View 3 Ben Lomond Drive Middletown, NY MLS# 1064561
  • Recently Listed
1 of 45
OPEN HOUSE: Sunday 11/8 12:00 PM - 2:00 PM
$589,000
5

Beds

2.0

Baths

2,263

Sq.Ft.

3 Ben Lomond Drive

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY
View 7 Maryland Avenue Middletown, NY MLS# 1061516
  • Recently Listed
1 of 19
$549,000
6

Beds

4.0

Baths

2,728

Sq.Ft.

7 Maryland Avenue

Middletown, NY

Courtesy of GREENE REALTY GROUP
View 23 Little Avenue Middletown, NY MLS# 1064439
  • Recently Listed
1 of 45
$340,000
3

Beds

1.1

Baths

1,543

Sq.Ft.

23 Little Avenue

Middletown, NY

Courtesy of KW HUDSON VALLEY UNITED
The time to sell is now! THE TIME TO SELL IS NOW!
View 42 Western Avenue Middletown, NY MLS# 1064186
  • Recently Listed with Virtual Tour
1 of 48
$529,000
4

Beds

3.0

Baths

1,880

Sq.Ft.

42 Western Avenue

Middletown, NY

Courtesy of SERHANT LLC
View 205 New Vernon Road Middletown, NY MLS# 1066003
  • Recently Listed
1 of 25
$599,000
5

Beds

2.0

Baths

2,864

Sq.Ft.

205 New Vernon Road

Middletown, NY

Courtesy of BOUKLIS GROUP MARKETING CORP
View 17 Lake Ridge Drive Middletown, NY MLS# 1065474
  • Recently Listed
1 of 33
$389,900
2

Beds

1.1

Baths

1,272

Sq.Ft.

17 Lake Ridge Drive

Middletown, NY

Courtesy of ARC REALTY 1 IN SALES
View 2 Durham Court Middletown, NY MLS# 1062845
  • Recently Listed
1 of 28
$349,500
2

Beds

2.1

Baths

1,241

Sq.Ft.

2 Durham Court

Middletown, NY

Courtesy of RELIABLE REALTY GROUP
View 8 Silo Lane Middletown, NY MLS# 1065141
  • Recently Listed
1 of 29
$360,000
3

Beds

2.1

Baths

1,692

Sq.Ft.

8 Silo Lane

Middletown, NY

Courtesy of RE/MAX BENCHMARK REALTY GROUP
View 95 Meadow View Drive Middletown, NY MLS# 1063951
  • Recently Listed
1 of 33
$495,000
3

Beds

3.1

Baths

1,781

Sq.Ft.

95 Meadow View Drive

Middletown, NY

Courtesy of KW HUDSON VALLEY UNITED
View 1 N Galleria Drive Middletown, NY MLS# 1065050
  • Recently Listed
1 of 8
$80,000
376,002

Sq.Ft.

1 N Galleria Drive

Middletown, NY

Courtesy of PREMIUM CHOICE INC
View 100 Hillside Drive B10 Middletown, NY MLS# 1060749
  • Recently Listed
1 of 35
$289,000
2

Beds

1.0

Baths

917

Sq.Ft.

100 Hillside Drive B10

Middletown, NY

Courtesy of KELLER WILLIAMS VALLEY REALTY
View 19-21 Dewitt Street Middletown, NY MLS# 1046601
  • Recently Listed
1 of 22
$439,000
3,223

Sq.Ft.

19-21 Dewitt Street

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY
View 83 Anthony Street Middletown, NY MLS# 1064064
  • Recently Listed
1 of 39
OPEN HOUSE: Tuesday 11/3 12:00 PM - 4:00 PM
$600,000
3

Beds

2.1

Baths

2,191

Sq.Ft.

83 Anthony Street

Middletown, NY

Courtesy of NICOLI REALTY
View 197 Deer Ct Drive Middletown, NY MLS# 1063819
  • Recently Listed
1 of 32
$339,000
2

Beds

2.1

Baths

1,473

Sq.Ft.

197 Deer Ct Drive

Middletown, NY

Courtesy of OWNER ENTRY.COM
View 405 County Route 22 Middletown, NY MLS# 1063876
  • Recently Listed
1 of 43
$448,000
3

Beds

4.0

Baths

2,360

Sq.Ft.

405 County Route 22

Middletown, NY

Courtesy of HOMESMART HOMES & ESTATES
View 61 Maureen Drive Middletown, NY MLS# 1063882
  • Recently Listed
1 of 13
$399,000
4

Beds

2.0

Baths

1,932

Sq.Ft.

61 Maureen Drive

Middletown, NY

Courtesy of HOMES BY YARA REALTY GROUP LLC
View 435 Tally Ho Road Middletown, NY MLS# 1063883
  • Recently Listed
1 of 22
$590,000
4

Beds

2.1

Baths

2,072

Sq.Ft.

435 Tally Ho Road

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY
View 102 Sproat Street Middletown, NY MLS# 1053243
$309,900
2

Beds

1.0

Baths

778

Sq.Ft.

102 Sproat Street

Middletown, NY

Courtesy of CURASI REALTY, INC.
View 56 Scott Drive Middletown, NY MLS# 1057888
  • Virtual Tour
1 of 49
$479,000
3

Beds

1.1

Baths

1,732

Sq.Ft.

56 Scott Drive

Middletown, NY

Courtesy of KELLER WILLIAMS REALTY
View 86 Woodlake Drive Middletown, NY MLS# 1063045
  • Recently Listed
1 of 41
$425,000
3

Beds

2.2

Baths

2,161

Sq.Ft.

86 Woodlake Drive

Middletown, NY

Courtesy of CRONIN & COMPANY REAL ESTATE

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.