Orangeville Real Estate | Orangeville Properties for Sale

Spacious. Versatile. Connected. Welcome to 27 Rustic Street in the heart of Orangeville-a beautifully maintained 3-level side split offering exceptional space, flexibility, and lifestyle. Ideally located within walking distance to schools and parks, and just minutes to shopping, recreation facilities, and downtown, this home also provides convenient access to Highways 9 and 10 for an easy commute.This thoughtfully designed home features 4 bedrooms and multiple living areas, ideal for growing families or multi-generational living. The garage has been converted to expand the main living space, creating an oversized living room along with a functional laundry/mudroom offering direct access to the backyard.The kitchen is well-appointed with stainless steel appliances, including a gas stove, and flows seamlessly into the dining area with a walk-out to the backyard deck-perfect for everyday living and entertaining.Upstairs, the primary suite has been reconfigured from two bedrooms into a spacious retreat complete with his and hers closets.The lower level offers excellent in-law potential with a separate entrance, two additional bedrooms, a 3-piece bathroom, and a laundry hookup. A second lower level with approximately 5-foot ceilings provides additional versatile space for storage or future use.Set on a fully fenced lot, the backyard is designed for both function and enjoyment. A fantastic opportunity to own a versatile home in a family-friendly community, offering both comfort and convenience in one of Orangeville's most desirable locations.

27 Rustic Crescent, Orangeville

$984,900

4 Beds ⋅ 4 Baths ⋅ W13547352 MLS

Welcome to 29 Alder Street in Orangeville, a beautifully maintained 3+1 bedroom, 4 bathroom home offering spacious family living w/ the added bonus of a finished lower level and the opportunity for a quick & easy in-law suite conversion. From the moment you arrive, this home makes a strong impression with its charming curb appeal, double-car garage, and inviting front entry. Inside features a bright and functional layout with a spacious foyer, convenient powder room, soaring ceiling over the dining area, and hardwood flooring through the principal living spaces. The living room is filled with natural light and a cozy fireplace, while the updated kitchen offers plenty of cabinet space, stainless steel appliances, ample prep space, and a breakfast bar overlooking the family room. This home offers 3 well-sized bedrooms, including a generous primary bedroom complete with a walk-in closet and a beautifully updated ensuite with double sinks, glass shower, and soaker tub. The upper level also offers another full bathroom and the added convenience of second-floor laundry. The finished basement extends your living space with a wet bar, bright living space, bedroom area, and full bathroom, creating excellent flexibility for extended family, guests, or multi-generational living. Step outside to enjoy a private backyard with mature trees, a large lawn, covered patio area, hot tub, and deck space for relaxing or entertaining. Located in a desirable Orangeville neighbourhood close to parks, schools, and amenities, this is a fantastic opportunity to own a spacious home with room for the whole family

29 Alder Street, Orangeville

$999,900

4 Beds ⋅ 3 Baths ⋅ W13543656 MLS

Welcome to this exceptional 4 Bedroom, 2,000+ sq. ft. detached home, ideally located in one of Orangeville's most sought-after family neighbourhoods. Set on a quiet street close to excellent schools, parks, walking trails, shopping & everyday amenities. This beautifully maintained all-brick two-story home offers the perfect blend of space, comfort & functionality for today's growing family. From the moment you arrive, the home's impressive curb appeal & newer front entry door create a warm welcome. Inside, the spacious foyer showcases a stunning oak staircase w/elegant iron railings, setting the tone for the quality found throughout. The bright & inviting living & dining room provide an ideal space for both everyday living & entertaining. The spacious eat-in kitchen offers ample cabinetry, generous counter space, making meal preparation a breeze. One of its standout features is the walkout to the back deck, creating the perfect setting for morning coffee, summer barbecues, or relaxing evenings overlooking the private, generously sized backyard. Just off the kitchen, the cozy family room is highlighted by a charming wood-burning fireplace, offering the perfect place to gather w/family & friends. Convenient main-floor laundry room w/direct access to the double-car garage adds practicality. Upstairs, you'll find 4 generously sized bedrooms, each featuring large windows that fill the rooms w/natural light & closet space. The spacious primary suite could accommodate a king-sized bedroom set & includes a walk-in closet along w/private 4-piece ensuite. 4-piece main bath serves the remaining bedrooms, all of which feature glass-door closets & multiple windows. Finished lower level provides an expansive rec room that's perfect for a games area, home theatre, fitness space or children's playroom. With abundant storage & endless possibilities, this level offers valuable add'l living space for the entire family. This exceptional property is one you won't want to miss.

