**Stunning Oversized Two-Family in Prime Roslindale Location!** Take a journey through this exceptional home to experience space, character, flexibility, and all the amenities you've been looking for. The spacious upper unit spans two level- the second floor features a bright living room, dining room with decorative beams with fireplace, eat-in kitchen with island and pantry area, large rear deck, and a dedicated home office with private front deck. Two bedrooms and a full bath complete this level. Then then third floor offers a spa-like bath, additional family room/living area (or 5th bedroom), and two large bedrooms with vaulted ceilings. A dedicated laundry room plus two heat/cool zones add comfort and convenience. The first-floor unit, currently rented, offers a welcoming foyer, living room, dining room with fireplace, eat-in kitchen with laundry in the pantry, two bedrooms, and a full bath. Also has direct access out to back deck and great backyard. The basement provides abundant storage, and direct walk-out access to the yard. The driveway accommodates 4+ cars, plus a small garage. This home is once-in-a-lifetime opportunity to mix home ownership with the investment quality of multi-family.
| Units | 2 |
| Living area | 3,669 sqft |
| Lot size | 6,000 sqft |
| Year built | 1925 |
| Price / sqft | $351 |
| County | Suffolk |
| MLS # | 73567199 |
| Days on market | 0 days |
| Listed on | August 24, 2026 |
| Annual property tax | $14,169 |
| Tax year | 2025 |
| Assessed value | $1,223,600 |
| Zoning | R2 |
| Gross income (actual) | $100,800/yr |
| Net operating income (actual) | $100,800/yr |
| Total actual rent | $8,400/mo |
| Stories | 3 |
| Total rooms | 15 |
| Lot size | 0.14 acres |
| Garage spaces | 1 |
| Parking spaces | 5 |
| Parking | Paved Drive, Off Street |
| Basement | Full |
| Foundation | Stone |
| Roof | Shingle |
| Construction | Frame |
| Flooring | Hardwood |
| Heating | Natural Gas, Central |
| Cooling | Central Air |
| Sewer | Public Sewer |
| Water | Public |
| Appliances | Range, Dishwasher, Refrigerator, Freezer, Washer, Dryer, Microwave |
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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 3,669 sqft of living area, built in 1925.
39 Ainsworth St, Boston MA 02131 has been listed for 0 days (since August 24, 2026).
At a list price of $1,286,500 across 2 units, that works out to roughly $643,250 per unit.
Annual property taxes are $14,169 (2025), on an assessed value of $1,223,600.
At $1,286,500 for 3,669 sqft, that's about $351 per square foot.
1 garage space and 5 total parking spaces (paved drive, off street).
39 Ainsworth St, Boston MA 02131 is in Boston, Suffolk County, MA 02131.

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.