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$1,449,900
6 Beds ⋅ 5 Baths ⋅ W13602198 MLS® #
Historic Elegance Meets Modern Luxury at 9 Wellington St. Experience the perfect blend of century-old charm and high-end functionality in this grand 1926 home located on one of Orangeville's most prestigious streets. Spanning an impressive 4201 sq ft, this residence features 2 kitchens with a self-contained apartment, and a total of 6 spacious bedrooms and 5 bathrooms, providing ample space for both grand living and cozy retreats. The main home welcomes you with a charming sunroom of wood and exposed brick, leading into a formal dining room & library space centered around one of the home's three gas fireplaces. Culinary enthusiasts will appreciate the open-concept kitchen's central island and rich wood cabinetry, which flows effortlessly into a great room anchored by a striking brick fireplace that walks out to your spacious back deck. Retreat to the primary suite to find 2 double closets and a spa-like 5-piece ensuite bathed in light from a large skylight. A 2nd stairwell to this level brings you to 3 more bedrooms and a shared 3 piece bathroom while yet another bedroom or additional living space can be found in the unique top-level loft. The 3 Level Apartment on the South side of the home features its own entrance through a stunning vestibule, a main floor eat-in kitchen that walks out to the back deck, lower level family room with walk-out to the yard, a 3rd story primary suite with gorgeous 3 piece ensuite & laundry hookups, and the convenience of its own furnace, and hot water tank. The perfect space for rental income or extended family. Set on a deep 63 x 188 ft lot, the private backyard serves as a secluded oasis with mature hedges, low-maintenance gardens, and a spacious, multi-level deck for entertaining. Located just moments from the award-winning restaurants & shops of Broadway, the Island Lake Conservation Area, and within walking distance to local schools, this home offers a peaceful lifestyle with every urban convenience at your doorstep. (id:5764)

9 Wellington Street, Orangeville

Listing courtesy of EXP REALTY.

$1,449,900
6 Beds ⋅ 5 Baths ⋅ W13602198 MLS® #
Historic Elegance Meets Modern Luxury at 9 Wellington St. Experience the perfect blend of century-old charm and high-end functionality in this grand 1926 home located on one of Orangeville's most prestigious streets. Spanning an impressive 4201 sq ft, this residence features 2 kitchens with a self-contained apartment, and a total of 6 spacious bedrooms and 5 bathrooms, providing ample space for both grand living and cozy retreats. The main home welcomes you with a charming sunroom of wood and exposed brick, leading into a formal dining room & library space centered around one of the home's three gas fireplaces. Culinary enthusiasts will appreciate the open-concept kitchen's central island and rich wood cabinetry, which flows effortlessly into a great room anchored by a striking brick fireplace that walks out to your spacious back deck. Retreat to the primary suite to find 2 double closets and a spa-like 5-piece ensuite bathed in light from a large skylight. A 2nd stairwell to this level brings you to 3 more bedrooms and a shared 3 piece bathroom while yet another bedroom or additional living space can be found in the unique top-level loft. The 3 Level Apartment on the South side of the home features its own entrance through a stunning vestibule, a main floor eat-in kitchen that walks out to the back deck, lower level family room with walk-out to the yard, a 3rd story primary suite with gorgeous 3 piece ensuite & laundry hookups, and the convenience of its own furnace, and hot water tank. The perfect space for rental income or extended family. Set on a deep 63 x 188 ft lot, the private backyard serves as a secluded oasis with mature hedges, low-maintenance gardens, and a spacious, multi-level deck for entertaining. Located just moments from the award-winning restaurants & shops of Broadway, the Island Lake Conservation Area, and within walking distance to local schools, this home offers a peaceful lifestyle with every urban convenience at your doorstep.

9 Wellington Street, Orangeville

Listing courtesy of EXP REALTY.

$1,499,900
5 Beds ⋅ 3 Baths ⋅ W13583264 MLS® #
Welcome to the esteemed 24 Faulkner, where history lives on in pristine perfection. Built in 1908 by John C. Reid, Dufferin County's first clerk, this Edwardian gem is a rare testament to Orangeville's past, gracefully preserved & lovingly updated for modern life. The stately facade of local red brick, stone accents, symmetrical lines, broad roofline & cedar shingled gables reflect timeless architecture. Imagine the conversations held over the last century on the covered front porch, w original features including stained glass window. Inside, floor-to-ceiling elegance sets this home apart. Soaring 9ft coved ceilings feature unique patterns in each room. 12" baseboards ground the space in historical craftsmanship while adding a sense of grandeur. The family & dining rooms are divided by an original pocket door, allowing for both flow and intimacy depending on the occasion. In the dining rm, a striking, original bay window offers views of the beautifully landscaped side yard. The heart of the home, a modern kitchen with center island, intentionally designed cupboard storage & beautiful quartz counters, leads out to a covered back porch, perfect for enjoying summer suppers alfresco. Hardwood floors grace much of the home, with softwood cleverly tucked under tables & rugs, an original builder's trick to balance beauty with budget. The 2nd floor hosts four generous bedrooms, with soaring ceilings, large closets & big, beautiful windows. A classic claw-foot tub & walk-in shower complete the luxurious main bath. Ascend to the third-floor primary suite, a tranquil retreat with spa-like ensuite, soaker tub, double vanity, walk-in shower, and your dream walk in closet. The rare finished basement adds yet another living space to this 2395 sq ft home. This property neighbours only the quiet grounds of ODSS, coming alive for just a few moments at bell time. With historical records from the original $1700 build cost still intact, this home is not only a treasure, it's a legacy. (id:5764)

24 Faulkner Street, Orangeville

Listing courtesy of EXP REALTY.

