Middletown, NY Homes

• 

  $415,000

  Sold May 18, 2026

  74 Pocatello Rd, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,736 Sq Ft
  • Built 2004

  Last Sold Summary

  • 6% Below List Price
  • $239/SF
  • 131 Days On Market

  Current Estimated Value $425,160

  Last Listing Agent Catherine Eichner Eichner Realty Group Inc.

  74 Pocatello Rd, Middletown, NY 10940
• 

  Est $476,825

  Not Listed For Sale

  12 Harvest Hill Ln, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 2,055 Sq Ft
  • Built 1980

  12 Harvest Hill Ln, Middletown, NY 10940

  Last Sold Summary

  • 90 Days On Market
• 

  

  

  /50

  $539,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,644 Sq Ft

  20 Park Circle Dr, Middletown, NY 10940

  Welcome to a truly exceptional home nestled in one of the most beautiful and peaceful areas of the Town of Wallkill, NY. Completely renovated with stunning modern upgrades, this rare and remarkably spacious single-family residence offers the perfect blend of elegance, comfort, and functionality. From the moment you enter, you’ll appreciate the bright open layout featuring a beautifully updated

  Moshe Ekstein eRealty Advisors, Inc

  20 Park Circle Dr, Middletown, NY 10940
• 

  

  

  /29

  $439,990

  Pending

  • 5 Beds
  • 2 Baths
  • 2,586 Sq Ft

  14 Bonnell St, Middletown, NY 10940

  Spacious Two-Family Home in the City of Middletown – Excellent Investment Opportunity Large, solid two-family home located in the City of Middletown, offering strong rental income and outstanding value. This well-maintained property features: Second Floor: 1,338 sq ft – 3 bedrooms, 1 full bath First Floor: 1,248 sq ft – 2 bedrooms, 1 full bath Current rents are $2,100 and $1,800 per month,

  Jonathon Lee KW Hudson Valley United

  14 Bonnell St, Middletown, NY 10940
• 

  Est $472,133

  Not Listed For Sale

  97 Rolling Meadows Rd, Middletown, NY 10940

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

  97 Rolling Meadows Rd, Middletown, NY 10940

  Last Sold Summary

  • 155 Days On Market
• 

  

  /44

  $799,999

  $50K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,000 Sq Ft

  TBD Brook Rd, Middletown, NY 10941

  New Construction LUXURY HOME in Valley Central Schools outside of SCOTCHTOWN! "Choose Your Finishes" on this Stunning 3,000 sq. ft. modern Colonial privately set atop a scenic 5-acre wooded lot offering privacy and natural beauty. Conveniently located 5-10 minutes to Middletown, Pine Bush, and Montgomery. The main level features a spacious open-concept floor plan with 9-foot ceilings, hardwood

  Philip Barnao eXp Realty

  TBD Brook Rd, Middletown, NY 10941
• 

  $780,000

  Sold Jul 21, 2025

  197 Elise Dr, Middletown, NY 10941

  • 4 Beds
  • 2.5 Baths
  • 3,217 Sq Ft
  • Built 2024

  Last Sold Summary

  • 1% Above List Price
  • $242/SF
  • 61 Days On Market

  Current Estimated Value $786,300

  Last Listing Agent Juan Bautista Serhant LLC

  197 Elise Dr, Middletown, NY 10941
• 

  Not Listed For Sale

  48 Inwood Rd, Middletown, NY 10941

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft
  • Built 1975

  48 Inwood Rd, Middletown, NY 10941

  Last Sold Summary

  • 29 Days On Market
• 

  

  /41

  $440,000

  $40K PRICE DROP Pending

  • 4 Beds
  • 2.5 Baths
  • 2,848 Sq Ft

  4 Thistle Ln, Middletown, NY 10940

  Spacious & Versatile Raised Ranch in Prime Middletown Location! Not your average bi-level! This move-in-ready, raised-ranch-style home in Middletown, within the Minisink Valley School District, offers the perfect blend of convenience and comfort. Located near Garnet Medical Center, Crystal Run, shopping centers, supermarkets, and with easy access to Metro-North and major highways, it’s an ideal

  Soleil Jackman Howard Hanna Rand Realty

  4 Thistle Ln, Middletown, NY 10940
• 

  $261,000

  Sold Jul 29, 2025

  67 Deer Court Dr, Middletown, NY 10940

  • 2 Beds
  • 2 Baths
  • 1,146 Sq Ft
  • Built 2002

  Last Sold Summary

  • 1% Above List Price
  • $228/SF
  • 30 Days On Market

  Current Estimated Value $265,294

  Last Listing Agent Gail Rachlin KW Hudson Valley United

  67 Deer Court Dr, Middletown, NY 10940
• 

  Est $293,173

  Not Listed For Sale

  6 Inwood Rd, Middletown, NY 10941

  • 3 Beds
  • 2.5 Baths
  • 1,520 Sq Ft
  • Built 1974

  6 Inwood Rd, Middletown, NY 10941

  Last Sold Summary

  • 31 Days On Market
• 

  

