St. Andrew-Windfields Homes for Sale

St. Andrew-Windfields Homes for Sale

Welcome to St. Andrew-Windfields, one of Toronto’s most prestigious neighborhoods, where elegance meets community spirit. Nestled in the heart of North York, this charming enclave is renowned for its lush landscapes, tree-lined streets, and a rich tapestry of cultural diversity. With its proximity to major highways and public transit, residents enjoy seamless access to downtown Toronto while relishing the tranquility of suburban living.

St. Andrew-Windfields boasts a variety of architectural styles, from stately custom-built homes to modern townhouses, offering something for everyone. Whether you're seeking a sprawling estate with manicured gardens or a chic, contemporary space, there are exceptional homes for sale that cater to diverse tastes and lifestyles. The neighborhood is particularly appealing to families, with top-rated schools, recreational facilities, and numerous parks, including the stunning Windfields Park, perfect for weekend picnics and leisurely strolls.

Residents here take pride in their community, with local events and gatherings fostering a strong sense of belonging. The area is also home to an array of upscale shopping options, gourmet dining, and cultural attractions, ensuring that everything you need is just a stone’s throw away.

If you're looking to invest in a home that combines luxury, comfort, and community, St. Andrew-Windfields is the perfect choice. Explore the homes for sale in this desirable neighborhood and discover the lifestyle that awaits you in this vibrant part of Toronto. Your dream home is just around the corner!

Newest St. Andrew-Windfields Homes for Sale

$2,900,000
5 Beds ⋅ 4 Baths ⋅ C13836588 MLS
Rarely available, this premium ravine-backed property presents an exceptional opportunity in the heart of St. Andrew-Windfields. Set on an approximately 12,800 sq. ft. lot, this may be one of the largest ravine lots in the area, offering exceptional privacy, a deep rear yard, mature landscaping, and a natural ravine setting rarely found in this sought-after neighbourhood.Build your dream home with the benefit of approved plans and permits already in place, making this a truly shovel-ready opportunity. Whether you're looking to bring the existing vision to life or create a custom residence of your own, the possibilities are exceptional.Surrounded by impressive custom homes and mature greenery, the property is ideally located near top-rated schools, Bayview Avenue amenities, York Mills, parks, and major transit routes.Opportunities to acquire a ravine lot of this size, with plans and permits in place, are exceptionally rare. A unique opportunity for an end-user, builder, or investor to secure a substantial parcel in one of North York's most established neighbourhoods.

11 Montressor Drive, Toronto
$4,599,000
6 Beds ⋅ 6 Baths ⋅ C13835204 MLS
Welcome to an exceptional custom residence in prestigious St. Andrews, where refined architecture, timeless finishes and sophisticated family living come together on a beautifully landscaped 50 x 136 ft lot. Meticulously maintained, the home offers striking curb appeal with stone and brick construction, copper accents and a professionally landscaped front rock garden. Inside, elegant details include oak hardwood, vaulted and coffered ceilings, wainscotting, crown moulding, beautiful lighting and 10-ft ceilings on both the main and second floors. Featuring 4 bedrooms, each with an ensuite bathroom and heated floors, including a spacious primary retreat with fireplace, sitting area, walk-in closet and spa-like 5-piece ensuite with steam shower. A skylight adds incredible light to primary ensuite. Two additional lower-level rooms are currently used as a gym and nanny suite. The main level offers formal living and dining rooms, a richly finished mahogany office, family room with fireplace and walkout to the backyard. Stunning chef's kitchen with Sub-Zero refrigerator, Dacor 6-burner gas range, double ovens, centre island and butler's pantry. The lower level is designed for entertaining with a large rec room, built-in maple bar w fridge, home theatre with gas fireplace, games area, heated floors and walkout to the backyard. Storage room roughed in for another bathroom or 2nd laundry room. 2 high efficiency Lennox furnaces and AC units. A double-car garage w EV charger and private drive provide parking for 6 cars. Over 5200 total square feet of elegant living space, it's truly an exceptional custom home in one of Toronto's most coveted neighbourhoods.

