Smithtown, NY Homes

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  /12

  $1,399,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 3,100 Sq Ft

  5 Sycamore Place, Smithtown, NY 11787

  THE EASTHAMPTON (3,100 SF and/or 4,200 SF): 5bdrm-3.5ba Classic Dutch Colonial Style Home as you will find in The Hamptons and unique gabled architecture facade. Features include spanning Master Suite, 2-story foyer and great rooms, office/guest quarters/en suite on the 1st floor, front or side entry 2-car garages. The full basement with outside entrance offers an addt'l ~1,900 SF of space.

  Peter Musso Realty Connect USA L I Inc

  5 Sycamore Place, Smithtown, NY 11787
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  /7

  $6,020 per month

  • 3 Beds
  • 2 Baths
  • 1,327 Sq Ft
  • Condo for Rent

  313 Avalon Cir Unit SI FL1-ID3605A, Smithtown, NY 11787

  Photos Coming SoonThese sample photos are meant to give you a sense of Blueground’s design style. Layout and furniture are subject to change. This apartment will be ready by the date indicated.Be the first to rent!Show up and start living from day one in Smithtown with this beautiful three bedroom Blueground apartment. You’ll love coming home to this thoughtfully

  313 Avalon Cir Unit SI FL1-ID3605A, Smithtown, NY 11787
• 

  $1,271,000 Sold May 20, 2025

  21 Franciscan Ln, Smithtown, NY 11787

  • 4 Beds
  • 2.5 Baths
  • 3,129 Sq Ft
  • Built 2006

  Last Sold Summary

  • 8% Above List Price
  • $406/SF
  • 13 Days On Market

  Current Estimated Value $1,328,246

  Last Listing Agent Gail Carillo Coldwell Banker American Homes

  21 Franciscan Ln, Smithtown, NY 11787
• 

  Est $615,618 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

  • 10% Above List Price
  • $545/SF
  • 22 Days On Market

  • Last Sold Price $560,000
  • Jan 22, 2025

  Last Listing Agent Andrew-Paul Ragusa REMI Realty
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  /35

  $1,250,000 Pending

  • 5 Beds
  • 3.5 Baths
  • 3,134 Sq Ft

  9 Sycamore Place, Smithtown, NY 11787

  THE DORCHESTER (3134 SF): 5bdrm-3.5ba Classic Center Hall Colonial. Features include spanning Master Suite, 2-story foyer and great rooms, office/guest quarters/ensuite on the 1st floor, front or side entry 2-car garages. The full basement with outside entrance offers an addt'l ~1,700 SF of space. Sycamore Estates is an 18-home new development consisting of 3 privately sidewalked cul-de-sacs

  Paul Musso Realty Connect USA L I Inc

  9 Sycamore Place, Smithtown, NY 11787
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  /13

  $5,300 per month

  • 2 Beds
  • 1 Bath
  • 1,130 Sq Ft
  • Condo for Rent

  313 Avalon Cir Unit SI FL1-ID3550A, Smithtown, NY 11787

  Staged photos of matching layout and similar décorImagery shows same floorplan and building, and similar décor as we finish photographing this new unit.Be the first to rent!Show up and start living from day one in Smithtown with this sophisticated two bedroom Blueground apartment. You’ll love coming home to this thoughtfully furnished, beautifully designed, and fully

  313 Avalon Cir Unit SI FL1-ID3550A, Smithtown, NY 11787
• 

  $899,000 Sold Jun 10, 2025

  8 Glacier Dr, Smithtown, NY 11787

  • 3 Beds
  • 3.5 Baths
  • Built 1965

  Last Sold Summary

  • 3% Below List Price
  • 114 Days On Market

  Current Estimated Value $920,947

  Last Listing Agent Ruth Chalco Compass Greater NY LLC

  8 Glacier Dr, Smithtown, NY 11787
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  Est $2,927,333 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

  • 5% Above List Price
  • $389/SF
  • 48 Days On Market

  • Last Sold Price $2,800,000
  • Jul 26, 2024

  Last Listing Agent Bonnie Glenn Daniel Gale Sotheby's
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  /18

