Off market dec 2009 for $965K

$1,655,103

Est. refi paymentEst. refi $5,261/mo

•

1,252

sq ft

39 Chestnut St #5, Boston, MA 02108

About this home

PRICE REDUCED ---- OPPORTUNITY TO OWN PENTHOUSE ON BEST STREET IN THE CITY. Two bedroom two and a half bath sun filled penthouse residence at the corner of Willow and Chestnut Streets. Each bedroom has an en suite bath, marble master with double sinks, glassed in shower. There are hardwood floors throughout, in-unit laundry, powder room on living level, wide open living / kitchen/ dining layout. Granite kitchen with Island, Spectacular City and Charles River views from PRIVATE ROOFDECK.

TownhomeProperty Type

1900Year Built

$1,322Est. Price/Sq.Ft.

Listed by Glenn Forger • Olde Forge Realty

Bought with John Ford • Ford Realty - Boston

Redfin checked: a few seconds ago

•Source:MLS PIN #70895295

Redfin Estimate

$1,655,103

$690K since sold in December 2009$86K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 30.6% lower than the average sale price ($2.38M) of 6 comparable homes.

SOLD OCT 20, 2026
$2,350,000
A
3 beds2.5 baths1,500 sq ft
93 Revere St #4, Boston, MA 02114
SOLD JUL 10, 2026
$3,230,000
B
2 beds2.5 baths1,764 sq ft
82 Mount Vernon St #1, Boston, MA 02108
SOLD JUN 30, 2026
$2,315,000
C
2 beds2.5 baths1,364 sq ft
41-43 Phillips St #8, Boston, MA 02114
SOLD APR 29, 2026
$1,800,000
D
2 beds2 baths1,260 sq ft
82 Chestnut St #30, Boston, MA 02108
SOLD OCT 28, 2026
$1,350,000
E
2 beds1 bath1,052 sq ft
41 Pinckney St #1, Boston, MA 02114
SOLD MAR 31, 2026
$3,262,500
F
2 beds2 baths1,589 sq ft
73 Mt Vernon St #2, Boston, MA 02108

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Earn from this home

Sell

$1,123,076

Est. take-home

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Refinance

Est. cash available

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Rent

$1,617/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

Provided by Redfin

Sale history for 39 Chestnut St #5

Date

Event

Price

MLSPIN #73379446

Jul 29, 2025

Rental Removed

$6,900

$6/sq ft

May 24, 2025

Listed for Rent

$6,900

$6/sq ft

MLS PIN #70895295

Dec 21, 2009

Sold

$965,000

$771/sq ft

Nov 24, 2009

Contingent

—

Oct 15, 2009

Price Changed

$999,000

$798/sq ft

Oct 1, 2009

Price Changed

$1,100,000

$879/sq ft

Jun 18, 2009

Price Changed

$1,195,000

$954/sq ft

Apr 30, 2009

Price Changed

$1,239,000

$990/sq ft

Mar 30, 2009

Listed

$1,295,000

$1,034/sq ft

Public Records

Jan 31, 2001

Sold

$795,000

$635/sq ft

Public Records

Jul 31, 1997

Sold

$420,000

$335/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$7,507 (+2.7%)

$699,000

2022

$7,311 (+4.0%)

$672,000

2021

$7,029 (+5.8%)

$658,800

2020

$6,643 (+4.2%)

$629,100

2019

$6,375 (+6.6%)

$604,800

2018

$5,980 (+1.9%)

$570,600

2017

$5,868 (+3.0%)

$554,100

2016

$5,696 (−10.6%)

$517,800

2015

$6,373 (+3.9%)

$526,300

2014

$6,131 (+3.4%)

$487,400

2013

$5,930 (+4.9%)

$451,300

2012

$5,654 (+1.9%)

$433,600

2009

$5,546 (+29.5%)

$433,600

2006

$4,281

$402,700

Tax history for 39 Chestnut St #5

Year

Property tax

Land + Additions

Assessment*

2023

$7,507 (+2.7%)

$699,000

2022

$7,311 (+4.0%)

$672,000

2021

$7,029 (+5.8%)

$658,800

2020

$6,643 (+4.2%)

$629,100

2019

$6,375 (+6.6%)

$604,800

2018

$5,980 (+1.9%)

$570,600

2017

$5,868 (+3.0%)

$554,100

2016

$5,696 (−10.6%)

$517,800

2015

$6,373 (+3.9%)

$526,300

2014

$6,131 (+3.4%)

$487,400

2013

$5,930 (+4.9%)

$451,300

2012

$5,654 (+1.9%)

$433,600

2009

$5,546 (+29.5%)

$433,600

2006

$4,281

$402,700

*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

Stories

Lot width

—

Lot depth

—

Lot size

—

Year renovated

1965

Sq. Ft.

