Smithtown, NY Homes

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  $768,000

  • 3 Beds
  • 3 Baths
  • 1,684 Sq Ft

  76 Burlington Blvd, Smithtown, NY 11787

  Move right in...76 Burlington Boulevard offers timeless modern comfort on one of Smithtown's most tranquil and sought-after neighborhoods in the Smithtown school district. This impeccably updated 3-bedroom, 3-full-bath residence showcases rich hardwood flooring throughout the spacious living room, formal dining room, and inviting family room, creating warm spaces for everyday living and

  Amaury Hernandez List 2 Sell Inc

  76 Burlington Blvd, Smithtown, NY 11787
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  /11

  $3,295 Per Month

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Apartment for Rent

  44 Route 25 A Unit 405, Smithtown, NY 11787

  Beautiful Private Lake community, Apartment Includes, Reserved Parking Spot, Fitness Room, 4x4x8 Storage Locker, Separate Laundry Centers.

  Mary Beth Donnelly Douglas Elliman Real Estate

  44 Route 25 A Unit 405, Smithtown, NY 11787
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  $795,000

  Sold Jan 23, 2026

  22 5th Ave, Smithtown, NY 11787

  • 4 Beds
  • 2 Baths
  • 1,575 Sq Ft
  • Built 1961

  Last Sold Summary

  • 6% Above List Price
  • $505/SF
  • 32 Days On Market

  Current Estimated Value $802,039

  Last Listing Agent Michael Scarito RE/MAX Integrity Leaders

  22 5th Ave, Smithtown, NY 11787
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  Est $709,477

  Not Listed For Sale

  87 Hidden Ponds Cir, Smithtown, NY 11787

  • 2 Beds
  • 2.5 Baths
  • 1,495 Sq Ft
  • Built 1987

  87 Hidden Ponds Cir, Smithtown, NY 11787

  Last Sold Summary

  • 50 Days On Market

  Last Listing Agent Richard Krug Coldwell Banker American Homes
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  /35

  $985,000

  $15K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,200 Sq Ft

  103 Redan Dr, Smithtown, NY 11787

  Come Live A Lifestyle in this very Desirable 24/7 Gated Golf Community with Amenities. This 4 Bdrm, 3 Bth Colonial style Home offers endless possibilities to make this the home of your Dreams! The Grand entrance foyer boasts a soaring 20 ft Ceiling/ chandelier on a power switch, as well as beautiful architectural moldings. The main level includes a Formal Living Room, Formal Dining Rm, Great

  Carol Flaherty Lynch Signature Premier Properties

  103 Redan Dr, Smithtown, NY 11787
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  /12

  $2,870 Per Month

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • Apartment for Rent

  44 Route 25 A Unit 113, Smithtown, NY 11787

  Beautiful Private Lake community, Apartment Includes, Reserved Parking Spot, Fitness Room, 4x4x8 Storage Locker, Separate Laundry Centers.

  Mary Beth Donnelly Douglas Elliman Real Estate

  44 Route 25 A Unit 113, Smithtown, NY 11787
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  $940,000

  Sold Jul 21, 2026

  16 Amherst Ln, Smithtown, NY 11787

  • 4 Beds
  • 2.5 Baths
  • 2,034 Sq Ft
  • Built 1969

  Last Sold Summary

  • 18% Above List Price
  • $462/SF
  • 13 Days On Market

  Current Estimated Value $821,643

  Last Listing Agent Robyn Schatz Compass Greater NY LLC

  16 Amherst Ln, Smithtown, NY 11787
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  Est $732,516

  Not Listed For Sale

  29 Paddington Cir, Smithtown, NY 11787

  • 2 Beds
  • 2.5 Baths
  • 1,479 Sq Ft
  • Built 2002

  29 Paddington Cir, Smithtown, NY 11787

  Last Sold Summary

  • 19 Days On Market

  Last Listing Agent Sophia Christodoulou Signature Premier Properties
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  /42

