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49 Red Oak Crescent in Oro-Medonte: Shanty Bay House for sale : MLS®# S13607350
49 Red Oak Crescent Oro-Medonte L0L 2L0 
$1,488,000Residential Freehold- Status:
- Active
- MLS® Num:
- S13607350
- Bedrooms:
- 8
- Bathrooms:
- 4
Rarely offered in the highly sought-after Shanty Bay community, this exceptional residence at 49 Red Oak Crescent presents a rare opportunity to own a beautifully maintained family home offering outstanding privacy, complete with an impressive gated entrance and an expansive lot just minutes from the lake. Offering over 4,600 sq. ft. of sun-filled living space, this impressive home seamlessly blends comfort, functionality, and thoughtful upgrades throughout. Designed with large families and multi-generational living in mind, the home features an ideal layout with two bedrooms on the main floor, two spacious bedrooms on the upper level, and four additional bedrooms in the fully finished basement featuring high ceilings and upgraded vinyl flooring. The spacious primary suite includes a large walk-in closet and a beautifully updated ensuite with double vanities. Expansive principal rooms and abundant natural light create a warm and inviting atmosphere perfect for both everyday living and entertaining. The professionally landscaped backyard, with over $50,000 invested in outdoor improvements, provides a stunning outdoor setting ideal for relaxing or hosting gatherings, while a premium pool table valued at approximately $25,000 is included with the home. Additional upgrades include a new furnace and hot water tank (2025) and roof replacement (2022), offering peace of mind for years to come. This special property has also been professionally reviewed by a Feng Shui master and comes with certification, adding a unique and meaningful touch to the home's already exceptional appeal. Surrounded by serene natural beauty and located just a 4-minute drive to the lake, this remarkable property offers the perfect balance of luxury, privacy, and convenience in one of Oro-Medonte's most peaceful and family-friendly neighbourhoods. Motivated Seller. More detailsListed by HOMELIFE LANDMARK REALTY INC.- LANCE CHILTON
- RE/MAX HALLMARK CHAY REALTY [218 BAYFIELD ST 100078 & 100431]
- 1 (705) 7955167
- Contact by Email
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1189 Woodland Drive in Oro-Medonte: Rural Oro-Medonte House for sale : MLS®# S13607388
1189 Woodland Drive Oro-Medonte L3V 0R8
$2,999,900Residential Freehold- Status:
- Active
- MLS® Num:
- S13607388
- Bedrooms:
- 4
- Bathrooms:
- 4
Some properties offer waterfront. Others offer a lifestyle that simply can't be replicated. From the curb appeal to the breathtaking lake views the moment you step inside, this is a home designed to be experienced. Along the shores of Lake Simcoe in Oro-Medonte, this luxury waterfront home offers peaceful lakeside living just 10 min from the amenities of Orillia. Rich in arts, culture, waterfront parks, dining & year-round events, putting the best of city conveniences & small-town charm just minutes from your doorstep. Every inch of 1189 Woodland Drive has been shaped with a commitment to premium materials & enduring craftsmanship. Redesigned in 2022, the thoughtfully re-imagined floor plan blends timeless design with modern comfort. Extensive upgrades & carefully selected finishes elevate this home well above the ordinary, including multiple heating zones. The open-concept main living area was designed to maximize the panoramic lake views, anchored by a beautifully appointed chef's kitchen at the heart of the home. A fully finished walkout lower level with a self-contained in-law suite offers outstanding flexibility for multi-generational living or guests. Outside, multiple outdoor living spaces embrace every aspect of waterfront living. Relax on the waterside patio, entertain on expansive decks, gather around the outdoor gas fireplace, unwind on the rooftop patio atop the rare double boathouse, or spend the day on the lake from your private dock. The sheltered shoreline provides calmer conditions and a more comfortable outdoor experience throughout the season. With over 100ft of private Lake Simcoe shoreline, extensive updates, a whole-home generator & finished walkout lower level, this property offers a truly distinctive waterfront setting. The combination of location, atmosphere & design must be experienced in person. This is more than a waterfront home-it's a lifestyle defined by luxury, connection to the water & memories waiting to be made. More detailsListed by RE/MAX RIGHT MOVE- LANCE CHILTON
