View 42 Rebecca Drive Middletown, NY MLS# 998305
    1 of 40
    OPEN HOUSE: Saturday 5/16 12:00 PM - 2:00 PM
    $530,000
    4

    Beds

    3.0

    Baths

    2,126

    Sq.Ft.

    42 Rebecca Drive

    Middletown, NY

    Courtesy of HOMESMART HOMES & ESTATES
    View 217 School House Road Middletown, NY MLS# 999323
    $680,000
    4

    Beds

    2.1

    Baths

    2,410

    Sq.Ft.

    217 School House Road

    Middletown, NY

    Courtesy of RE/MAX TOWN & COUNTRY
    View 5 Dubois Street Middletown, NY MLS# 993300
      1 of 28
      OPEN HOUSE: Sunday 5/17 12:00 PM - 2:00 PM
      $399,900
      3

      Beds

      2.0

      Baths

      1,278

      Sq.Ft.

      5 Dubois Street

      Middletown, NY

      Courtesy of EXP REALTY
      The time to sell is now! THE TIME TO SELL IS NOW!
      View 9 School House Road Middletown, NY MLS# 996900
        1 of 36
        OPEN HOUSE: Saturday 5/16 12:00 PM - 2:00 PM
        $699,900
        4

        Beds

        2.1

        Baths

        2,192

        Sq.Ft.

        9 School House Road

        Middletown, NY

        Courtesy of EXP REALTY
        View 428 Prosperous Valley Road Middletown, NY MLS# 993676
          1 of 48
          OPEN HOUSE: Friday 5/15 4:30 PM - 6:00 PM
          $725,000
          3

          Beds

          2.1

          Baths

          2,678

          Sq.Ft.

          428 Prosperous Valley Road

          Middletown, NY

          Courtesy of KELLER WILLIAMS REALTY
          View 153 Ridgewood Avenue Middletown, NY MLS# 992982
          • Recently Listed
          1 of 35
          OPEN HOUSE: Saturday 5/16 1:00 PM - 3:00 PM
          $475,000
          3

          Beds

          2.0

          Baths

          1,577

          Sq.Ft.

          153 Ridgewood Avenue

          Middletown, NY

          Courtesy of KELLER WILLIAMS HUDSON VALLEY
          View 205 Linden Avenue Middletown, NY MLS# 996009
          • Recently Listed
          1 of 25
          OPEN HOUSE: Sunday 5/17 1:00 PM - 3:00 PM
          $310,000
          3

          Beds

          2.0

          Baths

          1,061

          Sq.Ft.

          205 Linden Avenue

          Middletown, NY

          Courtesy of EPIQUE REALTY
          View 217-219 Highland Avenue Middletown, NY MLS# 977631
          • Recently Listed
          1 of 41
          $479,000
          3

          Beds

          2.1

          Baths

          2,228

          Sq.Ft.

          217-219 Highland Avenue

          Middletown, NY

          Courtesy of KELLER WILLIAMS HUDSON VALLEY
          View 126 Rolling Meadows Road Middletown, NY MLS# 998294
          • Recently Listed with Virtual Tour
          1 of 48
          $447,000
          4

          Beds

          2.1

          Baths

          2,155

          Sq.Ft.

          126 Rolling Meadows Road

          Middletown, NY

          Courtesy of HOWARD HANNA RAND REALTY
          View 8 Roberts Street Middletown, NY MLS# 998312
          • Recently Listed
          1 of 9
          $460,000
          5

          Beds

          2.0

          Baths

          2,132

          Sq.Ft.

          8 Roberts Street

          Middletown, NY

          Courtesy of KELLER WILLIAMS HUDSON VALLEY
          View 44 Commonwealth Avenue Middletown, NY MLS# 998424
          • Recently Listed
          1 of 23
          $298,900
          3

          Beds

          1.0

          Baths

          1,180

          Sq.Ft.

          44 Commonwealth Avenue

          Middletown, NY

          Courtesy of FRANK TANGREDI REALTY COMPANY
          View 225 Brown Road Middletown, NY MLS# 972182
          • Recently Listed
          1 of 48
          OPEN HOUSE: Saturday 5/16 12:00 PM - 2:00 PM
          $675,000
          4

          Beds

          3.0

          Baths

          4,080

          Sq.Ft.

          225 Brown Road

          Middletown, NY

          Courtesy of KELLER WILLIAMS HUDSON VALLEY
          View 90 M And M Road Middletown, NY MLS# 997326
          • Recently Listed with Virtual Tour
          1 of 50
          $729,999
          4

          Beds

          2.1

          Baths

          1,996

          Sq.Ft.

          90 M And M Road

          Middletown, NY

          Courtesy of KELLER WILLIAMS HUDSON VALLEY
          View 80 Sarah Lane Middletown, NY MLS# 998293
          • Recently Listed with Virtual Tour
          1 of 35
          $294,900
          3

          Beds

          1.1

          Baths

          1,440

          Sq.Ft.

