Smithtown, NY Homes

• 

  

  

  /43

  $680,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,929 Sq Ft

  4 Landing Meadow Rd, Smithtown, NY 11787

  Step into a piece of Smithtown history with this charming Colonial, where timeless character and thoughtful updates come together beautifully. Nestled on a picturesque half-acre property in North Smithtown, this 3-bedroom, 2-bath home offers warmth, personality, and the kind of craftsmanship that is hard to find. Inside, you’ll find an inviting foyer and living room highlighted by a cozy

  Dana Murillo-Romeo Howard Hanna Coach

  4 Landing Meadow Rd, Smithtown, NY 11787
• 

  $1,175,000

  Sold Apr 09, 2026

  17 Thide Ct, Smithtown, NY 11787

  • 5 Beds
  • 2.5 Baths
  • 3,495 Sq Ft
  • Built 1967

  Last Sold Summary

  • 10% Below List Price
  • $336/SF
  • 66 Days On Market

  Current Estimated Value $1,188,748

  Last Listing Agent Maryanne Perillo Coldwell Banker American Homes

  17 Thide Ct, Smithtown, NY 11787
• 

  Est $1,092,291

  Not Listed For Sale

  99 River Heights Dr, Smithtown, NY 11787

  • 3 Beds
  • 2.5 Baths
  • 2,121 Sq Ft
  • Built 1967

  99 River Heights Dr, Smithtown, NY 11787

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent Candace McCabe Signature Premier Properties
• 

  

  

  /20

  $1,300,000

  New Construction Pending

  • 4 Beds
  • 2.5 Baths
  • 2,841 Sq Ft

  14 Sycamore Place, Smithtown, NY 11787

  3 LOTS LEFT!!! THE BRIDGEHAMPTON (2841 sqft base, with an option of a bonus room to bring total sqft to 3,114 SF): 4bdrm-2.5ba Center Hall Modern Farmhouse, (our most cutting edge design). Features include 2-story foyer, a spanning almost 50' open kitchen-dining-great room combination perfect for entertaining, and front or side-entry 2-car garage. This home is easily customizable into a 5/6 bdrm

  Paul Musso Realty Connect USA L I Inc

  14 Sycamore Place, Smithtown, NY 11787
• 

  $915,000

  Sold Aug 15, 2025

  83 River Heights Dr, Smithtown, NY 11787

  • 4 Beds
  • 3 Baths
  • 2,100 Sq Ft
  • Built 1967

  Last Sold Summary

  • 2% Above List Price
  • $436/SF
  • 21 Days On Market

  Current Estimated Value $958,600

  Last Listing Agent Tracy Boucher Signature Premier Properties

  83 River Heights Dr, Smithtown, NY 11787
• 

  Est $923,521

  Not Listed For Sale

  45A Eckernkamp Dr, Smithtown, NY 11787

  • 3 Beds
  • 2 Baths
  • 2,135 Sq Ft
  • Built 1983

  45A Eckernkamp Dr, Smithtown, NY 11787

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Deborah Lettieri Signature Premier Properties
• 

  

  /50

  $969,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,899 Sq Ft

  39 Merrivale Dr, Smithtown, NY 11787

  Welcome to 39 Merrivale Drive, a beautifully updated 4-bedroom, 2.5-bath expanded ranch located in one of Smithtown's most desirable neighborhoods. From the moment you step through the inviting entrance foyer, sunlight pours in through the skylight and soaring picture windows. This home blends comfort and style at every turn. The Eat in kitchen shines with granite countertops, updated appliances

  Caroline DeLuca Century 21 Catapano Homes

  39 Merrivale Dr, Smithtown, NY 11787
• 

  $854,000

  Sold Apr 28, 2026

  49 Lexington Ave, Smithtown, NY 11787

  • 3 Beds
  • 3 Baths
  • 2,195 Sq Ft
  • Built 1968

  Last Sold Summary

  • 19% Above List Price
  • $389/SF
  • 18 Days On Market

  Current Estimated Value $795,787

  Last Listing Agent Deborah Lettieri Signature Premier Properties

  49 Lexington Ave, Smithtown, NY 11787
• 

  Est $716,678

  Not Listed For Sale

  13 Ursular Ct, Smithtown, NY 11787

  • 3 Beds
  • 2 Baths
  • Built 1951

  13 Ursular Ct, Smithtown, NY 11787

  Last Sold Summary

  • 25 Days On Market

  Last Listing Agent Bryan Karp Coldwell Banker American Homes
• 

  

