21,198

Middletown, NY Homes

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  • 853 Winterton Rd, Middletown, NY 10940

    $450,000

    Sold Oct 07, 2025

    853 Winterton Rd, Middletown, NY 10940

    • 3 Beds
    • 2 Baths
    • 2,108 Sq Ft
    • Built 1930

    Last Sold Summary

    • 33% Above List Price
    • $213/SF
    • 41 Days On Market

    Last Listing Agent Amanda Brehm KW Hudson Valley United

    853 Winterton Rd, Middletown, NY 10940
    • 57 Sarah Ln, Middletown, NY 10941

      Est $339,543

      Not Listed For Sale

      57 Sarah Ln, Middletown, NY 10941

      • 3 Beds
      • 1.5 Baths
      • 1,440 Sq Ft
      • Built 1979
      57 Sarah Ln, Middletown, NY 10941

      Last Sold Summary

      • 31 Days On Market

      Last Listing Agent Richard Heffernan John J Lease REALTORS Inc

  • 21 Manhattan Ave Unit 19, Middletown, NY 10940
    21 Manhattan Ave Unit 19, Middletown, NY 10940
    21 Manhattan Ave Unit 19, Middletown, NY 10940
    /46

    $450,000

    Pending
    • 3 Beds
    • 1.5 Baths
    • 1,640 Sq Ft

    21 Manhattan Ave Unit 19, Middletown, NY 10940

    **Opportunities on Manhattan Avenue are few and far between. If you've been waiting for a home in this desirable neighborhood, your wait is over! ** Situated on a beautiful .25-acre lot, this inviting split-level offers the perfect combination of comfort, space, and style with **3 bedrooms, 1.5 baths, a one-car garage, and central air**.From the moment you walk through the door, you'll

    Rosalie Cook Weichert Realtors

    21 Manhattan Ave Unit 19, Middletown, NY 10940
  • 3 Kohler Rd, Middletown, NY 10940

    $425,000

    Sold Sep 26, 2025

    3 Kohler Rd, Middletown, NY 10940

    • 3 Beds
    • 1.5 Baths
    • 1,920 Sq Ft
    • Built 1986

    Last Sold Summary

    • 6% Above List Price
    • $221/SF
    • 30 Days On Market

    Current Estimated Value $448,270

    Last Listing Agent Joseph Eugene eXp Realty

    3 Kohler Rd, Middletown, NY 10940
    • 19 Red Barn Ln, Middletown, NY 10940

      Est $370,985

      Not Listed For Sale

      19 Red Barn Ln, Middletown, NY 10940

      • 4 Beds
      • 3.5 Baths
      • 1,692 Sq Ft
      • Built 1974
      19 Red Barn Ln, Middletown, NY 10940

      Last Sold Summary

      • 30 Days On Market

      Last Listing Agent Dawn Payne Payne Team LLC

  • 50 Sycamore Dr, Middletown, NY 10940
    50 Sycamore Dr, Middletown, NY 10940
    50 Sycamore Dr, Middletown, NY 10940
    /35

    $329,900

    • 2 Beds
    • 1.5 Baths
    • 1,340 Sq Ft

    50 Sycamore Dr, Middletown, NY 10940

    Welcome to Clemson Park!Discover this beautifully updated and well-maintained townhouse in the desirable Clemson Park community. Featuring 2 bedrooms and 1.5 bathrooms, this home offers a spacious open floor plan perfect for both everyday living and entertaining.The bright living and dining area includes plush, well-maintained carpeted floors and sliding glass doors that open to a

    Maliki Cottrell Cottrell & Associates RE Corp.

    50 Sycamore Dr, Middletown, NY 10940
  • 121 Sprague Ave, Middletown, NY 10940

    $285,000

    Sold Apr 21, 2026

    121 Sprague Ave, Middletown, NY 10940

    • 2 Beds
    • 1.5 Baths
    • 1,200 Sq Ft
    • Built 1900

    Last Sold Summary

    • 4% Above List Price
    • $238/SF
    • 24 Days On Market

    Current Estimated Value $283,608

    Last Listing Agent Jean DiMatteo DiMatteo Realty LLC

    121 Sprague Ave, Middletown, NY 10940
    • 40 Red Barn Ln, Middletown, NY 10940

      Est $310,283

      Not Listed For Sale

      40 Red Barn Ln, Middletown, NY 10940

      • 3 Beds
      • 2.5 Baths
      • 1,452 Sq Ft
      • Built 1973
      40 Red Barn Ln, Middletown, NY 10940

