Middletown, NY Homes

• 

  Est $430,782

  Not Listed For Sale

  25 Karen Joy Dr, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 2,080 Sq Ft
  • Built 1978

  25 Karen Joy Dr, Middletown, NY 10940

  Last Sold Summary

  • 62 Days On Market

  Last Listing Agent Yara Roussos Homes By Yara Realty Group LLC
• 

  

  /2

  $55,000

  $10K PRICE DROP

  • Land
  • 10,454 Sq Ft
  • $229,167 per Acre

  1 S Shore Dr, Middletown, NY 10940

  Quarter acre waterfront parcel located on Pocatello Lake. Scenic water views, and a peaceful setting with convenient access to local amenities in the City of Middletown and Town of Wallkill. Rare opportunity for lakefront land ownership in a desirable location.

  Soleil Jackman Howard Hanna Rand Realty

  1 S Shore Dr, Middletown, NY 10940
• 

  $478,500

  Sold Nov 12, 2025

  138 Reinhardt Rd, Middletown, NY 10940

  • 3 Beds
  • 3 Baths
  • 2,542 Sq Ft
  • Built 1969

  Last Sold Summary

  • 2% Below List Price
  • $188/SF
  • 65 Days On Market

  Current Estimated Value $643,570

  Last Listing Agent Lynelle Alessi KW Hudson Valley United

  138 Reinhardt Rd, Middletown, NY 10940
• 

  Not Listed For Sale

  22 Witte Dr, Middletown, NY 10940

  • 3 Beds
  • 1 Bath
  • 1,316 Sq Ft
  • Built 1981

  22 Witte Dr, Middletown, NY 10940

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Nina Piacente Julia B Fee Sothebys Int. Rlty
• 

  

  

  /38

  $899,900

  • 5 Beds
  • 4.5 Baths
  • 4,200 Sq Ft

  255 Howells Rd, Middletown, NY 10940

  Enter the gates of this remarkable 36.8-acre estate to discover a distinguished 5-bedroom, 5-bathroom residence offering 4,200 square feet of living space. The property includes a substantial two-story post-and-beam barn with horse stalls, multiple wells, and an additional hay barn—ideal for equestrian or agricultural use. A serene natural pond and a mix of rolling pastures and wooded areas

  Jonathon Lee KW Hudson Valley United

  255 Howells Rd, Middletown, NY 10940
• 

  $445,000

  Sold Jun 18, 2026

  10 Renfrewshire Dr, Middletown, NY 10941

  • 3 Beds
  • 1.5 Baths
  • 1,788 Sq Ft
  • Built 1968

  Last Sold Summary

  • 5% Above List Price
  • $249/SF
  • 14 Days On Market

  Current Estimated Value $441,636

  Last Listing Agent Frank Muccari Cronin & Company Real Estate

  10 Renfrewshire Dr, Middletown, NY 10941
• 

  Not Listed For Sale

  31 Witte Dr, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,907 Sq Ft
  • Built 1989

  31 Witte Dr, Middletown, NY 10940

  Last Sold Summary

  • 42 Days On Market

  Last Listing Agent Frank Muccari Cronin & Company Real Estate
• 

  

  /50

  $549,999

  • 4 Beds
  • 3.5 Baths
  • 2,298 Sq Ft

  19 Davidge Rd, Middletown, NY 10940

  Welcome to 19 Davidge Road, where luxury, comfort, and functionality come together in one exceptional home. Nestled in the highly sought-after Presidential Heights neighborhood, this impressive 4-bedroom, 4-bathroom residence offers the perfect blend of elegant living spaces and incredible amenities designed for today's lifestyle.From the moment you enter, you'll be captivated by the soaring

  Kevin Grier KW Hudson Valley United

  19 Davidge Rd, Middletown, NY 10940
• 

  $390,000

  Sold Aug 19, 2026

  82 California Ave, Middletown, NY 10940

  • 4 Beds
  • 2 Baths
  • 1,376 Sq Ft
  • Built 1937

  Last Sold Summary

  • 4% Above List Price
  • $283/SF
  • 49 Days On Market

  Current Estimated Value $367,839

  Last Listing Agent JOHN SCARANO Keller Williams Realty

  82 California Ave, Middletown, NY 10940
• 

  Est $352,661

  Not Listed For Sale

  919 Winterton Rd, Middletown, NY 10940

  • 3 Beds
  • 1 Bath
  • 1,294 Sq Ft
  • Built 1980

  919 Winterton Rd, Middletown, NY 10940

  Last Sold Summary

  • 148 Days On Market

  Last Listing Agent Derek Greene Greene Realty Group
• 

  

  /9

  $399,900

  Pending

  • 4 Beds
  • 2 Baths
  • 1,472 Sq Ft

  25 Mill St, Middletown, NY 10940

  Completely renovated two-unit property with Residential/CMU zoning. Ideal opportunity for an owner-user or investor — operate your business on the first floor while generating rental income from the occupied second-floor unit. Property includes 2 car parking/off-street parking, with potential for expansion subject to city approvals.

