OFF MARKET

Off Market Oct 2020 for $1.9M

$2,765,397

Est. refi paymentEst. refi $2,132/mo

•

4,660

sq ft

37 Chestnut St, Wellesley, MA 02481

About this home

Wellesley Hills! An incredible combination of renovated/expanded home, flat backyard & ideal location! This home has been truly transformed. Open kitchen with center island, wet bar area and dining area. Window bank along entire back of home with access to patio with pergola and gorgeous flat yard on 20,000 sq ft lot. Family room with fireplace and built-ins. First floor with additional living room with fireplace and dining room plus private first floor office. 2 car garage and large mudroom with laundry. New master suite with cathedral ceilings, walk-in closet plus additional closets/built-ins and spa-like master marble bath. Second floor sitting area with bonus office nook. 3 additional bedrooms and 2 full baths. Finished lower level perfect for playroom and exercise plus huge storage. Impressive front entrance with stone pillars and circular front drive. Over 4600 sq feet of "new house" all just a short distance to the train, Wellesley Hills restaurants, coffee and shops!

Single-familyProperty Type

1979Year Built

0.48 acresLot Size

$593Est. Price/Sq.Ft.

2 garage spacesParking

Listed by Melissa Dailey • Coldwell Banker Realty - Wellesley

Bought with Keith Shirley • Meridian Realty Group LLC

Redfin checked: 7 minutes ago

•Source:MLS PIN #72705531

Redfin Estimate

$2,765,397

$855K since sold in October 2020$118K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 6% higher than the average sale price ($2.61M) of 6 comparable homes.

SOLD MAR 5, 2026
$2,500,000
A
4 beds3.5 baths4,870 sq ft
3 Garden Rd, Wellesley, MA 02481
SOLD JUL 16, 2026
$2,690,000
B
4 beds3.5 baths4,761 sq ft
21 Elm St, Wellesley, MA 02481
SOLD JUN 26, 2026
$2,525,000
C
4 beds3.5 baths3,497 sq ft
35 Arnold Rd, Wellesley, MA 02481
SOLD JAN 9, 2026
$3,115,000
D
4 beds3.5 baths4,294 sq ft
26 Edmunds Rd, Wellesley, MA 02481
SOLD APR 13, 2026
$2,500,000
E
5 beds4.5 baths5,261 sq ft
1 Clock Tower Dr, Wellesley, MA 02481
SOLD AUG 5, 2026
$2,325,000
F
4 beds3.5 baths3,406 sq ft
53 Audubon Rd, Wellesley, MA 02481

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Earn from this home

Sell

$1,275,344

Est. take-home

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Refinance

Est. cash available

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Rent

$5,767/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

101.2%

0.6% MoM

Median sale price

$2.6M

$189K MoM

Avg. days on market

15d

0 days MoM

Recently sold homes

0 MoM

New listings for sale

OPEN FRI, 4:30PM TO 6PM
$2,390,000
5 beds3.5 baths4,149 sq ft
76 Mclean St, Wellesley, MA 02481
$3,595,000
6 beds5 baths6,525 sq ft
151 Oakland St, Wellesley, MA 02481
See all

Provided by Redfin

Sale history for 37 Chestnut St

Year

Property tax

Land + Additions

Assessment*

2023

$24,160 (+6.5%)

$1,019,000 + $1,091,000

$2,110,000

2022

$22,683 (+11.4%)

$913,000 + $1,029,000

$1,942,000

2021

$20,363 (+9.1%)

$875,000 + $858,000

$1,733,000

2020

$18,669 (+1.1%)

$875,000 + $740,000

$1,615,000

2019

$18,466 (+1.3%)

$875,000 + $721,000

$1,596,000

2018

$18,236 (+1.4%)

$883,000 + $643,000

$1,526,000

2017

$17,992 (+23.6%)

$883,000 + $643,000

$1,526,000

2015

$14,554 (+2.0%)

$868,000 + $391,000

$1,259,000

2014

$14,263 (+4.2%)

$770,000 + $466,000

$1,236,000

2013

$13,689 (+1.9%)

$721,000 + $449,000

$1,170,000

2012

$13,432 (+5.6%)

$721,000 + $449,000

$1,170,000

2011

$12,722 (+4.6%)

$673,000 + $440,000

$1,113,000

2010

$12,167 (−5.8%)

$721,000 + $440,000

$1,161,000

2009

$12,917

$983,000 + $381,000

$1,364,000

Tax history for 37 Chestnut St

Year

Property tax

Land + Additions

Assessment*

2023

$24,160 (+6.5%)

$1,019,000 + $1,091,000

$2,110,000

2022

$22,683 (+11.4%)

$913,000 + $1,029,000

$1,942,000

2021

$20,363 (+9.1%)

$875,000 + $858,000

$1,733,000

2020

$18,669 (+1.1%)

$875,000 + $740,000

$1,615,000

2019

$18,466 (+1.3%)

$875,000 + $721,000

$1,596,000

2018

$18,236 (+1.4%)

$883,000 + $643,000

$1,526,000

2017

$17,992 (+23.6%)

$883,000 + $643,000

$1,526,000

2015

$14,554 (+2.0%)

$868,000 + $391,000

$1,259,000

2014

$14,263 (+4.2%)

$770,000 + $466,000

$1,236,000

2013

$13,689 (+1.9%)

$721,000 + $449,000

$1,170,000

2012

$13,432 (+5.6%)

$721,000 + $449,000

$1,170,000

2011

$12,722 (+4.6%)

$673,000 + $440,000

$1,113,000

2010

$12,167 (−5.8%)

$721,000 + $440,000

$1,161,000

2009

$12,917

$983,000 + $381,000

$1,364,000

*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

3.5

Stories

Lot width

—

Lot depth

—

Lot size

20,889

Year renovated

2021

Sq. Ft.

