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Smithtown, NY Homes for Sale with Acreage

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  • /40

    $1,899,999

    • 8 Beds
    • 6 Baths
    • 6,700 Sq Ft

    30 Lone Oak Path, Smithtown, NY 11787

    Welcome to 30 Lone Oak Path, a grand haven nestled in the heart of the highly sought hamlet of Smithtown Pines. This exquisite home offers the opportunity for multi-generational living, it is an expansive and distinctively designed custom-built 6500 plus square foot home sits on a one plus-acre lot. Open the double front doors and step into an exquisite open concept first floor grand entry foyer

    Thomas Diana Douglas Elliman Real Estate

    30 Lone Oak Path, Smithtown, NY 11787
  • /45

    $1,450,000

    • 4 Beds
    • 3.5 Baths
    • 2,400 Sq Ft

    109 Oakside Dr, Smithtown, NY 11787

    Welcome to 109 Oakside Dr., your dream equestrian retreat, set on 2 scenic acres in the heart of Smithtown. This updated 4-bed, 3.5-bath ranch blends easy single-level living with true equestrian amenities. An eat-in kitchen with granite counters and stainless appliances opens to a spacious family room anchored by a stone fireplace. Throughout the home you’ll find hardwood floors, custom

    George McKnight George Mcknight REALTORS Inc

    109 Oakside 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
  • /43

    $2,988,888 Open Sun 1:30PM - 3:30PM

    • 4 Beds
    • 5 Baths
    • 7,000 Sq Ft

    7 Riverview Terrace, Smithtown, NY 11787

    Welcome to 7 Riverview Terrace, an exceptional waterfront residence. Every inch of this home reflects modern Long Island luxury, designed for those who appreciate architecture, innovation, and tranquility in perfect harmony. With sweeping views of the Nissequogue River and a sense of privacy that feels worlds away, this home defines the North Shore lifestyle at its highest level. From the moment

    Vincent Chiaramonte Signature Premier Properties

    7 Riverview Terrace, Smithtown, NY 11787
  • /2

    $2,995,000

    • 6 Beds
    • 6.5 Baths
    • 6,000 Sq Ft

    326 Nissequogue River Rd, Saint James, NY 11780

    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 Fixtures, Frameless Bath

    Brian Hickey Hickey & Smith REALTORS

    326 Nissequogue River Rd, Saint James, NY 11780
  • /27

    $999,999

    • 4 Beds
    • 2 Baths
    • 2,300 Sq Ft

    769 Meadow Rd, Smithtown, NY 11787

    Great Opportunity with OVER 2 Acres in Prime Smithtown Location. Possible Sub Division, Horses, Dog Kennel, Family Compound, Landscapers, Tree Companies, Endless Room for Growth Here ! Current Home is Cape with 4 Bedrooms and 2 Baths, Detached 40x30 Garage in Rear, Circular Driveway, 200 Amp, Low Line Cesspool, Room for Extended Family, Smithtown Schools and MORE !

    Robert Scarito Douglas Elliman Real Estate

    769 Meadow Rd, Smithtown, NY 11787
  • /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

Home Trends in Smithtown, NY

Housing Trends

Median Sale Price
$820,000
Median Single Family Sale Price
$826,000
Median Townhouse Sale Price
$772,000
Median 2 Bedroom Sale Price
$657,500
Median 1 Bedroom Sale Price
$260,000
Average Price Per Sq Ft
$408
Number of Homes for Sale
24
Last 12 months Home Sales
309
Months of Supply
0.90
Median List Price
$799,000
Median Change From 1st List Price
-3%
Median Home Sale Price YoY Change
9%
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