Middle Island, NY Homes

• 

  

  

  /26

  $729,990

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,148 Sq Ft

  54 Winterberry Dr, Middle Island, NY 11953

  Beautifully landscaped 4-bedroom, 2.5-bath Colonial located in the Pine Ridge section of The Preserve in Middle Island. Built in 2001, this stunning home offers an open-concept kitchen and living room layout perfect for entertaining and everyday living. The second floor features a spacious primary suite with a private bath, along with three additional generously sized bedrooms. The home features

  

  Yoan Velazquez

  Real Broker NY LLC

  54 Winterberry Dr, Middle Island, NY 11953
• 

  

  

  /12

  $2,780 Per Month

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

  301 Tudor Ln Unit 301, 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

  301 Tudor Ln Unit 301, 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

  Current Estimated Value $305,187

  Last Listing Agent Kent Markgraf Compass Greater NY LLC

  372 Artist Lake Dr, Middle Island, NY 11953
• 

  Est $355,111

  Not Listed For Sale

  239 Fairview Cir, Middle Island, NY 11953

  • 2 Beds
  • 2 Baths
  • 1,086 Sq Ft
  • Built 1987

  239 Fairview Cir, Middle Island, NY 11953

  Last Sold Summary

  • 19 Days On Market
• 

  

  

  /31

  $595,000

  • 2 Beds
  • 2 Baths
  • 1,670 Sq Ft

  5 Charley Ln Unit 270, Middle Island, NY 11953

  Welcome home to this beautiful, move-in ready, completely renovated in 2023, Springfield model located in this 24/7 gated community with fantastic amenities. Beautifully landscaped with new front pavers leading to the front door. Walk inside to an open concept area with vaulted ceilings and recessed lighting. Kitchen offers stainless steel appliances, tile backsplash, soft close cabinets, gas

  

  Rita Tsoukaris

  Realty Connect USA LI

  5 Charley Ln Unit 270, Middle Island, NY 11953
• 

  

  /9

  $2,650 Per Month

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

  248 Lake Pointe Dr Unit 255, 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 Dr Unit 255, Middle Island, NY 11953
• 

  $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 $610,912

  Last Listing Agent Peter Grosso RE/MAX Integrity Leaders

  4 Lakeside Dr, Middle Island, NY 11953
• 

  Est $352,472

  Not Listed For Sale

  26 Country View Ln, Middle Island, NY 11953

  • 2 Beds
  • 1 Bath
  • 1,150 Sq Ft
  • Built 1995

  26 Country View Ln, Middle Island, NY 11953

  Last Sold Summary

  • 35 Days On Market
• 

  

  /19

  $192,500

  Open Sat 11:30AM - 1PM $5K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft

  129 Bailey Ct, Middle Island, NY 11953

  Spacious 1 Bedroom upper end unit featuring a new kitchen with window, oversized living room and dining area with wood floors. Generously sized primary bedroom with a large walk-in closet. This light and bright end unit offers added privacy and natural light along with newer appliances, new carpeting and wood floors. Beautiful deck for grilling or just sitting and relaxing. Conveniently located

  

  Rita Tsoukaris

  Realty Connect USA LI

  129 Bailey Ct, Middle Island, NY 11953
• 

  

  /10

  $2,400 Per Month

  • 2 Beds
  • 1.5 Baths
  • 947 Sq Ft
  • Condo for Rent

  9 Fairview Cir, Middle Island, NY 11953

  Beautiful 2 Bedrooms 1.5 Bath Apartment located at very convenient condo complex , Hardwood Floor, large windows, 2nd Floor , Balcony , washer and dryer in unit!

