Middletown, NY Homes

• 

  $465,000 Sold Jul 14, 2025

  335 Shawangunk Rd, Middletown, NY 10940

  • 5 Beds
  • 3 Baths
  • 2,660 Sq Ft
  • Built 1954

  Last Sold Summary

  • 3% Above List Price
  • $175/SF
  • 53 Days On Market

  Current Estimated Value $482,157

  Last Listing Agent Marion Bruhns Howard Hanna Rand Realty

  335 Shawangunk Rd, Middletown, NY 10940
• 

  Est $316,480 Not Listed For Sale

  57 Sarah Ln, Middletown, NY 10941

  • 3 Beds
  • 1.5 Baths
  • 1,440 Sq Ft
  • Built 1979

  57 Sarah Ln, Middletown, NY 10941

  Last Sold Summary

  • 5% Above List Price
  • $208/SF
  • 31 Days On Market

  Last Sold Price $300,000

  Last Listing Agent Richard Heffernan John J Lease REALTORS Inc
• 

  

  

  /26

  $335,000 Pre-Foreclosure

  • 3 Beds
  • 1 Bath
  • 914 Sq Ft

  55 Hulse Ave, Middletown, NY 10940

  Cute as a Button! Town of Wallkill now offers this starter home that can turn into that turn-key investment property that you’ve been searching for. Look no further as you have found it! An enclosed porch leads you into a living room followed by an eat-in kitchen that has been fully remodeled and equipped with fresh out the box stainless steel appliances, granite counters and backsplash. New

  Sandra Arnez Keller Williams Hudson Valley

  55 Hulse Ave, Middletown, NY 10940
• 

  $395,000 Sold Aug 28, 2025

  7 Randall Terrace, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,164 Sq Ft
  • Built 1953

  Last Sold Summary

  • 4% Below List Price
  • $339/SF
  • 53 Days On Market

  Current Estimated Value $400,149

  Last Listing Agent Desiree Beecham River Realty Services, Inc.

  7 Randall Terrace, Middletown, NY 10940
• 

  Est $341,408 Not Listed For Sale

  19 Red Barn Ln, Middletown, NY 10940

  • 4 Beds
  • 3.5 Baths
  • 1,692 Sq Ft
  • Built 1974

  19 Red Barn Ln, Middletown, NY 10940

  Last Sold Summary

  • 14% Above List Price
  • $177/SF
  • 30 Days On Market

  Last Sold Price $300,000

  Last Listing Agent Dawn Payne Payne Team LLC
• 

  

  /8

  $90,000 Pending

  • 1 Bath
  • 480 Sq Ft

  115 Concord Ln Unit 115, Middletown, NY 10940

  Looking for an affordable and convenient place to call home? This bright studio condo in the desirable Buttonwood Estates community offers comfort and value in one package! Features include a galley-style kitchen, open living/sleeping area, and low-maintenance living—perfect for first-time buyers, downsizers, or investors. Enjoy the benefits of a well-kept community close to shopping, dining, and

  Malik Subhani Weichert Realtors

  115 Concord Ln Unit 115, Middletown, NY 10940
• 

  $426,500 Sold Jan 22, 2026

  242 Derby Rd, Middletown, NY 10940

  • 3 Beds
  • 3 Baths
  • 2,214 Sq Ft
  • Built 1953

  Last Sold Summary

  • 2% Above List Price
  • $193/SF
  • 41 Days On Market

  Current Estimated Value $393,826

  Last Listing Agent Isaiah Lopez Keller Williams Hudson Valley

  242 Derby Rd, Middletown, NY 10940
• 

  Est $312,768 Not Listed For Sale

  40 Red Barn Ln, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 1,452 Sq Ft
  • Built 1973

  40 Red Barn Ln, Middletown, NY 10940

  Last Sold Summary

  • 18% Above List Price
  • $183/SF
  • 39 Days On Market

  Last Sold Price $265,000

  Last Listing Agent Annie Hansen Howard Hanna Rand Realty
• 

  

  /13

  $250,000 Pending

  • 3 Beds
  • 1 Bath
  • 1,464 Sq Ft

  212 Cottage St, Middletown, NY 10940

  Great home for the family! Come make this your home. Features 3 bedroom, 1 bath, formal dining room, enclosed porch, newer furnace and hot water heater, also has a great yard. Close to park and shopping.

