Settled in the heart of Wellesleys coveted Country Club neighborhood, 53 Windsor Road is an enchanting, thoughtfully updated Cape-style home that blends classic charm with modern comfort. The open floor plan features spacious sunlit rooms, including a welcoming living room with beamed ceiling and oversized fireplace that flows seamlessly into a formal dining room adorned with large picture windows. The kitchen with quartz counter tops and high end appliances boasts a central island, hardwood floors and a generous eat-in area with access to a deck - perfect for outdoor living. A bright family room with gas fireplace overlooks the beautifully landscaped level grounds. Upstairs find a lovely primary suite and 2 additional bedrooms with 2 baths. A finished lower level adds versatility with a guest suite with full bath and a playroom or exercise room. Ideally located close to town, the train, and shops, this home is a rare opportunity in one of Wellesleys most desirable locations!
- MLS# 73381532
- Date Listed05/28/2025
- Bedrooms 4
- Bathrooms 4 Full baths, 1 Half baths
- Lot Size 0.54 acres (23,694 sq. ft)
- Sewer Public Sewer
- Subdivision Country Club
- Property Type Single Family
- County Norfolk
- Year Built 1926
- Water Public
- Square Feet 3,272 sq. ft
- Price Per Sq. Ft $871.03
Interior Features
- Appliances Range, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer
- Flooring Tile, Carpet, Hardwood
- Cooling Central Air, Ductless
- Heating Natural Gas, Baseboard
Exterior / Lot Features
- Roof Shingle
- Lot Size Acres 0.54
- Lot Size SQFT 23,694.00
- Lot Features Level, Landscaped
Directions
Abbott Road to Windsor Road
Financial Considerations
- Tax Amount $25,083
- Terms Cash, Conventional, FHA, VA Loan
Nearby Schools
Source: School Digger
Preschool At Wellesley Schools
Public • PK - PK • Serves this home
1.12 mi
Distance
Public • 6 - 8 • Serves this home
2.03 mi
Distance
Public • 9 - 12 • Serves this home
1.32 mi
Distance
Preschool At Wellesley Schools
Public • PK - PK • Serves this home
1.12 mi
Distance
Public • PK - 5
2.64 mi
Distance
Public • PK - 3
5.9 mi
Distance
Public • PK - 3
6.19 mi
Distance
William F. Stanley Elementary School
Public • PK - 5
6.64 mi
Distance
Public • PK - PK
6.82 mi
Distance
Public • 1 - 5
7.07 mi
Distance
Public • PK - KG
7.19 mi
Distance
Public • PK - PK
9.07 mi
Distance
Public • PK - 5
9.53 mi
Distance
Public • 6 - 8 • Serves this home
2.03 mi
Distance
Public • 7 - 8
3.48 mi
Distance
Public • 6 - 6
3.86 mi
Distance
Public • 6 - 8
4.97 mi
Distance
Public • 6 - 8
5.45 mi
Distance
Public • 6 - 8
5.45 mi
Distance
Public • 4 - 5
6.19 mi
Distance
Public • 6 - 8
6.82 mi
Distance
Public • 5 - 8
7.18 mi
Distance
