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349502 4TH B Corners, Grey Highlands
$4,390,000
6 Beds ⋅ 4 Baths ⋅ X13809932 MLS® #
An extraordinary opportunity to acquire approximately 100 acres, your own private lake, a custom log residence and an established income-producing accommodation business-all within one remarkable four-season property. Welcome to Perry's Pond in McIntyre, ideally located south of Collingwood and Singhampton and within easy reach of Devil's Glen, Blue Mountain and the area's recreational amenities.At the heart of the property is a custom-built log home with an attached cottage residence, complemented by six rental cabins that form the foundation of a thriving short-term accommodation business. Lakeside cabins, many with woodstoves, create an authentic country retreat experience, while an outdoor wood-fired hot tub and sauna add to the year-round appeal. A detached double-car garage provides additional storage and utility.The diverse 100-acre setting includes approximately 25 acres of agricultural land, 25 acres of income-producing tree farm and an impressive 25-acre lake, creating a rare combination of productive land, water, recreation and natural beauty. The property also benefits from applicable property tax incentive programs, adding another dimension to its income and investment potential.Continue the existing accommodation business, create an exceptional private family compound, or explore opportunities for future expansion, subject to applicable approvals. With multiple existing income streams, substantial acreage and an established hospitality operation, Perry's Pond presents tremendous potential for an entrepreneurial buyer with vision.This is a truly unique opportunity where business, investment and an extraordinary country lifestyle come together. (id:5764)

349502 4TH B Corners, Grey Highlands

Listing courtesy of Engel & Volkers Toronto Central.

469273 Grey Rd 31 Road, Grey Highlands
$3,800,000
3 Beds ⋅ 3 Baths ⋅ X13534556 MLS® #
West Wind - 100 spectacular acres in the Singhampton Highlands, a short walk to Pretty River Valley Provincial Park and just 15 minutes to Osler and Devil's Glen. A newly built residence, crafted around the hand-hewn frame of a late-1800s Ontario barn, crowns the property's highest point with Escarpment valley views, complete privacy, and architectural plans for its next phase. The land is the estate: rolling meadows, mature forest, and thousands of acres of protected parkland just beyond the gate. Hay fields are maintained by a local farmer, preserving valuable farm-class taxes, while a winding driveway leads to a hilltop setting with no neighbours in sight. The home blends historic character with modern performance, featuring polished concrete floors with hydronic in-floor heat, heat pump heating and cooling, low-maintenance steel exterior, drilled well, new septic system, and a wood-burning stove. Soaring ceilings, walls of glass, a suspended staircase with glass railings, and oversized sliders open to a west-facing deck overlooking your own hundred acres. The chef's kitchen is appointed with Miele, Fisher & Paykel, and Bosch appliances, including an induction cooktop, wall oven, integrated refrigeration, and twin appliance garages. Interiors by Revision Four showcase custom millwork, designer lighting, and are offered fully furnished, including curated pieces with remarkable provenance. Included is a complete second barn kit with architect-designed plans for a garage, additional bedrooms, and a connecting breezeway. Positioned outside NEC development control, the property offers the rare advantage of Escarpment beauty without Escarpment permitting restrictions. Only 15 minutes to Osler and Devil's Glen ski clubs and, and 25 minutes to Creemore and Collingwood, with the Bruce Trail and Mad River nearby, and under two hours from Toronto. A remarkable legacy estate in the Pretty River Valley. (id:5764)

469273 Grey Rd 31 Road, Grey Highlands

Listing courtesy of Royal LePage Signature Realty.

469319 Grey Rd 31 Road, Grey Highlands
$3,400,000
8 Beds ⋅ 5 Baths ⋅ X13557820 MLS® #
Welcome to Pretty Pine, a remarkable 100-acre estate in the Singhampton Highlands, anchored by a striking 3,600 sq. ft. modern barndominium designed for entertaining, wellness and four-season country living.The dramatic open-concept main level features soaring ceilings, hydronic in-floor heating, a wood-burning fireplace and insulated glass garage doors with integrated automatic screens, allowing the living space to open fully to the surrounding meadows and countryside. A dedicated heated garage bay provides secure space for vehicles, recreational equipment, storage or workshop use.Upstairs, the private primary suite offers countryside views, a propane fireplace, a full ensuite with walk-in shower and a Japanese-style ofuro deep-soaking tub set within the bedroom. A loft, powder room and four additional bedrooms provide flexible space for guests, offices, fitness, studio or recreation.The estate's wellness amenities include a modern eight-person sauna with a full glass wall overlooking the landscape and an adjacent cold plunge pool, creating a complete hot-and-cold circuit at home.A separate three-bedroom, two-bathroom farmhouse overlooks the spring-fed ponds and offers comfortable main-floor living, a wood-burning stove and ideal accommodation for extended family, guests or a caretaker.Set across 100 acres of rolling meadow, forest, ponds and private trails, Pretty Pine offers exceptional privacy and recreation. Approximately 15 minutes to Osler Bluff, Devil's Glen and Creemore, 20 minutes to Collingwood, close to the Bruce Trail and less than two hours from Toronto. An extraordinary family compound, multi-generational retreat or four-season country estate. (id:5764)

469319 Grey Rd 31 Road, Grey Highlands

Listing courtesy of Royal LePage Signature Realty.