  Sammy Zambrano Keller Williams Realty

  25 Mill St, Middletown, NY 10940
• 

  $485,000

  Sold Oct 23, 2025

  38 Woodside Knolls Dr, Middletown, NY 10940

  • 3 Beds
  • 3.5 Baths
  • 1,899 Sq Ft
  • Built 2008

  Last Sold Summary

  • 1% Above List Price
  • $255/SF
  • 42 Days On Market

  Current Estimated Value $493,698

  Last Listing Agent Naomi Streicher Q Home Sales

  38 Woodside Knolls Dr, Middletown, NY 10940
• 

  Est $480,162

  Not Listed For Sale

  90 Upper Rd, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,580 Sq Ft
  • Built 1964

  90 Upper Rd, Middletown, NY 10940

  Last Sold Summary

  • 62 Days On Market

  Last Listing Agent Laurel Lustgarten Howard Hanna Rand Realty
• 

  

  /24

  $269,000

  Pending

  • 2 Beds
  • 1.5 Baths
  • 960 Sq Ft

  Unlisted Address

  Middletown! Vintage Colonial set mid-block among similar homes. The main level features a spacious living room, dining room, kitchen, and half bath. The second level offers two bedrooms and a full bath. Spacious rooms throughout with hardwood floors and a good-sized kitchen. Ideal opportunity for a first-time buyer or investor, with low taxes. Conveniently located close to shopping and major

  Naomi Streicher Q Home Sales

  Unlisted Address
• 

  $48,000

  Sold Mar 03, 2026

  8 Knapp Ave, Middletown, NY 10940

  • Land
  • 5,501 Sq Ft
  • $380,048 per Acre

  Last Sold Summary

  • 126% Above List Price
  • 9 Days On Market

  Current Estimated Value $292,647

  Last Listing Agent Neven Spralja REALHome Services & Solutions

  8 Knapp Ave, Middletown, NY 10940
• 

  Est $473,642

  Not Listed For Sale

  1 Silver Mine Estate Rd, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 1,930 Sq Ft
  • Built 1964

  1 Silver Mine Estate Rd, Middletown, NY 10940

  Last Sold Summary

  • 80 Days On Market

  Last Listing Agent Margaret Galatro ARC Realty 1 in Sales
• 

  

  /5

  $399,000

  $126K PRICE DROP Pending

  • Land
  • 3.8 Acres
  • $105,028 per Acre

  TBD Silver Lake-Scotchtown Rd, Middletown, NY 10940

  Attention Builders and Developers: Presenting a rare, fully-approved 3-lot subdivision on Silverlake Scotchtown Road in the desirable Town of Wallkill, ready for the construction of three new two-family homes. Each lot is designed to accomodate a 32x80 structure which is large enough for each unit to include 3 bedrooms, 2 baths and a 1 car garage. Seller does not have architectural plans so

  Jason McGovern KW Hudson Valley United

  TBD Silver Lake-Scotchtown Rd, Middletown, NY 10940
• 

  $325,000

  Sold Apr 28, 2026

  46 Silo Ln, Middletown, NY 10940

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

  Last Sold Summary

  • $224/SF
  • 20 Days On Market

  Current Estimated Value $325,996

  Last Listing Agent Jason Dillon eXp Realty

  46 Silo Ln, Middletown, NY 10940
• 

  Est $454,273

  Not Listed For Sale

  768 Winterton Rd, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft
  • Built 1960

  768 Winterton Rd, Middletown, NY 10940

  Last Sold Summary

  • 41 Days On Market

  Last Listing Agent Frank Cafarchio Keller Williams Realty
• 

  

  /21

  $324,999

  • 3 Beds
  • 1.5 Baths
  • 1,480 Sq Ft

  63 Greenway Terrace, Middletown, NY 10941

  On the market for the first time in nearly 20 years! Welcome to 63 Greenway Terrace, a well-loved and maintained three-level townhome offering comfort, convenience, and plenty of living space. The open floor plan creates an inviting flow throughout the main level, complemented by three generously sized bedrooms and 1.5 bathrooms. Enjoy the convenience of newer appliances and a private, fenced

