OFF MARKET

Off Market Nov 2023 for $2.3M

$3,050,318

Est. refi paymentEst. refi $1,241/mo

•

4,954

sq ft

21 Windsor Rd, Wellesley, MA 02481

About this home

Built in 1913, this stately stucco colonial is located in the sought-after Country Club neighborhood and offers classic charm with modern day conveniences. 12 gracious rooms, 6 bedrooms, 3 full baths, and 2 half baths sit on more than a half-acre of land. The elegant first floor with high ceilings & exposed beams includes a renovated kitchen, large formal dining room, expansive front-to-back family room, and cozy sunroom. The second floor can be accessed via the front or back staircase and enjoys 4 bedrooms & 2 full baths. The fully finished third floor has an additional bedroom & full bath, plus a huge bonus room/6th bedroom. There’s ample storage in the basement as well as a private office. With close proximity to the middle school & high school, the Wellesley Hills train stop, and the Mass Pike & Rte 95, this timeless treasure is ideally located for today's urban/suburban lifestyle!

Single-familyProperty Type

1913Year Built

0.54 acresLot Size

$616Est. Price/Sq.Ft.

1 garage spacesParking

Listed by The Madden David Real Estate Group • Coldwell Banker Realty - Wellesley

Bought with The Lara & Chelsea Collaborative • Gibson Sotheby's International Realty

Redfin checked: a few seconds ago

•Source:MLS PIN #73146566

Redfin Estimate

$3,050,318

$715K since sold in November 2023$5,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 4.9% higher than the average sale price ($2.91M) of 6 comparable homes.

SOLD JUL 22, 2026
$4,400,000
A
5 beds4.5 baths4,628 sq ft
133 Abbott Rd, Wellesley, MA 02481
SOLD AUG 14, 2026
$2,700,000
B
5 beds4.5 baths6,032 sq ft
47 Longfellow Rd, Wellesley, MA 02481
SOLD JUL 16, 2026
$2,690,000
C
4 beds3.5 baths4,761 sq ft
21 Elm St, Wellesley, MA 02481
SOLD JUL 8, 2026
$2,935,000
D
5 beds3.5 baths4,364 sq ft
49 Whittier Rd, Wellesley, MA 02481
SOLD APR 29, 2026
$2,500,000
E
6 beds4 baths3,694 sq ft
25 Washburn Ave, Wellesley, MA 02481
SOLD JUN 12, 2026
$2,225,000
F
5 beds3.5 baths2,590 sq ft
120 Forest St, Wellesley, MA 02481

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Earn from this home

Sell

$1,126,144

Est. take-home

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Refinance

Est. cash available

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Rent

$5,679/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 21 Windsor Rd

Date

Event

Price

MLS PIN #73146566

Nov 3, 2023

Sold

$2,335,000

$471/sq ft

Aug 15, 2023

Contingent

—

Aug 9, 2023

Listed

$2,565,000

$518/sq ft

MLS PIN #72450251

May 30, 2019

Sold

$1,875,000

$378/sq ft

Mar 30, 2019

Pending

—

Feb 6, 2019

Listed

$1,995,000

$403/sq ft

+24

Stucco & stone,copper & slate,beamed & coffered ceilings create the perfect image a craftsman's masterpiece.Enter the vestibule to the grand foyer with gracious curved bridal staircase.The livingrm with beamed ceilings &mahogany paneled fireplace is lined with built-ins perfect for well loved books,family photos or personal treasures.The lounge is bathed in sunlight from a dozen french windows creating a wall of light.After sunset the room is warmed by the glow of a cozy fireplace.Welcome yr guests to the banquet sized diningrm with bay window and flanked by decorative keystone windows.The Master bedrm rivals the comforts of a country inn.Three additional bedrms round out the 2nd floor.One bedroom,a perfect guest room with a fireplace trimmed with blue Delft tiles.The third flr has a large bedroom with a study or 6th bedroom and a 4 piece bath.Unlimited possibilities to create a private suite,hideaway,family room or home theater.Treat yourself to a tour of this Country Club classic.

