83-85 Highland Street, Boston MA 02119
Boston, MA 02119 • Roxbury's Fort Hill
$2,475,000
Est. $13,780/month
Estimate assumptions
20% down, a 30-year loan at 6.5%, and $200/month estimated insurance.
Includes the supplied property-tax and HOA inputs; missing inputs contribute $0. HOA fees with an unspecified frequency are treated as monthly. PMI and closing costs are excluded.
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Open House Schedule
17
Sep
Thursday, September 17
11:00 AM - 12:00 PM EDT
19
Sep
Saturday, September 19
11:00 AM - 12:00 PM EDT
About this home
Rarely available at this scale, this substantial Fort Hill three-family offers 15 bedrooms, 6 bathrooms, nearly 5,750 square feet of rentable living area, strong in-place income, and a current 6.76% cap rate in one of Boston’s most strategically located rental markets. Each of the three expansive residences features 5 bedrooms and 2 full bathrooms, with renovated kitchens and 2 full bathrooms and the added convenience of in-unit laundry. Fully leased through August 31, 2027, the property currently generates $16,725 per month and $200,700 in annual gross rental income, providing immediate, stabilized cash flow with a projected 7.28% cap rate by September 1, 2027. Ideally positioned in historic Fort Hill, the property combines neighborhood character with exceptional access to some of Boston’s largest employment, educational, and medical centers. Located between the Jackson Square and Roxbury Crossing Orange Line stations, with additional public transportation nearby, the property offers convenient connectivity throughout Boston and is close to Northeastern University, Wentworth, MassArt, and the Longwood Medical and Academic Area. Longwood, just down the road, is home to Brigham and Women’s Hospital, Boston Children’s Hospital, Beth Israel Deaconess Medical Center, Dana-Farber Cancer Institute, Harvard Medical School, and numerous other healthcare, research, and academic institutions. With three large 5-bedroom residences, renovated interiors, in-unit laundry, strong existing income, long-term leases, and proximity to transit, universities, and Longwood, this is a compelling opportunity to acquire a stabilized, high-capacity income-producing asset in a well-connected Boston neighborhood.
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Recently Sold Nearby
Property History
Property Timeline
Listed for Sale
Sep 15, 2026
$2,475,000
Original listing
Agent: Mission Realty Advisors
Office: Compass
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 09/15/2026 | 🏠 Listed for Sale | $2,475,000 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2027 | $12,776 | $730,000 |
Financial Details
Annual Property Tax
$12,776
Tax Year 2027
Assessed Value
$730,000
Facts & Features
Central AC
Home Facts
Type
Residential Income
Style
3 Family
Year Built
1900
Living Area
5,748 sq ft
Lot Size
0.04 acres
Stories
3
Bedrooms
15
Full Baths
6
Total Rooms
27
Investment Metrics
Units
3
Unit 1 Rent
$5,875/mo · Y
Unit 2 Rent
$5,400/mo · Y
Unit 3 Rent
$5,450/mo · Y
Total Monthly Rent
$16,725/mo
Gross Income
$200,700
Net Operating Income
$200,700
Cap Rate
8.11%
Interior
Heating
Natural Gas
Cooling
Central Air, Window Unit(s)
Flooring
Wood, Hardwood
Appliances
Oven, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer
Fireplace
None
Basement
Dirt Floor
Laundry
None
Features
Storage, Stone/granite/solid Counters, Bathroom With Shower Stall, Bathroom With Tub, Smart Thermostat, Open Floorplan, Living Room, Kitchen
Exterior
Construction
Brick
Architecture
None
Roof
Rubber
Features
None
Pool
None
Spa
None
Fencing
None
Patio/Porch
None
Parking
Features
On Street
Utilities
Electric
None
Water
Public
Sewer
Public Sewer
Gas
None
Other
None
Financial
Annual Tax
$12,776
Assessed Value
$730,000
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
MA Disclosures
Lead Paint
Unknown
Seller Disclosures
Buyer To Own Due Diligence.
Additional Details
Possession
None
Accepted Financing
None
Structure Type
[]
House Color
Brick
Sq Ft Source
Public Record
Documents
None
County
Suffolk
Property Overview
Property Type
3 Family
Listing Type
For Sale
Year Built
1900
Bedrooms
15
Full Bathrooms
6
Living Area
5,748 sq ft
Total Rooms
27
Stories
3
Levels
3
Floor Layout
Interactive room guide
Floor Layout
Finished Area
5,748 sq ft above grade
Display Options
Room Markers
OOffice (1)
KKitchen (1)
BRBedroom (5)
BABathroom (4)
DDining (1)
LLiving (2)
Conceptual diagram based on MLS room data. It is not to scale and is not a substitute for architectural plans or on-site measurements.
