St. Andrew-WindfieldsToronto / North YorkToronto
Toronto Area Property Listings
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53 33 Proudbank Millway Way in Toronto: St. Andrew-Windfields Condo Townhouse for sale (Toronto C12) : MLS®# C12348133
53 33 Proudbank Millway Way Toronto M2L 1P3 
$1,195,000Residential Condo & Other- Status:
- Active
- MLS® Num:
- C12348133
- Bedrooms:
- 4
- Bathrooms:
- 4
The Best Location In Toronto. Bayview & York Mills. Located Among Multi-Million Dollar Homes In The Prestigious Neighbourhood Of St. Andrew-Windfields. This 3 Bed & 4 Bath Stunning Home Is Nestled In One Of Toronto's Most Desired & Welcoming Communities On a Quiet (No Exit) Street. This Cozy Home Offers 3 Large Bedrooms Upstairs Plus a Finished Basement with Family Room, Office/Add'l Bedroom, Kitchen, & Bathroom. MANY Updates Include Newer Front Entry Door, Newer Washrooms, Hardwood Floors on Main Floor, A/C, Furnace, & Stainless Steel Appliances. California Shutters Through-Out, Stunning landscaping along the front walkway. This Premier Complex Offers Great Amenities. Condo Fees Include Outdoor Pool, Landscaping, Grass Cutting, Removal Of Leaves, & Convenience Of Being Close To 401, Great Shops, Bayview Village, Subway, Restaurants, Parks & Top Rated Schools (Harrison PS, Windfields & York Mills CI). More detailsListed by FOREST HILL REAL ESTATE INC.- ALEX PRASOULIS
- ILISTREALESTATE INC. BROKERAGE
- 1 (416) 856-5408
- info@ilistrealestate.ca
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11 Riderwood Drive E in Toronto: St. Andrew-Windfields House for sale (Toronto C12) : MLS®# C12345851
11 Riderwood Drive E Toronto M2L 2X4 OPEN HOUSE: Aug 23, 202502:00 PM - 04:00 PM EDTOpen House on Saturday, August 23, 2025 2:00PM - 4:00PMOPEN HOUSE: Aug 23, 202502:00 PM - 04:00 PM EDTOpen House on Saturday, August 23, 2025 2:00PM - 4:00PM
$2,490,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12345851
- Bedrooms:
- 5
- Bathrooms:
- 4
Beautiful Executive Family Home/Large Principal Rooms In The Bayview/Leslie/York Mills Area. 2 Storey Foyer With Marble Floors. Grand Living & Dining Rooms. 4 +1 Bedrooms, 4 Baths, Main Floor Office/Separate Entry. South Facing Lot. Manicured Front +(Private) Backyard. Steps To Prestigious Schools. Short Drive To Bayview Village/Shops At Don Mills/York Mills Gardens Plaza With Longos Supermarket. Close To Nygh, Granite Club, Donalda Golf & Country Club More detailsListed by RE/MAX IMPERIAL REALTY INC.- ALEX PRASOULIS
- ILISTREALESTATE INC. BROKERAGE
- 1 (416) 856-5408
- info@ilistrealestate.ca
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27 Junewood Crescent in Toronto: St. Andrew-Windfields House for lease (Toronto C12) : MLS®# C12345916
27 Junewood Crescent Toronto M2L 2C3
$7,980Residential Freehold- Status:
- For Lease
- MLS® Num:
- C12345916
- Bedrooms:
- 5
- Bathrooms:
- 7
Welcome to discover this extraordinary Georgina Revival hallmark. Quietly situated on a private enclave of the prestigious St. Andrew-Windfields neighborhood, this magnificent residence boasts approximately 6,348 sq ft above grade and features five (5) bedrooms, each with a full ensuite upstairs. The expansive central layout announces a formal entrance and graceful symmetry. Tasteful architectural refinements and recent upgrades throughout. An elegant circular stairwell, European oak panelling, splendid mirror walls, hand crafted vanities, and intricate beveled lead designs all mingling to create artistic and sensational aroma for the home. The main kitchen is equipped with a secondary kitchenette, offering a variety of cuisine options. Two sets of appliances plus a freezer in the lower level are all included. A wealth of sash windows and glass entrances, thoughtfully proportioned to provide abundant natural light. L-shape courtyard, lash backyard, and ample side yard provide a high level of privacy and comfort for garden gathering and family relaxation. A spectacular underground multi-purpose sport court and enormous game room is well-loved for year-round recreational activities. Extra large three-car garage, six additional ground parking spaces, and a basketball stand conveniently appointed at the north end of the building. Hot Water Tank owned. Partially furnished. The entire property and furniture presented are included, with the exception of the covered indoor pool wing, which is locked for safety. The location features a perfect proximity to top public and private schools, Granite Club, Sunnybrook Hospital, Hwy 401, golf courses, fine dinings and upscale shoppings. 27 Junewood Cres proudly enhances this exclusive community which is known for its sophisticated executive living and unparalleled social connectivity. More detailsListed by SOTHEBY'S INTERNATIONAL REALTY CANADA- ALEX PRASOULIS
