OFF MARKET

Off Market Mar 2023 for $1.4M

$1,653,604

Est. refi paymentEst. refi $5,426/mo

•

2,249

sq ft

44 Chesterton Rd, Wellesley, MA 02481

About this home

HOME IS UNDER AGREEMENT. OPEN HOUSE IS CANCELLED. Expanded NE Cape with open floor plan is beautifully sited on a level, conforming 10,218 sq ft lot in the coveted Bates School District. It is perfect for empty nesters, entry-level buyers or a developer. This prime, level lot with 105 ft frontage is near Boulder Brook Reservation and has great potential and value in a neighborhood of many newer and larger homes. 9 Rooms with traditional detail and 2.5 Baths include a desirable 1st floor Office w/custom built-ins and direct access to the attached garage, lovely Family Rm with a wall of glass opening onto a generous deck, pretty eat-in Kitchen wi/cherry cabinets, and two first-floor Bedrms. Primary Bedrm has walk-in closet and newer full bath.Lots of hardwood and recessed lighting. Two additional bedrms (one wi/dormer) and second full bath are on the second floor. Upgrade as desired or start new in this most sought-after neighborhood near the Weston line. Excellent commuter location.

Single-familyProperty Type

1950Year Built

10,218 sq ftLot Size

$735Est. Price/Sq.Ft.

1 garage spacesParking

Listed by Barclay & Sampson Team • Berkshire Hathaway HomeServices Commonwealth Real Estate

Bought with The Walsh Team and Partners • William Raveis R.E. & Home Services

Redfin checked: a minute ago

•Source:MLS PIN #73081271

Redfin Estimate

$1,653,604

$249K since sold in March 2023$39K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 5.6% lower than the average sale price ($1.75M) of 6 comparable homes.

SOLD JUL 9, 2026
$1,805,000
A
4 beds2.5 baths2,644 sq ft
22 Lafayette Cir, Wellesley, MA 02482
SOLD APR 17, 2026
$1,740,000
B
4 beds2.5 baths2,214 sq ft
31 Martin Rd, Wellesley, MA 02481
SOLD AUG 10, 2026
$1,500,000
C
3 beds2 baths2,300 sq ft
58 Manor Ave, Wellesley, MA 02482
SOLD AUG 3, 2026
$1,400,000
D
3 beds2.5 baths2,274 sq ft
107 Overbrook Dr, Wellesley, MA 02482
SOLD AUG 13, 2026
$2,562,000
E
4 beds3 baths3,099 sq ft
31 Shirley Rd, Wellesley, MA 02482
SOLD AUG 3, 2026
$1,500,000
F
4 beds3 baths2,901 sq ft
3 Berkeley Rd, Wellesley, MA 02482

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Earn from this home

Sell

$518,651

Est. take-home

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Est. cash available

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Rent

$4,177/mo

Redfin rental estimate

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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

OPEN TODAY, 12PM TO 2PM
$3,595,000
6 beds5 baths6,525 sq ft
151 Oakland St, Wellesley, MA 02481
$5,450,000
5 beds7 baths7,632 sq ft
44 Whiting Rd, Wellesley, MA 02481
3D WALKTHROUGH
$1,395,000
4 beds2.5 baths1,800 sq ft
560 Worcester St, 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
See all

Provided by Redfin

Sale history for 44 Chesterton Rd

Date

Event

Price

MLS PIN #73081271

Mar 31, 2023

Sold

$1,405,000

$625/sq ft

Feb 22, 2023

Listed

$1,100,000

$489/sq ft

MLS PIN #70311933

Apr 12, 2006

Sold

$709,000

$315/sq ft

Mar 23, 2006

Listing Removed

—

Jan 9, 2006

Listed

$769,900

$342/sq ft

MLS PIN #30243632

Oct 15, 1998

Sold

$439,000

$195/sq ft

Jul 27, 1998

Listing Removed

—

Jul 22, 1998

Listed

$439,000

$195/sq ft

MLS PIN #50327356

Aug 1, 1996

Sold

$335,000

$149/sq ft

Jun 4, 1996

Listing Removed

—

Apr 23, 1996

Listed

$345,000

$153/sq ft

Public Records

May 6, 1996

Sold

$335,000

$149/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$10,763 (+2.3%)

$767,000 + $173,000

$940,000

2022

$10,524 (−0.6%)

$657,000 + $244,000

$901,000

2021

$10,587 (+1.6%)

$657,000 + $244,000

$901,000

2020

$10,416

$657,000 + $244,000

$901,000

2019

$10,425 (+1.0%)