568

Year built

1860

Style

Condo/Co-op

County

Suffolk County

APN

3356550

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 20, 2023.

Property details

Parking

Parking Information
Has Open Parking
Parking Features: On Street

Interior

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

Basement Information
Basement: N

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

Interior Features
# of Rooms (Total): 6
Flooring: Wood, Marble

Exterior

Building Information
Building Area (Total): 1,252
StructureType: Townhouse
Stories (Total): 2
Year Built Source: Owner
Year Built Details: Approximate

Property Information
PropertySubType: Condominium
Entry Level: 5

Financial

Tax Information
Tax Annual Amount: $9,392.67
Tax Year: 2009

Utilities

Utility Information
Sewer: Public Sewer
Water Source: Public, City/Town Water, City/Town Sewer

Heating & Cooling
Has Heating
Has Cooling
Heating: Hot Water
Cooling: Central Air, Window Unit(s)

Location

HOA Information
Association Fee: $583
Association Fee Includes: Heat, Water, Sewer, Insurance
Association Amenities: Hot Water

Location Information
Directions: Mt Vernon to Willow to Chestnut
UnparsedAddress: 39 Chestnut Street # 5, Boston MA 02108

Community Information
Senior CommunityYN: No

Public facts

Beds: 1
Baths: 1.0
Sq. Ft.: 568
Stories: 1.0
Lot Size: —
Style: Condo/Co-op
Year Built: 1860
Year Renovated: 1965
County: Suffolk County
APN: 3356550

Home facts updated by county records on Jul 20, 2023

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

62% 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)

34°

23°

36°

24°

50°

35°

58°

43°

68°

54°

79°

65°

83°

69°

78°

64°

73°

61°

63°

51°

53°

41°

40°

28°

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

$1.57M – $1.90M

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Home values near 39 Chestnut St #5

Data from public records.

Address	Redfin Estimate
39 Chestnut St Apt 1, Boston, MA 1 Beds \| 1 Baths \| 730 Sq. Ft.	$829,477
39 Chestnut St Apt 4, Boston, MA 1 Beds \| 1 Baths \| 584 Sq. Ft.	$835,741
43 Chestnut St, Boston, MA 4 Beds \| 4 Baths \| 4290 Sq. Ft.	$5,043,393
35 Chestnut St, Boston, MA 6 Beds \| 5 Baths \| 4824 Sq. Ft.	$5,780,070
9 Willow St Apt 1, Boston, MA 1 Beds \| 1 Baths \| 465 Sq. Ft.	$557,077
9 Willow St Apt 42, Boston, MA - Beds \| 1 Baths \| 331 Sq. Ft.	$545,150
9 Willow St Apt 72, Boston, MA 1 Beds \| 1 Baths \| 312 Sq. Ft.	$570,936

Address	Redfin Estimate
39 Chestnut St Apt 2, Boston, MA 2 Beds \| 1 Baths \| 771 Sq. Ft.	$978,294
39 Chestnut St Apt 6, Boston, MA 1 Beds \| 2 Baths \| 684 Sq. Ft.	$925,206
45 Chestnut St, Boston, MA 5 Beds \| 4.5 Baths \| 4515 Sq. Ft.	$5,474,266
37 Chestnut St, Boston, MA 4 Beds \| 6 Baths \| 5416 Sq. Ft.	$8,028,262
9 Willow St Apt 21, Boston, MA 1 Beds \| 1 Baths \| 350 Sq. Ft.	$561,778
9 Willow St Apt 52, Boston, MA 1 Beds \| 1 Baths \| 331 Sq. Ft.	$596,083
9 Willow St Apt 82, Boston, MA 1 Beds \| 1 Baths \| 312 Sq. Ft.	$614,011

Address	Redfin Estimate
39 Chestnut St Apt 3, Boston, MA 1 Beds \| 1 Baths \| 568 Sq. Ft.	$853,247
41 Chestnut St, Boston, MA 5 Beds \| 3.5 Baths \| 3849 Sq. Ft.	$5,714,023
47 Chestnut St, Boston, MA 6 Beds \| 4 Baths \| 4010 Sq. Ft.	$5,164,276
7 Willow St, Boston, MA 3 Beds \| 3 Baths \| 2298 Sq. Ft.	$2,815,292
9 Willow St Apt 32, Boston, MA 1 Beds \| 1 Baths \| 331 Sq. Ft.	$583,027
9 Willow St Apt 71, Boston, MA 1 Beds \| 1 Baths \| 687 Sq. Ft.	$921,830
2 Acorn St, Boston, MA 4 Beds \| 3 Baths \| 2887 Sq. Ft.	$4,031,182

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 39 Chestnut St #5

Tax history for 39 Chestnut St #5

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

Home values near 39 Chestnut St #5

More real estate resources