      Last Sold Summary

      • 39 Days On Market

      Last Listing Agent Annie Hansen Howard Hanna Rand Realty

  • 4 Lorelei Dr, Middletown, NY 10940
    4 Lorelei Dr, Middletown, NY 10940
    4 Lorelei Dr, Middletown, NY 10940
    /36

    $349,000

    $50K PRICE DROP Pending
    • 2 Beds
    • 1.5 Baths
    • 1,800 Sq Ft

    4 Lorelei Dr, Middletown, NY 10940

    This 3 bedroom home is being offered by the original owners. Three spacious bedrooms. Family room with custom fireplace. Oversized garage with laundry. Elementary and middle schools just down the road. Middletown High School offers many college courses. Beautiful sunroom with pellet stove. Two 275 gal oil tanks. Beautiful spacious back yard with shed. Extra black topped parking for RV, boat

    Sue Laden ARC Realty 1 in Sales

    4 Lorelei Dr, Middletown, NY 10940
  • 20 Atwood Dr, Middletown, NY 10940

    $498,000

    Sold Jan 15, 2026

    20 Atwood Dr, Middletown, NY 10940

    • 3 Beds
    • 3.5 Baths
    • 1,723 Sq Ft
    • Built 2017

    Last Sold Summary

    • 2% Above List Price
    • $289/SF
    • 30 Days On Market

    Current Estimated Value $506,325

    Last Listing Agent Kevin Grier KW Hudson Valley United

    20 Atwood Dr, Middletown, NY 10940
    • 11 Black Stallion Ct, Middletown, NY 10940

      Est $317,989

      Not Listed For Sale

      11 Black Stallion Ct, Middletown, NY 10940

      • 3 Beds
      • 1.5 Baths
      • 1,188 Sq Ft
      • Built 1979
      11 Black Stallion Ct, Middletown, NY 10940

      Last Sold Summary

      • 132 Days On Market

      Last Listing Agent Bente Brown Hudson Premium Realty

  • 168 Pine Grove Rd, Middletown, NY 10940
    168 Pine Grove Rd, Middletown, NY 10940
    168 Pine Grove Rd, Middletown, NY 10940
    /38

    $659,999

    $69K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,284 Sq Ft

    168 Pine Grove Rd, Middletown, NY 10940

    Update - priced to sell! Imagine waking up surrounded by three private acres while still being just minutes from shopping and major commuter routes. This newly built colonial offers the peace of country living without sacrificing convenience. The open-concept kitchen, oversized island, fireplace, spacious primary suite and unfinished basement provide room to grow while giving buyers the

    Leeshai Lemish Panorama Realty

    168 Pine Grove Rd, Middletown, NY 10940
  • 231 Concord Ln, Middletown, NY 10940

    $215,000

    Sold Mar 11, 2026

    231 Concord Ln, Middletown, NY 10940

    • 2 Beds
    • 1.5 Baths
    • 924 Sq Ft
    • Built 1990

    Last Sold Summary

    • 4% Below List Price
    • $233/SF
    • 16 Days On Market

    Current Estimated Value $214,992

    Last Listing Agent Kerri Stretch Howard Hanna Rand Realty

    231 Concord Ln, Middletown, NY 10940
    • 24 Black Stallion Ct, Middletown, NY 10940

      Est $330,077

      Not Listed For Sale

      24 Black Stallion Ct, Middletown, NY 10940

      • 3 Beds
      • 2.5 Baths
      • 1,408 Sq Ft
      • Built 1979
      24 Black Stallion Ct, Middletown, NY 10940

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Mark Tierney Howard Hanna Rand Realty

  • 2467 Route 302, Middletown, NY 10941
    2467 Route 302, Middletown, NY 10941
    2467 Route 302, Middletown, NY 10941
    /8

    $659,000

    $41K PRICE DROP
    • 6 Beds
    • 4 Baths
    • 2,040 Sq Ft

    2467 Route 302, Middletown, NY 10941

    Excellent location and property seeking a savvy investor. Pine Bush schools, fully leased near Highway and less than 5 miles to train. Close to shopping too. Hurry to see before it is gone.

