11 Caldwell Drive

Set on over an acre just steps from Lake Simcoe, this distinctive Oro-Medonte estate invites you to live expansively with space, versatility, and endless possibilities. Behind its 150-foot frontage lies a multi-functional haven where lifestyle and investment potential align.The main residence is warm, updated, and sprawling with over 4,400 sq ft of finished living space, including a separate self-contained apartment ideal for multi-generational living or short-term stays. With six bedrooms total and multiple living areas, this home adapts to how you live, entertain, and grow.Outdoors, your personal resort awaits: an inground saltwater pool, hot tub, tiki bar, and private change house make summer days and starry nights unforgettable. The detached garage plus an expansive 3,200 sq ft shop with rear access provides the ultimate setup for hobbyists, collectors, or tradespeople. Backing onto Shellswell Park and mere steps to the lake, this is a property that elevates lifestyle but also holds untapped potential. With frontage on two streets, explore the possibility of a future severance. Whether you're dreaming of space to roam, a place to gather, or an opportunity to build long-term value this is where it all comes together.

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.

Luxury Meets Nature Brand New Modern Estate on 100x300 Ft Lot! Welcome to 76 Ruby Ridge, Oro-Medonte - a stunning luxury home where modern design meets serene surroundings. Set on a private, tree-lined lot, this 4-bedroom residence features ensuites and walk-in closets in every bedroom, a 3-car garage with high ceilings, and an airy open layout filled with natural light. $$ Thousands in high-end upgrades throughout, including 6" wide-plank hardwood floors, smooth ceilings, 50+ pot lights, and soaring ceiling heights. The chef's kitchen showcases quartz countertops, extended custom cabinetry, KitchenAid appliances, and elegant details. All bathrooms are fully upgraded with quartz vanities and designer tiles.The 100x300 ft flat lot offers exceptional possibilities for creating your dream outdoor living space - whether a pool and cabana, sports court, landscaped gardens, or a workshop, the backyard is a canvas for your vision. Located minutes to Barrie, Orillia, Horseshoe Valley, Lake Simcoe & Hwy 400, this estate perfectly blends modern luxury with peaceful country living.

Price is based on Buyer qualifying for HST Rebate. DON'T MISS THE OPPORTUNITY to build your dream home in Oro-Medonte. Just eight premium estate lots remain in Braestone Estates, the award-winning community by local builder and developer Georgian Communities. Today, nearly the entire community has been completed, with homeowners already enjoying what many call "Braestone Life." These homesites are set within a private enclave on generous estate lots of 1/2 acre or more, offering a peaceful countryside setting with nature nearby and access to the neighbouring Braestone Farm through the community trail network. Braestone is presently offering a substantial decor credit and is open to reviewing customization requests to help tailor your home to your needs. The list price reflects std finishes and lot cost. Featured here is the Oldenburg model, a 3,235 sq. ft. 2 storey with a two-car garage. A sampling of standard finishes includes: James Hardie siding, fiberglass shingles, stone accents (model specific), front porch with composite decking, dramatic open-concept floorplans, 9' smooth ceilings on the main floor, 35" Napoleon gas fireplace in the great room, 5" engineered wood plank flooring in the main hall, great room, dining room, office, and kitchen, stone countertops in the kitchen, tile-enclosed showers with frameless glass, and a high-efficiency gas furnace with HRV and humidifier. Full list of standards available. Many optional features are available, including a third garage bay, finished basement, coach house, covered rear porch or deck, and more. The builder will also consider floorplan modifications. Residents enjoy kilometres of walking trails and access to amenities at Braestone Farm, including pond skating, baseball, seasonal fruits and vegetables, maple syrup tapping, and numerous community and farm events throughout the year. Located between Barrie & Orillia, and approx 1 hr from Toronto. Skiing, hiking, biking, golf, dining, Horseshoe Resort minutes away

This exceptional executive-style corner residence showcases a refined blend of luxury, scale, and natural light throughout. The main living areas feature a dramatic open-concept design with soaring ceilings, expansive windows, and seamless transitions between the kitchen, dining, and living spaces-creating an atmosphere that feels both grand and warmly inviting. At the heart of the home, the chef-inspired kitchen impresses with a substantial island, premium cabinetry, sleek countertops, butler's pantry and high-end appliances. Designed to be both visually stunning and highly functional, it offers the perfect setting for entertaining or everyday living. Architectural details, a striking statement staircase, custom millwork, and carefully curated finishes elevate the home far beyond standard builder construction. The primary suite offers a true retreat experience with its expansive layout, oversized walkand in closet, and spa-inspired ensuite. A freestanding soaker tub, glass-enclosed shower, and double vanity are beautifully framed by large windows that flood the space with natural light. Additional bedrooms are generously proportioned with clean, modern finishes and excellent closet space, providing flexibility for family living, guests, or a sophisticated home office. Bathrooms throughout the home continue the same elevated design standard, featuring contemporary fixtures and timeless materials. Outdoor living is equally impressive. The exterior blends modern siding with elegant stonework, delivering polished curb appeal and a distinctly upscale presence. Set in a location that offers both privacy and a rare sense of openness for a newer community, this property stands apart. From its architectural character to its thoughtfully selected finishes, this home presents a rare opportunity to enjoy a luxury that feels custom-built-offering comfort, sophistication, and exceptional design at every turn.