$1,499,900
5 Beds ⋅ 3 Baths ⋅ W13583264 MLS® #
Welcome to the esteemed 24 Faulkner, where history lives on in pristine perfection. Built in 1908 by John C. Reid, Dufferin County's first clerk, this Edwardian gem is a rare testament to Orangeville's past, gracefully preserved & lovingly updated for modern life. The stately facade of local red brick, stone accents, symmetrical lines, broad roofline & cedar shingled gables reflect timeless architecture. Imagine the conversations held over the last century on the covered front porch, w original features including stained glass window. Inside, floor-to-ceiling elegance sets this home apart. Soaring 9ft coved ceilings feature unique patterns in each room. 12" baseboards ground the space in historical craftsmanship while adding a sense of grandeur. The family & dining rooms are divided by an original pocket door, allowing for both flow and intimacy depending on the occasion. In the dining rm, a striking, original bay window offers views of the beautifully landscaped side yard. The heart of the home, a modern kitchen with center island, intentionally designed cupboard storage & beautiful quartz counters, leads out to a covered back porch, perfect for enjoying summer suppers alfresco. Hardwood floors grace much of the home, with softwood cleverly tucked under tables & rugs, an original builder's trick to balance beauty with budget. The 2nd floor hosts four generous bedrooms, with soaring ceilings, large closets & big, beautiful windows. A classic claw-foot tub & walk-in shower complete the luxurious main bath. Ascend to the third-floor primary suite, a tranquil retreat with spa-like ensuite, soaker tub, double vanity, walk-in shower, and your dream walk in closet. The rare finished basement adds yet another living space to this 2395 sq ft home. This property neighbours only the quiet grounds of ODSS, coming alive for just a few moments at bell time. With historical records from the original $1700 build cost still intact, this home is not only a treasure, it's a legacy.

24 Faulkner Street, Orangeville

Listing courtesy of EXP REALTY.

$1,229,000
4 Beds ⋅ 3 Baths ⋅ W13578826 MLS® #
Welcome To 91 Biscayne Crescent In Orangeville. This Stunning, Fully Renovated Family Home Offers Over 2,400 Sq. Ft. Of Beautifully Finished Living Space And Has Been Thoughtfully Redesigned From Top To Bottom. The Open-Concept Main Level Showcases Rich Hardwood Flooring, Crown Moulding, Spacious Living And Dining Areas, And A Chef-Inspired Kitchen Featuring Custom Cabinetry, Premium Appliances, A Striking Range Hood, And A Large Centre Island Perfect For Entertaining. Step Outside To An Exceptional Outdoor Retreat, Extensively Updated In 2024-2025, Featuring An Expansive Deck, Stamped Concrete, Professionally Landscaped Gardens, And Generous Outdoor Living Space On A Private, Pool-Sized Pie-Shaped Lot. A Custom-Built Privacy Fence Creates A Secluded Setting For The New 2025 Hot Tub, Which Is Excluded But Negotiable. The Main Level Offers Three Generous Bedrooms, Including A Beautiful Primary Suite With Custom Closets And A Spa-Inspired Ensuite. The Bright, Fully Finished Walkout Lower Level Features A Spacious Recreation Room With Fireplace, Additional Bedroom, Full Bathroom, Dry Bar, And Laundry Room, Offering Excellent Flexibility For Guests Or Extended Family. Complete With Direct Access To A Heated Double Car Garage, This Turnkey Home Is Ideally Located Minutes From Schools, Parks, Trails, Recreation, Shopping, Dining, Downtown Orangeville, And Highway 10 For An Easy Commute. (id:5764)

91 Biscayne Crescent, Orangeville

Listing courtesy of REVEL REALTY INC..

$1,229,900
4 Beds ⋅ 2 Baths ⋅ W13560922 MLS® #
Built with craftsmanship that's stood the test of time and thoughtfully updated where it matters most, this beautiful character home offers warmth and personality that's felt from the moment you arrive. Set on one of Orangeville's most picturesque tree-lined streets, just a short walk from downtown shops, restaurants, cafés, and parks, the location is every bit as appealing as the home itself. A welcoming front porch and established gardens provide the perfect introduction before stepping inside to discover original hardwood floors, rich wood detailing, and a striking staircase that honour the home's history while blending seamlessly with thoughtful updates. Natural light fills the home, especially in the sunroom. Framed by exposed brick and oversized windows, it's a space you'll naturally gravitate toward for a morning coffee, an afternoon with a good book, or simply watching the seasons change. The main living spaces flow effortlessly from one to the next, creating an inviting setting for everyday living and entertaining alike. A fireplace anchors the living room before leading into the formal dining room, while the updated kitchen offers quartz countertops, stainless steel appliances, a gas range, and generous workspace. The adjoining family room features a second fireplace and French doors opening to the private backyard, where mature landscaping and a spacious deck create a peaceful extension of the home. The finished attic serves as a private primary retreat, while three additional bedrooms and a beautifully renovated bathroom with heated floors complete the upper levels. Downstairs, the finished lower level offers flexible space for a recreation room, home gym, games room, or creative studio, with a side entrance, garage access, and built-in storage adding everyday practicality. Beautifully maintained and thoughtfully updated, this is a home where timeless character and modern comfort come together just steps from everything downtown Orangeville has to offer. (id:5764)

9 York Street, Orangeville

Listing courtesy of ROYAL LEPAGE RCR REALTY.

