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Caledon detached homes for sale
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3 RUTLAND HILL Court in Caledon: Rural Caledon House for sale : MLS®# W10438905
3 RUTLAND HILL Court Caledon L7C 0B5 
$4,324,900 /For SaleResidential Freehold- Status:
- Active
- MLS® Num:
- W10438905
- Bedrooms:
- 6
- Bathrooms:
- 6
Stunning Victorian Reproduction home with over 6600 square feet of total living space, perfectly located on a dream 15+ acre oasis amongst a quiet collection of estate homes. Just minutes from Caledon East and Orangeville. The backyard includes a luxurious oversized copper-ionized pool with built-in safety ledge, custom cabana milled on site with wet bar, wood burning fireplace & laundry. 30' x 40' heated and insulated drive shed, approx. 5 acres of cleared land with 10+ acres of forest and trails, custom built stream and waterfall, fully engineered outdoor hockey rink with drainage & lighting (potential to convert to a pickleball or tennis court), tobogganing hill and play set, and fully manicured lawns with gorgeous gardens. Inside, find an expansive, yet cozy living space filled with natural light. Custom dove-tailed wood cabinetry in the kitchen with 2 dishwashers, stone countertops and heated slate flooring. Open concept living area with a beautiful view & walk out to the newly refinished patio (2024). Vaulted ceilings in the living room. Formal dining room which could be easily converted to a main floor primary with ensuite. Main floor laundry. High speed internet throughout the home and backyard. 5 large bedrooms on the second floor plus an additional bedroom in the basement. Bright primary bedroom with spa-like ensuite. 6 bathrooms total. Sauna and games room in the walk-out basement. More detailsListed by Harvey Kalles Real Estate Ltd., Brokerage, Port Carling,- WEI WANG
- Bay Street Group Inc.
- 1 (647) 9147337
- Contact by Email
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61 WILLIAM ST E in Caledon: Rural Caledon House for sale : MLS®# W10895408
61 WILLIAM ST E Caledon L7K 1N7
$1,280,000 /For SaleResidential Freehold- Status:
- Active
- MLS® Num:
- W10895408
- Bedrooms:
- 4
- Bathrooms:
- 3
Located in the coveted Hamlet of Cataract, abutting the Forks of the Credit Provincial Park, this fully renovated (2021-current), upgraded home features over 2,000 sq. ft. of living space just minutes from Belfountain, TPC Osprey Golf Course, Caledon Ski Club, and a quick drive to Erin, Orangeville, and Highway 10. Completely move-in ready, the interior includes engineered hardwood and pot lights throughout the main level (both '22). An abundance of natural light floods the open concept living room, dining room, and chef's kitchen from the recently replaced windows ('22). The kitchen includes beautiful white cabinetry, black stainless-steel appliances, quartz countertops, built-in wall oven, and stunning farmhouse sink (all '22). Main floor bathroom was upgraded with tub, tile, vanity and more in '24. Enjoy your luxurious primary bedroom, perfectly set up with it's own ensuite, walk-in closet (upgraded in '23) and walk-out to your private deck with hot tub. A separate entrance takes you to the fully finished basement, complete with a large recreation area, office and large basement bedroom with its own ensuite (completed in '22). A quiet, tree-lined and fully fenced yard is the perfect hide-away, complete with a beautiful wrap-around deck, quiet sitting area, fire pit and beautiful landscaping throughout. EV charging outlet on front drive and 200amp electrical panel upgrade completed in '21. The perfect low-maintenance home for empty nesters, retirees, or families! More detailsListed by Harvey Kalles Real Estate Ltd., Brokerage, Port Carling,- WEI WANG
- Bay Street Group Inc.