94 Munro Boulevard, Toronto
$4,388,000
6 Beds ⋅ 6 Baths ⋅ C13830874 MLS
***PRIDE OF OWNERSHIP------3Cars Garages(1Car Built-in/Front & 2Cars Detached Garages/Back)***Welcome to 158 Owen Blvd. This elegant & owner's own custom-built residence boasts blend of sophistication and warmth with exquisite materials thru-out and beautiful home nestled in a highly sought-after, prestigious St Andrew neighbourhood. This UNIQUE architectural masterpiece offers approximately 7000 sf luxurious living space(4800 sf for 1st/2nd floors), meticulously-maintained by its, original owner, to capture tranquil-private views of backyard. The main floor offers an expansive living & dining space, ideal for entertaining or relaxing at home with airy atmosphere and grand & open-feel. The gourmet kitchen is equipped with built-in appliances, a large island, spacious eat-in area, and direct flow into an outdoor deck and patio for effortless indoor-outdoor living. This residence features five spacious bedrooms upstairs, each with an ensuite or semi-ensuite for privacy and comfort. The primary suite is an private sanctuary with generous room size with hi ceiling, lavish 7-pc ensuite and walk-in closet. The basement is an entertainer's paradise, providing an ample space, functional wet bar. The additional two-bedrooms, one with an ensuite, provide ample space for family or guests.

158 Owen Boulevard, Toronto
$1,698,000
3 Beds ⋅ 2 Baths ⋅ C13830824 MLS
Welcome to 150 Upper Canada Drive, a beautifully renovated home in one of North Yorks most desirable neighbourhoods. Set on a rare 60 by 150 foot lot and surrounded by multi-million dollar homes, this property is move-in ready and offers outstanding long-term potential. The house has been completely updated from top to bottom with a brand new kitchen featuring stone counters & brand new stainless steel appliances, stylish new bathrooms including an added full bath in the basement, new flooring, pot lights, and updated windows with new window coverings. A detached garage provides parking and storage, and the large private backyard offers plenty of outdoor living space with the option to build a garden suite (assessment report available). Families will love the school district with Owen Public School, St. Andrews Middle School, and York Mills Collegiate all close by. York Mills Collegiate is one of Torontos top-ranked high schools with a 10 out of 10 rating from the Fraser Institute. Some of the city's most prestigious private schools are also within easy reach, including Crescent School, Toronto French School, Bayview Glen, Havergal College, St. Clements, Upper Canada College, and The York School. Enjoy a prime location just minutes from Bayview Village and York Mills Shopping Centre, with easy access to parks, transit, and major highways. This is a rare opportunity to own a fully updated home on a large lot in a blue-chip North York neighbourhood.

150 Upper Canada Drive, Toronto
$2,198,000
6 Beds ⋅ 3 Baths ⋅ C13830178 MLS
Nature and Tranquility in the City! Rarely does an opportunity arise to own a premium property offering an abundance of mature trees, exceptional privacy and a peaceful, cottage-inspired setting, all within the city. This lovingly maintained and thoughtfully updated family home is filled with natural light and offers over 3,000 sq. ft. of beautifully finished living space across the upper and walk out lower levels.The bright eat-in kitchen features a Frigidaire Professional refrigerator and quality built-in appliances, including a KitchenAid dishwasher, Maytag cooktop, Whirlpool oven and built-in microwave. The dining room offers a beautiful walkout to the upper deck, while the spacious living room features a fireplace and large picture and casement windows overlooking the backyard.The above-ground lower level features a separate entrance and walkout to the backyard, as well as wonderful flexibility for family living with a cozy den, office space with large built-in desk, bookshelves and cabinets, 3 bedrooms, one with a window seat, another with a bay window and fireplace, and abundant storage throughout. Unwind in your private sauna, sip coffee in the garden, relax beneath the gorgeous maple trees, or entertain and BBQ on one of the spacious decks. A 9' x 7' "s/he shed" provides additional flexible space for an office, reading nook, or whatever your heart desires.Located in the coveted St. Andrew's School District with French Immersion, within walking distance of parks and playgrounds, and just minutes from prestigious private schools, Bayview Village Shopping Centre, York Mills & Bayview subway stations, the Granite Club, Cricket Club, YMCA and Hwy 401. Buy with confidence - Carson Dunlop Home Inspection Report (Sept. 2026) available.

