St. Andrew-Windfields Homes for Sale

St. Andrew-Windfields Homes for Sale

Welcome to St. Andrew-Windfields, one of Toronto’s most coveted neighborhoods, where suburban charm meets urban convenience. Nestled in the prestigious North York district, this vibrant community is known for its tree-lined streets, spacious lots, and a welcoming atmosphere that feels like home the moment you arrive.

St. Andrew-Windfields boasts an impressive array of amenities, including top-rated schools, lush parks, and upscale shopping options. Families will appreciate the proximity to renowned educational institutions such as York Mills Collegiate Institute and Windfields Junior High School, ensuring quality education is just around the corner. For outdoor enthusiasts, the area is dotted with beautiful parks, including the expansive Edward Gardens, perfect for picnics, leisurely walks, and enjoying the great outdoors.

The neighborhood is also known for its luxurious homes, many of which feature stunning architectural designs and modern finishes. From sprawling estates to elegant bungalows, there is a diverse selection of properties for sale that cater to various lifestyles and preferences. Whether you’re seeking a family-friendly residence or a sophisticated retreat, St. Andrew-Windfields has something for everyone.

Transportation is a breeze, with easy access to major highways and public transit options, making commutes to downtown Toronto seamless. Additionally, the community's proximity to fine dining, cultural attractions, and recreational facilities means you’ll never be far from the excitement that the city has to offer.

Explore the charm of St. Andrew-Windfields and discover your dream home in this exceptional neighborhood. With homes for sale that reflect both luxury and comfort, this is a place where you can truly thrive.

Newest St. Andrew-Windfields Homes for Sale

$2,799,000
4 Beds ⋅ 3 Baths ⋅ C13792826 MLS
Welcome to 171 Old Yonge Street, a rare detached two storey residence on a generous 75 x 150 ft lot in the prestigious St. Andrew-Windfields enclave of North York. Set in a serene, country-like ambiance on a beautiful treelined street, this exceptional property offers space, charm, and distinction in one of Toronto's most sought-after neighbourhoods. Surrounded by top-ranked schools including Owen Public School and St. Andrew's Middle School, lush parks, and convenient amenities, it provides quick access to Highway 401, upscale shopping, and fine dining. Whether you're a builder, investor, or end-user, this is a unique opportunity to create your dream home in a community where families settle for generations. Properties of this calibre are rarely offered and highly coveted. Don't miss this one!

171 Old Yonge Street, Toronto
$4,990,000
5 Beds ⋅ 7 Baths ⋅ C13791646 MLS
Brand-New Custom-Built Luxury Residence In Prestigious St. Andrew-Windfields, One Of Toronto's Most Sought-After Executive Neighbourhoods. Offering Approx. 7,620 Sq.Ft. Of Total Living Space, Including 5,450 Sq.Ft. Above Grade + 2,170 Sq.Ft. Finished Walk-Up Basement. Situated On A Premium 60 X 125 Ft South-Facing Lot, This Modern Architectural Masterpiece Showcases Exceptional Craftsmanship, Sophisticated Design, And Top-Tier Finishes Throughout. Featuring 4+1 Bedrooms Above Grade, 6 Washrooms, A 3-Level Elevator, Control4 Smart Lighting System, Central Vacuum, Motorized Blinds, Surround Sound, Security Cameras, And Premium Custom Details. The Open-Concept Main Floor Offers Elegant Living, Dining And Family Rooms, Custom Kitchen Plus Secondary Kitchen, Miele Appliances, Two Dishwashers, White Oak Hardwood Flooring, Designer Lighting, Custom Millwork, Onyx Slab Hallway, And A Linear Gas Fireplace With Stunning 9 Ft Slab Feature Wall. The Upper Level Features Spacious Bedrooms, Spa-Inspired Ensuites With Heated Floors, Smart Toilets, Steam Shower, His & Hers Shower, Linear Drains, Custom Wood Paneling, And Luxury Finishes. The Finished Walk-Up Basement Is Designed For Entertaining And Family Enjoyment, Complete With Recreation Room, Media Room, Exercise Room, Cinema Projector, Sauna, Heated Floors, Surround Sound System, And Direct Walk-Up Access. Additional Highlights Include Two Low-Noise Lennox Furnaces, Two Lennox A/C Units, Smart Thermostats, Snow-Melt Driveway System, Lawn Sprinkler System, Smart Garage Opener, Mahogany Main Entrance Door, 7-Inch Selected White Oak Hardwood, And Extensive Custom Upgrades Throughout. Located In An Exclusive, Mature And Quiet Residential Community Surrounded By Multi-Million Dollar Custom Homes. Minutes To Top-Ranked Schools, Parks, Golf, York Mills, Bayview Village, Shops At Don Mills, Hwy 401/404/DVP, TTC, Fine Dining And Everyday Conveniences.

