$8,499,900 Set on 5 forested acres along the Milton/Halton Hills border, this estate designed by the celebrated David Small Designs stands as one of the most significant private residences ever to come to market in the Greater Toronto Area. With 16,260 sqft of finished living space, 6 bedrooms, and amenities that rival the finest private resorts, this is not a home that can be replicated. Properties of this scale, this pedigree, and this proximity to the city are extraordinarily rare. The Manor House - From the moment the stone manor facade comes into view, the architecture announces something genuinely exceptional. Inside, principal rooms flow with a rare combination of grandeur and warmth, where coffered ceilings, carved stone fireplaces, and oversized windows frame the surrounding forest at every turn. A chef's kitchen with granite-slab island anchors the heart of the home, while whole-home automation, integrated audio, and geothermal heating and cooling reflect the engineering behind the elegance. The primary wing occupies its own realm entirely, with a dedicated office, music room, wood-lined sauna suite, library with fireplace, private kitchenette, and a secluded hot tub deck exclusive to the primary wing and completely separate from the rest of the home. A fully self-contained in-law suite with its own private entrance offers a level of flexibility and independence that truly sets this estate apart. Outdoors, five forested acres offer a resort-style pool, outdoor kitchen, sport court, vegetable garden, and illuminated walking trails. Two triple-car garages with 2 vehicle lifts accommodate the most discerning collector. Below grade, a two-lane bowling alley, golf simulator, home theatre for 8, 800-bottle wine cellar, wet bar, and spa room with walkout make every weekend extraordinary.45 minutes to downtown Toronto. 30 minutes to Pearson International Airport. Absolute privacy without sacrificing connectivity. 6 Beds ⋅ 8 Baths ⋅ W12438371 MLS Set on 5 forested acres along the Milton/Halton Hills border, this estate designed by the celebrated David Small Designs stands as one of the most significant private residences ever to come to market in the Greater Toronto Area. With 16,260 sqft of finished living space, 6 bedrooms, and amenities that rival the finest private resorts, this is not a home that can be replicated. Properties of this scale, this pedigree, and this proximity to the city are extraordinarily rare. The Manor House - From the moment the stone manor facade comes into view, the architecture announces something genuinely exceptional. Inside, principal rooms flow with a rare combination of grandeur and warmth, where coffered ceilings, carved stone fireplaces, and oversized windows frame the surrounding forest at every turn. A chef's kitchen with granite-slab island anchors the heart of the home, while whole-home automation, integrated audio, and geothermal heating and cooling reflect the engineering behind the elegance. The primary wing occupies its own realm entirely, with a dedicated office, music room, wood-lined sauna suite, library with fireplace, private kitchenette, and a secluded hot tub deck exclusive to the primary wing and completely separate from the rest of the home. A fully self-contained in-law suite with its own private entrance offers a level of flexibility and independence that truly sets this estate apart. Outdoors, five forested acres offer a resort-style pool, outdoor kitchen, sport court, vegetable garden, and illuminated walking trails. Two triple-car garages with 2 vehicle lifts accommodate the most discerning collector. Below grade, a two-lane bowling alley, golf simulator, home theatre for 8, 800-bottle wine cellar, wet bar, and spa room with walkout make every weekend extraordinary.45 minutes to downtown Toronto. 30 minutes to Pearson International Airport. Absolute privacy without sacrificing connectivity. 13160 Nassagaweya Esquesing Townline, Milton
$5,849,999 A Rare Executive Estate. Unmatched Privacy. Limitless Possibilities. Set on 5.76 acres of private, tree-lined grounds, this custom-built estate offers a secluded retreat just minutes from the GTA. Meticulously crafted by its original owners, the home perfectly balances architectural presence with everyday livability, delivering space, privacy, and quality that is nearly impossible to replicate. Step inside to a dramatic 22-foot foyer with a floating staircase, where floor-to-ceiling windows frame serene natural views and flood the home with sunlight. Designed for both grand-scale entertaining and family living, the heart of the home is a chef's kitchen with dual oversized islands seating up to 14, premium appliances, and effortless flow to the sunroom and outdoor kitchen-perfect for gatherings year-round. Indulge in resort-style amenities: a private spa with a 10-person jacuzzi, steam room, and sauna, a fully equipped home theatre, gym, games area, and full bar, plus a private elevator for ultimate convenience. A three-bedroom guest suite above the garage offers flexibility for extended family, live-in support, or visitors. The outdoors is equally spectacular: heated saltwater pool, two fire pit areas, tennis and basketball courts, walking trails around a private pond, and multiple terraces for entertaining or quiet reflection-all in total privacy. Sustainably built with solar and geothermal systems, full smart-home integration, and dual septic systems, this estate blends luxury, efficiency, and enduring value. This is a rare legacy property offering privacy, land, lifestyle, and unmatched proximity to urban centres. Don't miss your chance-show your clients this extraordinary estate today. 9 Beds ⋅ 10 Baths ⋅ W13426054 MLS A Rare Executive Estate. Unmatched Privacy. Limitless Possibilities. Set on 5.76 acres of private, tree-lined grounds, this custom-built estate offers a secluded retreat just minutes from the GTA. Meticulously crafted by its original owners, the home perfectly balances architectural presence with everyday livability, delivering space, privacy, and quality that is nearly impossible to replicate. Step inside to a dramatic 22-foot foyer with a floating staircase, where floor-to-ceiling windows frame serene natural views and flood the home with sunlight. Designed for both grand-scale entertaining and family living, the heart of the home is a chef's kitchen with dual oversized islands seating up to 14, premium appliances, and effortless flow to the sunroom and outdoor kitchen-perfect for gatherings year-round. Indulge in resort-style amenities: a private spa with a 10-person jacuzzi, steam room, and sauna, a fully equipped home theatre, gym, games area, and full bar, plus a private elevator for ultimate convenience. A three-bedroom guest suite above the garage offers flexibility for extended family, live-in support, or visitors. The outdoors is equally spectacular: heated saltwater pool, two fire pit areas, tennis and basketball courts, walking trails around a private pond, and multiple terraces for entertaining or quiet reflection-all in total privacy. Sustainably built with solar and geothermal systems, full smart-home integration, and dual septic systems, this estate blends luxury, efficiency, and enduring value. This is a rare legacy property offering privacy, land, lifestyle, and unmatched proximity to urban centres. Don't miss your chance-show your clients this extraordinary estate today. 13311 Sixth Line, Milton