- RE/MAX HALLMARK CHAY REALTY [218 BAYFIELD ST 100078 & 100431]
- 1 (705) 7955167
- Contact by Email
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2330 Lakeshore Road E in Oro-Medonte: Hawkestone House for sale : MLS®# S13608066
2330 Lakeshore Road E Oro-Medonte L0L 1T0
$775,000Residential Freehold- Status:
- Active
- MLS® Num:
- S13608066
- Bedrooms:
- 3
- Bathrooms:
- 2
Charming Renovated Bungalow in Beautiful Oro-Medonte. Welcome to this beautifully renovated 2+1 bedroom bungalow nestled in the heart of Simcoe County's Oro-Medonte. Just 2 minutes from lake access, this home offers the perfect blend of cottage-country charm and modern convenience. Step inside to discover an open-concept layout flooded with natural light, highlighting the stylish upgrades and thoughtful finishes throughout. The spacious kitchen and living area flow seamlessly, ideal for entertaining or cozy family evenings. Set on a large, deep lot, the outdoor space is a dream come true for gardeners, families, or anyone looking to enjoy nature just steps from their door. Whether you're seeking a year-round residence or a peaceful retreat near the water, this move-in ready bungalow is a must-see! Only 1 minute walk to the beach! More detailsListed by RE/MAX HALLMARK CHAY REALTY- LANCE CHILTON
- RE/MAX HALLMARK CHAY REALTY [218 BAYFIELD ST 100078 & 100431]
- 1 (705) 7955167
- Contact by Email
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88 Huronwoods Drive in Oro-Medonte: Sugarbush House for sale : MLS®# S13609158
88 Huronwoods Drive Oro-Medonte L0K 1E0
$779,000Residential Freehold- Status:
- Active
- MLS® Num:
- S13609158
- Bedrooms:
- 4
- Bathrooms:
- 3
Welcome to 88 Huronwoods Drive, where nature, community, and thoughtful updates come together in one exceptional property. Nestled beneath the mature canopy of the Simcoe County Forrest, and steps away from endless trails that move through the Copeland Forest, this beautifully maintained home offers the rare opportunity to enjoy peaceful forest living while remaining just minutes from everyday conveniences.Located in one of Oro-Medonte's most sought-after family-friendly communities, this property is a dream for outdoor enthusiasts. Step outside your door to endless walking, hiking, biking, cross-country skiing, and snowshoeing trails, while Horseshoe Valley Resort, Vettä Nordic Spa, Hardwood Hills, golf courses, and year-round recreation are all just moments away.The home offers outstanding versatility with a fully equipped in-law suite, making it ideal for multigenerational families, guests, or additional income potential. Set on a truly unique lot surrounded by mature trees and natural beauty, the property delivers privacy, character, and an atmosphere that is difficult to replicate.Thoughtfully updated throughout, buyers will appreciate the extensive list of recent improvements, including a new roof (2026), front and side entry doors (2025), partial window replacements (2025), all-new siding (2025), upgraded soffit, fascia and eaves with insulated backing, new blown-in attic insulation (2023), high-efficiency heat pump (2023), owned hot water tank (2023), furnace serviced (2025), landscaped grounds (2024), and a 200-amp electrical service with pony panel.If you've been searching for a home that offers character, a welcoming community, exceptional outdoor living, and the flexibility to accommodate your family's changing needs, 88 Huronwoods Drive is a property you won't want to miss. More detailsListed by RE/MAX HALLMARK CHAY REALTY- LANCE CHILTON
- RE/MAX HALLMARK CHAY REALTY [218 BAYFIELD ST 100078 & 100431]
- 1 (705) 7955167
- Contact by Email
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3225 10 Line N in Oro-Medonte: Rural Oro-Medonte House for sale : MLS®# S13609502
3225 10 Line N Oro-Medonte L0L 1T0
$1,249,000Residential Freehold- Status:
- Active
- MLS® Num:
- S13609502
- Bedrooms:
- 6
- Bathrooms:
- 4
