




38 Landing Meadow Road, Smithtown, NY, 11787
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
Schools
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
- Strong Wind
- Winter Weather
- Tsunami
How This Home’s Risks Compare
FEMA Declared Disasters in Suffolk County and New York
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
| Monthly | Annual | |
|---|---|---|
| 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 |
Income You'd Need if You Spent...
New York FAIR Plan Programs
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.
Comparing Against the Market
Price Per Sq Ft
vs Other Active Listings
Avg $/sqft
vs Homes Sold Last Month
Median $/sqft
Current Market Trends
Median Price Per Square Foot
The median price per square foot of homes sold in this area each month. Compare this to this listing's price per square foot to gauge whether the home is priced in line with recent sales.
Historicals for This Listing
Zestimate History ($/sqft)
Price History
| Date | Event | Price |
|---|---|---|
| 2026-07-20 | Listed for sale | $3,995,000 |
| 2025-12-06 | Listing removed | $5,899,000 |
| 2025-06-05 | Listed for sale | $5,899,000 |
| 2016-05-06 | Sold | $1,333,000 |
| 2016-01-01 | Listing removed | $1,499,990 |
| 2015-10-27 | Listed for sale | $1,499,990 |
| 2015-08-01 | Listing removed | $1,499,990 |
| 2015-06-21 | Price change | $1,499,990 |
| 2015-04-05 | Price change | $1,599,000 |
| 2014-12-10 | Listed for sale | $1,999,990 |
| 2014-08-28 | Listing removed | $1,500,000 |
| 2014-02-11 | Price change | $1,500,000 |
| 2014-02-09 | Listed for sale | $3,500,000 |
