View 100 Hillside Drive E16 Middletown, NY MLS# 984017
  • Recently Listed
1 of 13
$298,000
2

Beds

2.0

Baths

1,140

Sq.Ft.

100 Hillside Drive E16

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 204 Brola Road Middletown, NY MLS# 981479
  • Recently Listed with Virtual Tour
1 of 50
OPEN HOUSE: Sunday 4/19 2:00 PM - 4:00 PM
$868,509
4

Beds

4.0

Baths

3,200

Sq.Ft.

204 Brola Road

Middletown, NY

Courtesy of KELLER WILLIAMS 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
The time to sell is now! THE TIME TO SELL IS NOW!
View 13 N Aspen Road Middletown, NY MLS# 986211
$369,000
3

Beds

1.1

Baths

1,484

Sq.Ft.

13 N Aspen Road

Middletown, NY

Courtesy of SERHANT LLC
View 206 W Main Street Middletown, NY MLS# 979822
  • Recently Listed
1 of 25
$325,000
4

Beds

1.0

Baths

1,248

Sq.Ft.

206 W Main Street

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 19 Livingston Street Middletown, NY MLS# 985594
  • Recently Listed
1 of 30
OPEN HOUSE: Sunday 4/19 1:00 PM - 3:00 PM
$499,000
4

Beds

2.1

Baths

1,944

Sq.Ft.

19 Livingston Street

Middletown, NY

Courtesy of HUDSON VALLEY GRIFFITH
View 13 Elm Street Middletown, NY MLS# 986504
  • Recently Listed
1 of 17
OPEN HOUSE: Sunday 4/19 1:00 PM - 3:00 PM
$365,000
3

Beds

1.1

Baths

1,405

Sq.Ft.

13 Elm Street

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 35 Black Stallion Court Middletown, NY MLS# 986787
  • Recently Listed
1 of 47
$370,000
3

Beds

1.1

Baths

1,764

Sq.Ft.

35 Black Stallion Court

Middletown, NY

Courtesy of JOHN J LEASE REALTORS INC
View 104-108 Highland Avenue Middletown, NY MLS# 980025
  • Recently Listed with Virtual Tour
1 of 50
OPEN HOUSE: Sunday 4/19 11:00 AM - 2:00 PM
$568,000
7

Beds

4.1

Baths

3,592

Sq.Ft.

104-108 Highland Avenue

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
View 19 Sunflower Street Middletown, NY MLS# 985640
  • Recently Listed
1 of 35
$499,900
2

Beds

2.0

Baths

1,868

Sq.Ft.

19 Sunflower Street

Middletown, NY

Courtesy of RE/MAX BENCHMARK REALTY GROUP
View 65 Maureen Drive Middletown, NY MLS# 970664
  • Recently Listed
1 of 36
$499,900
3

Beds

2.1

Baths

2,200

Sq.Ft.

65 Maureen Drive

Middletown, NY

Courtesy of CRONIN & COMPANY REAL ESTATE
View 15 Rivervale Road Middletown, NY MLS# 983798
  • Recently Listed
1 of 26
$319,000
3

Beds

1.1

Baths

1,484

Sq.Ft.

15 Rivervale Road

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 38 Putters Way Middletown, NY MLS# 984140
  • Recently Listed
1 of 50
$615,000
3

Beds

2.1

Baths

3,013

Sq.Ft.

38 Putters Way

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 301 3rd Avenue Middletown, NY MLS# 979868
  • Recently Listed
1 of 33
OPEN HOUSE: Sunday 4/19 12:00 PM - 2:00 PM
$100,000
2

Beds

2.0

Baths

800

Sq.Ft.

301 3rd Avenue

Middletown, NY

Courtesy of RE/MAX TOWN & COUNTRY
View 3 Arden Court Middletown, NY MLS# 957904
  • Recently Listed
1 of 43
$460,000
3

Beds

2.1

Baths

2,427

Sq.Ft.

3 Arden Court

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY
View 17 Ross Lane Middletown, NY MLS# 983429
  • Recently Listed
1 of 45
$499,000
4

Beds

2.1

Baths

2,000

Sq.Ft.

17 Ross Lane

Middletown, NY

Courtesy of BHHS HUDSON VALLEY PROPERTIES
View 225 Van Duzer Road Middletown, NY MLS# 981261
  • Recently Listed
1 of 50
$839,000
6

Beds

4.0

Baths

3,900

Sq.Ft.

225 Van Duzer Road

Middletown, NY

Courtesy of HOMESMART HOMES & ESTATES
View 60 Magnolia Park Road Middletown, NY MLS# 981574
  • Recently Listed with Virtual Tour
1 of 33
$499,000
3

Beds

2.1

Baths

2,211

Sq.Ft.

60 Magnolia Park Road

Middletown, NY

Courtesy of REDFIN REAL ESTATE
View 2467 Route 302 Middletown, NY MLS# 973999
  • Recently Listed
1 of 8
$699,999
6

Beds

4.0

Baths

2,040

Sq.Ft.

2467 Route 302

Middletown, NY

Courtesy of EREALTY ADVISORS, INC
View 481 Dosen Road Middletown, NY MLS# 968515
  • Recently Listed
1 of 42
$679,000
3

Beds

3.0

Baths

1,680

Sq.Ft.

481 Dosen Road

Middletown, NY

Courtesy of CRONIN & COMPANY REAL ESTATE

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

231

Estimated median home price

$449,000
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 - 200K16
$200K - 300K31
$300K - 400K46
$400K - 500K49
$500K - 600K22
$600K - 700K19
$700K - 800K6
$800K - 900K7
$900K - 1M4
$1M - Max21

Homes for Sale by Type in Middletown, NY

Property TypeCount
Single Family128
Townhouse0
Condo23
Commercial34
Rental120
Lots and Land30
Condo/Town/CoOp0
CoOp0
Multi Family11
Mobile Home5
Farms0

(Data as of 4/18/2026)

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 4/19/2026.

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.