Sold on May 2026

$2,280,000

•

3,533

sq ft

21 Cunningham Rd, Wellesley, MA 02481

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About this home

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.

Single-familyProperty Type

1930Year Built

9,810 sq ftLot Size

$645Price/Sq.Ft.

1 garage spacesParking

Listed by Teri Adler • MGS Group Real Estate LTD - Wellesley

Bought with Elke Cardella • Compass

Redfin checked: 2 minutes ago

•Source:MLS PIN #73493643

Redfin Estimate

$2,387,104

$107K since sold in May 2026$90K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 17.9% higher than the average sale price ($2.03M) of 6 comparable homes.

SOLD AUG 14, 2026
$2,480,000
A
4 beds3.5 baths3,610 sq ft
10 Kirkland Cir, Wellesley, MA 02481
SOLD JUL 6, 2026
$1,830,000
B
4 beds2.5 baths2,670 sq ft
14 Standish Rd, Wellesley, MA 02481
SOLD JUL 31, 2026
$2,100,000
C
4 beds3.5 baths2,953 sq ft
2 Woodlawn Oval, Wellesley, MA 02481
SOLD AUG 7, 2026
$1,700,000
D
4 beds2.5 baths2,994 sq ft
50 Dwhinda Rd, Waban, MA 02468
SOLD JUN 10, 2026
$2,090,000
E
4 beds3.5 baths3,283 sq ft
4 Fiske Rd, Wellesley, MA 02481
SOLD JUN 3, 2026
$1,953,000
F
4 beds2.5 baths2,627 sq ft
92 Woodlawn Ave, Wellesley, MA 02481

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Market trends in 02481, MA

Last updated July 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

101.8%

+0.1% MoM

Median sale price

$2.4M

$26K MoM

Avg. days on market

15d

0 days MoM

Recently sold homes

25 MoM

New listings for sale

EARLY ACCESS
$3,695,000
6 beds5 baths6,990 sq ft
151 Oakland St, Wellesley, MA 02481
3D WALKTHROUGH
$1,395,000
4 beds2.5 baths1,800 sq ft
560 Worcester St, Wellesley, MA 02481
$1,475,000
3 beds2 baths2,496 sq ft
7 Grantland Rd, Wellesley, MA 02481
EARLY ACCESS
$2,049,000
3 beds3 baths4,366 sq ft
53 Sheridan Rd, Wellesley, MA 02481
$1,950,000
3 beds1.5 baths1,595 sq ft
53 Elmwood Rd, Wellesley, MA 02481
EARLY ACCESS
$7,495,000
6 beds8 baths7,900 sq ft
38 Woodcliff Rd, Wellesley, MA 02481
$3,050,000
5 beds5 baths6,006 sq ft
23 Wareland Rd, Wellesley, MA 02481
EARLY ACCESS
$1,275,000
3 beds3 baths1,848 sq ft
22 Cedar St, Wellesley, MA 02482
$2,095,000
4 beds2.5 baths3,330 sq ft
42 Sheridan Rd, Wellesley, MA 02481
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Rental estimate

Est. $4,991 per month, based on comparable rentals

Sale and tax history for 21 Cunningham Rd

Sale History
Tax History

Date

Event

Price

MLS PIN #73493643

May 29, 2026

Sold

$2,280,000

$645/sq ft

Mar 30, 2026

Listed

$2,095,000

$593/sq ft

MLS PIN #72855080

Jul 30, 2021

Sold

$1,462,000

$414/sq ft

Jun 23, 2021

Listed

$1,349,000

$382/sq ft

+18

Charming arts and crafts home set on an ended way close to Centennial Park. This one-of-a-kind property has beautiful elements throughout including rich wood trim, hardwood floors and custom details. The heart of the home is the expansive family room with soaring ceilings, custom built-ins and walls of windows. French doors lead to the exquisite gardens bursting with color. The kitchen has granite counters, a breakfast bar opening to a sunny casual dining/sitting area. There is also a convenient home office. On the second level, the luxurious main suite has a sitting room, walk-in closet and bath with a shower room, rain head and two-person soaking tub. There are three additional family bedrooms and a bath. You'll appreciate the comforts of air conditioning and a heated garage. Walk to shops and restaurants from this lovely neighborhood in one of the best commuter locations.