$3,549,000 A truly one-of-a-kind legacy estate featuring two residences, an expansive workshop, indoor hockey rink, private aircraft hangar, resort-style backyard retreat, and countless other amenities. Escape to your own private countryside retreat on over 42.5 spectacular acres, where luxury, recreation, and natural beauty come together in perfect harmony. The grounds offer endless opportunities to explore, with scenic hiking and ATV trails, a charming chicken coop, mini barn for small animals, and an abundance of maple trees for syrup production. Adding to the property's unique appeal is a 50' x 100' barn currently configured as a private hockey rink, along with a private grass landing strip and airplane hangar for aviation enthusiasts. The main residence offers approximately 5,500 sq. ft. of finished living space with 4+1 bedrooms and 3.5 bathrooms. Designed for both comfort and functionality, it features spacious principal rooms, a dedicated office with custom built-ins, flexible studio space, and a large great room above the heated two-car garage. Outside, the property transforms into a resort-inspired oasis. Enjoy the inground fiberglass pool with waterfall features and lighting, hot tub, barrel sauna, and an expansive pavilion complete with a wood-burning stone fireplace and imported Portuguese pizza oven-ideal for year-round entertaining. A separate secondary residence provides exceptional flexibility for extended family, guests, or rental income. Featuring soaring 14-foot ceilings, an open-concept layout, one bedroom, one bathroom, and an attached heated four-car garage and barn, it is both stylish and functional. Whether you're searching for a family compound, recreational paradise, or luxury country estate, this remarkable property offers a lifestyle few can match. 5 Beds ⋅ 4 Baths ⋅ W13474578 MLS A truly one-of-a-kind legacy estate featuring two residences, an expansive workshop, indoor hockey rink, private aircraft hangar, resort-style backyard retreat, and countless other amenities. Escape to your own private countryside retreat on over 42.5 spectacular acres, where luxury, recreation, and natural beauty come together in perfect harmony. The grounds offer endless opportunities to explore, with scenic hiking and ATV trails, a charming chicken coop, mini barn for small animals, and an abundance of maple trees for syrup production. Adding to the property's unique appeal is a 50' x 100' barn currently configured as a private hockey rink, along with a private grass landing strip and airplane hangar for aviation enthusiasts. The main residence offers approximately 5,500 sq. ft. of finished living space with 4+1 bedrooms and 3.5 bathrooms. Designed for both comfort and functionality, it features spacious principal rooms, a dedicated office with custom built-ins, flexible studio space, and a large great room above the heated two-car garage. Outside, the property transforms into a resort-inspired oasis. Enjoy the inground fiberglass pool with waterfall features and lighting, hot tub, barrel sauna, and an expansive pavilion complete with a wood-burning stone fireplace and imported Portuguese pizza oven-ideal for year-round entertaining. A separate secondary residence provides exceptional flexibility for extended family, guests, or rental income. Featuring soaring 14-foot ceilings, an open-concept layout, one bedroom, one bathroom, and an attached heated four-car garage and barn, it is both stylish and functional. Whether you're searching for a family compound, recreational paradise, or luxury country estate, this remarkable property offers a lifestyle few can match. 13232 Fifth Line, Milton
$2,999,000 Escape to your own private 98 acre country estate where natural beauty, recreation, and rural living come together in perfect harmony. Featuring approximately 66 acres enrolled in the Managed Forest Tax Incentive Program, this remarkable property offers reduced property taxes while preserving a breathtaking landscape of enchanting forests, productive farm fields, rolling countryside, wetlands rich with wildlife, and a flowing creek. Nature lovers, bird watchers, hunters, hikers, and outdoor enthusiasts will appreciate the extensive private trail system, serene pond, fascinating caves, and the abundance of deer, wild turkeys, songbirds, and native wildlife that call this property home. Two separate driveways provide excellent access and flexibility for future use. A charming circa 1880 farmhouse, thoughtfully expanded with a substantial addition in 1998, offering +/- 2,800 sq. ft. above ground. Blending historic character with modern comfort, the updated home is designed to capture the surrounding views from nearly every room. A bright and spacious living room with vaulted ceilings creates an open and welcoming atmosphere, while the large dining room is ideal for entertaining family and friends. The modern kitchen features a beverage centre with its own sink, making gatherings effortless. Both the living and dining areas overlook the spectacular countryside, providing peaceful year round views. The 2nd floor offers the loft style primary bedroom, a cozy sitting dressing area and a 5 pc ensuite. The full unfinished walk out basement presents exceptional potential for additional living space, a recreation area, workshop, or multigenerational living. A rear deck overs panoramic views across your private four season paradise. The barn provides excellent storage, hobby, agricultural, or recreational opportunities. Conveniently located just 5 minutes to Rockwood, 10 minutes to Acton, 20 minutes to Guelph, and approximately 18 minutes to Highway 401. Paved Road. 2 Beds ⋅ 2 Baths ⋅ W13441158 MLS Escape to your own private 98 acre country estate where natural beauty, recreation, and rural living come together in perfect harmony. Featuring approximately 66 acres enrolled in the Managed Forest Tax Incentive Program, this remarkable property offers reduced property taxes while preserving a breathtaking landscape of enchanting forests, productive farm fields, rolling countryside, wetlands rich with wildlife, and a flowing creek. Nature lovers, bird watchers, hunters, hikers, and outdoor enthusiasts will appreciate the extensive private trail system, serene pond, fascinating caves, and the abundance of deer, wild turkeys, songbirds, and native wildlife that call this property home. Two separate driveways provide excellent access and flexibility for future use. A charming circa 1880 farmhouse, thoughtfully expanded with a substantial addition in 1998, offering +/- 2,800 sq. ft. above ground. Blending historic character with modern comfort, the updated home is designed to capture the surrounding views from nearly every room. A bright and spacious living room with vaulted ceilings creates an open and welcoming atmosphere, while the large dining room is ideal for entertaining family and friends. The modern kitchen features a beverage centre with its own sink, making gatherings effortless. Both the living and dining areas overlook the spectacular countryside, providing peaceful year round views. The 2nd floor offers the loft style primary bedroom, a cozy sitting dressing area and a 5 pc ensuite. The full unfinished walk out basement presents exceptional potential for additional living space, a recreation area, workshop, or multigenerational living. A rear deck overs panoramic views across your private four season paradise. The barn provides excellent storage, hobby, agricultural, or recreational opportunities. Conveniently located just 5 minutes to Rockwood, 10 minutes to Acton, 20 minutes to Guelph, and approximately 18 minutes to Highway 401. Paved Road. 13489 Fourth Line Nassagaweya N/A, Milton
