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29500 Main Road

Cutchogue, NY 11935
  • $2,250,000
  • STATUS: Active
  • ON SITE: 463 Days
  • MLS #: L3584002
UPDATED: 60 min ago
$2,250,000
  • 2
    BEDS
  • 2.42
    ACRES
  • 1
    BATHS
  • 0
    1/2 BATHS
Neighborhood:
Type:
Single-Family Home
Built:
1830
County:
Area:

Description

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.

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© 2026 OneKey MLS. All rights reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but is not guaranteed accurate by the MLS or Mark Seiden Real Estate Team. Data last updated: 2026-01-16T13:18:22.387.
www.lowerhudsonvalleyproperties.com/homes/156534082
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29500 Main Road Cutchogue, NY 11935

  • Price: $2,250,000
  • Status: Active
  • On Site: 463 Days
  • Updated: 60 min ago
  • MLS #: L3584002
2
Beds
1
Baths
0
½ Baths
2.42
Acres
1830
Built
Neighborhood:
Southold
County:
Suffolk
Area:
Southold
Elementary School:
Mattituck-Cutchogue Elementary Sch
Middle School:
Mattituck Junior-Senior High School
High School:
Mattituck Junior-Senior High School
School District:
Mattituck-Cutchogue
Property Description
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.
Exterior Features

Architectural Style Barndominium Construction Materials FrameCedar Cross Street Pequash Foundation Details Slab Levels Two Lot Features Near Public TransitNear SchoolNear ShopsLevel Parking Features PrivateDriveway Pool Private YN No Property Attached YN No

Interior Features

Appliances Gas Water HeaterCooktopDishwasherDryerWasher Attic Unfinished Basement Details Crawl Space Basement YN Yes Cooling Central Air Fireplaces Total 0 Flooring Hardwood Interior Features Cathedral Ceiling(s)Eat-in KitchenMaster DownstairsFirst Floor Bedroom Num Of1 Bed Rooms 0 Num Of2 Bed Rooms 0 Num Of3 Bed Rooms 0 Num Of4 Bed Rooms 0 Number Of Heating Zones 1 Number Of Kitchens 1 Rooms Total 5

Property Features

Additional Fees 0.00 Additional Fees YN No Association Amenities Park Association YN No Down Payment Resource YN No Heating Natural GasForced Air Lease Considered YN No Lot Size Dimensions 2.35 Property Sub Type Single Family Residence Senior Community YN No Sewer Cesspool Spa YN No Tax Annual Amount 14659.8 Tax Section 102 Water Source Public

Listing courtesy of Kristy B. Naddell of Douglas Elliman Real Estate: 631-354-8100
© 2026 OneKey MLS. All rights reserved.


© 2026 OneKey MLS. All rights reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but is not guaranteed accurate by the MLS or Mark Seiden Real Estate Team. Data last updated: 2026-01-16T13:18:22.387.
 
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Briarcliff Manor NY, 10510