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

21 Windsor Rd
Wellesley, MA 02481

  • 6 Beds
  • 4 Baths
  • 4,954 sqft (on 0.54 acres)

$2,918,100

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $17,434/mo*
Refinance Your Home

$2,918,100

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $17,434/mo*
Refinance Your Home
6 Beds
4 Baths
4,954 sqft
(on 0.54 acres)

Home Value

Trulia Estimate
$2.92M
Since last month
Decreased$20K (-0.7%)
Since last year
Increased$53K (+1.9%)
Since last sale
Increased$583K (+25%)
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 +57% in the last 10 years
MonthEstimated value
2026
August 2026$2.92M
July 2026$2.94M
June 2026$2.98M
May 2026$3M
April 2026$2.95M
March 2026$2.94M
February 2026$2.85M
January 2026$2.79M
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
0.19
Single-Family Home
$2,600,000
01/09/26
4
3.5
3,705
133 Abbott Rd, Wellesley, MA
0.14
Single-Family Home
$4,400,000
07/22/26
5
4.5
4,628
120 Forest St, Wellesley, MA
0.25
Single-Family Home
$2,225,000
06/12/26
5
3.5
2,590
117 Forest St, Wellesley, MA
0.29
Single-Family Home
$3,305,000
06/26/26
4
3.5
3,738
10 Allen Rd, Wellesley, MA
0.36
Single-Family Home
$2,625,000
11/03/25
4
3.5
4,720
28 Clovelly Rd, Wellesley, MA
0.40
Single-Family Home
$2,354,000
12/24/25
4
4.5
4,211
23 Inverness Rd, Wellesley, MA
0.10
Single-Family Home
$4,525,000
07/10/26
6
6.5
9,523
10 Clark Rd, Wellesley, MA
0.25
Single-Family Home
$5,100,000
07/23/26
6
7
6,148
108 Abbott Rd, Wellesley, MA
0.14
Single-Family Home
$6,187,500
11/12/25
6
7
7,037
51 Abbott Rd, Wellesley, MA
0.42
Single-Family Home
$2,700,000
09/03/25
6
4.5
7,830

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
23 Inverness Rd, Wellesley, MA 02482
0.10
$4,525,000
6
6.5
9,523
Recently Sold
123 Abbott Rd, Wellesley, MA 02481
0.13
$5,961,300
6
6.5
7,424
Off Market
133 Abbott Rd, Wellesley, MA 02481
0.14
$4,400,000
5
4.5
4,628
Recently Sold
53 Windsor Rd, Wellesley, MA 02481
0.15
$2,991,100
4
4.5
3,272
Off Market
108 Abbott Rd, Wellesley, MA 02481
0.14
$6,187,500
6
7
7,037
Recently Sold
46 Lincoln Rd, Wellesley, MA 02481
0.19
$2,600,000
4
3.5
3,705
Recently Sold
8 Lincoln Cir, Wellesley, MA 02481
0.24
$2,774,300
4
3.5
3,548
Off Market
10 Clark Rd, Wellesley, MA 02481
0.25
$5,100,000
6
7
6,148
Recently Sold
120 Forest St, Wellesley, MA 02481
0.25
$2,225,000
5
3.5
2,590
Recently Sold
117 Forest St, Wellesley, MA 02481
0.29
$3,305,000
4
3.5
3,738
Recently Sold
86 Abbott Rd, Wellesley, MA 02481
0.26
$2,277,100
4
3
2,801
Off Market

Local Information

  • Map ViewExplore the area around 21 Windsor Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1913
Lot Size
0.54 acres
Living Area
4,954 sqft
Price/Sqft
$589
Parking
Garage

About this House

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!
21 Windsor Rd, Wellesley, MA 02481 is a 6 bedroom, 5 bathroom, 4,954 sqft single-family home built in 1913. It last sold for $2,335,000 on Nov 3, 2023 (9% below the $2,565,000 asking price). It is currently off market. The Trulia Estimate is $2,918,100, with a rent estimate of $7,987/month.
Last check for updates: about 13 hours ago
Listed by The Madden David Real Estate Group, (617) 610-5057
Coldwell Banker Realty - Wellesley, (781) 237-9090
Bought with: The Lara & Chelsea Collaborative, (617) 852-7018, Gibson Sotheby's International Realty, (781) 237-8181
Source: MLS PIN, MLS#73146566