15 Aldershot Crescent, Toronto
$3,895,000
4 Beds ⋅ 5 Baths ⋅ C13790060 MLS
Tucked away on a quiet cul-de-sac, 11 Mead Court offers the perfect blend of privacy, and convenience, set on a beautifully treed lot that feels like your own personal retreat. This inviting ranch-style bungalow is filled with natural light from its many large windows and showcases cathedral ceilings in both the family room and primary bedroom, creating an airy, elegant atmosphere. Thoughtfully updated and meticulously maintained, the home features a striking stone front exterior, spacious bright open kitchen/ living area, huge master bedroom retreat, fully renovated basement, newer roof, two cozy wood-burning fireplaces, a Tesla car charger, and an irrigation system. Step outside to enjoy a serene slate patio, ideal for relaxing or entertaining. Located in a prestigious neighbourhood near Bayview & York Mills, and just moments from the Granite Club, Post Road, and Edwards Gardens, this home combines luxurious living with Toronto's natural beauty. You're minutes to top-rated schools, shops, dining, golf, and have easy highway access, all complemented by a two-car attached garage and ample driveway parking. Wonderful Opportunity to renovate or create your own Luxurious custom home in this idyllic location.Lot Area is over 16,000 sq. feet and pies to over 200 feet at rear.No contractors/work permitted without owner authorization.

11 Mead Court, Toronto
$5,199,000
10 Beds ⋅ 9 Baths ⋅ C13789330 MLS
Luxurious 8+2 bedroom with 5 bedrooms on second floor and 3 additional rooms on a private third floor. Stone front, located in prestigious Bayview and York Mills area. This unique home features over 10,870 square feet of Living Area with over 7,100 Sq ft above the ground. Large lot with over 100 feet frontage, huge garage (1,300 SQFT) that fits 5+ cars. Magnificent 2 storey hallway , 3 air conditioners, Master bedroom with dream newly built walk-in closet and a fabulous private lounge with fireplace, Main kitchen with attached private prep (wok) kitchen equipped with appliances is a chef's dream, and perfect for entertaining. 3 skylights, front main and service entrance. Great house for entertainment, in finest school district and in vicinity of the City's finest private schools and the Granite club. Proximity to Hwy 401/DVP and subway lines. Third floor bedrooms can be ideal for multigenerational families or for families/guests wanting a private upper floor.

17 Heathcote Avenue, Toronto
$2,125,000
4 Beds ⋅ 4 Baths ⋅ C13787376 MLS
Welcome to this beautifully maintained and lovingly cared-for family home in the heart of the prestigious St. Andrew's neighbourhood. From its warm and welcoming curb appeal to its exceptional interior layout, this is a rare opportunity to move right in, continue to update at your own pace, or build the custom home of your dreams. A rare main floor addition provides the extra living space so often sought yet seldom found in the area, featuring both a spacious family room and a private home office-an invaluable combination for today's family. Thoughtfully designed with two side entrances, convenient mudroom, powder room, and two staircases to the lower level, this home offers outstanding functionality for everyday living. The updated kitchen walks-out to the stunning backyard. Four generous bedrooms, four bathrooms including a private primary ensuite, and abundant storage space ensure comfort for growing families. Step outside to a bright west-facing backyard with exceptional privacy and beautifully landscaped gardens. The covered patio is the perfect setting for family meals, relaxing evenings, and effortless entertaining. Location is second to none. Ideally situated just one block from both highly coveted Owen Public School and St. Andrew's Middle School, children can walk to two of the area's most sought-after schools. Enjoy Owen Park just steps away, the heart of the neighbourhood, with its playground and expansive green space, along with nearby Tournament Park and its community tennis club, and St. Andrew's Park for endless family recreation. Enjoy the convenience of Bayview and York Mills with York Mills Shopping Centre offering groceries, banking, and Shoppers Drug Mart, while York Mills Arena features a playground, baseball diamond, and walking trails. Commuting is effortless with a quick bus ride to York Mills Subway Station and excellent access to Highway 401 for travel downtown or out of town. Enjoy one of Toronto's most desirable family neighbourhoods.

