St Andrew-Windfields is a Toronto neighbourhood in North York. It includes York Mills community, and is located south of Highway 401. The central intersection in the area is Bayview Avenue and York Mills Road. There are many single family homes in the area, along with apartments and North York condos along Yonge Street.
Welcome to St Andrew-Windfields-York Mills
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32 Truman Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12) : MLS®# C12739266
32 Truman Road Toronto M2L 2L5 
$5,790,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12739266
- Bedrooms:
- 7
- Bathrooms:
- 11
Stunning 3-STOREY Transitional Estate with ELEVATOR in Prestigious St. Andrew-Windfields. Only seven years new, this AMENITY-RICH masterpiece showcases over 12,000 SF of refined living space (approx. 9,000 SF above grade + 3,000 SF lower level) on an impressive 71' frontage, offering UNMATCHED CURB APPEAL and a true LUXURY experience. The grand foyer introduces expansive principal rooms, designer finishes, plaster moldings, coffered ceilings, and elegant fireplace features that anchor warm, welcoming gatherings. The chef-inspired kitchen is a showpiece, equipped with TOP-OF-THE-LINE Miele APPLANCES, custom cabinetry, quartz surfaces, pot filler, radiant HEATED FLOORS, and a large island, complemented by a fully equipped SEPARATE WOK KITCHEN. The breakfast area opens seamlessly to the landscaped backyard featuring natural stone, a fully enclosed NEW GAZEBO, and a pool-sized lot. Multiple skylights drench the home in NATURAL LIGHT. The opulent primary suite offers a sitting area with Juliette balcony, lavish 6-piece ensuite plus an additional 2-piece inner ensuite, and a spacious walk-in closet. All additional bedrooms include private ensuites, walk-in closets, and hardwood floors. The AMENITY-PACKED LOWER LEVEL includes a sound-insulated home theatre, wine cellar, wet bar, steam & dry saunas, large recreation/party area, gym, and a full GOLF SIMULATOR with exercise space. Walk-out access creates a seamless indoor/outdoor flow. Additional highlights include a 4-STOREY GRAND STAIRCASE, ELEVATOR, 3-CAR GARAGE with 14' ceilings (CAR-LIFT suitable), whole-home audio, CCTV surveillance, 400-amp service, 20KW backup GENERATOR, RADIANT FLOOR HEATING, two furnaces, two A/C units, HRV-fresh air system, water softener, and built-in smart home systems. Located steps to renowned schools, shops, parks, and upscale amenities, this exceptional residence offers luxury living at its finest in one of Toronto's most coveted neighbourhoods. More detailsListed by RE/MAX REALTRON REALTY INC.- JARROD ARMSTRONG
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5 Bachelor Place in Toronto: St. Andrew-Windfields House for sale (Toronto C12) : MLS®# C12738680
5 Bachelor Place Toronto M2L 1W9
$2,999,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12738680
- Bedrooms:
- 4
- Bathrooms:
- 3
Total land--13885.43 sq.ft (ONE-OF-A-KIND)****An exceptional opportunity****This home lovingly maintained by the same family for over 50 years, a residence that balances retro charm with endless potential with over 3,000 sq. ft of living space across three levels + spacious basement level. A functional layout with expansive principal room sizes, spacious sidesplit design offers immediate livability with limitless potential for redevelopment for your dream home in the future. Whether you envision a full-scale renovation or the creation of a luxurious custom-built residence that provides a canvas for endless possibilities, the setting of the land provides an ideal canvas for your vision. Surrounded by mature trees and elegant estate homes, the property offers a rare sense of privacy and serenity. From the moment you walk in, the large foyer gives you a welcoming invitation, and a formal and sun-filled living room provides a large space for functionality, and the dining room is perfectly tucked next to the eat-in kitchen. Upper level, you will discover 3 generously sized bedrooms including a primary bedroom with own 4pcs ensuite. The family room serves as a serene retreatm featuring a wet bar, fireplace, an easy access to a private backyard, an ideal private place for your family. The location also provides seamless access to transit and major routes, making day-to-day living both easy and convenient, to top-rated schools, renowned private schools, Granite Club and Rosedale Golf Club, Edward Garden, hospitals and major highways & shoppings More detailsListed by FOREST HILL REAL ESTATE INC.- JARROD ARMSTRONG