Absolute Dream Home! Set On A Private, Park-Like 2-Acre Lot In One Of Oro-Medonte's Most Desirable Locations, This Stunning Custom-Built Home Offers Luxury, Space & Lifestyle In One Incredible Package. With Nearly 3,800 Sq Ft Of Finished Living Space, This Home Is Loaded With Features & Designed For Modern Family Living. The Bright, Open Concept Main Floor Is Anchored By A Show-Stopping Great Room With 18 Ft. Vaulted Ceilings, Wood-Burning Fireplace & Floor-To-Ceiling Windows Overlooking The Peaceful Countryside. Beautiful Eat-In Kitchen Features Stone Countertops, Gas Stove & Walkout To Professionally Landscaped And Fully Fenced Backyard-Perfect For Entertaining. Formal Dining Room & Private Office/Music Room Add Flexibility & Function To The Main Floor Layout. Upstairs, The Spacious Primary Suite Offers A Massive Walk-In Closet & Spa-Like 5-Piece Ensuite, While Two Additional Bedrooms, A Stunning Full Bath & Bonus Family Room With Office Nook Provide Plenty Of Room For The Whole Family. Fully Finished Lower-Level Features A Complete 3-Bedroom In-Law Suite With Separate Entrance, Full Kitchen & Garage Access-Perfect For Multi-Generational Living Or Additional Income Potential. Step Outside To Your Private Backyard Oasis-Complete With Large Deck, Wrap-Around Porch, Fire Pit Area, Garden & Mature Fruit Trees, All Surrounded By Towering Trees For Ultimate Privacy. Backing Onto Braestone Golf Club & Minutes To Horseshoe Valley, Skiing, Golf, Trails & More - This Is A Rare Opportunity To Enjoy A Turnkey Lifestyle Property In The Heart Of Oro-Medonte. Located Just 10 Minutes To Orillia, 20 Minute To Barrie & 1.5 Hours To The GTA. More detailsListed by Royal LePage In Touch Realty- LANCE CHILTON
- RE/MAX HALLMARK CHAY REALTY [218 BAYFIELD ST 100078 & 100431]
- 1 (705) 7955167
- Contact by Email
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8570 Hwy 12 in Oro-Medonte: Rural Oro-Medonte House for sale : MLS®# S13609524
8570 Hwy 12 Oro-Medonte L3V 0K1
$779,900Residential Freehold- Status:
- Active
- MLS® Num:
- S13609524
- Bedrooms:
- 4
- Bathrooms:
- 2
Modern Design Meets Country Living! Your Oasis Awaits You! This Fully Renovated Raised Bungalow Is Situated On A Very Large Lot With Plenty Of Outdoor space To Entertain Family & Friends. Fully Updated Open Concept Floor Plan Just Completed August 2025. Kitchen Includes Stunning Granite Counter Tops And Matching Tile Backsplash. S/S Fridge (March 2026), S/S Stove (March 2026), S/S Dishwasher & Hood Range. Engineered Harwood Flooring throughout Main Floor, Vinyl Flooring Basement. No Carpet! New Windows, Upper & Lower Walkout Decks. Metal Roof, 200 Amp Breaker Panel, Owned Water Heater. White Front Loaded Washer & Dryer ( March 2026). All Necessary Amenities are very Close. Located just Outside of Orillia, Close to Bass Lake. More detailsListed by RE/MAX REALTY SERVICES INC.- LANCE CHILTON
- RE/MAX HALLMARK CHAY REALTY [218 BAYFIELD ST 100078 & 100431]
- 1 (705) 7955167
- Contact by Email
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2 Conder Drive in Oro-Medonte: Rural Oro-Medonte House for sale : MLS®# S13606354
2 Conder Drive Oro-Medonte L0K 1E0
$749,900Residential Freehold- Status:
- Active
- MLS® Num:
- S13606354
- Bedrooms:
- 3
- Bathrooms:
- 2
Move right into this beautifully maintained 3-bedroom, 2-bathroom home, perfectly situated on a quiet, family-friendly street in a highly sought-after location. Offering the ideal blend of comfort, convenience, and functionality, this property is ready for you to enjoy from day one.The home features a spacious attached garage for everyday convenience, while the detached workshop provides the perfect space for hobbies, projects, additional storage, or a home-based business. Outside, the mature trees create a private, picturesque setting with plenty of shade and timeless curb appeal.Located just minutes from ski hills, highway access, shopping, restaurants, schools, and all essential amenities, this home offers year-round recreation and effortless commuting. Whether you're looking for your first home, a place to raise a family, or simply a move-in ready property with exceptional outdoor space, this one checks all the boxes.Don't miss this fantastic opportunity to own a turnkey home in a peaceful neighbourhood with everything you need just moments away. More detailsListed by M1 Real Estate Brokerage Ltd- LANCE CHILTON
- RE/MAX HALLMARK CHAY REALTY [218 BAYFIELD ST 100078 & 100431]
- 1 (705) 7955167
- Contact by Email
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312 1102 Horseshoe Valley Road W in Oro-Medonte: Horseshoe Valley Condo Townhouse for sale : MLS®# S13600950
312 1102 Horseshoe Valley Road W Oro-Medonte L4M 4Y8
$398,900Residential Condo & Other- Status:
- Active
- MLS® Num:
- S13600950
- Bedrooms:
- 2
- Bathrooms:
- 2