4,660

Year built

1979

Style

Single Family Residential

County

Norfolk County

APN

259287

Parking Spaces

Basement

Yes

Accessible

HOA Dues

—

Garage

Yes

Features

—

Last updated by owner on Apr 27, 2021.

Property details

Parking

Parking Information
Has Garage
Has Open Parking
# of Garage Spaces: 2
# of Covered Spaces: 2
Parking Spaces: 10
AttachedGarageYN: Yes
Parking Features: Attached, Garage Door Opener, Paved Drive, Off Street

Interior

Master Bedroom Information
Area: 378
Length: 21
Width: 18
Level: Second
Features: Bathroom - Full,Bathroom - Double Vanity/Sink,Walk-In Closet(s),Closet

Bedroom #2 Information
Area: 192
Length: 12
Width: 16
Level: Second
Features: Closet

Bedroom #3 Information
Area: 210
Length: 15
Width: 14
Level: Second
Features: Closet

Bedroom #4 Information
Area: 170
Length: 17
Width: 10
Level: Second
Features: Closet

Bathroom Information
# of Bathrooms (Full): 3
# of Bathrooms (Half): 1
Master Bathroom Features: Yes

Bathroom #1 Information
Level: First
Features: Bathroom - Half

Bathroom #2 Information
Level: Second
Features: Bathroom - Full

Bathroom #3 Information
Level: Second
Features: Bathroom - Full

Living Room Information
Area: 330
Length: 22
Width: 15
Level: First
Features: Window(s) - Picture

Family Room Information
Area: 340
Length: 20
Width: 17
Level: First
Features: Closet/Cabinets - Custom Built

Dining Room Information
Area: 240
Length: 16
Width: 15
Level: First
Features: Exterior Access

Kitchen Information
Area: 285
Length: 19
Width: 15
Level: First
Features: Dining Area,Kitchen Island,Exterior Access,Open Floorplan,Wine Chiller

Office Room Information
Area: 140
Length: 10
Width: 14
Level: First
Features: Window(s) - Picture

Basement Information
Basement: Full

Laundry Information
Laundry Features: First Floor

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 2
Fireplace Features: Family Room, Living Room

Interior Features
# of Rooms (Total): 10
Window Features: Window(s) - Picture, Screens
Flooring: Wood, Flooring - Wall to Wall Carpet
Interior Features: Mud Room, Office, Sitting Room, Play Room, Exercise Room

Exterior

Building Information
Building Area (Total): 4,660
Foundation Details: Concrete Perimeter
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Renovated Since
Color: grey

Exterior Features
Roof: Shingle
Patio And Porch Features: Patio
Exterior Features: Patio, Rain Gutters, Professional Landscaping, Sprinkler System, Screens

Property Information
PropertySubType: Single Family Residence

Lot Information
Lot Size (Acres): 0.48
Road Frontage Type: Public

Financial

Tax Information
Tax Annual Amount: $18,669
Tax Year: 2020

Utilities

Utility Information
Utilities: for Gas Range, for Electric Oven
Sewer: Public Sewer
Water Source: Public

Heating & Cooling
Has Heating
Has Cooling
Heating: Forced Air, Natural Gas
Cooling: Central Air

Location

Location Information
Directions: Cliff Road to Chestnut
UnparsedAddress: 37 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 facts

Beds: 4
Baths: 3.5
Sq. Ft.: 4,660
Stories: 2.0
Parking Spaces: 12
Basement: Yes
Accessible: No
Lot Size: 0.48 acres
Style: Single Family Residential
Year Built: 1979
Year Renovated: 2021
County: Norfolk County
APN: 259287
HOA Dues: —
Garage: Yes
Features: —

Home facts updated by owner on Apr 27, 2021

Other

Miscellaneous Information
Heat Zones: 3

Listing Information
Exclusions: Blue And White Window Treatments In Front Bedroom
StandardStatus: Closed

Around this home

Schools

Sprague Elementary School

Public K-5 • Assigned • 1.3mi

9/10

Wellesley Middle School

Public 6-8 • Assigned • 1.0mi

8/10

Wellesley High School

Public 9-12 • Assigned • 1.0mi

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

56% 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

$2.63M – $3.18M

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Nearby similar homes

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New listings for sale in 02481

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Home values near 37 Chestnut St

Data from public records.

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

Address	Redfin Estimate
31 Chestnut St, Wellesley, MA 5 Beds \| 3.5 Baths \| 2982 Sq. Ft.	$2,168,224
41 Chestnut St, Wellesley, MA 8 Beds \| 3.5 Baths \| 5347 Sq. Ft.	$3,984,031

Address	Redfin Estimate
27 Chestnut St, Wellesley, MA 6 Beds \| 4.5 Baths \| - Sq. Ft.	$3,400,614
42 Chestnut St, Wellesley, MA 5 Beds \| 4.5 Baths \| 5112 Sq. Ft.	$3,139,239

Property information provided by MLS PIN when last listed in 2020. This data may not show owner updates. 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 37 Chestnut St

Tax history for 37 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 37 Chestnut St

More real estate resources