OFF MARKET

Off Market Jan 2022 for $3.1M

$4,236,292

•

6,000

sq ft

271 Chestnut St, Newton, MA 02465

About this home

Atop West Newton Hill sits this impeccably renovated 6,000 SF Craftsman style home on 30,000 SF of professionally landscaped grounds. Set back from the street with a porte cochere and covered front porch provides for a grand entrance yet ideal for everyday living. In 2016 the current owners undertook an extensive renovation hitting nearly every surface inside and out. Some of the highlights include the open kitchen family room and breakfast area with stainless Sub-Zero, double Wolf ovens with 6 burner cooktop, beveled edge granite counters, and large island complement this spectacular living space. The 2nd floor has 4 bedrooms with laundry. The Primary bedroom has 2 large custom walk-in closets, fire place, and large bath with soaking tub, steam shower, and 2 large vanities. The lower level has a mud room with radiant heat, gym, playroom, game room, 2nd laundry, and au-pair 5th bedroom with bath and kitchenette. Short walk to Peirce School and minutes to the pike and commuter rail.

Single-familyProperty Type

1905Year Built

0.69 acresLot Size

$706Est. Price/Sq.Ft.

2 garage spacesParking

Listed by Chamberlain Group • Historic Homes, Inc.

Bought with Gina Romm • William Raveis R.E. & Home Services

Redfin checked: a minute ago

•Source:MLS PIN #72894711

Redfin Estimate

$4,236,292

$1.1M since sold in January 2022$105K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 4.7% higher than the average sale price ($4.04M) of 6 comparable homes.

SOLD MAY 7, 2026
$4,500,000
A
6 beds6.5 baths6,301 sq ft
40 Sewall St, Newton, MA 02465
SOLD SEP 4, 2026
$3,180,000
B
6 beds5.5 baths6,478 sq ft
49 Shaw St, Newton, MA 02465
SOLD APR 24, 2026
$3,210,000
C
5 beds4 baths4,445 sq ft
26 Sewall St, Newton, MA 02465
SOLD DEC 2, 2025
$4,677,000
D
6 beds5 baths6,445 sq ft
222 Prince St, Newton, MA 02465
SOLD FEB 24, 2026
$4,200,000
E
5 beds5.5 baths4,848 sq ft
18 Sewall St, Newton, MA 02465
SOLD NOV 13, 2025
$4,500,000
F
5 beds6.5 baths6,000 sq ft
20 Birch Hill Rd, Newton, MA 02465

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Sell

$1,714,341

Est. take-home

List your home with Redfin and save $21,181

Rent

$7,095/mo

Redfin rental estimate

List your home for rent

Market trends in 02465, MA

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

102.5%

1.6% MoM

Median sale price

$1.3M

$108K MoM

Avg. days on market

19d

0 days MoM

Recently sold homes

0 MoM

New listings for sale

OPEN SUN, 2:15PM TO 3:15PM
$1,299,000
4 beds3.5 baths2,202 sq ft
123 Mount Vernon St #1, West Newton, MA 02465
$2,999,000
6 beds8 baths6,058 sq ft
42 Lindbergh Ave, Newton, MA 02465
OPEN TODAY, 1:30PM TO 2:30PM
$4,295,000
7 beds6 baths7,810 sq ft
14 Winthrop St, Newton, MA 02465
$6,195,000
7 beds6.5 baths8,989 sq ft
95 Temple St, Newton, MA 02465
OPEN TODAY, 1:30PM TO 3PM
$1,199,000
3 beds3 baths2,302 sq ft
15 Alden Pl #15, Newton, MA 02465
OPEN SUN, 12PM TO 1:30PM
$1,375,000
3 beds2.5 baths1,835 sq ft
155 Auburndale Ave, Newton, MA 02465
OPEN TODAY, 12:30PM TO 2PM
$975,000
3 beds1.5 baths1,318 sq ft
30 Gilbert St, Newton, MA 02465
OPEN SUN, 12PM TO 1:30PM
$2,295,000
5 beds4.5 baths2,989 sq ft
46 Myrtle St, Newton, MA 02465
OPEN SUN, 2PM TO 3:30PM
$3,900,000
6 beds5.5 baths6,097 sq ft
44 Putnam St, Newton, MA 02465
$2,750,000
4 beds3.5 baths4,468 sq ft
54 Hampshire St, Newton, MA 02465
See all