- ILISTREALESTATE INC. BROKERAGE
- 1 (416) 856-5408
- info@ilistrealestate.ca
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114 Upper Canada Drive in Toronto: St. Andrew-Windfields House for lease (Toronto C12) : MLS®# C12346737
114 Upper Canada Drive Toronto M2P 1S4
$3,500Residential Freehold- Status:
- For Lease
- MLS® Num:
- C12346737
- Bedrooms:
- 4
- Bathrooms:
- 2
Prestigious St. Andrew-Windfields Detached Home in Prime Location!Featuring hardwood floors and renovated washrooms, this home offers a large deck and a sunny, spacious backyard. Close to shopping, restaurants, top schools, TTC, parks, and major highways. Welcome newcomers! More detailsListed by SUPERSTARS REALTY LTD.- ALEX PRASOULIS
- ILISTREALESTATE INC. BROKERAGE
- 1 (416) 856-5408
- info@ilistrealestate.ca
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19 Chieftain Crescent in Toronto: St. Andrew-Windfields House for lease (Toronto C12) : MLS®# C12347160
19 Chieftain Crescent Toronto M2L 2H3
$7,000Residential Freehold- Status:
- For Lease
- MLS® Num:
- C12347160
- Bedrooms:
- 5
- Bathrooms:
- 4
Welcome to 19 Chieftain Crescent, a charming 2-storey family home located in St. Andrew-Windfields, one of Toronto's most prestigious neighbourhoods. This 4-bedroom, 4-bathroom residence features a bright, spacious walk-out basement, freshly painted interiors, brand new flooring throughout the second floor, and beautifully renovated primary ensuite. Home office with built in cabinetry in mail floor. Generous sized bedrooms, tons of storage. The property boasts a curved double driveway, a 2-car garage, and a massive backyard perfect for entertainment. Surrounded by multi million dollar homes; many with private security regularly patrolling the streets. This property is situated within one of Toronto's top-rated school district, with easy access to Highway 401, shopping, dining, and more. More detailsListed by FOREST HILL REAL ESTATE INC.- ALEX PRASOULIS
- ILISTREALESTATE INC. BROKERAGE
- 1 (416) 856-5408
- info@ilistrealestate.ca
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82 Munro Boulevard in Toronto: St. Andrew-Windfields House for sale (Toronto C12) : MLS®# C12347516
82 Munro Boulevard Toronto M2P 1C4
$3,998,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12347516
- Bedrooms:
- 6
- Bathrooms:
- 6
Custom-built residence located in prestigious Owen School neighborhood on a quiet and highly sought-after street, this elegant home offers the perfect blend of grand entertaining spaces and comfortable family living. Grand foyer that flows into an open-concept living and dining area. 10-foot ceilings, detailed plaster crown mouldings, and rich hardwood floors, marble finishes, and a sleek modern powder room further enhance the sense of luxury, paneled library with French doors provides a refined space for a home office, study, or library/reading retreat. A mudroom/side door with direct access to an oversized double-car garage with level 2 EVC outlet. Large chef/s kitchen is a standout feature, spacious center island, granite countertops, bright breakfast area with a walk-out to a stone patio. Open to the inviting family room with custom millwork, gas fireplace overlooking the gardens. Luxurious primary suite complete with its own fireplace, six piece ensuite bathrooms, hardwood floors, massive recreation room with a wet bar, fireplace, space for games area, wall to wall windows and two walk-outs lead to a second stone patio. A teen/nanny suite with three-piece bathroom or make this your exercise room...Additional highlights: Andersen windows, a new roof (2024), hardwood on two levels, security/cameras, natural light throughout the home, extremely private landscaped gardens: extensive stone patios, exterior gas fireplace, gas BBQ, night lighting, sprinkler system. superb public (Owen St. Andrew's & York Mills CI) and private schools close by, easy walk to transit and subway. This turnkey residence offers outstanding space, exceptional flow, impeccable finishes, making it an exceptional choice for executive family living. More detailsListed by ROYAL LEPAGE/J & D DIVISION- ALEX PRASOULIS