Public • 6 - 8
7.61 mi
Distance
Public • 9 - 12 • Serves this home
1.32 mi
Distance
Public • 9 - 12
2.86 mi
Distance
Public • 9 - 12
4.97 mi
Distance
Public • 9 - 12
5.45 mi
Distance
Public • 9 - 12
6.03 mi
Distance
Public • 9 - 12
7.33 mi
Distance
Public • 9 - 12
7.58 mi
Distance
Public • 9 - 12
9 mi
Distance
Private • UG - UG
1.47 mi
Distance
Private • 05 - 12
2.46 mi
Distance
Private • 08 - 11
3.23 mi
Distance
Private • 08 - 12
4.23 mi
Distance
Private • 06 - 12
4.48 mi
Distance
Private • UG - UG
5.18 mi
Distance
Private • 07 - 12
5.24 mi
Distance
Bais Yaakov Of Boston High School
Private • 09 - 12
5.88 mi
Distance
Brandon School & Residental Treatment
Private • 02 - 12
5.9 mi
Distance
Private • 07 - 12
6.49 mi
Distance
Sales & Tax History
Source: Public Records
| Street Address | Beds | Baths | Sold Date | List Price | Valuation Date | Valuation Price |
|---|---|---|---|---|---|---|
| 11 Holly Rd | 4 | 3 | Jan 28, 2026 | $1,349,000 | Feb 03, 2026 | - |
| 58 Norwich Road | Listing | 4 | 4 | Jan 16, 2026 | $2,249,000 | Mar 21, 2024 | $2,012,445 |
| 36 Oakridge Rd | 6 | 7 | Dec 06, 2025 | $4,999,000 | Feb 03, 2026 | - |
| 103 Thurston Road | 3 | 2 | Jan 14, 2026 | $2,200,000 | Feb 03, 2026 | - |
| 24 Jackson Rd | 6 | 5 | Jan 28, 2026 | $3,295,000 | Feb 03, 2026 | - |
| 36 Davenport Rd | 3 | 3 | Jan 09, 2026 | $950,000 | Feb 03, 2026 | - |
| 1 Williams Ct | 3 | 2 | Dec 17, 2025 | $669,900 | Feb 03, 2026 | - |
| 156 Woodbine Cir | 4 | 3 | Dec 05, 2025 | $1,799,000 | Feb 03, 2026 | - |
| 17 Deforest Rd | 3 | 3 | Dec 18, 2025 | $1,224,900 | Feb 03, 2026 | - |
| 28 Poplar Rd | 3 | 3 | Dec 04, 2025 | $1,098,000 | Feb 03, 2026 | - |
Population & Environment
Source: Sperling's Best Places
| Zip | City | County | National | |
|---|---|---|---|---|
| Population | N/A | 14,421 | 725,326 | 335,858,263 |
| Population Density | N/A | 2,879 | 1,831 | 95 |
| People per Household | N/A | 2.8 | 2.5 | 2.6 |
| Median Age | N/A | 33.9 | 43 | 39.1 |
| Median Income | N/A | $182,173 | $108,049 | $66,222 |
| Average Income | N/A | $96,489 | $57,162 | $35,475 |
| Cost of Living Index | 146 | 139 | 117 | 100 |
| Zip | City | County | National | |
|---|---|---|---|---|
| January Avg. High Temp | N/A°F | 17.29°F | 18.1°F | 22.6°F |
| July Avg. High Temp | N/A°F | 83.13°F | 81.2°F | 86.2°F |
| Annual Precipitation | N/A" | 45.45" | 51.22" | 38" |
21/100
Car-Dependent
Walk Score ®
22/100
Bikable
Bike Score ®
Overview
Almost all errands require a car. It is possible to get on a bus. Minimal bike infrastructure.Walkability averages in the surrounding area
The average walkability score in the surrounding area is Walk Score: 28/100, Transit Score: 12/100, Bike Score: 31/100.
