Middletown, NY Homes

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  $539,900

  • 4 Beds
  • 2.5 Baths
  • 2,176 Sq Ft

  31 Denman Rd, Middletown, NY 10940

  Welcome to this beautifully maintained Center Hall Colonial offering the perfect blend of classic design and comfortable everyday living. The heart of the home is the spacious kitchen, which opens seamlessly to the inviting family room, creating an ideal space for gathering with family and friends. The family room is highlighted by custom built-in shelving and a cozy wood-burning fireplace,

  Kenyatta Jones-Arietta R2M Realty Inc

  31 Denman Rd, Middletown, NY 10940
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  /12

  $2,425 Per Month

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

  48 North St Unit 303, Middletown, NY 10940

  Experience the pinnacle of luxury living at North Court Apartments, located in the heart of Middletown, NY. This beautifully restored building offers spacious and thoughtfully designed one- and two-bedroom apartments, where modern elegance meets timeless charm. Each unit features premium finishes, high ceilings, and open layouts that seamlessly blend comfort with style. Enjoy the convenience of

  Tehillah Deslandes Howard Hanna Rand Realty

  48 North St Unit 303, Middletown, NY 10940
• 

  $490,000

  Sold Mar 10, 2026

  1 Weather Vane Way, Middletown, NY 10940

  • 4 Beds
  • 2.5 Baths
  • 1,955 Sq Ft
  • Built 1977

  Last Sold Summary

  • 2% Below List Price
  • $251/SF
  • 22 Days On Market

  Current Estimated Value $489,697

  Last Listing Agent Jessica Evans KW Hudson Valley United

  1 Weather Vane Way, Middletown, NY 10940
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  Not Listed For Sale

  540 County Route 49, Middletown, NY 10940

  • 12 Beds
  • 3 Baths
  • 4,924 Sq Ft
  • Built 1986

  540 County Route 49, Middletown, NY 10940

  Last Sold Summary

  • 89 Days On Market

  Last Listing Agent John McCarey John I McCarey
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  /50

  $399,000

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,446 Sq Ft

  4 Saint Eve Ct, Middletown, NY 10940

  Situated on a quiet cul-de-sac, this spacious and versatile home offers the perfect blend of comfort, convenience, and flexibility. Enjoy a large yard ideal for entertaining, complete with a deck and patio for outdoor gatherings and relaxation. Inside, the home features ample parking, 3-zone heating for year-round comfort, and an all-inclusive room/office perfect for working from home, guests, or

  Robin Cohen Keller Williams Realty

  4 Saint Eve Ct, Middletown, NY 10940
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  /12

  $2,195 Per Month

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

  48 North St Unit 203, Middletown, NY 10940

  Experience the pinnacle of luxury living at North Court Apartments, located in the heart of Middletown, NY. This beautifully restored building offers spacious and thoughtfully designed one- and two-bedroom apartments, where modern elegance meets timeless charm. Each unit features premium finishes, high ceilings, and open layouts that seamlessly blend comfort with style. Enjoy the convenience of

  Tehillah Deslandes Howard Hanna Rand Realty

  48 North St Unit 203, Middletown, NY 10940
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  $415,000

  Sold Jun 12, 2026

  36 Vincent Dr, Middletown, NY 10940

  • 2 Beds
  • 1.5 Baths
  • 1,346 Sq Ft
  • Built 1961

  Last Sold Summary

  • 7% Above List Price
  • $308/SF
  • 17 Days On Market

  Current Estimated Value $397,653

  Last Listing Agent Donna Reese KW Hudson Valley United

  36 Vincent Dr, Middletown, NY 10940
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  Est $572,750

  Not Listed For Sale

  Unlisted Address

  • 4 Beds
  • 3 Baths
  • 2,091 Sq Ft
  • Built 2009

  Unlisted Address

  Last Sold Summary

  • 68 Days On Market

  Last Listing Agent Marilyn D'Andrea Integrity Real Estate, Inc.
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  /18

