Middle Island, NY Homes

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  /39

  $553,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,581 Sq Ft

  27 Huntingdale Way, Middle Island, NY 11953

  Welcome Home! Move right into the perfect 3 bedroom 2 bath Shady Grove model located at the secure gated community of Strathmore on the Green. Adjacent to Spring Lake golf course and fully renovated in 2018, this home provides a beautiful Great Room with vaulted ceilings and a formal dining room. The updates kitchen has white Shaker cabinets, subway-tiled backsplash, quartz countertops and

  

  Kerri McDonald

  Cornerstone Properties of LI

  (631) 237-9584

  27 Huntingdale Way, Middle Island, NY 11953
• Explore Middle Island

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  /11

  $3,725 per month

  The Villas at Oak Run

  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

  599 Middle Country Rd, Middle Island, NY 11953
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  $250,000 Sold Apr 08, 2025

  311 Fairview Cir, Middle Island, NY 11953

  • 2 Beds
  • 1.5 Baths
  • 870 Sq Ft
  • Built 1987

  Last Sold Summary

  • 14% Below List Price
  • $287/SF
  • 115 Days On Market

  Current Estimated Value $282,975

  Last Listing Agent John McConnell Douglas Elliman Real Estate

  311 Fairview Cir, Middle Island, NY 11953
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  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 750 Sq Ft

  279 Lake Pointe Cir, Middle Island, NY 11953

  279 Lake Pointe Cir, Middle Island, NY 11953
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  /14

  $175,000 Pending

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft

  136 Bailey Ct Unit 136, Middle Island, NY 11953

  Welcome to 136 Bailey Court, where homeownership meets affordability!Why keep renting when you can own this cozy and inviting one-bedroom, one-bath co-op? Perfect for first-time buyers or anyone looking to downsize, this home offers a spacious living room with plenty of natural light and wall-to-wall carpeting. The kitchen comes equipped with a refrigerator, dishwasher, and oven—everything

  

  Janniely Santiago

  OverSouth LLC

  (631) 528-1918

  136 Bailey Ct Unit 136, Middle Island, NY 11953
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  /10

  $2,435 per month

  • 2 Beds
  • 1 Bath
  • 740 Sq Ft
  • Apartment for Rent

  444 Lake Pointe Dr Unit 444, 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

  444 Lake Pointe Dr Unit 444, 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

  Last Listing Agent Amy Prego Shine Realty Group

  172 Fairview Cir, Middle Island, NY 11953
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  Not Listed For Sale

  • 2 Beds
  • 1 Bath

  12 Country View Ln, Middle Island, NY 11953

  12 Country View Ln, Middle Island, NY 11953
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  /29

  $419,990 Pending

  • 2 Beds
  • 1 Bath
  • 806 Sq Ft

  44 S Swezeytown Rd, Middle Island, NY 11953

  Welcome to 44 S Swezeytown Rd in Middle Island!This charming ranch sits on nearly half an acre and offers endless possibilities. The front porch leads you into a bright living room featuring a wood-burning stove—perfect for cozy winter days. The kitchen is outfitted with a quartz countertop that includes seating, as well as a gas range for the home chef. The dining area, which can also serve

  

  Lina Lopes

  Douglas Elliman Real Estate

  (631) 658-4007

  44 S Swezeytown Rd, Middle Island, NY 11953
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  /55

  $2,579 - $3,836 per month

  Stonegate

  1 - 3 Beds

  100 Stonegate Way, Middle Island, NY 11953

  Call for more information!

  100 Stonegate Way, Middle Island, NY 11953
• 

  $610,000 Sold May 12, 2025

  31 Park Ln, Middle Island, NY 11953

  • 4 Beds
  • 2 Baths
  • Built 2005

  Last Sold Summary

  • 5% Above List Price
  • 170 Days On Market

  Current Estimated Value $608,181

  Last Listing Agent Nakishia Dail Fave Realty Inc

  31 Park Ln, Middle Island, NY 11953
• 

  Est $341,275 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 947 Sq Ft

  47 Fairview Cir, Middle Island, NY 11953

  47 Fairview Cir, Middle Island, NY 11953
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  /39

  $949,500 Pending

  • 4 Beds
  • 3.5 Baths
  • 2,850 Sq Ft

  20 Bunker Ln, Middle Island, NY 11953

  A NEW HOME FOR THE HOLIDAYS! This is a 2850 sq foot DIAMOND New Construction on an ACRE ! Truly a Dream Home with Every Nuance you can Dream of! 2 Story Foyer , First level Master Suite or Room for Mom! CUSTOM Kitchen w/ 51 inch Cabinets, Quartz Counters & Backsplash, Farmhouse Sink and an 8 foot Island ! Included is all Stainless Steel Fisher Paykel Appliances ! Number 1 Oak Hardwood flooring !

