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For sale
    • $999,900

    258 Cross St, Winchester, MA 01890

    4beds
    1,719sqft
    : 
    $6,308/mo
    Get pre-qualified
    Single Family Residence
    Built in 1860
    7,700 Square Feet Lot
    $987,300 Zestimate®
    $582/sqft
    $-- HOA

    What's special

    Tiled showerUpdated kitchenHardwood floorsBrand new acArched openingsCentral heatStainless appliances
    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).
    52 days
    |
    1,815
    |
    89
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Justin Blankenship 617-918-7419,

    Fiv Realty Co 781-365-7984

    Source: MLS PIN,MLS#: 73541288

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 2
      • Full bathrooms: 2
      Primary bedroom
      • Features: Ceiling Fan(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Window(s) - Picture, Cable Hookup, High Speed Internet Hookup
      • Level: Second
      • Area: 244.38
      • Dimensions: 17.25 x 14.17
      Bedroom 2
      • Features: Closet, Flooring - Hardwood, Window(s) - Picture, Cable Hookup, High Speed Internet Hookup, Lighting - Overhead
      • Level: Second
      • Area: 161.21
      • Dimensions: 13.25 x 12.17
      Bedroom 3
      • Features: Closet, Flooring - Hardwood, Window(s) - Picture, Attic Access, Remodeled
      • Level: Third
      • Area: 149.81
      • Dimensions: 11.75 x 12.75
      Bedroom 4
      • Features: Closet, Flooring - Wall to Wall Carpet, Window(s) - Picture, Attic Access, Remodeled
      • Level: Third
      • Area: 143.94
      • Dimensions: 11.75 x 12.25
      Bathroom 1
      • Features: Bathroom - Full, Bathroom - Double Vanity/Sink, Bathroom - With Tub & Shower, Flooring - Stone/Ceramic Tile, Window(s) - Picture, Countertops - Stone/Granite/Solid, Countertops - Upgraded, Bidet, Cabinets - Upgraded, Remodeled, Lighting - Overhead, Soaking Tub
      • Level: Second
      • Area: 80.24
      • Dimensions: 9.08 x 8.83
      Bathroom 2
      • Features: Bathroom - Full, Bathroom - With Tub, Flooring - Stone/Ceramic Tile, Window(s) - Picture, Remodeled, Lighting - Overhead, Pedestal Sink, Soaking Tub
      • Level: Second
      • Area: 30.38
      • Dimensions: 6.75 x 4.5
      Dining room
      • Features: Flooring - Hardwood, Window(s) - Picture, Lighting - Pendant, Crown Molding
      • Level: Main,First
      • Area: 185.01
      • Dimensions: 12.83 x 14.42
      Kitchen
      • Features: Ceiling Fan(s), Flooring - Stone/Ceramic Tile, Window(s) - Picture, Countertops - Stone/Granite/Solid, Cabinets - Upgraded, Exterior Access, Recessed Lighting, Remodeled, Stainless Steel Appliances, Gas Stove, Vestibule
      • Level: Main,First
      • Area: 205.83
      • Dimensions: 13 x 15.83
      Living room
      • Features: Flooring - Hardwood, Window(s) - Bay/Bow/Box, Cable Hookup, High Speed Internet Hookup, Lighting - Overhead, Crown Molding, Vestibule
      • Level: Main,First
      • Area: 238.89
      • Dimensions: 13.33 x 17.92
      Heating
      • Central, Forced Air
      Cooling
      • Central Air
      Appliances
      • Included: Gas Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer
      • Laundry: In Basement
      Features
      • Internet Available - Unknown
      • Flooring: Wood, Tile, Carpet, Hardwood
      • Basement: Full,Concrete,Unfinished
      • Has fireplace: No
      Interior area
      • Total structure area: 1,719
      • Total interior livable area: 1,719 sqft
      • Finished area above ground: 1,719

      Property

      Parking
      • Total spaces: 4
      • Parking features: Off Street, Deeded, Paved
      • Uncovered spaces: 4
      Features
      • Patio & porch: Patio
      • Exterior features: Patio, Storage, Professional Landscaping, Fenced Yard, Garden
      • Fencing: Fenced/Enclosed,Fenced
      Lot
      • Size: 7,700 Square Feet
      • Features: Corner Lot, Level
      Details
      • Parcel number: 898140
      • Zoning: RG