- 1 (647) 9147337
- Contact by Email
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302 KING Street E in Caledon: Bolton East House for sale : MLS®# W10445488
302 KING Street E Caledon L7E 3J7
$1,689,000 /For SaleResidential Freehold- Status:
- Active
- MLS® Num:
- W10445488
- Bedrooms:
- 4
- Bathrooms:
- 4
Welcome to 302 King St, where serene landscapes meet endless potential. Nestled on nearly an acre of mature grounds, this expansive residence boasts over 3,700 sq ft of living space across three levels, including a walkout lower level. With an impressive 182 ft of road frontage and 148 ft of the famous Humber River shoreline which flows directly to lake Ontario, this property offers numerous development possibilities while maintaining its tranquil charm just minutes from historic Bolton Village. The versatile floor plan allows for customization, whether you choose to update the existing layout or create an open-concept living space. As you enter, you'll be greeted by a spacious living area featuring oversized windows that frame picturesque views of the river and lush trees. The dining room, kitchen, and a cozy secondary family room complete with a stunning fireplace flow seamlessly to a large outdoor deck, perfect for entertaining and relaxation or watching various species of wildlife. Upstairs, you'll find four generously sized bedrooms and two full baths, including a primary suite with a four piece ensuite and three closets! The lower level, with its full walkout design, is bathed in natural light and includes additional living spaces that could serve as an enviable home office or a media room with a bar ideal for gatherings. The beautifully landscaped, private property offers convenience with easy access to HWY 50 and the 427, as well as nearby schools and amenities in Bolton Village. Don't miss your chance to own this exceptional home that harmonizes tranquility and accessibility! More detailsListed by RE/MAX Escarpment Realty Inc., Brokerage- WEI WANG
- Bay Street Group Inc.
- 1 (647) 9147337
- Contact by Email
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18095 Horseshoe Hill Road in Caledon: Rural Caledon House for sale : MLS®# W12488116
18095 Horseshoe Hill Road Caledon L7K 2B8
$12,000,000Residential Freehold- Status:
- Active
- MLS® Num:
- W12488116
- Bedrooms:
- 5
- Bathrooms:
- 6
Experience the ultimate equestrian facility at this exceptional 46.5-acre horse farm, designed for both serious horse professionals and passionate equine enthusiasts. Every detail of this property has been thoughtfully planned to combine function, comfort and natural beauty, creating a world-class setting for breeding, training, rehab and boarding. Nestled amid rolling pastures and scenic countryside, this property features a state-of-the-art equestrian complex complete with a 41-stall main barn, dedicated foaling barn, indoor arena, outdoor ring and a private training track. Main barn - professionally designed ventilation system, so no dust or smell, wide aisles with heated floor and rubber mats, wash racks, tack rooms, feed storage, office space and staff apartment. Storage for 300 round bales and easy access for a tractor to take to the paddocks or into the barn. 16 foot high door in storage area makes for easy delivery of hay/feed. Broodmare barn - designed for safety and supervision, 9 large bright stalls, 2 can be converted to 12x24 for foaling season. Storage, office, washroom, cameras. Training track - 5/8 mile with chute and starting gate ideal for training, conditioning and exercise with excellent footing and drainage. Indoor arena - 100x200 attached to the main barn, large viewing area, kitchen, bathrooms, large office with view of arena. 30 paddocks - thoughtfully laid out for easy rotation, turnout and access to water. 9 rehab paddocks laid out close to main barn for easy observation. 60-foot lunging ring. 110x220 outdoor sand ring fully fenced. Equipment building with 3, 16 ft. overhead doors, parking for trailers and staff. Original farmhouse was extensively renovated and converted into 2 separate units for staff housing. Brand new 2 bedroom tiny house. Utilities and infrastructure ready to support full-scale operations. More detailsListed by MOFFAT DUNLAP REAL ESTATE LIMITED- WEI WANG
- Bay Street Group Inc.