  Qun Lin Sweet Key Realty Group Inc

  9 Fairview Cir, Middle Island, NY 11953
• 

  $300,000

  Sold Mar 19, 2026

  623 Lake Ct Unit 623, Middle Island, NY 11953

  • 2 Beds
  • 1.5 Baths
  • 900 Sq Ft
  • Built 1979

  Last Sold Summary

  • $333/SF
  • 288 Days On Market

  Last Listing Agent Maria Pascaretti Realty Connect USA L I Inc

  623 Lake Ct Unit 623, Middle Island, NY 11953
• 

  Est $324,661

  Not Listed For Sale

  44 Fairview Cir, Middle Island, NY 11953

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

  44 Fairview Cir, Middle Island, NY 11953

  Last Sold Summary

  • 93 Days On Market
• 

  

  /50

  $948,500

  New Construction Pending

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

  20 Bunker Ln, Middle Island, NY 11953

  DREAM HOME FOR SALE ! This is a 2850 Square 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 with 51" inch Cabinets, Quartz Counters & Backsplash, Farmhouse Sink ,and an Eight Foot Island ! Included is all Stainless Steel Fisher Paykel Appliances! Number 1 Oak Flooring Thru

  

  Rosemarie Costa

  Coldwell Banker American Homes

  20 Bunker Ln, Middle Island, NY 11953
• 

  

  /10

  $2,780 Per Month

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

  524 Tudor Ln Unit 524, 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

  524 Tudor Ln Unit 524, Middle Island, NY 11953
• 

  $255,000

  Sold Jun 16, 2026

  137 Fieldstone Ct, Middle Island, NY 11953

  • 3 Beds
  • 2 Baths
  • 1,133 Sq Ft
  • Built 1975

  Last Sold Summary

  • 2% Above List Price
  • $225/SF
  • 10 Days On Market

  Current Estimated Value $405,995

  Last Listing Agent Justin Pollio New Door Properties LLC

  137 Fieldstone Ct, Middle Island, NY 11953
• 

  Est $336,349

  Not Listed For Sale

  80 Fairview Cir, Middle Island, NY 11953

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

  80 Fairview Cir, Middle Island, NY 11953

  Last Sold Summary

  • 24 Days On Market
• 

  

  /43

  $749,999

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,260 Sq Ft

  37 Lakeview Dr, Middle Island, NY 11953

  Welcome to 37 Lakeview Drive! This brand-new 2025 Colonial has been crafted with modern luxury and timeless design. The door opens to a grand foyer with an open-concept and a ton of natural sun light. The built-in electric fireplace, recessed lighting, and seamless flow set the tone for both intimate evenings and vibrant gatherings. At the heart of the home, the chef’s kitchen shines with an

  Kevin Iglesias Signature Premier Properties

  37 Lakeview Dr, Middle Island, NY 11953
• 

  

  /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
• 

  $305,000

  Sold Mar 20, 2026

  35 Adams Ln, Middle Island, NY 11953

  • 4 Beds
  • 2 Baths
  • 1,418 Sq Ft
  • Built 1950

  Last Sold Summary

  • 2% Above List Price
  • $215/SF
  • 30 Days On Market

  Current Estimated Value $314,434

  Last Listing Agent Derek Greene Greene Realty Group

  35 Adams Ln, Middle Island, NY 11953
• 

  Est $315,140

  Not Listed For Sale

  219 Fairview Cir, Middle Island, NY 11953

  • 2 Beds
  • 2 Baths
  • 1,086 Sq Ft
  • Built 1988

  219 Fairview Cir, Middle Island, NY 11953

  Last Sold Summary

  • 18 Days On Market
• 

  

  /44

  $699,998

  $19K PRICE DROP

  • 6 Beds
  • 2 Baths
  • 2,100 Sq Ft

  130 Park Ln, Middle Island, NY 11953

  Welcome home to a beautifully renovated property that blends modern style with everyday comfort. The all-new kitchen is bright and inviting, featuring quartz countertops, stainless steel appliances, crisp white cabinetry, subway tile backsplash, updated LED lighting, and a clean layout designed for daily living and entertaining. The renovated bathroom offers a fresh, modern feel with a double

  Martin Hammer H & G Realty New York

  130 Park Ln, Middle Island, NY 11953
• 

  

  /6

  $2,075 Per Month

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

  229 Artist Lake Dr, Middle Island, NY 11953

  This is a full renovated first floor unit located in the Artist Lake Community. Enjoy Easy living with beautifully manicured grounds and great amenities, including an outdoor pool, clubhouse, and tennis courts. Must have excellent credit with proof of good previous rental history. Non Smoking tenants only

