Listing provided courtesy of Fiv Realty CoMLS# 73541288MLS Provider
  • 5 days on site
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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 the iconic, and picturesque downtown Winchester, lined with shops, dining and even a T stop!

Source: MLS PIN, MLS#: 73541288

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  • Property Type
    Residential
  • Lot
    0.18 acres

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  • Median Age
    42
  • Population Density
    3,585
  • College Educated
    78%
  • Estimated Median Income
    $173,058
  • Estimated Total Home Owners
    6,755
  • Estimated Total Renters
    1,310
  • Owner / Renter Divide
    84% / 16%
  • Estimated Average Household Size
    3
  • Total Population
    22,760
  • Community data courtesy of LiveBy, Inc.

Owning this Home

$
$ %
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* All calculations are estimates and provided by Reliance Network, for informational purposes only. Actual amounts may vary. ** Assumes 6.50% APR, 20% down payment, and conventional 30-year fixed rate first mortgage. Rates cited are for instructional purposes only; current rates are subject to change at any time without notice. You should not make any decisions based simply on the information provided. Additional required amounts such as taxes, insurance, homeowner association dues, assessments, mortgage insurance premiums, flood insurance or other such required payments should also be considered. Contact your mortgage company for current rates and additional information. Any mortgage broker or insurance agent that may appear is independent and is not affiliated with, endorsed by, or provided by the MLS.

Life at 258 Cross Street


Schools


School data courtesy of LiveBy, Inc.
Ratings are based on a scale of 1-5, with 5 being the highest rating and 1 being the lowest rating. The schools displayed on this website are for informational purposes only and may not represent a complete or up-to-date list. School assignments are subject to change and should be verified directly with the local school district. Please contact the appropriate school district to confirm school zoning and enrollment eligibility for this property.

History

Date Event Value Agent
6/28/2026Source: MLS PIN Status Change
Active
6/24/2026Source: MLS PIN Added to Database
June 24, 2026