39 Chatham St, Brookline, MA 02446
Property image
Property image
OFF MARKET

39 Chatham St
Brookline, MA 02446

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

$4,436,600

Trulia Estimate
as of Aug 23, 2026
Est. Refi. Payment $26,303/mo*
Refinance Your Home

$4,436,600

Trulia Estimate
as of Aug 23, 2026
Est. Refi. Payment $26,303/mo*
Refinance Your Home
5 Beds
4.5 Baths
3,740 sqft

Home Value

Trulia Estimate
$4.44M
Since last month
Decreased$111K (-2.4%)
Since last year
Increased$132K (+3.1%)
Since last sale
Increased$1M (+43.1%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +43% in the last 10 years
MonthEstimated value
2026
August 2026$4.44M
July 2026$4.55M
June 2026$4.62M
May 2026$4.67M
April 2026$4.57M
March 2026$4.53M
February 2026$4.41M
January 2026$4.28M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
57 Monmouth St, Brookline, MA
0.24
Single-Family Home
$3,750,000
05/27/26
5
3.5
3,500
95 Babcock St, Brookline, MA
0.51
Single-Family Home
$4,050,000
08/13/26
5
4.5
3,738
105 Babcock St, Brookline, MA
0.51
Single-Family Home
$3,595,000
05/04/26
5
4.5
4,882
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
157 Aspinwall Ave, Brookline, MA
0.51
Single-Family Home
$2,800,000
09/22/25
5
4
4,784
11 Abbottsford Rd, Brookline, MA
0.64
Single-Family Home
$2,621,500
12/29/25
8
4.5
4,720
61 Toxteth St, Brookline, MA
0.46
Single-Family Home
$2,525,000
04/15/26
5
1.5
2,484
80 Mason Ter, Brookline, MA
0.93
Single-Family Home
$3,100,000
08/05/26
5
3.5
3,680
123 Centre St, Brookline, MA
0.79
Single-Family Home
$4,070,000
06/30/26
5
4.5
4,800

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
40 Hawes St, Brookline, MA 02446
0.09
$4,284,900
6
6.5
5,709
Off Market
20 Chapel St #B607, Brookline, MA 02446
0.13
$1,070,100
2
1
992
Off Market
20 Chapel St #B606, Brookline, MA 02446
0.13
$592,700
Studio
1
564
Off Market
20 Chapel St #B603, Brookline, MA 02446
0.13
$771,000
1
1
742
Off Market
20 Chapel St #A503, Brookline, MA 02446
0.13
$819,800
1
1
780
Off Market
20 Chapel St #C1005, Brookline, MA 02446
0.13
$1,701,800
2
2
1,515
Off Market
20 Chapel St #B801, Brookline, MA 02446
0.13
$820,800
1
1
764
Off Market
20 Chapel St #BPH5, Brookline, MA 02446
0.13
$1,853,200
2
2
1,511
Off Market
20 Chapel St #CS1, Brookline, MA 02446
0.13
$2,375,900
Studio
0.5
5,560
Off Market
20 Chapel St #304, Brookline, MA 02446
0.13
$623,100
2
1
897
Off Market
20 Chapel St #B509, Brookline, MA 02446
0.13
$1,696,800
3
2
1,741
Off Market
20 Chapel St #B504, Brookline, MA 02446
0.13
$1,077,600
2
1
943
Off Market

Local Information

  • Map ViewExplore the area around 39 Chatham St.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1941
Living Area
3,740 sqft
Price/Sqft
$1,186
Parking
Garage

About this House

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".
39 Chatham St, Brookline, MA 02446 is a 5 bedroom, 5 bathroom, 3,740 sqft single-family home in Longwood, built in 1941. It last sold for $3,100,000 on Aug 22, 2016. It is currently off market. The Trulia Estimate is $4,436,600, with a rent estimate of $8,457/month.

Home Details for 39 Chatham St

Interior Features

Heating & Cooling
Heating: GasAir ConditioningHeating Fuel: Gas
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 and Tax history

DateEventPrice
Aug 22, 2016
Source: N/A
Sold
$3,100,000
Jun 14, 2016
Source: Agent Provided
Listed For Sale
$3,200,000
Apr 25, 2003
Source: N/A
Sold
$2,000,000

Market trends in Brookline

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.22M
$182KMoM
Sale-to-List Price
99.7%
0.2%MoM
Price per sq ft
$816
$19MoM
Available listings
216
37MoM

Around this home

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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    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 39 Chatham St

  • What is 39 Chatham St estimated to be worth?
    Trulia's estimated value for 39 Chatham St in Brookline, MA is $4,436,600.
  • What is the price history for 39 Chatham St?
    39 Chatham St in Brookline, MA last sold for $3,100,000 in August 2016.
  • Is Brookline a buyer's or seller's market?
    Brookline is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Brookline?
    The median sale price in Brookline is $1.22M. That is down $182K from the prior month.
  • How big is the lot at 39 Chatham St?
    The lot at 39 Chatham St in Brookline, MA is about 0.22 acres (9,583 sq ft).
  • Does 39 Chatham St have a garage?
    Yes, 39 Chatham St in Brookline, MA has a garage.

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Apartments for Rent

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Off Market Homes Near 39 Chatham St

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