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
The time to sell is now! THE TIME TO SELL IS NOW!
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
$359,999
3

Beds

1.1

Baths

1,160

Sq.Ft.

5 Mills Avenue

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY
View 652 Route 211 W 650 Middletown, NY MLS# 894144
$449,800
3

Beds

2.0

Baths

2,400

Sq.Ft.

652 Route 211 W 650

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
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 24 3rd Street Middletown, NY MLS# 894923
$589,000
4

Beds

3.0

Baths

2,732

Sq.Ft.

24 3rd Street

Middletown, NY

Courtesy of REALTY PROMOTIONS INC
View 34 Feiertag Road Middletown, NY MLS# 896163
$598,000
3

Beds

3.0

Baths

3,021

Sq.Ft.

34 Feiertag Road

Middletown, NY

Courtesy of 1ST INDEPENDENT REALTY GRP
View 295 Lybolt Road Middletown, NY MLS# 894234
$470,000
3

Beds

2.0

Baths

1,222

Sq.Ft.

295 Lybolt Road

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY
View 744 Mt Hope Road Middletown, NY MLS# 890021
$649,900
4

Beds

3.0

Baths

2,444

Sq.Ft.

744 Mt Hope Road

Middletown, NY

Courtesy of HOMESMART HOMES & ESTATES
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 125 Whipple Road Middletown, NY MLS# 886181
  • Virtual Tour
1 of 21
$599,000
4

Beds

3.0

Baths

2,552

Sq.Ft.

125 Whipple Road

Middletown, NY

Courtesy of JULIA B FEE SOTHEBYS INT. RLTY
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

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

242

Estimated median home price

$417,450
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 - 400K56
$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 Family145
Townhouse0
Condo23
Commercial35
Rental119
Lots and Land29
Condo/Town/CoOp0
CoOp0
Multi Family7
Mobile Home3
Farms0

(Data as of 12/28/2025)

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 ©2025 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 12/29/2025.

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.