    Myrna Lattore eRealty Advisors, Inc

    2467 Route 302, Middletown, NY 10941
  • 153 Ridge Dr, Middletown, NY 10940

    $585,000

    Sold Jul 31, 2026

    153 Ridge Dr, Middletown, NY 10940

    • 3 Beds
    • 3 Baths
    • 2,133 Sq Ft
    • Built 2022

    Last Sold Summary

    • 2% Above List Price
    • $274/SF
    • 22 Days On Market

    Current Estimated Value $622,770

    Last Listing Agent Lady Castro eXp Realty

    153 Ridge Dr, Middletown, NY 10940
    • 28 Black Stallion Ct, Middletown, NY 10940

      Est $325,988

      Not Listed For Sale

      28 Black Stallion Ct, Middletown, NY 10940

      • 3 Beds
      • 1.5 Baths
      • 1,188 Sq Ft
      • Built 1979
      28 Black Stallion Ct, Middletown, NY 10940

      Last Sold Summary

      • 38 Days On Market

      Last Listing Agent Beth Palma Keller Williams Realty

  • 4 Woodrose Ct, Middletown, NY 10940
    4 Woodrose Ct, Middletown, NY 10940
    4 Woodrose Ct, Middletown, NY 10940
    /36

    $475,000

    • 3 Beds
    • 2.5 Baths
    • 2,257 Sq Ft

    4 Woodrose Ct, Middletown, NY 10940

    Welcome to 4 Woodrose Court, located in the peaceful Highrose Ridge community! Built in 2019, this modern townhome offers a bright, open layout with high ceilings, oversized windows and plenty of natural light.Step inside to hardwood floors throughout the main level and an open-concept kitchen featuring granite countertops, stainless steel appliances, a center island and plenty of space for

    Alyssa Scancarello Howard Hanna Rand Realty

    4 Woodrose Ct, Middletown, NY 10940
  • 74 Pocatello Rd, Middletown, NY 10940

    $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 $413,278

    Last Listing Agent Catherine Eichner Eichner Realty Group Inc.

    74 Pocatello Rd, Middletown, NY 10940
    • 34 Black Stallion Ct, Middletown, NY 10940

      Est $298,688

      Not Listed For Sale

      34 Black Stallion Ct, Middletown, NY 10940

      • 3 Beds
      • 1.5 Baths
      • 1,188 Sq Ft
      • Built 1980
      34 Black Stallion Ct, Middletown, NY 10940

      Last Sold Summary

      • 38 Days On Market

      Last Listing Agent Pedro Garcia Curasi Realty, Inc.

  • 43 Mayer Dr, Middletown, NY 10940
    43 Mayer Dr, Middletown, NY 10940
    43 Mayer Dr, Middletown, NY 10940
    /43

    $385,000

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

    43 Mayer Dr, Middletown, NY 10940

    Welcome to this three-level townhouse in Middletown with no HOA, offering greater flexibility and no monthly association fees. The main level features a living room with hardwood flooring, a kitchen and dining area, and a half bathroom. The kitchen offers stainless steel appliances and ample cabinet and counter space. Sliding glass doors provide easy access to the rear deck and backyard for

    Wenpeng Guan KW Hudson Valley United

    43 Mayer Dr, Middletown, NY 10940
  • 14 Bonnell St, Middletown, NY 10940

    $446,000

    Sold Jun 25, 2026

    14 Bonnell St, Middletown, NY 10940

    • 5 Beds
    • 2 Baths
    • 2,586 Sq Ft
    • Built 1900

    Last Sold Summary

    • 1% Above List Price
    • $172/SF
    • 54 Days On Market

    Current Estimated Value $424,950

    Last Listing Agent Jonathon Lee KW Hudson Valley United

    14 Bonnell St, Middletown, NY 10940
    • 38 Black Stallion Ct, Middletown, NY 10940

      Est $303,643

      Not Listed For Sale

      38 Black Stallion Ct, Middletown, NY 10940

      • 3 Beds
      • 1.5 Baths
      • 1,188 Sq Ft
      • Built 1980
      38 Black Stallion Ct, Middletown, NY 10940

      Last Sold Summary

      • 140 Days On Market

      Last Listing Agent Kristie Jacques Century 21 Full Service Realty

  • 65 Maureen Dr, Middletown, NY 10940
    65 Maureen Dr, Middletown, NY 10940
    65 Maureen Dr, Middletown, NY 10940
    /29

