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$5,899,000

For Sale - Active
38 Landing Meadow Rd, Smithtown, NY 11787
7 Beds
6 Baths
6,000 Square Feet
23.00 Acres Lot
Built in 1828
For Sale - Active
Units n/a
Checked: 2 hours ago
Updated: Aug 06, 2025 at 01:35AM

Investment Summary


Monthly Cash Flow
-$24,795
Cap Rate
1.0%
Cash-on-Cash Return
-21.9%
Debt Coverage Ratio
0.17
Internal Rate of Return (5 years)
-17.2%

Property Description


23.00 Acres Lot
Built in 1828
For Sale - Active
Units n/a

BEAUTY AT A GLANCE: Whether you’re looking for a peaceful retreat, a platform to build something meaningful, or a flexible space that blends both — this estate offers the freedom to live your vision. Rooted in history, surrounded by nature, and ready for what’s next, it’s not just a place to own — it’s a place to belong. WHO IT'S MEANT FOR: a) The Private Visionary Your own riverfront retreat, where the world slows and peace of mind catches up. This is for the one seeking privacy without distance — Live in quiet elegance. Relax in the Manor. Ride horseback. Hike through the trees and meadows. Harvest fresh eggs or wildflowers. Host friends...Or don’t. Create and enjoy your own vision. b) The Entrepreneur A brand-scape awaits, already seeded. If you dream in ventures — this is your moment. The estate represents three creative brands in both the virtual and physical world, with operational frameworks, and narrative assets. Explore. Launch a boutique retreat, intimate club, regenerative farm-stay, seasonal experiences, gaming preserve, or immersive wellness escapes and more. Everything you need to thrive is already here. c) The Hybrid Steward Live here. Share here. On your terms. Maybe you only need it part of the year — a few seasons to reconnect and recalibrate. The rest, you rent, lease or activate with purpose: culinary weekends, curated workshops, community supported agriculture, intimate gatherings, accommodations, and more. Monetize without commercialization. Share beauty when you are away. On your terms. CLIFF NOTES: Some places you visit. Others you feel. This estate is the latter — a once-in-a-generation, riverfront sanctuary where heritage whispers, imagination lingers, and the land seems to know your name before you arrive. Just one hour from Manhattan, perched above the Nissequogue River and wrapped in the quiet protection of hundreds of preserved acres, this 23-acre venue is more than a property. It’s a living canvas — for those who seek to create, to retreat, to enjoy a legacy. Location: On Site: Nissequogue River Basin 2 Miles: Historic Smithtown Village, Golf 3 Miles: LI Sound, State Park, Railroad 5 Miles: Wineries, Breweries, Museums 6 Miles: Historic Stonybrook Village 9 Miles: Historic Northport Village 10 Miles: Macarthur Airport 11 Miles: Historic Port Jefferson - Ferry 14 Miles: Historic Huntington Village 15 Miles: Ocean, Fire Island, Casino 35 Miles: Hamptons 44 Miles: JFK and LGA Airports 49 Miles: New York City Within 90 Miles: 130+ Golf Courses The Heart of the Estate: The land rolls gently here, opening into meadows, sheltering within woodlands, winding with trails that pull you toward the river’s edge. The views stretch endlessly across the Nissequogue Basin — golden in the morning, sunset hued at dusk. Anchoring the property is a historic 19th-century residence, flanked by vintage barns and stables, echoing a bygone era. With flexible zoning and agricultural rights, the land welcomes possibility. Opportunities like this are rare— not just for the land itself, but for the freedom it offers. Whether your vision is personal, professional, or somewhere in between, this estate is ready to meet you there. The story has deep roots. Now, it’s simply waiting for your exciting chapter. PRIVATE INQUIRIES WELCOME: Current stewards are open to aligned transitions, insight sharing, and vision continuity.

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Location


Property Details


Parking

  • Details: Detached, Driveway, Garage, Private, Storage
  • Garage Spaces: 4
  • Spaces Total: 0

Bedroom Information

  • # of Bedrooms: 7

Bathroom Information

  • # of Baths (Full): 5
  • # of Baths (Partial): 1
  • # of Baths (Total): 6.0

Interior Features

  • # of Rooms: 21
  • # of Stories: 2
  • Basement: Yes
  • Basement Description: Full, Partially Finished, Walk-Out Access
  • Fireplace: Yes

Exterior Features

  • Exterior Walls Materials: Wood

Land Information

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

Lot Information

  • Parcel ID: 0800051.0007.00005.001
  • Lot Size: 1001880 sqft

Property Information

  • Property Type: Single Family Residence
  • Style: Estate
  • Year Built: 1828

Tax Information

  • Annual Tax: $5,001

Utilities

  • Water & Sewer: Private, Well, Public, Spring
  • Heating: Hot Water, Oil, Wood, Other
  • Cooling: Multi Units

Location

  • County: Suffolk

Listing Details


Listed by:
Derek J. Greene
Greene Realty Group
(860) 560-1006

Source:
OneKey MLS
MLS#: 873824
OneKey MLS

Investment Summary


Monthly Cash Flow
-$24,795
Cap Rate
1.0%
Cash-on-Cash Return
-21.9%
Debt Coverage Ratio
0.17
Internal Rate of Return (5 years)
-17.2%

Purchase Details

Find an Agent

Purchase price:
$5,899,000
Amount financed:
-$4,719,200
Down payment:
$1,179,800
Closing costs:
$176,970
Rehab costs:
$0
Initial cash invested:
$1,356,770
Square feet:
6,000
Cost per square foot:
$983
Monthly rent per square foot:
$1.32

Financing Details

Find a Lender

Loan amount:
$4,719,200
Loan to value ratio:
80.0%
Loan type:
Amortizing
Term:
30 years
Interest rate:
6.500%
Principal & interest:
$29,829
Property tax:
$417
Insurance:
$553
Private mortgage insurance (PMI):
$0
Monthly payment:
$30,799

Operating Income

Find a Property Manager

% Rent Monthly Yearly
Gross rent:
$7,900 $94,800
Vacancy loss: (6%)
6% -$474 -$5,688
Operating income:
$7,426 $89,112

Operating Expenses


% Rent Monthly Yearly
Property taxes: (5%)
5%-$417-$5,002
Insurance: (7%)
7%-$553-$6,636
Property management: (8%)
8%-$632-$7,584
Repairs & maintenance: (5%)
5%-$395-$4,740
Capital expenditures: (5%)
5%-$395-$4,740
HOA fees: (n/a)
n/an/an/a
Total operating expenses: (30%)
30%-$2,392-$28,702

Cash Flow


Monthly Yearly
Net operating income:
$5,034 $60,408
Mortgage payments:
-$29,829 -$357,948
Cash flow:
$24,795 $297,540