
185 Warren Street Brookline — Photo 1 of 27
$3,095,000
Investment Analysis — 185 Warren Street
Brookline, MA 02445
Based on HUD Small Area Fair Market Rent for Boston-Cambridge-Quincy, MA-NH HUD Metro FMR Area, a 5-bedroom in 02445 carries an estimated $5,240/mo in gross rent — about a 0.41% cap rate and $12,570/yr in estimated NOI at the $3,095,000 list price. Adjust every assumption in the calculator below.
Beds
5
Baths
3
SqFt
2,834
Style
Single Family
Built
1850
Set on .92AC in Brookline’s Estate area, this 5BD, 3BA home was ahead of its time. Built in 1850 as the carriage barn of the Old Greenhill Estate, it was converted to a single-family and extensively reimagined with open living spaces, expansive glass, and a strong connection to the landscape. 2,834SF home enjoys southwest light throughout, with long sight lines to the outdoors & rooms that feel distinct yet flow naturally together. Oversized windows & glass doors open to backyard. Kitchen connects to the dining area w/ fireplace, while a family room with built-ins & a vaulted living room with 2nd fireplace offer flexible gathering spaces. 2 main-level bedrooms and a full bath add versatility. 2nd floor offers primary suite w/ treetop views and en-suite bath. 2 add’l bedrooms, full bath, and laundry complete 2nd floor. LL w/ mudroom, storage, & access to 2-car garage. Outside, mature trees, open lawns, seasonal gardens, and privacy create a rare setting just minutes from Boston.
ADU Potential
Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 2,834 sq ft principal dwelling). Lot size: 40,000 sq ft.
Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.
Estimates — not financial advice
These figures are illustrative estimates for informational purposes only — not an appraisal, valuation, or guarantee of rent, income, or returns, and not financial, tax, or investment advice. Rent is either the figure reported on the MLS listing — in-place rent that may differ from market and is not verified against the actual leases — or, where the listing reports none, an estimate from HUD Small Area Fair Market Rents, a government benchmark that may differ from actual market rent. Each figure is labelled with its source. Cap rate, NOI, and returns depend on the assumptions shown, which you can change. MLS and other third-party data may be inaccurate or out of date. Verify all figures independently and consult your own financial, tax, and legal advisors before making any investment decision.
Open Houses
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Amenities & Appliances
Gas Water Heater • Range • Dishwasher • Microwave • Refrigerator • Freezer • Washer • Dryer
Neighborhood
Public Transportation • Shopping • Pool • Tennis Court(s) • Park • Walk/Jog Trails
Geography
Floorplan Breakdown
Structural Layout
Living Room
Lvl First15.5 x 15.166666666
Vaulted Ceiling(s), Closet/Cabinets - Custom Built, Exterior Access, Recessed Lighting, Slider
Dining Room
Lvl First18.75 x 12.166666666
Exterior Access, Recessed Lighting
Kitchen
Lvl First12.583333333 x 11.583333333
Exterior Access, Open Floorplan, Recessed Lighting, Stainless Steel Appliances, Gas Stove, Peninsula
Family Room
Lvl First12.583333333 x 11.583333333
Closet/Cabinets - Custom Built, Exterior Access, Recessed Lighting
Primary Bedroom
Lvl Second15.25 x 11.166666666
Bathroom - Full, Walk-In Closet(s)
Bedroom 2
Lvl First12.5 x 11.166666666
Bedroom 3
Lvl First13.666666666 x 11.166666666
Bathroom - Full, Closet, Recessed Lighting
Bedroom 4
Lvl Second15.25 x 12.25
Fireplace
Bedroom 5
Lvl Second11.75 x 11.166666666
Closet, Closet/Cabinets - Custom Built
Bathroom 1
Lvl First8.666666666 x 6.166666666
Bathroom - Full, Bathroom - With Shower Stall
Bathroom 2
Lvl Second9.583333333 x 4.833333333
Bathroom - Full, Bathroom - With Tub & Shower, Skylight
Bathroom 3
Lvl Second7.666666666 x 6.416666666
Bathroom - Full, Bathroom - With Tub & Shower
Property History
$3,095,000
Sep 1, 2026
MLS® 73570606
$3,295,000
Aug 27, 2026
MLS® 73508555
$3,295,000
Apr 28, 2026
MLS® 73508555
Listing Agent: Hilary Maddox Team
Listing Office: Compass
MLS® Number: 73570606