Provided by Redfin

Sale history for 271 Chestnut St

Date

Event

Price

MLS PIN #72894711

Jan 6, 2022

Sold

$3,175,000

$529/sq ft

Nov 3, 2021

Price Changed

$3,350,000

$558/sq ft

Sep 14, 2021

Listed

$3,399,000

$567/sq ft

MLS PIN #1

Jun 22, 2021

Price Changed

$3,399,000

$567/sq ft

MLS PIN #71979292

Jun 17, 2016

Sold

$1,725,000

$288/sq ft

Apr 1, 2016

Pending

—

Mar 30, 2016

Listed

$1,695,000

$283/sq ft

+25

Location! Location! Location! Outstanding Craftsman style home set back from the street on 30,000 square feet of lovely level land in the heart of West Newton Hill. Enter the property through a wrought iron gate and alight under the porte cochere to an inviting front to back porch. Gracious foyer, formal living room with ample size fireplace, opening to an entertainment size dining room with beamed ceiling, fireplace and French doors to the screened porch. Adjacent to the dining room flow through to the butler’s pantry and kitchen. A master bedroom, second bedroom or office & bath complete the first floor. The second floor has an open space landing with a handsome wrought iron railing from which one enters the upper level rooms: The 38x15 foot party room, bar, two bedrooms and charming wood paneled library and 2 baths. Close to T, commuter rail, express bus, Brae Burn Country Club & The Neighborhood Club. Bring your imagination & creativity. A rare one of a kind gem!!

Year

Property tax

Land + Additions

Assessment*

2026

$31,373 (+3.8%)

$1,533,300 + $1,704,400

$3,237,700

2025

$30,218 (+3.4%)

$1,460,300 + $1,623,200

$3,083,500

2024

$29,219 (+5.3%)

$1,417,800 + $1,575,900

$2,993,700

2023

$27,737 (+4.5%)

$1,135,200 + $1,589,500

$2,724,700

2022

$26,541 (+22.1%)

$1,051,100 + $1,471,800

$2,522,900

2021

$21,729 (+3.1%)

$991,600 + $1,027,800

$2,019,400

2020

$21,083 (+2.9%)

$991,600 + $1,027,800

$2,019,400

2019

$20,488 (+7.1%)

$962,700 + $997,900

$1,960,600

2018

$19,137 (+22.4%)

$853,700 + $915,000

$1,768,700

2017

$15,637 (+16.1%)

$805,400 + $600,800

$1,406,200

2016

$13,466 (+4.9%)

$752,600 + $430,700

$1,183,300

2015

$12,839 (−0.8%)

$703,400 + $402,500

$1,105,900

2014

$12,949 (+22.4%)

$641,200 + $427,200

$1,068,400

2013

$10,575 (+2.9%)

$641,200 + $279,200

$920,400

2012

$10,281 (+1.6%)

$641,200 + $279,200

$920,400

2011

$10,115 (+2.6%)

$628,900 + $299,100

$928,000

2010

$9,857 (+2.4%)

$641,700 + $305,200

$946,900

2009

$9,623

$654,800 + $311,400

$966,200

Tax history for 271 Chestnut St

Year

Property tax

Land + Additions

Assessment*

2026

$31,373 (+3.8%)

$1,533,300 + $1,704,400

$3,237,700

2025

$30,218 (+3.4%)

$1,460,300 + $1,623,200

$3,083,500

2024

$29,219 (+5.3%)

$1,417,800 + $1,575,900

$2,993,700

2023

$27,737 (+4.5%)

$1,135,200 + $1,589,500

$2,724,700

2022

$26,541 (+22.1%)

$1,051,100 + $1,471,800

$2,522,900

2021

$21,729 (+3.1%)

$991,600 + $1,027,800

$2,019,400

2020

$21,083 (+2.9%)

$991,600 + $1,027,800

$2,019,400

2019

$20,488 (+7.1%)

$962,700 + $997,900

$1,960,600

2018

$19,137 (+22.4%)

$853,700 + $915,000

$1,768,700

2017

$15,637 (+16.1%)

$805,400 + $600,800

$1,406,200

2016

$13,466 (+4.9%)

$752,600 + $430,700

$1,183,300

2015

$12,839 (−0.8%)

$703,400 + $402,500

$1,105,900

2014

$12,949 (+22.4%)

$641,200 + $427,200

$1,068,400

2013

$10,575 (+2.9%)

$641,200 + $279,200

$920,400

2012

$10,281 (+1.6%)

$641,200 + $279,200

$920,400

2011

$10,115 (+2.6%)

$628,900 + $299,100

$928,000

2010

$9,857 (+2.4%)

$641,700 + $305,200

$946,900

2009

$9,623

$654,800 + $311,400

$966,200

*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

5.5

Stories

Lot width

—

Lot depth

—

Lot size

0.69 Acres

Year renovated

—

Sq. Ft.

