View 408 County Route 22 Middletown, NY MLS# 905653
$379,999
3

Beds

1.1

Baths

1,132

Sq.Ft.

408 County Route 22

Middletown, NY

Courtesy of RITA LEVINE REAL ESTATE
View 1 Chestnut Street Middletown, NY MLS# 902008
$379,000
3

Beds

1.0

Baths

1,100

Sq.Ft.

1 Chestnut Street

Middletown, NY

Courtesy of HOMESMART HOMES & ESTATES
View 390 Hufcut Road Middletown, NY MLS# 925873
$379,000
2

Beds

1.0

Baths

1,142

Sq.Ft.

390 Hufcut Road

Middletown, NY

Courtesy of RE/MAX PRIME PROPERTIES
The time to sell is now! THE TIME TO SELL IS NOW!
View 715 Stony Ford Middletown, NY MLS# 899195
$375,000
3

Beds

1.1

Baths

1,706

Sq.Ft.

715 Stony Ford

Middletown, NY

Courtesy of JOHN J LEASE REALTORS INC
View 5 Raleigh Close Middletown, NY MLS# 918721
  • Adult Community
1 of 32
$375,000
3

Beds

1.1

Baths

1,608

Sq.Ft.

5 Raleigh Close

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 29 Little Avenue Middletown, NY MLS# 927332
$375,000
4

Beds

2.1

Baths

1,668

Sq.Ft.

29 Little Avenue

Middletown, NY

Courtesy of CHRISTIE'S INT. REAL ESTATE
View 7 Manhattan Avenue Middletown, NY MLS# 923151
$369,999
3

Beds

1.0

Baths

1,550

Sq.Ft.

7 Manhattan Avenue

Middletown, NY

Courtesy of R NEW YORK
View 8 Ebury Middletown, NY MLS# 924863
$368,800
4

Beds

3.0

Baths

1,505

Sq.Ft.

8 Ebury

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 28 Lake Ridge Drive Middletown, NY MLS# 931152
$365,000
3

Beds

2.1

Baths

1,460

Sq.Ft.

28 Lake Ridge Drive

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 71 Commonwealth Avenue Middletown, NY MLS# 936595
$360,000
3

Beds

1.0

Baths

1,344

Sq.Ft.

71 Commonwealth Avenue

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 5 Mills Avenue Middletown, NY MLS# 893182
$359,999
3

Beds

1.1

Baths

1,160

Sq.Ft.

5 Mills Avenue

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY
View 14 Knox Avenue Middletown, NY MLS# 931022
$359,000
3

Beds

1.1

Baths

1,344

Sq.Ft.

14 Knox Avenue

Middletown, NY

Courtesy of HOMESMART HOMES & ESTATES
View 14 Kensington Way Middletown, NY MLS# 944383
  • Recently Listed
1 of 23
$359,000
2

Beds

1.1

Baths

1,115

Sq.Ft.

14 Kensington Way

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 65 Monhagen Avenue Middletown, NY MLS# 933768
$350,000
3

Beds

2.1

Baths

930

Sq.Ft.

65 Monhagen Avenue

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 57 Overhill Road Middletown, NY MLS# 935730
$350,000
5

Beds

2.1

Baths

3,581

Sq.Ft.

57 Overhill Road

Middletown, NY

Courtesy of EXP REALTY
View 91 Mountain Avenue Middletown, NY MLS# 941164
$350,000
3

Beds

1.0

Baths

892

Sq.Ft.

91 Mountain Avenue

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 17 Little Avenue Middletown, NY MLS# H6310576
$349,999
5

Beds

2.0

Baths

1,670

Sq.Ft.

17 Little Avenue

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY
View 53 Richmond Place Middletown, NY MLS# 915824
$349,999
3

Beds

1.0

Baths

1,144

Sq.Ft.

53 Richmond Place

Middletown, NY

Courtesy of CURASI REALTY, INC.
View 16 Mountain Avenue Middletown, NY MLS# 937497
  • Virtual Tour
1 of 35
$349,900
3

Beds

1.1

Baths

1,598

Sq.Ft.

16 Mountain Avenue

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 1 Chancery Mews Middletown, NY MLS# 909891
$349,000
3

Beds

1.1

Baths

1,604

Sq.Ft.

1 Chancery Mews

Middletown, NY

Courtesy of KELLER WILLIAMS 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

245

Estimated median home price

$414,999
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 16
$200K - 300K 37
$300K - 400K 59
$400K - 500K 44
$500K - 600K 23
$600K - 700K 11
$700K - 800K 13
$800K - 900K 4
$900K - 1M 4
$1M - Max 28

Homes for Sale by Type in Middletown, NY

Property Type Count
Single Family 147
Townhouse 0
Condo 23
Commercial 35
Rental 119
Lots and Land 29
Condo/Town/CoOp 0
CoOp 0
Multi Family 8
Mobile Home 3
Farms 0

(Data as of 12/26/2025)

Information deemed reliable but not guaranteed.

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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