For sale

$5,797,999

84 Winthrop Rd, Brookline, MA 02445

10beds

7,898sqft

Est.:

2 Family - 2 Units Up/Down

Built in 1900

-- sqft lot

$5,536,800 Zestimate^®

$734/sqft

$-- HOA

What's special

Timeless styleSophisticated finishesLuxurious livingSpa-like bathsGrand open layoutsChef-inspired kitchensModern comfort

Welcome to 84 Winthrop Rd—an extraordinary two-family residence in the heart of Brookline, offering nearly 8,000 sq. ft. of luxurious living. With 10 bedrooms and 8 and half bathrooms across two expansive homes, this property is designed for both elegance and functionality. Inside, discover chef-inspired kitchens appointed with premium Miele and Viking appliances, custom cabinetry, and sophisticated finishes that set a new standard for multi-family living. Each residence showcases grand open layouts, spa-like baths, and abundant natural light, blending timeless style with modern comfort. Perfect as a trophy investment or multigenerational living, this rare opportunity combines scale, design, and prestige in one of Brookline’s most coveted locations.

161 days

427

6

Tour with a local agent

Facts & features

Interior

Bedrooms & bathrooms

Bedrooms: 10
Bathrooms: 10
Full bathrooms: 8
1/2 bathrooms: 2

Appliances

Included: Disposal, ENERGY STAR Qualified Refrigerator, Wine Refrigerator, ENERGY STAR Qualified Dryer, ENERGY STAR Qualified Dishwasher, ENERGY STAR Qualified Washer, Range Hood, Range, Microwave, Plumbed For Ice Maker

Features

Mudroom
Flooring: Tile, Hardwood, Stone / Slate, Wood
Basement: Finished,Walk-Out Access,Interior Entry,Garage Access
Number of fireplaces: 2

Interior area

Total structure area: 7,898
Total interior livable area: 7,898 sqft
Finished area above ground: 6,298
Finished area below ground: 1,600

Video & virtual tour

View virtual tour

Property

Parking

Total spaces: 2
Parking features: Paved Drive, Off Street
Garage spaces: 2
Has uncovered spaces: Yes

Features

Exterior features: Balcony, Rain Gutters, Sprinkler System
Fencing: Fenced

Lot

Size: 7,004 Square Feet

Details

Parcel number: B:218 L:0004 S:0000,37284
Zoning: T-6

Construction

Type & style

Home type: MultiFamily
Property subtype: 2 Family - 2 Units Up/Down

Materials

Frame, Brick
Foundation: Stone
Roof: Shingle

Condition

Year built: 1900

Utilities & green energy

Electric: 200+ Amp Service
Sewer: Public Sewer
Water: Public
Utilities for property: for Gas Range, for Gas Oven, Icemaker Connection

Community & HOA

Community

Features: Public Transportation, Shopping, Tennis Court(s), Park, Walk/Jog Trails, Golf, Medical Facility, Laundromat, Bike Path, Highway Access, House of Worship, Private School, Public School, T-Station, University

Location

Region: Brookline

Financial & listing details

Price per square foot: $734/sqft
Tax assessed value: $2,689,900
Annual tax amount: $26,549
Date on market: 11/1/2025
Total actual rent: 0

Estimated market value

$5,536,800

$5.26M - $5.81M

$4,261/mo

Price history

Date	Event	Price
10/2/2025	Listed for sale	$5,797,999+107.1%$734/sqft
Source: MLS PIN #73439005 Report a problem
2/28/2023	Sold	$2,800,000-13.8%$355/sqft
Source: MLS PIN #73072203 Report a problem
1/1/2023	Listing removed	$3,250,000$411/sqft
Source: MLS PIN #72990755 Report a problem
7/20/2022	Price change	$3,250,000-4.4%$411/sqft
Source: MLS PIN #72990755 Report a problem
6/24/2022	Price change	$3,399,000-2.9%$430/sqft
Source: MLS PIN #72990755 Report a problem
6/2/2022	Listed for sale	$3,499,000$443/sqft
Source: MLS PIN #72990755 Report a problem
12/9/2013	Listing removed	$4,600$1/sqft
Source: Penrose Realty Report a problem
8/17/2013	Price change	$4,600-5.2%$1/sqft
Source: Penrose Realty Report a problem
8/10/2013	Price change	$4,850-9.3%$1/sqft
Source: Penrose Realty Report a problem
8/8/2013	Listed for rent	$5,350$1/sqft
Source: Penrose Realty Report a problem

Public tax history

Year	Property taxes	Tax assessment
2025	$26,549 +0.6%	$2,689,900 -0.4%
2024	$26,382 -13.4%	$2,700,300 -11.7%
2023	$30,481 +2.7%	$3,057,300 +5%
2022	$29,670 +8.1%	$2,911,700 +4%
2021	$27,437 +4.4%	$2,799,700 +0.7%
2020	$26,271 +5.9%	$2,780,000 +5%
2019	$24,808 +10.1%	$2,647,600 +11.2%
2018	$22,530 +3.4%	$2,381,600 +8%
2017	$21,787 +4.3%	$2,205,200 +10%
2016	$20,890 +11%	$2,004,800 +13.7%
2015	$18,828 +3.2%	$1,762,900 +10.1%
2014	$18,239 +2.7%	$1,601,300 +5%
2013	$17,766 +2.2%	$1,525,000
2012	$17,385 +4.4%	$1,525,000 +3.5%
2011	$16,657 +3%	$1,474,100
2010	$16,171 +2.6%	$1,474,100 0%
2009	$15,759 +10.2%	$1,474,200 +5%
2008	$14,294 +2.8%	$1,404,100 -1.7%
2007	$13,900 +1.6%	$1,428,600 -0.3%
2006	$13,687 0%	$1,433,200 +7.1%
2005	$13,688 +9%	$1,338,000 +13.2%
2004	$12,561 +4.3%	$1,181,700 +10%
2003	$12,043 +10.3%	$1,074,300 +26.9%
2002	$10,920 +12.5%	$846,500 +47.4%
1999	$9,710	$574,200