$2,990,000 This 98 acres farmstead offers a rare combination of productive farmland, natural beauty and recreational opportunities. 30 +/- acres workable farmland, complemented by 66 acres of managed forest complete with private trails, a flowing creek, pond, remarkable natural caves. With two road frontage accesses on a paved road, the property offers flexibility for farming operations, recreational use, or multi-generational living. Ideal for horses, cattle, hobby farming, or outdoor enthusiasts seeking a private country retreat. The property includes a bank barn, chicken coop, and additional space for livestock, equipment, hobbies, or storage. Enjoy scenic trailways throughout the property, perfect for walking, horseback riding, ATV use, or exploring the peaceful countryside setting. 2,800 SF farmhouse offers an addition to the existing 1880 Farmhouse, which features a bright living room with cathedral ceiling and large windows overlooking the property. The spacious dining room is ideal for entertaining, while the updated kitchen includes a wet bar and ample cupboard space. Two staircases provide convenient access throughout the home and add to its character and functionality. Generous-sized bedrooms offer comfortable living space, including a loft-style primary bedroom with peaceful countryside views. Updated bathrooms on both the main and second floors add modern convenience. Additional bedroom, office, and walk out basement provide flexibility for growing families or working from home. The unfinished walk-out basement offers excellent potential for future living space or customization. Relax on the back deck while taking in panoramic views of the surrounding landscape. Conveniently located approximately 5 minutes to Rockwood, 10 minutes to Acton, 18 minutes to Highway 401, and 20 minutes to Guelph. Property is being sold in "as-is, where-is" condition. OFA farmed and HST maybe in addition to the purchase price. 2 Baths ⋅ W13443306 MLS This 98 acres farmstead offers a rare combination of productive farmland, natural beauty and recreational opportunities. 30 +/- acres workable farmland, complemented by 66 acres of managed forest complete with private trails, a flowing creek, pond, remarkable natural caves. With two road frontage accesses on a paved road, the property offers flexibility for farming operations, recreational use, or multi-generational living. Ideal for horses, cattle, hobby farming, or outdoor enthusiasts seeking a private country retreat. The property includes a bank barn, chicken coop, and additional space for livestock, equipment, hobbies, or storage. Enjoy scenic trailways throughout the property, perfect for walking, horseback riding, ATV use, or exploring the peaceful countryside setting. 2,800 SF farmhouse offers an addition to the existing 1880 Farmhouse, which features a bright living room with cathedral ceiling and large windows overlooking the property. The spacious dining room is ideal for entertaining, while the updated kitchen includes a wet bar and ample cupboard space. Two staircases provide convenient access throughout the home and add to its character and functionality. Generous-sized bedrooms offer comfortable living space, including a loft-style primary bedroom with peaceful countryside views. Updated bathrooms on both the main and second floors add modern convenience. Additional bedroom, office, and walk out basement provide flexibility for growing families or working from home. The unfinished walk-out basement offers excellent potential for future living space or customization. Relax on the back deck while taking in panoramic views of the surrounding landscape. Conveniently located approximately 5 minutes to Rockwood, 10 minutes to Acton, 18 minutes to Highway 401, and 20 minutes to Guelph. Property is being sold in "as-is, where-is" condition. OFA farmed and HST maybe in addition to the purchase price. 13489 Fourth Line Nassagaweya N/A, Milton
$2,500,000 Welcome to your private country retreat! A custom-built home where the journey home feels just as special as the destination. Built in 2010, set on approx 2.3 acres, this remarkable property offers a perfect blend of privacy, craftsmanship and modern country living. As you turn onto this quiet country court and follow the paved driveway, the feeling of seclusion begins immediately. As the home comes into view, the impressive stonework, cedar accents, exterior pot lighting and beautifully designed walkways welcome you to a home that has been thoughtfully crafted inside and out. Exterior hardscaping creates inviting outdoor spaces including covered front and rear porches. Open-concept main living area features soaring ceilings, rich architectural details and a dramatic floor-to-ceiling stone gas fireplace. A gourmet kitchen combines style and function with granite counters, large centre island and premium appliances. The adjoining breakfast area and great room are surrounded by large windows allowing natural light to pour in while showcasing the beautiful landscape beyond. The main floor offers a private primary bedroom with its own fireplace, a generous walk-in closet and a luxurious ensuite with a soaker tub & separate shower. Also on this level is a dedicated office overlooking the front of the property. Main level laundry. The second floor embraces the open design with a loft-style sitting/TV area, 2 additional bedrooms and 4-pc bathroom. In addition to approx 3475 sq. ft., the partially finished lower level offers 2,637 sq. ft. (approx) with roughed-in bathroom already in place. Oversized garage provides approx 800 sq. ft. for vehicles, hobbies, toys. Close to conservation areas, golf courses and surrounded by nature, this home offers peaceful country living with easy access to Milton, Guelph, Burlington, Oakville, Mississauga & Toronto. Mature trees, beautiful craftsmanship and thoughtful design come together to create a home you will be proud to call your own. 3 Beds ⋅ 3 Baths ⋅ W13480188 MLS Welcome to your private country retreat! A custom-built home where the journey home feels just as special as the destination. Built in 2010, set on approx 2.3 acres, this remarkable property offers a perfect blend of privacy, craftsmanship and modern country living. As you turn onto this quiet country court and follow