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185 Warren Street Brookline — Photo 1 of 27

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.

View Standard Listing

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

Original Price$3,095,000
Annual Taxes$35,219

Parking

Garage2
Off-Street8

Interior Specifications

Total Rooms9
Fireplaces3
Flooring--
BasementFull, Partially Finished, Walk-Out Access, Interior Entry, Garage Access

Climate & Utilities

HeatingForced Air, Electric Baseboard, Natural Gas
CoolingCentral Air
WaterPublic
SewerPublic Sewer

Building & Exterior

Construction--
RoofShingle
FoundationConcrete Perimeter
ZoningS-40

Property & Lot

Acres0.92
SqFt Lot40,000
Lot FeaturesWooded

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

Second
Primary BedroomBedroom 4Bedroom 5Bathroom 2Bathroom 3
First
Living RoomDining RoomKitchenFamily RoomBedroom 2Bedroom 3Bathroom 1
Living Room
Lvl First

15.5 x 15.166666666

Vaulted Ceiling(s), Closet/Cabinets - Custom Built, Exterior Access, Recessed Lighting, Slider

Dining Room
Lvl First

18.75 x 12.166666666

Exterior Access, Recessed Lighting

Kitchen
Lvl First

12.583333333 x 11.583333333

Exterior Access, Open Floorplan, Recessed Lighting, Stainless Steel Appliances, Gas Stove, Peninsula

Family Room
Lvl First

12.583333333 x 11.583333333

Closet/Cabinets - Custom Built, Exterior Access, Recessed Lighting

Primary Bedroom
Lvl Second

15.25 x 11.166666666

Bathroom - Full, Walk-In Closet(s)

Bedroom 2
Lvl First

12.5 x 11.166666666

Bedroom 3
Lvl First

13.666666666 x 11.166666666

Bathroom - Full, Closet, Recessed Lighting

Bedroom 4
Lvl Second

15.25 x 12.25

Fireplace

Bedroom 5
Lvl Second

11.75 x 11.166666666

Closet, Closet/Cabinets - Custom Built

Bathroom 1
Lvl First

8.666666666 x 6.166666666

Bathroom - Full, Bathroom - With Shower Stall

Bathroom 2
Lvl Second

9.583333333 x 4.833333333

Bathroom - Full, Bathroom - With Tub & Shower, Skylight

Bathroom 3
Lvl Second

7.666666666 x 6.416666666

Bathroom - Full, Bathroom - With Tub & Shower

Property History

Listed
$3,095,000

Sep 1, 2026

MLS® 73570606

Terminated
$3,295,000

Aug 27, 2026

MLS® 73508555

Listed
$3,295,000

Apr 28, 2026

MLS® 73508555

Listing Provided By

Listing Agent: Hilary Maddox Team

Listing Office: Compass

MLS® Number: 73570606