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$3,950,000
W13819008 MLS
14 Fifth Avenue offers an opportunity to purchase a fully tenanted, single storey commercial medical building in downtown Orangeville. Located within Orangeville's downtown core, this commercial property features C2 zoning and is currently occupied by established medical tenants, providing immediate rental income for an investor. The single storey layout offers convenient, accessible movement throughout the building and is well suited to its current medical use. The property is within walking distance of shopping, restaurants and other downtown Orangeville amenities, with access to public transportation nearby. Ample on site parking provides added convenience for patients, staff and visitors. For investors seeking a tenanted commercial property for sale in Orangeville, 14 Fifth Avenue combines established medical tenancy, C2 zoning, parking and a well connected downtown location.

14 Fifth Avenue, Orangeville
$2,850,000
2 Baths ⋅ W13622076 MLS
Exceptional Freestanding Industrial Warehouse with Outside Storage- Move-In Ready. Exceptional opportunity to acquire a freestanding industrial warehouse in Orangeville's established west-end industrial park, just minutes from Highway 10 with excellent access to major transportation routes. The versatile M1 zoning accommodates a wide range of industrial uses, making it ideal for owner-users, manufacturers, contractors, distributors, and service businesses. Extensively upgraded over the past two years, the property features a resurfaced yard, new perimeter security fencing with gated access, two new gas furnaces, updated plumbing, new hotwater tank, and fresh interior paint. The secure fenced yard provides valuable outside storage and enhanced security. Designed for efficient operations, the building offers six automatic drive-in doors, a truck level loading ramp with forklift capability, and an outdoor portable dock ramp allowing loading and unloading of up to two 53-foot trailers simultaneously. Ample electrical service supports most industrial applications, while the ground-floor office and mezzanine office provide functional administrative space without compromising warehouse efficiency. Conveniently located near commercial amenities, restaurants, and services, this exceptionally maintained turnkey facility delivers an outstanding combination of accessibility, functionality, security, and flexibility-an ideal opportunity to establish or expand yourbusiness in one of Orangeville's premier industrial locations.

9 Stewart Court, Orangeville
$2,549,900
7 Beds ⋅ 5 Baths ⋅ W13455468 MLS
Welcome to 15-17 York Street where old original meet new addition and an incredible 4 Car Garage And Carriage house! Located in the heart of Orangeville where you can walk to amazing restaurants, schools and shops. This home sits on a lot that widens to 118 feet with a depth of 288 feet backing on to green space. Beautiful design it has to be seen to be appreciated. Main floor boasts a spacious front office and entry, open space dining and living room with double sided gas fireplace. Fabulous Kitchen with Family size centre island and a chef's dream of a kitchen. Double Ovens, Gas cook top, all leading out to the wonderful covered porch with outdoor cook space and mounted outdoor TV! The deck with gas fireplace over looks the massive back yard that makes you feel like you are at the cottage. Rough in for in ground pool and hot tub just waiting for your final touch.

15 - 17 York Street, Orangeville
$2,350,000
4 Beds ⋅ 3 Baths ⋅ W13715960 MLS
Set on one of the most coveted streets in Orangeville, this rarely offered 3+1 bedroom Victorian residence combines timeless charm w modern luxury. Fully renovated, it features a striking 2 level addition & 26 x 16 heated garage. Defined by exceptional craftsmanship & refined finishes throughout, this award-winning home (Heritage Recognition Award 2022; magazine featured in 2020) is truly one of a kind.At the heart of the home is a chef's kitchen, complete with premium Monogram appliances, a large centre island, farmhouse sink, & separate custom pantry with elegant leaded glass. The adjoining family room is both welcoming & impressive, featuring a vaulted beamed ceiling & gas fireplace, perfect for everyday living & entertaining. This stunning home offers 3 baths & a versatile main floor office or 4th bedroom.Rich hickory hardwood flooring, coffered ceilings, crown moulding, & detailed wainscoting add character thruout, while heated tile floors in all bathrooms & mudroom, provide an elevated level of comfort.Extensive upgrades ensure peace of mind, including updated plumbing, electrical, windows, roof, soffits, and water/sewer lines. Additional highlights including dual-zone Lennox HVAC, an on demand tankless water system, reverse osmosis filtration, water softener, & hardwired security camera system. Custom blinds, new doors & trim, pot lighting complete the interior.Outdoors, a professionally landscaped backyard oasis showcases over $150K in upgrades, including irrigation, custom interlocking, heritage brick curved wall, gazebo, sauna, ambient lighting & gas line for BBQ. A 400 sq. ft. cabana/studio offers additional space w storage. Walk to Orangeville's historic downtown cafes restaurants, play championship golf at Osprey Valley Golf Course, ski Ontario's finest slopes, enjoy your daily hikes and walks through the Bruce Trails and Island Lake.This home has been meticulously reimagined for modern luxury while preserving the character that can never be recreated.

