View 13 Benton Avenue Middletown, NY MLS# 998257
  • Recently Listed
1 of 21
$450,000
1,450

Sq.Ft.

13 Benton Avenue

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
View 319 Reservoir Road Middletown, NY MLS# 968373
  • Recently Listed
1 of 34
$465,000
3

Beds

2.0

Baths

2,028

Sq.Ft.

319 Reservoir Road

Middletown, NY

Courtesy of CURASI REALTY, INC.
View 16 Woodland Road Middletown, NY MLS# 997655
  • Recently Listed
1 of 13
$249,000
3

Beds

1.0

Baths

1,250

Sq.Ft.

16 Woodland Road

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 543 Dosen Road Middletown, NY MLS# 997791
  • Recently Listed
1 of 25
OPEN HOUSE: Sunday 5/17 12:00 PM - 2:00 PM
$325,000
3

Beds

1.0

Baths

1,061

Sq.Ft.

543 Dosen Road

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
View 54 Whitman Court Middletown, NY MLS# 989180
  • Recently Listed
1 of 44
$299,999
3

Beds

1.1

Baths

1,428

Sq.Ft.

54 Whitman Court

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY
View 12 Weather Vane Way Middletown, NY MLS# 992510
  • Recently Listed
1 of 40
$474,999
3

Beds

2.1

Baths

2,055

Sq.Ft.

12 Weather Vane Way

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY
View 122 Rolling Meadows Road Middletown, NY MLS# 991496
  • Recently Listed
1 of 47
OPEN HOUSE: Saturday 5/16 12:00 PM - 2:00 PM
$465,000
3

Beds

2.0

Baths

2,055

Sq.Ft.

122 Rolling Meadows Road

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY
View 100 Crans Road Middletown, NY MLS# 997243
  • Recently Listed
1 of 25
$429,900
2

Beds

1.0

Baths

988

Sq.Ft.

100 Crans Road

Middletown, NY

Courtesy of CENTURY 21 E & M WILLIAMS RLTY
View 15 High Ridge Lane Middletown, NY MLS# 996214
  • Recently Listed
1 of 26
$479,900
2

Beds

2.1

Baths

1,762

Sq.Ft.

15 High Ridge Lane

Middletown, NY

Courtesy of RE/MAX BENCHMARK REALTY GROUP
View 9 Chestnut Street Middletown, NY MLS# 988951
  • Recently Listed with Virtual Tour
1 of 28
$434,999
3

Beds

2.0

Baths

1,614

Sq.Ft.

9 Chestnut Street

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
View 13 Hermanette Avenue Middletown, NY MLS# 995759
  • Recently Listed
1 of 29
$460,000
3

Beds

2.1

Baths

1,852

Sq.Ft.

13 Hermanette Avenue

Middletown, NY

Courtesy of Weichert Realtors - Monroe
View 29 Murray Road Middletown, NY MLS# 994440
  • Recently Listed
1 of 24
OPEN HOUSE: Sunday 5/17 12:00 PM - 2:00 PM
$579,000
5

Beds

3.0

Baths

2,202

Sq.Ft.

29 Murray Road

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 12 Oak Ridge Road Middletown, NY MLS# 994308
  • Recently Listed with Virtual Tour
1 of 48
OPEN HOUSE: Saturday 5/16 3:00 PM - 5:30 PM
$574,990
3

Beds

2.0

Baths

2,596

Sq.Ft.

12 Oak Ridge Road

Middletown, NY

Courtesy of JACKIE HENRY REALTY LLC
View 32 Genung Street Middletown, NY MLS# 992207
  • Recently Listed
1 of 19
$359,999
3

Beds

3.0

Baths

7,200

Sq.Ft.

32 Genung Street

Middletown, NY

Courtesy of Weichert Realtors - Monroe
View 83 Deer Ct Drive Middletown, NY MLS# 994032
  • Recently Listed with Virtual Tour
1 of 43
OPEN HOUSE: Saturday 5/16 1:00 PM - 3:00 PM
$425,000
3

Beds

2.1

Baths

1,919

Sq.Ft.

83 Deer Ct Drive

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 22 Oak Lane Middletown, NY MLS# 988510
  • Virtual Tour
1 of 36
$399,999
3

Beds

1.1

Baths

1,410

Sq.Ft.

22 Oak Lane

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
View 133 Blumel Road Middletown, NY MLS# 990211
  • Recently Listed
1 of 39
$449,000
3

Beds

2.0

Baths

1,756

Sq.Ft.

133 Blumel Road

Middletown, NY

Courtesy of HUDSON VALLEY GRIFFITH
View 9 Silo Farm Place Middletown, NY MLS# 992793
  • Recently Listed with Virtual Tour
1 of 50
$599,900
4

Beds

2.1

Baths

2,342

Sq.Ft.

9 Silo Farm Place

Middletown, NY

Courtesy of HOMESMART HOMES & ESTATES
View 66 Deer Ct Drive Middletown, NY MLS# 990896
  • Recently Listed
1 of 31
$290,000
2

Beds

2.0

Baths

1,146

Sq.Ft.

66 Deer Ct Drive

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 571 Route 17M Middletown, NY MLS# 984442
$829,000
4

Beds

2.2

Baths

3,340

Sq.Ft.

571 Route 17M

Middletown, NY

Courtesy of BHG REAL ESTATE GREEN TEAM

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

262

Estimated median home price

$449,900
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

PriceCount
$0 - 100K11
$100K - 200K19
$200K - 300K29
$300K - 400K52
$400K - 500K68
$500K - 600K28
$600K - 700K14
$700K - 800K7
$800K - 900K7
$900K - 1M8
$1M - Max19

Homes for Sale by Type in Middletown, NY

Property TypeCount
Single Family156
Townhouse0
Condo22
Commercial37
Rental113
Lots and Land28
Condo/Town/CoOp0
CoOp0
Multi Family13
Mobile Home6
Farms0

(Data as of 5/14/2026)

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 5/15/2026.

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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