  Nicholas Scarano John J Lease REALTORS Inc

  212 Cottage St, Middletown, NY 10940
• 

  $140,000 Sold Dec 02, 2025

  228 Concord Ln Unit 228, Middletown, NY 10940

  • 1 Bed
  • 1 Bath
  • 740 Sq Ft
  • Built 1989

  Last Sold Summary

  • 2% Below List Price
  • $189/SF
  • 95 Days On Market

  Current Estimated Value $141,766

  Last Listing Agent Yasmine Delgado BHG Real Estate Green Team

  228 Concord Ln Unit 228, Middletown, NY 10940
• 

  Est $326,683 Not Listed For Sale

  24 Black Stallion Ct, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 1,408 Sq Ft
  • Built 1979

  24 Black Stallion Ct, Middletown, NY 10940

  Last Sold Summary

  • 13% Above List Price
  • $206/SF
  • 13 Days On Market

  Last Sold Price $290,000

  Last Listing Agent Mark Tierney Howard Hanna Rand Realty
• 

  

  /6

  $1,550,000

  • 5 Beds
  • 5.5 Baths
  • 4,365 Sq Ft

  79 Bisch Rd, Middletown, NY 10940

  Discover the allure of 89 sprawling acres in Orange County, New York, featuring a charming farm house and a tranquil pond. The farmhouse, with its rustic charm and scenic surroundings, holds immense potential as a delightful Airbnb destination or a mini vacation retreat. Its spacious interior, cozy ambiance, and proximity to nature make it an idea I spot for relaxation and rejuvenation.

  Siang Liu P R O Links Realty Inc

  79 Bisch Rd, Middletown, NY 10940
• 

  $210,000 Sold May 08, 2025

  57 Jimal Dr, Middletown, NY 10940

  • 1 Bed
  • 1 Bath
  • 893 Sq Ft
  • Built 1990

  Last Sold Summary

  • $235/SF
  • 128 Days On Market

  Current Estimated Value $215,771

  Last Listing Agent LIENA HAMDI Exit Realty Connections

  57 Jimal Dr, Middletown, NY 10940
• 

  Est $318,723 Not Listed For Sale

  28 Black Stallion Ct, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,188 Sq Ft
  • Built 1979

  28 Black Stallion Ct, Middletown, NY 10940

  Last Sold Summary

  • 1% Above List Price
  • $265/SF
  • 38 Days On Market

  Last Sold Price $315,000

  Last Listing Agent Beth Palma Keller Williams Realty
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  /8

  $155,000

  • 1 Bed
  • 1 Bath
  • 735 Sq Ft

  234 Concord Ln, Middletown, NY 10940

  Welcome to this inviting 1-bedroom, 1-bath residence in the heart of Middletown. Featuring an open-living layout with abundant natural light, this unit offers a seamless flow from the living room to the kitchen and plenty of storage. The generously sized bedroom boasts a large closet and easy access to the full bath. Additional perks include in-unit laundry and assigned parking. Located in a

  Malik Subhani Weichert Realtors

  234 Concord Ln, Middletown, NY 10940
• 

  $345,000 Sold Jan 22, 2026

  98 Watkins Ave, Middletown, NY 10940

  • 3 Beds
  • 1 Bath
  • 1,300 Sq Ft
  • Built 1960

  Last Sold Summary

  • 3% Above List Price
  • $265/SF
  • 32 Days On Market

  Current Estimated Value $336,356

  Last Listing Agent John Biasi Howard Hanna Rand Realty

  98 Watkins Ave, Middletown, NY 10940
• 

  Est $357,573 Not Listed For Sale

  21 Old Anvil Ln, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 1,692 Sq Ft
  • Built 1974

  21 Old Anvil Ln, Middletown, NY 10940

  Last Sold Summary

  • 9% Above List Price
  • $195/SF
  • 20 Days On Market

  Last Sold Price $329,500

  Last Listing Agent Matthew Gibbs Keller Williams Hudson Valley
• 

  

