Refine Search
Map
Sort by
$1,485,000
5 Beds ⋅ 4 Baths ⋅ S13623426 MLS® #
Welcome to the Highlander at Craighurst Crossing, where timeless modern farmhouse architecture meets exceptional craftsmanship in one of Oro-Medonte's most desirable communities. Offering more than 3,500 square feet of beautifully finished living space, this thoughtfully designed home delivers the perfect balance of comfort, style, and versatility. The sun-filled main floor is designed for both everyday living and effortless entertaining. Soaring vaulted ceilings create an impressive sense of space, while the open-concept great room is anchored by a cozy gas fireplace. At the heart of the home, the chef-inspired kitchen features an oversized island, walk-in pantry, and seamless flow into the dining area-perfect for gathering with family and friends. Large windows flood the home with natural light, while the covered rear patio provides the ideal setting for outdoor dining, morning coffee, or relaxing evenings. The main floor is also thoughtfully appointed with a convenient laundry room, making everyday living both practical and efficient.Upstairs, the spacious primary retreat offers a walk-in closet and spa-inspired ensuite, complemented by two additional bedrooms and a full bathroom. The professionally finished lower level adds incredible flexibility, featuring a spacious recreation room with a custom wet bar, two additional bedrooms, a full bathroom, and ample room for guests, multigenerational living, a home gym, office, or media space. Set within the award-winning Craighurst Crossing community, you'll enjoy a tranquil setting surrounded by forests, walking trails, and protected greenspace, while remaining just minutes from Barrie, Orillia, Horseshoe Resort, Vettä Nordic Spa, championship golf courses, skiing, and everyday conveniences.Whether you're searching for a full-time residence or a refined retreat to enjoy Ontario's four-season lifestyle, this exceptional home offers the space, quality, and location to make every day feel like an escape. (id:5764)

15 Private McKay Drive, Oro-Medonte

Listing courtesy of Bosley Real Estate Ltd..

$1,225,000
5 Beds ⋅ 3 Baths ⋅ S13597980 MLS® #
Welcome to 46 Pine Ridge Trail in beautiful Horseshoe Valley. Located on one of the most sought after streets for mountain biking, cross country skiing and hiking enthusiasts, this jaw dropping chalet style home has a long list of upgrades and improvements and is only steps away from the Copeland Forest offering 4400 acres of groomed trails for biking, hiking and cross country skiing. A new and highly sought after elementary school is just up the hill as well as amenities for your immediate needs in the village of Craighurst and quick 400 access. With potentially 5 bedrooms in this over 3200 sf finished home, there is plenty of room for a large family and visitors. The lower level is partially above grade and opens into a large mud room with inside access to the garage. On the same level you'll enter from the mudroom into a large rec. room and a home gym which could also be used as a 5th bedroom. Take the stairs to the main level where the soaring ceilings and the open concept kitchen, dining and bonus space (Muskoka area) truly take your breath away. On the main level you'll also find a pantry, laundry area, full bath and 3 bedrooms, one currently being used as an office. Enjoy stepping out to your wrap around deck from the main level, or heading out back to over look your own private forest, watch the kids play in their playhouse in the woods, or enjoy a relaxing dip in the hot tub under the quiet night skies. The upper level is where you will find the private primary retreat. A spacious bedroom, large walk-in closet and bright 5 piece ensuite complete the inside of this dream home. Ski, mountain bike, hike, dine, visit the spa, a local brewery, or enjoy the peace and quiet of your beautiful home in this truly special location. Other notable improvements include newer forced air gas furnace (2021), A/C (2020), Windows - all replaced with quality Kempenfelt windows. (id:5764)

46 Pine Ridge Trail, Oro-Medonte

Listing courtesy of RE/MAX HALLMARK CHAY REALTY.

$1,738,000
6 Beds ⋅ 5 Baths ⋅ S13572976 MLS® #
Fully renovated from kitchen to bathrooms to new mechanicals! Welcome to 18 Pine Lane in Horseshoe Valley, Oro-Medonte-a true character estate home that provides luxury, comfort, unmatched privacy, and a rare generational opportunity for your family. This stunning home is part of the Cathedral Pines neighbourhood, an exclusive enclave made up entirely of custom-built homes where fewer than 25 properties have changed hands over the past decade. Once people arrive here, they tend to stay; on this quiet cul-de-sac of only six homes, the last time a property became available was 2014. Offering 4,400 square feet of finished living area, the spacious layout features six bedrooms and five bathrooms, completely renovated with a new kitchen and bathrooms, and brand-new mechanicals-leaving nothing to do but move in and enjoy. The estate sits on an exceptionally private pie-shaped lot of more than half an acre, backing onto nothing but managed forest, and features four outbuildings including a pool equipment shed, change hut, garden shed, and a fully wired studio. Perfectly located for active living, Horseshoe Valley offers endless seasonal opportunities with two downhill ski areas, 43 km of cross-country and mountain bike trails, hiking, and golf. Families will love being steps from the new Horseshoe Heights elementary school and community centre, while still only 15 minutes to Royal Victoria Hospital and Georgian College, and approximately one hour to Pearson Airport. (id:5764)