12 York Street, Orangeville
$2,199,900
4 Beds ⋅ 4 Baths ⋅ W13067060 MLS
Bring your sketchbook, your contractor & your boldest ideas to transform this iconic estate into this neighbourhood's next masterpiece. Experience the timeless grandeur of one of Orangeville's most iconic homes and massive property. Admired for over 140 years, this stately .70-acre property is a rare gem nestled in the heart of downtown, offering a sprawling 164' x 187' private lot and endless possibilities. The home's quality craftsmanship is evident in every detail, from the original doors and trim to the soaring ceilings and elegant hardwood floors. The main level invites grand-scale entertaining with its expansive foyer, formal living room featuring an original fireplace, and a massive dining room with a second fireplace. Quiet retreats abound in the dedicated library, or enjoy a good read in the cozy den. A spacious kitchen offers lots of space for meal prep and a sun-filled breakfast area that opens to a private side patio. Upper-level highlights 3 bedrooms, with an open landing leading to the primary bedroom featuring a walk-in closet and 3-piece ensuite bath. A unique secondary, rear staircase to the 2nd level provides access to a self-contained guest or in-law suite, complete with its own living/dining area, kitchen, bedroom, and full bath. Outside, the park-like grounds feature mature trees, a massive yard, and a historic driveshed/storage building. This is a rare opportunity to own a piece of local history on a one-of-a-kind downtown lot.

11 Third Avenue, Orangeville
$1,999,900
W13771786 MLS
A prime asset in one of Orangeville's most sought-after historic neighbourhoods. Positioned on an expansive parcel within the newly designated Heritage Conservation District, this property combines immediate residential charm with exceptional long-term strategic value. You may have read about this unique "U-shaped" property at 11A York Street in recent months, see attached property sketch and aerial view for this rare .7 acre town lot with approx. 151.8 ft across rear which backs onto Kay Cee Gardens and offers a prime location near local amenities, shops, cafes, restaurants and Theatre. Previous application documents are available for review, along with studies done. The existing bungalow features 3 bedrooms, spacious updated kitchen/dining room with large pantry, built-in desk and convenient closet laundry. Bright open concept family room with walkout to upper sundeck and living room with cozy gas fireplace. The lower level features a massive recreation room with 2nd gas fireplace, 4th bedroom, office and 3 piece bathroom. There is also a large workshop and lots of dedicated storage for hobbies and off season items, most closets are cedar lined. The lower level offers the potential of an in-law suite with it's separate side entrance/mudroom and garage access. Home has been well maintained and updating includes windows, doors and extra insulation blown in. The west frontage of the property is approx. 9.5 ft. and has a paved driveway that leads to the garage and parking area, as well as the sprawling rear yard with towering, mature trees and gardens.

11A York Street, Orangeville
$1,999,900
4 Beds ⋅ 2 Baths ⋅ W13771778 MLS
A prime asset in one of Orangeville's most sought-after historic neighbourhoods. Positioned on an expansive parcel within the newly designated Heritage Conservation District, this property combines immediate residential charm with exceptional long-term strategic value. You may have read about this unique "U-shaped" property at 11A York Street in recent months, see attached property sketch and aerial view for this rare .7 acre town lot with approx. 151.8 ft across rear which backs onto Kay Cee Gardens and offers a prime location near local amenities, shops, cafes, restaurants and Theatre. Previous application documents are available for review, along with studies done. The existing bungalow features 3 bedrooms, spacious updated kitchen/dining room with large pantry, built-in desk and convenient closet laundry. Bright open concept family room with walkout to upper sundeck and living room with cozy gas fireplace. The lower level features a massive recreation room with 2nd gas fireplace, 4th bedroom, office and 3 piece bathroom. There is also a large workshop and lots of dedicated storage for hobbies and off season items, most closets are cedar lined. The lower level offers the potential of an in-law suite with it's separate side entrance/mudroom and garage access. Home has been well maintained and updating includes windows, doors and extra insulation blown in. The west frontage of the property is approx. 9.5 ft. and has a paved driveway that leads to the spacious garage and parking area, as well as the sprawling rear yard with towering, mature trees and gardens.

