View 42 Rebecca Drive Middletown, NY MLS# 998305
  • Recently Listed
1 of 40
OPEN HOUSE: Saturday 5/16 12:00 PM - 2:00 PM
$530,000
4

Beds

3.0

Baths

2,126

Sq.Ft.

42 Rebecca Drive

Middletown, NY

Courtesy of HOMESMART HOMES & ESTATES
View 5 Dubois Street Middletown, NY MLS# 993300
  • Recently Listed
1 of 28
OPEN HOUSE: Sunday 5/17 12:00 PM - 2:00 PM
$399,900
3

Beds

2.0

Baths

1,278

Sq.Ft.

5 Dubois Street

Middletown, NY

Courtesy of EXP REALTY
View 5 Kendal Lane Middletown, NY MLS# 1000252
  • Recently Listed
1 of 11
OPEN HOUSE: Sunday 5/17 1:30 PM - 3:30 PM
$339,900
2

Beds

2.1

Baths

1,241

Sq.Ft.

5 Kendal Lane

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
The time to sell is now! THE TIME TO SELL IS NOW!
View 28 Cyprus Drive Middletown, NY MLS# 998266
  • Recently Listed
1 of 36
$499,900
2

Beds

2.0

Baths

1,473

Sq.Ft.

28 Cyprus Drive

Middletown, NY

Courtesy of RE/MAX BENCHMARK REALTY GROUP
View 37 California Avenue Middletown, NY MLS# 1000309
  • Recently Listed
1 of 10
$339,900
3

Beds

2.0

Baths

1,152

Sq.Ft.

37 California Avenue

Middletown, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
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 32 Hidden Valley Drive Middletown, NY MLS# 1000657
  • Recently Listed
1 of 22
$165,000
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
  • Recently Listed
1 of 35
OPEN HOUSE: Saturday 5/16 1:00 PM - 3:00 PM
$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
  • Recently Listed
1 of 25
OPEN HOUSE: Sunday 5/17 1:00 PM - 3:00 PM
$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 10
OPEN HOUSE: Sunday 5/17 11:00 AM - 1:00 PM
$539,900
4

Beds

3.0

Baths

2,560

Sq.Ft.

55 Eisenhower Drive

Middletown, NY

Courtesy of EREALTY ADVISORS, INC
View 366 Van Burenville Road Middletown, NY MLS# 999926
  • Recently Listed
1 of 31
$410,000
3

Beds

2.0

Baths

1,513

Sq.Ft.

366 Van Burenville Road

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
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
$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 80 Sarah Lane Middletown, NY MLS# 998293
  • Recently Listed with Virtual Tour
1 of 35
$294,900
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 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

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

269

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 - 100K11
$100K - 200K19
$200K - 300K28
$300K - 400K53
$400K - 500K71
$500K - 600K28
$600K - 700K16
$700K - 800K7
$800K - 900K7
$900K - 1M8
$1M - Max21

Homes for Sale by Type in Middletown, NY

Property TypeCount
Single Family163
Townhouse0
Condo23
Commercial36
Rental114
Lots and Land27
Condo/Town/CoOp0
CoOp0
Multi Family14
Mobile Home6
Farms0

(Data as of 5/16/2026)

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 5/17/2026.

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.