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
2 beds 1 bath 900 sqft $1,575
8 Peace Drive Middletown, NY 10941
Photo of 8 Peace Drive, Middletown, NY 10941 (MLS # 6005519)
3 beds 2 baths 1,670 sqft $275,000
48 Industrial Place, Unit Upstairs Middletown, NY 10940
Photo of 48 Industrial Place, Unit Upstairs, Middletown, NY 10940 (MLS # 6004120)
0 beds 0 baths 8,000 sqft $12
228 Linden Avenue Middletown, NY 10940
Photo of 228 Linden Avenue, Middletown, NY 10940 (MLS # 6006912)
3 beds 1 bath 1,222 sqft $139,900
162 Bloomingburg Road Middletown, NY 10940
Photo of 162 Bloomingburg Road, Middletown, NY 10940 (MLS # 4940407)
0 beds 0 baths 1,550 sqft $2,200
Evergreen Drive Middletown, NY 10940
0 beds 0 baths $35,000
Evergreen Middletown, NY 10940
0 beds 0 baths $95,000
99 Woodlake Drive, Unit 26 Middletown, NY 10940
Photo of 99 Woodlake Drive, Unit 26, Middletown, NY 10940 (MLS # 6004334)
2 beds 4 baths 2,161 sqft $2,000
228 Wickham (211) Avenue, Unit Middletown Middletown, NY 10940
Photo of 228 Wickham (211) Avenue, Unit Middletown, Middletown, NY 10940 (MLS # 6005680)
0 beds 0 baths 1,663 sqft $159,900
225 Deer Ct Drive Middletown, NY 10940
Photo of 225 Deer Ct Drive, Middletown, NY 10940 (MLS # 6006708)
2 beds 3 baths 1,831 sqft $219,000
414 Kirbytown Road Middletown, NY 10940
Photo of 414 Kirbytown Road, Middletown, NY 10940 (MLS # 6006218)
3 beds 2 baths 1,440 sqft $299,000
202-204 Wickham Avenue Middletown, NY 10940
Photo of 202-204 Wickham Avenue, Middletown, NY 10940 (MLS # 6006564)
0 beds 0 baths 6,000 sqft $499,000
36 Old Anvil Lane Middletown, NY 10940
Photo of 36 Old Anvil Lane, Middletown, NY 10940 (MLS # 6006512)
3 beds 2 baths 1,452 sqft $1,700
38 Lafayette Avenue Middletown, NY 10940
Photo of 38 Lafayette Avenue, Middletown, NY 10940 (MLS # 6006006)
4 beds 2 baths 1,516 sqft $235,000
28 Sofia Court Middletown, NY 12589
Photo of 28 Sofia Court, Middletown, NY 12589 (MLS # 6005319)
0 beds 0 baths $130,000

Sold Listings in Middletown

209 Elise Drive Middletown, NY 10941
Photo of 209 Elise Drive, Middletown, NY 10941 (MLS # 4800816)
5 beds 3 baths 3,572 sqft $480,000
17 Kennedy Terrace Middletown, NY 10940
Photo of 17 Kennedy Terrace, Middletown, NY 10940 (MLS # 4852810)
4 beds 3 baths 2,088 sqft $280,000
176 Elise Drive Middletown, NY 10941
Photo of 176 Elise Drive, Middletown, NY 10941 (MLS # 4710746)
4 beds 3 baths 2,588 sqft $415,150
517 East Main Street Middletown, NY 10940
Photo of 517 East Main Street, Middletown, NY 10940 (MLS # 5124227)
0 beds 0 baths 944 sqft $130,000
152 Sycamore Drive Middletown, NY 10940
Photo of 152 Sycamore Drive, Middletown, NY 10940 (MLS # 5121152)
2 beds 2 baths 1,110 sqft $190,000
1 North Aspen Road Middletown, NY 10940
Photo of 1 North Aspen Road, Middletown, NY 10940 (MLS # 5120987)
3 beds 2 baths 1,496 sqft $114,000
226 Cottage Street Middletown, NY 10940
Photo of 226 Cottage Street, Middletown, NY 10940 (MLS # 4909526)
0 beds 0 baths 2,400 sqft $365,000
117 Highland Lake Road Middletown, NY 10940
Photo of 117 Highland Lake Road, Middletown, NY 10940 (MLS # 5070407)
3 beds 2 baths 1,024 sqft $240,000
21 Highland View Place Middletown, NY 10940
Photo of 21 Highland View Place, Middletown, NY 10940 (MLS # 5118457)
4 beds 3 baths 3,557 sqft $280,000
20 Rockwell Avenue Middletown, NY 10940
Photo of 20 Rockwell Avenue, Middletown, NY 10940 (MLS # 4939732)
2 beds 1 bath 864 sqft $175,000
354 Concord Lane Middletown, NY 10940
Photo of 354 Concord Lane, Middletown, NY 10940 (MLS # 5116439)
2 beds 2 baths 924 sqft $102,000
18 Beers Drive Middletown, NY 10940
Photo of 18 Beers Drive, Middletown, NY 10940 (MLS # 4994877)
3 beds 2 baths 1,810 sqft $160,000
17 Prospect Avenue Middletown, NY 10940
Photo of 17 Prospect Avenue, Middletown, NY 10940 (MLS # 5111845)
4 beds 2 baths 2,184 sqft $155,000
4 Harrison Street Middletown, NY 10940
Photo of 4 Harrison Street, Middletown, NY 10940 (MLS # 5110329)
5 beds 2 baths 2,059 sqft $235,000
1 Allerton Avenue Middletown, NY 10940
Photo of 1 Allerton Avenue, Middletown, NY 10940 (MLS # 4919793)
3 beds 2 baths 1,884 sqft $187,500

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/