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 15 Commonwealth Avenue Middletown, NY MLS# 891691
$299,000
3

Beds

1.0

Baths

1,092

Sq.Ft.

15 Commonwealth Avenue

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY
View 143 N Beacon Street Middletown, NY MLS# 925978
$295,000
3

Beds

1.0

Baths

1,264

Sq.Ft.

143 N Beacon Street

Middletown, NY

Courtesy of CORCORAN COUNTRY LIVING
The time to sell is now! THE TIME TO SELL IS NOW!
View 143 N Beacon Street Middletown, NY MLS# 20255140
$295,000
3

Beds

1.0

Baths

1,264

Sq.Ft.

143 N Beacon Street

Middletown, NY

UlsterCountyNY
Courtesy of CORCORAN COUNTRY LIVING
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
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 14 Spruce Peak Road Middletown, NY MLS# 923725
$325,000
3

Beds

1.1

Baths

1,496

Sq.Ft.

14 Spruce Peak Road

Middletown, NY

Courtesy of CRONIN & COMPANY REAL ESTATE
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 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 12-14 Union Street Middletown, NY MLS# 921611
$300,000
15,299

Sq.Ft.

12-14 Union Street

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 727 Route 17M Middletown, NY MLS# 917365
$350,000
1

Beds

1.0

Baths

1,088

Sq.Ft.

727 Route 17M

Middletown, NY

Courtesy of CRONIN & COMPANY REAL ESTATE
View 136 & 140 Gillen Road Middletown, NY MLS# 894968
$329,000
3

Beds

1.0

Baths

1,344

Sq.Ft.

136 & 140 Gillen Road

Middletown, NY

Courtesy of CRONIN & COMPANY REAL ESTATE
View 328 Bloomingburg Road Middletown, NY MLS# 915106
$299,999
Studio

Beds

0.0

Baths

1,184,832

Sq.Ft.

328 Bloomingburg Road

Middletown, NY

Courtesy of CURASI REALTY, INC.
View 38 Prospect Street Middletown, NY MLS# 914007
$349,000
4

Beds

1.0

Baths

1,790

Sq.Ft.

38 Prospect Street

Middletown, NY

Courtesy of CURASI REALTY, INC.
View 20 Benton Avenue Middletown, NY MLS# 907148
$319,999
3

Beds

2.0

Baths

1,504

Sq.Ft.

20 Benton Avenue

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY
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
View 9 Genung Street Middletown, NY MLS# 907464
$299,999
3

Beds

2.0

Baths

1,240

Sq.Ft.

9 Genung Street

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
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 111 Apple Lane Drive Middletown, NY MLS# 900782
$305,000
2

Beds

1.1

Baths

1,150

Sq.Ft.

111 Apple Lane Drive

Middletown, NY

Courtesy of RE/MAX BENCHMARK REALTY GROUP
View 2024 Mount Hope Road Middletown, NY MLS# 899476
$300,000
Studio

Beds

0.0

Baths

1,467,972

Sq.Ft.

2024 Mount Hope Road

Middletown, NY

Courtesy of HUDSON VALLEY GRIFFITH

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

$429,900
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 18
$200K - 300K 38
$300K - 400K 50
$400K - 500K 43
$500K - 600K 22
$600K - 700K 12
$700K - 800K 13
$800K - 900K 5
$900K - 1M 4
$1M - Max 28

Homes for Sale by Type in Middletown, NY

Property Type Count
Single Family 142
Townhouse 0
Condo 24
Commercial 34
Rental 115
Lots and Land 29
Condo/Town/CoOp 0
CoOp 0
Multi Family 7
Mobile Home 3
Farms 0

(Data as of 1/6/2026)

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.