20 Winthrop Rd, Brookline, MA 02445
7864W56aa75abcb714
7864W56aa75bc5b2f4
OFF MARKET

$2,538,900

Trulia Estimate
  • 4 Beds
  • 2.5 Baths
  • 2,489 sqft

20 Winthrop Rd, Brookline, MA 02445

Aspinwall Hill
Est. Refi. Payment $15,125/mo*
Refinance Your Home
Currently Off Market - Sold Jun 6, 1994 for $427,500

Home Value

Trulia Estimate
$2.54M
Since last month
Decreased$55K (-2.1%)
Since last year
Increased$172K (+7.3%)
Since last sale
Increased$2M (+493%)
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 +63% in the last 10 years
MonthEstimated value
2026
August 2026$2.54M
July 2026$2.59M
June 2026$2.61M
May 2026$2.64M
April 2026$2.56M
March 2026$2.53M
February 2026$2.42M
January 2026$2.36M
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
21 Hancock Rd, Brookline, MA
0.13
Single-Family Home
$2,385,000
12/17/25
4
3
2,286
71 Greenough St, Brookline, MA
0.22
Single-Family Home
$3,019,999
04/03/26
4
3
3,422
9 Greenough St, Brookline, MA
0.20
Single-Family Home
$2,050,500
01/15/26
6
3.5
2,104
50 Waverly St, Brookline, MA
0.37
Single-Family Home
$2,445,000
05/12/26
4
2
2,383
29 Mason Ter, Brookline, MA
0.32
Single-Family Home
$2,650,000
01/07/26
4
2
2,600
24 Blake Rd, Brookline, MA
0.33
Single-Family Home
$2,850,000
04/08/26
4
2.5
3,377
43 Waverly St, Brookline, MA
0.38
Single-Family Home
$3,350,000
06/30/26
4
2.5
2,676
30 York Ter, Brookline, MA
0.35
Single-Family Home
$2,210,000
04/13/26
3
2.5
1,740
61 Toxteth St, Brookline, MA
0.67
Single-Family Home
$2,525,000
04/15/26
5
1.5
2,484
14-14A Linden Pl, Brookline, MA
0.56
Single-Family Home
$1,750,000
06/23/26
3
1.5
1,380

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
35-37 Winthrop Rd, Brookline, MA 02445
0.05
-
8
3
3,544
Off Market
139 University Rd #2, Brookline, MA 02445
0.07
$1,660,700
3
1.5
1,946
Off Market
51 Winthrop Rd #51, Brookline, MA 02445
0.07
-
4
2.5
2,237
Off Market
57 Winthrop Rd #2, Brookline, MA 02445
0.08
$1,983,800
3
2.5
2,848
Off Market
46 Gardner Rd #2, Brookline, MA 02445
0.08
$1,935,800
4
2
2,890
Off Market
520 Washington St, Brookline, MA 02446
0.10
$1,550,300
2
1.5
1,400
Off Market
580 Washington St #1, Brookline, MA 02446
0.11
$1,078,300
3
2
1,296
Off Market
63 Winthrop Rd #1, Brookline, MA 02445
0.10
$1,350,000
3
2
2,012
Recently Sold
576 Washington St #6, Brookline, MA 02445
0.11
-
3
2
1,490
Off Market
576 Washington St #1, Brookline, MA 02445
0.11
-
2
1
1,290
Off Market
128 Gardner Rd, Brookline, MA 02445
0.09
$2,084,800
2
1
1,104
Off Market
500 Washington St #2, Brookline, MA 02446
0.11
$1,100,000
3
1.5
1,338
Recently Sold

Local Information

  • Map ViewExplore the area around 20 Winthrop Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1935
Living Area
2,489 sqft
Price/Sqft
$1,020
Parking
Garage

About this House

This single-family home is located at 20 Winthrop Rd, Brookline, MA. 20 Winthrop Rd is in the Aspinwall Hill neighborhood in Brookline, MA and in ZIP code 02445. This property has 4 bedrooms, 3 bathrooms and approximately 2,489 sqft of floor space. This property has a lot size of 4844 sqft and was built in 1935.
20 Winthrop Rd, Brookline, MA 02445 is a 4 bedroom, 3 bathroom, 2,489 sqft single-family home in Aspinwall Hill, built in 1935. It last sold for $427,500 on Jun 6, 1994. More recently, it was listed as a rental in February 2017 with an asking price of $2,300 per month. That rental listing was removed on May 22, 2017. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,538,900, with a rent estimate of $7,580/month.

Home Details for 20 Winthrop Rd

Interior Features

Interior Details
BasementAtticNumber of Rooms: 9Types of Rooms: Dining Room, Family Room, Laundry Room, Master Bath, OfficeCeiling Fan
Heating & Cooling
Heating: Radiant, GasHeating Fuel: Radiant
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Hardwood
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: MetalGardenPatioPorch
Parking & Garage
GarageParking Spaces: 3Parking: Garage Detached, Off Street

Property Information

Year Built
Year Built: 1935Year Updated: 1973
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 4844 sqft

Price and Tax history

DateEventPrice
May 22, 2017
Source: Agent Provided
ListingRemoved
$2,300
Feb 17, 2017
Source: Agent Provided
Listed For Rent
$2,300
Jun 6, 1994
Source: N/A
Sold
$427,500

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

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

Neighborhood Overview

Aspinwall Hill
See Local Highlights
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. "
    0
    Flag
  • Billy W.
    "There is a leash law, and dog owners must pick up their dog's poop in a bag."
    0
    Flag
  • Billy W.
    "It has a public park at the very top of the hill."
    0
    Flag
  • Billy W.
    "I can either drive or take public transportation."
    0
    Flag
  • Billy W.
    "There is only one park on this hill, but a short walk can lead you to bigger parks and playgrounds."
    1
    Flag
  • 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. "
    0
    Flag
  • Harumi T.
    "It is so nice to live here. "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 20 Winthrop Rd

  • What is 20 Winthrop Rd estimated to be worth?
    Trulia's estimated value for 20 Winthrop Rd in Brookline, MA is $2,538,900.
  • What is the price history for 20 Winthrop Rd?
    20 Winthrop Rd in Brookline, MA last sold for $427,500 in June 1994.
  • 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 20 Winthrop Rd have laundry facilities?
    Yes, 20 Winthrop Rd in Brookline, MA has in-unit laundry.
  • How big is the lot at 20 Winthrop Rd?
    The lot at 20 Winthrop Rd in Brookline, MA is about 0.11 acres (4,844 sq ft).

Explore by feature - Pet Friendly

279 pet-friendly rentals in Brookline, MA

Explore by feature - Garage

64 rentals with a garage in Brookline, MA

Explore by feature - Air Conditioning

547 rentals with air conditioning in Brookline, MA

Explore by feature - Pool

57 rentals with a pool in Brookline, MA

Explore by feature - Washer/dryer

818 rentals with a washer/dryer in Brookline, MA

Explore by feature - Outdoor Space

18 rentals with an outdoor space in Brookline, MA

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 20 Winthrop Rd

Skip to last item
Skip to first item

Homes for sale near 20 Winthrop Rd

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item