11A York 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
$1,449,900
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
$1,399,000
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
$1,349,000
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
$1,311,990
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
$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
$1,200,000
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
$1,190,000
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
$1,179,999
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
$1,175,000
4 Beds ⋅ 3 Baths ⋅ W13778264 MLS
This Is The One You've Been Waiting For! Welcome To A Home That Truly Checks All The Boxes, Space, Style, Location, And An Incredible Backyard Oasis! This Beautifully Maintained 4-Bedroom, 3-Bathroom, Home With A Finished Basement Offers Plenty Of Room For The Entire Family, Inside And Out. Step Outside And You May Never Want To Leave! The Private Resort-Style Backyard Is An Entertainer's Dream Featuring A Sparkling Inground Swimming Pool, Hot Tub, Extensive Professional Landscaping And Beautiful Landscape Lighting That Transforms The Yard Into Something Truly Special After Sunset. Whether You're Hosting Summer Pool Parties, Relaxing In The Hot Tub Or Enjoying A Quiet Evening Outdoors, This Backyard Was Made For Making Memories. And Then There's The Finished 3-Car Garage, The Kind Of Garage That Just Might Make The Neighbours Jealous! Whether You're A Car Enthusiast, Or Need Extra Storage Or Simply Appreciate A Clean, Finished Space, This Is A Feature You'll Love. Inside, Enjoy A Completely Carpet-Free Home, A Freshly Painted Main Floor, Generous Living Space And A Finished Basement Offering Even More Room For The Family. Add A Durable Metal Roof And No Rental Equipment, And You Have A Home Designed For Both Comfort And Peace Of Mind. The Location Is Just As Impressive. Situated In A Family-Friendly Neighbourhood, You're Within Walking Distance Of A K-8 Public School, Playgrounds And Parks, Island Lake Conservation Area, As Well As The Shops, Restaurants And Pubs Of Downtown. A Beautiful Family Home, An Incredible 3-Car Garage, A Backyard That Feels Like Your Own Private Resort And A Location Where You Can Walk To Almost Everything, This Isn't Just Another House. This Could Be The One You Call Home.

119 Oak Ridge Drive, 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
$1,149,900
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
$1,129,900
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
$1,100,000
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
$1,099,000
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
$1,099,000
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
$1,079,000
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
$1,059,900
5 Beds ⋅ 4 Baths ⋅ W13805938 MLS
Welcome to this 4+1 bedroom, fully finished home designed for practical family living. Featuring bright, open-to-above ceilings and great layout flow, this property is located in a prime Orangeville neighborhood-just minutes from the hospital, Highways 9 & 10, scenic Orangeville Reservoir, shopping, and historic downtown Broadway. Main Level Features: Modern Kitchen: Custom cabinets with pull-out organizers, granite countertops, stainless steel appliances, gas stove, and a large center island with a attached dining table. Main Floor Highlights: Engineered hardwood flooring throughout and high, light-filled ceilings. Backyard Setup: Walk out to a stone patio, wooden deck, and custom gazebo-perfect for summer BBQs and relaxing outdoors. Upper Level Living: Primary Suite: Double-door entry opens to a large bedroom with a walk-in closet and a private 4-piece ensuite bathroom. Bedrooms & Family Lounge: Three additional spacious bedrooms plus an open upper lounge-ideal for a study area, reading nook, or extra TV lounge. Fully Finished Basement: Extra Living Space: Features a rec room, a private 5th bedroom, a dedicated exercise room, and a 3-piece bathroom. Perfect for guests or an in-law suite. A move-in-ready home offering plenty of space and comfort on every floor!