  $179,000

  New Construction $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 924 Sq Ft

  412 4th Ave, Middletown, NY 10940

  This beautiful high end home is located in the desirable Valley View Community. The home is brand new and offers a modern contemporary feel and it is ready to be yours! Ideal commuter friendly location just minutes to the train to NYC. Bright and airy 2 bedroom, 2 bath home with close to 1,000 square feet of space! Gorgeous gourmet kitchen with upgraded cabinets featuring an abundance of

  Sandra Spector Howard Hanna Rand Realty

  412 4th Ave, Middletown, NY 10940
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  /17

  $2,595 Per Month

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

  48 North St Unit 207, Middletown, NY 10940

  Experience the pinnacle of luxury living at North Court Apartments, located in the heart of Middletown, NY. This beautifully restored building offers spacious and thoughtfully designed one- and two-bedroom apartments, where modern elegance meets timeless charm. Each unit features premium finishes, high ceilings, and open layouts that seamlessly blend comfort with style. Enjoy the convenience of

  Tehillah Deslandes Howard Hanna Rand Realty

  48 North St Unit 207, Middletown, NY 10940
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  $490,000

  Sold Jul 13, 2026

  53 Cornwall Ln, Middletown, NY 10940

  • 3 Beds
  • 3.5 Baths
  • 2,521 Sq Ft
  • Built 2009

  Last Sold Summary

  • 1% Above List Price
  • $194/SF
  • 69 Days On Market

  Current Estimated Value $482,696

  Last Listing Agent Dulce M Ferrera KW Hudson Valley United

  53 Cornwall Ln, Middletown, NY 10940
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  Est $492,158

  Not Listed For Sale

  338 van Duzer Rd, Middletown, NY 10940

  • 4 Beds
  • 3.5 Baths
  • 2,758 Sq Ft
  • Built 1801

  338 van Duzer Rd, Middletown, NY 10940

  Last Sold Summary

  • 62 Days On Market

  Last Listing Agent Nicholas Cuomo Keller Williams Realty
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  $1,650,000

  • Land
  • 7.5 Acres
  • $220,000 per Acre

  32 Gibbs Ct, Middletown, NY 10940

  32 Gibbs Court | Wallkill, NYPrime 3.20 Acre Commercial Development PAD on 7.5-acre lot Opportunity in the Heart of WallkillUnlock the full potential of this premier 3.20 PAD on a 7.5-acre commercial parcel, ideally located in the thriving Town of Wallkill. Situated within the highly desirable Town Center District, 32 Gibbs Court offers a rare development opportunity with broad zoning

  Peter Janis Berkshire Hathaway HS NE Prop.

  32 Gibbs Ct, Middletown, NY 10940
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  /9

  $3,100 Per Month

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

  48 North St Unit 402, Middletown, NY 10940

  Experience the pinnacle of luxury living at North Court Apartments, located in the heart of Middletown, NY. This beautifully restored building offers spacious and thoughtfully designed one- and two-bedroom apartments, where modern elegance meets timeless charm. Each unit features premium finishes, high ceilings, and open layouts that seamlessly blend comfort with style. Enjoy the convenience of

  Tehillah Deslandes Howard Hanna Rand Realty

  48 North St Unit 402, Middletown, NY 10940
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  $475,000

  Sold Dec 04, 2025

  38 Highrose Ridge Way, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 2,763 Sq Ft
  • Built 2019

  Last Sold Summary

  • 3% Below List Price
  • $172/SF
  • 73 Days On Market

  Current Estimated Value $488,755

  Last Listing Agent Donna Reese KW Hudson Valley United

  38 Highrose Ridge Way, Middletown, NY 10940
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  Not Listed For Sale

  704 Route 211 W Unit 706, Middletown, NY 10940

  • 9 Beds
  • 3 Baths
  • 3,090 Sq Ft
  • Built 1925

  704 Route 211 W Unit 706, Middletown, NY 10940

  Last Sold Summary

  • 105 Days On Market

  Last Listing Agent Joao Rodrigues Preferred Properties Real Esta
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  /37

