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

132 York Mills Road, Toronto
$2,895,000
5 Beds ⋅ 6 Baths ⋅ C14166246 MLS
A rare opportunity in prestigious York Mills: a beautifully maintained and extensively upgraded detached home on a generous 50' x 125' lot. Thoughtful improvements enhance comfort, style and everyday function, including a newly redone driveway (2022-24) with easy access, turnaround and generous parking; new landscaping, privacy hedging, rebuilt front steps, refreshed porch, stone walkways, and new front and rear doors. The renovated main-floor family room (2021) features a stone feature wall, electric fireplace, built-ins and an added centre window for abundant natural light. The primary ensuite and basement were also renovated in 2021, while all second-floor bedrooms and bathrooms were freshly painted in 2026. South-facing triple-pane windows (2024), upgraded attic/roof insulation (2021), new furnace and air conditioning (2021), and updated lighting (2026) provide added comfort and efficiency. The private backyard extends the living space with a new deck, gazebo, shed and basketball court, which can be converted to a hockey rink in winter. The basketball hoop, removable court tiles and protective netting are all included, offering exceptional added value for year-round recreation. Ideally located in the sought-after Bridle Path-Sunnybrook-York Mills area, close to York Mills Subway, TTC, shopping, parks, schools, the Granite Club and major highways. A truly special home offering substantial improvements, exceptional functionality and outstanding value.

132 York Mills Road, Toronto
110 Upper Canada Drive, Toronto
$2,380,000
6 Beds ⋅ 5 Baths ⋅ C14162074 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
67 Munro Boulevard, Toronto
$1,898,000
4 Beds ⋅ 2 Baths ⋅ C14158978 MLS
One of the lowest prices to be found in the Bayview/Yorkmill area, take advantage of this rare opportunity to own a 3 bedroom detached table land bungalow in this prestigious and highly desirable neighborhood. Surrounded by luxury multi-million dollar customized homes, top-ranked schools, premium transit access, major highways, and beautiful parks. Plenty of renovation potential: you can live in or customize your dream home!

67 Munro Boulevard, Toronto
88 Yorkminster Road, Toronto
$3,999,000
6 Beds ⋅ 7 Baths ⋅ C14155620 MLS
Sun-Filled, Renovated Custom Residence In A Prestigious Neighbourhood! Soaring 2-Storey Skylight Foyer & 10' Ceilings On Main. Gleaming Hardwood Floors Throughout Main & 2nd Levels. Spacious Gourmet Kitchen W/ Large Breakfast Area, Plus Main Flr Family Rm & Private Library/Office. 5 Generous Bdrms-Each W/ Its Own Ensuite Bath! Finished Lower Level Boasts Rec/Games Rm & Nanny Suite. 3-Car Garage Equipped W/ Tesla Level 2 Charger. Resort-Style Backyard W/ Professional Landscaping & Pool W/ Waterfall!

88 Yorkminster Road, Toronto
3 Legacy Court, Toronto
$4,750,000
5 Beds ⋅ 6 Baths ⋅ C14142594 MLS
Stunning Custom Residence, Windermere Homes Built On A Quiet Exclusive Cul-De-Sac In Prestigious Family-Friendly Neighbourhood of St. Andrew-Windfields. 187' Of Frontage, Soaring Ceilings, Crown Moulding, Integrated Speakers, And Luxurious Finishes Throughout. Generously-Sized Principal Rooms Overlooking The Serene Rear Rock Garden Set Against A Lush Verdant Landscape. Open Concept Gourmet Kitchen With Breakfast Area And Family Room Features Custom Finishes, Cathedral Ceiling And Sun-Drenched Interior With Walkouts To The Sprawling Side Garden. The Tranquil Primary Retreat Features Ante-Room Entrance, Vaulted Ceiling, Sitting Area With Custom Fireplace, Walk-In Closet, And Lavish 8-Piece Ensuite With Spa-Like Amenities. Three More Bedrooms With Ensuites Plus Convenient Laundry Complete The 2nd Floor. The Lower Level Offers A Sprawling Rec Room With Fireplace Plus Exercise Room With 3-Piece Ensuite And Steam Shower, And Nanny Suite. The Impeccably Maintained Interior Is Elevated Even Further By The Residence's Stunning Curb Appeal - Custom Stucco Exterior And Refined Architecture Set Within An Exclusive Lot Featuring 187.99' Frontage With Mature Trees, Manicured Lawns And Custom Landscaping Including Water Feature And Two-Level Stone Terrace. Conveniently Located Within Minutes Of Hwy 401, Top-Rated Golf, Renowned Public And Private Schools, Granite Club, High-End Shops And Eateries.

