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

92 Woodlake Drive, Unit 11 Middletown, NY 10940
Photo of 92 Woodlake Drive, Unit 11, Middletown, NY 10940 (MLS # 4828668)
3 beds 4 baths 2,177 sqft $2,000
17 Millsburg Road Middletown, NY 10940
Photo of 17 Millsburg Road, Middletown, NY 10940 (MLS # 4746410)
4 beds 3 baths 2,089 sqft $249,900
11 Millsburg Road Middletown, NY 10940
Photo of 11 Millsburg Road, Middletown, NY 10940 (MLS # 4746622)
4 beds 2 baths 2,162 sqft $155,000
3 Dogwood Drive Middletown, NY 10940
Photo of 3 Dogwood Drive, Middletown, NY 10940 (MLS # 4828621)
4 beds 3 baths 2,038 sqft $259,000
90 Hufcut Road Middletown, NY 10941
Photo of 90 Hufcut Road, Middletown, NY 10941 (MLS # 4828658)
3 beds 1 bath 1,388 sqft $220,000
3 Harcourt Mews Middletown, NY 10940
Photo of 3 Harcourt Mews, Middletown, NY 10940 (MLS # 4828552)
3 beds 2 baths 1,248 sqft $215,000
147 Wisner Avenue Middletown, NY 10940
Photo of 147 Wisner Avenue, Middletown, NY 10940 (MLS # 4828523)
4 beds 2 baths 1,560 sqft $145,000
71 Montgomery Street Middletown, NY 10940
Photo of 71 Montgomery Street, Middletown, NY 10940 (MLS # 4828526)
7 beds 8 baths 4,536 sqft $260,000
4 Hill Road Middletown, NY 10941
Photo of 4 Hill Road, Middletown, NY 10941 (MLS # 4828512)
2 beds 2 baths 1,056 sqft $209,900
Cortright Road Middletown, NY 10940
Photo of Cortright Road, Middletown, NY 10940 (MLS # 4828521)
0 beds 0 baths $85,000
29-31 Rockwell Avenue Middletown, NY 10940
Photo of 29-31 Rockwell Avenue, Middletown, NY 10940 (MLS # 4827824)
4 beds 2 baths 1,442 sqft $199,900
15 Wells Avenue Middletown, NY 10940
Photo of 15 Wells Avenue, Middletown, NY 10940 (MLS # 4828504)
5 beds 3 baths 1,737 sqft $189,000
Cortright Road Middletown, NY 10940
Photo of Cortright Road, Middletown, NY 10940 (MLS # 4828502)
0 beds 0 baths $85,000
630 Van Burenville Road Middletown, NY 10940
Photo of 630 Van Burenville Road, Middletown, NY 10940 (MLS # 4828329)
0 beds 0 baths $85,000
16 Bonnell Place Middletown, NY 10940
Photo of 16 Bonnell Place, Middletown, NY 10940 (MLS # 4827752)
3 beds 1 bath 1,056 sqft $175,000

Sold Listings in Middletown

186 Watkins Avenue Middletown, NY 10940
Photo of 186 Watkins Avenue, Middletown, NY 10940 (MLS # 4804571)
3 beds 2 baths 1,736 sqft $229,950
91 Bowser Road Middletown, NY 10940
Photo of 91 Bowser Road, Middletown, NY 10940 (MLS # 4745964)
4 beds 3 baths 2,514 sqft $379,900
12 Highrose Ridge Way Middletown, NY 10940
Photo of 12 Highrose Ridge Way, Middletown, NY 10940 (MLS # 4739082)
3 beds 3 baths 3,057 sqft $285,000
32 Madelaine Terrace Middletown, NY 10940
Photo of 32 Madelaine Terrace, Middletown, NY 10940 (MLS # 4816813)
4 beds 2 baths 2,336 sqft $97,000
34 Juniper Circle Middletown, NY 10940
Photo of 34 Juniper Circle, Middletown, NY 10940 (MLS # 4802358)
2 beds 2 baths 2,368 sqft $420,000
716 Route 17m Middletown, NY 10940
Photo of 716 Route 17m, Middletown, NY 10940 (MLS # 4727480)
4 beds 2 baths 2,294 sqft $204,000
384 Concord Middletown, NY 10940
Photo of 384 Concord, Middletown, NY 10940 (MLS # 4800228)
2 beds 2 baths 924 sqft $64,900
100 Hillside Drive, Unit E16 Middletown, NY 10941
Photo of 100 Hillside Drive, Unit E16, Middletown, NY 10941 (MLS # 4818624)
2 beds 2 baths 1,140 sqft $140,000
271 Grahamtown Road Middletown, NY 10940
Photo of 271 Grahamtown Road, Middletown, NY 10940 (MLS # 4818143)
3 beds 2 baths 2,009 sqft $237,500
100 Hillside Drive, Unit A14 Middletown, NY 10941
Photo of 100 Hillside Drive, Unit A14, Middletown, NY 10941 (MLS # 4817537)
2 beds 2 baths 1,012 sqft $140,000
504 Shoddy Hollow Road Middletown, NY 10940
Photo of 504 Shoddy Hollow Road, Middletown, NY 10940 (MLS # 4816882)
4 beds 3 baths 1,850 sqft $338,000
4 Kent Court Middletown, NY 10940
Photo of 4 Kent Court, Middletown, NY 10940 (MLS # 4816311)
2 beds 3 baths 1,241 sqft $169,000
175 Ruth Court Middletown, NY 10940
Photo of 175 Ruth Court, Middletown, NY 10940 (MLS # 4816029)
2 beds 2 baths 1,049 sqft $116,000
933 Tower Ridge Circle Middletown, NY 10941
Photo of 933 Tower Ridge Circle, Middletown, NY 10941 (MLS # 4706123)
1 bed 1 bath 888 sqft $147,000
15 Sproat Street Middletown, NY 10940
Photo of 15 Sproat Street, Middletown, NY 10940 (MLS # 4815036)
4 beds 2 baths 2,180 sqft $208,900

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/