21,198

Middletown, NY Homes

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  • 7 Wilbur Ave, Middletown, NY 10940

    $300,000

    Sold Oct 14, 2025

    7 Wilbur Ave, Middletown, NY 10940

    • 3 Beds
    • 1 Bath
    • 1,922 Sq Ft
    • Built 1892

    Last Sold Summary

    • 20% Below List Price
    • $156/SF
    • 128 Days On Market

    Current Estimated Value $367,413

    Last Listing Agent John Bilancione Nicoli Realty

    7 Wilbur Ave, Middletown, NY 10940
    • 658 Mt Orange Rd, Middletown, NY 10940

      Est $660,778

      Not Listed For Sale

      658 Mt Orange Rd, Middletown, NY 10940

      • 4 Beds
      • 2.5 Baths
      • 2,482 Sq Ft
      • Built 2005
      658 Mt Orange Rd, Middletown, NY 10940

      Last Sold Summary

      • 100 Days On Market

      Last Listing Agent Christina Biagini Weichert Realtors

  • 194 White Bridge Rd, Middletown, NY 10940
    194 White Bridge Rd, Middletown, NY 10940
    194 White Bridge Rd, Middletown, NY 10940
    /50

    $935,000

    • 3 Beds
    • 3.5 Baths
    • 2,340 Sq Ft

    194 White Bridge Rd, Middletown, NY 10940

    Set on 9.4 private acres, this extraordinary custom home offers high-function living, privacy, and expansive outdoor space. Designed by the renowned architectural firm, Pendergast & Terach, and inspired by contemporary craftsman design, the open single-level layout creates a seamless flow throughout. The home features a soaring cathedral ceiling, anchored by an impressive stone fireplace and

    Jody Atkinson Ellis Sotheby's Intl Realty

    194 White Bridge Rd, Middletown, NY 10940
  • 47 Liberty St, Middletown, NY 10940

    $440,000

    Sold Jun 07, 2026

    47 Liberty St, Middletown, NY 10940

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 1890

    Last Sold Summary

    • 1% Above List Price
    • $357/SF
    • 18 Days On Market

    Current Estimated Value $426,239

    Last Listing Agent Jonathon Lee KW Hudson Valley United

    47 Liberty St, Middletown, NY 10940
    • 427 Kirbytown Rd, Middletown, NY 10940

      Est $852,858

      Not Listed For Sale

      427 Kirbytown Rd, Middletown, NY 10940

      • 4 Beds
      • 3 Baths
      • 3,350 Sq Ft
      • Built 1999
      427 Kirbytown Rd, Middletown, NY 10940

      Last Sold Summary

      • 110 Days On Market

      Last Listing Agent Kewin Garabito eXp Realty

  • 0 Joe Todd Rd Unit R1680388, Middletown, NY 10940
    0 Joe Todd Rd Unit R1680388, Middletown, NY 10940
    0 Joe Todd Rd Unit R1680388, Middletown, NY 10940
    /18

    $55,000

    Under Contract
    • Land
    • 5.26 Acres
    • $10,456 per Acre

    0 Joe Todd Rd Unit R1680388, Middletown, NY 10940

    Near the end of a quiet town-maintained dead-end road, you’ll find this ideal building lot in the town of Fleischmanns. This parcel has a mix of evergreens, deciduous trees, open clearings, and a seasonal stream, most of which is on level terrain ideal for a driveway and building site. Enjoy the peace and tranquility of a wooded sanctuary just minutes up the hill from the happening main street of

    Peter Kleeman Listing by Jewett and Jewett LLC

    0 Joe Todd Rd Unit R1680388, Middletown, NY 10940
  • 227 Deer Ct Dr, Middletown, NY 10940

    $436,000

    Sold Apr 24, 2026

    227 Deer Ct Dr, Middletown, NY 10940

    • 3 Beds
    • 2.5 Baths
    • 1,919 Sq Ft
    • Built 1991

    Last Sold Summary

    • 7% Above List Price
    • $227/SF
    • 22 Days On Market

    Current Estimated Value $422,743

    Last Listing Agent Jie Liu KW Hudson Valley United

    227 Deer Ct Dr, Middletown, NY 10940
    • 1053 Kirby Place, Middletown, NY 10940

      Est $626,120

      Not Listed For Sale

      1053 Kirby Place, Middletown, NY 10940

      • 4 Beds
      • 3 Baths
      • 2,912 Sq Ft
      • Built 1986
      1053 Kirby Place, Middletown, NY 10940