3 Legacy Court, Toronto
21 Heathcote Avenue, Toronto
$2,999,999
4 Beds ⋅ 4 Baths ⋅ C14142064 MLS
Exceptional Family Home in Prime St. Andrews-WindfieldsIdeally situated on a premium 100 x 125 ft corner lot in the highly prestigious St. Andrews-Windfields neighborhood, this elegantly renovated family residence offers an unmissable opportunity.Offering 3,317 sq ft of total fine living space (2,185 sq ft above grade plus a 1,132 sq ft finished basement), the home is thoughtfully designed for both refined living and effortless entertaining. The spacious living room flows seamlessly into a gourmet kitchen featuring a central island, granite countertops, and premium stainless steel appliances. Highlights include a generous primary retreat along with abundant, light-filled living areas throughout.Surrounded by top-tier schools, lush parks, and convenient shopping at Bayview/York Mills, this beautiful property combines unmatched convenience with timeless charm. A must-see!

21 Heathcote Avenue, Toronto
36 Medalist Road, Toronto
$2,700,000
7 Beds ⋅ 4 Baths ⋅ C13794274 MLS
Exceptionally rare 73 feet of frontage on a deep ravine 137 ft. lot with significant table land featuring a Classic red-brick 6 bedroom family home on a lush, private lot in coveted St. Andrews. This beautiful property is adorned with perennial gardens, mature trees, and plenty of room to grow and play. The sunny eat-in kitchen and elegant dining room offer park-like private garden views. Family-friendly features include a bright and spacious living room to accommodate your whole family and friends, fully covered front porch with access to the garage, side entrance attached to main floor laundry and mud room, finished basement with a 7th bedroom, large recreation room with high ceilings and exceptional storage and functionality throughout. Leafy Medalist Road offers wide boulevards between street and sidewalk for both safety and beauty, with close proximity to parks, top public and private schools and clubs. Within minutes you can reach Bayview Village, York Mills Subway Station, be on the highway for access to cottage country or the airport, York Mills, Tournament Park, Granite Club, Cricket Club, or walk to York Mills Plaza for Baskin-Robbins/Shoppers Drug Mart/Metro & Dineen Coffee - or simply stay home to enjoy your peaceful backyard overlooking on St. Andrews Park in this idyllic and family-friendly community.

36 Medalist Road, Toronto
67 Montressor Drive, Toronto
$4,990,000
5 Beds ⋅ 7 Baths ⋅ C14126312 MLS
An exceptional custom-built French Chateau in coveted St. Andrew-Windfields, offering approximately 7,500 sq. ft. of luxurious living space. Soaring ceilings, expansive windows, elegant millwork and sophisticated finishes create a striking first impression. The showpiece kitchen features custom cabinetry, premium appliances, a 43" La Cornue range, built in coffee machine, oversized centre island and separate spice kitchen.Four spacious bedrooms each offer a private ensuite, while the primary retreat features his-and-hers walk-in closets, a private balcony and spa-inspired ensuite. The impressive walkout lower level is designed for entertaining with heated floors, a glass-enclosed gym, home theatre, wet bar, recreation area and nanny/in-law suite. Complete with smart-home automation, built-in sound, heated driveway and garage, and three gas fireplaces. Ideally located near Toronto's top private schools, golf clubs, parks and the conveniences of Yonge & York Mills. *See feature sheet*

67 Montressor Drive, Toronto
37 Shouldice Court, Toronto
$1,890,000
5 Beds ⋅ 6 Baths ⋅ C14124534 MLS
****CITY--PERMITTED--FULL--INTERIOR--RENOVATION(SPENT $$$ -- approximately $300K in 2021-2023 as per seller)***Seeing is believing***Nestled on a quiet cul-de-sac & BACKING TO Dunlace Park! - this luxuriously renovated home offers 4 spacious bedrooms, total 6 washrooms, and a 2-car garage, with a desirable west-facing backyard providing excellent privacy & comfort. Step inside to a bright, open concept interior designed for both everyday living and effortless entertaining. The spacious & modern interior living room overlooks open-views, the frontyard and dining room overlooks the serene backyard and provides direct access to a covered-patio for hosting. The modern kitchen is both functional and inviting, featuring centre island, ample storage, under-mount lighting and stainless steeles appliances, and a window that fills the space with natural light. The spacious primary bedroom offers a beautifully updated 5-piece ensuite, large walk-in closet. The 2nd primary bedroom provides a 3-piece ensuite for privacy. The finished basement adds even more versatility, featuring an expansive family room with a fireplace and large windows. The recreation room offers versatility for a bedroom or open family gathering with a 3-piece ensuite, designed with flexibility in mind, this home is ideal for growing family or multi-generational living. Conveniently located to North York General Hospital, Highway 401/DVP and Top-Ranked Schools, Dunlace PS, Windfield MS and York Mills Ci & Close to Renowned private schools close by -- 2021-2023 Expansive-Permitted Reno'd Features:Expanded Living Space,Newer Insulation,Enlarged/Newer Windows,Newer Furance,Newer Cac,Newer Roof Shingle,Newer 200Ams Elc Breaker,Newer U/G Sprinkler,Newer EV Charger,Newer Kit W/S-S Appl,Cabinet,Newer Washrms,Newer Hardwd/Laminate Flrs,Newer Pot Lightings,Newer Drs/Main Dr/Added Interior Dr(Fm Garage to Inside) & More!-Note : Full lot size 40.47 ft x 99.72 ft x 115.93 ft x 137.43 ft as per Geowarehouse(Irreg-Shaped)

