29500 Main Rd

Cutchogue, NY 11935

$2,250,000
Price
2
Beds
—Sq. Ft.
— / Sq. Ft.
—
Sq. Ft.
—
per Sq. Ft.
Virtual Tour
Virtual Tour
View of barn featuring a lawn
View of front of property featuring a gambrel roof, roof with shingles, and a barn
Aerial view of property's location
View of home's exterior
Kitchen featuring white cabinets, appliances with stainless steel finishes, beamed ceiling, dark wood-type flooring, and wall chimney exhaust hood
Kitchen with dark wood finished floors, a kitchen island with sink, beam ceiling, white cabinetry, and appliances with stainless steel finishes
Living area featuring high vaulted ceiling, a chandelier, beamed ceiling, wood walls, and dark wood finished floors
Living area featuring wooden walls, a chandelier, and wood ceiling
Kitchen with white cabinets, appliances with stainless steel finishes, and wood walls
Living room featuring healthy amount of natural light, wood walls, beam ceiling, and high vaulted ceiling
Living area featuring beam ceiling, healthy amount of natural light, wood walls, and high vaulted ceiling
Bedroom featuring wood walls and wood ceiling
Bedroom with dark wood-style floors and wooden walls
Bedroom with wooden walls and wood ceiling
Full bath with hardwood / wood-style flooring and vanity
Bathroom with dark wood finished floors and wooden walls
View of bathroom
Exterior view
Sunroom with healthy amount of natural light, an outdoor living space, and a patio area
Dining room featuring a towering ceiling
Misc room with healthy amount of natural light and a high ceiling
Misc room featuring a towering ceiling, concrete flooring, and wooden walls
Living room featuring brick floors, a wood ceiling with exposed beams, and wooden walls
Entryway featuring wood-type flooring, a wood ceiling with exposed beams, and wood walls
Entrance to property with a shingled roof
View of front of property with a gambrel roof, a shingled roof, and a barn
View of green lawn with a patio
View of property exterior
View of side of home featuring a chimney, a shingled roof, a barn, and a gambrel roof
View of outdoor structure
View of barn with a yard
View of home's exterior
Property entrance
View of front of property featuring a patio and a chimney
Surrounding community
View of barn featuring a lawn
Aerial view of property and surrounding area
Bird's eye view
View of green lawn

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...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.
  1. Listed by Kristy B. Naddell • Douglas Elliman Real Estate
    P: (631)-354-8100 C: (631)-905-8584 kristy.naddell@elliman.com
  2. Listed by Thomas J. Uhlinger • Douglas Elliman Real Estate
    P: (631)-354-8100 C: (516)-319-0323 tuhlinger@elliman.com

Property Details for 29500 Main Road

City/Township
Southold
Architectural Style
Barndominium
Section Area
Pequash
LISTING UPDATED: 01/08/2026 09:19 AM

Property Details for 29500 Main Road

StatusActive
MLS #L3584002
Days on Market477
Taxes$14,660 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeSingle Family
Year Built1830
Lot Size2.42 AC / 105,415 SF
CountySuffolk County

Location

Listing Courtesy of Douglas Elliman Real Estate, Kristy B. Naddell; Douglas Elliman Real Estate, Thomas J. Uhlinger
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Virtual Tour