  /13

  $990,000

  $160K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,974 Sq Ft

  45 Croft Ln, Smithtown, NY 11787

  Nestled on a sprawling and picturesque property in the heart of Smithtown, this whole house renovated in year 2022, 4-bedroom, 3-bathroom residence offers the perfect blend of privacy, space, and country-style living and very close the horse trails at Blydenburgh Park and minutes to Routes 347 & 454. Set on beautifully maintained grounds, the property features its own horse stable and equestrian

  Min Xiao Welhome Realty Inc

  45 Croft Ln, Smithtown, NY 11787
• 

  $1,100,000

  Sold Aug 07, 2026

  50 Abbot Rd, Smithtown, NY 11787

  • 4 Beds
  • 2.5 Baths
  • 2,500 Sq Ft
  • Built 1960

  Last Sold Summary

  • 10% Above List Price
  • $440/SF
  • 16 Days On Market

  Current Estimated Value $988,828

  Last Listing Agent Michele Flaumenbaum Signature Premier Properties

  50 Abbot Rd, Smithtown, NY 11787
• 

  Est $697,214

  Not Listed For Sale

  5 Stone Gate Ct, Smithtown, NY 11787

  • 2 Beds
  • 3.5 Baths
  • Built 1993

  5 Stone Gate Ct, Smithtown, NY 11787

  Last Sold Summary

  • 36 Days On Market

  Last Listing Agent Stella DeRosa Signature Premier Properties
• 

  

  /29

  $1,099,999

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,239 Sq Ft

  17 Lower Rd, Smithtown, NY 11787

  Welcome to this beautifully updated 4 bedroom, 2.5 bath Colonial, nestled at the end of quiet dead-end street in the desirable Town of Smithtown. From the moment you arrive, the newly paved circular driveway, manicured grounds, and exceptional curb appeal set the stage for what awaits inside. Step through the front door into a stunning open foyer where natural light and elegant design create an

  Janet Foley Daniel Gale Sothebys Intl Rlty

  17 Lower Rd, Smithtown, NY 11787
• 

  $687,000

  Sold Dec 02, 2025

  12 Wadsworth Place, Smithtown, NY 11787

  • 3 Beds
  • 1 Bath
  • 1,283 Sq Ft
  • Built 1959

  Last Sold Summary

  • 15% Above List Price
  • $535/SF
  • 12 Days On Market

  Current Estimated Value $686,748

  Last Listing Agent Robin Rosenberg Signature Premier Properties

  12 Wadsworth Place, Smithtown, NY 11787
• 

  Est $969,601

  Not Listed For Sale

  54 River Heights Dr, Smithtown, NY 11787

  • 4 Beds
  • 2.5 Baths
  • Built 1964

  54 River Heights Dr, Smithtown, NY 11787

  Last Sold Summary

  • 24 Days On Market

  Last Listing Agent Lori Zamore Signature Premier Properties
• 

  

  /39

  $899,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,613 Sq Ft

  17 Leslie Ln, Smithtown, NY 11787

  Welcome to 17 Leslie Lane...a Beautifully updated Colonial Splanch nestled in a tree-lined neighborhood in Smithtown with Commack SD, this spacious home features 4 possibly 5 bedrooms and 2.5 Baths..Large Entry Foyer, Formal Dining Room, Expansive Kitchen with large Island..and Sitting/Den area with Fireplace and steps up to a Large Living Room, Gas Cooking and Heat, CAC. Hardwood Floors, Step

  Karen Orrach Signature Premier Properties

  17 Leslie Ln, Smithtown, NY 11787
• 

  $999,999

  Sold Jan 06, 2026

  22 Whispering Woods Dr, Smithtown, NY 11787

  • 4 Beds
  • 2.5 Baths
  • 2,791 Sq Ft
  • Built 1997

  Last Sold Summary

  • 15% Below List Price
  • $358/SF
  • 54 Days On Market

  Current Estimated Value $1,051,478

  Last Listing Agent Lynn Witz Howard Hanna Coach

  22 Whispering Woods Dr, Smithtown, NY 11787
• 

  Est $835,482

  Not Listed For Sale

  31 Eckernkamp Dr, Smithtown, NY 11787

  • 3 Beds
  • 2 Baths
  • Built 1955

  31 Eckernkamp Dr, Smithtown, NY 11787

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Kelley Taylor Douglas Elliman Real Estate
• 

  

  /50

  $1,199,999

  • 4 Beds
  • 3 Baths
  • 2,800 Sq Ft

  79 Oakside Rd, Smithtown, NY 11787

  Once-in-a-lifetime opportunity to own this spectacular custom-built Colonial, completed in 2022 and perfectly positioned on an incredibly private three-quarter-acre property within the highly desirable Smithtown School District. Tucked away at the end of a long private driveway, this exceptional estate offers the perfect combination of luxury, privacy, and resort-style living. A sprawling

