21 Cunningham Rd, Wellesley, MA 02481
SOLD
MAY 29, 2026

21 Cunningham Rd
Wellesley, MA 02481

  • 4 Beds
  • 2.5 Baths
  • 3,533 sqft

$2,280,000

Last Sold: May 29, 2026
9% over list $2.1M
$645/sqft
Est. Refi. Payment $13,650/mo*
Refinance Your Home

$2,280,000

Last Sold: May 29, 2026
9% over list $2.1M
$645/sqft
Est. Refi. Payment $13,650/mo*
Refinance Your Home
4 Beds
2.5 Baths
3,533 sqft

Home Value

Trulia Estimate
$2.29M
Since last month
Increased$6K (+0.3%)
Since last year
Increased$317K (+16.1%)
Since last sale
Increased$7K (+0.3%)
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 +106% in the last 10 years
MonthEstimated value
2026
August 2026$2.29M
July 2026$2.29M
June 2026$2.28M
May 2026$2.2M
April 2026$2.19M
March 2026$2M
February 2026$1.92M
January 2026$1.89M
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
2 Woodlawn Oval, Wellesley, MA
0.31
Single-Family Home
$2,100,000
07/31/26
4
3.5
2,953
14 Standish Rd, Wellesley, MA
0.39
Single-Family Home
$1,830,000
07/06/26
4
2.5
2,670
28 Cunningham Rd, Wellesley, MA
0.04
Single-Family Home
$1,420,000
09/03/25
3
2.5
2,118
6 Oakland Cir, Wellesley, MA
0.08
Single-Family Home
$1,016,000
08/12/26
3
2
1,521
6 Wareland Rd, Wellesley, MA
0.18
Single-Family Home
$1,282,000
07/15/26
3
2
2,122
43 Bancroft Rd, Wellesley, MA
0.28
Single-Family Home
$1,330,000
04/24/26
3
2
2,231
7 Bemis Rd, Wellesley, MA
0.42
Single-Family Home
$2,350,000
06/09/26
5
5.5
4,550
17 Longfellow Rd, Wellesley, MA
0.40
Single-Family Home
$1,690,762
10/23/25
4
2.5
3,040

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
15 Cunningham Rd, Wellesley, MA 02481
0.04
$1,391,000
3
1.5
1,505
Off Market
28 Cunningham Rd, Wellesley, MA 02481
0.04
$1,478,700
3
2.5
2,118
Off Market
35 Grantland Rd, Wellesley, MA 02481
0.07
$2,563,300
5
4.5
3,904
Off Market
14 Oakland Cir, Wellesley, MA 02481
0.06
$2,137,600
4
3
3,555
Off Market
6 Oakland Cir, Wellesley, MA 02481
0.08
$1,016,000
3
2
1,521
Recently Sold
39 Grantland Rd, Wellesley, MA 02481
0.09
$2,278,000
4
3.5
4,524
Off Market
37 Oakland St, Wellesley Hills, MA 02481
0.12
$2,280,000
5
4.5
3,600
For Sale
368 Worcester St, Wellesley, MA 02481
0.13
$1,375,300
6
3.5
3,005
Off Market
23 Wareland Rd, Wellesley, MA 02481
0.14
$3,050,000
5
5
6,006
For Sale
373 Worcester St, Wellesley, MA 02481
0.17
$1,225,000
3
1.5
2,006
Off Market
12 Wareland Rd, Wellesley, MA 02481
0.16
$1,250,000
3
3
1,808
Recently Sold

Local Information

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

Home Highlights

Property Type
Single-Family Home
Year Built
1930
Living Area
3,533 sqft
Price/Sqft
$645/sqft
Parking
1 Car Garage

About this House

Charm blends effortlessly with modern style at this classic gem. Rich wood trim, light floors, and thoughtful custom details define the quality here. The dramatic family room—with its soaring ceilings, elegant built-ins, and expansive windows—serve as an impressive gathering place. There is also a stunning dining/breakfast room that offers flexible space. Stone counters and stainless appliances lend to the beauty of the eat-in kitchen. The formal living room is anchored by a fireplace and the at-home-office is the perfect spot to work from home. Upstairs, the primary suite is a true retreat: a private sitting room, walk-in closet, and a spa-inspired bath. Three additional bedrooms and a well-appointed bath accommodate family or guests with ease. A magazine worthy playroom in the lower level. Outdoor entertaining is easy with the expansive blue stone patio and sitting area. The property is set on a cul-de-sac with walking trails. Fabulous commuting location and near shops and the train.
21 Cunningham Rd, Wellesley, MA 02481 is a 4 bedroom, 3 bathroom, 3,533 sqft single-family home built in 1930. It last sold for $2,280,000 on May 29, 2026 (9% above the $2,095,000 asking price). It is currently off market. The Trulia Estimate is $2,291,400, with a rent estimate of $6,475/month.