9420 Ewing Road, Clearview
$1,799,900
S13622230 MLS® #
Twenty spectacular acres where the Mad River winds through mature escarpment forest beneath dramatic stone cliffs and towering hardwoods. Welcome to Mad River Retreat at Devil's Glen, an extraordinary opportunity to create a legacy four-season retreat in one of Ontario's premier recreational destinations. Private woodland trails invite hiking, snowshoeing, cross-country skiing and endless exploration in every season. Development approvals are in place, including an approved building footprint of approximately 2,700 sq. ft., allowing you to focus on designing your dream chalet. Ideally located just minutes from Devil's Glen Ski Club, the Bruce Trail, Creemore, Collingwood, Blue Mountain and Georgian Bay. A rare offering where natural beauty, privacy and development readiness come together. Comprehensive due diligence package available. (id:5764)

9420 Ewing Road, Clearview

Listing courtesy of Chestnut Park Real Estate.

429573 8TH CONCESSION B Line, Grey Highlands
$1,599,900
4 Beds ⋅ 3 Baths ⋅ X13454092 MLS® #
5-Acre Luxury Four-Season Retreat in Singhampton, Near Prestigious Osler Bluff & Devil's Glen Ski Clubs and Duntroon Highlands Golf Club. Ideally located approximately 20 minutes from Collingwood and 25 minutes to Blue Mountain and Wasaga Beach, this exceptional country estate offers privacy, natural beauty, and year-round recreation. Set on five picturesque acres featuring two private ponds, including one stocked with rainbow trout, mature landscaping, and a private golf practice area, this custom-crafted residence combines refined luxury with tranquility. Offering approximately 3,000 sq. ft. of finished living space, this beautifully maintained home features 4 bedrooms, 3 bathrooms, a gourmet kitchen, open-concept living and dining areas, a gas fireplace, and multiple walkouts to a covered wraparound white cedar deck. Designed for relaxation and entertaining, the home features a whirlpool tub, steam shower, and outdoor sauna, creating a private wellness retreat. The upper level offers a lounge, kitchenette, wine fridge, spa-inspired bathroom, and elevated deck, while the finished lower level provides additional living and recreation space, a fourth bedroom, and a 3-piece bathroom. Outdoors, enjoy expansive green spaces, peaceful natural surroundings, and exceptional privacy. A detached 2-car garage with a finished multi-purpose studio and bar fridge provides versatile space for fitness, creative pursuits, or a home office. Whether you're seeking a luxury country residence, private weekend getaway, or four-season recreational property near Blue Mountain, enjoy skiing, golf, hiking, biking, water sports, and Southern Georgian Bay's celebrated lifestyle. (id:5764)

429573 8TH CONCESSION B Line, Grey Highlands

Listing courtesy of Sotheby's International Realty Canada.

188 Highpoint Crescent, Grey Highlands
$1,199,000
5 Beds ⋅ 3 Baths ⋅ X13648622 MLS® #
Captivating Waterfront Estate on Brewster's Lake~5.14 Acres with 167 Feet of Shoreline! Welcome to your private lakeside retreat in the heart of Grey Highlands where nature and lifestyle converge. Situated on the serene shores of Brewster's Lake, this 5 bedroom, 3-bathroom chalet- style home offers over 3800 sq. ft. of beautifully designed living space with unspoiled waterfront and panoramic western vistas that promise unforgettable sunsets. Whether you're seeking a full-time residence, a seasonal getaway, or an investment opportunity, this property delivers (Property ~ Seller is currently using Lower Level as a licensed Air BnB and lives full time on the main level. Perfect for generational living opportunities). HIGHLIGHTS *New Metal Roof 2025 *Expansive deck (walk out~1157 sf) *Patio with hot tub, *Bunkie *Sauna *Waterfront dock *Open concept design ideal for entertaining *Cathedral Ceiling *Double garage with inside entrance *2 Exquisite Stone Fireplaces with Wood Inserts (WETT Certified) *Main Floor Laundry *Lower Level Laundry *4 Season Sunroom *Lower level walk out. LOCATION: Just minutes from ski clubs~ Devils Glen, Osler Bluff, Blue Mountain *Championship Golf Courses~ Mad River, Osler Brook, Duntroon Highlands *Georgian Bay, *Waterfalls *Farmers Markets *Historic Downtown Collingwood *Village at Blue *Extensive Hiking/Biking Trails *ATV/Snowmobile Routes *Top-Tier Fishing right off your dock. Live where you play, Grey Highlands is the Home of Four-Season Adventure: kayak, swim, snowshoe, cross-country ski, or relax by the waters edge. With its proximity to both private and public recreational hubs, this property suits families, active retirees, weekenders, or those seeking a peaceful escape. Elevate your Lifestyle. Live your Legacy~ Your Waterfront Dream Starts Here! View Virtual Tour and Book your Showing Today! (id:5764)

