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Canceled

258 Cross Street, Winchester MA 01890

$999,900

Estimated $6,960/month Calculator

Single Family

4 Bedrooms

Baths

1719

Total Parking: 4

7,700 (0.18)

Built in 1860

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).

This home has been viewed 20 times

Last Checked: September 14th, 2026 at 10:25am (Source: MLS PIN #73541288)

Air Conditioning

Waterview

Lead Paint Free

General Information for 258 Cross Street, Winchester MA 01890

Listing ID73541288

Property TypeSingle Family / Detached

Price$999,900 ($581.68/SqFt)

StyleColonial

CityWinchester

CountyMiddlesex

MLS AreaWinchester Highlands

Neighborhood(s)

Garage Parking0

ZoningRG

Year Built1860

Year Built SourcePublic Records

Year Built DetailsApproximate

Interior Features for 258 Cross Street, Winchester MA 01890

Approximate Living Area Total1719

Living Area Includes BasementNo

Rooms7

Bedrooms4

Primary En Suite BathroomYes

BasementFull

Cooling1, Split

Fireplaces

AppliancesRange

FlooringTile

Electric

Exterior Features for 258 Cross Street, Winchester MA 01890

Approximate Lot Size (Acres)0.18

Approximate Lot Size (Square Feet)7700

Total Parking4

Garage Parking0

WaterPublic

SewerPublic Sewer

Lot FeaturesGentle Sloping

Parking Features1

Exterior FeaturesPorch

Foundation Materials

Construction MaterialsFrame

Road Frontage Type

Patio & PorchCovered

Roof MaterialAsphalt/fiberglass Shingles

Utility Connections110 Volts

Water ViewsNo

Water Views Features

Waterfront0

Waterfront Features

Pool Features

Horse Permitted0

Horse Amenities

Disclosures for 258 Cross Street, Winchester MA 01890

Lead PaintNone

UFFI

Living Area Includes BasementNo

Living Area Disclosure

Building Area SourcePublic Records

Special Listing Conditions

ExclusionsAll Tenant Possessions

Compensation Based On

Financial Information for 258 Cross Street, Winchester MA 01890

Association Fee

Association Fee Frequency

Association Fee Includes

Real Estate Tax9591.95

Tax Year2026

Assessed Value$865,700

Location Information for 258 Cross Street, Winchester MA 01890

Elementary SchoolLynch Elementary School

Middle SchoolMccall Middle School

High SchoolWinchester High School

Neighborhood(s)

MLS AreaWinchester Highlands

Area AmenitiesWalk/jog Trails

Contact Information for 258 Cross Street, Winchester MA 01890

Agent

Name: Justin Blankenship

Office

Name: Fiv Realty Co

Phone: 781-365-7984

Payment Calculator

, Interest

Property Taxes 799.33

Principal & Interest 6161.07

HOA Dues

Term

Interest

Home Price

Down Payment

Exclusive Listing Agent

Fiv Realty Co

Justin Blankenship

Agent Phone

Office Phone

(781) 365-7984

Text Agent Call Agent Call Office

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EXIT

36 More Photos