      Last Sold Summary

      • 75 Days On Market

      Last Listing Agent Tolga Erzene Keller Williams Rlty Integrity

  • 143 Deer Ct Dr, Middletown, NY 10940
    143 Deer Ct Dr, Middletown, NY 10940
    143 Deer Ct Dr, Middletown, NY 10940
    /35

    $299,000

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

    143 Deer Ct Dr, Middletown, NY 10940

    Welcome to your move-in ready sanctuary at Deer Run! Located in desirable Middletown, NY, this freshly painted second-floor condo offers effortless turnkey living with an abundance of natural light throughout. The thoughtfully designed layout features a modern kitchen equipped with granite countertops, a brand-new fridge, a brand-new stove, and a surprisingly spacious pantry. Relax in the

    Martha Randazzo Howard Hanna Rand Realty

    143 Deer Ct Dr, Middletown, NY 10940
  • 8 Park Row, Middletown, NY 10941

    $340,000

    Sold Dec 19, 2025

    8 Park Row, Middletown, NY 10941

    • 4 Beds
    • 1.5 Baths
    • 1,496 Sq Ft
    • Built 1965

    Last Sold Summary

    • 4% Above List Price
    • $227/SF
    • 27 Days On Market

    Current Estimated Value $332,639

    Last Listing Agent Vanessa Wight BHG Real Estate Green Team

    8 Park Row, Middletown, NY 10941
    • 148 Camp Stadie Rd, Middletown, NY 10940

      Est $474,100

      Not Listed For Sale

      148 Camp Stadie Rd, Middletown, NY 10940

      • 3 Beds
      • 2 Baths
      • 1,720 Sq Ft
      • Built 1959
      148 Camp Stadie Rd, Middletown, NY 10940

      Last Sold Summary

      • 26 Days On Market

      Last Listing Agent Kathy Eubanks Keller Williams Realty

  • 2 White Horse Rd, Middletown, NY 10940
    2 White Horse Rd, Middletown, NY 10940
    2 White Horse Rd, Middletown, NY 10940
    /47

    $1,249,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 4,225 Sq Ft

    2 White Horse Rd, Middletown, NY 10940

    Offered for sale for the very first time by its original owners, this custom-designed and thoughtfully upgraded 3-bedroom, 2.5-bath private luxury estate is nestled on 12.7 level acres in the Town of Greenville. Built in 2014 with quality craftsmanship and comfort in mind, this expansive home offers the perfect blend of space, functionality, and modern efficiency. The chef’s kitchen outfitted

    Vanessa Wight BHG Real Estate Green Team

    2 White Horse Rd, Middletown, NY 10940
  • 4 Wayne Ct, Middletown, NY 10941

    $538,900

    Sold Mar 31, 2026

    4 Wayne Ct, Middletown, NY 10941

    • 4 Beds
    • 2.5 Baths
    • 2,404 Sq Ft
    • Built 2004

    Last Sold Summary

    • $224/SF
    • 33 Days On Market

    Current Estimated Value $551,873

    Last Listing Agent Antoinette Gundersen HomeSmart Homes & Estates

    4 Wayne Ct, Middletown, NY 10941
    • 634 Pocatello Rd, Middletown, NY 10940

      Est $492,833

      Not Listed For Sale

      634 Pocatello Rd, Middletown, NY 10940

      • 4 Beds
      • Built 1880
      634 Pocatello Rd, Middletown, NY 10940

      Last Sold Summary

      • 185 Days On Market

      Last Listing Agent Bryan Dale eXp Realty

  • 40 Silo Ln, Middletown, NY 10940
    40 Silo Ln, Middletown, NY 10940
    40 Silo Ln, Middletown, NY 10940
    /47

    $329,990

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

    40 Silo Ln, Middletown, NY 10940

    Hardwood Floors As Seen,Don't miss out on this recently renovated townhouse in Middletown. Freshened up with new paint interiors. Updated kitchen with new cabinets and Brand new stainless steel appliances. Dining room and living room combo. Up the stairs into your primary bedroom with primary bathroom. There are three bedrooms and two full bathroom. The Meadows offers community pool, clubhouse,

    Zhiheng Tang KW Hudson Valley United

    40 Silo Ln, Middletown, NY 10940
  • 2 Durham Ct Unit 82, Middletown, NY 10940

    $285,000

    Sold Aug 27, 2026

    2 Durham Ct Unit 82, Middletown, NY 10940

    • 2 Beds
    • 2.5 Baths
    • 1,241 Sq Ft
    • Built 1992

    Last Sold Summary

    • 3% Below List Price
    • $230/SF
    • 54 Days On Market

    Current Estimated Value $283,718

    Last Listing Agent Melissa Terman River Realty Services, Inc.

