83-85 Highland Street, Boston, MA 02119

$2,450,000 · For sale

83-85 Highland Street, Boston

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.

About this address

83-85 Highland Street is a multi-family home for sale in Boston, MA 02119 with 5,748 square feet, asking $2,450,000. It was built in 1900. It has been on our site since October 15, 2026.

At $426 a square foot, it compares with a median of $417 among the 293 other multi-family homes for sale in Boston with a stated size.

The whole property at this address is assessed at $772,500 for fiscal year 2023. The assessor lists a lot of 0.04 acres.

It scores 93 out of 100 for walkability, from how close everyday places are.

The closest train or subway stop is Roxbury Crossing (MBTA Orange Line), about 0.3 miles away. The closest bus stop is Centre St @ Cedar St (MBTA routes 14, 41), about 0.1 miles away.

The closest public schools by level are Hale Elementary School (0.1 miles), Higginson-Lewis K-8 School (0.5 miles) and Fenway High School (0.4 miles). The district decides which school serves an address.

Listing information from MLS Property Information Network (MLS PIN), MLS #73577201, deemed reliable but not guaranteed. Prices are compared with other homes listed on this site today. Trains and buses come from the transit agencies’ published schedules and schools from the National Center for Education Statistics. Distances are straight-line. Assessed values and past sales are public records from municipal assessors, published by MassGIS. An assessed value is set for taxation and may differ from market value.

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