20 Winslow Rd, Unit 2

$3,500
Price
3
Beds
1,100 Sq. Ft.
$38 / Sq. Ft.
1,100
Sq. Ft.
$38
per Sq. Ft.

Description

Spacious 3-Bedroom duplex in Prime Brookline Location with off-street parking available! Live in the heart of Brookline in this expansive 3-bedroom, 1-bathroom home offering over 1,100 sq. ft. of living space across two levels. This townhouse unit feels more like a single-family home, with beautifully maintained hardwood floors throughout and generously sized bedrooms. Upstairs, you'll find the largest bedroom, bonus storage space, and a bright, versatile area perfect for a home office—ideal for...Spacious 3-Bedroom duplex in Prime Brookline Location with off-street parking available! Live in the heart of Brookline in this expansive 3-bedroom, 1-bathroom home offering over 1,100 sq. ft. of living space across two levels. This townhouse unit feels more like a single-family home, with beautifully maintained hardwood floors throughout and generously sized bedrooms. Upstairs, you'll find the largest bedroom, bonus storage space, and a bright, versatile area perfect for a home office—ideal for remote work. One off-street parking spaces included in rent, and additional off-street spot available at $250/per month. Professionally managed for convenience and peace of mind. Available now. Don’t miss this opportunity to live in one of Brookline’s most sought-after neighborhoods! Available now!
  1. Listed by Gretchen Devine • Berkshire Hathaway HomeServices Warren Residential

Property Details for 20 Winslow Road, Unit 2

Town
Brookline
Area
MA-Brookline
Parking Spaces
2.00
Parking Spaces Total
2
LISTING UPDATED: 12/21/2025 03:09 AM

Property Details for 20 Winslow Road, Unit 2

StatusActive
MLS #73462680
Days on Market4
Rental Incentives-
Available Date12/21/2025
Furnished-
Compass TypeRental
MLS TypeRental / Apartment
Year Built-
CountyNorfolk County

Location

Listing Courtesy of Berkshire Hathaway HomeServices Warren Residential, Gretchen Devine
Add your commute

Building Information for 20 Winslow Road, Unit 2

Building/Complex20 Winslow RdFloor-Stories-Residences-Pet Policy-Pet Policy DetailsYes w/ RestrictionsYear Built-Lot Size22.96 AC / 999,999 SF

Property Information for 20 Winslow Road, Unit 2

General Details
Property Details
  • Building Area Units: Square Feet
  • Community Features: Public Transportation, Shopping, Park, Walk/Jog Trails, Medical Facility, Laundromat, Bike Path, Conservation Area, Highway Access, House of Worship, Private School, Public School, T-Station, University
  • Living Area: 1100.0
  • SqFt with Basement: No
  • Property Attached: Yes
  • Waterfront: No
Features
Interior Features
  • Appliances: Range, Oven, Dishwasher, Refrigerator, Freezer, Washer
  • Num of Baths: 1.0
  • Num of Full Baths: 1
  • Num of Half Baths: 0
  • Bathrooms Total Decimal: 1.00
  • Bathrooms Total Integer: 1
  • FireplaceYN: No
  • Fireplaces: 0
  • Laundry Features: In Unit
  • SpaYN: No
Exterior Features
  • Exterior Features: Porch
  • Exterior Features: Porch
  • Patio And Porch Features: Porch
Utilities
  • Cooling: No
  • Heating: Natural Gas
  • Heating: Yes
Property Information
Property Info
  • Farm Land Area Units: Square Feet
  • WARRANTY: No
  • Lot Size Units: Acres
Building / Association Information
Living Characteristics
  • Beds Total: 3
Income / Expenses
  • Insurance Required: Yes
Complex & Association Information
  • Adult Community: No
Unit Information
Unit Information
  • Unit Building: 2
  • Unit Floor Level Integer: 2.0
Rental Info
Rental Info
  • Date Available: 12-21-2025
  • Available Now: Yes

Property History for 20 Winslow Road, Unit 2

DateEvent & SourcePriceAppreciation
Dec 17, 2025

Listed (Active)

MLS PIN #73462680

$3,500
Dec 15, 2025

Expired

MLS PIN #73452182

$3,500
Nov 12, 2025

Price Change

MLS PIN #73452182

$3,900
Nov 6, 2025

Listed (Active)

MLS PIN #73452182

$4,000
Oct 31, 2025

Expired

MLS PIN #73442363

$4,000
Oct 10, 2025

Listed (Active)

MLS PIN #73442363

$4,000
Sep 30, 2025

Expired

MLS PIN #73426410

$4,000
Sep 4, 2025

Listed (Active)

MLS PIN #73426410

$4,000
Aug 31, 2025

Expired

MLS PIN #73413493

$4,000
Aug 4, 2025

Listed (Active)

MLS PIN #73413493

$4,500
Jul 31, 2025

Expired

MLS PIN #73373592

$4,500
Jun 3, 2025

Temporarily Withdrawn

MLS PIN #73373592

$4,500
May 13, 2025

Listed (Active)

MLS PIN #73373592

$4,800
Sep 1, 2024

Rented

MLS PIN #73256870

$4,500
Aug 7, 2024

Under Agreement

MLS PIN #73256870

Aug 7, 2024

Contingent

MLS PIN #73256870

Aug 7, 2024

Under Agreement

MLS PIN #73256870

Jun 30, 2024

Expired

MLS PIN #73220030

$4,000
Jun 25, 2024

Listed (Active)