  $535,000

  Pending

  • 4 Beds
  • 4 Baths
  • 2,088 Sq Ft

  19 Randall Terrace, Middletown, NY 10940

  STUNNING Colonial located in a quiet neighborhood of Middletown minutes from OCC. This home is in mint condition with the upgrades it offers. Enter into an oversized living room with a fireplace that leads to a formal dining room & gorgeous new kitchen. This modern eat in kitchen features self closing cabinets, granite countertops, backsplash & beautiful fresh out the box stainless steel

  Sandra Arnez KW Hudson Valley United

  19 Randall Terrace, Middletown, NY 10940
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  /10

  $2,700 Per Month

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

  48 North St Unit 308, Middletown, NY 10940

  Experience the pinnacle of luxury living at North Court Apartments, located in the heart of Middletown, NY. This beautifully restored building offers spacious and thoughtfully designed unit with one bedroom with a Den , where modern elegance meets timeless charm. Each unit features premium finishes, high ceilings, and open layouts that seamlessly blend comfort with style. Enjoy the convenience of

  Tehillah Deslandes Howard Hanna Rand Realty

  48 North St Unit 308, Middletown, NY 10940
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  $195,000

  Sold Mar 13, 2026

  36 Mountain Ave Unit 34, Middletown, NY 10940

  • 3 Beds
  • 1 Bath
  • 1,040 Sq Ft
  • Built 1956

  Last Sold Summary

  • 22% Below List Price
  • $188/SF
  • 333 Days On Market

  Current Estimated Value $369,253

  Last Listing Agent Arduino Colomban Skyler Realty LLC

  36 Mountain Ave Unit 34, Middletown, NY 10940
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  Est $490,737

  Not Listed For Sale

  27 Cornwall Ln, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 2,427 Sq Ft
  • Built 2009

  27 Cornwall Ln, Middletown, NY 10940

  Last Sold Summary

  • 25 Days On Market

  Last Listing Agent Cindy Hayes Compass Greater NY, LLC
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  /41

  $375,000

  • 3 Beds
  • 1.5 Baths
  • 1,650 Sq Ft

  7 Allan Park Mews, Middletown, NY 10940

  Welcome to the community of Canterbury Knolls! Lovely townhouses on flat land with well kept landscaping. This home is at the end of a dead end street for extra privacy. With three-bedrooms, 1 1/2 baths, dining area, living room and a bonus room you have all the space you need. The sunroom (WITH A HOT TUB!!) and attached patio gives you lots of room to relax or entertain. Second floors bedrooms

  John Nahass Century 21 Full Service Realty

  7 Allan Park Mews, Middletown, NY 10940
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  /12

  $2,450 Per Month

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

  48 North St Unit 403, Middletown, NY 10940

  Experience the pinnacle of luxury living at North Court Apartments, located in the heart of Middletown, NY. This beautifully restored building offers spacious and thoughtfully designed one- and two-bedroom apartments, where modern elegance meets timeless charm. Each unit features premium finishes, high ceilings, and open layouts that seamlessly blend comfort with style. Enjoy the convenience of

  Tehillah Deslandes Howard Hanna Rand Realty

  48 North St Unit 403, Middletown, NY 10940
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  $193,000

  Sold Oct 01, 2025

  129 Foster Rd, Middletown, NY 10941

  • 1 Bed
  • 1 Bath
  • 512 Sq Ft
  • Built 1950

  Last Sold Summary

  • 3% Below List Price
  • $377/SF
  • 65 Days On Market

  Current Estimated Value $185,904

  Last Listing Agent Shannon Stewart Curasi Realty, Inc.

