Homes Recently Sold in Chester, NY

price
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1-25 of 25 Homes
Sold, last 90 days
an aerial view of a house with garden space and street view

Listing Courtesy of HomeSmart Homes & Estates

Closed 1/7/26

$419,999

3
Bedrooms
1,698
Square Feet
Unavailable
Acres

354 Rande Road, Monroe, NY 10950

front view of a house with a yard

Listing Courtesy of Keller Williams Hudson Valley

Closed 1/12/26

$669,000

4
Bedrooms
3,092
Square Feet
0.18
Acres

2 Dawn Court, Chester, NY 10918

$415,000 | 47 Greycourt Avenue, Chester, NY 10918

Listing Courtesy of Curasi Realty, Inc.

Closed 1/23/26

$415,000

4
Bedrooms
1,386
Square Feet
1.3
Acres

47 Greycourt Avenue, Chester, NY 10918

$429,000 | 451 Meri Lane, Monroe, NY 10950

Listing Courtesy of Keller Williams Valley Realty

Closed 2/6/26

$429,000

3
Bedrooms
1,698
Square Feet

451 Meri Lane, Monroe, NY 10950

$740,000 | 48 Brennan Court, Chester, NY 10918

Listing Courtesy of Keller Williams Realty

Closed 11/21/25

$740,000

4
Bedrooms
3,063
Square Feet
5
Acres

48 Brennan Court, Chester, NY 10918

a front view of a house with a yard

Listing Courtesy of Christie's Int. Real Estate

Closed 11/18/25

$675,000

4
Bedrooms
2,548
Square Feet
0.47
Acres

165 Creamery Pond Road, Chester, NY 10918

a front view of house with yard and green space

Listing Courtesy of Keller Williams Realty

Closed 12/18/25

$845,000

4
Bedrooms
3,489
Square Feet
2.3
Acres

11 Saddle Hill Road, Chester, NY 10918

a front view of a house with a garden and trees

Listing Courtesy of HomeSmart Homes & Estates

Closed 12/9/25

$515,000

5
Bedrooms
1,888
Square Feet
0.30
Acres

6 Moffatt Lane, Chester, NY 10918

$369,000 | 252 Heritage Lane, Monroe, NY 10950

Listing Courtesy of Howard Hanna Rand Realty

Closed 1/9/26Virtual Tour

$369,000

3
Bedrooms
1,585
Square Feet

252 Heritage Lane, Monroe, NY 10950

$498,000 | 22 Bridle Lane, Chester, NY 10918

Listing Courtesy of Keller Williams Realty

Closed 11/21/25

$498,000

4
Bedrooms
1,570
Square Feet
0.36
Acres

22 Bridle Lane, Chester, NY 10918

a front view of a house with a yard

Listing Courtesy of Howard Hanna Rand Realty

Closed 12/11/25

$375,000

3
Bedrooms
1,355
Square Feet

4309 Whispering Hills Drive, Chester, NY 10918

a front view of a house with a garden

Listing Courtesy of Keller Williams Realty

Closed 1/22/26

$369,900

2
Bedrooms
1,084
Square Feet
0.36
Acres

18 Oakland Avenue, Chester, NY 10918

a front view of a house with a yard

Listing Courtesy of HomeSmart Homes & Estates

Closed 12/12/25Virtual Tour

$320,000

2
Bedrooms
1,072
Square Feet

2317 Whispering Hills Drive, Chester, NY 10918

a front view of a house with swimming pool

Listing Courtesy of Howard Hanna Rand Realty

Closed 2/2/26

$350,000

3
Bedrooms
1,376
Square Feet

264 Heritage Lane, Monroe, NY 10950

a view of a house with a yard

Listing Courtesy of Hudson Valley Griffith

Closed 11/14/25

$365,000

3
Bedrooms
1,331
Square Feet

2409 Whispering Hills Drive, Chester, NY 10918

a front view of a house with a yard and garage

Listing Courtesy of Master Realty Group Inc.

Closed 12/10/25

$310,000

2
Bedrooms
1,086
Square Feet

3107 Whispering Hills Drive, Chester, NY 10924

$382,000 | 4703 Whispering Hills Drive, Chester, NY 10918

Listing Courtesy of Artisan Realty

Closed 1/12/26

$382,000

3
Bedrooms
1,331
Square Feet

4703 Whispering Hills Drive, Chester, NY 10918

a front view of a house with a yard

Listing Courtesy of Howard Hanna Rand Realty

Closed 1/26/26

$480,000

3
Bedrooms
1,662
Square Feet
0.40
Acres

24 Oak Drive, Monroe, NY 10950

Sold 12/11/25

$800,000

4
Bedrooms
2,446
Square Feet
4.1
Acres

126 Beverly Road, Chester, NY 10918

Sold 12/23/25

$899,500

4
Bedrooms
2
Bathrooms
2,102
Square Feet
1.9
Acres

893 Laroe Road, Monroe, NY 10950

Sold 11/12/25

$200,750

4
Bedrooms
2,842
Square Feet
7.1
Acres

57 Whitetail Run, Chester, NY 10918

Sold 11/12/25

$257,500

3
Bedrooms
2,071
Square Feet
13.7
Acres

61 Whitetail Run, Chester, NY 10918

Sold 11/20/25

$100,000

2
Bedrooms
1
Bathrooms
840
Square Feet
1
Acres

82 Goosepond Mountain Road, Chester, NY 10918

Sold 1/8/26

$425,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
2.1
Acres

74 Main Street, Chester, NY 10918

Sold 11/13/25

$614,225

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet
84.5
Acres

940 Craigville Road, Chester, NY 10918

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