  $789,000

  Pending

  • 4 Beds
  • 2 Baths
  • 1,284 Sq Ft

  50 Amsterdam Rd, Smithtown, NY 11787

  Welcome to 50 Amsterdam Road, an inviting 4-bedroom home ideally situated in one of Smithtown's most desirable neighborhoods. Set on a generous lot, this residence offers comfortable living spaces, room to grow, and endless potential to make it your own. The private backyard provides a peaceful setting for relaxing, entertaining, and enjoying the outdoors, enhanced by architectural landscape

  Maeve McDonald Cornerstone Properties of LI

  50 Amsterdam Rd, Smithtown, NY 11787
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  /10

  $2,870 Per Month

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • Apartment for Rent

  44 Route 25 A Unit 304, Smithtown, NY 11787

  Beautiful Private Lake Community. Apartment Includes, Reserved Parking Spot, Fitness Rm/Snow Removal/Garbage/Sewer/4'X4'X8' Storage Locker, Central Air Conditioning, Separate Laundry Centers., 2 Cats and 1 Dog Per Apartment.

  Mary Beth Donnelly Douglas Elliman Real Estate

  44 Route 25 A Unit 304, Smithtown, NY 11787
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  $975,000

  Sold Nov 13, 2025

  3 Ingram Ct, Smithtown, NY 11787

  • 4 Beds
  • 3.5 Baths
  • 2,977 Sq Ft
  • Built 1970

  Last Sold Summary

  • $328/SF
  • 181 Days On Market

  Current Estimated Value $1,021,459

  Last Listing Agent Oakar Reinstein Shoreline Real Estate Advisors

  3 Ingram Ct, Smithtown, NY 11787
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  Est $589,730

  Not Listed For Sale

  45 Oak Ave, Smithtown, NY 11787

  • 3 Beds
  • 1 Bath
  • Built 1948

  45 Oak Ave, Smithtown, NY 11787

  Last Sold Summary

  • 15 Days On Market

  Last Listing Agent Dorothy Cheswick Howard Hanna Coach
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  /31

  $849,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  7 Talbot Ln, Smithtown, NY 11787

  Nestled on a quarter acre of beautifully maintained property in the sought-after Morewood Estates section of North Smithtown, this immaculate ranch offers the perfect blend of comfort, updates, and flow. Walk the paver path from the oversized driveway into this updated home with gleaming hardwood floors, crown molding throughout, updated light fixtures and so much more! Updated bathrooms, 200-amp

  Carolyn Burton-Gajda Executive Group Realty

  7 Talbot Ln, Smithtown, NY 11787
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  /11

  $3,295 Per Month

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Apartment for Rent

  44 Route 25 A Unit 416, Smithtown, NY 11787

  Beautiful Private Lake Community. Apartment Includes, Reserved Parking Spot, Fitness Rm/Snow Removal/Garbage/Sewer/4'X4'X8' Storage Locker, Cen Air Conditioning, Separate Laundry Centers.

  Mary Beth Donnelly Douglas Elliman Real Estate

  44 Route 25 A Unit 416, Smithtown, NY 11787
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  $772,000

  Sold Oct 09, 2025

  24 Ursular Ct, Smithtown, NY 11787

  • 3 Beds
  • 1.5 Baths
  • 2,167 Sq Ft
  • Built 1955

  Last Sold Summary

  • 2% Above List Price
  • $356/SF
  • 40 Days On Market

  Current Estimated Value $819,153

  Last Listing Agent Kerrilynn Prokop Signature Premier Properties

  24 Ursular Ct, Smithtown, NY 11787
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  Est $1,271,651

  Not Listed For Sale

  3 Candlelight Ct, Smithtown, NY 11787

  • 6 Beds
  • 5.5 Baths
  • 1,924 Sq Ft
  • Built 1910

  3 Candlelight Ct, Smithtown, NY 11787

  Last Sold Summary

  • 52 Days On Market

  Last Listing Agent Ashley Tanenblatt Daniel Gale Sothebys Intl Rlty
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  /45

