16 Winthrop Rd, Brookline, MA 02445
OFF MARKET

$2,370,000

Trulia Estimate
  • 3 Beds
  • 3 Baths
  • 2,141 sqft

16 Winthrop Rd, Brookline, MA 02445

Aspinwall Hill
Est. Refi. Payment $14,149/mo*
Refinance Your Home
Currently Off Market - Sold Jul 6, 1990 for $1

Home Value

Trulia Estimate
$2.37M
Since last month
Decreased$46K (-1.9%)
Since last year
Increased$166K (+7.5%)
Since last sale
Increased$2M (+236,659,900%)
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 +62% in the last 10 years
MonthEstimated value
2026
August 2026$2.37M
July 2026$2.41M
June 2026$2.43M
May 2026$2.47M
April 2026$2.38M
March 2026$2.36M
February 2026$2.26M
January 2026$2.2M
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
0.12
Single-Family Home
$2,385,000
12/17/25
4
3
2,286
0.19
Single-Family Home
$2,050,500
01/15/26
6
3.5
2,104
0.36
Single-Family Home
$2,210,000
04/13/26
3
2.5
1,740
0.21
Single-Family Home
$3,019,999
04/03/26
4
3
3,422
0.37
Single-Family Home
$3,350,000
06/30/26
4
2.5
2,676
0.32
Single-Family Home
$2,850,000
04/08/26
4
2.5
3,377
0.36
Single-Family Home
$2,445,000
05/12/26
4
2
2,383
0.33
Single-Family Home
$2,650,000
01/07/26
4
2
2,600
0.56
Single-Family Home
$1,750,000
06/23/26
3
1.5
1,380
0.65
Single-Family Home
$1,820,000
09/26/25
3
1.5
1,943

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
0.06
-
8
3
3,544
Off Market
0.08
$1,660,700
3
1.5
1,946
Off Market
0.08
-
4
2.5
2,237
Off Market
0.09
$1,983,800
3
2.5
2,848
Off Market
0.08
$1,954,800
4
2
2,890
Off Market
0.11
$1,550,300
2
1.5
1,400
Off Market
0.12
$1,078,300
3
2
1,296
Off Market
0.11
$1,350,000
3
2
2,012
Recently Sold
0.12
-
3
2
1,490
Off Market
0.12
-
2
1
1,290
Off Market
0.09
$2,065,700
2
1
1,104
Off Market
0.11
$1,100,000
3
1.5
1,338
Recently Sold

Local Information

  • Map ViewExplore the area around 16 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
2,141 sqft
Price/Sqft
$1,107
Parking
Garage

About this House

This single-family home is located at 16 Winthrop Rd, Brookline, MA. 16 Winthrop Rd is in the Aspinwall Hill neighborhood in Brookline, MA and in ZIP code 02445. This property has 3 bedrooms, 3 bathrooms and approximately 2,141 sqft of floor space. This property has a lot size of 4791 sqft and was built in 1935.
16 Winthrop Rd, Brookline, MA 02445 is a 3 bedroom, 3 bathroom, 2,141 sqft single-family home in Aspinwall Hill, built in 1935. It last sold for $1 on Jul 6, 1990. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,370,000, with a rent estimate of $6,024/month.

Home Details for 16 Winthrop Rd

Interior Features

Interior Details
BasementNumber of Rooms: 8
Heating & Cooling
Heating: GasHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: SlateExterior: Brick
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1935Year Updated: 1969
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 4791 sqft

Price and Tax history

DateEventPrice
Jul 6, 1990
Source: N/A
Sold
$1

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 16 Winthrop Rd

  • What is 16 Winthrop Rd estimated to be worth?
    Trulia's estimated value for 16 Winthrop Rd in Brookline, MA is $2,370,000.
  • What is the price history for 16 Winthrop Rd?
    16 Winthrop Rd in Brookline, MA last sold for $1 in July 1990.
  • 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 16 Winthrop Rd?
    The lot at 16 Winthrop Rd in Brookline, MA is about 0.11 acres (4,791 sq ft).
  • Does 16 Winthrop Rd have a garage?
    Yes, 16 Winthrop Rd in Brookline, MA has a garage.

Explore by feature - Pet Friendly

Explore by feature - Garage

Explore by feature - Air Conditioning

Explore by feature - Pool

Explore by feature - Washer/dryer

Explore by feature - Outdoor Space

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 16 Winthrop Rd

Skip to last item
Skip to first item

Homes for sale near 16 Winthrop Rd

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