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

599 Guymard Turnpike Middletown, NY 10940
Photo of 599 Guymard Turnpike, Middletown, NY 10940 (MLS # 4922494)
3 beds 2 baths 1,852 sqft $279,500
12 Crane Road Middletown, NY 10941
Photo of 12 Crane Road, Middletown, NY 10941 (MLS # 4920883)
4 beds 2 baths 2,104 sqft $288,888
1024 Greenville Turnpike Middletown, NY 10940
Photo of 1024 Greenville Turnpike, Middletown, NY 10940 (MLS # 4854021)
2 beds 1 bath 1,138 sqft $249,900
63 Liberty Street Middletown, NY 10940
Photo of 63 Liberty Street, Middletown, NY 10940 (MLS # 4919951)
2 beds 1 bath 936 sqft $1,550
37 California Avenue Middletown, NY 10940
Photo of 37 California Avenue, Middletown, NY 10940 (MLS # 4919220)
3 beds 1 bath 1,152 sqft $1,550
161 South Street Middletown, NY 10940
Photo of 161 South Street, Middletown, NY 10940 (MLS # 4922199)
4 beds 2 baths 1,746 sqft $209,000
281 New Vernon Road Middletown, NY 10940
Photo of 281 New Vernon Road, Middletown, NY 10940 (MLS # 4852062)
3 beds 2 baths 2,304 sqft $209,900
14 Putters Way Middletown, NY 10940
Photo of 14 Putters Way, Middletown, NY 10940 (MLS # 4922341)
2 beds 3 baths 2,000 sqft $2,500
92 Jordan Lane Middletown, NY 10940
Photo of 92 Jordan Lane, Middletown, NY 10940 (MLS # 4922353)
3 beds 3 baths 1,507 sqft $1,850
140 West Main Street Middletown, NY 10940
Photo of 140 West Main Street, Middletown, NY 10940 (MLS # 4922265)
4 beds 2 baths 2,847 sqft $264,900
101 Monhagen Avenue, Unit 2 Middletown, NY 10940
Photo of 101 Monhagen Avenue, Unit 2, Middletown, NY 10940 (MLS # 4922261)
0 beds 0 baths 1,000 sqft $1,200
22 Revere Drive Middletown, NY 10940
Photo of 22 Revere Drive, Middletown, NY 10940 (MLS # 4914456)
3 beds 2 baths 1,161 sqft $165,000
19 Grandview Avenue Middletown, NY 10940
Photo of 19 Grandview Avenue, Middletown, NY 10940 (MLS # 4908200)
4 beds 1 bath 1,286 sqft $129,000
588 Van Burenville Road Middletown, NY 10940
Photo of 588 Van Burenville Road, Middletown, NY 10940 (MLS # 4921787)
4 beds 3 baths 2,112 sqft $334,900
14 Keystone Park Middletown, NY 10940
Photo of 14 Keystone Park, Middletown, NY 10940 (MLS # 4921214)
3 beds 1 bath 960 sqft $189,900

Sold Listings in Middletown

62 Jasmine Drive Middletown, NY 10940
Photo of 62 Jasmine Drive, Middletown, NY 10940 (MLS # 4844984)
2 beds 3 baths 2,454 sqft $370,000
37 Oak Hill Road Middletown, NY 10941
Photo of 37 Oak Hill Road, Middletown, NY 10941 (MLS # 4911109)
2 beds 3 baths 1,814 sqft $251,000
2 Bonnell Street Middletown, NY 10940
Photo of 2 Bonnell Street, Middletown, NY 10940 (MLS # 4908935)
3 beds 1 bath 1,260 sqft $118,000
738 Manning Road Middletown, NY 10940
Photo of 738 Manning Road, Middletown, NY 10940 (MLS # 4904323)
3 beds 2 baths 1,568 sqft $260,000
37 Jordan Lane Middletown, NY 10940
Photo of 37 Jordan Lane, Middletown, NY 10940 (MLS # 4904088)
2 beds 3 baths 1,348 sqft $175,000
100 Hillside Drive, Unit B12 Middletown, NY 10941
Photo of 100 Hillside Drive, Unit B12, Middletown, NY 10941 (MLS # 4904546)
2 beds 1 bath 875 sqft $130,000
9 Gardner Avenue Middletown, NY 10940
Photo of 9 Gardner Avenue, Middletown, NY 10940 (MLS # 4904273)
3 beds 1 bath 1,600 sqft $138,000
37 Maple Drive Middletown, NY 10940
Photo of 37 Maple Drive, Middletown, NY 10940 (MLS # 4904356)
3 beds 2 baths 1,144 sqft $149,500
28 Kent Court Middletown, NY 10940
Photo of 28 Kent Court, Middletown, NY 10940 (MLS # 4903765)
2 beds 3 baths 1,241 sqft $171,000
547 Route 17m Middletown, NY 10940
Photo of 547 Route 17m, Middletown, NY 10940 (MLS # 4851844)
2 beds 2 baths 1,186 sqft $126,800
179 Wisner Avenue Middletown, NY 10940
Photo of 179 Wisner Avenue, Middletown, NY 10940 (MLS # 4811795)
3 beds 2 baths 1,392 sqft $204,900
112 Patio Road Middletown, NY 10941
Photo of 112 Patio Road, Middletown, NY 10941 (MLS # 4902043)
3 beds 2 baths 1,440 sqft $130,000
42 Mayer Drive Middletown, NY 10940
Photo of 42 Mayer Drive, Middletown, NY 10940 (MLS # 4900668)
2 beds 2 baths 1,280 sqft $185,000
59 Mulberry Street Middletown, NY 10940
Photo of 59 Mulberry Street, Middletown, NY 10940 (MLS # 4902686)
4 beds 1 bath 1,384 sqft $50,100
316 Concord Lane Middletown, NY 10940
Photo of 316 Concord Lane, Middletown, NY 10940 (MLS # 4902532)
1 bed 1 bath 735 sqft $48,000

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/