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

37 Bowser Road Middletown, NY 10940
Photo of 37 Bowser Road, Middletown, NY 10940 (MLS # 4816393)
3 beds 2 baths 1,352 sqft $240,000
632 Route 211 Middletown, NY 10940
Photo of 632 Route 211, Middletown, NY 10940 (MLS # 4816533)
3 beds 1 bath 1,250 sqft $130,000
649 Mt Orange Road Middletown, NY 10940
Photo of 649 Mt Orange Road, Middletown, NY 10940 (MLS # 4816403)
3 beds 4 baths 2,675 sqft $479,999
128 Ridgewood Avenue Middletown, NY 10940
Photo of 128 Ridgewood Avenue, Middletown, NY 10940 (MLS # 4743804)
2 beds 1 bath 336 sqft $65,000
198 Elise Drive Middletown, NY 10941
Photo of 198 Elise Drive, Middletown, NY 10941 (MLS # 4816496)
4 beds 3 baths 2,588 sqft $461,900
116 Guymard Turnpike Middletown, NY 10940
Photo of 116 Guymard Turnpike, Middletown, NY 10940 (MLS # 4816480)
3 beds 4 baths 2,073 sqft $295,000
TBD Otis Road Middletown, NY 10940
Photo of TBD Otis Road, Middletown, NY 10940 (MLS # 4816453)
0 beds 0 baths $245,000
33 Cobblestone Middletown, NY 10940
Photo of 33 Cobblestone, Middletown, NY 10940 (MLS # 4816401)
3 beds 3 baths 2,450 sqft $285,000
Pocatello Road Middletown, NY 10940
Photo of Pocatello Road, Middletown, NY 10940 (MLS # 4815046)
0 beds 0 baths $49,000
44 Highrose Ridge Way Middletown, NY 10940
Photo of 44 Highrose Ridge Way, Middletown, NY 10940 (MLS # 4816302)
3 beds 3 baths 2,996 sqft $333,888
312 East Main Street Middletown, NY 10940
Photo of 312 East Main Street, Middletown, NY 10940 (MLS # 4816381)
3 beds 2 baths 1,152 sqft $165,000
53 Jimal Drive, Unit 53 Middletown, NY 10940
Photo of 53 Jimal Drive, Unit 53, Middletown, NY 10940 (MLS # 4814395)
1 bed 1 bath 893 sqft $100,000
25 Miller Heights Road Middletown, NY 10940
Photo of 25 Miller Heights Road, Middletown, NY 10940 (MLS # 4814144)
3 beds 2 baths 1,632 sqft $235,000
55 Sproat Street Middletown, NY 10940
Photo of 55 Sproat Street, Middletown, NY 10940 (MLS # 4815501)
3 beds 2 baths 1,274 sqft $149,000
37 California Avenue Middletown, NY 10940
Photo of 37 California Avenue, Middletown, NY 10940 (MLS # 4815459)
3 beds 1 bath 1,152 sqft $139,900

Sold Listings in Middletown

18 Eisenhower Drive Middletown, NY 10940
Photo of 18 Eisenhower Drive, Middletown, NY 10940 (MLS # 4744355)
3 beds 3 baths 1,736 sqft $147,000
35-37 Highland Avenue Middletown, NY 10940
Photo of 35-37 Highland Avenue, Middletown, NY 10940 (MLS # 4744436)
7 beds 2 baths 4,333 sqft $200,000
410 Sands Road Middletown, NY 10941
Photo of 410 Sands Road, Middletown, NY 10941 (MLS # 4747312)
0 beds 0 baths $28,000
21 Park Circle Drive Middletown, NY 10940
Photo of 21 Park Circle Drive, Middletown, NY 10940 (MLS # 4809594)
4 beds 2 baths 1,924 sqft $76,000
9 Sproat Street Middletown, NY 10940
Photo of 9 Sproat Street, Middletown, NY 10940 (MLS # 4746730)
4 beds 2 baths 1,741 sqft $105,000
11 Talcott Place Middletown, NY 10940
Photo of 11 Talcott Place, Middletown, NY 10940 (MLS # 4806247)
3 beds 1 bath 1,445 sqft $75,000
119 Academy Avenue Middletown, NY 10940
Photo of 119 Academy Avenue, Middletown, NY 10940 (MLS # 4805266)
3 beds 1 bath 1,484 sqft $67,000
41 Richmond Place Middletown, NY 10940
Photo of 41 Richmond Place, Middletown, NY 10940 (MLS # 4804575)
2 beds 1 bath 1,168 sqft $75,000
217-219 Highland Avenue Middletown, NY 10940
Photo of 217-219 Highland Avenue, Middletown, NY 10940 (MLS # 4751695)
3 beds 3 baths 2,228 sqft $171,000
27 Lake Avenue Middletown, NY 10940
Photo of 27 Lake Avenue, Middletown, NY 10940 (MLS # 4803869)
4 beds 2 baths 1,936 sqft $185,000
15 Canterbury Drive Middletown, NY 10940
Photo of 15 Canterbury Drive, Middletown, NY 10940 (MLS # 4803706)
4 beds 2 baths 1,836 sqft $234,000
35 Woodlawn Avenue Middletown, NY 10940
Photo of 35 Woodlawn Avenue, Middletown, NY 10940 (MLS # 4801987)
3 beds 2 baths 1,658 sqft $200,000
3 Magdalene Close, Unit 3 Middletown, NY 10940
Photo of 3 Magdalene Close, Unit 3, Middletown, NY 10940 (MLS # 4802677)
3 beds 2 baths 1,480 sqft $188,000
39 Rose Middletown, NY 10940
Photo of 39 Rose, Middletown, NY 10940 (MLS # 4802439)
3 beds 3 baths 2,844 sqft $211,000
480 Midland Lake Road Middletown, NY 10941
Photo of 480 Midland Lake Road, Middletown, NY 10941 (MLS # 4753126)
3 beds 3 baths 2,168 sqft $264,300

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