- 1 (647) 9147337
- Contact by Email
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18161 Heart Lake Road in Caledon: Rural Caledon House for sale : MLS®# W12655746
18161 Heart Lake Road Caledon L7K 2A4
$2,399,000Residential Freehold- Status:
- Active
- MLS® Num:
- W12655746
- Bedrooms:
- 3
- Bathrooms:
- 3
Price Drop $200,000. Stone House Farm; Modernized century stone-built farmhouse on 30 acres of paddocks, farmland and hardwood forest. A nearly 3,000 sq. ft. sophisticated residence with spacious living rooms, wood-burning fireplaces and open concept kitchen, all surrounded by new picture framed thermal windows with views over the countryside. The primary bedroom wing has a walk-through closet and a 4-piece ensuite. Large organic vegetable garden compliments the 1,800 sq. ft. barn and a further 1,000 sq. ft. insulated workshop/barn - both with lifetime metal roofing. Ample room to grow. Minutes away from Caledon Village and East Caledon. 10 minutes south of Orangeville. Super convenient. The airport is 40 minutes. More detailsListed by MOFFAT DUNLAP REAL ESTATE LIMITED- WEI WANG
- Bay Street Group Inc.
- 1 (647) 9147337
- Contact by Email
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15316 Mount Wolfe Road in Caledon: Rural Caledon House for sale : MLS®# W12966534
15316 Mount Wolfe Road Caledon L7E 3N7
$3,690,000Residential Freehold- Status:
- Active
- MLS® Num:
- W12966534
- Bedrooms:
- 5
- Bathrooms:
- 4
Here is your opportunity to acquire 2 houses on 52 acres in Caledon. AAA location near Bolton and Nobleton. Long views over the majestic Caledon Hills. The main residence has 3 finished levels including a bright lower level walk-out to the pool and patio. The long extended paved driveway leads to the 2nd residence. A barn with office and loads of storage space and even a meeting room and basketball court is just past the 2nd residence. Down by the pond is a sand volleyball court and beach with tiki hut. Miles of walking, ATV trails. Spring-fed pond with dock and beach. Potential for main floor bedroom alongside existing full bathroom. Large main floor office plus a wonderful open floor plan which joins the kitchen, breakfast room, family room and large dining room. The finished lower level could be further developed into a separate suite with existing bedroom, existing bathroom and large existing finished living area and bar. New propane furnace (2026). Value priced for today's market! More detailsListed by MOFFAT DUNLAP REAL ESTATE LIMITED- WEI WANG
- Bay Street Group Inc.
- 1 (647) 9147337
- Contact by Email
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4 Valley Hill Drive in Caledon: Palgrave House for sale : MLS®# W12998200
4 Valley Hill Drive Caledon L7E 0B8
$2,799,000Residential Freehold- Status:
- Active
- MLS® Num:
- W12998200
- Bedrooms:
- 6
- Bathrooms:
- 6
Luxury living in this 4600+ Sq.Ft. custom home on quiet cul-de-sac in Stonehart Estates. Just over 2 acres, mins from town & easy access to major highways for easy commute. 4 oversized garages with long paved driveways, 1 with large parking pad to accommodate guest parking. 6 bedrooms total, 4 Large Bedrooms each with ensuites and 3 have a private balcony. Luxurious primary Suite features walkout private balcony, gas fireplace, huge Walk-in dressing room and 6pc ensuite. Third level boasts boasts separate sitting area, bedroom with balcony, walk-in closet and 4pc ensuite. Perfect for extended family or guest suite. Main floor is open concept high coffered custom molded ceilings and 2 story floor to ceiling windows. New gourmet eat in kitchen offers Thermador high-end appliances, Large island adding wonderful prep area, coffee bar and Multiple walkouts to great deck for outdoor entertaining overlooking a private backyard with mature trees. Formal dining/living room combination with custom moldings and large windows. Impressive foyer entrance features new double doors with walk-in closet and 2pc powder room. Main floor office for work from home comfort. Additional level has extra media family room and office great for movie nights and also an additional guest bedroom. Lower-level walkout offers the perfect entertaining area with its large above grade windows, sunken games room, fabulous large Wet bar area to a covered patio and access to the yard, extra bedroom, gym room, cold cellar, 3pc bath and lots of extra storage. Approximately 90% of windows & doors replaced '23/24, kitchen '21, ceilings '21, deck '23. Hardwood floors thru-out. Excellent Value! Fabulous home for entertaining or also multi-generational family! More detailsListed by COLDWELL BANKER SELECT REAL ESTATE- WEI WANG
- Bay Street Group Inc.