18 Pine Lane, Oro-Medonte

Listing courtesy of RE/MAX HALLMARK CHAY REALTY.

$949,000
3 Beds ⋅ 2 Baths ⋅ S13521792 MLS® #
Nestled on a quiet cul-de-sac in the sought-after Cathedral Pines community of Horseshoe Valley, this custom-built chalet-style bungalow is a rare offering. Lovingly maintained by its original owner, the home backs onto a ravine-like setting and is surrounded by mature trees and nature, creating a private retreat just minutes from year-round recreation. The sun-filled main floor features soaring cathedral ceilings and a stunning picture window that frames picturesque views of the natural landscape beyond. A true bird lover's paradise, enjoy regular visits from hummingbirds, blue jays, cardinals and other local wildlife from the comfort of your living room. The spacious primary bedroom offers a private 4-piece ensuite, while the bright walkout lower level includes two additional bedrooms, a full bathroom, and direct access to the patio and backyard. After a day outdoors, unwind and relax in your own sauna. An attached single-car garage and ample driveway parking provide plenty of space for family and guests. Located in the vibrant Horseshoe Valley community, you'll enjoy easy access to the scenic Copeland Forest, skiing and golf at Horseshoe Resort, rejuvenating spa experiences at Vettä Nordic Spa, and an extensive network of walking and biking trails. A new community centre and elementary school are also nearby, making this an ideal location for families and outdoor enthusiasts alike. Experience the perfect blend of comfort, privacy, and four-season living in one of Horseshoe Valley's most desirable neighbourhoods. Welcome Home. (id:5764)

5 Pine Point, Oro-Medonte

Listing courtesy of RIGHT AT HOME REALTY.

$1,349,000
5 Beds ⋅ 5 Baths ⋅ S13467448 MLS® #
TIMELESS ESTATE-STYLE LIVING IN DISTINGUISHED CATHEDRAL PINES WITH NEARLY 2,900 SQ FT ON OVER HALF AN ACRE! Hidden behind a veil of mature evergreens in the Cathedral Pines neighbourhood, this English country manor-inspired residence sits on over half an acre, revealing nearly 2,900 square feet above grade, timeless architecture, and traditional craftsmanship. The home features a circular driveway, metal roof (2006), established gardens, a double garage with an EV charger, and a secluded backyard with a deck and expansive lawn. A significant investment has also been made in new windows and doors throughout the home, completed in 2025. Oak flooring, wood doors, detailed trim, and wood accents bring character to the interior, while dual living spaces shape the main level, each with a wood-burning fireplace, including a family room with a beamed ceiling and full-height masonry-style surround. The kitchen features wood cabinetry, pantry storage, updated high-end appliances, abundant prep space, and a breakfast area with a garden door walkout to the backyard. All five bedrooms are positioned on the second level, along with laundry for added ease, including a spacious primary bedroom with three closets and a newly renovated 4-piece ensuite. With five bathrooms in total, the home is well suited for a family-sized layout. The insulated and drywalled basement offers room for storage, hobbies, a workshop area, or future finishing potential, while high-speed Fibe internet options through both Rogers and Bell are an uncommon advantage for the area. Moments from Vettä Nordic Spa, Horseshoe Valley Resort, ski hills, golf, forested trails, biking, and dining, this address captures the best of Horseshoe Valley across all four seasons. (id:5764)

26 Cathedral Pines Road, Oro-Medonte

Listing courtesy of RE/MAX HALLMARK PEGGY HILL GROUP REALTY.

