Houses for Sale in Middletown, NY

We’ll help you discover the wonderful homes for sale in Middletown, NY and find the perfect fit for your needs, desires and lifestyle.

Middletown is a city in Orange County, New York, U.S., in New York’s Hudson Valley region, near the Wallkill River, in the foothills of the Shawangunk Mountains. It is the second largest city in Orange County and is situated off Routes 17 and I-84 at the foot of the Catskill region.

Downtown Middletown

The downtown area has a number of historic churches, and Highland Avenue has a number of large Victorian houses. Many of these homes are occupied by medical doctors and their families, with a section devoted to the doctor’s office.

Middletown’s Many Shopping Centers

It is also known for its many shopping centers including The Galleria at Crystal Run, which is the second largest mall in New York’s Hudson Valley region.

Some Middletown Attractions

Each July the Fair comes to town and are located at the Orange County Fairgrounds. The Speedway at the same site is thought by some to be “the oldest continuously operating racing surface in the world,” having been constructed for horse racing in 1857. Several unique eateries and the landmark Paramount Theatre are located downtown. The beautiful Morrison Mansion, on the campus of SUNY Orange, is open to the public during the holiday season for a fabulous themed floral display.

Other Middletown attractions include the National Carmelite Shrine, hot air balloon rides departing Randall Airport, Soons Orchards and Maples Farm, several flea markets, and Highland Lakes State Park, an undeveloped area available for fishing, hiking and horseback riding. Many well-known chain hotels make Middletown a convenient stop for visitors.

Linda Ross Realty has been helping clients find, tour, and purchase houses for sale in Chester, NY for over 20 years. Contact us for more information on homes for sale in the Chester, NY area.

Middletown Real Estate Listings

Active Listings in Middletown

100 Hillside Drive, Unit A14 Middletown, NY 10941
Photo of 100 Hillside Drive, Unit A14, Middletown, NY 10941 (MLS # 5026449)
2 beds 2 baths 1,012 sqft $1,600
South Centerville Road Middletown, NY 10940
Photo of South Centerville Road, Middletown, NY 10940 (MLS # 5027694)
0 beds 0 baths $338,000
Karen Drive Middletown, NY 10940
Photo of Karen Drive, Middletown, NY 10940 (MLS # 5027423)
0 beds 0 baths $320,000
Pocatello Road Middletown, NY 10940
Photo of Pocatello Road, Middletown, NY 10940 (MLS # 5027385)
0 beds 0 baths $780,000
Greenville Turnpike Middletown, NY 10940
Photo of Greenville Turnpike, Middletown, NY 10940 (MLS # 5027302)
0 beds 0 baths $279,000
California Drive Middletown, NY 10940
Photo of California Drive, Middletown, NY 10940 (MLS # 5027173)
0 beds 0 baths $35,000
Route 211 Middletown, NY 10940
Photo of Route 211, Middletown, NY 10940 (MLS # 5027162)
0 beds 0 baths $20,000
46 Benjamin Avenue Middletown, NY 10940
Photo of 46 Benjamin Avenue, Middletown, NY 10940 (MLS # 5024701)
3 beds 1 bath 1,473 sqft $149,500
8 Silo Lane Middletown, NY 10940
Photo of 8 Silo Lane, Middletown, NY 10940 (MLS # 5026177)
3 beds 3 baths 1,692 sqft $169,900
MLS # 5024903 Middletown, NY
Photo of Middletown, NY (MLS # 5024903)
3 beds 2 baths 1,440 sqft $1,750
129 Apple Lane Drive Middletown, NY 10940
Photo of 129 Apple Lane Drive, Middletown, NY 10940 (MLS # 5025294)
2 beds 1 bath 2,436 sqft $1,500
22 Crane Road Middletown, NY 10941
Photo of 22 Crane Road, Middletown, NY 10941 (MLS # 5025720)
4 beds 2 baths 1,620 sqft $269,000
68 Scott Drive Middletown, NY 10941
Photo of 68 Scott Drive, Middletown, NY 10941 (MLS # 5022125)
3 beds 2 baths 1,824 sqft $160,500
181 Howells Road Middletown, NY 10940
Photo of 181 Howells Road, Middletown, NY 10940 (MLS # 5022585)
3 beds 3 baths 2,591 sqft $2,500
1343 St Hwy 211 Middletown, NY 10940
Photo of 1343 St Hwy 211, Middletown, NY 10940 (MLS # 5020707)
3 beds 2 baths 1,700 sqft $249,900

