OFF MARKET

Off Market Aug 2020 for $1.4M

$1,928,680

Est. refi paymentEst. refi $1,787/mo

•

2,644

sq ft

21 Chestnut St, Wellesley, MA 02481

About this home

Nestled in the heart of the Cliff Estates, a charming Victorian maintains the character of yesterday with the updates today's buyers are looking for.The front walk guides you to a lovely screened porch perfect for summer evenings. The foyer with turned stair case is flanked by a large dining room and double parlor. Pristine maple floors throughout the home are warm and welcoming. Always the heart of the home an updated chef's kitchen,granite counters,6 burner gas stove and adjacent family room. A mudroom entry way with slate floor rounds out the first floor.The second floor has three good size bedrooms and family bath in addition to a large master suite with private bath and dressing area which creates a quiet retreat. Exquisite gardens,lovingly tended, enhance the grounds,everywhere you turn specimen plantings and flowering shrubs. Enjoy dinner on the deck off the kitchen,relax in the serene setting. A quick stroll to Boston Train,Cafe Nero,Post Office,restaurants and walking trails.

Single-familyProperty Type

1880Year Built

0.25 acresLot Size

$729Est. Price/Sq.Ft.

3 garage spacesParking

Listed by Gail Lockberg • Berkshire Hathaway HomeServices Town and Country Real Estate

Bought with Patricia Bradley • Rutledge Properties

Redfin checked: 2 minutes ago

•Source:MLS PIN #72692037

Redfin Estimate

$1,928,680

$482K since sold in August 2020$11K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 16.1% higher than the average sale price ($1.66M) of 6 comparable homes.

SOLD JUN 3, 2026
$1,953,000
A
4 beds2.5 baths2,627 sq ft
92 Woodlawn Ave, Wellesley, MA 02481
SOLD AUG 19, 2026
$1,895,000
B
4 beds3 baths2,695 sq ft
25 Riverdale Rd, Wellesley, MA 02481
SOLD JUL 6, 2026
$1,830,000
C
4 beds2.5 baths2,670 sq ft
14 Standish Rd, Wellesley, MA 02481
SOLD JUL 31, 2026
$2,100,000
D
4 beds3.5 baths2,953 sq ft
2 Woodlawn Oval, Wellesley, MA 02481
SOLD AUG 6, 2026
$1,177,000
E
3 beds2.5 baths3,129 sq ft
642 Worcester St, Wellesley, MA 02482
SOLD AUG 12, 2026
$1,016,000
F
3 beds2 baths1,521 sq ft
6 Oakland Cir, Wellesley, MA 02481

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Earn from this home

Sell

$812,095

Est. take-home

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Refinance

Est. cash available

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Rent

$4,870/mo

Redfin rental estimate

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Market trends in 02481, MA

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

99.8%

1.3% MoM

Median sale price

$2.5M

$91K MoM

Avg. days on market

17d

2 days MoM

Recently sold homes

8 MoM

New listings for sale

NEW 32 HRS AGO
$1,299,000
3 beds1.5 baths2,384 sq ft
41-A Hunnewell St, Wellesley Hills, MA 02481
OPEN SUN, 11AM TO 1PM
$1,885,000
4 beds3.5 baths3,093 sq ft
35 Forest St, Wellesley, MA 02481
OPEN SUN, 1PM TO 2:15PM
$2,150,000
5 beds4.5 baths4,404 sq ft
32 Lantern Ln, Wellesley, MA 02481
OPEN SUN, 12PM TO 2PM
$4,980,000
5 beds4.5 baths5,296 sq ft
97 Arnold Rd, Wellesley, MA 02481
OPEN SUN, 11AM TO 12PM
$1,799,000
4 beds3.5 baths2,714 sq ft
8 Cypress Rd, Wellesley, MA 02481
OPEN SUN, 12PM TO 2PM
$2,495,000
4 beds4 baths3,746 sq ft
54 Edmunds Rd, Wellesley, MA 02481
OPEN SUN, 12PM TO 1:30PM
$2,195,000
5 beds4 baths3,200 sq ft
6 Intervale Rd, Wellesley, MA 02481
OPEN SUN, 12PM TO 1:30PM
$3,995,000
5 beds5.5 baths5,059 sq ft
39 Fairbanks Ave, Wellesley, MA 02481
OPEN SUN, 11:30AM TO 1PM
$2,390,000
5 beds3.5 baths4,692 sq ft
76 Mclean St, Wellesley, MA 02481
See all