  

  Rosemarie Costa

  Coldwell Banker American Homes

  (631) 446-6080

  20 Bunker Ln, Middle Island, NY 11953
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  /9

  $2,650 per month

  • 2 Beds
  • 1.5 Baths
  • 750 Sq Ft
  • Apartment for Rent

  449 Lake Pointe Dr Unit 449, 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

  449 Lake Pointe Dr Unit 449, Middle Island, NY 11953
• 

  $259,000 Sold Feb 26, 2025

  245 Artist Lake Dr, Middle Island, NY 11953

  • 2 Beds
  • 2 Baths
  • Built 1974

  Last Sold Summary

  • 50 Days On Market

  Current Estimated Value $281,174

  Last Listing Agent Jeanne De Frisco Netter Real Estate Inc

  245 Artist Lake Dr, Middle Island, NY 11953
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  Est $335,602 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 947 Sq Ft

  140 Fairview Cir, Middle Island, NY 11953

  140 Fairview Cir, Middle Island, NY 11953
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  /39

  $420,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  205 Haddon Hollow Ct, Middle Island, NY 11953

  Rare Corner Unit in Coventry Manor!Welcome to 205 Haddon Hollow Ct, a beautifully maintained and uniquely designed condo in one of Middle Island’s most desirable communities. This sun-filled corner unit offers exceptional privacy, an ideal location within the neighborhood, and a flexible layout that stands out from the rest. Originally a 3-bedroom model, this home has been thoughtfully

  

  Michael Ragosta

  Coldwell Banker M&D Good Life

  (631) 318-7864

  205 Haddon Hollow Ct, Middle Island, NY 11953
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  /97

  $2,470 - $2,850 per month

  Pinewood Estates A Vibrant 55 + Community

  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

  203 Pinewoods Crescent, Middle Island, NY 11953
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  $322,500 Sold Mar 18, 2025

  245 Fairview Cir, Middle Island, NY 11953

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

  Last Sold Summary

  • 1% Above List Price
  • $341/SF
  • 12 Days On Market

  Current Estimated Value $320,057

  Last Listing Agent Josue Sandoval Realty Connect USA L I Inc

  245 Fairview Cir, Middle Island, NY 11953
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  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft

  19 Bailey Ct Unit 19, Middle Island, NY 11953

  19 Bailey Ct Unit 19, Middle Island, NY 11953
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  /13

  $299,000 Pending

  • 2 Beds
  • 1.5 Baths
  • 900 Sq Ft

  623 Lake Ct Unit 623, Middle Island, NY 11953

  Welcome Home to this immaculate, spacious, sun drenched, and nicely updated 2BR/1.5 bath coop in desirable Lake Pointe Owners community. White & Gray EIK features plenty of counter top space, beautiful grey laminate floors & room for a 4/5 person table. Open out to the expansive 21.7X11.5 LR with wood floors, allowing for ease of entertaining. Primary BR is 14/11.5 and features a 1/2 bath. Second

  

  Maria Pascaretti

  Realty Connect USA L I Inc

  (631) 527-3599

  623 Lake Ct Unit 623, Middle Island, NY 11953
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  /17

  $1,950 per month

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Property for Rent

  10 Bailey Ct, Middle Island, NY 11953

  Welcome home to this bright and inviting one-bedroom rental located in the desirable Hidden Meadows community of Middle Island. This well-maintained upper unit features beautiful vinyl flooring throughout and an abundance of natural light. The spacious living area flows seamlessly from the living room/dining into the kitchen, which offers a convenient cut-out overlooking the living room—perfect

  Cathy Holownia Meridian Commercial Mgmt Inc

  10 Bailey Ct, Middle Island, NY 11953
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  $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

  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

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft

  131 Bailey Ct, Middle Island, NY 11953

  131 Bailey Ct, Middle Island, NY 11953
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  /48

  $699,950

  • 4 Beds
  • 2 Baths
  • 2,176 Sq Ft

  9 Lake Dr, Middle Island, NY 11953

  Experience rare lakefront living on Long Island! Set along the shores of Artist Lake in Middle Island, this spacious home offers over 2,000 sq. ft. of light-filled living space and a layout designed for comfort, flexibility, and breathtaking views. The open-concept kitchen and dining area are the heart of the home, featuring white cabinetry, warm wood floors, rich countertops, and panoramic lake

  

  Keith Dawson

  Signature Premier Properties

  (631) 250-5960

  9 Lake Dr, Middle Island, NY 11953
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  /81

  $2,405 - $2,855 per month

  Fairfield Village At Middle Island

  1 - 2 Beds

  248 Lake Pointe Cir, Middle Island, NY 11953

  SELECT UNITS GET Free Rent For February-2026 With Move-In By 2/15/26 And 12-, 15-, 18- Or 24-Month Lease With No Increase* Rent Special 2BR and Select 2BR+Den $2650* $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

  248 Lake Pointe Cir, Middle Island, NY 11953
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  $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
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  Not Listed For Sale