45 Fieldgate Drive, Orangeville

$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

$579,900

2 Beds ⋅ 3 Baths ⋅ W13540630 MLS ⋅ Midtown BLDG.

Welcome to this stunning, fully finished 2-bedroom, 3-bathroom condo offering over 1,200 sq. ft. of beautifully designed living space. Thoughtfully upgraded with modern finishes and a highly sought-after open-concept layout, this home perfectly blends style, comfort, and functionality.The bright and spacious main level is filled with natural light thanks to additional bonus windows and features a beautifully appointed kitchen complete with a large family-sized centre island-perfect for entertaining, casual dining, or gathering with friends and family. Enjoy the convenience of a main floor laundry room and powder room, along with abundant storage throughout.Step through the large sliding doors to your own cozy and truly private balcony-the perfect place to enjoy your morning coffee or unwind at the end of the day.Upstairs, you'll find two generous bedrooms, including a spacious primary retreat featuring a walk-in closet and a luxurious 4-piece ensuite with a sleek glass walk-in shower. A second full bathroom provides added convenience for family or guests.Ideally located close to all amenities, parks, shopping, restaurants, schools, and the charming shops and cafés of downtown Orangeville, this exceptional condo offers low-maintenance living without compromising space or style. Simply move in and enjoy!

17 Centre Street Unit 312, Orangeville

$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

$879,000

5 Beds ⋅ 3 Baths ⋅ W13538418 MLS

Welcome to this beautifully renovated and exceptionally versatile home in one of Orangeville's most desirable neighbourhoods, just a short walk to vibrant downtown shops, restaurants, cafés, festivals, parks, schools, and everyday amenities. Situated on a rare 66 x 165 ft private lot, this move-in-ready property offers the perfect blend of charm, functionality, and endless possibilities.The main home has been extensively updated with new flooring, a stunning modern kitchen featuring granite countertops and custom built-in shelving, bright open-concept living and dining areas, spacious bedrooms, updated bathrooms, and quality finishes throughout. Whether you're upsizing, downsizing, or looking for multi-generational living, this home is designed to adapt to your lifestyle.A standout feature is the self-contained legal studio apartment, complete with soaring ceilings, skylights, a full kitchen, full bathroom, and laundry rough-in. Ideal as an Airbnb, income-generating rental, private guest suite, home office, or independent living space for extended family or teenagers.The lower level adds even more flexibility with additional 2 bedrooms and 1 bath, making this home ideal for large or growing families.Step outside and enjoy your own private backyard oasis featuring mature trees, new concrete patio, and plenty of room to entertain, relax, or let the kids play. The new interlock on driveway adds outstanding curb appeal, while the oversized drive-through double garage and parking for up to six vehicles provide convenience that's hard to find.Beautifully updated, incredibly functional, and located in one of Orangeville's most walkable communities, this is far more than just a home-it's a unique opportunity offering flexibility, income potential, and a lifestyle you'll love for years to come.

