Location, location, location! Set in one of Swampscott’s most convenient neighborhoods, 37-39 Orchard Circle offers a fantastic opportunity for an owner-occupant, investor, or multi-generational household just moments from the new elementary school, local shops, restaurants, beaches, and everything that makes Swampscott such a desirable place to call home. This well-maintained two-family features two similarly laid-out units, each offering three bedrooms, one full bath, beautiful hardwood floors throughout, and in-unit laundry. The first-floor unit has been freshly painted and is bright, clean, and move-in ready, while the second-floor unit offers additional updates including real wood kitchen cabinetry and a tiled bath. A newer roof and low-maintenance vinyl siding add peace of mind, while the two-car garage provides valuable parking and additional flexibility. With six total bedrooms, separate living spaces, great updates, and an exceptional location close to schools, shopping, beaches, and transportation, this is a rare opportunity to own a turn-key two-family in the heart of Swampscott.
| Units | 2 |
| Living area | 2,936 sqft |
| Lot size | 6,625 sqft |
| Year built | 1920 |
| Price / sqft | $324 |
| County | Essex |
| MLS # | 73595695 |
| Days on market | 0 days |
| Listed on | October 27, 2026 |
| Annual property tax | $10,375 |
| Tax year | 2026 |
| Assessed value | $864,600 |
| Zoning | A-2 |
| Total actual rent | $0/mo |
| Stories | 2 |
| Total rooms | 13 |
| Lot size | 0.15 acres |
| Garage spaces | 2 |
| Parking spaces | 6 |
| Parking | Paved Drive, Off Street |
| Basement | Full, Unfinished |
| Foundation | Stone |
| Construction | Frame |
| Flooring | Hardwood |
| Sewer | Public Sewer |
| Water | Public |
| Appliances | Range, Dishwasher, Refrigerator, Freezer, 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 2,936 sqft of living area, built in 1920.
37-39 Orchard Cir, Swampscott MA 01907 has been listed for 0 days (since October 27, 2026).
At a list price of $950,000 across 2 units, that works out to roughly $475,000 per unit.
Annual property taxes are $10,375 (2026), on an assessed value of $864,600.
At $950,000 for 2,936 sqft, that's about $324 per square foot.
2 garage spaces and 6 total parking spaces (paved drive, off street).
37-39 Orchard Cir, Swampscott MA 01907 is in Swampscott, Essex County, MA 01907.

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.