  /31

  $349,999 Pending

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

  17 Little Ave, Middletown, NY 10940

  Fully Available...Opportunity Knocks to acquire this fully detached One family home in the heart of the Hudson Valley. This home offers five large bedrooms and two full bathrooms. The Kitchen features granite countertops and Stainless-steel appliances, pocket doors. fully enclosed front Porch, back deck, fenced back yard for Outdoor leisure, dinning, entertaining and endless Possibilities.

  Samar Tarazi Keller Williams Realty

  17 Little Ave, Middletown, NY 10940
• 

  $405,000 Sold Sep 26, 2025

  15 Rowan St Unit 13, Middletown, NY 10940

  • 5 Beds
  • 2 Baths
  • 1,920 Sq Ft
  • Built 1900

  Last Sold Summary

  • 3% Below List Price
  • $211/SF
  • 16 Days On Market

  Current Estimated Value $390,900

  Last Listing Agent Juan Bautista Serhant LLC

  15 Rowan St Unit 13, Middletown, NY 10940
• 

  Est $335,369 Not Listed For Sale

  11 Silo Ln, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 1,452 Sq Ft
  • Built 1974

  11 Silo Ln, Middletown, NY 10940

  Last Sold Summary

  • 18% Above List Price
  • $196/SF
  • 147 Days On Market

  Last Sold Price $285,000

  Last Listing Agent Jie Liu Keller Williams Hudson Valley
• 

  

  /36

  $615,000

  • 4 Beds
  • 3 Baths
  • 3,350 Sq Ft

  9 Crane Rd, Middletown, NY 10941

  Back on the market! Welcome to 9 Crane Road, in Middletown, New York where comfort meets charm, and every day feels like home, all you have to do is move in.Step into this beautifully well maintained residence, nestled on a quiet, tree-lined block. This move-in-ready home is designed for those who crave warmth, flexibility, and room to grow. From the moment you enter, natural light pours

  Shanese Williams Real Broker NY LLC

  9 Crane Rd, Middletown, NY 10941
• 

  $375,000 Sold Sep 12, 2025

  22 Maryland Ave, Middletown, NY 10940

  • 3 Beds
  • 1 Bath
  • 1,440 Sq Ft
  • Built 1920

  Last Sold Summary

  • 4% Below List Price
  • $260/SF
  • 80 Days On Market

  Current Estimated Value $375,092

  Last Listing Agent Patricia Lucey Picture It Sold, LLC

  22 Maryland Ave, Middletown, NY 10940
• 

  Est $337,987 Not Listed For Sale

  29 Silo Ln, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 1,452 Sq Ft
  • Built 1974

  29 Silo Ln, Middletown, NY 10940

  Last Sold Summary

  • 14% Above List Price
  • $204/SF
  • 222 Days On Market

  Last Sold Price $295,500

  Last Listing Agent Feng Chang Acer Realty Inc
• 

  

  /6

  $99,000

  • Land
  • 6.48 Acres
  • $15,278 per Acre

  0 Fox Meadow Ln, Middletown, NY 12455

  Surveyed 6.4-Acre Hilltop Parcel with perc test, septic plans to be provided, and with electric on property. Perched atop one of the most beautiful and sought-after hills in Margaretville, this exceptional 6+ acre parcel offers a rare opportunity to own your own private slice of Catskills paradise. Located at the very end of a quiet, private road, this property features breathtaking 180-degree

  Susan Doig Listing by Coldwell Banker Timberland Properties

  