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30 Bobwhite Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12) : MLS®# C12737752
30 Bobwhite Crescent Toronto M2L 2E1
$3,280,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12737752
- Bedrooms:
- 6
- Bathrooms:
- 5
Stunning home on a premium ravine lot in the prestigious St. Andrew-Windfields enclave. This elegant 5+1 bedroom, 5-bathroom residence offers over 4,700 sq. ft. above grade with a layout designed for both family comfort and sophisticated entertaining. Situated on a large premium 69 x 128 ft lot and widens To 113 Ft. In The Rear. Backing onto lush ravine views , it combines space, prestige, and natural beauty. Highlights include spacious principal rooms with Sitting Room, a main floor office, direct garage access, and a sun-filled family room overlooking the ravine. The primary retreat features a sitting area and oversized spa-inspired ensuite, creating a true private sanctuary. The finished lower level adds a versatile recreation room, extra bedroom, and abundant storage perfect for in-laws, guests, or a nanny suite.Additional features include central vacuum, irrigation system, and dual furnaces for year-round comfort. With a 2-car garage plus 4-car driveway, this home is ideally located near parks, trails, York Mills & Bayview, transit, Hwy 401, and top schools including Dunlace P.S. , Windfields M.S. and York Mills C.I. A rare opportunity to secure a ravine lot in one of Toronto's most prestigious neighbourhoods. More detailsListed by HOMELIFE LANDMARK REALTY INC.- JARROD ARMSTRONG
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2706 Bayview Avenue in Toronto: St. Andrew-Windfields House for sale (Toronto C12) : MLS®# C12736608
2706 Bayview Avenue Toronto M2L 1B9
$4,749,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12736608
- Bedrooms:
- 7
- Bathrooms:
- 9
Welcome to this exquisite custom-built luxury residence, a true masterpiece offering timeless elegance and modern convenience. Set on a rare 100-foot wide by 220-foot deep lot, this stunning home features over 5,586 sq. ft. of refined living space, plus an additional 2,636 sq. ft. finished walk-out basement that opens to a private Outdoor Oasis. Beyond the dramatic curb appeal and auto-gated entry, you'll find an impeccably designed home showcasing top-tier luxury finishes throughout. The grand two-storey foyer with skylight sets the tone for soaring ceilings, rich Brazilian cherry hardwood, and heated marble floors. The gourmet chefs kitchen is open to the breakfast area with walkout and overlooks the spacious family room complete with fireplace and custom built-ins. Additional highlights include an elevator, a main floor library, and five fireplaces throughout. Enjoy two lavish primary retreats, each with gas fireplaces, walk-in closets, and luxurious 5-piece ensuites. The lower level is ideal for entertaining and relaxation with a recreation room, gym, nanny or guest suite, roughed-in home theatre, and direct walkout to the expansive garden and pool. Additional features include two furnaces, A/C, and close proximity to top-rated schools, Bayview Village, York Mills Plaza, and Highway 401. More detailsListed by HOMEWISE REAL ESTATE and KINGSWAY REAL ESTATE- JARROD ARMSTRONG
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11 Montressor Drive in Toronto: St. Andrew-Windfields House for sale (Toronto C12) : MLS®# C12733676
11 Montressor Drive Toronto M2P 1Y9
$3,300,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12733676
- Bedrooms:
- 5
- Bathrooms:
- 4