Welcome to 1102 Horseshoe Valley Rd W, Unit 312. Enjoy four-season living in this prime Horseshoe Valley location, directly across from Horseshoe Resort and just steps to The Heights Ski Club.This immaculate third-floor, end-unit condo is one of the largest in the building and has been extensively upgraded throughout, offering two bedrooms, two bathrooms, and two front balconies showcasing beautiful ski hill and resort views.The open-concept layout features a spacious living room and dedicated dining area, perfect for entertaining or relaxing after a day on the slopes or trails. The fully upgraded kitchen includesmodern cabinetry, stainless steel appliances, updated plumbing behind the walls, and a clean contemporarydesign. Both bathrooms have been renovated with stylish finishes and behind-the-wall plumbing upgrades,providing long-term peace of mind. Updated windows and sliding doors throughout the unit improve energyefficiency, natural light, and year-round comfort.The large primary bedroom includes a private ensuite andgenerous closet space. The second bedroom features a sliding divider, making it ideal for a guest room,home office, or expanded living area.This unit also offers rare forced-air heating, in-suite laundry, and an owned hot water tank. Enjoy direct access to Copeland Forest's hiking and biking trails, a pet-friendly building (with restrictions), and plenty of parking for owners and guests.Located minutes to Vettä NordicSpa, multiple golf courses, the new Horseshoe Heights Elementary School, and the upcoming community recreation centre, this move-in-ready suite delivers exceptional comfort, lifestyle, and location in one ofHorseshoe Valley's most desirable settings More detailsListed by RE/MAX HALLMARK CHAY REALTY- LANCE CHILTON
- RE/MAX HALLMARK CHAY REALTY [218 BAYFIELD ST 100078 & 100431]
- 1 (705) 7955167
- Contact by Email
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6 Slalom Drive in Oro-Medonte: Rural Oro-Medonte House for sale : MLS®# S13602292
6 Slalom Drive Oro-Medonte L0K 1N0 OPEN HOUSE: Aug 01, 202612:00 PM - 02:00 PM EDTOpen House on Saturday, August 1, 2026 12:00PM - 2:00PM
$625,000Residential Freehold- Status:
- Active
- MLS® Num:
- S13602292
- Bedrooms:
- 2
- Bathrooms:
- 3
PRIVATE CHALET RETREAT NESTLED IN NATURE WITH FOUR-SEASON OUTDOOR RECREATION AT YOUR DOORSTEP! Imagine waking up surrounded by towering trees, stepping outside to the sounds of nature, and spending your days exploring forest trails just minutes from home. This enchanting 1970s chalet-style retreat offers an unparalleled four-season lifestyle in one of Simcoe's most desirable locations. Tucked away on a quiet, forest-lined street and set on over half an acre of beautifully treed land, this property feels like your own private escape. Located just 2 minutes from Mount St. Louis Moonstone Ski Resort, with the expansive Copeland Forest just down the road, adventure awaits in every season, from morning hikes and bike rides to snowshoeing, skiing, snowmobiling, and ATV excursions. Golf, spa days, and additional resort amenities are all nearby at Settler's Ghost Golf Club, Vetta Nordic Spa, and Horseshoe Valley Resort, while Hwy 400 provides effortless connections to Barrie, Orillia, Midland, and cottage country. Step inside and be welcomed by a warm, inviting atmosphere filled with character. The open-concept living space is designed for gathering, featuring a natural gas fireplace, a bright dining area surrounded by expansive windows that bring the beauty of the outdoors inside, and a walkout leading to a private deck nestled among the trees. Upstairs, two bedrooms offer peaceful retreats, including a loft-style primary suite overlooking the living area below. The basement provides added flexibility with a rec room, a full bath, and office space, offering room to create whatever your lifestyle needs. Outside, follow a whimsical winding nature path, enjoy the fenced yard space, or simply relax beneath the trees. With a durable steel roof, ample driveway space, and a location surrounded by some of the region's best outdoor experiences, this #HomeToStay invites you to slow down, reconnect with nature, and create memories in every season. More detailsListed by RE/MAX HALLMARK PEGGY HILL GROUP REALTY- LANCE CHILTON
- RE/MAX HALLMARK CHAY REALTY [218 BAYFIELD ST 100078 & 100431]
- 1 (705) 7955167
- Contact by Email
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4408 12 Line N in Oro-Medonte: Rural Oro-Medonte House for sale : MLS®# S13604310
4408 12 Line N Oro-Medonte L0K 1E0
$824,900Residential Freehold- Status:
- Active
- MLS® Num:
- S13604310
- Bedrooms:
- 4
- Bathrooms:
- 2