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Colonial
      • Property subtype: Single Family Residence
      Materials
      • Frame
      • Foundation: Stone
      • Roof: Shingle
      Condition
      • Year built: 1860

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: for Gas Range

      Community & HOA

      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
      HOA
      • Has HOA: No
      Location
      • Region: Winchester

      Financial & listing details

      • Price per square foot: $582/sqft
      • Tax assessed value: $865,700
      • Annual tax amount: $9,591
      • Date on market: 6/24/2026
      • Listing terms: Contract
      • Road surface type: Paved

        Estimated market value

        $987,300

        $938,000 - $1.04M

        $4,243/mo

        Price history

        DateEventPrice
        6/24/2026Listed for sale$999,900+43%$582/sqft
        Source: MLS PIN #73541288 Report a problem
        6/1/2020Sold$699,000$407/sqft
        Source: Public Record Report a problem
        3/26/2020Pending sale$699,000$407/sqft
        Source: Leading Edge Real Estate #72585005 Report a problem
        12/5/2019Price change$699,000-6.2%$407/sqft
        Source: Leading Edge Real Estate #72585005 Report a problem
        10/25/2019Listed for sale$745,000+22.6%$433/sqft
        Source: Leading Edge Real Estate #72585005 Report a problem
        1/25/2019Sold$607,500-6.5%$353/sqft
        Source: Public Record Report a problem
        11/28/2018Pending sale$649,999$378/sqft
        Source: Leading Edge Real Estate #72380664 Report a problem
        10/31/2018Price change$649,999-4.3%$378/sqft
        Source: Leading Edge Real Estate #72380664 Report a problem
        10/1/2018Price change$679,000-2.9%$395/sqft
        Source: Leading Edge Real Estate #72380664 Report a problem
        8/9/2018Price change$699,000-5.4%$407/sqft
        Source: Leading Edge Real Estate #72380664 Report a problem
        7/27/2018Price change$739,000-2.6%$430/sqft
        Source: Leading Edge Real Estate #72380664 Report a problem
        7/6/2018Listed for sale$759,000+64.1%$442/sqft
        Source: Leading Edge Real Estate #72380664 Report a problem
        8/10/2004Sold$462,500+65.2%$269/sqft
        Source: Public Record Report a problem
        11/24/1998Sold$279,900+86.6%$163/sqft
        Source: Public Record Report a problem
        9/22/1995Sold$150,000$87/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$9,148 0%$824,900 +2.1%
        2024$9,151 +4.9%$807,700 +9.2%
        2023$8,725 +4.3%$739,400 +10.6%
        2022$8,362 +1.1%$668,400 +3.7%
        2021$8,273 +2.7%$644,800 -0.8%
        2020$8,054 +7.3%$650,000 +4.8%
        2019$7,508 +0.3%$620,000 +1%
        2018$7,482 +4.4%$613,800 +5.1%
        2017$7,169 +9.3%$583,800 +3.9%
        2016$6,562 +0.3%$561,800 +4.2%
        2015$6,543 +6.9%$539,000 +11.5%
        2014$6,120 +9.9%$483,400 +10.9%
        2013$5,568 +1.8%$436,000
        2012$5,472 +3.7%$436,000
        2011$5,276 +5.6%$436,000 +0.4%
        2010$4,998 +2.1%$434,200
        2009$4,893 +4.6%$434,200 -1.9%
        2008$4,677 -0.3%$442,500 -2.6%
        2007$4,691 +1.7%$454,100 +2.1%
        2006$4,612 +2.8%$444,700 +3.3%
        2005$4,487 +6.1%$430,600 +15.9%
        2004$4,228 +4.9%$371,500 +4.9%
        2003$4,029 +11.2%$354,000 +8%
        2002$3,624 +65.3%$327,700 +55.6%
        2000$2,193 -5.6%$210,600 +32.7%
        1999$2,323 $158,700
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
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        Climate risks

        Neighborhood: 01890

        Getting around

        60 / 100
        Somewhat Walkable
        53 / 100
        Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Lynch Elementary School
        • Middle: Mccall Middle School
        • High: Winchester High School

        Source: MLS PIN. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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