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.
For sale
Price cut: $200K (6/2)
$3,295,000
185 Warren St, Brookline, MA 02445
5beds
2,834sqft
Single Family Residence
Built in 1850
0.92 Acres Lot
$3,162,600 Zestimate®
$1,163/sqft
$-- HOA
What's special
Family room with built-insMature treesSeasonal gardensOpen lawnsSouthwest light throughoutExpansive glassOpen living spaces
- 58 days |
- 703 |
- 25 |
Zillow last checked:
Listing updated:
Listed by:
Hilary Maddox Team 617-921-2097,
Compass 617-752-6845
Source: MLS PIN,MLS#: 73508555
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 3
- Full bathrooms: 3
Primary bedroom
- Features: Bathroom - Full, Walk-In Closet(s)
- Level: Second
- Area: 170.29
- Dimensions: 15.25 x 11.17
Bedroom 2
- Features: Bathroom - Full, Closet, Recessed Lighting
- Level: First
- Area: 139.58
- Dimensions: 12.5 x 11.17
Bedroom 3
- Features: Bathroom - Full, Closet, Recessed Lighting
- Level: First
- Area: 152.61
- Dimensions: 13.67 x 11.17
Bedroom 4
- Features: Fireplace
- Level: Second
- Area: 186.81
- Dimensions: 15.25 x 12.25
Bedroom 5
- Features: Closet, Closet/Cabinets - Custom Built
- Level: Second
- Area: 131.21
- Dimensions: 11.75 x 11.17
Primary bathroom
- Features: Yes
Bathroom 1
- Features: Bathroom - Full, Bathroom - With Shower Stall
- Level: First
- Area: 53.44
- Dimensions: 8.67 x 6.17
Bathroom 2
- Features: Bathroom - Full, Bathroom - With Tub & Shower, Skylight
- Level: Second
- Area: 46.32
- Dimensions: 9.58 x 4.83
Bathroom 3
- Features: Bathroom - Full, Bathroom - With Tub & Shower
- Level: Second
- Area: 49.19
- Dimensions: 7.67 x 6.42
Dining room
- Features: Exterior Access, Recessed Lighting
- Level: First
- Area: 228.13
- Dimensions: 18.75 x 12.17
Family room
- Features: Closet/Cabinets - Custom Built, Exterior Access, Recessed Lighting
- Level: First
- Area: 145.76
- Dimensions: 12.58 x 11.58
Kitchen
- Features: Exterior Access, Open Floorplan, Recessed Lighting, Stainless Steel Appliances, Gas Stove, Peninsula
- Level: First
- Area: 145.76
- Dimensions: 12.58 x 11.58
Living room
- Features: Vaulted Ceiling(s), Closet/Cabinets - Custom Built, Exterior Access, Recessed Lighting, Slider
- Level: First
- Area: 235.08
- Dimensions: 15.5 x 15.17
Heating
- Forced Air, Electric Baseboard, Natural Gas
Cooling
- Central Air
Appliances
- Included: Gas Water Heater, Range, Dishwasher, Microwave, Refrigerator, Freezer, Washer, Dryer
- Laundry: Second Floor
Features
- Mud Room, Wet Bar
- Basement: Full,Partially Finished,Walk-Out Access,Interior Entry,Garage Access
- Number of fireplaces: 3
- Fireplace features: Dining Room
Interior area
- Total structure area: 2,834
- Total interior livable area: 2,834 sqft
- Finished area above ground: 2,834
Video & virtual tour
Property
Parking
- Total spaces: 8
- Parking features: Attached, Under, Storage, Garage Faces Side, Off Street
- Attached garage spaces: 2
- Uncovered spaces: 6
Features
- Patio & porch: Patio
- Exterior features: Patio, Rain Gutters, Fenced Yard, Garden
- Fencing: Fenced/Enclosed,Fenced
- Has view: Yes
- View description: City View(s)
Lot
- Size: 0.92 Acres
- Features: Wooded
Details
- Parcel number: 41445
- Zoning: S-40
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Contemporary
- Property subtype: Single Family Residence
Materials
- Foundation: Concrete Perimeter
- Roof: Shingle
Condition
- Year built: 1850
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: for Gas Range
Community & HOA
Community
- Features: Public Transportation, Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Golf, Medical Facility, Laundromat, Bike Path, Conservation Area, Highway Access, House of Worship, Private School, Public School, T-Station, University
- Security: Security System
HOA
- Has HOA: No
Location
- Region: Brookline
Financial & listing details
- Price per square foot: $1,163/sqft
- Tax assessed value: $3,760,300
- Annual tax amount: $35,219
- Date on market: 4/28/2026
Estimated market value
$3,162,600
$3.00M - $3.32M
$7,133/mo
Price history
| Date | Event | Price |
|---|---|---|
| 6/2/2026 | Price change | $3,295,000-5.7%$1,163/sqft |
Source: MLS PIN #73508555 Report a problem | ||
| 4/28/2026 | Listed for sale | $3,495,000$1,233/sqft |
Source: MLS PIN #73508555 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $34,582 +5.2% | $3,503,700 +4.2% |
| 2024 | $32,863 +13.2% | $3,363,700 +15.5% |
| 2023 | $29,032 +2.7% | $2,911,900 +5% |
| 2022 | $28,259 +8.1% | $2,773,200 +4% |
| 2021 | $26,133 +12.4% | $2,666,600 +8.4% |
| 2020 | $23,241 +6.2% | $2,459,400 +5.3% |
| 2019 | $21,885 +4.8% | $2,335,600 +5.8% |
| 2018 | $20,886 +1.5% | $2,207,800 +6% |
| 2017 | $20,577 +1.5% | $2,082,700 +7% |
| 2016 | $20,281 +4.4% | $1,946,400 +7% |
| 2015 | $19,428 +3.2% | $1,819,100 +10.1% |
| 2014 | $18,817 +0.7% | $1,652,100 +3% |
| 2013 | $18,687 +2.2% | $1,604,000 |
| 2012 | $18,286 +4.7% | $1,604,000 +3.8% |
| 2011 | $17,460 +2.8% | $1,545,100 -0.2% |
| 2010 | $16,990 +2.6% | $1,548,800 |
| 2009 | $16,557 +6.1% | $1,548,800 +1.1% |
| 2008 | $15,600 +0.4% | $1,532,400 -4% |
| 2007 | $15,531 +1.9% | $1,596,200 0% |
| 2006 | $15,245 -1.6% | $1,596,300 +5.4% |
| 2005 | $15,498 +3% | $1,515,000 +7% |
| 2004 | $15,051 +4.3% | $1,415,900 +10% |
| 2003 | $14,430 +4.9% | $1,287,200 +20.7% |
| 2002 | $13,754 -4.5% | $1,066,200 +25.2% |
| 1999 | $14,406 | $851,900 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
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HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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Climate risks
Neighborhood: 02445
Nearby schools
GreatSchools rating
- 9/10William H Lincoln SchoolGrades: K-8Distance: 0.4 mi
- 8/10Brookline High SchoolGrades: 9-12Distance: 0.8 mi
- 8/10Roland Hayes SchoolGrades: PK-8Distance: 0.9 mi
Schools provided by the listing agent
- Elementary: Hayes/Lincoln
- Middle: Hayes/Lincoln
- High: Brookline High
Source: MLS PIN. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
A local agent can set up tours, give advice and negotiate with sellers.
A local lender can help you make sure your offer is ready when you are.
- Massachusetts
- Norfolk County
- Brookline
- 02445
- 185 Warren St
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