Middle Island, NY Homes

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  $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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  /13

  $2,000 per month

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

  83 Bailey Ct, Middle Island, NY 11953

  Beautiful upper unit co-op in the lovely Hidden Meadows Community. Cherry cabinets, granite counter tops in kitchen and breakfast bar. King-size bedroom with walk-in closet and sliding doors to private balcony. Updated bathroom. Plenty of closet space. Laundry room on premises. In-ground pool and tennis court. Assigned parking space and plenty of parking for guests.

  Cathy Holownia Meridian Commercial Mgmt Inc

  83 Bailey Ct, 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 $598,896

  Last Listing Agent Peter Grosso RE/MAX Integrity Leaders

  4 Lakeside Dr, Middle Island, NY 11953
• 

  Est $357,686 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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  $769,999

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

  39 Lakeview Dr, Middle Island, NY 11953

  Welcome to 39 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

  39 Lakeview Dr, Middle Island, NY 11953
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  /6

  $2,000 per month

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

  41 Artist Lake Dr, Middle Island, NY 11953

  Welcome to a newly renovated, spacious, and functional condo unit. Featured on the first floor featuring 1br, LR, kitchen, and full bathroom. BR will is ideal for a king size bed, and offers plenty of closet space. To move in 1 month rent, security deposit. Conveniently close to Brookhaven State Park, Middle Island country club, and Mill Pond Golf Course. A must see to endure.

  Elrick Meyers Meyers Enterprise Realty Group

  41 Artist Lake Dr, Middle Island, NY 11953
• 

  $500,000 Sold Apr 02, 2025

  17 Park Ln, Middle Island, NY 11953

  • 4 Beds
  • 2 Baths
  • 1,543 Sq Ft
  • Built 1993

  Last Sold Summary

  • 18% Above List Price
  • $324/SF
  • 14 Days On Market

  Current Estimated Value $519,978

  Last Listing Agent Lisa Jaeger Douglas Elliman Real Estate

  17 Park Ln, Middle Island, NY 11953
• 

  Est $304,717 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 947 Sq Ft

  26 Fairview Cir, Middle Island, NY 11953

  26 Fairview Cir, Middle Island, NY 11953
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  $749,999

  • 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
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  /11

  $2,780 per month

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

  401 Tudor Ln Unit 401, 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

  401 Tudor Ln Unit 401, Middle Island, NY 11953
• 

  $400,000 Sold May 08, 2025

  15 Westchester Ct, Middle Island, NY 11953

  • 3 Beds
  • 2 Baths
  • 1,169 Sq Ft
  • Built 1997

  Last Sold Summary

  • 3% Above List Price
  • $342/SF
  • 43 Days On Market

  Current Estimated Value $421,735

  Last Listing Agent Daniel Birnbaum Daniel Gale Sothebys Intl Rlty

  15 Westchester Ct, Middle Island, NY 11953
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  Est $334,193 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 947 Sq Ft

  44 Fairview Cir, Middle Island, NY 11953

  44 Fairview Cir, Middle Island, NY 11953
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  $799,900 Pending

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

  111 Currans Rd, Middle Island, NY 11953

  New Construction - Stunning and spectacular modern and traditional center hall colonial. Very few new homes on the market as nice as this one. features are gourmet kitchen with center Island and cooktop, including wall oven and convection microwave. Wine and beverage cooler area, living room with centerpiece fireplace and custom molding throughout the first floor. Formal dining room, den and full

  C Reade Stewart Brookhampton Realty

  111 Currans Rd, Middle Island, NY 11953
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  /2

  $2,640 per month

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

  317 Tudor Ln Unit 317, 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

  317 Tudor Ln Unit 317, Middle Island, NY 11953
• 

  $535,000 Sold Jan 28, 2025

  23 Madison Cir, Middle Island, NY 11953

  • 2 Beds
  • 2 Baths
  • Built 2001

  Last Sold Summary

  • 7% Above List Price
  • 10 Days On Market

  Current Estimated Value $558,466

  Last Listing Agent Lilly Kaklamanis Realty Connect USA LI Inc

  23 Madison Cir, Middle Island, NY 11953
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  Est $620,637 Not Listed For Sale

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

  21 Ariel Dr, Middle Island, NY 11953

  21 Ariel Dr, Middle Island, NY 11953
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  $625,000 Pending

  • 5 Beds
  • 3.5 Baths
  • 2,832 Sq Ft

  32 Artist Lake Blvd, Middle Island, NY 11953

  This 5 Bedroom, 3.5 Bath Colonial offers the perfect blend of space and comfort. The main level features a large eat-in kitchen ideal for gatherings and a welcoming living room with a fireplace. Upstairs, the primary suite includes a walk-in closet and private full bath, while additional bedrooms provide plenty of room for family or guests. With proper permits, there is potential for a

  Peter Grosso RE/MAX Integrity Leaders

  32 Artist Lake Blvd, Middle Island, NY 11953
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  $1,600 per month

  • 1 Bath
  • Apartment for Rent

  23 Wellington Rd, Middle Island, NY 11953

  Beautiful Bright & Sunny Furnished or Unfurnished studio apartment on ground level with separate entrance. $1,650 includes all!!! NO SMOKING/NO PETS/ SINGLE OCCUPANCY

  Rachel Cole Harmony Homes Signature Prop

  23 Wellington Rd, Middle Island, NY 11953
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  $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 $803,551

  Last Listing Agent Jan Josephson-Lynch Cornerstone Properties of LI

  2 Cathedral Ct, Middle Island, NY 11953
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  Est $572,400 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,106 Sq Ft

  9 Richard Ln, Middle Island, NY 11953

  9 Richard Ln, Middle Island, NY 11953
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  $239,999

  • 1 Bed
  • 1 Bath
  • 836 Sq Ft

  301 Artist Lake Dr, Middle Island, NY 11953

  This beautifully updated 1 bedroom ground level home offers an efficient kitchen, a comfortable living room, and a cozy dining area perfect for everyday use. Additional highlights include a new bathroom, central air conditioning, and stunning oak hardwood floors throughout. Ideally located near shops. transportation and everything you need. Why rent when you can own!

