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

129 Concord Lane Middletown, NY 10940
Photo of 129 Concord Lane, Middletown, NY 10940 (MLS # 4967734)
2 beds 2 baths 1,230 sqft $105,000
125 Wickham Avenue, Unit 3B Middletown, NY 10940
Photo of 125 Wickham Avenue, Unit 3B, Middletown, NY 10940 (MLS # 4966636)
2 beds 1 bath 700 sqft $1,500
3 Brewster Drive Middletown, NY 10940
Photo of 3 Brewster Drive, Middletown, NY 10940 (MLS # 4921250)
3 beds 2 baths 1,776 sqft $262,500
568 County Route 49 Middletown, NY 10940
Photo of 568 County Route 49, Middletown, NY 10940 (MLS # 4967421)
3 beds 3 baths 1,593 sqft $2,095
7 Wilcox Avenue Middletown, NY 10940
Photo of 7 Wilcox Avenue, Middletown, NY 10940 (MLS # 4967351)
3 beds 2 baths 1,914 sqft $275,000
7 Bartlett Drive Middletown, NY 10941
Photo of 7 Bartlett Drive, Middletown, NY 10941 (MLS # 4967240)
2 beds 1 bath 1,100 sqft $219,000
1138 Dolsontown Road Middletown, NY 10940
Photo of 1138 Dolsontown Road, Middletown, NY 10940 (MLS # 4966332)
0 beds 0 baths 6,400 sqft $749,000
59 Roosevelt Avenue Middletown, NY 10940
Photo of 59 Roosevelt Avenue, Middletown, NY 10940 (MLS # 4962856)
2 beds 1 bath 869 sqft $124,500
69 Commonwealth Avenue Middletown, NY 10940
Photo of 69 Commonwealth Avenue, Middletown, NY 10940 (MLS # 4923337)
3 beds 2 baths 1,822 sqft $219,000
330 North Street Middletown, NY 10940
Photo of 330 North Street, Middletown, NY 10940 (MLS # 4935469)
3 beds 1 bath 1,320 sqft $59,900
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
37 California Avenue Middletown, NY 10940
Photo of 37 California Avenue, Middletown, NY 10940 (MLS # 4964772)
3 beds 1 bath 1,152 sqft $1,550
232 Concord Lane Middletown, NY 10940
Photo of 232 Concord Lane, Middletown, NY 10940 (MLS # 4965038)
2 beds 2 baths 995 sqft $78,000
94 Fairways Drive Middletown, NY 10940
Photo of 94 Fairways Drive, Middletown, NY 10940 (MLS # 4964716)
5 beds 3 baths 3,098 sqft $515,000
6 Estate Drive Middletown, NY 10940
Photo of 6 Estate Drive, Middletown, NY 10940 (MLS # 4964588)
3 beds 2 baths 1,177 sqft $145,000

Sold Listings in Middletown

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
6 Allan Park Middletown, NY 10940
Photo of 6 Allan Park, Middletown, NY 10940 (MLS # 4928707)
3 beds 2 baths 1,248 sqft $185,000
54 Phillips Street Middletown, NY 10940
Photo of 54 Phillips Street, Middletown, NY 10940 (MLS # 4924044)
3 beds 2 baths 928 sqft $90,000
36 Horton Avenue Middletown, NY 10940
Photo of 36 Horton Avenue, Middletown, NY 10940 (MLS # 4915465)
3 beds 2 baths 1,384 sqft $230,000
11 Richmond Place Middletown, NY 10940
Photo of 11 Richmond Place, Middletown, NY 10940 (MLS # 4923306)
3 beds 1 bath 1,416 sqft $121,000
1024 Greenville Turnpike Middletown, NY 10940
Photo of 1024 Greenville Turnpike, Middletown, NY 10940 (MLS # 4854021)
2 beds 1 bath 1,138 sqft $261,000
48 Liberty Street Middletown, NY 10940
Photo of 48 Liberty Street, Middletown, NY 10940 (MLS # 4921142)
8 beds 2 baths 2,402 sqft $107,500
47 Horton Avenue Middletown, NY 10940
Photo of 47 Horton Avenue, Middletown, NY 10940 (MLS # 4920831)
3 beds 1 bath 1,008 sqft $186,500
512 County Route 49 Middletown, NY 10940
Photo of 512 County Route 49, Middletown, NY 10940 (MLS # 4920259)
4 beds 3 baths 2,906 sqft $438,000
3 Christopher Court Middletown, NY 10941
Photo of 3 Christopher Court, Middletown, NY 10941 (MLS # 4920330)
3 beds 3 baths 1,748 sqft $320,000
38 Watkins Avenue Middletown, NY 10940
Photo of 38 Watkins Avenue, Middletown, NY 10940 (MLS # 4837237)
4 beds 2 baths 1,872 sqft $160,000
7 Danielle Court Middletown, NY 10940
Photo of 7 Danielle Court, Middletown, NY 10940 (MLS # 4918060)
3 beds 3 baths 1,456 sqft $178,500
240 Phillips Street Middletown, NY 10940
Photo of 240 Phillips Street, Middletown, NY 10940 (MLS # 4917170)
3 beds 1 bath 1,300 sqft $164,000
16 Eagles Way Middletown, NY 10940
Photo of 16 Eagles Way, Middletown, NY 10940 (MLS # 4842482)
3 beds 5 baths 3,300 sqft $455,000
944 Tower Ridge Circle Middletown, NY 10941
Photo of 944 Tower Ridge Circle, Middletown, NY 10941 (MLS # 4916524)
2 beds 2 baths 1,249 sqft $193,000

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/