OFF MARKET

Off market may 2025 for $2.2M

$2,297,492

Est. refi paymentEst. refi $1,767/mo

•

4,552

sq ft

20 Windsor Rd, Needham, MA 02492

About this home

20 Windsor Road is a charming home situated on an acre of land in Needham’s desirable estate neighborhood. As you enter, you'll be welcomed by the spacious entryway, the bright and oversized living and dining rooms, and an eat-in kitchen offering views of the spacious yard and new deck leading to the patio and backyard. The first floor also features a home office with its own deck and separate entrance. A few steps down, the large family room offers a bar, billiard area, and ample space for entertaining. This level also connects to the patio, yard, mudroom, and 2-car garage. Upstairs, enjoy new wood floors and three spacious bedrooms, one en suite and the other two sharing a renovated bathroom. Up a level, the oversized primary suite offers views of the yard, new California Closets, and a luxurious spa-like bathroom. The private, sprawling backyard is perfect for a pool, sports court, or any custom addition you desire.

Single-familyProperty Type

1962Year Built

1.05 acresLot Size

$505Est. Price/Sq.Ft.

2 garage spacesParking

Listed by The Samantha Eisenberg Group • Compass

Bought with The Samantha Eisenberg Group • Compass

Redfin checked: a minute ago

•Source:MLS PIN #73338878

Redfin Estimate

$2,297,492

$8,492 since sold in May 2025$9,000 since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 4.2% lower than the average sale price ($2.40M) of 6 comparable homes.

SOLD SEP 28, 2026
$1,530,000
A
4 beds3.5 baths3,560 sq ft
150 Dedham St, Dover, MA 02030
SOLD AUG 20, 2026
$2,700,000
B
3 beds3.5 baths5,149 sq ft
98 Bridle Trail Rd, Needham, MA 02492
SOLD FEB 25, 2026
$1,700,000
C
4 beds3.5 baths2,293 sq ft
362 Country Way, Needham, MA 02492
SOLD JUN 25, 2026
$2,650,000
D
5 beds4.5 baths7,023 sq ft
20 Burr Dr, Needham, MA 02492
SOLD JUN 22, 2026
$1,830,000
E
4 beds2.5 baths3,104 sq ft
88 Robinwood Ave, Needham, MA 02492
SOLD APR 16, 2026
$3,980,000
F
4 beds4 baths4,420 sq ft
37 Carleton Dr, Needham, MA 02492

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Earn from this home

Sell

$401,628

Est. take-home

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Est. cash available

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Rent

$6,815/mo

Redfin rental estimate

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Market trends in 02492, MA

Last updated October 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

99.4%

1.1% MoM

Median sale price

$1.7M

$42K MoM

Avg. days on market

27d

6 days MoM

Recently sold homes

4 MoM

New listings for sale

$2,786,000
6 beds5 baths6,100 sq ft
57 Mayflower Rd, Needham, MA 02492
$1,895,000
5 beds3 baths5,232 sq ft
178 South St, Needham, MA 02492
$1,875,000
5 beds4.5 baths3,548 sq ft
18 Grant St, Needham, MA 02492
$2,039,000
4 beds3.5 baths4,120 sq ft
829 Greendale Ave, Needham, MA 02492
$529,000
2 beds2 baths1,353 sq ft
1212 Greendale Ave #333, Needham, MA 02492
See all

Provided by Redfin

Sale history for 20 Windsor Rd

Date

Event

Price

MLS PIN #73338878

May 2, 2025

Sold

$2,289,000

$503/sq ft

Feb 26, 2025

Listed

$2,099,000

$461/sq ft

MLS PIN #72846007

Jul 30, 2021

Sold

$1,800,000

$395/sq ft

Jun 14, 2021

Contingent

—

Jun 9, 2021

Listed

$1,699,000

$373/sq ft

Beautiful colonial in estate area w/ a sophisticated interior design. Large sun filled living room includes fireplace, hardwood floors & area for the piano. Fabulously renovated kitchen w/ center island, Subzero & breakfast area has access to the deck & overlooks the level private one acre yard. The dining room provides a large open entertaining space to host holidays w/ friends & family. Just off the dining room is an office which has both a private deck & a separate entrance from the street. The enormous family room also looks out to the amazing yard. The master suite offers a beautiful updated spa like full bath & his & hers walk-in closets. Three additional bedrooms are on the second floor w/ two updated full baths. The lower level has an additional family room or excise room to complete this picturesque property. The oversized private back yard is a great setting for Pool, Tennis Court or Putting Green. Feel free to message me if you would like the Matteport video emailed to you

