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355 Boylston St / (617) 233-5800

258 Cross Street

Winchester Highlands - Winchester, MA ID #73541288

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258 Cross Street

Winchester Highlands - Winchester, MA ID #73541288

Property Description

A rare Winchester opportunity under $1M, 258 Cross Street blends timeless character, meaningful updates, everyday function, and exciting long-term upside. Set on a level, fenced corner lot, this 4 bed, 2 bath Colonial offers the space buyers need today with the flexibility to evolve over time. Inside - hardwood floors, crown molding, arched openings, bay windows, and detailed trim add warmth, while the updated kitchen features stone counters, upgraded cabinetry, stainless appliances, gas cooking, and great natural light. Both full baths have been tastefully updated, including a larger bath with double vanity, tiled shower, and soaking tub. Four bedrooms on the upper levels create options for guests, office, fitness, hobbies, or future needs. Brand new AC, central heat, full basement with laundry/storage, patio, fenced yard, shed, and 4-car parking add real utility. Previously prepared conceptual expansion plans are available for review. Minutes from the iconic, and picturesque downtown. Rear vestibule is the perfect place for a 1st floor half bath (see attached rendering). Smaller upstairs bathroom could be converted to a 1/2 bath with stackable laundry or a dedicated laundry room (SEE ATTACHED RENDERINGS).

Additional Details

  • Status: ACT
  • Type: Single Family, Single Family Residence
  • Area: Winchester Highlands
  • Zip Code: 01890
  • Taxes: 9,592
  • Acres: 0.18

Parking

  • Garage Capacity: 4
  • Parking: Off Street,Deeded,Paved
  • Parking Spaces: 4

Rooms/Dimensions

  • Total Rooms: 7
  • Has Basement: Yes

Location

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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 Justin Blankenship of Fiv Realty Co. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations or warranties as to the accuracy of this information.