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For sale
    • $3,995,000

    38 Landing Meadow Road, Smithtown, NY 11787

    7beds
    6,000sqft
    Single Family Residence, Residential
    Built in 1828
    23 Acres Lot
    $-- Zestimate®
    $666/sqft
    $-- HOA

    What's special

    Grand den with fireplaceEmerald lawnsLong private drivewayWide open vistasMagnificent mature treesButlers pantryForever-preserved backdrop
    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.
    65 days
    1,270
    97

    Zillow last checked:

    Listing updated:

    Listed by:

    LAFFEY REAL ESTATE 516-328-3233,

    Philip C. Laffey 516-359-1489,

    Mark T. Laffey 516-818-1919,

    LAFFEY REAL ESTATE

    Source: OneKey® MLS as distributed by MLS GRID,MLS#: 1022766MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 7
      • Bathrooms: 6
      • Full bathrooms: 5
      • 1/2 bathrooms: 1
      Primary bedroom
      • Description: Primary suite with fireplace, huge walk-in closet and bathroom
      • Level: Second
      Bedroom 1
      • Description: Ensuite with a Grand Wet Bar and Private Seperate Entrance
      • Level: First
      Bedroom 2
      • Description: Fireplace
      • Level: Second
      Bedroom 3
      • Description: Access to Jack and Jill bathroom
      • Level: Second
      Bedroom 4
      • Description: Access to Jack and Jill bathroom
      • Level: Second
      Bedroom 5
      • Level: Second
      Bathroom 1
      • Description: Half Bathroom
      • Level: First
      Bathroom 2
      • Description: Full Bathroom
      • Level: First
      Bathroom 3
      • Description: Full Hall Bathroom
      • Level: Second
      Other
      • Description: Entry Foyer: Front to hallway with rear door to a covered grand patio
      • Level: First
      Other
      • Description: Grand Hallway with Extensive Closets
      • Level: Second
      Other
      • Description: Rear foyer with access to a grand balcony overlooking the grounds
      • Level: Second
      Basement
      • Description: Full, Unfinished, Laundry Room, Storage, Mechanical
      • Level: Basement
      Bonus room
      • Description: Butlers Pantry
      • Level: First
      Den
      • Description: With fireplace and multiple doors to outside and patio
      • Level: First
      Dining room
      • Description: Formal Dining Room with fireplace and door to outside
      • Level: First
      Kitchen
      • Description: Large and open eat-in-kitchen, gas cooking and access to a back staircase
      • Level: First
      Living room
      • Description: Living Room or Music Room
      • Level: First
      Office
      • Description: Office or library with fireplace
      • Level: First
      Heating
      • Hot Water, Oil
      Cooling
      • Wall/Window Unit(s)
      Appliances
      • Included: Oven, Range, Refrigerator
      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
      • Flooring: Hardwood
      • Basement: Full,Walk-Out Access
      • Attic: Full,Walkup
      • Number of fireplaces: 5
      Interior area
      • Total structure area: 6,000
      • Total interior livable area: 6,000 sqft

      Property

      Parking
      • Parking features: Oversized, Private
      Features
      • Levels: Two
      • Patio & porch: Deck, Patio, Porch
      • Exterior features: Balcony
      • Has view: Yes
      • View description: Open, Panoramic, River, Trees/Woods, Water
      • Has water view: Yes
      • Water view: River,Water
      • Waterfront features: River Front, Water Access, Waterfront
      Lot
      • Size: 23 Acres
      • Features: Level, Sloped
      • Residential vegetation: Partially Wooded
      Details
      • Additional structures: Barn(s), Outbuilding, Stable(s), Workshop
      • Parcel number: 0800051000700005001
      • Special conditions: None
      • Horses can be raised: Yes

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Estate
      • Property subtype: Single Family Residence, Residential
      Materials
      • Clapboard, Frame, Wood Siding
      Condition
      • Year built: 1828
      • Major remodel year: 2016

      Utilities & green energy

      • Sewer: Cesspool
      • Water: Well, Private, Public
      • Utilities for property: See Remarks

      Community & HOA

      HOA
      • Has HOA: No
      Location
      • Region: Smithtown

      Financial & listing details

      • Price per square foot: $666/sqft
      • Tax assessed value: $1,455,000
      • Annual tax amount: $37,095
      • Date on market: 7/20/2026
      • Cumulative days on market: 66 days
      • Listing agreement: Exclusive Right To Sell
      • Listing terms: Contract

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        7/20/2026Listed for sale$3,995,000-32.3%$666/sqft
        Source: OneKey® MLS as distributed by MLS GRID #1022766 Report a problem
        12/6/2025Listing removed$5,899,000$983/sqft
        Source: OneKey® MLS as distributed by MLS GRID #873824 Report a problem
        6/5/2025Listed for sale$5,899,000+342.5%$983/sqft
        Source: OneKey® MLS as distributed by MLS GRID #873824 Report a problem
        5/6/2016Sold$1,333,000-11.1%$222/sqft
        Source: OneKey® MLS as distributed by MLS GRID #L2806549 Report a problem
        1/1/2016Listing removed$1,499,990$250/sqft
        Source: RE/MAX Integrity Leaders #2806549 Report a problem
        10/27/2015Listed for sale$1,499,990$250/sqft
        Source: RE/MAX Integrity Leaders #2806549 Report a problem
        8/1/2015Listing removed$1,499,990$250/sqft
        Source: RE/MAX Integrity Leaders #2719461 Report a problem
        6/21/2015Price change$1,499,990-6.2%$250/sqft
        Source: RE/MAX Integrity Leaders #2719461 Report a problem
        4/5/2015Price change$1,599,000-20%$267/sqft
        Source: RE/MAX Integrity Leaders #2719461 Report a problem
        12/10/2014Listed for sale$1,999,990+33.3%$333/sqft
        Source: RE/MAX Integrity Leaders #2719461 Report a problem
        8/28/2014Listing removed$1,500,000$250/sqft
        Source: Long Island Horse Properties #2646033 Report a problem
        2/11/2014Price change$1,500,000-57.1%$250/sqft
        Source: Long Island Horse Properties #2646033 Report a problem
        2/9/2014Listed for sale$3,500,000$583/sqft
        Source: Long Island Horse Properties #2646033 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025-- $11,640
        2024-- $11,640
        2023-- $11,640
        2022-- $11,640
        2021-- $11,640
        2020-- $11,640
        2019-- $11,640
        2018-- $11,640
        2017$24,356 $11,640
        2016-- $11,640
        2015-- $11,640
        2014-- $11,640
        2013-- $11,640
        2012-- $11,640
        2011-- $11,640
        2007$20,523 +19.7%$11,640
        2005$17,143 +7.1%$11,640
        2004$16,012 +8%$11,640
        2003$14,830 +7.8%$11,640
        2002$13,755 $11,640
        2001-- $11,640
        2000$12,769 $11,640
        Find assessor info on the county website

        Monthly payment

        Estimated monthly payment$1,822
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
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        Climate risks

        Neighborhood: 11787

        Getting around

        1 / 100
        Car-Dependent
        2 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Accompsett Elementary School
        • Middle: Accompsett Middle School
        • High: Smithtown High School-East

        Source: OneKey® MLS as distributed by MLS GRID. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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