22 Windsor Rd.
22 Windsor Rd.
22 Windsor Rd.
22 Windsor Rd.
22 Windsor Rd.
22 Windsor Rd.
22 Windsor Rd.
22 Windsor Rd.
22 Windsor Rd.
22 Windsor Rd.
22 Windsor Rd.
22 Windsor Rd.
22 Windsor Rd.
22 Windsor Rd.
SEE ALL PHOTOS
22 Windsor Rd.
22 Windsor Rd.
22 Windsor Rd.
22 Windsor Rd.
22 Windsor Rd.
22 Windsor Rd.
22 Windsor Rd.
22 Windsor Rd.
22 Windsor Rd.
22 Windsor Rd.
22 Windsor Rd.
22 Windsor Rd.
22 Windsor Rd.
22 Windsor Rd.
For Sale

22 Windsor Rd.

22 Windsor Rd., Brookline, MA 02445

$2,350,018
Built in 1910, this classic Colonial offers timeless character and strong potential in a highly desirable neighborhood. Rich original woodwork, hardwood floors, and a striking wooden stairwell showcase the home's historic charm, while the spacious layout provides a solid foundation for renovation. The home features 5 bedrooms and 3.5 baths across three levels, with 2,845 square feet of interior living space plus an unfinished basement and part of the attic with high ceilings, both which are ideal for expansion. A flexible floor plan includes a private bedroom off the kitchen with its own bath, perfect for guests, an au pair, or in-law suite. A sunroom, backyard, three fireplaces, and ample parking enhance the property. Walk to restaurants, shops, grocery stores and the T. This home has great bones and significant renovation potential. The property is sold as is. Open houses Saturday 3/7 & Sunday 3/8 from 12-2PM. Listings begins immediately. Offers due Tuesday March 10th by noon.

3/3/2026 12:00PM - 1:00PM EST

3/7/2026 12:00PM - 2:00PM EST

3/8/2026 12:00PM - 2:00PM EDT

5
beds

4
baths

2,845 Sq.Ft. LIVING AREA

8,499 Sq.Ft. lot

Eric Glassoff

Eric Glassoff

Features & Amenities

Interior

  • total bedrooms5
  • Total bathrooms4
  • full bathrooms3
  • half bathroom1
  • Flooring Hardwood
  • other interior Features Bathroom

Area & Lot

  • Status For Sale
  • OPEN HOUSE

    3/3/2026 12:00PM - 1:00PM EST

    3/7/2026 12:00PM - 2:00PM EST

    3/8/2026 12:00PM - 2:00PM EDT

  • Living Area2,845 Sq.Ft.
  • Total Area2,845 Sq.Ft.
  • Lot Area8,499 Sq.Ft.
  • MLS® ID73481267
  • TypeResidential
  • YEAR BUILT1910
  • NeighborhoodBrookline
  • Architecture StylesColonial
  • Elementary SchoolDriscoll/Runkle (K-8)
  • Middle SchoolDriscoll/Runkle (K-8)
  • High SchoolBrookline High School

Exterior

  • water SourcePublic
  • roofSlate
  • lot featuresLevel
  • parkingOff Street
  • HEAT TYPEBaseboard, Oil
  • AIR CONDITIONINGNone
  • sewerPublic Sewer
  • SubstructureOther
  • other exterior FeaturesPorch - Enclosed

Financial

  • Sales Price$2,350,018
  • Real Estate Tax $19,515/yr
  • Zoning S-7
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Schedule a Showing

I would love to show you my beautiful property. Please select your preferred date and time below. I will be in touch shortly to confirm your appointment.

Thank you for your interest in 22 Windsor Rd., Brookline, MA 02445. We are reviewing your request and will be in touch shortly!

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Work With Eric

Eric’s knowledge of the area and its many unique neighborhoods is a distinct advantage to buyers, whether they’re looking for a condo or a luxury home. Having been a Mortgage Broker, Eric also has vast knowledge of securing and recommending favorable financing. After obtaining an MBA from Babson College and a Dale Carnegie sales degree, Eric has accomplished 21 years of highly successful real estate results and has a sterling reputation in the community, guiding his clients through the real estate buying and selling process seamlessly.

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