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38 Landing Meadow Road, Smithtown, NY, 11787

7beds
6baths
6,000sqft
$3,995,000
$666price/sqft
$27,880/moest. monthly cost
$1,115,200/yrincome needed

About This Home

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.

Getting Around

1
WalkingCar-Dependent
0
TransitVery Limited Transit
2
BikeSomewhat Bikeable

Schools

7/10
7/10
Accompsett Middle SchoolGrades 6-82.4 mi
10/10

Construction

Condition

  • Year built: 1828

Materials

  • Construction materials: Clapboard,Frame,Wood Siding

Notable Dates

  • Major remodel year: 2016

Type & Style

  • Home type: SingleFamily
  • Architectural style: Estate
  • Property subType: Single Family Residence,Residential

Interior

Appliances

  • Appliances included: Oven,Range,Refrigerator

Basement

  • Level: Basement

Basement

  • Has basement: Yes
  • Basement: Full,Walk-Out Access

Bathroom1

  • Level: First

Bathroom2

  • Level: First

Bathroom3

  • Level: Second

Bedroom1

  • Level: First

Bedroom2

  • Level: Second

Bedroom3

  • Level: Second

Bedroom4

  • Level: Second

Bedroom5

  • Level: Second

Bedrooms & Bathrooms

  • Bedrooms: 7
  • Bathrooms: 6
  • Full bathrooms: 5
  • 1/2 bathrooms: 1

Bonus Room

  • Level: First

Den

  • Level: First

Dining Room

  • Level: First

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
  • Number of fireplaces: 5
  • Fireplace: Yes
  • Attic: Full,Walkup

Heating & Cooling

  • Heating features: Hot Water,Oil
  • Cooling features: Wall/Window Unit(s)

Interior Area

  • Total structure area: 6,000
  • Total interior livable area: 6,000 sqft

Kitchen

  • Level: First

Living Room

  • Level: First

Master Bedroom

  • Level: Second

Office

  • Level: First

Other

  • Level: First

Other

  • Level: Second

Other

  • Level: Second

Property

Details

  • Parcel number: 0800051000700005001
  • Special condition: None

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
  • On waterfront: Yes
  • Waterfront features: River Front,Water Access,Waterfront
  • Residential vegetation: Partially Wooded
  • Horses can be raised: Yes

Lot

  • Lot size: 23 Acres
  • Features: Level,Sloped

Parking

  • Parking features: Oversized,Private

Climate Risk is Financial Risk

Every home has a financial story beyond the listing price. Below, you’ll see the climate risks that could affect this property — and in Bills & Affordability, how those risks may influence repairs, insurance, utilities, and long-term value.

Biggest Threats for This Home

  • Hurricane
    HurricaneModerate
  • Strong Wind
    Strong WindModerate
  • Winter Weather
    Winter WeatherModerate
  • Tsunami
    TsunamiInsufficient Data

How This Home’s Risks Compare

Hurricane
Strong Wind
Winter Weather
Tsunami

FEMA Declared Disasters in Suffolk County and New York

Flood
Severe Storm
Snowstorm
Straight Line Winds
Tropical Storm
Winter Storm

Understanding the Costs

Financial advisors generally recommend spending no more than 30% of your gross household income on housing costs. In practice, many households stretch to 35% or beyond — especially in high-cost markets.

Estimated Costs Today

MonthlyAnnual
Mortgage $20,200$242,400
Home Insurance *$1,296$15,552
Property Taxes $5,393$64,716
Electricity $991$11,898
Total$27,880$334,560
*Does not include cost of any FAIR Plan premiums

Income You'd Need if You Spent...

35% on housing$955,885/yr
40% on housing$836,400/yr
45% on housing$743,466/yr

New York FAIR Plan Programs

New York Property Insurance Underwriting Association

Covered
WildfireWildfire
HailHail
WindWind
Visit Website →
Current Policies
Residential: 20,669Commercial: 1,556
Total Premiums$32.27M
Total Exposure$7.63B

How Costs Could Change Over Time

Climate risk is quickly impacting all of the major home ownership costs. Adjust the growth rates and percentage of income spent on housing below to see how your housing costs could change over the next 10 years — and what income you'd need to keep up.

Insurance Growth Rate5-year average: 4.6%
4.6%
0%30.0%
Electricity Growth Rate10-year average: 7.1%
7.1%
0%15.0%
Property Taxes Growth Rate2-year average: 1.0%
1.0%
0%15.0%
Income Spent on Housing
30%
30%45%

Comparing Against the Market

Price Per Sq Ft

$666This listing

vs Other Active Listings

Avg $/sqft

ZIP 11787$424
Suffolk County$724

vs Homes Sold Last Month

Median $/sqft

ZIP 11787$400
Suffolk County$412

Current Market Trends

Median Price Per Square Foot

The median price per square foot of homes sold in this area each month. Compare this to this listing's price per square foot to gauge whether the home is priced in line with recent sales.

Historicals for This Listing

Zestimate History ($/sqft)

Price History

DateEventPrice
2026-07-20Listed for sale$3,995,000
2025-12-06Listing removed$5,899,000
2025-06-05Listed for sale$5,899,000
2016-05-06Sold$1,333,000
2016-01-01Listing removed$1,499,990
2015-10-27Listed for sale$1,499,990
2015-08-01Listing removed$1,499,990
2015-06-21Price change$1,499,990
2015-04-05Price change$1,599,000
2014-12-10Listed for sale$1,999,990
2014-08-28Listing removed$1,500,000
2014-02-11Price change$1,500,000
2014-02-09Listed for sale$3,500,000

For Sale by Agent

AgentPhilip C. Laffey
BrokerageLAFFEY REAL ESTATE

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