Orangeville Real Estate | Orangeville Properties for Sale

Exceptional Investment Opportunity in the Heart of Orangeville! Welcome to 5 Fourth Avenue, a well-maintained triplex offering an excellent opportunity for investors or those looking to expand their real estate portfolio. Ideally located just off First Street, this property is within walking distance to downtown Orangeville's shops, restaurants, parks, schools, and everyday amenities, making it a highly desirable location for tenants. The building features three self-contained units, including two spacious main floor 2-bedroom apartments and one upper-level 1-bedroom apartment. Each unit offers a functional layout complete with a 4-piece bathroom. Both main floor units include the convenience of in-suite laundry. Each unit has its own separate hydro meter, simplifying utility management. Whether you're looking to generate strong rental income, add to your investment portfolio, or live in one unit while renting the others, this versatile property offers incredible potential in one of Orangeville's most convenient locations. Don't miss your chance to own a solid income-producing property in a thriving community.

5 Fourth Avenue, Orangeville

$769,900

4 Beds ⋅ 2 Baths ⋅ W13568990 MLS

Welcome to this beautifully maintained detached bungalow with an attached garage, ideally located in a highly sought-after family-friendly neighbourhood just steps from Harvey Curry Park. This spacious bungalow offers the perfect blend of comfort, style and functionality, making it an excellent choice for families, downsizers, or anyone looking for the convenience of main-floor living with additional finished space below. The bright and inviting living and dining room is filled with natural light from large windows, creating a warm and welcoming atmosphere. The well-designed kitchen features modern appliances, generous counterspace, and plenty of cabinetry for storage. The main level offers three spacious bedrooms and a full bathroom, while the fully finished basement provides even more room to enjoy with a large recreation room featuring a cozy gas fireplace, a fourth bedroom that is perfect for guests, a teenager, or an in-law suite, and a second full bathroom for added convenience. Step outside to your private, fully fenced backyard oasis complete with beautiful gardens, a garden shed, a fire pit, and a screened-in deck that is perfect for relaxing or entertaining family and friends. Conveniently located close to parks, schools, shopping, and everyday amenities, this exceptional bungalow offers everything you need in a location you will love. Do not miss your opportunity to make this beautiful property your next home!

88 Shirley Street, Orangeville

$897,900

3 Beds ⋅ 3 Baths ⋅ W13565194 MLS

Welcome to 39 Passmore Avenue in Orangeville, a well cared for 2 storey home located in a quiet, family friendly neighbourhood. Lovingly maintained by the original owner, this property reflects true pride of ownership both inside and out, from the beautifully landscaped front gardens to the inviting curb appeal that creates a lasting first impression. Offering approximately 1,929 square feet of thoughtfully designed living space plus a fully finished lower level, this home provides plenty of room for comfortable everyday living and entertaining. Upon entering, you are welcomed by formal living and dining rooms featuring rich hardwood flooring, creating an ideal space for family gatherings and special occasions. The heart of the home is the bright eat in kitchen, which opens to a sunny breakfast area with a walk out to the back deck. The kitchen also overlooks the family room, where a gas fireplace creates a warm and inviting atmosphere.The main floor also includes a convenient 2 piece powder room and laundry area, adding practical function to the layout. Upstairs, the spacious primary bedroom retreat features a private 4 piece ensuite, while two additional bedrooms share a second full bathroom, providing comfortable accommodation for family members or guests. The finished lower level offers additional living space with a large recreation room, a dedicated workshop, and a cold storage room, making it ideal for hobbies, storage, or a flexible family space. Outside, the fully fenced backyard is perfect for outdoor enjoyment, whether relaxing, gardening, or hosting summer barbecues. The property also features an attached 2 car garage and has benefited from numerous upgrades over the years. Located close to parks, schools, and everyday amenities, 39 Passmore Avenue offers a wonderful opportunity to enjoy comfortable living in one of Orangeville's established neighbourhoods. Seller is willing to replace carpet upstairs for new buyers.

39 Passmore Avenue, Orangeville

$199,999

W13565184 MLS

LOCATION - LOCATION - LOCATION - near and just beside Orangeville Hospital, in a busy plaza with medical shops, a great neighbourhood with stable income, and a super turnkey opportunity. Exceptional opportunity to acquire a successful, turnkey shawarma restaurant in one of Orangeville's busiest retail plazas. Located at 50 Rolling Hills Drive, Unit 8, this established business offers a fully equipped commercial kitchen, an efficient operating layout, and a strong foundation for continued success. Positioned in a high-visibility, high-traffic location surrounded by growing residential communities, schools, and complementary businesses, the restaurant enjoys consistent customer traffic and excellent exposure. The business is well suited for an owner-operator, family business, or investor looking to capitalize on the continued demand for quality quick-service dining. An attractive lease is in place, with significant upside potential to increase revenue through expanded operating hours, online delivery services, catering, corporate lunch programs, and strategic marketing initiatives. This is a rare opportunity to take over an established operation with immediate income potential and room for substantial future growth. A true turnkey business-step in and start operating from day one.

