Boston Luxury Condos and Apartments
355 Boylston St / (617) 233-5800

85 High St

Winchester, MA ID #73565817

Property Description

Classic Colonial nestled within one of Winchester’s most desirable neighborhoods, offering timeless architecture, exceptional flexibility, and an enviable setting. The first floor features an updated kitchen with slider to the scenic rear yard and oversized brick patio, casual den, half bath, formal dining room, and gracious living room with fireplace and classic built-ins. Double doors lead to a spectacular all-season porch, perfectly positioned for effortless entertaining indoors or out. The second floor offers four corner bedrooms, including a spacious primary suite with double closets, ensuite bath, and convenient laundry. The walk-up third floor invites endless possibilities with an additional bedroom and abundant closet space. Approximately 500 square feet of finished lower-level flex space provides room for a home gym, teen retreat, playroom, or office. Outside, a private, level yard offers ample space for gardens, play, and entertaining, with a generous brick patio for relaxing and gathering. The two-car heated garage features a full walk-up second floor, ideal for storage or future finishing as a studio, office, or home-away-from-home retreat. Simply a beautiful home in an exceptional location—ready to be loved from day one.

Additional Details

  • Status: ACT
  • Type: Single Family, Single Family Residence
  • Zip Code: 01890
  • Taxes: 15,671
  • Acres: 0.29

Parking

  • Garage: 2
  • Garage Capacity: 2
  • Parking: Detached,Garage Door Opener,Heated Garage,Storage,Off Street,Paved
  • Parking Spaces: 6

Rooms/Dimensions

  • Total Rooms: 12
  • Has Basement: Yes

Location

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85 High St, Winchester, MA

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Content © 2026 MLS Property Information Network, Inc.
The information in this listing was gathered from third party resources including the seller and public records. Listing information provided courtesy of Catherine Albiani of Better Homes and Gardens Real Estate - The Shanahan Group. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations or warranties as to the accuracy of this information.