157 Winthrop Rd, Brookline, MA 02445
Property image
Property image
OFF MARKET

$2,893,600

Trulia Estimate
  • 5 Beds
  • 3.5 Baths
  • 3,919 sqft

157 Winthrop Rd, Brookline, MA 02445

Aspinwall Hill
Est. Refi. Payment $18,123/mo*
Refinance Your Home
Currently Off Market - Sold Oct 2, 2020 for $1,925,000

Home Value

Trulia Estimate
$2.89M
Since last month
Decreased$18K (-0.6%)
Since last year
Increased$258K (+9.6%)
Since last sale
Increased$1M (+52.5%)
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 +39% in the last 10 years
MonthEstimated value
2026
September 2026$2.94M
August 2026$2.95M
July 2026$2.95M
June 2026$3.03M
May 2026$2.93M
April 2026$2.87M
March 2026$2.87M
February 2026$2.83M
January 2026$2.8M
2025
2024
2023

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
22 Windsor Rd, Brookline, MA
0.38
Single-Family Home
$2,050,000
03/31/26
5
3.5
2,845
333 Clark Rd, Brookline, MA
0.33
Single-Family Home
$2,487,000
12/11/25
5
3.5
3,100
80 Mason Ter, Brookline, MA
0.34
Single-Family Home
$3,100,000
08/05/26
5
3.5
3,680
323 Clark Rd, Brookline, MA
0.32
Single-Family Home
$2,995,000
03/04/26
5
4.5
3,370
24 Blake Rd, Brookline, MA
0.40
Single-Family Home
$2,850,000
04/08/26
4
2.5
3,377
30 York Ter, Brookline, MA
0.29
Single-Family Home
$2,210,000
04/13/26
3
2.5
1,740
29 Mason Ter, Brookline, MA
0.25
Single-Family Home
$2,650,000
01/07/26
4
2
2,600
213 Gardner Rd, Brookline, MA
0.30
Single-Family Home
$3,330,000
11/25/25
5
4.5
5,507
9 Greenough St, Brookline, MA
0.51
Single-Family Home
$2,050,500
01/15/26
6
3.5
2,104
189 Clinton Rd, Brookline, MA
0.37
Single-Family Home
$3,318,000
04/23/26
6
4
4,633

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
41 University Rd #3, Brookline, MA 02445
0.02
-
3
3.5
2,302
Off Market
41 University Rd #1, Brookline, MA 02445
0.02
-
3
3.5
2,180
Off Market
41 University Rd #2, Brookline, MA 02445
0.02
-
3
3.5
2,180
Off Market
149 Winthrop Rd #5, Brookline, MA 02445
0.01
$836,100
2
1
1,038
Off Market
149 Winthrop Rd #2, Brookline, MA 02445
0.02
$521,500
2
1
740
Off Market
175 Winthrop Rd #3, Brookline, MA 02445
0.04
$1,657,900
5
2.5
2,650
Off Market
177 Winthrop Rd #3, Brookline, MA 02445
0.05
$1,600,000
4
2
1,654
For Sale
181 Winthrop Rd, Brookline, MA 02445
0.05
-
10
12
7,392
Off Market
47 University Rd, Brookline, MA 02445
0.03
$2,640,000
8
4
3,530
Off Market
40 University Rd #2, Brookline, MA 02445
0.04
$2,579,500
4
3.5
2,965
Off Market
15 University Rd #32, Brookline, MA 02445
0.06
-
1
1
490
Off Market
15-17 University Rd #A, Brookline, MA 02445
0.06
-
1
1
407
Off Market

Local Information

  • Map ViewExplore the area around 157 Winthrop Rd.
  • Schools1 Preschool School2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1890
3,919 sqft
$738/sqft
Garage

About this House

Built in 1890 by celebrated architect Ralph Adams Cram, this exceptional home in the heart of Washington Square, rich with period details, has been renovated to provide a layout for entertaining & family comfort. The honeycomb leaded glass windows in the foyer frame views of the gardens, & the formal dining & living room offer fireplaces & original pocket doors. The kitchen, with granite countertops, large island & radiant heated floors, provides treetop views; there is a half bath & laundry on this floor. A grand staircase takes you up to the 2nd floor with a lovely seating area & 3 bedrooms, including a master bedroom option w/a fireplace & bath; there is also a family bath on this floor. The 3rd floor offers 2 bedrooms, including a spacious master bedroom suite with fireplace & views of the Boston skyline. The top floor provides a play area or studio. Additionally, there are 4 prkg spaces, including a garage. Easy access to the T, shops, & restaurants completes this unique offering.
157 Winthrop Rd, Brookline, MA 02445 is a 5 bedroom, 4 bathroom, 3,919 sqft single-family home in Aspinwall Hill, built in 1890. It last sold for $1,925,000 on Oct 2, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,893,600, with a rent estimate of $8,961/month.

Home Details for 157 Winthrop Rd

Interior Features

Heating & Cooling
Heating: GasHeating Fuel: Gas
Appliances & Utilities
DishwasherDryerRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Hardwood

Exterior Features

Exterior Home Features
Roof: Asphalt
Parking & Garage
GarageParking Spaces: 4Parking: Garage Detached

Property Information

Year Built
Year Built: 1890
Property Type / Style
Property Type: Single Family Home

Lot Information

Lot Area: 871 sqft

Building

Fitness & Sports
Tennis Court

Price and Tax history

DateEventPrice
Oct 2, 2020
Source: N/A
Sold
$1,925,000
Sep 8, 2020
Source: Agent Provided
Listed For Sale
$1,995,000

Market trends in Brookline

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.24M
$23.33KMoM
Sale-to-List Price
99.3%
0.4%MoM
Price per sq ft
$811
$6MoM
Available listings
186
30MoM

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 157 Winthrop Rd

  • What is 157 Winthrop Rd estimated to be worth?
    Trulia's estimated value for 157 Winthrop Rd in Brookline, MA is $2,893,600.
  • What is the price history for 157 Winthrop Rd?
    157 Winthrop Rd in Brookline, MA last sold for $1,925,000 in October 2020.
  • Is Brookline a buyer's or seller's market?
    Brookline is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Brookline?
    The median sale price in Brookline is $1.24M. That is up $23.33K from the prior month.
  • Does 157 Winthrop Rd have laundry facilities?
    Yes, 157 Winthrop Rd in Brookline, MA has in-unit laundry.
  • How big is the lot at 157 Winthrop Rd?
    The lot at 157 Winthrop Rd in Brookline, MA is about 0.02 acres (871 sq ft).

Explore by feature - Pet Friendly

233 pet-friendly rentals in Brookline, MA

Explore by feature - Garage

56 rentals with a garage in Brookline, MA

Explore by feature - Air Conditioning

439 rentals with air conditioning in Brookline, MA

Explore by feature - Pool

50 rentals with a pool in Brookline, MA

Explore by feature - Washer/dryer

711 rentals with a washer/dryer in Brookline, MA

Explore by feature - Outdoor Space

17 rentals with an outdoor space in Brookline, MA

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 157 Winthrop Rd

Skip to last item
Skip to first item

Homes for sale near 157 Winthrop Rd

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