185 Winthrop Rd, Brookline, MA 02445
MVIMG_20180220_121003 (1)
MVIMG_20180220_120856
OFF MARKET

185 Winthrop Rd
Brookline, MA 02445

Aspinwall Hill
  • 3 Beds
  • 1 Bath
  • 5,790 sqft

$2,731,400

Trulia Estimate
as of Jul 18, 2026
Est. Refi. Payment $16,151/mo*
Refinance Your Home

$2,731,400

Trulia Estimate
as of Jul 18, 2026
Est. Refi. Payment $16,151/mo*
Refinance Your Home
3 Beds
1 Bath
5,790 sqft

Local Information

  • Map ViewExplore the area around 185 Winthrop Rd.
  • Schools1 Preschool School2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

This amazing 3 bed gem is just steps to the Green Line. Inside of this unit are shiny hardwood floors and lots of sunlight. All of the rooms are reasonably large and bright. Off-street parking is available and plenty of street parking is in the area. Great
location on a quiet, residential street, close to shops, banks, supermarkets, restaurants and nightlife.

(RLNE3895793)
185 Winthrop Rd, Brookline, MA 02445 is a 3 bedroom, 1 bathroom, 5,790 sqft multi-family in Aspinwall Hill, built in 1900. More recently, it was listed as a rental in February 2018 with an asking price of $2,950 per month. That rental listing was removed on March 6, 2018. It is currently off market. The Trulia Estimate is $2,731,400, with a rent estimate of $4,140/month.

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 185 Winthrop Rd

Interior Features

Interior Details
BasementNumber of Rooms: 18
Heating & Cooling
Heating: Forced Air, GasHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3Floors: Hardwood
Appliances & Utilities
DishwasherDisposal

Exterior Features

Exterior Home Features
Roof: OtherExterior: Brick

Property Information

Year Built
Year Built: 1900Year Updated: 1984
Property Type / Style
Property Type: Multi FamilyArchitecture: Row House

Community

Units in Building: 1

Lot Information

Lot Area: 4356 sqft

Price History for 185 Winthrop Rd

DatePriceEventSource
03/06/2018$2,950ListingRemovedAgent Provided
02/21/2018$2,950Listed For RentAgent Provided
08/02/2016$2,000ListingRemovedAgent Provided
08/31/2014$3,950ListingRemovedAgent Provided
06/03/2014$3,950Listed For RentAgent Provided
06/14/2013$750ListingRemovedAgent Provided
05/24/2013$750Listed For RentAgent Provided

Market trends in Brookline

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.4M
$16.67KMoM
Sale-to-List Price
99.9%
Price per sq ft
$796
$17MoM
Available listings
253
15MoM
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Property Tax and Assessment

Year2025
Tax$27,301
Assessment$2,766,100
Home facts updated by county records

Comparable Sales for 185 Winthrop Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1572 Beacon St, Brookline, MA
0.21
Multi-Family Home
$2,200,000
02/02/26
5
3
3,978
126 Westbourne Ter, Brookline, MA
0.34
Multi-Family Home
$2,200,000
06/10/26
6
2
4,369
589-591 Washington St, Brookline, MA
0.30
Multi-Family Home
$1,800,000
01/13/26
9
4
3,102
255 Tappan St, Brookline, MA
0.23
Multi-Family Home
$2,820,000
12/23/25
7
5
4,171
65 Atherton Rd, Brookline, MA
0.52
Multi-Family Home
$2,650,000
12/12/25
6
3.5
3,277
19-21 Orkney Rd, Brighton, MA
0.65
Multi-Family Home
$1,255,000
12/03/25
4
3
3,630
9 Searle Ave, Brookline, MA
0.71
Multi-Family Home
$1,690,000
08/15/25
5
2
2,310
19-21 Orkney Rd, Brighton, MA
0.65
Multi-Family Home
$1,255,000
12/02/25
5
3
3,630
19-21 Elm St, Brookline, MA
0.74
Multi-Family Home
$1,800,000
10/31/25
5
2
2,252
5 Fiske Ter, Allston, MA
0.75
Multi-Family Home
$1,250,000
12/23/25
5
2
2,644

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Assigned Schools

These are the assigned schools for 185 Winthrop Rd.
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
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  • 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
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  • Billy W.
    "I can either drive or take public transportation."
    0
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  • 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

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Apartments for Rent

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Homes for sale near 185 Winthrop Rd

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Off Market Homes Near 185 Winthrop Rd

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