- ILISTREALESTATE INC. BROKERAGE
- 1 (416) 856-5408
- info@ilistrealestate.ca
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187 19 Snowshoe Mill Way in Toronto: St. Andrew-Windfields Condo Townhouse for sale (Toronto C12) : MLS®# C12345226
187 19 Snowshoe Mill Way Toronto M2L 1T4
$979,000Residential Condo & Other- Status:
- Active
- MLS® Num:
- C12345226
- Bedrooms:
- 3
- Bathrooms:
- 3
Under $1M at Bayview & York Mills with two-car parking, three bedrooms and a private backyard. Full stop. Welcome to this rare, high-end townhome in the prestigious St. Andrews-Winfield pocket where luxury meets urban convenience. This corner end unit offers an open-concept living space drenched in natural light, with hardwood floors, pot lights and huge windows throughout. The spacious open concept living room flows effortlessly into the dining room / breakfast nook which is the perfect spot to start your mornings with a coffee and newspaper while looking out at your private backyard oasis. The large kitchen with stainless steel appliances is the perfect spot for showing off your culinary skills or taking out your phone to order uber eats if your culinary skills fail you. Did I mention the private backyard oasis with enough space to host anything from lazy Sunday brunches to late-night wine nights. All lawn maintenance and snow removal is taken care for you included in the maintence fees so just sit back and relax. Upstairs, you'll find three generous bedrooms, including a primary suite with an ensuite, walk-in closet, and windows that frame the seasons like art. The other two other bedrooms are light-filled retreats for family, guests, or your home office. The basement offers a finished rec room perfect for whatever your heart desires along with a laundry room and large storage room ready to be made yours. Location? You're minutes from York Mills subway, top-rated schools (including York Mills Collegiate), ravines, shops, restaurants, and the 401 and DVP. In other words: convenience without compromise. Bonus: New roof (2024), new windows (2022), freshly painted (2025), and totally move-in ready. More detailsListed by FOREST HILL REAL ESTATE INC.- ALEX PRASOULIS
- ILISTREALESTATE INC. BROKERAGE
- 1 (416) 856-5408
- info@ilistrealestate.ca
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68 Montressor Drive in Toronto: St. Andrew-Windfields House for sale (Toronto C12) : MLS®# C12341895
68 Montressor Drive Toronto M2P 1Z4
$2,650,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12341895
- Bedrooms:
- 4
- Bathrooms:
- 3
Presenting 68 Montressor Drive, an impeccably cared-for 4-bedroom residence offering over 70 ft of frontage, situated within the esteemed St. Andrew-Windfields neighbourhood. Beautifully landscaped front gardens offer a warm and welcoming first impression, hinting at the elegance that continues inside. The spacious foyer and graceful circular staircase provide a grand entrance, with a main floor office situated just off the foyer, offering serene views of the lush front gardens. Beyond, the open-concept living and dining rooms flow seamlessly, presenting an ideal arrangement for both elegant entertaining and daily family living. The renovated kitchen features high-end stainless-steel appliances and ample countertops, blending function and elegance. Central to the home and drenched in natural light is a stunning family room addition with large glass panels, warm wood accents, and a gas fireplace with stone surround, flowing seamlessly onto a second patio for effortless indoor-outdoor living. Upstairs, youll find four spacious bedrooms, each with lovely hardwood floors throughout. The updated primary bedroom is a peaceful retreat, featuring custom floor-to-ceiling wardrobes and a beautifully renovated ensuite bathroom. A second updated bathroom serves the other bedrooms, ensuring comfort and convenience for the entire family. The open-plan layout of the lower level offers incredible versatility, featuring an ultra-spacious rec room, with potential gym area or a fifth bedroom. The large, renovated laundry room is thoughtfully designed with built-in storage and new appliances. The private west-facing backyard offers a serene retreat, surrounded by mature trees and vibrant landscaping that feels like a gardeners dream. Further features include a side door entrance, W/O to a cedar deck with a B/I gas line for BBQs, and easy access to the attached two-car garage. Moments away from Owen PS, St. Andrew's MS & transit, the highway system, and upscale shopping and dining. More detailsListed by ROYAL LEPAGE REAL ESTATE SERVICES HEAPS ESTRIN TEAM- ALEX PRASOULIS