  /43

  $745,000

  $670K PRICE INCREASE

  • 4 Beds
  • 2 Baths
  • 1,395 Sq Ft

  903 Rd, Middletown, NY 12421

  Rare Catskills Investment Retreat — Pool, Views & Proven Short-Term Rental Income. One of the few properties in the Catskills with a private pool and the income to match, this turnkey 4-bedroom, 2-bath mountain retreat on 5+ acres offers a competitive edge that most area listings simply cannot. The private pool extends peak demand well beyond the winter ski season, attracting premium summer

  Ashley O'Malley Listing by Jewett and Jewett LLC

  

  903 Rd, Middletown, NY 12421
• 

  $430,000

  Sold Jul 01, 2025

  17 Ingalls St, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,824 Sq Ft
  • Built 1925

  Last Sold Summary

  • 10% Above List Price
  • $236/SF
  • 27 Days On Market

  Current Estimated Value $385,565

  Last Listing Agent Isaiah Lopez KW Hudson Valley United

  17 Ingalls St, Middletown, NY 10940
• 

  Est $286,613

  Not Listed For Sale

  36 Poplar Ln, Middletown, NY 10941

  • 3 Beds
  • 2.5 Baths
  • 1,520 Sq Ft
  • Built 1974

  36 Poplar Ln, Middletown, NY 10941

  Last Sold Summary

  • 82 Days On Market
• 

  

  /13

  $45,000

  • Land
  • 1.4 Acres
  • $32,143 per Acre

  Pocatello Road Pocatello Rd, Middletown, NY 10940

  Country Living. yet just ten minutes to Middletown NY. area of nice homes. over 249 feet county road frontage. no close neighbors private. Rt 17 Rt 24 Rt 35 all close by. for easy commute to work. Orange County is a leader in population and company relocating more jobs Avalible. five minutes to Maple Hill Elementary School zoned R2 with no water and no sewer one would need 3 Acres so this

  John Melchior Howard Hanna Rand Realty

  Pocatello Road Pocatello Rd, Middletown, NY 10940
• 

  $790,000

  Sold Jan 09, 2026

  273 Pine Grove Rd, Middletown, NY 10940

  • 4 Beds
  • 2.5 Baths
  • 3,129 Sq Ft
  • Built 2004

  Last Sold Summary

  • $252/SF
  • 28 Days On Market

  Current Estimated Value $772,723

  Last Listing Agent Douglas McVicker Suburban Investment Realty

  273 Pine Grove Rd, Middletown, NY 10940
• 

  Est $418,870

  Not Listed For Sale

  21 Crane Rd, Middletown, NY 10941

  • 3 Beds
  • 2.5 Baths
  • 1,796 Sq Ft
  • Built 1974

  21 Crane Rd, Middletown, NY 10941

  Last Sold Summary

  • 29 Days On Market
• 

  

  /41

  $749,900

  • 4 Beds
  • 2.5 Baths
  • 2,906 Sq Ft

  512 County Route 49, Middletown, NY 10940

  Welcome to this stunning, meticulously maintained Chesterfield Colonial offering breathtaking views, exceptional updates, and true move-in-ready condition. From the moment you enter the impressive two-story foyer, you'll appreciate the bright, open-concept design and abundance of natural light streaming through every window. The spacious main living areas are perfect for both everyday living and

  Jonathon Lee KW Hudson Valley United

  512 County Route 49, Middletown, NY 10940
• 

  $315,000

  Sold Oct 30, 2025

  38 Sheffield Dr, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,220 Sq Ft
  • Built 1974

  Last Sold Summary

  • $258/SF
  • 53 Days On Market

  Current Estimated Value $308,698

  Last Listing Agent Malik Subhani Weichert Realtors

  38 Sheffield Dr, Middletown, NY 10940
• 

  Est $297,765

  Not Listed For Sale

  26 Chaucer Ct, Middletown, NY 10941

  • 3 Beds
  • 1.5 Baths
  • 1,428 Sq Ft
  • Built 1975

  26 Chaucer Ct, Middletown, NY 10941

  Last Sold Summary

  • 20 Days On Market
• 

  

  /48

  $435,000

  Open Sun 12PM - 2PM $14K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 2,041 Sq Ft