  Jennifer Lenzo Island Advantage Realty LLC

  229 Artist Lake Dr, Middle Island, NY 11953
• 

  $790,000

  Sold Aug 11, 2025

  2 Cathedral Ct, Middle Island, NY 11953

  • 4 Beds
  • 3.5 Baths
  • 2,700 Sq Ft
  • Built 1993

  Last Sold Summary

  • 1% Below List Price
  • $293/SF
  • 42 Days On Market

  Current Estimated Value $811,160

  Last Listing Agent Jan Josephson-Lynch Cornerstone Properties of LI

  2 Cathedral Ct, Middle Island, NY 11953
• 

  Not Listed For Sale

  102 Whistler Ct Unit 102, Middle Island, NY 11953

  • 1 Bed
  • 1 Bath
  • Built 1972

  102 Whistler Ct Unit 102, Middle Island, NY 11953

  Last Sold Summary

  • 12 Days On Market
• 

  

  /50

  $589,999

  Pending

  • 3 Beds
  • 2.5 Baths
  • 1,184 Sq Ft

  20 Middle Island Rd, Middle Island, NY 11953

  Welcome to 20 Middle Island Rd, a fully renovated, move-in-ready home for sale in Middle Island, NY. Nestled in the heart of Long Island, this stunning property backs directly onto a protected Suffolk County nature preserve, offering unparalleled privacy and tranquil woodland views with no rear neighbors. This beautifully updated 3-bedroom, 2.5-bathroom home seamlessly blends modern upgrades with

  Jeffrey Jimenez EXP Realty

  20 Middle Island Rd, Middle Island, NY 11953
• 

  

  /9

  $2,650 Per Month

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

  248 Lake Pointe Dr Unit 394, 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 Dr Unit 394, Middle Island, NY 11953
• 

  $700,000

  Sold May 07, 2026

  9 Lake Dr, Middle Island, NY 11953

  • 4 Beds
  • 2 Baths
  • 2,176 Sq Ft
  • Built 1950

  Last Sold Summary

  • $322/SF
  • 116 Days On Market

  Current Estimated Value $695,399

  Last Listing Agent Keith Dawson Signature Premier Properties

  9 Lake Dr, Middle Island, NY 11953
• 

  Est $214,278

  Not Listed For Sale

  81 Artist Lake Dr, Middle Island, NY 11953

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

  81 Artist Lake Dr, Middle Island, NY 11953

  Last Sold Summary

  • 36 Days On Market
• 

  

  /20

  $600,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 1,872 Sq Ft

  62 W Bartlett Rd, Middle Island, NY 11953

  Spacious 4-bedroom, 2.5-bath home situated on a beautiful .55-acre corner lot featuring: Fireplace, 2-car garage, generous yard space, strong layout & incredible potential with .55-acre corner lot offer strong upside potential. This home offers a fantastic opportunity for buyers looking to customize and add value in the Longwood area location. Perfect for End users ready to renovate, investors

  Nadjamy Jean-Claude Exit Realty Edge

  62 W Bartlett Rd, Middle Island, NY 11953
• 

  $215,000

  Sold Oct 07, 2025

  262 Artist Lake Dr, Middle Island, NY 11953

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

  Last Sold Summary

  • $257/SF
  • 11 Days On Market

  Current Estimated Value $217,142

  Last Listing Agent Kandice Morales Signature Premier Properties

  262 Artist Lake Dr, Middle Island, NY 11953
• 

  Est $496,889

  Not Listed For Sale

  45 N Swezeytown Rd, Middle Island, NY 11953

  • 3 Beds
  • 1 Bath
  • 1,094 Sq Ft
  • Built 1955

  45 N Swezeytown Rd, Middle Island, NY 11953

  Last Sold Summary

  • 36 Days On Market
• 

  