$929,000
3 Beds ⋅ 4 Baths ⋅ S13448576 MLS® #
Welcome to Horseshoe Valley living, where space, privacy, and four-season recreation come together beautifully. Set on a premium double lot surrounded by mature trees, this 3-bedroom, 2-storey home offers over 2,700 sq. ft. of finished living space and an incredible lifestyle just minutes from skiing, golf, trails, and the new Horseshoe Heights School. The main floor features areas of updated flooring, refreshed trim, pot lights, and inviting custom fireplace details that add warmth and character throughout. The bright, kitchen offers stainless steel appliances and a classic subway tile backsplash, creating a stylish and functional space for everyday living. Upstairs, you'll find three generous bedrooms, including a spacious primary suite with a renovated 4-piece ensuite complete with a soaker jet tub and glass shower. The finished walkout basement adds excellent flexibility with the ability for a second kitchen and large family room, making it ideal for extended family, teens, guests, or additional living space. Major updates include 200-amp electrical, concrete construction, a newer 2-zone heating/AC system, and an owned gas water heater. Outside, enjoy a multi-level deck, above-ground pool, and a private, tree-lined yard designed for relaxing, entertaining, and making the most of the outdoors. This is a wonderful opportunity to secure a standout property in one of Simcoe County's most desirable lifestyle communities. Your Horseshoe Valley escape awaits. Please note: The property is currently tenanted. Some photos have been virtually staged. (id:5764)

1 Pine Spring Road, Oro-Medonte

Listing courtesy of RE/MAX HALLMARK CHAY REALTY.

$774,900
3 Beds ⋅ 2 Baths ⋅ S13249470 MLS® #
Welcome to Cathedral Pines, a sought after subdivision in Horseshoe Valley. Enjoy a fantastic view of the Valley from the back of this timber framed house. Great chalet or home on 0.5-acre lot south facing. Walk out to deck with sunset views over forested ravine. Open concept main floor with stunning timber ceilings and no carpeting throughout. Spacious dining area, lots of windows with a great view and a gas fireplace on thermostat. Well laid out kitchen with island. Great room with a wood burning stove. Main level also has a powder room and laundry. 3 bedrooms on upper level. Spacious primary, bedrooms also have skylights. Pine flooring on upper level. Desired area in the valley close to hiking, biking and cross-country trails, ski hills, golf, Horseshoe Resort and Vetta Spa. Subdivision across the road from the new Horseshoe Heights school and rec center. (id:5764)

47 Cathedral Pines Road, Oro-Medonte

Listing courtesy of RE/MAX HALLMARK CHAY REALTY.

$769,900
2 Beds ⋅ 3 Baths ⋅ S13146568 MLS® #
Welcome to 3514 Penetanguishene Rd in Oro-Medonte. This well-maintained bungalow blends comfort and style, set on nearly an acre of land with no development behind, offering exceptional privacy and peaceful surroundings. The home features an inviting eat-in kitchen and a separate dining area with walkout access to a deck overlooking the beautifully landscaped yard.The expansive primary bedroom serves as a private retreat, complete with hardwood floors, a 3-piece ensuite with convenient laundry facilities, His & Hers closets, and direct access to an oversized deck perfect for relaxing outdoors.The fully finished basement provides excellent additional living space, featuring a bedroom with a cozy gas fireplace, a 3-piece bathroom, den, recreation room, and ample storage. A walkout adds flexibility and convenience, making it ideal for guests or potential in-law suite possibilities.Additional highlights include a durable metal roof and a natural gas BBQ hookup. Located in desirable Oro, this property offers the perfect balance of rural tranquility and accessibility, just minutes from skiing, Barrie, Orillia, and Highway 400 for an easy commute. Property is zoned potential for a small agricultural business. (id:5764)

3514 PENETANGUISHENE Road, Oro-Medonte

Listing courtesy of KELLER WILLIAMS EXPERIENCE REALTY.

$1,178,000
4 Beds ⋅ 3 Baths ⋅ S13020196 MLS® #
Exceptional home backing onto a prestigious golf course and cross-country ski trails, offering a unique year-round lifestyle. Extensively renovated with over $300,000 in upgrades (2024-2025), this property features soaring cathedral ceilings, an abundance of natural light from the octagon cupola, and an elegant open staircase. Offering approximately 3,400 sq. ft. of finished living space, including a walk-out basement and double garage with insulated workshop. The main floor boasts a spacious family room with stone wood-burning fireplace, floor-to-ceiling windows, and walk-out to a large deck overlooking the golf course. Bright eat-in kitchen and main floor primary bedroom with 3-piece ensuite.Lower level includes a large recreation room with gas fireplace, three additional bedrooms,Sauna,and 3-piece bath. (id:5764)

23 Country Club Lane, Oro-Medonte

Listing courtesy of HOMELIFE/BAYVIEW REALTY INC..

