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

$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 your morning Coffee. The spacious main floor offers Brazilian Cherry hardwood throughout the Sun filled Open Concept Living & Dining areas, Crown moulding, Tranquil 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, Schools include Dunlace PS, Windfields Middle School & York Mills Collegiate, all offering French immersion & Crescent Private school for Boys, this is the place to live!

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
$6,799,000
8 Beds ⋅ 10 Baths ⋅ C13805786 MLS
Welcome to 46 Wimpole Drive, an extraordinary estate residence in the prestigious St. Andrew's community, where timeless architecture, refined interiors and exceptional scale come together in a truly distinguished setting. Surrounded by mature landscaping and expansive private grounds, the residence offers an exceptional sense of arrival with a four-car garage and sweeping circular driveway accommodating approximately 10 vehicles.Inside, a dramatic skylight and soaring vaulted ceiling extending to the second level create an impressive architectural focal point, introducing an abundance of natural light and a sense of grandeur. The main level is beautifully appointed for both sophisticated entertaining and effortless family living, featuring elegant living and dining rooms, a generous family room and a private office with custom built-ins. Two powder rooms, a dedicated laundry room and an expansive kitchen with breakfast area and walkout to the deck complete the level.The second floor offers six generously proportioned bedrooms. The serene primary retreat features a private sitting area beneath a skylight, his-and-hers walk-in closets and a luxurious six-piece ensuite with sauna. Five additional bedrooms and well-appointed four-piece bathrooms provide exceptional comfort for family and guests.The finished lower level extends the living experience with a spacious recreation room, wet bar, exercise room, private office, fireplace, full kitchen, cold room and abundant storage. A separate nanny's suite with three-piece ensuite, additional laundry facilities and a three-piece bathroom with sauna provide remarkable versatility.Five fireplaces, a private elevator servicing all levels, two furnace rooms, two sump pumps, generator and two dry wells reflect the home's exceptional infrastructure. All chandeliers are included.A rare offering of scale, privacy and enduring elegance in one of Toronto's most coveted residential neighbourhoods.

46 Wimpole Drive, Toronto
$849,800
4 Beds ⋅ 2 Baths ⋅ C13800822 MLS
Location, location, location! Affordable and adorable, this charming 4-bedroom home is brimming with potential. With a little updating, it offers a fantastic opportunity to create a home that truly reflects your style. Ideally situated close to sought-after schools, parks, shopping, and everyday conveniences, with easy access to both the 401 and DVP for effortless commuting. A wonderful opportunity in a highly desirable neighbourhood!

32 Northey Drive, Toronto
$6,995,000
6 Beds ⋅ 8 Baths ⋅ C13797004 MLS
Bespoke Residence Set On A Stunning 121' Wide Manicured Lot Which Stands Among The Finest In Prestigious Estates On The Much Sought After St. Andrew-Windfields Neighborhood. Encompassing Approximately 8,300 Square Feet Of Curated Living Space With Ideal Entertainment Flow, The Residence Is Defined By Imported Marble, Rich Hardwood, Tailored Lighting, And Refined Designer Detailing Throughout. Beyond A Tree-Lined Circular Drive, The Stately 6+1 Bedroom, 9 Bathroom Home Reveals A Grand Foyer Of Striking Elegance, Where A Soaring Cathedral Ceiling With Skylight Bathes The Interiors In Natural Light, Accentuating A Sweeping Natural Stone Staircase With Custom Brass And Wrought Iron Railings. Gracious Formal Living And Dining Rooms, Alongside A Distinguished Library Adorned In Brazilian Redwood, And A Custom Chef's Kitchen, Anchor The Main Level With Timeless Sophistication. A Charming Breakfast Area And Expansive Family Room Seamlessly Extend To The Rear Garden Oasis, Creating An Effortless Setting For Both Intimate Gatherings And Entertaining. The Primary Retreat Is A Sanctuary Unto Itself, Featuring A Tranquil Sitting Area With A Custom Fireplace, His And Hers Walk-In Closets, And Accompanying His-And-Hers Ensuites. Five Additional Bedrooms Complete The Second Level. The Lower Level Offers An Exceptional Extension Of Living Space, Including A Nanny Suite, Oversized Recreation Room, Full Bar, Exercise Room With Ensuite Sauna, Cedar Closet, And A Walk-Up To The Gardens, With Ample Opportunity For Further Customization. Outdoors, The Estate Impresses With A 20' X 40' Pool, Multiple Lounging And Entertaining Areas, An Expansive Stone Terrace, And A Serene Koi Pond, All Enveloped By Lush Landscaping To Ensure Ultimate Privacy. A Rare And Distinguished Offering In One Of The City's Most Coveted Enclaves.

21 Fifeshire Road, Toronto
$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
$4,499,000
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
Start Your Search