17 Windermere Road, Boston MA 02125
Boston, MA 02125 • Dorchester
$1,075,000
Est. $6,529/month
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'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.
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Recently Sold Nearby
Property History
Property Timeline
Listed for Sale
Jul 16, 2026
$1,075,000
Original listing
Agent: David Cahill
Office: Century 21 Cityside
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 07/16/2026 | 🏠 Listed for Sale | $1,075,000 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2026 | $10,721 | $857,000 |
Financial Details
Annual Property Tax
$10,721
Tax Year 2026
Assessed Value
$857,000
Facts & Features
Home Facts
Type
Residential Income
Style
Multi Family
Year Built
1890
Living Area
2,875 sq ft
Lot Size
0.11 acres
Bedrooms
4
Full Baths
2
Half Baths
1
Total Rooms
11
Investment Metrics
Units
2
Unit 1 Rent
— · N
Unit 2 Rent
— · N
Interior
Heating
None
Cooling
None
Flooring
Wood
Appliances
None
Fireplace
None
Basement
Full
Laundry
None
Features
None
Exterior
Construction
Frame
Architecture
None
Roof
Wood, Slate
Features
None
Pool
None
Spa
None
Fencing
None
Patio/Porch
Porch, Deck
Parking
Features
Paved Drive, On Street
Utilities
Electric
100 Amp Service
Water
Public
Sewer
Public Sewer
Gas
None
Other
None
Financial
Annual Tax
$10,721
Assessed Value
$857,000
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
MA Disclosures
Seller Disclosures
Both Units Currently Occupied, But At Below Market Rates ($1, 950 And $3, 100). Will Be Vacant At Closing. Taxes Do Not Reflect Potential $4, 353.74 Credit For Owner Occupants. First Floor Furnace Is From 2009 And Hot Water Tank Is 2025.
Additional Details
Possession
None
Accepted Financing
None
Structure Type
[]
Sq Ft Source
Public Record
Documents
None
County
Suffolk
Total market time (incl. prior listings)
4 days
Property Overview
Property Type
Multi Family
Listing Type
For Sale
Year Built
1890
Bedrooms
4
Full Bathrooms
2
Half Bathrooms
1
Living Area
2,875 sq ft
Total Rooms
11
Stories
3
Levels
3
Room Details
Other Floor
Bathroom1
Bedroom5
Bedroom4
Bedroom3
Dining Room
Kitchen
Bathroom2
Bedroom2
Living Room
Bathroom3
Master Bedroom
Office
Family Room
Master Bathroom
Interior Features
Flooring:
Wood
Appliances:
Interior Features:
Windows:
Basement:
Full
Laundry:
Security:
Construction & Materials
Year Built:
1890
Structure Type:
Exterior Materials:
Frame
Roof:
Wood, Slate
Foundation:
Granite
Stories:
3
Heating, Cooling & Utilities
Heating:
Heating Zones:
3
Cooling:
Hot Water:
Natural Gas
Water Source:
Public
Sewer:
Public Sewer
Energy Features:
Exterior & Lot
Exterior Features:
Patio & Porch:
Porch, Deck
Fencing:
Other Structures:
Lot Features:
Gentle Sloping, Sloped
Road Surface:
Paved
Parking & Garage
Parking Features:
Paved Drive, On Street
Nearby Schools
School District
Boston School District local
C-
Where Graduates Go
Class of 2021
52%
attend college
38%
4-Year
14%
2-Year
7%
Out of State
7%
Working
School Safety
2024-25
3.7%
Above Average
3.2%
Suspensions
0.3%
In-School
0.5%
Emergency
1.8% below state avg
Elementary Schools
10 schools
C-
Everett Elementary School
0.2 mi
|
#728 of 824
|
Score: 33.7
Dropped 53 spots from last year
-24.5 below state avg
288 students
Diverse
Diverse Student Body
Grades PK-06
C
Conservatory Lab Charter School
0.4 mi
|
#261 of 352
|
Score: 35.6
Dropped 4 spots from last year
-22.6 below state avg
454 students
Diverse
Grades PK-08
D
Mather Elementary School
0.5 mi
|
#754 of 824
|
Score: 32.2
Dropped 257 spots from last year
-26 below state avg
473 students
Very Diverse
Diverse Student Body
Grades PK-06
Saint John Paul II Academy - Columbia
0.5 mi
Grades PK-08
B
Boston Collegiate Charter School
0.5 mi
|
#167 of 346
|
Score: 53.7
Improved 31 spots from last year
-4.5 below state avg
708 students
Diverse
Rising School
College Ready Curriculum
Diverse Student Body
Grades 05-12
Compass School
0.5 mi