    $499,900

    • 3 Beds
    • 2.5 Baths
    • 2,200 Sq Ft

    65 Maureen Dr, Middletown, NY 10940

    THIS IS YOUR CHANCE!!! MINISINK VALLEY SCHOOL DISTRICT!!! ROBINN MEADOWS!!!! Welcome to the perfect place to purchase your home in the highly sought after Minisink Valley School District! Perfectly situated in the desirable Robinn Meadows community, this lovingly maintained raised ranch offers the ideal balance of comfort, style, and everyday convenience, all set within a peaceful, friendly

    Frank Muccari Cronin & Company Real Estate

    65 Maureen Dr, Middletown, NY 10940
  • 580 van Burenville Rd, Middletown, NY 10940

    $320,000

    Sold Jul 07, 2026

    580 van Burenville Rd, Middletown, NY 10940

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • Built 1966

    Last Sold Summary

    • $303/SF
    • 130 Days On Market

    Current Estimated Value $316,811

    Last Listing Agent Valerie Jewis Keller Williams Realty

    580 van Burenville Rd, Middletown, NY 10940
    • 7 Old Anvil Ln, Middletown, NY 10940

      Est $299,083

      Not Listed For Sale

      7 Old Anvil Ln, Middletown, NY 10940

      • 3 Beds
      • 2.5 Baths
      • 1,692 Sq Ft
      • Built 1974
      7 Old Anvil Ln, Middletown, NY 10940

      Last Sold Summary

      • 27 Days On Market

      Last Listing Agent Joanne Finochio Howard Hanna Rand Realty

  • 0 Red Kill Rd, Middletown, NY 12430
    0 Red Kill Rd, Middletown, NY 12430
    0 Red Kill Rd, Middletown, NY 12430
    /11

    $1,475,000

    • Land
    • 92.31 Acres
    • $15,979 per Acre

    0 Red Kill Rd, Middletown, NY 12430

    92.30 acres for sale in the Catskill Mountains New York.This secluded and versatile property is now for sale for the first time since 1996. Set above the charming Village of Fleischmanns and just 0.6 miles from Main Street, this 92-acre parcel offers the privacy of a wilderness retreat with the convenience of a village doorstep.-Interior roadways.-A large man-made spring-fed pond and

    peter neumann Listing by Keller Williams Upstate NY Properties

    0 Red Kill Rd, Middletown, NY 12430
  • 273 Pine Grove 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 $792,684

    Last Listing Agent Douglas McVicker Suburban Investment Realty

    273 Pine Grove Rd, Middletown, NY 10940
    • 17 Old Anvil Ln, Middletown, NY 10940

      Est $380,077

      Not Listed For Sale

      17 Old Anvil Ln, Middletown, NY 10940

      • 3 Beds
      • 2.5 Baths
      • 1,692 Sq Ft
      • Built 1974
      17 Old Anvil Ln, Middletown, NY 10940

      Last Sold Summary

      • 38 Days On Market

      Last Listing Agent Dulce M Ferrera KW Hudson Valley United

  • 3 Sharon Dr, Middletown, NY 10941
    3 Sharon Dr, Middletown, NY 10941
    3 Sharon Dr, Middletown, NY 10941
    /22

    $479,000

    Pending
    • 3 Beds
    • 1.5 Baths
    • 1,592 Sq Ft

    3 Sharon Dr, Middletown, NY 10941

    Welcome Home to 3 Sharon Drive! Sitting on just under half an acre in a tranquil, quiet neighborhood, this beautiful split-level home offers 3 bedrooms, 1.5 baths, and over 1,500 square feet — you'll feel right at home the moment you walk in the door!As you enter, you're greeted by tall ceilings that complement the spacious, open layout throughout. Just off the living room you have a

    Ryan Barrett Keller Williams Realty

    3 Sharon Dr, Middletown, NY 10941
  • 38 Sheffield Dr, 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 $314,295

    Last Listing Agent Malik Subhani Weichert Realtors

    38 Sheffield Dr, Middletown, NY 10940
    • 21 Old Anvil Ln, Middletown, NY 10940

      Est $354,369

      Not Listed For Sale

      21 Old Anvil Ln, Middletown, NY 10940

      • 3 Beds
      • 2.5 Baths
      • 1,692 Sq Ft
      • Built 1974
      21 Old Anvil Ln, Middletown, NY 10940

