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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.

Features
Heating System:
Natural Gas, Forced Air
Cooling System:
Central Air
Basement:
Crawl Space
Appliances:
Dishwasher, Dryer, Washer, Cooktop, Gas Water Heater
Community Features:
Near Public Transportation
Exterior Features:
Private Entrance
Fireplaces Total:
0
Flooring:
Hardwood
Garage Spaces:
2
Interior Features:
Eat-in Kitchen, Master Downstairs, Cathedral Ceiling(s), First Floor Bedroom
Lot Features:
Near Public Transit, Level, Near School, Near Shops
Parking Features:
Driveway, Private
Sewer:
Cesspool
Address Map
City:
Southold
State:
NY
County:
Suffolk County
Directions:
From Mattituck, east on route 25/main Road, house on the right.
Property and Construction
Architectural Style:
Barndominium
Association Amenities:
Park
Construction Materials:
Frame, Wood Siding, Stone, Energy Star, Vinyl Siding, Advanced Framing Technique, Fiberglass Insulation
Development Status:
Frame, Cedar
Elementary School:
Mattituck-Cutchogue Elementary Sch
High School:
Mattituck Junior-Senior High School
Inclusions:
Dishwasher, Refrigerator, Microwave, Energy Star Appliance(s)
Levels:
Two
Agent MlsId:
171098
Office MlsId:
DERE72
MiddleOrJunior School:
Mattituck Junior-Senior High School
New Construction:
1
Number Of Units:
1
Property Condition:
New
Senior Community:
1
Tax Annual Amount:
$14,081
Water Source:
Public
PhotosCount:
47

Residential For Sale

29500 Main Road, Southold, NY

2 Bedrooms
1 Bathrooms
2.42 Acre
$2,250,000
Listing ID #L3584002
Basic Details
Property Type :
Residential
Property SubType :
Single Family Residence
Listing ID :
L3584002
Price :
$2,250,000
Rooms :
5
Bedrooms :
2
Bathrooms :
1
Bathrooms Total :
1
Lot Area :
2.42 Acre
Year Built :
1830
Status :
Active
Status :
Active
Listing Office :
Douglas Elliman Real Estate
Listing Agent :
Kristy B. Naddell
Agent info
Kasner Properties
284 W Park Ave Long Beach, NY 11561
Contact Agent
Walkscore
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