74 John Street, Orangeville

$798,000

3 Beds ⋅ 2 Baths ⋅ W13537296 MLS

Step into a piece of Orangeville's history with this beautifully preserved 1876 century home, situated on an impressive 1/3 acre lot with the rare benefit of a 4 car detached workshop. This one-of-a-kind property offers exceptional outdoor space, a fully fenced backyard, mature landscaping, a wraparound covered porch, patio, firepit, vegetable garden, and room to enjoy every season. Inside, the home is rich with original architectural details, including hardwood plank floors, 10-foot ceilings, stunning stained glass, original staircase, heavy hardwood doors, 12-inch baseboards, crown mouldings, ceiling medallions, and beautiful millwork throughout. The bright main floor features a welcoming foyer, spacious family room, versatile third bedroom or home office, convenient main floor laundry, and a charming country kitchen with butcher block countertops that walks out to the private backyard. Upstairs, you'll find two generous bedrooms and a beautifully updated Victorian-inspired bathroom featuring an enclosed clawfoot tub and separate shower. The stone coated metal roofing offers lifetime peace of mind. A truly rare highlight is the detached 1000 sq ft insulated garage/shop with 100-amp service, 220V power, lifetime roof, polished concrete floors, woodstove, and space for up to four vehicles. Combined with the fully paved driveway, this property offers parking for an incredible 16 vehicles - an unmatched feature in town, perfect for hobbyists, collectors, home businesses, or anyone needing exceptional storage and workspace. Awarded the Town of Orangeville Heritage Awareness Plaque while not being heritage designated, this remarkable home offers all the charm of a century property without any restrictions. Located just steps to Orangeville's favourite parks, schools, downtown amenities, and the GO Bus, this is a rare opportunity to own one of Orangeville's most distinctive homes.

39 Townline N/A, Orangeville

$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

$689,000

3 Beds ⋅ 4 Baths ⋅ W13533272 MLS

Why does Preston stand out from the rest? No monthly fees, one of the biggest lots on the street (no neighbours behind!!) and garage loft storage space most of the others don't have! 117 Preston is a true freehold townhouse that delivers what most townhouses can't - starting with an oversized private lot with no home behind you. That means real privacy, real outdoor space, and room for swing sets, gardens, and summer dinners outside. Inside, three generous bedrooms and four bathrooms give a growing family room to spread out. The kitchen has been thoughtfully updated for busy weeknights and weekend gatherings, and custom California Closet built-ins frame the living room television - a polished, organized touch you rarely see at this price point. The fully finished lower level adds the flex space every family wants, anchored by a cozy electric fireplace - family retreat, media room, or home office, your call. And that storage? A rare loft space in the garage keeps seasonal gear and extras neatly tucked away without giving up your parking spot. With a garage space plus a driveway spot, parking is covered too. Between the oversized lot, the updated kitchen, the finished basement, and zero monthly fees, 117 Preston stacks up as one of the strongest values in the neighbourhood. Tucked into a family-friendly pocket close to schools, parks, and everything Orangeville has to offer, this is the rare townhouse that lives like a detached - a place to settle in and grow! New Furnace Aug 2026, AC 2020

117 Preston Drive, Orangeville

$799,900

3 Beds ⋅ 2 Baths ⋅ W13531000 MLS

Welcome to 17 First Street, a charming Queen Anne-style two-storey semi-detached century home in the heart of Orangeville. This tastefully modernized residence beautifully blends historical elegance with contemporary comforts. Step inside to discover a main floor adorned with pot lights and a bright, inviting atmosphere. The main floor and second-storey windows have been replaced but retain the original stained glass arch transoms, filling the home with natural light and showcasing its heritage. The gourmet kitchen boasts quartz countertops and stainless-steel appliances, offering modern convenience while complementing the home's classic charm. Convenience is key with a full bathroom and a laundry room located on the main floor, adding to the home's functionality. Upstairs, you'll find three generous bedrooms and an additional bathroom, providing ample space for family living. The large unfinished attic presents a fantastic opportunity to expand your living space imagine a cozy loft, home office, or studio tailored to your needs. Outdoor living is equally impressive with a large private deck in the backyard, ideal for entertaining or enjoying quiet evenings. Parking is convenient with space for two cars. The property's C5 zoning provides the flexibility to use the space for much more than just a residence, opening doors to various possibilities. Location is everything, and this home delivers. You're less than a five-minute walk to the vibrant shops and restaurants on Broadway, allowing you to fully embrace the downtown lifestyle. Don't miss this amazing opportunity to own a piece of Orangeville's history while enjoying all the modern amenities you desire. **EXTRAS** This C5-zoned property offers a range of business opportunities, with the added option to convert the attic into extra living space. Imagine the potential for your business and lifestyle here it's a canvas ready for your vision! Seller will offer financing to qualified buyers.