  Raymond Matthews H & G Realty New York

  301 Artist Lake Dr, Middle Island, NY 11953
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  /10

  $2,435 per month

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

  442 Lake Pointe Dr Unit 442, 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

  442 Lake Pointe Dr Unit 442, Middle Island, NY 11953
• 

  $315,000 Sold Jun 20, 2025

  274 Artist Lake Dr Unit 274, Middle Island, NY 11953

  • 2 Beds
  • 2 Baths
  • 950 Sq Ft
  • Built 1974

  Last Sold Summary

  • 2% Above List Price
  • $332/SF
  • 343 Days On Market

  Current Estimated Value $314,510

  Last Listing Agent Michael Welsh Douglas Elliman Real Estate

  274 Artist Lake Dr Unit 274, Middle Island, NY 11953
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  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 775 Sq Ft

  86 Bailey Ct, Middle Island, NY 11953

  86 Bailey Ct, Middle Island, NY 11953
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  /3

  $510,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,426 Sq Ft

  56 E Bartlett Rd, Middle Island, NY 11953

  Attention investors and builders! This private Colonial sits on almost 3 acres and offers incredible potential. The home needs TLC but provides solid bones, generous size of over 2400sq feet, and a peaceful setting. Ideal for those looking to customize or rebuild.

  Frank Mirando Realty Connect USA L I Inc

  56 E Bartlett Rd, Middle Island, NY 11953
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  /6

  $2,425 per month

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

  401 Lake Pointe Dr Unit 401, 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

  401 Lake Pointe Dr Unit 401, Middle Island, NY 11953
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  $245,000 Sold Mar 26, 2025

  624 Lake Ct Unit 624, Middle Island, NY 11953

  • 2 Beds
  • 1.5 Baths
  • 950 Sq Ft
  • Built 1978

  Last Sold Summary

  • $258/SF
  • 18 Days On Market

  Last Listing Agent Patricia Shaffer Signature Premier Properties

  624 Lake Ct Unit 624, Middle Island, NY 11953
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  Not Listed For Sale

  • 2 Beds
  • 1 Bath

  166 Artist Lake Dr Unit A, Middle Island, NY 11953

  166 Artist Lake Dr Unit A, Middle Island, NY 11953
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  $925,000

  • 6 Beds
  • 3 Baths
  • 3,700 Sq Ft

  0 Daniel Ln Unit KEY823323, Middle Island, NY 11953

  Calling all Car/Sports/Hobby or Toy Enthusiasts- This home features a Custom Built Detached 3-car garage! New Construction to be built upon 1 acre of land on a quiet dead-end street. Perfect for Generational Living with a total of 6 Generously Sized Bedrooms and 3 Full Bathrooms. There is still time to customize and choose finishes. Amazing Opportunity!

  Katheryn Correa Realty Connect USA L I Inc

  0 Daniel Ln Unit KEY823323, Middle Island, NY 11953
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  /9

  $2,425 per month

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

  29 Lake Pointe Ct Unit 293, 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

  29 Lake Pointe Ct Unit 293, 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

  Last Listing Agent Kandice Morales Signature Premier Properties

  262 Artist Lake Dr, Middle Island, NY 11953
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  Est $546,753 Not Listed For Sale

  • 2 Beds
  • 2 Baths

  568 Birchwood Park Dr, Middle Island, NY 11953

  568 Birchwood Park Dr, Middle Island, NY 11953
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  /21

  $525,000

  • 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
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  /9

  $2,405 per month

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

  463 Lake Pointe Dr Unit 463, 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

  463 Lake Pointe Dr Unit 463, 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

  Last Listing Agent Karen Roth RE/MAX Integrity Leaders

  125 W Bartlett Rd, Middle Island, NY 11953
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  Est $486,018 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,628 Sq Ft

  3 Ashton Rd, Medford, NY 11763

  3 Ashton Rd, Medford, NY 11763
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  /29

  $499,999

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

  1 Kate Cir, Middle Island, NY 11953

  Enjoy Country Club Living! Corner Lot! Perfectly Maintained 2 Bedroom 2 Bath Devon 2 Model with Updates That Include: Tile Entry, Newer Flooring, Newer Dishwasher, Updated Baths And Hi Hat Lighting!Amenities Include: Private 9 Hole Golf Course, 2 Clubhouses, 4 Pools, Tennis, Pickleball, Racquetball, 2 Gyms, and Many Social Activities All In A 24 Hr Gated Community!

  Thomas Annunziato Howard Hanna Coach

  1 Kate Cir, Middle Island, NY 11953
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  $2,650 per month

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

  470 Lake Pointe Dr Unit 470, 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

  470 Lake Pointe Dr Unit 470, 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
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  Est $601,468 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,422 Sq Ft

  3 Wagner Rd, Medford, NY 11763

  3 Wagner Rd, Medford, NY 11763

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