View 28 Spring Street Middletown, NY MLS# 930885
$329,000
4

Beds

2.0

Baths

1,696

Sq.Ft.

28 Spring Street

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
View 14 Spruce Peak Road Middletown, NY MLS# 923725
$325,000
3

Beds

1.1

Baths

1,496

Sq.Ft.

14 Spruce Peak Road

Middletown, NY

Courtesy of CRONIN & COMPANY REAL ESTATE
View 24 Kent Court Middletown, NY MLS# 936117
$325,000
2

Beds

2.1

Baths

1,241

Sq.Ft.

24 Kent Court

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
The time to sell is now! THE TIME TO SELL IS NOW!
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 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 6 Eaton Court Middletown, NY MLS# 938529
$319,999
3

Beds

1.1

Baths

1,248

Sq.Ft.

6 Eaton Court

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY
View 14 Pennsylvania Avenue Middletown, NY MLS# 924814
$315,000
3

Beds

1.0

Baths

1,058

Sq.Ft.

14 Pennsylvania Avenue

Middletown, NY

Courtesy of RE/MAX BENCHMARK REALTY GROUP
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
View 927 Tower Ridge Circle Middletown, NY MLS# 948020
  • Recently Listed
1 of 36
$314,900
2

Beds

2.0

Baths

1,216

Sq.Ft.

927 Tower Ridge Circle

Middletown, NY

Courtesy of CRONIN & COMPANY REAL ESTATE
View 146 Deer Ct Drive Middletown, NY MLS# 936284
$310,000
2

Beds

2.1

Baths

1,473

Sq.Ft.

146 Deer Ct Drive

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY
View 36 Bert Crawford Road Middletown, NY MLS# 932531
$309,900
2

Beds

1.0

Baths

836

Sq.Ft.

36 Bert Crawford Road

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 0 County Hwy 67 Middletown, NY MLS# H5123677
$300,000
48,787

Sq.Ft.

0 County Hwy 67

Middletown, NY

Courtesy of KELLER WILLIAMS 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 12-14 Union Street Middletown, NY MLS# 921611
$300,000
15,299

Sq.Ft.

12-14 Union Street

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
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 328 Bloomingburg Road Middletown, NY MLS# 915106
$299,999
Studio

Beds

0.0

Baths

1,184,832

Sq.Ft.

328 Bloomingburg Road

Middletown, NY

Courtesy of CURASI REALTY, INC.
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 15 Commonwealth Avenue Middletown, NY MLS# 891691
$299,000
3

Beds

1.0

Baths

1,092

Sq.Ft.

15 Commonwealth Avenue

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY
View 401 East Main Street Middletown, NY MLS# 932809
$299,000
976

Sq.Ft.

401 East Main Street

Middletown, NY

Courtesy of R J KATZ 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

239

Estimated median home price

$429,900
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 - 300K38
$300K - 400K50
$400K - 500K43
$500K - 600K22
$600K - 700K12
$700K - 800K13
$800K - 900K5
$900K - 1M4
$1M - Max28

Homes for Sale by Type in Middletown, NY

Property TypeCount
Single Family142
Townhouse0
Condo24
Commercial34
Rental115
Lots and Land29
Condo/Town/CoOp0
CoOp0
Multi Family7
Mobile Home3
Farms0

(Data as of 1/6/2026)

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.