3,324

Year built

1905

Style

Other

County

Middlesex County

APN

2387366S

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Sep 10, 2026.

Property details

Parking

Parking Information
Has Garage
Has Open Parking
# of Garage Spaces: 2
# of Covered Spaces: 2
Parking Spaces: 6
Parking Features: Detached, Paved Drive, Off Street

Interior

Master Bedroom Information
Area: 345
Length: 23
Width: 15
Level: Second

Bedroom #2 Information
Area: 238
Length: 17
Width: 14
Level: Second

Bedroom #3 Information
Area: 182
Length: 14
Width: 13
Level: Second

Bedroom #4 Information
Area: 130
Length: 13
Width: 10
Level: Second

Bedroom #5 Information
Area: 140
Length: 14
Width: 10
Level: Basement

Bathroom Information
# of Bathrooms (Full): 5
# of Bathrooms (Half): 1

Bathroom #1 Information
Level: Second

Bathroom #2 Information
Level: Second

Bathroom #3 Information
Level: Second

Living Room Information
Area: 384
Length: 24
Width: 16
Level: First

Family Room Information
Area: 288
Length: 18
Width: 16
Level: First

Dining Room Information
Area: 256
Length: 16
Width: 16
Level: First

Kitchen Information
Area: 208
Length: 16
Width: 13
Level: First

Office Room Information
Area: 2,058
Length: 147
Width: 14
Level: First

Basement Information
Basement: Full, Finished

Laundry Information
Laundry Dimen: 11X10
Laundry Features: Second Floor

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 3

Interior Features
# of Rooms (Total): 14
Flooring: Hardwood
Interior Features: Home Office, Play Room, Exercise Room, Media Room, Bathroom, Inlaw Apt.

Exterior

Building Information
Building Area (Total): 6,000
Foundation Details: Stone
Year Built Source: Public Records
Year Built Details: Approximate

Exterior Features
Fencing: Fenced/Enclosed, Fenced
Patio And Porch Features: Screened, Patio
Exterior Features: Porch - Screened, Patio, Rain Gutters, Hot Tub/Spa, Professional Landscaping, Sprinkler System, Fenced Yard

Pool Information
Has Spa
Spa Features: Private

Property Information
PropertySubType: Single Family Residence

Lot Information
Lot Size (Acres): 0.69
Lot Features: Gentle Sloping, Level
Road Frontage Type: Public

Financial

Tax Information
Tax Annual Amount: $21,729
Tax Year: 2021

Utilities

Utility Information
Sewer: Public Sewer
Water Source: Public

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

Location

Location Information
Directions: Commonwealth Ave. to Chestnut Street
UnparsedAddress: 271 Chestnut St, Newton MA 02465

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Tennis Court(s), Park, Walk/Jog Trails, Bike Path, Public School

Public facts

Beds: 4
Baths: 5.5
Sq. Ft.: 3,324
Stories: 2.0
Lot Size: 0.69 acres
Style: Other
Year Built: 1905
Year Renovated: —
County: Middlesex County
APN: 2387366S

Home facts updated by county records on Sep 10, 2026

Other

Miscellaneous Information
Heat Zones: 8

Listing Information
StandardStatus: Closed

Around this home

Schools

Peirce Elementary School

Public K-5 • Assigned • 0.4mi

8/10

F A Day Middle School

Public 6-8 • Assigned • 1.3mi

9/10

Newton North 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 96° expected this year, 13 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, 3 days in 30 years

Provided by First Street

Historical weather

Newton, MA • 02465

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

$4.03M – $4.87M

Reach more buyers when you sell with Redfin. Save up to $42,363 in fees. 3 minutes to get started.

Need the cash from your home fast? Sell to .

