13,235

Smithtown, NY Homes

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  • 2 Cindy St, Smithtown, NY 11787
    2 Cindy St, Smithtown, NY 11787
    2 Cindy St, Smithtown, NY 11787
    /36

    $849,999

    $75K PRICE INCREASE Pending
    • 4 Beds
    • 1.5 Baths
    • 1,900 Sq Ft

    2 Cindy St, Smithtown, NY 11787

    BACK ON MARKET BUYERS FAILED TO PRODUCE - Say Hello To Your New Home! This Colonial Is A True Stunner Featuring Hardwood Floors And A Great Open Layout That Just Makes Sense. Brand New Chef’s Kitchen With Stainless Steel Appliances And Plenty Of Cabinet Space, Flowing Right Into Your Main Living Areas. The First Floor Also Offers A Comfortable Living Room With A Fireplace, A Separate Den For

    Nicholas Pappas Coldwell Banker American Homes

    2 Cindy St, Smithtown, NY 11787
  • 34 Brooksite Dr, Smithtown, NY 11787

    $775,000

    Sold Jan 02, 2026

    34 Brooksite Dr, Smithtown, NY 11787

    • 3 Beds
    • 3 Baths
    • 2,525 Sq Ft
    • Built 1960

    Last Sold Summary

    • 3% Above List Price
    • $307/SF
    • 8 Days On Market

    Current Estimated Value $792,125

    Last Listing Agent Pedro velez Deal House Realty Inc.

    34 Brooksite Dr, Smithtown, NY 11787
  • 4 Sherbrooke Dr, Smithtown, NY 11787
    4 Sherbrooke Dr, Smithtown, NY 11787
    4 Sherbrooke Dr, Smithtown, NY 11787
    /38

    $799,000

    • 5 Beds
    • 2 Baths
    • 2,800 Sq Ft

    4 Sherbrooke Dr, Smithtown, NY 11787

    Welcome to this beautifully maintained move in ready Hi-ranch, nestled in the desirable Sherbrooke Drive section of Smithtown. This home offers 2800 sq. ft. of living space with 11 rooms and exceptional versatility. RARE BONUS: Legal Garage Conversion to a gorgeous suite that includes a bedroom, living room, walk in closet, bathroom, summer kitchen & two separate entrances! In addition, new

    Kathleen Micozzi Howard Hanna Coach

    4 Sherbrooke Dr, Smithtown, NY 11787
  • 203 Pond View Ln, Smithtown, NY 11787

    $485,000

    Sold Dec 03, 2025

    203 Pond View Ln, Smithtown, NY 11787

    • 1 Bed
    • 1.5 Baths
    • 1,044 Sq Ft
    • Built 1987

    Last Sold Summary

    • 2% Above List Price
    • $465/SF
    • 15 Days On Market

    Current Estimated Value $498,317

    Last Listing Agent Brandi Everett Coldwell Banker American Homes

    203 Pond View Ln, Smithtown, NY 11787
  • 48 River Heights Dr, Smithtown, NY 11787
    48 River Heights Dr, Smithtown, NY 11787
    48 River Heights Dr, Smithtown, NY 11787
    /40

    $1,499,999

    • 5 Beds
    • 3.5 Baths
    • 4,800 Sq Ft

    48 River Heights Dr, Smithtown, NY 11787

    Welcome to 48 River Heights Drive where a tree lined street meets a true custom masterpiece in beautiful North Smithtown. This luxurious 4,800 sq ft home offers 5 bedrooms, 4 baths, a private office, and an incredible blend of high-end design, comfort, and functionality. Custom built, expanded, and fully renovated by the current owner, this home features Brazilian cherry and hardwood oak floors,

    Dina Powers Signature Premier Properties

    48 River Heights Dr, Smithtown, NY 11787
  • 365 Route 111 Unit C-4, Smithtown, NY 11787

    $269,000

    Sold Dec 17, 2025

    365 Route 111 Unit C-4, Smithtown, NY 11787

    • 1 Bed
    • 1 Bath
    • 1,000 Sq Ft
    • Built 1964

    Last Sold Summary

    • 10% Above List Price
    • $269/SF
    • 13 Days On Market

    Current Estimated Value $247,000

    Last Listing Agent Victoria Seeger Signature Premier Properties

    365 Route 111 Unit C-4, Smithtown, NY 11787
  • 6 Magnolia Ln, Smithtown, NY 11787
    6 Magnolia Ln, Smithtown, NY 11787
    6 Magnolia Ln, Smithtown, NY 11787
    /48