Provided by Redfin

Sale history for 21 Chestnut St

Year

Property tax

Land + Additions

Assessment*

2023

$12,320 (−1.8%)

$813,000 + $263,000

$1,076,000

2022

$12,544 (+2.3%)

$728,000 + $346,000

$1,074,000

2021

$12,267 (+1.6%)

$698,000 + $346,000

$1,044,000

2020

$12,069

$698,000 + $346,000

$1,044,000

2019

$12,079 (−8.4%)

$698,000 + $346,000

$1,044,000

2018

$13,193 (+1.4%)

$833,000 + $271,000

$1,104,000

2017

$13,016 (+6.6%)

$833,000 + $271,000

$1,104,000

2015

$12,207 (+11.8%)

$819,000 + $237,000

$1,056,000

2014

$10,917 (+5.0%)

$654,000 + $292,000

$946,000

2013

$10,401 (+9.9%)

$613,000 + $276,000

$889,000

2012

$9,460 (+0.8%)

$613,000 + $211,000

$824,000

2011

$9,384 (+1.1%)

$593,000 + $228,000

$821,000

2010

$9,285 (−0.2%)

$658,000 + $228,000

$886,000

2009

$9,300

$787,000 + $195,000

$982,000

Tax history for 21 Chestnut St

Year

Property tax

Land + Additions

Assessment*

2023

$12,320 (−1.8%)

$813,000 + $263,000

$1,076,000

2022

$12,544 (+2.3%)

$728,000 + $346,000

$1,074,000

2021

$12,267 (+1.6%)

$698,000 + $346,000

$1,044,000

2020

$12,069

$698,000 + $346,000

$1,044,000

2019

$12,079 (−8.4%)

$698,000 + $346,000

$1,044,000

2018

$13,193 (+1.4%)

$833,000 + $271,000

$1,104,000

2017

$13,016 (+6.6%)

$833,000 + $271,000

$1,104,000

2015

$12,207 (+11.8%)

$819,000 + $237,000

$1,056,000

2014

$10,917 (+5.0%)

$654,000 + $292,000

$946,000

2013

$10,401 (+9.9%)

$613,000 + $276,000

$889,000

2012

$9,460 (+0.8%)

$613,000 + $211,000

$824,000

2011

$9,384 (+1.1%)

$593,000 + $228,000

$821,000

2010

$9,285 (−0.2%)

$658,000 + $228,000

$886,000

2009

$9,300

$787,000 + $195,000

$982,000

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

2.5

Stories

Lot width

—

Lot depth

—

Lot size

0.25 Acres

Year renovated

1983

Sq. Ft.

2,644

Year built

1880

Style

Single Family Residential

County

Norfolk County

APN

259291

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 20, 2023.

Property details

Parking

Parking Information
Has Garage
Has Open Parking
# of Garage Spaces: 3
# of Covered Spaces: 3
Parking Spaces: 2
AttachedGarageYN: Yes
Parking Features: Attached, Workshop in Garage, Paved Drive, Off Street

Interior

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

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 1

Interior Features
# of Rooms (Total): 9
Flooring: Wood, Stone / Slate

Exterior

Building Information
Building Area (Total): 2,644
Foundation Details: Stone
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Actual

Exterior Features
Roof: Shingle
Patio And Porch Features: Screened, Deck
Exterior Features: Porch - Screened, Deck, Rain Gutters, Garden

Property Information
Accessibility Features: No
PropertySubType: Single Family Residence

Lot Information
Lot Size (Acres): 0.25
Lot Features: Corner Lot
Road Frontage Type: Public

Financial

Tax Information
Tax Annual Amount: $12,068
Tax Year: 2020

Utilities

Utility Information
Utilities: for Gas Range
Sewer: Public Sewer
Water Source: Public

Heating & Cooling
Has Heating
Has Cooling
Heating: Hot Water, Natural Gas
Cooling: Window Unit(s)

