View 4 Harding Street Middletown, NY MLS# 1061283
$299,900
4

Beds

2.0

Baths

1,416

Sq.Ft.

4 Harding Street

Middletown, NY

Courtesy of KW HUDSON VALLEY UNITED
View 21 Fair Avenue Middletown, NY MLS# 1060943
$319,000
2

Beds

2.0

Baths

1,360

Sq.Ft.

21 Fair Avenue

Middletown, NY

Courtesy of HOMESMART HOMES & ESTATES
View 311 Howells Road Middletown, NY MLS# 1056653
  • Virtual Tour
1 of 37
$399,999
3

Beds

1.0

Baths

1,188

Sq.Ft.

311 Howells Road

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 18 Pine Street Middletown, NY MLS# 1030008
$400,000
3

Beds

2.0

Baths

1,508

Sq.Ft.

18 Pine Street

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
View 21 Willow Place Middletown, NY MLS# 1058807
$319,900
3

Beds

1.0

Baths

1,032

Sq.Ft.

21 Willow Place

Middletown, NY

Courtesy of EREALTY ADVISORS, INC
View 54 Western Avenue Middletown, NY MLS# 1058671
$330,000
2

Beds

1.0

Baths

962

Sq.Ft.

54 Western Avenue

Middletown, NY

Courtesy of EXP REALTY
View 34 Chaucer Court Middletown, NY MLS# 1059605
$360,000
3

Beds

1.1

Baths

1,428

Sq.Ft.

34 Chaucer Court

Middletown, NY

Courtesy of DIAMOND QUALITY REAL ESTATE
View 367 Route 211 W Middletown, NY MLS# 1060758
$350,000
2

Beds

1.0

Baths

1,078

Sq.Ft.

367 Route 211 W

Middletown, NY

Courtesy of EXP REALTY
View 21 Old Timers Road Middletown, NY MLS# 1061045
$390,000
3

Beds

1.1

Baths

1,440

Sq.Ft.

21 Old Timers Road

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
View 14 Columbia Avenue Middletown, NY MLS# 1058581
$311,000
3

Beds

1.0

Baths

954

Sq.Ft.

14 Columbia Avenue

Middletown, NY

Courtesy of KW HUDSON VALLEY UNITED
View 30 Reservoir Road Middletown, NY MLS# 1060554
$385,000
3

Beds

1.0

Baths

1,072

Sq.Ft.

30 Reservoir Road

Middletown, NY

Courtesy of REAL ESTATE CIRCUIT INC
View 136 Sycamore Drive Middletown, NY MLS# 1058492
$299,900
2

Beds

2.0

Baths

1,110

Sq.Ft.

136 Sycamore Drive

Middletown, NY

Courtesy of CURASI REALTY, INC.
View 15 N Aspen Road Middletown, NY MLS# 1058387
$299,000
2

Beds

1.1

Baths

1,144

Sq.Ft.

15 N Aspen Road

Middletown, NY

Courtesy of SERHANT LLC
View 34 Houston Avenue Middletown, NY MLS# 1058232
$315,000
3

Beds

2.0

Baths

5,450

Sq.Ft.

34 Houston Avenue

Middletown, NY

Courtesy of I REALTY LLC
View 138 Prospect Avenue Middletown, NY MLS# 1053196
$369,000
2

Beds

1.0

Baths

1,422

Sq.Ft.

138 Prospect Avenue

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
View 243 Howells Turnpike Middletown, NY MLS# 1046716
$399,000
2

Beds

1.0

Baths

960

Sq.Ft.

243 Howells Turnpike

Middletown, NY

Courtesy of HOMESMART HOMES & ESTATES
View 63 Orchard Hill Road Middletown, NY MLS# 1056390
$389,000
3

Beds

2.0

Baths

1,062

Sq.Ft.

63 Orchard Hill Road

Middletown, NY

Courtesy of REALTY PROMOTIONS INC
View 8 Keystone Park Middletown, NY MLS# 1055264
$399,000
3

Beds

1.0

Baths

912

Sq.Ft.

8 Keystone Park

Middletown, NY

Courtesy of CRONIN & COMPANY REAL ESTATE
View 19 Putters Way 9 Middletown, NY MLS# 1055933
$394,900
2

Beds

2.1

Baths

1,337

Sq.Ft.

19 Putters Way 9

Middletown, NY

Courtesy of RE/MAX BENCHMARK REALTY GROUP
View 55 Orange Terrace Middletown, NY MLS# 1052724
  • Virtual Tour
1 of 39
$325,000
3

Beds

1.0

Baths

1,092

Sq.Ft.

55 Orange Terrace

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

318

Estimated median home price

$419,500
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 - 100K10
$100K - 200K24
$200K - 300K39
$300K - 400K82
$400K - 500K55
$500K - 600K36
$600K - 700K19
$700K - 800K11
$800K - 900K12
$900K - 1M4
$1M - Max26

Homes for Sale by Type in Middletown, NY

Property TypeCount
Single Family201
Townhouse0
Condo32
Commercial41
Rental121
Lots and Land29
Condo/Town/CoOp0
CoOp0
Multi Family13
Mobile Home2
Farms0

(Data as of 11/9/2026)

Information deemed reliable but not guaranteed.

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.