122 Fenn Avenue, Toronto
$4,549,999
5 Beds ⋅ 5 Baths ⋅ C13784786 MLS
A rare legacy estate awaits! Seize the opportunity to build your dream home on one of Toronto's most prestigious streets. Nestled in the heart of the coveted Bayview and York Mills enclave, 38 Fifeshire Road presents an exceptional offering to create a bespoke masterpiece in one of the city's most distinguished neighbourhoods. Spanning nearly 1/2 an acre, this expansive ravine lot is a canvas of serenity and prestige, framed by lush greenery, mature trees, and the tranquil beauty of its natural surroundings. With exceptional frontage, depth, and breathtaking ravine vistas, this property is a dream for visionary architects and discerning homeowners. The existing residence, boasting nearly 5,000 square feet of well-appointed living space, provides a foundation of grandeur, yet the true allure lies in the lands potential. Imagine a custom-designed estate with sweeping outdoor terraces, infinity pools, or private gardens all tailored to your unique vision of luxury. Located just moments from Toronto's finest offerings, including Bayview Villages upscale shopping, elite private and public schools, gourmet dining, exclusive clubs, and seamless access to Highway 401 & DVP, this address marries tranquility with connectivity. 38 Fifeshire Road is not merely a home its a legacy in the making, a rare chance to define timeless elegance on one of Toronto's most iconic streets.

38 Fifeshire Road, Toronto
$6,680,000
8 Beds ⋅ 8 Baths ⋅ C13779464 MLS
A Country Estate in the Heart of the City. Hidden behind private gates and enveloped by nearly an acre of magnificent, tree-canopied grounds, 372 Old Yonge Street is a remarkable Tudor residence offering a level of privacy, character and architectural presence rarely found in Toronto. Offering **over 10,000 sq. ft. of living space across three expansive storeys plus the lower level**, this substantial residence presents an extraordinary canvas for its next chapter. Evoking the timeless character of an English country manor, the home is distinguished by its Tudor rooflines, intricate brickwork, stately chimneys, leaded windows, rich millwork, magnificent beamed ceilings and distinctive fireplaces. Grand principal rooms and impressive proportions create exceptional spaces for entertaining and family living, while **eight bedrooms and eight bathrooms** speak to the remarkable scale of the residence. Its rare three-storey configuration offers tremendous flexibility and potential to reimagine the interiors while preserving the architectural character that makes this home so distinctive. Beyond the residence, expansive lawns, towering mature trees and established gardens create a secluded sanctuary that feels worlds removed from the city. Ideally situated in prestigious **York Mills**, within easy reach of many of Toronto's renowned private schools, including **Crescent School, Toronto French School, Havergal College and The Bishop Strachan School**, along with excellent public schools, private clubs, parks, shops and restaurants. Convenient access to Yonge Street, Highway 401 and the city's major thoroughfares places the best of Toronto within easy reach. **An extraordinary estate of remarkable scale, character and possibility-ready for its next chapter.**

372 Old Yonge Street, Toronto
$2,995,000
5 Beds ⋅ 4 Baths ⋅ C13779070 MLS
Located on one of Toronto's most prestigious streets, 176 Old Yonge Street offers a rare opportunity to build a custom estate in the coveted Bayview and York Mills neighbourhood. Set on a spectacular ravine lot surrounded by mature trees and lush greenery, the property boasts exceptional frontage, depth, and picturesque views.The existing ranch-style bungalow provides comfortable living space, while the true value lies in the property's extraordinary redevelopment potential. Imagine creating a bespoke residence with expansive outdoor living areas, private gardens, and resort-inspired amenities tailored to your vision.Just minutes from the TTC subway line, top-rated schools, fine dining, private clubs, and major highways, this exceptional address combines natural tranquility with unmatched convenience. Enjoy the home as it stands today or create a legacy estate in one of Toronto's most sought-after locations.

