Property Details
Basic Information
- Property SubType: Single Family Residence
- Property Style: Colonial
- MLS Number: 73541288
- Mls Status: New
- List Price: $999,900
- Date Listed: 06/24/2026
- Virtual Tour: Virtual Tour
- Description: 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 downtown Winchester with the most scenic downtown around, lined with shops, dining and even the T
Building
- Acreage: 0.18
- Square Feet: 1,719
- Year Built: 1860
- Zoning: RG
- Rooms: 7
- Roof: Shingle
- Foundation: Stone
Location
- County: Middlesex
- Neighborhood: Winchester Highlands
- Subdivision: Winchester Highlands
- Town: Winchester
Finance
- Taxes: $9,591
Interior Features
Bedrooms
- Bedrooms: 4
- Bedroom 2: Second,13.25 x 12.166666666
Bathrooms
- Bathrooms: 2
- Full Baths: 2
Basement
- Basement: Full, Concrete, Unfinished
Utilities and Appliances
Utilities and Appliances
- Appliances Included: Gas Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer
Community
Schools
- Elementary School: Lynch Elementary School
Amenities
- Amenities: Public Transportation, Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Stable(s), Golf, Medical Facility, Bike Path, Conservation Area, Highway Access, House of Worship, Private School, Public School, T-Station, University, Sidewalks
- Other Amenities: Basement, Garden, Golf, Tennis