Nearby similar homes

$989,000

4 beds2 baths1,437 sq ft

122 Austin St, Newton, MA 02460

$3,150,000

6 beds5.5 baths5,378 sq ft

1058 Beacon St #2, Newton, MA 02459

VIDEO TOUR

$1,250,000

5 beds2.5 baths2,477 sq ft

39 Holman Rd, Auburndale, MA 02466

OPEN TODAY, 12:30PM TO 2PM3D WALKTHROUGH

$2,895,000

5 beds4.5 baths5,615 sq ft

27 Gammons Rd, Waban, MA 02468

$2,599,000

4 beds3.5 baths3,467 sq ft

956 Walnut St #2, Newton, MA 02461

$1,499,000

4 beds4 baths3,188 sq ft

1935 Commonwealth Ave #1935, Auburndale, MA 02466

New listings for sale in 02465

OPEN SUN, 2:15PM TO 3:15PM

$1,299,000

4 beds3.5 baths2,202 sq ft

123 Mount Vernon St #1, West Newton, MA 02465

$2,999,000

6 beds8 baths6,058 sq ft

42 Lindbergh Ave, Newton, MA 02465

OPEN TODAY, 1:30PM TO 2:30PM

$4,295,000

7 beds6 baths7,810 sq ft

14 Winthrop St, Newton, MA 02465

$6,195,000

7 beds6.5 baths8,989 sq ft

95 Temple St, Newton, MA 02465

OPEN TODAY, 1:30PM TO 3PM

$1,199,000

3 beds3 baths2,302 sq ft

15 Alden Pl #15, Newton, MA 02465

OPEN SUN, 12PM TO 1:30PM3D WALKTHROUGH

$1,375,000

3 beds2.5 baths1,835 sq ft

155 Auburndale Ave, Newton, MA 02465

OPEN TODAY, 12:30PM TO 2PMHOT HOME

$975,000

3 beds1.5 baths1,318 sq ft

30 Gilbert St, Newton, MA 02465

OPEN SUN, 12PM TO 1:30PM

$2,295,000

5 beds4.5 baths2,989 sq ft

46 Myrtle St, Newton, MA 02465

OPEN SUN, 2PM TO 3:30PM

$3,900,000

6 beds5.5 baths6,097 sq ft

44 Putnam St, Newton, MA 02465

Home values near 271 Chestnut St

Data from public records.

Address	Redfin Estimate
257 Chestnut St, Newton, MA 7 Beds \| 4.5 Baths \| 6432 Sq. Ft.	$4,217,450
288 Chestnut St, Newton, MA 5 Beds \| 6 Baths \| 7836 Sq. Ft.	$4,057,198

Address	Redfin Estimate
279 Chestnut St, Newton, MA 4 Beds \| 4.5 Baths \| 4297 Sq. Ft.	$3,280,137
272 Chestnut St, Newton, MA 3 Beds \| 3.5 Baths \| 1919 Sq. Ft.	$1,678,041

Address	Redfin Estimate
287 Chestnut St, Newton, MA 6 Beds \| 4.5 Baths \| 5951 Sq. Ft.	$3,201,153
260 Chestnut St, Newton, MA 6 Beds \| 3.5 Baths \| 5391 Sq. Ft.	$3,875,472

Property information provided by MLS PIN when last listed in 2021. This data may not match . Learn more.

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

02493 homes for sale
02132 homes for sale
02467 homes for sale
02135 homes for sale
02472 homes for sale

Brighton homes for sale
South Brookline homes for sale
Chestnut Hill homes for sale
Newton Highlands homes for sale
West Roxbury homes for sale

Houses for rent in Newton	Agents near me	Quincy, MA homes for sale	Newton Housing Market
Houses for sale near me	Boston, MA homes for sale	Brookline, MA homes for sale
Land for sale near me	Newton, MA homes for sale	Arlington, MA homes for sale
Open Houses near me	Cambridge, MA homes for sale	Newton Property Records
Condos for sale near me	Lexington, MA homes for sale	MA New Listings

Cambridge homes for sale
Boston homes for sale
Lexington homes for sale

About this home

Redfin Estimate

Earn from this home

Market trends in 02465, MA

Sale history for 271 Chestnut St

Tax history for 271 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 02465

Home values near 271 Chestnut St

More real estate resources