13

Smithtown, NY Homes for Sale with Acreage

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  • /42

    $1,645,000

    $150K PRICE DROP
    • 7 Beds
    • 5.5 Baths
    • 6,087 Sq Ft

    60 Winston Dr, Smithtown, NY 11787

    FSBO. At $270 per square foot, this impressive contemporary is the best value in the Smithtown Pines! Set on a beautifully landscaped level 1.06-acre property in the desirable Hamlet of Smithtown Pines, this expansive 6,087 square foot under roof, 17-room contemporary offers an exceptional blend of space, elegance and resort-style living. Featuring 7 bedrooms, 5.5 bathrooms, and a dedicated

    Derek Greene Greene Realty Group

    60 Winston Dr, Smithtown, NY 11787
  • /48

    $2,599,000

    • 6 Beds
    • 8 Baths
    • 3,946 Sq Ft

    2 Riverview Terrace, Smithtown, NY 11787

    Paradise on the Nissequogue River with 65 feet of waterfront, ideal for canoeing, kayaking, and serene relaxation. This impressive 5,500+ sq ft contemporary with traditional accents offers 15 rooms and two fully separate living quarters, each with its own basement—perfect for extended or multi-generational living. Both residences feature updated granite eat-in kitchens with wood cabinetry and

    Jamie Marcantonio Signature Premier Properties

    2 Riverview Terrace, Smithtown, NY 11787
  • /50

    $1,200,000

    • 3 Beds
    • 3 Baths
    • 2,118 Sq Ft

    30 Landing Meadow Rd, Smithtown, NY 11787

    Welcome to your private 1.09-acre retreat, offering the perfect blend of comfort, space, and outdoor living. This beautifully maintained home features wood flooring throughout the main living areas, with tile flooring in the foyer, bathrooms, and laundry room for added durability and convenience. The spacious primary suite is conveniently located on the first floor and includes a walk-in closet

    Linda Wilson Exit Realty Achieve

    30 Landing Meadow Rd, Smithtown, NY 11787
  • /44

    $1,686,000

    $102K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 3,851 Sq Ft

    589 Landing Ave, Smithtown, NY 11787

    Nestled at the end of a private long drive shared with only 2 other homes and Not directly on Landing, this magnificent custom brick home offering Luxurious living space on a private 1.2 acre setting. features include a dramatic two-story grand entry foyer with two staircases, soaring vaulted ceilings, gourmet chef's kitchen with cherry cabinetry, granite countertops and Viking appliances,

    Jin Tao Realty Connect USA L I Inc

    589 Landing Ave, Smithtown, NY 11787
  • /15

    $3,499,000

    New Construction $504K PRICE INCREASE
    • 6 Beds
    • 6.5 Baths
    • 6,000 Sq Ft

    326 Nissequogue River Rd, Saint James, NY 11780

    **Starting Summer 2026!** Brand New Waterfront 6000 sq ft Modern Barn Home on 2acre Lot, *PRE-CONSTRUCTION PRICE*6 Bdrm 6.5 Bath,2 acre lot, 10ft Ceilings w 8'ft Interior Doors,2x4 2x6 Framing, Oversized Andersen400 Windows,Exterior Doors, 5/8 sheetrock, Energy Star Insulation, interior soundproofing. Pre wired A/V, alarm, cameras, Wi-Fi. Custom Kitchen Cabinetry & Bath Vanities. Kohler Bath

    Brian Hickey Hickey & Smith REALTORS

    326 Nissequogue River Rd, Saint James, NY 11780
  • /44

    $1,680,000

    • 5 Beds
    • 2.5 Baths
    • 3,851 Sq Ft

    589 Landing Ave, Smithtown, NY 11787

    Nestled at the end of a private long drive shared with only 2 other homes and Not directly on Landing, this magnificent custom brick home offering Luxurious living space on a private 1.2 acre setting. features include a dramatic two-story grand entry foyer with two staircases, soaring vaulted ceilings, gourmet chef's kitchen with cherry cabinetry, granite countertops and Viking appliances,

    Jin Tao Realty Connect USA L I Inc

    589 Landing Ave, Smithtown, NY 11787
  • /2

    $799,999

    Coming Soon
    • 4 Beds
    • 2 Baths

    191 Old Willets Path, Smithtown, NY 11787

    Smithtown opportunity awaits! This Hi-Ranch horse property home is situated on a beautiful 1-acre lot, set back off the road for added privacy and a peaceful setting. This versatile property features a possible mother/daughter setup with proper permits, providing flexibility for a variety of living arrangements. Additional features include central air conditioning, a wood-burning stove, full

