Chester, NY Homes for Sale & Real Estate

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1-60 of 85 Homes
$355,000 | 255 Heritage Lane, Monroe, NY 10950
1/2
Coldwell Banker Realty Coming Soon

$355,000

3
Bedrooms
1,585
Square Feet

255 Heritage Lane, Monroe, NY 10950

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$565,000 | 74 Heaton Road, Monroe, NY 10950
1/22
Listed By Coldwell Banker Realty

$565,000

3
Bedrooms
1,676
Square Feet
0.36
Acres

74 Heaton Road, Monroe, NY 10950

$495,000 | 8 Bridle Lane, Chester, NY 10918
1/45

Listing Courtesy of Keller Williams Realty

Coming Soon

$495,000

4
Bedrooms
1,820
Square Feet
0.37
Acres

8 Bridle Lane, Chester, NY 10918

$799,000 | 3 Garnett Hill, Chester, NY 10918
1/50

Listing Courtesy of Keller Williams Realty

Coming Soon

$799,000

4
Bedrooms
2,516
Square Feet
3
Acres

3 Garnett Hill, Chester, NY 10918

$615,000 | 412 Laroe Road, Chester, NY 10918
1/46

Listing Courtesy of Howard Hanna Rand Realty

Open: 8/15 01:00PM - 03:00PM

$615,000

3
Bedrooms
1,848
Square Feet
2.4
Acres

412 Laroe Road, Chester, NY 10918

$340,000 | 166 Bull Mill Road, Chester, NY 10918
1/37

Listing Courtesy of Keller Williams Valley Realty

$340,000

2
Bedrooms
1,004
Square Feet
1.8
Acres

166 Bull Mill Road, Chester, NY 10918

$389,900 | 213 Eagleton Drive, Monroe, NY 10950
1/32

Listing Courtesy of Keller Williams Valley Realty; DeSimone Real Estate

$389,900

3
Bedrooms
1,694
Square Feet

213 Eagleton Drive, Monroe, NY 10950

$475,000 | 21 Trotting Drive, Chester, NY 10918
1/50

Listing Courtesy of Keller Williams Realty

$475,000

3
Bedrooms
1,624
Square Feet
0.39
Acres

21 Trotting Drive, Chester, NY 10918

$375,000 | 1310 Whispering Hills Drive, Chester, NY 10918
1/36

Listing Courtesy of Hudson Premium Realty

$375,000

3
Bedrooms
1,331
Square Feet

1310 Whispering Hills Drive, Chester, NY 10918

$699,900 | 176 Beverly Road, Chester, NY 10918
1/39

Listing Courtesy of Owner Entry.com

Open: 8/15 01:00PM - 03:00PM

$699,900

4
Bedrooms
2,715
Square Feet
2.5
Acres

176 Beverly Road, Chester, NY 10918

$469,000 | 70 Main Street, Chester, NY 10918
1/27

Listing Courtesy of Curasi Realty, Inc.

$469,000

3
Bedrooms
1,357
Square Feet
0.76
Acres

70 Main Street, Chester, NY 10918

$449,000 | 66 Whitetail Run, Chester, NY 10918
1/50

Listing Courtesy of Howard Hanna Rand Realty

Open: 8/15 12:00PM - 02:00PM

$449,000

3
Bedrooms
1,500
Square Feet
0.92
Acres

66 Whitetail Run, Chester, NY 10918

a front view of a house with a yard
1/35

Listing Courtesy of Howard Hanna Rand Realty

$369,000

3
Bedrooms
1,331
Square Feet

2522 Whispering Hills Drive, Chester, NY 10918

$425,000 | 23 Pike Court, Monroe, NY 10950
1/8

Listing Courtesy of RE/MAX Benchmark Realty Group

$425,000

3
Bedrooms
2,460
Square Feet
0.75
Acres

23 Pike Court, Monroe, NY 10950

$370,000 | 33 Meadow Avenue, Chester, NY 10918
1/21

Listing Courtesy of River Realty Services, Inc.

