258 Cross St

Taxes: $9,591.95 (2026)

About this home

Looking for a quiet retreat, with a SIDE STREET DRIVEWAY, built in privacy but still connected to the urban hustle and bustle of Boston metro? A rare Winchester opportunity, has arrived, priced comfortably 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, 2.5 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. Owners JUST put in an unused half bathroom on the first floor PERFECT for entertaining and preserving the privacy of your 2nd floor bathrooms. 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. Minutes from the iconic, and picturesque downtown Winchester where you'll find quaint coffee shops, local boutiques, and even a Commuter rail stop! Quick entry to Boston, Burlington, and the surrounding metro Boston area via nearby I95, Rt2, Rt3. Like spending your free time outdoors? You are mere minutes from the Medford Fells, one of Greater Boston's greenest and most resident friendly (humans and dogs alike) stretches of nature. Smaller upstairs bathroom could be converted to a 1/2 bath with stackable laundry or a dedicated laundry room (SEE ATTACHED RENDERINGS). Some of the previously prepared conceptual expansion plans are in the photos, the rest are available for review upon request.

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