$1,229,900
4 Beds ⋅ 2 Baths ⋅ W13560922 MLS® #
Built with craftsmanship that's stood the test of time and thoughtfully updated where it matters most, this beautiful character home offers warmth and personality that's felt from the moment you arrive. Set on one of Orangeville's most picturesque tree-lined streets, just a short walk from downtown shops, restaurants, cafés, and parks, the location is every bit as appealing as the home itself. A welcoming front porch and established gardens provide the perfect introduction before stepping inside to discover original hardwood floors, rich wood detailing, and a striking staircase that honour the home's history while blending seamlessly with thoughtful updates. Natural light fills the home, especially in the sunroom. Framed by exposed brick and oversized windows, it's a space you'll naturally gravitate toward for a morning coffee, an afternoon with a good book, or simply watching the seasons change. The main living spaces flow effortlessly from one to the next, creating an inviting setting for everyday living and entertaining alike. A fireplace anchors the living room before leading into the formal dining room, while the updated kitchen offers quartz countertops, stainless steel appliances, a gas range, and generous workspace. The adjoining family room features a second fireplace and French doors opening to the private backyard, where mature landscaping and a spacious deck create a peaceful extension of the home. The finished attic serves as a private primary retreat, while three additional bedrooms and a beautifully renovated bathroom with heated floors complete the upper levels. Downstairs, the finished lower level offers flexible space for a recreation room, home gym, games room, or creative studio, with a side entrance, garage access, and built-in storage adding everyday practicality. Beautifully maintained and thoughtfully updated, this is a home where timeless character and modern comfort come together just steps from everything downtown Orangeville has to offer.

9 York Street, Orangeville

Listing courtesy of ROYAL LEPAGE RCR REALTY.

$1,099,000
3 Beds ⋅ 3 Baths ⋅ W13557118 MLS® #
Welcome to 7 Henry Street, a beautifully crafted newly built, two storey home blending refined design with thoughtful everyday functionality. Built with exceptional attention to detail and premium materials, this residence offers a sophisticated living experience with a layout designed for both comfortable family living and elegant entertaining. The open concept main level is bright and inviting, highlighted by 9 foot ceilings and White Oak "Toffee Crunch" engineered hardwood flooring throughout. At the centre of the home is the stunning kitchen featuring custom Barzotti cabinetry, elegant Taj Mahal quartz countertops, and a spacious centre island with breakfast bar. A cleverly designed hidden walk in pantry provides additional storage while maintaining the kitchen's aesthetic. The living and dining areas are thoughtfully defined by custom white oak shelving, adding architectural interest while preserving the open flow. From the dining area, a walk out to the yard creates an ideal connection between indoor and outdoor living. The main level also features a 2 piece powder room and a functional mudroom with storage and direct access to the garage. Upstairs offers three spacious bedrooms, two full bathrooms, and convenient second floor laundry. The primary suite is a private retreat with a vaulted ceiling, two walk in closets, and a beautifully appointed 4 piece ensuite featuring a double vanity, oversized walk in shower, and private water closet. Bedroom two includes a walk in closet, while bedroom three offers a double closet, providing excellent storage. The unfinished lower level presents excellent future potential with large windows, storage under the stairs, and a rough in for a full bathroom. Landscaping to be completed Spring 2026, with glass installation for the primary ensuite shower also scheduled. Customization options are available. (id:5764)

7 Henry Street, Orangeville

Listing courtesy of ROYAL LEPAGE RCR REALTY.

$1,099,000
3 Beds ⋅ 3 Baths ⋅ W13557118 MLS® #
Welcome to 7 Henry Street, a beautifully crafted newly built, two storey home blending refined design with thoughtful everyday functionality. Built with exceptional attention to detail and premium materials, this residence offers a sophisticated living experience with a layout designed for both comfortable family living and elegant entertaining. The open concept main level is bright and inviting, highlighted by 9 foot ceilings and White Oak "Toffee Crunch" engineered hardwood flooring throughout. At the centre of the home is the stunning kitchen featuring custom Barzotti cabinetry, elegant Taj Mahal quartz countertops, and a spacious centre island with breakfast bar. A cleverly designed hidden walk in pantry provides additional storage while maintaining the kitchen's aesthetic. The living and dining areas are thoughtfully defined by custom white oak shelving, adding architectural interest while preserving the open flow. From the dining area, a walk out to the yard creates an ideal connection between indoor and outdoor living. The main level also features a 2 piece powder room and a functional mudroom with storage and direct access to the garage. Upstairs offers three spacious bedrooms, two full bathrooms, and convenient second floor laundry. The primary suite is a private retreat with a vaulted ceiling, two walk in closets, and a beautifully appointed 4 piece ensuite featuring a double vanity, oversized walk in shower, and private water closet. Bedroom two includes a walk in closet, while bedroom three offers a double closet, providing excellent storage. The unfinished lower level presents excellent future potential with large windows, storage under the stairs, and a rough in for a full bathroom. Landscaping to be completed Spring 2026, with glass installation for the primary ensuite shower also scheduled. Customization options are available.

7 Henry Street, Orangeville

Listing courtesy of ROYAL LEPAGE RCR REALTY.

$1,180,000
5 Beds ⋅ 4 Baths ⋅ W13491076 MLS® #
Welcome to 77 Macmaster Road, Orangeville. This stunning home boasts amazing curb appeal, situated on a 55 by 121-foot lot with a three-car garage and a wide driveway. As you step inside, the main floor welcomes you with high ceilings in the living and dining areas, offering a grand, contemporary feel. The open layout is filled with natural light and features hardwood floors throughout main floor. The spacious kitchen is a chef's dream, with stainless steel appliances, Stone backsplash ,abundant counter and cupboard space, pantry and a large central island perfect for entertaining. Upstairs, you'll find a versatile loft overlooking the great room, a spacious master bedroom with a 4-piece ensuite overlooking the family room, and three additional large bedrooms. The fully finished basement offers laminate floors, a fully open concept space for a gym, theater, or play area, plus an extra bedroom and full bath.Enjoy outdoor entertaining in your private backyard, featuring a beautiful stone patio and a pool-sized space, fully surrounded by mature trees for complete privacy.Perfectly located, this home is close to schools, parks, hospitals, and all other essential amenities. (id:5764)

77 McMaster Road, Orangeville

Listing courtesy of RE/MAX REALTY SPECIALISTS INC..