Location

Location Information
Directions: Cliff Rd to Chestnut St
UnparsedAddress: 21 Chestnut Street, Wellesley MA 02481

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Park, Walk/Jog Trails, Highway Access, House of Worship, Public School, T-Station

Public facts

Beds: 4
Baths: 2.5
Sq. Ft.: 2,644
Stories: 2.0
Lot Size: 0.25 acres
Style: Single Family Residential
Year Built: 1880
Year Renovated: 1983
County: Norfolk County
APN: 259291

Home facts updated by county records on Jul 20, 2023

Other

Miscellaneous Information
Heat Zones: 3

Listing Information
Exclusions: Refrigerator,Freezer, Some Plantings And Garden Statuary,Excluded
StandardStatus: Closed

Around this home

Schools

Sprague Elementary School

Public K-5 • Assigned • 1.2mi

9/10

Wellesley Middle School

Public 6-8 • Assigned • 1.0mi

8/10

Wellesley High School

Public 9-12 • Assigned • 0.9mi

10/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

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

54% 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

In this area, properties receive around 9 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

9 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.83M – $2.22M

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Nearby similar homes

OPEN SUN, 1:30PM TO 3PM

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OPEN SUN, 12PM TO 2PM

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4 beds4 baths3,746 sq ft

54 Edmunds Rd, Wellesley, MA 02481

New listings for sale in 02481

NEW 32 HRS AGO

$1,299,000

3 beds1.5 baths2,384 sq ft

41-A Hunnewell St, Wellesley Hills, MA 02481

OPEN SUN, 11AM TO 1PM

$1,885,000

4 beds3.5 baths3,093 sq ft

35 Forest St, Wellesley, MA 02481

OPEN SUN, 1PM TO 2:15PM

$2,150,000

5 beds4.5 baths4,404 sq ft

32 Lantern Ln, Wellesley, MA 02481

OPEN SUN, 12PM TO 2PM

$4,980,000

5 beds4.5 baths5,296 sq ft

97 Arnold Rd, Wellesley, MA 02481

OPEN SUN, 11AM TO 12PM

$1,799,000

4 beds3.5 baths2,714 sq ft

8 Cypress Rd, Wellesley, MA 02481

OPEN SUN, 12PM TO 2PM

$2,495,000

4 beds4 baths3,746 sq ft

54 Edmunds Rd, Wellesley, MA 02481

OPEN SUN, 12PM TO 1:30PM

$2,195,000

5 beds4 baths3,200 sq ft

6 Intervale Rd, Wellesley, MA 02481

OPEN SUN, 12PM TO 1:30PM

$3,995,000

5 beds5.5 baths5,059 sq ft

39 Fairbanks Ave, Wellesley, MA 02481

OPEN SUN, 11:30AM TO 1PM

$2,390,000

5 beds3.5 baths4,692 sq ft

76 Mclean St, Wellesley, MA 02481

Home values near 21 Chestnut St

Data from public records.

Address	Redfin Estimate
15 Chestnut Street, Wellesley, MA 8 Beds \| 2.5 Baths \| 3614 Sq. Ft.	$1,508,638
31 Chestnut Street, Wellesley, MA 5 Beds \| 3.5 Baths \| 2982 Sq. Ft.	$2,168,224

Address	Redfin Estimate
11 Chestnut Street, Wellesley, MA 6 Beds \| 4.5 Baths \| - Sq. Ft.	$2,725,364
27 Chestnut Street, Wellesley, MA 6 Beds \| 4.5 Baths \| - Sq. Ft.	$3,400,614

Address	Redfin Estimate
33 Chestnut Street, Wellesley, MA 4 Beds \| 4.5 Baths \| 3845 Sq. Ft.	$2,628,149
23 Chestnut Street, Wellesley, MA 5 Beds \| 3.5 Baths \| 4068 Sq. Ft.	$3,002,016

Property information provided by MLS PIN when last listed in 2020. This data may not match . Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 02481, MA

Sale history for 21 Chestnut St

Tax history for 21 Chestnut St

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 02481

Home values near 21 Chestnut St

More real estate resources