  $1,375,000 Pending

  • 5 Beds
  • 3.5 Baths
  • 3,700 Sq Ft

  12 Sycamore Place, Smithtown, NY 11787

  THE CONCORD (3,700 SF): 5bdrm-3.5ba Classic Center Hall Colonial. Features include spanning Master Suite, 2-story foyer and great rooms, office/guest quarters/en suite on the 1st floor, front or side entry 2-car garages. The full basement with outside entrance offers an addt'l ~1,900 SF of space. Sycamore Estates is an 18-home new development consisting of 3 privately sidewalked cul-de-sacs

  Paul Musso Realty Connect USA L I Inc

  12 Sycamore Place, Smithtown, NY 11787
• 

  $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

  Last Listing Agent Michael Scarito RE/MAX Integrity Leaders

  22 5th Ave, Smithtown, NY 11787
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  Est $992,741 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

  • 41% Above List Price
  • $276/SF
  • 14 Days On Market

  • Last Sold Price $705,000
  • Sep 19, 2023

  Last Listing Agent Lorraine A Dileo Executive Group Realty
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  /38

  $1,288,888 Pending

  • 4 Beds
  • 3 Baths
  • 3,662 Sq Ft

  5 Poplar Dr, Smithtown, NY 11787

  Welcome to this completely renovated and expanded split ranch located in the highly sought- after Smithtown School District. Meticulously rebuilt taken down to the studs, with no detail overlooked. This stunning home offers 4 spacious bedrooms and 3 full bathrooms, including an impressive primary suite with a spa-like ensuite bathroom and 2 oversized closets. Show stopping kitchen, complete with

  Styliani Cannata Real Broker NY LLC

  5 Poplar Dr, 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 $979,284

  Last Listing Agent Oakar Reinstein Realty Connect USA L I Inc

  3 Ingram Ct, Smithtown, NY 11787
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  Est $908,837 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

  • 3% Above List Price
  • $404/SF
  • 17 Days On Market

  • Last Sold Price $885,000
  • Jan 27, 2025

  Last Listing Agent Diane Mascellaro Exit Realty Achieve
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  /36

  $1,199,888 Open Sun 1PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 2,495 Sq Ft

  17 Erita Ln, Smithtown, NY 11787

  BUYERS LOOK NO FURTHER! PRIME LOCATION! ALL NEW! ALL HIGH END! ABSOLUTELY NOTHING TO DO BUT TURN THE KEY OR JUST SIMPLY SCAN YOUR FINGERPRINT! THEY DEALT WITH ALL OF THE CONTRACTORS AND PERMITS SO THAT YOU DON’T HAVE TO! IMMERSE YOURSELF IN THE RESORT STYLE BACKYARD OASIS YOU ALWAYS DREAMED OF BUT NEVER THOUGHT EXISTED! AND THAT’S JUST THE BEGINNING! THIS HOUSE IS A GEM! Pride of ownership and

  Jonathan Minerick HomeCoin.com

  17 Erita Ln, Smithtown, NY 11787
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  $999,999 Sold Jun 30, 2025

  4 Crystal Ct, Smithtown, NY 11787

  • 4 Beds
  • 2.5 Baths
  • 2,700 Sq Ft
  • Built 2000

  Last Sold Summary

  • 5% Above List Price
  • $370/SF
  • 13 Days On Market

  Current Estimated Value $1,055,641

  Last Listing Agent Scott Paisley Signature Premier Properties

  4 Crystal Ct, Smithtown, NY 11787
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  Est $650,520 Not Listed For Sale

  10 South Ave, Smithtown, NY 11787

  • 3 Beds
  • 2 Baths
  • Built 1945

  10 South Ave, Smithtown, NY 11787

  Last Sold Summary

  • 7% Above List Price
  • 62 Days On Market

  • Last Sold Price $605,500
  • Dec 20, 2024

  Last Listing Agent Robert Scarito Douglas Elliman Real Estate
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  /45

  $999,000 Open Sun 12PM - 1:30PM

  • 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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  $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 $794,531

  Last Listing Agent Kerrilynn Prokop Signature Premier Properties

  24 Ursular Ct, Smithtown, NY 11787
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  Est $576,618 Not Listed For Sale

  33 Princeton Ave, Smithtown, NY 11787

  • 2 Beds
  • 2 Baths
  • Built 1940

  33 Princeton Ave, Smithtown, NY 11787

  Last Sold Summary

  • 11% Above List Price
  • 25 Days On Market

  • Last Sold Price $520,000
  • Jan 27, 2025

  Last Listing Agent Oksana Foster Signature Premier Properties
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  /23

  $1,250,000 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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  $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