Grades PK-12
F
Clap Elementary School
0.6 mi
|
#808 of 824
|
Score: 26.3
Dropped 23 spots from last year
-31.9 below state avg
140 students
Diverse
Diverse Student Body
Grades PK-06
C-
Winthrop Elementary School
0.7 mi
|
#665 of 824
|
Score: 37.6
Dropped 171 spots from last year
-20.6 below state avg
226 students
Diverse
Grades PK-06
F
King Elementary School
0.8 mi
|
#823 of 824
|
Score: 22.7
Dropped 3 spots from last year
-35.6 below state avg
464 students
Diverse
Grades PK-06
C-
UP Academy Holland School
0.8 mi
|
#721 of 824
|
Score: 34.1
Improved 98 spots from last year
-24.1 below state avg
641 students
Diverse
Rising School
Grades PK-06
Middle Schools
10 schools
A
Uncommon Schools - Roxbury Preparatory Dorchester Campus Middle School
0.6 mi
|
#4 of 16
|
Score: 41.9
Improved 187 spots from last year
-16.3 below state avg
1,126 students
Diverse
Rising School
College Ready Curriculum
Grades 05-08
Dearborn Middle School
1.1 mi
Mother Caroline Academy
1.2 mi
Grades 05-08
F
Higginson/Lewis K-8 School
1.3 mi
|
#349 of 352
|
Score: 23.6
Improved 3 spots from last year
-34.6 below state avg
213 students
Diverse
Grades 03-08
Middle School Academy
1.4 mi
Epiphany School
1.5 mi
Grades 05-08
Nativity Prep School
2.1 mi
Grades 05-08
C
Ohrenberger School
5.8 mi
|
#265 of 352
|
Score: 34.9
Improved 20 spots from last year
-23.3 below state avg
477 students
Diverse
Rising School
Diverse Student Body
Grades 03-08
Frederick Pilot Middle
0.8 mi
McCormack Middle
1.0 mi
High Schools
10 schools
C
Ruth Batson Academy
1.0 mi
|
#19 of 25
|
Score: 27.6
Improved 346 spots from last year
-30.6 below state avg
604 students
Diverse
8 sports
• 128 athletes
Early College Program
Rising School
Grades 07-12
A+
Boston Latin Academy
1.1 mi
|
#2 of 25
|
Score: 63.9
Improved 214 spots from last year
+5.7 above state avg
1,693 students
Very Diverse
17 sports
• 1,298 athletes
High Graduation Rate
Rising School
Strong Athletics
Diverse Student Body
Grades 07-12
B
Dearborn STEM Academy
1.3 mi
|
#13 of 25
|
Score: 31.7
Improved 356 spots from last year
-26.6 below state avg
565 students
Diverse
10 sports
• 242 athletes
Early College Program
Rising School
Grades 07-12
A-
O'Bryant School of Math & Science
1.8 mi
|
#90 of 346
|
Score: 61.1
Improved 94 spots from last year
+2.9 above state avg
1,509 students
Very Diverse
High Graduation Rate
Rising School
College Ready Curriculum
Diverse Student Body
Grades 07-12
Cathedral High School
1.9 mi
9 sports
• 430 athletes
Grades 07-12
Meridian Academy
2.1 mi
Grades 06-09
B+
TechBoston Academy
2.2 mi
|
#11 of 25
|
Score: 34.1
Improved 349 spots from last year
-24.1 below state avg
850 students
Diverse
Rising School
Grades 07-12
C
Quincy Upper School
2.3 mi
|
#268 of 346
|
Score: 44.6
Improved 4 spots from last year
-13.6 below state avg
557 students
Very Diverse
12 sports
• 208 athletes
High Graduation Rate
Diverse Student Body
Grades 06-12
D
English High School
2.5 mi
|
#324 of 346
|
Score: 29.7
Improved 34 spots from last year
-28.5 below state avg
720 students
Moderate
8 sports
• 332 athletes
Rising School
Career Tech Programs
Grades 07-12
A+
Boston Latin School
2.5 mi
|
#19 of 346
|
Score: 73.3
Improved 61 spots from last year
+15.1 above state avg
2,424 students
Very Diverse
18 sports
• 2,006 athletes
Strong AP Program
High Graduation Rate
Rising School
Strong Athletics
Grades 07-12
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95% Interest
Year 15
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Location
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Neighborhood
Dorchester
17 Windermere Road, Boston MA 02125
Boston, MA 02125
Listing Information
Listing Agent
David Cahill
Listing Office
Century 21 Cityside
Office Phone
617-262-2600
Agent MLS ID
BB803079
Office MLS ID
BB6400
Listing Data Updated
Jul 20, 2026 3:05 AM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.
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