View 521 E Main Street Middletown, NY MLS# 964168
  • Recently Listed
1 of 19
$499,900
4

Beds

2.0

Baths

7,600

Sq.Ft.

521 E Main Street

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
View Van Burenville Road Middletown, NY MLS# 965294
  • Recently Listed
1 of 5
$125,000
Studio

Beds

0.0

Baths

278,784

Sq.Ft.

Van Burenville Road

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 57 Boorman Road Middletown, NY MLS# 955621
  • Recently Listed
1 of 44
$475,000
3

Beds

3.0

Baths

2,074

Sq.Ft.

57 Boorman Road

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
The time to sell is now! THE TIME TO SELL IS NOW!
View Lot 2 South Centerville Road Middletown, NY MLS# 965712
$140,000
Studio

Beds

0.0

Baths

126,324

Sq.Ft.

Lot 2 South Centerville Road

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
View 18 Jordan Lane Middletown, NY MLS# 961715
$359,000
3

Beds

2.1

Baths

1,345

Sq.Ft.

18 Jordan Lane

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 21 Philcox Road Middletown, NY MLS# 964656
$379,000
3

Beds

2.0

Baths

1,314

Sq.Ft.

21 Philcox Road

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 11 Philcox Road Middletown, NY MLS# 964665
$269,000
2

Beds

1.0

Baths

802

Sq.Ft.

11 Philcox Road

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 8 Atwood Drive Middletown, NY MLS# 963043
  • Virtual Tour
1 of 30
$479,000
3

Beds

3.1

Baths

1,723

Sq.Ft.

8 Atwood Drive

Middletown, NY

Courtesy of REDFIN REAL ESTATE
View 24 E Main Street Middletown, NY MLS# 963920
$180,000
5,653

Sq.Ft.

24 E Main Street

Middletown, NY

Courtesy of HOMESMART HOMES & ESTATES
View 599 Guymard Turnpike Middletown, NY MLS# 927166
$499,000
3

Beds

2.0

Baths

1,852

Sq.Ft.

599 Guymard Turnpike

Middletown, NY

Courtesy of EXP REALTY
View 109 Watkins Avenue Middletown, NY MLS# 962056
$299,000
2

Beds

1.0

Baths

800

Sq.Ft.

109 Watkins Avenue

Middletown, NY

Courtesy of R2M REALTY INC.
View 41 Monhagen Avenue 39 Middletown, NY MLS# 960537
$410,000
5

Beds

4.0

Baths

15,707

Sq.Ft.

41 Monhagen Avenue 39

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 54 Ogden Street Middletown, NY MLS# 962828
$399,900
5

Beds

3.0

Baths

3,103

Sq.Ft.

54 Ogden Street

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 138-1/2 Linden Avenue Middletown, NY MLS# 961697
$27,000
Studio

Beds

0.0

Baths

1,392

Sq.Ft.

138-1/2 Linden Avenue

Middletown, NY

Courtesy of DONNA RUFFINO REALTY CORP
View 55 Hulse Avenue Middletown, NY MLS# 961603
$335,000
3

Beds

1.0

Baths

914

Sq.Ft.

55 Hulse Avenue

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 14 Scotchtown Drive Middletown, NY MLS# 957282
$369,900
3

Beds

2.1

Baths

1,522

Sq.Ft.

14 Scotchtown Drive

Middletown, NY

Courtesy of HUDSON VALLEY GRIFFITH
View 3 Ben Lomond Drive Middletown, NY MLS# 951695
  • Virtual Tour
1 of 39
$525,000
5

Beds

2.0

Baths

2,515

Sq.Ft.

3 Ben Lomond Drive

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 227 Deer Ct Drive Middletown, NY MLS# 959466
$409,000
3

Beds

2.1

Baths

1,919

Sq.Ft.

227 Deer Ct Drive

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 4 Kless Court Middletown, NY MLS# 960173
$429,000
3

Beds

2.1

Baths

2,097

Sq.Ft.

4 Kless Court

Middletown, NY

Courtesy of YOURHOMESOLD GUARANTEED REALTY
View 79 Stern Scenic Drive Middletown, NY MLS# 959521
$150,000
3

Beds

2.0

Baths

1,500

Sq.Ft.

79 Stern Scenic Drive

Middletown, NY

Courtesy of EXIT REALTY CONNECTIONS

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

224

Estimated median home price

$425,000
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 - 100K9
$100K - 200K17
$200K - 300K33
$300K - 400K44
$400K - 500K45
$500K - 600K22
$600K - 700K15
$700K - 800K5
$800K - 900K5
$900K - 1M4
$1M - Max25

Homes for Sale by Type in Middletown, NY

Property TypeCount
Single Family127
Townhouse0
Condo16
Commercial35
Rental109
Lots and Land32
Condo/Town/CoOp0
CoOp0
Multi Family9
Mobile Home5
Farms0

(Data as of 3/18/2026)

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 web site comes in part from The Internet Data Exchange Program of ©2026 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 3/20/2026.

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.