Property Change History
Points of Interest near 53 Windsor Rd, Wellesley, MA 02481
0.34 mi
Distance
0.34 mi
Distance
0.37 mi
Distance
0.38 mi
Distance
0.42 mi
Distance
898 ft
Distance
0.27 mi
Distance
0.3 mi
Distance
898 ft
Distance
0.37 mi
Distance
0.3 mi
Distance
0.3 mi
Distance
0.38 mi
Distance
0.29 mi
Distance
0.34 mi
Distance
0.35 mi
Distance
0.37 mi
Distance
0.38 mi
Distance
0.39 mi
Distance
0.39 mi
Distance
0.4 mi
Distance
0.4 mi
Distance
Nearby Properties
-
$2,499,000 Active Under Contract5 bds • 3 ba • 3,690 sqft
138 Waban Avenue, Newton, MA 02468
Ideally located on one of Waban's prettiest streets, this elegant Colonial Revival-style residence, situated on a level corner lot, is spectacular. The welcoming entrance, with gleaming hardwood floor, is light and bright, and opens to a grand livin...Listing by: -
$2,475,000 Active4 bds • 4 ba • 3,483 sqft
55 Evelyn Rd, Newton, MA 02468
Elegant Tudor residence, beautifully sited on .36 acres in one of Waban’s most sought-after neighborhoods. This gracious home offers 4 bedrooms and 3.5 baths, seamlessly blending timeless architectural character with inviting modern comfort. The main...Listing by: -
New$2,495,000 Active5 bds • 4 ba • 3,398 sqft
31 College Road, Wellesley, MA 02482
5 bedroom home on Morses Pond with the most incredible water views. Swim, paddle board, kayak or fish from your own backyard. Large open kitchen family room with full picture windows offering stunning views of the pond. Kitchen with stainless applian...Listing by: -
$2,995,000 Active6 bds • 2 ba • 3,408 sqft
1208 Walnut St, Newton, MA 02461
Classic 1920 stucco two-family in the heart of Newton Highlands Village about a one-minute walk to the D-line MBTA. Each generous residence is ~1,700± SF with 3 bedrooms and 1 full bath (one unit with fireplace). Detached two-car garage plus driveway...Listing by: -
$2,899,000 Active5 bds • 5 ba • 3,662 sqft
956 Walnut Street 6, Newton, MA 02461
Welcome to The Residences at Four Corners, a collection of seven spacious townhomes in the Four Corners neighborhood of Newton Highlands. Crystal Lake, Whole Foods, village shops, Cold Spring Park, and Newton Centre are all nearby, and both the Newto...Listing by: -
$2,899,000 Active5 bds • 5 ba • 3,660 sqft
956 Walnut Street 6, Newton, MA 02461
Welcome to The Residences at Four Corners, a collection of seven spacious townhomes in the Four Corners neighborhood of Newton Highlands. Crystal Lake, Whole Foods, village shops, Cold Spring Park, & Newton Centre are all nearby, and both the Newton...Listing by: -
$2,495,000 Active5 bds • 5 ba • 3,404 sqft
956 Walnut Street 7, Newton, MA 02461
Welcome to The Residences at Four Corners, a collection of seven spacious townhomes in the Four Corners neighborhood of Newton Highlands. Crystal Lake, Whole Foods, village shops, Cold Spring Park, and Newton Centre are all nearby, and both the Newto...Listing by: -
$2,495,000 Active5 bds • 5 ba • 3,404 sqft
956 Walnut Street 7, Newton, MA 02461
Welcome to The Residences at Four Corners, a collection of seven spacious townhomes in the Four Corners neighborhood of Newton Highlands. Crystal Lake, Whole Foods, village shops, Cold Spring Park, and Newton Centre are all nearby, and both the Newto...Listing by: -
New$2,890,000 Active4 bds • 4 ba • 3,714 sqft
1151 Commonwealth Ave, Newton, MA 02465
Timeless Tudor architecture elevated by a masterfully executed, full studs-in renovation delivering a light-filled, sophisticated interior w/ exceptional flow. Set on the coveted Commonwealth Ave Carriage Lane w/ traffic-free outdoor recreation beyon...Listing by: -
