149 m
Distance
Winfield Estates, Toronto, ON, Canada
Winfield Estates - Nearby Homes for Sale
Toronto, Ontario, Canada
Living Near Winfield Estates
Buyers searching for homes near Winfield Estates usually want two things: access and context. This page is built to make that comparison easier by combining available listings, street-level location details, and nearby amenities in one place. Instead of jumping between different tools, you can review homes and local points of interest side by side, then decide which streets or neighborhoods match your priorities. For Toronto, ON, that means you can quickly compare options around a known destination before spending time on private tours.
Right now, this page shows 47 nearby homes and 20 surrounding points of interest. You can use the listing table to compare address, bed and bath counts, and list price, then use the categories section to understand what types of amenities are clustered around the area. This structure helps you compare convenience, neighborhood activity, and market options without leaving the page.
If you are relocating or narrowing your search, start with the homes shown here, then expand your review to nearby categories and additional location details. This workflow gives a more complete picture than price alone and helps avoid shortlisting homes that do not fit your day-to-day needs. Availability and pricing can change quickly, so checking this page regularly is useful when you are actively searching near Winfield Estates. Once a property looks promising, contact an agent to confirm the latest status and schedule a showing.
Frequently Asked Questions
How many homes are currently listed near Winfield Estates?
There are currently 47 active or coming-soon homes displayed near Winfield Estates on this page.
What information does this page include for homes near Winfield Estates?
This page includes nearby home listings, home prices, bedroom and bathroom counts, and nearby points of interest around Winfield Estates in Toronto.
How can I compare neighborhoods around Winfield Estates?
Use the nearby homes table and points-of-interest sections to compare listing prices, surrounding amenities, and local access points before scheduling a tour.
Homes for sale near Winfield Estates, Toronto, ON, Canada
| Address | Bed / Bath | Listing Price |
|---|---|---|
30 Blue Ridge Road, Toronto ON M2K 1R7
Rare-Find!! Bayview Village! Premium ~70ft Frontage! 4+1 Bedrooms & 3 Bathrooms! Luxury Kitchen With Sub-Zero Fridge & Viking Gas Cooktop, Oven & Built-In Microwave + Granite Countertop! Top Rated Schools Including Earl Haig Secondary School! Steps To Bayview Village Shopping Centre + Bessarion & Le
Living Area:
1600 Sqft.
|
5
Beds,
3
Baths
|
$1,988,000 |
88 OLSEN DRIVE
Attention Investors, Builders, and End-Users! Exceptional real estate opportunity to acquire a premium detached executive residence backing onto Graydon Hall Park under Power of Sale provisions. This spacious 4+3 bedroom, 4-bathroom 2-storey brick home features an expansive 2, 500-3, 000 sq ft footp
Living Area:
Sqft.
|
7
Beds,
4
Baths
|
$2,390,000 |
34 ELLIOTWOOD COURT
Nestled on a quiet cul-de-sac in sought-after St. Andrew-Windfields, this fully renovated home offers 4 spacious bedrooms, 5 bathrooms, and a 2-car garage, with a desirable west-facing backyard providing excellent privacy and comfort.Thoughtfully redesigned, the home features a functional layout wit
Living Area:
Sqft.
|
4
Beds,
5
Baths
|
$1,995,000 |
45 CLAREVILLE CRESCENT
Spacious, well-maintained family home situated on a premium lot in one of North York's most desirable neighbourhoods. Offering approximately 2, 100 sq. ft. of above-grade living space, this property features generous principal rooms, a functional layout, and abundant natural light throughout. The ma
Living Area:
Sqft.
|
3
Beds,
2
Baths
|
$1,585,000 |
20 MOSSGROVE TRAIL
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 an
Living Area:
Sqft.
|
4
Beds,
4
Baths
|
$1,890,000 |
7 PURLING PLACE
Beautifully renovated and offering over 5, 000 square feet of finished living space, this exceptional bungalow sits on an estate-sized lot of more than half an acre, tucked away at the end of a private cul-de-sac with just seven homes. The remarkable 328-foot-wide backyard is a feature rarely found
Living Area:
Sqft.
|
4
Beds,
5
Baths
|
$5,880,000 |
15 SULGRAVE CRESCENT
A Truly Extraordinary Gated Custom Estate Situated On A Quiet Crescent In One Of York Mills' Most Prestigious Enclaves. Spanning Nearly 9, 000 Sqft. Of Impeccably Designed Living Space. This Architectural Masterpiece Showcases Exceptional Craftsmanship, Timeless Elegance & Unparalleled Attention To
Living Area:
Sqft.