  Bryan Karp Coldwell Banker American Homes

  79 Oakside Rd, Smithtown, NY 11787
• 

  $795,000

  Sold Oct 10, 2025

  2 Clearbrook Dr, Smithtown, NY 11787

  • 3 Beds
  • 2 Baths
  • 2,159 Sq Ft
  • Built 1959

  Last Sold Summary

  • 6% Below List Price
  • $368/SF
  • 40 Days On Market

  Current Estimated Value $831,221

  Last Listing Agent Diane Mascellaro Exit Realty Achieve

  2 Clearbrook Dr, Smithtown, NY 11787
• 

  Est $1,012,883

  Not Listed For Sale

  17 Stengel Place, Smithtown, NY 11787

  • 4 Beds
  • 4 Baths
  • 3,056 Sq Ft
  • Built 1959

  17 Stengel Place, Smithtown, NY 11787

  Last Sold Summary

  • 22 Days On Market

  Last Listing Agent Joyce Calcasola Douglas Elliman Real Estate
• 

  $499,000

  Sold Sep 04, 2025

  9 Annette Ave, Smithtown, NY 11787

  • 2 Beds
  • 1 Bath
  • 9,583 Sq Ft
  • Built 1958

  Last Sold Summary

  • 14% Below List Price
  • $52/SF
  • 73 Days On Market

  Current Estimated Value $567,652

  Last Listing Agent Janet Elliott Realty Connect USA LLC

  9 Annette Ave, Smithtown, NY 11787
• 

  Est $940,541

  Not Listed For Sale

  2 Ursular Ct, Smithtown, NY 11787

  • 4 Beds
  • 3.5 Baths
  • Built 1970

  2 Ursular Ct, Smithtown, NY 11787

  Last Sold Summary

  • 33 Days On Market

  Last Listing Agent Nicholas Albanese Douglas Elliman Real Estate
• 

  $775,000

  Sold Jul 22, 2026

  34 Hunter Place, Smithtown, NY 11787

  • 3 Beds
  • 2 Baths
  • 1,085 Sq Ft
  • Built 1955

  Last Sold Summary

  • 3% Below List Price
  • $714/SF
  • 27 Days On Market

  Current Estimated Value $773,602

  Last Listing Agent Rory Sherman Charles Rutenberg Realty Inc

  34 Hunter Place, Smithtown, NY 11787
• 

  Est $962,934

  Not Listed For Sale

  37 River Heights Dr, Smithtown, NY 11787

  • 5 Beds
  • 2.5 Baths
  • 2,368 Sq Ft
  • Built 1964

  37 River Heights Dr, Smithtown, NY 11787

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Andrea Jordano Compass Greater NY LLC
• 

  $950,000

  Sold Dec 09, 2025

  20 Villa Ln, Smithtown, NY 11787

  • 4 Beds
  • 2.5 Baths
  • 2,400 Sq Ft
  • Built 1962

  Last Sold Summary

  • $396/SF
  • 18 Days On Market

  Current Estimated Value $957,051

  Last Listing Agent Michael Scarito RE/MAX Integrity Leaders

  20 Villa Ln, Smithtown, NY 11787
• 

  Est $884,334

  Not Listed For Sale

  35 River Heights Dr, Smithtown, NY 11787

  • 3 Beds
  • 3 Baths

  35 River Heights Dr, Smithtown, NY 11787

  Last Sold Summary

  • 215 Days On Market

  Last Listing Agent Suleyma Hernandez EVP Realty Inc
• 

  $1,495,000

  Sold Dec 23, 2025

  158 Landing Meadow Rd, Smithtown, NY 11787

  • 4 Beds
  • 3.5 Baths
  • 3,634 Sq Ft
  • Built 1959

  Last Sold Summary

  • 20% Below List Price
  • $411/SF
  • 291 Days On Market

  Current Estimated Value $1,507,333

  Last Listing Agent John Canino BERKSHIRE HATHAWAY

  158 Landing Meadow Rd, Smithtown, NY 11787
• 

  Est $1,063,263

  Not Listed For Sale

  55 River Heights Dr, Smithtown, NY 11787

  • 4 Beds
  • 2.5 Baths
  • 2,730 Sq Ft
  • Built 1963

  55 River Heights Dr, Smithtown, NY 11787

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Deborah Lettieri Signature Premier Properties
• 