Public Records

Mar 1, 1992

Sold

$195,000

$39/sq ft

Public Records

Dec 1, 1982

Sold

$312,000

$63/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$21,457 (−1.7%)

$1,312,000 + $562,000

$1,874,000

2022

$21,818 (+3.9%)

$1,176,000 + $692,000

$1,868,000

2021

$20,997 (+1.6%)

$1,095,000 + $692,000

$1,787,000

2020

$20,658 (−1.9%)

$1,095,000 + $692,000

$1,787,000

2019

$21,057 (+7.4%)

$1,135,000 + $685,000

$1,820,000

2018

$19,610 (+1.4%)

$893,000 + $748,000

$1,641,000

2017

$19,347 (+2.7%)

$893,000 + $748,000

$1,641,000

2015

$18,831 (−3.4%)

$878,000 + $751,000

$1,629,000

2014

$19,491 (+5.6%)

$779,000 + $910,000

$1,689,000

2013

$18,463 (+12.4%)

$730,000 + $848,000

$1,578,000

2012

$16,428 (+1.4%)

$730,000 + $701,000

$1,431,000

2011

$16,196 (+5.4%)

$681,000 + $736,000

$1,417,000

2010

$15,364 (+1.6%)

$730,000 + $736,000

$1,466,000

2009

$15,124

$908,000 + $689,000

$1,597,000

Tax history for 21 Windsor Rd

Year

Property tax

Land + Additions

Assessment*

2023

$21,457 (−1.7%)

$1,312,000 + $562,000

$1,874,000

2022

$21,818 (+3.9%)

$1,176,000 + $692,000

$1,868,000

2021

$20,997 (+1.6%)

$1,095,000 + $692,000

$1,787,000

2020

$20,658 (−1.9%)

$1,095,000 + $692,000

$1,787,000

2019

$21,057 (+7.4%)

$1,135,000 + $685,000

$1,820,000

2018

$19,610 (+1.4%)

$893,000 + $748,000

$1,641,000

2017

$19,347 (+2.7%)

$893,000 + $748,000

$1,641,000

2015

$18,831 (−3.4%)

$878,000 + $751,000

$1,629,000

2014

$19,491 (+5.6%)

$779,000 + $910,000

$1,689,000

2013

$18,463 (+12.4%)

$730,000 + $848,000

$1,578,000

2012

$16,428 (+1.4%)

$730,000 + $701,000

$1,431,000

2011

$16,196 (+5.4%)

$681,000 + $736,000

$1,417,000

2010

$15,364 (+1.6%)

$730,000 + $736,000

$1,466,000

2009

$15,124

$908,000 + $689,000

$1,597,000

*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

Stories

Lot width

—

Lot depth

—

Lot size

0.54 Acres

Year renovated

—

Sq. Ft.

4,098

Year built

1913

Style

Single Family Residential

County

Norfolk County

APN

258720

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: 1
# of Covered Spaces: 1
Parking Spaces: 6
Parking Features: Detached, Paved Drive, Off Street

Interior

Master Bedroom Information
Area: 324
Length: 18
Width: 18
Level: Second
Features: Bathroom - Full

Bedroom #2 Information
Area: 180
Length: 15
Width: 12
Level: Second
Features: Flooring - Hardwood

Bedroom #3 Information
Area: 180
Length: 15
Width: 12
Level: Second
Features: Flooring - Hardwood

Bedroom #4 Information
Area: 110
Length: 11
Width: 10
Level: Second
Features: Flooring - Hardwood

Bedroom #5 Information
Area: 230
Length: 23
Width: 10
Level: Third
Features: Flooring - Hardwood

Bathroom Information
# of Bathrooms (Full): 3
# of Bathrooms (Half): 2
Master Bathroom Features: Yes

Bathroom #1 Information
Level: Second
Features: Bathroom - With Shower Stall

Bathroom #2 Information
Level: Second
Features: Bathroom - Tiled With Tub & Shower

