Exceptional Multi-Generational Opportunity! Discover the remarkable flexibility of the historic Bartlett House at 8 Leonard Circle. A legal two-family currently enjoyed as a spacious single-family home, this distinctive Federal/Greek Revival residence offers the space and separation to bring generations together while still providing privacy and room to spread out. With kitchens and living spaces on both levels, the home lends itself beautifully to extended family, guests, work-from-home needs or separate living areas. The expansive first floor features a gracious living room, dining room, kitchen with eat-in area/family-room, den/bedroom and full bath. Upstairs are additional bedrooms, an office, family room, baths, kitchen and dining area. Two staircases further enhance the versatility of this unique layout. Dating to approximately 1820–1830, the home is filled with character rarely found today. Step from the inviting three-sided wraparound porch into generously proportioned rooms featuring stunning hardwood floors with intricate inlaid designs, stained-glass windows, antique lighting, a built-in hutch and four fireplaces. Period details and craftsmanship create warmth and personality throughout. An unfinished third-floor walk-up attic featuring a distinctive turret adds another layer of character and offers exciting possibilities for future use. Whether you envision generations living together, separate spaces under one roof, or simply want the freedom that comes with an exceptionally flexible floor plan, 8 Leonard Circle offers a rare opportunity to create a home that evolves with you. Rich in history, character and possibility, come discover all that this one-of-a-kind Medford home has to offer.
| Units | 2 |
| Living area | 3,116 sqft |
| Lot size | 9,212 sqft |
| Year built | 1820 |
| Price / sqft | $394 |
| County | Middlesex |
| MLS # | 73573418 |
| Days on market | 22 days |
| Listed on | September 8, 2026 |
| Annual property tax | $11,796 |
| Tax year | 2026 |
| Assessed value | $1,366,900 |
| Zoning | SF2 |
| Total actual rent | $0/mo |
| Stories | 2 |
| Total rooms | 12 |
| Lot size | 0.21 acres |
| Garage spaces | 0 |
| Parking spaces | 3 |
| Parking | Paved Drive, Off Street |
| Basement | Full, Interior Entry, Bulkhead |
| Foundation | Stone, Granite |
| Roof | Shingle |
| Flooring | Tile, Hardwood |
| Heating | Hot Water, Steam, Natural Gas |
| Sewer | Public Sewer |
| Water | Public |
| Utilities | for Gas Range, for Electric Range, for Gas Dryer, Washer Hookup, Varies per Unit |
| Appliances | Range, Dishwasher, 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 2-unit multi-family property with 3,116 sqft of living area, built in 1820.
8 Leonard Cir, Medford MA 02155 has been listed for 22 days (since September 8, 2026).
At a list price of $1,229,000 across 2 units, that works out to roughly $614,500 per unit.
Annual property taxes are $11,796 (2026), on an assessed value of $1,366,900.
At $1,229,000 for 3,116 sqft, that's about $394 per square foot.
3 total parking spaces (paved drive, off street).
8 Leonard Cir, 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.