258 Cross Street
$999,900
4
Beds
2
Baths
1,719
Sqft
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$999,900
4
Beds
2
Baths
1,719
Living Area
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Property Description
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).
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Highlights
- Area: Winchester Highlands
- Heating: Central, Forced Air
- Property Class: Residential
- Style: Colonial
- Year Built: 1860
- Cooling: Central Air
- Parking Spots: 4
- Property Type: Single Family Residence
- Total Rooms: 7
- Status: Active
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Additional Details
- Appliances: Gas Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer
- Construction: Frame
- Flooring: Wood, Tile, Carpet, Hardwood
- Interior Features: Internet Available - Unknown
- Road Frontage Type: Public
- SqFt Source: Public Record
- Year Built Source: Public Records
- Basement: Full, Concrete, Unfinished
- Exterior Features: Patio, Storage, Professional Landscaping, Fenced Yard, Garden
- Foundation: Stone
- Lot Features: Corner Lot, Level
- Roof: Shingle
- Year Built Details: Approximate
- Zoning: Rg
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Amenities
- Community Features: 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
- Parking Features: Off Street, Deeded, Paved
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Utilities
- Sewer: Public Sewer
- Water Source: Public
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Fees / Taxes
- Assessed Value: $865,700
- Taxes: $9,591
- Tax Year: 2026
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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 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.