View 20 John Street Middletown, NY MLS# 1003208
  • Recently Listed
1 of 19
$575,000
3

Beds

3.0

Baths

5,157

Sq.Ft.

20 John Street

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 153 Ridge Drive Middletown, NY MLS# 996792
  • Recently Listed
1 of 47
$575,000
3

Beds

3.0

Baths

2,133

Sq.Ft.

153 Ridge Drive

Middletown, NY

Courtesy of EXP REALTY
View 180 Mt Orange Road Middletown, NY MLS# 998755
  • Recently Listed with Virtual Tour
1 of 46
$574,900
5

Beds

2.0

Baths

2,432

Sq.Ft.

180 Mt Orange Road

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
The time to sell is now! THE TIME TO SELL IS NOW!
View 120 Prospect Avenue Middletown, NY MLS# 999664
  • Recently Listed with Virtual Tour
1 of 40
$385,000
3

Beds

1.1

Baths

1,382

Sq.Ft.

120 Prospect Avenue

Middletown, NY

Courtesy of HOMESMART HOMES & ESTATES
View TBD Brook Road Middletown, NY MLS# 999740
  • Recently Listed with Virtual Tour
1 of 44
$849,900
4

Beds

2.1

Baths

3,000

Sq.Ft.

TBD Brook Road

Middletown, NY

Courtesy of EXP REALTY
View 568 County Route 49 2C Middletown, NY MLS# 1001539
  • Recently Listed
1 of 30
$399,900
3

Beds

2.1

Baths

1,593

Sq.Ft.

568 County Route 49 2C

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 430 Kirbytown Road Middletown, NY MLS# 1002004
  • Recently Listed
1 of 37
$1,600,000
4

Beds

2.1

Baths

2,774

Sq.Ft.

430 Kirbytown Road

Middletown, NY

Courtesy of ARC REALTY 1 IN SALES
View 215 Linden Avenue Middletown, NY MLS# 1001604
$599,900
6

Beds

2.0

Baths

3,190

Sq.Ft.

215 Linden Avenue

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 21 Albert Street Middletown, NY MLS# 1001050
  • Recently Listed
1 of 25
$390,000
4

Beds

2.0

Baths

1,652

Sq.Ft.

21 Albert Street

Middletown, NY

Courtesy of RE/MAX BENCHMARK REALTY GROUP
View 25 Mill Street Middletown, NY MLS# 1001186
  • Recently Listed
1 of 9
$399,900
4

Beds

2.0

Baths

1,472

Sq.Ft.

25 Mill Street

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY
View 37 California Drive Middletown, NY MLS# 1008642
$499,000
4

Beds

2.1

Baths

2,136

Sq.Ft.

37 California Drive

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 12 Hidden Valley Drive Middletown, NY MLS# 1006256
$125,000
2

Beds

2.0

Baths

1,152

Sq.Ft.

12 Hidden Valley Drive

Middletown, NY

Courtesy of EPIQUE REALTY
View 16 Houston Ext Avenue Middletown, NY MLS# 1006867
$550,000
4

Beds

2.1

Baths

2,069

Sq.Ft.

16 Houston Ext Avenue

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
View 22 Chestnut Street Middletown, NY MLS# 1006581
$278,000
4

Beds

1.1

Baths

1,548

Sq.Ft.

22 Chestnut Street

Middletown, NY

Courtesy of YOURHOMESOLD GUARANTEED REALTY
View 8 Wayne Court Middletown, NY MLS# 1006739
  • Virtual Tour
1 of 50
$529,999
4

Beds

2.1

Baths

2,486

Sq.Ft.

8 Wayne Court

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
View 411 Mt Joy Road Middletown, NY MLS# 998261
$949,500
4

Beds

2.1

Baths

3,296

Sq.Ft.

411 Mt Joy Road

Middletown, NY

Courtesy of PICTURE IT SOLD, LLC
View 7 Harcourt Mews Middletown, NY MLS# 1001545
$275,000
3

Beds

1.1

Baths

1,604

Sq.Ft.

7 Harcourt Mews

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
View 2 White Horse Road Middletown, NY MLS# 996623
  • Virtual Tour
1 of 47
$1,249,000
3

Beds

2.1

Baths

4,225

Sq.Ft.

2 White Horse Road

Middletown, NY

Courtesy of BHG REAL ESTATE GREEN TEAM
View 217 School House Road Middletown, NY MLS# 999323
$680,000
4

Beds

2.1

Baths

2,410

Sq.Ft.

217 School House Road

Middletown, NY

Courtesy of RE/MAX TOWN & COUNTRY
View 9 School House Road Middletown, NY MLS# 996900
$699,900
4

Beds

2.1

Baths

2,192

Sq.Ft.

9 School House 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

274

Estimated median home price

$450,000
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 - 100K9
$100K - 200K25
$200K - 300K26
$300K - 400K50
$400K - 500K66
$500K - 600K38
$600K - 700K16
$700K - 800K7
$800K - 900K9
$900K - 1M6
$1M - Max22

Homes for Sale by Type in Middletown, NY

Property TypeCount
Single Family167
Townhouse0
Condo20
Commercial36
Rental96
Lots and Land28
Condo/Town/CoOp0
CoOp0
Multi Family15
Mobile Home8
Farms0

(Data as of 6/6/2026)

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 6/8/2026.

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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