$657,000 + $244,000

$901,000

2018

$10,325 (+1.5%)

$651,000 + $213,000

$864,000

2017

$10,175 (+4.0%)

$650,000 + $213,000

$863,000

2015

$9,780 (+9.9%)

$640,000 + $206,000

$846,000

2014

$8,897 (+6.8%)

$505,000 + $266,000

$771,000

2013

$8,330 (+1.9%)

$451,000 + $261,000

$712,000

2012

$8,174 (+14.8%)

$451,000 + $261,000

$712,000

2011

$7,121 (+4.1%)

$421,000 + $202,000

$623,000

2010

$6,843 (+5.9%)

$451,000 + $202,000

$653,000

2009

$6,459

$501,000 + $181,000

$682,000

Tax history for 44 Chesterton Rd

Year

Property tax

Land + Additions

Assessment*

2023

$10,763 (+2.3%)

$767,000 + $173,000

$940,000

2022

$10,524 (−0.6%)

$657,000 + $244,000

$901,000

2021

$10,587 (+1.6%)

$657,000 + $244,000

$901,000

2020

$10,416

$657,000 + $244,000

$901,000

2019

$10,425 (+1.0%)

$657,000 + $244,000

$901,000

2018

$10,325 (+1.5%)

$651,000 + $213,000

$864,000

2017

$10,175 (+4.0%)

$650,000 + $213,000

$863,000

2015

$9,780 (+9.9%)

$640,000 + $206,000

$846,000

2014

$8,897 (+6.8%)

$505,000 + $266,000

$771,000

2013

$8,330 (+1.9%)

$451,000 + $261,000

$712,000

2012

$8,174 (+14.8%)

$451,000 + $261,000

$712,000

2011

$7,121 (+4.1%)

$421,000 + $202,000

$623,000

2010

$6,843 (+5.9%)

$451,000 + $202,000

$653,000

2009

$6,459

$501,000 + $181,000

$682,000

*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

10,019 Sq. Ft.

Year renovated

—

Sq. Ft.

2,249

Year built

1950

Style

Single Family Residential

County

Norfolk County

APN

264239

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: 1
# of Covered Spaces: 1
Parking Spaces: 4
AttachedGarageYN: Yes
Parking Features: Attached, Paved Drive, Off Street, Paved

Interior

Bedroom Information
Main Level Bedrooms: 1

Master Bedroom Information
Area: 180
Length: 12
Width: 15
Level: Main,First
Features: Bathroom - Full,Walk-In Closet(s),Flooring - Hardwood,Remodeled,Lighting - Overhead

Bedroom #2 Information
Area: 168
Length: 14
Width: 12
Level: First
Features: Closet,Flooring - Hardwood,Recessed Lighting

Bedroom #3 Information
Area: 289
Length: 17
Width: 17
Level: Second
Features: Closet

Bedroom #4 Information
Area: 165
Length: 15
Width: 11
Level: Second
Features: Closet

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

Bathroom #1 Information
Length: 5
Level: First
Features: Bathroom - Half,Flooring - Stone/Ceramic Tile

Bathroom #2 Information
Area: 54
Length: 9
Width: 6
Level: First
Features: Bathroom - Tiled With Shower Stall

Bathroom #3 Information
Area: 49
Length: 7
Width: 7
Level: Second
Features: Bathroom - Full,Bathroom - With Shower Stall

Living Room Information
Area: 228
Length: 19
Width: 12
Level: First
Features: Flooring - Hardwood,Window(s) - Picture

Family Room Information
Area: 154
Length: 11
Width: 14
Level: Main,First
Features: Flooring - Wall to Wall Carpet,French Doors,Deck - Exterior,Open Floorplan,Remodeled

Dining Room Information
Area: 120
Length: 10
Width: 12
Level: First
Features: Flooring - Hardwood,Open Floorplan,Recessed Lighting

Kitchen Information
Area: 208
Length: 13
Width: 16
Level: First
Features: Flooring - Stone/Ceramic Tile,Dining Area,Countertops - Stone/Granite/Solid,Countertops - Upgraded,Cabinets - Upgraded,Exterior Access,Recessed Lighting,Remodeled,Lighting - Pendant

Office Room Information
Area: 165
Length: 11
Width: 15
Level: Main
Features: Closet/Cabinets - Custom Built,Flooring - Hardwood,Exterior Access,Recessed Lighting

Basement Information
Basement: Full, Partially Finished, Sump Pump

Laundry Information
Laundry Features: In Basement, Electric Dryer Hookup, Washer Hookup

