SOLD NOV 18, 2025

Off market nov 2025 for $10M

$11,254,838

Est. refi paymentEst. refi $3,253/mo

•

6,653

sq ft

21 Chestnut St, Boston, MA 02108

About this home

Exquisitely marrying historic Beacon Hill character with contemporary design, this 2017 gut renovated 4 bedroom + 2 office townhouse has been thoughtfully designed and expertly crafted! 6 levels of living connected by an elegantly draping oval staircase, this home boasts a parlor level eat in kitchen with concealed top-of-the-line appliances & storage, walk in pantry and breakfast room that are accessible to the enclosed garden. Ideal for formal entertaining the parlor also offers formal living with South facing views of Chestnut St and a large formal dining room. A 2nd floor double parlor features dual gas fireplaces, a fully equipped bar, floor to ceiling windows and a juliet balcony. A private office with access to the deck is also located on this level. A serene primary suite with dressing room, and ultra luxurious marble bath. Separate entrance with enormous mudroom, home gym, A/V system, concealed storage throughout, many custom built-ins, and excellent southern sun light!

Single-familyProperty Type

1830Year Built

2,000 sq ftLot Size

$1,692Est. Price/Sq.Ft.

Listed by Michael Harper • Coldwell Banker Realty - Boston

Bought with Michael Harper • Coldwell Banker Realty - Boston

Redfin checked: a minute ago

•Source:MLS PIN #73337575

Redfin Estimate

$11,254,838

$855K since sold in November 2025$399K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 62.2% higher than the average sale price ($6.94M) of 5 comparable homes.

SOLD JUL 17, 2026
$9,600,000
A
4 beds6 baths4,886 sq ft
126 Marlborough St, Boston, MA 02116
SOLD JUN 10, 2026
$6,700,000
B
5 beds4.5 baths4,996 sq ft
90 Mount Vernon St, Boston, MA 02108
SOLD APR 3, 2026
$10,000,000
C
4 beds5.5 baths6,138 sq ft
22 Brimmer St, Boston, MA 02108
SOLD JAN 28, 2026
$4,800,000
D
4 beds4 baths4,013 sq ft
32 West Cedar St, Boston, MA 02108
SOLD SEP 30, 2026
$3,600,000
E
5 beds3 baths3,900 sq ft
51 Pinckney St, Boston, MA 02114

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Earn from this home

Sell

$2,513,048

Est. take-home

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Refinance

Est. cash available

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Rent

$4,594/mo

Redfin rental estimate

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Market trends in South Slope, MA

Last updated October 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-list price

96.5%

+1.7% MoM

Median sale price

$3.3M

$2M MoM

Avg. days on market

29d

33 days MoM

Recently sold homes

3 MoM

New listings for sale

3D WALKTHROUGH
$599,000
1 bed1 bath591 sq ft
21 Beacon St Unit 4T, Boston, MA 02108
$7,800,000
3 beds3.5 baths2,882 sq ft
46 Beacon St #2, Boston, MA 02108
$1,449,000
2 beds2 baths1,378 sq ft
45 Province St #1402, Boston, MA 02108
See all

Provided by Redfin

Sale history for 21 Chestnut St

Date

Event

Price

MLS PIN #73337575

Nov 18, 2025

Sold

$10,400,000

$1,563/sq ft

Feb 24, 2025

Listed

$11,800,000

$1,774/sq ft

MLSPIN #73372237

Oct 4, 2025

Rental Removed

$35,000

$5/sq ft

May 9, 2025

Listed for Rent

$35,000

$5/sq ft

MLS PIN #71657486

Apr 22, 2014

Sold

$5,200,000

$782/sq ft

Apr 11, 2014

Contingent

—

Apr 8, 2014

Listed

$5,500,000

$827/sq ft

Public Records

Jun 15, 2011

Sold

$500,000

$75/sq ft

Public Records

Jul 23, 1992

Sold

$1,352,500

$203/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$95,750 (+3.6%)

$2,819,100 + $6,096,200

$8,915,300

2022

$92,380 (+4.0%)

$2,684,900 + $5,805,900

$8,490,800

2021

$88,819 (+3.7%)

$2,632,200 + $5,692,000

$8,324,200

2020

$85,658 (+5.2%)

$1,969,400 + $6,142,200

$8,111,600

2019

$81,391 (+7.6%)