Home Details for 21 Windsor Rd

Interior Features

Interior Details
Basement: Full,Partially Finished,Walk-Out Access,Sump PumpNumber of Rooms: 12Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Master Bathroom, Bathroom 1, Bathroom 2, Bathroom 3, Dining Room, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 6Number of Bathrooms: 5Number of Bathrooms (full): 3Number of Bathrooms (half): 2
Dimensions and Layout
Living Area: 4954 Square Feet
Appliances & Utilities
Utilities: for Gas Range, for Electric Dryer, Washer HookupAppliances: Gas Water Heater, Range, Dishwasher, Disposal, Refrigerator, Freezer, Washer, Dryer, Range HoodDishwasherDisposalDryerLaundry: In Basement,Electric Dryer Hookup,Washer HookupRefrigeratorWasher
Heating & Cooling
Heating: Baseboard,Natural Gas,Fireplace(s)Has CoolingAir Conditioning: Window Unit(s)Has HeatingHeating Fuel: Baseboard
Fireplace & Spa
Number of Fireplaces: 4Fireplace: Family Room, Living Room, BedroomHas a FireplaceNo Spa
Windows, Doors, Floors & Walls
Flooring: Tile, Carpet, Hardwood, Flooring - Hardwood
Levels, Entrance, & Accessibility
Floors: Tile, Carpet, Hardwood, Flooring Hardwood

Exterior Features

Exterior Home Features
Roof: SlatePatio / Porch: PatioExterior: Patio, Professional Landscaping, Sprinkler System, Garden, Stone WallFoundation: Concrete PerimeterGardenSprinkler System
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1Open Parking Spaces: 6No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 7Parking: Detached,Paved Drive,Off Street
Frontage
Road Frontage: PublicNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Property Information

Year Built
Year Built: 1913
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: FrameNot Attached PropertyDoes Not Include Home Warranty
Property Information
Not Included in Sale: Excludes Sunroom Chandelier, Mounted Tvs, Washers, Dryer & Refrigerator In Basement.Parcel Number: M:056 R:036 S:, 258720

Price & Status

Price
List Price: $2,565,000
Status Change & Dates
Off Market Date: Mon Aug 28 2023

Active Status

MLS Status: Sold

Location

Direction & Address
City: WellesleyCommunity: Country Club
School Information
Elementary School: WpsJr High / Middle School: WmsHigh School: Whs

Building

Building Area
Building Area: 4954 Square Feet

Community

Community Features: Public Transportation, Shopping, Tennis Court(s), Park, Walk/Jog Trails, Golf, Conservation Area, Highway Access, Private School, Public School, T-Station, UniversityNot Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.54 acres

Offer

Contingencies: Financing

Miscellaneous

BasementMls Number: 73146566

Additional Information

Public TransportationShoppingTennis Court(s)ParkWalk/Jog TrailsGolfConservation AreaHighway AccessPrivate SchoolPublic SchoolT-StationUniversity

Price and Tax history

DateEventPrice
Nov 3, 2023
Source: MLS PIN #73146566
Sold
$2,335,000
Aug 15, 2023
Source: MLS PIN #73146566
Contingent
$2,565,000
Aug 9, 2023
Source: MLS PIN #73146566
Listed For Sale
$2,565,000
Jun 7, 2019
Source: N/A
Sold
$1,875,000
Mar 30, 2019
Source: Agent Provided
Pending
$1,995,000

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
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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
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  • 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

The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.

Frequently asked questions about 21 Windsor Rd

  • What is 21 Windsor Rd estimated to be worth?
    Trulia's estimated value for 21 Windsor Rd in Wellesley, MA is $2,918,100.
  • What is the price history for 21 Windsor Rd?
    21 Windsor Rd in Wellesley, MA last sold for $2,335,000 in November 2023.
  • 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 21 Windsor Rd have air conditioning?
    Yes, 21 Windsor Rd in Wellesley, MA has air conditioning.
  • Does 21 Windsor Rd have laundry facilities?
    Yes, 21 Windsor Rd in Wellesley, MA has in-unit laundry.

Explore by feature - Pet Friendly

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