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St. Andrew-Windfields, Toronto, ON Luxury Homes

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With Square Yards Canada, you can find your dream luxury homes for sale in St. Andrew-Windfields. Explore your options from condo apartments, condo townhouses, detached houses, semi detached homes posted by agencies/owners who provide spacious and luxurious amenities in luxury houses for sale in St. Andrew-Windfields

Last Updated: March 25, 2026

1 Photos

48 Silvergrove Road St. Andrew-Windfields, Toronto, ON MLS® C12803436

Residential Freehold (Detached)

$4988000.0

6 +6 Beds
6 Baths
5000 + sq-ft

MAGNIFICANT LARGE LOT in highly sought after prestigious neighbourhood. Almost HALF-ACRE lot (125' x 184') of 23,000 sq ft in Bayview St. Andrew-Wind

39 Photos

15 Fairmeadow Avenue, Toronto, ON , MLS #C12908050 , Image - 1

15 Fairmeadow Avenue St. Andrew-Windfields, Toronto, ON MLS® C12908050

Residential Freehold (Detached)

$3888000.0

4 +1 Beds
6 Baths
3500-5000 sq-ft

Welcome To This Exceptional Executive Home In The St Andrew-Windfields Neighbourhood! This Impeccable Over 6,200 Sq Ft Home Impresses From The Moment

44 Photos

67 Montressor Drive N, Toronto, ON , MLS #C12208553 , Image - 1

67 Montressor Drive N St. Andrew-Windfields, Toronto, ON MLS® C12208553

Residential Freehold (Detached)

$5599000.0

4 +1 Beds
7 Baths
5000 + sq-ft

Feng Shui Certified!! Welcome to 67 Montressor Drive, An Extraordinary Custom-Built French Chateau in St.Andrew-Windfields Toronto's Sought After Enc

39 Photos

32 Truman Road, Toronto, ON , MLS #C12739266 , Image - 1

32 Truman Road St. Andrew-Windfields, Toronto, ON MLS® C12739266

Residential Freehold (Detached)

$5790000.0

7 Beds
11 Baths
5000 + sq-ft

Stunning 3-STOREY Transitional Estate with ELEVATOR in Prestigious St. Andrew-Windfields. Only seven years new, this AMENITY-RICH masterpiece showcase

Pre-Construction

Lily at Crosstown

844 Don Mills Road, North York, Toronto

From $573,990 - $1,358,990

Project Info

2 Buildings
220 Units
Condos

Property Mix

Studio(2)
1 Bed(95)
2 Bed(79)
3 Bed(44)

Developer:Aspen Ridge Homes

40 Photos

42 Foursome Crescent, Toronto, ON , MLS #C11952601 , Image - 1

42 Foursome Crescent St. Andrew-Windfields, Toronto, ON MLS® C11952601

Residential Freehold (Detached)

$4688000.0

Price drop by 28.9%

4 +1 Beds
7 Baths
3500-5000 sq-ft

Spectacular Bayview & Yorkmills Masterful Customized Residence Designed By Famous Architect Richard Wengle. This French Transition Mansion Nestled in

31 Photos

40 Old Colony Road, Toronto, ON , MLS #C12223199 , Image - 1

40 Old Colony Road St. Andrew-Windfields, Toronto, ON MLS® C12223199

Residential Freehold (Detached)

$6995000.0

6 +1 Beds
10 Baths
5000 + sq-ft

Nestled Within Bayview Gardens Most Iconic Street - Old Colony Road. This Magnificent Residence Boasts A 100' Frontage And Over 12,000 SqFt Of Living

42 Photos

103 Old Colony Road, Toronto, ON , MLS #C12795056 , Image - 1

103 Old Colony Road St. Andrew-Windfields, Toronto, ON MLS® C12795056

Residential Freehold (Detached)

$18000000.0

5 +1 Beds
11 Baths
5000 + sq-ft

Architecturally Significant New Build On Outstanding Pie Shaped Tennis Court And Pool Lot. New Residence Spanning An Impressive 21,000 Sf Of The Most

33 Photos

29 Junewood Crescent, Toronto, ON , MLS #C12733628 , Image - 1

29 Junewood Crescent St. Andrew-Windfields, Toronto, ON MLS® C12733628

Residential Freehold (Detached)

