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3D

258 Cross Street, 
Winchester, MA 01890

$999,900

4

Beds

2

Baths

1,719

Sq Ft

Single Family

Active

Listed by

Justin Blankenship

Fiv Realty Co

781-365-7984

Last updated:

July 25, 2026, 10:45 AM

MLS#

73541288

Source:

MLSPIN

About This Home

258 Cross Street

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

Home Facts

Single Family

2 Baths

4 Bedrooms

Built in 1860

Price Summary

999,900

$581 per Sq. Ft.

MLS #:

73541288

Last Updated:

July 25, 2026, 10:45 AM

Rooms & Interior

Bedrooms

Total Bedrooms:

4

Bathrooms

Total Bathrooms:

2

Full Bathrooms:

2

Interior

Living Area:

1,719 Sq. Ft.

Structure

Structure

Architectural Style:

Colonial

Building Area:

1,719 Sq. Ft.

Year Built:

1860

Lot

Lot Size (Sq. Ft):

7,700

Finances & Disclosures

Finances

Price:

$999,900

Price per Sq. Ft:

$581 per Sq. Ft.

Source:MLSPIN
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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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.