  $999,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,448 Sq Ft

  185 Plymouth Blvd, Smithtown, NY 11787

  Prestine 4-Bedroom Colonial with FULL BASEMENT in the Smithtown School District! Welcome to this beautifully maintained Colonial offering the perfect blend of elegance, space, and comfort. A charming wraparound porch sets the tone as you enter into an impressive entry foyer with soaring ceilings and a bright, open feel. The home features high ceilings throughout, a spacious den with vaulted

  Michail Konstas Signature Premier Properties

  185 Plymouth Blvd, Smithtown, NY 11787
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  $5,900 Per Month

  • 4 Beds
  • 2 Baths
  • 1,728 Sq Ft
  • House for Rent

  26 Valleywood Rd, ComMacK, NY 11725

  Immaculate Wide Line Hi-Ranch in the desirable Pines community. Sparkling hardwood floors. 2 Car garage. 20 x 40 in ground pool with extensive multi-level decks. Serviced by the Hauppauge school district.

  Steve Rainone Netter Real Estate Inc

  26 Valleywood Rd, ComMacK, NY 11725
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  $825,000

  Sold Jan 22, 2026

  106 Fifty Acre Rd S, Smithtown, NY 11787

  • 5 Beds
  • 2.5 Baths
  • 3,001 Sq Ft
  • Built 1968

  Last Sold Summary

  • 9% Above List Price
  • $275/SF
  • 10 Days On Market

  Current Estimated Value $842,081

  Last Listing Agent Sarah Fox Signature Premier Properties

  106 Fifty Acre Rd S, Smithtown, NY 11787
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  Est $624,237

  Not Listed For Sale

  25 Pineacre Dr, Smithtown, NY 11787

  • 3 Beds
  • 2 Baths
  • 1,028 Sq Ft
  • Built 1955

  25 Pineacre Dr, Smithtown, NY 11787

  Last Sold Summary

  • 22 Days On Market

  Last Listing Agent Andrew-Paul Ragusa REMI Realty
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  /19

  $749,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,040 Sq Ft

  23 Stone Gate Ct, Smithtown, NY 11787

  Nestled on a quiet cul-de-sac in the heart of Smithtown, this hidden gem is surrounded by a beautiful wooded backdrop, offering exceptional privacy, comfort, and convenience. This spacious end-unit townhome features 3 bedrooms, 2.5 baths, an open-concept layout, and a full basement, providing ample living and storage space. The home also offers a large eat-in kitchen complete with stainless steel

  Stella DeRosa Signature Premier Properties

  23 Stone Gate Ct, Smithtown, NY 11787
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  /14

  $3,295 Per Month

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Apartment for Rent

  44 Route 25 A Unit 401, Smithtown, NY 11787

  Beautiful Private Lake Community. Apartment Includes, Reserved Parking Spot, Fitness Rm/Snow Removal/Garbage/Sewer/4'X4'X8' Storage Locker, Central Air Conditioning, Separate Laundry Centers.

  Mary Beth Donnelly Douglas Elliman Real Estate

  44 Route 25 A Unit 401, Smithtown, NY 11787
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  $900,000

  Sold Dec 18, 2025

  9 Lorraine Ct, Smithtown, NY 11787

  • 4 Beds
  • 2.5 Baths
  • 2,400 Sq Ft
  • Built 1982

  Last Sold Summary

  • $375/SF
  • 18 Days On Market

  Current Estimated Value $927,127

  Last Listing Agent Lori Zamore Signature Premier Properties

  9 Lorraine Ct, Smithtown, NY 11787
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  Est $3,030,667

  Not Listed For Sale

  146 Oakside Dr, Smithtown, NY 11787

  • 6 Beds
  • 5.5 Baths
  • 7,200 Sq Ft
  • Built 1927

  146 Oakside Dr, Smithtown, NY 11787

  Last Sold Summary

  • 48 Days On Market

  Last Listing Agent Bonnie Glenn Daniel Gale Sothebys Intl Rlty
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  /27

