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

99 Sycamore Drive Middletown, NY 10940
Photo of 99 Sycamore Drive, Middletown, NY 10940 (MLS # 4849041)
1 bed 1 bath 830 sqft $125,000
72 Spruce Road Middletown, NY 10940
Photo of 72 Spruce Road, Middletown, NY 10940 (MLS # 4848852)
3 beds 2 baths 1,624 sqft $260,000
11 Robertson Drive Middletown, NY 10940
Photo of 11 Robertson Drive, Middletown, NY 10940 (MLS # 4849003)
2 beds 1 bath 720 sqft $134,900
315 Derby Road Middletown, NY 10940
Photo of 315 Derby Road, Middletown, NY 10940 (MLS # 4846903)
4 beds 3 baths 2,546 sqft $279,000
55 School House Road Middletown, NY 10940
Photo of 55 School House Road, Middletown, NY 10940 (MLS # 4845205)
3 beds 1 bath 1,000 sqft $249,000
864 Rte 17M Middletown, NY 12589
Photo of 864 Rte 17M, Middletown, NY 12589 (MLS # 4848899)
3 beds 1 bath 1,248 sqft $58,900
68 Eisenhower Drive Middletown, NY 10940
Photo of 68 Eisenhower Drive, Middletown, NY 10940 (MLS # 4848879)
4 beds 3 baths 1,938 sqft $183,750
8 Charlotte Mews Middletown, NY 10940
Photo of 8 Charlotte Mews, Middletown, NY 10940 (MLS # 4834676)
0 beds 0 baths $83,400
360 Crystal Run Road Middletown, NY 10941
Photo of 360 Crystal Run Road, Middletown, NY 10941 (MLS # 4848815)
0 beds 0 baths 31,534 sqft $3,500,000
396 North Street Middletown, NY 10940
Photo of 396 North Street, Middletown, NY 10940 (MLS # 4848774)
5 beds 2 baths 2,302 sqft $124,900
32 3rd Street Middletown, NY 10940
Photo of 32 3rd Street, Middletown, NY 10940 (MLS # 4848754)
4 beds 3 baths 2,254 sqft $300,000
580 East Main Street Middletown, NY 10940
Photo of 580 East Main Street, Middletown, NY 10940 (MLS # 4847576)
0 beds 0 baths 1,752 sqft $389,900
55 Midland Avenue Middletown, NY 10940
Photo of 55 Midland Avenue, Middletown, NY 10940 (MLS # 4847672)
0 beds 0 baths 47,000 sqft $7
8 Winthrop Avenue Middletown, NY 10940
Photo of 8 Winthrop Avenue, Middletown, NY 10940 (MLS # 4848537)
3 beds 2 baths 1,316 sqft $184,900
17-39 Midland Avenue, Unit 1 Middletown, NY 10940
Photo of 17-39 Midland Avenue, Unit 1, Middletown, NY 10940 (MLS # 4847678)
0 beds 0 baths 12,216 sqft $8

Sold Listings in Middletown

29 Maple Fields Drive Middletown, NY 10940
Photo of 29 Maple Fields Drive, Middletown, NY 10940 (MLS # 4753473)
3 beds 3 baths 2,581 sqft $305,000
22 Fortune Road Middletown, NY 10941
Photo of 22 Fortune Road, Middletown, NY 10941 (MLS # 4834336)
3 beds 3 baths 1,732 sqft $285,000
40 Fox Hill Drive Middletown, NY 10940
Photo of 40 Fox Hill Drive, Middletown, NY 10940 (MLS # 4832026)
4 beds 3 baths 3,144 sqft $395,000
200 Lewis Landing Road Middletown, NY 10940
Photo of 200 Lewis Landing Road, Middletown, NY 10940 (MLS # 4801776)
3 beds 3 baths 2,354 sqft $359,900
228 White Bridge Road Middletown, NY 10940
Photo of 228 White Bridge Road, Middletown, NY 10940 (MLS # 4826555)
3 beds 2 baths 2,422 sqft $155,000
151 Watkins Avenue Middletown, NY 10940
Photo of 151 Watkins Avenue, Middletown, NY 10940 (MLS # 4753500)
3 beds 1 bath 996 sqft $130,000
106 Fairways Drive Middletown, NY 10940
Photo of 106 Fairways Drive, Middletown, NY 10940 (MLS # 4818222)
3 beds 3 baths 2,430 sqft $475,000
MLS # 4838815 Middletown, NY
Photo of Middletown, NY (MLS # 4838815)
3 beds 2 baths 1,620 sqft $151,200
12 Bonnie Brae Drive Middletown, NY 10941
Photo of 12 Bonnie Brae Drive, Middletown, NY 10941 (MLS # 4836374)
3 beds 2 baths 1,446 sqft $250,000
43 Brick Pond Road Middletown, NY 10940
Photo of 43 Brick Pond Road, Middletown, NY 10940 (MLS # 4831510)
3 beds 3 baths 1,460 sqft $200,000
467 Union School Road Middletown, NY 10941
Photo of 467 Union School Road, Middletown, NY 10941 (MLS # 4837677)
3 beds 3 baths 1,890 sqft $200,000
64 Howells Turnpike Middletown, NY 10940
Photo of 64 Howells Turnpike, Middletown, NY 10940 (MLS # 4813266)
3 beds 2 baths 1,092 sqft $180,000
632 Route 211 Middletown, NY 10940
Photo of 632 Route 211, Middletown, NY 10940 (MLS # 4816533)
3 beds 1 bath 1,250 sqft $117,500
24 Blake Middletown, NY 10940
Photo of 24 Blake, Middletown, NY 10940 (MLS # 4218969)
2 beds 0 baths $300,000
90 Jordan Lane Middletown, NY 10940
Photo of 90 Jordan Lane, Middletown, NY 10940 (MLS # 4837053)
3 beds 3 baths 1,507 sqft $199,900

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/