$1,606,200 + $6,115,900

$7,722,100

2018

$75,661 (+3.9%)

$1,606,200 + $5,613,400

$7,219,600

2017

$72,815 (+82.5%)

$1,606,200 + $5,269,600

$6,875,800

2016

$39,903 (−38.0%)

$1,092,216 + $2,535,312

$3,627,528

2015

$64,378 (+1.1%)

$1,235,600 + $4,080,500

$5,316,100

2014

$63,691 (+6.4%)

$1,235,600 + $3,827,300

$5,062,900

2013

$59,865 (+12.4%)

$1,235,600 + $3,320,300

$4,555,900

2012

$53,281 (+8.1%)

$655,700 + $3,430,300

$4,086,000

2009

$49,284 (+21.0%)

$655,700 + $3,197,600

$3,853,300

2006

$40,724

$643,800 + $3,187,200

$3,831,000

Tax history for 21 Chestnut St

Year

Property tax

Land + Additions

Assessment*

2023

$95,750 (+3.6%)

$2,819,100 + $6,096,200

$8,915,300

2022

$92,380 (+4.0%)

$2,684,900 + $5,805,900

$8,490,800

2021

$88,819 (+3.7%)

$2,632,200 + $5,692,000

$8,324,200

2020

$85,658 (+5.2%)

$1,969,400 + $6,142,200

$8,111,600

2019

$81,391 (+7.6%)

$1,606,200 + $6,115,900

$7,722,100

2018

$75,661 (+3.9%)

$1,606,200 + $5,613,400

$7,219,600

2017

$72,815 (+82.5%)

$1,606,200 + $5,269,600

$6,875,800

2016

$39,903 (−38.0%)

$1,092,216 + $2,535,312

$3,627,528

2015

$64,378 (+1.1%)

$1,235,600 + $4,080,500

$5,316,100

2014

$63,691 (+6.4%)

$1,235,600 + $3,827,300

$5,062,900

2013

$59,865 (+12.4%)

$1,235,600 + $3,320,300

$4,555,900

2012

$53,281 (+8.1%)

$655,700 + $3,430,300

$4,086,000

2009

$49,284 (+21.0%)

$655,700 + $3,197,600

$3,853,300

2006

$40,724

$643,800 + $3,187,200

$3,831,000

*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

5.5

Stories

—

Lot width

—

Lot depth

—

Lot size

2,178 Sq. Ft.

Year renovated

2015

Sq. Ft.

6,653

Year built

1830

Style

Single Family Residential

County

Suffolk County

APN

3356683

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Feb 24, 2025.

Jan 10, 2016 • Final

Amendment to a long form

Work on a fire alarm.

Fire sprinkler

Oct 20, 2015 • Final

Certificate of occupancy

Perform interior and exterior work on a residential building.

Remodel

Permit history is from public records and may be incomplete or inaccurate. Redfin and its agents make no representations about the property condition or permit status. Buyers should independently verify all information.

Property details

Interior

Bathroom Information
# of Bathrooms (Full): 4
# of Bathrooms (Half): 3
Master Bathroom Features: Yes

Basement Information
Basement: Full, Finished, Walk-Out Access

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 4

Interior Features
# of Rooms (Total): 13

Exterior

Building Information
Building Area (Total): 6,653
Foundation Details: Concrete Perimeter
Construction Materials: Frame, Brick
Year Built Source: Public Records
Year Built Details: Approximate,Renovated Since

Exterior Features
Patio And Porch Features: Deck, Patio
Exterior Features: Deck, Patio

Property Information
PropertySubType: Single Family Residence
Property AttachedYN: Yes

Lot Information
Lot Size (Acres): 0.05
Road Frontage Type: Public

Financial

Tax Information
Tax Annual Amount: $97,177
Tax Year: 2024

Utilities

Utility Information
Sewer: Public Sewer
Water Source: Public

Heating & Cooling
Has Heating
Has Cooling
Heating: Forced Air, Baseboard
Cooling: Central Air

Location

Location Information
Directions: Upper Chestnut St between Spruce & Walnut
UnparsedAddress: 21 Chestnut St, Boston MA 02108

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Shopping, Park, Medical Facility, Bike Path, Conservation Area, Highway Access, Public School

