OFF MARKET

Off Market Sep 2024 for $1M

$1,217,230

Est. refi paymentEst. refi $1,532/mo

•

3,467

sq ft

20 Windermere Rd, Dorchester, MA 02125

About this home

Amazing opportunity for three units nestled atop Jones Hill with panoramic city views. Originally built as a Victorian single-family home and converted decades ago, the new owner will have many terrific opportunities depending on what their investing goals are. The first floor has three bedrooms in the finished basement and would be an excellent income-producing bi-level apartment with four or even five bedrooms. The second floor, where many period details remain, could be one or two bedrooms and the third unit is an open and airy studio. Combining the top two floors into one home could result in a great bi-level owner's unit with a top-floor primary suite. An astute developer could always completely re-imagine the layouts all around to produce two or three amazing condos or the new owner could always keep everything as it currently is and enjoy passive income. Preferred closing on 9/30/24. Showings by appointment. Some notice required.

Multi-familyProperty Type

1890Year Built

4,913 sq ftLot Size

$351Est. Price/Sq.Ft.

Listed by David Cahill • Century 21 Cityside

Bought with Sobel Group • Compass

Redfin checked: 3 minutes ago

•Source:MLS PIN #73252211

Redfin Estimate

$1,217,230

$217K since sold in September 2024$18K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 0.7% higher than the average sale price ($1.21M) of 6 comparable homes.

SOLD JUN 30, 2026
$1,395,000
A
6 beds3 baths3,462 sq ft
18 Peverell St, Dorchester, MA 02125
SOLD JUL 1, 2026
$1,299,000
B
8 beds3 baths3,522 sq ft
7 Dawes St, Dorchester, MA 02125
SOLD MAY 27, 2026
$990,000
C
10 beds3 baths3,642 sq ft
8 Elder St, Dorchester, MA 02125
SOLD OCT 7, 2025
$1,100,000
D
7 beds4 baths3,082 sq ft
17 Downer Ct, Dorchester, MA 02122
SOLD NOV 26, 2025
$1,245,000
E
8 beds3 baths3,519 sq ft
8 Dawes St, Dorchester, MA 02125
SOLD MAY 8, 2026
$1,225,000
F
10 beds3 baths3,321 sq ft
42 Monadnock St, Dorchester, MA 02125

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Earn from this home

Sell

$383,904

Est. take-home

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Refinance

Est. cash available

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Market trends in Uphams Corner-Jones Hill, MA

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

100.6%

0.3% MoM

Median sale price

$632K

$784 MoM

Avg. days on market

26d

1 days MoM

Recently sold homes

2 MoM

New listings for sale

NEW 14 HRS AGO
$534,900
2 beds1 bath933 sq ft
121 E Cottage St Unit U-4, Dorchester, MA 02125
NEW 30 HRS AGO
$499,000
2 beds2 baths1,095 sq ft
161 E Cottage #2, Dorchester, MA 02125
NEW 33 HRS AGO
$1,225,000
4 beds3.5 baths3,054 sq ft
17 Buttonwood, Dorchester, MA 02125
$609,000
3 beds2 baths971 sq ft
995 Dorchester Ave #1, Dorchester, MA 02125
EARLY ACCESS
$575,000
3 beds2 baths1,217 sq ft
Dorchester, MA 02125
OPEN SAT, 12PM TO 1PM
$1,200,000
6 beds4 baths2,634 sq ft
20 Rill, Dorchester, MA 02125
$975,000
9 beds3 baths4,446 sq ft
5 Woodward Park St, Dorchester, MA 02125
$1,175,000
2 beds2.5 baths1,679 sq ft
37 Pearl St #4, Dorchester, MA 02125
$1,050,000
8 beds3 baths2,832 sq ft
29 East Cottage, Dorchester, MA 02125
See all

Provided by Redfin

Sale history for 20 Windermere Rd

Year

Property tax

Land + Additions

Assessment*

2023

$10,668 (+4.6%)

$290,000 + $703,300

$993,300

2022

$10,195 (+5.0%)

$273,600 + $663,400

$937,000

2021

$9,705 (+9.0%)

$265,600 + $644,000

$909,600

2020

$8,905 (+15.2%)

