38 Landing Meadow Road

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Active
$3,995,000
7 beds6,000 sqft
38 Landing Meadow Rd, Smithtown, NY 11787
Est: $23,736/moGet pre-approved
Single FamilyProperty Type
23 acresLot Size
1828Year Built
$666/sq ftPrice per sq ft

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...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.
61 days on Market
  • Listed by: Philip C. Laffey 516.328.3233 plaffey@laffeyre.com • LAFFEY REAL ESTATE
  • Listed by: Mark T. Laffey 516.922.9800 mark@laffeyre.com • LAFFEY REAL ESTATE
Last updated: 09/18/2026 11:37 AM • Source: ONEKEY as distributed by MLS GRID, MLS#: 1022766

Location

Listing Courtesy of LAFFEY REAL ESTATE, Philip C. Laffey; LAFFEY REAL ESTATE, Mark T. Laffey
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$23,736 per month

30 year fixed, 6.71% Interest

Principal and Interest

$20,644

Property Taxes

$3,091

HOA Dues

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Property Information for 38 Landing Meadow Road

Property Details
  • Taxes: $37,095 / year
  • MLS Type: Single Family
  • County: Suffolk County
  • City/Township: Smithtown
  • View: Open, Panoramic, River, Trees/Woods, Water
  • Architectural Style: Estate
  • Waterfront: Yes
  • Section Area: Salt Hay
Building Information
  • Year Built: 1828
  • Lot Size: 23.00 AC / 1,001,880 SF
Summary
Location and General Information
  • Senior Community YN: No
  • Tax Block: 4/5
  • Year Built Effective: 2016
  • Property Attached: No
  • Structure Type: Detached
  • Levels: Two
  • State Or Province: NY
School Information
  • School District: Smithtown
  • Elementary School District: Smithtown
  • Elementary School: Accompsett Elementary School
  • Middle Or Junior School District: Smithtown
  • Middle Or Junior School: Accompsett Middle School
  • High School District: Smithtown
  • High School: Smithtown High School-East
Rental
Rental
  • Lease Considered: No
Unit Information
Unit Information
  • Building Units Total: 1
Room Information
Room 1 Information
  • Room Level: Basement
  • Room Type: Basement
  • RoomDescription 1: Full, Unfinished, Laundry Room, Storage, Mechanical
Room 2 Information
  • Room Level: First
  • Room Type: Auxiliary Room
  • Room Description: Entry Foyer: Front to hallway with rear door to a covered grand patio
Room 3 Information
  • Room Level: First
  • Room Type: Bathroom 1
  • Room Description: Half Bathroom
Room 4 Information
  • Room Level: First
  • Room Type: Living Room
  • Room Description: Living Room or Music Room
Room 5 Information
  • Room Level: First
  • Room Type: Den
  • Room Description: With fireplace and multiple doors to outside and patio
Room 6 Information
  • Room Level: First
  • Room Type: Office
  • Room Description: Office or library with fireplace
Room 7 Information
  • Room Level: First
  • Room Type: Dining Room
  • Room Description: Formal Dining Room with fireplace and door to outside
Room 8 Information
  • Room Level: First
  • Room Type: Bonus Room
  • Room Description: Butlers Pantry
Room 9 Information
  • Room Level: First
  • Room Type: Kitchen
  • Room Description: Large and open eat-in-kitchen, gas cooking and access to a back staircase
Room 10 Information
  • Room Level: First
  • Room Type: Bedroom 1
  • Room Description: Ensuite with a Grand Wet Bar and Private Seperate Entrance
Room 11 Information
  • Room Level: Second
  • Room Type: Primary Bedroom
  • Room Description: Primary suite with fireplace, huge walk-in closet and bathroom
Room 12 Information
  • Room Level: Second
  • Room Type: Bedroom 2
  • Room Description: Fireplace
Room 13 Information
  • Room Level: Second
  • Room Type: Bedroom 3
  • Room Description: Access to Jack and Jill bathroom
Room 14 Information
  • Room Level: Second
  • Room Type: Bedroom 4
  • Room Description: Access to Jack and Jill bathroom
Room 15 Information
  • Room Level: Second
  • Room Type: Bedroom 5
Room 16 Information
  • Room Level: Second
  • Room Type: Bathroom 3
  • Room Description: Full Hall Bathroom
Room 17 Information
  • Room Level: Second
  • Room Type: Auxiliary Room
  • Room Description: Grand Hallway with Extensive Closets
Room 18 Information
  • Room Level: Second
  • Room Type: Auxiliary Room
  • Room Description: Rear foyer with access to a grand balcony overlooking the grounds
Room 19 Information
  • Room Level: First
  • Room Type: Bathroom 2
  • Room Description: Full Bathroom
Taxes and HOA Information
Taxes and HOA Information
  • Parcel Number: 0800-051-00-07-00-005-001
  • Tax Source: Municipality
  • Tax Year: 2025
  • Association: No
Interior and Exterior Features
Interior Features
  • Amenities: 1st Floor Bedrm, Balcony, Barn(s), Built-in Features, Chefs Kitchen, Crown Molding, Deck, Eat in Kitchen, Entertainment Cabinets, Entrance Foyer, Estate, First Floor Full Bath, Formal Dining, Hardwood Floors As Seen, In-Law Floorplan, Natural Woodwork, Open, Original Details, Outbuilding, Panoramic, Pantry, Patio, Porch, Primary Bathroom, Privacy, Public, River, River Front, Stable(s), Trees/Woods, Walk In Closet, Water Access, Water View, Waterfront, Well, Wet Bar, Workshop
  • Interior Features: First Floor Bedroom, First Floor Full Bath, Built-in Features, Chefs Kitchen, Crown Molding, Eat-in Kitchen, Entertainment Cabinets, Entrance Foyer, Formal Dining, In-Law Floorplan, Natural Woodwork, Original Details, Pantry, Primary Bathroom, Walk-In Closet(s), Wet Bar
  • Appliances: Oven, Range, Refrigerator
  • Total Rooms: 17
  • Basement: Full, Walk-Out Access
  • Attic Description: Full,Walkup
  • Fireplace: Yes
  • Fireplaces Total: 5
  • Location Amenities: Walk Out Basement, Balcony, Hardwood Floors As Seen, 1st Fl Master Bedroom, Chef's Kitchen, Eat in Kitchen, Entry Foyer, Foyer, Formal Dining Room, Original Details, Pantry, Walk In Closet, Wetbar, Barn(s), Out Building, Workshop, Deck, Patio, Porch, Open View, River, River Views, Water View, Water Access
  • Spa: No
  • Flooring: Hardwood
  • Living Area: 6000
  • Basement: Yes
Exterior Features
  • Exterior Features: Balcony
  • Exterior Property Features: Balcony, Deck, Patio, Porch, Oversized, Private, Level, Part Wooded, Sloped
  • Elevation Certificate: No
  • Patio And Porch Features: Deck, Patio, Porch
  • Construction Materials: Clapboard, Frame, Wood Siding
  • Other Structures: Barn(s), Outbuilding, Stable(s), Workshop
  • Waterfront Features: River Front, Water Access, Waterfront
  • Horse: Yes
  • Pool Private: No
Lot Information
  • Lot Features: Level, Part Wooded, Sloped
  • Site Features: Level, Part Wooded, Sloped
  • Building Area Units: Square Feet
Parking
  • Parking Features: Oversized, Private
  • Garage: No
  • Carport: No
Utilities
  • Cooling: Wall/Window Unit(s)
  • Heating: Hot Water, Oil
  • Heat Fuel Type: Hot Water, Oil
  • Sewer: Cesspool
  • Water Source: Well, Private, Public
  • Utilities: See Remarks
Green Features
  • Green Features: Oven, Range, Refrigerator, Hot Water, Oil, Balcony
Agent
Payment and Rate
  • Down Payment Resource: No