Interior Features
Flooring:
Wood, Hardwood
Appliances:
Oven, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer
Interior Features:
Storage, Stone/Granite/Solid Counters, Bathroom with Shower Stall, Bathroom With Tub, Smart Thermostat, Open Floorplan, Living Room, Kitchen
Windows:
Basement:
Dirt Floor
Laundry:
Security:
Construction & Materials
Year Built:
1900
Structure Type:
Exterior Materials:
Brick
Roof:
Rubber
Foundation:
Concrete Perimeter
Stories:
3
Heating, Cooling & Utilities
Heating:
Natural Gas
Cooling:
Central Air, Window Unit(s)
Hot Water:
Natural Gas
Water Source:
Public
Sewer:
Public Sewer
Energy Features:
Exterior & Lot
Exterior Features:
Patio & Porch:
Fencing:
Other Structures:
Lot Features:
Corner Lot
Road Surface:
Parking & Garage
Parking Features:
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
Hale Elementary School
0.1 mi
|
#590 of 825
|
Score: 41.3
Dropped 289 spots from last year
-16.9 below state avg
167 students
Diverse
Diverse Student Body
Grades PK-06
F
Tobin K-8 School
0.5 mi
|
#344 of 352
|
Score: 24.6
Dropped 8 spots from last year
-33.6 below state avg
355 students
Diverse
Grades PK-08
Our Lady of Perpetual Help Mission Grammar School
0.6 mi
Grades K-08
Parkside Christian Academy/Cross Factor Academy
0.7 mi
Grades PK-12
F
Hennigan Elementary School
0.7 mi
|
#814 of 825
|
Score: 25.1
Dropped 1 spots from last year
-33.1 below state avg
361 students
Moderate
Grades PK-06
F
Ellis Elementary School
0.7 mi
|
#818 of 825
|
Score: 24.8
Dropped 58 spots from last year
-33.4 below state avg
418 students
Moderate
Grades PK-06
C
John F Kennedy School
0.8 mi
|
#637 of 825
|
Score: 38.9
Dropped 62 spots from last year
-19.3 below state avg
366 students
Diverse
Diverse Student Body
Grades PK-06
D
Perkins Elementary School
0.8 mi
|
#766 of 825
|
Score: 31.2
Improved 35 spots from last year
-27 below state avg
201 students
Diverse
Rising School
Diverse Student Body
Grades PK-06
D
Orchard Gardens K-8 School
0.8 mi
|
#325 of 352
|
Score: 28.8
Improved 14 spots from last year
-29.4 below state avg
716 students
Diverse
Grades PK-08
D
Trotter Elementary School
0.8 mi
|
#788 of 825
|
Score: 29.5
Same rank as last year
-28.7 below state avg
360 students
Diverse
Grades PK-06
Middle Schools
10 schools
F
Higginson/Lewis K-8 School
0.5 mi
|
#349 of 352
|
Score: 23.2
Improved 3 spots from last year
-35 below state avg
246 students
Diverse
Grades 03-08
Nativity Prep School
0.6 mi
Grades 05-08
Mother Caroline Academy
1.4 mi
Grades 05-08
A
Uncommon Schools - Roxbury Preparatory Dorchester Campus Middle School
1.5 mi
|
#4 of 16
|
Score: 42.5
Improved 187 spots from last year
-15.7 below state avg
1,225 students
Diverse
Rising School
College Ready Curriculum
Grades 05-08
Dearborn Middle School
1.5 mi
Middle School Academy
2.2 mi
Epiphany School
2.7 mi
Grades 05-08
C
Ohrenberger School
5.4 mi
|
#266 of 352
|
Score: 35.0
Improved 19 spots from last year
-23.2 below state avg
458 students
Diverse
Diverse Student Body
Grades 03-08
Timilty Middle
0.3 mi
Frederick Pilot Middle
1.5 mi
High Schools
10 schools
A-
O'Bryant School of Math & Science
0.3 mi
|
#90 of 346
|
Score: 61.6
Improved 94 spots from last year
+3.4 above state avg
1,518 students
Very Diverse
High Graduation Rate
Rising School
College Ready Curriculum
Diverse Student Body
Grades 07-12
B
Dearborn STEM Academy
0.6 mi
|
#13 of 25
|
Score: 33.4
Improved 356 spots from last year
-24.8 below state avg
565 students
Moderate
10 sports
• 242 athletes
Early College Program
Rising School
Grades 07-12
A+
Boston Latin School
0.9 mi
|
#20 of 346
|
Score: 73.7
Improved 60 spots from last year
+15.5 above state avg
2,382 students
Very Diverse
18 sports
• 2,006 athletes
Strong AP Program
High Graduation Rate
Rising School
Strong Athletics
Grades 07-12
A+
Boston Latin Academy
0.9 mi
|
#2 of 25
|
Score: 64.9
Improved 214 spots from last year
+6.7 above state avg
1,669 students
Very Diverse
17 sports
• 1,298 athletes
Strong AP Program
High Graduation Rate
Rising School
Strong Athletics
Grades 07-12
Meridian Academy
1.1 mi
Grades 06-09
Cathedral High School
1.6 mi
9 sports
• 430 athletes
Grades 07-12
D
English High School
1.7 mi
|
#328 of 346
|
Score: 28.9
Improved 30 spots from last year
-29.3 below state avg
653 students
Diverse
8 sports
• 332 athletes
Rising School
Career Tech Programs
Grades 07-12
B-
Margarita Muniz Academy
1.8 mi
|
#14 of 25
|
Score: 31.6
Improved 349 spots from last year
-26.7 below state avg
480 students
Less Diverse
Rising School
Grades 07-12
Newman School
1.8 mi
Grades 07-12
C
Quincy Upper School
2.1 mi
|
#279 of 346
|
Score: 44.4
Dropped 7 spots from last year
-13.8 below state avg
575 students
Very Diverse
12 sports
• 208 athletes
Diverse Student Body
Grades 06-12
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Down: $0
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Monthly Payment Breakdown
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Property Tax
$1,065
Homeowners Insurance
$200
PMI (if <20% down)
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Loan Summary
Total of 360 payments
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Payment Over Time
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
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Location
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Neighborhood
Roxbury's Fort Hill
83-85 Highland Street, Boston MA 02119
Boston, MA 02119
Listing Information
Listing Agent
Mission Realty Advisors
Listing Office
Compass
Office Phone
617-752-6845
Agent MLS ID
TM334200
Office MLS ID
AN3337
Listing Data Updated
Sep 15, 2026 11:02 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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