Bathroom #3 Information
Level: Third
Features: Bathroom - With Tub & Shower

Living Room Information
Area: 432
Length: 24
Width: 18
Level: First
Features: Flooring - Hardwood

Family Room Information
Area: 242
Length: 22
Width: 11
Level: First
Features: Flooring - Hardwood

Dining Room Information
Area: 306
Length: 18
Width: 17
Level: First
Features: Flooring - Hardwood

Kitchen Information
Area: 304
Length: 19
Width: 16
Level: First
Features: Countertops - Stone/Granite/Solid

Basement Information
Basement: Full, Partially Finished, Walk-Out Access, Sump Pump

Laundry Information
Laundry Dimen: 13X12
Laundry Features: In Basement, Electric Dryer Hookup, Washer Hookup

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 4
Fireplace Features: Family Room, Living Room, Bedroom

Interior Features
# of Rooms (Total): 12
Flooring: Tile, Carpet, Hardwood, Flooring - Hardwood
Interior Features: Bathroom - Half, Bedroom, Bathroom

Exterior

Building Information
Building Area (Total): 4,954
Foundation Details: Concrete Perimeter
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Actual,Renovated Since
Color: Cream

Exterior Features
Roof: Slate
Patio And Porch Features: Patio
Exterior Features: Patio, Professional Landscaping, Sprinkler System, Garden, Stone Wall

Property Information
PropertySubType: Single Family Residence

Lot Information
Lot Size (Acres): 0.54
Road Frontage Type: Public

Financial

Tax Information
Tax Annual Amount: $21,457
Tax Year: 2023

Utilities

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

Heating & Cooling
Has Heating
Has Cooling
Heating: Baseboard, Natural Gas, Fireplace(s)
Cooling: Window Unit(s)

Location

Location Information
Directions: Abbott Road to Windsor Road
UnparsedAddress: 21 Windsor Rd, Wellesley MA 02481

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Tennis Court(s), Park, Walk/Jog Trails, Golf, Conservation Area, Highway Access, Private School, Public School, T-Station, University

Public facts

Beds: 6
Baths: 4.0
Sq. Ft.: 4,098
Stories: 3.0
Lot Size: 0.54 acres
Style: Single Family Residential
Year Built: 1913
Year Renovated: —
County: Norfolk County
APN: 258720

Home facts updated by county records on Jul 20, 2023

Other

Miscellaneous Information
Heat Zones: 1

Listing Information
Exclusions: Excludes Sunroom Chandelier, Mounted Tvs, Washers, Dryer & Refrigerator In Basement.
StandardStatus: Closed

Around this home

Schools

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

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

$2.90M – $3.51M

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Nearby similar homes

OPEN FRI, 3PM TO 4:30PM

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186 Oakland St, Wellesley, MA 02481

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New listings for sale in 02481

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 ACCESSCOMPASS COMING SOON

$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

Home values near 21 Windsor Rd

Data from public records.

Address	Redfin Estimate
33 Windsor Road, Wellesley, MA 5 Beds \| 4.5 Baths \| 4601 Sq. Ft.	$4,135,200
46 Windsor Road, Wellesley, MA 5 Beds \| 4 Baths \| 3751 Sq. Ft.	$3,403,674

Address	Redfin Estimate
39 Windsor Road, Wellesley, MA 6 Beds \| 7 Baths \| 6560 Sq. Ft.	$4,324,966
38 Windsor Road, Wellesley, MA 5 Beds \| 7 Baths \| 7750 Sq. Ft.	$6,702,538

Address	Redfin Estimate
45 Windsor Road, Wellesley, MA 4 Beds \| 3 Baths \| 2815 Sq. Ft.	$2,810,202
28 Windsor Road, Wellesley, MA 5 Beds \| 6.5 Baths \| 5287 Sq. Ft.	$4,461,060

Property information provided by MLS PIN when last listed in 2023. 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 21 Windsor Rd

Tax history for 21 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 21 Windsor Rd

More real estate resources