$294,500 + $548,800

$843,300

2019

$7,730 (+15.7%)

$191,000 + $542,400

$733,400

2018

$6,683 (+4.0%)

$191,000 + $446,700

$637,700

2017

$6,429 (+6.9%)

$191,000 + $416,100

$607,100

2016

$6,016 (+7.9%)

$191,000 + $355,900

$546,900

2015

$5,574 (+7.8%)

$151,900 + $308,400

$460,300

2014

$5,172 (+6.2%)

$151,900 + $259,200

$411,100

2013

$4,870 (+7.3%)

$151,900 + $218,700

$370,600

2012

$4,537 (+2.0%)

$122,000 + $225,900

$347,900

2011

$4,450

$122,000 + $225,900

$347,900

2009

$4,450 (−2.8%)

$122,000 + $225,900

$347,900

2006

$4,577

$145,900 + $284,700

$430,600

Tax history for 20 Windermere Rd

Year

Property tax

Land + Additions

Assessment*

2023

$10,668 (+4.6%)

$290,000 + $703,300

$993,300

2022

$10,195 (+5.0%)

$273,600 + $663,400

$937,000

2021

$9,705 (+9.0%)

$265,600 + $644,000

$909,600

2020

$8,905 (+15.2%)

$294,500 + $548,800

$843,300

2019

$7,730 (+15.7%)

$191,000 + $542,400

$733,400

2018

$6,683 (+4.0%)

$191,000 + $446,700

$637,700

2017

$6,429 (+6.9%)

$191,000 + $416,100

$607,100

2016

$6,016 (+7.9%)

$191,000 + $355,900

$546,900

2015

$5,574 (+7.8%)

$151,900 + $308,400

$460,300

2014

$5,172 (+6.2%)

$151,900 + $259,200

$411,100

2013

$4,870 (+7.3%)

$151,900 + $218,700

$370,600

2012

$4,537 (+2.0%)

$122,000 + $225,900

$347,900

2011

$4,450

$122,000 + $225,900

$347,900

2009

$4,450 (−2.8%)

$122,000 + $225,900

$347,900

2006

$4,577

$145,900 + $284,700

$430,600

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Public record
Zoning
Permits

Beds

Baths

3.5

Stories

Lot width

—

Lot depth

—

Lot size

4,792 Sq. Ft.

Year renovated

—

Sq. Ft.

2,467

Year built

1890

Style

Multi-Family (2-4 Unit)

County

Suffolk County

APN

1304531

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 20, 2023.

DORCHESTER NEIGHBORHOOD-2F-5000

NDOD-JONES HILL

Dorchester Neighborhood-Two-Family Residential Subdistrict

The Two-Family Residential Subdistricts are established to preserve, maintain, and promote two-family neighborhoods, to preserve existing structures, to provide for new infill construction appropriate to the existing fabric, and to allow minor changes to occur as of right. In a 2F Subdistrict, the maximum number of Dwelling Units allowed in a single building shall be 2.

Zone overlays

Permitted uses

Include but are not limited to:

Religious facility
Day care facility
Housing-Group
Housing-Single unit
Park & open space

Property details

Parking

Parking Information
Has Open Parking
Parking Features: Paved Drive

Interior

Bathroom Information
# of Bathrooms (Full): 3
# of Bathrooms (Half): 1

Basement Information
Basement: Full, Finished

Fireplace Information
Has Fireplace
# of Fireplaces (Total): 1

Interior Features
# of Rooms (Total): 14
Flooring: Tile, Varies, Hardwood

Unit #1 Information
# of Levels: 2
# of Floors: 1
Lease: N

Unit #2 Information
# of Levels: 1
# of Floors: 2
Lease: N

Unit #3 Information
# of Levels: 1
# of Floors: 3
Lease: N

Exterior

Building Information
Building Area (Total): 3,467
Foundation Details: Stone
Construction Materials: Frame
Stories (Total): 4
Year Built Source: Public Records
Year Built Details: Actual

