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

105 Sands Road Middletown, NY 10941
Photo of 105 Sands Road, Middletown, NY 10941 (MLS # 4855535)
0 beds 0 baths $59,900
175 Sands Road Middletown, NY 10941
Photo of 175 Sands Road, Middletown, NY 10941 (MLS # 4855510)
0 beds 0 baths $67,900
13 Georges Road Middletown, NY 10941
Photo of 13 Georges Road, Middletown, NY 10941 (MLS # 4855013)
5 beds 3 baths 4,240 sqft $387,500
5 Ontario Avenue Middletown, NY 10940
Photo of 5 Ontario Avenue, Middletown, NY 10940 (MLS # 4855399)
3 beds 2 baths 1,559 sqft $1,500
Lot #6 Rebecca Drive Middletown, NY 10940
Photo of Lot #6 Rebecca Drive, Middletown, NY 10940 (MLS # 4855416)
4 beds 3 baths 2,056 sqft $359,900
36 Prospect Street Middletown, NY 10940
Photo of 36 Prospect Street, Middletown, NY 10940 (MLS # 4855341)
3 beds 2 baths 1,854 sqft $208,000
296 Concord Lane Middletown, NY 10940
Photo of 296 Concord Lane, Middletown, NY 10940 (MLS # 4853353)
2 beds 2 baths 995 sqft $1,450
156 West Main Street Middletown, NY 10940
Photo of 156 West Main Street, Middletown, NY 10940 (MLS # 4855363)
1 bed 2 baths 1,078 sqft $1,150
5 Windsor Mews Middletown, NY 10940
Photo of 5 Windsor Mews, Middletown, NY 10940 (MLS # 4855338)
3 beds 2 baths 1,234 sqft $165,000
18 Maryland Avenue Middletown, NY 10940
Photo of 18 Maryland Avenue, Middletown, NY 10940 (MLS # 4854819)
3 beds 2 baths 1,635 sqft $1,800
5 Belgrave Middletown, NY 10940
Photo of 5 Belgrave, Middletown, NY 10940 (MLS # 4855262)
3 beds 3 baths 1,608 sqft $229,900
690 Route 211 East Middletown, NY 10941
Photo of 690 Route 211 East, Middletown, NY 10941 (MLS # 4855160)
0 beds 0 baths 2,400 sqft $11
690 Route 211 East Middletown, NY 10941
Photo of 690 Route 211 East, Middletown, NY 10941 (MLS # 4855110)
0 beds 0 baths 2,146 sqft $16
27 Oliver Avenue Middletown, NY 10940
Photo of 27 Oliver Avenue, Middletown, NY 10940 (MLS # 4855184)
3 beds 2 baths 1,126 sqft $1,750
6 Watkins Avenue Middletown, NY 10940
Photo of 6 Watkins Avenue, Middletown, NY 10940 (MLS # 4855129)
2 beds 1 bath 1,259 sqft $1,700

Sold Listings in Middletown

48 Last Road Middletown, NY 10941
Photo of 48 Last Road, Middletown, NY 10941 (MLS # 4844618)
2 beds 2 baths 1,455 sqft $165,000
81 Kensington Way Middletown, NY 10940
Photo of 81 Kensington Way, Middletown, NY 10940 (MLS # 4850578)
2 beds 2 baths 1,185 sqft $160,000
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
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
70 Sycamore Drive Middletown, NY 10940
Photo of 70 Sycamore Drive, Middletown, NY 10940 (MLS # 4846009)
3 beds 3 baths 1,521 sqft $202,000
76 Reinhardt Road Middletown, NY 10940
Photo of 76 Reinhardt Road, Middletown, NY 10940 (MLS # 4846002)
3 beds 2 baths 1,500 sqft $320,000
28 Chestnut Avenue Middletown, NY 10940
Photo of 28 Chestnut Avenue, Middletown, NY 10940 (MLS # 4845526)
3 beds 2 baths 1,400 sqft $219,500
28 Morningside Drive Middletown, NY 10941
Photo of 28 Morningside Drive, Middletown, NY 10941 (MLS # 4845507)
3 beds 2 baths 1,764 sqft $156,719
220 Kirbytown Road Middletown, NY 10940
Photo of 220 Kirbytown Road, Middletown, NY 10940 (MLS # 4844434)
3 beds 2 baths 1,300 sqft $235,000
46 Last Road Middletown, NY 10941
Photo of 46 Last Road, Middletown, NY 10941 (MLS # 4844233)
3 beds 2 baths 1,612 sqft $305,000
110 Reinhardt Road Middletown, NY 10940
Photo of 110 Reinhardt Road, Middletown, NY 10940 (MLS # 4844348)
3 beds 1 bath 1,224 sqft $145,000
35 Pleasant Avenue Middletown, NY 10940
Photo of 35 Pleasant Avenue, Middletown, NY 10940 (MLS # 4843916)
3 beds 2 baths 1,572 sqft $190,000
123 Linden Avenue Middletown, NY 10940
Photo of 123 Linden Avenue, Middletown, NY 10940 (MLS # 4844054)
0 beds 0 baths $12,500
8 Corwin Avenue Middletown, NY 10940
Photo of 8 Corwin Avenue, Middletown, NY 10940 (MLS # 4825011)
4 beds 2 baths 2,339 sqft $125,500

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/