    $1,250,000

    Pending
    • 4 Beds
    • 3 Baths
    • 2,884 Sq Ft

    6 Magnolia Ln, Smithtown, NY 11787

    Welcome to this stately brick Colonial offering timeless character, exceptional space, all set on a quiet double cul-de-sac. This impressive home features a two-story foyer with an oak staircase and tons of natural light. Offering 4 spacious bedrooms and 3 full baths, this home’s large-scale primary suite is complete with walk-in closets and a luxurious en-suite bathroom with radiant heat

    Lisa Kass Coldwell Banker American Homes

    6 Magnolia Ln, Smithtown, NY 11787
  • 392 N Country Rd, Smithtown, NY 11787

    $750,000

    Sold Nov 12, 2025

    392 N Country Rd, Smithtown, NY 11787

    • 3 Beds
    • 3 Baths
    • 1,400 Sq Ft
    • Built 1910

    Last Sold Summary

    • 5% Below List Price
    • $536/SF
    • 28 Days On Market

    Current Estimated Value $749,609

    Last Listing Agent Fabian Sookoo Howard Hanna Coach

    392 N Country Rd, Smithtown, NY 11787
  • 4 Jerome St, Smithtown, NY 11787
    4 Jerome St, Smithtown, NY 11787
    4 Jerome St, Smithtown, NY 11787
    /46

    $779,999

    Pending
    • 5 Beds
    • 3 Baths
    • 1,989 Sq Ft

    4 Jerome St, Smithtown, NY 11787

    Incredible opportunity to own a newer, oversized high ranch offering five bedrooms, three full bathrooms, and a flexible layout ideal for multigenerational living, or those who love to entertain, all set on a flat, oversized corner lot with outstanding curb appeal and modern functionality. The property features a blacktop driveway with a Belgium block border, a paver front entry, and a fully

    Bryan Karp Coldwell Banker American Homes

    4 Jerome St, Smithtown, NY 11787
  • 7 Henlee Ct, Smithtown, NY 11787

    $745,000

    Sold Jun 30, 2025

    7 Henlee Ct, Smithtown, NY 11787

    • 4 Beds
    • 2 Baths
    • 2,000 Sq Ft
    • Built 1963

    Last Sold Summary

    • 3% Above List Price
    • $372/SF
    • 45 Days On Market

    Current Estimated Value $792,792

    Last Listing Agent Christine Jansson Realty Maintained LLC

    7 Henlee Ct, Smithtown, NY 11787
    • Unlisted Address

      Est $652,827

      Not Listed For Sale

      Unlisted Address

      • 4 Beds
      • 2 Baths
      • Built 1945
      Unlisted Address

      Last Sold Summary

      • 27 Days On Market

  • 31 Brooksite Dr, Smithtown, NY 11787
    31 Brooksite Dr, Smithtown, NY 11787
    /2

    $500,000

    Pending
    • 4 Beds
    • 2 Baths

    31 Brooksite Dr, Smithtown, NY 11787

    Home needs updating, Additional information: Appearance:Poor

    Barbara Ner Real Estate Plan LLC

    31 Brooksite Dr, Smithtown, NY 11787
  • 1 Charter Ln, Smithtown, NY 11787

    $766,500

    Sold Dec 15, 2025

    1 Charter Ln, Smithtown, NY 11787

    • 3 Beds
    • 2.5 Baths
    • 2,144 Sq Ft
    • Built 1967

    Last Sold Summary

    • 9% Below List Price
    • $358/SF
    • 198 Days On Market

    Current Estimated Value $794,589

    Last Listing Agent Verria Hairston Opendoor Brokerage LLC

    1 Charter Ln, Smithtown, NY 11787
  • 326A River Rd, Saint James, NY 11780
    326A River Rd, Saint James, NY 11780
    326A River Rd, Saint James, NY 11780
    /34