$370,000

3
Bedrooms
1,561
Square Feet
0.37
Acres

33 Meadow Avenue, Chester, NY 10918

$750,000 | 3 Hilltop Lane, Chester, NY 10918

Listing Courtesy of MK Realty Inc

$750,000

5
Bedrooms
2,700
Square Feet
0.08
Acres

3 Hilltop Lane, Chester, NY 10918

$325,000 | 151 Main Street, Chester, NY 10918
1/16

Listing Courtesy of Hudson Valley Griffith

$325,000

4
Bedrooms
1,504
Square Feet
0.08
Acres

151 Main Street, Chester, NY 10918

$279,999 | 2007 Whispering Hills Drive, Chester, NY 10918
1/44

Listing Courtesy of Keller Williams Realty

$279,999

2
Bedrooms
1,086
Square Feet

2007 Whispering Hills Drive, Chester, NY 10918

$575,000 | 68 Conklingtown Road, Unit 1&2, Chester, NY 10918
1/38

Listing Courtesy of MS Realty Group USA, Inc

$575,000

6
Bedrooms
Unavailable
Square Feet
1
Acres

68 Conklingtown Road, Unit 1&2, Chester, NY 10918

a front view of a house with a yard
1/33

Listing Courtesy of Howard Hanna Rand Realty

$315,000

2
Bedrooms
1,072
Square Feet

4008 Whispering Hills Drive, Chester, NY 10918

$750,000 | 1 Hilltop Lane, Chester, NY 10918

Listing Courtesy of MK Realty Inc

$750,000

5
Bedrooms
2,700
Square Feet
0.08
Acres

1 Hilltop Lane, Chester, NY 10918

a front view of house with yard and trees
1/34

Listing Courtesy of eXp Realty

$650,000

3
Bedrooms
2,520
Square Feet
1.9
Acres

29 Murray Drive, Chester, NY 10918

a front view of house with yard and green space
1/29

Listing Courtesy of Terrie OConnor

$550,000

3
Bedrooms
1,644
Square Feet
0.28
Acres

56 Poplar Drive, Monroe, NY 10950

a view of a backyard with a garden
1/49

Listing Courtesy of Keller Williams Hudson Valley

$389,000

3
Bedrooms
1,062
Square Feet
0.95
Acres

185 Oxford Road, Chester, NY 10918

a front view of a house with garden
1/29

Listing Courtesy of Howard Hanna Rand Realty

$549,999

4
Bedrooms
2,098
Square Feet
1
Acres

7 Lake View Drive, Chester, NY 10918

a front view of a house with a yard
1/36

Listing Courtesy of Howard Hanna Rand Realty

$799,000

4
Bedrooms
3,070
Square Feet
1.7
Acres

197 Oxford Road, Chester, NY 10918

$579,900 | 50 Hambletonian Avenue, Chester, NY 10918
1/19

Listing Courtesy of Greene Realty Group

$579,900

3
Bedrooms
1,583
Square Feet
4
Acres

50 Hambletonian Avenue, Chester, NY 10918

$374,999 | 241 Meadow Avenue, Chester, NY 10918
1/35

Listing Courtesy of Keller Williams Realty

$374,999

4
Bedrooms
1,560
Square Feet
0.94
Acres

241 Meadow Avenue, Chester, NY 10918

$389,900 | 4114 Whispering Hills Drive, Chester, NY 10918
1/29
Listed By Coldwell Banker Realty

$389,900

3
Bedrooms
1,393
Square Feet

4114 Whispering Hills Drive, Chester, NY 10918

a front view of a house with garden
1/35

Listing Courtesy of HomeSmart Homes & Estates

$350,000

3
Bedrooms
1,086
Square Feet

2604 Whispering Hills Drive, Chester, NY 10918

$360,000 | 154 Eagleton Drive, Monroe, NY 10950
1/18

Listing Courtesy of Keller Williams Realty

$360,000

3
Bedrooms
1,585
Square Feet

154 Eagleton Drive, Monroe, NY 10950

$750,000 | 2 Hemlock Court, Chester, NY 10918
1/3

Listing Courtesy of MK Realty Inc

$750,000

5
Bedrooms
2,700
Square Feet
0.08
Acres

2 Hemlock Court, Chester, NY 10918

$345,000 | 402 Mountain Laurel Drive, Monroe, NY 10950
1/31

Listing Courtesy of Keller Williams Realty

Open: 8/15 11:00AM - 03:00PM

$345,000

3
Bedrooms
1,840
Square Feet

402 Mountain Laurel Drive, Monroe, NY 10950

a view of a brick house with large windows

Listing Courtesy of MK Realty Inc

$725,000

3
Bedrooms
2,677
Square Feet

1 Arborvitae Court, Chester, NY 10918

a view of a house with wooden deck and a yard
1/40

Listing Courtesy of Epique Realty

$649,999

4
Bedrooms
2,316
Square Feet
2.5
Acres

424 Laroe Road, Chester, NY 10918

$635,000 | 10 Hidden Drive, Monroe, NY 10950
1/46

Listing Courtesy of Century 21 Full Service Realty

$635,000

4
Bedrooms
3,636
Square Feet
1.3
Acres

10 Hidden Drive, Monroe, NY 10950

$349,999 | 3414 Whispering Hills Drive, Chester, NY 10918
1/34

Listing Courtesy of KW Hudson Valley United

$349,999

3
Bedrooms
1,316
Square Feet

3414 Whispering Hills Drive, Chester, NY 10918

$575,000 | 11 Chandler Drive, Chester, NY 10918
1/32
Listed By Coldwell Banker RealtyOpen: 8/16 11:00AM - 01:00PM