  129 Foster Rd, Middletown, NY 10941
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  Est $483,437

  Not Listed For Sale

  51 Cornwall Ln, Middletown, NY 10940

  • 3 Beds
  • 3.5 Baths
  • 1,790 Sq Ft
  • Built 2009

  51 Cornwall Ln, Middletown, NY 10940

  Last Sold Summary

  • 65 Days On Market

  Last Listing Agent Sol Perry BHG Real Estate Green Team
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  /19

  $359,999

  Pending

  • 3 Beds
  • 3 Baths

  32 Genung St, Middletown, NY 10940

  Calling all investors. Opportunity to own a two-unit income property in a great location. The 1-bedroom unit is rented **currently rented below market** It has an updated kitchen. I will have some pictures of that unit shortly. The 2-bedroom unit is vacant but currently also listed for rent. It does need some updating but has great potential. The primary bedroom on the first floor is very large

  Evelyn Unger Tmimi Weichert Realtors

  32 Genung St, Middletown, NY 10940
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  /6

  $2,000 Per Month

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

  125 Wickham Ave Unit 3B, Middletown, NY 10940

  This updated 2-bedroom, 1-bathroom apartment in the heart of Middletown, NY is move-in ready with a renovated kitchen, updated appliances, and a fully remodeled bathroom. Hardwood-style flooring runs throughout the unit, and both bedrooms offer generous space and plenty of natural light. The apartment also includes washer/dryer connections, adding everyday convenience right at home. Located in a

  Ryan Barrett Keller Williams Realty

  125 Wickham Ave Unit 3B, Middletown, NY 10940
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  $139,999

  Sold Mar 27, 2026

  5 Sayer Ln, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,080 Sq Ft
  • Built 2017

  Last Sold Summary

  • 8% Above List Price
  • $130/SF
  • 42 Days On Market

  Last Listing Agent Pete Wolven Hudson Valley Home Connection

  5 Sayer Ln, Middletown, NY 10940
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  Est $501,762

  Not Listed For Sale

  20 Avoncroft Ln, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 2,521 Sq Ft
  • Built 2009

  20 Avoncroft Ln, Middletown, NY 10940

  Last Sold Summary

  • 157 Days On Market

  Last Listing Agent D'Wana Haynesworth YourHomeSold Guaranteed Realty
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  /42

  $639,000

  $40K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,680 Sq Ft

  481 Dosen Rd, Middletown, NY 10940

  ABSOLUTELY GORGEOUS!!! MUST SEE!! QUALITY BUILT WITH BRAND NEW ADDITION AND BRAND NEW DETACHED POLE BARN!!! OVER 7 ACRES !!! 481 Dosen Road offers a rare combination of quality construction, privacy, and usable space, set on 7.4 peaceful acres. This custom-built Lok-N-Logs log home was thoughtfully designed to blend the character of a true log cabin with the comforts needed for everyday living.

  Frank Muccari Cronin & Company Real Estate

  481 Dosen Rd, Middletown, NY 10940
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  /11

  $3,125 Per Month

  • 2 Beds
  • 2 Baths
  • 850 Sq Ft
  • Apartment for Rent

  48 North St Unit 405, Middletown, NY 10940

  Experience the pinnacle of luxury living at North Court Apartments, located in the heart of Middletown, NY. This beautifully restored building offers spacious and thoughtfully designed unit with 2 bedrooms and 2 full bathrooms, where modern elegance meets timeless charm. Each unit features premium finishes, high ceilings, and open layouts that seamlessly blend comfort with style. Enjoy the

  Tehillah Deslandes Howard Hanna Rand Realty

  48 North St Unit 405, Middletown, NY 10940
• 

  $285,000

  Sold Sep 10, 2025

  234 Howells Rd, Middletown, NY 10940

  • Land
  • 41.6 Acres
  • $6,851 per Acre

  Last Sold Summary

  • 24% Below List Price
  • 40 Days On Market

  Last Listing Agent Jonathon Lee KW Hudson Valley United

  234 Howells Rd, Middletown, NY 10940
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  Est $509,544

  Not Listed For Sale

  5 Avoncroft Ln, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 2,521 Sq Ft
  • Built 2009

  5 Avoncroft Ln, Middletown, NY 10940

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent Angelique Tapia KFortuna All Aspects Realty
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  /33

