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 luxury living meets suburban charm. Nestled in the heart of North York, this vibrant community is known for its lush green spaces, top-tier schools, and a strong sense of community. With its tree-lined streets and beautifully manicured lawns, St. Andrew-Windfields offers an idyllic setting for families, professionals, and retirees alike.

The neighborhood boasts an array of amenities that cater to all lifestyles. Residents can enjoy the tranquility of nearby parks, such as the stunning Edwards Gardens, where you can stroll through breathtaking botanical displays or enjoy a peaceful picnic. For those who crave a bit more activity, the Don Valley Golf Course is just around the corner, providing a perfect retreat for golf enthusiasts.

St. Andrew-Windfields is also renowned for its excellent educational institutions, including top public and private schools, making it a desirable location for families seeking a nurturing environment for their children. The community is well-connected, with easy access to major highways and public transit, ensuring that downtown Toronto is just a short commute away.

For those looking to make St. Andrew-Windfields their home, there are a variety of stunning properties available for sale. From elegant single-family homes to luxurious estates, the real estate offerings here cater to diverse tastes and preferences. Each home is a testament to quality craftsmanship and design, providing the perfect backdrop for creating lasting memories.

Discover the charm and sophistication of St. Andrew-Windfields—where your dream home awaits!

Newest St. Andrew-Windfields Homes for Sale

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 $$$$ -- Over $300K in 2021-2023)****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 and the 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 Hardwood & 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 ⋅ 5 Baths ⋅ C14119282 MLS
One of the bigest lot on the Quiet Court! *This inviting detached two-storey home blends classic character with thoughtfully updated spaces. A striking curved staircase welcomes you inside, where 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, plus a wood-panelled office with built-in shelving. Upstairs, spacious bedrooms provide room to relax. The finished basement offers a large recreation area, saunna and jacuzi, while the backyard features a patio, 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
158 Owen Boulevard, Toronto
$3,500,000
6 Beds ⋅ 6 Baths ⋅ C14108984 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
15 Mellowood Drive, Toronto
$2,390,000
5 Beds ⋅ 4 Baths ⋅ C14105706 MLS
Prestigious St. Andrew-Windfields! Spacious 4+1 Bedroom, 4-Bath Family Home Situated On An Impressive Approx. 57 X 120 Ft Lot. Functional Layout Featuring Generous Living & Dining Areas, Family Room With Fireplace, And Eat-In Kitchen With Centre Island & Walk-Out To A Beautifully Landscaped Backyard. Primary Retreat With 5-Pc Ensuite & His/Her Closets. Finished Lower Level With Large Rec Room & Additional Bedroom. Double Garage & Tesla Charger. Excellent Location Close To Top Schools, Parks, Shopping, TTC, Bayview Village, York Mills & Hwy 401.

15 Mellowood Drive, Toronto
108 Yorkminster Road, Toronto
$4,650,000
6 Beds ⋅ 6 Baths ⋅ C14096276 MLS
Stunning Custom-Built Family Home In The Prestigious St. Andrew-Windfields neiboorhood. Offering over 7,200 Sq. Ft. Of Luxury Living Space. Sun Filled Living room oversees the front yard garden, connected to the spacious Dining room surrounded professional millwork and coffered ceiling. Featured Family room equipped with a fireplace and B/I Shelves, and overlooks the backyard Oasis. Chef inspired kitchen includes a large centre island, beautiful granite countertops and backsplash, top of the line appliances, Custom Kitchen Cabinetry, and a Built-in Pantry. The private office with Mahogany panelled wood walls. Classic Wrought iron Staircase with a skylight leads to the upper floor, which features a luxurious primary bedroom with a fireplace, sitting area, walk in dressing room and 6pc ensuite with heated floors. Four other bedrooms all with access to ensuites. The lower level Boasts an entertainment and relaxation paradise, Large Rec Room with Wet Bar, Exercise Rm, Red Wood Rack Wine Cellar, Home Cinema and Cedar Closet. Also an extra bedroom with 3pc Bath. Walk up to the backyard. Radiant Heated Floors on Main Floor & Basement. Minutes To Golf, Highway and Public Transit. Top tier Private & Public Schools, branding Shopping & Dining. An exceptional family home offering timeless craftsmanship, refined living, and an enviable address in one of Toronto's most prestigious neighbourhoods.

