View 38 Prospect Street Middletown, NY MLS# 914007
$349,000
4

Beds

1.0

Baths

1,790

Sq.Ft.

38 Prospect Street

Middletown, NY

Courtesy of CURASI REALTY, INC.
View 20 Benton Avenue Middletown, NY MLS# 907148
$319,999
3

Beds

2.0

Baths

1,504

Sq.Ft.

20 Benton Avenue

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY
View 34 Poplar Lane Middletown, NY MLS# 910306
$250,000
2

Beds

1.1

Baths

1,240

Sq.Ft.

34 Poplar Lane

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 11 Cobblestone Lane Middletown, NY MLS# 910643
$465,000
3

Beds

2.1

Baths

1,899

Sq.Ft.

11 Cobblestone Lane

Middletown, NY

Courtesy of HOMESMART HOMES & ESTATES
View 302 Concord Lane Middletown, NY MLS# 908658
$220,000
2

Beds

2.0

Baths

995

Sq.Ft.

302 Concord Lane

Middletown, NY

Courtesy of R2M REALTY INC
View 55 Glen Avenue Middletown, NY MLS# 910952
$150,000
2

Beds

1.0

Baths

1,200

Sq.Ft.

55 Glen Avenue

Middletown, NY

Courtesy of YOURHOMESOLD GUARANTEED REALTY
View 9 Genung Street Middletown, NY MLS# 907464
$299,999
3

Beds

2.0

Baths

1,240

Sq.Ft.

9 Genung Street

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 2 Danielle Court Middletown, NY MLS# 908591
$513,999
3

Beds

3.0

Baths

2,696

Sq.Ft.

2 Danielle Court

Middletown, NY

Courtesy of YOURHOMESOLD GUARANTEED REALTY
View 211 Midland Lake Road Middletown, NY MLS# 902330
$180,000
Studio

Beds

0.0

Baths

91,476

Sq.Ft.

211 Midland Lake Road

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
View 3 Bonnie Brae Drive Middletown, NY MLS# 901822
$450,000
3

Beds

1.1

Baths

1,584

Sq.Ft.

3 Bonnie Brae Drive

Middletown, NY

Courtesy of HUDSON VALLEY HOME CONNECTION
View 4 Putters Way Middletown, NY MLS# 905387
$479,000
2

Beds

2.1

Baths

2,000

Sq.Ft.

4 Putters Way

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
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 29 Keasel Road Middletown, NY MLS# 900143
$499,000
3

Beds

2.1

Baths

2,032

Sq.Ft.

29 Keasel Road

Middletown, NY

Courtesy of EXP REALTY
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
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

    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.