21 Madison Rd, Wellesley, MA 02481
Property image
Property image
SOLD
AUG 3, 2026

$2,125,000

Trulia Estimate
  • 4 Beds
  • 3.5 Baths
  • 2,609 sqft (on 0.29 acres)

21 Madison Rd, Wellesley, MA 02481

Est. Refi. Payment $12,693/mo*
Refinance Your Home
Currently Off Market - Sold Aug 3, 2026 for $2,130,000 (7% above list price)

Home Value

Trulia Estimate
$2.13M
Since last month
Increased$23K (+1.1%)
Since last year
Increased$257K (+13.7%)
Since last sale
Decreased$2K (-0.1%)
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 +92% in the last 10 years
MonthEstimated value
2026
August 2026$2.13M
August 2026$2.13M
July 2026$2.11M
June 2026$2.16M
May 2026$2.08M
April 2026$2.07M
March 2026$1.95M
February 2026$1.9M
January 2026$1.86M
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
42 Jackson Rd, Wellesley, MA
0.30
Single-Family Home
$1,625,000
06/04/26
3
2.5
1,996
6 Dunedin Rd, Wellesley, MA
0.27
Single-Family Home
$2,295,000
09/17/25
4
4.5
3,560
10 Fife Rd, Wellesley, MA
0.27
Single-Family Home
$2,600,000
03/30/26
4
4
3,282
206-206 Cedar St #R, Wellesley Hills, MA
0.23
Single-Family Home
$1,180,000
02/18/26
3
2
2,421
14 Standish Rd, Wellesley, MA
0.61
Single-Family Home
$1,830,000
07/06/26
4
2.5
2,670
23 Thackeray Rd, Wellesley, MA
0.55
Single-Family Home
$1,880,000
06/05/26
4
3
2,332
319 Oakland St, Wellesley, MA
0.26
Single-Family Home
$2,270,000
08/26/26
5
4
4,507
14 Hunnewell St, Needham, MA
0.39
Single-Family Home
$2,165,000
11/05/25
4
4.5
4,691
34 Sheridan Rd, Wellesley, MA
0.12
Single-Family Home
$1,250,000
08/03/26
3
1.5
1,478

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
7 Madison Rd, Wellesley, MA 02481
0.08
$1,729,200
5
2.5
2,028
Off Market
42 Sheridan Rd, Wellesley, MA 02481
0.06
$2,095,000
4
2.5
3,330
For Sale
36 Sheridan Rd, Wellesley, MA 02481
0.10
$3,102,900
5
4.5
5,496
Off Market
19 Hastings St, Wellesley, MA 02481
0.11
$860,000
3
1
1,053
Recently Sold
34 Sheridan Rd, Wellesley, MA 02481
0.12
$1,250,000
3
1.5
1,478
Recently Sold
29 Sheridan Rd, Wellesley, MA 02481
0.13
$2,697,600
4
3.5
3,815
Off Market
8 Hastings St, Wellesley, MA 02481
0.15
$1,282,600
3
1.5
1,871
Off Market
7 Hastings St, Wellesley, MA 02481
0.16
$1,424,600
4
2.5
1,967
Off Market
53 Madison Rd, Wellesley, MA 02481
0.15
$1,709,100
4
2.5
2,514
Off Market
19 Sheridan Rd, Wellesley, MA 02481
0.16
$3,933,500
5
5.5
6,240
Off Market
33 Hunnewell St, Wellesley, MA 02481
0.16
$2,285,000
4
4
4,867
Off Market

Local Information

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

Home Highlights

Property Type
Single-Family Home
Year Built
1940
Lot Size
0.29 acres
Living Area
2,609 sqft
Price/Sqft
$816/sqft
Parking
1 Car Garage

