Smithtown, NY Homes

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  $635,000

  • 2 Beds
  • 2.5 Baths
  • 1,358 Sq Ft

  4 Chelsea Dr, Smithtown, NY 11787

  Welcome to 4 Chelsea Drive, Smithtown! Set within the desirable Windcrest Community sits this beautifully maintained 2 bedroom, 2.5 bath Townhouse that offers an open concept living room with fireplace, an updated kitchen with stainless steel appliances. Hardwood floors throughout the first floor, Upstairs, Primary en-suite with Updated Bathroom, 2 WIC's. Generous size 2nd Bedroom and 2nd Full

  Gina DiBenedetto Signature Premier Properties

  4 Chelsea Dr, Smithtown, NY 11787
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  $919,000 Sold Dec 19, 2025

  49 Dorchester Rd, Smithtown, NY 11787

  • 4 Beds
  • 2.5 Baths
  • 2,200 Sq Ft
  • Built 1968

  Last Sold Summary

  • $418/SF
  • 25 Days On Market

  Last Listing Agent Justin Soriano Signature Premier Properties

  49 Dorchester Rd, Smithtown, NY 11787
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  Est $809,424 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths

  45 Carnegie Dr, Smithtown, NY 11787

  45 Carnegie Dr, Smithtown, NY 11787
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  $1,300,000 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
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  $1,650,000 Sold Mar 07, 2025

  20 Winston Dr, Smithtown, NY 11787

  • 5 Beds
  • 3.5 Baths
  • 3,400 Sq Ft
  • Built 2024

  Last Sold Summary

  • $485/SF
  • 40 Days On Market

  Current Estimated Value $1,549,536

  Last Listing Agent Natalie Carey Exit Realty Achieve

  20 Winston Dr, Smithtown, NY 11787
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  Est $839,703 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,380 Sq Ft

  44 Carnegie Dr, Smithtown, NY 11787

  44 Carnegie Dr, Smithtown, NY 11787
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  $999,990

  • 4 Beds
  • 3.5 Baths
  • 2,700 Sq Ft

  45 Roundabout Rd, Smithtown, NY 11787

  Welcome to 45 Roundabout Road, a stunning 4-bedroom, 3.5-bathroom contemporary home situated on an expansive .84-acre lot in the sought-after community of Smithtown. This tranquil property is a "little piece of Nissequogue". Inside, vaulted ceilings with abundant natural lighting highlights an open and inviting floor plan. The spacious living room with large windows and wood burning fireplace

  Elaine Patterson Signature Premier Properties

  45 Roundabout Rd, Smithtown, NY 11787
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  $840,000 Sold Nov 05, 2025

  32 Hemlock Ln, Smithtown, NY 11787

  • 4 Beds
  • 4 Baths
  • 3,000 Sq Ft
  • Built 1975

  Last Sold Summary

  • 2% Above List Price
  • $280/SF
  • 11 Days On Market

  Last Listing Agent Felicita Cartagena Nocella Property Professionals Realty

  32 Hemlock Ln, Smithtown, NY 11787
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  Est $848,822 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths

  3 Carnegie Dr, Smithtown, NY 11787

  3 Carnegie Dr, Smithtown, NY 11787
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  $915,000 Sold Oct 10, 2025

  21 Kent Place, Smithtown, NY 11787

  • 4 Beds
  • 2.5 Baths
  • 2,500 Sq Ft
  • Built 1991

  Last Sold Summary

  • 2% Above List Price
  • $366/SF
  • 26 Days On Market

  Current Estimated Value $903,415

  Last Listing Agent Michele Targovnik Daniel Gale Sothebys Intl Rlty

  21 Kent Place, Smithtown, NY 11787
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  Est $797,210 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,774 Sq Ft

  18 Carnegie Dr, Smithtown, NY 11787

  18 Carnegie Dr, Smithtown, NY 11787
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  $830,000 Sold Aug 11, 2025

  58 Oak St, Smithtown, NY 11787

  • 4 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • Built 1965

  Last Sold Summary

  • 2% Below List Price
  • $415/SF
  • 41 Days On Market

  Current Estimated Value $844,940

  Last Listing Agent Tammy Gatto Signature Premier Properties

  58 Oak St, Smithtown, NY 11787
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  Est $913,954 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,380 Sq Ft