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

Interior Features
# of Rooms (Total): 9
Flooring: Tile, Carpet, Hardwood, Flooring - Hardwood, Flooring - Wall to Wall Carpet
Interior Features: Closet/Cabinets - Custom Built, Recessed Lighting, Lighting - Overhead, Home Office, Game Room

Exterior

Building Information
Building Area (Total): 2,249
Foundation Details: Concrete Perimeter
Construction Materials: Frame
Year Built Source: Public Records
Year Built Details: Approximate,Renovated Since
Color: Grey

Exterior Features
Roof: Shingle
Patio And Porch Features: Deck
Exterior Features: Deck, Sprinkler System

Property Information
Accessibility Features: No
PropertySubType: Single Family Residence

Lot Information
Lot Size (Acres): 0.23
Lot Features: Level
Road Frontage Type: Public

Financial

Tax Information
Tax Annual Amount: $10,524
Tax Year: 2022

Utilities

Utility Information
Utilities: for Electric Range, for Electric Oven, for Electric Dryer, Washer Hookup
Sewer: Public Sewer
Water Source: Public

Heating & Cooling
Has Heating
Has Cooling
Heating: Baseboard, Oil
Cooling: Ductless

Location

Location Information
Directions: Open House cancelled
UnparsedAddress: 44 Chesterton Rd, Wellesley MA 02481

Community Information
Senior CommunityYN: No
Community Features: Tennis Court(s), Park, Walk/Jog Trails, Conservation Area, Public School

Public facts

Beds: 3
Baths: 2.5
Sq. Ft.: 2,249
Stories: 2.0
Lot Size: 10,019 square feet
Style: Single Family Residential
Year Built: 1950
Year Renovated: —
County: Norfolk County
APN: 264239

Home facts updated by county records on Jul 20, 2023

Other

Miscellaneous Information
Heat Zones: 2

Listing Information
StandardStatus: Closed

Around this home

Schools

Katharine Lee Bates Elementary School

Public K-5 • Assigned • 0.4mi

8/10

Wellesley Middle School

Public 6-8 • Assigned • 1.5mi

8/10

Wellesley High School

Public 9-12 • Assigned • 2.0mi

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

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

$1.57M – $1.90M

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Nearby similar homes

$5,450,000

5 beds7 baths7,632 sq ft

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3 beds1.5 baths1,320 sq ft

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VIDEO TOUR

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3D WALKTHROUGH

$1,395,000

4 beds2.5 baths1,800 sq ft

560 Worcester St, Wellesley, MA 02481

$3,195,000

5 beds5 baths5,735 sq ft

31 Alba Rd, Wellesley, MA 02481

$3,299,000

6 beds4.5 baths4,424 sq ft

209 Bristol Rd, Wellesley, MA 02481

New listings for sale in 02481

OPEN TODAY, 12PM TO 2PM

$3,595,000

6 beds5 baths6,525 sq ft

151 Oakland St, Wellesley, MA 02481

$5,450,000

5 beds7 baths7,632 sq ft

44 Whiting Rd, Wellesley, MA 02481

3D WALKTHROUGH

$1,395,000

4 beds2.5 baths1,800 sq ft

560 Worcester St, Wellesley, MA 02481

EARLY ACCESSCOMPASS COMING SOON

$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

Home values near 44 Chesterton Rd

Data from public records.

Address	Redfin Estimate
40 Chesterton Road, Wellesley, MA 4 Beds \| 4.5 Baths \| 4600 Sq. Ft.	$3,069,004
56 Chesterton Road, Wellesley, MA 3 Beds \| 1.5 Baths \| - Sq. Ft.	$1,740,054

Address	Redfin Estimate
48 Chesterton Road, Wellesley, MA 3 Beds \| 2.5 Baths \| 2125 Sq. Ft.	$1,616,842
53 Chesterton Road, Wellesley, MA 5 Beds \| 5.5 Baths \| 5779 Sq. Ft.	$3,312,122

Address	Redfin Estimate
52 Chesterton Road, Wellesley, MA 4 Beds \| 2 Baths \| 2085 Sq. Ft.	$1,497,101
49 Chesterton Road, Wellesley, MA 5 Beds \| 5 Baths \| 5500 Sq. Ft.	$3,026,902

Property information provided by MLS PIN when last listed in 2023. 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 44 Chesterton Rd

Tax history for 44 Chesterton Rd

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 44 Chesterton Rd

More real estate resources