          80 Sarah Lane

          Middletown, NY

          Courtesy of Weichert Realtors - Monroe
          View 47 Wickham Avenue 45 Middletown, NY MLS# 997491
          • Recently Listed
          1 of 18
          $450,000
          3

          Beds

          1.0

          Baths

          1,478

          Sq.Ft.

          47 Wickham Avenue 45

          Middletown, NY

          Courtesy of HOWARD HANNA RAND REALTY
          View 13 Benton Avenue Middletown, NY MLS# 998257
          • Recently Listed
          1 of 21
          $450,000
          1,450

          Sq.Ft.

          13 Benton Avenue

          Middletown, NY

          Courtesy of HOWARD HANNA RAND REALTY
          View 319 Reservoir Road Middletown, NY MLS# 968373
          • Recently Listed
          1 of 34
          $465,000
          3

          Beds

          2.0

          Baths

          2,028

          Sq.Ft.

          319 Reservoir Road

          Middletown, NY

          Courtesy of CURASI REALTY, INC.
          View 16 Woodland Road Middletown, NY MLS# 997655
          • Recently Listed
          1 of 13
          $249,000
          3

          Beds

          1.0

          Baths

          1,250

          Sq.Ft.

          16 Woodland Road

          Middletown, NY

          Courtesy of HOWARD HANNA RAND REALTY
          View 543 Dosen Road Middletown, NY MLS# 997791
          • Recently Listed
          1 of 25
          OPEN HOUSE: Sunday 5/17 12:00 PM - 2:00 PM
          $325,000
          3

          Beds

          1.0

          Baths

          1,061

          Sq.Ft.

          543 Dosen Road

          Middletown, NY

          Courtesy of HOWARD HANNA RAND REALTY
          View 54 Whitman Court Middletown, NY MLS# 989180
          • Recently Listed
          1 of 44
          $299,999
          3

          Beds

          1.1

          Baths

          1,428

          Sq.Ft.

          54 Whitman Court

          Middletown, NY

          Courtesy of KELLER WILLIAMS REALTY

          About Middletown

          Surrounded by such communities as Goshen and Wallkill, Middletown offers the expanded educational opportunities of Orange County Community College to the regional amenities.  Tranquil and yet convenient, Middletown is home to retail and commercial activity.  For expansive shopping, regional malls are just minutes from home.  Although the city is home to a number of businesses and light industry, it is primarily a residential community with a pleasing variety of single-family homes.  Both newer construction and fine older homes combine with multi-family options.  Commuters can travel to New York City via Metro-North rail or catch buses into the Port Authority.  An abundance of county and local parks ensure outdoor enjoyment.  Attractions include picnic areas and miles of hiking and biking trails as well as tennis courts and golf courses.

          Listings in Middletown, NY

          262

          Estimated median home price

          $449,900
          Middletown NY Homes for Sale & Properties

          Weichert Realtors is one of the nation's leading providers of Middletown, New York real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Middletown, NY.

          Homes for Sale by Price in Middletown, NY

          PriceCount
          $0 - 100K11
          $100K - 200K19
          $200K - 300K29
          $300K - 400K52
          $400K - 500K68
          $500K - 600K28
          $600K - 700K14
          $700K - 800K7
          $800K - 900K7
          $900K - 1M8
          $1M - Max19

          Homes for Sale by Type in Middletown, NY

          Property TypeCount
          Single Family156
          Townhouse0
          Condo22
          Commercial37
          Rental113
          Lots and Land28
          Condo/Town/CoOp0
          CoOp0
          Multi Family13
          Mobile Home6
          Farms0

          (Data as of 5/14/2026)

          Information deemed reliable but not guaranteed.

          The data relating to real estate for sale on this web site comes in part from The Internet Data Exchange Program of ©2026 Global Multiple Listing Service, Inc. The data relating to real estate on this website comes in part from the Internet Data Exchange program of the GMLS. All information is deemed reliable but not guaranteed and should be independently verified. All properties subject to prior sale, change, or withdrawal. Neither listing broker(s), GMLS shall be responsible for any typographical errors, misinformation, or misprints, and shall be held totally harmless from any damages arising from reliance upon these data. IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties they may be interested in purchasing.

          Data is updated as of 5/14/2026.

          All information provided is deemed reliable but is not guaranteed and should be independently verified.

          Copyright 2026 by the Multiple Listing service of Ulster County, Inc. All Rights Reserved.

          The data relating to real estate on this web site comes in part from the IDX of the Multiple Listing service of Ulster County, Inc. Real estate listings held by brokerage firms other that Weichert Realtors are marked with IDX logo and the detailed information about them includes the name of the listing broker.

          The data relating to real estate for sale on this website comes in part from the IDX Program of OneKey® MLS.

          The source of the displayed data is either the property owner or public record provided by non-governmental third parties. It is believed to be reliable but not guaranteed. This information is provided exclusively for consumers’ personal, non-commercial use.

          Information Copyright 2021, OneKey® MLS. All Rights Reserved.