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 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
The time to sell is now! THE TIME TO SELL IS NOW!
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 1 Chestnut Street Middletown, NY MLS# 902008
$379,000
3

Beds

1.0

Baths

1,100

Sq.Ft.

1 Chestnut Street

Middletown, NY

Courtesy of HOMESMART HOMES & ESTATES
View 1538 Route 211 W Middletown, NY MLS# 900456
$300,000
2

Beds

2.0

Baths

1,536

Sq.Ft.

1538 Route 211 W

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY
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 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
$359,999
3

Beds

1.1

Baths

1,160

Sq.Ft.

5 Mills Avenue

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY
View 105 Sheffield Drive Middletown, NY MLS# 893551
$295,000
3

Beds

1.1

Baths

1,400

Sq.Ft.

105 Sheffield Drive

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
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 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
$335,000
3

Beds

2.0

Baths

1,484

Sq.Ft.

2 Rivervale Road

Middletown, NY

Courtesy of YOURHOMESOLD GUARANTEED 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

245

Estimated median home price

$414,999
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 - 200K16
$200K - 300K37
$300K - 400K59
$400K - 500K44
$500K - 600K23
$600K - 700K11
$700K - 800K13
$800K - 900K4
$900K - 1M4
$1M - Max28

Homes for Sale by Type in Middletown, NY

Property TypeCount
Single Family147
Townhouse0
Condo23
Commercial35
Rental119
Lots and Land29
Condo/Town/CoOp0
CoOp0
Multi Family8
Mobile Home3
Farms0

(Data as of 12/26/2025)

Information deemed reliable but not guaranteed.

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

Copyright 2025 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.