      Last Sold Summary

      • 20 Days On Market

      Last Listing Agent Matthew Gibbs KW Hudson Valley United

  • 111 Jasmine Dr, Middletown, NY 10940
    111 Jasmine Dr, Middletown, NY 10940
    111 Jasmine Dr, Middletown, NY 10940
    /39

    $505,000

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

    111 Jasmine Dr, Middletown, NY 10940

    Welcome to Wildflower at Wallkill, one of the Hudson Valley's premier 55+ communities, where beautifully maintained grounds, outstanding amenities, and a true sense of community create an exceptional place to call home. Residents enjoy a beautiful clubhouse, fitness center, business center, indoor and outdoor swimming pools, tennis courts, recreation facilities, gated entry, and professionally

    Christina D'Altilio Coldwell Banker Choice Prop.

    111 Jasmine Dr, Middletown, NY 10940
  • 13 Smith St, 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 $241,984

    Last Listing Agent Dulce M Ferrera KW Hudson Valley United

    13 Smith St, Middletown, NY 10940
    • 36 Old Anvil Ln, Middletown, NY 10940

      Est $330,878

      Not Listed For Sale

      36 Old Anvil Ln, Middletown, NY 10940

      • 3 Beds
      • 1.5 Baths
      • 1,452 Sq Ft
      • Built 1974
      36 Old Anvil Ln, Middletown, NY 10940

      Last Sold Summary

      • 27 Days On Market

      Last Listing Agent Wenpeng Guan KW Hudson Valley United

  • 15 Anthony St, Middletown, NY 10940
    15 Anthony St, Middletown, NY 10940
    15 Anthony St, Middletown, NY 10940
    /11

    $305,000

    $10K PRICE DROP Pending
    • 2 Beds
    • 1 Bath
    • 689 Sq Ft

    15 Anthony St, Middletown, NY 10940

    *Welcome Home!* This exceptional *fully furnished single-family residence simply bring your personal belongings and move right in.The home offers *2 comfortable bedrooms* and *1 full bathroom*,Offered *fully furnished, this home includes , living room furnishings, bedroom sets with beds and linens, making it a true move-in-ready opportunity.Step outside to enjoy a spacious

    Eliezer Salcer Preferred Properties Real Esta

    15 Anthony St, Middletown, NY 10940
  • 190 Crans Rd, Middletown, NY 10941

    $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 $958,230

    Last Listing Agent Deb Cor Exclusively Equine Prop LLC

    190 Crans Rd, Middletown, NY 10941
    • 8 Silo Ln, Middletown, NY 10940

      Est $354,742

      Not Listed For Sale

      8 Silo Ln, Middletown, NY 10940

      • 3 Beds
      • 2.5 Baths
      • 1,692 Sq Ft
      • Built 1976
      8 Silo Ln, Middletown, NY 10940

      Last Sold Summary

      • 40 Days On Market

      Last Listing Agent Elsie Nunez Keller Williams Realty

  • 81 Silver Lake Scotchtown Rd Unit 4, Middletown, NY 10940
    81 Silver Lake Scotchtown Rd Unit 4, Middletown, NY 10940
    81 Silver Lake Scotchtown Rd Unit 4, Middletown, NY 10940
    /49

    $499,999

    • 3 Beds
    • 2.5 Baths
    • 1,660 Sq Ft

    81 Silver Lake Scotchtown Rd Unit 4, Middletown, NY 10940

    Experience modern living in this newly built 3-bedroom, 2.5-bath home designed with comfort and style in mind. Featuring an open floor plan with soaring 10-foot ceilings, this home offers spacious living and entertaining areas filled with natural light. The gourmet kitchen boasts granite countertops, stainless steel appliances, and ample cabinetry, all flowing seamlessly into the main living

    Antoinette Gundersen HomeSmart Homes & Estates

    81 Silver Lake Scotchtown Rd Unit 4, Middletown, NY 10940
  • 29 Columbia Ave, Middletown, NY 10940

    $425,000

    Sold Aug 13, 2026

    29 Columbia Ave, Middletown, NY 10940

    • 8 Beds
    • 3 Baths
    • 2,121 Sq Ft
    • Built 1923

    Last Sold Summary

    • 6% Above List Price
    • $200/SF
    • 33 Days On Market

    Current Estimated Value $400,556

    Last Listing Agent Sharon Pehush HomeSmart Homes & Estates

    29 Columbia Ave, Middletown, NY 10940

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