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

164 Ridgewood Avenue Middletown, NY 10940
Photo of 164 Ridgewood Avenue, Middletown, NY 10940 (MLS # 4909558)
0 beds 0 baths $40,000
226 Cottage Street Middletown, NY 10940
Photo of 226 Cottage Street, Middletown, NY 10940 (MLS # 4909526)
0 beds 0 baths 2,400 sqft $450,000
40 Hampton Court Middletown, NY 10941
Photo of 40 Hampton Court, Middletown, NY 10941 (MLS # 4909325)
3 beds 2 baths 1,440 sqft $1,600
0 Goshen Turnpike Middletown, NY 10941
Photo of 0 Goshen Turnpike, Middletown, NY 10941 (MLS # 4909520)
0 beds 0 baths $599,000
17 East Avenue Middletown, NY 10940
Photo of 17 East Avenue, Middletown, NY 10940 (MLS # 4908697)
7 beds 2 baths 2,249 sqft $65,000
25 Fairways Drive, Unit 10 Middletown, NY 10940
Photo of 25 Fairways Drive, Unit 10, Middletown, NY 10940 (MLS # 4900430)
2 beds 3 baths 1,337 sqft $2,000
6 The Lane Middletown, NY 10940
Photo of 6 The Lane, Middletown, NY 10940 (MLS # 4909281)
3 beds 2 baths 2,365 sqft $359,900
375 Blumel Road & Goshen Turnpike Middletown, NY 10941
Photo of 375 Blumel Road & Goshen Turnpike, Middletown, NY 10941 (MLS # 4909476)
5 beds 1 bath 2,080 sqft $139,000
225 Dolson Avenue, Unit 302 Middletown, NY 10940
Photo of 225 Dolson Avenue, Unit 302, Middletown, NY 10940 (MLS # 4909331)
0 beds 0 baths 2,085 sqft $275,000
85 Fairways Drive, Unit 539 Middletown, NY 10940
Photo of 85 Fairways Drive, Unit 539, Middletown, NY 10940 (MLS # 4909346)
3 beds 3 baths 2,430 sqft $469,000
39 Highland View Place Middletown, NY 10940
Photo of 39 Highland View Place, Middletown, NY 10940 (MLS # 4909302)
4 beds 3 baths 2,667 sqft $375,500
39 West Main Street, Unit 2A Middletown, NY 10940
Photo of 39 West Main Street, Unit 2A, Middletown, NY 10940 (MLS # 4908987)
1 bed 1 bath 750 sqft $1,250
0 Schutt & Avenue F Road Middletown, NY 10940
Photo of 0 Schutt & Avenue F Road, Middletown, NY 10940 (MLS # 4909189)
0 beds 0 baths $295,000
12 Poplar Lane Middletown, NY 10941
Photo of 12 Poplar Lane, Middletown, NY 10941 (MLS # 4906146)
3 beds 3 baths 1,520 sqft $1,900
725 Silver Lake Scotchtown Road Middletown, NY 10941
Photo of 725 Silver Lake Scotchtown Road, Middletown, NY 10941 (MLS # 4908438)
4 beds 3 baths 2,188 sqft $289,500

Sold Listings in Middletown

9 Brewster Drive Middletown, NY 10940
Photo of 9 Brewster Drive, Middletown, NY 10940 (MLS # 4901078)
3 beds 1 bath 1,056 sqft $130,900
39 Kensington Way Middletown, NY 10940
Photo of 39 Kensington Way, Middletown, NY 10940 (MLS # 4856894)
2 beds 2 baths 1,115 sqft $172,500
2 Linden Place Middletown, NY 10940
Photo of 2 Linden Place, Middletown, NY 10940 (MLS # 4845448)
0 beds 0 baths 3,715 sqft $140,000
39 Rose Lane Middletown, NY 10940
Photo of 39 Rose Lane, Middletown, NY 10940 (MLS # 4824401)
3 beds 3 baths 2,844 sqft $360,000
8 Charlotte Middletown, NY 10940
Photo of 8 Charlotte, Middletown, NY 10940 (MLS # 4854039)
2 beds 2 baths 1,270 sqft $46,000
119 Highland Avenue Middletown, NY 10940
Photo of 119 Highland Avenue, Middletown, NY 10940 (MLS # 4849916)
5 beds 4 baths 3,300 sqft $335,000
171 Watkins Avenue Middletown, NY 10940
Photo of 171 Watkins Avenue, Middletown, NY 10940 (MLS # 4853667)
3 beds 2 baths 1,560 sqft $195,000
109 Deer Ct Drive Middletown, NY 10940
Photo of 109 Deer Ct Drive, Middletown, NY 10940 (MLS # 4853618)
3 beds 2 baths 1,508 sqft $143,000
8-10 Crescent Place Middletown, NY 10940
Photo of 8-10 Crescent Place, Middletown, NY 10940 (MLS # 4853589)
4 beds 2 baths 2,340 sqft $167,500
9 Prince Street Middletown, NY 10940
Photo of 9 Prince Street, Middletown, NY 10940 (MLS # 4852964)
4 beds 2 baths 2,460 sqft $149,000
4 Marsham Court Middletown, NY 10940
Photo of 4 Marsham Court, Middletown, NY 10940 (MLS # 4852272)
3 beds 2 baths 1,604 sqft $199,000
48 Last Road Middletown, NY 10941
Photo of 48 Last Road, Middletown, NY 10941 (MLS # 4844618)
2 beds 2 baths 1,455 sqft $165,000
12 Poplar Lane Middletown, NY 10941
Photo of 12 Poplar Lane, Middletown, NY 10941 (MLS # 4852115)
3 beds 3 baths 1,520 sqft $165,000
54 Sprague Avenue Middletown, NY 10940
Photo of 54 Sprague Avenue, Middletown, NY 10940 (MLS # 4852396)
4 beds 2 baths 1,812 sqft $160,000
122 Gillen Road Middletown, NY 10940
Photo of 122 Gillen Road, Middletown, NY 10940 (MLS # 4852278)
3 beds 1 bath 1,242 sqft $120,500

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/