View 58 Wawayanda Avenue Middletown, NY MLS# 888435
$220,000
2

Beds

1.0

Baths

820

Sq.Ft.

58 Wawayanda Avenue

Middletown, NY

Courtesy of CRONIN & COMPANY REAL ESTATE
View 125 Whipple Road Middletown, NY MLS# 886181
  • Virtual Tour
1 of 21
$599,000
4

Beds

3.0

Baths

2,552

Sq.Ft.

125 Whipple Road

Middletown, NY

Courtesy of JULIA B FEE SOTHEBYS INT. RLTY
View 551 5th Avenue Middletown, NY MLS# 888408
$150,000
3

Beds

2.0

Baths

1,344

Sq.Ft.

551 5th Avenue

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
The time to sell is now! THE TIME TO SELL IS NOW!
View 264 Lybolt Road Middletown, NY MLS# 886597
  • Virtual Tour
1 of 45
$739,900
4

Beds

3.1

Baths

2,823

Sq.Ft.

264 Lybolt Road

Middletown, NY

Courtesy of REALTY PROMOTIONS INC
View 274 Wisner Avenue Middletown, NY MLS# 883358
$1,200,000
1,500

Sq.Ft.

274 Wisner Avenue

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
View 40 Ivory Lane Middletown, NY MLS# 884982
$40,000
Studio

Beds

0.0

Baths

550

Sq.Ft.

40 Ivory Lane

Middletown, NY

Courtesy of EXP REALTY
View 83 Dosen Road Middletown, NY MLS# 873908
  • Virtual Tour
1 of 38
$585,000
3

Beds

2.0

Baths

4,240

Sq.Ft.

83 Dosen Road

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 32 Nicaj Court Middletown, NY MLS# 859545
$279,000
Studio

Beds

0.0

Baths

919,116

Sq.Ft.

32 Nicaj Court

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
View 87 Dolson Avenue Middletown, NY MLS# 875298
$225,000
43,560

Sq.Ft.

87 Dolson Avenue

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
View 482 Scotchtown Avenue Middletown, NY MLS# 875217
$759,000
5

Beds

3.0

Baths

2,828

Sq.Ft.

482 Scotchtown Avenue

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 24 John Street Middletown, NY MLS# 874957
  • Virtual Tour
1 of 46
$399,000
4,147

Sq.Ft.

24 John Street

Middletown, NY

Courtesy of GREEN TEAM COMMERCIAL
View 593 Route 211 E Middletown, NY MLS# 869688
$985,000
2,575

Sq.Ft.

593 Route 211 E

Middletown, NY

Courtesy of CRONIN & COMPANY REAL ESTATE
View 708 Kirbytown Road Middletown, NY MLS# 863721
  • Virtual Tour
1 of 36
$575,000
4

Beds

2.1

Baths

2,292

Sq.Ft.

708 Kirbytown Road

Middletown, NY

Courtesy of SHAHAR MANAGEMENT LLC
View 2 Rivervale Road Middletown, NY MLS# 869398
$335,000
3

Beds

2.0

Baths

1,484

Sq.Ft.

2 Rivervale Road

Middletown, NY

Courtesy of YOURHOMESOLD GUARANTEED REALTY
View 115 Vincent Drive Middletown, NY MLS# 872206
$320,000
3

Beds

2.0

Baths

1,964

Sq.Ft.

115 Vincent Drive

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 1 Country Club Drive Middletown, NY MLS# 867762
$624,900
3

Beds

3.1

Baths

3,013

Sq.Ft.

1 Country Club Drive

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
View 26 Kyleigh Way Middletown, NY MLS# 863142
$599,999
4

Beds

3.1

Baths

2,188

Sq.Ft.

26 Kyleigh Way

Middletown, NY

Courtesy of LIST 4 LESS REALTY
View 29 Hubbard Road Middletown, NY MLS# 861061
$849,900
4

Beds

3.1

Baths

3,407

Sq.Ft.

29 Hubbard Road

Middletown, NY

Courtesy of REALTY PROMOTIONS INC
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 21 Lake Claire Drive Middletown, NY MLS# 857177
$209,999
2

Beds

2.0

Baths

990

Sq.Ft.

21 Lake Claire Drive

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

241

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 - 200K16
$200K - 300K37
$300K - 400K56
$400K - 500K43
$500K - 600K23
$600K - 700K11
$700K - 800K13
$800K - 900K4
$900K - 1M4
$1M - Max28

Homes for Sale by Type in Middletown, NY

Property TypeCount
Single Family144
Townhouse0
Condo23
Commercial35
Rental120
Lots and Land29
Condo/Town/CoOp0
CoOp0
Multi Family7
Mobile Home3
Farms0

(Data as of 12/29/2025)

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 12/29/2025.

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.

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