Property History for 38 Landing Meadow Road

DateEvent & SourcePriceAppreciation
Jul 20, 2026

Listed (Active)

ONEKEY #1022766

$3,995,000—
Dec 6, 2025

Expired

ONEKEY #873824

$5,899,000—
Jun 5, 2025

Listed (Active)

ONEKEY #873824

$5,899,000—
DateEvent & SourcePrice
07/20/2026

Listed (Active)

ONEKEY #1022766

$3,995,000
12/06/2025

Expired

ONEKEY #873824

$5,899,000
06/05/2025

Listed (Active)

ONEKEY #873824

$5,899,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 38 Landing Meadow Road

Taxable ValueLand$700Additions$1,135Total$1,835
Tax Record2024$5,002 ($417 / month)
Home Facts
Lot Size879,912 SqFtStyleMiscellaneous AgriculturalCountySUFFOLKAPN0800-051.00-07.00-005.004

Schools near 38 Landing Meadow Road

This home is within Smithtown Central School District.
Rating
School
Type
Grades
Distance
Smithtown Elementary School
Public - K to 5
Nesaquake Middle School
Public - 6 to 8
Smithtown High School East
Public - 9 to 12
Accompsett Middle School
Public - 6 to 8
Rating
School
Distance
Smithtown Elementary School
PublicK to 5

Nesaquake Middle School
Public6 to 8

Smithtown High School East
Public9 to 12

Accompsett Middle School
Public6 to 8

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 38 Landing Meadow Road, Smithtown, NY 11787

38 Landing Meadow Road is a single family home for sale in Smithtown, NY 11787. This property was listed for sale on July 20, 2026 by LAFFEY REAL ESTATE, it's currently listed at $3,995,000. It has been on the market for a total of 61 days and was last sold on May 6, 2016. This listing's school district is Smithtown Central School District. Nearby schools include Smithtown Elementary School, Nesaquake Middle School and Smithtown High School East. 38 Landing Meadow Road is a 7-bed, 6-bath, 6,000 sqft single family home built in 1828.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim 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 seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of LAFFEY REAL ESTATE, Philip C. Laffey; LAFFEY REAL ESTATE, Mark T. Laffey

Based on information submitted to the MLS GRID as of 09/18/2026 11:37 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.