Public Records

Feb 1, 1990

Sold

$147,000

$42/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$15,137 (+23.2%)

$794,000 + $528,000

$1,322,000

2022

$12,287 (+10.2%)

$652,000 + $400,000

$1,052,000

2021

$11,151 (+1.6%)

$652,000 + $297,000

$949,000

2020

$10,970 (+3.2%)

$652,000 + $297,000

$949,000

2019

$10,633 (−5.7%)

$622,000 + $297,000

$919,000

2018

$11,281 (+1.5%)

$646,000 + $298,000

$944,000

2017

$11,118 (+4.3%)

$645,000 + $298,000

$943,000

2015

$10,658 (+4.1%)

$633,000 + $289,000

$922,000

2014

$10,236 (+4.7%)

$524,000 + $363,000

$887,000

2013

$9,781 (+1.9%)

$491,000 + $345,000

$836,000

2012

$9,597 (+3.1%)

$491,000 + $345,000

$836,000

2011

$9,304 (−4.9%)

$458,000 + $356,000

$814,000

2010

$9,788 (+8.8%)

$491,000 + $443,000

$934,000

2009

$8,997

$556,000 + $394,000

$950,000

Public record

Beds

Baths

2.5

Stories

Lot width

—

Lot depth

—

Lot size

9,810

Year renovated

2026

Sq. Ft.

3,533

Year built

1930

Style

Single Family Residential

County

Norfolk County

APN

258620

Parking Spaces

Basement

Yes

Accessible

HOA Dues

—

Garage

Yes

Features

Pool

Last updated by owner on Jul 20, 2026.

Property details

Parking

Parking Information
Has Garage
Has Open Parking
# of Garage Spaces: 1
# of Covered Spaces: 1
Open Parking Spaces: 3
Parking Spaces: 4
AttachedGarageYN: Yes
Parking Features: Attached, Paved Drive, Off Street, Paved

Interior

Master Bedroom Information
Level: Second
Features: Ceiling Fan(s),Vaulted Ceiling(s),Walk-In Closet(s),Closet,Closet/Cabinets - Custom Built,Flooring - Wall to Wall Carpet,Lighting - Overhead

Bedroom #2 Information
Level: Second
Features: Ceiling Fan(s),Beamed Ceilings,Closet,Flooring - Wood,Lighting - Overhead

Bedroom #3 Information
Level: Second
Features: Closet,Flooring - Wood,Lighting - Overhead,Crown Molding

Bedroom #4 Information
Level: Second
Features: Closet,Flooring - Wood,Lighting - Overhead,Crown Molding

Bathroom Information
# of Bathrooms (Full): 2
# of Bathrooms (Half): 1
Master Bathroom Features: Yes

Bathroom #1 Information
Level: Second
Features: Bathroom - Full,Bathroom - Double Vanity/Sink,Bathroom - Tiled With Tub & Shower,Flooring - Stone/Ceramic Tile,Countertops - Stone/Granite/Solid,Countertops - Upgraded,Crown Molding

Bathroom #2 Information
Level: Second
Features: Bathroom - Tiled With Tub & Shower,Flooring - Stone/Ceramic Tile,Countertops - Stone/Granite/Solid,Recessed Lighting,Steam / Sauna,Lighting - Sconce

Bathroom #3 Information
Level: First
Features: Bathroom - Half,Flooring - Wood,Recessed Lighting

Living Room Information
Level: First
Features: Beamed Ceilings,Flooring - Wood,Recessed Lighting,Crown Molding

Family Room Information
Level: First
Features: Closet/Cabinets - Custom Built,Flooring - Wood,Exterior Access,Recessed Lighting,Crown Molding,Decorative Molding

Dining Room Information
Level: First
Features: Flooring - Wood,Lighting - Overhead,Crown Molding,Decorative Molding

Kitchen Information
Level: First
Features: Flooring - Wood,Dining Area,Wet Bar,Exterior Access,Open Floorplan,Recessed Lighting,Remodeled,Gas Stove

Office Room Information
Level: First
Features: Skylight,Flooring - Wall to Wall Carpet,Lighting - Overhead

Laundry Information
Laundry Features: Flooring - Vinyl, Recessed Lighting, Sink, In Basement

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 1
Fireplace Features: Living Room

Appliances
Appliances: Range, Dishwasher, Microwave, Refrigerator, Freezer, Washer, Dryer