    2 Durham Ct Unit 82, Middletown, NY 10940
    • 661 Pocatello Rd, Middletown, NY 10940

      Est $510,212

      Not Listed For Sale

      661 Pocatello Rd, Middletown, NY 10940

      • 4 Beds
      • 2.5 Baths
      • 2,304 Sq Ft
      • Built 1986
      661 Pocatello Rd, Middletown, NY 10940

      Last Sold Summary

      • 49 Days On Market

      Last Listing Agent Christian Baez KW Hudson Valley United

  • 4 Lincoln St, Middletown, NY 10940
    4 Lincoln St, Middletown, NY 10940
    4 Lincoln St, Middletown, NY 10940
    /50

    $299,000

    $11K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,398 Sq Ft

    4 Lincoln St, Middletown, NY 10940

    This 3-bedroom, 2-bath Colonial offers 1,398 square feet of comfortable living space on a 0.11-acre lot. Built in 1890, the home blends timeless style with thoughtful upgrades while keeping its original charm. Enjoy bright mornings with natural light, cozy evenings at home, and a neighborhood close to shopping, restaurants, parks, schools, and local services. All utilities are available, making

    Matthew Gibbs KW Hudson Valley United

    4 Lincoln St, Middletown, NY 10940
  • 1538 Route 211 W, Middletown, NY 10940

    $270,000

    Sold Jan 05, 2026

    1538 Route 211 W, Middletown, NY 10940

    • 2 Beds
    • 2 Baths
    • 1,536 Sq Ft
    • Built 1920

    Last Sold Summary

    • 10% Below List Price
    • $176/SF
    • 68 Days On Market

    Current Estimated Value $309,995

    Last Listing Agent John Olivero Keller Williams Realty

    1538 Route 211 W, Middletown, NY 10940
    • 168 Camp Stadie Rd, Middletown, NY 10940

      Est $306,675

      Not Listed For Sale

      168 Camp Stadie Rd, Middletown, NY 10940

      • 2 Beds
      • 1 Bath
      • 1,000 Sq Ft
      • Built 1961
      168 Camp Stadie Rd, Middletown, NY 10940

      Last Sold Summary

      • 201 Days On Market

      Last Listing Agent Ann Marie D'Onofrio Briante Realty Group, LLC

  • 16 Houston Ext Ave, Middletown, NY 10940
    16 Houston Ext Ave, Middletown, NY 10940
    16 Houston Ext Ave, Middletown, NY 10940
    /46

    $550,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,069 Sq Ft

    16 Houston Ext Ave, Middletown, NY 10940

    Welcome to this beautiful, young Colonial, built in 2016 and ideally situated on a quiet street of newer homes in Middletown. Offering 4 spacious bedrooms and 2.5 bathrooms, this move-in-ready property seamlessly combines modern convenience with timeless style. The main level features gleaming hardwood floors, complemented by durable tile in the kitchen, half bath, and garage entry. Designed for

    Karleen Jedziniak Howard Hanna Rand Realty

    16 Houston Ext Ave, Middletown, NY 10940
  • 48 Beacon St, Middletown, NY 10940

    $380,000

    Sold Feb 12, 2026

    48 Beacon St, Middletown, NY 10940

    • 6 Beds
    • 2 Baths
    • 2,738 Sq Ft
    • Built 1900

    Last Sold Summary

    • $139/SF
    • 9 Days On Market

    Current Estimated Value $384,761

    Last Listing Agent Kewin Garabito eXp Realty

    48 Beacon St, Middletown, NY 10940
    • 17 Milo Dr, Middletown, NY 10941

      Est $436,134

      Not Listed For Sale

      17 Milo Dr, Middletown, NY 10941

      • 3 Beds
      • 1.5 Baths
      • 1,592 Sq Ft
      • Built 1992
      17 Milo Dr, Middletown, NY 10941

      Last Sold Summary

      • 34 Days On Market

      Last Listing Agent Lisa McAteer Scranton Wilkes Barre Regional

  • 23 Harrison St Unit 25, Middletown, NY 10940
    23 Harrison St Unit 25, Middletown, NY 10940
    23 Harrison St Unit 25, Middletown, NY 10940
    /19

    $333,000

    • 3 Beds
    • 1 Bath
    • 1,152 Sq Ft

    23 Harrison St Unit 25, Middletown, NY 10940

    Come see this well maintained 2 story colonial style home. Centrally located in the City of Middletown which allows you to be minutes away to all the great eateries and to all major shopping and public transportation. The home has taken a few updates over the years. Home has a spacious living room that leads into a formal dining room. Kitchen has plenty of cabinet space as well. The central a.c

    Pedro Garcia Curasi Realty, Inc.