$1,100,000
4 Beds ⋅ 3 Baths ⋅ W13550588 MLS® #
Welcome to 225 Zina Street, a breathtaking brick bungalow that perfectly blends sophisticated interior updates with a massive, country-sized property. From the moment you arrive, the incredible curb appeal, pristine landscaping, and premium hardscaping hint at the quality within. Step inside to a beautifully modernized main level featuring gorgeous updated flooring and a brand-new chef's kitchen. The kitchen boasts a large center island, gleaming quartz countertops, & all-new appliances. Right off the kitchen, you'll find a spacious living room centered around a beautiful gas fireplace, featuring a large window that floods the space with natural light & overlooks the front porch & lush gardens. The primary suite serves as a peaceful retreat, complete with a private 3-pce ensuite and scenic views of the mature backyard. A second bedroom and a newly renovated 4-piece main bathroom with lovely quartz finishes complete this level. The fully finished basement expands your living space significantly. It offers a large, versatile recreation room-the perfect space for a family lounge. There are also two additional bedrooms and another 3-pce bathroom, making it a perfect setup for guests or older children. Outside, the property truly shines. Situated on a phenomenal 80' x 142' lot, the backyard is an entertainer's paradise. Relax on the 800 sq ft expansive deck under the shade of your private gazebo, or utilize the massive green space, which offers plenty of room to install your dream pool. The oversized, heated double-car garage is a rare find, complemented by a driveway that comfortably parks 8 vehicles. Located in a highly desirable neighborhood, this home is within walking distance to top-tier schools, beautiful parks, vibrant restaurants, & all the amenities Orangeville has to offer. Whether you are a young family looking for a phenomenal school zone or seniors seeking the ease of bungalow living without sacrificing space, this home shows beautifully and is a must-see! (id:5764)

225 Zina Street, Orangeville

Listing courtesy of ROYAL LEPAGE RCR REALTY.

$1,100,000
4 Beds ⋅ 3 Baths ⋅ W13550588 MLS® #
Welcome to 225 Zina Street, a breathtaking brick bungalow that perfectly blends sophisticated interior updates with a massive, country-sized property. From the moment you arrive, the incredible curb appeal, pristine landscaping, and premium hardscaping hint at the quality within. Step inside to a beautifully modernized main level featuring gorgeous updated flooring and a brand-new chef's kitchen. The kitchen boasts a large center island, gleaming quartz countertops, & all-new appliances. Right off the kitchen, you'll find a spacious living room centered around a beautiful gas fireplace, featuring a large window that floods the space with natural light & overlooks the front porch & lush gardens. The primary suite serves as a peaceful retreat, complete with a private 3-pce ensuite and scenic views of the mature backyard. A second bedroom and a newly renovated 4-piece main bathroom with lovely quartz finishes complete this level. The fully finished basement expands your living space significantly. It offers a large, versatile recreation room-the perfect space for a family lounge. There are also two additional bedrooms and another 3-pce bathroom, making it a perfect setup for guests or older children. Outside, the property truly shines. Situated on a phenomenal 80' x 142' lot, the backyard is an entertainer's paradise. Relax on the 800 sq ft expansive deck under the shade of your private gazebo, or utilize the massive green space, which offers plenty of room to install your dream pool. The oversized, heated double-car garage is a rare find, complemented by a driveway that comfortably parks 8 vehicles. Located in a highly desirable neighborhood, this home is within walking distance to top-tier schools, beautiful parks, vibrant restaurants, & all the amenities Orangeville has to offer. Whether you are a young family looking for a phenomenal school zone or seniors seeking the ease of bungalow living without sacrificing space, this home shows beautifully and is a must-see!

225 Zina Street, Orangeville

Listing courtesy of ROYAL LEPAGE RCR REALTY.

$1,049,000
4 Beds ⋅ 2 Baths ⋅ W13542600 MLS® #
Exceptional investment opportunity in the heart of Orangeville! Situated on a prominent corner lot at First Street and Fead Street, this solid two-storey brick duplex offers incredible potential for investors or those looking to live in one unit while generating rental income from the other. The property features two self-contained units, each offering 2 bedrooms, 1 full bathroom, and laundry, providing comfortable layouts that appeal to A++ tenants. With parking for up to five vehicles, this is a rare and valuable feature for a duplex in such a desirable central location. Ideally positioned within walking distance to Orangeville's vibrant downtown Broadway, residents will enjoy easy access to restaurants, cafés, boutique shopping, parks, schools, and everyday amenities. Whether you're looking to expand your investment portfolio, generate steady rental income, or take advantage of a fantastic live-in investment opportunity, this well-located duplex offers outstanding value in one of Orangeville's most sought-after neighbourhoods. Don't miss your chance to own a versatile income property with excellent long-term potential. (id:5764)

52 First Street, Orangeville

Listing courtesy of EXP REALTY.