|
7
Beds,
9
Baths
|
$10,200,000 |
12 LONGHOPE PLACE
Rare opportunity to own this fabulous 4-bedroom family home backing onto a ravine for exceptional privacy and peaceful views. Thoughtfully designed for family living, this home features a fantastic layout with spacious principal rooms, a large eat-in kitchen, and a dining room with walk-out to an ov
Living Area:
Sqft.
|
4
Beds,
4
Baths
|
$1,199,900 |
4 QUINCY CRESCENT
This Is A Fabulous Home You've Been Looking For. Situated At Most Sought After Neighborhood , Mature , Perfect For All Ages, Among Multi-Million Homes, Easy To Transit , Close To All Amenities, Easily Accessible But Surrounded By Parks, Trees And Lawns, Privacy, Tranquil And Calming Down Whenever Dr
Living Area:
Sqft.
|
4
Beds,
2
Baths
|
$1,598,000 |
25 BURBANK DRIVE
Oversized renovated bungalow situated on a premium 62 x 134 ft lot in the highly sought-after Bayview Village neighbourhood. A rare opportunity for families, investors, or builders to own a move-in ready home in one of North York's most prestigious neighbourhoods. The bright, spacious main level fea
Living Area:
Sqft.
|
5
Beds,
4
Baths
|
$1,950,000 |
18 DERVOCK CRESCENT
Incredible opportunity in prestigious Bayview Village! This well-maintained 3-bedroom, 4-bathroom detached home offers exceptional flexibility for homeowners, investors, and those exploring future redevelopment potential. Surrounded by newer townhouse developments and situated in one of North York's
Living Area:
Sqft.
|
3
Beds,
4
Baths
|
$1,495,000 |
15 TOFINO CRESCENT
Nestled in one of Toronto's most prestigious and family-oriented neighbourhoods, this exceptional home is within walking distance to the highly sought-after Denlow Public School, with priority access to the Gifted Program, and is also zoned for top-ranked Windfields Middle School and York Mills Coll
Living Area:
Sqft.
|
6
Beds,
4
Baths
|
$2,399,900 |
20 ARROWSTOOK ROAD
Stunning modern custom home in prestigious Bayview Village on a 50x151 ft lot with 5, 000+ sq. ft. of premium living space. Features include sleek contemporary finishes, custom millwork, a mudroom with garage access, and four spacious bedrooms each with its own ensuite. The walk-up basement offers a
Living Area:
Sqft.
|
5
Beds,
7
Baths
|
$3,188,888 |
10 SILVERDALE CRESCENT
As Per City Confirmation, EHON provisions do apply to this property and for the proposed 10-unit apartment building, there is potential that Site Plan Approval may not be required under the applicable Planning Act exemptions. However, this would need to be confirmed by the Zoning Examiner through a
Living Area:
Sqft.
|
6
Beds,
4
Baths
|
$1 |
59 VALENTINE DRIVE
Rare opportunity to own a spacious raised bungalow with an insulated double car garage on one of the most desirable streets in Parkwoods-Donalda, backing directly onto greenspace. Nestled in one of the area's most sought-after family neighbourhoods, this property offers a unique blend of privacy, co
Living Area:
Sqft.
|
5
Beds,
3
Baths
|
$1,349,999 |
17 VALENTINE DRIVE
Fully Renovated Executive Residence Offering 5+1 Bedrooms with a stunning second-floor addition featuring a private primary retreat in its own separate wing. This sun-filled home is designed for comfortable family living and effortless entertaining. The gourmet kitchen walks out to a spacious deck o
Living Area:
Sqft.
|
6
Beds,
3
Baths
|
$1,988,000 |
10 GRANGEMILL CRESCENT
Welcome to an enclave of elegance and sophistication, where timeless luxury meets modern comfort. This custom-built masterpiece boasts exceptional design and craftsmanship, with stunning architectural details, high-end finishes, and an open floor plan that blends style and functionality. This except
Living Area:
Sqft.
|
7
Beds,
8
Baths
|
$5,388,000 |
48 WIMPOLE DRIVE
Welcome Home to 48 Wimpole Drive, a breathtaking, freshly renovated home nestled on a gated, estate-sized lot in the prestigious St. Andrews neighborhood. ***VTB Option Available Offered By Seller*** Surrounded by mature trees and lush landscaping, this remarkable home offers true resort-style livin
Living Area:
Sqft.