- 1 (647) 9147337
- Contact by Email
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98 William Crisp Drive in Caledon: Alton House for sale : MLS®# W13041394
98 William Crisp Drive Caledon L7K 2R7
$2,099,900Residential Freehold- Status:
- Active
- MLS® Num:
- W13041394
- Bedrooms:
- 4
- Bathrooms:
- 4
Luxury Executive Detached Estate Home In Prestigious Osprey Mills, 3252 Sqft Of Above Ground on 98' x 215' Estate Lot. Featuring 10 Ft Main Floor Ceilings,9' Basement & 2nd Floor. Engineered Hardwood Flooring Throughout, Extended Height Kitchen Uppers + Stacked Uppers, Quartz Countertops Throughout, Stainless Steel Kitchen Appliances. See Schedule For Standard Features And Finishes. Taxes Not Assessed. OPEN HOUSE EVERY SATURDAY AND SUNDAY 12-5! Rent To Own Program available. More detailsListed by ASHLEY, C., REALTY INC.- WEI WANG
- Bay Street Group Inc.
- 1 (647) 9147337
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20 Chinaberry Road in Caledon: Alton House for sale : MLS®# W13242142
20 Chinaberry Road Caledon L7K 2R7
$2,299,900Residential Freehold- Status:
- Active
- MLS® Num:
- W13242142
- Bedrooms:
- 5
- Bathrooms:
- 5
Luxury Executive Detached Estate Home In Prestigious Osprey Mills on 3/4 Acre CORNER Lot, 4331 Sq.ft. Of Above Ground Featuring 10'+ Ceilings on Main Floor,9' Basement & 2nd Floor. Engineered Hardwood Flooring and Quartz Counters Throughout. See Schedule For Standard Features & Finishes and Floorplan. Home is For Sale by Builder. Purchaser to sign Builder APS and Responsible for All Closing Costs. Taxes Not Assessed. RENT TO OWN PROGRAM AVAILABLE. More detailsListed by ASHLEY, C., REALTY INC.- WEI WANG
- Bay Street Group Inc.
- 1 (647) 9147337
- Contact by Email
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1670 Boston Mills Road in Caledon: Rural Caledon House for sale : MLS®# W13424280
1670 Boston Mills Road Caledon L7C 0L9
$1,898,000Residential Freehold- Status:
- Active
- MLS® Num:
- W13424280
- Bedrooms:
- 4
- Bathrooms:
- 3
Greeted by towering maple trees that frame this enchanting Cape Cod-inspired home and nestled on one picturesque acre backing onto serene farm pastures, this is where timeless charm, modern comfort & everyday elegance exist in perfect harmony. From the moment you arrive, you feel as though the home was lifted straight from the pages of a country living magazine. The privacy. The tranquility. The unmistakable sense that you've found something special. Inside, every inch of this home has been thoughtfully curated. Sunlight pours through oversized windows, illuminating beautifully crafted living spaces that effortlessly blend warmth, character & refinement. The exquisite kitchen serves as the heart of the home, showcasing a charming coffee bar & dreamy breakfast area with bay windows, while thoughtful farmhouse-inspired details & inviting gathering spaces throughout the home create an atmosphere that feels both elevated and deeply welcoming. The main floor primary bedroom is an idyllic retreat, complete with a beautifully appointed ensuite. A soaring cathedral ceiling & wood-burning fireplace anchor the main living space, creating the perfect setting for cozy evenings, family gatherings & quiet mornings with coffee before the hustle & bustle of the day ahead. Step outside and discover where this property truly shines. The expansive deck overlooks a backyard oasis designed for enjoying radiant sunsets that never get old & making lifetime memories. From summer dinners under the stars & evenings storytelling around the fire pit, to rejuvenating sessions in the sauna & immersing in all things country, this is more than a home. It's slow mornings on the deck. Reading a book while soaking in the tub. Family dinners that linger a little longer. Children's laughter in the distance. Witnessing the magic of farming. It's room to relax & exhale. Room to grow. Room to be. It's a bespoke lifestyle & exactly what dreams are made of. Welcome to the country. Welcome home. More detailsListed by MAZZEFLYNN REAL ESTATE LIMITED- WEI WANG
- Bay Street Group Inc.