    $499,000

    Pending
    • Land
    • 2.1 Acres
    • $237,619 per Acre

    326A River Rd, Saint James, NY 11780

    History and Riverfront combine to create an unparalleled ambiance on this special property Prominently situated along the Nissequogue Riverfront. Rolling Lawn leads to River Level clearing previously home to the original estate horse paddock. Along the path to deeded river access stands what has been said to be the original rum running bunker room that fueled Smithtowns famed history.

    t johnson Daniel Gale Sothebys Intl Rlty

    326A River Rd, Saint James, NY 11780
  • 12 Friendly Rd, Smithtown, NY 11787

    $810,000

    Sold Aug 27, 2025

    12 Friendly Rd, Smithtown, NY 11787

    • 5 Beds
    • 2.5 Baths
    • 4,625 Sq Ft
    • Built 1990

    Last Sold Summary

    • 10% Below List Price
    • $175/SF
    • 83 Days On Market

    Current Estimated Value $918,596

    Last Listing Agent Monica Rea Signature Premier Properties

    12 Friendly Rd, Smithtown, NY 11787
  • 28 Willow Ridge Dr, Smithtown, NY 11787
    28 Willow Ridge Dr, Smithtown, NY 11787
    28 Willow Ridge Dr, Smithtown, NY 11787
    /43

    $699,999

    Pending
    • 2 Beds
    • 2.5 Baths
    • 1,863 Sq Ft

    28 Willow Ridge Dr, Smithtown, NY 11787

    Welcome to the highly sought-after Willow Ridge community in North Smithtown, where lifestyle, convenience, and opportunity come together.This "Canterbury" model offers a rare chance to create your dream home within one of the area’s most desirable townhome communities. Currently configured as a spacious 2-bedroom, 2-bath unit, this residence presents incredible potential to be converted into

    Brandon Cusma Realty Connect USA LLC

    28 Willow Ridge Dr, Smithtown, NY 11787
  • 32 Derby Place, Smithtown, NY 11787

    $785,000

    Sold Jun 23, 2026

    32 Derby Place, Smithtown, NY 11787

    • 3 Beds
    • 2.5 Baths
    • 1,609 Sq Ft
    • Built 1966

    Last Sold Summary

    • 1% Above List Price
    • $488/SF
    • 33 Days On Market

    Current Estimated Value $797,756

    Last Listing Agent Joseph Donofrio Douglas Elliman Real Estate

    32 Derby Place, Smithtown, NY 11787
  • 37 Pine Ridge Dr, Smithtown, NY 11787
    37 Pine Ridge Dr, Smithtown, NY 11787
    37 Pine Ridge Dr, Smithtown, NY 11787
    /49

    $1,275,000

    $275K PRICE INCREASE Pending
    • 4 Beds
    • 3.5 Baths
    • 3,013 Sq Ft

    37 Pine Ridge Dr, Smithtown, NY 11787

    Impeccably maintained and lovingly cared for, this DIAMOND oversized ranch is located in the coveted Smithtown Pines! This 4 bedroom, 3 1/2 bath home has beautiful hard wood floors with radiant heat (10 zones), soaring ceilings in many of the rooms, 2 fireplaces, one gas and one wood burning, CAC with 2 systems and 2 zones, in ground sprinklers, alarm system, natural gas service including a

    Veronica Mannarino Douglas Elliman Real Estate

    37 Pine Ridge Dr, Smithtown, NY 11787
  • 7 Village Way, Smithtown, NY 11787

    $755,000

    Sold Nov 19, 2025

    7 Village Way, Smithtown, NY 11787

    • 3 Beds
    • 2.5 Baths
    • 2,400 Sq Ft
    • Built 1965

    Last Sold Summary

    • 3% Below List Price
    • $315/SF
    • 49 Days On Market

    Current Estimated Value $804,228

    Last Listing Agent Rowena Nedvin Signature Premier Properties

    7 Village Way, Smithtown, NY 11787
  • 106 Summit Dr, Smithtown, NY 11787
    106 Summit Dr, Smithtown, NY 11787
    106 Summit Dr, Smithtown, NY 11787
    /27

