83-85 Highland Street, Boston, MA

$2,475,000

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15

Beds

6

Baths

5,748

Square feet

0.04

Acres

About 83-85 Highland Street

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.

Open House

Sat, Sep 19th, 2026 @ 11am - 12pm

Features of 83-85 Highland Street

MLS® # 73577201
Price $2,475,000
Bedrooms 15
Bathrooms 6.00
Full Baths 6
Square Footage 5,748
Acres 0.04
Year Built 1900
Type Residential Income
Sub-Type 3 Family
Status Active

Community Information

Address 83-85 Highland Street
Area Roxbury's Fort Hill
City Boston
County Suffolk
State MA
Zip Code 02119

Amenities

Parking On Street
Is Waterfront No
Has Pool No

Interior

Fireplace No
# of Stories 3
Stories 3

Additional Information

Zoning 0013

Listing Details

Agent Mission Realty Advisors
Office Compass

Listing Map

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