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

258 Cross St

Winchester Highlands - Winchester, MA ID #73575764

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258 Cross St

Winchester Highlands - Winchester, MA ID #73575764

Property Description

A rare opportunity to own a detached home in Winchester under $1M—with the space, privacy and flexibility often missing from condo or townhome living. Tired of or can't imagine paying an HOA fee on top of fighting rising interest rates? Skip the added cost, lock in (REFI LATER) a lower monthly payment, and get more value at 258 Cross Street! The property is set on a level, fenced corner lot with a side-street driveway, ACCESSIBLE FROM RIVER STREET, parking for 4 cars, and offering 3 bedrooms, a versatile bonus room (4 beds on public record), 2.5 baths and a layout that can adapt as your needs change. The main level blends classic character with everyday function, featuring hardwood floors, crown molding, arched openings, bay windows and an updated eat-in kitchen with stone counters, upgraded cabinetry, stainless appliances and gas cooking. A brand-new first-floor powder room adds convenience for everyday living and entertaining. Upstairs, two generously sized bedrooms are joined by two updated full baths, including a larger bath with double vanity, tiled shower and soaking tub. The finished third floor provides a third bedroom plus an additional flex space ideal for a home office, fitness room, playroom, hobby space or guests. Major recent improvements, besides the unused, first floor half bath, include brand-new central AC and a newly sodded yard. Current owners have also invested considerably into improvements from the kitchen (countertops/appliances/backsplash/flooring), to the main bathroom remodel on the 2nd floor, and even a rebuilding of the lower two staircases to increase functionality. Outside, enjoy a fenced backyard, patio, storage shed and rare off-street parking for four vehicles. The full basement provides additional laundry and storage space. Convenient to Winchester Center, local shops and dining, the commuter rail, the Middlesex Fells and major routes connecting Boston, Cambridge, Burlington and the surrounding metro area. Previously prepared conceptual expansion plans are available for buyers interested in exploring future possibilities.

Additional Details

  • Status: Active
  • 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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258 Cross 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 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.