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
Schools near 02481
Explore the local neighborhood highlights and top-rated schools near 02481 in Wellesley, MA.
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 |
|---|---|---|---|---|
| 110 Rosemary Way | 3 | 2 | Jun 19, 2026 | $305,000 |
| 12 Bird Hill Ave | 5 | 6 | May 09, 2026 | $3,795,000 |
| 18 Evergreen Rd | 4 | 4 | Jun 16, 2026 | $1,995,000 |
| 19 Mason Road | 6 | 6 | Jul 02, 2026 | $2,799,900 |
| 58 Morton St | 3 | 3 | May 12, 2026 | $1,525,000 |
| 510 Webster Street | 3 | 3 | May 16, 2026 | $1,295,000 |
| 44 Bradford Rd | 5 | 6 | Jun 02, 2026 | $3,150,000 |
| 70 Briarwood Circle | 5 | 5 | May 09, 2026 | $2,379,000 |
| 28 Mercer Rd | 5 | 4 | May 20, 2026 | $1,898,000 |
| 36 Eliot Rd | 4 | 4 | Jun 02, 2026 | $1,500,000 |
Local Neighborhood Highlights for 02481
Discover key demographics, population statistics, and environmental insights for the Wellesley, MA area.
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" |
26/100
Car-Dependent
Walk Score ®
0/100
Minimal Transit
Transit Score ®
22/100
Bikable
Bike Score ®
Overview
Most 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: 30/100.
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
-
$2,480,000 Active5 bds • 5 ba • 3,600 sqft
37 Oakland St, Wellesley, MA 02481
STUNNING NEW-CONSTRUCTION-QUALITY RENOVATION! Completely gut-renovated 5BR/4.5BA home featuring an open, sun-filled floor plan, designer finishes, and a chef’s kitchen with premium appliances. Bright sunroom, spacious living areas, and a fully finish...Listing by: -
$2,495,000 Active Under Contract4 bds • 4 ba • 3,105 sqft
14 Homestead, Newton, MA 02468
Nestled on a quiet street in Waban, this beautifully updated Tudor blends timeless charm with modern comfort. Filled with natural light, this well-maintained home features 4 bedrooms, 3.5 baths, and thoughtfully designed living spaces ideal for every...Listing by: -
$2,599,000 Active4 bds • 4 ba • 3,467 sqft
956 Walnut Street 2, 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: -
$2,599,000 Active4 bds • 4 ba • 3,467 sqft
956 Walnut Street 2, 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: -
$2,600,000 Active6 bds • 3 ba • 3,145 sqft
140 Pleasant St, Newton, MA 02459
Attention buyers, developers, and renovators! Rare opportunity to own nearly an acre of land in the heart of Newton Centre, directly across from Mason-Rice Elementary School. This charming antique home, which has been in the same family for 63 years,...Listing by: -
$2,650,000 Active4 bds • 5 ba • 3,307 sqft
287 Langley Rd 6, Newton, MA 02459
This beautifully reimagined 4-bedroom, 4-ensuite-bath home with a powder room offers over 3,300 sq ft of thoughtfully curated space. An architect-led renovation creates a clean, sophisticated aesthetic, opening the main level into a light-filled layo...Listing by: -
$2,595,000 Active2 bds • 3 ba • 2,843 sqft
120 Seaver St B204, Brookline, MA 02445
Experience refined single-level living in this elegant 2-bedroom, 3-bath residence at Longyear at Fisher Hill, an exclusive gated community on the former Longyear Museum estate. Spanning 2,843 SF, this sun-filled condominium offers beautifully design...Listing by: -
$2,698,000 Active5 bds • 4 ba • 3,738 sqft
140 Dudley St, Brookline, MA 02445
This classic brick Colonial, set on one of Brookline’s most coveted streets near the Brookline Reservoir, offers stunning views and exceptional spaces for both family living and entertaining. This 5-bedroom, 3.5-bath home features a front-to-back liv...Listing by: -
$2,500,000 Active5 bds • 4 ba • 3,219 sqft
128 Dudley St, Brookline, MA 02445
Set in the coveted estate area of Brookline, this residence offers a rare opportunity to create a truly spectacular home overlooking the serene beauty of the Brookline Reservoir. Rich in architectural character, the home is defined by its striking pr...Listing by: -
$2,800,000 Active4 bds • 4 ba • 3,498 sqft
91 University Rd 2, Brookline, MA 02445
