OPEN TODAY, 1PM TO 2PM

For sale

$999,000

Est. $6,580/mo —

•

2,875

sq ft

17 Windermere Rd, Dorchester, MA 02125

About this home

Don't miss this fantastic 2-unit opportunity on the north side of vibrant Jones Hill, boasting breathtaking views of downtown, Back Bay, and Dorchester Bay. Owner just installed brand-new gleaming hardwood floors on portions of the second floor and painted the entire home. "Owner's Unit" is comfortably spread out over top 2 levels w/ a private entrance. Main level flows seamlessly from the living area to the formal dining room, bordered by the kitchen, a spacious BR, and a versatile office/flex space with potential for a 4th BR conversion. Upstairs features 2 well-proportioned BR, w/ a rear primary suite with a en suite 1/2 bath and a private deck—perfect for relaxing on warm summer evenings. The 1st-floor unit is a spacious 1-BR featuring original inlaid ornamental wood flooring, a private porch, and layout flexibility to easily convert into a 2-BR. Major property upgrades include a 2020 Navien on-demand heating & hot water system, durable stainless-steel countertops, and well-maintained slate roof. Short walk to Red Line & for gardeners, a charming neighborhood community garden sits 2 doors down.

Multi-familyProperty Type

1890Year Built

4,638 sq ftLot Size

$347Price/Sq.Ft.

Listed by David Cahill • Century 21 Cityside

Listed by • Century 21 Cityside

Listing updated: Oct 17, 2026 at 03:09am

Redfin checked: 2 minutes ago

•Source:MLS PIN #73551214

Payment calculator

$6,580 per month

Principal and interest$5,520

Property taxes

$893

HOA dues

Home insurance

$167

Utilities

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Open houses

Sunday, Oct 25

1:00pm - 2:00pm

Nearby open houses (10)

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Around this home

Schools

K - 12
Preschool & daycare

Everett Elementary School

Public PreK-6 • Assigned • 0.2mi

5/10

Lilla G. Frederick Middle School

Public 7-8 • Assigned • 0.8mi

3/10

Carter School

Public 8-12 • Assigned • 0.8mi

Ruth Batson Academy

Public 7-12 • Assigned • 0.9mi

2/10

Provided by GreatSchools

About Uphams Corner-Jones

Hill

Uphams Corner-Jones Hill, located between Dorchester Avenue and Columbia Road, is a residential and commercial Boston neighborhood with a hilltop streetscape and a historic main-street core. The neighborhood’s character concentrates around the busy Four Corners at Dudley Street and Columbia Road, where corner markets, Caribbean bakeries, barbershops, and takeout counters keep the sidewalks in motion. The Strand Theatre anchors the cultural calendar, while the Dorchester Art Project adds gallery energy in a former church. Triple Decker blocks climb Jones Hill, mixing porches, bay windows, and tight-knit side streets. Parks and schoolyards stitch together walking routes, and the MBTA Fairmount Line adds a commuter rhythm.

Provided by Walk Score and Local Logic

Offer insights

17 Windermere Rd · $999,000

Strong offer

$999K and above

75% chance or better to win

Why $999K+ is a strong offer

DAYS ON MARKET

The average home goes pending in 48 days.

SALE-TO-LIST

Most homes are selling 2% below list price.

About offer insights

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Interior features
11 total rooms
Full basement
Has waterview (bay)

Bathrooms
2 full bathrooms
1 half bathroom

Flooring
Wood flooring

Heating & cooling
2 heating units
3 heat zones

Sale and tax history for 17 Windermere Rd

Sale History
Tax History

Date

Event

Price

MLS PIN #73551214

Oct 13, 2026

Price Changed

$999,000

$347/sq ft

Oct 5, 2026

Price Changed

$1,049,000

$365/sq ft

Sep 23, 2026

Relisted

—

Aug 11, 2026

Listing Removed

—

Jul 16, 2026

Listed

$1,075,000

$374/sq ft

MLS PIN #70586762

May 1, 2008

Sold

$343,000

$119/sq ft

Apr 17, 2008

Listing Removed

—

May 29, 2007

Listed

$409,900

$143/sq ft

JONES HILL. LOCATION! VIEWS! 2-family in move-in condition offers striking skyline views from two levels. The first unit is a 1-bedroom with great income potential. The second unit has 2 levels of living, the first level offering spacious open living/dining areas, 2 bedrooms or a bedroom and office, kitchen, full bath, and the skyline. On the second level, 2 large bedrooms, a half bath, and from the large deck, panoramic city & water views. In move-in condition or a great choice for conversion

Year

Property tax

Land + Additions

Assessment*

2023

$8,252 (+8.6%)

$269,400 + $498,900

$768,300

2022

$7,599 (+2.0%)

$244,900 + $453,500

$698,400

2021

$7,452 (+6.5%)

$244,900 + $453,500

$698,400

2020

$6,997 (+15.8%)

$261,000 + $401,600

$662,600

2019

$6,040 (+12.7%)

$175,400 + $397,700

$573,100

2018

$5,361 (+3.9%)

$175,400 + $336,100

$511,500

2017

$5,159 (+5.8%)

$175,400 + $311,800

$487,200

2016

$4,877 (+13.2%)

$175,400 + $268,000

$443,400

2015

$4,309 (+11.3%)

$135,800 + $220,000

$355,800

2014

$3,871 (+1.5%)

$135,800 + $171,900

$307,700

2013

$3,815 (−1.6%)

$135,800 + $154,500

$290,300

2012

$3,878 (+1.9%)

$119,100 + $178,300

$297,400

2011

$3,804

$119,100 + $178,300

$297,400

2009

$3,804 (−6.6%)

$119,100 + $178,300

$297,400

2006

$4,072

$142,400 + $240,700

$383,100

Public record

Public record
Zoning
Permits

Beds

Baths

2.5

Stories

Lot width

—

Lot depth

—

Lot size

4,792 Sq. Ft.

Year renovated

—

Finished Sq. Ft.

2,875

Unfinished Sq. Ft.

—

Total Sq. Ft.

2,875

Year built

1890

Style

Multi-Family (2-4 Unit)

County

Suffolk County

APN

1303626

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

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

74/ 100

Good sunlight

Sunscore

This home receives average direct sun exposure in Dorchester. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

8.8 hrs

2.1 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 17 Windermere Rd

$981,665

$17K under list price of $999K

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $860K to $1.4M.

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SOLD SEP 4, 2026
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Details provided by MLS PIN and may not match the public record. Learn more.

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About this home

Payment calculator

Affordability tools

See this home in person

Nearby open houses (10)

Around this home

Schools

Offer insights

Property details

Sale and tax history for 17 Windermere Rd

Public record

Climate risks

Historical weather

Sun exposure

Redfin Estimate for 17 Windermere Rd

Early Access listings

Nearby similar homes

New listings for sale in 02125

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