176 Old Yonge Street, Toronto
$10,880,000
8 Beds ⋅ 11 Baths ⋅ C13771198 MLS
Designed & Built By Its Owner. Stunning. Designer Palette. Exquisite Custom Residence On A Premium South Lush Ravine-Like Lot W/ Almost 300' Deep. Built W/ The Highest Standard Of Luxury Appointments, This Is An Exceptional Custom-Built Estate. Located Within One Of Toronto's Most Sought-After & Prestigious Enclaves. Offering Over 12,000 Sq. Ft. Of Exquisitely Designed Living Space, Blending Grand Architectural Proportions W/ Refined Contemporary Luxury. A Striking Foyer Introduces Sophisticated Principal Rooms Defined By Soaring Ceilings, Rich Hardwood Flooring, & Expansive Windows Framing Views Of The Magnificent Grounds. Sauna, Spa Room, Surround System On All 3 Levels. The Gourmet Kitchen Is Beautifully Appointed W/ Premium Appliances, Marble Countertops, Oversized Centre Island, & Seamless Walk-Out To The Terrace For Alfresco Dining & Entertaining. A Separate L/L Service Kitchen Further Enhances The Home's Exceptional Entertaining Capabilities. The Main-Floor Primary Suite Is A Serene Private Retreat Featuring A Spa-Inspired Ensuite, Bespoke Dressing Room, & Direct Garden Walk-Out. Impressive Upper-Level Primary Suite Offers A Fireplace, Private Sitting Area, Luxurious Ensuite & Walk-In Closet, & A Private Terrace Overlooking The Grounds. 8 Generously Sized Bedrooms, Each W/ Ensuite Access, Provide Exceptional Comfort & Flexibility For Family & Multi-Generational Living. Featuring 2 Laundry Rooms, A Main-Floor Office W/ A Separate Side Entrance & Private Hallway, A L/L Library, & A Custom Elevator Servicing All Levels. Expansive L/L Complete W/ A Rec Room, Surround Sound System, Gym, Wet Bar, & Direct Walk-Out To The Professionally Landscaped Grounds. Ambient Exterior Lighting Enhances The Property's Impressive Setting. Exceptional Space For Outdoor Entertaining, A Future Pool, Or A Private Garden Retreat. A Circular Driveway & 4-Car Garage Complete This Exceptional Estate. Ideally Positioned Near Bayview Avenue, York Mills, & The Rosedale Golf Club.

101 Forest Heights Boulevard, Toronto
$3,595,000
5 Beds ⋅ 5 Baths ⋅ C13768906 MLS
In the elite St. Andrews neighbourhood you could be living in a sanctuary of luxury. Build your dream mansion in the heart of Fifeshire, one of Toronto's most desirable communities. This spectacular showcase corner lot within a coveted Toronto district awaits a new home and a visionary's creation. This appealing property is a true gem . You will be ideally located close to top-rated schools with easy transportation all while being surrounded by exquisite homes. Some room photos show virtually staged furnishings. There are also renderings of conceptual homes. The proposed concepts labeled with Sharf Architecture Inc. have site plan, floor plans, and area calculations. Also a schematic zoning-ready proposal is done for 3 floors with 8,500+ Sq.Ft. of above ground living space. Now is the time to move on this exceptional opportunity.

2 Chieftain Crescent, Toronto
$1,148,000
4 Beds ⋅ 3 Baths ⋅ C13766956 MLS
Located in the highly sought-after St. Andrew's neighbourhood of North York, this well-maintained home is nestled within a top-ranked school district and offers exceptional convenience with easy access to the GO Train, TTC, major highways, shopping, parks, and everyday amenities. Situated on a generous lot, this home features one of the largest floor plans of its type in the neighbourhood, offering a spacious and functional layout with separate living and family rooms, a main-floor powder room, and a bright eat-in kitchen. The finished basement provides excellent additional living space, complete with a large recreation room, an extra bedroom, and a full washroom-ideal for extended family, guests, or a home office. Meticulously maintained and move-in ready, this home has been thoughtfully updated throughout and offers outstanding comfort, space, and value!!

334 Woodsworth Road, Toronto
$2,500,000
6 Beds ⋅ 5 Baths ⋅ C13755708 MLS
An Incredible Opportunity In North York's Prestigious St. Andrews Enclave! This Expansive 6+1 Bedroom, 5-Bathroom Residence Offers An Exceptional Combination Of Scale, Comfort, And Functionality, Perfectly Suited For Growing Families And Effortless Entertaining. The Beautifully Updated Kitchen Overlooks The Private, Landscaped Backyard And Flows Seamlessly Into Bright Principal Living Spaces Anchored By A Warm Gas Fireplace. A Rare Main Floor In-Law Suite Adds Outstanding Versatility For Multi-Generational Living, Guests, Or A Dedicated Home Office. Upstairs, Soaring Ceilings Enhance The Spacious Second Level, While The Sun-Filled, South-Facing Primary Suite Offers A Walk-In Closet And A Well-Appointed 4-Piece Ensuite. Outside, Discover A Private Backyard Retreat Complete With Your Own Basketball Court and Plenty Of Space To Relax, Play, Or Entertain. Ideally Located In One Of North York's Most Coveted Neighbourhoods, Just Moments From Top-Ranked Schools, Parks, TTC, Fine Dining, And Everyday Amenities. A Rare Offering In One Of Toronto's Most Established And Desirable Family Communities.

110 Upper Canada Drive, Toronto
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