|
7
Beds,
9
Baths
|
$7,380,000 |
68 OLD COLONY ROAD
A True Architectural Masterpiece Built And Designed By Danieli Development, This Extraordinary Custom Estate Exemplifies The Highest Level Of Craftsmanship, Innovation, Premium Imported European Limestone, And Modern Luxury. Showcasing Exceptional Scale And Impeccable Attention To Detail, This One-O
Living Area:
Sqft.
|
9
Beds,
17
Baths
|
$30,000,000 |
101 GEORGE HENRY BOULEVARD
Amazing 4 bedroom, 4 level backsplit on a premium 61' X 125' landscaped lot in desirable " Henry Farm " ! Upgraded oak kitchen with centre island, built - in appliances, bay window, Corian countertops and upgraded ceramics. Sunken family room with gas fireplace and walk-out, open concept rec room wi
Living Area:
Sqft.
|
4
Beds,
2
Baths
|
$1,529,000 |
40 OLD COLONY ROAD
Nestled Within Bayview Gardens Most Iconic Street - Old Colony Road. This Magnificent Residence Boasts A 100' Frontage And Over 12, 000 SqFt Of Living Space. Offers Unparalleled Curb Appeal And A Grand Entrance. A Spacious Living Room With Soaring Vaulted Ceilings, Inviting An Abundance Of Natural L
Living Area:
Sqft.
|
7
Beds,
10
Baths
|
$6,995,000 |
23 LAUDERDALE DRIVE
For The Discerning Buyer W/ An Architectural Eye & An Appreciation For The Finest Luxury Finishes, This Award-Winning Smart Home Is A True Design Masterpiece. Situated On A Prestigious Crescent, This Custom Estate Offers Over 10, 341 Sq. Ft. Of Exceptional Living Space & Showcases An Extraordinary B
Living Area:
Sqft.
|
6
Beds,
7
Baths
|
$9,995,000 |
41 HURLINGHAM CRESCENT
Stunning architect-designed contemporary home on 50-foot-wide pie-shaped lot located on one of Toronto's most coveted, quiet crescents. Surrounded by lush gardens, a tranquil pond, and exceptional privacy, this custom home blends luxury, warmth, and natural light throughout. Featuring floor-to-ceili
Living Area:
Sqft.
|
4
Beds,
4
Baths
|
$2,795,000 |
18 CHIPSTEAD ROAD
Welcome to 18 Chipstead Road, an entertainer's dream home, conveniently located in the heart of Denlow near Bayview and 401 with great schools and lots of local shopping nearby. This fully renovated 4200 + square foot home is one of the nicest homes in the area. Interior designers Jeffrey Douglas an
Living Area:
Sqft.
|
5
Beds,
5
Baths
|
$4,688,000 |
3 VERNHAM COURT
Dramatic Curb Appeal - Rich In Architecture, Finest In Luxurious Appointments And Landscaping. Custom Residence - By And For Its Designer Owners. Premium Corner Locale On Quiet Cul-De-Sac In Prestigious St. Andrew-Windfields, This Exceptional Residence Offers Over 6, 356 Sq. Ft. Of Refined Living Sp
Living Area:
Sqft.
|
6
Beds,
7
Baths
|
$4,950,000 |
34 ADDISON CRESCENT
Situated on an expansive 11, 452 sq. ft. lot, this charming 1.5 storey home offers endless possibilities to renovate, expand, or build your dream home. Nestled in one of Toronto's most sought-after neighbourhoods, the property backs directly onto the scenic Don Mills Trail, providing a peaceful natu
Living Area:
Sqft.
|
4
Beds,
2
Baths
|
$1,799,800 |
11 CHIPSTEAD ROAD
Exceptional custom-built 4+1 bedroom, 6-bath residence on a quiet, tree-lined street in prestigious York Mills. Soaring 10' ceilings on the main floor and 9' ceilings on the second and lower levels create a bright, open feel, highlighted by dramatic two-storey (20') full-height glass windows overloo
Living Area:
Sqft.
|
5
Beds,
6
Baths
|
$4,990,000 |
27 HURLINGHAM CRESCENT
Brand new, never lived in luxury family home in a desirable neighbourhood! Rare opportunity to own a 5, 381 sq ft luxury home (+2, 086 sq ft finished basement), 7, 467 total living space, on a 13, 928 sq. ft. lot with mature trees in one of the city's most prestigious, family-oriented neighbourhoods
Living Area:
Sqft.