Experience refined living on a quiet one-way street in Washington Square. This distinctive two-level condo occupies the third and fourth floors of a classic five-story building, blending historic character with modern updates. The main level features...Listing by: -
$3,200,000 Active4 bds • 4 ba • 3,261 sqft
197 Winchester Street 1, Brookline, MA 02446
Price to SELL: Newly renovated 3,250+ SF residence delivers sweeping skyline views from Cambridge to Back Bay, four private outdoor spaces, and the scale of a single-family home. The expansive second floor main living level includes 3 bedrooms, 2.5 b...Listing by: -
$2,550,000 Active4 bds • 4 ba • 3,364 sqft
42 Hillside Terrace, Belmont, MA 02478
Nestled at the end of coveted Hillside Terrace this picturesque Colonial features 4 floors of sunlit, beautifully renovated living space. Welcoming foyer opens to the spacious living room with fireplace. Dining room with adjoining screen porch for al...Listing by: -
$2,600,000 Active4 bds • 5 ba • 3,601 sqft
4 Madison St, Belmont, MA 02478
This recently renovated Grand Tudor in the highly desirable Presidential neighborhood is situated on an oversized 7,664 corner lot. This home combines classic charm and modern sophistication delivering a light filled interior with an exceptional floo...Listing by: -
$2,695,000 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: -
$2,499,000 Active4 bds • 4 ba • 2,787 sqft
4 Griswold 3, Cambridge, MA 02138
"UNDER CONSTRUCTION" Unit 3 at The Griswold Collective offers a rare opportunity to own a detached luxury residence within a thoughtfully designed four-home micro-community in Cambridge Highlands. This home delivers the privacy of single-family livi...Listing by: -
$2,575,000 Active5 bds • 4 ba • 3,137 sqft
22 Garfield Rd., Belmont, MA 02478
Tranquil grounds envelop this gracious ten room residence blending timeless architecture and craftsmanship with modern amenities. An elegant foyer is flanked by a living room with custom built ins and gas fireplace, a dining room that opens to a chef...Listing by: -
$2,599,000 Active Under Contract9 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 5 rooms. There is an eat-in-kitchen that leads to a back porch overlooking a tree lined yard. Separate systems and laundry in each unit. Unit 1 has central air. In ad...Listing by: -
$2,500,000 Active6 bds • 3 ba • 3,159 sqft
17-19 Orrin Street, Cambridge, MA 02138
Handsome three-family property on a larger lot. Current leases in place through May 31, 2027 for units 1 & 3, and through September 1, 2026 for unit 2. The building features three sunny, floor-through units, each offering high ceilings, hardwood floo...Listing by: -
$2,750,000 Active5 bds • 4 ba • 3,423 sqft
96 Lexington Road, Lincoln, MA 01773
Majestically set at the end of a tree-lined drive, this distinguished 10-room residence captures the timeless elegance of classic New England living. Rich hardwood floors, paneled walls, gracious proportions & sun-filled interiors define this beautif...Listing by: -
$2,725,000 Active4 bds • 3 ba • 3,149 sqft
135 Milton Street, Milton, MA 02186
A rare and private Blue Hills retreat set on 2.6 wooded acres abutting conservation land, approached by a winding drive. Designed for those who value privacy and refined living, this exceptional property offers a peaceful escape just minutes from Bos...Listing by:
Similar Priced Comparison
-
$2,480,000 Active5 bds • 5 ba • 3600 sqft
37 Oakland St
- Home larger by 328 sqft
- Lot smaller by 10,405 sqft
- Newer by 100 years
Listing by: -
$2,270,000 Active Under Contract5 bds • 5 ba • 4507 sqft
319 Oakland St
- Home larger by 1,235 sqft
- Lot smaller by 4,575 sqft
- Older by 26 years
Listing by: -
$3,295,000 Active5 bds • 5 ba • 5105 sqft
18 Rockland Street
- Home larger by 1,833 sqft
- Lot smaller by 12,242 sqft
- Newer by 100 years
Listing by: -
$3,500,000 Active5 bds • 6 ba • 5800 sqft
144 Washington Street
- Home larger by 2,528 sqft
- Lot smaller by 12,214 sqft
- Newer by 100 years
Listing by: -
$2,395,000 Active Under Contract4 bds • 4 ba • 3610 sqft
