258 Cross Street

Taxes: $9,591.95 (2026)

About this home

Welcome to 258 Cross Street, a masterfully updated Winchester Colonial blending timeless character, modern comfort, and everyday function. Set on a level, fenced corner lot, this 4 bed, 2 bath home offers endless outdoor opportunity to relax, entertain, play, or dine al fresco. Inside, hardwood floors, crown molding, arched openings, bay windows, and ornate detail bring warmth and personality. The modernized kitchen beams with natural light and features upgraded cabinetry, stone counters, stainless appliances, and gas cooking. Both full baths have been tastefully updated with the larger featuring a tiled stand up shower, free standing soaking tub and a double vanity. Four bedrooms across the upper levels create flexibility for growing families, guests, WFH, fitness, or hobbies. Brand new central AC, central heat, full basement with laundry, and 4-car parking add functionality. Minutes from the iconic, and picturesque downtown Winchester, lined with shops, dining and even a T stop!

Property details

Sewer

Private

Style

Single Wide

Water

City/Town Water

Cooling

Central Air

Heating

Central Heat, Forced Air

Type

Detached

Flooring

Wood, Tile, Wall to Wall Carpet, Hardwood

Road type

Public, Paved, Publicly Maint., Sidewalk

Appliances

Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer

Construction

Aluminum

Roof

Aluminum

Lot

Corner, Fenced/Enclosed, Level

Parking

1-10 Spaces, Deeded, Paved Driveway

Basement

Full, Concrete Floor, Unfinished Basement

Exterior

Patio, Storage Shed, Professional Landscaping, Fenced Yard, Garden Area

Interior

Cable Available, Internet Available - Unknown