New$2,495,000 Active4 bds • 4 ba • 3,357 sqft
333 Goddard Ave 333, Brookline, MA 02445
Exceptional and rarely available end residence at The Townhouses at Larz Anderson, offering turnkey living with southern exposure, a first-floor primary suite, and serene, wooded outlooks amid parklike grounds in a coveted Brookline location. Beautif...Listing by: -
$2,600,000 Active4 bds • 5 ba • 3,395 sqft
416 Conant Rd, Weston, MA 02493
Built in 2022 with a blend on modern and traditional. Excellent open floorplan with 4 bedrooms, each with ensuite bathroom. 9' ceilings with large windows on the first and second floors make this smaller house spacious. Large deck that overlooks a...Listing by: -
$2,995,000 Active5 bds • 5 ba • 3,370 sqft
323 Clark Rd, Brookline, MA 02445
Exceptional opportunity to own a beautifully renovated and thoughtfully designed 5-bedroom home on coveted Clark Road. The 1st floor offers a sun-filled eat-in kitchen, a generously proportioned living room with a wood-burning fireplace, an elegant d...Listing by: -
$3,195,000 Active5 bds • 4 ba • 3,250 sqft
90 Addington 2, Brookline, MA 02445
Located on Aspinwall Hill just across from across from Schick park is this gut renovated 5 bed, 3.5 bath 3,250 sq. ft. duplex that artfully blends luxury with comfort. The expansive foyer leads you to a state-of-the-art chef's kitchen, complete with...Listing by: -
$2,995,000 Active5 bds • 4 ba • 3,450 sqft
90 Addington 1, Brookline, MA 02445
Located on Aspinwall Hill just across from Schick park is this gut renovated 5 bed, 4 full bath 3,450 sq. ft. duplex that artfully blends luxury with comfort. The expansive foyer leads you to a state-of-the-art chef's kitchen, complete with stone cou...Listing by: -
New$2,900,000 Active4 bds • 3 ba • 3,377 sqft
24 Blake Rd, Brookline, MA 02445
Classic brick and slate Colonial thoughtfully updated for sophisticated, modern living. Beautifully reimagined with a fabulous, functional floor plan, designer baths, a modern eat-in kitchen with stone counters and stainless appliances, updated syste...Listing by: -
$2,749,000 Active4 bds • 4 ba • 3,483 sqft
11 Goodwin Place Unit 11-1, Brookline, MA 02445
50% Reserved. Dream single fam alternative. Welcome home to this exclusive development in the heart of Brookline Village. This boutique collection of four newly created townhome condos sets a new standard for elegant urban living. Each expansive resi...Listing by: -
$2,780,000 Active4 bds • 5 ba • 2,900 sqft
65 Francis A, Brookline, MA 02446
Last Unit Available! Thoughtfully renovated, this 2025 Coolidge Corner condominium blends classic charm with modern comfort. A welcoming mudroom opens to a sunlit kitchen with generous counter space, perfect for cooking or hosting. The main level fea...Listing by: -
$2,799,000 Active4 bds • 3 ba • 2,985 sqft
49 Grozier, Cambridge, MA 02138
Ideally situated on a quiet side street, this home has been thoughtfully renovated offering exceptional space & modern interior. Enter to a spacious living room/family room with gas fireplace, a fully renovated kitchen with premium appliances & doubl...Listing by: -
$2,495,000 Active5 bds • 3 ba • 3,000 sqft
17 Smith Place, Cambridge, MA 02138
Tucked beside Fresh Pond, this modern, highly efficient single-family home spans three light-filled levels. The flexible 1st floor includes 3 bedrooms, a full bath, laundry room, and access to a covered deck and rear patio. The main level features so...Listing by: -
