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PA: 215.699.5555
Middletown
Orange County, New York
29 Single Homes offered from $300,000 to $500,000
Page
1
2
3
$324,999
44
20 Benton Avenue
Middletown
3 Beds, 2 Full Bath
6,750 sqft, 0.15 Acre
Age 112, Listed on Sep 12, 2025
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$325,000
41
138 Camp Orange Road
Middletown
3 Beds, 1 Full Bath
60,984 sqft, 1.4 Acres, 2 Garage
Age 85, Listed on Oct 02, 2025
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$339,000
17
23 Albert Street
Middletown
4 Beds, 2 Full Bath
5,250 sqft, 0.12 Acre, 1 Garage
Age 105, Listed on Jan 29, 2025
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$339,900
34
28 Spring Street
Middletown
4 Beds, 2 Full Bath
7,854 sqft, 0.18 Acre
Age 105, Listed on Sep 23, 2024
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$360,000
17
24 Edinburgh Road
Middletown
4 Beds, 2 Full Bath
15,200 sqft, 0.35 Acre
Age 58, Listed on Jun 27, 2025
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$366,900
17
24 Kirbytown Road
Middletown
3 Beds, 1 Full Bath, 1 Half Bath
30,928 sqft, 0.71 Acre
Age 75
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$369,900
10
9 Fairview Avenue
Middletown
3 Beds, 1 Full Bath, 1 Half Bath
5,249 sqft, 0.12 Acre
Age 109, Listed on Feb 25, 2025
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$375,000
25
71 Commonwealth Avenue
Middletown
3 Beds, 1 Full Bath
4,985 sqft, 0.11 Acre, 1 Garage
Age 78, Listed on Jul 25, 2025
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$379,999
25
408 County Route 22
Middletown
3 Beds, 1 Full Bath, 1 Half Bath
52,272 sqft, 1.2 Acres, 2 Garage
Age 59, Listed on Aug 28, 2025
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$380,000
36
25 Meyer Road
Middletown
3 Beds, 2 Full Bath
52,272 sqft, 1.2 Acres
Age 53, Listed on Jan 08, 2025
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$385,000
45
12 State Street
Middletown
2 Beds, 1 Full Bath, 1 Half Bath
5,000 sqft, 0.11 Acre
Age 31, Listed on Oct 23, 2025
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Page
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$385,000
44
100 Academy Avenue
Middletown
4 Beds, 2 Full Bath
10,261 sqft, 0.24 Acre
Age 125, Listed on Aug 08, 2025
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$389,000
32
15 Morningside Drive
Middletown
3 Beds, 1 Full Bath, 1 Half Bath
15,856 sqft, 0.36 Acre
Age 52, Listed on Nov 07, 2024
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$399,000
30
77 Prince Street
Middletown
3 Beds, 2 Full Bath, 1 Half Bath
5,406 sqft, 0.12 Acre, 1 Garage
Age 35, Listed on Aug 07, 2025
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$399,000
34
3 Allerton Avenue
Middletown
3 Beds, 2 Full Bath, 1 Half Bath
1 Garage
Age 59, Listed on Nov 23, 2024
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$399,900
33
727 Route 17m
Middletown
1 Beds, 1 Full Bath
18,150 sqft, 0.42 Acre, 2 Garage
Age 97, Listed on Oct 01, 2025
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$403,000
25
35 Brookline Avenue
Middletown
4 Beds, 2 Full Bath
10,001 sqft, 0.23 Acre
Age 38, Listed on Sep 27, 2024
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$414,999
27
11 Dolson
Middletown
3 Beds, 2 Full Bath, 1 Half Bath
Sqft Not Included
Age 113, Listed on Aug 13, 2025
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$425,000
37
7 Commonwealth Avenue
Middletown
4 Beds, 1 Full Bath, 1 Half Bath
4,500 sqft, 0.1 Acre, 1 Garage
Age 98, Listed on Feb 26, 2025
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$429,000
2
16 Beth Place
Middletown
3 Beds, 3 Full Bath
10,799 sqft, 0.25 Acre
Age 39, Listed on Oct 25, 2024
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$429,900
27
55 Beverly Drive
Middletown
3 Beds, 2 Full Bath
23,040 sqft, 0.53 Acre, 2 Garage
Age 62, Listed on Feb 14, 2025
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$429,900
31
49 Bedford Avenue
Middletown
3 Beds, 2 Full Bath
7,500 sqft, 0.17 Acre
Age 75, Listed on Mar 02, 2025
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$439,889
32
674 Dosen Road
Middletown
3 Beds, 2 Full Bath
43,560 sqft, 1 Acre
Age 27, Listed on Jul 24, 2024
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$440,000
41
4 Thistle Lane
Middletown
4 Beds, 2 Full Bath, 1 Half Bath
52,272 sqft, 1.2 Acres, 2 Garage
Age 38, Listed on Mar 20, 2025
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$460,000
50
7 Orchard Street
Middletown
5 Beds, 2 Full Bath, 1 Half Bath
5,715 sqft, 0.13 Acre, 2 Garage
Age 155, Listed on Oct 07, 2025
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$489,900
30
22 Mark Drive
Middletown
3 Beds, 2 Full Bath, 1 Half Bath
74,052 sqft, 1.7 Acres, 2 Garage
Age 45, Listed on Oct 01, 2025
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$489,900
35
61 Jasmine Drive
Middletown
2 Beds, 2 Full Bath
436 sqft, 0.01 Acre, 2 Garage
Age 18, Listed on Jan 12, 2025
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$499,000
47
29 Keasel Road
Middletown
3 Beds, 2 Full Bath, 1 Half Bath
56,628 sqft, 1.3 Acres, 2 Garage
Age 63, Listed on Aug 13, 2025
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$499,999
46
23 Wilkin Avenue
Middletown
3 Beds, 2 Full Bath
5,000 sqft, 0.11 Acre, 1 Garage
Age 93, Listed on Jan 18, 2025
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