39 Chatham St, Brookline, MA 02446
OFF MARKET

39 Chatham St
Brookline, MA 02446

Longwood
  • 5 Beds
  • 4.5 Baths
  • 3,740 sqft

$4,633,200

Trulia Estimate
as of May 25, 2026
Est. Refi. Payment $27,028/mo*
Refinance Your Home

$4,633,200

Trulia Estimate
as of May 25, 2026
Est. Refi. Payment $27,028/mo*
Refinance Your Home
5 Beds
4.5 Baths
3,740 sqft

Local Information

Map showing home location
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-- mins to
Commute Destination

Description

Exquisite home on Brookline's coveted Longwood Mall Park with its historic European Beech trees. This gracious Federal Revival on a private lot and quiet street features an abundance of flowering trees & plants and a wonderful private courtyard with a fountain, perennial plantings and brick patio. This wonderful home, with gorgeous original details, has been meticulously cared for by the current owners. Spacious formal living room with a handcrafted mantle and lovely built ins. Enormous master suite with private bath featuring radiant heat and a soaking tub. The lower level is perfect for an au pair or in-law and offers direct access two car garage.The best of suburban living yet minutes to Boston, Longwood medical, shops and restaurants and the "T".
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 39 Chatham St

Interior Features

Heating & Cooling
Heating: Other, GasAir ConditioningHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 11
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: SlateExterior: Brick
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1941Year Updated: 1978
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 9583 sqft

Price History for 39 Chatham St

DatePriceEventSource
08/22/2016$3,100,000Sold
N/A
06/14/2016$3,200,000Listed For SaleAgent Provided
04/25/2003$2,000,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$37,917
Assessment$3,841,600
Home facts updated by county records

Comparable Sales for 39 Chatham St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
232 Kent St, Brookline, MA
0.30
Single-Family Home
$4,000,000
08/01/25
5
4.5
5,296
53 Worthington Rd, Brookline, MA
0.42
Single-Family Home
$2,876,250
08/14/25
5
3.5
3,994
105 Babcock St, Brookline, MA
0.51
Single-Family Home
$3,595,000
05/04/26
5
4.5
4,882
212 Aspinwall Ave, Brookline, MA
0.51
Single-Family Home
$2,350,000
05/30/25
7
3.5
3,796
6 Elba St, Brookline, MA
0.55
Single-Family Home
$3,000,000
12/09/25
5
4.5
2,997
157 Aspinwall Ave, Brookline, MA
0.51
Single-Family Home
$2,800,000
09/22/25
5
4
4,784
87 Crowninshield Rd, Brookline, MA
0.53
Single-Family Home
$3,865,000
07/28/25
4
2.5
3,838
157 Aspinwall Ave, Brookline, MA
0.51
Single-Family Home
$2,800,000
09/22/25
4
4
3,515
61 Centre St, Brookline, MA
0.66
Single-Family Home
$3,475,000
06/26/25
5
3.5
4,699
11 Abbottsford Rd, Brookline, MA
0.64
Single-Family Home
$2,621,500
12/29/25
8
4.5
4,720

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Assigned Schools

These are the assigned schools for 39 Chatham St.
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Neighborhood Overview

Longwood
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Longwood

  • Kelly G.
    "It feels like an oasis from Boston while still being so close to the city. I can be in our buildings backyard but still walk to fenway in 5 minutes"
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39 Chatham St, Brookline, MA 02446 is a 5 bedroom, 5 bathroom, 3,740 sqft single-family home built in 1941. 39 Chatham St is located in Longwood, Brookline. This property is not currently available for sale. 39 Chatham St was last sold on Aug 22, 2016 for $3,100,000. The current Trulia Estimate for 39 Chatham St is $4,633,200.