10 Kirkland Circle
- Home larger by 338 sqft
- Lot smaller by 13,694 sqft
- Newer by 10 years
Listing by: -
$2,799,000 Active Under Contract5 bds • 6 ba • 5400 sqft
17 Whiting Way
- Home larger by 2,128 sqft
- Lot smaller by 15,418 sqft
- Newer by 100 years
Listing by: -
$2,899,000 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: -
$2,746,000 Active6 bds • 5 ba • 6114 sqft
57 Mayflower Rd
- Home larger by 2,842 sqft
- Lot smaller by 12,804 sqft
- Newer by 100 years
Listing by: -
$3,195,000 Active5 bds • 6 ba • 5735 sqft
31 Alba Rd
- Home larger by 2,463 sqft
- Lot smaller by 10,360 sqft
- Newer by 24 years
Listing by: -
$2,150,000 Active5 bds • 4 ba • 3704 sqft
77 Cedar Street
- Home larger by 432 sqft
- Lot smaller by 12,694 sqft
- Newer by 85 years
Listing by: -
$2,360,000 Active5 bds • 4 ba • 4000 sqft
11 Greenough St
- Home larger by 728 sqft
- Lot smaller by 15,853 sqft
- Newer by 100 years
Listing by: -
$2,250,000 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: -
$2,250,000 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: -
$2,725,000 Active7 bds • 6 ba • 6061 sqft
8 Noanett Rd
- 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: -
$3,325,000 Active2 bds • 3 ba • 1937 sqft
580 Washington Street 304
- Home smaller by 1,335 sqft
- Lot smaller by 23,694 sqft
- Newer by 89 years
Listing by: -
$2,975,000 Active2 bds • 3 ba • 1800 sqft
580 Washington Street 104
- Home smaller by 1,472 sqft
- Lot smaller by 23,694 sqft
- Newer by 89 years
Listing by: -
$2,885,000 Active5 bds • 4 ba • 4110 sqft
100 Albion Rd
- Home larger by 838 sqft
- Lot larger by 10,027 sqft
- Newer by 52 years
Listing by: -
$2,395,000 Active2 bds • 2 ba • 1374 sqft
100 Linden St 205
- Home smaller by 1,898 sqft
- Lot smaller by 23,694 sqft
- Newer by 95 years
Listing by: -
$3,400,000 Active10 bds • 9 ba • 10318 sqft
5-7 Abbott Street
- Home larger by 7,046 sqft
- Lot smaller by 13,466 sqft
- Older by 26 years
Listing by:
Nearby Locations
Communities
- Fells Homes For Sale
- Overbrook Homes For Sale
- Wellesley Hills Homes For Sale
- Cochituate Homes For Sale
- Needham Heights Homes For Sale
- Auburndale Homes For Sale
- Cochituate Homes For Sale
- Waban Homes For Sale
- Birds Hill Homes For Sale
- West Newton Homes For Sale
- Four Corners Homes For Sale
- Saxonville Homes For Sale
- Newtonville Homes For Sale
- Newton Centre Homes For Sale
- Oak Hill Homes For Sale
- Dexter Homes For Sale
- Bowen - Thompsonville Homes For Sale
- Watertown West End Homes For Sale
- West End Homes For Sale
- Downtown 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
- 02030 Homes For Sale
- 02494 Homes For Sale
- 02468 Homes For Sale
- 01778 Homes For Sale
- 02465 Homes For Sale
- 02453 Homes For Sale
- 02461 Homes For Sale
- 01770 Homes For Sale
- 02460 Homes For Sale
- 02451 Homes For Sale
- 02459 Homes For Sale
- 02052 Homes For Sale
- 02090 Homes For Sale
- 02452 Homes For Sale
- 02458 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
- Cochituate, MA Homes for Sale
- Dover, MA Homes for Sale
- Needham Heights, MA Homes for Sale
- Wayland, MA Homes for Sale
- Newton, MA Homes for Sale
- Sherborn, MA Homes for Sale
- Waltham, MA Homes for Sale
- Medfield, MA Homes for Sale
- Westwood, MA Homes for Sale
- Lincoln, MA Homes for Sale
- Dedham, MA Homes for Sale
- Framingham, MA Homes for Sale
- Watertown Town, MA Homes for Sale
- Millis, MA Homes for Sale
- East Holliston, MA Homes for Sale
- Sudbury, 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 in Country Club, Wellesley, MA 02481 is a single family listed at $2,850,000. Highlights include 4 bedrooms, 5 bathrooms, 3,272 sq. ft., built in 1926, 0.54 acre lot, $871 per sq. ft.. Realty.com has 42 photos, sales history, school insights, and mortgage tools for this listing.
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
Most 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: 30/100.
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 2026-07-08 00:45:27. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.