$999,900

258 Cross Street, Winchester, MA 01890

4 beds |
2 baths |
1,719 sqft

Single-Family Home
Built in 1860
7,841sqft lot
—— car garage
$582/sqft
Listed 12 days ago

Property Description

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!

Listing Status:: Active
Date Added:: June 24, 2026
Data Last Updated:: July 6, 2026 at 4:06PM
Listing Office:: Fiv Realty Co : 781-365-7984
Listing Agent:: Justin Blankenship : 617-918-7419
MLS ID:: 73541288

General: Internet Available - Unknown
Appliances: Gas Water HeaterRangeDishwasherDisposalMicrowaveRefrigeratorFreezerWasherDryer
Laundry: In Basement
Basement: FullConcreteUnfinished
Flooring: WoodTileCarpetHardwood
A/C: Central Air
Heating: CentralForced Air
Fireplace: Fireplaces: 0

General: PatioStorageProfessional LandscapingFenced YardGarden
Style: Colonial
Parking: Off StreetDeededPavedParking spaces: 4

Roofing: Shingle
General: FrameStone

Road/Access: Public
Originating MLS: MLS Property Information Network
County: Middlesex

Zoning: RG898140
Fencing: Fenced/EnclosedFenced

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

Source: MLS Property Information Network

This listing courtesy of Justin Blankenship , Fiv Realty Co

Monthly Payment

$Est. Payment

Principal & Interest $
Property Taxes $
Home Insurance $
VA Funding Fee $

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