  0 Fox Meadow Ln, Middletown, NY 12455
• 

  $305,000 Sold Apr 08, 2025

  11 Black Stallion Ct, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,188 Sq Ft
  • Built 1979

  Last Sold Summary

  • 2% Below List Price
  • $257/SF
  • 132 Days On Market

  Current Estimated Value $316,601

  Last Listing Agent Bente Brown John J Lease REALTORS Inc

  11 Black Stallion Ct, Middletown, NY 10940
• 

  Est $362,386 Not Listed For Sale

  8 Silo Ln, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 1,692 Sq Ft
  • Built 1976

  8 Silo Ln, Middletown, NY 10940

  Last Sold Summary

  • 5% Above List Price
  • $204/SF
  • 40 Days On Market

  Last Sold Price $344,900

  Last Listing Agent Elsie Nunez Keller Williams Realty
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  /24

  $325,000 Pre-Foreclosure

  • 2 Beds
  • 2.5 Baths
  • 1,831 Sq Ft

  6 Deer Ct Dr, Middletown, NY 10940

  Bright and well-maintained 2-bedroom, 2.5-bath unit located in the desirable Deer Run community in Middletown. This home offers a spacious open floor plan with abundant natural light, including a comfortable living room with a wood-burning fireplace and a separate dining area that connects to the kitchen . Additional highlights include a private garage and driveway, full laundry area, and

  Michelle Gruberger Real Estate Circuit Inc

  6 Deer Ct Dr, Middletown, NY 10940
• 

  $330,000 Sold Oct 30, 2025

  3 Chappell Pkwy, Middletown, NY 10940

  • 2 Beds
  • 1 Bath
  • 1,016 Sq Ft
  • Built 1960

  Last Sold Summary

  • $325/SF
  • 37 Days On Market

  Current Estimated Value $331,067

  Last Listing Agent Antonio Sanchez Harbor Gray Real Estate LLC

  3 Chappell Pkwy, Middletown, NY 10940
• 

  Est $364,081 Not Listed For Sale

  45 Silo Ln, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 1,692 Sq Ft
  • Built 1973

  45 Silo Ln, Middletown, NY 10940

  Last Sold Summary

  • 8% Above List Price
  • $199/SF
  • 27 Days On Market

  Last Sold Price $337,000

  Last Listing Agent Stephanie Ruzzo RE/MAX
• 

  

  /37

  $625,000 Open Sun 12PM - 1:30PM

  • 4 Beds
  • 2.5 Baths
  • 2,128 Sq Ft

  2066 Route 6, Middletown, NY 10940

  Set on over 5 acres and beautifully landscaped, this inviting home delivers space, comfort, and resort-style living at home. A true backyard oasis designed for relaxation and entertaining. Step outside to your private retreat featuring an above-ground heated pool with surrounding deck, an extended patio with a pergola swim-up bar, and multiple spaces to gather, unwind, and enjoy the outdoors. A

  Juliska Martino Compass Greater NY, LLC

  2066 Route 6, Middletown, NY 10940
• 

  $484,000 Sold Apr 07, 2025

  295 Spruce Rd, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,881 Sq Ft
  • Built 1922

  Last Sold Summary

  • 8% Below List Price
  • $257/SF
  • 68 Days On Market

  Current Estimated Value $520,209

  Last Listing Agent Nicola Friedman Windsor Realty Services Inc

  295 Spruce Rd, Middletown, NY 10940
• 

  Est $460,203 Not Listed For Sale

  106 Rolling Meadows Rd, Middletown, NY 10940

  • 4 Beds
  • 2 Baths
  • 1,305 Sq Ft
  • Built 1979

  106 Rolling Meadows Rd, Middletown, NY 10940

  Last Sold Summary

  • 28% Above List Price
  • $276/SF
  • 110 Days On Market

  Last Sold Price $360,000

  Last Listing Agent Lindsey Gordon Signature Premier Properties
• 

  

