Monroe Woodbury School District
Orange County, New York
22 Single Homes offered from $800,000+

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Photo of 31 Jill Road
$800,000
40
31 Jill Road
Highland Mills
 
4 Beds, 2 Full Bath, 1 Half Bath
82,764 sqft, 1.9 Acres
Age 24, Listed on Oct 23, 2024
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Photo of 13 Mansion Ridge Boulevard
$839,999
0
13 Mansion Ridge Boulevard
Monroe
 
6 Beds, 4 Full Bath, 1 Half Bath
30,544 sqft, 0.7 Acre, 2 Garage
Age 24, Listed on Mar 25, 2024
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Photo of 444 Bramertown Road
$849,900
26
444 Bramertown Road
Tuxedo Park
 
3 Beds, 2 Full Bath
1 Garage
Age 44, Listed on Jan 30, 2025
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Photo of 7 Maidstone Lane
$850,000
50
7 Maidstone Lane
Monroe
 
4 Beds, 3 Full Bath
20,482 sqft, 0.47 Acre, 3 Garage
Age 15, Listed on Mar 18, 2026
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Photo of 651 Lakes Road
$874,400
7
651 Lakes Road
Monroe
 
4 Beds, 2 Full Bath
43,950 sqft, 1.01 Acres, 2 Garage
Age 76, Listed on Nov 07, 2025
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Photo of 4 Makan Road
$875,000
50
4 Makan Road
Monroe
 
5 Beds, 4 Full Bath
22,779 sqft, 0.52 Acre, 2 Garage
Age 15, Listed on Sep 03, 2025
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Photo of 19 Mansion Ridge Boulevard
$879,000
33
19 Mansion Ridge Boulevard
Monroe
 
4 Beds, 2 Full Bath, 1 Half Bath
25,265 sqft, 0.58 Acre, 2 Garage
Age 24, Listed on Feb 27, 2025
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Photo of 46 Mansion Ridge Boulevard
$895,000
35
46 Mansion Ridge Boulevard
Monroe
 
3 Beds, 2 Full Bath, 1 Half Bath
43,560 sqft, 1 Acre, 2 Garage
Age 24, Listed on Mar 12, 2026
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Photo of 27 Union Transfer
$899,000
48
27 Union Transfer
Monroe
 
2 Beds, 2 Full Bath
10,890 sqft, 0.25 Acre, 1 Garage
Age 1, Listed on Feb 06, 2026
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Photo of 8 Alloway Crescent
$899,000
50
8 Alloway Crescent
Highland Mills
 
4 Beds, 3 Full Bath
35,284 sqft, 0.81 Acre, 2 Garage
Age 24, Listed on Nov 06, 2025
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Photo of 57 Southfield Falls
$900,000
37
57 Southfield Falls
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 24 Union Transfer
$925,000
7
24 Union Transfer
Monroe
 
2 Beds, 2 Full Bath
9,583 sqft, 0.22 Acre, 1 Garage
No Age, Listed on Feb 06, 2026
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Photo of 208 Oakland Avenue
$929,000
50
208 Oakland Avenue
Monroe
 
4 Beds, 4 Full Bath, 1 Half Bath
17,170 sqft, 0.39 Acre, 2 Garage
Age 22, Listed on Oct 29, 2025
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Photo of 27 Catskill High Rail
$940,000
26
27 Catskill High Rail
Monroe
 
7 Beds, 3 Full Bath, 1 Half Bath
30,056 sqft, 0.69 Acre, 1 Garage
Age 7, Listed on Mar 25, 2026
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Photo of 4 Lambros Drive
$999,000
34
4 Lambros Drive
Monroe
 
5 Beds, 4 Full Bath, 1 Half Bath
65,340 sqft, 1.5 Acres, 3 Garage
Age 80, Listed on Feb 17, 2026
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Photo of 12 Damian Court
$999,000
34
12 Damian Court
Chester
 
5 Beds, 4 Full Bath
130,680 sqft, 3 Acres, 3 Garage
Age 21, Listed on Jan 16, 2026
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Photo of 53 Gibson Hill Road
$999,999
45
53 Gibson Hill Road
Chester
 
5 Beds, 4 Full Bath
135,036 sqft, 3.1 Acres, 3 Garage
Age 16,
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Photo of 556 Lakes Road
$1,025,000
22
556 Lakes Road
Monroe
 
4 Beds, 3 Full Bath
56,628 sqft, 1.3 Acres, 1 Garage
Age 85, Listed on Jan 13, 2026
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Photo of 11 Cliff Court
$1,095,000
10
11 Cliff Court
Monroe
 
4 Beds, 2 Full Bath, 1 Half Bath
28,140 sqft, 0.65 Acre, 2 Garage
Age 58, Listed on Dec 29, 2025
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Photo of 221 Smith Clove Road
$1,395,000
50
221 Smith Clove Road
Highland Mills
 
4 Beds, 4 Full Bath, 1 Half Bath
283,140 sqft, 6.5 Acres, 3 Garage
Age 16, Listed on Feb 11, 2026
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Photo of 43 Van Arsdale Road
$1,500,000
0
43 Van Arsdale Road
Monroe
 
5 Beds, 3 Full Bath, 1 Half Bath
5,220 sqft, 0.12 Acre, 2 Garage
Age 3,
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Photo of 24 Jill Road
$1,750,000
43
24 Jill Road
Highland Mills
 
6 Beds, 3 Full Bath, 1 Half Bath
248,292 sqft, 5.7 Acres
Age 171, Listed on Aug 08, 2025
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