Building Information for 29500 Main Road

Stories-Year Built1830Building Size-Lot Size2.42 AC / 105,415 SF

Payment Calculator

$12,188 per month

30 year fixed, 6.15% Interest

Principal and Interest

$10,966

Property Taxes

$1,222

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 29500 Main Road

Summary
Location and General Information
  • Senior Community YN: No
  • MLS District Code: 1000
  • Directions: From Mattituck, east on route 25/main Road, house on the right.
  • Tax Block: 3
  • Tax Lot: 10
  • Year Built Effective: 2003
  • Property Attached: No
  • Structure Type: false
  • Levels: Two
  • State Or Province: NY
School Information
  • School District: Mattituck-Cutchogue
  • Elementary School District: Mattituck-Cutchogue
  • Elementary School: Mattituck-Cutchogue Elementary Sch
  • Middle Or Junior School District: Mattituck-Cutchogue
  • Middle Or Junior School: Mattituck Junior-Senior High School
  • High School District: Mattituck-Cutchogue
  • High School: Mattituck Junior-Senior High School
Rental
Rental
  • Lease Considered: No
  • RentSpree Y/N: false
Unit Information
Unit Information
  • Number Of 1 Bedrooms: 0
  • Number Of 2 Bedrooms: 0
  • Number Of 3 Bedrooms: 0
  • Number Of 4 Bedrooms: 0
  • Building Units Total: 1
Room Information
Room 1 Information
  • Room Level: First
  • Room Type: Auxiliary Room
  • RoomDescription 1: EIK, Living Room, 2 bedrooms, 1 bath, laundry.
Room 2 Information
  • Room Type: Auxiliary Room
  • Room Description: Huge Barn area can be converted to living space.
Taxes and HOA Information
Taxes and HOA Information
  • Parcel Number: 1000-102-00-03-00-010-000
  • Additional Fees: No
  • Association Amenities: Park
  • Association: No
Interior and Exterior Features
Interior Features
  • Amenities: 1st Floor Bedrm, Barndominium, Cathedral/Vaulted/High Ceiling, Eat in Kitchen, Hardwood Floors As Seen, Park, Public
  • Interior Features: Cathedral Ceiling(s), Eat-in Kitchen, 1st Fl Master Bedroom, First Floor Bedroom
  • Appliances: Gas Water Heater, Cooktop, Dishwasher, Dryer, Washer
  • Number Of Kitchens: 1.0
  • Total Rooms: 5
  • Primary on Main: Yes
  • Basement: Crawl Space
  • Attic Description: Unfinished
  • Fireplaces Total: 0
  • Location Amenities: Hardwood Floors As Seen, Cathedral/Vaulted/High Ceiling, Eat in Kitchen, 1st Fl Master Bedroom
  • Spa: No
  • Flooring: Hardwood
  • Foundation Details: Slab
  • Basement: Yes
Exterior Features
  • Exterior Property Features: Private, Driveway, Near Public Transit, Near School, Near Shops, Level
  • Elevation Certificate: No
  • Construction Materials: Frame, Cedar
  • Pool Private: No
Lot Information
  • Lot Features: Near Public Transit, Near School, Near Shops, Level
  • Lot Size Dimensions: 2.35
  • Additional Parcel: No
  • Site Features: Near Public Transit, Near School, Near Shops, Level
Parking
  • Parking Features: Private, Driveway
Utilities
  • Cooling: Central Air
  • Heating: Natural Gas, Forced Air
  • Heat Fuel Type: Natural Gas, Forced Air
  • Number Of Heating Zones: 1
  • Sewer: Cesspool
  • Water Source: Public
Green Features
  • Green Features: Gas Water Heater, Cooktop, Dishwasher, Dryer, Washer, Natural Gas, Forced Air
Virtual Tour
Agent
Payment and Rate
  • Down Payment Resource: No

Public Records for 29500 Main Road

Taxable ValueLand$2,100Additions$6,500Total$8,600
Home Facts
Beds0Lot Size105,415 SqFtStyleSingle Family ResidenceZoningR-40CountySUFFOLKAPN1000-102.00-03.00-010.000

Schools near 29500 Main Road

This home is within Mattituck-Cutchogue Union Free School District.
Rating
School
Type
Grades
Distance
Mattituck Cutchogue Elementary School
Public - K to 6
Mattituck Junior Senior High School
Public - 7 to 12
Our Lady Of Mercy Regional School
Private - PK to 6
Rating
School
Distance
Mattituck Cutchogue Elementary School
PublicK to 6

Mattituck Junior Senior High School
Public7 to 12

Our Lady Of Mercy Regional School
PrivatePK to 6

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 29500 Main Road, Cutchogue, NY 11935

29500 Main Road is a single family home for sale in Cutchogue, NY 11935. This property was listed for sale on October 9, 2024 by Douglas Elliman Real Estate, it's currently listed at $2,250,000. This listing's school district is Mattituck-Cutchogue Union Free School District. Nearby schools include Mattituck Cutchogue Elementary School, Mattituck Junior Senior High School and Our Lady Of Mercy Regional School. 29500 Main Road is a 2-bed, 1-bath, single family home built in 1830.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Douglas Elliman Real Estate, Kristy B. Naddell; Douglas Elliman Real Estate, Thomas J. Uhlinger

Based on information submitted to the MLS GRID as of 01/08/2026 09:19 AM. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. 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. The data is deemed reliable but is not guaranteed by MLS GRID. Use of the MLS GRID data may be subject to an end user license agreement prescribed by the applicable MLS of the Member Participant, if any, and as amended from time to time.