$575,000

3
Bedrooms
1,908
Square Feet
0.46
Acres

11 Chandler Drive, Chester, NY 10918

$549,000 | 44 Wilson Road, Monroe, NY 10950
1/42

Listing Courtesy of Keller Williams Realty

$549,000

3
Bedrooms
2,374
Square Feet
0.35
Acres

44 Wilson Road, Monroe, NY 10950

a front view of a house with a yard
1/5

Listing Courtesy of MK Realty Inc

$850,000

5
Bedrooms
3,200
Square Feet
0.08
Acres

5 Hilltop Lane, Chester, NY 10918

$800,000 | 985 Craigville Road, Chester, NY 10918
1/36

Listing Courtesy of Serhant LLC

$800,000

4
Bedrooms
3,100
Square Feet
3
Acres

985 Craigville Road, Chester, NY 10918

a front view of a house with a yard
1/50

Listing Courtesy of MK Realty Inc

$750,000

5
Bedrooms
2,700
Square Feet
0.08
Acres

3 Hemlock Court, Chester, NY 10918

a front view of a house with a garden and trees
1/31

Listing Courtesy of Howard Hanna Rand Realty

$295,000

2
Bedrooms
1,086
Square Feet

2119 Whispering Hills Drive, Chester, NY 10918

$280,000 | 815 Craigville Road, Chester, NY 10918
1/50

Listing Courtesy of Ellis Sotheby's Intl Realty

$280,000

3
Bedrooms
2,016
Square Feet
0.69
Acres

815 Craigville Road, Chester, NY 10918

$789,900 | 19 Grand View Terrace, Chester, NY 10918
1/37

Listing Courtesy of eXp Realty

$789,900

5
Bedrooms
4,697
Square Feet
0.42
Acres

19 Grand View Terrace, Chester, NY 10918

a front view of a house with garden
1/50

Listing Courtesy of Howard Hanna Rand Realty

$1,195,000

4
Bedrooms
4,281
Square Feet
2.3
Acres

22 Goshen Road, Chester, NY 10918

$900,000 | 651 Lakes Road, Monroe, NY 10950
1/7

Listing Courtesy of Howard Hanna Rand Realty

$900,000

4
Bedrooms
2,466
Square Feet
1.01
Acres

651 Lakes Road, Monroe, NY 10950

$1,299,000 | 16 Sunset Ridge, Monroe, NY 10950
1/9

Listing Courtesy of Serhant LLC

$1,299,000

4
Bedrooms
5,712
Square Feet
5.9
Acres

16 Sunset Ridge, Monroe, NY 10950

$990,000 | 1 Oakland Avenue, Chester, NY 10918
1/50

Listing Courtesy of Howard Hanna Rand Realty

$990,000

4
Bedrooms
3,955
Square Feet
6.8
Acres

1 Oakland Avenue, Chester, NY 10918

a house with trees in the background
1/35

Listing Courtesy of eRealty Advisors, Inc

$875,000

4
Bedrooms
3,656
Square Feet
7.1
Acres

49 Stone Mountain Trail, Chester, NY 10918

a front view of a house with a yard and garage
1/38

Listing Courtesy of SPIRAL NY Real Estate LLC

$1,200,000

4
Bedrooms
2,711
Square Feet
6
Acres

63 Whitetail Run, Chester, NY 10918

$675,000 | 335 Laroe Road, Chester, NY 10918
1/35

Listing Courtesy of Coldwell Banker Choice Prop.

$675,000

4
Bedrooms
2,784
Square Feet
3.2
Acres

335 Laroe Road, Chester, NY 10918

$549,900 | 3318 Highway 94, Chester, NY 10918
1/29

Listing Courtesy of Howard Hanna Rand Realty

$549,900

3
Bedrooms
2,138
Square Feet
0.45
Acres

3318 Highway 94, Chester, NY 10918

a front view of house with yard and green space
1/42

Listing Courtesy of BHG Real Estate Green Team

$949,000

4
Bedrooms
3,332
Square Feet
2.3
Acres

19 Bull Mine Road, Chester, NY 10918

$429,000 | 4 Maple Lane, Monroe, NY 10950
1/19

Listing Courtesy of Flag Realty Group

$429,000

3
Bedrooms
1,460
Square Feet
0.33
Acres

4 Maple Lane, Monroe, NY 10950

$999,900 | 206 Greycourt Road, Chester, NY 10918
1/49

Listing Courtesy of Cronin & Company Real Estate

$999,900

Unavailable
Bedrooms
Unavailable
Bathrooms
4,032
Square Feet
3.2
Acres

206 Greycourt Road, Chester, NY 10918

$520,000 | 94 Booth Road, Chester, NY 10918
1/23
Listed By Compass

$520,000

3
Bedrooms
2,083
Square Feet
1.8
Acres

94 Booth Road, Chester, NY 10918

$785,000 | 4 Debbie Court, Chester, NY 10918
1/49

Listing Courtesy of Flag Realty Group

$785,000

5
Bedrooms
5,403
Square Feet
5.4
Acres

4 Debbie Court, Chester, NY 10918

$559,000 | 24 Walnut Street, Chester, NY 10918
1/28

Listing Courtesy of Keller Williams Village Sq Rlt

$559,000

4
Bedrooms
2,698
Square Feet
0.56
Acres

24 Walnut Street, Chester, NY 10918

$825,000 | 45 Whitetail Run, Chester, NY 10918
1/46

Listing Courtesy of Hudson Valley Home Connection

$825,000

4
Bedrooms
2,732
Square Feet
10.9
Acres

45 Whitetail Run, Chester, NY 10918

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