  $825,000

  • 4 Beds
  • 3.5 Baths
  • 2,860 Sq Ft

  718 Mountain Rd, Middletown, NY 10940

  Welcome to a timeless 1821 farmhouse set on more than five private acres in the heart of Sullivan County, where historic character meets effortless modern living. Surrounded by mature gardens, handcrafted stone walls, and sweeping mountain views, this is Upstate living at its finest. Offering more than 2,800 square feet, the home features four bedrooms, three and a half bathrooms, including two

  Davina Thomasula Four Seasons Sotheby's Int'l-K

  718 Mountain Rd, Middletown, NY 10940
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  /30

  $1,800 Per Month

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

  2 Fortune Rd W Unit 3C, Middletown, NY 10941

  Welcome to this clean, well-maintained one-bedroom, one-bath townhouse, ideally located just minutes from major highways, hospitals, public transportation, shopping, restaurants, and more. Situated on the top floor, this inviting home offers a bright, open-concept layout with a spacious living and dining area that flows into the kitchen. Glass sliding doors off the living room lead to a private

  Susan Giordano Hudson Premium Realty

  2 Fortune Rd W Unit 3C, Middletown, NY 10941
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  $490,000

  Sold Mar 12, 2026

  9 Randall Heights, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,868 Sq Ft
  • Built 1964

  Last Sold Summary

  • 7% Below List Price
  • $262/SF
  • 70 Days On Market

  Current Estimated Value $490,183

  Last Listing Agent Naomi Streicher Q Home Sales

  9 Randall Heights, Middletown, NY 10940
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  Est $469,966

  Not Listed For Sale

  68 Anthony St, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,350 Sq Ft
  • Built 2014

  68 Anthony St, Middletown, NY 10940

  Last Sold Summary

  • 22 Days On Market

  Last Listing Agent Aracelis Rosario Minaya Century 21 Full Service Realty
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  /35

  $450,000

  • 3 Beds
  • 2 Baths
  • 1,577 Sq Ft

  153 Ridgewood Ave Unit 155, Middletown, NY 10940

  Welcome to 153 Ridgewood Avenue, a beautifully maintained 2021 built ranch offering the ease and comfort of modern single level living. Vaulted ceilings, an open concept layout, stylish finishes, and abundant natural light create a warm and inviting feel from the moment you enter. With more than 1,500 square feet, the home features a spacious kitchen with stone countertops, generous prep space,

  Isaiah Lopez KW Hudson Valley United

  153 Ridgewood Ave Unit 155, Middletown, NY 10940
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  /16

  $3,400 Per Month

  • 3 Beds
  • 2 Baths
  • 1,852 Sq Ft
  • House for Rent

  14 Smith St, Middletown, NY 10940

  See all this spacious rental has to offer, located on a quiet side street in Middletown. This home is ideal for those seeking extra space and convenience. This home provides all the space you need, plus a backyard for relaxing, BBQ's, and group get-togethers. Pets Ok and utilities included. Close to schools, shopping, restaurants, hospital, and public transportation. Book your showing today and

  Dawn Bulson Century 21 Geba Realty

  14 Smith St, Middletown, NY 10940
• 

  $415,000

  Sold Jul 24, 2026

  366 van Burenville Rd, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,513 Sq Ft
  • Built 1870

  Last Sold Summary

  • 1% Above List Price
  • $274/SF
  • 27 Days On Market

  Current Estimated Value $408,190

  Last Listing Agent John Biasi Howard Hanna Rand Realty

  366 van Burenville Rd, Middletown, NY 10940
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  Est $261,023

  Not Listed For Sale

  133 Fairfax Ave, Middletown, NY 10940

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • Built 1950

  133 Fairfax Ave, Middletown, NY 10940

  Last Sold Summary

  • 45 Days On Market

  Last Listing Agent Dov Tessler Keller Williams Hudson Valley

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