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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
More Info
Basic Information
- Bedrooms4
- Mls StatusActive
- Bathroom2
- Listing Terms Contract
- Lot Features Corner Lot, Level
- Parcel Number 898140
- Road Frontage DescriptionPaved
Tax Information
- Tax Assessed Value $865,700
- Tax Year 2026
- Taxes$9,591
School Information
- High School Winchester High School
- Elementary SchoolLynch Elementary School
- Junior HighMccall Middle School
Parking
- Parking Spaces4
- Open Parking YN Yes
- Parking Features Off Street, Deeded, Paved
Rooms
- Bathroom 1 Second,9.083333333 x 8.833333333
- Bathroom 2 Second,6.75 x 4.5
- Bathrooms Total Decimal 2
- Bedroom 2 Second,13.25 x 12.166666666
- Bedroom 3 Third,11.75 x 12.75
- Bedroom 4 Third,11.75 x 12.25
- Dining Room Main, First,12.833333333 x 14.416666666
- Full Bath2
- Kitchen Main, First,13 x 15.833333333
- Living Room Main, First,13.333333333 x 17.916666666
- Master Bedroom Second,17.25
Basic Information
- List Price$999,900
- MLS Number73541288
- Modification Date07/08/2026
- Property SubTypeSingle Family Residence
- Virtual TourView Tour
Location
- NeighborhoodWinchester Highlands
- SubdivisionWinchester Highlands
- Address258 Cross Street
- Building Number258
- CountyMiddlesex
- StateMA
- StreetCross Street
- TownWinchester
- Zip01890
Building
- BasementFull, Concrete, Unfinished
- Building Area Units Square Feet
- Construction Materials Frame
- FoundationStone
- Patio And Porch Features Patio
- Property StyleColonial
- Rooms7
- Utilities For Gas Range
- Year Built1860
- Year Built Details Approximate
- Year Built Source Public Records
Property
- Acreage0.18
Interior
- Flooring Wood, Tile, Carpet, Hardwood
- Interior Features Internet Available - Unknown
Exterior
- Exterior Features Patio, Storage, Professional Landscaping, Fenced Yard, Garden
- Fencing Fenced/Enclosed, Fenced
- RoofShingle
Utilities
- Cooling Central Air
- Cooling YN Yes
- Heat SystemYes
- Heating Central, Forced Air
- Sewer Public Sewer
- Water Source Public
Property Information
- Square Feet1,719
- Building Area Source Public Records
- Living Area 1,719
- Lot Size Square Feet 7,700
- Lot Size Units Acres
- Road Responsibility Public Maintained Road
Amenities
- Amenities
- Bike Path
- Conservation Area
- Golf
- Highway Access
- House of Worship
- Medical Facility
- Park
- Pool
- Private School
- Public School
- Public Transportation
- Shopping
- Sidewalks
- Stable(s)
- T-Station
- Tennis Court(s)
- University
- Walk/Jog Trails
- Appliances IncludedGas Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer
Legal
- ZoningRG
Other
- Date Listed06/24/2026
- Farm Land Area Units Square Feet
Map Location
Listed by Justin Blankenship of Fiv Realty Co
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