$1,049,000
4 Beds ⋅ 2 Baths ⋅ W13542600 MLS® #
Exceptional investment opportunity in the heart of Orangeville! Situated on a prominent corner lot at First Street and Fead Street, this solid two-storey brick duplex offers incredible potential for investors or those looking to live in one unit while generating rental income from the other. The property features two self-contained units, each offering 2 bedrooms, 1 full bathroom, and laundry, providing comfortable layouts that appeal to A++ tenants. With parking for up to five vehicles, this is a rare and valuable feature for a duplex in such a desirable central location. Ideally positioned within walking distance to Orangeville's vibrant downtown Broadway, residents will enjoy easy access to restaurants, cafés, boutique shopping, parks, schools, and everyday amenities. Whether you're looking to expand your investment portfolio, generate steady rental income, or take advantage of a fantastic live-in investment opportunity, this well-located duplex offers outstanding value in one of Orangeville's most sought-after neighbourhoods. Don't miss your chance to own a versatile income property with excellent long-term potential.

52 First Street, Orangeville

Listing courtesy of EXP REALTY.

$1,099,000
4 Beds ⋅ 5 Baths ⋅ W13539166 MLS® #
Located in one of Orangeville's most sought-after family neighbourhoods, surrounded by parks, scenic walking trails, excellent schools, and some of the town's newest and most thoughtfully designed homes, this beautifully upgraded executive home offers nearly 3,000 sq. ft. of bright, elegant living space. Extensively enhanced with impressive hardscaping, warm-toned stamped concrete surrounds the driveway, front porch, walkways, and backyard, creating exceptional curb appeal and upscale outdoor living. Large architectural windows fill the home with natural light while the open-concept layout offers both comfort and versatility. Features include high ceilings, crown moulding, smooth ceilings, pot lights, California shutters, hardwood flooring, main floor office, laundry room, and a custom kitchen complete with premium countertops, abundant cabinetry, coffee/bar area, and a massive waterfall island overlooking the living space with natural gas fireplace. The spacious dining room offers flexibility as either an elegant entertaining area or additional family room space. Upstairs features 4 exceptionally large bedrooms including 2 primary-style suites with private ensuites. The main primary retreat offers double door entry, built-in closet cabinetry, double sinks, soaker tub, walk-in shower, and private water closet. Two additional oversized bedrooms share a beautifully designed Jack & Jill bathroom with double sinks and separate shower/toilet area. The finished basement extends the living space with stylish vinyl flooring, pot lights, kitchenette area, cold cellar, finished bathroom with walk-in shower, large rec room, additional storage, and a charming nook perfect for a children's play area or hobby space. A rare opportunity to own a standout family home in one of Orangeville's finest communities. (id:5764)

27 Drew Brown Boulevard, Orangeville

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

$1,099,000
4 Beds ⋅ 5 Baths ⋅ W13539166 MLS® #
Located in one of Orangeville's most sought-after family neighbourhoods, surrounded by parks, scenic walking trails, excellent schools, and some of the town's newest and most thoughtfully designed homes, this beautifully upgraded executive home offers nearly 3,000 sq. ft. of bright, elegant living space. Extensively enhanced with impressive hardscaping, warm-toned stamped concrete surrounds the driveway, front porch, walkways, and backyard, creating exceptional curb appeal and upscale outdoor living. Large architectural windows fill the home with natural light while the open-concept layout offers both comfort and versatility. Features include high ceilings, crown moulding, smooth ceilings, pot lights, California shutters, hardwood flooring, main floor office, laundry room, and a custom kitchen complete with premium countertops, abundant cabinetry, coffee/bar area, and a massive waterfall island overlooking the living space with natural gas fireplace. The spacious dining room offers flexibility as either an elegant entertaining area or additional family room space. Upstairs features 4 exceptionally large bedrooms including 2 primary-style suites with private ensuites. The main primary retreat offers double door entry, built-in closet cabinetry, double sinks, soaker tub, walk-in shower, and private water closet. Two additional oversized bedrooms share a beautifully designed Jack & Jill bathroom with double sinks and separate shower/toilet area. The finished basement extends the living space with stylish vinyl flooring, pot lights, kitchenette area, cold cellar, finished bathroom with walk-in shower, large rec room, additional storage, and a charming nook perfect for a children's play area or hobby space. A rare opportunity to own a standout family home in one of Orangeville's finest communities.

27 Drew Brown Boulevard, Orangeville

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

$1,149,900
4 Beds ⋅ 3 Baths ⋅ W13534286 MLS® #
Welcome to 23 Clarke Avenue, a beautifully appointed 4-bedroom family home nestled in one of the area's most sought-after neighbourhoods. From the moment you step inside, you'll be welcomed by a bright formal living room, offering an elegant space to relax or entertain. The heart of the home features a spacious open-concept kitchen overlooking a warm and inviting family room with a cozy fireplace-perfect for everyday living and hosting family and friends. Walk outside to your private inground pool which features stamped concrete throughout making it effortless to maintain. A formal dining room completes the main level, providing the ideal setting for holiday dinners and special occasions. Upstairs, you'll find four generously sized bedrooms, including a spacious primary retreat featuring a spa-inspired ensuite with a luxurious soaker tub, creating the perfect place to unwind at the end of the day. The lower level is partially finished, offering endless possibilities for a recreation room, kids' play area, home gym, or additional storage. Step outside to your own private backyard oasis, complete with an in-ground pool that's ready for summer entertaining, weekend barbecues, and relaxing afternoons with family and friends. Offering exceptional space, comfort, and a prime location, this is the perfect place to call home. Don't miss your opportunity to make 23 Clarke Avenue yours! (id:5764)

