OFF MARKET

Off Market Jul 2025 for $2.9M

$3,212,932

Est. refi paymentEst. refi $4,562/mo

•

3,272

sq ft

53 Windsor Rd, Wellesley, MA 02481

About this home

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!

Single-familyProperty Type

1926Year Built

0.54 acresLot Size

$982Est. Price/Sq.Ft.

2 garage spacesParking

Listed by Debi Benoit • William Raveis R.E. & Home Services

Bought with Fleet Homes Group • Keller Williams Realty

Redfin checked: a minute ago

•Source:MLS PIN #73381532

Redfin Estimate

$3,212,932

$313K since sold in July 2025$24K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 22.5% higher than the average sale price ($2.62M) of 6 comparable homes.

SOLD JUN 26, 2026
$3,305,000
A
4 beds3.5 baths3,738 sq ft
117 Forest St, Wellesley, MA 02481
SOLD JAN 9, 2026
$2,600,000
B
4 beds3.5 baths3,705 sq ft
46 Lincoln Rd, Wellesley, MA 02481
SOLD JUN 12, 2026
$2,225,000
C
5 beds3.5 baths2,590 sq ft
120 Forest St, Wellesley, MA 02481
SOLD MAY 19, 2026
$2,833,000
D
4 beds3.5 baths4,151 sq ft
15 Standish Cir, Wellesley, MA 02481
SOLD JUN 10, 2026
$2,090,000
E
4 beds3.5 baths3,283 sq ft
4 Fiske Rd, Wellesley, MA 02481
SOLD JUL 16, 2026
$2,690,000
F
4 beds3.5 baths4,761 sq ft
21 Elm St, Wellesley, MA 02481

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Earn from this home

Sell

$777,699

Est. take-home

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Refinance

Est. cash available

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Rent

$5,414/mo

Redfin rental estimate

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Market trends in 02481, MA

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

101.8%

+0.1% MoM

Median sale price

$2.4M

$26K MoM

Avg. days on market

15d

0 days MoM

Recently sold homes

25 MoM

New listings for sale

OPEN FRI, 3PM TO 4:30PM
$1,995,000
4 beds3.5 baths3,216 sq ft
186 Oakland St, Wellesley, MA 02481
$3,595,000
6 beds5 baths6,525 sq ft
151 Oakland St, Wellesley, MA 02481
$5,450,000
5 beds7 baths7,632 sq ft
44 Whiting Rd, Wellesley, MA 02481
3D WALKTHROUGH
$1,395,000
4 beds2.5 baths1,800 sq ft
560 Worcester St, Wellesley, MA 02481
EARLY ACCESS
$2,049,000
3 beds3 baths4,366 sq ft
53 Sheridan Rd, Wellesley, MA 02481
$1,950,000
3 beds1.5 baths1,595 sq ft
53 Elmwood Rd, Wellesley, MA 02481
See all

Provided by Redfin

Sale history for 53 Windsor Rd

Date

Event

Price

MLS PIN #73381532

Jul 24, 2025

Sold

$2,900,000

$886/sq ft

May 28, 2025

Listed

$2,850,000

$871/sq ft

MLS PIN #71509295

Jul 29, 2013

Sold

$1,191,000

$364/sq ft

Jun 10, 2013

Contingent

—

Jun 7, 2013

Price Changed

$1,220,000

$373/sq ft

May 4, 2013

Price Changed

$1,245,000

$381/sq ft

May 4, 2013

Relisted

—

Apr 26, 2013

Contingent

—

Apr 15, 2013

Listed

$1,275,000

$390/sq ft

+16

Enchanting updated Cape nestled in the heart of the Country Club offers open floor plan and generous rooms. Living room with beamed ceiling and oversized fireplace leads to dining room with french doors and picture windows. Kitchen incl center island, hw floors and expansive eat in area with exterior access to deck. Sun filled family room overlooks private, level back yard. Fabulous lower level incl playroom, exercise room & full bath. Close to town, train and shops! A rare opportunity!

MLS PIN #70872490

Oct 1, 2009

Sold

$1,035,000

$316/sq ft

Aug 4, 2009

Contingent

—

Jul 16, 2009

Price Changed

$1,099,000

$336/sq ft

Jun 29, 2009

Relisted

—

Jun 26, 2009

Contingent

—

May 8, 2009

Price Changed

$1,220,000

$373/sq ft

Feb 5, 2009

Listed

$1,299,000

$397/sq ft

Rare Country Club offering. Woodsy setting in highly coveted location of more expensive homes. First floor: LR w/fireplace, elegant DR, informal dining area, library/bedroom, family room and half bath off kitchen. Second floor: 3 bedrooms with en suite baths. LL offers ample storage, finished playroom, full bath, bonus room with bedroom potential, separate entrance. Improvements include 2007 economical 7-zone gas furnace. Over-sized detached 2C garage w/workshop. Close to commuter rail & shops.

