44 Winslow Rd., Brookline, MA 02446

$35,000/mo · For rent

44 Winslow Rd., Brookline

Welcome to the Winslow House in Brookline. A grand co-living space offering 13 bedrooms, 11 bathrooms in total, comprising 9 luxurious suites with private bathrooms and 4 bedrooms sharing 2 common bathrooms. The main level boasts a spacious furnished living room seamlessly connected to a beautifully crafted kitchen and dining area. Featuring custom cabinetry, sleek quartz countertops, stainless steel appliances, dual refrigerators, two stoves, and ample dining space with a breakfast bar and banquet area. Convenient kitchenettes on each floor. Bedrooms are fully furnished with beds, dressers, desks, seating, and TVs. Enjoy the expansive wrap-around porch for alfresco dining and unwinding. Admire the grand staircase adorned with banquet seating. Laundry facilities in the basement. Off-street parking. All utilities and internet included. Property is fully furnished. Situated near Coolidge Corner Brookline, BU and Green Line (B) (C). Whole property leased or individual rooms; Dec/Jan availability.

About this address

44 Winslow Rd. is a 13-bedroom, 11-bath rental in Brookline, MA 02446 with 5,500 square feet, asking $35,000 a month. It has been on our site since October 5, 2026.

The whole property at this address is assessed at $2,817,000 for fiscal year 2027. It last sold for $1,855,800 in June 2022. The assessor lists a lot of 0.17 acres.

It scores 100 out of 100 for walkability, from how close everyday places are.

The closest train or subway stop is Babcock Street (MBTA Green Line B), about 0.1 miles away. The closest bus stop is Commonwealth Ave @ Babcock St (MBTA route 57), about 0.1 miles away.

The closest public schools by level are Florida Ruffin Ridley School (0.4 miles) and Horace Mann School for the Deaf Hard of Hearing (0.8 miles). The district decides which school serves an address.

Listing information from MLS Property Information Network (MLS PIN), MLS #73585655, deemed reliable but not guaranteed. Prices are compared with other homes listed on this site today. Trains and buses come from the transit agencies’ published schedules and schools from the National Center for Education Statistics. Distances are straight-line. Assessed values and past sales are public records from municipal assessors, published by MassGIS. An assessed value is set for taxation and may differ from market value.

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To ask about this home or book a tour, call Benjamin Realty at (617) 734-5050 or email [email protected].