Welcome to 38 Landing Meadow Road, Smithtown. Nestled on almost 23 picturesque and serene waterfront acres overlooking the renowned Nissequogue River this is a truly extraordinary North Shore retreat. Driving down the long private driveway your senses are alive to the possibilities of what is to appear. Surrounded by breathtaking natural beauty, the property includes agricultural land adjoining approx. 60 acres of protected preserve, creating an unmatched sense of privacy and tranquility. Wide open vistas, emerald lawns, magnificent mature trees and the grand nature of this idyllic scene are unmatched. Barns, stables, paddock, workshops, and multiple outbuildings provide endless possibilities for equestrian pursuits, farming, recreation, or creating your own private compound or purpose. This timeless Manor House built in 1828 offers nearly 6,000 square feet of living space, featuring 7 stately and spacious bedrooms and 6 bathrooms. The magnificent Estate is highlighted on the first floor by a warm and opening center hall with access to the rear property and patio, a formal living room, grand den with fireplace and the first floor is side property, den or library with a fireplace, truly formal dining room with a fireplace, an inviting eat-in kitchen designed for everyday living and entertaining and butlers pantry, family room or bedroom with a wet bar and two bathrooms. The charm and character of all of the rooms with so many original details of fireplace mantles and surrounds, stair mouldings and hardwood floors take you to another time. Besides the grand Manor home the property outside has an antique barn of approx. 7,500 square feet which offers the possibility of future use, and a caretakers suite inside. Also on the property is a “bank” barn with four 12x14’ horse stalls, a tack room and hayloft. Besides this barn is another smaller barn also with four 12x12’ horse stalls. On the grand 20 acre land preserve is extensive paddock and other fenced areas. Conveniently located near parks, golf clubs, beaches, wineries, charming villages, museums, and fine dining, this exceptional estate offers a rare opportunity to experience waterfront living at its finest. Walking in to this one-of-a-kind Estate you feel that 38 Landing Meadow Road Smithtown is a rare opportunity where history, nature and endless potential come together. Since the property adjoins multiple land preserve woodlands it ensures a forever-preserved backdrop and an exceptional North Shore lifestyle in which this legacy Estate can be yours and protected.
Long Island, located between New York Harbor and the Atlantic Ocean, is a coastal and suburban New York neighborhood with barrier beaches and commuter rail hubs. The neighborhood’s energy concentrates around the Jamaica Station complex, where LIRR platforms, bus bays, and street-level storefronts create a constant current of movement. Housing shifts from compact prewar village centers to postwar capes and split-levels, with marinas and bayfront parks shaping daily routines. Jones Beach State Park and the Long Island Aquarium serve as signature day-trip anchors. The Paramount in Huntington and the Nassau County Museum of Art add a cultural throughline beyond the shoreline. Farm stands, delis, and small main streets stitch together a landscape defined by parkways, dunes, and bays.
Provided by Walk Score and Local Logic
Offer insights
38 Landing Meadow Rd · $3,995,000
$3.98M and above
75% chance or better to win
Why $3.98M+ is a strong offer
DAYS ON MARKET
86 days
The average home goes pending in 31 days.
SALE-TO-LIST
102.4%
Most homes are selling 2% above list price.
