OFF MARKET

Off Market Aug 2021 for $2.7M

$3,633,882

•

5,026

sq ft

66 Windsor Rd, Wellesley, MA 02481

About this home

Beautifully sited on over half an acre in the heart of the Country Club neighborhood. The sprawling first floor offers a sophisticated fireplaced living room w custom built-in cabinets, two home offices and spectacular screened porch. Enter the gourmet chef's kitchen w an open floor plan and eat-in area that flows effortlessly into the fabulous sun-filled, two-story fireplaced family room w an exquisite wall of windows looking out to sweeping views of the lush manicured grounds abutting Wellesley's Centennial Park. The impressive primary suite includes a fireplace, generous master bathroom, sitting area, and two walk-in closets. Two additional bedrooms, two en suite bedrooms, laundry room, and a full bathroom complete the second floor. The lower level offers ample, versatile space that includes an exercise room, playroom, bonus room, and fifth full bath w shower. A heated three-car garage and sizeable mudroom complete this fabulous property. Move right in and make this home your own!

Single-familyProperty Type

1924Year Built

0.57 acresLot Size

$723Est. Price/Sq.Ft.

3 garage spacesParking

Listed by Benoit | Robinson | ORourke • Gibson Sotheby's International Realty

Bought with Benoit | Robinson | ORourke • Gibson Sotheby's International Realty

Redfin checked: a minute ago

•Source:MLS PIN #72830323

Redfin Estimate

$3,633,882

$884K since sold in August 2021$40K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 6.9% higher than the average sale price ($3.40M) 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 JUL 23, 2026
$5,100,000
B
6 beds7 baths6,148 sq ft
10 Clark Rd, Wellesley, MA 02481
SOLD JUL 8, 2026
$2,935,000
C
5 beds3.5 baths4,364 sq ft
49 Whittier Rd, Wellesley, MA 02481
SOLD AUG 14, 2026
$2,565,000
D
5 beds5 baths5,000 sq ft
47 Rolling Ln, Needham, MA 02492
SOLD AUG 14, 2026
$2,700,000
E
5 beds4.5 baths6,032 sq ft
47 Longfellow 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

$1,466,787

Est. take-home

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Rent

$5,803/mo

Redfin rental estimate

List your home for rent

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 66 Windsor Rd

Date

Event

Price

MLS PIN #72830323

Aug 3, 2021

Sold

$2,750,000

$547/sq ft

May 28, 2021

Contingent

—

May 12, 2021

Listed

$2,850,000

$567/sq ft

MLS PIN #72318999

Aug 10, 2018

Sold

$2,400,000

$478/sq ft

Jul 12, 2018

Pending

—

May 30, 2018

Price Changed

$2,549,000

$507/sq ft

May 12, 2018

Relisted

—

May 4, 2018

Pending

—

May 2, 2018

Listed

$2,695,000

$536/sq ft

+19

An exceptional property set in one of Wellesley's most sought after locations. Abutting Centennial Park and in the heart of the Wellesley Country Club area, this gorgeous home has it all. The sensational two-story family room has a grand stone fireplace and a wall of windows that provides sweeping views of glorious grounds through every season. The generous-sized kitchen has rich wood cabinetry, an expansive center island and a breakfast area that is filled with natural light and views. There is a front-to- back living room with fireplace and built-ins, an elegant dining room and a study. Each of the bedrooms are spacious and three are ensuite, including the master with its four walk in closets and tastefully designed bath. The finished lower level has two playrooms and a workshop area. This very special property is complete with a three-car garage and central air conditioning . This is a home to treasure! Close to shops, the train and restaurants.