- ILISTREALESTATE INC. BROKERAGE
- 1 (416) 856-5408
- info@ilistrealestate.ca
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612 53 York Mills Road in Toronto: St. Andrew-Windfields Condo Townhouse for lease (Toronto C12) : MLS®# C12343015
612 53 York Mills Road Toronto M2P 1B6
$4,500Residential Condo & Other- Status:
- For Lease
- MLS® Num:
- C12343015
- Bedrooms:
- 3
- Bathrooms:
- 3
This luxury townhouse is situated in the highly sought-after Hoggs Hollow neighborhood, just a short walk to the York Mills TTC subway station for easy access to transit. Located at the intersection of York Mills and Yonge, enjoy proximity to top schools, shopping, dining, parks, and major highways. This 3-bedroom, 3-bathroom home offers over 1,000 sq ft of space with a rooftop terrace ideal for outdoor entertaining. Experience the convenience and lifestyle benefits of living in one of Toronto's most desirable communities. More detailsListed by CONDOWONG REAL ESTATE INC.- ALEX PRASOULIS
- ILISTREALESTATE INC. BROKERAGE
- 1 (416) 856-5408
- info@ilistrealestate.ca
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176 Fenn Avenue in Toronto: St. Andrew-Windfields House for lease (Toronto C12) : MLS®# C12338627
176 Fenn Avenue Toronto M2P 1X9
$4,950Residential Freehold- Status:
- For Lease
- MLS® Num:
- C12338627
- Bedrooms:
- 4
- Bathrooms:
- 4
Lovely South-Facing Detached Home In The Coveted St. Andrew's Neighbourhood. Steps Away From All The Best Schools In Toronto, Highways And Ttc. This Well-Loved, 2-Storey Home Is Charming And Full Of Character - The Perfect Place To Raise A Family. Main Floor Boasts High Ceilings, Lots Of Light And Crown Molding Throughout. Fireplace, Wainscotting And Two Piece Bathroom Adjacent To Family Room. Functional Second Floor Layout With Four Large Bedroom Laid With. And freshly painted. More detailsListed by HOMELIFE NEW WORLD REALTY INC.- ALEX PRASOULIS
- ILISTREALESTATE INC. BROKERAGE
- 1 (416) 856-5408
- info@ilistrealestate.ca
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38 Fifeshire Road in Toronto: St. Andrew-Windfields House for sale (Toronto C12) : MLS®# C12340461
38 Fifeshire Road Toronto M2L 2G6
$5,495,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12340461
- Bedrooms:
- 5
- Bathrooms:
- 5
Nestled on one of Toronto's most coveted streets, 38 Fifeshire Road offers an unparalleled opportunity to craft a bespoke masterpiece in the heart of the illustrious Bayview and York Mills enclave. Spanning nearly 1/2 an acre, this expansive ravine lot is a canvas of serenity and prestige, framed by lush greenery, mature trees, and the tranquil beauty of its natural surroundings. With exceptional frontage, depth, and breathtaking ravine vistas, this property is a dream for visionary architects and discerning homeowners. The existing residence, boasting nearly 5,000 square feet of well-appointed living space, provides a foundation of grandeur, yet the true allure lies in the lands potential. Imagine a custom-designed estate with sweeping outdoor terraces, infinity pools, or private gardens all tailored to your unique vision of luxury. Located just moments from Toronto's finest offerings, including Bayview Villages upscale shopping, elite private and public schools, gourmet dining, exclusive clubs, and seamless access to Highway 401 & DVP, this address marries tranquility with connectivity.38 Fifeshire Road is not merely a home its a legacy in the making, a rare chance to define timeless elegance on one of Toronto's most iconic streets. Seize this moment to build your dream. A rare legacy estate awaits! More detailsListed by HARVEY KALLES REAL ESTATE LTD.- ALEX PRASOULIS
- ILISTREALESTATE INC. BROKERAGE
- 1 (416) 856-5408
- info@ilistrealestate.ca
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2706 Bayview Avenue in Toronto: St. Andrew-Windfields House for sale (Toronto C12) : MLS®# C12330676
2706 Bayview Avenue Toronto M2L 1B9
$5,799,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12330676
- 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- ALEX PRASOULIS
- ILISTREALESTATE INC. BROKERAGE
- 1 (416) 856-5408
- info@ilistrealestate.ca
Data was last updated August 18, 2025 at 06:15 AM (UTC)