2 Family - 2 Units Up/Down at 84 Winthrop Rd, Brookline MA 02445
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$5,797,999

84 Winthrop Rd, Brookline MA 02445
Brookline, MA 02445
Listed by Jorge Sariego
Bedrooms
10
Bathrooms
9
Living area
7,898 sqft
Year built
1900

About this home

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.

Highlights

Fireplace

Property details

MLS
MLS Property Information Network
MLS #
73439005
Property type
2 Family - 2 Units Up/Down
Subdivision
N/A
Status
Active
Days on market
386
On market date
October 2, 2025
Stories
4
Total bathrooms
9
Garage spaces
2
Parking spaces
2
Lot size
0.16 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
Michael Driscoll
0.35 mi away · Grades 0-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
454
Student:teacher ratio
11.1:1
District
Brookline
Middle
James P Timilty Middle
2.12 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
205
Student:teacher ratio
8.2:1
District
Boston
High
Brookline High
0.32 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
2,087
Student:teacher ratio
10.9:1
District
Brookline

Walkability

Blended score for Brookline's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

85
Highly walkable
out of 100
EPA National Walkability Index
15.0 / 20 -- Above average walkable
Google Places amenity density
100 / 100
Restaurants & cafes20
Grocery stores16
Parks20
Schools20
Transit stops20
Pharmacies13

Market position

How this listing compares to current activity in Brookline, from live MLS data.

On the market 386 days -- 279 more days than Brookline's current average of 107 days.
For reference, the median list price across 885 active listings in Brookline right now is $9,000.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

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Est. monthly payment
$35,066/mo
$1,159,600 down
$4,638,399 loan
Principal & interest$30,085
Property tax (est.)$4,832
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated February 8, 2026.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.