$5980000.0

4 +1 Beds
5 Baths
5000 + sq-ft

Striking Architectural Masterpiece Showcasing Exceptional Craftsmanship And Refined Finishes. Ideally Situated In The Coveted St. Andrew-Windfields En

Pre-Construction

The Clove Condos

2 East Mall Cres, Toronto

From $440,990

Project Info

1 Building
606 Units
Condos

Property Mix

Studio(32)
1 Bed(379)
2 Bed(127)
3 Bed(68)

Developer:Mattamy Homes, QuadReal Property Group

41 Photos

82 Munro Boulevard, Toronto, ON , MLS #C12869946 , Image - 1

82 Munro Boulevard St. Andrew-Windfields, Toronto, ON MLS® C12869946

Residential Freehold (Detached)

$3885000.0

5 +1 Beds
6 Baths
3500-5000 sq-ft

Custom-built residence located in prestigious Owen School neighborhood on a quiet and highly sought-after street, this elegant home offers the perfect

50 Photos

72 Lord Seaton Road, Toronto, ON , MLS #C12848578 , Image - 1

72 Lord Seaton Road St. Andrew-Windfields, Toronto, ON MLS® C12848578

Residential Freehold (Detached)

$5589900.0

5 +2 Beds
8 Baths
5000 + sq-ft

Luxurious Detached Home in Prestigious York Mills / St. AndrewsNestled in the highly sought-after York Mills / St. Andrews neighbourhood, this excepti

40 Photos

38 Fifeshire Road, Toronto, ON , MLS #C12818298 , Image - 1

38 Fifeshire Road St. Andrew-Windfields, Toronto, ON MLS® C12818298

Residential Freehold (Detached)

$5195000.0

4 +1 Beds
5 Baths
3000-3500 sq-ft

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

50 Photos

15 Silvergrove Road, Toronto, ON , MLS #C12811824 , Image - 1

15 Silvergrove Road St. Andrew-Windfields, Toronto, ON MLS® C12811824

Residential Freehold (Detached)

$3498000.0

4 +2 Beds
5 Baths
3000-3500 sq-ft

Luxury Living Meets Ravine Serenity in Prestigious St. Andrew-Windfields. A masterfully reimagined residence blending nearly 5,000 sq ft of refined li

37 Photos

113 Lord Seaton Road, Toronto, ON , MLS #C12186620 , Image - 1

113 Lord Seaton Road St. Andrew-Windfields, Toronto, ON MLS® C12186620

Residential Freehold (Detached)

$2498000.0

Price drop by 28.6%

5 Beds
4 Baths
3000-3500 sq-ft

Situated on a 70 x 110 ft. (7,700 sq ft) flat, premium lot in the prestigious St. Andrew-Windfields' enclave (Bayview/Yonge & York Mills), this except

39 Photos

62 Wimpole Drive, Toronto, ON , MLS #C12781094 , Image - 1

62 Wimpole Drive St. Andrew-Windfields, Toronto, ON MLS® C12781094

Residential Freehold (Detached)

$5500000.0

4 +1 Beds
6 Baths
3000-3500 sq-ft

Architecturally Distinct Residence Situated On An Exceptional 128.75 x 159.17 Ft Treed Lot In A Prestigious And Highly Sought-After Enclave. This Rema

28 Photos

15 Farrington Drive, Toronto, ON , MLS #C12779088 , Image - 1

15 Farrington Drive St. Andrew-Windfields, Toronto, ON MLS® C12779088

Residential Freehold (Duplex)

$3558000.0

3 +1 Beds
4 Baths
2000-2500 sq-ft

Welcome To 15 Farrington Dr A Beautifully Renovated Family Home Situated On A Prime Lot In One Of Toronto's Most Coveted Enclaves. This Spacious Resid

36 Photos

48 Wimpole Drive, Toronto, ON , MLS #C12700656 , Image - 1

48 Wimpole Drive St. Andrew-Windfields, Toronto, ON MLS® C12700656

Residential Freehold (Detached)

$7800000.0

5 +2 Beds
9 Baths
5000 + sq-ft

Welcome Home to 48 Wimpole Drive, a breathtaking, freshly renovated home nestled on a gated, estate-sized lot in the prestigious St. Andrews neighborh

39 Photos

4 Fifeshire Road, Toronto, ON , MLS #C12476750 , Image - 1

4 Fifeshire Road St. Andrew-Windfields, Toronto, ON MLS® C12476750

Residential Freehold (Detached)

