Middle Island, NY Homes

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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

  Signature Premier Properties

  (631) 528-1918

  136 Bailey Ct Unit 136, Middle Island, NY 11953
• Explore Middle Island

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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
• 

  $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 $283,342

  Last Listing Agent John McConnell Douglas Elliman Real Estate

  311 Fairview Cir, Middle Island, NY 11953
• 

  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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  /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
• 

  

  /18

  $3,000 per month

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

  334 Artist Lake Dr, Middle Island, NY 11953

  Just Unpack And Move Right Into This Beautiful, Mint Condition Upper Level Condo. This Unit Features 2 Bedrooms, One Full Bath And A Primary Bedroom Half Bath. This Desirable FURNISHED End Unit Also Features An Outdoor Private Balcony For Relaxing. Community Amenities Include A Pool, Fitness Center, Tennis and Clubhouse.

  Joseph Cordani H & G Realty New York

  334 Artist Lake Dr, 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
• 

  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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  /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
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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
• 

  $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 $609,314

  Last Listing Agent Nakishia Dail Fave Realty Inc

  31 Park Ln, Middle Island, NY 11953
• 

  Est $340,171 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
• 

  

  /23

  $449,990

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

  8 Ariel Dr, Middle Island, NY 11953

  Don't miss this opportunity to own the popular Devon style ranch in the Birchwood community!! Home features great sized rooms with high ceilings, eat-in-kitchen, formal dining room, living room, and den with sliders leading to nice patio and fenced yard. Two bedrooms, primary bedroom includes ensuite, laundry room, walk-up attic for great storage, and 1 car garage all in a 24hr guard-gated and

  

  Gina Ferraro

  Century 21 Anchor Real Estate

  (631) 238-9114

  8 Ariel Dr, Middle Island, NY 11953
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  /10

  $2,435 per month

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

  342 Lake Pointe Dr Unit 342, 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

  342 Lake Pointe Dr Unit 342, 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 $278,179

  Last Listing Agent Jeanne De Frisco Netter Real Estate Inc

  245 Artist Lake Dr, Middle Island, NY 11953
• 

  Est $334,494 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
• 

  

  /35

  $630,000

  • 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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  /37

  $2,405 - $2,855 per month

  Fairfield Village At Middle Island

  1 - 2 Beds

  248 Lake Pointe Cir, Middle Island, NY 11953

  Free Rent Until 1/1/2026 Move-In By 1/1/26 And 12*, 15, 18, Or 24-Month Lease No Increase* Or Receive $1200 Off 1-Time Move-In By 1/15/2026 With 15- Or 24-Month 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

  248 Lake Pointe Cir, Middle Island, NY 11953
• 

  $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 $321,909

  Last Listing Agent Josue Sandoval Realty Connect USA L I Inc

  245 Fairview Cir, Middle Island, NY 11953
• 

  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
• 

  /2

  $409,990 Pending

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft

  11 Mauritz Blvd, Middle Island, NY 11953

  3 Bedroom Ranch with 1 Car Garage and Full basement * Wood Flooring * Needs Updating

  

  Evan Greene

  RE/MAX Signature Real Estate

  (631) 641-7938

  11 Mauritz Blvd, Middle Island, NY 11953
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  /10

  $2,425 per month

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

  447 Lake Pointe Dr, 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

  447 Lake Pointe Dr, 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

  Last Listing Agent Angela Mandarino Listing Pro Realty Services

  10 Cedar Branch St, Middle Island, NY 11953
• 

  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
• 

  

  /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
• 

  

  /35

  $2,340 - $2,780 per month

  Fairfield Courtyard At Middle Island

  1 - 2 Beds

  101 Tudor Ln, Middle Island, NY 11953

   Free Rent Until 1/1/2026 Move-In By 1/1/26 And 12*, 15, 18, Or 24-Month Lease No Increase* Or Receive $1200 Off 1-Time Move-In By 1/15/26 On 15- Or 24-Month No Increase* $99 Security* *Restrictions Apply. Property FeaturesOutstanding Exterior RenovationsProfessionally Landscaped Grounds And PlantingsEntry from Middle Country RoadPaver and Bluestone Walkways ThroughoutLeasing

  101 Tudor Ln, Middle Island, NY 11953
• 

  $497,500 Sold Dec 19, 2024

  1 Sophia Dr, Middle Island, NY 11953

  • 3 Beds
  • 2.5 Baths
  • Built 1999

  Last Sold Summary

  • 10% Below List Price
  • 81 Days On Market

  Last Listing Agent Thomas Annunziato Howard Hanna Coach

  1 Sophia Dr, Middle Island, NY 11953
• 

  Not Listed For Sale

  • 4 Beds
  • 3 Baths

  20 Park Ln, Middle Island, NY 11953

  20 Park Ln, Middle Island, NY 11953
• 

  

  /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
• 

  

  /7

  $2,435 per month

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

  356 Lake Pointe Dr, 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

  356 Lake Pointe Dr, 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
• 

  Est $234,686 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
• 

  

  /15

  $219,900 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

  (631) 658-4045

  43 Artist Lake Dr, Middle Island, NY 11953
• 

  

  /10

  $2,100 per month

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

  250 Artist Lake Dr, Middle Island, NY 11953

  This beautifully updated 1-bedroom 2nd-floor unit offers an efficient kitchen, a comfortable living room, and a cozy dining area perfect for everyday use. Additional highlights includes 2 bathrooms, central air conditioning, and stunning oak hardwood floors throughout. Ideally located near shops. transportation and everything you need.

  Frank Castelli Signature Premier Properties

  250 Artist Lake Dr, 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 $575,118

  Last Listing Agent Laura Kraker Exit Realty Achieve

  20 Church Ln, Middle Island, NY 11953
• 

  Est $593,530 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
• 

  

  /33

  $399,990

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

  825 Spring Lake Dr, Middle Island, NY 11953

  Welcome to Birchwood at Spring Lake! This non-age restricted gated community boasts a host of amenities including both indoor and outdoor pools, playground, tennis, Pickleball, clubhouse, gym and 9 hole golf course - Enjoy a true country club lifestyle every day. This two bedroom, two full bath Galaxy model has an open floor plan, and is perfect to personalize your way. Snow removal, landscaping

  

  Jo Ann Boettcher

  Douglas Elliman Real Estate

  (631) 443-4275

  825 Spring Lake Dr, Middle Island, NY 11953
• 

  

  /16

  $2,000 per month

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

  26 Bailey Ct, Middle Island, NY 11953

  Welcome to one of the best locations in the Hidden Meadows Community! Whether you gaze out of your living room windows onto the meadow or sit on your balcony and enjoy the beautiful view of trees, you are surrounded by peace and tranquility. This co-op provides you with all the space you need to make this your home. Gas cooking, central air, conveniently located to laundry, inground pool and

  Cathy Holownia Meridian Commercial Mgmt Inc

  26 Bailey Ct, 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
• 

  Est $625,198 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,220 Sq Ft

  5 Putter Ln, Middle Island, NY 11953

  5 Putter Ln, Middle Island, NY 11953

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