23 Clarke Avenue, Orangeville

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

$1,149,900
4 Beds ⋅ 3 Baths ⋅ W13534286 MLS® #
Welcome to 23 Clarke Avenue, a beautifully appointed 4-bedroom family home nestled in one of the area's most sought-after neighbourhoods. From the moment you step inside, you'll be welcomed by a bright formal living room, offering an elegant space to relax or entertain. The heart of the home features a spacious open-concept kitchen overlooking a warm and inviting family room with a cozy fireplace-perfect for everyday living and hosting family and friends. Walk outside to your private inground pool which features stamped concrete throughout making it effortless to maintain. A formal dining room completes the main level, providing the ideal setting for holiday dinners and special occasions. Upstairs, you'll find four generously sized bedrooms, including a spacious primary retreat featuring a spa-inspired ensuite with a luxurious soaker tub, creating the perfect place to unwind at the end of the day. The lower level is partially finished, offering endless possibilities for a recreation room, kids' play area, home gym, or additional storage. Step outside to your own private backyard oasis, complete with an in-ground pool that's ready for summer entertaining, weekend barbecues, and relaxing afternoons with family and friends. Offering exceptional space, comfort, and a prime location, this is the perfect place to call home. Don't miss your opportunity to make 23 Clarke Avenue yours!

23 Clarke Avenue, Orangeville

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

$1,199,000
4 Beds ⋅ 4 Baths ⋅ W13527730 MLS® #
A private backyard retreat, complete with a saltwater pool, rock waterfall, mature trees, and no neighbours behind, sets the stage for one of Orangeville's most impressive family homes. Whether you're spending quiet summer afternoons by the pool or hosting friends and family, this is a home designed to be enjoyed.Inside, the home reveals itself through thoughtful updates and a layout that balances everyday living with entertaining. The kitchen anchors the main floor with a massive island, tasteful finishes, and a walk-out to the elevated deck overlooking the backyard. Separate family and living rooms, each with their own fireplace, provide inviting spaces to gather or unwind, while the open loft above creates the perfect spot for a home office, reading nook, or lounge.Upstairs offers four spacious bedrooms, including a beautifully updated primary suite with a walk-in closet and renovated ensuite. The loft just outside the primary adds another layer of flexibility for today's lifestyle.The finished walk-out basement features a full bathroom, wet bar, third fireplace, and a versatile office with closet storage that adapts to your family's needs.Outside, the elevated deck, poolside patio, stone walkways, and mature greenery create multiple spaces to relax, entertain, and enjoy the outdoors all summer. Set on a fully fenced corner lot, the backyard feels remarkably private while remaining connected to the home.Located close to schools, the hospital, Island Lake Conservation Area, parks, and everyday amenities, this property offers the perfect balance of privacy and convenience.Recent updates over the past five years include renovations to the main floor, primary ensuite, basement, windows, air conditioning, pool liner, and more.With more than 3,200 square feet of finished living space, a three-car garage, exceptional outdoor living, and a layout that works just as well for everyday life as it does for entertaining, this home brings it all together. (id:5764)

118 Oak Ridge Drive, Orangeville

Listing courtesy of ROYAL LEPAGE RCR REALTY.

$1,199,000
4 Beds ⋅ 4 Baths ⋅ W13527730 MLS® #
A private backyard retreat, complete with a saltwater pool, rock waterfall, mature trees, and no neighbours behind, sets the stage for one of Orangeville's most impressive family homes. Whether you're spending quiet summer afternoons by the pool or hosting friends and family, this is a home designed to be enjoyed.Inside, the home reveals itself through thoughtful updates and a layout that balances everyday living with entertaining. The kitchen anchors the main floor with a massive island, tasteful finishes, and a walk-out to the elevated deck overlooking the backyard. Separate family and living rooms, each with their own fireplace, provide inviting spaces to gather or unwind, while the open loft above creates the perfect spot for a home office, reading nook, or lounge.Upstairs offers four spacious bedrooms, including a beautifully updated primary suite with a walk-in closet and renovated ensuite. The loft just outside the primary adds another layer of flexibility for today's lifestyle.The finished walk-out basement features a full bathroom, wet bar, third fireplace, and a versatile office with closet storage that adapts to your family's needs.Outside, the elevated deck, poolside patio, stone walkways, and mature greenery create multiple spaces to relax, entertain, and enjoy the outdoors all summer. Set on a fully fenced corner lot, the backyard feels remarkably private while remaining connected to the home.Located close to schools, the hospital, Island Lake Conservation Area, parks, and everyday amenities, this property offers the perfect balance of privacy and convenience.Recent updates over the past five years include renovations to the main floor, primary ensuite, basement, windows, air conditioning, pool liner, and more.With more than 3,200 square feet of finished living space, a three-car garage, exceptional outdoor living, and a layout that works just as well for everyday life as it does for entertaining, this home brings it all together.

118 Oak Ridge Drive, Orangeville

Listing courtesy of ROYAL LEPAGE RCR REALTY.

$1,200,000
4 Beds ⋅ 4 Baths ⋅ W13499634 MLS® #
Exceptional opportunity with this fully rented four plex in a great Orangeville location. Easy walking distance to all amenities (theatre, shopping, fine dining, parks, trails and more). Well maintained and upgraded bungalow style building with four one bedroom units. Each unit has separate hydro meters. Zoned RM2 multi residential. Lower level has coin operated laundry, storage, and private storage unit for each apartment. Awesome lot with private rear grounds. Very unique with a long waiting list. See list of extras and upgrades attached. (id:5764)

44 Church Street, Orangeville

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

$1,200,000
4 Beds ⋅ 4 Baths ⋅ W13499634 MLS® #
Exceptional opportunity with this fully rented four plex in a great Orangeville location. Easy walking distance to all amenities (theatre, shopping, fine dining, parks, trails and more). Well maintained and upgraded bungalow style building with four one bedroom units. Each unit has separate hydro meters. Zoned RM2 multi residential. Lower level has coin operated laundry, storage, and private storage unit for each apartment. Awesome lot with private rear grounds. Very unique with a long waiting list. See list of extras and upgrades attached.

