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

27 Winthrop Rd
Brookline, MA 02445

Aspinwall Hill
  • 1 Bed
  • 1 Bath
  • 1,000 sqft
1 Bed
1 Bath
1,000 sqft

Local Information

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  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

JUNE 1st Move-In!

Beautifully renovated one-bedroom plus office apartment located in a stunning single-family home in the highly desirable Washington Square section of Brookline. This thoughtfully updated unit features a modern kitchen with stainless steel appliances, stylish finishes, and a functional layout that offers both comfort and flexibility perfect for working professionals or anyone needing a dedicated home office space.

All utilities are included in the rent heat, hot water, electricity, and even cable/internet providing true all-inclusive convenience and predictable monthly expenses.

Enjoy the privacy of a separate apartment within a charming home, along with the added benefit of in-unit laundry for everyday ease. Ideally situated near shops, restaurants, public transportation, and everything Washington Square has to offer.

A rare opportunity for a turnkey, all-inclusive rental in one of Brookline's most sought-after neighborhoods.

Heat, hot water, water, sewer, and electricity included in the price of rent.
27 Winthrop Rd, Brookline, MA 02445 is a 1 bedroom, 1 bathroom, 1,000 sqft apartment in Aspinwall Hill. More recently, it was listed as a rental in March 2026 with an asking price of $2,750 per month. That rental listing was removed on March 31, 2026. It is currently off market. The Trulia Estimate rent is $2,981/month.

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
125 days ago

Home Details for 27 Winthrop Rd

Interior Features

Heating & Cooling
Heating: Forced AirHeating Fuel: Forced Air
Appliances & Utilities
DryerMicrowaveRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Hardwood

Property Information

Property Type / Style
Property Type: Apartment

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Price History for 27 Winthrop Rd

DatePriceEventSource
03/31/2026$2,750ListingRemovedZillow Rentals
03/03/2026$2,750Listed For RentZillow Rentals
04/26/2023ListingRemovedZillow Rentals
04/06/2023$2,100Listed For RentZillow Rentals
03/22/2022ListingRemovedZillow Rental Manager
03/09/2022$2,100Listed For RentZillow Rental Manager
07/31/2019$1,825ListingRemovedAgent Provided
07/25/2019$1,825PriceChange
Agent Provided
06/06/2019$6,350Listed For RentAgent Provided
11/07/2017$1,575ListingRemovedAgent Provided
10/12/2017$1,575PriceChange
Agent Provided
09/22/2017$1,750Listed For RentAgent Provided
07/04/2017$1,725ListingRemovedAgent Provided
05/24/2017$1,725PriceChange
Agent Provided
03/15/2017$6,900PriceChange
Agent Provided
03/13/2017$1,725Listed For RentAgent Provided

Market trends in Brookline

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.42M
$333MoM
Sale-to-List Price
99.9%
0.9%MoM
Price per sq ft
$814
$5MoM
Available listings
238
11MoM
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Comparable Sales for 27 Winthrop Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
369 Tappan St #12, Brookline, MA
0.50
Apartment
$500,000
10/17/25
1
1
678
21 Westbourne Ter #3, Brookline, MA
0.37
Apartment
$580,000
10/30/25
2
1
876
36 Saint Paul St #B, Brookline, MA
0.51
Apartment
$470,000
06/12/26
2
1
-
49 Harvard Ave #4, Brookline, MA
0.28
Apartment
$974,000
06/15/26
1
1
700
28 Saint Paul St #1, Brookline, MA
0.50
Apartment
$663,000
08/12/25
2
1
715
97 Sewall Ave #5, Brookline, MA
0.68
Apartment
$542,500
06/30/26
1
1
650
20 Saint Paul St #2, Brookline, MA
0.50
Apartment
$400,000
10/14/25
2
1
703
13 Linden St #8, Brookline, MA
0.59
Apartment
$714,474
01/23/26
2
1
1,088
6 Perry St, Brookline, MA
0.59
-
-
-
3
1
960
60 Longwood Ave #602, Brookline, MA
0.62
Apartment
$630,000
06/30/26
1
2
950
Home facts updated by county records

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Assigned Schools

These are the assigned schools for 27 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
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  • 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."
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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
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  • Harumi T.
    "It is so nice to live here. "
    0
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Apartments for Rent

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Homes for sale near 27 Winthrop Rd

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Off Market Homes Near 27 Winthrop Rd

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