About offer insights
Property details
Interior
Exterior
Finance
Kitchen
Bathroom
Bedroom
Dining
Interior features
First-floor bedroom
First-floor full bath
Built-in features
Chef’s kitchen
Crown molding
Eat-in kitchen
Entertainment cabinets
Entrance foyer
Formal dining room
In-law floorplan
Natural woodwork
Original details
Pantry
Primary bathroom
Walk-in closet(s)
Wet bar
Bedrooms
Beds on the first floor available
Bathrooms
Five full bathrooms
One half bathroom
Kitchen
Oven
Range
Refrigerator
Laundry & utility
Basement available for utilities
Flooring
Hardwood floors
Heating & cooling
Hot water heating
Oil heating
Wall/window air conditioning units
Exterior features
Balcony
Deck
Patio
Porch
Barn(s)
Outbuilding
Stable(s)
Workshop
Waterfront property
Level, partially wooded and sloped terrain
Home design
Single family residence
Two levels
Full walkup attic
Parking
Oversized private parking
Construction
Clapboard, frame and wood siding construction
Utilities
Cesspool sewer
Utilities described in remarks
Electricity and solar
View estimated energy costs and solar savings for this home
Magnificent 5,400 Sq. Ft. Estate Set On 23 Spectacular Acres Along The Nissequogue River. Breath Taking Views, Rolling Hills, Privacy Galore. Property Abuts Hundreds Of Acres Of Preserved Woodlands & Riverfront. Perfect For An Organic Agricultural Or Horse Farm. Subdivision Rights Sold To County. Woodlands Donated To The Land Trust., Additional information: Appearance:Mint -,Separate Hotwater Heater:Yes
OneKey® MLS as Distributed by MLS Grid #L2719461
Jul 31, 2015
Listing Removed
—
Nov 5, 2014
Listed
$1,499,990
$250/sq ft
OneKey® MLS as Distributed by MLS Grid #L2646029
Aug 27, 2014
Listing Removed
—
Feb 8, 2014
Listed
$2,900,000
$483/sq ft
OneKey® MLS as Distributed by MLS Grid #L2646033
Aug 27, 2014
Listing Removed
—
Feb 8, 2014
Listed
$1,500,000
$250/sq ft
OneKey® MLS as Distributed by MLS Grid #L2646014
Jun 1, 2014
Listing Removed
—
Feb 8, 2014
Listed
$1,500,000
$250/sq ft
Year
Property tax
Land + Additions
Assessment*
2026
$31,612
$3,000 + $8,640
$11,640
2025
$31,612 (+4.1%)
$3,000 + $8,640
$11,640
2024
$30,353 (+2.6%)
$3,000 + $8,640
$11,640
2023
$29,587 (+2.8%)
$3,000 + $8,640
$11,640
2022
$28,782
$3,000 + $8,640
$11,640
2021
$28,782 (+1.6%)
$3,000 + $8,640
$11,640
2020
$28,334 (+0.2%)
$3,000 + $8,640
$11,640
2019
$28,285 (+2.8%)
$3,000 + $8,640
$11,640
2018
$27,515 (+3.7%)
$3,000 + $8,640
$11,640
2017
$26,545 (+1.3%)
$3,000 + $8,640
$11,640
2016
$26,214 (+2.2%)
$3,000 + $8,640
$11,640
2015
$25,656 (+2.2%)
$3,000 + $8,640
$11,640
2014
$25,097 (+3.6%)
$3,000 + $8,640
$11,640
2013
$24,215 (+1.9%)
$3,000 + $8,640
$11,640
2012
$23,758 (+5.1%)
$3,000 + $8,640
$11,640
2011
$22,614 (+3.3%)
$3,000 + $8,640
$11,640
2010
$21,883 (+5.1%)
$3,000 + $8,640
$11,640
2009
$20,811
$3,000 + $8,640
$11,640
Public record
Beds
6
Baths
5.5
Stories
—
Lot width
—
Lot depth
—
Lot size
2.2 Acres
Year renovated
—
Finished Sq. Ft.
3,891
Unfinished Sq. Ft.
—
Total Sq. Ft.
3,891
Year built
1900
Style
Single Family Residential
County
Suffolk County
APN
0800051000700005001
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Aug 31, 2026.
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
5/10 Heat Factor
7 days above 95° expected this year, 16 days in 30 years
8/10 Wind Factor
80% chance of strong winds in next 30 years
4/10 Air Factor
3 unhealthy days expected this year, 5 days in 30 years
Provided by First Street
Historical weather
Smithtown, NY • 11787
Average low and high temperatures (°F)
36
24
39
26
53
36
61
44
70
53
82
63
86
69
81
63
76
60
67
50
55
40
42
29
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
63/ 100
Moderate sunlight
Sunscore
There appears to be some shading by surrounding buildings, terrain, and vegetation.
7.8 hrs
3.7 hrs
JuneDecember
Provided by Shadowmap
Redfin Estimate for 38 Landing Meadow Rd
We cannot show automated home-value estimates for this home.
Nearby homes have recently sold between $999,000 and $1,750,000.
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $999K to $1.8M.