44 Church Street, Orangeville

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

$1,149,900
4 Beds ⋅ 3 Baths ⋅ W13490510 MLS® #
Fabulous 4-Bedroom Family Home Backing Onto Conservation in Orangeville!Welcome to this beautifully maintained home in one of Orangeville's most sought-after neighbourhoods, offering the perfect blend of style, comfort, and function. A stamped concrete driveway, stairs, and walkway (2019) lead to a grand front entrance with vaulted ceiling and ceramic flooring. The open-concept main level features a spacious living room with abundant natural light and a cozy gas fireplace, an oversized eat-in kitchen with breakfast bar and walkout to a newer deck, railings, and fenced backyard. A versatile dining room, hardwood flooring, and a 2-pc bath complete the main floor, with direct access to the 2-car garage from inside and convenient loft storage in the garage.Upstairs, the primary suite impresses with a large walk-in closet, 4-pc ensuite with soaker tub and separate shower. Three additional generously sized bedrooms provide plenty of space for a growing family. The finished lower level offers a recreation room, perfect for entertaining guests.This move-in ready home combines family living with a serene setting backing onto conservation land. Recent Renos include Hardwood floor and baseboards, staircase(2023), Windows(2023), Attic insulation(2024), Water softener (2025), Garage door and opener(2024). The home is carpet free! (id:5764)

53 Abbey Road, Orangeville

Listing courtesy of CENTURY 21 GREEN REALTY INC..

$1,180,000
5 Beds ⋅ 4 Baths ⋅ W13491076 MLS® #
Welcome to 77 Macmaster Road, Orangeville. This stunning home boasts amazing curb appeal, situated on a 55 by 121-foot lot with a three-car garage and a wide driveway. As you step inside, the main floor welcomes you with high ceilings in the living and dining areas, offering a grand, contemporary feel. The open layout is filled with natural light and features hardwood floors throughout main floor. The spacious kitchen is a chef's dream, with stainless steel appliances, Stone backsplash ,abundant counter and cupboard space, pantry and a large central island perfect for entertaining. Upstairs, you'll find a versatile loft overlooking the great room, a spacious master bedroom with a 4-piece ensuite overlooking the family room, and three additional large bedrooms. The fully finished basement offers laminate floors, a fully open concept space for a gym, theater, or play area, plus an extra bedroom and full bath.Enjoy outdoor entertaining in your private backyard, featuring a beautiful stone patio and a pool-sized space, fully surrounded by mature trees for complete privacy.Perfectly located, this home is close to schools, parks, hospitals, and all other essential amenities.

77 McMaster Road, Orangeville

Listing courtesy of RE/MAX REALTY SPECIALISTS INC..

$1,149,900
4 Beds ⋅ 3 Baths ⋅ W13490510 MLS® #
Fabulous 4-Bedroom Family Home Backing Onto Conservation in Orangeville!Welcome to this beautifully maintained home in one of Orangeville's most sought-after neighbourhoods, offering the perfect blend of style, comfort, and function. A stamped concrete driveway, stairs, and walkway (2019) lead to a grand front entrance with vaulted ceiling and ceramic flooring. The open-concept main level features a spacious living room with abundant natural light and a cozy gas fireplace, an oversized eat-in kitchen with breakfast bar and walkout to a newer deck, railings, and fenced backyard. A versatile dining room, hardwood flooring, and a 2-pc bath complete the main floor, with direct access to the 2-car garage from inside and convenient loft storage in the garage.Upstairs, the primary suite impresses with a large walk-in closet, 4-pc ensuite with soaker tub and separate shower. Three additional generously sized bedrooms provide plenty of space for a growing family. The finished lower level offers a recreation room, perfect for entertaining guests.This move-in ready home combines family living with a serene setting backing onto conservation land. Recent Renos include Hardwood floor and baseboards, staircase(2023), Windows(2023), Attic insulation(2024), Water softener (2025), Garage door and opener(2024). The home is carpet free!

53 Abbey Road, Orangeville

Listing courtesy of CENTURY 21 GREEN REALTY INC..

$1,299,000
4 Beds ⋅ 2 Baths ⋅ W13483036 MLS® #
Welcome to 17 First Avenue, a truly stunning red brick Century Home, built in 1933 and rich with timeless charm. Perfectly located in the heart of downtown Orangeville, this home is just steps to the town's best restaurants, cafes, and shops, offering walkable convenience with small-town charm. Set on an impressive 65 ft x 155 ft lot, the property features mature trees, lush gardens, and a massive fully fenced backyard backing onto a laneway that provides many opportunities including adding a detached garage or garden sweet with an in-law apartment- a rare find in such a prime location. Inside, you'll find nearly 2,500 sq ft of beautifully maintained living space with hardwood flooring throughout. The home offers 4 large bedrooms and 2 fully renovated bathrooms. The newly renovated kitchen is a showstopper, featuring cream-coloured custom cabinetry, quartz countertops, and a picturesque view overlooking the backyard. The back deck is brand new, this is the perfect space to enjoy the warm Summer months! The spacious dining room comfortably seats 8 guests and is ideal for hosting family and friends. The living room and family room are warm and inviting, each with a gas fireplace and tasteful updates that blend character with modern comfort. Just off the living room, a charming sunroom provides the perfect spot for morning coffee or quiet reading. The finished basement adds exceptional value, complete with a cozy movie theatre room with a third gas fireplace and a dedicated craft room. This home is full of warmth, charm, and thoughtful updates. A true haven for century home lovers seeking character, space, and an unbeatable downtown location. (id:5764)

17 First Avenue, Orangeville

Listing courtesy of ROYAL LEPAGE RCR REALTY.