Stunning 5-year-old home built on 100 ft. wide lot offers space, modern design and functionality. Perfectly situated just two streets away from Lake Simcoe, with beaches, neighbourhood trails, fishing docks, and a great community school, all just minutes away. This residence boasts over 3,500 sq. ft of style and beauty, tons of natural light, 10 ft ceilings on the main floor, ample storage throughout, and 4 spacious bedrooms each with an ensuite and walk-in closet. The open plan living room has a floor-to-ceiling stone fireplace, dining conveniently overlooks the kitchen, and a great layout for entertaining. Spacious kitchen has timeless quartz counters with lots of prep space, a walk-in pantry, and Samsung appliances. The finished basement adds additional living space with a family/media room, home gym, extra office space, sauna and a 3-piece bathroom. The garage has an entry into the mud room and easy access to the backyard.This home offers a comfortable, luxurious life surrounded by privacy & tranquility.

Experience luxury estate living in the prestigious, sold-out **Eagles' Rest Estates** in Oro-Medonte. This brand-new, never-lived-in **Elevation A "Croft" model** sits on a premium**75' estate lot** and offers over **3,600 sq. ft.** of beautifully designed living space, plus a finished basement foyer. Surrounded by rolling hills and mature forests, this modern farmhouse-style residence features grand proportions throughout, including **10 ft ceilings on the main floor** and **9 ft ceilings on the second level and basement**. The chef-inspired kitchen offers quartz countertops, upgraded cabinetry, and premium finishes, flowing seamlessly into a spacious great room with a natural gas fireplace. With **4 spacious bedrooms, 3.5 designer bathrooms**, and a rare **tandem garage**, this home blends elegance, comfort, and functionality. Thousands have been spent on builder upgrades, including engineered hardwood flooring, quartz countertops, high-end cabinetry, and refined finishes throughout. Located minutes from **Horseshoe Valley Resort, The Heights Ski & Country Club, Vetta Nordic Spa**, trails, golf, skiing, and year-round recreation, while still being just **15 minutes from Barrie**. A rare opportunity to own a brand-new luxury estate home in one of Oro-Medonte's most desirable communities.

Rare opportunity to own a modern home on a private 1.27-acre estate lot in the sought-after Braestone community, minutes from Horseshoe Valley Resort and Braestone Golf Club. Built in 2023, this 2-storey Georgian model offers nearly 3,000 sq. ft. of finished living space and is surrounded by mature trees, providing privacy within a community setting. The home features 4 bedrooms and 3.5 bathrooms with a bright open-concept layout connecting the kitchen, dining, and living areas. Large windows throughout provide abundant natural light and views of the treed property. The kitchen includes a large quartz centre island, stainless steel appliances, and custom cabinetry. A separate prep kitchen and butler's pantry offers additional functionality with a second fridge, sink, and built-in oven, ideal for entertaining. The main living area features a fireplace wall, hardwood flooring, pot lights, and upgraded lighting throughout the main floor. A main-floor office/library with a second fireplace provides a dedicated workspace or reading area. The primary bedroom includes large windows overlooking the property and a 5-piece ensuite with quartz countertops and double vanities. The second bedroom features a 3-piece ensuite and walk-in closet. Bedrooms three and four share a Jack-and-Jill bathroom with separate sinks and a walk-in shower. The home includes four walk-in closets for additional storage. Exterior features include a 9' x 27' covered rear deck with gas BBQ line, irrigation system in the front and backyard, and a treed private setting. Additional highlights include an oversized 1,095 sq. ft. 3-car garage, 80-amp pony panel in the garage, central vacuum rough-in, and parking for up to 12 vehicles. Braestone offers walking trails, Braestone Farm, pond skating in winter, baseball diamond, seasonal pumpkin and berry picking, and a maple sugar shack. Located approximately 10 minutes to Orillia and 25 minutes to Barrie.

Exceptional Luxury Value! Experience refined Luxury in this Stunning Executive Residence offering over 3,550 sq. ft. of thoughtfully designed, open-concept living space. Set on a quiet court on a premium 1.37-acre lot, this exceptional Home is surrounded by a private forest backdrop-your own serene Oasis.The Grand main level Welcomes you with unique 10-ft Ceilings and Elegant formal Living and Dining rooms, ideal for entertaining. A main-floor Office provides a perfect work or study space. The upgraded chef-inspired Kitchen features extended-height custom Cabinetry, high-end built-in Appliances, a walk-in pantry, and a sleek Coffee/Servery station. Overlooking the spacious breakfast area with walkout to the backyard, it flows seamlessly into the inviting family room with fireplace ideal for creating lasting memories. Upstairs, the Luxurious primary retreat offers two walk-in closets and a Spa-like ensuite with a soaking tub and glass shower. Three additional oversized bedrooms, each feature their own ensuite bath, walk-in closet, and large windows for natural light. Refined finishes include 8-ft doors, hardwood flooring, a modern staircase, pot lighting, and abundant natural light throughout. Custom 9-ft Ceilings continue on the Second Level and in the Bright walk-out Basement-an ideal space to customize. A separate side entrance leads to a functional mudroom, 3 car Garage inside access, Powder room, and finished Laundry. With approximately $300K in premium upgrades, this Home is located in a sought-after Oro-Medonte Estate Community, just minutes to Ski Resorts, Trails, and year-round Recreation. Conveniently close to Barrie, Orillia, with easy connectivity to Highways 11 & 400 for commuting to the GTA. A rare offering where Modern Luxury meets Natural Beauty. Vacant with flexible closing available. Private viewings offered.