Public facts

Beds: 3
Baths: 5.5
Sq. Ft.: 6,653
Stories: —
Lot Size: 2,178 square feet
Style: Single Family Residential
Year Built: 1830
Year Renovated: 2015
County: Suffolk County
APN: 3356683

Home facts updated by county records on Feb 24, 2025

Other

Listing Information
StandardStatus: Closed

Around this home

Schools

K - 12
Preschool & daycare

Josiah Quincy Elementary School

Public PreK-5 • Assigned • 0.7mi

8/10

Quincy Upper School

Public 6-12 • Assigned • 0.7mi

3/10

Boston Adult Academy

Public 11-12 • Assigned • 0.6mi

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

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

$10.69M – $12.94M

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3D WALKTHROUGH

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Common rooftop deck • $465 HOA • Garage

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Renovated townhouse • Granite countertops • Private patio

New listings for sale in 02108

3D WALKTHROUGH

$599,000

1 bed1 bath591 sq ft

21 Beacon St Unit 4T, Boston, MA 02108

Common roof deck • Updated open kitchen • Large closets

$7,800,000

3 beds3.5 baths2,882 sq ft

46 Beacon St #2, Boston, MA 02108

Concierge services • Front facing views • Parlor level living

$1,449,000

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Private terrace • Designer finishes • Gas cooking

Home values near 21 Chestnut St

Data from public records.

Address	Redfin Estimate
19 Chestnut Street #1, Boston, MA 1 Beds \| 1 Baths \| 302 Sq. Ft.	$506,994
19 Chestnut Street #2A, Boston, MA 1 Beds \| 1 Baths \| 530 Sq. Ft.	$717,429
19 Chestnut Street #3B, Boston, MA 1 Beds \| 1 Baths \| 551 Sq. Ft.	$732,696
19 Chestnut Street #5A, Boston, MA 1 Beds \| 1 Baths \| 426 Sq. Ft.	$599,464
20 Chestnut Street #2, Boston, MA 2 Beds \| 1 Baths \| 1699 Sq. Ft.	$1,679,764
25 Chestnut Street #1, Boston, MA 3 Beds \| 2 Baths \| 1021 Sq. Ft.	$1,690,980
25 Chestnut Street #3, Boston, MA 2 Beds \| 1 Baths \| 953 Sq. Ft.	$1,365,244

Address	Redfin Estimate
19 Chestnut Street #1A, Boston, MA 1 Beds \| 1 Baths \| 541 Sq. Ft.	$717,999
19 Chestnut Street #2B, Boston, MA 1 Beds \| 1 Baths \| 537 Sq. Ft.	$725,670
19 Chestnut Street #4A, Boston, MA 1 Beds \| 1 Baths \| 527 Sq. Ft.	$716,903
19 Chestnut Street #5B, Boston, MA 1 Beds \| 1 Baths \| 441 Sq. Ft.	$658,537
20 Chestnut Street #3, Boston, MA 2 Beds \| 2.5 Baths \| 2436 Sq. Ft.	$3,625,684
25 Chestnut Street #7, Boston, MA 1 Beds \| 1 Baths \| 504 Sq. Ft.	$1,212,025
25 Chestnut Street #4, Boston, MA 2 Beds \| 1 Baths \| 967 Sq. Ft.	$1,219,385

Address	Redfin Estimate
19 Chestnut Street #1B, Boston, MA 1 Beds \| 1 Baths \| 591 Sq. Ft.	$728,419
19 Chestnut Street #3A, Boston, MA 1 Beds \| 1 Baths \| 515 Sq. Ft.	$724,612
19 Chestnut Street #4B, Boston, MA 1 Beds \| 1 Baths \| 520 Sq. Ft.	$723,698
20 Chestnut Street #20A, Boston, MA 2 Beds \| 1 Baths \| 1435 Sq. Ft.	$2,704,940
23 Chestnut Street, Boston, MA 4 Beds \| 3 Baths \| 4396 Sq. Ft.	$5,227,879
25 Chestnut Street #2, Boston, MA 2 Beds \| 2 Baths \| 1706 Sq. Ft.	$2,539,039
25 Chestnut Street #5, Boston, MA 2 Beds \| 1 Baths \| 1043 Sq. Ft.	$2,055,155

Property information provided by MLS PIN when last listed in 2025. 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 South Slope, 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 02108

Home values near 21 Chestnut St

More real estate resources