117 Oak Ridge 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
$1,039,900
4 Beds ⋅ 4 Baths ⋅ W13817252 MLS
Welcome to 12 Maude Court, an exceptional Karleton model on a quiet cul de sac in Orangeville's popular Settlers Creek neighbourhood. This spacious 4-bedroom, 3-bathroom home has been beautifully updated and tastefully decorated, offering plenty of room for a growing or multi-generational family. The bright, open-concept main floor features new flooring, fresh paint and new baseboards, along with stylish feature walls that add warmth and character throughout. At the heart of the home is the spacious eat-in kitchen, where a large picture window overlooks the private backyard and inground pool - with the added bonus of no neighbours directly behind. Need flexible living space? A separate main-floor room can easily adapt to your lifestyle as a formal dining room, home office, craft room or even an additional bedroom. Upstairs, you'll find four generously sized bedrooms plus a charming loft/library area - a perfect spot for reading, homework or a quiet workspace. The recently updated lower level provides even more finished living space and includes a rough-in for an additional bathroom, giving you options for the future. Additional updates include a new air conditioner, making this home truly move-in ready. With its spacious layout, thoughtful updates, flexible living areas and a backyard made for summer days around the pool, 12 Maude Court is a home designed for both everyday family living and entertaining.

12 Maude Court, Orangeville
$999,999
6 Beds ⋅ 4 Baths ⋅ W13629292 MLS
Welcome to this spacious family home backing onto a premium ravine lot with breathtaking views of forested conservation land. Designed with growing or multi-generational families in mind, this 4-bedroom, 3 + 1 bathroom home offers generous living space, a functional layout, and a beautifully finished in-law suite with a separate entrance. An attached 2-car garage and private driveway provide plenty of parking and everyday convenience. The main floor features a bright eat-in kitchen with ceramic flooring, pot lights, and a breakfast area with a walkout to the multi-level deck overlooking the private backyard. The adjoining family room is warmed by a cozy gas fireplace, while the separate living room showcases hardwood flooring and a charming bay window. A formal dining room with hardwood flooring, convenient main floor laundry, and a 2-piece powder room complete this level. Upstairs, you'll find four well-sized bedrooms, including a spacious primary retreat with a double closet and private 3-piece ensuite. A 4-piece main bathroom serves the additional bedrooms, each offering a closet and large window. The finished basement provides an excellent in-law suite with its own separate entrance, featuring a full kitchen, living room, dining area, 2 spacious bedrooms, and 3-piece bathroom-ideal for extended family or guests. Outside, enjoy the stamped concrete walkway and patio leading to the front entrance, along with multiple levels of deck space perfect for entertaining while taking in the peaceful ravine setting. This is a rare opportunity to own a versatile family home in a sought-after location with exceptional privacy and room for everyone. Updates: Deck (2019), Upper windows (2001&4). Furnace, CAC 2022

113 Meadow Drive, Orangeville
$999,900
4 Beds ⋅ 3 Baths ⋅ W13779632 MLS
The backyard is where this one separates itself. Off the kitchen's garden doors, it boasts armour stone, interlock patio, a cedar pergola on stone piers, a shaded gazebo set on concrete footings, and deep perennial beds and ornamental grasses against a fully fenced corner lot - all of it done between 2013 and 2015 and well grown in since. Inside, this 2011 two-storey has been kept current. New laminate and tile went through the main level in 2025. The kitchen has cream shaker cabinetry, subway tile backsplash (2021), stainless appliances and a breakfast bar peninsula, and it opens to a dining area in a bright bay with garden doors to the patio. The tiled foyer and front living room carry panelled wainscoting. Upstairs, an open landing overlooks the main floor, and the primary bedroom has a five-piece ensuite with a corner soaker tub, separate glass shower and double vanity, alongside two more bedrooms and a four-piece bath. The lower level, finished by the owners in 2015, is the other surprise: a rec room under pot lights and a custom barn board bar with a live edge top and lit display niches, plus a fourth bedroom, a three-piece rough-in and cold storage under the front porch. Attached two-car garage with doors and frames replaced in 2025, and parking for four more in the drive. Recent work includes the furnace and air conditioning (2026), hot water heater (2024, rental), garage doors (2025), main floor flooring and tile (2025), kitchen backsplash (2021), and water softener and reverse osmosis system (2012). Forced air gas, central air, 100 amp copper wiring, central vac and HRV rough-ins. Nothing is excluded - the appliances, washer and dryer, workbench and garden shed all stay.

170 Elaine Drive, Orangeville
$999,900
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