the paved driveway, the feeling of seclusion begins immediately. As the home comes into view, the impressive stonework, cedar accents, exterior pot lighting and beautifully designed walkways welcome you to a home that has been thoughtfully crafted inside and out. Exterior hardscaping creates inviting outdoor spaces including covered front and rear porches. Open-concept main living area features soaring ceilings, rich architectural details and a dramatic floor-to-ceiling stone gas fireplace. A gourmet kitchen combines style and function with granite counters, large centre island and premium appliances. The adjoining breakfast area and great room are surrounded by large windows allowing natural light to pour in while showcasing the beautiful landscape beyond. The main floor offers a private primary bedroom with its own fireplace, a generous walk-in closet and a luxurious ensuite with a soaker tub & separate shower. Also on this level is a dedicated office overlooking the front of the property. Main level laundry. The second floor embraces the open design with a loft-style sitting/TV area, 2 additional bedrooms and 4-pc bathroom. In addition to approx 3475 sq. ft., the partially finished lower level offers 2,637 sq. ft. (approx) with roughed-in bathroom already in place. Oversized garage provides approx 800 sq. ft. for vehicles, hobbies, toys. Close to conservation areas, golf courses and surrounded by nature, this home offers peaceful country living with easy access to Milton, Guelph, Burlington, Oakville, Mississauga & Toronto. Mature trees, beautiful craftsmanship and thoughtful design come together to create a home you will be proud to call your own. 4320 Random Acres Road, Milton
$2,400,000 Discover a rare opportunity to own a fully equipped 10-acre rural estate designed for multigenerational living, hobby farming, equestrian use & luxury country living. Offering unmatched privacy, versatility & lifestyle amenities, this exceptional property blends functionality w/resort-style outdoor living just minutes from key amenities & commuter routes. The impressive 4,100 sq ft side-split residence is ideal for large or extended families, featuring 5 bdrms, 3 full baths, 2 full kitchens, home office & home theatre. The layout supports in-law suite potential & multigenerational living, w/2 main-floor bdrms each offering ensuite baths. The chef-inspired kitchen showcases 10' vaulted ceilings, oversized island, w/i pantry & abundant natural light, creating a warm & functional gathering space. Designed for both comfort & entertaining, the home includes multiple walkouts to an expansive deck overlooking the property, ideal for indoor-outdoor living & hosting. The land is a true highlight; offering a private, fully developed outdoor lifestyle experience. Features include a professional beach volleyball court, ATV jump track, forest paintball bunkers, horse sand ring, hot tub, fire pit, & covered entertainment pavilion w/hydro. This property is built for recreation, gatherings, and year-round enjoyment. Equestrian and hobby farm buyers will appreciate the 5-stall horse barn, large quonset hut, drive shed & extensive storage options for equipment, vehicles, & recreational toys. A second driveway w/parking for 10+ vehicles provides excellent access for guests, trailers, or extended family use. Additional features include high-speed fibre optic internet, geothermal heating & cooling for energy efficiency, paved and regularly maintained road access, year-round usability, & a short, easy-maintenance driveway. This is a turnkey country estate, hobby farm & lifestyle property offering flexibility for families, outdoor enthusiasts & buyers seeking space to live, work & play. 5 Beds ⋅ 3 Baths ⋅ W13170790 MLS Discover a rare opportunity to own a fully equipped 10-acre rural estate designed for multigenerational living, hobby farming, equestrian use & luxury country living. Offering unmatched privacy, versatility & lifestyle amenities, this exceptional property blends functionality w/resort-style outdoor living just minutes from key amenities & commuter routes. The impressive 4,100 sq ft side-split residence is ideal for large or extended families, featuring 5 bdrms, 3 full baths, 2 full kitchens, home office & home theatre. The layout supports in-law suite potential & multigenerational living, w/2 main-floor bdrms each offering ensuite baths. The chef-inspired kitchen showcases 10' vaulted ceilings, oversized island, w/i pantry & abundant natural light, creating a warm & functional gathering space. Designed for both comfort & entertaining, the home includes multiple walkouts to an expansive deck overlooking the property, ideal for indoor-outdoor living & hosting. The land is a true highlight; offering a private, fully developed outdoor lifestyle experience. Features include a professional beach volleyball court, ATV jump track, forest paintball bunkers, horse sand ring, hot tub, fire pit, & covered entertainment pavilion w/hydro. This property is built for recreation, gatherings, and year-round enjoyment. Equestrian and hobby farm buyers will appreciate the 5-stall horse barn, large quonset hut, drive shed & extensive storage options for equipment, vehicles, & recreational toys. A second driveway w/parking for 10+ vehicles provides excellent access for guests, trailers, or extended family use. Additional features include high-speed fibre optic internet, geothermal heating & cooling for energy efficiency, paved and regularly maintained road access, year-round usability, & a short, easy-maintenance driveway. This is a turnkey country estate, hobby farm & lifestyle property offering flexibility for families, outdoor enthusiasts & buyers seeking space to live, work & play. 11170 Fifth Line, Milton
$2,399,000 Personal Sanctuary in Prestigious Ennisclare Woods. Tucked away on 2.85 private acres, this property feels like your own exclusive resort. A fenced saltwater pool with a waterfall feature and a spacious pavilion with ample seating and a bar set the stage for unforgettable gatherings. Surrounded by mature trees, lush perennial gardens, and a private forest, this home is truly an oasis of tranquillity. This custom-built residence makes an impression at every turn. Step into the stately foyer, leading to the upgraded chef's kitchen complete with a walk-in pantry, hidden pull-out spice and pan storage, and a dedicated dining area. The great room, anchored by a grand fireplace, flows effortlessly into a private office/study and out to the elevated veranda. With retractable awnings and sweeping views of the grounds, it's the perfect spot to relax or entertain. The oversized primary suite offers a romantic fireplace, generous closets, and a spa-inspired ensuite retreat. A second bedroom enjoys its own ensuite, while the third and fourth bedrooms share a well-appointed bathroom. The fully finished lower level expands the living space with a recreation room (featuring yet another fireplace), a fifth bedroom, a full bath, an additional home office, and abundant storage. Ennisclare Woods is a one-of-a-kind community of 29 estate homes surrounded by 90 acres of protected woodland trails (just $200/year). Highlights include:4+1 bedrooms, 4.5 bathrooms, 3 fireplaces, Home office + mudroom, inside entry from an attached 2-car garage, Detached garage/workshop + shed, Resort-style saltwater pool & pavilion. This home truly offers something for everyone, privacy, luxury, and a setting unlike any other. 