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258 Cross Street, Winchester, MA 01890

$999,900 (Active)
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Listed by: - Fiv Realty Co

258 Cross Street, Winchester, MA 01890

$$999,900
Active
est.$999,900/month.
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4 beds. 2 baths. 7,700 Sqft.

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258 Cross Street, Winchester, MA 01890

$999,900
Active
est.$999,900/month.
Start My Approval
4 beds 2 baths 7,700 Sq.ft.
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Property details for 258 Cross Street, Winchester, MA 01890
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

Listed by: Justin Blankenship
Broker details: Fiv Realty Co
Property Description

MLS Information

  • Listing: 73541288
  • Listing Last Modified: 2026-07-08

Property Details

  • Standard Status: Active
  • MLS Status: Active
  • Property style: Colonial
  • Built in: 1860
  • Lot size area: 0.18 Acres

Geographic Data

  • County: Middlesex
  • Directions: GPS
Features

Interior Features

  • Flooring: Wood, Tile, Carpet, Hardwood
  • Bedrooms: 4
  • Full baths: 2
  • Living area: 1719
  • Interior Features: Crown Molding

Exterior Features

  • Roof type: Shingle
  • Lot description: Corner Lot, Level, Landscaped
  • Foundation: Stone

Parking

    Utilities

    • Sewer: Public Sewer
    • Water: Public
    • Heating: Central, Forced Air
    Property Information

    Tax Information

    • Tax Annual Amount: $9,592

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    The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information 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. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.

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    Home Description

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