View 14 Kensington Way Middletown, NY MLS# 944383
$349,000
2

Beds

1.1

Baths

1,115

Sq.Ft.

14 Kensington Way

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 29 Lafayette Avenue Middletown, NY MLS# 971493
$349,000
3

Beds

1.0

Baths

1,132

Sq.Ft.

29 Lafayette Avenue

Middletown, NY

Courtesy of RE/MAX BENCHMARK REALTY GROUP
View 16 Mountain Avenue Middletown, NY MLS# 968044
$344,900
4

Beds

1.1

Baths

1,598

Sq.Ft.

16 Mountain Avenue

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 164 Brookline Avenue Middletown, NY MLS# 202613576
$340,000
2

Beds

1.0

Baths

1,050

Sq.Ft.

164 Brookline Avenue

Middletown, NY

Courtesy of REMAX SOLUTIONS
View 5 Mills Avenue Middletown, NY MLS# 893182
$339,999
3

Beds

1.1

Baths

1,160

Sq.Ft.

5 Mills Avenue

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY
View 5 Kendal Lane Middletown, NY MLS# 1000252
  • Recently Listed
1 of 11
$339,900
2

Beds

2.1

Baths

1,241

Sq.Ft.

5 Kendal Lane

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 37 California Avenue Middletown, NY MLS# 1000309
  • Recently Listed
1 of 10
$339,900
3

Beds

2.0

Baths

1,152

Sq.Ft.

37 California Avenue

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
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 51 Deer Ct Drive Middletown, NY MLS# 973106
$335,000
2

Beds

2.1

Baths

1,473

Sq.Ft.

51 Deer Ct Drive

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 36 Bert Crawford Road Middletown, NY MLS# 987165
$330,000
2

Beds

1.0

Baths

836

Sq.Ft.

36 Bert Crawford Road

Middletown, NY

Courtesy of PANORAMA REALTY
View 26 Ridge Street Middletown, NY MLS# 927011
$329,000
3

Beds

1.0

Baths

1,400

Sq.Ft.

26 Ridge Street

Middletown, NY

Courtesy of BLOOMING REALTY
View 209 Deer Ct Drive Middletown, NY MLS# 978576
$329,000
2

Beds

2.1

Baths

1,473

Sq.Ft.

209 Deer Ct Drive

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
View 15 N Aspen Road Middletown, NY MLS# 982545
$329,000
2

Beds

1.1

Baths

1,144

Sq.Ft.

15 N Aspen Road

Middletown, NY

Courtesy of SERHANT LLC
View 50 Brola Road Middletown, NY MLS# 974449
$325,000
3

Beds

1.0

Baths

1,196

Sq.Ft.

50 Brola Road

Middletown, NY

Courtesy of HOMESMART HOMES & ESTATES
View 64 Patio Road Middletown, NY MLS# 981682
$325,000
3

Beds

1.1

Baths

1,440

Sq.Ft.

64 Patio Road

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 206 W Main Street Middletown, NY MLS# 979822
$325,000
4

Beds

1.0

Baths

1,248

Sq.Ft.

206 W Main Street

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 543 Dosen Road Middletown, NY MLS# 997791
  • Recently Listed
1 of 25
$325,000
3

Beds

1.0

Baths

1,061

Sq.Ft.

543 Dosen Road

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
View 34 Hampton Court Middletown, NY MLS# 955434
$324,000
3

Beds

1.1

Baths

1,508

Sq.Ft.

34 Hampton Court

Middletown, NY

Courtesy of CURASI REALTY, INC.
View 16 Liberty Street Middletown, NY MLS# 962558
$320,000
5

Beds

2.0

Baths

6,750

Sq.Ft.

16 Liberty Street

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 15 Rivervale Road Middletown, NY MLS# 983798
$319,000
3

Beds

1.1

Baths

1,484

Sq.Ft.

15 Rivervale 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

269

Estimated median home price

$449,900
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 - 100K11
$100K - 200K20
$200K - 300K27
$300K - 400K55
$400K - 500K69
$500K - 600K29
$600K - 700K17
$700K - 800K6
$800K - 900K7
$900K - 1M7
$1M - Max21

Homes for Sale by Type in Middletown, NY

Property TypeCount
Single Family161
Townhouse0
Condo23
Commercial36
Rental112
Lots and Land27
Condo/Town/CoOp0
CoOp0
Multi Family15
Mobile Home7
Farms0

(Data as of 5/19/2026)

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 ©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 5/19/2026.

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.