, privacy, and lifestyle you've been dreaming of. (id:5764)

12 Glenn Court, Caledon

Listing courtesy of RE/MAX REALTY SERVICES INC..

$1,699,000

6 Beds ⋅ 3 Baths ⋅ W13462988 MLS® #

Welcome to the country escape everyone talks about but rarely finds. Tucked away on a private, quiet court in rural Caledon, this beautifully renovated home sits on 2.72 acres of pure tranquility, offering the perfect blend of modern comfort and peaceful country living, just a short drive from Caledon East, Caledon Village, and Orangeville. Step outside and experience your own backyard haven: a heated inground saltwater pool, a cozy fire pit for unforgettable evenings under the stars, ample space for kids to run and play freely, concrete pad for basketball court or ice rink in the Winter, garden beds and a walking trail, all framed by mature trees for the ultimate privacy. With a driveway that accommodates 10 vehicles, this property is designed for both relaxation and gathering. Inside, over $300K in upgrades have transformed this home into a turnkey retreat. Stunning wide-plank luxury vinyl flooring, fresh paint and pot lights throughout. The thoughtful main floor layout includes a formal living room with bay window, and a beautiful kitchen open to the dining area with extended cabinetry, additional sink and walkout to the patio. A spacious mudroom/laundry room offers direct garage access and sliding doors to a fenced dog pen. The two-car garage includes a convenient mezzanine for extra storage. With two bedrooms and a full 3-piece bath on the main level, plus a second-floor primary retreat, additional bedroom, charming playroom with reading nook, and a spa-inspired 5-piece bath, there's space for the whole family. The newly renovated basement adds even more versatility with two bedrooms, a full 3-piece bath, and a large, bright recreation space complete with an electric fireplace, perfect for movie nights, games, or a home gym. Professionally landscaped and meticulously maintained, this is your opportunity to leave behind the city grind and subdivision life and finally own the space, privacy, and lifestyle you've been dreaming of.

12 Glenn Court, Caledon

Listing courtesy of RE/MAX REALTY SERVICES INC..

$8,000,000

5 Beds ⋅ 5 Baths ⋅ W13462682 MLS® #

Exceptional 10-acre country estate offering privacy, versatility, and outstanding lifestyle amenities. This spacious 2-storey brick home features a renovated kitchen (2022) with large island, farmhouse sink, pot fillers, stainless steel appliances, and abundant cabinetry. Enjoy oversized principal rooms, a cozy family room with fireplace and walkout to a deck and interlocking patio, plus 4 bedrooms including a primary suite with spa-inspired ensuite. The finished basement with separate entrance includes a second kitchen, rec room, 5-pc bath, laundry, and ample storage. A bright self-contained studio apartment with separate entrance, kitchen, bedroom, bath, and laundry provides ideal space for extended family or rental income. Outside, discover an above ground heated saltwater pool, pond, greenhouse with hydro, detached workshop with hydro, water, 2 bays and room for 5 vehicles, 2 woodsheds, and a heated 4-car attached garage. Updates include septic and furnace (2022), exterior doors (2022), and roof, soffits & eaves (2016).Located outside of the Greenbelt, close to the proposed HWY 413, this exceptional property offers the perfect blend of immediate multi generational enjoyment and long-term potential, positioned within an evolving and transitioning area poised for future growth. PROPERTY (INTERIOR -OR- EXTERIOR) TO BE VIEWED BY APPOINTMENT ONLY - PLEASE DO NOT APPROACH THE LOT UNLESS A REALTOR IS ACCOMPANYING YOU FOR YOUR SCHEDULED APPOINTMENT - THANKS FOR BEING RESPECTFUL TO THE SELLER(S).

13289 Innis Lake Road, Caledon

Listing courtesy of RE/MAX PROFESSIONALS INC..

$1,125,000

4 Beds ⋅ 2 Baths ⋅ W13455320 MLS® #

A Storybook Country Escape in the Heart of Caledon! Tucked among mature trees and rolling hills, this one-of-a-kind country retreat offers the perfect blend of character, privacy, and outdoor living. Set on just over an acre, the property feels worlds away from the hustle of everyday life, yet remains conveniently close to charming villages, trails, ski hills, and local amenities. Inside, warmth and authenticity greet you at every turn. Soaring beamed ceilings, wide plank floors, and a stunning stone fireplace create an atmosphere that is both inviting and unforgettable. The spacious living and dining areas are designed for gathering with family and friends, while large windows frame beautiful views of the surrounding landscape. Upstairs, the primary suite is a peaceful sanctuary with its own sitting area and direct access to the backyard oasis. A third-level loft and additional bedroom provide flexible space for guests, a home office, creative studio, or quiet retreat. Outside is where this property truly shines. Wander along flagstone pathways through established perennial gardens, spend summer afternoons lounging by the pool, and gather around the firepit under a canopy of stars. The detached workshop offers endless possibilities for hobbyists, artists, gardeners, or extra storage. Whether you're searching for a full-time residence or a weekend escape, this remarkable property offers something increasingly difficult to find - a home with soul, surrounded by nature, where every season brings a new reason to fall in love.

20909 Shaws Creek Road, Caledon

Listing courtesy of CENTURY 21 MILLENNIUM INC..

$2,899,999

5 Beds ⋅ 6 Baths ⋅ W13453766 MLS® #

Rarely does a property come to market that truly offers it all. Welcome to 11 Damascus Drive, a beautifully renovated estate home set on a private 2.55-acre lot in one of Caledon East's most sought-after cul-de-sacs.Boasting over 3,800 sq. ft. of finished living space, including a legal in-law suite, this exceptional property has been extensively updated from top to bottom and is completely move-in ready. The heart of the home is a stunning chef-inspired kitchen featuring quartz countertops, a waterfall island, premium built-in appliances including a JennAir refrigerator, and a fully equipped spice kitchen. Hardwood flooring, designer finishes, updated windows and doors, modern lighting, and beautifully renovated bathrooms elevate every space.Designed with both family living and entertaining in mind, the home offers spacious principal rooms, a welcoming family room with a striking fireplace feature wall, and a luxurious primary retreat complete with a spa-inspired ensuite and walk-through dressing area. The finished lower level provides additional living space for family, guests, or recreation.A standout feature is the legal in-law suite with its own entrance, kitchen, bedroom area, and full bathroom, offering incredible flexibility for multigenerational living or future income potential.Step outside and discover your own private backyard oasis. Surrounded by mature trees, enjoy summer days by the large in-ground pool, recently updated with a new liner, pump, heater, and filtration system, along with an expansive deck perfect for relaxing or entertaining. A triple-car garage and circular driveway complete this impressive estate setting.Offering the perfect balance of privacy and convenience, this remarkable property is just minutes from schools, shopping, and everyday amenities. Luxury, space, and versatility-11 Damascus Drive truly has it all.

11 Damacus Drive, Caledon

Listing courtesy of FLOWER CITY SIGNATURE REALTY INC..

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