50 Rolling Hills Drive, Orangeville

$539,900

2 Beds ⋅ 1 Baths ⋅ W13556978 MLS

Experience carefree condo living in the heart of downtown Orangeville! This bright and spacious 2-bedroom, 1-bathroom suite offers approximately 965 sq. ft. of thoughtfully designed living space on the 5th floor, complete with beautiful views overlooking Broadway. Step outside your door and enjoy the ultimate walkable lifestyle with restaurants, cafés, boutique shopping, the Orangeville Farmers' Market, flower shops, and more just moments away. The open-concept living and dining area is perfect for both everyday living and entertaining, while the enclosed sunroom-style balcony extends your living space and fills the home with natural light year-round. The kitchen offers generous counter space and a peninsula with seating on both sides, making it ideal for casual meals or hosting family and friends. The spacious primary bedroom features a walk-in closet and semi-ensuite access to the well-appointed 4-piece bathroom, complete with a linen closet and ample vanity storage. A bright second bedroom provides flexibility for guests, a home office, or hobby space. Enjoy the convenience of in-suite laundry, adding everyday comfort.This well-maintained building offers fantastic amenities including a party room, billiards room, fitness/activity room, guest parking, an exclusive parking space, and a private storage locker. Located just minutes from Island Lake Conservation Area, you'll enjoy easy access to walking trails, kayaking, and nature, while Highway 10 offers convenient commuting to Brampton, Mississauga, and the GTA. Whether you're downsizing, purchasing your first home, or looking for a low-maintenance lifestyle in one of Orangeville's most desirable locations, this exceptional condo is one you won't want to miss.

200 Broadway N/A Unit 507, Orangeville

$625,000

3 Beds ⋅ 3 Baths ⋅ W13552646 MLS

Excellent Opportunity Charming Brand New 3-Bedroom Townhome Nestled in the Heart of Orangeville! Featuring 9ft Ceilings ,Open-Concept Layout, Wood Flooring, Stainless Steel Appliances, Two Balconies, Large Windows and Stylish Finishes No Carpet Wood Flooring Throughout Balcony Off The Master Bedroom Ensuite Bath & Balcony On Main Floor With Deck. Conveniently Located Near Essential Amenities. Shops, Schools, Parks, and Groceries. This Townhouse is the Ideal Blend of Luxury and Convenience! Excellent Location & Opportunity

68 First Street Unit 34, 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

$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

$1,079,000

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, mini 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

$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

$735,000

4 Beds ⋅ 2 Baths ⋅ W13506774 MLS

When Lot Size Matters to you. Opportunities like this don't come along often! This spacious and beautifully maintained 4-bedroom family home offers exceptional value in a sought-after neighborhood. With parking for up to 6 vehicles and a large, private backyard with no rear neighbors, you'll have all the space your family needs. The outdoor oasis features a large above-ground pool (approx. 2020), multiple decks and patios, storage sheds, and plenty of room for entertaining, relaxing, and enjoying summer with family and friends. Inside, you'll find a bright, open-concept layout designed for comfortable family living. The welcoming foyer features a new front door in 2025, pot lights, with additional pot lighting in the family room and finished basement. The cozy family room showcases a beautiful wood-burning fireplace with an iron insert and offers a walkout to the fully fenced backyard. The spacious living and dining rooms flow seamlessly into the kitchen, creating an ideal space for both everyday living and entertaining. The primary bedroom features his-and-hers closets with convenient semi-Ensuite access to the main bathroom. Interior access to the garage from the foyer adds everyday convenience. This home has been lovingly cared for and updated throughout, including: Furnace, central air conditioning, and on-demand water heater (2021), roof (2023), paved driveway (2023), patio door (2020), front door (2025), and above-ground pool (approx. 2020).Ideally located within walking distance to shopping, schools, the recreation centre, public transit, and other everyday amenities, this move-in-ready home truly offers the perfect combination of space, privacy, location, and value. Don't miss your chance to make this exceptional family home your own! PS the big front tree is a beautiful Mulberry Tree. Basement also has a huge Storage area for all your stuff and more.

111 Diane Drive, Orangeville

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