New$2,850,000 Active6 bds • 3 ba • 3,675 sqft
164 Calumet Street, Boston, MA 02120
Spectacular Views of Boston! Lovely, owner occupied 3 family. Each unit consists of 2 bedrooms, an office, living room, 1 bath, and an eat-in-kitchen that leads to a back porch overlooking a tree lined yard. Separate systems and laundry in each unit...Listing by:
Similar Priced Comparison
-
New$2,999,000 Active7 bds • 8 ba • 7000 sqft
365 Worcester St
- Home larger by 3,728 sqft
- Lot smaller by 172 sqft
- Newer by 99 years
Listing by: -
$2,590,000 Active5 bds • 5 ba • 5261 sqft
1 Clock Tower Drive
- Home larger by 1,989 sqft
- Lot smaller by 3,394 sqft
- Newer by 73 years
Listing by: -
$2,789,888 Active5 bds • 7 ba • 5130 sqft
12 Hill Street
- Home larger by 1,858 sqft
- Lot smaller by 15,853 sqft
- Newer by 99 years
Listing by: -
New$2,400,000 Active Under Contract6 bds • 7 ba • 6553 sqft
5 Homsy Lane
- Home larger by 3,281 sqft
- Lot smaller by 11,261 sqft
- Newer by 90 years
Listing by: -
$2,995,000 Active6 bds • 6 ba • 5806 sqft
42 Edmunds Road
- Home larger by 2,534 sqft
- Lot larger by 2,191 sqft
- Newer by 7 years
Listing by: -
$2,625,000 Active Under Contract5 bds • 6 ba • 5515 sqft
345 Central Avenue
- Home larger by 2,243 sqft
- Lot smaller by 12,325 sqft
- Newer by 99 years
Listing by: -
$3,198,000 Active6 bds • 8 ba • 6501 sqft
34 Pershing Rd
- Home larger by 3,229 sqft
- Lot smaller by 12,924 sqft
- Newer by 99 years
Listing by: -
$3,180,000 Active Under Contract6 bds • 7 ba • 5830 sqft
3 Hancock Road
- Home larger by 2,558 sqft
- Lot smaller by 4,658 sqft
- Newer by 100 years
Listing by: -
$2,495,000 Active8 bds • 6 ba • 5559 sqft
9-11 Hampden Street
- Home larger by 2,287 sqft
- Lot smaller by 7,385 sqft
- Older by 6 years
Listing by: -
$2,495,000 Active8 bds • 5 ba • 5559 sqft
9-11 Hampden Street
- Home larger by 2,287 sqft
- Lot smaller by 7,385 sqft
- Older by 6 years
Listing by: -
$2,799,999 Active7 bds • 6 ba • 6061 sqft
212 Central Ave
- Home larger by 2,789 sqft
- Lot smaller by 13,719 sqft
- Newer by 100 years
Listing by: -
$3,269,900 Active6 bds • 8 ba • 7340 sqft
52 Hancock Street
- Home larger by 4,068 sqft
- Lot smaller by 13,685 sqft
- Newer by 100 years
Listing by: -
$2,499,000 Active Under Contract5 bds • 5 ba • 5850 sqft
15 Jenna Circle
- Home larger by 2,578 sqft
- Lot smaller by 8,683 sqft
- Newer by 77 years
Listing by: -
$2,499,000 Active5 bds • 6 ba • 4550 sqft
62 Evelyn Road
- Home larger by 1,278 sqft
- Lot smaller by 12,456 sqft
- Newer by 99 years
Listing by: -
$3,268,000 Active6 bds • 7 ba • 6100 sqft
177 Varick Rd
- Home larger by 2,828 sqft
- Lot smaller by 11,883 sqft
- Newer by 99 years
Listing by: -
$2,999,000 Active6 bds • 6 ba • 5977 sqft
40 High Street
- Home larger by 2,705 sqft
- Lot smaller by 10,154 sqft
- Newer by 100 years
Listing by: -
New$3,285,000 Active6 bds • 7 ba • 7405 sqft
108 Woodbine Circle
- Home larger by 4,133 sqft
- Lot smaller by 12,830 sqft
- Newer by 100 years
Listing by: -
$2,150,000 Active4 bds • 6 ba • 3400 sqft
27 Hamilton Pl
- Home larger by 128 sqft
- Lot smaller by 3,569 sqft
- Older by 76 years
Listing by: -
$2,499,000 Active Under Contract5 bds • 3 ba • 3690 sqft
138 Waban Avenue
- Home larger by 418 sqft
- Lot smaller by 9,924 sqft
- Older by 16 years
Listing by: -
$2,695,900 Active5 bds • 6 ba • 5897 sqft
5 Hazel Lane
- Home larger by 2,625 sqft
- Lot smaller by 11,105 sqft
- Newer by 100 years
Listing by:
Nearby Locations
Communities
- Wellesley Hills Homes For Sale
- Needham Heights Homes For Sale
