66 Windsor Rd, Wellesley, MA 02481
Property image
Property image
OFF MARKET

66 Windsor Rd
Wellesley, MA 02481

  • 5 Beds
  • 6 Baths
  • 5,026 sqft (on 0.57 acres)

$4,072,600

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $24,045/mo*
Refinance Your Home

$4,072,600

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $24,045/mo*
Refinance Your Home
5 Beds
6 Baths
5,026 sqft
(on 0.57 acres)

Home Value

Trulia Estimate
$4.07M
Since last month
Decreased$11K (-0.3%)
Since last year
Increased$129K (+3.3%)
Since last sale
Increased$1M (+49%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +61% in the last 10 years
MonthEstimated value
2026
August 2026$4.1M
July 2026$4.11M
June 2026$4.28M
May 2026$4.24M
April 2026$4.06M
March 2026$4.14M
February 2026$4.01M
January 2026$3.92M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
46 Lincoln Rd, Wellesley, MA
0.10
Single-Family Home
$2,600,000
01/09/26
4
3.5
3,705
133 Abbott Rd, Wellesley, MA
0.33
Single-Family Home
$4,400,000
07/22/26
5
4.5
4,628
22 Priscilla Cir, Wellesley, MA
0.37
Single-Family Home
$3,600,000
10/22/25
6
5.5
5,900
23 Priscilla Cir, Wellesley, MA
0.35
Single-Family Home
$3,675,000
06/01/26
6
4.5
5,500
15 Standish Cir, Wellesley, MA
0.44
Single-Family Home
$2,833,000
05/19/26
4
3.5
4,151
23 Inverness Rd, Wellesley, MA
0.27
Single-Family Home
$4,525,000
07/10/26
6
6.5
9,523
28 Clovelly Rd, Wellesley, MA
0.60
Single-Family Home
$2,354,000
12/24/25
4
4.5
4,211
10 Clark Rd, Wellesley, MA
0.45
Single-Family Home
$5,100,000
07/23/26
6
7
6,148
279 Oakland St, Wellesley, MA
0.65
Single-Family Home
$2,230,000
08/19/26
5
3.5
4,512
117 Forest St, Wellesley, MA
0.51
Single-Family Home
$3,305,000
06/26/26
4
3.5
3,738

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
53 Windsor Rd, Wellesley, MA 02481
0.08
$2,991,100
4
4.5
3,272
Off Market
46 Lincoln Rd, Wellesley, MA 02481
0.10
$2,600,000
4
3.5
3,705
Recently Sold
8 Lincoln Cir, Wellesley, MA 02481
0.12
$2,774,300
4
3.5
3,548
Off Market
21 Windsor Rd, Wellesley, MA 02481
0.22
$2,918,100
6
4
4,954
Off Market
144 Oakland St, Wellesley, MA 02481
0.23
$1,715,700
4
2
1,950
Off Market
23 Inverness Rd, Wellesley, MA 02482
0.27
$4,525,000
6
6.5
9,523
Recently Sold
133 Abbott Rd, Wellesley, MA 02481
0.33
$4,400,000
5
4.5
4,628
Recently Sold
123 Abbott Rd, Wellesley, MA 02481
0.34
$5,961,300
6
6.5
7,424
Off Market
108 Abbott Rd, Wellesley, MA 02481
0.35
$6,187,500
6
7
7,037
Recently Sold
23 Priscilla Cir, Wellesley, MA 02481
0.35
$3,675,000
6
4.5
5,500
Recently Sold
22 Priscilla Cir, Wellesley, MA 02481
0.37
$3,742,000
6
5.5
5,900
Off Market
59 Standish Rd, Wellesley, MA 02481
0.38
$2,496,900
7
6.5
5,914
Off Market

Local Information

  • Map ViewExplore the area around 66 Windsor Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1930
Lot Size
0.57 acres
Living Area
5,026 sqft
Price/Sqft
$810

About this House

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.
66 Windsor Rd, Wellesley, MA 02481 is a 5 bedroom, 7 bathroom, 5,026 sqft single-family home built in 1930. It last sold for $2,750,000 on Aug 3, 2021. It is currently off market. The Trulia Estimate is $4,072,600, with a rent estimate of $15,066/month.