5 Beds ⋅ 5 Baths ⋅ W13088030 MLS Personal Sanctuary in Prestigious Ennisclare Woods. Tucked away on 2.85 private acres, this property feels like your own exclusive resort. A fenced saltwater pool with a waterfall feature and a spacious pavilion with ample seating and a bar set the stage for unforgettable gatherings. Surrounded by mature trees, lush perennial gardens, and a private forest, this home is truly an oasis of tranquillity. This custom-built residence makes an impression at every turn. Step into the stately foyer, leading to the upgraded chef's kitchen complete with a walk-in pantry, hidden pull-out spice and pan storage, and a dedicated dining area. The great room, anchored by a grand fireplace, flows effortlessly into a private office/study and out to the elevated veranda. With retractable awnings and sweeping views of the grounds, it's the perfect spot to relax or entertain. The oversized primary suite offers a romantic fireplace, generous closets, and a spa-inspired ensuite retreat. A second bedroom enjoys its own ensuite, while the third and fourth bedrooms share a well-appointed bathroom. The fully finished lower level expands the living space with a recreation room (featuring yet another fireplace), a fifth bedroom, a full bath, an additional home office, and abundant storage. Ennisclare Woods is a one-of-a-kind community of 29 estate homes surrounded by 90 acres of protected woodland trails (just $200/year). Highlights include:4+1 bedrooms, 4.5 bathrooms, 3 fireplaces, Home office + mudroom, inside entry from an attached 2-car garage, Detached garage/workshop + shed, Resort-style saltwater pool & pavilion. This home truly offers something for everyone, privacy, luxury, and a setting unlike any other. 4220 Ennisclare Drive, Milton
$1,800,000 Team Tiger presents a once-in-a-lifetime opportunity that awaits the most discerning of buyers.Introducing Arbour Gates - an extraordinarily rare, private gated community, nestled in one ofMilton's most coveted settings, where prestige, privacy, and natural beauty converge in perfect harmony. A secure entrance that gives one peace of mind and a sense of safety for families.With only four exclusive lots available, this is an invitation to join an intimate community, unlike anything else the market has to offer. Grand private gates set the tone from the moment you arrive, commanding an immediate sense of arrival and distinction that few addresses in the region can rival.Each lot is graced with breathtaking, sweeping views and surrounded by the serene natural beauty that makes this location truly irreplaceable. Yet despite its sense of seclusion, ArbourGates places you within effortless reach of Milton's finest amenities - top-rated schools, premier shopping, dining, hiking, golfing, major highways, and everything a sophisticated lifestyle demands.This is not simply a home - it is a legacy property. Opportunities of this calibre surface only once in a generation. Whether you envision a custom-built architectural masterpiece or a timeless family estate, Arbour Gates provides the rarest of canvases. W13065996 MLS Team Tiger presents a once-in-a-lifetime opportunity that awaits the most discerning of buyers.Introducing Arbour Gates - an extraordinarily rare, private gated community, nestled in one ofMilton's most coveted settings, where prestige, privacy, and natural beauty converge in perfect harmony. A secure entrance that gives one peace of mind and a sense of safety for families.With only four exclusive lots available, this is an invitation to join an intimate community, unlike anything else the market has to offer. Grand private gates set the tone from the moment you arrive, commanding an immediate sense of arrival and distinction that few addresses in the region can rival.Each lot is graced with breathtaking, sweeping views and surrounded by the serene natural beauty that makes this location truly irreplaceable. Yet despite its sense of seclusion, ArbourGates places you within effortless reach of Milton's finest amenities - top-rated schools, premier shopping, dining, hiking, golfing, major highways, and everything a sophisticated lifestyle demands.This is not simply a home - it is a legacy property. Opportunities of this calibre surface only once in a generation. Whether you envision a custom-built architectural masterpiece or a timeless family estate, Arbour Gates provides the rarest of canvases. 4250 Donaldson Lane, Milton
$1,699,900 A long maple tree-lined lane leads through a private, park-like setting with mature trees and perennial gardens to this attractive custom-built 2-storey brick and cedar siding home. The house features a centre hall plan, large living room, separate dining room, eat-in kitchen, main floor family room with wood-burning brick fireplace and sliding glass door to west facing deck, office with closet and which could be used as a 4th bedroom, 2-piece powder room off the back hall, three bedrooms on the second floor including the primary bedroom with two double closets, second bedroom with double closet and a second closet, third bedroom with double closet and a 5-piece bathroom with two sinks and large vanity offering ample storage. The basement is full and unfinished with three windows, storage and the utility room with propane gas furnace installed in the fall of 2025. The property also offers a 5 box stall barn with tack/feed room and hay loft above. There is hydro and water available to the barn. The land is gently rolling with paddocks, a hay field and wooded areas on approximately 17 acres. Conveniently located in the Greater Toronto Area (GTA) in the Township of Milton, minutes to Hwy 401, GO-Trains in Milton, Acton and Georgetown, shopping, schools, sports fields, libraries and community centres, extensive Niagara Escarpment recreation areas including the Bruce Trail, conservation hiking trails, mountain bike trails, swimming and camping, the velodrome in Milton offering a track cycling facility and more, breathtaking and challenging road cycling, downhill and cross country skiing in an area of great natural beauty. 3 Beds ⋅ 2 Baths ⋅ W13568776 MLS A long maple tree-lined lane leads through a private, park-like setting with mature trees and perennial gardens to this attractive custom-built 2-storey brick and cedar siding home. The house features a centre hall plan, large living room, separate dining room, eat-in kitchen, main floor family room with wood-burning brick fireplace and sliding glass door to west facing deck, office with closet and which could be used as a 4th bedroom, 2-piece powder room off the back hall, three bedrooms on the second floor including the primary bedroom with two double closets, second bedroom with double closet and a second closet, third bedroom with double closet and a 5-piece bathroom with two sinks and large vanity offering ample storage. The basement is full and unfinished with three windows, storage and the utility room with propane gas furnace installed in the fall of 2025. The property also offers a 5 box stall barn with tack/feed room and hay loft above. There is hydro and water available to the barn. The land is gently rolling with paddocks, a hay field and wooded areas on approximately 17 acres. Conveniently located in the Greater Toronto Area (GTA) in the Township of Milton, minutes to Hwy 401, GO-Trains in Milton, Acton and Georgetown, shopping, schools, sports fields, libraries and community centres, extensive Niagara Escarpment recreation areas including the Bruce Trail, conservation hiking trails, mountain bike trails, swimming and camping, the velodrome in Milton offering a track cycling facility and more, breathtaking and challenging road cycling, downhill and cross country skiing in an area of great natural beauty. 12170 Sixth Line Nassagaweya N/A, Milton
