Multi Family at 79 Winthrop Road, Brookline MA 02445, Brookline
Multi Family at 79 Winthrop Road, Brookline MA 02445, Brookline, photo 2 of 10
Multi Family at 79 Winthrop Road, Brookline MA 02445, Brookline, photo 3 of 10
Multi Family at 79 Winthrop Road, Brookline MA 02445, Brookline, photo 4 of 10
Multi Family at 79 Winthrop Road, Brookline MA 02445, Brookline, photo 5 of 10
Multi Family at 79 Winthrop Road, Brookline MA 02445, Brookline, photo 6 of 10
Multi Family at 79 Winthrop Road, Brookline MA 02445, Brookline, photo 7 of 10
Multi Family at 79 Winthrop Road, Brookline MA 02445, Brookline, photo 8 of 10
Multi Family at 79 Winthrop Road, Brookline MA 02445, Brookline, photo 9 of 10
Multi Family at 79 Winthrop Road, Brookline MA 02445, Brookline, photo 10 of 10
10 photos

$2,299,000

79 Winthrop Road, Brookline MA 02445
Brookline, MA 02445
Listed by Collin Bray
Bedrooms
5
Bathrooms
2
Living area
3,161 sqft
Year built
1922

About this home

FIRST TIME in 30+ Years, Washington Square 2-FAMILY, 5,749 SF Gross Square Feet! "Opportunity" to turn this into your future Trophy Brookline Residence. Beautiful hillside VIEWS towards Back Bay & downtown Boston! Unit #2 is a Top Floor 3 Bedroom Duplex & Unit #1 is a large single-level floor through 2 BR+ Office / 1BA. Close to both Driscoll School and Runkle School and only a few blocks to Brookline High School. Top notch Brookline location, walking distance to Washington Square & Brookline Village. Each with bustling Cafes & Restaurants. Walk up the path to Schick Park: Grassy ball field, basketball court & playground.

Highlights

Fireplace

Property details

MLS #
73511051
Property type
Multi Family
Subdivision
N/A
Status
Active
Days on market
156
On market date
May 1, 2026
Stories
4
Total bathrooms
2
Garage spaces
2
Parking spaces
2
Lot size
0.14 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 (e.g. NC Dept. of Public Instruction, SC 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
2.11 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
0.33 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).

82
Highly walkable
out of 100
EPA National Walkability Index
14.0 / 20 -- Above average walkable
Google Places amenity density
100 / 100
Restaurants & cafes20
Grocery stores17
Parks20
Schools20
Transit stops20
Pharmacies14

Market position

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

On the market 156 days -- 57 more days than Brookline's current average of 99 days.
For reference, the median list price across 821 active listings in Brookline right now is $9,500.

Mortgage calculator

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Est. monthly payment
$13,995/mo
$459,800 down
$1,839,200 loan
Principal & interest$11,929
Property tax (est.)$1,916
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated August 9, 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.