  Last Listing Agent Sarah Fox Signature Premier Properties

  106 Fifty Acre Rd S, Smithtown, NY 11787
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  Not Listed For Sale

  26 Thomas Place, Smithtown, NY 11787

  • 5 Beds
  • 4 Baths
  • 2,700 Sq Ft
  • Built 1902

  26 Thomas Place, Smithtown, NY 11787

  Last Sold Summary

  • $293/SF
  • 28 Days On Market

  • Last Sold Price $790,000
  • Apr 30, 2025

  Last Listing Agent Homa Mohmand Realty Connect USA LLC
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  /22

  $950,000

  • 4 Beds
  • 3 Baths
  • 1,905 Sq Ft

  43 Grassy Pond Dr, Smithtown, NY 11787

  Located in the award-winning Hauppauge School District, consistently ranked among the top districts on Long Island. Enjoy Smithtown-area amenities with noticeably lower taxes than Smithtown proper — the best of both worlds. Quiet, tree-lined neighborhood with easy access to the LIE and Northern State Parkway, and both north and south shore beaches.Central ACWhole house generatorOver

  William Esslinger HomeSmart Premier Living Rlty

  43 Grassy Pond Dr, 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 $896,988

  Last Listing Agent Lori Zamore Signature Premier Properties

  9 Lorraine Ct, Smithtown, NY 11787
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  Est $822,600 Not Listed For Sale

  50 Parnell Dr, Smithtown, NY 11787

  • 4 Beds
  • 2 Baths
  • Built 1960

  50 Parnell Dr, Smithtown, NY 11787

  Last Sold Summary

  • 16% Above List Price
  • 37 Days On Market

  • Last Sold Price $710,000
  • Jan 24, 2024

  Last Listing Agent Kerry Protain Developing Dreams Realty USA
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  /40

  $989,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,546 Sq Ft

  330 Edgewood Ave, Smithtown, NY 11787

  Welcome to this beautiful Colonial set on a private 1-acre property in Smithtown featuring an inground pool, 2-car garage, and expansive driveway. This home offers a spacious layout with a primary bedroom featuring an en-suite bath, plus three additional bedrooms and 1.5 additional baths. The main floor includes formal living room, formal dining room, family room, and eat-in kitchen ideal for

  William Brown Gotham City Realty Group LLC

  330 Edgewood Ave, Smithtown, NY 11787
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  $1,250,000 Sold Jun 13, 2025

  14 Franciscan Ln, Smithtown, NY 11787

  • 4 Beds
  • 2.5 Baths
  • 2,742 Sq Ft
  • Built 2006

  Last Sold Summary

  • 19% Above List Price
  • $456/SF
  • 14 Days On Market

  Current Estimated Value $1,285,516

  Last Listing Agent Cecelia Schmidt Coldwell Banker American Homes

  14 Franciscan Ln, Smithtown, NY 11787
• 

  Est $810,774 Not Listed For Sale

  52 Parnell Dr, Smithtown, NY 11787

  • 4 Beds
  • 3 Baths

  52 Parnell Dr, Smithtown, NY 11787

  Last Sold Summary

  • 9% Above List Price
  • 51 Days On Market

  • Last Sold Price $745,000
  • Sep 19, 2024

  Last Listing Agent Thomas Diana Douglas Elliman Real Estate
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  /45

  $1,249,000

  • 5 Beds
  • 4.5 Baths
  • 3,937 Sq Ft

  144 Landing Meadow Rd, Smithtown, NY 11787

  Original owner, clean and well maintained 4000 square foot colonial on 1.2 acres in Point of Woods Section. Featuring 5 beds/4 baths including an ensuite bedroom with full bath on the first floor (see floor plan). Double height entry foyer with large open living spaces. Huge kitchen, dining and family room with wood burning fireplace. Full basement with outside entrance. Two car garage with long

  Shahzad Qureshi Pinnacle R E Consulting Inc

  144 Landing Meadow Rd, Smithtown, NY 11787
• 

  $800,000 Sold Jul 09, 2025

  467 Landing Ave, Smithtown, NY 11787

  • 4 Beds
  • 2.5 Baths
  • 1,094 Sq Ft
  • Built 1900

  Last Sold Summary

  • 23% Above List Price
  • $731/SF
  • 20 Days On Market

  Current Estimated Value $784,870

  Last Listing Agent Ed Shine Shine Realty Group

  467 Landing Ave, Smithtown, NY 11787
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  Est $648,511 Not Listed For Sale

