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$1,129,900
5 Beds ⋅ 4 Baths ⋅ W13739178 MLS
Welcome to 77 McMaster Rd, a beautifully maintained detached 2 storey home offering exceptional curb appeal with a rare triple-car garage and spacious driveway. The bright, open concept main floor features hardwood flooring, a stunning great room with soaring cathedral ceilings and gas fireplace, formal living and dining areas and a gourmet eat-in kitchen complete with granite countertops, centre island, pantry, tumble stone backsplash and walkout to backyard. Upper level boasts a versatile loft overlooking the great room, spacious primary retreat with walk-in closet and 4 pc ensuite, plus 3 additional generously sized bedrooms. The finished basement provides valuable extra living space with a large family/rec room and exercise area. Enjoy outdoor entertaining in the private backyard featuring a stone patio. Close to schools, parks, hospital, HWY, and all the essential amenities. A perfect family home offering space, comfort and style.

77 McMaster Road, Orangeville
$1,099,000
2 Baths ⋅ W13679074 MLS
Welcome to 4 Clara Street, a beautiful freestanding building for sale in a highly desirable area of Orangeville with parking for 12. This charming property is zoned C2 commercial, offering fantastic versatility and flexible permits for a wide variety of business operations. Vacant possession as of November 1st. The interior features 7 private offices, 2 bathrooms, a private boardroom, open bright reception area, sitting areas, 3 entrances and has a warm and inviting atmosphere throughout. Lower level is perfect for storage, but also could be renovated for more working space. There's a rear deck that creates an inviting seating spot for both staff and clients. Set on a large lot with two entrances from Clara Street just off Broadway, you can enjoy high street exposure and clear sign visibility to main Broadway. Finished with gorgeous landscaping, mature trees and in a beautiful neighborhood. A truly unique property combining character, professional functionality, and a prime location.

4 Clara Street, Orangeville
$1,039,900
3 Beds ⋅ 3 Baths ⋅ W13674430 MLS
Welcome to this exceptional two-storey residence on a large, fully fenced corner lot in a highly desirable neighbourhood close to excellent schools and shopping. Soaring cathedral ceilings create an open, light-filled main level perfect for modern living and entertaining. The chef inspired eat in kitchen offers sparkling views of the in ground pool and features an extra large built-in refrigerator and freezer, gas range, and ample counter/prep space. A separate large dining room is ideal for gatherings. The expansive family room centers on a gas fireplace flanked by custom built-in bookcases. Upstairs you'll find three incredibly spacious bedrooms. The primary suite includes a luxurious four piece ensuite and generous walk-in closet. A double car garage plus driveway parking for four vehicles provides exceptional convenience. For complete peace of mind, a built-in Generac gas generator powers the entire home indefinitely during any prolonged or massive power outage. This rare combination of thoughtful design, private outdoor oasis, desirable location, and reliable whole home backup power is ready for its next owners .House Roof - 2023Generator hardwired to house - 2024Shed Roof - 2026

1 St. Paul's Place, Orangeville
$1,200,000
4 Beds ⋅ 2 Baths ⋅ W13656710 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
$1,200,000
3 Beds ⋅ 2 Baths ⋅ W13621854 MLS
Perfectly situated in the heart of Orangeville, this beautifully renovated home delivers an exceptional lifestyle just steps from Kaycee Gardens, scenic trails, and all the amenities and charm that downtown Orangeville is known for. The property harmoniously blends historic character with modern farmhouse chic, evident in its meticulous craftsmanship and attention to detail, creating a welcoming and stylish retreat. The spacious, private backyard is a true oasis, featuring lush gardens, a relaxing sauna, outdoor shower, and a brand-new deck with pergola-ideal for savouring warm summer evenings in comfort and privacy. For added convenience, the two-car detached garage with loft, completed in 2022, offers a cement floor and is roughed in for electrical, as well as a mini split heat pump and air conditioning system, presenting the potential for liveable space. Inside, this 1 3/4 storey home, the 3-bedroom layout impresses with a bright eat-in kitchen, highlighted by floor-to-ceiling custom cabinetry, soaring ceilings, and a generous centre island. The main floor also features a stunning office space outfitted with built-ins and a wet bar, easily convertible into a formal dining room, along with a spacious living room and a sun-drenched three-season porch, ideal for an afternoon nap or enjoying a cocktail while reading your favourite book. Upstairs, you'll find three well-appointed bedrooms and a four-piece bathroom, ensuring a perfect blend of comfort, style, and functionality throughout. Renovations include:, new deck and pergola, built-in desk, drawers and shelving in the office, rough-in for garage electrical and mini heat pump and A/C (2025), a new dishwasher, swing gate on the driveway to fully fence in the backyard (2024), outdoor shower and sauna, new furnace and AC, fence, front yard retaining wall (2021), as well as all new electrical and plumbing (2020). See attached for a full list of upgrades and video tour for full tour of all this home has to offer

22 John Street, Orangeville
$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
$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
$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
$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
$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
$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
$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
$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
$1,149,900
4 Beds ⋅ 3 Baths ⋅ W13490510 MLS
Welcome to this beautifully maintained, carpet-free 4-bedroom family home backing directly onto conservation land in one of Orangeville's desirable neighbourhoods. Offering a peaceful backyard setting with no home directly behind, this property combines comfortable family living with an impressive list of recent updates.The bright, open-concept main floor 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 the backyard, plus a versatile dining room with hardwood flooring. Step outside to enjoy the newer deck, updated railings and fully fenced backyard - a great space for relaxing or entertaining.Upstairs, the generous primary bedroom features a walk-in closet and private 4-piece ensuite with soaker tub and separate shower. Three additional well-sized bedrooms provide plenty of room for family, guests or a home office.The finished lower level adds valuable living space with a spacious recreation room, while the 2-car garage offers direct interior access and convenient loft storage.Recent updates include hardwood flooring, baseboards and staircase (2023), windows (2023), attic insulation (2024), garage door and opener (2024), and water softener (2025). Stamped concrete driveway, front stairs and walkway (2019).

