View 2 S Aspen Road Middletown, NY MLS# 1005556
$299,900
3

Beds

1.1

Baths

1,884

Sq.Ft.

2 S Aspen Road

Middletown, NY

Courtesy of GREENE REALTY GROUP
View 35 Lexington Way Middletown, NY MLS# 1043648
$299,900
2

Beds

2.1

Baths

1,348

Sq.Ft.

35 Lexington Way

Middletown, NY

Courtesy of KW HUDSON VALLEY UNITED
View 136 Sycamore Drive Middletown, NY MLS# 1058492
$299,900
2

Beds

2.0

Baths

1,110

Sq.Ft.

136 Sycamore Drive

Middletown, NY

Courtesy of CURASI REALTY, INC.
The time to sell is now! THE TIME TO SELL IS NOW!
View 4 Harding Street Middletown, NY MLS# 1061283
  • Recently Listed
1 of 17
$299,900
4

Beds

2.0

Baths

1,416

Sq.Ft.

4 Harding Street

Middletown, NY

Courtesy of KW HUDSON VALLEY UNITED
View 4 Lincoln Street Middletown, NY MLS# 1014764
$299,000
3

Beds

1.1

Baths

1,398

Sq.Ft.

4 Lincoln Street

Middletown, NY

Courtesy of KW HUDSON VALLEY UNITED
View 41 Irwin Avenue Middletown, NY MLS# 20265132
$299,000
3

Beds

1.0

Baths

1,248

Sq.Ft.

41 Irwin Avenue

Middletown, NY

UlsterCountyNY
Courtesy of KELLER WILLIAMS REALTY HV NORT
View 41 Irwin Avenue Middletown, NY MLS# 1045708
$299,000
3

Beds

1.0

Baths

1,248

Sq.Ft.

41 Irwin Avenue

Middletown, NY

Courtesy of KW HUDSON VALLEY NORTH
View 143 Deer Ct Drive Middletown, NY MLS# 974627
$299,000
2

Beds

2.0

Baths

1,291

Sq.Ft.

143 Deer Ct Drive

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
View 15 N Aspen Road Middletown, NY MLS# 1058387
$299,000
2

Beds

1.1

Baths

1,144

Sq.Ft.

15 N Aspen Road

Middletown, NY

Courtesy of SERHANT LLC
View 8 Parsons Lane Middletown, NY MLS# 1031169
  • Recently Listed
1 of 19
$299,000
3

Beds

2.0

Baths

1,365

Sq.Ft.

8 Parsons Lane

Middletown, NY

Courtesy of KW HUDSON VALLEY UNITED
View 43 Brick Pond Road Middletown, NY MLS# 1044127
$295,000
3

Beds

2.1

Baths

1,460

Sq.Ft.

43 Brick Pond Road

Middletown, NY

Courtesy of KW HUDSON VALLEY UNITED
View 40 Academy Avenue Middletown, NY MLS# 1047286
$295,000
2

Beds

1.0

Baths

1,248

Sq.Ft.

40 Academy Avenue

Middletown, NY

Courtesy of KW HUDSON VALLEY UNITED
View 141 Ruth Court Middletown, NY MLS# 1000877
$289,900
2

Beds

2.0

Baths

1,049

Sq.Ft.

141 Ruth Court

Middletown, NY

Courtesy of CURASI REALTY, INC.
View 63 Sycamore Drive 63 Middletown, NY MLS# 1041811
$289,000
2

Beds

2.0

Baths

1,110

Sq.Ft.

63 Sycamore Drive 63

Middletown, NY

Courtesy of PATRICIA SCHILLER REAL EST CO.
View 100 Hillside Drive B10 Middletown, NY MLS# 1060749
  • Recently Listed
1 of 35
$289,000
2

Beds

1.0

Baths

917

Sq.Ft.

100 Hillside Drive B10

Middletown, NY

Courtesy of KELLER WILLIAMS VALLEY REALTY
View 132 Sycamore Drive Middletown, NY MLS# 1053223
$284,900
2

Beds

2.0

Baths

1,342

Sq.Ft.

132 Sycamore Drive

Middletown, NY

Courtesy of CURASI REALTY, INC.
View 122 Castle High Road Middletown, NY MLS# 1021833
$280,000
3

Beds

1.0

Baths

1,830

Sq.Ft.

122 Castle High Road

Middletown, NY

Courtesy of CURASI REALTY, INC.
View 256 Cottage Street Middletown, NY MLS# 1041109
  • Virtual Tour
1 of 31
OPEN HOUSE: Saturday 11/7 2:00 PM - 4:00 PM
$279,900
3

Beds

1.0

Baths

860

Sq.Ft.

256 Cottage Street

Middletown, NY

Courtesy of KW HUDSON VALLEY UNITED
View 18 Deer Court Drive Middletown, NY MLS# 1044653
$277,000
2

Beds

2.0

Baths

1,291

Sq.Ft.

18 Deer Court Drive

Middletown, NY

Courtesy of HUDSON PREMIUM REALTY
View 13 Jimal Drive Middletown, NY MLS# 1058739
$272,000
3

Beds

2.1

Baths

1,245

Sq.Ft.

13 Jimal Drive

Middletown, NY

Courtesy of HUDSON PREMIUM 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

326

Estimated median home price

$415,000
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 - 100K10
$100K - 200K24
$200K - 300K42
$300K - 400K85
$400K - 500K56
$500K - 600K40
$600K - 700K19
$700K - 800K11
$800K - 900K10
$900K - 1M4
$1M - Max25

Homes for Sale by Type in Middletown, NY

Property TypeCount
Single Family213
Townhouse0
Condo32
Commercial40
Rental123
Lots and Land28
Condo/Town/CoOp0
CoOp0
Multi Family11
Mobile Home2
Farms0

(Data as of 11/4/2026)

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.