Welcome to 4408 Line 12 N in Oro-Medonte! Set on 2.28 private acres, this fully finished 4-bedroom, 2-bathroom bungalow offers plenty of space both inside and out.The bright interior features large windows, modern kitchen updates, and a functional layout ideal for everyday living and entertaining. The finished basement provides additional living space, perfect for a family room, home office, gym, or guest area. Outside, enjoy privacy and natural beauty along with a welcoming covered porch, double car garage, and ample parking. Located within minutes of Orillia, golf, skiing, and major commuter routes, this property offers rural living without sacrificing accessibility. More detailsListed by RE/MAX RIGHT MOVE- LANCE CHILTON
- RE/MAX HALLMARK CHAY REALTY [218 BAYFIELD ST 100078 & 100431]
- 1 (705) 7955167
- Contact by Email
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49 Huronwoods Drive in Oro-Medonte: Sugarbush House for sale : MLS®# S13596272
49 Huronwoods Drive Oro-Medonte L0K 1E0
$799,900Residential Freehold- Status:
- Active
- MLS® Num:
- S13596272
- Bedrooms:
- 4
- Bathrooms:
- 3
Top 5 Reasons You Will Love This Home: 1) Stunning designer home tucked away among the trees, showcasing extensive upgrades throughout and offering a truly turn-key lifestyle just minutes from skiing, golf courses, and scenic bike trails 2) Beautifully updated modern kitchen featuring stainless-steel appliances, quartz countertops, and a new stove and range hood, all seamlessly integrated into a bright and inviting open-concept layout designed for everyday living and entertaining 3) Soaring vaulted ceiling in the dining room complemented by a striking stacked stone fireplace that efficiently warms the home during the winter months, along with a cozy all-season living room that provides the perfect setting for year-round relaxation 4) Thoughtfully added bedroom and full bathroom in the walkout lower level, offering exceptional flexibility and direct access to a private deck overlooking Sugarbush, complete with a premium Jacuzzi brand hot tub for the ultimate retreat experience 5) Extensive updates, including a newer metal roof, windows, septic line, water softener, and front retaining wall, providing lasting value, enhanced functionality, and peace of mind for years to come. 1,591 above grade sq.ft. plus a finished lower level. More detailsListed by FARIS TEAM REAL ESTATE BROKERAGE- LANCE CHILTON
- RE/MAX HALLMARK CHAY REALTY [218 BAYFIELD ST 100078 & 100431]
- 1 (705) 7955167
- Contact by Email
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14 Northland Court in Oro-Medonte: Craighurst House for sale : MLS®# S13596874
14 Northland Court Oro-Medonte L9J 1C4
$1,399,000Residential Freehold- Status:
- Active
- MLS® Num:
- S13596874
- Bedrooms:
- 4
- Bathrooms:
- 4
Welcome to refined country living in the sought-after Craighurst Crossing neighbourhood. Set on a premier lot, this beautifully finished 3+1 bedroom bungalow offers the perfect blend of modern design, everyday function, and small-town charm, all just minutes from Barrie, Orillia, Horseshoe Valley Resort, Copeland Forest trails, golf, skiing, and everyday amenities. The bright open-concept main floor features soaring ceilings, oversized windows, warm wood-toned flooring, and a stylish kitchen with white cabinetry, quartz counters, stainless steel appliances, subway tile backsplash, and a large dark contrasting island perfect for gathering and entertaining. The primary bedroom is conveniently located on the main floor, offering true bungalow-style living, while the upper loft level provides additional bedroom space ideal for family, guests, or a private retreat. A covered front porch adds charming curb appeal and a welcoming place to enjoy the neighbourhood, while the insulated and drywalled garage with a garage door opener adds comfort, convenience, and everyday practicality. The finished basement expands the living space even further with a fourth bedroom, recreation area, and flexible space for work, play, fitness, or extended family, plus a rough-in for a future kitchen or wet bar, offering excellent potential for added functionality. With 3875 sqft of finished living space, this home is a showstopper. Set in a growing master-planned community surrounded by the beauty of Oro-Medonte, this home delivers new-build comfort, stylish finishes, and four-season lifestyle appeal in one of the area's most exciting neighbourhoods. More detailsListed by Strive Realty Ltd.- LANCE CHILTON
- RE/MAX HALLMARK CHAY REALTY [218 BAYFIELD ST 100078 & 100431]
- 1 (705) 7955167
- Contact by Email
Data was last updated July 27, 2026 at 08:15 PM (UTC)
RE/MAX Hallmark Chay Realty
218 Bayfield St
Barrie, ON, L4M 3B6