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

93 Edinburgh Road Middletown, NY 10941
Photo of 93 Edinburgh Road, Middletown, NY 10941 (MLS # 4837291)
4 beds 2 baths 2,044 sqft $273,000
14 Avenue C Middletown, NY 10940
Photo of 14 Avenue C, Middletown, NY 10940 (MLS # 4838706)
3 beds 1 bath 1,162 sqft $2,100
46 Chaucer Court Middletown, NY 10941
Photo of 46 Chaucer Court, Middletown, NY 10941 (MLS # 4838670)
3 beds 2 baths 1,428 sqft $1,700
68 Ridgewood Avenue Middletown, NY 10940
Photo of 68 Ridgewood Avenue, Middletown, NY 10940 (MLS # 4838609)
2 beds 1 bath 1,117 sqft $1,750
74 Wallkill Avenue Middletown, NY 10940
Photo of 74 Wallkill Avenue, Middletown, NY 10940 (MLS # 4838611)
4 beds 2 baths 1,870 sqft $224,900
68 Eisenhower Drive Middletown, NY 10940
Photo of 68 Eisenhower Drive, Middletown, NY 10940 (MLS # 4838575)
4 beds 3 baths 1,938 sqft $183,750
138 Linden Avenue Middletown, NY 10940
Photo of 138 Linden Avenue, Middletown, NY 10940 (MLS # 4838522)
0 beds 0 baths $2,900
16 Charles Street Middletown, NY 10940
Photo of 16 Charles Street, Middletown, NY 10940 (MLS # 4835363)
1 bed 1 bath 700 sqft $1,200
20 Pine Street Middletown, NY 10940
Photo of 20 Pine Street, Middletown, NY 10940 (MLS # 4836989)
3 beds 2 baths 1,776 sqft $209,900
77 Jordan Lane Middletown, NY 10940
Photo of 77 Jordan Lane, Middletown, NY 10940 (MLS # 4837485)
3 beds 3 baths 1,345 sqft $1,800
81 Jordan Lane Middletown, NY 10940
Photo of 81 Jordan Lane, Middletown, NY 10940 (MLS # 4838352)
3 beds 3 baths 1,507 sqft $209,900
96 Sarah Lane Middletown, NY 10941
Photo of 96 Sarah Lane, Middletown, NY 10941 (MLS # 4838043)
3 beds 2 baths 1,440 sqft $130,000
43 Mountain Avenue Middletown, NY 10940
Photo of 43 Mountain Avenue, Middletown, NY 10940 (MLS # 4829019)
4 beds 2 baths 1,746 sqft $209,000
35 Lake Claire Drive Middletown, NY 10940
Photo of 35 Lake Claire Drive, Middletown, NY 10940 (MLS # 4823641)
2 beds 1 bath 742 sqft $79,900
56 Brewster Drive Middletown, NY 10940
Photo of 56 Brewster Drive, Middletown, NY 10940 (MLS # 4837172)
3 beds 3 baths 1,658 sqft $185,999

Sold Listings in Middletown

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
9 Comfort Road Middletown, NY 10941
Photo of 9 Comfort Road, Middletown, NY 10941 (MLS # 4831171)
4 beds 2 baths 2,096 sqft $250,000
618 Lybolt Road Middletown, NY 10941
Photo of 618 Lybolt Road, Middletown, NY 10941 (MLS # 4828345)
3 beds 3 baths 2,312 sqft $230,000
23 Wilkin Avenue Middletown, NY 10940
Photo of 23 Wilkin Avenue, Middletown, NY 10940 (MLS # 4827718)
5 beds 2 baths 1,877 sqft $128,100
75 Brown Road Middletown, NY 10941
Photo of 75 Brown Road, Middletown, NY 10941 (MLS # 4826782)
2 beds 1 bath 2,704 sqft $132,000
111 Ruth Court Middletown, NY 10940
Photo of 111 Ruth Court, Middletown, NY 10940 (MLS # 4826719)
2 beds 2 baths 1,049 sqft $117,500
11 Silo Lane Middletown, NY 10940
Photo of 11 Silo Lane, Middletown, NY 10940 (MLS # 4823526)
3 beds 3 baths 1,452 sqft $148,000
6 Mckenzie Court Middletown, NY 10940
Photo of 6 Mckenzie Court, Middletown, NY 10940 (MLS # 4821617)
4 beds 3 baths 2,440 sqft $329,827
588 Van Burenville Road Middletown, NY 10940
Photo of 588 Van Burenville Road, Middletown, NY 10940 (MLS # 4811889)
4 beds 2 baths 2,112 sqft $125,000
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
15 East Avenue Middletown, NY 10940
Photo of 15 East Avenue, Middletown, NY 10940 (MLS # 4801288)
3 beds 2 baths 1,530 sqft $79,000
154 Prospect Avenue Middletown, NY 10940
Photo of 154 Prospect Avenue, Middletown, NY 10940 (MLS # 4753386)
3 beds 2 baths 1,710 sqft $200,000
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

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/