Middle Island, NY Homes

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  $189,900

  $10K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 775 Sq Ft

  86 Bailey Ct, Middle Island, NY 11953

  Welcome to 86 Bailey, a beautifully maintained and move-in ready home nestled in the quiet, sought-after Hidden Meadows Co-Op in Middle Island. Perfectly positioned for both privacy and convenience, this inviting unit offers a designated parking spot directly in front of your door, along with ample guest parking for visitors. Step inside to discover a spacious and sun-filled one-bedroom,

  

  Rita Tsoukaris

  Realty Connect USA LI

  86 Bailey Ct, Middle Island, NY 11953
• Explore Middle Island

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  /12

  Starting at $3,725 Per Month

  • 2 Beds

  599 Middle Country Rd, Middle Island, NY 11953

  Welcome to The Villas at Oak Run, the newest luxury rental community from The Crest Group.Discover the perfect balance of comfort, style, and convenience in our thoughtfully designed 2-bedroom, 2-bathroom homes. Each residence features a modern stainless steel kitchen package—including a side-by-side refrigerator with water and ice, dishwasher, range oven, and over-the-range microwave

  The Villas at Oak Run

  

  599 Middle Country Rd, Middle Island, NY 11953
• 

  $257,000

  Sold Nov 05, 2025

  172 Fairview Cir, Middle Island, NY 11953

  • 1 Bed
  • 1.5 Baths
  • 947 Sq Ft
  • Built 1985

  Last Sold Summary

  • 8% Below List Price
  • $271/SF
  • 26 Days On Market

  Current Estimated Value $265,316

  Last Listing Agent Amy Prego Shine Realty Group

  172 Fairview Cir, Middle Island, NY 11953
• 

  Est $262,048

  Not Listed For Sale

  258 Artist Lake Dr, Middle Island, NY 11953

  • 1 Bed
  • 1 Bath
  • 1,000 Sq Ft
  • Built 1974

  258 Artist Lake Dr, Middle Island, NY 11953

  Last Sold Summary

  • 59 Days On Market
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  /39

  $625,000

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

  28 Artist Lake Blvd, Middle Island, NY 11953

  This spacious 4-bedroom, 2.5-bath Colonial sits on a beautiful .43-acre lot backing a peaceful preserve, offering privacy and tranquility. Built in 1972, this home features quartz countertops, tile backsplash, stainless steel appliances, and a center island—perfect for everyday living and entertaining.Enjoy a warm and inviting den with a wood-burning fireplace and crown molding, along with

  

  Michele Mullady

  Exit Realty Island Elite

  28 Artist Lake Blvd, Middle Island, NY 11953
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  /97

  Starting at $2,395 Per Month

  • 1 - 2 Beds

  203 Pinewoods Crescent, Middle Island, NY 11953

  Suffolk County's premiere, 55 and up rental community has been carefully designed to fit your active lifestyle. Nestled among beautiful trees, Pinewood Estates provides the amenities and conveniences you want. Pinewood Estates apartment homes are beautifully appointed, with spacious floor plans and special features which rival those of many private luxury residences. At Pinewood Estates, the

  Pinewood Estates A Vibrant 55 + Community

  

  203 Pinewoods Crescent, Middle Island, NY 11953
• 

  $241,500

  Sold Mar 09, 2026

  301 Artist Lake Dr, Middle Island, NY 11953

  • 1 Bed
  • 1 Bath
  • 836 Sq Ft
  • Built 1974

  Last Sold Summary

  • 1% Above List Price
  • $289/SF
  • 51 Days On Market

  Current Estimated Value $236,089

  Last Listing Agent Raymond Matthews H & G Realty New York

  301 Artist Lake Dr, Middle Island, NY 11953
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  Not Listed For Sale

  279 Lake Pointe Cir, Middle Island, NY 11953

  • 2 Beds
  • 1 Bath
  • 750 Sq Ft
  • Built 1973

  279 Lake Pointe Cir, Middle Island, NY 11953

  Last Sold Summary

  • 20 Days On Market
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  /28

  $519,900

  Pending

  • 3 Beds
  • 2 Baths
  • 1,348 Sq Ft

  50 Rocky Point Rd, Middle Island, NY 11953

  This meticulously cared-for, move-in-ready home sits on a generous .66-acre lot and features over 1,300 square feet of living space. 2 Bedrooms on Main Level with 3rd on Lower Level. The updated kitchen shines with Corian countertops, newer appliances and tile flooring, while the living room boasts a five-year-young triple-pane bow window that fills the space with natural light. An office area

  

  Rita Tsoukaris

  Realty Connect USA LI

  50 Rocky Point Rd, Middle Island, NY 11953
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  /55

  Starting at $2,579 Per Month

  • 1 - 3 Beds

  100 Stonegate Way, Middle Island, NY 11953

  Call for more information!