Welcome to 1563 15 16 Sideroad A Picturesque Newly Renovated Residence Boasting over 4,000 Square Feet Of Finished Living Space With Indoor Salt Water Pool, Radiant Heating For The Entire Lower Level Including Garage, South Exposed Backyard & Much More. Endless Possibilities With Large Lower Level Rec Room.

Brand new Cloister Model - Elevation B in Eagles Rest Estates, offering 3,244 sq. ft. of upgraded living on a premium lot in a quiet, estate-style community. The bright open-concept main floor features soaring ceilings, large windows, and a beautifully appointed chef-inspired kitchen with quartz countertops, upgraded cabinetry, and a spacious centre island-perfect for everyday living and entertaining. Upstairs, you'll find four generously sized bedrooms, including a luxurious primary retreat with a spa-style ensuite, plus ample space for family, guests, or a home office. Ideally located just 10 minutes to Barrie and 15 minutes to Orillia, with convenient access to amenities, schools, and year-round recreation.

Prestigious. Spacious. Versatile. Nestled in the coveted Horseshoe Valley community, this stunning residence sits on a generously sized, naturally surrounded lot and offers over 2700 sq. ft. above grade and 2600 sq ft fully finished lower level, thoughtfully designed as two distinct and fully functional living spaces. The main level features a striking refreshed kitchen, four large bedrooms, three well-appointed bathrooms, and its own laundry-ideal for refined family living and entertaining. The lower level is intentionally elevated to feel like a private in-law or multigenerational suite, complete with a separate entrance, abundant natural light, a full secondary kitchen, dedicated laundry, and a spacious family room anchored by a double-sided fireplace. Garden doors lead directly to the backyard and covered patio beneath the upper deck, while three oversized bedrooms provide exceptional comfort and privacy for extended family or guests. A triple-car garage with direct access to the lower level further enhances the independence and functionality of this space. Outdoors, the property offers privacy and tranquility, surrounded by mature natural landscapes with ample room to relax or entertain. Recent upgrades include fresh paint throughout, brand-new appliances, updated basement flooring, and new garage doors, ensuring a move-in-ready experience. Located just minutes from the Simcoe Woods Community Centre and the newly opened Horseshoe Heights School (2025), and set within the prestigious Horseshoe Valley lifestyle, this home offers year-round recreation including ski hills, trails, golf, and outdoor amenities-while remaining conveniently connected to surrounding communities.

2024-BUILT 4,200+ SQ FT CHALET-STYLE RESIDENCE MEETS FOUR-SEASON ADVENTURE IN HORSESHOE VALLEY! Indulge in the artistry of modern design at this custom-built 2024 home in Horseshoe Valley, capturing panoramic western views and sunsets from its commanding hilltop setting. Boasting over 4,200 sq ft of above-grade living space, this modern chalet showcases striking black Hardie Board siding, stone facade accents, a fibreglass roof, and multiple glass-railed decks designed to celebrate the surrounding scenery. The open-concept main level is ideal for entertaining, highlighted by a 24-ft vaulted ceiling, floor-to-ceiling windows, and a double-sided Napoleon fireplace connecting the great room to the dining/family areas. The gourmet kitchen features Caesarstone quartz countertops, custom two-tone cabinetry, a dramatic X-leg island, a chevron tile backsplash, a pantry, and modern lighting, all flowing to a dining area with built-in shelving and a walkout. A private main-floor office provides a peaceful workspace, while the third level hosts the luxurious primary suite with its own fireplace, balcony, walk-in closet, and spa-inspired ensuite with a freestanding tub, double vanity, and glass shower, along with two additional bedrooms, a full bathroom, and a laundry room. The ground level extends the home's versatility with 9'9" ceilings, a bright rec room, an additional bedroom, and a full bathroom. Engineered hardwood, ceramic tile finishes, and meticulous craftsmanship are complemented by superior construction featuring an ICF foundation, LVL beams, and double-studded 2x6 walls. Within walking or golf cart distance to Horseshoe Resort, The Valley Club, tennis courts, and scenic trails, and just minutes to Vetta Nordic Spa, Copeland Forest, Lake Horseshoe, local dining, and Highway 400, this exceptional home is also near a new school, community centre, clinic, and fire station, defining sophisticated four-season living in one of Ontario's most prestigious destinations.

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.