$9790000.0

5 +1 Beds
7 Baths
5000 + sq-ft

***Magnificent***chateau-inspired***an exclusive-gated entrance & circular driveway lead to the L-U-X-U-R-Y grand residence on a beautiful 100ftx206ft

40 Photos

18 Heathcote Avenue, Toronto, ON , MLS #C12121819 , Image - 1

18 Heathcote Avenue St. Andrew-Windfields, Toronto, ON MLS® C12121819

Residential Freehold (Detached)

$5980000.0

Price drop by 13.1%

5 +1 Beds
8 Baths
5000 + sq-ft

Location! Location! Location! York mills & Bayview area! Welcome home to Fabulous & Elegant Custom build Family residence nestled on Prized Heathcote

40 Photos

11 Vernham Avenue, Toronto, ON , MLS #C12536768 , Image - 1

11 Vernham Avenue St. Andrew-Windfields, Toronto, ON MLS® C12536768

Residential Freehold (Detached)

$3498800.0

5 +1 Beds
7 Baths
5000 + sq-ft

Discover an exceptional opportunity at 11 Vernham Avenue, a custom-built estate offering the best value in one of North York's most prestigious neighb

49 Photos

26 Danville Drive, Toronto, ON , MLS #C12612106 , Image - 1

26 Danville Drive St. Andrew-Windfields, Toronto, ON MLS® C12612106

Residential Freehold (Detached)

$4790000.0

4 +2 Beds
7 Baths
3500-5000 sq-ft

This Stunning Luxury Home Offers a Meticulously Designed Multi-Level Layout, Where No Detail Has Been Overlooked. Situated on a Quiet Street near Top

27 Photos

71 Gordon Road, Toronto, ON , MLS #C12500386 , Image - 1

71 Gordon Road St. Andrew-Windfields, Toronto, ON MLS® C12500386

Residential Freehold (Detached)

$4388000.0

Price drop by 2.2%

5 +2 Beds
8 Baths
5000 + sq-ft

A rare opportunity to purchase one of the largest and most refined homes in the St. Andrews area. This 5,400 sq ft custom residence, plus a 2,200 sq f

42 Photos

101 Forest Heights Boulevard, Toronto, ON , MLS #C12485067 , Image - 1

101 Forest Heights Boulevard St. Andrew-Windfields, Toronto, ON MLS® C12485067

Residential Freehold (Detached)

$10880000.0

8 +1 Beds
11 Baths
5000 + sq-ft

Welcome To 101 Forest Heights Boulevard, A Majestic Custom-Built Residence Situated On An Extraordinary 100.06 X 286 Ft Lot In One Of Toronto's Most P

27 Photos

88 Old Colony Road, Toronto, ON , MLS #C12202360 , Image - 1

88 Old Colony Road St. Andrew-Windfields, Toronto, ON MLS® C12202360

Residential Freehold (Detached)

$5380000.0

4 +1 Beds
5 Baths
3500-5000 sq-ft

Lucky #88 Old Colony Road,The Most Prestigious Address in Bayview, York Mills, and The Bridle Path.A truly rare and exceptional opportunity set amongs

40 Photos

372 Old Yonge Street, Toronto, ON , MLS #C12178366 , Image - 1

372 Old Yonge Street St. Andrew-Windfields, Toronto, ON MLS® C12178366

Residential Freehold (Detached)

$8990000.0

8 Beds
8 Baths
5000 + sq-ft

One and only. Nestled privately in Toronto's exclusive St Andrew enclave, appx 0.86-acre (37,507.72 sf) hillside ground adores the expansive tableland

50 Photos

21 Forest Heights Boulevard, Toronto, ON , MLS #C12399281 , Image - 1

21 Forest Heights Boulevard St. Andrew-Windfields, Toronto, ON MLS® C12399281

Residential Freehold (Detached)

$5998000.0

5 +1 Beds
7 Baths
3500-5000 sq-ft

Exceptional Red-brick Georgian Estate In A Prestigious Neighbourhood. Welcome To This Timeless Luxury Residence Offering Approximately 6,260 Sq Ft Of

Shortlisted Properties

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St. Andrew-Windfields, Toronto, ON Luxury Homes

Lily at Crosstown

The Clove Condos

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