Sold Listings in Middletown

89 Camp Orange Road Middletown, NY 10941
Photo of 89 Camp Orange Road, Middletown, NY 10941 (MLS # 4832950)
3 beds 3 baths 3,056 sqft $830,000
29 Peach Place Middletown, NY 10940
Photo of 29 Peach Place, Middletown, NY 10940 (MLS # 4968026)
3 beds 4 baths 1,864 sqft $225,000
33 Rivervale Road Middletown, NY 10940
Photo of 33 Rivervale Road, Middletown, NY 10940 (MLS # 4929210)
3 beds 2 baths 1,528 sqft $158,000
34 Lafayette Avenue Middletown, NY 10940
Photo of 34 Lafayette Avenue, Middletown, NY 10940 (MLS # 4968832)
3 beds 2 baths 1,536 sqft $214,000
151 Academy Avenue Middletown, NY 10940
Photo of 151 Academy Avenue, Middletown, NY 10940 (MLS # 4914666)
4 beds 3 baths 1,287 sqft $156,000
20 Jasmine Drive Middletown, NY 10940
Photo of 20 Jasmine Drive, Middletown, NY 10940 (MLS # 4965504)
2 beds 2 baths 1,909 sqft $425,000
232 Concord Lane Middletown, NY 10940
Photo of 232 Concord Lane, Middletown, NY 10940 (MLS # 4965038)
2 beds 2 baths 995 sqft $79,000
20 John Street Middletown, NY 10940
Photo of 20 John Street, Middletown, NY 10940 (MLS # 4917908)
0 beds 0 baths 5,157 sqft $160,000
24 Ogden Street Middletown, NY 10940
Photo of 24 Ogden Street, Middletown, NY 10940 (MLS # 4962679)
3 beds 2 baths 1,582 sqft $141,000
18 Chaucer Court Middletown, NY 10941
Photo of 18 Chaucer Court, Middletown, NY 10941 (MLS # 4953369)
3 beds 2 baths 1,428 sqft $115,000
23 Davidge Road Middletown, NY 10940
Photo of 23 Davidge Road, Middletown, NY 10940 (MLS # 4916050)
4 beds 3 baths 2,457 sqft $267,000
36 Park Circle Drive Middletown, NY 10940
Photo of 36 Park Circle Drive, Middletown, NY 10940 (MLS # 4947155)
3 beds 1 bath 1,368 sqft $218,000
98 Blumel Road Middletown, NY 10941
Photo of 98 Blumel Road, Middletown, NY 10941 (MLS # 4945408)
4 beds 2 baths 1,894 sqft $150,000
62 Sarah Lane Middletown, NY 10941
Photo of 62 Sarah Lane, Middletown, NY 10941 (MLS # 4944847)
3 beds 2 baths 1,440 sqft $107,500
3 Neptune Lane Middletown, NY 10940
Photo of 3 Neptune Lane, Middletown, NY 10940 (MLS # 4816020)
3 beds 2 baths 1,620 sqft $237,500

Walk Score for Middletown



Middletown School Data

Middletown School Districts

Middletown City School District
K-12
Minisink Valley Central School District
K-12

Middletown Schools

John W Chorley School
K-1, public
William A Carter School
K-5, public
Middletown Twin Towers Middle School
6-8, public
Middletown High School
9-12, public
Truman Moon School
K-5, public
Monhagen Middle School
6-8, public
http://www.middletowncityschools.org/Domain/12
Maple Hill Elementary School
K-5, public
http://middletowncityschools.org/Page/14
Minisink Valley Elementary School
K-2, public
https://www.minisink.com/index.php?id=6
Minisink Valley High School
9-12, public
Minisink Valley Middle School
6-8, public
http://www.minisink.com/index.php?id=3
Otisville Elementary School
K-5, public
https://www.minisink.com/index.php?id=5
Minisink Valley Intermediate School
3-5, public
https://minisink.com/index.php?id=4
Our Lady Of Mount Carmel School
PK-8, private
St. Joseph School
PK-8, private
Middletown Christian School-Sda
PK-8, private
Harmony Christian School
PK-12, private
New Beginnings Montessori
PK-2, private
Arc Orange County Chapter
1, private
Presidential Park Elementary School
K-5, public
http://www.middletowncityschools.org/