Home Details for 66 Windsor Rd

Interior Features

Heating & Cooling
Heating: GasAir ConditioningHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 11
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1930Year Updated: 1999
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

Exterior Home Features
Exterior: Wood

Community

Units in Building: 1

Lot Information

Lot Area: 0.57 acres

Price and Tax history

DateEventPrice
Aug 3, 2021
Source: N/A
Sold
$2,750,000
Aug 10, 2018
Source: N/A
Sold
$2,400,000
May 30, 2018
Source: Agent Provided
PriceChange
$2,549,000
Price decreased by 5%
May 13, 2018
Source: Agent Provided
PendingToActive
$2,695,000
May 13, 2018
Source: Agent Provided
Pending
$2,695,000

Market trends in Wellesley

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.15M
$161KMoM
Sale-to-List Price
100.6%
0.4%MoM
Price per sq ft
$666
$18MoM
Available listings
87
25MoM

Around this home

View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Wellesley

At least 124 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 87 % Say parking is easy

  • 85 % Say people would walk alone at night

  • 84 % Say yards are well-kept

  • 80 % Say car is needed

  • 79 % Say there are sidewalks

  • 76 % Say kids play outside

  • 75 % Say there's holiday spirit

  • 74 % Say streets are well-lit

  • 73 % Say there's wildlife

  • 72 % Say it's quiet

  • 70 % Say they plan to stay for at least 5 years

  • 67 % Say it's walkable to restaurants

  • 66 % Say neighbors are friendly

  • 65 % Say there are community events

  • 63 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Mike Holiday
    "Everyone walks their dogs and lets their dogs say hello, most often. People know each other. It’s a great community"
    0
    Flag
  • Emilyperrottet
    "Nothing. It’s a changing neighborhood with a mix of old and new homes. Most of the homes are old and run down. "
    0
    Flag
  • Emilyperrottet
    "I take the Commuter rail from Wellesley to the T subway. 1.5 hours to Cambridge from south station. "
    0
    Flag
  • Trulia User
    "Lots of trails and other dogs in the area, many pet stores in the area as well. Dogs are well behaved and friendly. "
    0
    Flag
  • Shirley L.
    "The walking paths and yearly town celebrations are wonderful! A great sense of community and great schools. "
    0
    Flag
  • Sdipietro369
    "I am a visitor to this area. The neighborhood seems very nice with Babson College right around the corner. Shops within a close distance. "
    3
    Flag
  • Katrina C.
    "You feel you're kids are safe here in town. Everyone is friendly and we're all neighbors. It's a lovely town with a community feeling. "
    2
    Flag
  • Jamie.solomon1
    "I lived in Weston for two years and it’s a delightful town, with gorgeous land and large houses. Usually at least an acre"
    1
    Flag
  • Cmt138
    "Great access to commuter rail from either Wellesley Square or Wellesley Hills. Easy 10-15 min walk. Better parking from Wellesley Square. Usually takes about 1/2 hour to Back Bay. Driving into Boston can take a little more time with traffic to cross town to Mass Pike."
    2
    Flag
  • Laura M.
    "There are lots of dogs in our neighborhood- people walk them all the time. Dogs are welcome at Morse’s pond in the off season. "
    1
    Flag
  • Bruce C.
    "Lots of other dog owners who walk their dogs all the time. Also plenty of space to run with dogs on a trail or away from streets. "
    1
    Flag
  • Keith S.
    "Lots of trails and public spaces. Nationally acclaimed colleges. Variety of great shops and restaurants."
    0
    Flag
  • Srodousakis
    "Wellesley is a beautiful but very privileged neighborhood. It is very safe and people are friendly. Schools are great! There is a cute downtown and generally it’s a great place to raise kids. "
    0
    Flag
  • Molly R.
    "i love my neighborhood. everyone is so kind and welcoming. we often times have little gatherings or block parties. everyone knows each other and we are a very close community. "
    0
    Flag
  • Victoria V.
    "That I live on route 16 and nobody lets me out of my driveway in the morning and I have to leave for work an hour early just because of that."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 66 Windsor Rd

  • What is 66 Windsor Rd estimated to be worth?
    Trulia's estimated value for 66 Windsor Rd in Wellesley, MA is $4,072,600.
  • What is the price history for 66 Windsor Rd?
    66 Windsor Rd in Wellesley, MA last sold for $2,750,000 in August 2021.
  • Is Wellesley a buyer's or seller's market?
    Wellesley is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Wellesley?
    The median sale price in Wellesley is $2.15M. That is up $161K from the prior month.
  • How big is the lot at 66 Windsor Rd?
    The lot at 66 Windsor Rd in Wellesley, MA is about 0.57 acres (24,829 sq ft).

Explore by feature - Pet Friendly

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