  $775,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,522 Sq Ft

  11 Sandalwood Dr, Smithtown, NY 11787

  Welcome home! This pristine 3-bedroom, 2-bathroom Splanch sits perfectly on a flat, fenced .25-acre lot in a sought-after, sidewalk-lined neighborhood. Beautifully merging modern updates with exceptional energy efficiency, this residence is entirely turn-key. From the moment you arrive, the new double-wide paver driveway provides the convenience for parking multiple cars without the chaos. Enjoy

  Carrie Trezza All Village Properties Inc

  11 Sandalwood Dr, Smithtown, NY 11787
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  /11

  $3,295 Per Month

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Apartment for Rent

  44 Route 25A Unit 504, Smithtown, NY 11787

  Beautiful Private Lake Community. Apartment Includes, Reserved Parking Spot, Fitness Rm/Snow Removal/Garbage/Sewer/4'X4'X8' Storage Locker, Cen Air Conditioning, Separate Laundry Centers. 2 Cats and 1 Dog Per Apartment

  Mary Beth Donnelly Douglas Elliman Real Estate

  44 Route 25A Unit 504, Smithtown, NY 11787
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  $1,125,000

  Sold Jul 17, 2026

  66 Cygnet Dr, Smithtown, NY 11787

  • 4 Beds
  • 3.5 Baths
  • 2,200 Sq Ft
  • Built 1964

  Last Sold Summary

  • 13% Above List Price
  • $511/SF
  • 10 Days On Market

  Current Estimated Value $1,097,373

  Last Listing Agent Deborah Lettieri Signature Premier Properties

  66 Cygnet Dr, Smithtown, NY 11787
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  Est $984,577

  Not Listed For Sale

  506 Landing Ave, Smithtown, NY 11787

  • 4 Beds
  • 3.5 Baths
  • 2,550 Sq Ft
  • Built 1955

  506 Landing Ave, Smithtown, NY 11787

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Lorraine A Dileo Executive Group Realty
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  /23

  $1,250,000

  New Construction Pending

  • 3 Beds
  • 2.5 Baths
  • 2,024 Sq Ft

  7 Sycamore Place, Smithtown, NY 11787

  THE HAMPTON (2,024 SF): 3bdrm-2.5ba Ranch. Features include an open floor plan with vaulted ceilings throughout for perfect first floor living. The full basement with outside entrance offers an addt'l ~2,000 SF of space. Sycamore Estates is an 18-home new development consisting of 3 privately sidewalked cul-de-sacs conveniently located 5 minutes to the LIE and 9 minutes to the LIRR. Move walls,

  Paul Musso Realty Connect USA L I Inc

  7 Sycamore Place, Smithtown, NY 11787
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  /12

  $3,000 Per Month

  • 2 Beds
  • 1.5 Baths
  • 1,000 Sq Ft
  • Apartment for Rent

  1 Gilbert Ave Unit 5, Smithtown, NY 11787

  Mint 2 Bedroom, 2 Story Apt. with bedrooms upstairs. Front & Rear ground level access. Stone counter tops! Incredible wood floors, all re-done - Close to all! Includes 1 car garage! All new appliances, W/D, dishwasher, interior features: separate thrmostat.

  Willard Hough H & G Realty New York

  1 Gilbert Ave Unit 5, Smithtown, NY 11787
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  $920,000

  Sold Jul 31, 2026

  53 Mobrey Ln, Smithtown, NY 11787

  • 6 Beds
  • 3 Baths
  • 2,513 Sq Ft
  • Built 1965

  Last Sold Summary

  • 15% Above List Price
  • $366/SF
  • 24 Days On Market

  Current Estimated Value $840,625

  Last Listing Agent Danielle Lenard Signature Premier Properties

  53 Mobrey Ln, Smithtown, NY 11787
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  Est $937,918

  Not Listed For Sale

  19 Format Ln, Smithtown, NY 11787

  • 4 Beds
  • 2.5 Baths
  • 2,193 Sq Ft
  • Built 1972

  19 Format Ln, Smithtown, NY 11787

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Diane Mascellaro Exit Realty Achieve
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  /50

