39 Winthrop Rd, Brookline, MA 02445
OFF MARKET

$2,006,900

Trulia Estimate
  • 3 Beds
  • 4 Baths
  • 2,268 sqft

39 Winthrop Rd, Brookline, MA 02445

Aspinwall Hill
Est. Refi. Payment $11,992/mo*
Refinance Your Home

Home Value

Trulia Estimate
$2.01M
Since last month
Decreased$29K (-1.4%)
Since last year
Increased$103K (+5.5%)
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 +34% in the last 10 years
MonthEstimated value
2026
August 2026$1.99M
July 2026$2.02M
June 2026$2.05M
May 2026$2.07M
April 2026$2.01M
March 2026$1.99M
February 2026$1.91M
January 2026$1.87M
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
0.28
Condo
$1,700,000
04/30/26
3
2.5
1,529
0.35
Condo
$1,635,000
12/08/25
3
2
1,804
0.70
Condo
$2,400,000
07/07/26
3
2.5
2,613
0.16
Condo
$2,600,000
05/01/26
3
3.5
1,837
0.67
Condo
$2,410,000
09/22/25
4
3.5
2,690
0.47
Condo
$2,750,000
09/24/25
5
4.5
3,259
0.66
Condo
$2,300,000
06/09/26
4
4.5
2,722
0.06
Condo
$1,350,000
08/07/26
3
2
2,012
0.15
Condo
$1,850,000
01/30/26
3
2.5
1,850
0.26
Condo
$3,019,999
04/03/26
3
3.5
2,552

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
0.03
-
4
2.5
2,237
Off Market
0.04
$1,983,800
3
2.5
2,848
Off Market
0.01
-
8
3
3,544
Off Market
0.03
$1,660,700
3
1.5
1,946
Off Market
0.06
$1,350,000
3
2
2,012
Recently Sold
0.09
$3,540,900
7
3.5
3,624
Off Market
0.09
$2,299,000
5
2
3,161
For Sale
0.11
$3,506,800
3
2.5
2,541
Off Market
0.07
$1,078,300
3
2
1,296
Off Market
0.11
$4,005,800
3
2.5
3,003
Off Market
0.11
$1,452,600
3
2
1,817
Off Market
0.08
-
3
2
1,490
Off Market

Local Information

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

Home Highlights

Property Type
Condo
Year Built
1910
Living Area
2,268 sqft
Price/Sqft
$885

About this House

This condo is located at 39 Winthrop Rd, Brookline, MA. 39 Winthrop Rd is in the Aspinwall Hill neighborhood in Brookline, MA and in ZIP code 02445. This property has 3 bedrooms, 4 bathrooms and approximately 2,268 sqft of floor space. This property has a lot size of 5662 sqft and was built in 1910.
39 Winthrop Rd, Brookline, MA 02445 is a 3 bedroom, 4 bathroom, 2,268 sqft condo in Aspinwall Hill, built in 1910. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,006,900, with a rent estimate of $7,086/month.

Home Details for 39 Winthrop Rd

Interior Features

Heating & Cooling
Heating: GasAir ConditioningHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 7
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1910
Property Type / Style
Property Type: CondoArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 5662 sqft

Price and Tax history

YearProperty taxTax assessment
2025
$16,592
$1,681,100
Home facts updated by county records

Market trends in Brookline

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

Around this home

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Neighborhood stats provided by third party data sources.

What Locals Say about Aspinwall Hill

  • Magdalene M.
    "Right by the T and walking distance to Fenway! Blue bikes and scooters near by. Lots of ways to go. "
  • Billy W.
    "There is a leash law, and dog owners must pick up their dog's poop in a bag."
  • Billy W.
    "It has a public park at the very top of the hill."
  • Billy W.
    "I can either drive or take public transportation."
  • Billy W.
    "There is only one park on this hill, but a short walk can lead you to bigger parks and playgrounds."
  • Jessicalmartin
    "Beautiful and quiet streets, shops, near to the T. Gorgeous in the snow! A really lovely place to live, I’ve been here about 3 years so far. "
  • Harumi T.
    "It is so nice to live here. "

LGBTQ Local Legal Protections

Frequently asked questions about 39 Winthrop Rd

  • What is 39 Winthrop Rd estimated to be worth?
    Trulia's estimated value for 39 Winthrop Rd in Brookline, MA is $2,006,900.
  • 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.
  • What are the closest schools to 39 Winthrop Rd?
    The closest schools to 39 Winthrop Rd in Brookline, MA are Brookline High School (rated 8/10), Pierce School (Elementary/Middle, rated 10/10).

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