Google street view image for 20 Windsor Rd, Wellesley, MA 02481

Off market may 1995 for $710K

$3,037,369

Est. refi paymentEst. refi $2,763/mo

•

5 ba

•

5,393

sq ft

20 Windsor Rd, Wellesley, MA 02481

About this home

20 Windsor Rd is a 5,393 square foot house on a 0.34 acre lot with 6 bedrooms and 5 bathrooms. - it last sold on May 12, 1995 for $710,000. Based on Redfin's Wellesley data, we estimate the home's value is $3,037,369.

Single-familyProperty Type

1935Year Built

0.34 acresLot Size

$563Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$3,037,369

$2.3M since sold in May 1995$85K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 16% lower than the average sale price ($3.62M) of 6 comparable homes.

SOLD OCT 29, 2026
$2,900,000
A
5 beds3.5 baths4,054 sq ft
104 Fairbanks Ave, Wellesley, MA 02481
SOLD OCT 9, 2026
$5,005,000
B
6 beds4.5 baths7,013 sq ft
32 Arlington Rd, Wellesley, MA 02481
SOLD AUG 14, 2026
$2,565,000
C
5 beds5 baths5,000 sq ft
47 Rolling Ln, Needham, MA 02492
SOLD JUL 22, 2026
$4,400,000
D
5 beds4.5 baths4,628 sq ft
133 Abbott Rd, Wellesley, MA 02481
SOLD JUN 1, 2026
$3,675,000
E
6 beds4.5 baths5,500 sq ft
23 Priscilla Cir, Wellesley, MA 02481
SOLD SEP 10, 2026
$3,150,000
F
5 beds4.5 baths5,105 sq ft
18 Rockland St, Wellesley Hills, MA 02481

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Earn from this home

Sell

$2,885,837

Est. take-home

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Est. cash available

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Rent

$6,338/mo

Redfin rental estimate

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Market trends in 02481, MA

Last updated October 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

98.1%

0.6% MoM

Median sale price

$2.3M

$359K MoM

Avg. days on market

19d

0 days MoM

Recently sold homes

6 MoM

New listings for sale

$3,395,000
5 beds4.5 baths4,834 sq ft
32 Wall St, Wellesley, MA 02481
See all

Provided by Redfin

Sale history for 20 Windsor Rd

Year

Property tax

Land + Additions

Assessment*

2023

$25,831 (+0.9%)

$1,044,000 + $1,212,000

$2,256,000

2022

$25,591 (+2.4%)

$935,000 + $1,256,000

$2,191,000

2021

$24,992 (+1.6%)

$871,000 + $1,256,000

$2,127,000

2020

$24,588 (−1.6%)

$871,000 + $1,256,000

$2,127,000

2019

$24,980 (−4.6%)

$903,000 + $1,256,000

$2,159,000

2018

$26,182 (+1.3%)

$856,000 + $1,335,000

$2,191,000

2017

$25,844 (+0.1%)

$857,000 + $1,335,000

$2,192,000

2015

$25,813 (+1.1%)

$842,000 + $1,391,000

$2,233,000

2014

$25,526 (−6.4%)

$746,000 + $1,466,000

$2,212,000

2013

$27,261 (+1.9%)

$700,000 + $1,630,000

$2,330,000

2012

$26,748 (−10.9%)

$700,000 + $1,630,000

$2,330,000

2011

$30,004 (+7.1%)

$653,000 + $1,972,000

$2,625,000

2010

$28,013 (+7.4%)

$700,000 + $1,973,000

$2,673,000

2009

$26,080

$871,000 + $1,883,000

$2,754,000

Tax history for 20 Windsor Rd

Year

Property tax

Land + Additions

Assessment*

2023

$25,831 (+0.9%)

$1,044,000 + $1,212,000

$2,256,000

2022

$25,591 (+2.4%)

$935,000 + $1,256,000

$2,191,000

2021

$24,992 (+1.6%)

$871,000 + $1,256,000

$2,127,000

2020

$24,588 (−1.6%)

$871,000 + $1,256,000

$2,127,000

2019

$24,980 (−4.6%)

$903,000 + $1,256,000

$2,159,000

2018

$26,182 (+1.3%)

$856,000 + $1,335,000

$2,191,000

2017

$25,844 (+0.1%)

$857,000 + $1,335,000

$2,192,000

2015

$25,813 (+1.1%)

$842,000 + $1,391,000

$2,233,000

2014

$25,526 (−6.4%)

$746,000 + $1,466,000

$2,212,000

2013

$27,261 (+1.9%)

$700,000 + $1,630,000

$2,330,000

2012

$26,748 (−10.9%)

$700,000 + $1,630,000

$2,330,000

2011

$30,004 (+7.1%)

$653,000 + $1,972,000

$2,625,000

2010

$28,013 (+7.4%)

$700,000 + $1,973,000

$2,673,000

2009

$26,080

$871,000 + $1,883,000

$2,754,000

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

Property details

Interior

Basement Information
Basement Sq. Ft: 600
Basement Type: Full

Bathroom Information
# of Full Baths: 4
# of 1/2 Baths: 2

Heating & Cooling
Heating Type: Forced Air

Fireplace Information
# of Fireplaces: 3
Has Fireplace

Room Information
# of Rooms: 12

Exterior

Exterior Information
Physical Condition: Average
Building Style Type: Colonial
Construction Type: Frame
Exterior Wall: Wood Siding/Shingle