MLS PIN #50334191

Oct 15, 1996

Sold

$555,000

$170/sq ft

Jun 26, 1996

Listing Removed

—

Jun 4, 1996

Listed

$575,000

$176/sq ft

Public Records

May 31, 1988

Sold

$510,000

$156/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$24,583 (+12.3%)

$1,313,000 + $834,000

$2,147,000

2022

$21,888 (+16.2%)

$1,176,000 + $698,000

$1,874,000

2021

$18,835 (+1.6%)

$1,095,000 + $508,000

$1,603,000

2020

$18,531 (+12.9%)

$1,095,000 + $508,000

$1,603,000

2019

$16,418 (+18.5%)

$1,137,000 + $282,000

$1,419,000

2018

$13,850 (+1.4%)

$894,000 + $265,000

$1,159,000

2017

$13,653 (+1.8%)

$893,000 + $265,000

$1,158,000

2016

$13,415 (+2.3%)

$878,000 + $256,000

$1,134,000

2015

$13,109 (+3.6%)

$879,000 + $255,000

$1,134,000

2014

$12,648 (+4.4%)

$779,000 + $317,000

$1,096,000

2013

$12,110 (+1.9%)

$730,000 + $305,000

$1,035,000

2012

$11,882 (+9.3%)

$730,000 + $305,000

$1,035,000

2011

$10,870 (+5.3%)

$681,000 + $270,000

$951,000

2010

$10,323 (−2.9%)

$730,000 + $255,000

$985,000

2009

$10,635

$908,000 + $215,000

$1,123,000

Tax history for 53 Windsor Rd

Year

Property tax

Land + Additions

Assessment*

2023

$24,583 (+12.3%)

$1,313,000 + $834,000

$2,147,000

2022

$21,888 (+16.2%)

$1,176,000 + $698,000

$1,874,000

2021

$18,835 (+1.6%)

$1,095,000 + $508,000

$1,603,000

2020

$18,531 (+12.9%)

$1,095,000 + $508,000

$1,603,000

2019

$16,418 (+18.5%)

$1,137,000 + $282,000

$1,419,000

2018

$13,850 (+1.4%)

$894,000 + $265,000

$1,159,000

2017

$13,653 (+1.8%)

$893,000 + $265,000

$1,158,000

2016

$13,415 (+2.3%)

$878,000 + $256,000

$1,134,000

2015

$13,109 (+3.6%)

$879,000 + $255,000

$1,134,000

2014

$12,648 (+4.4%)

$779,000 + $317,000

$1,096,000

2013

$12,110 (+1.9%)

$730,000 + $305,000

$1,035,000

2012

$11,882 (+9.3%)

$730,000 + $305,000

$1,035,000

2011

$10,870 (+5.3%)

$681,000 + $270,000

$951,000

2010

$10,323 (−2.9%)

$730,000 + $255,000

$985,000

2009

$10,635

$908,000 + $215,000

$1,123,000

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

4.5

Stories

Lot width

—

Lot depth

—

Lot size

0.54 Acres

Year renovated

2018

Sq. Ft.

3,272

Year built

1926

Style

Single Family Residential

County

Norfolk County

APN

258301

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 20, 2023.

Property details

Parking

Parking Information
Has Garage
Has Open Parking
# of Garage Spaces: 2
# of Covered Spaces: 2
Parking Spaces: 4
Parking Features: Detached, Paved Drive, Off Street, Paved

Interior

Master Bedroom Information
Area: 288
Length: 16
Width: 18
Level: Second
Features: Bathroom - Full,Closet - Linen,Closet,Flooring - Wall to Wall Carpet

Bedroom #2 Information
Area: 168
Length: 14
Width: 12
Level: Second
Features: Bathroom - Full,Walk-In Closet(s),Flooring - Hardwood

Bedroom #3 Information
Area: 120
Length: 12
Width: 10
Level: Second
Features: Bathroom - Full,Closet,Flooring - Hardwood

Bathroom Information
# of Bathrooms (Full): 4
# of Bathrooms (Half): 1
Master Bathroom Features: Yes

Bathroom #1 Information
Level: First
Features: Bathroom - Half,Flooring - Stone/Ceramic Tile

Bathroom #2 Information
Level: Basement
Features: Bathroom - Full,Flooring - Stone/Ceramic Tile

Living Room Information
Area: 286
Length: 22
Width: 13
Level: Main,First
Features: Beamed Ceilings,Flooring - Hardwood,Window(s) - Picture,French Doors,Open Floorplan,Recessed Lighting