$1,699,900 This majestic 1832 Century Stone Farmhouse, set on a private and picturesque 10-acre property is ideal for families seeking space, comfort, and a connection to nature. With more than 3,442 sq ft living space, this treasured home blends 1800 century charm with thoughtful modern updates. The warm, inviting interior features soaring ceilings, open hearth wood-burning fireplaces, deep window sills and other preserved original details. The versatile and sprawling main floor provides a flexible layout to support extended family and an in-law suite. The recently renovated kitchen showcases a striking stone wall with timber beam accents, stone countertops, hardwood flooring, a vintage-style Elmira Stove, and a centre island with breakfast bar. Separate family, living and dining rooms provide ample space for both everyday living and special occasions. The formal dining room currently serves as a main-floor primary bedroom, complete with a walk-in closet/office. The 2nd dining room has ample space for a harvest table. Currently used as a gym provides oversized windows, a striking stone wall and a walkout to the garden. More conveniences include an enclosed sunroom, a mudroom with access to the 2 car garage, main-floor laundry, and a stately wood staircase to the 2nd floor bedrooms and 4th bathroom. The 2019 energy-efficient heat pump provides heat and air conditioning, R50 attic insulation and updated shingles. Enjoy an organic vegetable garden and gently rolling open fields that are perfect for exploring and pasture. The barn and chicken coop are ideal for horses, animals or additional storage. An attached two-car garage offers ample space for cars, motorbikes, outdoor gear and more. The generous driveway and laneway provide plenty of room for parking cars, equipment and campers. Located on a paved road just minutes to Town convenience, schools, churches, Blue Springs Golf Club and GO service offering the perfect blend of country living. 4 Beds ⋅ 4 Baths ⋅ W13469504 MLS This majestic 1832 Century Stone Farmhouse, set on a private and picturesque 10-acre property is ideal for families seeking space, comfort, and a connection to nature. With more than 3,442 sq ft living space, this treasured home blends 1800 century charm with thoughtful modern updates. The warm, inviting interior features soaring ceilings, open hearth wood-burning fireplaces, deep window sills and other preserved original details. The versatile and sprawling main floor provides a flexible layout to support extended family and an in-law suite. The recently renovated kitchen showcases a striking stone wall with timber beam accents, stone countertops, hardwood flooring, a vintage-style Elmira Stove, and a centre island with breakfast bar. Separate family, living and dining rooms provide ample space for both everyday living and special occasions. The formal dining room currently serves as a main-floor primary bedroom, complete with a walk-in closet/office. The 2nd dining room has ample space for a harvest table. Currently used as a gym provides oversized windows, a striking stone wall and a walkout to the garden. More conveniences include an enclosed sunroom, a mudroom with access to the 2 car garage, main-floor laundry, and a stately wood staircase to the 2nd floor bedrooms and 4th bathroom. The 2019 energy-efficient heat pump provides heat and air conditioning, R50 attic insulation and updated shingles. Enjoy an organic vegetable garden and gently rolling open fields that are perfect for exploring and pasture. The barn and chicken coop are ideal for horses, animals or additional storage. An attached two-car garage offers ample space for cars, motorbikes, outdoor gear and more. The generous driveway and laneway provide plenty of room for parking cars, equipment and campers. Located on a paved road just minutes to Town convenience, schools, churches, Blue Springs Golf Club and GO service offering the perfect blend of country living. 5595 25 Side Road, Milton
$1,699,000 12613 Second Line is a home that speaks to quality craftsmanship and thoughtful preservation. A long private driveway slows the pace of life, setting the tone for the peaceful country retreat that awaits. Rich wood siding creates contrast between the home and the surrounding nature. Inside, the unique layout features a center stairwell that's open to the living and dining room. The kitchen offers ample space for cooking and entertaining, with plenty of cabinetry and a center island for prep. Just off this, a half bathroom and designated laundry room complete the shared living spaces. The primary bedroom is conveniently located on the mainfloor, ideal for generational living, and complete with its own ensuite bathroom. On the lower level, find three additional bedrooms, walk-out access, a five-piece ensuite bathroom, and a large recreational room with large windows overlooking the yard and pond. The upper balcony and lower patio are ideal for indoor-outdoor entertaining and are accessed off the main living room and lower rec room. Families and outdoorsy buyers will appreciate the hidden trails woven in the forest and the beauty of nature around them, with deer, blue herons, ducks, hawks, and other wildlife making frequent visits to the property. Estately in its nature, yet warm and cozy, this home is the perfect home for mature families or retirees looking for an accessible living setup with room for their grandkids. This thoughtfully equipped property has practical, well-planned amenities for equestrian endeavors and hobby farming, including fenced grass paddocks, a spacious, fenced riding arena, a dedicated wash station, and three storage sheds for tack, feed, and equipment. Completing the setting is a picturesque spring-fed pond with a floating dock, offering both natural beauty and utility. This home provides buyers with the peace, tranquility and flexibility that's only found in a rural setting. 