Middletown, NY Homes

• 

  

  

  /30

  $844,000

  $5K PRICE DROP

  • 5 Beds
  • 2.5 Baths
  • 3,764 Sq Ft

  238 S Centerville Rd, Middletown, NY 10940

  Spacious Country Retreat on 22.6 Acres in Minisink Valley School District This exceptional property offers privacy, comfort, and extensive amenities set on 22.6 picturesque acres. The master bedroom and bathroom were updated in 2016, complemented by a wet bar in the family room—perfect for entertaining. The home features three fireplaces and a wood stove, creating warmth and character throughout.

  Linda VanDeWeert BHG Real Estate Green Team

  238 S Centerville Rd, Middletown, NY 10940
• 

  $435,000

  Sold Jan 26, 2026

  6 Knapp Ave, Middletown, NY 10940

  • 1,986 Sq Ft
  • Built 1870

  Last Sold Summary

  • $219/SF
  • 47 Days On Market

  Current Estimated Value $432,497

  Last Listing Agent Joao Rodrigues Preferred Properties Real Esta

  6 Knapp Ave, Middletown, NY 10940
• 

  Est $353,205

  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
• 

  

  

  /26

  $134,999

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  79 Stern Scenic Dr, Middletown, NY 10940

  Welcome to this updated 3-bedroom, 2-bath double-wide mobile home offering comfort, space, and convenience in Middletown. Recent updates enhance both style and functionality, while the open and spacious layout provides plenty of room to relax or entertain. The primary bedroom features a private bath, and the additional bedrooms are generously sized. Conveniently located near local shopping,

  Ivan Carvalho Exit Realty Connections

  79 Stern Scenic Dr, Middletown, NY 10940
• 

  $441,000

  Sold Apr 30, 2026

  262 Cottage St, Middletown, NY 10940

  • 5 Beds
  • 2 Baths
  • 2,547 Sq Ft
  • Built 1962

  Last Sold Summary

  • 11% Above List Price
  • $173/SF
  • 28 Days On Market

  Last Listing Agent Avraham Weinberger Keller Williams Valley Realty

  262 Cottage St, Middletown, NY 10940
• 

  Est $478,742

  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
• 

  

  /15

  $95,000

  $10K PRICE DROP

  • Land
  • 5.1 Acres
  • $18,627 per Acre

  Lot 11 Meadow Brook Dr, Middletown, NY 12455

  Tucked away in the pastoral rolling hills, just a short drive from down town Margaretville, this very special 5 acre parcel is sure to check many boxes on your wish list. A peaceful and serene setting with beautiful scenic views and rolling open meadows backed by magical woods to explore. With several possible building sites this parcels offers what most are looking for. Easy access, and close to

  Rosalie Glauser Listing by Frank Lumia Real Estate Plus!, LLC

  

  Lot 11 Meadow Brook Dr, Middletown, NY 12455
• 

  $620,000

  Sold Oct 27, 2025

  58 White Bridge Rd, Middletown, NY 10940

  • 4 Beds
  • 3 Baths
  • 3,328 Sq Ft
  • Built 1992

  Last Sold Summary

  • 2% Below List Price
  • $186/SF
  • 21 Days On Market

  Current Estimated Value $627,890

  Last Listing Agent Patricia Sassi RE/MAX Benchmark Realty Group

  58 White Bridge Rd, Middletown, NY 10940
• 

  Est $470,064

  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
• 

  

  /12

  $410,000

  Pending

  • 5 Beds
  • 4 Baths

  41 Monhagen Ave Unit 39, Middletown, NY 10940

  Sold as is?This versatile property offers the perfect blend of comfortable living and passive income generation. Whether you are a first-time homebuyer looking to offset your mortgage or a seasoned investor seeking a high-yield asset, this legal two-family home is a standout choice. The Strategy: Live for Less, Earn MoreThe property is ideally configured for an owner-occupant strategy: Main