$1,398,000
4 Beds ⋅ 4 Baths ⋅ S12922430 MLS® #
17 Pine Ridge Trail offers luxury estate living in the heart of Horseshoe Valley, set on a private maple-treed lot backing onto forest on a quiet dead-end street. Step inside and you'll immediately appreciate the bright, open-concept design with high ceilings, pot lighting, and oversized rear windows that bring the outdoors in. The chef-inspired kitchen is truly the heart of the home, featuring a massive centre island with stone countertops, oversized double stainless fridge, gas range, dishwasher, bar fridge, and range hood-perfect for everyday living and entertaining. Between the kitchen and living room, you'll love the dedicated dining area with custom built-in cabinetry, this area is ideal for family meals, homework space, or a functional work-from-home setup, with walkout to the timber-framed covered porch complete with multiple gas lines for year-round outdoor enjoyment. The inviting living room is anchored by a stunning gas fireplace and views of the private backyard. Also on the main level is a versatile office, playroom, or potential additional bedroom, along with a 2-piece bath and oversized mudroom. The triple car garage offers two convenient interior access points-one into the mudroom and another directly to the basement stairway-providing exceptional everyday functionality. Upstairs features four spacious bedrooms including a primary suite with vaulted ceilings, walk-in closet with direct access to the laundry room, and a spa-like 5-piece ensuite with soaker tub, separate shower, and double sinks. A guest bedroom includes its own 4-piece ensuite, while bedrooms two and three share a semi 5 piece ensuite. Located minutes to Horseshoe Resort, Vettä Nordic Spa, trails, the new school, and recreation centre, you'll enjoy privacy, comfort, and true four-season living. Property has available - Residential Building / Apartment Dwelling (Finished Basement) Permit. (id:5764)

17 Pine Ridge Trail, Oro-Medonte

Listing courtesy of RE/MAX HALLMARK CHAY REALTY.

$1,249,999
6 Beds ⋅ 4 Baths ⋅ S12922472 MLS® #
Welcome to this exceptional, one-of-a-kind home in the highly sought-after community of Simcoe Estates. Situated on a private, mature lot spanning over two acres, this residence offers the perfect blend of luxury and tranquility. Step inside to a naturally bright, open-conceptliving space. Gleaming hardwood floors, recessed pot lights, and a stunning glass railing onthe oak staircase create a sophisticated, modern atmosphere. It boasts custom storage units, a beautiful waterfall-edge quartz counter and backsplash, and a cozy gas fireplace that seamlessly connects to the living room. From the living area, walk out to a magnificent three-tiered deck, ideal for enjoying the surrounding natural beauty. After a long day, retreat to the spa-like primary bathroom, complete with heated floors, a large soaker tub, and a refreshing rain shower. (id:5764)

11 Woodland Crescent, Oro-Medonte

Listing courtesy of RIGHT AT HOME REALTY.

$1,099,000
3 Beds ⋅ 3 Baths ⋅ S12916908 MLS® #
.Welcome to your perfect four-season home and retreat, just a stone's throw from the Horseshoe Valley Resort. Step inside to a bright, open-concept main floor where style meets comfort. The beautifully designed kitchen anchors the space with crisp white cabinetry, sleek countertops, a farmhouse sink stepping out to an expansive deck overlooking the Caribbean style pool and backyard oasis. The layout flows effortlessly into the living and dining areas-perfect for entertaining or unwinding after a day around the pool, golfing, biking or skiing. The main-floor primary suite offers views of the ski hill with a soaker tub to indulge and enjoy after a day on the slopes. Downstairs, the full walkout basement features a recreational room, large bathroom and two additional bedrooms-perfect for guests, family, or even a home office setup-along with direct access to the backyard oasis. Step outside and you'll discover what truly sets this property apart, a beautiful private treed 3/4 acre lot with a large heated saltwater pool surrounded by a 3000 sq ft. stone patio, armor stone, mature perennial gardens and fire pit offering a private resort-style setting right at home. The lush fully fenced grounds are kept effortlessly green with unground sprinkler system, so you can spend more time enjoying the space and less time maintaining it. Whether it's backyard BBQ pool parties around the campfire, ATVing or biking through the local trails, golfing at the resort, hitting the slopes or snowmobile trails this property is built for making memories. Additional highlights include, gas barbecue hookup, perennial gardens and fruit trees surrounding the property. Horseshoe valley is known for its prestige and is a rapidly growing location with a new public school , medical and community center and new grocery store currently being built down the road in nearby Craighurst. This is more than a home-it's a lifestyle. (id:5764)

24 Birch Grove Drive, Oro-Medonte

Listing courtesy of Realty Executives Plus Ltd.