Property Information
Living Sq. Ft: 5,393
# of Units: 1
# of Stories: 3

Lot Information
# of Buildings: 1
Land Sq. Ft: 14,810
Municipality Name: WELLESLEY
Acres: 0.34
Zoning Code: SR20
State Use Description: 1-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2023

Public facts

Beds: 6
Baths: 5.0
Sq. Ft.: 5,393
Stories: 3.0
Lot Size: 0.34 acres
Style: Single Family Residential
Year Built: 1935
Year Renovated: 1996
County: Norfolk County
APN: 258718

Home facts updated by county records on Jul 20, 2023

Around this home

Schools

K - 12
Preschool & daycare

Joseph E. Fiske Elementary School

Public K-5 • Assigned • 1.1mi

10/10

Wellesley Middle School

Public 6-8 • Assigned • 1.2mi

8/10

Wellesley High School

Public 9-12 • Assigned • 0.7mi

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

58% 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

$2.89M – $3.49M

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Nearby similar homes

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3 beds2 baths1,474 sq ft

56 Curve St, Wellesley, MA 02482

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22 Cedar St, Wellesley, MA 02482

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$1,450,000

5 beds2 baths1,705 sq ft

764 Central Ave, Needham, MA 02492

Ornamental pond • Convenient access • Recreational space

$1,775,000

4 beds2.5 baths3,342 sq ft

14 Powder House Cir, Needham, MA 02492

Spacious kitchen • Ample storage • 0.24 acre lot

$1,995,000

5 beds3.5 baths3,850 sq ft

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Single floor living • Elevator • Wine cellar

New listings for sale in 02481

$3,395,000

5 beds4.5 baths4,834 sq ft

32 Wall St, Wellesley, MA 02481

Gourmet kitchen • Oversized island • Bespoke cabinetry

Home values near 20 Windsor Rd

Data from public records.

Address	Redfin Estimate
33 Windsor Road, Wellesley, MA 5 Beds \| 4.5 Baths \| 4601 Sq. Ft.	$4,209,937
38 Windsor Road, Wellesley, MA 5 Beds \| 7 Baths \| 7750 Sq. Ft.	$6,852,891
24 Windsor Road, Wellesley, MA 5 Beds \| 4 Baths \| 3741 Sq. Ft.	$2,655,452
11 Windsor Road, Wellesley, MA 4 Beds \| 2.5 Baths \| 2119 Sq. Ft.	$2,135,174
8 Inverness Road, Wellesley, MA 5 Beds \| 2.5 Baths \| 3127 Sq. Ft.	$2,370,565
60 Arlington Road, Wellesley, MA 5 Beds \| 5.5 Baths \| 5440 Sq. Ft.	$4,385,648
108 Abbott Road, Wellesley, MA 6 Beds \| 7 Baths \| 7037 Sq. Ft.	$6,024,407

Address	Redfin Estimate
39 Windsor Road, Wellesley, MA 6 Beds \| 7 Baths \| 6560 Sq. Ft.	$4,101,809
28 Windsor Road, Wellesley, MA 5 Beds \| 6.5 Baths \| 5287 Sq. Ft.	$4,362,224
21 Windsor Road, Wellesley, MA 6 Beds \| 4 Baths \| 4954 Sq. Ft.	$3,212,421
27 Windsor Road, Wellesley, MA 6 Beds \| 3 Baths \| 2916 Sq. Ft.	$2,877,787
20 Inverness Road, Wellesley, MA 5 Beds \| 6.5 Baths \| 4911 Sq. Ft.	$3,738,682
117 Abbott Road, Wellesley, MA 6 Beds \| 7 Baths \| 7555 Sq. Ft.	$5,234,605
112 Abbott Road, Wellesley, MA 5 Beds \| 5 Baths \| 4654 Sq. Ft.	$3,355,366

Address	Redfin Estimate
46 Windsor Road, Wellesley, MA 5 Beds \| 4 Baths \| 3751 Sq. Ft.	$3,215,777
14 Windsor Road, Wellesley, MA 6 Beds \| 3.5 Baths \| 3787 Sq. Ft.	$3,239,996
15 Windsor Road, Wellesley, MA 5 Beds \| 3.5 Baths \| 2972 Sq. Ft.	$3,388,783
8 Windsor Road, Wellesley, MA 6 Beds \| 5 Baths \| 4921 Sq. Ft.	$3,379,311
14 Inverness Road, Wellesley, MA 3 Beds \| 3.5 Baths \| 2591 Sq. Ft.	$2,674,778
113 Abbott Road, Wellesley, MA 6 Beds \| 3.5 Baths \| 3449 Sq. Ft.	$3,462,877
11 Inverness Road, Wellesley, MA 5 Beds \| 3.5 Baths \| 3217 Sq. Ft.	$3,255,241

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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 20 Windsor Rd

Tax history for 20 Windsor Rd

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 20 Windsor Rd

More real estate resources