17 First Street, Orangeville

$479,000

1 Beds ⋅ 1 Baths ⋅ W13530882 MLS

Welcome to modern, carefree living in the heart of Orangeville! This bright, chic, and well appointed one bedroom, condo is only three years old and offers the perfect blend of style, comfort, and affordability. Whether you are a first time buyer looking to enter the market or a savvy investor, this property delivers incredible value in a great location. The contemporary design features an open concept layout with beautiful finishes, high ceilings, and plenty of light. The chic kitchen is equipped with stainless steel appliances, quartz countertops, and modern cabinetry perfect for culinary enthusiasts. You can unwind with your morning coffee on the private, west facing balcony, which is perfect for catching stunning evening sunsets. The comfortable bedroom serves as a spacious retreat. Living area is cozy and a perfect place to put your feet up and relax at the end of a long day. The Large spacious bathroom has glass shower, tile floors and oversized cabinetry for storage. Enjoy the peace of mind that comes with secure building access, along with the convenience of an exclusive use parking spot and storage locker. Living in Orangeville gives you a vibrant community with small town charm and all the modern amenities you could ask for. You are just steps away from local shops, cafes along Broadway, scenic walking trails, and major commuter routes. Experience affordable luxury without compromising on location or lifestyle.

310 Broadway Avenue Unit 309, Orangeville

$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

$799,900

4 Beds ⋅ 4 Baths ⋅ W13523460 MLS

Welcome To This Well-Designed 3+1 Bedroom Detached Home In A Desirable South Orangeville Location. Offering A Functional Layout With Durable Ceramic And Laminate Flooring Throughout, This Home Is Perfect For Growing Families.Enjoy The Convenience Of Direct Garage Access Into The Home And Main Floor Laundry. The Family-Size Kitchen Is A Chef's Dream, Featuring Elegant Quartz Countertops, A Single/Double Size Sink, And A Breakfast Bar - Ideal For Casual Dining. Step Out From The Kitchen To Your Private Deck, Perfect For Entertaining Or Relaxing Outdoors.Upstairs, You'll Find A Spacious Second Floor Family Room With Fireplace - Great For Family Movie Nights Or Easily Modified Into A 4th Bedroom To Suit Your Needs.The Primary Bedroom Is A True Retreat, Boasting A Spa-Like Ensuite With A Soak Tub And Separate Shower, Plus A Walk-In Closet Complete With Custom Organizers.The Finished Basement Adds Valuable Living Space With A Fourth Bedroom, Semi-Ensuite Bathroom, Second Kitchen, Spacious Rec Room, And A Workshop - Perfect For Extended Family, Guests, Or A Home-Based Business.Don't Miss This Move-In-Ready Gem, Available This Summer!

452 Jay Crescent, Orangeville

$919,900

5 Beds ⋅ 4 Baths ⋅ W13520780 MLS

Welcome to 103 Hunter Road, a rare income generating opportunity in Orangeville's sought after West End! This exceptional property stands out for its incredible versatility, offering 2 fully self contained lower level units in addition to the main family home - ideal for rental income, multi-generational living, or mortgage support. With 3 separate living spaces in total, this property combines modern updates, flexible functionality, and natural beauty in one turnkey package. The main floor showcases an open concept design with a bright kitchen, spacious living and dining areas, and a walkout to an elevated deck overlooking serene green space. Two generous bedrooms on this level each feature their own private ensuite bathrooms. Downstairs, the fully finished walkout basement includes 2 private in-law suites, each with its own entrance, kitchen, living area, bedroom, and 4 piece ensuite. Set on a beautifully landscaped lot backing onto lush green space, this meticulously maintained home offers both privacy and strong income potential - a true investment in comfort and versatility. Don't miss your chance to own this one-of-a-kind property. Take a look for yourself today! ** Versatile main floor family room can also function as and is being listed as a third bedroom **

103 Hunter Road, Orangeville

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