53 Windsor Rd, Wellesley, MA 02481
Property image
Property image
OFF MARKET

53 Windsor Rd
Wellesley, MA 02481

  • 4 Beds
  • 4.5 Baths
  • 3,272 sqft (on 0.54 acres)

$2,991,100

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $17,868/mo*
Refinance Your Home

$2,991,100

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $17,868/mo*
Refinance Your Home
4 Beds
4.5 Baths
3,272 sqft
(on 0.54 acres)

Home Value

Trulia Estimate
$2.99M
Since last month
Decreased$2K (-0.1%)
Since last year
Increased$78K (+2.7%)
Since last sale
Increased$88K (+3%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +99% in the last 10 years
MonthEstimated value
2026
August 2026$2.99M
July 2026$2.99M
June 2026$2.99M
May 2026$2.97M
March 2026$2.91M
February 2026$2.93M
January 2026$2.9M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
46 Lincoln Rd, Wellesley, MA
0.07
Single-Family Home
$2,600,000
01/09/26
4
3.5
3,705
117 Forest St, Wellesley, MA
0.44
Single-Family Home
$3,305,000
06/26/26
4
3.5
3,738
133 Abbott Rd, Wellesley, MA
0.25
Single-Family Home
$4,400,000
07/22/26
5
4.5
4,628
15 Standish Cir, Wellesley, MA
0.51
Single-Family Home
$2,833,000
05/19/26
4
3.5
4,151
120 Forest St, Wellesley, MA
0.39
Single-Family Home
$2,225,000
06/12/26
5
3.5
2,590
28 Clovelly Rd, Wellesley, MA
0.54
Single-Family Home
$2,354,000
12/24/25
4
4.5
4,211
15 Alden Rd, Wellesley, MA
0.51
Single-Family Home
$2,625,000
04/30/26
4
3.5
3,433
10 Allen Rd, Wellesley, MA
0.50
Single-Family Home
$2,625,000
11/03/25
4
3.5
4,720
23 Priscilla Cir, Wellesley, MA
0.41
Single-Family Home
$3,675,000
06/01/26
6
4.5
5,500
23 Inverness Rd, Wellesley, MA
0.19
Single-Family Home
$4,525,000
07/10/26
6
6.5
9,523

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
46 Lincoln Rd, Wellesley, MA 02481
0.07
$2,600,000
4
3.5
3,705
Recently Sold
8 Lincoln Cir, Wellesley, MA 02481
0.11
$2,774,300
4
3.5
3,548
Off Market
21 Windsor Rd, Wellesley, MA 02481
0.15
$2,918,100
6
4
4,954
Off Market
23 Inverness Rd, Wellesley, MA 02482
0.19
$4,525,000
6
6.5
9,523
Recently Sold
151 Oakland St, Wellesley, MA 02481
0.26
$3,695,000
6
5
6,990
For Sale
144 Oakland St, Wellesley, MA 02481
0.29
$1,665,800
4
2
1,950
Off Market
133 Abbott Rd, Wellesley, MA 02481
0.25
$4,400,000
5
4.5
4,628
Recently Sold
123 Abbott Rd, Wellesley, MA 02481
0.26
$5,961,300
6
6.5
7,424
Off Market
108 Abbott Rd, Wellesley, MA 02481
0.28
$6,187,500
6
7
7,037
Recently Sold
23 Priscilla Cir, Wellesley, MA 02481
0.41
$3,675,000
6
4.5
5,500
Recently Sold
75 Maugus Ave, Wellesley, MA 02481
0.39
$4,658,200
5
5.5
5,267
Off Market

Local Information

  • Map ViewExplore the area around 53 Windsor Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1926
Lot Size
0.54 acres
Living Area
3,272 sqft
Price/Sqft
$914
Parking
Garage

About this House

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 $2,991,100, with a rent estimate of $7,924/month.
Last check for updates: about 13 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

Home Details for 53 Windsor Rd

Interior Features

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

Exterior Features

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

Property Information

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

Price & Status

Price
List Price: $2,850,000
Status Change & Dates
Off Market Date: Sun Jun 01 2025

Active Status

MLS Status: Sold

Location

Direction & Address
City: WellesleyCommunity: Country Club
School Information
Elementary School: WellesleyJr High / Middle School: WellesleyHigh School: Wellesley

Building

Building Area
Building Area: 3272 Square Feet

Community

Community Features: Public Transportation, Shopping, Walk/Jog Trails, Golf, Bike Path, Conservation Area, T-StationNot Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.54 acres