4 Beds ⋅ 3 Baths ⋅ W13578896 MLS 12613 Second Line is a home that speaks to quality craftsmanship and thoughtful preservation. A long private driveway slows the pace of life, setting the tone for the peaceful country retreat that awaits. Rich wood siding creates contrast between the home and the surrounding nature. Inside, the unique layout features a center stairwell that's open to the living and dining room. The kitchen offers ample space for cooking and entertaining, with plenty of cabinetry and a center island for prep. Just off this, a half bathroom and designated laundry room complete the shared living spaces. The primary bedroom is conveniently located on the mainfloor, ideal for generational living, and complete with its own ensuite bathroom. On the lower level, find three additional bedrooms, walk-out access, a five-piece ensuite bathroom, and a large recreational room with large windows overlooking the yard and pond. The upper balcony and lower patio are ideal for indoor-outdoor entertaining and are accessed off the main living room and lower rec room. Families and outdoorsy buyers will appreciate the hidden trails woven in the forest and the beauty of nature around them, with deer, blue herons, ducks, hawks, and other wildlife making frequent visits to the property. Estately in its nature, yet warm and cozy, this home is the perfect home for mature families or retirees looking for an accessible living setup with room for their grandkids. This thoughtfully equipped property has practical, well-planned amenities for equestrian endeavors and hobby farming, including fenced grass paddocks, a spacious, fenced riding arena, a dedicated wash station, and three storage sheds for tack, feed, and equipment. Completing the setting is a picturesque spring-fed pond with a floating dock, offering both natural beauty and utility. This home provides buyers with the peace, tranquility and flexibility that's only found in a rural setting. 12613 Second Line, Milton
$1,650,000 Welcome to this exceptional 15-acre nature retreat offering the perfect blend of privacy, functionality, and rural charm. Set in a picturesque setting with a serene pond and fountain and private trails throughout the property, this unique offering is ideal for nature lovers and outdoor enthusiasts. The well-maintained 2-storey home is perfectly suited for extended family living or flexible use, featuring a bright living area, sunroom with beautiful views, primary bedroom, two full bathrooms, and an additional playroom or flex space on the main floor. The second floor includes a full kitchen, dining room, spacious family room, two additional bedrooms, and a 3-piece bathroom. A finished trailer with hydro connection provides excellent potential for guests, in-laws, or additional income. The property also includes two firewood storage sheds, a Fire-Pit, a large 30' x 40' storage shed/workshop, and additional storage space above the garage, along with 200 AMP electrical service. Conveniently located between Milton and Acton, and just a short drive to Highway 401, this property offers peaceful country living with easy access to urban amenities. 3 Beds ⋅ 3 Baths ⋅ W13231054 MLS Welcome to this exceptional 15-acre nature retreat offering the perfect blend of privacy, functionality, and rural charm. Set in a picturesque setting with a serene pond and fountain and private trails throughout the property, this unique offering is ideal for nature lovers and outdoor enthusiasts. The well-maintained 2-storey home is perfectly suited for extended family living or flexible use, featuring a bright living area, sunroom with beautiful views, primary bedroom, two full bathrooms, and an additional playroom or flex space on the main floor. The second floor includes a full kitchen, dining room, spacious family room, two additional bedrooms, and a 3-piece bathroom. A finished trailer with hydro connection provides excellent potential for guests, in-laws, or additional income. The property also includes two firewood storage sheds, a Fire-Pit, a large 30' x 40' storage shed/workshop, and additional storage space above the garage, along with 200 AMP electrical service. Conveniently located between Milton and Acton, and just a short drive to Highway 401, this property offers peaceful country living with easy access to urban amenities. 11099 Sixth Line Nassagaweya N/A, Milton
$1,595,000 Discover the charm of this 2,066 sq ft brick bungalow, perfectly nestled on 1.4 acres backing onto conservation land along 16 Mile Creek. Step inside to a welcoming eat-in kitchen, a bright dining room, and a cozy living room complete with a wood-burning fireplace-ideal for relaxing evenings. The home offers three comfortable bedrooms, all with hardwood floors, including a primary with a 3-piece semi-ensuite. The spacious full basement with 9-foot ceilings provides endless possibilities, already equipped with a roughed-in bathroom and a wine cellar tucked under the garage. With an efficient electric furnace, heat pump, new central air (all 2023), and 200-amp service, upgraded windows, this home is ready for modern living. Outdoors, enjoy a large 16 x25 ft deck, a double attached garage, and a 36' x 24' shop-perfect for hobbies, storage, or workspace. This property seamlessly blends comfort, nature, and opportunity in a stunning natural setting with- in walking distance to Hilton Falls Conservation 3 Beds ⋅ 2 Baths ⋅ W13488064 MLS Discover the charm of this 2,066 sq ft brick bungalow, perfectly nestled on 1.4 acres backing onto conservation land along 16 Mile Creek. Step inside to a welcoming eat-in kitchen, a bright dining room, and a cozy living room complete with a wood-burning fireplace-ideal for relaxing evenings. The home offers three comfortable bedrooms, all with hardwood floors, including a primary with a 3-piece semi-ensuite. The spacious full basement with 9-foot ceilings provides endless possibilities, already equipped with a roughed-in bathroom and a wine cellar tucked under the garage. With an efficient electric furnace, heat pump, new central air (all 2023), and 200-amp service, upgraded windows, this home is ready for modern living. Outdoors, enjoy a large 16 x25 ft deck, a double attached garage, and a 36' x 24' shop-perfect for hobbies, storage, or workspace. This property seamlessly blends comfort, nature, and opportunity in a stunning natural setting with- in walking distance to Hilton Falls Conservation 4101 Campbellville Road, Milton