  61 Plymouth Blvd, Smithtown, NY 11787

  • 3 Beds
  • 2 Baths
  • 1,021 Sq Ft
  • Built 1966

  61 Plymouth Blvd, Smithtown, NY 11787

  Last Sold Summary

  • 21% Above List Price
  • $524/SF
  • 39 Days On Market

  • Last Sold Price $535,000
  • Sep 13, 2023

  Last Listing Agent Cynthia McKenna Real Broker NY LLC
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  /46

  $899,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,074 Sq Ft

  16 Ursular Ct, Smithtown, NY 11787

  Step inside this Beautiful & Spacious 4 Bedroom, 3 Full Bath Farm Ranch! This home features a beautiful open floor plan with an Updated EIK with Granite Countertops & Center Island, Spacious Great Room with Tons of Natural light pouring in ,Formal dining room, Recently Updated Bathrooms including a Main Floor Full Bath w/ Radiant Heated Floors, 1st floor primary bedroom and additional

  Deborah Lettieri Signature Premier Properties

  16 Ursular Ct, Smithtown, NY 11787
• 

  $787,500 Sold Jul 01, 2025

  12 Graystone Ln, Smithtown, NY 11787

  • 3 Beds
  • 3 Baths
  • 1,250 Sq Ft
  • Built 1980

  Last Sold Summary

  • 13% Above List Price
  • $630/SF
  • 13 Days On Market

  Current Estimated Value $793,876

  Last Listing Agent Natalia Hernandez Lopez DirectKey Properties LLC

  12 Graystone Ln, Smithtown, NY 11787
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  Est $855,730 Not Listed For Sale

  25 Smithtown Crescent, Smithtown, NY 11787

  • 4 Beds
  • 2.5 Baths
  • 2,105 Sq Ft
  • Built 1972

  25 Smithtown Crescent, Smithtown, NY 11787

  Last Sold Summary

  • 13% Above List Price
  • $361/SF
  • 29 Days On Market

  • Last Sold Price $760,500
  • Oct 03, 2024

  Last Listing Agent Kristen Toffales Serhant LLC
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  /50

  $989,990 Open Sun 12PM - 1:30PM

  • 5 Beds
  • 3 Baths
  • 2,537 Sq Ft

  45 Woodland Dr, Smithtown, NY 11787

  Location, Location, Location!!! This classic, VERY spacious and well maintained farm ranch home has loads of character and charm with hardwood floors throughout. 5-bedrooms, 3 full -baths and 2 car garage set on a picturesque, quite, tree lined and manicured street. This lovely and traditional home blends timeless elegance with thoughtful updates and TONS of storage. Some recent improvements

  Veronica Mannarino Douglas Elliman Real Estate

  45 Woodland Dr, Smithtown, NY 11787
• 

  $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 $1,514,625

  Last Listing Agent Bryan Karp Coldwell Banker American Homes

  1 Crystal Ct, Smithtown, NY 11787
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  Est $923,957 Not Listed For Sale

  5 Smithtown Crescent, Smithtown, NY 11787

  • 4 Beds
  • 2.5 Baths
  • 1,756 Sq Ft
  • Built 1973

  5 Smithtown Crescent, Smithtown, NY 11787

  Last Sold Summary

  • 5% Above List Price
  • $501/SF
  • 8 Days On Market

  • Last Sold Price $880,000
  • Jun 27, 2024

  Last Listing Agent Lisa Kass Coldwell Banker American Homes
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  /29

  $915,000 Pending

  • 6 Beds
  • 2.5 Baths
  • 2,998 Sq Ft

  159 Shady Ln, Smithtown, NY 11787

  This beautiful sprawling California ranch in the highly desirable area of Smithtown offers 6 generously sized bedrooms and 2.5 bathrooms, tucked away on a quiet dead end street. Designed for comfort, the L-shaped layout creates a tranquil oasis that fills the home with light. With 3 bedrooms on the main floor and 3 bedrooms downstairs, this home is a legal duplex perfect for multi-generation

  Anita Gordon Realty Connect USA L I Inc

  159 Shady Ln, Smithtown, NY 11787
• 

  $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 $586,668

  Last Listing Agent Edward Martella HomeSmart Premier Living Rlty

  347 Forest Ln, Smithtown, NY 11787

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