  60 Peach Place, Middletown, NY 10940

  Welcome to Swan Village Estates conveniently located just minutes from Highways, stores and shopping. If space is what you need, this three-level , corner lot townhome offers that and more inside and out! The main level features a bright living room with plenty of natural window light followed by a dining area and a spacious eat-in kitchen with stainless steel appliances with plenty of cabinet

  Sandra Arnez KW Hudson Valley United

  60 Peach Place, Middletown, NY 10940
• 

  $230,000

  Sold Dec 16, 2025

  13 Smith St, Middletown, NY 10940

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft
  • Built 1900

  Last Sold Summary

  • 23% Below List Price
  • $205/SF
  • 161 Days On Market

  Current Estimated Value $237,526

  Last Listing Agent Dulce M Ferrera KW Hudson Valley United

  13 Smith St, Middletown, NY 10940
• 

  Est $283,438

  Not Listed For Sale

  18 Chaucer Ct, Middletown, NY 10941

  • 3 Beds
  • 1.5 Baths
  • 1,428 Sq Ft
  • Built 1975

  18 Chaucer Ct, Middletown, NY 10941

  Last Sold Summary

  • 45 Days On Market
• 

  

  /10

  $299,999

  • Land
  • 27.2 Acres
  • $11,029 per Acre

  328 Bloomingburg Rd, Middletown, NY 10940

  Fully Available!! Vacant Property directly across from Fair Oaks Drive in Movie theater and a gas station with plenty of road frontage!! Minutes to RT17. 27.2 ACRES!!! Electric on road at the front of the property! Possible small farm, Big enough for horses, growing crops, family compound. R2 Zoning.The owner is currently using the property to grow crops and has an Agricultural tax exemption.

  Jeffrey Lyons Curasi Realty, Inc.

  328 Bloomingburg Rd, Middletown, NY 10940
• 

  $950,000

  Sold Oct 27, 2025

  190 Crans Rd, Middletown, NY 10941

  • 3 Beds
  • 2.5 Baths
  • 2,000 Sq Ft
  • Built 2000

  Last Sold Summary

  • $475/SF
  • 24 Days On Market

  Current Estimated Value $922,673

  Last Listing Agent Deb Cor Exclusively Equine Prop LLC

  190 Crans Rd, Middletown, NY 10941
• 

  Est $295,919

  Not Listed For Sale

  18 Shelley Ct, Middletown, NY 10941

  • 3 Beds
  • 1.5 Baths
  • 1,428 Sq Ft
  • Built 1973

  18 Shelley Ct, Middletown, NY 10941

  Last Sold Summary

  • 43 Days On Market
• 

  

  /15

  $399,999

  Open Sun 1PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 1,496 Sq Ft

  21 Evan Ct, Middletown, NY 10940

  Welcome to 21 Evan Court, a beautifully maintained 3-bedroom, 2.5-bath home offering approximately 1,500 square feet of comfortable living space, plus additional finished basement space and a one-car garage. Situated on a quiet cul-de-sac in a desirable Middletown neighborhood, this home delivers the perfect blend of space, functionality, and convenience.Step inside to discover bright and

  Marquise Fulmore HomeSmart Homes & Estates

  21 Evan Ct, Middletown, NY 10940
• 

  $260,000

  Sold Jul 18, 2025

  189 Ruth Ct, Middletown, NY 10940

  • 2 Beds
  • 2 Baths
  • 1,049 Sq Ft
  • Built 2006

  Last Sold Summary

  • 4% Above List Price
  • $248/SF
  • 48 Days On Market

  Current Estimated Value $265,675

  Last Listing Agent Rosalie Cook Weichert Realtors

  189 Ruth Ct, Middletown, NY 10940
• 

  Est $308,111

  Not Listed For Sale

  36 Whitman Ct, Middletown, NY 10941

  • 3 Beds
  • 1.5 Baths
  • 1,428 Sq Ft
  • Built 1974

  36 Whitman Ct, Middletown, NY 10941

  Last Sold Summary

  • 97 Days On Market
• 

  

  /43

  $333,000

  $2K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,473 Sq Ft

  51 Deer Ct Dr, Middletown, NY 10940

  Welcome to this townhouse-style condo in Middletown, offering 2 bedrooms and 2.5 bathrooms. The first floor features a functional layout with a kitchen that opens to a dining area, a spacious living room, and a half bath. The kitchen offers a practical galley-style layout with ample cabinetry and counter space for everyday living. The open-concept living area provides a flexible layout for