Rare opportunity to acquire a premium ravine-backed property in the heart of St. Andrew-Windfields. Situated on an approximately 12,800 sq. ft. lot, this property offers exceptional privacy, a deep rear yard, and a natural ravine setting rarely available in this pocket. The existing home can be renovated to create a comfortable move-in-ready residence, or the property can be redeveloped to suit the buyer's vision. Ideal for end-users, builders, or investors seeking a prime lot with long-term upside. Surrounded by custom homes and mature landscaping, with easy access to top-rated schools, Bayview amenities, York Mills, and major transit routes. Opportunities to secure large ravine lots in this neighbourhood are extremely limited. Property being sold as is, where is. No representations or warranties. More detailsListed by CENTURY 21 REGAL REALTY INC.- JARROD ARMSTRONG
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27 Snowshoe Mill Way in Toronto: St. Andrew-Windfields Condo Townhouse for sale (Toronto C12) : MLS®# C12732440
27 Snowshoe Mill Way Toronto M2L 1T4
$1,238,000Residential Condo & Other- Status:
- Active
- MLS® Num:
- C12732440
- Bedrooms:
- 4
- Bathrooms:
- 3
Nestled in the Exclusive Community of Bayview Mills, You Will Find This Beauty! An Extraordinarily Spacious 2 Storey, 4 Bedroom Corner Unit Townhouse with a Coveted Double Car Garage and Enough Space to Park 4 Vehicles. A Sprawling 2299 Sq Ft Including Lower Level, This is the Perfect Condo Alternative. An Ideal Property for the Downsizer Looking for a Pied-A-Terre in the City or for a Growing Family Searching for Their Forever Home. 4 Generously Sized Bedrooms Upstairs and a Renovated 4 Piece Ensuite Off the Primary That Exudes Luxury. Floor to Ceiling Windows on the Main Floor and a Walk Out to Your Private Garden Create a Bright Space Flooded with Natural Light. Located Just South of the 401and Minutes Away from the Yonge Street Subway Line. Close to Excellent Schools. A Short Walk to Restaurants & Shopping at Bayview/York Mills and an Easy Commute to Downtown. Close to the Granite Club, Cricket Club and Donalda Club. Maintenance Fees Include Snow Removal, Front Landscaping, Water, Parking, Building Insurance and Common Elements. Your Very Own Outdoor Pool! Private and Secluded, An Oasis in the Heart of Midtown. Don't Miss This Hidden Gem More detailsListed by KELLER WILLIAMS PORTFOLIO REALTY- JARROD ARMSTRONG
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29 Junewood Crescent in Toronto: St. Andrew-Windfields House for sale (Toronto C12) : MLS®# C12733628
29 Junewood Crescent Toronto M2L 2C3
$5,980,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12733628
- Bedrooms:
- 5
- Bathrooms:
- 5
Striking Architectural Masterpiece Showcasing Exceptional Craftsmanship And Refined Finishes. Ideally Situated In The Coveted St. Andrew-Windfields Enclave. This Custom Estate Offers Nearly 9,000 Square Feet Of Sophisticated Living Space Where Modern Style Meets Elevated Comfort. Tucked Away On A Quiet Crescent With An Impressive 90-Foot Rear Lot Width Featuring A Natural Limestone Facade, Intricate Wood Detailing, Soaring Ceiling Heights, And A Heated Three-Car Garage. Appointed With World-Class Features And Thoughtful Amenities, Including A Private Elevator, An Elegant White Oak Library, Integrated Sonos Audio, And A Gourmet Kitchen Equipped With Premium Appliances, Servery, And Walk-In Pantry. The Sumptuous Primary Suite Serves As A Personal Sanctuary With A Private Balcony, Wet Bar, Dual Dressing Rooms, And A Spa-Inspired Marble Seven-Piece Ensuite. Abundant Skylights And Multiple Fireplaces Throughout Enhance The Ambiance And Invite Natural Light. The Walk-Up Lower Level Is Designed For Both Leisure And Entertaining, Offering A Home Theatre, Wine Cellar, Fitness Studio, Spa Area, Recreation Space, And A Separate Nanny's Quarters. Heated Flooring On This Level, Marble Flooring On The Main Floor, And Ensuite Baths For Every Bedroom Provide Consistent Luxury Throughout. The Private Backyard Retreat Rivals A Five-Star Resort, Complete With A Swimming Pool, Hot Tub, Stone Patio, Mature Landscaping, Putting Green, And An Exclusive Cabana. This Exceptional Residence Seamlessly Unites Contemporary Architecture With Timeless Opulence. More detailsListed by RE/MAX REALTRON BARRY COHEN HOMES INC.- JARROD ARMSTRONG
