Middle Island, NY Homes

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  /50

  $899,950

  • 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

  (631) 557-5583

  1 Lake Dr, Middle Island, NY 11953
• Explore Middle Island

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  /13

  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

  (631) 448-3727

  

  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 $266,858

  Last Listing Agent Amy Prego Shine Realty Group

  172 Fairview Cir, Middle Island, NY 11953
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  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

  • $230/SF
  • 59 Days On Market

  • Last Sold Price $230,000
  • Apr 22, 2025

  Last Listing Agent Anthony Frabizio Rice Realty Group Inc
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  /30

  $450,000

  • 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

  (631) 570-8737

  738 Birchwood Park Dr, 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

  (934) 451-1164

  

  100 Stonegate Way, Middle Island, NY 11953
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  $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 $617,936

  Last Listing Agent Nakishia Dail Fave Realty Inc

  31 Park Ln, 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

  • $373/SF
  • 20 Days On Market

  • Last Sold Price $280,000
  • Apr 10, 2024

  Last Listing Agent Melissa King Compass Greater NY LLC
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  /23

  $569,999 Pending

  • 4 Beds
  • 1.5 Baths
  • 2,210 Sq Ft

  6 Shelley Dr, Middle Island, NY 11953

  Spacious Ranch offering 2,200 square feet of living space with 4 bedrooms and 1.5 bathrooms, and packed with updates throughout! Major improvements within the last 10 years include a new roof, siding, windows, skylight, sliding glass door, and gutters with leaf guards. Bathrooms have been tastefully updated, and recessed lighting was added within the last 5 years. Enjoy peace of mind with a Busch

  

  Rita Tsoukaris

  Realty Connect USA LI

  (631) 529-1321

  6 Shelley Dr, Middle Island, NY 11953
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  /97

  Starting at $2,470 Per Month

  • 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

  (631) 869-7255

  

  203 Pinewoods Crescent, Middle Island, NY 11953
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  $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 $235,443

  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

  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

  • Last Sold Price $315,000
  • Jul 31, 2023

  Last Listing Agent Bryan Elsesser Exit Realty Island Elite
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  /16

  $199,900

  • 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

  (631) 502-3899

  86 Bailey Ct, Middle Island, NY 11953
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  /91

  Starting at $2,405 Per Month

  • 1 - 2 Beds

  248 Lake Pointe Cir, Middle Island, NY 11953

  MAY-2026 FREE When You Lease APT 130* All Other Units GET $1000 Off One-Time With Move-In By 5/31/26* Rent Special On 1BR+Den $2650 * And Move-In By 6/15/26 Lease For 12-, 14- 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

  Fairfield Village At Middle Island

  (631) 869-7347

  

  248 Lake Pointe Cir, 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
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  Est $309,089 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

  • 3% Above List Price
  • $317/SF
  • 18 Days On Market

  • Last Sold Price $300,000
  • Jun 29, 2023

  Last Listing Agent Krista DeLuca Herrick Real Estate LLC
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  /50

  $589,999

  • 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

  (631) 735-5957

  20 Middle Island Rd, Middle Island, NY 11953
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  /35

  Starting at $2,340 Per Month

  • 1 - 2 Beds

  101 Tudor Ln, Middle Island, NY 11953

  LEASE UNIT 301 GET MAY-2026 FREE with Move In By 5/31/26* And All GET Inflation Buster Special of 12-, 14- Or 24-Month Lease With No Increase With Move In By 6/15/26* $99 Security* *Restrictions. Property FeaturesLedgestone and Vinyl ExteriorProfessionally Landscaped Grounds And PlantingsEntry from Middle Country RoadPaver and Bluestone Walkways ThroughoutLeasing CenterResidence

  Fairfield Courtyard At Middle Island

  (631) 869-7239

  

  101 Tudor Ln, Middle Island, NY 11953
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  $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 $453,997

  Last Listing Agent Gina Ferraro Century 21 Anchor Real Estate

  8 Ariel Dr, Middle Island, NY 11953
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  Est $320,603 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

  • 2% Above List Price
  • $333/SF
  • 17 Days On Market

  • Last Sold Price $315,000
  • Sep 27, 2024

  Last Listing Agent Kenneth Kroncke Realty Connect USA L I Inc
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  /50

  $948,500 Open Sat 1PM - 4PM

  • 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

  (631) 206-5598

  20 Bunker Ln, Middle Island, NY 11953
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  /14

  $2,500 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
• 

  $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 $613,630

  Last Listing Agent Antonella Solano-Knoeller Howard Hanna Coach

  19 Raymond Ave, 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

  • $268/SF
  • 71 Days On Market

  • Last Sold Price $187,500
  • Dec 03, 2024

  Last Listing Agent Cathy Holownia Meridian Commercial Mgmt Inc
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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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  /2

  $2,650 Per Month

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

  388 Lake Pointe Dr Unit 388, 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

  388 Lake Pointe Dr Unit 388, Middle Island, NY 11953
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  $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

  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

  • $257/SF
  • 22 Days On Market

  • Last Sold Price $180,000
  • Sep 05, 2024

  Last Listing Agent Michael Hejmej Signature Premier Properties
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  /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
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  /7

  $1,975 Per Month

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

  285 Artist Lake Dr, Middle Island, NY 11953

  1 Bedroom , 1 Bath Garden apartment located on the first floor in the Artist Lake Community. Well landscaped and maintained complex with easy Living lifestyle. Amenities include Outdoor swimming pool, Clubhouse, Tennis courts, dog park and walking path. Good Credit, Proof of income and positive rental history. Non-Smoking only

  Jennifer Lenzo Island Advantage Realty LLC

  285 Artist Lake Dr, 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 $485,970

  Last Listing Agent Thomas Annunziato Howard Hanna Coach

  1 Kate Cir, Middle Island, NY 11953
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  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

  • Last Sold Price $525,000
  • Apr 10, 2024

  Last Listing Agent Lucille DiLorenzo Realty Connect USA L I Inc
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  /18

  $197,500

  • 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

  (631) 731-5336

  129 Bailey Ct, Middle Island, NY 11953
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  /10

  $2,405 Per Month

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

  135 Lake Pointe Ct Unit 135, 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

  135 Lake Pointe Ct Unit 135, 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 $607,675 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

  • 19% Above List Price
  • $294/SF
  • 15 Days On Market

  • Last Sold Price $509,700
  • Aug 28, 2023

  Last Listing Agent Bryn Elliott Signature Premier Properties
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  /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
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  /10

  $2,405 Per Month

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

  465 Lake Pointe Dr Unit 465, 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

  465 Lake Pointe Dr Unit 465, 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 $453,503

  Last Listing Agent Cheryl Figueroa Coldwell Banker American Homes

  38 Huntingdale Way, Middle Island, NY 11953
• 

  Est $357,913 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

  • 2% Above List Price
  • $322/SF
  • 19 Days On Market

  • Last Sold Price $350,000
  • Mar 11, 2025

  Last Listing Agent John McSherry Douglas Elliman Real Estate

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