Middletown School District
Orange County, New York
18 Single Homes offered from $300,000 to $500,000

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Photo of 55 Hulse Avenue
$335,000
26
55 Hulse Avenue
Middletown
 
3 Beds, 1 Full Bath
7,500 sqft, 0.17 Acre
Age 96, Listed on Feb 13, 2026
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Photo of 23 Albert Street
$339,000
17
23 Albert Street
Middletown
 
4 Beds, 2 Full Bath
5,250 sqft, 0.12 Acre, 1 Garage
Age 106, Listed on Jan 29, 2025
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Photo of 16 Mountain Avenue
$344,900
23
16 Mountain Avenue
Middletown
 
4 Beds, 1 Full Bath, 1 Half Bath
11,250 sqft, 0.26 Acre
Age 54, Listed on Mar 10, 2026
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Photo of 91 Mountain Avenue
$350,000
22
91 Mountain Avenue
Middletown
 
3 Beds, 1 Full Bath
6,260 sqft, 0.14 Acre
Age 86, Listed on Dec 05, 2025
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Photo of 24 Kirbytown Road
$366,900
17
24 Kirbytown Road
Middletown
 
3 Beds, 1 Full Bath, 1 Half Bath
30,928 sqft, 0.71 Acre
Age 76,
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Photo of 3 Allerton Avenue
$399,000
34
3 Allerton Avenue
Middletown
 
3 Beds, 2 Full Bath, 1 Half Bath
1 Garage
Age 60, Listed on Nov 23, 2024
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Photo of 10 Wisner Avenue
$399,998
31
10 Wisner Avenue
Middletown
 
4 Beds, 1 Full Bath
8,446 sqft, 0.19 Acre
Age 65, Listed on Mar 19, 2026
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Photo of 35 Brookline Avenue
$403,000
25
35 Brookline Avenue
Middletown
 
4 Beds, 2 Full Bath
10,001 sqft, 0.23 Acre
Age 39, Listed on Sep 27, 2024
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Photo of 39 Hanford Street
$425,000
27
39 Hanford Street
Middletown
 
4 Beds, 2 Full Bath
3,824 sqft, 0.09 Acre, 1 Garage
Age 126, Listed on Mar 30, 2026
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Photo of 7 Commonwealth Avenue
$425,000
37
7 Commonwealth Avenue
Middletown
 
4 Beds, 1 Full Bath, 1 Half Bath
4,500 sqft, 0.1 Acre, 1 Garage
Age 99, Listed on Feb 26, 2025
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Photo of 16 Beth Place
$429,000
2
16 Beth Place
Middletown
 
3 Beds, 3 Full Bath
10,799 sqft, 0.25 Acre
Age 40, Listed on Oct 25, 2024
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Photo of 49 Bedford Avenue
$429,900
31
49 Bedford Avenue
Middletown
 
3 Beds, 2 Full Bath
7,500 sqft, 0.17 Acre
Age 76, Listed on Mar 02, 2025
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Photo of 674 Dosen Road
$439,889
32
674 Dosen Road
Middletown
 
3 Beds, 2 Full Bath
43,560 sqft, 1 Acre
Age 28, Listed on Jul 24, 2024
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Photo of 225 Monhagen Avenue
$455,000
13
225 Monhagen Avenue
Middletown
 
4 Beds, 2 Full Bath
13,600 sqft, 0.31 Acre, 3 Garage
Age 54, Listed on Mar 26, 2026
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Photo of 171 High Barney Road
$469,000
22
171 High Barney Road
Middletown
 
3 Beds, 2 Full Bath
20,864 sqft, 0.48 Acre
Age 53, Listed on Dec 10, 2025
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Photo of 61 Jasmine Drive
$489,900
35
61 Jasmine Drive
Middletown
 
2 Beds, 2 Full Bath
436 sqft, 0.01 Acre, 2 Garage
Age 19, Listed on Jan 12, 2025
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Photo of 20 Tammy Drive
$489,999
28
20 Tammy Drive
Middletown
 
3 Beds, 2 Full Bath, 1 Half Bath
24,849 sqft, 0.57 Acre, 1 Garage
Age 24, Listed on Mar 28, 2026
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Photo of 23 Wilkin Avenue
$499,999
46
23 Wilkin Avenue
Middletown
 
3 Beds, 2 Full Bath
5,000 sqft, 0.11 Acre, 1 Garage
Age 94, Listed on Jan 18, 2025
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