  Stonegate

  

  100 Stonegate Way, Middle Island, NY 11953
• 

  $670,000

  Sold Aug 12, 2025

  10 Cedar Branch St, Middle Island, NY 11953

  • 4 Beds
  • 2.5 Baths
  • 1,900 Sq Ft
  • Built 2025

  Last Sold Summary

  • 3% Above List Price
  • $353/SF
  • 21 Days On Market

  Current Estimated Value $779,715

  Last Listing Agent Angela Mandarino Listing Pro Realty Services

  10 Cedar Branch St, Middle Island, NY 11953
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  Not Listed For Sale

  12 Country View Ln, Middle Island, NY 11953

  • 2 Beds
  • 1 Bath
  • Built 1995

  12 Country View Ln, Middle Island, NY 11953

  Last Sold Summary

  • 40 Days On Market
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  /50

  $899,950

  Open Sat 2PM - 3PM

  • 5 Beds
  • 3.5 Baths
  • 3,955 Sq Ft

  1 Lake Dr, Middle Island, NY 11953

  Welcome to a rare lakefront opportunity set on 1.28 acres along the shores of Artist Lake in Middle Island—uniquely positioned on a peninsula with water views throughout the home. Offering nearly 4,000 square feet, this 5-bedroom, 3.5-bath colonial provides a combination of space, setting, and potential that’s hard to find on Long Island. The home is filled with natural light and scenic views,

  

  Keith Dawson

  Signature Premier Properties

  1 Lake Dr, Middle Island, NY 11953
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  /35

  Starting at $2,405 Per Month

  • 1 - 2 Beds

  248 Lake Pointe Cir, Middle Island, NY 11953

  Rent Special On 1BR+Den $2650 * And Move-In By 7/15/26 Lease For 12- Or 24-Month Lease With No Increase* $99 Security* *Restrictions Apply.  Modern and spacious apartments with granite kitchen countertops and bath vanity top, stainless steel appliances and Tuscany kitchen cabinetry with brushed nickel hardware. Some with vinyl plank, granite, ceramic tile flooring*. Central-air,

  Fairfield Village At Middle Island

  

  248 Lake Pointe Cir, Middle Island, NY 11953
• 

  $440,000

  Sold Mar 19, 2026

  8 Ariel Dr, Middle Island, NY 11953

  • 2 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 1999

  Last Sold Summary

  • 6% Below List Price
  • $293/SF
  • 143 Days On Market

  Current Estimated Value $455,374

  Last Listing Agent Gina Ferraro Century 21 Anchor Real Estate

  8 Ariel Dr, Middle Island, NY 11953
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  Not Listed For Sale

  31 Country View Ln, Middle Island, NY 11953

  • 2 Beds
  • 1 Bath
  • 1,189 Sq Ft
  • Built 1995

  31 Country View Ln, Middle Island, NY 11953

  Last Sold Summary

  • 17 Days On Market
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  /49

  $899,000

  • 5 Beds
  • 2.5 Baths
  • 2,896 Sq Ft

  3 Sander Ct, Middle Island, NY 11953

  Welcome to this spacious contemporary home situated on a shy 1-acre corner lot in the desirable High School Woods section of Middle Island! Built in 2002 and offering approximately 2,896 sq ft of living space, this beautifully maintained residence features 5 bedrooms and 4 full bathrooms, including two oversized primary suites. Designed for both comfortable living and entertaining, the main level

  

  Victoria Chang

  Winzone Realty Inc

  3 Sander Ct, Middle Island, NY 11953
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  /35

  Starting at $2,360 Per Month

  • 1 - 2 Beds

  101 Tudor Ln, Middle Island, NY 11953

  GET BALANCE OF JUNE-2026 FREE with Move In By 6/30/26* And All GET Inflation Buster Special of 12 Or 24-Month Lease With No Increase With Move In By 7/15/26* $99 Security* *Restrictions Apply.Property FeaturesLedgestone and Vinyl ExteriorProfessionally Landscaped Grounds And PlantingsEntry from Middle Country RoadPaver and Bluestone Walkways ThroughoutLeasing CenterResidence Features~selected

  Fairfield Courtyard At Middle Island

  

