- Median Sale Price
- # of Homes Sold
- Median Days on Market
Median Sale Price (All Home Types)
$522,500
+52.6% YoY | Oct 2025
- 1 year
- 3 year
- 5 year
$650,000
5 beds3.5 baths3,617 sq ft
65 Oxford Springs Rd, Chester, NY 10918Rich hardwood floors • Stone fireplace • Custom trim work
Listing by eXp Realty
$779,000
3 beds3 baths2,870 sq ft
16 Oxford Springs Rd, Chester, NY 109184.1 acre lot • 2 garage spots • Built 1988
Listing by RE/MAX Benchmark Realty Group
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$290,000
2 beds1 bath1,084 sq ft
2812 Whispering Hls, Chester, NY 10918$420 HOA • Garage • Community pool
Listing by Exit Realty Connections
$339,900
3 beds2.5 baths1,331 sq ft
1503 Whispering Hls, Chester, NY 10918Clubhouse • Private patio • Pool
Listing by Century 21 E & M Williams Rlty
$299,900
3 beds2.5 baths1,331 sq ft
2104 Whispering Hls, Chester, NY 10918Eat in kitchen • Master bedroom suite • Walk in closet
Listing by ARC Realty 1 in Sales
18 Oakland Ave, Chester, NY 10918
220 Oxford Rd, Chester, NY 10918
4 Camelback Rd, Chester, NY 10918$1,098,888
5 beds3 baths5,080 sq ft
4 Camelback Rd, Chester, NY 10918Listing by Prominent Properties Sotheby's
1401 Whispering Hls, Chester, NY 10918$295,000
2 beds1 bath1,084 sq ft
1401 Whispering Hls, Chester, NY 10918Listing by Howard Hanna Rand Realty
2 Pine Hill Rd, Chester, NY 10918
9 Country Woods Dr, Chester, NY 10918$739,900
5 beds2.5 baths3,124 sq ft
9 Country Woods Dr, Chester, NY 10918Listing by Howard Hanna Rand Realty
80 Pewter Cir, Chester, NY 10918$534,900
3 beds2.5 baths1,946 sq ft
80 Pewter Cir, Chester, NY 10918Listing by BHG Real Estate Green Team
7 Park Pl, Chester, NY 10918$740,000
4 beds3.5 baths2,780 sq ft
7 Park Pl, Chester, NY 10918Listing by Century 21 Full Service Realty
10 Damian Ct, Chester, NY 10918$1,375,000
11 beds6.5 baths4,327 sq ft
10 Damian Ct, Chester, NY 10918Listing by MS Realty Group USA, Inc
16 Mari Rd, Chester, NY 10918
3 Derose Ln, Chester, NY 10918Loading...
25 High St, Chester, NY 10918$515,000
4 beds2.5 baths2,898 sq ft
25 High St, Chester, NY 10918Listing by Christie's Int. Real Estate
84 Pine Hill Rd, Chester, NY 10918
278 Gibson Hill Rd, Chester, NY 10918$722,000
4 beds2.5 baths3,977 sq ft
278 Gibson Hill Rd, Chester, NY 10918Listing by Keller Williams Realty
39 Shore Dr, Blooming Grove, NY 10914$465,000
2 beds2.5 baths2,282 sq ft
39 Shore Dr, Blooming Grove, NY 10914Listing by Windsor Realty Services Inc
391 Bull Mill Rd, Chester, NY 10918$519,999
3 beds2 baths1,800 sq ft
391 Bull Mill Rd, Chester, NY 10918Listing by Century 21 Realty Center
33 Meadow Ave, Chester, NY 10918$430,000
3 beds1 bath1,561 sq ft
33 Meadow Ave, Chester, NY 10918Listing by River Realty Services, Inc.
69 Cedar Pond Ln, Chester, NY 10918$1,975,000
6 beds7.5 baths7,034 sq ft
69 Cedar Pond Ln, Chester, NY 10918Listing by Four Seasons Sothebys Intl
507 Bull Mill Rd, Chester, NY 10918$674,999
5 beds2.5 baths3,115 sq ft
507 Bull Mill Rd, Chester, NY 10918Listing by Keller Williams Hudson Valley
70 Main St, Chester, NY 10918$475,000
4 beds2.5 baths1,357 sq ft
70 Main St, Chester, NY 10918Listing by Keller Williams Hudson Valley
32 Mountainside Dr, Chester, NY 10918$849,900
4 beds2.5 baths2,603 sq ft
32 Mountainside Dr, Chester, NY 10918Listing by Our House Real Estate Group
15 Old Dominion Rd, Blooming Grove, NY 10914$774,000
4 beds2.5 baths3,112 sq ft
15 Old Dominion Rd, Blooming Grove, NY 10914Listing by Blooming Realty
34 Mountainside Dr, Chester, NY 10918$699,990
4 beds3 baths1,867 sq ft
34 Mountainside Dr, Chester, NY 10918Listing by Our House Real Estate Group
53 Odyssey Dr, Chester, NY 10918$1,100,000
4 beds3.5 baths4,467 sq ft
53 Odyssey Dr, Chester, NY 10918Listing by Howard Hanna Rand Realty
37-39 Main St, Chester, NY 10918
20 Goshen Rd, Chester, NY 10918
5 Gabriels Dr, Chester, NY 10918$1,099,000
4 beds2.5 baths2,722 sq ft
5 Gabriels Dr, Chester, NY 10918Listing by Keller Williams Realty
206 Greycourt Rd #190, Chester, NY 10918
15 Deer Run, Olmsteadville, NY 12817
8 Camelback Rd, Chester, NY 10918
Shaw Rd Off Oxford Rd, Blooming Grove, NY 10914$85,000
— beds— baths— sq ft
Shaw Rd Off Oxford Rd, Blooming Grove, NY 10914Listing by Keller Williams Realty
Odyssey Dr, Chester, NY 10918
Oxford Rd, Blooming Grove, NY 10918$325,000
— beds— baths— sq ft
Oxford Rd, Blooming Grove, NY 10918Listing by RE/MAX Benchmark Realty Group
1414 Kings Hwy, Chester, NY 10918
Main St, Chester, NY 10918Viewing page 1 of 1 (Download All)
Based on information submitted to the MLS GRID as of Thu Nov 27 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
Average home prices near Chester, NY
Cities
- New Windsor homes for sale$450,000
- Woodbury homes for sale$599,999
- New City homes for sale$825,000
- Goshen homes for sale$707,450
- Beacon homes for sale$692,000
- Warwick homes for sale$599,900
Zip Codes
- 10924 homes for sale$727,000
- 10981 homes for sale
- 10918 homes for sale$674,999
- 10950 homes for sale$639,000
Chester, NY real estate trends
All Home Types trends in Chester, NY
Based on Redfin calculations of home data from MLS and/or public records.
Location
Data
Oct 2025
Growth
% YoY
Chester, NY
$522,500
+52.6%
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- Scarsdale homes for sale$4,175,000
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