  /50

  $535,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 3,013 Sq Ft

  9 Country Club Dr, Middletown, NY 10940

  This 3-bed townhouse in The Fairways offers over 3000 square feet of living space across three finished levels, including a walkout basement and an attached two-car garage. Built in 2005 and located in a gated Middletown community, this home features a renovated kitchen with granite countertops, stainless steel appliances, and a walk-through layout connecting to a formal dining room. The entrance

  Kewin Garabito eXp Realty

  9 Country Club Dr, Middletown, NY 10940
• 

  $440,000 Sold Sep 02, 2025

  225 Highland Ave, Middletown, NY 10940

  • 6 Beds
  • 2 Baths
  • 2,748 Sq Ft
  • Built 1910

  Last Sold Summary

  • 4% Above List Price
  • $160/SF
  • 101 Days On Market

  Current Estimated Value $445,172

  Last Listing Agent Mark Karten Karten Real Estate Svcs LLC

  225 Highland Ave, Middletown, NY 10940
• 

  Est $472,002 Not Listed For Sale

  1 Twin Wells Ct, Middletown, NY 10940

  • 4 Beds
  • 2.5 Baths
  • 2,055 Sq Ft
  • Built 1979

  1 Twin Wells Ct, Middletown, NY 10940

  Last Sold Summary

  • 8% Above List Price
  • $213/SF
  • 126 Days On Market

  Last Sold Price $438,500

  Last Listing Agent Megan Brown William Raveis Real Estate
• 

  

  /18

  $169,900

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  985 Route 17m, Middletown, NY 10940

  Welcome to your brand-new home! This beautiful 2024-built 2-bedroom, 2-bathroom mobile home offers 900+ square feet of thoughtfully designed living space — perfectly blending comfort, style, and affordability. Features Include: Open-Concept Living Area: Spacious layout filled with natural light, featuring stylish wood-look flooring throughout.Modern Kitchen: Equipped with brand-new stainless

  Steven Brown Hudson Valley Realty & Busines

  985 Route 17m, Middletown, NY 10940
• 

  $269,900 Sold May 16, 2025

  247 Shaw Rd, Middletown, NY 10941

  • 2 Beds
  • 1 Bath
  • 1,020 Sq Ft
  • Built 1945

  Last Sold Summary

  • 4% Below List Price
  • $265/SF
  • 190 Days On Market

  Current Estimated Value $285,235

  Last Listing Agent Christina Gordon I Realty LLC

  247 Shaw Rd, Middletown, NY 10941
• 

  Est $469,899 Not Listed For Sale

  3 Twin Wells Ct, Middletown, NY 10940

  • 4 Beds
  • 3 Baths
  • 1,805 Sq Ft
  • Built 1979

  3 Twin Wells Ct, Middletown, NY 10940

  Last Sold Summary

  • 8% Above List Price
  • $240/SF
  • 55 Days On Market

  Last Sold Price $433,800

  Last Listing Agent Catherine Eichner Eichner Realty Group Inc.
• 

  

  /20

  $249,900 Pending

  • 3 Beds
  • 1 Bath
  • 900 Sq Ft

  193 Schutt Rd, Middletown, NY 10940

  Why rent when you can purchase this updated, move-in-ready 3-bedroom home? This property presents an excellent opportunity for first-time homebuyers, especially with its low taxes. The kitchen features granite countertops, ample cabinet space, stainless steel appliances, and a breakfast bar open to the living room. The spacious living room is filled with natural light, making it a welcoming

  Jeanmarie Valentin HomeSmart Homes & Estates

  193 Schutt Rd, Middletown, NY 10940
• 

  $737,500 Sold Aug 21, 2025

  3 Mulberry Run, Middletown, NY 10941

  • 4 Beds
  • 2.5 Baths
  • 2,929 Sq Ft
  • Built 2020

  Last Sold Summary

  • 8% Below List Price
  • $252/SF
  • 169 Days On Market

  Current Estimated Value $732,094

  Last Listing Agent Michelle Getty HVG Realty, Inc.

  3 Mulberry Run, Middletown, NY 10941

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