Meticulously maintained Medford 2-family with lots of updates by the current owner that still offers an opportunity for upside improvements. Both units have had regular updates, including recently refinished hardwood floors, regular paint updates, and updated kitchens and baths. Both units are currently rented under leases, making it a great investment property with an opportunity for future owner-occupancy. The walk-up heated attic provides a great opportunity for expanding the 2nd-floor unit. Electric was updated to 200amp, boilers were done in the early 2000s, and water heaters were recently replaced. The roof was done in 2008. Full basement waterproofing just completed. Mini splits were added to unit 2 in 2020, and 1st floor windows have just been updated.
| Units | 2 |
| Living area | 2,630 sqft |
| Lot size | 4,050 sqft |
| Year built | 1920 |
| Price / sqft | $456 |
| County | Middlesex |
| MLS # | 73536452 |
| Days on market | 44 days |
| Listed on | June 16, 2026 |
| Annual property tax | $9,173 |
| Tax year | 2026 |
| Assessed value | $1,062,900 |
| Zoning | GR |
| Gross income (actual) | $67,200/yr |
| Net operating income (actual) | $67,200/yr |
| Total actual rent | $5,600/mo |
| Stories | 3 |
| Total rooms | 14 |
| Lot size | 0.09 acres |
| Garage spaces | 0 |
| Parking spaces | 2 |
| Parking | Paved Drive, Off Street, Tandem |
| Basement | Full, Walk-Out Access |
| Foundation | Block, Stone |
| Roof | Shingle |
| Construction | Frame |
| Flooring | Wood, Tile |
| Sewer | Public Sewer |
| Water | Public |
| Appliances | Range, Dishwasher, Microwave, Refrigerator |
More about investing in Medford →
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 2-unit multi-family property with 2,630 sqft of living area, built in 1920.
38-40 Cherry St, Medford MA 02155 has been listed for 44 days (since June 16, 2026).
At a list price of $1,200,000 across 2 units, that works out to roughly $600,000 per unit.
Annual property taxes are $9,173 (2026), on an assessed value of $1,062,900.
At $1,200,000 for 2,630 sqft, that's about $456 per square foot.
2 total parking spaces (paved drive, off street, tandem).
38-40 Cherry St, Medford MA 02155 is in Medford, Middlesex County, MA 02155.

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.