Public Records

Sep 1, 1983

Sold

$275,000

$60/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$21,543 (+11.8%)

$719,700 + $932,400

$1,652,100

2022

$19,276 (+14.9%)

$547,200 + $894,500

$1,441,700

2021

$16,783 (+0.9%)

$547,200 + $740,800

$1,288,000

2020

$16,632 (+1.1%)

$547,200 + $784,400

$1,331,600

2019

$16,453 (+4.3%)

$547,200 + $780,700

$1,327,900

2018

$15,775 (+7.4%)

$547,200 + $780,700

$1,327,900

2017

$14,690 (+10.5%)

$547,200 + $688,300

$1,235,500

2016

$13,294

$547,200 + $604,800

$1,152,000

2014

$13,286 (+7.5%)

$547,200 + $594,200

$1,141,400

2013

$12,361 (+3.2%)

$547,200 + $546,700

$1,093,900

2012

$11,978 (+3.9%)

$547,200 + $546,700

$1,093,900

2011

$11,533 (+3.5%)

$547,200 + $510,900

$1,058,100

2010

$11,142 (+5.7%)

$547,200 + $510,900

$1,058,100

2009

$10,539

$547,200 + $510,900

$1,058,100

Tax history for 20 Windsor Rd

Year

Property tax

Land + Additions

Assessment*

2023

$21,543 (+11.8%)

$719,700 + $932,400

$1,652,100

2022

$19,276 (+14.9%)

$547,200 + $894,500

$1,441,700

2021

$16,783 (+0.9%)

$547,200 + $740,800

$1,288,000

2020

$16,632 (+1.1%)

$547,200 + $784,400

$1,331,600

2019

$16,453 (+4.3%)

$547,200 + $780,700

$1,327,900

2018

$15,775 (+7.4%)

$547,200 + $780,700

$1,327,900

2017

$14,690 (+10.5%)

$547,200 + $688,300

$1,235,500

2016

$13,294

$547,200 + $604,800

$1,152,000

2014

$13,286 (+7.5%)

$547,200 + $594,200

$1,141,400

2013

$12,361 (+3.2%)

$547,200 + $546,700

$1,093,900

2012

$11,978 (+3.9%)

$547,200 + $546,700

$1,093,900

2011

$11,533 (+3.5%)

$547,200 + $510,900

$1,058,100

2010

$11,142 (+5.7%)

$547,200 + $510,900

$1,058,100

2009

$10,539

$547,200 + $510,900

$1,058,100

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

Public record

Public record
Permits

Beds

Baths

3.5

Stories

Lot width

—

Lot depth

—

Lot size

1.05 Acres

Year renovated

2010

Sq. Ft.

3,078

Year built

1962

Style

Single Family Residential

County

Norfolk County

APN

146055

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 21, 2023.

Property details

Parking

Parking Information
Has Garage
Has Open Parking
# of Garage Spaces: 2
# of Covered Spaces: 2
Parking Spaces: 6
AttachedGarageYN: Yes
Parking Features: Attached, Paved Drive

Interior

Master Bedroom Information
Area: 418
Length: 19
Width: 22
Features: Bathroom - Full,Closet/Cabinets - Custom Built,Flooring - Hardwood,Closet - Double

Bedroom #2 Information
Area: 224
Length: 16
Width: 14
Features: Bathroom - Full,Closet,Flooring - Hardwood,Recessed Lighting

Bedroom #3 Information
Area: 192
Length: 12
Width: 16
Features: Closet,Flooring - Hardwood,Recessed Lighting

