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

38 Windsor Rd
Wellesley, MA 02481

  • 5 Beds
  • 7 Baths
  • 7,750 sqft (on 0.62 acres)

$6,126,700

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $36,295/mo*
Refinance Your Home

$6,126,700

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $36,295/mo*
Refinance Your Home
5 Beds
7 Baths
7,750 sqft
(on 0.62 acres)

Home Value

Trulia Estimate
$6.13M
Since last month
Decreased$51K (-0.8%)
Since last year
Decreased$315K (-4.9%)
Since last sale
Increased$915K (+17.6%)
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 +358% in the last 10 years
MonthEstimated value
2026
August 2026$6.13M
July 2026$6.18M
June 2026$6.35M
May 2026$6.27M
April 2026$6.28M
March 2026$6.24M
February 2026$6.05M
January 2026$5.95M
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
23 Inverness Rd, Wellesley, MA
0.15
Single-Family Home
$4,525,000
07/10/26
6
6.5
9,523
108 Abbott Rd, Wellesley, MA
0.19
Single-Family Home
$6,187,500
11/12/25
6
7
7,037
10 Clark Rd, Wellesley, MA
0.31
Single-Family Home
$5,100,000
07/23/26
6
7
6,148
133 Abbott Rd, Wellesley, MA
0.20
Single-Family Home
$4,400,000
07/22/26
5
4.5
4,628
46 Lincoln Rd, Wellesley, MA
0.15
Single-Family Home
$2,600,000
01/09/26
4
3.5
3,705
18 Maugus Ave, Wellesley, MA
0.59
Single-Family Home
$5,775,000
05/01/26
8
7
7,366
22 Priscilla Cir, Wellesley, MA
0.46
Single-Family Home
$3,600,000
10/22/25
6
5.5
5,900
51 Abbott Rd, Wellesley, MA
0.46
Single-Family Home
$2,700,000
09/03/25
6
4.5
7,830
117 Forest St, Wellesley, MA
0.36
Single-Family Home
$3,305,000
06/26/26
4
3.5
3,738
23 Priscilla Cir, Wellesley, MA
0.43
Single-Family Home
$3,675,000
06/01/26
6
4.5
5,500

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
21 Windsor Rd, Wellesley, MA 02481
0.07
$2,918,100
6
4
4,954
Off Market
53 Windsor Rd, Wellesley, MA 02481
0.09
$2,991,100
4
4.5
3,272
Off Market
46 Lincoln Rd, Wellesley, MA 02481
0.15
$2,600,000
4
3.5
3,705
Recently Sold
23 Inverness Rd, Wellesley, MA 02482
0.15
$4,525,000
6
6.5
9,523
Recently Sold
108 Abbott Rd, Wellesley, MA 02481
0.19
$6,187,500
6
7
7,037
Recently Sold
123 Abbott Rd, Wellesley, MA 02481
0.19
$5,961,300
6
6.5
7,424
Off Market
8 Lincoln Cir, Wellesley, MA 02481
0.19
$2,774,300
4
3.5
3,548
Off Market
133 Abbott Rd, Wellesley, MA 02481
0.20
$4,400,000
5
4.5
4,628
Recently Sold
86 Abbott Rd, Wellesley, MA 02481
0.29
$2,277,100
4
3
2,801
Off Market
75 Maugus Ave, Wellesley, MA 02481
0.31
$4,604,600
5
5.5
5,267
Off Market
144 Oakland St, Wellesley, MA 02481
0.32
$1,715,700
4
2
1,950
Off Market
10 Clark Rd, Wellesley, MA 02481
0.31
$5,100,000
6
7
6,148
Recently Sold

Local Information

  • Map ViewExplore the area around 38 Windsor Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2020
Lot Size
0.62 acres
Living Area
7,750 sqft
Price/Sqft
$791
Parking
Garage

About this House

Introducing 38 Windsor Road. Situated in the heart of Wellesley's coveted Country Club location. This 17 room custom built home exceeds all expectations with unparalleled craftsmanship, functionality of design while sited to maximize the hilltop wooded views to the back yard conservation land. Over 7750 sq ft of living space on 3 floors with walkout lower level plus a 3 car heated garage. Extensive landscape architect design plan with oversized patio and built-in grill. Designed for everyday living along with fabulous spaces for entertaining. The luxuries of multiple office/work spaces and exercise room , wine room, bar/entertainment area and sports simulator space have been carefully integrated into this home. Enjoy short distance to train, coffee shops, Babson and Wellesley Country Club with access to walking trails from your backyard.
38 Windsor Rd, Wellesley, MA 02481 is a 5 bedroom, 8 bathroom, 7,750 sqft single-family home built in 2020. It last sold for $5,211,250 on Nov 13, 2020. It is currently off market. The Trulia Estimate is $6,126,700, with a rent estimate of $7,994/month.

Home Details for 38 Windsor Rd

Interior Features

Interior Details
BasementAtticNumber of Rooms: 11
Heating & Cooling
Heating: Forced Air, Radiant, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
Cable ReadyDishwasherDisposalMicrowaveRefrigerator
Fireplace & Spa
FireplaceHot Tub or Spa
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: WoodPatioSprinkler System
Parking & Garage
GarageParking Spaces: 8Parking: Garage Attached

Property Information

Year Built
Year Built: 2020
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.62 acres

Building

Pool
Sauna

Price and Tax history

DateEventPrice
Nov 13, 2020
Source: N/A
Sold
$5,211,250
Aug 14, 2020
Source: Agent Provided
Pending
$5,495,000
Jul 6, 2020
Source: Agent Provided
Listed For Sale
$5,495,000
Jan 3, 2019
Source: N/A
Sold
$1,410,000

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 38 Windsor Rd

  • What is 38 Windsor Rd estimated to be worth?
    Trulia's estimated value for 38 Windsor Rd in Wellesley, MA is $6,126,700.
  • What is the price history for 38 Windsor Rd?
    38 Windsor Rd in Wellesley, MA last sold for $5,211,250 in November 2020.
  • 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.
  • Does 38 Windsor Rd have air conditioning?
    Yes, 38 Windsor Rd in Wellesley, MA has air conditioning.
  • How big is the lot at 38 Windsor Rd?
    The lot at 38 Windsor Rd in Wellesley, MA is about 0.62 acres (27,007 sq ft).

Explore by feature - Pet Friendly

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Explore by feature - Outdoor Space

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Off Market Homes Near 38 Windsor Rd

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