About this House

Beautifully renovated and thoughtfully updated, this stunning four-bedroom home offers the perfect blend of timeless charm and modern comfort. Nestled on a picturesque setting the property enjoys exceptional privacy, peaceful views, and a true connection to nature. Sun-filled interiors feature spacious living areas, refined finishes, and an inviting floor plan designed for both everyday living and effortless entertaining. The renovated kitchen opens seamlessly to warm and welcoming family spaces, while oversized windows bring the outdoors in at every turn. Generously sized bedrooms, updated baths, and flexible living areas provide comfort and versatility for today’s lifestyle. Outside, expansive outdoor spaces create the ideal backdrop for relaxing, dining, or enjoying the tranquil natural surroundings. Rarely does a home combine such beautiful renovations with an idyllic setting, all while remaining close to top schools, commuting routes & all Wellesley has to offer.
21 Madison Rd, Wellesley, MA 02481 is a 4 bedroom, 4 bathroom, 2,609 sqft single-family home built in 1940. It last sold for $2,130,000 on Aug 3, 2026 (7% above the $1,995,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,125,000, with a rent estimate of $7,030/month.
Last check for updates: about 2 hours ago
Listed by The Lara & Chelsea Collaborative, (617) 852-7018
Coldwell Banker Realty - Wellesley, (781) 237-9090
The Lara & Chelsea Collaborative, (617) 852-7018
Bought with: Coleman Group, (617) 548-3987, William Raveis R.E. & Home Services, (781) 861-9600
Source: MLS PIN, MLS#73529338

Home Details for 21 Madison Rd

Interior Features

Interior Details
Basement: Full,Partially FinishedNumber of Rooms: 9Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Master Bathroom, Bathroom 1, Bathroom 2, Bathroom 3, Dining Room, Family Room, Kitchen
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 2609 Square Feet
Appliances & Utilities
Utilities: for Gas Range, Washer HookupAppliances: Range, Refrigerator, Wine RefrigeratorLaundry: Washer Hookup,Second FloorRefrigerator
Heating & Cooling
Heating: Forced Air,Natural GasHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 2Fireplace: Dining RoomHas a FireplaceNo Spa
Windows, Doors, Floors & Walls
Window: Insulated WindowsDoor: Storm Door(s)Flooring: Carpet, Hardwood, Flooring - Wall to Wall Carpet, Laminate
Levels, Entrance, & Accessibility
Floors: Carpet, Hardwood, Flooring Wall To Wall Carpet, Laminate
View
Has a ViewView: Scenic View(s)

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Porch, PatioExterior: Porch, Patio, Professional LandscapingFoundation: Concrete Perimeter
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1Open Parking Spaces: 4No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 5Parking: Attached,Off Street,Paved
Frontage
Road Frontage: PublicResponsible for Road Maintenance: Public Maintained RoadRoad Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 2109Finished Area (below surface): 500

Property Information

Year Built
Year Built: 1940
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Garrison
Building
Construction Materials: FrameNot Attached PropertyDoes Not Include Home Warranty
Property Information
Parcel Number: M:016 R:028 S:, 257142

Price & Status

Price
List Price: $1,995,000Price Per Sqft: $816/sqft
Status Change & Dates
Off Market Date: Fri Jun 05 2026

Active Status

MLS Status: Sold

Location

Direction & Address
City: Wellesley
School Information
Elementary School: WellesleyJr High / Middle School: WmsHigh School: Whs

Building

Building Area
Building Area: 2609 Square Feet

Community

Community Features: Public Transportation, Shopping, Park, Walk/Jog Trails, Medical Facility, Bike Path, Conservation Area, Highway Access, House of Worship, Public School, UniversityNot Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.29 acres

Miscellaneous

BasementMls Number: 73529338Above Grade Unfinished Area: 2109

Additional Information

Public TransportationShoppingParkWalk/Jog TrailsMedical FacilityBike PathConservation AreaHighway AccessHouse of WorshipPublic SchoolUniversity

Price and Tax history

DateEventPrice
Aug 3, 2026
Source: MLS PIN #73529338
Sold
$2,130,000
Jun 5, 2026
Source: MLS PIN #73529338
Pending
$1,995,000
Jun 3, 2026
Source: MLS PIN #73529338
Listed For Sale
$1,995,000
Aug 12, 2024
Source: MLS PIN #73248316
Sold
$1,800,000
Jun 8, 2024
Source: MLS PIN #73248316
Contingent
$1,675,000

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

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 Madison Rd

  • What is 21 Madison Rd estimated to be worth?
    Trulia's estimated value for 21 Madison Rd in Wellesley, MA is $2,125,000.
  • What is the price history for 21 Madison Rd?
    21 Madison Rd in Wellesley, MA last sold for $2,130,000 in August 2026.
  • 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 Madison Rd have air conditioning?
    Yes, 21 Madison Rd in Wellesley, MA has air conditioning.
  • Does 21 Madison Rd have laundry facilities?
    Yes, 21 Madison Rd in Wellesley, MA has laundry facilities.

Explore by feature - Pet Friendly

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