258 Cross Street, Winchester, MA 01890

Winchester
Local realty services provided by:Better Homes and Gardens Real Estate The Shanahan Group
258 Cross Street,Winchester, MA 01890
$999,900
  • 4 Beds
  • 2 Baths
  • 1,719 sq. ft.
  • Single family
  • Active
Listed by: justin blankenship
Office: fiv realty co
MLS#:73541288
Source:MLSPIN

Price summary

  • Price:$999,900
  • Price per sq. ft.:$581.68

About this home

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...

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Home facts

  • Year built:1860
  • Listing ID #:73541288
  • Updated:August 14, 2026 at 11:19 AM

Rooms and interior

  • Bedrooms:4
  • Total bathrooms:2
  • Full bathrooms:2
  • Rooms Total:7
  • Flooring:Carpet, Hardwood, Tile, Wood
  • Dining Description:Crown Molding, Hardwood, Pendant, Window(s) - Picture
  • Kitchen Description:Cabinets - Upgraded, Ceiling Fan(s), Countertops - Stone/Granite/Solid, Dishwasher, Disposal, Exterior Access, Flooring - Stone/Ceramic Tile, Freezer, Gas Stove, Microwave, Range, Recessed Lighting, Refrigerator, Remodeled, Stainless Steel Appliances, Vestibule, Window(s) - Picture
  • Basement Description:Concrete, Full, Unfinished
  • Living area:1,719 sq. ft.

Heating and cooling

  • Cooling:1 Cooling Zone, Central Air
  • Heating:Central, Forced Air
  • Central air:Yes

Structure and exterior

  • Roof:Shingle
  • Year built:1860
  • Building area:1,719 sq. ft.
  • Lot area:0.18 Acres
  • Lot Features:Corner Lot, Level
  • Architectural Style:Colonial
  • Construction Materials:Frame
  • Exterior Features:Garden, Patio, Professional Landscaping, Storage
  • Foundation Description:Stone

Schools

  • High school:Winchester High School
  • Middle school:Mccall Middle School
  • Elementary school:Lynch Elementary School

Utilities

  • Water:Public
  • Sewer:Public Sewer

Finances and disclosures

  • Price:$999,900
  • Price per sq. ft.:$581.68
  • Tax amount:$9,591 (2026)

Features and amenities

  • Appliances:Dishwasher, Disposal, Dryer, Freezer, Microwave, Range, Refrigerator, Washer
  • Laundry features:Dryer, In Basement, Washer
  • Amenities:Gas Water Heater

Parking

  • Total parking spaces:4
  • Parking description:Deeded, Off Street, Paved
The property listing data and information, or the Images, 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, 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. 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, or as to the accuracy of any of the Images, set forth herein.

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