St. Andrew-Windfields Real Estate

St. Andrew-Windfields Real Estate

Welcome to St. Andrew-Windfields, a hidden gem nestled in the heart of Toronto, Ontario. This prestigious neighborhood is renowned for its serene environment, lush green spaces, and an array of luxurious homes that cater to discerning buyers seeking both comfort and elegance.

St. Andrew-Windfields is characterized by its tree-lined streets and beautifully manicured lawns, creating an inviting atmosphere that feels like a retreat from the bustling city. The area boasts a mix of stunning detached homes, many of which showcase exquisite architectural designs, spacious interiors, and sprawling backyards—perfect for families and those who appreciate outdoor living.

Residents enjoy access to top-tier amenities, including some of Toronto's finest schools, making it an ideal community for families. The neighborhood is also conveniently located near the prestigious York Mills Collegiate Institute and Windfields Junior High School, providing educational excellence at every level.

For the outdoor enthusiast, St. Andrew-Windfields is home to several parks, including the picturesque Windfields Park and the expansive Edwards Gardens. These green spaces offer walking trails, picnic areas, and beautiful gardens, perfect for leisurely strolls or family outings.

Shopping and dining options abound, with the upscale Bayview Village Shopping Centre just a short drive away. Here, you can indulge in a variety of boutiques, gourmet restaurants, and cafes, ensuring that you have everything you need right at your fingertips.

With its perfect blend of tranquility, luxury, and community spirit, St. Andrew-Windfields is not just a place to live; it’s a lifestyle. Discover the charm of this remarkable neighborhood and make it your new home today!

Newest Listings in St. Andrew-Windfields

$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
$679,000
2 Beds ⋅ 2 Baths ⋅ C13825664 MLS ⋅ Bayview Mills BLDG.
Welcome to this modern, spacious, and thoughtfully designed condo townhouse in the upscale, safe, and sought-after Bayview & York Mills community, with access to top-tier TDSB schools. The main level offers bright, open-concept living and dining areas paired with an updated kitchen, perfect for entertaining or everyday comfort. A generous bedroom and built-in desk/den space provide flexible options for working from home or guest use. The fully finished, self-contained lower level adds versatility with a second full three-piece bathroom and Murphy bed, ideal as a private office, guest suite, or additional living area. Enjoy peace of mind with updated windows and doors (2024), refreshed exterior details including the roof and balcony, and two full bathrooms. The home is equipped with a built-in Bose surround sound system, wired data and cable connectivity, and a smart thermostat for modern convenience. A private garage plus compact driveway parking offers direct interior access to both the main level and basement, a rare feature in this community. Professionally managed and exceptionally maintained, this residence blends comfort, style, and practicality. Nestled in a quiet yet connected neighbourhood, you'll appreciate easy access to highways, transit, local amenities, and green spaces. A perfect balance of space, sophistication, and location-ready to move in and enjoy!

25 Proudbank Millway N/A, Toronto
$399,000
C13824024 MLS
FAT BASTARD BURRITO Business in NORTH YORK, ON is For Sale. Located at the busy intersection of York Mills Rd/Leslie St. Surrounded by Fully Residential Neighbourhood, Close to Schools, Highway, Offices, Banks, Major Big Box Store and Much More. Business with so much opportunity to grow the business even more. Yearly Net Sales: Approx $600,000, Rent: $7534/m including TMI & HST, Lease Term: Existing 5 years + Option to renew, Royalty: 8%, Advertising: 2%, Operating Since: July 2022.

808 York Mills Road Unit 7, 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
$799,000
3 Beds ⋅ 2 Baths ⋅ C13818214 MLS
A Rare Opportunity To Own A Ground-Floor 2-Bedroom + Den, 2-Bathroom Home With A Private Terrace, 2 Parking Spots, And A Locker In A Highly Convenient North York Location. Offering A Fantastic Combination Of Space, Functionality, And Outdoor Living, This Exceptional Home Is Perfect For Families, Professionals, First-Time Buyers, Downsizers, And Investors Alike. Enjoy The Convenience Of Ground-Floor Living With Your Own Private Terrace, Creating An Inviting Outdoor Extension Of The Home That Is Perfect For Relaxing, Entertaining, Or Enjoying Your Morning Coffee. The Versatile Den Provides Valuable Additional Space That Can Be Used As A Home Office, Study, Or Flex Room. Two Full Bathrooms Add Convenience, While 2 Parking Spaces And 1 Locker Provide The Parking And Storage Space That Today's Buyers Are Looking For. Ideally Located In North York, This Home Puts You Close To An Excellent Variety Of Restaurants, Cafes, Grocery Stores, Shopping, Schools, Parks, And Recreational Amenities. The Nearby Yonge Street Corridor Offers A Wide Range Of Dining And Everyday Conveniences, While Convenient Transit Options Provide Easy Access Throughout North York And The GTA. Major Roadways, Including Highway 401, Are Also Readily Accessible, Making Commuting And Getting Around The City A Breeze. Whether You're Looking For A Comfortable Home With Exceptional Outdoor Space, A Convenient Location Close To Everything, Or A Smart Investment Opportunity, 38 William Carson Cres #116 Offers An Outstanding Opportunity To Enjoy All That North York Has To Offer. Don't Miss This One!

38 William Carson Crescent Unit 116, Toronto
$2,150,000
2 Beds ⋅ 3 Baths ⋅ C13818172 MLS ⋅ The Antiquary BLDG.
Welcome to Suite 102 at 11 William Carson Crescent, The Antiquary. Nestled in a highly sought-after enclave, this beautifully appointed condominium with newly renovated common areas, party rooms, and elevators offers a rare blend of luxury and convenience. This oversized suite-the result of combining two units-spans an impressive 2,525 sq. ft. and features 5 walkouts to an expansive 1,000 sq. ft. terrace that looks onto a garden oasis overlooking a private ravine, the perfect setting for morning coffee or afternoon relaxation. A thoughtful split-bedroom plan offers two bedrooms, each with its own ensuite, plus a third washroom, providing privacy and comfort for all. The Private Dining Room, Den, and full Living Room round out the principal rooms, creating a refined living experience. Custom upgrades throughout include herringbone hardwood flooring, a custom fireplace mantle, and two separate walk-in closets in the Primary Bedroom. Also included are two parking spots (conveniently located nearest the elevator) and an oversized private locker (13' 6"). Residents enjoy exceptional building amenities, including 24-hour concierge, visitor parking, a guest suite, indoor swimming pool, fitness centre, party room, and sauna. With easy access to York Mills Subway and Highway 401, this is a rare opportunity in a truly prime location.

11 William Carson Crescent Unit 102, 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 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, 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
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