  Jie Liu KW Hudson Valley United

  51 Deer Ct Dr, Middletown, NY 10940
• 

  $750,000

  Sold Aug 21, 2025

  22 Restorative Ln, Middletown, NY 10940

  • 4 Beds
  • 2.5 Baths
  • 2,629 Sq Ft
  • Built 2010

  Last Sold Summary

  • 9% Above List Price
  • $285/SF
  • 33 Days On Market

  Current Estimated Value $734,377

  Last Listing Agent Susanne Dermigny Howard Hanna Rand Realty

  22 Restorative Ln, Middletown, NY 10940
• 

  Est $439,500

  Not Listed For Sale

  44 Crane Rd, Middletown, NY 10941

  • 3 Beds
  • 2 Baths
  • 1,904 Sq Ft
  • Built 1977

  44 Crane Rd, Middletown, NY 10941

  Last Sold Summary

  • 188 Days On Market
• 

  

  /50

  $479,000

  $21K PRICE DROP

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

  9 Cornwall Ln, Middletown, NY 10940

  Step into luxury with this meticulously maintained home featuring rich hardwood floors, exquisite crown molding and recessed lighting with dimmable features throughout. The well appointed kitchen is a chef's dream, boasting GE stainless steel appliances, a beautiful tile backsplash, double sink, pantry and great cabinet space. Enjoy a wonderful formal dining area with a large window that floods

  Theresa Russo Coldwell Banker Realty

  9 Cornwall Ln, Middletown, NY 10940
• 

  $255,000

  Sold Apr 07, 2026

  17 N Aspen Rd, Middletown, NY 10940

  • 2 Beds
  • 1.5 Baths
  • 1,144 Sq Ft
  • Built 1974

  Last Sold Summary

  • 5% Below List Price
  • $223/SF
  • 27 Days On Market

  Current Estimated Value $256,122

  Last Listing Agent Jonathon Lee KW Hudson Valley United

  17 N Aspen Rd, Middletown, NY 10940
• 

  Est $309,229

  Not Listed For Sale

  32 Whitman Ct, Middletown, NY 10941

  • 3 Beds
  • 1.5 Baths
  • 1,428 Sq Ft
  • Built 1974

  32 Whitman Ct, Middletown, NY 10941

  Last Sold Summary

  • 87 Days On Market
• 

  

  /36

  $420,000

  Pending

  • 3 Beds
  • 1 Bath
  • 1,616 Sq Ft

  525 Bloomingburg Rd, Middletown, NY 10940

  Your next chapter begins here! The bright, spacious living room sets the tone—an inviting space where you can unwind and recharge after a busy day. The generous open concept kitchen is ready for you to craft your favorite recipes and enjoy effortless everyday living.Convenience shines with a first floor bedroom and full bathroom offering comfort and flexibility. Upstairs, you’ll find two

  Kichka Pascaru Douglas Elliman Real Estate

  525 Bloomingburg Rd, Middletown, NY 10940
• 

  $565,000

  Sold Nov 12, 2025

  2213 Mount Hope Rd, Middletown, NY 10940

  • 4 Beds
  • 3 Baths
  • 2,800 Sq Ft
  • Built 1949

  Last Sold Summary

  • 6% Below List Price
  • $202/SF
  • 76 Days On Market

  Current Estimated Value $565,097

  Last Listing Agent Chris Scibelli Keller Williams Realty

  2213 Mount Hope Rd, Middletown, NY 10940
• 

  Est $445,241

  Not Listed For Sale

  10 Crane Rd, Middletown, NY 10941

  • 4 Beds
  • 1.5 Baths
  • 2,138 Sq Ft
  • Built 1975

  10 Crane Rd, Middletown, NY 10941

  Last Sold Summary

  • 22 Days On Market
• 

  

  /35

  $589,000

  Pending

  • 4 Beds
  • 3 Baths
  • 2,732 Sq Ft

  24 3rd St, Middletown, NY 10940

  BETTER THAN NEW! SPACIOUS 4-Bedroom, 3-Full Bath Bi-Level ColonialWelcome to this meticulously maintained home offering over 2,700 sq ft of beautifully finished living space that blends modern style with timeless charm. Step into the gorgeous eat-in kitchen, thoughtfully designed with: A large center island with ample seating Gleaming hardwood floors Vaulted ceilings that create a bright,

  Jane Panico Realty Promotions Inc

  24 3rd St, Middletown, NY 10940
• 

  $295,000

  Sold Aug 21, 2025

  87 Sycamore Dr, Middletown, NY 10940

  • 2 Beds
  • 2 Baths
  • 1,342 Sq Ft
  • Built 1977

  Last Sold Summary

  • $220/SF
  • 64 Days On Market

  Current Estimated Value $307,095

  Last Listing Agent Jacqueline Henry-Thompson Jackie Henry Realty LLC

  87 Sycamore Dr, Middletown, NY 10940

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