  Zhiheng Tang KW Hudson Valley Untied

  41 Monhagen Ave Unit 39, Middletown, NY 10940
• 

  $605,000

  Sold Sep 19, 2025

  344 Ingrassia Rd, Middletown, NY 10940

  • 4 Beds
  • 2.5 Baths
  • 2,410 Sq Ft
  • Built 2006

  Last Sold Summary

  • 3% Below List Price
  • $251/SF
  • 71 Days On Market

  Current Estimated Value $598,331

  Last Listing Agent Travis Thompson KW Hudson Valley Untied

  344 Ingrassia Rd, Middletown, NY 10940
• 

  Est $447,637

  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
• 

  

  /18

  $250,000

  Pending

  • 2 Beds
  • 1.5 Baths
  • 1,240 Sq Ft

  34 Poplar Ln, Middletown, NY 10941

  This well-maintained home offers comfort, space, and convenience in a desirable location close to shopping, dining, and public transportation. Step inside to find generously sized bedrooms with vaulted ceilings that create an open and airy feel. The rear bedroom features a private balcony—perfect for morning coffee or unwinding at the end of the day. A full basement provides ample storage space,

  John Olivero Keller Williams Realty

  34 Poplar Ln, Middletown, NY 10941
• 

  $425,000

  Sold Aug 11, 2025

  44 Karen Joy Dr, Middletown, NY 10940

  • 4 Beds
  • 1.5 Baths
  • 2,706 Sq Ft
  • Built 1977

  Last Sold Summary

  • $157/SF
  • 97 Days On Market

  Current Estimated Value $453,538

  Last Listing Agent Frank Muccari Cronin & Company Real Estate

  44 Karen Joy Dr, Middletown, NY 10940
• 

  Est $361,496

  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
• 

  

  /46

  $599,000

  $19K PRICE DROP Pending

  • 3 Beds
  • 2.5 Baths
  • 1,977 Sq Ft

  70 King Rd, Middletown, NY 10941

  Welcome to a truly special property, a wonderful home that combines style, comfort, and a park-like location. Close to all Middletown has to offer. The heart of the home is the living room — this sunny room features a fireplace, hardwood floors, and a cathedral ceiling, making it the perfect place to retreat to after sharing a meal in the connected dining room. Cooking in the new kitchen on the

  Jeanine Stoddard Coldwell Banker Village Green

  70 King Rd, Middletown, NY 10941
• 

  $955,000

  Sold May 18, 2026

  535 County Route 22, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 3,315 Sq Ft
  • Built 2022

  Last Sold Summary

  • 4% Below List Price
  • $288/SF
  • 140 Days On Market

  Last Listing Agent John Biasi Howard Hanna Rand Realty

  535 County Route 22, Middletown, NY 10940
• 

  Est $625,490

  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
• 

  

  /12

  $280,250

  $15K PRICE DROP Pending

  • 2 Beds
  • 2.5 Baths
  • 1,241 Sq Ft

  2 Durham Ct Unit 82, Middletown, NY 10940

  A Rare Find Just Got Better with a price improvement. Finding a place that balances a peaceful nature retreat with the reality of needing everyday essentials and good takeout close by is a rare find. Enter Waters Edge, Middletown’s premier condo community right on Silver Lake. This large end-unit townhome gives you all the perks of homeownership with none of the weekend-ruining yard work, meaning

  Melissa Terman River Realty Services, Inc.

  2 Durham Ct Unit 82, Middletown, NY 10940
• 

  $157,200

  Sold Dec 05, 2025

  10 Hoffman St, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1920

  Last Sold Summary

  • 17% Below List Price
  • $131/SF
  • 70 Days On Market

  Current Estimated Value $195,325

  Last Listing Agent Jamarr Zellner REALHome Services & Solutions

  10 Hoffman St, Middletown, NY 10940
• 

  Est $594,226

  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
• 

  

  /36

  $359,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 1,345 Sq Ft

  18 Jordan Ln, Middletown, NY 10940

  Mountainside Hills in Middletown offers this townhouse-style condo featuring 3 bedrooms and 2.5 bathrooms. The main level provides a comfortable and functional layout with a spacious living room, a dining area, and a convenient half bath. Sliding glass doors lead to the rear deck, offering a nice space for outdoor relaxation. The kitchen offers generous cabinet and counter space and tile