Bedroom #4 Information
Area: 143
Length: 13
Width: 11
Features: Flooring - Hardwood,Closet - Double

Bathroom Information
# of Bathrooms (Full): 3
# of Bathrooms (Half): 1
Master Bathroom Features: Yes

Bathroom #1 Information
Features: Bathroom - Full,Bathroom - Tiled With Tub & Shower,Flooring - Stone/Ceramic Tile,Countertops - Stone/Granite/Solid,Double Vanity,Recessed Lighting,Remodeled

Bathroom #2 Information
Features: Bathroom - Tiled With Shower Stall,Flooring - Stone/Ceramic Tile,Countertops - Stone/Granite/Solid,Recessed Lighting,Remodeled

Bathroom #3 Information
Features: Bathroom - Full,Bathroom - Tiled With Tub,Flooring - Stone/Ceramic Tile,Countertops - Stone/Granite/Solid,Recessed Lighting,Remodeled

Living Room Information
Area: 420
Length: 20
Width: 21
Level: Main
Features: Flooring - Hardwood,Open Floorplan,Recessed Lighting

Family Room Information
Area: 756
Length: 28
Width: 27
Features: Bathroom - Half,Closet/Cabinets - Custom Built,Flooring - Hardwood,Exterior Access,Open Floorplan,Recessed Lighting

Dining Room Information
Area: 180
Length: 15
Width: 12
Level: Main
Features: Flooring - Hardwood,Window(s) - Picture,Open Floorplan,Recessed Lighting

Kitchen Information
Area: 240
Length: 16
Width: 15
Level: Main
Features: Flooring - Stone/Ceramic Tile,Window(s) - Picture,Dining Area,Countertops - Stone/Granite/Solid,Kitchen Island,Cabinets - Upgraded,Deck - Exterior,Dryer Hookup - Electric,Exterior Access,Recessed Lighting,Stainless Steel Appliances,Washer Hookup,Lighting - Pendant

Office Room Information
Area: 180
Length: 12
Width: 15
Level: Main
Features: Closet/Cabinets - Custom Built,Flooring - Wall to Wall Carpet,Deck - Exterior,Slider

Basement Information
Basement: Finished

Laundry Information
Laundry Features: Electric Dryer Hookup, Washer Hookup

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 3
Fireplace Features: Family Room, Living Room

Interior Features
# of Rooms (Total): 10
Flooring: Tile, Vinyl, Carpet, Hardwood, Flooring - Wall to Wall Carpet, Flooring - Vinyl
Interior Features: Closet/Cabinets - Custom Built, Slider, Walk-In Closet(s), Cedar Closet(s), Bathroom - Half, Home Office, Play Room, Bathroom

Exterior

Building Information
Building Area (Total): 4,552
Foundation Details: Concrete Perimeter
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Actual

Exterior Features
Fencing: Fenced/Enclosed, Fenced
Roof: Shingle
Patio And Porch Features: Deck - Exterior, Porch, Deck, Patio
Exterior Features: Porch, Deck, Patio, Rain Gutters, Storage, Professional Landscaping, Sprinkler System, Fenced Yard

Property Information
PropertySubType: Single Family Residence
Levels: Multi/Split

Lot Information
Lot Size (Acres): 1.05
Road Frontage Type: Public
Road Responsibility: Public Maintained Road

Financial

Tax Information
Tax Annual Amount: $21,497
Tax Year: 2024

Utilities

Utility Information
Utilities: for Electric Range, for Electric Oven, for Electric Dryer, Washer Hookup, Icemaker Connection
Sewer: Private Sewer
Water Source: Public
Electric: 200+ Amp Service

Heating & Cooling
Has Heating
Has Cooling
Heating: Baseboard, Oil, Ductless
Cooling: Central Air, Ductless

Location

Location Information
Directions: Country Way to Stratford to Windsor.
UnparsedAddress: 20 Windsor Road, Needham MA 02492

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Pool, Tennis Court(s), Park, Walk/Jog Trails, Stable(s), Golf, Medical Facility, Bike Path, Conservation Area, Highway Access, House of Worship, Private School, Public School, T-Station, University