    $749,000

    $50K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 2,100 Sq Ft

    106 Summit Dr, Smithtown, NY 11787

    Great Hi Ranch with 2 Sep Living Areas plus Garage, Fenced Yard, Oversize Driveway, Smithtown Schools, Central Air

    Robert Scarito Douglas Elliman Real Estate

    106 Summit Dr, Smithtown, NY 11787
  • 40 Ridge Rd, Smithtown, NY 11787

    $865,000

    Sold Jul 25, 2025

    40 Ridge Rd, Smithtown, NY 11787

    • 4 Beds
    • 2.5 Baths
    • 1,806 Sq Ft
    • Built 1967

    Last Sold Summary

    • 1% Above List Price
    • $479/SF
    • 17 Days On Market

    Current Estimated Value $905,139

    Last Listing Agent Robert Scarito Douglas Elliman Real Estate

    40 Ridge Rd, Smithtown, NY 11787
  • 260 Old Mill Rd, Smithtown, NY 11780
    260 Old Mill Rd, Smithtown, NY 11780
    260 Old Mill Rd, Smithtown, NY 11780
    /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
  • 3 Five Acre Ct, Smithtown, NY 11787

    $950,000

    Sold Dec 03, 2025

    3 Five Acre Ct, Smithtown, NY 11787

    • 3 Beds
    • 2 Baths
    • 1,706 Sq Ft
    • Built 1973

    Last Sold Summary

    • 12% Above List Price
    • $557/SF
    • 14 Days On Market

    Current Estimated Value $952,667

    Last Listing Agent Szabolcs Muharay HomeSmart Dynamic Realty

    3 Five Acre Ct, Smithtown, NY 11787
  • 23 Whitney Gate, Smithtown, NY 11787
    23 Whitney Gate, Smithtown, NY 11787
    23 Whitney Gate, Smithtown, NY 11787
    /48

    $800,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,500 Sq Ft

    23 Whitney Gate, Smithtown, NY 11787

    .Welcome to this classic Smithtown Colonial set on a beautiful .66-acre property surrounded by mature trees and a peaceful, private setting. This 4-bedroom, 2.5-bath home offers generous living space, timeless charm, and plenty of opportunity to make it your own. A welcoming front porch leads inside to a spacious layout featuring a bright living room, formal gathering spaces, hardwood floors, and

    James Haydon Realty Connect USA L I Inc

    23 Whitney Gate, Smithtown, NY 11787
  • 335 Landing Ave, Smithtown, NY 11787

    $850,000

    Sold Mar 24, 2026

    335 Landing Ave, Smithtown, NY 11787

    • 4 Beds
    • 2.5 Baths
    • 2,500 Sq Ft
    • Built 1975

    Last Sold Summary

    • 23% Above List Price
    • $340/SF
    • 19 Days On Market

    Current Estimated Value $843,895

    Last Listing Agent Kristin Lettieri Signature Premier Properties

    335 Landing Ave, Smithtown, NY 11787
  • 20 Veronica Ct, Smithtown, NY 11787
    20 Veronica Ct, Smithtown, NY 11787
    20 Veronica Ct, Smithtown, NY 11787
    /48

    $725,000

    Open Sun 2:30PM - 4PM $24K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,196 Sq Ft

    20 Veronica Ct, Smithtown, NY 11787

    Welcome to 20 Veronica Court, Smithtown — a spacious ranch-style home nestled on a quiet cul-de-sac in a desirable residential setting.This 5-bedroom, 3-bathroom ranch offers comfortable single-level living with additional space to grow. The primary bedroom features a private en-suite bathroom and direct access to its own secluded deck — the perfect spot to enjoy your morning coffee or unwind

    Daren Debel Keller Williams Points North

    20 Veronica Ct, Smithtown, NY 11787
  • 24 South Ave, Smithtown, NY 11787

    $630,000

    Sold Jul 30, 2025

    24 South Ave, Smithtown, NY 11787

    • 4 Beds
    • 2 Baths
    • Built 1940

    Last Sold Summary

    • 5% Above List Price
    • 19 Days On Market

    Current Estimated Value $665,306

    Last Listing Agent Nancy Stein Douglas Elliman Real Estate

    24 South Ave, Smithtown, NY 11787

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