  101 Tudor Ln, Middle Island, NY 11953
• 

  $630,000

  Sold Mar 27, 2026

  19 Raymond Ave, Middle Island, NY 11953

  • 3 Beds
  • 2.5 Baths
  • 1,498 Sq Ft
  • Built 2018

  Last Sold Summary

  • 2% Above List Price
  • $421/SF
  • 14 Days On Market

  Current Estimated Value $624,581

  Last Listing Agent Antonella Solano-Knoeller Howard Hanna Coach

  19 Raymond Ave, Middle Island, NY 11953
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  Est $324,572

  Not Listed For Sale

  47 Fairview Cir, Middle Island, NY 11953

  • 2 Beds
  • 1.5 Baths
  • 947 Sq Ft
  • Built 1988

  47 Fairview Cir, Middle Island, NY 11953

  Last Sold Summary

  • 18 Days On Market
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  /30

  $450,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 1,870 Sq Ft

  738 Birchwood Park Dr, Middle Island, NY 11953

  This Spacious MALIBU MODEL Townhouse located in the Well maintained gated community at Spring Lake condominium! This lovely young home offers approximately 1,870 sq ft of comfortable, two-level living with an functional floor plan. it comes with three bedrooms 2.5 bathrooms over look the Golf course, providing a scenic and serene backdrop year-round ! The interior features a bright eat-in

  

  Yan Wong

  Modern Realty and Management

  738 Birchwood Park Dr, Middle Island, NY 11953
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  /9

  $2,380 Per Month

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

  215 Tudor Ln Unit 215, Middle Island, NY 11953

  Ask About Our Amazing Rent Specials*. Granite Kitchen Floor & Countertops, Granite & Marble Bath Stainless Steel Appliances & In Unit Washer/Dryer, Sliders To Covered Terrace, Central-Air Conditioning & More! *Restrictions Apply., Additional information: Appearance:Diamond

  Michelle Holmes Fairfield Properties

  215 Tudor Ln Unit 215, Middle Island, NY 11953
• 

  $495,000

  Sold Sep 29, 2025

  777 Spring Lake Dr, Middle Island, NY 11953

  • 2 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • Built 1995

  Last Sold Summary

  • $344/SF
  • 25 Days On Market

  Current Estimated Value $482,906

  Last Listing Agent Gina Ficentise Century 21 Adams Real Estate

  777 Spring Lake Dr, Middle Island, NY 11953
• 

  Est $327,233

  Not Listed For Sale

  140 Fairview Cir, Middle Island, NY 11953

  • 2 Beds
  • 2 Baths
  • 947 Sq Ft
  • Built 1987

  140 Fairview Cir, Middle Island, NY 11953

  Last Sold Summary

  • 17 Days On Market
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  /38

  $689,000

  • 4 Beds
  • 3.5 Baths
  • 1,920 Sq Ft

  4 Redbud Ct, Middle Island, NY 11953

  Welcome to this beautifully maintained 4-bedroom, 3.5-bath Center Hall Colonial, perfectly situated on a quiet cul-de-sac in one of Middle Island's newer communities, built in 2000. Set on a level, fenced .52-acre lot backing to green space, the backyard is designed for entertaining with an above-ground pool featuring a newer liner and filter, spacious deck, patio, and storage shed. Inside,

  

  Yoan Velazquez

  Real Broker NY LLC

  4 Redbud Ct, Middle Island, NY 11953
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  /12

  $2,405 Per Month

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

  248 Lake Pointe Ct Unit 329, Middle Island, NY 11953

  *Ask About Our Rent Specials*. $99 Sec.Dep Special*. Restrictions Apply* Luxury living w/Spacious Bedrooms Featuring Designer Baths.Private Entry!Tuscan Cabs/Granite Ctrtops/Gas Heat & Cooking Gas Incl!Clubhouse W/Fitness Center,Laundry Rm & Pool! Pet Friendly! Conv. To Middle Country Rd,Rte 112 & Rte 83.Nr Shopping! Prices/policies subject to change without notice. *Restrictions Apply.

  Michelle Holmes Fairfield Properties

  248 Lake Pointe Ct Unit 329, Middle Island, NY 11953
• 

  $172,000

  Sold Mar 03, 2026

  136 Bailey Ct Unit 136, Middle Island, NY 11953

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Built 1971

  Last Sold Summary

  • 2% Below List Price
  • $246/SF
  • 51 Days On Market

  Last Listing Agent Janniely Santiago OverSouth LLC

  136 Bailey Ct Unit 136, Middle Island, NY 11953
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  Not Listed For Sale

  19 Bailey Ct Unit 19, Middle Island, NY 11953

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Built 1970

  19 Bailey Ct Unit 19, Middle Island, NY 11953

  Last Sold Summary

  • 71 Days On Market
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  /6

  $200,000

  • 1 Bed
  • 1 Bath
  • 836 Sq Ft

  279 Artist Lake Dr, Middle Island, NY 11953

  Priced for Action...As Is Sale..some pictures digitally enhanced

  

  Renee Steinberg

  RE/MAX Signature Real Estate

  279 Artist Lake Dr, Middle Island, NY 11953
• 

  /2

  $2,635 Per Month

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

  420 Tudor Ln, Middle Island, NY 11953

  Ask About Our Amazing Rent Specials*. Granite Kitchen Floor & Countertops, Granite & Marble Bath Stainless Steel Appliances & In Unit Washer/Dryer, Sliders To Covered Terrace, Central-Air Conditioning & More! *Restrictions Apply., Additional information: Appearance:Diamond