Year

Property tax

Land + Additions

Assessment*

2023

$30,926 (−1.1%)

$1,342,000 + $1,359,000

$2,701,000

2022

$31,267 (+9.6%)

$1,203,000 + $1,474,000

$2,677,000

2021

$28,529 (+1.5%)

$1,120,000 + $1,308,000

$2,428,000

2020

$28,102 (−1.7%)

$1,120,000 + $1,311,000

$2,431,000

2019

$28,601 (+6.5%)

$1,161,000 + $1,311,000

$2,472,000

2018

$26,864 (+1.4%)

$858,000 + $1,390,000

$2,248,000

2017

$26,504 (+1.1%)

$858,000 + $1,390,000

$2,248,000

2015

$26,207 (+0.8%)

$843,000 + $1,424,000

$2,267,000

2014

$26,011 (−9.0%)

$748,000 + $1,506,000

$2,254,000

2013

$28,583 (+3.7%)

$701,000 + $1,742,000

$2,443,000

2012

$27,575

$701,000 + $1,701,000

$2,402,000

2011

$27,569 (+7.0%)

$654,000 + $1,758,000

$2,412,000

2010

$25,770 (+9.5%)

$701,000 + $1,758,000

$2,459,000

2009

$23,542

$872,000 + $1,614,000

$2,486,000

Tax history for 66 Windsor Rd

Year

Property tax

Land + Additions

Assessment*

2023

$30,926 (−1.1%)

$1,342,000 + $1,359,000

$2,701,000

2022

$31,267 (+9.6%)

$1,203,000 + $1,474,000

$2,677,000

2021

$28,529 (+1.5%)

$1,120,000 + $1,308,000

$2,428,000

2020

$28,102 (−1.7%)

$1,120,000 + $1,311,000

$2,431,000

2019

$28,601 (+6.5%)

$1,161,000 + $1,311,000

$2,472,000

2018

$26,864 (+1.4%)

$858,000 + $1,390,000

$2,248,000

2017

$26,504 (+1.1%)

$858,000 + $1,390,000

$2,248,000

2015

$26,207 (+0.8%)

$843,000 + $1,424,000

$2,267,000

2014

$26,011 (−9.0%)

$748,000 + $1,506,000

$2,254,000

2013

$28,583 (+3.7%)

$701,000 + $1,742,000

$2,443,000

2012

$27,575

$701,000 + $1,701,000

$2,402,000

2011

$27,569 (+7.0%)

$654,000 + $1,758,000

$2,412,000

2010

$25,770 (+9.5%)

$701,000 + $1,758,000

$2,459,000

2009

$23,542

$872,000 + $1,614,000

$2,486,000

*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

0.57 Acres

Year renovated

1999

Sq. Ft.

5,004

Year built

1924

Style

Single Family Residential

County

Norfolk County

APN

258306

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: 3
# of Covered Spaces: 3
Parking Spaces: 7
AttachedGarageYN: Yes
Parking Features: Attached, Heated Garage, Paved Drive, Off Street, Paved

Interior

Master Bedroom Information
Area: 272
Length: 16
Width: 17
Level: Second
Features: Bathroom - Full,Vaulted Ceiling(s),Walk-In Closet(s),Hot Tub / Spa,Recessed Lighting,Lighting - Sconce

Bedroom #2 Information
Area: 143
Length: 13
Width: 11
Level: Second
Features: Closet,Flooring - Hardwood,Crown Molding

Bedroom #3 Information
Area: 130
Length: 13
Width: 10
Level: Second
Features: Closet,Flooring - Hardwood,Crown Molding

Bedroom #4 Information
Area: 182
Length: 14
Width: 13
Level: Second
Features: Bathroom - Full,Walk-In Closet(s),Flooring - Hardwood,Crown Molding

Bedroom #5 Information
Area: 270
Length: 15
Width: 18
Level: Second
Features: Bathroom - Full,Ceiling Fan(s),Vaulted Ceiling(s),Flooring - Hardwood

Bathroom Information
# of Bathrooms (Full): 5
# of Bathrooms (Half): 2
Main Level Bathrooms: 2
Master Bathroom Features: Yes

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

Bathroom #2 Information
Level: Main,First
Features: Bathroom - Half,Flooring - Stone/Ceramic Tile,Pedestal Sink

Bathroom #3 Information
Level: Second
Features: Bathroom - Full,Flooring - Stone/Ceramic Tile

Living Room Information
Area: 299
Length: 13
Width: 23
Level: Main,First
Features: Closet/Cabinets - Custom Built,Flooring - Hardwood,French Doors,Exterior Access,Lighting - Sconce,Crown Molding

