OFF MARKET

Off market aug 2022 for $3.6M

$3,898,473

Est. refi paymentEst. refi $361/mo

•

3,170

sq ft

88 Chestnut St, Boston, MA 02108

About this home

Flat of the Hill gem showcasing private outdoor space, open/airy layout, and wonderful natural sunlight awaits your customization. This 3+ bedroom single family home features an expansive first floor living room (open to the 2nd floor), dining area+bar, and eat-in kitchen with direct access to a large private patio. Enjoy iconic views of Chestnut Street from the front-facing cozy window seat. The 2nd floor family room features extraordinary wall space for art, the beautifully paneled ceiling, custom built-ins, and 2 bonus spaces - currently used as offices. A tranquil sunroom lends optionality for additional space. Well-proportioned bedrooms and closets throughout. Completing this sensational home is the private roof deck, providing a quiet oasis in the heart of Boston. Fireplaces, skylights, and extra storage complete this special Beacon Hill home.

Single-familyProperty Type

1850Year Built

1,325 sq ftLot Size

$1,230Est. Price/Sq.Ft.

1 spaceParking

Listed by Jeannemarie Conley • Compass

Bought with Gail Roberts, Ed Feijo & Team • Coldwell Banker Realty - Cambridge

Redfin checked: a minute ago

•Source:MLS PIN #72990301

Redfin Estimate

$3,898,473

$298K since sold in August 2022$23K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 8.6% higher than the average sale price ($3.59M) of 6 comparable homes.

SOLD AUG 24, 2026
$4,075,000
A
4 beds2.5 baths3,490 sq ft
108 Pembroke St, Roxbury, MA 02118
SOLD AUG 31, 2026
$4,000,000
B
4 beds3.5 baths3,288 sq ft
70 Montgomery St, Boston, MA 02116
SOLD MAY 27, 2026
$2,615,000
C
3 beds2.5 baths1,837 sq ft
5 Rollins Pl, Boston, MA 02114
SOLD APR 30, 2026
$3,750,000
D
3 beds2.5 baths2,480 sq ft
28 Bradford St, Roxbury, MA 02118
SOLD SEP 9, 2026
$4,500,000
E
4 beds3.5 baths3,303 sq ft
5 Charles River Sq, Boston, MA 02114
SOLD APR 10, 2026
$2,600,121
F
3 beds2 baths1,945 sq ft
121 Pinckney St, Boston, MA 02114

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

Earn from this home

Sell

$1,054,265

Est. take-home

List your home with Redfin and save $19,492

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$2,705/mo

Redfin rental estimate

List your home for rent

Market trends in Flat of the Hill, MA

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

93.2%

0.0% MoM

Median sale price

$1.3M

$0 MoM

Avg. days on market

46d

0 days MoM

Recently sold homes

0 MoM

New listings for sale

$525,000
1 bed1 bath438 sq ft
21 Beacon St Unit 6B, Boston, MA 02108
$425,500
Studio1 bath298 sq ft
8 Brimmer St Unit 1A, Boston, MA 02108
See all

Provided by Redfin

Sale history for 88 Chestnut St

Year

Property tax

Land + Additions

Assessment*

2023

$38,959 (+3.7%)

$2,078,500 + $1,549,000

$3,627,500

2022

$37,587 (+4.0%)

$1,979,500 + $1,475,200

$3,454,700

2021

$36,139 (+7.4%)

$1,940,700 + $1,446,300

$3,387,000

2020

$33,637 (+5.8%)

$1,576,300 + $1,609,000

$3,185,300

2019

$31,801 (+7.6%)

$1,285,600 + $1,731,600

$3,017,200

2018

$29,563 (+3.9%)

$1,285,600 + $1,535,300

$2,820,900

2017

$28,451 (+0.1%)

$1,285,600 + $1,401,000

$2,686,600

2016

$28,416 (−1.1%)

$1,285,600 + $1,297,700

$2,583,300

2015

$28,721 (+1.1%)

$1,044,600 + $1,327,100

$2,371,700

2014

$28,416 (+3.4%)

$1,044,600 + $1,214,200

$2,258,800

2013

$27,481 (+8.7%)

$1,044,600 + $1,046,800

$2,091,400

2012

$25,292 (+8.1%)

$635,565 + $1,303,995

$1,939,560

2009

$23,396 (+23.5%)

$635,565 + $1,193,640

$1,829,205

2006

$18,942

$594,300 + $1,187,600

$1,781,900

Tax history for 88 Chestnut St

Year

Property tax

Land + Additions

Assessment*

2023

$38,959 (+3.7%)

$2,078,500 + $1,549,000

$3,627,500

2022

$37,587 (+4.0%)

$1,979,500 + $1,475,200

$3,454,700

2021

$36,139 (+7.4%)

$1,940,700 + $1,446,300

$3,387,000

2020

$33,637 (+5.8%)

$1,576,300 + $1,609,000

$3,185,300

2019

$31,801 (+7.6%)

$1,285,600 + $1,731,600

$3,017,200

2018

$29,563 (+3.9%)

$1,285,600 + $1,535,300

$2,820,900

2017

$28,451 (+0.1%)

$1,285,600 + $1,401,000

$2,686,600

2016

$28,416 (−1.1%)

$1,285,600 + $1,297,700

$2,583,300

2015

$28,721 (+1.1%)

$1,044,600 + $1,327,100

$2,371,700

2014

$28,416 (+3.4%)

$1,044,600 + $1,214,200

$2,258,800

2013

$27,481 (+8.7%)

$1,044,600 + $1,046,800

$2,091,400

2012

$25,292 (+8.1%)

$635,565 + $1,303,995

$1,939,560

2009

$23,396 (+23.5%)

$635,565 + $1,193,640

$1,829,205

2006

$18,942

$594,300 + $1,187,600

$1,781,900

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

Public record

Public record
Permits

Beds

Baths

1.5

Stories

Lot width

—

Lot depth

—

Lot size

1,307 Sq. Ft.

