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.
| Units | 3 |
| Living area | 5,748 sqft |
| Lot size | 1,931 sqft |
| Year built | 1900 |
| Price / sqft | $431 |
| County | Suffolk |
| MLS # | 73577201 |
| Days on market | 0 days |
| Listed on | September 15, 2026 |
| Annual property tax | $12,776 |
| Tax year | 2027 |
| Assessed value | $730,000 |
| Zoning | 0013 |
| Gross income (actual) | $200,700/yr |
| Net operating income (actual) | $200,700/yr |
| Total actual rent | $16,725/mo |
| Stories | 3 |
| Total rooms | 27 |
| Lot size | 0.04 acres |
| Garage spaces | 0 |
| Parking spaces | 0 |
| Parking | On Street |
| Basement | Dirt Floor |
| Foundation | Concrete Perimeter |
| Roof | Rubber |
| Construction | Brick |
| Flooring | Wood, Hardwood |
| Heating | Natural Gas |
| Cooling | Central Air, Window Unit(s) |
| Sewer | Public Sewer |
| Water | Public |
| Appliances | Oven, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer |
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Listing courtesy of a MLS PIN member office. Listing data © MLS PIN.
Auto-generated from the listing data — richer AI answers coming with the live site.
It is a 3-unit multi-family property with 5,748 sqft of living area, built in 1900.
83-85 Highland Street, Boston MA 02119 has been listed for 0 days (since September 15, 2026).
At a list price of $2,475,000 across 3 units, that works out to roughly $825,000 per unit.
Annual property taxes are $12,776 (2027), on an assessed value of $730,000.
At $2,475,000 for 5,748 sqft, that's about $431 per square foot.
83-85 Highland Street, Boston MA 02119 is in Boston, Suffolk County, MA 02119.

Justin Rollo is a Broker Associate with Signal Real Estate (MA Lic. #9534264) and a lifelong Massachusetts resident. Over 14 years and hundreds of transactions, he has worked investment properties — multi-families and house-hacking — across Greater Boston full-time. Away from real estate, Justin is a proud dad, youth coach and local school-committee member — and a former professional poker player who still loves golf and following local sports.