  Michelle Holmes Fairfield Properties

  420 Tudor Ln, Middle Island, NY 11953
• 

  $489,900

  Sold Feb 27, 2026

  1 Kate Cir, Middle Island, NY 11953

  • 2 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 2001

  Last Sold Summary

  • 9% Below List Price
  • $327/SF
  • 199 Days On Market

  Current Estimated Value $490,744

  Last Listing Agent Thomas Annunziato Howard Hanna Coach

  1 Kate Cir, Middle Island, NY 11953
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  Not Listed For Sale

  131 Bailey Ct, Middle Island, NY 11953

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Built 1971

  131 Bailey Ct, Middle Island, NY 11953

  Last Sold Summary

  • 22 Days On Market
• 

  

  /30

  $849,990

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,365 Sq Ft

  58 Coram Swezeytown Rd, Middle Island, NY 11953

  This is a True Must See!; More Than Meets The Eye!; 1 Property, Just Shy 2 Acres, 2 Houses, 2 Barns, Endless Potential! Possible AirBNB, Compound, Possible Sub-Division, Room for Mom with Proper Permits. Room For Horses! Original House Dates Back From 1880 and is Drenched in Charm, 2 Bedrooms, 2 Bathrooms, Historical Walk-Up Attic, Covered Porch. Much of The Home Is Original and in Pristine

  

  Robert Privitera

  Coldwell Banker Reliable R E

  58 Coram Swezeytown Rd, Middle Island, NY 11953
• 

  /2

  $2,635 Per Month

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

  305 Tudor Ln Unit 305, Middle Island, NY 11953

  Ask About Our Amazing Rent Specials*. Granite Kitchen Floor & Countertops, Granite & Marble Bath Stainless Steel Appliances & In Unit Washer/Dryer, Sliders To Covered Terrace, Central-Air Conditioning & More! *Restrictions Apply., Additional information: Appearance:Diamond

  Michelle Holmes Fairfield Properties

  305 Tudor Ln Unit 305, Middle Island, NY 11953
• 

  $203,000

  Sold Aug 19, 2025

  99 Whistler Ct Unit 99, Middle Island, NY 11953

  • 1 Bed
  • 1 Bath
  • 675 Sq Ft
  • Built 1980

  Last Sold Summary

  • 2% Above List Price
  • $301/SF
  • 44 Days On Market

  Last Listing Agent Rita Tsoukaris Realty Connect USA LI

  99 Whistler Ct Unit 99, Middle Island, NY 11953
• 

  Not Listed For Sale

  20 Park Ln, Middle Island, NY 11953

  • 4 Beds
  • 3 Baths
  • Built 1959

  20 Park Ln, Middle Island, NY 11953

  Last Sold Summary

  • 19 Days On Market
• 

  

  /15

  $219,900

  $5K PRICE INCREASE Pending

  • 1 Bed
  • 1 Bath
  • 830 Sq Ft

  43 Artist Lake Dr, Middle Island, NY 11953

  Welcome to 43 Artist Lake Dr! This second floor, 1-Bed 1-Bath condo features hardwood floors, central air and heat, gas cooking, in-unit laundry and a balcony overlooking the courtyard. The community features a community pool, a dog park, a basketball court, a tennis court and a playground! Enjoy everything the clubhouse has to offer; featuring a gym, a pool table and ping pong! There are plenty

  

  Mario Arias

  Oversouth LLC

  43 Artist Lake Dr, Middle Island, NY 11953
• 

  

  /23

  $2,450 Per Month

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

  238 Artist Lake Dr, Middle Island, NY 11953

  upper-level condo features club house pool gas heat water included sect 8 welcome close to stores buses Amenities include Outdoor swimming pool, Clubhouse, Tennis courts, dog park and walking path

  Rainer Jessen Coldwell Banker American Homes

  238 Artist Lake Dr, Middle Island, NY 11953
• 

  $455,000

  Sold Feb 18, 2026

  38 Huntingdale Way, Middle Island, NY 11953

  • 2 Beds
  • 2 Baths
  • 1,320 Sq Ft
  • Built 1987

  Last Sold Summary

  • 1% Below List Price
  • $345/SF
  • 24 Days On Market

  Current Estimated Value $455,576

  Last Listing Agent Cheryl Figueroa Coldwell Banker American Homes

  38 Huntingdale Way, Middle Island, NY 11953
• 

  Est $593,434

  Not Listed For Sale

  15 Raymond Ave, Middle Island, NY 11953

  • 5 Beds
  • 2 Baths
  • 1,732 Sq Ft
  • Built 1970

  15 Raymond Ave, Middle Island, NY 11953

  Last Sold Summary

  • 15 Days On Market

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