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 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 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
The time to sell is now! THE TIME TO SELL IS NOW!
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 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 256 Cottage Street Middletown, NY MLS# 1041109
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OPEN HOUSE: Saturday 11/14 2:30 PM - 4:30 PM
$279,900
3

Beds

1.0

Baths

860

Sq.Ft.

256 Cottage Street

Middletown, NY

Courtesy of KW HUDSON VALLEY UNITED
View 243-247 Monhagen Avenue Middletown, NY MLS# 1043571
$239,000
3

Beds

2.0

Baths

1,161

Sq.Ft.

243-247 Monhagen Avenue

Middletown, NY

Courtesy of REAL BROKER NY LLC
View 13 Ogden Street Middletown, NY MLS# 1040507
$260,000
3

Beds

1.0

Baths

1,342

Sq.Ft.

13 Ogden Street

Middletown, NY

Courtesy of HUDSON PREMIUM REALTY
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 195 Commonwealth Avenue Middletown, NY MLS# 1038167
$305,000
3

Beds

1.0

Baths

1,176

Sq.Ft.

195 Commonwealth Avenue

Middletown, NY

Courtesy of NEXLVL REAL ESTATE 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 45 John Street Middletown, NY MLS# 1011268
$225,000
2

Beds

1.0

Baths

921

Sq.Ft.

45 John Street

Middletown, NY

Courtesy of CURASI REALTY, INC.
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 Address not provided Middletown, NY MLS# 949982
$269,000
2

Beds

1.1

Baths

960

Sq.Ft.

Address not provided

Middletown, NY

Courtesy of Q HOME SALES
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 328 Bloomingburg Road Middletown, NY MLS# 915106
$299,999
0.0

Baths

1,184,832

Sq.Ft.

328 Bloomingburg Road

Middletown, NY

Courtesy of CURASI REALTY, INC.
View 18 Ohaire Road Middletown, NY MLS# H6298115
$250,000
0.0

Baths

1,023,660

Sq.Ft.

18 Ohaire Road

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY
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

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

309

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 - 100K10
$100K - 200K22
$200K - 300K40
$300K - 400K76
$400K - 500K55
$500K - 600K35
$600K - 700K19
$700K - 800K11
$800K - 900K11
$900K - 1M4
$1M - Max26

Homes for Sale by Type in Middletown, NY

Property TypeCount
Single Family193
Townhouse0
Condo32
Commercial41
Rental128
Lots and Land29
Condo/Town/CoOp0
CoOp0
Multi Family13
Mobile Home1
Farms0

(Data as of 11/12/2026)

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.