  • 4 Beds
  • 3 Baths

  20 Park Ln, Middle Island, NY 11953

  20 Park Ln, Middle Island, NY 11953
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  /35

  $630,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,880 Sq Ft

  1 Casey Ln Unit 255, Middle Island, NY 11953

  Welcome to Birchwood at Spring Lake, a premier gated community offering resort-style living in the heart of Middle Island. This beautifully updated corner 2-bedroom, 2-bathroom townhouse spans approximately 1,800 sqft (one of the largest townhouses in complex) and features an extended loft and office on second level. Step inside to find an open and airy layout with hi-hat lighting throughout, a

  

  Joyce Roe

  Signature Premier Properties

  (631) 353-6011

  1 Casey Ln Unit 255, Middle Island, NY 11953
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  /10

  $2,360 per month

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

  302 Tudor Ln Unit 302, 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

  302 Tudor Ln Unit 302, Middle Island, NY 11953
• 

  $565,000 Sold Mar 20, 2025

  20 Church Ln, Middle Island, NY 11953

  • 2 Beds
  • 1 Bath
  • 1,379 Sq Ft
  • Built 1945

  Last Sold Summary

  • 7% Above List Price
  • $410/SF
  • 24 Days On Market

  Current Estimated Value $580,005

  Last Listing Agent Laura Kraker Exit Realty Achieve

  20 Church Ln, Middle Island, NY 11953
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  Est $228,254 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 900 Sq Ft

  100 Artist Lake Dr, Middle Island, NY 11953

  100 Artist Lake Dr, Middle Island, NY 11953
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  /12

  $219,000 Pending

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft

  44 Bailey Unit 44, Middle Island, NY 11953

  Spectacular Ground Level unit in Hidden Meadows. This spacious 1 Bedroom was completely redone and sports Stainless appliances, granite counter tops, luxury vinyl flooring and a few more bells & whistles. Bedroom features a walk in closet and also sliders to your private backyard oasis. These tend to go very quickly so don't wait.

  

  Maria Pascaretti

  Realty Connect USA L I Inc

  (631) 502-3309

  44 Bailey Unit 44, Middle Island, NY 11953
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  /35

  $2,340 - $2,780 per month

  Fairfield Courtyard At Middle Island

  1 - 2 Beds

  101 Tudor Ln, Middle Island, NY 11953

   Free Rent For February-2026 With Move-In By 2/15/26 And 12-, 15-, 18- Or 24-Month Lease With No Increase* PLUS APT #301 Gets $100 OFF Monthly* $99 Security* *Restrictions Apply.  Property FeaturesOutstanding Exterior RenovationsProfessionally Landscaped Grounds And PlantingsEntry from Middle Country RoadPaver and Bluestone Walkways ThroughoutLeasing CenterResidence

  101 Tudor Ln, Middle Island, NY 11953
• 

  $305,000 Sold Nov 05, 2025

  372 Artist Lake Dr, Middle Island, NY 11953

  • 2 Beds
  • 1.5 Baths
  • 900 Sq Ft
  • Built 1987

  Last Sold Summary

  • 2% Above List Price
  • $339/SF
  • 29 Days On Market

  Last Listing Agent Kent Markgraf Compass Greater NY LLC

  372 Artist Lake Dr, Middle Island, NY 11953
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  Est $581,710 Not Listed For Sale

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

  15 Raymond Ave, Middle Island, NY 11953

  15 Raymond Ave, Middle Island, NY 11953
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  /20

  $339,000 Pending

  • 2 Beds
  • 2 Baths
  • 947 Sq Ft

  5 Fairview Cir, Middle Island, NY 11953

  Look no further than this totally transformed 2-bedroom, 2-bath unit that comes packed with incredible community amenities that'll make you feel like you're living in a mini-resort. Enjoy the swimming pool, fitness center, clubhouse, and so much more. Inside the unit, walk into 2 large bedrooms & bathrooms that offer plenty of space and privacy for all occupants. Ground floor walk-in access to

  

  Michael Watts

  Michael J Watts & Assoc Inc

  (631) 634-6678

  5 Fairview Cir, Middle Island, NY 11953
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  /10

  $2,000 per month

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Property for Rent

  9 Bailey Ct, Middle Island, NY 11953

  Welcome to Hidden Meadows in Middle Island! This beautifully maintained lower-level rental offers comfort, style, and convenience. The apartment has been recently painted and features new carpeting throughout. The updated kitchen showcases stainless steel appliances, rich dark cabinetry, and elegant stone countertops. Large, spacious rooms and abundant natural light create an open, inviting feel.

  Cathy Holownia Meridian Commercial Mgmt Inc

  9 Bailey Ct, Middle Island, NY 11953
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  $600,000 Sold Jul 16, 2025

  4 Lakeside Dr, Middle Island, NY 11953

  • 3 Beds
  • 2 Baths
  • 1,573 Sq Ft
  • Built 1953

  Last Sold Summary

  • 9% Above List Price
  • $381/SF
  • 14 Days On Market

  Current Estimated Value $599,647

  Last Listing Agent Peter Grosso RE/MAX Integrity Leaders

  4 Lakeside Dr, Middle Island, NY 11953
• 

  Est $356,984 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,150 Sq Ft

  26 Country View Ln, Middle Island, NY 11953

  26 Country View Ln, Middle Island, NY 11953

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