$1,299,000
4 Beds ⋅ 2 Baths ⋅ W13483036 MLS® #
Welcome to 17 First Avenue, a truly stunning red brick Century Home, built in 1933 and rich with timeless charm. Perfectly located in the heart of downtown Orangeville, this home is just steps to the town's best restaurants, cafes, and shops, offering walkable convenience with small-town charm. Set on an impressive 65 ft x 155 ft lot, the property features mature trees, lush gardens, and a massive fully fenced backyard backing onto a laneway that provides many opportunities including adding a detached garage or garden sweet with an in-law apartment- a rare find in such a prime location. Inside, you'll find nearly 2,500 sq ft of beautifully maintained living space with hardwood flooring throughout. The home offers 4 large bedrooms and 2 fully renovated bathrooms. The newly renovated kitchen is a showstopper, featuring cream-coloured custom cabinetry, quartz countertops, and a picturesque view overlooking the backyard. The back deck is brand new, this is the perfect space to enjoy the warm Summer months! The spacious dining room comfortably seats 8 guests and is ideal for hosting family and friends. The living room and family room are warm and inviting, each with a gas fireplace and tasteful updates that blend character with modern comfort. Just off the living room, a charming sunroom provides the perfect spot for morning coffee or quiet reading. The finished basement adds exceptional value, complete with a cozy movie theatre room with a third gas fireplace and a dedicated craft room. This home is full of warmth, charm, and thoughtful updates. A true haven for century home lovers seeking character, space, and an unbeatable downtown location.

17 First Avenue, Orangeville

Listing courtesy of ROYAL LEPAGE RCR REALTY.

$1,349,000
4 Beds ⋅ 2 Baths ⋅ W13473022 MLS® #
Excellent opportunities with this well maintained and updated duplex in a great location on Broadway. Close to all amenities that Orangeville has to offer (theatre, dining, trails, parks, shopping and fine dining) Units show well. Floor plans attached. Detached oversize garage. Paved rear lot allows for ample parking. Ideal situation for home occupation with a rental unit or simply as a solid investment opportunity. Walk in basement has tons of potential. New roof in fall of 2025. Portion of rear yard is rented to neighbouring commercial business for client parking. 2 furnaces (tenants pay their own heat). Garage (24' x 34') is heated. Shared laundry in basement. Interior stairs from basement to main entry and apartments. Endless possibilities. Building will be vacant on closing so you can set your own rents. (id:5764)

300 A Broadway, Orangeville

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

$1,349,000
4 Beds ⋅ 2 Baths ⋅ W13473022 MLS® #
Excellent opportunities with this well maintained and updated duplex in a great location on Broadway. Close to all amenities that Orangeville has to offer (theatre, dining, trails, parks, shopping and fine dining) Units show well. Floor plans attached. Detached oversize garage. Paved rear lot allows for ample parking. Ideal situation for home occupation with a rental unit or simply as a solid investment opportunity. Walk in basement has tons of potential. New roof in fall of 2025. Portion of rear yard is rented to neighbouring commercial business for client parking. 2 furnaces (tenants pay their own heat). Garage (24' x 34') is heated. Shared laundry in basement. Interior stairs from basement to main entry and apartments. Endless possibilities. Building will be vacant on closing so you can set your own rents.

300 A Broadway N/A, Orangeville

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

$1,165,000
4 Beds ⋅ 3 Baths ⋅ W13468052 MLS® #
Welcome to one of Orangeville's most sought-after addresses. Nestled on a premium ravine lot (69x173 ft)on prestigious Chapman Road, this beautifully maintained 2+2 bedroom finished bungalow with walkout basement offers the perfect blend of privacy, comfort, and exceptional indoor-outdoor living. Surrounded by mature trees and backing onto greenspace, the pool size fenced landscaped backyard feels like your own private retreat. Spend summer evenings entertaining beneath the charming pergola with family and friends while enjoying the peaceful natural setting, or visit under the private covered front porch. Rarely do properties offer this level of privacy and outdoor enjoyment in such a desirable neighbourhood. Inside, the bright open-concept design is ideal for both everyday living and entertaining. The spacious eat-in kitchen features granite countertops, a gas stove, abundant cabinetry, and a walkout to the deck with glassed in railing overlooking the backyard. The welcoming living and dining areas offer plenty of space for hosting family gatherings and special occasions. The main level features two generous bedrooms, including a spacious primary suite with vaulted ceilings and a beautifully renovated spa like ensuite. The finished walkout basement expands the living space with two additional bedrooms, a renovated 3-pc bathroom, a large recreation area, gas fireplace/stove, games/dining room, kitchenette and direct access to the backyard. Perfect for multi-generational living, extended family, teenagers, guests, or in-law suite. Additional features include a 2.5-car garage with professionally built mezzanine for extra organized storage, parking for 6 vehicles, main bedrooms hardwood flooring,(2018) owned hot water tank (2023) and water softener, (2021) shingles (2016), renovated ensuite (2022), renovated basement bathroom (2023), furnace (2024), basement update (2020) replaced garage door, whole-home surge protection, and wiring in place for a future hot tub. (id:5764)

26 Chapman Road, Orangeville

Listing courtesy of MCCARTHY REALTY.