View 100 Hillside Drive E16 Middletown, NY MLS# 984017
$298,000
2

Beds

2.0

Baths

1,140

Sq.Ft.

100 Hillside Drive E16

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 104-108 Highland Avenue Middletown, NY MLS# 980025
$568,000
7

Beds

4.1

Baths

3,592

Sq.Ft.

104-108 Highland Avenue

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
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
View 10 Renfrewshire Drive Middletown, NY MLS# 974615
  • Recently Listed
1 of 31
$425,000
3

Beds

1.1

Baths

1,788

Sq.Ft.

10 Renfrewshire Drive

Middletown, NY

Courtesy of CRONIN & COMPANY REAL ESTATE
View 64 Patio Road Middletown, NY MLS# 981682
  • Recently Listed
1 of 28
$332,000
3

Beds

1.1

Baths

1,440

Sq.Ft.

64 Patio Road

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 239 Millsburg Road Middletown, NY MLS# 981486
  • Recently Listed
1 of 41
$449,900
3

Beds

1.1

Baths

1,344

Sq.Ft.

239 Millsburg Road

Middletown, NY

Courtesy of CRONIN & COMPANY REAL ESTATE
View 39 Bloomingburg Road Middletown, NY MLS# 981966
  • Recently Listed
1 of 40
$700,000
3,679

Sq.Ft.

39 Bloomingburg Road

Middletown, NY

Courtesy of RAND COMMERCIAL
View 48 Connors Road Middletown, NY MLS# 973784
  • Recently Listed
1 of 49
$590,000
5

Beds

1.1

Baths

1,790

Sq.Ft.

48 Connors Road

Middletown, NY

Courtesy of EXP REALTY
View 129 Concord Lane Middletown, NY MLS# 982111
  • Recently Listed
1 of 33
$259,000
2

Beds

1.1

Baths

1,230

Sq.Ft.

129 Concord Lane

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 42 Mayer Drive Middletown, NY MLS# 973651
  • Recently Listed
1 of 25
$329,000
2

Beds

2.0

Baths

1,730

Sq.Ft.

42 Mayer Drive

Middletown, NY

Courtesy of RE/MAX BENCHMARK REALTY GROUP
View 18-20 Bedford Avenue Middletown, NY MLS# 977561
  • Recently Listed
1 of 39
$249,999
2

Beds

1.0

Baths

864

Sq.Ft.

18-20 Bedford Avenue

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY
View 209 Deer Ct Drive Middletown, NY MLS# 978576
  • Recently Listed
1 of 22
$329,000
2

Beds

2.1

Baths

1,473

Sq.Ft.

209 Deer Ct Drive

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
View 464 Union School Road Middletown, NY MLS# 974281
  • Recently Listed
1 of 48
$900,000
3

Beds

3.0

Baths

4,090

Sq.Ft.

464 Union School Road

Middletown, NY

Courtesy of RE/MAX BENCHMARK REALTY GROUP

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

226

Estimated median home price

$432,500
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 - 300K30
$300K - 400K46
$400K - 500K50
$500K - 600K19
$600K - 700K18
$700K - 800K6
$800K - 900K7
$900K - 1M4
$1M - Max20

Homes for Sale by Type in Middletown, NY

Property TypeCount
Single Family124
Townhouse0
Condo22
Commercial34
Rental126
Lots and Land29
Condo/Town/CoOp0
CoOp0
Multi Family12
Mobile Home5
Farms0

(Data as of 4/13/2026)

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 4/13/2026.

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.

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