53 Winthrop Rd, Brookline, MA 02445
OFF MARKET

$1,877,000

Trulia Estimate
  • 4 Beds
  • 4 Baths
  • 1,955 sqft

53 Winthrop Rd, Brookline, MA 02445

Aspinwall Hill
Currently Off Market - Sold Dec 1, 2004 for $790,000

Home Value

Trulia Estimate
$1.88M
Since last month
Decreased$3K (-0.1%)
Since last year
Increased$125K (+7.1%)
Since last sale
Increased$1M (+137.5%)
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 +30% in the last 10 years
MonthEstimated value
2026
August 2026$1.88M
July 2026$1.88M
June 2026$1.89M
May 2026$1.9M
April 2026$1.85M
March 2026$1.83M
February 2026$1.77M
January 2026$1.72M
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
0.03
Condo
$1,350,000
08/07/26
3
2
2,012
0.15
Condo
$2,600,000
05/01/26
3
3.5
1,837
0.15
Condo
$1,850,000
01/30/26
3
2.5
1,850
0.12
Condo
$1,399,000
03/27/26
3
2
2,120
0.19
Condo
$3,265,000
05/01/26
4
3.5
2,605
0.11
Condo
$1,380,000
06/09/26
3
2
1,397
0.18
Condo
$1,100,000
11/03/25
3
1.5
1,338
0.28
Condo
$2,150,000
02/03/26
4
4
2,925
0.20
Condo
$2,100,000
05/08/26
4
3
3,003
0.10
Condo
$1,000,000
11/14/25
2
1.5
1,369

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
0.00
-
4
2.5
2,237
Off Market
0.01
$1,983,800
3
2.5
2,848
Off Market
0.04
-
8
3
3,544
Off Market
0.03
$1,660,700
3
1.5
1,946
Off Market
0.03
$1,350,000
3
2
2,012
Recently Sold
0.06
$3,544,000
7
3.5
3,624
Off Market
0.06
$2,299,000
5
2
3,161
For Sale
0.08
$3,494,300
3
2.5
2,541
Off Market
0.08
$1,078,300
3
2
1,296
Off Market
0.08
$4,005,800
3
2.5
3,003
Off Market
0.08
$1,429,100
3
2
1,817
Off Market
0.09
-
3
2
1,490
Off Market

Local Information

  • Map ViewExplore the area around 53 Winthrop Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Condo
Year Built
1924
Living Area
1,955 sqft
Price/Sqft
$960

About this House

This condo is located at 53 Winthrop Rd, Brookline, MA. 53 Winthrop Rd is in the Aspinwall Hill neighborhood in Brookline, MA and in ZIP code 02445. This property has 4 bedrooms, 4 bathrooms and approximately 1,955 sqft of floor space. This property was built in 1924.
53 Winthrop Rd, Brookline, MA 02445 is a 4 bedroom, 4 bathroom, 1,955 sqft condo in Aspinwall Hill, built in 1924. It last sold for $790,000 on Dec 1, 2004. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,877,000, with a rent estimate of $7,430/month.

Home Details for 53 Winthrop Rd

Interior Features

Interior Details
BasementNumber of Rooms: 10Types of Rooms: Walk In Closet, Dining Room, Family Room, Laundry Room, Master Bath, Mud Room
Heating & Cooling
Heating: Baseboard, GasAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 3Floors: Hardwood
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows

Exterior Features

Exterior Home Features
Roof: SlateExterior: Stucco, BrickGardenPorch
Parking & Garage
Parking: Off Street

Property Information

Year Built
Year Built: 1924Year Updated: 1998
Property Type / Style
Property Type: CondoArchitecture: Craftsman

Community

Units in Building: 2

Building

Pool
Sauna

Price and Tax history

DateEventPrice
Dec 1, 2004
Source: N/A
Sold
$790,000

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 53 Winthrop Rd

  • What is 53 Winthrop Rd estimated to be worth?
    Trulia's estimated value for 53 Winthrop Rd in Brookline, MA is $1,877,000.
  • What is the price history for 53 Winthrop Rd?
    53 Winthrop Rd in Brookline, MA last sold for $790,000 in December 2004.
  • 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.
  • Does 53 Winthrop Rd have air conditioning?
    Yes, 53 Winthrop Rd in Brookline, MA has air conditioning.
  • Does 53 Winthrop Rd have laundry facilities?
    Yes, 53 Winthrop Rd in Brookline, MA has in-unit laundry.

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