Property Information
PropertySubType: 3 Family - 3 Units Up/Down

Lot Information
Lot Size (Acres): 0.11

Financial

Tax Information
Tax Annual Amount: $11,799
Tax Year: 2024

Utilities

Utility Information
Utilities: for Gas Range, for Electric Range, for Electric Oven
Sewer: Public Sewer
Water Source: Public

Heating & Cooling
Heating Units: 3

Location

Location Information
Directions: Pleasant Street to Sawyer Avenue to Cushing Avenue to Windermere Road. One-way to Stoughton Street.
UnparsedAddress: 20 Windermere Road, Boston MA 02125

Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Laundromat, Highway Access, House of Worship, Public School, T-Station

Public facts

Beds: 7
Baths: 3.5
Sq. Ft.: 2,467
Stories: 3.0
Lot Size: 4,792 square feet
Style: Multi-Family (2-4 Unit)
Year Built: 1890
Year Renovated: —
County: Suffolk County
APN: 1304531

Home facts updated by county records on Jul 20, 2023

Other

Miscellaneous Information
Heat Zones: 4

Listing Information
StandardStatus: Closed

Around this home

Schools

Everett Elementary School

Public PreK-6 • Assigned • 0.1mi

5/10

Lilla G. Frederick Middle School

Public 7-8 • Assigned • 0.8mi

3/10

Carter School

Public 8-12 • Assigned • 0.8mi

Community Academy Of Science And Health

Public 9-12 • Assigned • 0.9mi

2/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

6/10 Heat Factor

7 days above 96° expected this year, 15 days in 30 years

6/10 Wind Factor

64% chance of strong winds in next 30 years

3/10 Air Factor

3 unhealthy days expected this year, 3 days in 30 years

Provided by First Street

Historical weather

Dorchester, MA • 02125

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 9 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

9 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.16M – $1.40M

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Nearby similar homes

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New listings for sale in 02125

NEW 14 HRS AGO

$534,900

2 beds1 bath933 sq ft

121 E Cottage St Unit U-4, Dorchester, MA 02125

NEW 30 HRS AGO

$499,000

2 beds2 baths1,095 sq ft

161 E Cottage #2, Dorchester, MA 02125

NEW 33 HRS AGO

$1,225,000

4 beds3.5 baths3,054 sq ft

17 Buttonwood, Dorchester, MA 02125

$609,000

3 beds2 baths971 sq ft

995 Dorchester Ave #1, Dorchester, MA 02125

EARLY ACCESSCOMPASS COMING SOON

$575,000

3 beds2 baths1,217 sq ft

Dorchester, MA 02125

OPEN SAT, 12PM TO 1PM

$1,200,000

6 beds4 baths2,634 sq ft

20 Rill, Dorchester, MA 02125

$975,000

9 beds3 baths4,446 sq ft

5 Woodward Park St, Dorchester, MA 02125

$1,175,000

2 beds2.5 baths1,679 sq ft

37 Pearl St #4, Dorchester, MA 02125

$1,050,000

8 beds3 baths2,832 sq ft

29 East Cottage, Dorchester, MA 02125

Home values near 20 Windermere Rd

Data from public records.

Address	Redfin Estimate
21 Windermere Rd, Dorchester, MA 6 Beds \| 2 Baths \| 2862 Sq. Ft.	$873,791
25 Windermere Rd, Dorchester, MA 6 Beds \| 2.5 Baths \| 2246 Sq. Ft.	$1,144,456

Address	Redfin Estimate
17 Windermere Rd, Dorchester, MA 5 Beds \| 2.5 Baths \| 2876 Sq. Ft.	$1,039,607
28 Windermere Rd, Dorchester, MA 6 Beds \| 2 Baths \| 2992 Sq. Ft.	$1,066,529

Address	Redfin Estimate
19 Windermere Rd, Dorchester, MA 3 Beds \| 2 Baths \| 2751 Sq. Ft.	$1,440,370
16 Windermere Rd, Dorchester, MA 6 Beds \| 2.5 Baths \| 2404 Sq. Ft.	$883,863

Property information provided by MLS PIN when last listed in 2024. This data may not match . Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in Uphams Corner-Jones Hill, MA

Sale history for 20 Windermere Rd

Tax history for 20 Windermere Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 02125

Home values near 20 Windermere Rd

More real estate resources