  Valerie Jewis Keller Williams Realty

  63 Greenway Terrace, Middletown, NY 10941
• 

  $380,000

  Sold Feb 10, 2026

  7 Manhattan Ave, Middletown, NY 10940

  • 3 Beds
  • 1 Bath
  • 1,550 Sq Ft
  • Built 1958

  Last Sold Summary

  • 3% Above List Price
  • $245/SF
  • 46 Days On Market

  Current Estimated Value $377,980

  Last Listing Agent Darnell Williams R New York

  7 Manhattan Ave, Middletown, NY 10940
• 

  Est $374,529

  Not Listed For Sale

  24 Kirbytown Rd, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,536 Sq Ft
  • Built 1950

  24 Kirbytown Rd, Middletown, NY 10940

  Last Sold Summary

  • 238 Days On Market

  Last Listing Agent Dulce M Ferrera KW Hudson Valley United
• 

  

  /20

  $420,000

  • 3 Beds
  • 1.5 Baths
  • 1,344 Sq Ft

  4 Westminster Dr, Middletown, NY 10940

  Welcome home to this beautifully updated 3-bedroom, 1.5-bathroom house located in a quiet neighborhood! This home features new flooring and fresh paint throughout, an updated kitchen, and a large deck with an expansive yard—perfect for relaxing or entertaining.The property includes private driveway parking and a full basement providing ample storage. With the added convenience of an

  Elena James Keller Williams Realty

  4 Westminster Dr, Middletown, NY 10940
• 

  $285,000

  Sold Sep 17, 2026

  19 Hulse Ave, Middletown, NY 10940

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Built 1930

  Last Sold Summary

  • 2% Above List Price
  • $238/SF
  • 54 Days On Market

  Current Estimated Value $279,053

  Last Listing Agent Juan Bautista Serhant LLC

  19 Hulse Ave, Middletown, NY 10940
• 

  Est $644,809

  Not Listed For Sale

  283 Kirbytown Rd, Middletown, NY 10940

  • 4 Beds
  • 3.5 Baths
  • 2,490 Sq Ft
  • Built 1998

  283 Kirbytown Rd, Middletown, NY 10940

  Last Sold Summary

  • 66 Days On Market

  Last Listing Agent Annie Hansen Howard Hanna Rand Realty
• 

  

  /26

  $199,000

  $51K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 360 Sq Ft

  51 S Shore Dr, Middletown, NY 10940

  Welcome to 51 S Shore Drive, a charming and thoughtfully updated bungalow retreat nestled on a private, wooded 9,374 sq ft lot with sparkling lake views in scenic Middletown, NY. This beautifully curated 1-bedroom, 1-bath lakefront getaway offers 360 square feet of smart, stylish living space perfect for a weekend escape, vacation rental, or year-round peaceful living. Step inside to a crisp,

  Arya Rabinovits eRealty Advisors, Inc

  51 S Shore Dr, Middletown, NY 10940
• 

  $800,000

  Sold Aug 21, 2026

  48 Lone Indian Trail, Middletown, NY 10940

  • 4 Beds
  • 3.5 Baths
  • 2,462 Sq Ft
  • Built 1995

  Last Sold Summary

  • $325/SF
  • 18 Days On Market

  Current Estimated Value $791,520

  Last Listing Agent Olivia Cappelli Donna Ruffino Realty Corp

  48 Lone Indian Trail, Middletown, NY 10940
• 

  Est $613,282

  Not Listed For Sale

  291 Kirbytown Rd, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 2,064 Sq Ft
  • Built 1998

  291 Kirbytown Rd, Middletown, NY 10940

  Last Sold Summary

  • 32 Days On Market

  Last Listing Agent Ryan Degnan Howard Hanna Rand Realty
• 

  

  /46

  $789,900

  Open Sat 12PM - 3PM $10K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,958 Sq Ft

  158 Reiss Rd, Middletown, NY 10940

  This spacious farmhouse colonial pairs timeless style with thoughtful design, custom details and an exceptional setting in the Minisink Valley School District. Built in 2019, this home is like new construction but with smart upgrades and additions. Inside, rustic elegance takes center stage with beautiful wood accents, barn doors and warm finishes throughout. Designed with entertaining in mind,

  Danielle Bartula Howard Hanna Rand Realty

  158 Reiss Rd, Middletown, NY 10940
• 

  $360,000

  Sold Nov 07, 2025

  55 Prince St, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,537 Sq Ft
  • Built 1893

  Last Sold Summary

  • 16% Above List Price
  • $234/SF
  • 36 Days On Market

  Current Estimated Value $357,410

  Last Listing Agent Andi Berisha BHHS Hudson Valley Properties

  55 Prince St, Middletown, NY 10940
• 

  Est $630,431

  Not Listed For Sale

  31 Arbor Way, Middletown, NY 10940

  • 4 Beds
  • 3.5 Baths
  • 2,860 Sq Ft
  • Built 2007

  31 Arbor Way, Middletown, NY 10940

  Last Sold Summary

  • 48 Days On Market

  Last Listing Agent Dominick Tufano RE/MAX Benchmark Realty Group
• 

  