Home Details for 21 Cunningham Rd

Interior Features

Interior Details
Number of Rooms: 11Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Master Bathroom, Bathroom 1, Bathroom 2, Bathroom 3, Dining Room, Family Room, Kitchen, Living Room, Office
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3533 Square Feet
Appliances & Utilities
Appliances: Range, Dishwasher, Microwave, Refrigerator, Freezer, Washer, DryerDishwasherDryerLaundry: Flooring - Vinyl,Recessed Lighting,Sink,In BasementMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Steam,Radiant,Natural GasHas CoolingAir Conditioning: Central Air,DuctlessHas HeatingHeating Fuel: Steam
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Living RoomHas a FireplaceNo Spa
Windows, Doors, Floors & Walls
Window: Skylight(s)Door: French DoorsFlooring: Wood, Tile, Flooring - Wall to Wall Carpet
Levels, Entrance, & Accessibility
Floors: Wood, Tile, Flooring Wall To Wall Carpet

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: PatioFencing: InvisibleExterior: Patio, Decorative Lighting, Invisible Fence, Stone WallFoundation: Concrete Perimeter
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1Open Parking Spaces: 3No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 4Parking: Attached,Paved Drive,Off Street,Paved
Frontage
Road Frontage: PublicNot on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 2933Finished Area (below surface): 600

Property Information

Year Built
Year Built: 1930
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial,Craftsman
Building
Construction Materials: FrameNot Attached PropertyDoes Not Include Home Warranty
Property Information
Parcel Number: M:054 R:027 S:, 258620

Price & Status

Price
List Price: $2,095,000Price Per Sqft: $645/sqft
Status Change & Dates
Off Market Date: Wed Apr 01 2026

Active Status

MLS Status: Sold

Location

Direction & Address
City: Wellesley
School Information
Elementary School: FiskeJr High / Middle School: WellesleyHigh School: Wellesley

Building

Building Area
Building Area: 3533 Square Feet

Community

Community Features: Public Transportation, Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Golf, Medical Facility, Bike Path, Highway Access, House of Worship, Private School, Public School, T-Station, UniversityNot Senior Community

HOA

No HOA

Lot Information

Lot Area: 9810 sqft

Miscellaneous

Mls Number: 73493643Power Production Type Annual: 15.7Power Production Type Annual Status: EstimatedPower Production Type Year Install: 2023Above Grade Unfinished Area: 2933

Additional Information

Public TransportationShoppingPoolTennis Court(s)ParkWalk/Jog TrailsGolfMedical FacilityBike PathHighway AccessHouse of WorshipPrivate SchoolPublic SchoolT-StationUniversity
Last check for updates: about 1 hour ago
Listed by Teri Adler, (617) 306-3642
MGS Group Real Estate LTD - Wellesley, (617) 714-4544
Teri Adler, (617) 306-3642
Bought with: Elke Cardella, (443) 610-6233, Compass, (781) 365-9954
Source: MLS PIN, MLS#73493643

Price and Tax history

DateEventPrice
May 29, 2026
Source: MLS PIN #73493643
Sold
$2,280,000
Mar 30, 2026
Source: MLS PIN #73493643
Listed For Sale
$2,095,000
Jul 30, 2021
Source: N/A
Sold
$1,462,000
Feb 9, 1990
Source: N/A
Sold
$147,000

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
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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
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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
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LGBTQ Local Legal Protections

Apartments for Rent

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Explore by feature - Pet Friendly

14 pet-friendly rentals in Wellesley, MA

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Explore by feature - Outdoor Space

6 rentals with an outdoor space in Wellesley, MA

Homes for sale near 21 Cunningham Rd

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Off Market Homes Near 21 Cunningham Rd

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Frequently asked questions about 21 Cunningham Rd

  • What is 21 Cunningham Rd estimated to be worth?
    Trulia's estimated value for 21 Cunningham Rd in Wellesley, MA is $2,291,400.
  • What is the price history for 21 Cunningham Rd?
    21 Cunningham Rd in Wellesley, MA last sold for $2,280,000 in May 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 Cunningham Rd have air conditioning?
    Yes, 21 Cunningham Rd in Wellesley, MA has air conditioning.
  • Does 21 Cunningham Rd have a pool?
    Yes, 21 Cunningham Rd in Wellesley, MA has a pool.
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.