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

$3,314,900

Trulia Estimate
  • 2 Beds
  • 1 Bath
  • 3,913 sqft

135 Winthrop Rd, Brookline, MA 02445

Aspinwall Hill
Est. Refi. Payment $19,707/mo*
Refinance Your Home
Currently Off Market - Sold May 2, 2014 for $1,500,000

Home Value

Trulia Estimate
$3.31M
Since last month
Decreased$20K (-0.6%)
Since last year
Increased$280K (+9.2%)
Since last sale
Increased$2M (+121%)
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 +98% in the last 10 years
MonthEstimated value
2026
August 2026$3.31M
August 2026$3.3M
July 2026$3.34M
June 2026$3.3M
May 2026$3.3M
April 2026$3.2M
March 2026$3.22M
February 2026$3.11M
January 2026$2.98M
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
29 Mason Ter, Brookline, MA
0.24
Single-Family Home
$2,650,000
01/07/26
4
2
2,600
144 Jordan Rd, Brookline, MA
0.48
Single-Family Home
$1,820,000
09/26/25
3
1.5
1,943
8 Woodstock Ave, Brighton, MA
0.59
Single-Family Home
$800,000
12/02/25
2
1
1,070
24 Blake Rd, Brookline, MA
0.36
Single-Family Home
$2,850,000
04/08/26
4
2.5
3,377
71 Greenough St, Brookline, MA
0.41
Single-Family Home
$3,019,999
04/03/26
4
3
3,422
30 York Ter, Brookline, MA
0.29
Single-Family Home
$2,210,000
04/13/26
3
2.5
1,740
21 Hancock Rd, Brookline, MA
0.38
Single-Family Home
$2,385,000
12/17/25
4
3
2,286
22 Windsor Rd, Brookline, MA
0.44
Single-Family Home
$2,050,000
03/31/26
5
3.5
2,845
333 Clark Rd, Brookline, MA
0.37
Single-Family Home
$2,487,000
12/11/25
5
3.5
3,100
18 Cushing Rd, Brookline, MA
0.70
Single-Family Home
$1,351,000
01/23/26
2
2
1,230

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
53 University Rd #2, Brookline, MA 02445
0.03
$2,100,000
4
3
3,003
Recently Sold
47 University Rd, Brookline, MA 02445
0.04
$2,676,700
8
4
3,530
Off Market
57 University Rd #3, Brookline, MA 02445
0.02
$3,265,000
4
3.5
2,605
Recently Sold
57 University Rd #2, Brookline, MA 02445
0.02
$2,094,200
3
2.5
1,570
Off Market
57 University Rd #1, Brookline, MA 02445
0.02
$3,299,000
3
2.5
1,410
Off Market
41 University Rd #1, Brookline, MA 02445
0.05
-
3
3.5
2,180
Off Market
40 University Rd #2, Brookline, MA 02445
0.06
$2,596,700
4
3.5
2,965
Off Market
41 University Rd #2, Brookline, MA 02445
0.05
-
3
3.5
2,180
Off Market
41 University Rd #3, Brookline, MA 02445
0.05
-
3
3.5
2,302
Off Market
58-60 University Rd, Brookline, MA 02445
0.05
-
5
3.5
3,319
Off Market
149 Winthrop Rd #5, Brookline, MA 02445
0.04
$833,400
2
1
1,038
Off Market
149 Winthrop Rd #2, Brookline, MA 02445
0.04
$527,100
2
1
740
Off Market

Local Information

  • Map ViewExplore the area around 135 Winthrop Rd.
  • Schools1 Preschool School2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1892
3,913 sqft
$847/sqft
Garage

About this House

GRAND QUEEN ANNE VICTORIAN IN WASH SQUARE PERFECT FOR FAMILY LIVING AND ENTERTAINING! ORNATE WOODWORK, SPACIOUS ROOMS, HI CEILINGS, 5 FPS & WRAP-AROUND PORCH W/ BOSTON VIEWS. FLOORPLAN OFFERS BOTH LR & FAMILY ROOMS ON FIRST FLOOR, 3-4 BRS ON SECOND FLOOR, & A FLEXIBLE 3RD FLR W/ 2BRS, A GREAT ROOM, FULL BATH & KITCHENETTE- GREAT FOR AU PAIR OR EXTENDED FAMILY VISITS. LOWER LEVEL WALK-OUT W/EXPANSION POTENTIAL, SUPER STORAGE, WORKROOM. GARAGE + 2 SPOTS. WALK TO SHOPS, T, PARKS & SCHOOLS.TERRIFIC!

Take the Virtual Tour:
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Watch the YouTube Video!
http://www.smartfloorplan.com/orders/bin/video.php?folder=il/v331460&video=https://www.youtube.com/v/9hMYHdrNlIU?version=3&f=user_uploads&c=SmartFloorPlanVideoA&d=AfeCzDy8yP22olLxEzMetZEO88HsQjpE1a8d1GxQnGDm&app=youtube_gdata
135 Winthrop Rd, Brookline, MA 02445 is a 2 bedroom, 1 bathroom, 3,913 sqft single-family home in Aspinwall Hill, built in 1892. It last sold for $1,500,000 on May 2, 2014. More recently, it was listed as a rental in January 2017 with an asking price of $2,400 per month. That rental listing was removed on February 19, 2017. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,314,900, with a rent estimate of $3,024/month.

Home Details for 135 Winthrop Rd

Interior Features

Heating & Cooling
Heating: GasAir ConditioningHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 3
Interior Details
Number of Rooms: 12

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood
Parking & Garage
GarageParking: Garage Detached, Off Street

Property Information

Year Built
Year Built: 1892Year Updated: 1975
Property Type / Style
Property Type: Single Family HomeArchitecture: Victorian

Community

Units in Building: 1

Lot Information

Lot Area: 7405 sqft

Price and Tax history

DateEventPrice
Feb 19, 2017
Source: Agent Provided
ListingRemoved
$2,400
Jan 24, 2017
Source: Agent Provided
Listed For Rent
$2,400
May 2, 2014
Source: N/A
Sold
$1,500,000
Jan 22, 2014
Source: Agent Provided
PriceChange
$1,525,000
Price decreased by 2%
Jun 6, 2013
Source: Agent Provided
PriceChange
$1,550,000
Price decreased by 3%

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
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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 135 Winthrop Rd

  • What is 135 Winthrop Rd estimated to be worth?
    Trulia's estimated value for 135 Winthrop Rd in Brookline, MA is $3,314,900.
  • What is the price history for 135 Winthrop Rd?
    135 Winthrop Rd in Brookline, MA last sold for $1,500,000 in May 2014.
  • 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 135 Winthrop Rd?
    The lot at 135 Winthrop Rd in Brookline, MA is about 0.17 acres (7,405 sq ft).
  • Does 135 Winthrop Rd have a garage?
    Yes, 135 Winthrop Rd in Brookline, MA has a garage.

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