Miscellaneous

BasementMls Number: 73381532Above Grade Unfinished Area: 3272

Additional Information

Public TransportationShoppingWalk/Jog TrailsGolfBike PathConservation AreaT-Station

Price and Tax history

DateEventPrice
Jul 24, 2025
Source: MLS PIN #73381532
Sold
$2,900,000
Jun 2, 2025
Source: William Raveis Real Estate, Mortgage & Insurance #73381532
Pending
$2,850,000
May 28, 2025
Source: MLS PIN #73381532
Listed For Sale
$2,850,000
Apr 29, 2021
Source: N/A
Sold
$2,290,000
Apr 4, 2018
Source: N/A
Sold
$1,125,000

Market trends in Wellesley

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.15M
$161KMoM
Sale-to-List Price
100.6%
0.4%MoM
Price per sq ft
$666
$18MoM
Available listings
87
25MoM

Around this home

View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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.
  • Mike Holiday
    "Everyone walks their dogs and lets their dogs say hello, most often. People know each other. It’s a great community"
    0
    Flag
  • Emilyperrottet
    "Nothing. It’s a changing neighborhood with a mix of old and new homes. Most of the homes are old and run down. "
    0
    Flag
  • Emilyperrottet
    "I take the Commuter rail from Wellesley to the T subway. 1.5 hours to Cambridge from south station. "
    0
    Flag
  • Trulia User
    "Lots of trails and other dogs in the area, many pet stores in the area as well. Dogs are well behaved and friendly. "
    0
    Flag
  • Shirley L.
    "The walking paths and yearly town celebrations are wonderful! A great sense of community and great schools. "
    0
    Flag
  • Sdipietro369
    "I am a visitor to this area. The neighborhood seems very nice with Babson College right around the corner. Shops within a close distance. "
    3
    Flag
  • Katrina C.
    "You feel you're kids are safe here in town. Everyone is friendly and we're all neighbors. It's a lovely town with a community feeling. "
    2
    Flag
  • Jamie.solomon1
    "I lived in Weston for two years and it’s a delightful town, with gorgeous land and large houses. Usually at least an acre"
    1
    Flag
  • Cmt138
    "Great access to commuter rail from either Wellesley Square or Wellesley Hills. Easy 10-15 min walk. Better parking from Wellesley Square. Usually takes about 1/2 hour to Back Bay. Driving into Boston can take a little more time with traffic to cross town to Mass Pike."
    2
    Flag
  • Laura M.
    "There are lots of dogs in our neighborhood- people walk them all the time. Dogs are welcome at Morse’s pond in the off season. "
    1
    Flag
  • Bruce C.
    "Lots of other dog owners who walk their dogs all the time. Also plenty of space to run with dogs on a trail or away from streets. "
    1
    Flag
  • Keith S.
    "Lots of trails and public spaces. Nationally acclaimed colleges. Variety of great shops and restaurants."
    0
    Flag
  • Srodousakis
    "Wellesley is a beautiful but very privileged neighborhood. It is very safe and people are friendly. Schools are great! There is a cute downtown and generally it’s a great place to raise kids. "
    0
    Flag
  • Molly R.
    "i love my neighborhood. everyone is so kind and welcoming. we often times have little gatherings or block parties. everyone knows each other and we are a very close community. "
    0
    Flag
  • Victoria V.
    "That I live on route 16 and nobody lets me out of my driveway in the morning and I have to leave for work an hour early just because of that."
    0
    Flag

LGBTQ Local Legal Protections

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.

Frequently asked questions about 53 Windsor Rd

  • What is 53 Windsor Rd estimated to be worth?
    Trulia's estimated value for 53 Windsor Rd in Wellesley, MA is $2,991,100.
  • What is the price history for 53 Windsor Rd?
    53 Windsor Rd in Wellesley, MA last sold for $2,900,000 in July 2025.
  • Is Wellesley a buyer's or seller's market?
    Wellesley is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Wellesley?
    The median sale price in Wellesley is $2.15M. That is up $161K from the prior month.
  • Does 53 Windsor Rd have air conditioning?
    Yes, 53 Windsor Rd in Wellesley, MA has air conditioning.
  • Does 53 Windsor Rd have laundry facilities?
    Yes, 53 Windsor Rd in Wellesley, MA has in-unit laundry.

Explore by feature - Pet Friendly

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