**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. ** Offers due Monday, August 31 by 6pm** Multiple offer situation.
| Units | 2 |
| Living area | 3,669 sqft |
| Lot size | 6,000 sqft |
| Year built | 1925 |
| Price / sqft | $373 |
| County | Suffolk |
| MLS # | 73567199 |
| Days on market | 6 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 sold after about 53 days on the market (listed August 24, 2026, closed October 16, 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 $373 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.