Sold Jul 10, 2026$962,500
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Active
258 Cross Street
Winchester, MA 01890
Offered at$999,900
Residential · Active · MLS #73541288
Listing Courtesy of Hartley Realty Group | Justin Blankenship
4Bedrooms
2Bathrooms
1,719Square feet
1860Year built
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MLS PIN data
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 information
Details at a glance
Interior
- Rooms
- 7
- Heating
- Central, Forced Air
- Cooling
- Central Air
- Flooring
- Wood, Tile, Carpet, Hardwood
Building
- Style
- Single Family Residence
- Year built
- 1860
- Parking
- 4
- Foundation
- Stone
- Roof
- Shingle
Land & utilities
- Lot size
- 0.18 acres
- Water
- Public
- Sewer
- Public Sewer
- Zoning
- RG
Financial
- Annual taxes
- $9,592
- Assessment year
- 2026
Listing history
Price and status timeline
No additional public listing history was supplied for this property.
Property value estimate
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Comparable sales
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Condition signals
Overall presentationabove average
Generated from listing photography; not a substitute for an inspection.
Local market context
How this home compares in Winchester
MetricThis propertyWinchester
List price$999,900$1,549,00035% below local
Price / sq ft$582$5653% above local
Days on market715139% above local
Active city listing statistics from MLS PIN as of September 6, 2026. Asking prices are not completed-sale values.
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About 258 Cross Street
Can I schedule a private showing?
Yes. Request a tour of 258 Cross Street and a Bean Group agent will help coordinate an available time with the listing side.
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Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.
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