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38 Landing Meadow Road

Smithtown, NY 11787
  • $3,995,000
  • STATUS: Active
  • ON SITE: 49 Days
  • MLS #: 1022766
UPDATED: 2 min ago
$3,995,000
  • 7
    BEDS
  • 22.3
    ACRES
  • 5
    BATHS
  • 1
    1/2 BATHS
  • 6,000
    SQFT
  • $666
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
1828
County:
Area:

School Information

Elementary School:
Middle School:
School District:

Description

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.

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© 2026 OneKey MLS. All rights reserved. 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. Information is deemed reliable but is not guaranteed accurate by the MLS or Mark Seiden Real Estate Team. Data last updated: 2026-09-08T14:21:13.66.
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38 Landing Meadow Road Smithtown, NY 11787

  • Price: $3,995,000
  • Status: Active
  • On Site: 49 Days
  • Updated: 2 min ago
  • MLS #: 1022766
7
Beds
5
Baths
1
½ Baths
22.3
Acres
6,000
SQFT
$666
$/SQFT
1828
Built
Neighborhood:
Smithtown
County:
Suffolk
Area:
Smithtown
Elementary School:
Accompsett Elementary School
Middle School:
Accompsett Middle School
High School:
Smithtown High School-East
School District:
Smithtown
Property Description
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.
Exterior Features

Architectural Style Estate Carport YN No Construction Materials ClapboardFrameWood Siding Cross Street Salt Hay Exterior Features Balcony Garage YN No Levels Two Lot Features LevelPart WoodedSloped Parking Features OversizedPrivate Patio And Porch Features DeckPatioPorch Pool Private YN No Property Attached YN No View OpenPanoramicRiverTrees/WoodsWater Waterfront Features River FrontWater AccessWaterfront Waterfront YN Yes

Interior Features

Appliances OvenRangeRefrigerator Attic FullWalkup Basement Details FullWalk-Out Access Basement YN Yes Cooling Wall/Window Unit(s) Fireplace YN Yes Fireplaces Total 5 Flooring Hardwood Interior Features First Floor BedroomFirst Floor Full BathBuilt-in FeaturesChefs KitchenCrown MoldingEat-in KitchenEntertainment CabinetsEntrance FoyerFormal DiningIn-Law FloorplanNatural WoodworkOriginal DetailsPantryPrimary BathroomWalk-In Closet(s)Wet Bar Rooms Total 17

Property Features

Association YN No Building Area Total 6000 Down Payment Resource YN No Heating Hot WaterOil Horse YN Yes Lease Considered YN No Listing Terms Contract Other Structures Barn(s)OutbuildingStable(s)Workshop Property Sub Type Single Family Residence Senior Community YN No Sewer Cesspool Spa YN No Special Listing Conditions None Tax Annual Amount 37095 Tax Source Municipality Utilities See Remarks Water Source WellPrivatePublic

Listing courtesy of Philip C. Laffey of LAFFEY REAL ESTATE: 516-328-3233
© 2026 OneKey MLS. All rights reserved.


© 2026 OneKey MLS. All rights reserved. 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. Information is deemed reliable but is not guaranteed accurate by the MLS or Mark Seiden Real Estate Team. Data last updated: 2026-09-08T14:21:13.66.
 
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1238 Pleasantville Rd
Briarcliff Manor NY, 10510