    Traci Conforti Realty Connect USA L I Inc

    191 Old Willets Path, Smithtown, NY 11787
  • /27

    $995,000

    Open Sun 12PM - 2PM $4K PRICE DROP
    • 7 Beds
    • 3 Baths
    • 2,456 Sq Ft

    80 Mount Pleasant Rd, Smithtown, NY 11787

    Calling all land lovers! Step into this beautiful Smithtown home exclusively located in the Village of the Branch! This move-in ready ranch carries 7 bedrooms & 3 full bathrooms with a brick walkway to the entrance, a wrap around driveway & a 2 car attached garage nestled on a whole 1 acre of beautiful land. Part the Smithtown School District, it is zoned for Mt. Pleasant Elementary School, Great

    Sophia Wu Homes By Mara

    80 Mount Pleasant Rd, Smithtown, NY 11787
  • /38

    $1,890,000

    • 4 Beds
    • 2.5 Baths
    • 3,211 Sq Ft

    225 Old Willets Path, Smithtown, NY 11787

    Welcome to this one-of-a-kind custom estate-quality residence rebuilt in 2018 by a professional contractor as his personal home with attention to detail and premium materials throughout. Situated on a private 1-acre property, this exceptional 4-bedroom, 2 1/2 bath home welcomes you with a striking stone façade and dramatic arched entryway that sets the tone for the extraordinary craftsmanship

    carol hurnyak Long Island Homes & Horse Prop

    225 Old Willets Path, Smithtown, NY 11787
  • /2

    $949,000

    • 4 Beds
    • 2.5 Baths
    • 2,600 Sq Ft

    434 Meadow Rd, Kings Park, NY 11754

    BUILDERS INVESTORS!!!IDEAL PROPRTY IN PRIME KINGS PARK LOCATIONSUBDIVISION WAS APPROVED IN 2005( WITH BOARD OF HEALTH APPROVAL) INTO 2 PARCELSHOUSE AND ONE LOT PREVIOUS OWNER LET IT EXPIRE IT CAN BE ARROVED AGAIN!!!ORIGINAL SURVEY IS ATTACHED (REVISED SURVEYS SHALL BE COMPLETED WITHIN 2-3 WEEKS)

    Pedro velez Deal House Realty Inc.

    434 Meadow Rd, Kings Park, NY 11754
  • /5

    $499,000

    • Land
    • 2.25 Acres
    • $221,778 per Acre

    260 Old Mill Rd, Smithtown, NY 11780

    Build Your Dream Home in Spectacular and Peaceful Nissequogue Village. Building permit was issued on 12/9/25.Located in the heart of the serene and prestigious Nissequogue Village, this exceptional property offers the rare opportunity to bring your vision to life.Key Features:• Approved blueprints for a luxurious 5-bedroom, 5.5-bathroom home designed with modern elegance and

    Bryan Whalen VYLLA Home

    260 Old Mill Rd, Smithtown, NY 11780
  • /27

    $1,200,000

    • 5 Beds
    • 3 Baths
    • 3,000 Sq Ft

    451 River Rd, Saint James, NY 11780

    Nestled on 2.5 private acres in the picturesque Village of Nissequogue, this beautifully remodeled Colonial offers a rare opportunity to enjoy peaceful country-style living with seasonal water views of the Nissequogue River in one of Long Island’s most sought-after communities.This well-maintained home features numerous updates, including a newer roof, siding, driveway, eat-in kitchen, and

    Marianne Koke Daniel Gale Sothebys Intl Rlty

    451 River Rd, Saint James, NY 11780
  • /50

    $2,499,999

    • 6 Beds
    • 5 Baths
    • 4,375 Sq Ft

    15 the Chase, Saint James, NY 11780

    Nestled within one of Long Island’s most coveted North Shore enclaves, 15 The Chase presents a rare opportunity to experience refined estate living in the prestigious Village of Head of the Harbor. Privately set amid mature trees and manicured grounds in the highly coveted White Spruce Farms community. This exceptional residence combines timeless architectural elegance with modern comfort, with

    William Galati Signature Premier Properties

    15 the Chase, Saint James, NY 11780

Home Price Trends

Median Sale Price
$815,000
Median Single Family Sale Price
$825,000
Median Townhouse Sale Price
$774,999
Median 2 Bedroom Sale Price
$629,000
Median 1 Bedroom Sale Price
$270,000
Average Price Per Sq Ft
$418
Number of Homes for Sale
65
Last 12 months Home Sales
291
Months of Supply
2.70
Median List Price
$799,000
Median Change From 1st List Price
-3%
Median Home Sale Price YoY Change
4%
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