|
7
Beds,
9
Baths
|
$5,499,000 |
63 HOPPERTON DRIVE
Welcome to 63 Hopperton Dr, A Rarely Offered 4+1 Bedroom Backsplit House In The Prestigious St. Andrew-Windfields Community Of North York. This Bright Family Home Sits on a Generous Lot, Surrounded by Multi-million Dollar Residences, Offering Exceptional Potential for End-users, Investors, Builders,
Living Area:
Sqft.
|
5
Beds,
2
Baths
|
$2,200,000 |
16 SAGEWOOD DRIVE
Nestled in the coveted Banbury community, this 5-bedroom, 6-bathroom home offers over 6, 000 sq. ft. of beautifully updated living space on an 84 x 125 ft lot, complete with a 3-car garage. Thoughtfully renovated throughout, the home showcases exceptional craftsmanship, custom millwork, pot-lit moul
Living Area:
Sqft.
|
5
Beds,
6
Baths
|
$3,900,000 |
45 HURLINGHAM CRESCENT
Welcome to 45 Hurlingham Crescent, a bright, beautifully and immaculately updated 3+1 bedrooms, 2 bathrooms, move-in-ready raised bungalow, and prime redevelopment lot nestled on a quiet, tree-lined street in one of Toronto's most coveted neighbourhoods. Featuring a sun-filled open-concept layout, m
Living Area:
Sqft.
|
4
Beds,
2
Baths
|
$1,780,000 |
3 NOMAD CRESCENT
Stunning Custom Home on a Premium Landscaped Lot in a Quiet Crescent.Beautifully renovated with $$$ in upgrades, this exceptional custom-built residence sits on a large, professionally landscaped lot in a highly sought-after, family-friendly crescent.The unique open-concept main floor boasts impress
Living Area:
Sqft.
|
6
Beds,
4
Baths
|
$4,280,000 |
88 OLSEN DRIVE
Rarely Offered Exceptional 4+3 bedroom detached home backing onto Graydon Hall Park in the highly desirable Donalda Club community. Fully renovated from top to bottom and in excellent condition, the main floor features a spacious family room, laundry, and updated kitchen and bathrooms, all finished
Living Area:
Sqft.
|
7
Beds,
4
Baths
|
$2,488,000 |
48 HURLINGHAM CRESCENT E
Welcome to 48 Hurlingham Crescent, The Epiphany of Luxurious Living. Nestled in the coveted York Mills area in Toronto, exquisitely positioned near the hustle of Highways 401 and 404, granting effortless access to the city's vibrant plus. This residence also boasts a plethora of amenities, curated t
Living Area:
Sqft.
|
5
Beds,
6
Baths
|
$4,198,000 |
6 ARROWSTOOK ROAD
***Extraordinary----------"50Ft x 151.75Ft"-------------PREMIUM VALUE, POOL-SIZED----------DEEP LOT**Spacious**Updated**Upgraded**Charming & Livable**existing bungalow TO LIVE-----FACING TO A CITY PARK----- In prestigious Bayview Village------Convenient Location to Subway, Hwys, School and Ravine, P
Living Area:
Sqft.
|
4
Beds,
3
Baths
|
$1,888,000 |
50 CLARINDA DRIVE
Fabulous Kelbar built 4+1 bedroom, 4 bathroom family home on an expansive pie-shaped 130 ft-167 ft deep lot with heated inground pool and extra-long driveway for 6 cars plus 2 more in the garage! Approximately 2900 sqft of wonderfully updated space. Great layout with formal living and dining rooms p
Living Area:
Sqft.
|
5
Beds,
4
Baths
|
$2,288,000 |
18 OLSEN DRIVE
Welcome To This Gorgeous Rare Found Detached Sidesplit 4 House Located On Prestigious Don Mills/York Mills Parkwoods-Donalda Community. Surrounded By Lots Of Rebuilt Houses. Good Land Value For Rebuild As Well. Steps To Private Club Donalda Golf Club.Large Corner Lot With Triple Car Garage, Large Dr
Living Area:
Sqft.
|
5
Beds,
3
Baths
|
$1,930,000 |
20 BERKINDALE DRIVE
Spectacular Custom Residence With Unsurpassed Beauty & Elegance! Exceptional 6000 Sf. 5 Bdrm Home Exquisitely Designed W/Sophisticated & Luxurious Finishes, Elaborate Plaster Crown Mouldings, Custom Kitchen & Family Rm Combination Provide Venues For Casual Gatherings W/ French Doors Opening To A Bac
Living Area:
Sqft.