  Jie Liu KW Hudson Valley Untied

  18 Jordan Ln, Middletown, NY 10940
• 

  $550,000

  Sold Mar 02, 2026

  21 Cyprus Dr, Middletown, NY 10940

  • 2 Beds
  • 2 Baths
  • 1,868 Sq Ft
  • Built 2016

  Last Sold Summary

  • $294/SF
  • 38 Days On Market

  Current Estimated Value $551,621

  Last Listing Agent Patricia Sassi RE/MAX Benchmark Realty Group

  21 Cyprus Dr, Middletown, NY 10940
• 

  Est $594,109

  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
• 

  /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
• 

  $450,000

  Sold Dec 19, 2025

  6 Tice Ln, Middletown, NY 10941

  • 3 Beds
  • 2 Baths
  • 2,070 Sq Ft
  • Built 1986

  Last Sold Summary

  • $217/SF
  • 43 Days On Market

  Current Estimated Value $452,983

  Last Listing Agent John Olivero Keller Williams Realty

  6 Tice Ln, Middletown, NY 10941
• 

  Est $509,686

  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
• 

  

  /43

  $469,900

  Pending

  • 3 Beds
  • 2.5 Baths
  • 1,508 Sq Ft

  80 Excelsior Ave, Middletown, NY 10940

  Welcome to 80 Excelsior Ave in Middletown! This well maintained and thoughtfully updated home offers both comfort and functionality. The first floor features a spacious living room and dining room with durable laminate flooring, a convenient half bath, and a tiled kitchen with stainless steel appliances. Upstairs, you'll find three generously sized bedrooms and two full baths, along with a

  Melanie Potter Curasi Realty, Inc.

  80 Excelsior Ave, Middletown, NY 10940
• 

  $402,000

  Sold Sep 12, 2025

  19 Morningside Dr, Middletown, NY 10941

  • 4 Beds
  • 1.5 Baths
  • 1,984 Sq Ft
  • Built 1971

  Last Sold Summary

  • 9% Above List Price
  • $203/SF
  • 15 Days On Market

  Current Estimated Value $403,191

  Last Listing Agent Paul Halpern Hudson Valley Griffith

  19 Morningside Dr, Middletown, NY 10941
• 

  Est $461,107

  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
• 

  

  /9

  $399,900

  • 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
• 

  $195,000

  Sold Jan 30, 2026

  21 Lake Claire Dr, Middletown, NY 10940

  • 2 Beds
  • 2 Baths
  • 990 Sq Ft
  • Built 1955

  Last Sold Summary

  • 22% Below List Price
  • $197/SF
  • 142 Days On Market

  Current Estimated Value $207,841

  Last Listing Agent Nelson Dominguez eXp Realty

  21 Lake Claire Dr, Middletown, NY 10940
• 

  Est $426,777

  Not Listed For Sale

  35 Roger Ave, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,132 Sq Ft
  • Built 1983

  35 Roger Ave, Middletown, NY 10940

  Last Sold Summary

  • 33 Days On Market
• 

  

  /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
• 

  $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 $634,276

  Last Listing Agent Lynelle Alessi KW Hudson Valley Untied

  138 Reinhardt Rd, Middletown, NY 10940
• 

  Est $470,941

  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
• 

  

  /50

  $589,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 1,904 Sq Ft

  16 Fawn Ct, Middletown, NY 10940

  Tucked away at the end of a quiet cul-de-sac, 16 Fawn Court offers the kind of setting that feels like a retreat, yet remains incredibly connected to everything the Hudson Valley has to offer. Located in the desirable Minisink Valley School District, right on the edge of the Otisville Elementary zone, this location provides a thoughtful balance, making everyday routines both convenient and

  Amanda Brehm KW Hudson Valley Untied

  16 Fawn Ct, 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 $423,573

  Last Listing Agent Frank Muccari Cronin & Company Real Estate

  10 Renfrewshire Dr, Middletown, NY 10941
• 

  Est $429,852

  Not Listed For Sale

  16 Roger Ave, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,132 Sq Ft
  • Built 1983

  16 Roger Ave, Middletown, NY 10940

  Last Sold Summary

  • 21 Days On Market
• 

  

  /5

  $399,000

  $126K PRICE DROP

  • 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 Untied

  TBD Silver Lake-Scotchtown Rd, Middletown, NY 10940

Showing Results 321 - 360, Page 9 of 18