53 Abbey Road, Orangeville
$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
$1,179,999
5 Beds ⋅ 4 Baths ⋅ W13153844 MLS
Stunning 2015 Summit model with high-end craftsmanship and thoughtful design throughout. Enter through double doors into a grand foyer with ceramic tile, coat room and a dramatic wrought iron staircase. The open main level offers luxurious living - gleaming hardwood floors, formal dining room, separate living room with gas fireplace, and an elegant chef's kitchen with quartz countertops, center island, high-end stainless appliances, ceramic flooring, custom lighting and a bright breakfast area. Large oversized windows flood the home with brilliant natural light. Primary suite is a true retreat with rich hardwood floors, an extra-large window provides an abundance of natural light and a luxurious 5-piece ensuite with soaker tub & glass shower. Additional bedrooms feature hardwood floors, generous closets and abundant light. Three full bathrooms provide convenience for family and guests. Outdoor living is exceptional: fully fenced yard, no rear neighbors, and striking double decker timbered deck - perfect for entertaining and serene privacy. Beautifully finished walkout lower level adds flexible living space for relaxation or recreation. Key Features- Built 2015 by reputable builder; upgraded finishes throughout- Luxurious main-level living: hardwood & ceramic floors, formal dining, separate living room- Chef's kitchen: quartz counters, center island, high-end S/S appliances, custom lighting- Breakfast area with W/O access to a Large Sunlit Deck- Primary bedroom with large 5-pc ensuite- 3 full bathrooms- Fully finished walk-out basement- Fully fenced backyard, double-decker timbered deck, no rear neighbors- Grand foyer with ceramic tile and wrought-iron staircase This Summit model delivers "WOW" finishes at every turn - move-in ready and built for elegant everyday living.

21 Paula Court, Orangeville
$1,399,000
W13126752 MLS
Seize the opportunity to own a corner lot with unmatched visibility and access from both Riddell Road and Richardson Road. Positioned on the Bypass in the west end of Orangeville, conveniently close to Highway 10, ensuring high traffic and easy accessibility. Whether you are investing or developing, this prime location presents endless potential in a thriving area.

495 Richardson Road, Orangeville
$1,250,000
W12992560 MLS
Located on a high visibility corner lot, 53 Townline offers a flexible opportunity for investors and business owners seeking M1 zoned commercial space. With approximately 0.717 acres and frontage on two roadways, the property provides excellent access, exposure, and functionality for a variety of permitted industrial and commercial uses. The property includes a detached block workshop measuring approximately 20 by 30 feet, complete with hydro, making it well suited for storage, service based operations, or light industrial use. At the front of the property sits a two storey brick Victorian building that has been updated and maintained, offering adaptable space for offices, client facing business use, or a showroom setting. The combination of character and usability allows for a professional presence while maintaining practical day to day function. Currently tenanted, the property provides existing income with the potential for future repositioning, expansion, or end user occupancy depending on business needs.

53 Town Line, Orangeville
$1,311,990
4 Beds ⋅ 4 Baths ⋅ W12490892 MLS
Offered by the Builder. Welcome to Five Creeks by Great Gulf - where luxury, nature, and modern living come together. This brand-new Fendley Model (Elevation B) sits on a premium ravine lot with a walkout to deck, offering sweeping natural views and the rare opportunity for a walkout basement. Designed with over 2,230 sq ft of elegant living space, this 4-bedroom, 4-bath detached home showcases 9-ft ceilings, an inviting gas fireplace, and sun-filled, open-concept living areas that seamlessly connect to the outdoors. The chef-inspired kitchen boasts quartz countertops, extended cabinetry, a stainless range hood, and a bright breakfast area with a convenient walk-in pantry and walkout to the deck overlooking the ravine - perfect for family gatherings or morning coffee. Upstairs, the primary retreat features his and hers walk-in closets, a freestanding tub, glass-enclosed shower, and double-sink vanity. Each secondary bedroom offers generous space, ensuite or semi-ensuite access, and walk-in closets - ideal for growing families. Built by one of Canada's most award-winning builders, Great Gulf, this home delivers quality craftsmanship and energy efficiency at every turn: triple-pane Energy Star windows, HRV air system, 200 AMP electrical service, rough-in EV charger, and full Tarion warranty for lasting peace of mind. Experience the privacy and tranquility of ravine living in Orangeville's newest master-planned community, just minutes from schools, shopping, and major highways. Walkout, finished basement available. A rare chance to own a luxury new-build backing onto nature - where every detail enhances comfort, connection, and lifestyle.

52 Meyer Drive Unit Lot 46, Orangeville