69 Montressor Drive, Toronto
$1,700,000
4 Beds ⋅ 4 Baths ⋅ C13826622 MLS
*Offers anytime* Make it yours! Builders, renovators and dream chasers, York Mills is calling. This is the mid-century detached home on a 50 x 125 foot lot calling for your creativity and best ideas. An executive and ideal 4 bedroom layout with a main floor office, curved staircase, extra large primary bedroom, and circular driveway. A walk-out basement with full sized windows, leading to a private backyard with mature greenery. ***** This is the family home maintained and loved for over 50 years waiting for your personal touch. Or, take advantage of Toronto's EHON program and build multi-units on the property to maximize your ROI. ***** All this placed conveniently at Bayview & York Mills, walkable to grocery stores & shops, and a quick drive to Bayview Village, the Granite Club, Miller Tavern, York Mills subway station, and the 401 to bring you anywhere in the city. *Some photos enhanced to show the home's potential.

234 York Mills Road, Toronto
$1,995,000
4 Beds ⋅ 4 Baths ⋅ C13823524 MLS
Welcome to 20 Riderwood Drive, an exceptional opportunity in the prestigious St. Andrew-Windfields neighbourhood. Offering over 4,000 sq ft of living space and designed with generous proportions throughout, this home features four spacious bedrooms, expansive principal rooms and a layout designed for comfortable family living and effortless entertaining. A huge living room and formal dining room provide elegant gathering spaces while the oversized kitchen with breakfast area serves as the heart of the home. The large family room with fireplace and built in bookshelves, offers a warm and inviting setting for everyday living. The finished lower level provides additional living space, featuring a large recreation room with a fireplace, sauna, wet bar and ample storage. An attached double car garage and private driveway provide parking for four vehicles. Lovingly maintained by the same family for many years, the home presents an exceptional opportunity to renovate, reinvent or completely reimagine to suit your vision. Located in one of Toronto's most sought after communities in close proximity to top ranked schools, beautiful parks, premier shopping, dining and convenient transit options Bring your contractor, designer or architect and bring your vision to life! Please note that this is an estate sale and the property and inclusions are being sold in as is, where is condition.

20 Riderwood Drive, Toronto
$2,398,000
5 Beds ⋅ 4 Baths ⋅ C13814398 MLS
Fabulous Family home in highly sought after 'Windfield Estates' area. Wonderful 'Country French' Kitchen for the Gourmet...Granite Counters, Island, Desk area, B/I Appliances, Ceramic floors, Sun filled Breakfast nook with double Bay windows & Walk out to private Deck overlooking fenced yard, a perfect place to enjoy morning Coffee. The spacious main floor offers Brazilian Cherry hardwood throughout the Open Concept Living & Dining areas, Crown moulding, Inviting Family Room w/Fireplace & walk out to deck, Main floor Laundry w/walk out to yard. Finished Lower level with multiple walk outs, Large Rec Room w/Fireplace, Separate Family Room, Second kitchen w/Pantry & Eating area, perfect for extended family & guests, this home has it all & is a Must See! Minutes to TTC, 401, DVP for an easy commute to the City. Exceptional neighbourhood with all Amenities including Parks, Tennis, Granite club, ample Shopping, Great Hospitals, Schools include Dunlace PS, Windfields Middle School & York Mills Collegiate, all offering French immersion & Crescent Private school for Boys, this is the place to be!

45 Pinnacle Road, Toronto
$18,000,000
6 Beds ⋅ 11 Baths ⋅ C13813742 MLS
THE LEGACY AT OLD COLONY Inspired by Frank Lloyd Wright's philosophy of organic architecture, this exceptional residence brings together timeless design, natural materials and a deep connection to its surroundings. Strong horizontal lines, expansive walls of glass, rich wood and stone, and a seamless relationship between interior and exterior create a home of rare scale, warmth and architectural presence. Set amid beautifully landscaped grounds and mature trees, the estate is designed for a life well lived. Expansive terraces extend the living space outdoors, while a professional tennis and multi-sport court, dedicated wellness spa, wine cellar and tasting room, gallery walls, and professional home theatre offer a remarkable setting for recreation, entertaining and quiet retreat.At its centre, the Cameo kitchen is both beautifully composed and highly functional, complemented by generous gathering spaces and private bedroom suites with refined ensuites and separate dressing rooms. Throughout, natural light, thoughtful proportions and carefully selected finishes create an atmosphere that is elevated yet entirely livable.Ideally positioned in one of Toronto's most sought-after residential enclaves, this private estate is moments to the Granite Club, Toronto Cricket & Curling Club, Donalda Club, Rosedale Golf Club and Bayview Golf & Country Club. Yorkville, Bayview Village, York Mills and Shops at Don Mills offer exceptional dining and shopping, while leading independent schools, major highways, downtown Toronto, private aviation and Pearson International Airport are all within convenient reach.A distinctive architectural offering for those who value privacy, design and an exceptional way of living. A World of Magnificence Awaits....

