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$2,250,000

For Sale - Active
29500 Main Rd, Cutchogue, NY 11935
2 Beds
1 Bath
0 Square Feet
2.42 Acres Lot
Built in 1830
For Sale - Active
1 Units
Checked: 3 hours ago
Updated: Oct 15, 2025 at 10:02AM

Investment Summary


Monthly Cash Flow
-$6,340
Cap Rate
2.7%
Cash-on-Cash Return
-14.7%
Debt Coverage Ratio
0.44
Internal Rate of Return (5 years)
-10.2%

Property Description


2.42 Acres Lot
Built in 1830
For Sale - Active
1 Units

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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Location


Property Details


Parking

  • Description: Private, Driveway
  • Details: Private, Driveway
  • Garage Spaces: 0
  • Spaces Total: 0

Bedroom Information

  • # of Bedrooms: 2

Bathroom Information

  • # of Baths (Full): 1
  • # of Baths (Total): 1.0

Interior Features

  • # of Rooms: 5
  • Basement Description: Crawl Space

Land Information

  • Land Use: Residential
  • Land Use Subtype: Single Family Residential

Lot Information

  • Parcel ID: 1000102.0003.00010.000
  • Lot Size: 105415 sqft

Property Information

  • Property Type: Single Family Residence
  • Style: Barndominium
  • Year Built: 1830

Tax Information

  • Annual Tax: $14,081

Utilities

  • Water & Sewer: Public
  • Heating: Natural Gas, Forced Air
  • Cooling: Central Air

Location

  • County: Suffolk

Listing Details


Listed by:
Kristy B. Naddell
Douglas Elliman Real Estate
(631) 905-8584

Source:
OneKey MLS
MLS#: L3584002
OneKey MLS

Investment Summary


Monthly Cash Flow
-$6,340
Cap Rate
2.7%
Cash-on-Cash Return
-14.7%
Debt Coverage Ratio
0.44
Internal Rate of Return (5 years)
-10.2%

Purchase Details

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Purchase price:
$2,250,000
Amount financed:
-$1,800,000
Down payment:
$450,000
Closing costs:
$67,500
Rehab costs:
$0
Initial cash invested:
$517,500
Square feet:
0
Cost per square foot:
n/a
Monthly rent per square foot:
n/a

Financing Details

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Loan amount:
$1,800,000
Loan to value ratio:
80.0%
Loan type:
Amortizing
Term:
30 years
Interest rate:
6.500%
Principal & interest:
$11,377
Property tax:
$1,173
Insurance:
$630
Private mortgage insurance (PMI):
$0
Monthly payment:
$13,180

Operating Income

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% Rent Monthly Yearly
Gross rent:
$9,000 $108,000
Vacancy loss: (6%)
6% -$540 -$6,480
Operating income:
$8,460 $101,520

Operating Expenses


% Rent Monthly Yearly
Property taxes: (13%)
13%-$1,173-$14,081
Insurance: (7%)
7%-$630-$7,560
Property management: (8%)
8%-$720-$8,640
Repairs & maintenance: (5%)
5%-$450-$5,400
Capital expenditures: (5%)
5%-$450-$5,400
HOA fees: (n/a)
n/an/an/a
Total operating expenses: (38%)
38%-$3,423-$41,081

Cash Flow


Monthly Yearly
Net operating income:
$5,037 $60,444
Mortgage payments:
-$11,377 -$136,524
Cash flow:
-$6,340 -$76,080