  /33

  $589,000

  $86K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,481 Sq Ft

  5 Decker Dr, Middletown, NY 10940

  Charming Farmhouse Retreat on 2.9 Acres! Nestled on a quiet country road in the Town of Greenville and located within the desirable Minisink Valley Central School District. This beautiful farmhouse-style home offers the perfect blend of comfort, charm, and country living. Inviting home features 3 bedrooms and 2.5 baths with attractive Pergo wood flooring throughout the downstairs, while upstairs

  Dominick Tufano RE/MAX Benchmark Realty Group

  5 Decker Dr, Middletown, NY 10940
• 

  $525,000

  Sold Jun 18, 2026

  10 Cyprus Dr, Middletown, NY 10940

  • 2 Beds
  • 2 Baths
  • 1,612 Sq Ft
  • Built 2014

  Last Sold Summary

  • 7% Above List Price
  • $326/SF
  • 29 Days On Market

  Current Estimated Value $510,832

  Last Listing Agent Hilary Ryan Goldman Howard Hanna Rand Realty

  10 Cyprus Dr, Middletown, NY 10940
• 

  Est $527,360

  Not Listed For Sale

  11 Maplewood Dr, Middletown, NY 10940

  • 4 Beds
  • 3 Baths
  • 2,432 Sq Ft
  • Built 1988

  11 Maplewood Dr, Middletown, NY 10940

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Frank Muccari Cronin & Company Real Estate
• 

  

  /22

  $285,000

  • 2 Beds
  • 1.5 Baths
  • 1,133 Sq Ft

  65 Jimal Dr, Middletown, NY 10940

  Welcome to 65 Jimal Drive, where comfortable living meets the convenience of a low-maintenance lifestyle. This well-kept two-bedroom, one-and-a-half-bath condo offers a bright and inviting layout with updated vinyl flooring flowing through the main living spaces. The spacious living room provides plenty of room to relax or entertain and opens naturally into the dining area and kitchen, creating

  Rebecca Kane KW Hudson Valley United

  65 Jimal Dr, Middletown, NY 10940
• 

  $480,000

  Sold Dec 05, 2025

  95 Rolling Meadows Rd, Middletown, NY 10940

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

  Last Sold Summary

  • 5% Above List Price
  • $234/SF
  • 14 Days On Market

  Current Estimated Value $487,876

  Last Listing Agent Kevin Grier KW Hudson Valley United

  95 Rolling Meadows Rd, Middletown, NY 10940
• 

  Est $474,589

  Not Listed For Sale

  8 Maureen Dr, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,584 Sq Ft
  • Built 1985

  8 Maureen Dr, Middletown, NY 10940

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent Sharon Pehush HomeSmart Homes & Estates
• 

  

  /26

  $295,000

  $25K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,291 Sq Ft

  18 Deer Ct Dr, Middletown, NY 10940

  Welcome to 18 Deer Court Dr, located in the desirable Deer Run community. This well-appointed second floor end unit offers approximately 1,291sqft, with 2 bedrooms, and 2 full bathrooms. This spacious condo combines comfort, style, and convenience in a wonderful Hudson Valley setting.Step inside to an open and inviting living and dining area featuring beautiful hardwood floors, creating a

  David Wilson Hudson Premium Realty

  18 Deer Ct Dr, Middletown, NY 10940
• 

  $338,500

  Sold Nov 26, 2025

  12 Columbine Ct, Middletown, NY 10940

  • 4 Beds
  • 1.5 Baths
  • 1,408 Sq Ft
  • Built 1979

  Last Sold Summary

  • 1% Above List Price
  • $240/SF
  • 33 Days On Market

  Current Estimated Value $336,230

  Last Listing Agent Christina Gilligan HomeSmart Homes & Estates

  12 Columbine Ct, Middletown, NY 10940
• 

  Est $485,878

  Not Listed For Sale

  80 Maureen Dr, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,584 Sq Ft
  • Built 1988

  80 Maureen Dr, Middletown, NY 10940

  Last Sold Summary

  • 26 Days On Market

  Last Listing Agent Frank Muccari Cronin & Company Real Estate

Showing Results 361 - 400, Page 10 of 18