View 5 Decker Drive Middletown, NY MLS# 999526
  • Recently Listed with Virtual Tour
1 of 33
$649,000
3

Beds

2.1

Baths

2,481

Sq.Ft.

5 Decker Drive

Middletown, NY

Courtesy of RE/MAX BENCHMARK REALTY GROUP
View 20 Park Circle Drive Middletown, NY MLS# 998648
  • Recently Listed
1 of 50
$539,000
4

Beds

2.1

Baths

2,644

Sq.Ft.

20 Park Circle Drive

Middletown, NY

Courtesy of EREALTY ADVISORS, INC
View 317 E Main Street 309 Middletown, NY MLS# 997729
  • Recently Listed
1 of 6
$630,000
10

Beds

4.0

Baths

27,555

Sq.Ft.

317 E Main Street 309

Middletown, NY

Courtesy of Q HOME SALES
The time to sell is now! THE TIME TO SELL IS NOW!
View 32 Hidden Valley Drive Middletown, NY MLS# 1000657
  • Recently Listed
1 of 22
$159,900
2

Beds

2.0

Baths

1,296

Sq.Ft.

32 Hidden Valley Drive

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 153 Ridgewood Avenue Middletown, NY MLS# 992982
$475,000
3

Beds

2.0

Baths

1,577

Sq.Ft.

153 Ridgewood Avenue

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 205 Linden Avenue Middletown, NY MLS# 996009
$310,000
3

Beds

2.0

Baths

1,061

Sq.Ft.

205 Linden Avenue

Middletown, NY

Courtesy of EPIQUE REALTY
View 217-219 Highland Avenue Middletown, NY MLS# 977631
  • Recently Listed
1 of 41
$479,000
3

Beds

2.1

Baths

2,228

Sq.Ft.

217-219 Highland Avenue

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 55 Eisenhower Drive Middletown, NY MLS# 999918
  • Recently Listed
1 of 12
$539,900
4

Beds

3.0

Baths

2,560

Sq.Ft.

55 Eisenhower Drive

Middletown, NY

Courtesy of EREALTY ADVISORS, INC
View 126 Rolling Meadows Road Middletown, NY MLS# 998294
  • Recently Listed with Virtual Tour
1 of 48
$447,000
4

Beds

2.1

Baths

2,155

Sq.Ft.

126 Rolling Meadows Road

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
View 8 Roberts Street Middletown, NY MLS# 998312
  • Recently Listed
1 of 9
OPEN HOUSE: Sunday 6/7 2:00 PM - 4:00 PM
$460,000
5

Beds

2.0

Baths

2,132

Sq.Ft.

8 Roberts Street

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 44 Commonwealth Avenue Middletown, NY MLS# 998424
  • Recently Listed
1 of 23
$298,900
3

Beds

1.0

Baths

1,180

Sq.Ft.

44 Commonwealth Avenue

Middletown, NY

Courtesy of FRANK TANGREDI REALTY COMPANY
View 90 M And M Road Middletown, NY MLS# 997326
  • Virtual Tour
1 of 50
$680,000
4

Beds

2.1

Baths

1,996

Sq.Ft.

90 M And M Road

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 80 Sarah Lane Middletown, NY MLS# 998293
  • Virtual Tour
1 of 35
$294,901
3

Beds

1.1

Baths

1,440

Sq.Ft.

80 Sarah Lane

Middletown, NY

Courtesy of Weichert Realtors - Monroe
View 47 Wickham Avenue 45 Middletown, NY MLS# 997491
  • Recently Listed
1 of 18
$450,000
3

Beds

1.0

Baths

1,478

Sq.Ft.

47 Wickham Avenue 45

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
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 16 Woodland Road Middletown, NY MLS# 997655
$249,000
3

Beds

1.0

Baths

1,250

Sq.Ft.

16 Woodland Road

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
View 543 Dosen Road Middletown, NY MLS# 997791
$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
$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
$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
$465,000
3

Beds

2.0

Baths

2,055

Sq.Ft.

122 Rolling Meadows Road

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

277

Estimated median home price

$450,000
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 - 100K10
$100K - 200K24
$200K - 300K27
$300K - 400K55
$400K - 500K68
$500K - 600K34
$600K - 700K18
$700K - 800K6
$800K - 900K7
$900K - 1M7
$1M - Max21

Homes for Sale by Type in Middletown, NY

Property TypeCount
Single Family166
Townhouse0
Condo24
Commercial35
Rental92
Lots and Land29
Condo/Town/CoOp0
CoOp0
Multi Family15
Mobile Home8
Farms0

(Data as of 6/1/2026)

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 6/2/2026.

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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