Google street view image for 165 Chestnut St, Brookline, MA 02445

Off market

—

•

122.5 ba

•

—

sq ft

165 Chestnut St, Brookline, MA 02445

About this home

165 Chestnut St is a property on a 6.03 acre lot with 95 bedrooms and 122.5 bathrooms.

1996Year Built

6.03 acresLot Size

Source:Public Records

Redfin Estimate

Unfortunately, we don't have enough data to generate an accurate Estimate at this time.

Market trends in 02445, MA

Last updated September 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-list price

97.3%

1.5% MoM

Median sale price

$1.0M

$142K MoM

Avg. days on market

56d

14 days MoM

Recently sold homes

16 MoM

New listings for sale

OPEN SUN, 3:30PM TO 5PM
$798,800
2 beds2 baths1,099 sq ft
22 Chestnut Pl #114, Brookline, MA 02445
COMING SOON
$685,000
2 beds1 bath970 sq ft
8 Homer #4, Brookline, MA 02445
EARLY ACCESS
$7,900,000
6 beds14 baths8,934 sq ft
125 Rockwood St, Brookline, MA 02445
OPEN TODAY, 11AM TO 12:30PM
$1,199,000
2 beds2 baths1,220 sq ft
89 Glen Rd #5, Brookline, MA 02445
$2,195,000
3 beds3.5 baths3,525 sq ft
301 Goddard Ave #301, Brookline, MA 02445
OPEN TODAY, 11AM TO 1PM
$899,000
2 beds2 baths1,095 sq ft
127 Winthrop Rd Unit 1A, Brookline, MA 02445
OPEN TODAY, 1:45PM TO 2:45PM
$479,000
1 bed1 bath632 sq ft
133 Beaconsfield Rd #14, Brookline, MA 02445
OPEN SUN, 1:15PM TO 2:30PM
$1,595,000
3 beds2 baths1,105 sq ft
69 Walnut St #7, Brookline, MA 02445
$499,000
1 bed1 bath615 sq ft
136 Beaconsfield Rd #2, Brookline, MA 02445
$635,000
2 beds1 bath806 sq ft
1834 Beacon St #5, Brookline, MA 02445
See all

Provided by Redfin

Sale history for 165 Chestnut St

As the MLS and public records start to fill up, we'll list the details here.

Tax history for 165 Chestnut St

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

Permits

Jul 27, 2026 • Active

Commercial gas

Gas

HVAC

Jul 17, 2026 • Active

Commercial plumbing

Plumbing

Water heater

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

Exterior

Property Information
Legal Description: MAPNUM:000000 WARDNUM:00 BLOCKNUM:000330 LOTNUM:000002 UNITNUM:00000
Property Type: Condo/Apt
Exterior: Wood
Roof: Asphalt
Heating/Cooling: Has Heating and Cooling
Heating: Forced Air
#of Rooms: 143

Public facts

Beds: 95
Baths: 122.5
Sq. Ft.: —
Stories: 3.0
Lot Size: 6.03 acres
Style: Other
Year Built: 1996
Year Renovated: —
County: Norfolk County
APN: B330L0002S0015

Home facts updated by county records on Aug 14, 2019

Around this home

Schools

William H Lincoln School

Public K-8 • Assigned • 0.5mi

9/10

Brookline High School

Public 9-12 • Assigned • 0.7mi

8/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Local insights from Redfin agents

Brookline will continue to be a Seller's market for the foreseeable future, driven by restrictive zoning laws that have limited increases in housing production and a stable population with relatively low turnover. This has resulted in a massive...
1 month ago • Brookline
Benjamin Ginsburg
Redfin Premier agent
155 deals
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Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

3/10 Fire Factor

0.15% chance of being in a wildfire in next 30 years

5/10 Heat Factor

7 days above 96° 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

Brookline, MA • 02445

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

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Sun exposure

Try the sun simulator tool to see how light moves across the property at different times of day and year.

Provided by Shadowmap

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Nearby similar homes

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New listings for sale in 02445

OPEN SUN, 3:30PM TO 5PM

$798,800

2 beds2 baths1,099 sq ft

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COMING SOON

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Top-floor sanctuary • In-unit laundry • Tree-top views

EARLY ACCESSCOLDWELL BANKER REALTY COMING SOON

$7,900,000

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OPEN TODAY, 11AM TO 12:30PM

$1,199,000

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Private terrace • Renovated kitchen • Rear garden area

$2,195,000

3 beds3.5 baths3,525 sq ft

301 Goddard Ave #301, Brookline, MA 02445

Expansive deck • Renovated kitchen • Walkout lower level

OPEN TODAY, 11AM TO 1PM3D & VIDEO TOUR

$899,000

2 beds2 baths1,095 sq ft

127 Winthrop Rd Unit 1A, Brookline, MA 02445

Two private porches • Updated kitchen • In unit laundry

OPEN TODAY, 1:45PM TO 2:45PM

$479,000

1 bed1 bath632 sq ft

133 Beaconsfield Rd #14, Brookline, MA 02445

On-site laundry • Nearby parks • Waldstein playground

OPEN SUN, 1:15PM TO 2:30PM

$1,595,000

3 beds2 baths1,105 sq ft

69 Walnut St #7, Brookline, MA 02445

Private balcony • Elevator • Storage closets

$499,000

1 bed1 bath615 sq ft

136 Beaconsfield Rd #2, Brookline, MA 02445

Oversized windows • Hardwood floors • Pet-friendly complex

Home values near 165 Chestnut St

Data from public records.

Address	Redfin Estimate
166 Chestnut St Apartment 1, Brookline, MA 3 Beds \| 2 Baths \| 1079 Sq. Ft.	$805,137
162 Chestnut St, Brookline, MA 8 Beds \| 3 Baths \| 3588 Sq. Ft.	$1,961,099

Address	Redfin Estimate
166 Chestnut St Apartment 2, Brookline, MA 2 Beds \| 1 Baths \| 945 Sq. Ft.	$647,068
160 Chestnut St, Brookline, MA 6 Beds \| 3 Baths \| 4212 Sq. Ft.	—

Address	Redfin Estimate
166 Chestnut St Apartment 3, Brookline, MA 2 Beds \| 1 Baths \| 948 Sq. Ft.	$685,583
156 Chestnut St Apartment 1, Brookline, MA 2 Beds \| 2 Baths \| 1118 Sq. Ft.	$810,610

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GreatSchools Ratings provided by GreatSchools.org.

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