188 Highpoint Crescent, Grey Highlands

Listing courtesy of RE/MAX Four Seasons Realty Limited.

449686 10th Concession Road, Grey Highlands
$1,150,000
4 Beds ⋅ 2 Baths ⋅ X13697776 MLS® #
Finding 50 acres in Grey Highlands just 15 minutes from Collingwood gives you a pretty great combination of country living, usable land and convenience. With approximately 15 workable acres, multiple ponds, a wonderful wetland area and mixed bush throughout the remainder, this property offers a great mix for anyone looking for space to farm, explore and enjoy the outdoors. The brick bungalow offers approximately 1,060 sq. ft. of main-floor living space with an open-concept layout, three bedrooms, two bathrooms and a large back deck overlooking the property. A wood-burning fireplace with a stone surround adds warmth and character to the living room. Heating is provided by a wood furnace, along with the fireplace and a ductless wall unit that provides both supplemental heat and air conditioning. An attached garage provides everyday convenience, while the full, partially finished basement with 4th bedroom adds additional space and includes a walk-up directly into the garage. Outside, established flower beds and vegetable gardens surround the home, with plenty of room to expand the gardens for anyone who wants to grow more of their own food. For those who need a barn or additional storage, the two-level 40' x 24' barn has hydro, a waterline, and a large sliding door measuring approximately 9' wide by 7'11" high. There is a lot of variety within these 50 acres. The workable land provides options for farming or pasture, while the ponds, wetlands and mixed bush create habitat for wildlife and plenty of space to explore and enjoy throughout the seasons. And with Collingwood only about 15 minutes away, you can enjoy the space and privacy of a Grey Highlands country property while keeping shopping, restaurants and four-season recreation close by. NOTE: The road is signed "Road Closed, Bridge is out" due to a bridge repair farther along the road. The closure does not affect access to this property. (id:5764)

449686 10th Concession Road, Grey Highlands

Listing courtesy of RE/MAX Summit Group Realty Brokerage.

449686 10th Concession Road, Grey Highlands
$1,150,000
2 Baths ⋅ X13697780 MLS® #
Finding 50 acres in Grey Highlands just 15 minutes from Collingwood gives you a pretty great combination of country living, usable land and convenience. With approximately 15 workable acres, multiple ponds, a wonderful wetland area and mixed bush throughout the remainder, this property offers a great mix for anyone looking for space to farm, explore and enjoy the outdoors. The brick bungalow offers approximately 1,060 sq. ft. of main-floor living space with an open-concept layout, three bedrooms, two bathrooms and a large back deck overlooking the property. A wood-burning fireplace with a stone surround adds warmth and character to the living room. Heating is provided by a wood furnace, along with the fireplace and a ductless wall unit that provides both supplemental heat and air conditioning. An attached garage provides everyday convenience, while the full, partially finished basement with 4th bedroom adds additional space and includes a walk-up directly into the garage. Outside, established flower beds and vegetable gardens surround the home, with plenty of room to expand the gardens for anyone who wants to grow more of their own food. For those who need a barn or additional storage, the two-level 40' x 24' barn has hydro, a waterline, and a large sliding door measuring approximately 9' wide by 7'11" high. There is a lot of variety within these 50 acres. The workable land provides options for farming or pasture, while the ponds, wetlands and mixed bush create habitat for wildlife and plenty of space to explore and enjoy throughout the seasons. And with Collingwood only about 15 minutes away, you can enjoy the space and privacy of a Grey Highlands country property while keeping shopping, restaurants and four-season recreation close by. NOTE: The road is signed "Road Closed, Bridge is out" due to a bridge repair farther along the road. The closure does not affect access to this property. (id:5764)

449686 10th Concession Road, Grey Highlands

Listing courtesy of RE/MAX Summit Group Realty Brokerage.

