29500 Main Road, Cutchogue, NY 11935

Local realty services provided by:ERA Caputo Realty
29500 Main Road,Cutchogue, NY 11935
$2,250,000
  • 2 Beds
  • 1 Baths
  • - sq. ft.
  • Single family
  • Active
Listed by: kristy b. naddell, thomas j. uhlinger
Office: douglas elliman real estate
MLS#:L3584002
Source:OneKey MLS

Price summary

  • Price:$2,250,000

About this home

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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Home facts

  • Year built:1830
  • Listing ID #:L3584002
  • Added:456 day(s) ago
  • Updated:January 09, 2026 at 11:41 AM

Rooms and interior

  • Bedrooms:2
  • Total bathrooms:1
  • Full bathrooms:1

Heating and cooling

  • Cooling:Central Air
  • Heating:Forced Air, Natural Gas

Structure and exterior

  • Year built:1830
  • Lot area:2.42 Acres

Schools

  • High school:Mattituck Junior-Senior High School
  • Middle school:Mattituck Junior-Senior High School
  • Elementary school:Mattituck-Cutchogue Elementary Sch

Utilities

  • Water:Public
  • Sewer:Cesspool

Finances and disclosures

  • Price:$2,250,000
  • Tax amount:$14,660 (2026)
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