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
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
The time to sell is now! THE TIME TO SELL IS NOW!
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
  • Recently Listed
1 of 9
$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 2850 State Route 17k Middletown, NY MLS# H6282727
$1,899,999
1,754

Sq.Ft.

2850 State Route 17k

Middletown, NY

Courtesy of RE/MAX BENCHMARK REALTY GROUP
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 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
  • Recently Listed
1 of 4
$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# 839738
$1,299,900
7,523

Sq.Ft.

1 Royal Acres Drive

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 80 Pine Grove Road Middletown, NY MLS# 933382
$1,299,000
6

Beds

5.1

Baths

4,650

Sq.Ft.

80 Pine Grove Road

Middletown, NY

Courtesy of REALTY PROMOTIONS INC
View 422 M and M Road Middletown, NY MLS# H6314994
  • Virtual Tour
1 of 36
$1,200,000
Studio

Beds

0.0

Baths

1,768,536

Sq.Ft.

422 M and M Road

Middletown, NY

Courtesy of EXP 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

239

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 - 100K6
$100K - 200K17
$200K - 300K37
$300K - 400K54
$400K - 500K43
$500K - 600K23
$600K - 700K11
$700K - 800K13
$800K - 900K4
$900K - 1M4
$1M - Max27

Homes for Sale by Type in Middletown, NY

Property TypeCount
Single Family142
Townhouse0
Condo24
Commercial34
Rental120
Lots and Land29
Condo/Town/CoOp0
CoOp0
Multi Family7
Mobile Home3
Farms0

(Data as of 12/30/2025)

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 ©2025 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 12/30/2025.

All information provided is deemed reliable but is not guaranteed and should be independently verified.

Copyright 2025 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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