Monroe Woodbury School District
Orange County, New York
30 Single Homes offered from $500,000 to $800,000

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Photo of 172 Ridge Road
$514,999
25
172 Ridge Road
Highland Mills
 
3 Beds, 2 Full Bath
21,240 sqft, 0.49 Acre, 2 Garage
Age 63, Listed on Nov 01, 2025
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Photo of 468 Hillside Road .
$529,000
36
468 Hillside Road .
Monroe
 
4 Beds, 2 Full Bath
Sqft Not Included
Age 74,
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Photo of 62 Woodland Road
$537,500
50
62 Woodland Road
Highland Mills
 
4 Beds, 2 Full Bath, 1 Half Bath
26,289 sqft, 0.6 Acre, 2 Garage
Age 41, Listed on Mar 26, 2026
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Photo of 13 Eagle St
$550,000
37
13 Eagle St
Monroe
 
4 Beds, 3 Full Bath
1 Garage
Age 70, Listed on Dec 04, 2024
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Photo of 21 Crescent Place
$550,000
23
21 Crescent Place
Monroe
 
3 Beds, 2 Full Bath, 1 Half Bath
11,500 sqft, 0.26 Acre, 1 Garage
Age 66, Listed on Mar 16, 2026
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Photo of 36 Ironworks Road
$559,500
37
36 Ironworks Road
Monroe
 
4 Beds, 2 Full Bath, 1 Half Bath
22,002 sqft, 0.51 Acre, 2 Garage
Age 46, Listed on Dec 24, 2025
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Photo of 12 Round Lake Avenue
$570,000
18
12 Round Lake Avenue
Monroe
 
3 Beds, 1 Full Bath, 1 Half Bath
10,960 sqft, 0.25 Acre
Age 54, Listed on Dec 31, 2025
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Photo of 11 Hoffman Drive
$599,000
11 Hoffman Drive
Monroe
 
4 Beds, 2 Full Bath
21,501 sqft, 0.49 Acre
Age 61, Listed on Aug 07, 2024
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Photo of 11 Cunningham Drive
$599,000
22
11 Cunningham Drive
Monroe
 
4 Beds, 2 Full Bath, 1 Half Bath
20,000 sqft, 0.46 Acre, 1 Garage
Age 54, Listed on Mar 09, 2026
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Photo of 33 Winchester Drive
$620,000
48
33 Winchester Drive
Monroe
 
5 Beds, 2 Full Bath
20,000 sqft, 0.46 Acre, 2 Garage
Age 49, Listed on May 01, 2025
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Photo of 52 Woodland Road
$625,000
49
52 Woodland Road
Highland Mills
 
4 Beds, 2 Full Bath
13,068 sqft, 0.3 Acre, 2 Garage
Age 58, Listed on Mar 16, 2026
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Photo of 67 Carol Drive
$630,000
67 Carol Drive
Monroe
 
5 Beds, 3 Full Bath
52,272 sqft, 1.2 Acres
Age 51, Listed on Aug 07, 2024
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Photo of 64 Bayberry Drive
$639,000
45
64 Bayberry Drive
Monroe
 
5 Beds, 3 Full Bath, 1 Half Bath
91,476 sqft, 2.1 Acres
Age 53, Listed on Dec 23, 2025
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Photo of 22 Dogwood Drive
$649,900
50
22 Dogwood Drive
Central Valley
 
4 Beds, 2 Full Bath, 1 Half Bath
23,522 sqft, 0.54 Acre, 2 Garage
Age 40, Listed on Mar 28, 2026
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Photo of 24 Pearsall Drive
$650,000
1
24 Pearsall Drive
Monroe
 
4 Beds, 1 Full Bath, 1 Half Bath
9,375 sqft, 0.22 Acre, 2 Garage
Age 45, Listed on Feb 18, 2026
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Photo of 10 Leone Court
$659,950
50
10 Leone Court
Woodbury
 
5 Beds, 3 Full Bath, 1 Half Bath
2 Garage
Age 42, Listed on Mar 12, 2025
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Photo of 425 Stage Road
$669,000
35
425 Stage Road
Monroe
 
3 Beds, 2 Full Bath, 1 Half Bath
28,750 sqft, 0.66 Acre, 1 Garage
Age 96, Listed on Mar 06, 2025
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Photo of 70 Woodland Road
$699,000
41
70 Woodland Road
Monroe
 
4 Beds, 3 Full Bath
36,830 sqft, 0.85 Acre, 2 Garage
Age 27, Listed on Feb 16, 2026
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Photo of 360 Prospect Road
$699,000
50
360 Prospect Road
Chester
 
3 Beds, 3 Full Bath
139,392 sqft, 3.2 Acres, 2 Garage
Age 18, Listed on Dec 22, 2025
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Photo of 35 Peddler Hill Road
$699,000
23
35 Peddler Hill Road
Monroe
 
3 Beds, 1 Full Bath
28,349 sqft, 0.65 Acre
Age 55, Listed on Mar 30, 2026
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Photo of 120 Pine Tree Road
$699,999
50
120 Pine Tree Road
Monroe
 
4 Beds, 2 Full Bath, 1 Half Bath
45,090 sqft, 1.04 Acres, 1 Garage
Age 41, Listed on Nov 19, 2025
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Photo of 7 Country Hollow
$740,000
36
7 Country Hollow
Highland Mills
 
4 Beds, 2 Full Bath, 1 Half Bath
66,660 sqft, 1.53 Acres, 2 Garage
Age 27, Listed on Feb 26, 2026
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Photo of 57 Fawn Hill Road
$749,999
50
57 Fawn Hill Road
Tuxedo Park
 
5 Beds, 2 Full Bath, 1 Half Bath
47,916 sqft, 1.1 Acres, 2 Garage
Age 62, Listed on Feb 26, 2026
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Photo of 82 Winchester Drive
$759,000
36
82 Winchester Drive
Monroe
 
4 Beds, 2 Full Bath, 1 Half Bath
20,312 sqft, 0.47 Acre
Age 33, Listed on Nov 18, 2024
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Photo of 41 Serpi Road
$779,000
1
41 Serpi Road
Highland Mills
 
5 Beds, 2 Full Bath, 1 Half Bath
43,560 sqft, 1 Acre, 1 Garage
Age 50, Listed on Mar 24, 2026
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Photo of 9 Prestwick Drive
$790,000
48
9 Prestwick Drive
Monroe
 
4 Beds, 3 Full Bath
19,500 sqft, 0.45 Acre, 3 Garage
Age 18, Listed on Mar 14, 2026
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Photo of 47 Post Road
$799,000
33
47 Post Road
Monroe
 
4 Beds, 2 Full Bath, 2 Half Bath
59,002 sqft, 1.35 Acres
Age 21, Listed on Nov 06, 2024
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Photo of 4 Stillman Wye
$799,000
22
4 Stillman Wye
Monroe
 
2 Beds, 2 Full Bath
9,583 sqft, 0.22 Acre, 1 Garage
Age 1, Listed on Feb 06, 2026
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Photo of 18 Union Transfer
$799,000
2
18 Union Transfer
Monroe
 
2 Beds, 2 Full Bath
17,424 sqft, 0.4 Acre, 1 Garage
No Age, Listed on Feb 06, 2026
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Photo of 39 Southfield Falls
$799,000
1
39 Southfield Falls
Monroe
 
2 Beds, 2 Full Bath
20,473 sqft, 0.47 Acre, 1 Garage
No Age, Listed on Feb 06, 2026
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