- Four Corners Homes For Sale
- Dexter Homes For Sale
- West End Homes For Sale
- Downtown Homes For Sale
- Zimbles Homes For Sale
- West Roxbury Homes For Sale
- Six Moon Hill Homes For Sale
- Camp Bob White Homes For Sale
- North Framingham Homes For Sale
- Hyde Park Homes For Sale
- West Concord Homes For Sale
- West Concord Homes For Sale
- Great Meadows Homes For Sale
- Arlington Historic Center Homes For Sale
- Downtown Homes For Sale
- Westview Homes For Sale
- Back Bay Homes For Sale
- Scott's Woods Homes For Sale
Nearby Zips
- 02482 Homes For Sale
- 02481 Homes For Sale
- 01760 Homes For Sale
- 02493 Homes For Sale
- 02492 Homes For Sale
- 02494 Homes For Sale
- 02451 Homes For Sale
- 02459 Homes For Sale
- 02090 Homes For Sale
- 02026 Homes For Sale
- 01701 Homes For Sale
- 02467 Homes For Sale
- 02132 Homes For Sale
- 01776 Homes For Sale
- 02421 Homes For Sale
- 02062 Homes For Sale
- 02445 Homes For Sale
- 01742 Homes For Sale
- 02420 Homes For Sale
- 02136 Homes For Sale
Nearby Cities
- Wellesley, MA Homes for Sale
- Natick, MA Homes for Sale
- Weston, MA Homes for Sale
- Needham, MA Homes for Sale
- Needham Heights, MA Homes for Sale
- Newton, MA Homes for Sale
- Waltham, MA Homes for Sale
- Westwood, MA Homes for Sale
- Dedham, MA Homes for Sale
- Framingham, MA Homes for Sale
- Sudbury, MA Homes for Sale
- East Dedham, MA Homes for Sale
- North Sudbury, MA Homes for Sale
- East Watertown, MA Homes for Sale
- Norwood, MA Homes for Sale
- Walpole, MA Homes for Sale
- Brookline, MA Homes for Sale
- Lexington, MA Homes for Sale
- Concord, MA Homes for Sale
- West Concord, MA Homes for Sale
Similar Searches
- Wellesley Land for Sale
- Wellesley New Homes for Sale
- Wellesley Single Story Homes for Sale
- Wellesley Homes with Pools for Sale
- Wellesley Cheap Homes for Sale
- Wellesley Luxury Homes for Sale
- Wellesley Condos for Sale
- Wellesley Town Homes for Sale
- Wellesley Commercial for Sale
- Wellesley Open Houses for Sale
- Wellesley Two Car Garage Homes for Sale
- Wellesley Large Lots for Sale
- National Listings
- National Home Values
- Properties in MA
- Home Values in MA
- Other properties in Norfolk, MA
- Other properties in 02481, MA
- Home Values in Wellesley, MA
Frequently Asked Questions for 53 Windsor Rd
Source: Realty.com
53 Windsor Rd, Wellesley, MA 02481 is a Single Family 3,272 sq. ft. home listed for sale. Realty.com has 42 photos available of this 4 bed, 5 bath house, listed at $2,850,000. View sales and tax history, use our mortgage calculator and more on Realty.com
Realty.com has 42 photos of 53 Windsor Rd.
Our records indicate that 53 Windsor Rd was built in 1926.
The full address for this home is 53 Windsor Rd, Wellesley, MA 02481.
53 Windsor Rd has been listed on Realty.com since Wed May 28, 2025
Almost all errands require a car. It is possible to get on a bus. Minimal bike infrastructure.
The average walkability score in the surrounding area is Walk Score: 28/100, Transit Score: 12/100, Bike Score: 31/100.
There are 3 schools assigned to this home. Check out the schools near 53 Windsor Rd. Preschool At Wellesley Schools (Grades: PK - PK), Wellesley Middle School (Grades: 6 - 8), Wellesley Senior High School (Grades: 9 - 12)
Listing provided courtesy of:
William Raveis R.e. & Home Services
(tel: 781-235-5000)
Listing agent:
Debi Benoit
(tel: 617-962-9292)
(#BB980372)
This content last refreshed on 2026-02-03 14:47:14. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.
Export listing data of 53 Windsor Rd, Wellesley, MA 02481 : MLS# 73381532