108 Yorkminster Road, Toronto
50 Owen Boulevard, Toronto
$3,960,000
5 Beds ⋅ 5 Baths ⋅ C14095920 MLS
**Motivated Sellers!!! )*Spacious Modern Art Deco (Aprox 6518Sf-Liv'g/Space ).**Gorgeous New Roof with snow melt system,2 Brand new 2nd floor bathroom and basement-Just Completed!! Newly renovated kitchen with Bosch & JennAir appliances!!Plus Heavy-Duty 4 Ton Lennox AC(2024)**Hi Demand Owen Blvd & **Heart of the neighbourhood**Hi Demand School Area, Clse To T.T.C& Hwy. Spectac Uniq Details & Finishes. This Property Boasts 60X180 Lot In Deep B/Yard Oasis!! Inground Concrete Pool (2024)+ Cabana(new roof 2024), New plumbing, new gas heating & filtration system, Chnge Rm,3 Pce, dedicated equipment room, Plus lush garden, Huge Safe Space For Childrens Play,***Definite Must See!!

50 Owen Boulevard, Toronto
110 Munro Boulevard, Toronto
$4,099,000
5 Beds ⋅ 7 Baths ⋅ C14093442 MLS
An elegant custom residence in prestigious St. Andrews, offering approximately 5,800 sq. ft. of total living space, including the finished lower level, on a beautifully landscaped 50 136 ft lot. A striking stone and brick exterior introduces spacious interiors featuring hardwood floors, crown mouldings, detailed millwork and multiple fireplaces. Designed for comfortable family living and entertaining, the main level offers formal living and dining rooms, a dedicated office and an expansive chef's kitchen featuring a Sub-Zero refrigerator, six-burner Wolf range, wall oven, microwave and large centre island. The adjoining family room overlooks the backyard, with walkout access to the deck for outdoor gatherings. Four generous upper-level bedrooms each feature a private ensuite and walk-in closet, including a spacious primary retreat with vaulted ceiling and six-piece ensuite. The finished walk-up lower level provides an expansive recreation room, guest bedroom with ensuite, exercise area and sauna. Recent updates include furnaces and air-conditioning systems installed in 2022,new skylights in 2026 with a transferable warranty. A double garage and private driveway complete the property. Enjoy an exceptional location, minutes from leading public and private schools, fine dining and upscale shopping, with convenient access to the Granite Club, Rosedale Golf Club and Toronto Cricket Club.

110 Munro Boulevard, Toronto
20 Mossgrove Trail, Toronto
$2,030,000
4 Beds ⋅ 4 Baths ⋅ C14087978 MLS
Beautifully maintained home nestled on a quiet, family-friendly street in one of Toronto's most desirable neighbourhoods. Bright, functional layout with spacious principal rooms, abundant natural light, and thoughtful updates throughout. The well-appointed kitchen flows seamlessly into the dining and living areas, creating an ideal space for everyday living and entertaining. Generous-sized bedrooms provide comfort and flexibility for growing families, professionals, or guests. Step outside to a private backyard perfect for relaxing, gardening, or hosting summer gatherings. Conveniently located close to top-rated schools, parks, walking trails, shopping, restaurants, transit, and major highways.

20 Mossgrove Trail, Toronto
13 Legacy Court, Toronto
$6,390,000
6 Beds ⋅ 8 Baths ⋅ C14032204 MLS
Welcome to 13 Legacy Court, a European-inspired estate on a quiet, prestigious cul-de-sac in St. Andrew-Windfields. Offering approximately 5,394 sq. ft. above grade and 3,111 sq. ft. of finished lower-level space, this residence features over 8,500 sq. ft. of total living space, 5+1 bedrooms and 8 bathrooms. Fully renovated on the main and upper floors, the home showcases premium materials and outstanding craftsmanship. The grand foyer features book-matched stone slabs, custom wainscoting and a sweeping curved staircase beneath a domed skylight. Engineered hardwood, coffered ceilings and finely crafted millwork enhance the formal living and dining rooms, private office and family room. The new gourmet kitchen offers custom cabinetry, an oversized waterfall island, two sinks, a generous pantry and brand-new Miele appliances: six-burner gas cooktop with griddle, built-in oven and speed oven, coffee maker, side-by-side refrigerator and freezer, and two dishwashers. The breakfast area overlooks the private backyard oasis. Five upper-level bedrooms offer comfort and privacy. The primary suite features a sitting area with fireplace, private balcony overlooking the pool, expansive custom walk-in closet and newly renovated spa-inspired ensuite with premium stone finishes, freestanding bathtub and designer fixtures. The lower level includes a recreation room, fireplace, custom bar, home theatre, fitness area, sauna, secondary kitchen and additional bedroom with ensuite. Walk-up access connects to the backyard. Mature trees, lush gardens and privacy hedges frame a resort-inspired oasis with an in-ground pool, integrated Jacuzzi, stone terraces, outdoor entertainment bar and poolside pavilion.A natural stone and brick exterior, grand circular driveway and three-car garage with a vehicle lift accommodating a fourth vehicle complete this estate.

13 Legacy Court, Toronto
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