Public facts

Beds: 4
Baths: 3.5
Sq. Ft.: 3,078
Stories: 1.0
Lot Size: 1.05 acres
Style: Single Family Residential
Year Built: 1962
Year Renovated: 2010
County: Norfolk County
APN: 146055

Home facts updated by county records on Jul 21, 2023

Other

Miscellaneous Information
Heat Zones: 5

Listing Information
StandardStatus: Closed

Around this home

Schools

K - 12
Preschool & daycare

High Rock School

Public 6 • Assigned • 1.1mi

10/10

Needham High School

Public 9-12 • Assigned • 2.2mi

9/10

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

3/10 Fire Factor

0.15% chance of being in a wildfire in next 30 years

5/10 Heat Factor

7 days above 96° 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

Needham, MA • 02492

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

$2.18M – $2.64M

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Deeded parking • $859 HOA • Parking

Home values near 20 Windsor Rd

Data from public records.

Address	Redfin Estimate
29 Windsor Road, Needham, MA 5 Beds \| 4 Baths \| 4191 Sq. Ft.	$2,307,042
70 Windsor Road, Needham, MA 4 Beds \| 3 Baths \| 3726 Sq. Ft.	$2,142,766
1 Windsor Road, Needham, MA 6 Beds \| 9 Baths \| 10334 Sq. Ft.	—
79 Stratford Road, Needham, MA 5 Beds \| 3.5 Baths \| 3594 Sq. Ft.	$1,992,756
88 Stratford Road, Needham, MA 4 Beds \| 3.5 Baths \| 3902 Sq. Ft.	$2,292,530
324 Country Way, Needham, MA 2 Beds \| 2.5 Baths \| 1874 Sq. Ft.	—
325 Country Way, Needham, MA 5 Beds \| 2.5 Baths \| 3499 Sq. Ft.	$1,814,304

Address	Redfin Estimate
51 Windsor Road, Needham, MA 4 Beds \| 3.5 Baths \| 3566 Sq. Ft.	$1,921,584
50 Windsor Road, Needham, MA 5 Beds \| 3.5 Baths \| 4300 Sq. Ft.	$2,157,776
30 Windsor Road, Needham, MA 4 Beds \| 3 Baths \| 4360 Sq. Ft.	$2,206,041
91 Stratford Road, Needham, MA 5 Beds \| 3.5 Baths \| 5200 Sq. Ft.	$2,574,214
34 Stratford Road, Needham, MA 7 Beds \| 7.5 Baths \| 10047 Sq. Ft.	$5,425,781
304 Country Way, Needham, MA 4 Beds \| 2.5 Baths \| 3270 Sq. Ft.	$2,649,901
339 Country Way, Needham, MA 5 Beds \| 2.5 Baths \| 2945 Sq. Ft.	$2,027,519

Address	Redfin Estimate
69 Windsor Road, Needham, MA 6 Beds \| 6.5 Baths \| 6890 Sq. Ft.	$3,776,850
40 Windsor Road, Needham, MA 5 Beds \| 4.5 Baths \| 5930 Sq. Ft.	$4,056,023
63 Stratford Road, Needham, MA 3 Beds \| 3 Baths \| 2300 Sq. Ft.	$1,508,957
103 Stratford Road, Needham, MA 4 Beds \| 2.5 Baths \| 2514 Sq. Ft.	$1,597,242
8 Stratford Road, Needham, MA 5 Beds \| 3.5 Baths \| 3715 Sq. Ft.	$1,954,489
15 White Pine Road, Needham, MA 5 Beds \| 4.5 Baths \| 4685 Sq. Ft.	$2,403,138
48 Moseley Avenue, Needham, MA 3 Beds \| 3 Baths \| 1409 Sq. Ft.	$1,167,816

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About this home

Redfin Estimate

Earn from this home

Market trends in 02492, MA

Sale history for 20 Windsor Rd

Tax history for 20 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 02492

Home values near 20 Windsor Rd

More real estate resources