    23 Harrison St Unit 25, Middletown, NY 10940
  • 18 Jordan Ln, Middletown, NY 10940

    $348,000

    Sold Aug 26, 2026

    18 Jordan Ln, Middletown, NY 10940

    • 3 Beds
    • 2.5 Baths
    • 1,345 Sq Ft
    • Built 2003

    Last Sold Summary

    • 3% Below List Price
    • $259/SF
    • 87 Days On Market

    Current Estimated Value $375,986

    Last Listing Agent Jie Liu KW Hudson Valley United

    18 Jordan Ln, Middletown, NY 10940
    • 100 Hillside Dr Unit G2, Middletown, NY 10941

      Not Listed For Sale

      100 Hillside Dr Unit G2, Middletown, NY 10941

      • 2 Beds
      • 2 Baths
      • 1,140 Sq Ft
      • Built 1987
      100 Hillside Dr Unit G2, Middletown, NY 10941

      Last Sold Summary

      • 25 Days On Market

      Last Listing Agent Deniece Carter Curasi Realty, Inc.

  • 13 Avenue B, Middletown, NY 10940
    13 Avenue B, Middletown, NY 10940
    13 Avenue B, Middletown, NY 10940
    /29

    $550,000

    Pending
    • 4 Beds
    • 3 Baths
    • 2,018 Sq Ft

    13 Avenue B, Middletown, NY 10940

    THIS BI LEVEL FEATURES 2018 SQUARE FEET, WITH AN OPEN CONCEPT, VAULTED CEILINGS, MASTER SUITE, THREE ADDITIONAL BEDROOMS WITH TWO MORE FULL BATHS, HARD WOOD FLOORING ON THE SECOND LEVEL, KITCHEN WITH ISLAND, GRANITE COUNTER TOP, STAINLESS STEEL APPLIANCES, TWO CAR ATTACHED GARAGE WITH AN EXTENDED DRIVEWAY TO ACCOMODATE MANY MORE CARS

    Christopher Hosten Charles Rutenberg Realty, Inc.

    13 Avenue B, Middletown, NY 10940
  • 13-15 Phillips St, Middletown, NY 10940

    $510,000

    Sold Mar 27, 2026

    13-15 Phillips St, Middletown, NY 10940

    • 4 Beds
    • 2 Baths
    • 1,901 Sq Ft
    • Built 1880

    Last Sold Summary

    • 2% Above List Price
    • $268/SF
    • 38 Days On Market

    Current Estimated Value $409,605

    Last Listing Agent Jason Nadeau Compass Greater NY, LLC

    13-15 Phillips St, Middletown, NY 10940
    • 100 Hillside Dr Unit B9, Middletown, NY 10941

      Not Listed For Sale

      100 Hillside Dr Unit B9, Middletown, NY 10941

      • 1 Bed
      • 1 Bath
      • 917 Sq Ft
      • Built 1987
      100 Hillside Dr Unit B9, Middletown, NY 10941

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Christina Rowan Howard Hanna Rand Realty

  • 182 Pocatello Rd, Middletown, NY 10940
    182 Pocatello Rd, Middletown, NY 10940
    182 Pocatello Rd, Middletown, NY 10940
    /3

    $179,900

    • Land
    • 3.15 Acres
    • $57,111 per Acre

    182 Pocatello Rd, Middletown, NY 10940

    Build your dream home on this fully engineered and Town of Wallkill-approved 3+ acre parcel, located within the desirable Middletown School District. This ready-to-build lot offers the perfect combination of privacy and convenience, with a peaceful setting while remaining just minutes from major highways, shopping, dining, and everyday amenities. A rare opportunity to own a fully approved

    Jonathon Lee KW Hudson Valley United

    182 Pocatello Rd, Middletown, NY 10940
  • 80 Excelsior Ave, Middletown, NY 10940

    $481,000

    Sold Jul 17, 2026

    80 Excelsior Ave, Middletown, NY 10940

    • 3 Beds
    • 2.5 Baths
    • 1,508 Sq Ft
    • Built 2001

    Last Sold Summary

    • 2% Above List Price
    • $319/SF
    • 30 Days On Market

    Current Estimated Value $461,091

    Last Listing Agent Melanie Potter Curasi Realty, Inc.