Family Room Information
Area: 552
Length: 23
Width: 24
Level: Main,First
Features: Skylight,Flooring - Hardwood,Recessed Lighting

Dining Room Information
Area: 168
Length: 14
Width: 12
Level: Main,First
Features: Flooring - Hardwood,Crown Molding

Kitchen Information
Area: 273
Length: 21
Width: 13
Level: Main,First
Features: Flooring - Hardwood,Dining Area,French Doors,Breakfast Bar / Nook,Exterior Access,Open Floorplan,Recessed Lighting,Stainless Steel Appliances,Gas Stove,Lighting - Pendant,Crown Molding

Office Room Information
Area: 110
Length: 10
Width: 11
Level: Main
Features: Exterior Access

Basement Information
Basement: Full, Partially Finished, Sump Pump

Laundry Information
Laundry Features: Flooring - Stone/Ceramic Tile, Sink, Second Floor

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

Appliances
Other Equipment: Intercom

Interior Features
# of Rooms (Total): 14
Door Features: French Doors
Window Features: Skylight
Flooring: Tile, Concrete, Hardwood, Flooring - Stone/Ceramic Tile, Flooring - Wall to Wall Carpet
Interior Features: Closet/Cabinets - Custom Built, Bathroom - Full, Recessed Lighting, Lighting - Overhead, Office, Bathroom, Bonus Room, Play Room, Exercise Room

Exterior

Building Information
Building Area (Total): 5,026
Foundation Details: Concrete Perimeter
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Actual
Color: Cream

Exterior Features
Roof: Shingle
Patio And Porch Features: Screened, Deck
Exterior Features: Porch - Screened, Deck, Rain Gutters, Hot Tub/Spa, Professional Landscaping, Sprinkler System, Stone Wall

Pool Information
Has Spa
Spa Features: Private

Property Information
PropertySubType: Single Family Residence
Security Features: Security System

Lot Information
Lot Size (Acres): 0.57
Road Surface Type: Paved
Road Frontage Type: Public

Financial

Tax Information
Tax Annual Amount: $28,529
Tax Year: 2021

Utilities

Utility Information
Utilities: for Gas Range, Icemaker Connection
Sewer: Public Sewer
Water Source: Public

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

Location

Location Information
Directions: Abbott Road to Windsor Road
UnparsedAddress: 66 Windsor Rd, Wellesley MA 02481

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Park, Walk/Jog Trails, Golf, Conservation Area

Public facts

Beds: 5
Baths: 6.0
Sq. Ft.: 5,004
Stories: 2.0
Lot Size: 0.57 acres
Style: Single Family Residential
Year Built: 1924
Year Renovated: 1999
County: Norfolk County
APN: 258306

Home facts updated by county records on Jul 20, 2023

Other

Miscellaneous Information
Heat Zones: 16

Listing Information
Exclusions: See List Agent.
StandardStatus: Closed

Around this home

Schools

Joseph E. Fiske Elementary School

Public K-5 • Assigned • 0.9mi

10/10

Wellesley Middle School

Public 6-8 • Assigned • 1.4mi

8/10

Wellesley High School

Public 9-12 • Assigned • 0.9mi

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

$3.45M – $4.18M

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Home values near 66 Windsor Rd

Data from public records.

Address	Redfin Estimate
4 Windsor Rd, Wellesley, MA 3 Beds \| 2.5 Baths \| 2618 Sq. Ft.	$2,333,422
49 Windsor Rd, Wellesley, MA 3 Beds \| 4 Baths \| 3541 Sq. Ft.	$3,316,922

Address	Redfin Estimate
69 Windsor Rd, Wellesley, MA 5 Beds \| 3.5 Baths \| 2861 Sq. Ft.	$2,828,023
53 Windsor Rd, Wellesley, MA 4 Beds \| 4.5 Baths \| 3272 Sq. Ft.	$3,212,932

Address	Redfin Estimate
45 Windsor Rd, Wellesley, MA 4 Beds \| 3 Baths \| 2815 Sq. Ft.	$2,810,202
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 2021. 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 66 Windsor Rd

Tax history for 66 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 66 Windsor Rd

More real estate resources