View 136 Sycamore Drive Middletown, NY MLS# 1058492
$299,900
2

Beds

2.0

Baths

1,110

Sq.Ft.

136 Sycamore Drive

Middletown, NY

Courtesy of CURASI REALTY, INC.
View 960 Mt Hope Road Middletown, NY MLS# 1058673
$425,000
4

Beds

1.0

Baths

1,306

Sq.Ft.

960 Mt Hope Road

Middletown, NY

Courtesy of HANSON REAL ESTATE PARTNERS
View 15 N Aspen Road Middletown, NY MLS# 1058387
    1 of 15
    OPEN HOUSE: Sunday 11/1 11:00 AM - 1:00 PM
    $299,000
    2

    Beds

    1.1

    Baths

    1,144

    Sq.Ft.

    15 N Aspen Road

    Middletown, NY

    Courtesy of SERHANT LLC
    The time to sell is now! THE TIME TO SELL IS NOW!
    View 34 Houston Avenue Middletown, NY MLS# 1058232
    $315,000
    3

    Beds

    2.0

    Baths

    5,450

    Sq.Ft.

    34 Houston Avenue

    Middletown, NY

    Courtesy of I REALTY LLC
    View 138 Prospect Avenue Middletown, NY MLS# 1053196
      1 of 46
      OPEN HOUSE: Sunday 11/1 11:00 AM - 1:00 PM
      $369,000
      2

      Beds

      1.0

      Baths

      1,422

      Sq.Ft.

      138 Prospect Avenue

      Middletown, NY

      Courtesy of HOWARD HANNA RAND REALTY
      View 539 (Lot 1) Mt Orange Road Middletown, NY MLS# 1057754
      $185,000
      0.0

      Baths

      87,120

      Sq.Ft.

      539 (Lot 1) Mt Orange Road

      Middletown, NY

      Courtesy of HOWARD HANNA RAND REALTY
      View 243 Howells Turnpike Middletown, NY MLS# 1046716
      $399,000
      2

      Beds

      1.0

      Baths

      960

      Sq.Ft.

      243 Howells Turnpike

      Middletown, NY

      Courtesy of HOMESMART HOMES & ESTATES
      View 287 Derby Road Middletown, NY MLS# 1058020
      $160,000
      0.0

      Baths

      287,496

      Sq.Ft.

      287 Derby Road

      Middletown, NY

      Courtesy of RE/MAX BENCHMARK REALTY GROUP
      View 159 Wawayanda Avenue Middletown, NY MLS# 1055220
      $425,000
      3

      Beds

      2.0

      Baths

      1,352

      Sq.Ft.

      159 Wawayanda Avenue

      Middletown, NY

      Courtesy of CRONIN & COMPANY REAL ESTATE
      View 1040 Route 211 W Middletown, NY MLS# 1056459
      • Virtual Tour
      1 of 45
      $416,000
      3

      Beds

      2.0

      Baths

      960

      Sq.Ft.

      1040 Route 211 W

      Middletown, NY

      Courtesy of KELLER WILLIAMS REALTY
      View 122 Sycamore Drive Middletown, NY MLS# 1054352
      $175,000
      1

      Beds

      1.0

      Baths

      830

      Sq.Ft.

      122 Sycamore Drive

      Middletown, NY

      Courtesy of RE/MAX BENCHMARK REALTY GROUP
      View 63 Orchard Hill Road Middletown, NY MLS# 1056390
      $389,000
      3

      Beds

      2.0

      Baths

      1,062

      Sq.Ft.

      63 Orchard Hill Road

      Middletown, NY

      Courtesy of REALTY PROMOTIONS INC
      View 8 Keystone Park Middletown, NY MLS# 1055264
      $399,000
      3

      Beds

      1.0

      Baths

      912

      Sq.Ft.

      8 Keystone Park

      Middletown, NY

      Courtesy of CRONIN & COMPANY REAL ESTATE
      View 19 Putters Way 9 Middletown, NY MLS# 1055933
      $394,900
      2

      Beds

      2.1

      Baths

      1,337

      Sq.Ft.

      19 Putters Way 9

      Middletown, NY

      Courtesy of RE/MAX BENCHMARK REALTY GROUP
      View 13 Columbia Avenue Middletown, NY MLS# 1020678
      $385,000
      3

      Beds

      1.0

      Baths

      1,320

      Sq.Ft.

      13 Columbia Avenue

      Middletown, NY

      Courtesy of EXP REALTY
      View 55 Orange Terrace Middletown, NY MLS# 1052724
      • Virtual Tour
      1 of 39
      $325,000
      3

      Beds

      1.0

      Baths

      1,092

      Sq.Ft.

      55 Orange Terrace

      Middletown, NY

      Courtesy of EXP REALTY
      View 88 Grand Avenue Middletown, NY MLS# 1054997
      • Virtual Tour
      1 of 29
      $425,000
      5

      Beds

      2.0

      Baths

      1,736

      Sq.Ft.

      88 Grand Avenue

      Middletown, NY

      Courtesy of DONNA RUFFINO REALTY CORP
      View 143 Deer Ct Drive Middletown, NY MLS# 974627
      $299,000
      2

      Beds

      2.0

      Baths

      1,291

      Sq.Ft.

      143 Deer Ct Drive

      Middletown, NY

      Courtesy of HOWARD HANNA RAND REALTY
      View 132 Sycamore Drive Middletown, NY MLS# 1053223
      $284,900
      2

      Beds

      2.0

      Baths

      1,342

      Sq.Ft.

      132 Sycamore Drive

      Middletown, NY

      Courtesy of CURASI REALTY, INC.
      View 191 Wickham Avenue Middletown, NY MLS# 1050322
      $245,000
      4

      Beds

      1.1

      Baths

      1,613

      Sq.Ft.

      191 Wickham Avenue

      Middletown, NY

      Courtesy of EXP 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

      331

      Estimated median home price

      $416,000
      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 - 100K7
      $100K - 200K25
      $200K - 300K44
      $300K - 400K86
      $400K - 500K59
      $500K - 600K41
      $600K - 700K17
      $700K - 800K12
      $800K - 900K11
      $900K - 1M4
      $1M - Max25

      Homes for Sale by Type in Middletown, NY

      Property TypeCount
      Single Family220
      Townhouse0
      Condo33
      Commercial39
      Rental127
      Lots and Land26
      Condo/Town/CoOp0
      CoOp0
      Multi Family11
      Mobile Home2
      Farms0

      (Data as of 11/1/2026)

      Information deemed reliable but not guaranteed.

      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.