  /17

  $545,000

  Pending

  • 4 Beds
  • 2 Baths
  • 1,476 Sq Ft

  12 Lakeview Dr, Middle Island, NY 11953

  Nestled on a quiet, tree-lined street, this turnkey home offers an ideal blend of modern upgrades and comfort. Featuring 4 bedrooms, 2 full bathrooms and just under 1,500 sq ft of well-maintained space, plus a finished basement with entrances from the interior or through the Bilco doors on the exterior. Situated on a generous .34-acre lot, the property boasts a spacious fully fenced-in yard and

  Eric Boorum Douglas Elliman Real Estate

  12 Lakeview Dr, Middle Island, NY 11953
• 

  $650,000

  Sold Nov 17, 2025

  125 W Bartlett Rd, Middle Island, NY 11953

  • 3 Beds
  • 2.5 Baths
  • 2,376 Sq Ft
  • Built 1994

  Last Sold Summary

  • $274/SF
  • 33 Days On Market

  Current Estimated Value $758,169

  Last Listing Agent Karen Roth RE/MAX Integrity Leaders

  125 W Bartlett Rd, Middle Island, NY 11953
• 

  Est $604,435

  Not Listed For Sale

  21 Ariel Dr, Middle Island, NY 11953

  • 3 Beds
  • 2.5 Baths
  • 2,500 Sq Ft
  • Built 1995

  21 Ariel Dr, Middle Island, NY 11953

  Last Sold Summary

  • 56 Days On Market
• 

  

  /21

  $565,000

  $34K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 888 Sq Ft

  1 Pine Rd, Middle Island, NY 11953

  This newly three-bedroom Ranch fully renovated on a corner lot property fully fenced. Driveway re-done all cement. All wood flooring throughout the house, Waser/Dryer hook up. New electrical system. Great starter home or looking to downsize. Low taxes close to all shopping and hospitals nearby. Don't let this opportunity pass you by.

  Eman Prestyly H & G Realty New York

  1 Pine Rd, Middle Island, NY 11953
• 

  $305,000

  Sold Jul 28, 2025

  106 Fairview Cir Unit 106, Middle Island, NY 11953

  • 2 Beds
  • 2 Baths
  • Built 1987

  Last Sold Summary

  • 5% Below List Price
  • 280 Days On Market

  Last Listing Agent Daniel Randazzo HomeSmart Premier Living Rlty

  106 Fairview Cir Unit 106, Middle Island, NY 11953
• 

  Est $535,815

  Not Listed For Sale

  10 Tracie Ln Unit 1, Middle Island, NY 11953

  • 2 Beds
  • 2 Baths
  • 1,716 Sq Ft
  • Built 2001

  10 Tracie Ln Unit 1, Middle Island, NY 11953

  Last Sold Summary

  • 18 Days On Market
• 

  

  /15

  $254,000

  $5K PRICE DROP Pending

  • 1 Bed
  • 1 Bath
  • 836 Sq Ft

  289 Artist Lake Dr, Middle Island, NY 11953

  This beautifully updated 1 bedroom ground level condo offers efficient kitchen, a comfortable living room, and a cozy dining area perfect for everyday use. The community features a community pool, a dog park, a basketball court, a tennis court and a playground. Enjoy everything a club house has to offer featuring a gym, a pool table and ping pong. there is plenty of parking space available

  Sham Lal Blackstone Realty

  289 Artist Lake Dr, Middle Island, NY 11953
• 

  $455,000

  Sold Mar 13, 2026

  1 Philip Ln, Middle Island, NY 11953

  • 2 Beds
  • 2 Baths
  • 1,504 Sq Ft
  • Built 2002

  Last Sold Summary

  • 3% Below List Price
  • $303/SF
  • 62 Days On Market

  Current Estimated Value $463,621

  Last Listing Agent Thomas Roden Coldwell Banker American Homes

  1 Philip Ln, Middle Island, NY 11953
• 

  Not Listed For Sale

  49 Fairview Cir Unit 49, Middle Island, NY 11953

  • 1 Bed
  • 1.5 Baths
  • 954 Sq Ft
  • Built 1987

  49 Fairview Cir Unit 49, Middle Island, NY 11953

  Last Sold Summary

  • 31 Days On Market

Showing Results 41 - 80, Page 2 of 18