Family Room Information
Area: 225
Length: 15
Width: 15
Level: Main,First
Features: Skylight,Flooring - Wall to Wall Carpet,Exterior Access,Open Floorplan,Recessed Lighting

Dining Room Information
Area: 176
Length: 16
Width: 11
Level: Main,First
Features: Coffered Ceiling(s),Flooring - Hardwood,Window(s) - Picture,Open Floorplan

Kitchen Information
Area: 156
Length: 12
Width: 13
Level: Main,First
Features: Flooring - Hardwood,Dining Area,Countertops - Stone/Granite/Solid,Kitchen Island,Deck - Exterior,Open Floorplan,Recessed Lighting

Office Room Information
Area: 144
Length: 16
Width: 9
Level: First
Features: Closet,Closet/Cabinets - Custom Built,Flooring - Wall to Wall Carpet,Exterior Access

Basement Information
Basement: Full, Finished, Bulkhead

Laundry Information
Laundry Features: Closet/Cabinets - Custom Built, First Floor, Washer Hookup

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 2
Fireplace Features: Living Room

Interior Features
# of Rooms (Total): 9
Door Features: French Doors
Flooring: Tile, Carpet, Hardwood, Flooring - Wall to Wall Carpet
Interior Features: Closet, Closet/Cabinets - Custom Built, Cable Hookup, Recessed Lighting, Home Office, Exercise Room, Play Room

Exterior

Building Information
Building Area (Total): 3,272
Foundation Details: Concrete Perimeter
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Actual
Color: Grey

Exterior Features
Roof: Shingle
Patio And Porch Features: Deck
Exterior Features: Deck, Professional Landscaping

Property Information
PropertySubType: Single Family Residence

Lot Information
Lot Size (Acres): 0.54
Lot Features: Level

Financial

Tax Information
Tax Annual Amount: $25,083
Tax Year: 2025

Utilities

Utility Information
Utilities: for Gas Range, for Gas Oven, Washer Hookup
Sewer: Public Sewer
Water Source: Public

Heating & Cooling
Has Heating
Has Cooling
Heating: Baseboard, Natural Gas
Cooling: Central Air, Ductless

Location

Location Information
Directions: Abbott Road to Windsor Road
UnparsedAddress: 53 Windsor Rd, Wellesley MA 02481

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Walk/Jog Trails, Golf, Bike Path, Conservation Area, T-Station

Public facts

Beds: 3
Baths: 4.5
Sq. Ft.: 3,272
Stories: 2.0
Lot Size: 0.54 acres
Style: Single Family Residential
Year Built: 1926
Year Renovated: 2018
County: Norfolk County
APN: 258301

Home facts updated by county records on Jul 20, 2023

Other

Miscellaneous Information
Heat Zones: 7

Listing Information
StandardStatus: Closed

Around this home

Schools

Joseph E. Fiske Elementary School

Public K-5 • Assigned • 1.0mi

10/10

Wellesley Middle School

Public 6-8 • Assigned • 1.3mi

8/10

Wellesley High School

Public 9-12 • Assigned • 0.8mi

10/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

5/10 Heat Factor

7 days above 97° expected this year, 15 days in 30 years

6/10 Wind Factor

54% chance of strong winds in next 30 years

2/10 Air Factor

1 unhealthy days expected this year, 2 days in 30 years

Provided by First Street

Historical weather

Wellesley, MA • 02481

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 9 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

9 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$3.05M – $3.70M

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New listings for sale in 02481

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3D WALKTHROUGH

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EARLY ACCESSCOMPASS COMING SOON

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Home values near 53 Windsor Rd

Data from public records.

Address	Redfin Estimate
69 Windsor Rd, Wellesley, MA 5 Beds \| 3.5 Baths \| 2861 Sq. Ft.	$2,828,023
45 Windsor Rd, Wellesley, MA 4 Beds \| 3 Baths \| 2815 Sq. Ft.	$2,810,202

Address	Redfin Estimate
33 Windsor Rd, Wellesley, MA 5 Beds \| 4.5 Baths \| 4601 Sq. Ft.	$4,135,200
49 Windsor Rd, Wellesley, MA 3 Beds \| 4 Baths \| 3541 Sq. Ft.	$3,316,922

Address	Redfin Estimate
39 Windsor Rd, Wellesley, MA 6 Beds \| 7 Baths \| 6560 Sq. Ft.	$4,324,966
57 Windsor Rd, Wellesley, MA 5 Beds \| 5.5 Baths \| 4500 Sq. Ft.	$3,293,663

Property information provided by MLS PIN when last listed in 2025. This data may not match . Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 02481, MA

Sale history for 53 Windsor Rd

Tax history for 53 Windsor Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 02481

Home values near 53 Windsor Rd

More real estate resources