  20 Carnegie Dr, Smithtown, NY 11787

  20 Carnegie Dr, Smithtown, NY 11787
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  $775,000 Sold Feb 25, 2025

  40 Valleywood Rd, ComMacK, NY 11725

  • 4 Beds
  • 2.5 Baths
  • 2,217 Sq Ft
  • Built 1967

  Last Sold Summary

  • 6% Below List Price
  • $350/SF
  • 75 Days On Market

  Current Estimated Value $870,202

  Last Listing Agent David Cohen SRG Residential LLC

  40 Valleywood Rd, ComMacK, NY 11725
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  Est $988,078 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,421 Sq Ft

  8 Hurtin Blvd, Smithtown, NY 11787

  8 Hurtin Blvd, Smithtown, NY 11787
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  $850,000 Sold Jan 08, 2026

  677 Meadow Rd, Smithtown, NY 11787

  • 4 Beds
  • 2.5 Baths
  • 2,080 Sq Ft
  • Built 1971

  Last Sold Summary

  • $409/SF
  • 55 Days On Market

  Last Listing Agent Melissa D'Angelo Compass Greater NY LLC

  677 Meadow Rd, Smithtown, NY 11787
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  Est $826,323 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 1,951 Sq Ft

  1 Hurtin Blvd, Smithtown, NY 11787

  1 Hurtin Blvd, Smithtown, NY 11787
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  $670,000 Sold Jul 24, 2025

  3 Baylor Dr, Smithtown, NY 11787

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Built 1958

  Last Sold Summary

  • 6% Above List Price
  • $515/SF
  • 17 Days On Market

  Current Estimated Value $686,779

  Last Listing Agent Rowena Nedvin Signature Premier Properties

  3 Baylor Dr, Smithtown, NY 11787
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  Est $875,421 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,341 Sq Ft

  23 Moore St, Smithtown, NY 11787

  23 Moore St, Smithtown, NY 11787
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  $1,295,000 Sold Sep 16, 2025

  5 Hills Park Ln, Smithtown, NY 11787

  • 4 Beds
  • 4 Baths
  • 3,430 Sq Ft
  • Built 1969

  Last Sold Summary

  • 10% Above List Price
  • $378/SF
  • 12 Days On Market

  Current Estimated Value $1,283,494

  Last Listing Agent Cecelia Schmidt Coldwell Banker American Homes

  5 Hills Park Ln, Smithtown, NY 11787
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  Est $1,155,038 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,235 Sq Ft

  6 Hartsdale St, Saint James, NY 11780

  6 Hartsdale St, Saint James, NY 11780
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  $715,000 Sold Feb 03, 2025

  3 Paddington Cir, Smithtown, NY 11787

  • 3 Beds
  • 2.5 Baths
  • Built 2002

  Last Sold Summary

  • 10% Above List Price
  • 19 Days On Market

  Last Listing Agent Trish Bergin Signature Premier Properties

  3 Paddington Cir, Smithtown, NY 11787
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  Est $1,081,215 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,380 Sq Ft

  103 Glenrich Dr S, Saint James, NY 11780

  103 Glenrich Dr S, Saint James, NY 11780
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  $880,000 Sold Sep 18, 2025

  4 Charter Ln, Smithtown, NY 11787

  • 5 Beds
  • 2.5 Baths
  • 2,144 Sq Ft
  • Built 1968

  Last Sold Summary

  • 4% Above List Price
  • $410/SF
  • 26 Days On Market

  Current Estimated Value $857,494

  Last Listing Agent Carol Rodriguez List 2 Sell Inc

  4 Charter Ln, Smithtown, NY 11787
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  Est $1,108,182 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,000 Sq Ft

  2 Harness Rd, Saint James, NY 11780

  2 Harness Rd, Saint James, NY 11780
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  $1,170,000 Sold Jun 03, 2025

  35 Woodland Ln, Smithtown, NY 11787

  • 5 Beds
  • 2.5 Baths
  • 2,600 Sq Ft
  • Built 1972

  Last Sold Summary

  • 2% Below List Price
  • $450/SF
  • 54 Days On Market

  Current Estimated Value $1,173,332

  Last Listing Agent Christine Daddio Howard Hanna Coach

  35 Woodland Ln, Smithtown, NY 11787
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  Est $1,051,861 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,573 Sq Ft