Year renovated

1998

Sq. Ft.

2,332

Year built

1890

Style

Townhouse

County

Suffolk County

APN

3353818

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 20, 2023.

Property details

Parking

Parking Information
Parking Spaces: 1
Parking Features: Leased

Interior

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

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 2

Interior Features
# of Rooms (Total): 10

Exterior

Building Information
Building Area (Total): 3,170
Foundation Details: Granite
Year Built Source: Owner
Year Built Details: Approximate

Property Information
PropertySubType: Single Family Residence
Property AttachedYN: Yes

Lot Information
Lot Size (Acres): 0.03

Financial

Tax Information
Tax Annual Amount: $37,587
Tax Year: 2022

Utilities

Utility Information
Sewer: Public Sewer
Water Source: Public

Heating & Cooling
Has Heating
Has Cooling
Heating: Central
Cooling: Central Air

Location

Location Information
Directions: Flat of the Hill Chestnut Street between River and Brimmer
UnparsedAddress: 88 Chestnut Street, Boston MA 02108

Community Information
Senior CommunityYN: No

Public facts

Beds: 3
Baths: 1.5
Sq. Ft.: 2,332
Stories: 3.0
Lot Size: 1,307 square feet
Style: Townhouse
Year Built: 1890
Year Renovated: 1998
County: Suffolk County
APN: 3353818

Home facts updated by county records on Jul 20, 2023

Other

Listing Information
Exclusions: Kitchen Light Fixture.
StandardStatus: Closed

Around this home

Schools

Josiah Quincy Elementary School

Public PreK-5 • Assigned • 0.7mi

8/10

Quincy Upper School

Public 6-12 • Assigned • 0.7mi

3/10

Snowden Int'L High School

Public 9-12 • Assigned • 0.6mi

2/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

9/10 Flood Factor

Estimated 80%+ chance 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

6/10 Heat Factor

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

6/10 Wind Factor

64% chance of strong winds in next 30 years

3/10 Air Factor

3 unhealthy days expected this year, 3 days in 30 years

Provided by First Street

Historical weather

Boston, MA • 02108

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 9.2 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

9.2 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$3.70M – $4.48M

Reach more buyers when you sell with Redfin. Save up to $38,985 in fees. 3 minutes to get started.

Need the cash from your home fast? Sell to .

Nearby similar homes

$5,950,000

6 beds6 baths6,106 sq ft

1 West Hill Pl, Boston, MA 02114

$8,950,000

6 beds5.5 baths6,100 sq ft

1 Fairfield St, Boston, MA 02116

$6,750,000

3 beds3.5 baths2,983 sq ft

19 Charles River Sq, Boston, MA 02114

$3,995,000

5 beds5 baths3,228 sq ft

54 Brimmer St, Boston, MA 02108

$7,250,000

5 beds3.5 baths5,165 sq ft

381 Beacon St, Boston, MA 02116

$3,625,000

5 beds4 baths3,160 sq ft

20 Shawmut St, Boston, MA 02116

New listings for sale in 02108

$525,000

1 bed1 bath438 sq ft

21 Beacon St Unit 6B, Boston, MA 02108

$425,500

Studio1 bath298 sq ft

8 Brimmer St Unit 1A, Boston, MA 02108

Home values near 88 Chestnut St

Data from public records.

Address	Redfin Estimate
96 Chestnut Street #3, Boston, MA 2 Beds \| 2 Baths \| 1316 Sq. Ft.	$1,999,199
94 Chestnut Street, Boston, MA 6 Beds \| 5 Baths \| 4778 Sq. Ft.	$4,368,929

Address	Redfin Estimate
96 Chestnut Street #2, Boston, MA 3 Beds \| 2.5 Baths \| 1473 Sq. Ft.	$2,113,341
90 Chestnut Street #90A, Boston, MA 5 Beds \| 5.5 Baths \| 4992 Sq. Ft.	$5,237,349

Address	Redfin Estimate
96 Chestnut Street #5, Boston, MA 2 Beds \| 2 Baths \| 1432 Sq. Ft.	$2,283,031
90 Chestnut Street, Boston, MA 5 Beds \| 5.5 Baths \| 6421 Sq. Ft.	$5,894,501

Property information provided by MLS PIN when last listed in 2022. 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.

02127 homes for sale
02129 homes for sale
02130 homes for sale
02132 homes for sale
02135 homes for sale

Houses for rent in Boston	Agents near me	Quincy, MA homes for sale	Boston 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	Boston Property Records
Condos for sale near me	Lexington, MA homes for sale	MA New Listings

Cambridge homes for sale
Newton homes for sale
Lexington homes for sale

Fenway-Kenmore homes for sale
Flat of the Hill homes for sale
Beacon Hill homes for sale