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.

Facts and features

Schools

• Smithtown Elementary School

  elementary · K-5 · 1.3 mi

  7

• Nesaquake Middle School

  middle · 6-8 · 0.9 mi

  7

• St Patrick Elementary School

  elementary · K-8 · 1.5 mi

• Smithtown High School East

  high · 9-12 · 1.6 mi

  10

• Dogwood Elementary School

  elementary · K-5 · 1.3 mi

  8

• Smithtown Christian School

  elementary · K-12 · 1.7 mi

Price history

• Jul 20, 2026 · Listed$3,995,000
• Dec 6, 2025 · Listing Removed$5,899,000
• Jun 5, 2025 · Listed$5,899,000
• Jun 2, 2022 · Sold$2,100,000
• Jun 14, 2016 · Sold$1,333,000
• May 6, 2016 · Sold$1,333,000
• Oct 27, 2015 · Listed$1,499,990
• Jul 31, 2015 · Listing Removed$1,499,990

Tax history

• 2025$31,612 tax · $11,640 assessed
• 2024$29,587 tax · $11,640 assessed
• 2022$28,781 tax · $11,640 assessed
• 2021$28,333 tax · $11,640 assessed
• 2020$28,285 tax · $11,640 assessed
• 2018$27,515 tax · $11,640 assessed
• 2017$26,545 tax · $11,640 assessed
• 2016$26,214 tax · $11,640 assessed

Home value

$3,955,000

• Collateral Analytics$3,955,000
• Cotality$1,616,500

Where it is