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5355 New York 23, 
Windham, NY 12496

$689,000


5

Beds


Bath


2,500

Sq Ft


Multi-Family

Active

Listed by

Carol Shaw

Shaw Country Realty, Inc.

518-734-3500

Last updated:

June 3, 2026, 03:08 PM

MLS#

20262874

Source:

NY MLSUC

About This Home

5355 New York 23

CALLING INVESTORS - PRIME WINDHAM VILLAGE OPPORTUNITY Rare opportunity in the heart of Windham Village with exceptional commercial and residential development potential. Positioned in one of the Catskills' most desirable four-season destinations, this property offers investors the chance to capitalize on the continued growth and popularity of Windham. Windham is truly ''the place to be,'' attracting visitors year-round with its breweries, restaurants, movie theater, live entertainment venues, walking paths, golf, and outdoor recreation -- all just minutes to skiing at Windham Mountain Club. This property presents tremendous upside potential for: • Mixed-use commercial/residential development • Retail with upscale apartments above • Boutique hospitality or vacation rental concepts • Restaurant, brewery, or entertainment venue • Expanded multi-unit residential use A major value-added component already exists through participation in the NYC Watershed/CWC flood mitigation program. The current ownership has completed the first three phases of approvals and applications, positioning the project for construction application status. Approximately 3/4 of associated cost is covered for: • Elevating the building due to flood zone • Constructing a new foundation • Relocating utilities to the first floor To preserve continuity within the approved program, ownership is structured through 5355 Main Street, LLC, allowing a purchaser to step directly into the existing approval process and benefits already secured. Additionally, prior approvals from the Town of Windham included: • A rear addition • Expanded first-floor commercial space • Relocation of apartments to upper levels Ownership was also advised that a future third floor of apartments would likely receive approval, creating even greater residential income potential. With strong tourism, growing demand, and limited village inventory, this is a strategic opportunity for investors and developers seeking a high-visibility property with approvals, infrastructure planning, and substantial upside already in motion

Home Facts

Multi-Family

5 Bedrooms

Built in 1965

Price Summary

689,000

$275 per Sq. Ft.

MLS #:

20262874

Last Updated:

June 3, 2026, 03:08 PM

Added:

6 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

5

Interior

Living Area:

2,500 Sq. Ft.


Structure

Structure

Building Area:

2,500 Sq. Ft.

Year Built:

1965


Lot

Lot Size (Sq. Ft):

10,454


Finances & Disclosures

Finances

Price:

$689,000

Price per Sq. Ft:

$275 per Sq. Ft.

Source:NY MLSUC
The information being provided by Hudson Valley Catskill Mls is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information is deemed reliable but not guaranteed and should therefore be independently verified. © 2026 Hudson Valley Catskill Mls All rights reserved.

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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.