429560 8th B Corners, Grey Highlands
$1,100,000
X13538548 MLS® #
The subject property is located just north of Singhampton with frontage on Concession 8B. This property, in the same family for multiple generations, contains rolling topography with gravelly loam type soils. A portion of the property contains a cedar forested area surrounded by upland hardwoods and regenerating areas. Vernal pools and small wetlands are located throughout the adjacent landscape as well as on this property. The surrounding area is comprised of similar terrain on adjacent properties to the South and West. During the early settlement of the area, a large portion of the site was cleared for agricultural purposes. This land use was abandoned many decades ago due to the marginal soils. The original cabin and barn were located at the northwest corner of the property where the foundations and well pump remain. The former fields are still legible through the remains of grassy areas, stone fences and large tree lines. There is also the foundation of a lime kiln. There is a residual field in the interior of the property near a small natural pond with a seasonal stream that connects to the main stream in the middle of the property. The field is bounded by pioneer stone fencing and lines of heritage maple trees. A substantial portion of the property is maple forest and was last logged in 1991. There is a section of Bedrock drift on the northeast portion of the property. There is a Wetlands designation under the MNRF and a related Conservation Land Tax Incentive Plan (CLTIP). As of 2022, there is also a Managed Forest Tax Incentive Plan. This is a gem! (id:5764)

429560 8th B Corners, Grey Highlands

Listing courtesy of Engel & Volkers Toronto Central.

794116 Grey Rd 124 Road, Grey Highlands
$549,900
3 Beds ⋅ 2 Baths ⋅ S13812480 MLS® #
Welcome to this beautifully updated two-storey home featuring 3 bedrooms and 2 bathrooms located in the charming village of Singhampton. The primary has a large attached room currently used as a walk in closet which has a closet. Full of character and thoughtfully modernized, the home showcases a gorgeous large island kitchen with patio doors opening to an **extra-large rear deck** overlooking the expansive, fully fenced backyard. Original details have been lovingly preserved, including the glass doorknobs, oak hardwood floors, and distinctive wood staircase and railing. Extensive updates include new windows, a complete electrical system, flooring and drywall, sewage and well pumps, spray foam insulation in the attic and crawl space, brand new ductwork, and a woodstove professionally completed to WETT certification. Outside, enjoy the double asphalt driveway and a fabulous post-and-beam built shed offering exceptional storage or workspace. A wonderful blend of timeless character and modern convenience-this is a home with a story, beautifully updated for today. (id:5764)

794116 Grey Rd 124 Road, Grey Highlands

Listing courtesy of RE/MAX By The Bay Brokerage.

794097 124 Grey Road, Clearview (Singhampton)
$499,000
3 Beds ⋅ 2 Baths ⋅ S13715586 MLS® #
Welcome to this beautifully upgraded home in the heart of Singhampton, where convenience meets four-season outdoor adventure. This 3-bedroom, 2-bathroom home has been thoughtfully updated while preserving the warmth and charm of its original features. Step inside through the welcoming front foyer, a practical space for everyday essentials. From there, the home opens into an open-concept living room featuring beautiful exposed wood accents and a cozy wood-burning heat source that creates the perfect atmosphere for relaxing. The updated kitchen blends modern function with timeless character, featuring soft-close cabinetry complemented by the original brick as backsplash. A newly installed oak staircase adds another beautiful feature and highlights the quality of the recent improvements throughout the home. The main floor is designed for both comfort and convenience, with a main floor a primary bedroom complete with its own ensuite and in-floor heating, along with a convenient main-floor laundry. Two additional bedrooms and a second bathroom provide plenty of space for family, guests, or a home office. In-floor heating in both bathrooms and the primary bedroom. Outside, the 10' x 16' detached shed offers excellent storage or workshop potential and is equipped with hydro and a 7' x 8' garage door, making it ideal for storing equipment, recreational toys, or tackling your next project. Recent upgrades include an on-demand water heater and water softener (2026), exterior concrete work (2025), steel roof, windows, septic, well pump, siding, soffit and fascia, flooring, kitchen, bathrooms, and stairs. With versatile C1 zoning, the possibilities extend beyond residential living. Located across from Mylar & Loretta's Restaurant, just 7 minutes to Devil's Glen Ski Club, approximately 20 minutes to Collingwood, and close to hiking destinations including the Singhampton Caves Trailhead, Nottowasaga Bluffs Conservation, Devils Glen Provincial Park, and Nottowasaga Lookout. (id:5764)

794097 124 Grey Road, Clearview (Singhampton)

Listing courtesy of .