  $1,699,000

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

  14 Loft Rd, Smithtown, NY 11787

  Experience the pinnacle of luxury living on this sprawling 1.25+ acre equestrian-ready estate. Recently renovated to perfection, this five-bedroom, five-bathroom residence seamlessly blends sophisticated design with modern efficiency, featuring brand-new utilities and owned solar panels.The heart of the home is a dream kitchen, boasting radiant heated floors, a high-end Subzero panel

  Richard Iorio Douglas Elliman Real Estate

  14 Loft Rd, Smithtown, NY 11787
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  $1,115,000

  Sold Apr 09, 2026

  1 Crystal Ct, Smithtown, NY 11787

  • 4 Beds
  • 4 Baths
  • 2,757 Sq Ft
  • Built 2000

  Last Sold Summary

  • 2% Above List Price
  • $404/SF
  • 22 Days On Market

  Current Estimated Value $1,102,921

  Last Listing Agent Bryan Karp Coldwell Banker American Homes

  1 Crystal Ct, Smithtown, NY 11787
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  Est $633,240

  Not Listed For Sale

  54 Prospect Ave, Smithtown, NY 11787

  • 4 Beds
  • 2 Baths
  • 1,684 Sq Ft
  • Built 1976

  54 Prospect Ave, Smithtown, NY 11787

  Last Sold Summary

  • 48 Days On Market

  Last Listing Agent Marianne Koke Daniel Gale Sothebys Intl Rlty
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  /33

  $999,000

  $51K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,986 Sq Ft

  57 Brooksite Dr, Smithtown, NY 11787

  When opportunity knocks the door must be opened. Welcome to 57 Brooksite Drive. A stunning single unit home in the heart of Smithtown NY sitting on nearly a half an acre of property. Renovated just over 1 year ago this home is being offered to the market at an amazing opportunity to be purchased as turn key as they come. Enjoy the state of the art renovations throughout the property including a

  Minas Styponias Realty Executives Today

  57 Brooksite Dr, Smithtown, NY 11787
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  $580,000

  Sold Sep 18, 2025

  347 Forest Ln, Smithtown, NY 11787

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Built 1961

  Last Sold Summary

  • 16% Above List Price
  • $580/SF
  • 53 Days On Market

  Current Estimated Value $600,640

  Last Listing Agent Edward Martella HomeSmart Premier Living Rlty

  347 Forest Ln, Smithtown, NY 11787
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  Est $664,879

  Not Listed For Sale

  24 South Ave, Smithtown, NY 11787

  • 4 Beds
  • 2 Baths
  • Built 1940

  24 South Ave, Smithtown, NY 11787

  Last Sold Summary

  • 19 Days On Market

  Last Listing Agent Nancy Stein Douglas Elliman Real Estate
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  /43

  $699,999

  $35K PRICE DROP Pending

  • 3 Beds
  • 1.5 Baths
  • 1,045 Sq Ft

  79 Brooksite Dr, Smithtown, NY 11787

  Welcome to 79 Brooksite Drive in Smithtown, where privacy, space, and natural beauty come together in an exceptional setting just minutes from Main Street Smithtown. Situated on over a half acre of lush property and within walking distance to the scenic trails of Blydenburgh County Park, this 3-bedroom, 1.5-bath ranch offers a rare opportunity to enjoy a peaceful, retreat-like lifestyle without

  Nicole Chimento Coldwell Banker American Homes

  79 Brooksite Dr, Smithtown, NY 11787
• 

  $745,000

  Sold Aug 27, 2025

  2 Cornell Ct N, Smithtown, NY 11787

  • 3 Beds
  • 2 Baths
  • 1,305 Sq Ft
  • Built 1955

  Last Sold Summary

  • 6% Above List Price
  • $571/SF
  • 11 Days On Market

  Current Estimated Value $773,103

  Last Listing Agent Kate Works Compass Greater NY LLC

  2 Cornell Ct N, Smithtown, NY 11787

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