$1,499,555 - This one is a must see in person. - MUST WATCH YOUTUBE VIDEO!!! - Motivated seller!!! - Priced under market comparables. - Nearly 11 acres (5+ clear canvas, 5+ treeline). - Prestigious 410 ft wide lot with rolling hills. - A perfect canvas for all the things you can dream of. - The existing owner can rent if the new owners allow. - New kitchen, 2 new bathrooms, 3 bedrooms. - New appliances, including Fridge, Washer, Dryer, Microwave and Range Hood. - Vinyl windows. - House, Barndominium + Garage, Barn [Combined 3,390 SQFT]. - 12 mins over Highway 401, close to Highway 413. - Furniture virtually staged. - Use the property for Commercial Business, Add a Custom Home extension, Multi-Family, Wedding, Golf, Cricket, Homestead, etc.). A ton of permitted uses under Zoning A by-laws, including Short-Term Rental, Shared Housing, Cottage Industry, Cannabis Production & Processing Facility, Boarding kennel, Veterinary Clinic, Veterinary Hospital, Agricultural Rural, Agricultural operation, Detached dwelling, Equestrian centre, Storage Building for Agricultural Equipment/Produce, Forestry use, Home industry, Home occupation, Horticultural nursery, Conservation use. 3 Beds ⋅ 2 Baths ⋅ W13429716 MLS - This one is a must see in person. - MUST WATCH YOUTUBE VIDEO!!! - Motivated seller!!! - Priced under market comparables. - Nearly 11 acres (5+ clear canvas, 5+ treeline). - Prestigious 410 ft wide lot with rolling hills. - A perfect canvas for all the things you can dream of. - The existing owner can rent if the new owners allow. - New kitchen, 2 new bathrooms, 3 bedrooms. - New appliances, including Fridge, Washer, Dryer, Microwave and Range Hood. - Vinyl windows. - House, Barndominium + Garage, Barn [Combined 3,390 SQFT]. - 12 mins over Highway 401, close to Highway 413. - Furniture virtually staged. - Use the property for Commercial Business, Add a Custom Home extension, Multi-Family, Wedding, Golf, Cricket, Homestead, etc.). A ton of permitted uses under Zoning A by-laws, including Short-Term Rental, Shared Housing, Cottage Industry, Cannabis Production & Processing Facility, Boarding kennel, Veterinary Clinic, Veterinary Hospital, Agricultural Rural, Agricultural operation, Detached dwelling, Equestrian centre, Storage Building for Agricultural Equipment/Produce, Forestry use, Home industry, Home occupation, Horticultural nursery, Conservation use. 5273 25 Side Road, Milton
$1,225,000 Amazing 1.3 acre park-like peaceful setting for this beautifully renovated home. Almost 2400 square feet with stunning open concept kitchen (2020) with huge island perfect for the entertaining chef. A very bright home accented by large upgraded windows through the main level living room, family room with woodstove-style gas fireplace plus two main level bedrooms complimented by an oversize main bathroom. Unique oversized primary bedroom with vast sitting area adjacent to an ensuite washroom plus an open jacuzzi style tub. Secluded oasis bedroom area with gas fireplace and walk-in closet. Lower level boasts of vast bar/games room, cozy rec/theatre room plus extensive utility/storage area. You'll love the tree-lined perimeter from the huge flagstone patio. Bonus features of oversized attached double garage, separate 20' X 30' insulated workshop, new furnace 2025, fridge and stove 2024 and central air 2025, new heat pump delivering efficient comfort to the upper level 2026. New (July 2026) Generac Generator. Enjoy the quiet countryside. 3 Beds ⋅ 2 Baths ⋅ W13599556 MLS Amazing 1.3 acre park-like peaceful setting for this beautifully renovated home. Almost 2400 square feet with stunning open concept kitchen (2020) with huge island perfect for the entertaining chef. A very bright home accented by large upgraded windows through the main level living room, family room with woodstove-style gas fireplace plus two main level bedrooms complimented by an oversize main bathroom. Unique oversized primary bedroom with vast sitting area adjacent to an ensuite washroom plus an open jacuzzi style tub. Secluded oasis bedroom area with gas fireplace and walk-in closet. Lower level boasts of vast bar/games room, cozy rec/theatre room plus extensive utility/storage area. You'll love the tree-lined perimeter from the huge flagstone patio. Bonus features of oversized attached double garage, separate 20' X 30' insulated workshop, new furnace 2025, fridge and stove 2024 and central air 2025, new heat pump delivering efficient comfort to the upper level 2026. New (July 2026) Generac Generator. Enjoy the quiet countryside. 11113 Fifth Line, Milton
$1,200,000 Well-maintained detached home with Three bedrooms on a rare 1.2-acre lot. Bright, functional layout with an eat-in kitchen, hardwood flooring, and a spacious dining area featuring oversized windows and a private backyard. The expansive property offers exceptional outdoor space with endless potential, the perfect balance of space, privacy, and convenience. 3 Beds ⋅ 3 Baths ⋅ W13652096 MLS Well-maintained detached home with Three bedrooms on a rare 1.2-acre lot. Bright, functional layout with an eat-in kitchen, hardwood flooring, and a spacious dining area featuring oversized windows and a private backyard. The expansive property offers exceptional outdoor space with endless potential, the perfect balance of space, privacy, and convenience. 4014 Twenty Side Road, Milton
$825,000 Imagine waking each morning to birdsong, open sky, and the quiet privacy that only true country living can offer. This remarkable 5-acre parcel along Fourth Line in Nassagaweya presents a rare canvas for those ready to build something extraordinary in one of Milton's most coveted rural pockets. Measuring a generous 350 feet by 625 feet, the lot is surrounded by million-dollar country estates, ensuring your future home will be in distinguished company. A long, meandering clearing already carves the path for a private driveway, leading you deep into the property to a secluded building site tucked at the rear-far from the road and beautifully sheltered by nature. From here, the possibilities are wide open: a modern retreat, or a timeless family homestead designed entirely around your lifestyle. A drilled well (as is) on site. Despite its peaceful seclusion, this location keeps you wonderfully connected. Highway 401 sits within easy reach, while downtown Milton and downtown Georgetown are each roughly 20 minutes away. Outdoor enthusiasts will love the proximity to scenic hiking trails, winter skiing, and a variety of nearby golf courses. Opportunities to build on land like this-private, expansive, and thoughtfully positioned-rarely come along. Your dream home begins with the perfect setting, and it starts here. W13551438 MLS Imagine waking each morning to birdsong, open sky, and the quiet privacy that only true country living can offer. This remarkable 5-acre parcel along Fourth Line in Nassagaweya presents a rare canvas for those ready to build something extraordinary in one of Milton's most coveted rural pockets. Measuring a generous 350 feet by 625 feet, the lot is surrounded by million-dollar country estates, ensuring your future home will be in distinguished company. A long, meandering clearing already carves the path for a private driveway, leading you deep into the property to a secluded building site tucked at the rear-far from the road and beautifully sheltered by nature. From here, the possibilities are wide open: a modern retreat, or a timeless family homestead designed entirely around your lifestyle. A drilled well (as is) on site. Despite its peaceful seclusion, this location keeps you wonderfully connected. Highway 401 sits within easy reach, while downtown Milton and downtown Georgetown are each roughly 20 minutes away. Outdoor enthusiasts will love the proximity to scenic hiking trails, winter skiing, and a variety of nearby golf courses. Opportunities to build on land like this-private, expansive, and thoughtfully positioned-rarely come along. Your dream home begins with the perfect setting, and it starts here. -- Fourth Line Nassagaweya N/A, Milton