    80 Excelsior Ave, Middletown, NY 10940
    • 12 Acorn Ave, Middletown, NY 10941

      Est $472,244

      Not Listed For Sale

      12 Acorn Ave, Middletown, NY 10941

      • 4 Beds
      • 3 Baths
      • 1,838 Sq Ft
      • Built 1988
      12 Acorn Ave, Middletown, NY 10941

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Patricia Sassi RE/MAX Benchmark Realty Group

  • 15 Old Anvil Ln, Middletown, NY 10940
    15 Old Anvil Ln, Middletown, NY 10940
    15 Old Anvil Ln, Middletown, NY 10940
    /49

    $370,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 1,692 Sq Ft

    15 Old Anvil Ln, Middletown, NY 10940

    Welcome to 15 Old Anvil Ln, Middletown, a lovingly cared for end unit townhouse in the sought after "The Meadows" community. This unit has been lived in and cared for by the same owners for approximately 40 years. The owner is a builder so he has not skipped on his own improvements and care. The unit offers 3 bedrooms and 2.5 bathrooms, a kitchen and formal dining room with a slider to a

    Valeria Rios KW Hudson Valley United

    15 Old Anvil Ln, Middletown, NY 10940
  • 264 Lybolt Rd, Middletown, NY 10941

    $753,000

    Sold Mar 11, 2026

    264 Lybolt Rd, Middletown, NY 10941

    • 4 Beds
    • 3.5 Baths
    • 2,823 Sq Ft
    • Built 2025

    Last Sold Summary

    • 3% Below List Price
    • $267/SF
    • 198 Days On Market

    Current Estimated Value $722,776

    Last Listing Agent Chris Ogden Realty Promotions Inc

    264 Lybolt Rd, Middletown, NY 10941
    • 28 Shagbark St, Middletown, NY 10941

      Est $506,477

      Not Listed For Sale

      28 Shagbark St, Middletown, NY 10941

      • 4 Beds
      • 3 Baths
      • 2,100 Sq Ft
      • Built 1988
      28 Shagbark St, Middletown, NY 10941

      Last Sold Summary

      • 27 Days On Market

      Last Listing Agent Patricia Sassi RE/MAX Benchmark Realty Group

  • Lot 11 Meadowbrook Dr, Middletown, NY 12455
    Lot 11 Meadowbrook Dr, Middletown, NY 12455
    Lot 11 Meadowbrook Dr, Middletown, NY 12455
    /13

    $85,000

    • Land
    • 5.1 Acres
    • $16,667 per Acre

    Lot 11 Meadowbrook Dr, Middletown, NY 12455

    Just a short drive from down town Margaretville, tucked away in the pastoral rolling hills, sits this very special 5 acre parcel with lovely open views. What this parcel has to offer is sure to check many boxes on your wish list. A peaceful and serene setting with beautiful scenic views, rolling open meadows backed by magical woods to explore, surrounded by the sounds of nature. With several

    Rosalie Glauser Frank Lumia Real Estate Plus

    Lot 11 Meadowbrook Dr, Middletown, NY 12455
  • 242 Derby Rd, 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 $426,747

    Last Listing Agent Isaiah Lopez KW Hudson Valley United

    242 Derby Rd, Middletown, NY 10940
    • 8 Buckingham Mews, Middletown, NY 10940

      Est $350,633

      Not Listed For Sale

      8 Buckingham Mews, Middletown, NY 10940

      • 3 Beds
      • 1.5 Baths
      • 1,262 Sq Ft
      • Built 1987
      8 Buckingham Mews, Middletown, NY 10940

      Last Sold Summary

      • 56 Days On Market

      Last Listing Agent Zhiheng Tang KW Hudson Valley United

  • 55 Orange Terrace, Middletown, NY 10940
    55 Orange Terrace, Middletown, NY 10940
    55 Orange Terrace, Middletown, NY 10940
    /39

    $325,000

    Coming Soon
    • 3 Beds
    • 1 Bath
    • 1,092 Sq Ft

    55 Orange Terrace, Middletown, NY 10940

    This 3-bedroom, 1 bath raised ranch in Middletown offers 1,092 square feet of living space on a 0.22-acre lot, with a practical layout, hardwood floors, an attached two-car garage, just needs a little cosmetic refreshing to make it shine. The main level features a spacious living and dining area with hardwood flooring and a large picture window, creating an open, comfortable setting for everyday

    Virginia Corbett eXp Realty

    55 Orange Terrace, Middletown, NY 10940
  • 228 Concord Ln Unit 228, 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 $147,490

    Last Listing Agent Yasmine Delgado BHG Real Estate Green Team

    228 Concord Ln Unit 228, Middletown, NY 10940

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