  $1,380,000

  Sold Jul 09, 2026

  41 Landing Meadow Rd, Smithtown, NY 11787

  • 4 Beds
  • 4.5 Baths
  • 3,149 Sq Ft
  • Built 1961

  Last Sold Summary

  • 11% Above List Price
  • $438/SF
  • 13 Days On Market

  Current Estimated Value $1,237,923

  Last Listing Agent Kristin Lettieri Signature Premier Properties

  41 Landing Meadow Rd, Smithtown, NY 11787
• 

  Est $494,582

  Not Listed For Sale

  765 Meadow Rd, Smithtown, NY 11787

  • 2 Beds
  • 1 Bath
  • 503 Sq Ft
  • Built 1949

  765 Meadow Rd, Smithtown, NY 11787

  Last Sold Summary

  • 135 Days On Market

  Last Listing Agent Jonathan Bedoya Coldwell Banker American Homes
• 

  $705,000

  Sold Jan 02, 2026

  2 Fawn Place, Smithtown, NY 11787

  • 4 Beds
  • 2 Baths
  • 1,398 Sq Ft
  • Built 1957

  Last Sold Summary

  • 8% Above List Price
  • $504/SF
  • 23 Days On Market

  Current Estimated Value $727,767

  Last Listing Agent Frank Castelli Signature Premier Properties

  2 Fawn Place, Smithtown, NY 11787
• 

  Est $539,675

  Not Listed For Sale

  763 Meadow Rd, Smithtown, NY 11787

  • 2 Beds
  • 1 Bath
  • 866 Sq Ft
  • Built 1935

  763 Meadow Rd, Smithtown, NY 11787

  Last Sold Summary

  • 98 Days On Market

  Last Listing Agent Pamela Zaid Howard Hanna Coach
• 

  $915,000

  Sold Dec 08, 2025

  25 Whispering Woods Dr, Smithtown, NY 11787

  • 4 Beds
  • 2.5 Baths
  • 2,405 Sq Ft
  • Built 1995

  Last Sold Summary

  • 15% Below List Price
  • $380/SF
  • 411 Days On Market

  Current Estimated Value $1,014,156

  Last Listing Agent Peter Hirschhorn Coldwell Banker American Homes

  25 Whispering Woods Dr, Smithtown, NY 11787
• 

  Est $733,524

  Not Listed For Sale

  Unlisted Address

  • 4 Beds
  • 2 Baths
  • 1,212 Sq Ft
  • Built 1954

  Unlisted Address

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Sharyn Guzzi Long Island Homes & Horse Prop
• 

  $735,000

  Sold Mar 10, 2026

  15 Mobrey Ln, Smithtown, NY 11787

  • 3 Beds
  • 1.5 Baths
  • 1,473 Sq Ft
  • Built 1967

  Last Sold Summary

  • 5% Above List Price
  • $499/SF
  • 21 Days On Market

  Current Estimated Value $746,801

  Last Listing Agent Doris Rose Piazza Coldwell Banker American Homes

  15 Mobrey Ln, Smithtown, NY 11787
• 

  Est $676,259

  Not Listed For Sale

  4 Dillmont Dr, Smithtown, NY 11787

  • 3 Beds
  • 2 Baths
  • Built 1958

  4 Dillmont Dr, Smithtown, NY 11787

  Last Sold Summary

  • 19 Days On Market

  Last Listing Agent Humayun Zaman LINY Real Estate
• 

  $840,000

  Sold Oct 22, 2025

  16 Crawford St, Smithtown, NY 11787

  • 4 Beds
  • 2.5 Baths
  • 2,890 Sq Ft
  • Built 1966

  Last Sold Summary

  • 4% Below List Price
  • $291/SF
  • 19 Days On Market

  Current Estimated Value $889,888

  Last Listing Agent Victor Stabile Douglas Elliman Real Estate

  16 Crawford St, Smithtown, NY 11787
• 

  Est $865,064

  Not Listed For Sale

  697 Meadow Rd, Smithtown, NY 11787

  • 4 Beds
  • 4 Baths
  • 2,249 Sq Ft
  • Built 1974

  697 Meadow Rd, Smithtown, NY 11787

  Last Sold Summary

  • 42 Days On Market

  Last Listing Agent Amy Cassidy Realty Connect USA L I Inc
• 

  $1,050,000

  Sold Jul 07, 2026

  22 Marquette Dr, Smithtown, NY 11787

  • 5 Beds
  • 2.5 Baths
  • 2,384 Sq Ft
  • Built 1964

  Last Sold Summary

  • 5% Above List Price
  • $440/SF
  • 14 Days On Market

  Current Estimated Value $996,316

  Last Listing Agent Shahzad Qureshi Pinnacle R E Consulting Inc

  22 Marquette Dr, Smithtown, NY 11787

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