  5 Denise Ct, Saint James, NY 11780

  5 Denise Ct, Saint James, NY 11780
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  $635,000 Sold Nov 25, 2025

  10 Mcarthur Ln, Smithtown, NY 11787

  • 3 Beds
  • 2 Baths
  • Built 1965

  Last Sold Summary

  • 3% Above List Price
  • 26 Days On Market

  Last Listing Agent Nicholas Pappas Coldwell Banker American Homes

  10 Mcarthur Ln, Smithtown, NY 11787
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  Est $1,019,872 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,160 Sq Ft

  39 Twixt Hills Rd, Saint James, NY 11780

  39 Twixt Hills Rd, Saint James, NY 11780
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  $880,000 Sold Feb 07, 2025

  47 Holly Dr, Smithtown, NY 11787

  • 4 Beds
  • 2.5 Baths
  • Built 1968

  Last Sold Summary

  • 4% Above List Price
  • 13 Days On Market

  Current Estimated Value $895,929

  Last Listing Agent Rita Bender Howard Hanna Coach

  47 Holly Dr, Smithtown, NY 11787
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  Est $1,098,492 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths

  10 Regal Ct, Saint James, NY 11780

  10 Regal Ct, Saint James, NY 11780
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  $450,000 Sold Jan 31, 2025

  765 Meadow Rd, Smithtown, NY 11787

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

  Last Sold Summary

  • $895/SF
  • 135 Days On Market

  Current Estimated Value $491,052

  Last Listing Agent Jonathan Bedoya Coldwell Banker American Homes

  765 Meadow Rd, Smithtown, NY 11787
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  Est $1,000,436 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths

  8 Regal Ct, Saint James, NY 11780

  8 Regal Ct, Saint James, NY 11780
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  $999,000 Sold Jan 29, 2025

  18 Poplar Dr, Smithtown, NY 11787

  • 4 Beds
  • 2.5 Baths
  • 2,800 Sq Ft
  • Built 1989

  Last Sold Summary

  • 1% Above List Price
  • $357/SF
  • 46 Days On Market

  Current Estimated Value $1,073,623

  Last Listing Agent Lori Zamore Signature Premier Properties

  18 Poplar Dr, Smithtown, NY 11787
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  Est $1,083,559 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,926 Sq Ft

  15 Glenrich Dr, Saint James, NY 11780

  15 Glenrich Dr, Saint James, NY 11780
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  $825,000 Sold Nov 20, 2025

  30 Twixt Hills Rd, Saint James, NY 11780

  • 4 Beds
  • 2 Baths
  • 2,200 Sq Ft
  • Built 1970

  Last Sold Summary

  • 8% Below List Price
  • $375/SF
  • 61 Days On Market

  Last Listing Agent Ronni Tranes Douglas Elliman Real Estate

  30 Twixt Hills Rd, Saint James, NY 11780
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  Est $1,161,684 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,750 Sq Ft

  287 River Rd, Saint James, NY 11780

  287 River Rd, Saint James, NY 11780
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  $1,175,301 Sold Nov 25, 2025

  36 Woodland Ln, Smithtown, NY 11787

  • 5 Beds
  • 3 Baths
  • 2,850 Sq Ft
  • Built 1975

  Last Sold Summary

  • 6% Below List Price
  • $412/SF
  • 97 Days On Market

  Last Listing Agent Deborah Dooley Signature Premier Properties

  36 Woodland Ln, Smithtown, NY 11787
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  Est $863,132 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,116 Sq Ft

  16 Pia Blvd, Smithtown, NY 11787

  16 Pia Blvd, Smithtown, NY 11787
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  $650,000 Sold Jul 30, 2025

  7 Chelsea Dr, Smithtown, NY 11787

  • 2 Beds
  • 2.5 Baths
  • 1,358 Sq Ft
  • Built 2001

  Last Sold Summary

  • 9% Above List Price
  • $479/SF
  • 14 Days On Market

  Current Estimated Value $665,241

  Last Listing Agent Eliot Lonardo Signature Premier Properties

  7 Chelsea Dr, Smithtown, NY 11787

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