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

49 Broad Street Middletown, NY 10940
Photo of 49 Broad Street, Middletown, NY 10940 (MLS # 4805459)
1 bed 1 bath 616 sqft $1,000
133 Highland Avenue Middletown, NY 10940
Photo of 133 Highland Avenue, Middletown, NY 10940 (MLS # 4805106)
4 beds 3 baths 2,064 sqft $189,000
29 Bennett Street Middletown, NY 10940
Photo of 29 Bennett Street, Middletown, NY 10940 (MLS # 4730165)
3 beds 3 baths 2,874 sqft $169,000
67 Hulse Avenue Middletown, NY 10940
Photo of 67 Hulse Avenue, Middletown, NY 10940 (MLS # 4806336)
3 beds 2 baths 1,413 sqft $149,900
21 Center Street Middletown, NY 10940
Photo of 21 Center Street, Middletown, NY 10940 (MLS # 4806353)
2 beds 2 baths 1,000 sqft $1,500
Pocatello Road Middletown, NY 10940
Photo of Pocatello Road, Middletown, NY 10940 (MLS # 4736518)
0 beds 0 baths $179,500
213½ Highland Avenue Middletown, NY 10940
Photo of 213½ Highland Avenue, Middletown, NY 10940 (MLS # 4803713)
3 beds 2 baths 1,300 sqft $1,600
156 Dolson Avenue Middletown, NY 10940
Photo of 156 Dolson Avenue, Middletown, NY 10940 (MLS # 4805123)
0 beds 0 baths 54,065 sqft $12
144 Dolson Avenue Middletown, NY 10940
Photo of 144 Dolson Avenue, Middletown, NY 10940 (MLS # 4805122)
0 beds 0 baths 66,880 sqft $12
163 South Street Middletown, NY 10940
Photo of 163 South Street, Middletown, NY 10940 (MLS # 4806285)
2 beds 1 bath 1,032 sqft $72,800
31 Brick Pond Road Middletown, NY 10940
Photo of 31 Brick Pond Road, Middletown, NY 10940 (MLS # 4806274)
1 bed 2 baths 785 sqft $109,900
11 Talcott Place Middletown, NY 10940
Photo of 11 Talcott Place, Middletown, NY 10940 (MLS # 4806247)
3 beds 1 bath 1,445 sqft $67,500
150 Timothy Collard Road Middletown, NY 10940
Photo of 150 Timothy Collard Road, Middletown, NY 10940 (MLS # 4805720)
0 beds 0 baths $59,000
5 Windsor Mews Middletown, NY 10940
Photo of 5 Windsor Mews, Middletown, NY 10940 (MLS # 4805767)
3 beds 2 baths 1,234 sqft $159,000
35 Robertson Drive Middletown, NY 10940
Photo of 35 Robertson Drive, Middletown, NY 10940 (MLS # 4748024)
2 beds 1 bath 1,128 sqft $110,400

Sold Listings in Middletown

1308 Dolsontown Road Middletown, NY 10940
Photo of 1308 Dolsontown Road, Middletown, NY 10940 (MLS # 4553424)
3 beds 2 baths 1,652 sqft $315,000
3 Pine Street Middletown, NY 10940
Photo of 3 Pine Street, Middletown, NY 10940 (MLS # 4801789)
3 beds 1 bath 1,164 sqft $95,000
44 Amy Middletown, NY 10941
Photo of 44 Amy, Middletown, NY 10941 (MLS # 4742333)
4 beds 3 baths 2,004 sqft $135,000
17 Jimal Drive Middletown, NY 10940
Photo of 17 Jimal Drive, Middletown, NY 10940 (MLS # 4752918)
2 beds 2 baths 1,082 sqft $110,000
2 Rondack Road Middletown, NY 10941
Photo of 2 Rondack Road, Middletown, NY 10941 (MLS # 4752203)
3 beds 2 baths 2,124 sqft $145,000
84-86 Highland Avenue Middletown, NY 10940
Photo of 84-86 Highland Avenue, Middletown, NY 10940 (MLS # 4751802)
7 beds 6 baths 6,536 sqft $350,000
106 Lake Avenue Middletown, NY 10940
Photo of 106 Lake Avenue, Middletown, NY 10940 (MLS # 4745971)
3 beds 1 bath 1,152 sqft $145,000
8 Sarah Middletown, NY 10941
Photo of 8 Sarah, Middletown, NY 10941 (MLS # 4751470)
3 beds 2 baths 1,440 sqft $80,000
4 East Fortune Road, Unit E Middletown, NY 10941
Photo of 4 East Fortune Road, Unit E, Middletown, NY 10941 (MLS # 4751012)
1 bed 1 bath 775 sqft $60,000
22 Ross Lane Middletown, NY 10941
Photo of 22 Ross Lane, Middletown, NY 10941 (MLS # 4751075)
4 beds 3 baths 2,000 sqft $190,000
100 Hillside Drive, Unit E10 Middletown, NY 10941
Photo of 100 Hillside Drive, Unit E10, Middletown, NY 10941 (MLS # 4750803)
2 beds 3 baths 1,450 sqft $169,000
78 Inwood Road Middletown, NY 10941
Photo of 78 Inwood Road, Middletown, NY 10941 (MLS # 4724029)
1 bed 1 bath 750 sqft $62,000
2 West Fortune Road, Unit A Middletown, NY 10941
Photo of 2 West Fortune Road, Unit A, Middletown, NY 10941 (MLS # 4749934)
2 beds 2 baths 1,112 sqft $97,000
9 Dun Donald Circle Middletown, NY 10941
Photo of 9 Dun Donald Circle, Middletown, NY 10941 (MLS # 4750400)
3 beds 2 baths 1,402 sqft $210,000
479 Stony Ford Road Middletown, NY 10941
Photo of 479 Stony Ford Road, Middletown, NY 10941 (MLS # 4750432)
3 beds 2 baths 2,000 sqft $297,000

Walk Score for Middletown



Middletown School Data

Middletown School Districts

Middletown City 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
Maple Hill Elementary School
K-5, public
Otisville Elementary School
K-5, public
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