$999,900
About this home
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).
Property details
- MLS
- MLS Property Information Network
- MLS #
- 73541288
- Property type
- Single Family Residence
- Subdivision
- N/A
- Status
- Active
- Days on market
- 119
- On market date
- June 24, 2026
- Stories
- N/A
- Total bathrooms
- 2
- Garage spaces
- N/A
- Parking spaces
- 4
- Lot size
- 0.18 acres
Location
Get directions →Nearby schools
Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.
- Enrollment
- 345
- Student:teacher ratio
- 11.9:1
- District
- Winchester
- Enrollment
- 1,059
- Student:teacher ratio
- 11.8:1
- District
- Winchester
- Enrollment
- 1,349
- Student:teacher ratio
- 13.8:1
- District
- Winchester
Walkability
Blended score for Winchester's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).
Market position
How this listing compares to current activity in Winchester, from live MLS data.
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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated August 4, 2026.
Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.