
36 Milton Road Brookline — Photo 1 of 31
$1,950,000
36 Milton Road, Brookline, MA 02445
Brookline, MA 02445
Beds
4
Baths
2
SqFt
2,616
Style
2 Family - 2 Units Up/Down
Built
1929
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.
Open Houses
Market Value Analysis
* Analysis is based on 24 actively listed and recently sold comparable properties strictly within Brookline, MA.
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Amenities & Appliances
Washer • Dryer • Range • Dishwasher • Microwave • Refrigerator
Neighborhood
Public Transportation • Shopping • Pool • Park • Walk/Jog Trails • Medical Facility
Geography
Population
22,560
U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)
Median Household Income
$140K
U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)
Renter-Occupied Homes
47.9%
U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)
New Construction Permits — Norfolk County
1,524 housing units permitted in the last 12 months (+52% vs the prior 12 months) — 1,030 in 5+ unit buildings
U.S. Census Bureau, Building Permits Survey (through Jul '26)
Listing Agent: Susan And Jen Rothstein Team
Listing Office: Hammond Residential Real Estate
MLS® Number: 73577225
Open Houses
Related Insights

Brookline First-Time Buyer Grant Stacking Guide

Brookline Down Payment Grants in the August Market

Brookline Buyers: MassHousing Limit Hits $205,335

Brookline Property Taxes After the 2026 Override

Brookline Sellers: The Pricing Trap to Avoid

Brookline’s Price-Per-Square-Foot Mirage Explained

Brookline’s Two-Speed Market: Why May’s Price Surge Signals a Structural Shift

Massachusetts Down Payment Help: Your August Plan
Browse More Homes in Brookline
Explore other active listings in the area.
$2,195,0003 High Street PlBrookline, MA6 bd3 ba2,819 sqft
$4,650,000129 Rangeley RdBrookline, MA6 bd7 ba6,359 sqft
$1,790,00075 Hammond Pond ParkwayBrookline, MA4 bd3 ba2,274 sqft
$4,950,000220 Aspinwall AveBrookline, MA6 bd6 ba5,487 sqft
$23,000,000381 Warren StreetBrookline, MA7 bd12 ba16,856 sqft
$1,295,000428 Boylston StBrookline, MA3 bd2 ba1,748 sqft