- 1 (647) 9147337
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1 Cedar Drive in Caledon: Rural Caledon House for sale : MLS®# W13450524
1 Cedar Drive Caledon L7K 1H4
$1,928,888Residential Freehold- Status:
- Active
- MLS® Num:
- W13450524
- Bedrooms:
- 4
- Bathrooms:
- 4
Welcome to 1 Cedar Drive, an exceptional estate set on nearly 3 acres of mature forest with a picturesque private spring-fed pond. Beautifully renovated throughout the main and second levels, this remarkable property offers the perfect blend of luxury, privacy, and natural beauty.The thoughtfully designed interior features a stunning chef's kitchen with quartz countertops and stainless steel appliances, bright open-concept living and dining spaces, new hardwood flooring, oversized windows that flood the home with natural light, a main-floor office, and a spacious laundry/mudroom. The impressive family room showcases soaring cathedral ceilings, a cozy fireplace, and a walkout to the breathtaking backyard. Upstairs, the primary retreat offers a spa-inspired 5-piece ensuite, walk-in closet, and tranquil views of the surrounding landscape, while three additional generously sized bedrooms provide ample space for family and guests. The finished walkout lower level offers exceptional versatility with multiple rooms and two separate entrances, creating endless possibilities for recreation, a home gym, office space, or multi-generational living. Outside, enjoy your own private oasis where the spring-fed pond provides year-round enjoyment-from swimming in the summer to skating in the winter-all surrounded by the serenity of nature. A long private driveway accommodates 10+ vehicles, and the property is conveniently serviced by natural gas and Bell Fibe internet. Ideally located on a quiet estate road just minutes from the Caledon Ski Club, Belfountain, premier golf courses, scenic trails, and the Credit River, this is a rare opportunity to own an extraordinary country estate while remaining close to everyday amenities. More detailsListed by CORNERSTONE MARKETING REALTY INC.- WEI WANG
- Bay Street Group Inc.
- 1 (647) 9147337
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14 Antrim Court E in Caledon: Caledon East House for sale : MLS®# W13494190
14 Antrim Court E Caledon L7C 1R1
$1,249,000Residential Freehold- Status:
- Active
- MLS® Num:
- W13494190
- Bedrooms:
- 4
- Bathrooms:
- 3
Welcome to 14 Antrim Court, located on a quiet court in the established community of Caledon East. Situated on a generous 77' x 167.91' lot with privacy fencing, this property offers plenty of space both inside and out. The home features 3+1 bedrooms and a functional layout with a living room, formal dining room, and separate family room with a fireplace. Hardwood flooring can be found throughout much of the main living areas, and the kitchen offers ample space for family meals and gatherings. A main-floor bedroom provides flexibility for guests, a home office, or multi-generational living. The primary bedroom includes an ensuite bathroom with a Jacuzzi tub. A standout feature of the property is the heated detached brick building with services, offering a variety of potential uses including a workshop, studio, storage space, or home-based business. Additional features include two attached garages, a detached garage/workshop, and parking for numerous vehicles. Conveniently located close to schools, the community centre, arena, City Hall, and the Caledon Trailway, this property presents an opportunity for buyers looking to add their own updates and personal touches in a desirable Caledon East location. More detailsListed by CHESTNUT PARK REALTY(SOUTHWESTERN ONTARIO) LTD- WEI WANG
- Bay Street Group Inc.
- 1 (647) 9147337
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Data was last updated August 18, 2026 at 06:15 AM (UTC)
Wei Wang @ Bay Street Group Inc. Brokerage
Location
#500 – 8300 Woodbine Ave
Markham, ON L3R9Y7