53 Windsor Rd
Wellesley, MA 02481
- 4 Beds
- 4.5 Baths
- 3,272 sqft (on 0.54 acres)
4 Beds
4.5 Baths
3,272 sqft
(on 0.54 acres)
Local Information
-- mins to
Description
Settled in the heart of Wellesley’s 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 Wellesley’s most desirable locations!
53 Windsor Rd, Wellesley, MA 02481 is a 4 bedroom, 5 bathroom, 3,272 sqft single-family home built in 1926. It last sold for $2,900,000 on Jul 24, 2025 (2% above the $2,850,000 asking price). It is currently off market. The Trulia Estimate is $2,991,300, with a rent estimate of $7,924/month.
Home Highlights
Parking
Garage
Outdoor
Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
164 days ago
Home Details for 53 Windsor Rd
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Interior Details Basement: Full,Finished,BulkheadNumber of Rooms: 9Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Master Bathroom, Bathroom 1, Bathroom 2, Dining Room, Family Room, Kitchen, Living Room, Office |
Beds & Baths Number of Bedrooms: 4Number of Bathrooms: 5Number of Bathrooms (full): 4Number of Bathrooms (half): 1 |
Dimensions and Layout Living Area: 3272 Square Feet |
Appliances & Utilities Utilities: for Gas Range, for Gas Oven, Washer HookupAppliances: Range, Disposal, Microwave, Refrigerator, Freezer, Washer, DryerDisposalDryerLaundry: Closet/Cabinets - Custom Built,First Floor,Washer HookupMicrowaveRefrigeratorWasher |
Heating & Cooling Heating: Baseboard,Natural GasHas CoolingAir Conditioning: Central Air,DuctlessHas HeatingHeating Fuel: Baseboard |
Fireplace & Spa Number of Fireplaces: 2Fireplace: Living RoomHas a FireplaceNo Spa |
Windows, Doors, Floors & Walls Door: French DoorsFlooring: Tile, Carpet, Hardwood, Flooring - Wall to Wall Carpet |
Levels, Entrance, & Accessibility Floors: Tile, Carpet, Hardwood, Flooring Wall To Wall Carpet |
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Exterior Home Features Roof: ShinglePatio / Porch: DeckExterior: Deck, Professional LandscapingFoundation: Concrete Perimeter |
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2Open Parking Spaces: 4No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 6Parking: Detached,Paved Drive,Off Street,Paved |
Frontage Not on Waterfront |
Water & Sewer Sewer: Public Sewer |
Finished Area Finished Area (above surface): 3272 |
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Year Built Year Built: 1926 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Cape |
Building Construction Materials: FrameNot Attached PropertyDoes Not Include Home Warranty |
Property Information Parcel Number: M:047 R:017 S:, 258301 |
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Price List Price: $2,850,000 |
Status Change & Dates Off Market Date: Sun Jun 01 2025 |
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MLS Status: Sold |
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Direction & Address City: WellesleyCommunity: Country Club |
School Information Elementary School: WellesleyJr High / Middle School: WellesleyHigh School: Wellesley |
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Building Area Building Area: 3272 Square Feet |
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Community Features: Public Transportation, Shopping, Walk/Jog Trails, Golf, Bike Path, Conservation Area, T-StationNot Senior Community |
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No HOA |
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Lot Area: 0.54 acres |
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BasementMls Number: 73381532Above Grade Unfinished Area: 3272 |
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Public TransportationShoppingWalk/Jog TrailsGolfBike PathConservation AreaT-Station |
Last check for updates: about 21 hours ago
Listed by Debi Benoit, (617) 962-9292
William Raveis R.E. & Home Services, (781) 235-5000
Bought with: Fleet Homes Group, (617) 831-1099, Keller Williams Realty, (617) 969-9000
Source: MLS PIN, MLS#73381532
Price History for 53 Windsor Rd
| Date | Price | Event | Source |
|---|---|---|---|
| 07/24/2025 | $2,900,000 | Sold | MLS PIN #73381532 |
| 06/02/2025 | $2,850,000 | Pending | William Raveis Real Estate, Mortgage & Insurance #73381532 |
| 05/28/2025 | $2,850,000 | Listed For Sale | MLS PIN #73381532 |
| 04/29/2021 | $2,290,000 | Sold | N/A |
| 04/04/2018 | $1,125,000 | Sold | N/A |
| 07/29/2013 | $1,191,000 | Sold | N/A |
| 06/07/2013 | $1,220,000 | PriceChange | Agent Provided |
| 05/05/2013 | $1,245,000 | PriceChange | Agent Provided |
| 04/16/2013 | $1,275,000 | Listed For Sale | Agent Provided |
| 10/02/2009 | $1,035,000 | Sold | N/A |
| 10/16/1996 | $555,000 | Sold | N/A |
| 05/31/1988 | $510,000 | Sold | N/A |
Market trends in Wellesley
Last updated May 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
111
3MoM
Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $25,083 |
| Assessment | $2,440,000 |
Home facts updated by county records
Comparable Sales for 53 Windsor Rd
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.07 | Single-Family Home | $2,600,000 | 01/09/26 | 4 | 3.5 | 3,705 | |
0.44 | Single-Family Home | $3,305,000 | 06/26/26 | 4 | 3.5 | 3,738 | |
0.51 | Single-Family Home | $2,833,000 | 05/19/26 | 4 | 3.5 | 4,151 | |
0.39 | Single-Family Home | $2,225,000 | 06/12/26 | 5 | 3.5 | 2,590 | |
0.54 | Single-Family Home | $2,354,000 | 12/24/25 | 4 | 4.5 | 4,211 | |
0.51 | Single-Family Home | $2,625,000 | 04/30/26 | 4 | 3.5 | 3,433 | |
0.50 | Single-Family Home | $2,625,000 | 11/03/25 | 4 | 3.5 | 4,720 | |
0.60 | Single-Family Home | $3,300,000 | 08/01/25 | 4 | 4.5 | 4,200 | |
0.71 | Single-Family Home | $2,350,000 | 07/30/25 | 4 | 4.5 | 4,300 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 53 Windsor Rd.
What Locals Say about Wellesley
At least 124 Trulia users voted on each feature.
92 % Say it's dog friendly
87 % Say parking is easy
85 % Say people would walk alone at night
84 % Say yards are well-kept
80 % Say car is needed
79 % Say there are sidewalks
76 % Say kids play outside
75 % Say there's holiday spirit
74 % Say streets are well-lit
73 % Say there's wildlife
72 % Say it's quiet
70 % Say they plan to stay for at least 5 years
67 % Say it's walkable to restaurants
66 % Say neighbors are friendly
65 % Say there are community events
63 % Say it's walkable to grocery stores
Sourced by Trulia users. Learn more about our methodology.
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Apartments for Rent
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Off Market Homes Near 53 Windsor Rd
The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.