Interior Features
# of Rooms (Total): 11
Door Features: French Doors
Window Features: Skylight(s)
Flooring: Wood, Tile, Flooring - Wall to Wall Carpet
Interior Features: Lighting - Overhead, Closet, Recessed Lighting, Office, Play Room

Exterior

Building Information
Building Area (Total): 3,533
Foundation Details: Concrete Perimeter
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Actual,Renovated Since

Exterior Features
Fencing: Invisible
Roof: Shingle
Patio And Porch Features: Patio
Exterior Features: Patio, Decorative Lighting, Invisible Fence, Stone Wall

Property Information
PropertySubType: Single Family Residence
Above Grade Finished Area: 2933
Below Grade Finished Area: 600
ADU: N

Lot Information
Lot Size (Acres): 0.23
Lot Features: Cul-De-Sac, Wooded
Road Frontage Type: Public

Financial

Tax Information
Tax Annual Amount: $16,495.74
Tax Year: 2026

Utilities

Utility Information
Sewer: Public Sewer
Water Source: Public
Power Production Annual: 15.7
Power Production Annual Status: B
Power Production Size: 0
Power Production Type: A
Power Production Year Install: 2023

Heating & Cooling
Has Heating
Has Cooling
Heating: Steam, Radiant, Natural Gas
Cooling: Central Air, Ductless

Location

School Information
Elementary School: Fiske
Middle Or Junior School: Wellesley
High School: Wellesley

Location Information
Directions: Oakland Street to Grantland Road to Cunningham Road
UnparsedAddress: 21 Cunningham Road, Wellesley MA 02481

Community Information
Senior CommunityYN: No
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, University

Public facts

Beds: 4
Baths: 2.5
Sq. Ft.: 3,533
Stories: 2.0
Parking Spaces: 4
Basement: Yes
Accessible: No
Lot Size: 9,810 square feet
Style: Single Family Residential
Year Built: 1930
Year Renovated: 2026
County: Norfolk County
APN: 258620
HOA Dues: —
Garage: Yes
Features: Pool

Home facts updated by owner on Jul 20, 2026

Other

Listing Information
StandardStatus: Closed

Around this home

Schools

Joseph E. Fiske Elementary School

Public K-5 • Assigned • 1.0mi

10/10

Wellesley Middle School

Public 6-8 • Assigned • 1.3mi

8/10

Wellesley High School

Public 9-12 • Assigned • 0.9mi

10/10

Provided by GreatSchools

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

5/10 Heat Factor

7 days above 97° expected this year, 15 days in 30 years

6/10 Wind Factor

53% chance of strong winds in next 30 years

2/10 Air Factor

1 unhealthy days expected this year, 2 days in 30 years

Provided by First Street

Historical weather

Wellesley, MA • 02481

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

78/ 100

Good sunlight

Sunscore

There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

8 hrs

3.9 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$2.27M – $2.75M

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New listings for sale in 02481

EARLY ACCESSCOMPASS COMING SOON

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Home values near 21 Cunningham Rd

Data from public records.

Address	Redfin Estimate
10 Cunningham Road, Wellesley, MA 3 Beds \| 1.5 Baths \| 1634 Sq. Ft.	$1,554,889
22 Cunningham Road, Wellesley, MA 2 Beds \| 1.5 Baths \| 1226 Sq. Ft.	$1,224,516

Address	Redfin Estimate
14 Cunningham Road, Wellesley, MA 3 Beds \| 1.5 Baths \| - Sq. Ft.	$1,440,682
24 Cunningham Road, Wellesley, MA 3 Beds \| 2.5 Baths \| 1950 Sq. Ft.	$1,357,574

Address	Redfin Estimate
18 Cunningham Road, Wellesley, MA 4 Beds \| 2 Baths \| 2354 Sq. Ft.	$1,542,898
30 Cunningham Road, Wellesley, MA 3 Beds \| 2.5 Baths \| 1772 Sq. Ft.	$1,550,234

Property information provided by MLS PIN when last listed in 2026. This data may not show owner updates. Learn more.

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21 Cunningham Rd, Wellesley, MA 02481

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About this home

Redfin Estimate

Market trends in 02481, MA

Homeowner tools

Sale and tax history for 21 Cunningham Rd

Public record

Property details

Parking

Interior

Exterior

Financial

Utilities

Location

Public facts

Other

Around this home

Schools

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 02481

Home values near 21 Cunningham Rd

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