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29500 Main Road, 
Cutchogue, NY 11935

$2,250,000


2

Beds


1

Bath


-

Sq Ft


Single Family

Active

Listed by

Kristy B. Naddell

Thomas J. Uhlinger

Douglas Elliman Real Estate

Last updated:

December 28, 2025, 04:44 AM

MLS#

L3584002

Source:

OneKey MLS

About This Home

29500 Main Road

Some homes tell a story. This one tells the North Fork’s. A rare opportunity to own one of Cutchogue’s most iconic historic properties, this mid-1800s barn was once part of the original Fleet family farm. With hand-hewn beams, circular-sawn pine, and timeless proportions, it captures the soul of North Fork heritage—a living piece of history ready for new vision. Set on 2.42 private acres bordering preserved farmland, the property offers open, lasting views and complete privacy within mature Skip Laurel and 16-foot Leyland hedges. Fifteen years ago, key updates were made, including a new roof, foundation restoration, new cesspools, and upgraded electrical systems. Move-in ready, the main residence combines rustic charm with modern comfort, while the rear barn area offers endless potential for a stunning guesthouse, studio, or expanded compound. Iconic, historic, and full of character, this is a rare chance to revive a true North Fork landmark.

Home Facts

Single Family

1 Bath

2 Bedrooms

Built in 1830

Price Summary

2,250,000

MLS #:

L3584002

Last Updated:

December 28, 2025, 04:44 AM

Added:

a year ago


Rooms & Interior

Bedrooms

Total Bedrooms:

2

Bathrooms

Total Bathrooms:

1

Full Bathrooms:

1


Structure

Structure

Year Built:

1830


Lot

Lot Size (Sq. Ft):

105,415


Finances & Disclosures

Finances

Price:

$2,250,000

Source:OneKey MLS
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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.