3 Family at 83-85 Highland Street, Boston MA 02119, Boston
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31 photos

$2,475,000

83-85 Highland Street, Boston MA 02119
Boston, MA 02119
Listed by Mission Realty Advisors
Bedrooms
15
Bathrooms
6
Living area
5,748 sqft
Year built
1900

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.

Property details

MLS #
73577201
Property type
3 Family
Subdivision
N/A
Status
Active
Days on market
9
On market date
September 15, 2026
Stories
3
Total bathrooms
6
Garage spaces
N/A
Parking spaces
N/A
Lot size
0.04 acres
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Nearby schools

Within 10 miles · public school directory data (NCES)

Elementary
Nathan Hale
0.14 mi away · Grades -1-6
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
172
Student:teacher ratio
14.3:1
District
Boston
Middle
James P Timilty Middle
0.27 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
205
Student:teacher ratio
8.2:1
District
Boston
HighCharter
City on a Hill Charter Public School Circuit Street
0.35 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
229
Student:teacher ratio
11.5:1
District
City on a Hill Charter Public School (District)

Walkability

Blended score for Boston's center: EPA's National Walkability Index (street network, transit, land-use mix) combined with nearby-amenity density. 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

89
Highly walkable
out of 100
EPA National Walkability Index
16.3 / 20 -- Most walkable
Nearby-amenity density
100 / 100
Restaurants & cafes20
Grocery stores20
Parks20
Schools20
Transit stops20
Pharmacies16

Market position

How this listing compares to current activity in Boston, from live MLS data.

On the market 9 days -- 107 fewer days than Boston's current average of 116 days.
For reference, the median list price across 7,888 active listings in Boston right now is $7,500.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

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Est. monthly payment
$15,055/mo
$495,000 down
$1,980,000 loan
Principal & interest$12,842
Property tax (est.)$2,063
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated 6 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.