View 408 County Route 22 Middletown, NY MLS# 905653
$379,999
3

Beds

1.1

Baths

1,132

Sq.Ft.

408 County Route 22

Middletown, NY

Courtesy of RITA LEVINE REAL ESTATE
View 111 Apple Lane Drive Middletown, NY MLS# 900782
$305,000
2

Beds

1.1

Baths

1,150

Sq.Ft.

111 Apple Lane Drive

Middletown, NY

Courtesy of RE/MAX BENCHMARK REALTY GROUP
View 11 Dolson Middletown, NY MLS# 901050
$414,999
3

Beds

2.1

Baths

1,795

Sq.Ft.

11 Dolson

Middletown, NY

Courtesy of COLDWELL BANKER REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 2024 Mount Hope Road Middletown, NY MLS# 899476
$300,000
Studio

Beds

0.0

Baths

1,467,972

Sq.Ft.

2024 Mount Hope Road

Middletown, NY

Courtesy of HUDSON VALLEY GRIFFITH
View 143 Shawangunk Road Middletown, NY MLS# 898875
$115,000
Studio

Beds

0.0

Baths

91,476

Sq.Ft.

143 Shawangunk Road

Middletown, NY

Courtesy of RAND COMMERCIAL
View 77 Prince Street Middletown, NY MLS# 894700
$399,000
3

Beds

2.1

Baths

1,245

Sq.Ft.

77 Prince Street

Middletown, NY

Courtesy of HOMESMART HOMES & ESTATES
View 5 Mills Avenue Middletown, NY MLS# 893182
    1 of 30
    OPEN HOUSE: Sunday 1/18 12:00 PM - 2:00 PM
    $359,999
    3

    Beds

    1.1

    Baths

    1,160

    Sq.Ft.

    5 Mills Avenue

    Middletown, NY

    Courtesy of KELLER WILLIAMS REALTY
    View 580 Van Burenville Road Middletown, NY MLS# 886062
    $299,900
    3

    Beds

    1.0

    Baths

    1,056

    Sq.Ft.

    580 Van Burenville Road

    Middletown, NY

    Courtesy of KELLER WILLIAMS HUDSON VALLEY
    View 58 Wawayanda Avenue Middletown, NY MLS# 888435
    $220,000
    2

    Beds

    1.0

    Baths

    820

    Sq.Ft.

    58 Wawayanda Avenue

    Middletown, NY

    Courtesy of CRONIN & COMPANY REAL ESTATE
    View 551 5th Avenue Middletown, NY MLS# 888408
    $150,000
    3

    Beds

    2.0

    Baths

    1,344

    Sq.Ft.

    551 5th Avenue

    Middletown, NY

    Courtesy of KELLER WILLIAMS HUDSON VALLEY
    View 40 Ivory Lane Middletown, NY MLS# 884982
    $40,000
    Studio

    Beds

    0.0

    Baths

    550

    Sq.Ft.

    40 Ivory Lane

    Middletown, NY

    Courtesy of EXP REALTY
    View 44 Houston Avenue Middletown, NY MLS# 879210
    $369,900
    5

    Beds

    2.0

    Baths

    2,440

    Sq.Ft.

    44 Houston Avenue

    Middletown, NY

    Courtesy of KELLER WILLIAMS HUDSON VALLEY
    View 32 Nicaj Court Middletown, NY MLS# 859545
    $279,000
    Studio

    Beds

    0.0

    Baths

    919,116

    Sq.Ft.

    32 Nicaj Court

    Middletown, NY

    Courtesy of HOWARD HANNA RAND REALTY
    View 87 Dolson Avenue Middletown, NY MLS# 875298
    $225,000
    43,560

    Sq.Ft.

    87 Dolson Avenue

    Middletown, NY

    Courtesy of HOWARD HANNA RAND REALTY
    View 24 John Street Middletown, NY MLS# 874957
    • Virtual Tour
    1 of 46
    $399,000
    4,147

    Sq.Ft.

    24 John Street

    Middletown, NY

    Courtesy of GREEN TEAM COMMERCIAL
    View 2 Rivervale Road Middletown, NY MLS# 869398
    $330,000
    3

    Beds

    2.0

    Baths

    1,484

    Sq.Ft.

    2 Rivervale Road

    Middletown, NY

    Courtesy of YOURHOMESOLD GUARANTEED REALTY
    View 115 Vincent Drive Middletown, NY MLS# 872206
    $320,000
    3

    Beds

    2.0

    Baths

    1,964

    Sq.Ft.

    115 Vincent Drive

    Middletown, NY

    Courtesy of KELLER WILLIAMS HUDSON VALLEY
    View 21 Lake Claire Drive Middletown, NY MLS# 857177
    $209,999
    2

    Beds

    2.0

    Baths

    990

    Sq.Ft.

    21 Lake Claire Drive

    Middletown, NY

    Courtesy of EXP REALTY
    View Rebecca Drive Middletown, NY MLS# 839331
    $275,000
    Studio

    Beds

    0.0

    Baths

    1,751,112

    Sq.Ft.

    Rebecca Drive

    Middletown, NY

    Courtesy of HOWARD HANNA RAND REALTY
    View 10 Myrtle Avenue Middletown, NY MLS# 835018
    $314,900
    3

    Beds

    2.0

    Baths

    1,608

    Sq.Ft.

    10 Myrtle Avenue

    Middletown, NY

    Courtesy of BHHS HUDSON VALLEY PROPERTIES

    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

    244

    Estimated median home price

    $415,000
    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 - 100K6
    $100K - 200K18
    $200K - 300K40
    $300K - 400K54
    $400K - 500K42
    $500K - 600K24
    $600K - 700K13
    $700K - 800K11
    $800K - 900K5
    $900K - 1M4
    $1M - Max27

    Homes for Sale by Type in Middletown, NY

    Property TypeCount
    Single Family148
    Townhouse0
    Condo25
    Commercial34
    Rental110
    Lots and Land28
    Condo/Town/CoOp0
    CoOp0
    Multi Family6
    Mobile Home3
    Farms0

    (Data as of 1/16/2026)

    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.