37 Shouldice Court, Toronto
24 Tullamore Drive, Toronto
$2,490,000
6 Beds ⋅ 6 Baths ⋅ C14119282 MLS
One of the bigest house and lot in the Quiet Court! *blends classic character with thoughtfully updated spaces. A striking curved staircase welcomes you inside, 2 stair lead to finished basement, generous living and dining rooms offer an elegant setting for entertaining. The renovated kitchen features white cabinetry, stainless steel appliances, ample counter space and a bright breakfast area overlooking the backyard. Enjoy the warmth of a separate family room with exposed ceiling beams and fire place, plus a wood-panelled office with built-in shelving. spacious bedrooms provide room to relax. The finished basement offers a large recreation area, saunna and jacuzi, while the backyard features a Cabana, mature trees and heated outdoor pool. An attached double garage completes this appealing North York home. Explore the photos and 3D tour to appreciate the layout and possibilities.

24 Tullamore Drive, Toronto
21 Don Ridge Drive, Toronto
$7,495,000
7 Beds ⋅ 7 Baths ⋅ C14118410 MLS
Set On A Spectacular Ravine Lot, 21 Don Ridge Is A Remarkable Custom Residence Designed And Built By Renowned Architect Lorne Rose. A Refined Expression Of Timeless Architecture, Pairing An Elegant Palette With Elevated Interiors, 10ft Ceilings And Impressive Wainscotting And Millwork Throughout, Plus Generously Proportioned Principal Rooms For Everyday Living And Entertaining. A Sun-Filled Main Floor Office/Study Offers The Perfect Work-From-Home Retreat. The Kitchen Anchors The Home With Custom Cabinetry, Sub-Zero And Wolf Appliances And A Large Centre Island With Butler's Pantry. The Primary Retreat Overlooks The Rear Grounds, With A Statement Gas Fireplace, Custom Built-Ins, His-And-Hers Walk-In Closets And A Spa-Like Ensuite. Heated Floors Run Throughout, And The Lower Level Features A Temperature-Controlled Wine Cellar. 5 Bedrooms, 7 Bathrooms & A 3-Car Heated Garage. Mature Landscaping Surrounds A Private Heated Pool. Moments To Top Private Schools, TTC And Rosedale Golf Club.

21 Don Ridge Drive, Toronto
62 Wimpole Drive, Toronto
$4,498,000
5 Beds ⋅ 6 Baths ⋅ C14114480 MLS
Architecturally Distinct Residence Situated On An Exceptional 128.75 x 159.17 Ft Treed Lot In A Prestigious And Highly Sought-After Enclave. This Remarkable Split-Level Home Presents A Rare Opportunity For Buyers Seeking Space, Privacy, And True Architectural Character.Dramatic Ceiling Heights, Expansive Skylights, And Walls Of Windows Fill The Home With Natural Light, Creating A Bright And Airy Atmosphere Throughout. Elegant White Brick Accents, Rich Hardwood Floors, And Custom Railings Define The Interior's Timeless Design. Generous Principal Rooms Offer Outstanding Flow For Both Everyday Living And Entertaining, Enhanced By Multiple Fireplaces And Inviting Gathering Spaces.The Bedroom Level Provides Comfortable And Private Accommodations, Including A Well-Appointed Primary Retreat With Walk-In Closet. Updated Bathrooms Add A Polished Contemporary Touch While Maintaining The Home's Refined Aesthetic.The Finished Lower Level Adds Exceptional Versatility Featuring A Large Recreation Area, Custom Wet Bar Ideal For Entertaining, Dedicated Fitness / Yoga Studio With Mirrored Walls, And A Bright Nanny Room With Ample Storage.Private Driveway And Expansive Backyard Setting Complete This Exceptional Property. Ideally Located Near Top-Rated Schools, Parks, And Outstanding Amenities.A Rare Offering Combining Architectural Identity, Exceptional Lot Size, And Enduring Appeal.

62 Wimpole Drive, Toronto
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