103 Old Colony Road, Toronto
$3,890,000
6 Beds ⋅ 9 Baths ⋅ C13809838 MLS
Beautiful renovated York Mills Custom Built Cut Stone Home. Totally updated in 2026. 5bedrooms and nine bathrooms. Gracious and expansive main floor with wonderful flow. Perfect for family get togethers and marvelous entertaining. New Bosch appliances, two new furnaces, two new air conditioners, new water heater. Kitchen cabinetry and island refinished. Living and Dining room enhance this home with more formal possibilities. Discreet main floor office with walnut panelling. Walk out to two car garage with refinished wood doors from main floor. Primary Bedroom has two walk in closets and enormous six piece ensuite with gas fireplace. Each of the four other bedrooms has closets with built ins and four piece ensuites. Lower level has gym, steam room, nanny's room, family room with full bar and screening room potential + walk out to fully landscaped yard with mature cedars. Mostly new cedar roof, and soffits whole exterior and interior repainted, floors, railings and risers all refinished. Second Floor laundry and lower level rough in laundry. All fireplaces have entirely new hardware. Truly move in condition. Come, show and buy this incredible new mechanically perfect York Mills home. Quick on/off from 401 and DVP. Neighborhood bus at the door goes to York Mills station. TDSB area schools are: Owen French immersion, St Andrews Gifted Athlete, York Mill Collegiate. Havergal, Crescent and Toronto French 15 minute drive. Bayview Village, Shops at York Mills and extensive ravine system all close by.

1B Carluke Crescent, Toronto
$3,190,000
5 Beds ⋅ 5 Baths ⋅ C13808274 MLS
A Rare Opportunity In Prestigious St. Andrew-Windfields! Set On An Exceptional 80.77 X 170 Ft South-Facing Lot, This Beautifully Maintained And Updated Residence Offers An Outstanding Combination Of Location, Land And Lifestyle. Surrounded By Mature Trees And Distinguished Homes, The Property Features A Sun-Filled, Private Backyard And Generous Outdoor Space-Ideal For Family Living And Entertaining. Inside, Large Windows And Well-Proportioned Principal Rooms Create A Bright And Inviting Atmosphere, While The Flexible Layout Provides Excellent Space For Growing Or Multi-Generational Families. A Versatile Suite Above The Garage Is Perfect For Extended Family, Guests, A Private Home Office Or Study. One Of The Property's Greatest Assets Is Its Impressive Approx. 13,551 Sq. Ft. Lot, Offering Exceptional Width And Depth In One Of Toronto's Most Established Luxury Neighbourhoods. Enjoy The Home Today While Benefiting From Outstanding Long-Term Potential, Including The Opportunity To Create A Future Custom Residence. Ideally Located Within Walking Distance To York Mills Subway, With Convenient Access To Yonge Street, Highway 401, Parks, Shopping And Everyday Amenities. Situated In The Sought-After Owen Junior Public School, St. Andrew's Middle School, York Mills Collegiate Institute Districts And Other Top Private Schools . An Exceptional York Mills Offering-A Beautiful Family Home, A Remarkable South-Facing Lot, And An Opportunity With Tremendous Future Potential.

19 Lower Links Road, Toronto
$2,190,000
4 Beds ⋅ 3 Baths ⋅ C13806918 MLS
Welcome to this stunning family home located in one of North York's most prestigious and sought-after enclave neighborhoods. Situated on a magnificent lot surrounded by mature trees, this property offers an exceptional blend of tranquility, privacy, and classic elegance.Featuring a bright, functional layout with spacious principal rooms, a sun-filled living area, and generous bedrooms-perfect for both daily family living and effortless entertaining. Exceptional opportunity to move in, renovate to your personal taste, or build your dream luxury estate among multi-million-dollar custom homes.Unbeatable location just minutes to top-ranked public and private schools, Bayview Village, York Mills Shopping Centre, parks, subway, and quick access to Hwy 401/DVP. A rare opportunity in an top-tier neighborhood-don't miss out!

-17 Ealing Drive, Toronto
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