|
6
Beds,
8
Baths
|
$6,995,000 |
84 BANNATYNE DRIVE
Expansive Tree-Lined Ravine Lot Backing Onto Picturesque Vyner Greenbelt. Coveted Opportunity To Build Your Dream Home In One Of Torontos Most Desirable Family Neighbourhoods. Update To Your Desires. Vast Fenced Backyard Overlooking Forested Ravine Offers Incredible Privacy And Potential. Main Floor
Living Area:
Sqft.
|
6
Beds,
4
Baths
|
$2,695,000 |
62 WIMPOLE DRIVE
This stunning custom-built residence, designed by renowned designer, boasts a premium lot measuring 128 by 159 feet. Situated in one of the most sought-after pockets of the prestigious St. Andrew area, this home offers over 7, 000 square feet of living space on an expansive 18, 000 square feet lot,
Living Area:
Sqft.
|
5
Beds,
6
Baths
|
$6,980,000 |
40 OLD COLONY ROAD
Nestled Within Bayview Gardens Most Iconic Street - Old Colony Road. This Magnificent Residence Boasts A 100' Frontage And Over 12, 000 SqFt Of Living Space. Offers Unparalleled Curb Appeal And A Grand Entrance. A Spacious Living Room With Soaring Vaulted Ceilings, Inviting An Abundance Of Natural L
Living Area:
Sqft.
|
7
Beds,
10
Baths
|
$7,998,000 |
3 PURLING PLACE
**Magnificent**Extraordinary--Architecturally Significant Ultra ""STEEL"" Frame Design, Constructed To ""Commercial Standards"" Built For Its Owner On Exclusive Cul-De-Sac Location**Expansive Living Space Apx 10, 000Sf(6500Sf:1st/2nd Flrs) Crafted For Family Comfort & Zen Inspired Clean--Seamless Li
Living Area:
4999.96 Sqft.
|
5
Beds,
7
Baths
|
$8,600,000 |
55 GLENTWORTH ROAD
Welcome to your dream retreat in North York! This stunning 4 bed/2 bath back-split is a masterpiece of luxury living, boasting over $300k in top-tier custom renovations from top to bottom. Step inside to discover a world of elegance and sophistication - every detail has been meticulously crafted to
Living Area:
0 Sqft.
|
5
Beds,
2
Baths
|
$1,399,999 |
42 KAREN ROAD
Desirable ""York Mill"" location! This property boasts numerous upgrades and features two separate entries to a 2-bedroom and a 1-bedroom apartment, making it ideal for families with potential rental income. Highlights include new hardwood floors, a new roof, ample pot lights, and an open- concept k
Living Area:
0 Sqft.
|
6
Beds,
4
Baths
|
$1,899,000 |
48A CHATFIELD DRIVE
A rare opportunity awaits in Banbury/Don Millsa city-severance approved lot for sale. Fronting 54.3ft x 101.6ft - 5952.09sqft. Nestled in Toronto's prestigious upper scale, near Edward Gardens, Bridle Path, and Sunny-brook Hospital, this locale blends urban sophistication with natural tranquility. S
Living Area:
0 Sqft.
|
4
Beds,
2
Baths
|
$1,500,000 |
48 CHATFIELD DRIVE
A rare opportunity awaits in Banbury/Don Mills, a city-approved double lot for sale. Nestled in Toronto's prestigious upper scale, near Edward Gardens, Bridle Path, and Sunny-brook Hospital, this locale blends urban sophistication with natural tranquility. Surrounded by homes selling for $4 million+
Living Area:
0 Sqft.
|
4
Beds,
2
Baths
|
$2,400,000 |
103 OLD COLONY ROAD
Uniquely Distinguished. Exceptionally Designed Nestled In One Of Toronto's Most Prestigious Neighbourhoods. Conceptualized, Designed & Executed Collaboratively Btwn Michael McCann, World Renowned Arch. Visionary/Artist & Lisa Mandel McCann, Archit'l Design/Builder. Unique Inspired By The Property It
Living Area:
0 Sqft.
|
6
Beds,
11
Baths
|
$25,000,000 |
Points of Interest near Winfield Estates
Additional information
- Website : www.ucciproperties.com