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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

Basic Information

  • List Price$999,900
  • MLS Number73541288
  • Modification Date06/24/2026
  • Property SubTypeSingle Family Residence
  • Virtual TourView Tour

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

Other

  • Date Listed06/24/2026
  • Farm Land Area Units Square Feet

Tax Information

  • Tax Assessed Value $865,700
  • Tax Year 2026
  • Taxes$9,591

Parking

  • Parking Spaces4
  • Open Parking YN Yes
  • Parking Features Off Street, Deeded, Paved

Location

  • NeighborhoodWinchester Highlands
  • SubdivisionWinchester Highlands
  • Address258 Cross Street
  • Building Number258
  • CountyMiddlesex
  • StateMA
  • StreetCross Street
  • TownWinchester
  • Zip01890

Property

  • Acreage0.18

Exterior

  • Exterior Features Patio, Storage, Professional Landscaping, Fenced Yard, Garden
  • Fencing Fenced/Enclosed, Fenced
  • RoofShingle

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

School Information

  • High School Winchester High School
  • Elementary SchoolLynch Elementary School
  • Junior HighMccall Middle School

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

Interior

  • Flooring Wood, Tile, Carpet, Hardwood
  • Interior Features Internet Available - Unknown

Utilities

  • Cooling Central Air
  • Cooling YN Yes
  • Heat SystemYes
  • Heating Central, Forced Air
  • Sewer Public Sewer
  • Water Source Public

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

Map Location

Listed by Justin Blankenship of Fiv Realty Co

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. (MLSPIN) from third party sources, including sellers, lessors and public records, and were compiled by MLSPIN. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLSPIN and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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