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11 Montressor Drive in Toronto: St. Andrew-Windfields House for sale (Toronto C12) : MLS®# C12733814
11 Montressor Drive Toronto M2P 1Y9
$7,300,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12733814
- Bedrooms:
- 7
- Bathrooms:
- 10
An exceptional opportunity to purchase a brand new, custom-built luxury home in the prestigious St. Andrew-Windfields neighbourhood, situated on a rare ravine-backed lot of approximately 12,800 sq. ft. This offering allows a buyer to acquire the property as a fully designed and approved new build, with all architectural plans, engineering, and approvals already completed and a reputable builder prepared to deliver the home. The approved design features over 7,600 sq. ft. of living space, thoughtfully planned to maximize scale, natural light, and the ravine setting. All major pre-construction work has been completed, including architectural design by Contempo Studio, HVAC and grading design, and building permit submission-providing a streamlined path from purchase to construction. Buyers benefit from significantly reduced timelines and risk compared to starting a custom build from scratch. The home design includes grand principal rooms, high ceilings, elevator provision, expansive outdoor terraces, and a backyard concept ideal for entertaining and enjoying the natural surroundings. Finishes may be customized within the builder's specifications, offering a balance of personalization and certainty. A rare chance to secure a brand new luxury residence without the typical delays associated with design, approvals, and permitting. Full drawings, specifications, and build details available upon request. More detailsListed by CENTURY 21 REGAL REALTY INC.- JARROD ARMSTRONG
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8 Orchid Court in Toronto: St. Andrew-Windfields House for sale (Toronto C12) : MLS®# C12734000
8 Orchid Court Toronto M2L 2X8
$2,390,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12734000
- Bedrooms:
- 6
- Bathrooms:
- 4
Gorgeous 5-bedroom executive home on a child safe cul-de-sac, conveniently located in the prestigious St. Andrew-Windfields community, minutes to Highway 401 and 404, walk to parks, shops, restaurants & close to all amenities.Grand skylite foyer opens to a high ceiling hallway flowing into the kitchen, breakfast area & custom-designed family room with built in wall units - both cozy & ideal for gathering. newer roof, furnace & air-cond system. most windows have been replaced. landscaped & treed backyard offers privacy. modern finished basement features office (or used as a bedroom), recreation & game room, media centre & wet bar - perfect for entertaining More detailsListed by RE/MAX CROSSROADS REALTY INC.- JARROD ARMSTRONG
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32 Scenic Mill Way in Toronto: St. Andrew-Windfields Condo Townhouse for sale (Toronto C12) : MLS®# C12734150
32 Scenic Mill Way Toronto M2L 1S5
$849,900Residential Condo & Other- Status:
- Active
- MLS® Num:
- C12734150
- Bedrooms:
- 2
- Bathrooms:
- 6
Welcome to this spacious townhome nestled in a quiet, established neighborhood surrounded by mature trees and gardens. This rarely offered large two-bedroom home features an oversized primary retreat and a bright, versatile layout designed for modern family living. Beautifully updated throughout with brand-new flooring and stairs, a new second-floor bathtub, a freshly finished basement washroom, new laundry appliances, and fresh paint from top to bottom. The walkout basement opens to a private, fully fenced yard, perfect for children, pets, or outdoor entertaining, and offers excellent POTENTIAL for a third bedroom, guest suite, or home office. Located within the sought-after catchment area of Harrison PS, Windfields MS, and York Mills CI, this home combines exceptional convenience with top-tier education. Minutes to Hwy 401, TTC, shops, parks, and York Mills Arena-everything your family needs is right at your doorstep. BBQs Allowed, ample visitor parking, outdoor swimming pool, and meticulously landscaped grounds. More detailsListed by FIRST CLASS REALTY INC.- JARROD ARMSTRONG
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2638A Bayview Avenue in Toronto: St. Andrew-Windfields House for sale (Toronto C12) : MLS®# C12724848
2638A Bayview Avenue Toronto M2L 1B7
$2,850,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12724848
- Bedrooms:
- 4
- Bathrooms:
- 4
Show Your Most Discerning Clients This Rarely Offered And Most Coveted Executive Townhome At Bayview & Fifeshire! Situated In The Prestigeous And Sought After St. Andrew-Windfields Neighbourhood, This Stunning & Exquisite 3 Bed (Was 4) And 4 Bath Home Boasts 3800 SF Of Living Space & Over 700 SF Of Terraces, Balconies & Outdoor Living Spaces. Meticulously Designed With Attention To Detail And An Unwavering Commitment to Quality Craftsmanship With More Than $300,000 In Custom Upgrades & Finishes, This One-Of-A-Kind Offering Features A Private Elevator Providing Access To All Levels, 10' Ceilings, High-End Hardwood Flooring, A Chef-Inspired Gourmet Kitchen With Custom Cabinetry, An Over-Sized Island, Built-In Pantry, Integrated Appliances Including Sub-Zero Fridge, Bluesta Gas Stove, 2 Wine Fridges, Quartz Countertops & Backsplash And A Walk-Out To A Private, West-Facing Terrace. Coffered Ceilings Effortlessly Connect The Kitchen With The Main Floor Family Room Featuring Panelled Walls, Gas Fireplace And A Walk-Out To The Terrace. Retreat Upstairs To A Primary Bedroom Oasis With An Extensive Walk-In Closet, Fireplace, Private Balcony And A 5-Pc Spa-Like Ensuite That Includes A Glass Shower And Steam Bath, His & Her Vanity, Jacuzzi, Radiant Floor Heating & A 2-Sided Fireplace. The Second Floor Also Features A Spacious Yet Cozy Family Room/Study. Third Floor Is Enhanced With A Second Primary Bedroom With 4-Pc Ensuite, Large Walk-In Closet And A Sundeck, A The Third Bedroom That Has Its Own 4-pc Ensuite & Walk-In And A Spacious Laundry Room With Sink And Custom Built-In Cabinets. The Top Floor, While Having Additional Storage Rooms & Skylights, Leads You To A Beautiful 397 SF West-Facing Rooftop Terrace With 1" Thick Porcelain Tiles, BBQ Gas Hook-Up & Water Bib. Lower Level Has An Additional Bedroom, Mudroom And Direct Access To The Garage.Your Sanctuary In The Heart Of The City Located Just Steps To Parks, Retail, Transit,Top-Rated Schools And Mere Mins To Hwy 401. More detailsListed by HARVEY KALLES REAL ESTATE LTD.- JARROD ARMSTRONG
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60 Hopperton Drive in Toronto: St. Andrew-Windfields House for sale (Toronto C12) : MLS®# C12721238
60 Hopperton Drive Toronto M2L 2S6
$1,699,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12721238
- Bedrooms:
- 4
- Bathrooms:
- 3
Welcome to 60 Hopperton Drive - a beloved family home, lived in by the same family since 1973, offered now for the first time. Nestled on a generous lot in the prestigious St. Andrew-Windfields enclave of North York, this property presents exceptional flexibility: move in now with minor renovations, or capitalize on the lot's potential with a full renovation or brand-new build. Great for Builders & Renovators! Located near excellent schools: Dunlace P.S. (French Immersion), Windfields J.H.S. & York Mills Collegiate. Steps away from Dunlace Park, Tennis Club & the Silver Hills Bus Stop to take you downtown! Short drive to 401 & exclusive Bayview Village. This is a rare opportunity to craft your dream residence in one of North York's most desirable neighbourhoods. More detailsListed by SAGE REAL ESTATE LIMITED- JARROD ARMSTRONG
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- 1 (416) 457-1722
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Data was last updated February 2, 2026 at 01:15 AM (UTC)
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