Open House
Listing Tools
Success!
While you wait to hear back from us:
Hi there! How can we help you?
Contact us using the form below or give us a call.
Success!
While you wait to hear back from us:
Send to a friend
Forward this listing to a friend
Send A Message:
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
More Info
Basic Information
- Bedrooms4
- Mls StatusNew
- 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 Date06/24/2026
- 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
Success!
While you wait to hear back from us:
Hi there! How can we help you?
Contact us using the form below or give us a call.
Send Us A Message:
Success!
While you wait to hear back from us:
Hi there! How can we help you?
Contact us using the form below or give us a call.
Send Us A Message:
Success!
While you wait to hear back from us:
Hi there! How can we help you?
Contact us using the form below or give us a call.
Send Us A Message: