A rare opportunity to own a beautifully maintained traditional two-family home on a desirable, tree-lined residential street. Offering exceptional flexibility for multigenerational living, an owner-occupant seeking rental income, or an investment property, this inviting home combines classic character with thoughtful updates. Both spacious apartments feature welcoming entry halls, living rooms with fireplace, sunrooms, elegant dining rooms with double china cabinets, renovated kitchens with granite countertops, tile floors and stainless-steel appliances, two bedrooms, and a full hall bathroom. The second-floor residence offers exciting expansion potential in the walk-up attic. Glowing natural woodwork, hardwood floors and custom cabinetry add warmth and timeless appeal throughout. Outdoor living includes a welcoming front porch, second-floor deck, and patio in a backyard. A spacious basement with extensive storage and laundry, along with a two-car garage and wide driveway, offers exceptional convenience for parking and storage. Ideally located near the Brookline Hills T, Brookline High School, Lincoln School, Brookline Reservoir, parks, cafés, markets, and shops, with easy access to the Longwood Medical Area and Downtown Boston. An active neighborhood association further enhances this vibrant and welcoming community.
| Units | 2 |
| Living area | 2,616 sqft |
| Lot size | 6,743 sqft |
| Year built | 1929 |
| Price / sqft | $745 |
| County | Norfolk |
| MLS # | 73577225 |
| Days on market | 0 days |
| Listed on | September 15, 2026 |
| Annual property tax | $16,750 |
| Tax year | 2027 |
| Assessed value | $1,883,000 |
| Zoning | T-6 |
| Gross income (actual) | $39,000/yr |
| Net operating income (actual) | $24,259/yr |
| Total actual rent | $3,250/mo |
| Electric expense | $3,000/yr |
| Insurance expense | $4,770/yr |
| Stories | 3 |
| Total rooms | 12 |
| Lot size | 0.15 acres |
| Garage spaces | 2 |
| Parking spaces | 5 |
| Parking | Paved Drive, Off Street, Paved |
| Basement | Walk-Out Access, Interior Entry, Concrete |
| Foundation | Granite |
| Roof | Shingle |
| Construction | Frame |
| Flooring | Tile, Hardwood, Stone/Ceramic Tile |
| Heating | Hot Water, Natural Gas, Common |
| Cooling | Window Unit(s) |
| Sewer | Public Sewer |
| Water | Public |
| Utilities | for Gas Range, Washer Hookup |
| Appliances | Washer, Dryer, Range, Dishwasher, Microwave, Refrigerator |
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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 2,616 sqft of living area, built in 1929.
36 Milton Road, Brookline MA 02445 has been listed for 0 days (since September 15, 2026).
At a list price of $1,950,000 across 2 units, that works out to roughly $975,000 per unit.
Annual property taxes are $16,750 (2027), on an assessed value of $1,883,000.
At $1,950,000 for 2,616 sqft, that's about $745 per square foot.
2 garage spaces and 5 total parking spaces (paved drive, off street, paved).
36 Milton Road, Brookline MA 02445 is in Brookline, Norfolk County, MA 02445.

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.