View 39 California Avenue Middletown, NY MLS# 1063370
  • Recently Listed
1 of 33
$349,900
4

Beds

1.0

Baths

1,204

Sq.Ft.

39 California Avenue

Middletown, NY

Courtesy of DALTON WADE REAL ESTATE GROUP
View 5 Sayer Lane Middletown, NY MLS# 1062620
  • Recently Listed
1 of 26
$330,000
3

Beds

2.0

Baths

1,080

Sq.Ft.

5 Sayer Lane

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
View 4 Francis Drive Middletown, NY MLS# 1061004
  • Virtual Tour
1 of 44
$499,999
4

Beds

2.0

Baths

2,188

Sq.Ft.

4 Francis Drive

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 17 Grant Street Middletown, NY MLS# 1062037
  • Recently Listed
1 of 22
$265,000
2

Beds

1.1

Baths

960

Sq.Ft.

17 Grant Street

Middletown, NY

Courtesy of Q HOME SALES
View 512 County Route 49 Middletown, NY MLS# 1062924
  • Recently Listed
1 of 41
$680,000
4

Beds

2.1

Baths

2,906

Sq.Ft.

512 County Route 49

Middletown, NY

Courtesy of KW HUDSON VALLEY UNITED
View 4 Harding Street Middletown, NY MLS# 1061283
  • Recently Listed
1 of 17
$299,900
4

Beds

2.0

Baths

1,416

Sq.Ft.

4 Harding Street

Middletown, NY

Courtesy of KW HUDSON VALLEY UNITED
View 33 Roosevelt Avenue Middletown, NY MLS# 1059870
  • Recently Listed
1 of 13
$234,900
2

Beds

1.0

Baths

848

Sq.Ft.

33 Roosevelt Avenue

Middletown, NY

Courtesy of BHG REAL ESTATE GREEN TEAM
View 59 Webb Road Middletown, NY MLS# 1060361
  • Recently Listed with Virtual Tour
1 of 50
$659,000
5

Beds

5.1

Baths

3,960

Sq.Ft.

59 Webb Road

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
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
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 5 Oak Ridge Road Middletown, NY MLS# 1062548
  • Recently Listed
1 of 18
$499,000
4

Beds

3.0

Baths

2,392

Sq.Ft.

5 Oak Ridge Road

Middletown, NY

Courtesy of REDFIN REAL ESTATE
View 21 Willow Place Middletown, NY MLS# 1058807
  • Recently Listed
1 of 12
$324,900
3

Beds

1.0

Baths

1,032

Sq.Ft.

21 Willow Place

Middletown, NY

Courtesy of EREALTY ADVISORS, INC
View 13 S Shore Drive Middletown, NY MLS# 1060643
  • Recently Listed
1 of 34
$488,000
4

Beds

2.1

Baths

2,544

Sq.Ft.

13 S Shore Drive

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
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 542 Dosen Road Middletown, NY MLS# 1061154
$180,000
2

Beds

1.0

Baths

826

Sq.Ft.

542 Dosen Road

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY
View 6 Beverly Road Middletown, NY MLS# 1056583
$549,900
4

Beds

3.0

Baths

2,520

Sq.Ft.

6 Beverly Road

Middletown, NY

Courtesy of HOMESMART HOMES & ESTATES
View 5 Pilgrim Corners Road Middletown, NY MLS# 1057338
$475,000
3

Beds

3.0

Baths

2,128

Sq.Ft.

5 Pilgrim Corners Road

Middletown, NY

Courtesy of HOWARD HANNA RAND REALTY
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

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

330

Estimated median home price

$417,500
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 - 100K8
$100K - 200K24
$200K - 300K43
$300K - 400K86
$400K - 500K60
$500K - 600K40
$600K - 700K17
$700K - 800K12
$800K - 900K11
$900K - 1M4
$1M - Max25

Homes for Sale by Type in Middletown, NY

Property TypeCount
Single Family219
Townhouse0
Condo32
Commercial40
Rental126
Lots and Land26
Condo/Town/CoOp0
CoOp0
Multi Family11
Mobile Home2
Farms0

(Data as of 11/2/2026)

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.