MLS PIN #73256870

$4,750
May 15, 2024

Temporarily Withdrawn

MLS PIN #73220030

$4,000
Apr 4, 2024

Listed (Active)

MLS PIN #73220030

$4,000
Mar 31, 2024

Expired

MLS PIN #73195870

$4,000
Jan 23, 2024

Listed (Active)

MLS PIN #73195870

$4,000
Sep 1, 2023

Expired

MLS PIN #73141050

$3,800
Aug 17, 2023

Temporarily Withdrawn

MLS PIN #73141050

$3,800
Jul 26, 2023

Listed (Active)

MLS PIN #73141050

$4,000
Oct 30, 2022

Rented

MLS PIN #73041786

$3,600
Oct 22, 2022

Under Agreement

MLS PIN #73041786

Oct 22, 2022

Contingent

MLS PIN #73041786

Oct 22, 2022

Under Agreement

MLS PIN #73041786

Sep 28, 2022

Listed (Active)

MLS PIN #73041786

$3,600
Sep 1, 2021

Rented

MLS PIN #72815135

$2,995
Jul 1, 2021

Contingent

MLS PIN #72815135

Jul 1, 2021

Under Agreement

MLS PIN #72815135

Apr 15, 2021

Listed (Active)

MLS PIN #72815135

$3,200
Jun 1, 2018

Rented

MLS PIN #72227827

$3,700
Jan 4, 2018

Contingent

MLS PIN #72227827

Jan 4, 2018

Under Agreement

MLS PIN #72227827

Sep 13, 2017

Listed (Active)

MLS PIN #72227827

$3,000
DateEvent & SourcePrice
12/17/2025

Listed (Active)

MLS PIN #73462680

$3,500
12/15/2025

Expired

MLS PIN #73452182

$3,500
11/12/2025

Price Change

MLS PIN #73452182

$3,900
11/06/2025

Listed (Active)

MLS PIN #73452182

$4,000
10/31/2025

Expired

MLS PIN #73442363

$4,000
10/10/2025

Listed (Active)

MLS PIN #73442363

$4,000
09/30/2025

Expired

MLS PIN #73426410

$4,000
09/04/2025

Listed (Active)

MLS PIN #73426410

$4,000
08/31/2025

Expired

MLS PIN #73413493

$4,000
08/04/2025

Listed (Active)

MLS PIN #73413493

$4,500
07/31/2025

Expired

MLS PIN #73373592

$4,500
06/03/2025

Temporarily Withdrawn

MLS PIN #73373592

$4,500
05/13/2025

Listed (Active)

MLS PIN #73373592

$4,800
09/01/2024

Rented

MLS PIN #73256870

$4,500
08/07/2024

Under Agreement

MLS PIN #73256870

08/07/2024

Contingent

MLS PIN #73256870

08/07/2024

Under Agreement

MLS PIN #73256870

06/30/2024

Expired

MLS PIN #73220030

$4,000
06/25/2024

Listed (Active)

MLS PIN #73256870

$4,750
05/15/2024

Temporarily Withdrawn

MLS PIN #73220030

$4,000
04/04/2024

Listed (Active)

MLS PIN #73220030

$4,000
03/31/2024

Expired

MLS PIN #73195870

$4,000
01/23/2024

Listed (Active)

MLS PIN #73195870

$4,000
09/01/2023

Expired

MLS PIN #73141050

$3,800
08/17/2023

Temporarily Withdrawn

MLS PIN #73141050

$3,800
07/26/2023

Listed (Active)

MLS PIN #73141050

$4,000
10/30/2022

Rented

MLS PIN #73041786

$3,600
10/22/2022

Under Agreement

MLS PIN #73041786

10/22/2022

Contingent

MLS PIN #73041786

10/22/2022

Under Agreement

MLS PIN #73041786

09/28/2022

Listed (Active)

MLS PIN #73041786

$3,600
09/01/2021

Rented

MLS PIN #72815135

$2,995
07/01/2021

Contingent

MLS PIN #72815135

07/01/2021

Under Agreement

MLS PIN #72815135

04/15/2021

Listed (Active)

MLS PIN #72815135

$3,200
06/01/2018

Rented

MLS PIN #72227827

$3,700
01/04/2018

Contingent

MLS PIN #72227827

01/04/2018

Under Agreement

MLS PIN #72227827

09/13/2017

Listed (Active)

MLS PIN #72227827

$3,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Schools near 20 Winslow Road, Unit 2

This home is within Brookline School District.
Rating
School
Type
Grades
Distance
Public - PK to 8
Public - 9 to 12
Private - 8 to 12
Private - 7 to 12
Rating
School
Distance
Florida Ruffin Ridley School
PublicPK to 8

Brookline High School
Public9 to 12

Bay Cove Academy
Private8 to 12

Beacon High School
Private7 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

20 Winslow Road, Unit 2 is available for rent in Brookline, MA 02446. This property was listed on December 17, 2025 by Berkshire Hathaway HomeServices Warren Residential, it's currently listed at $3,500. It has been on the market for a total of 4 days and was last rented on September 1, 2024. This listing's school district is Brookline School District. Nearby schools include Florida Ruffin Ridley School, Brookline High School and Bay Cove Academy. 20 Winslow Road, Unit 2 is a 3-bed, 1-bath, 1,100 sqft a property.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the owner. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Berkshire Hathaway HomeServices Warren Residential, Gretchen Devine

The property listing data and information, or the images, set forth herein were provided to MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS. The property listing data and information, and the images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the images, set forth herein.