View Maples Road Middletown, NY MLS# 883753
$8,900,000
Studio

Beds

0.0

Baths

9,365,400

Sq.Ft.

Maples Road

Middletown, NY

Courtesy of FIRST HAMPTON INT'L REALTY LLC
View 14-20 Cottage Street Middletown, NY MLS# 906087
$3,500,000
42,392

Sq.Ft.

14-20 Cottage Street

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY
View 22 Cottage Street Middletown, NY MLS# 906495
$3,000,000
23,400

Sq.Ft.

22 Cottage Street

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 633 Route 211 E Middletown, NY MLS# 927056
$2,995,000
16,938

Sq.Ft.

633 Route 211 E

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 104 North Street Middletown, NY MLS# 947750
  • Recently Listed
1 of 14
$2,550,000
11,750

Sq.Ft.

104 North Street

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 22 Railroad Avenue 10 Middletown, NY MLS# 829482
$2,400,000
3,091

Sq.Ft.

22 Railroad Avenue 10

Middletown, NY

Courtesy of PREFERRED PROPERTIES REAL ESTA
View Shawangunk Road Middletown, NY MLS# H6301772
$2,300,000
Studio

Beds

0.0

Baths

5,965,978

Sq.Ft.

Shawangunk Road

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
View 105 Sprague Avenue Middletown, NY MLS# 945497
$2,300,000
26,000

Sq.Ft.

105 Sprague Avenue

Middletown, NY

Courtesy of PREFERRED PROPERTIES REAL ESTA
View 23 Crystal Run Crossing Middletown, NY MLS# 844588
$2,000,000
6,960

Sq.Ft.

23 Crystal Run Crossing

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY
View 27 Maltese Drive Middletown, NY MLS# 924493
$1,850,000
6,148

Sq.Ft.

27 Maltese Drive

Middletown, NY

Courtesy of HOMESMART HOMES & ESTATES
View 2850 State Route 17k Middletown, NY MLS# 947735
  • Recently Listed
1 of 27
$1,800,000
1,754

Sq.Ft.

2850 State Route 17k

Middletown, NY

Courtesy of RE/MAX BENCHMARK REALTY GROUP
View 3 Bristol Drive Middletown, NY MLS# 812635
  • Virtual Tour
1 of 32
$1,799,000
5

Beds

7.2

Baths

7,794

Sq.Ft.

3 Bristol Drive

Middletown, NY

Courtesy of ALL AMERICAN REALTY MANAGEMENT
View 32 Gibbs Court Middletown, NY MLS# 944792
$1,650,000
Studio

Beds

0.0

Baths

326,700

Sq.Ft.

32 Gibbs Court

Middletown, NY

Courtesy of BERKSHIRE HATHAWAY HS NE PROP.
View 565 Prosperous Valley Road Middletown, NY MLS# 858885
$1,600,000
4

Beds

2.1

Baths

4,000

Sq.Ft.

565 Prosperous Valley Road

Middletown, NY

Courtesy of REAL ESTATE CIRCUIT INC
View 79 Bisch Road Middletown, NY MLS# 938715
$1,550,000
5

Beds

5.1

Baths

4,365

Sq.Ft.

79 Bisch Road

Middletown, NY

Courtesy of P R O LINKS REALTY INC
View Shawangunk Road Middletown, NY MLS# 901472
$1,499,000
Studio

Beds

0.0

Baths

4,011,876

Sq.Ft.

Shawangunk Road

Middletown, NY

Courtesy of MCGRATH REALTY INC
View 39 W Main Street Middletown, NY MLS# 928638
$1,380,000
4,533

Sq.Ft.

39 W Main Street

Middletown, NY

Courtesy of I REALTY LLC
View Industrial Drive Middletown, NY MLS# H6205621
$1,350,000
Studio

Beds

0.0

Baths

771,012

Sq.Ft.

Industrial Drive

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY
View 0 Crystal Run Road Middletown, NY MLS# H6324370
$1,330,000

0 Crystal Run Road

Middletown, NY

Courtesy of RAND COMMERCIAL
View 1 Royal Acres Drive Middletown, NY MLS# 947946
  • Recently Listed
1 of 48
$1,299,900
7,523

Sq.Ft.

1 Royal Acres Drive

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

240

Estimated median home price

$422,450
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

Price Count
$0 - 100K 6
$100K - 200K 18
$200K - 300K 39
$300K - 400K 49
$400K - 500K 45
$500K - 600K 22
$600K - 700K 13
$700K - 800K 11
$800K - 900K 5
$900K - 1M 4
$1M - Max 28

Homes for Sale by Type in Middletown, NY

Property Type Count
Single Family 141
Townhouse 0
Condo 25
Commercial 35
Rental 110
Lots and Land 28
Condo/Town/CoOp 0
CoOp 0
Multi Family 8
Mobile Home 3
Farms 0

(Data as of 1/11/2026)

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 1/13/2026.

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.

Information Copyright 2021, OneKey® MLS. All Rights Reserved.