Chester, NY Real Estate & Homes For Sale

65 homes

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OPEN SUN, 12-2PM
3 ACRES
$750,000
4 Beds
3.5 Baths
3,100 sqft
985 Craigville Road,
Chester, NY 10918
Listing by: Houlihan Lawrence Inc.
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3 ACRES
$599,000
4 Beds
4.5 Baths
3,326 sqft
111 Ayr Road,
Chester, NY 10918
Listing by: Curasi Realty, Inc.
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9.6 ACRES
$1,850,000
3 Beds
2.5 Baths
2,404 sqft
7 Greycourt Road,
Chester, NY 10918
Listing by: KW Hudson Valley United
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$339,900
2 Beds
1.5 Baths
1,086 sqft
3706 Whispering Hills,
Chester, NY 10918
Listing by: eXp Realty
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$299,000
2 Beds
1.5 Baths
1,086 sqft
2107 Whispering Hills,
Chester, NY 10918
Listing by: Wansor Realty
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OPEN SAT, 12-2PM
1.8 ACRES
$485,000
3 Beds
2.5 Baths
2,441 sqft
94 Booth Road,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
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$549,000
4 Beds
2 Baths
2,824 sqft
147 Main Street,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
$269,000
2 Beds
1 Bath
1,084 sqft
1212 Whispering Hills,
Chester, NY 10918
Listing by: Keller Williams Realty
AUCTION
$299,900
3 Beds
2 Baths
1,316 sqft
1223 Whispering Hills,
Chester, NY 10918
Listing by: KW Hudson Valley United
3D VIEW
0.49 ACRES
$339,900
2 Beds
1 Bath
960 sqft
18 Schueler Road,
Chester, NY 10918
Listing by: Weichert Realtors
2.3 ACRES
$779,900
4 Beds
2.5 Baths
2,616 sqft
1168 Craigville Road,
Chester, NY 10918
Listing by: ARC Realty 1 in Sales
0.4 ACRES
$499,999
2 Beds
2 Baths
1,910 sqft
19 Meadow Avenue,
Chester, NY 10918
Listing by: RE/MAX Town & Country
1.9 ACRES
$879,000
4 Beds
3 Baths
3,764 sqft
101 Beverly Road,
Chester, NY 10918
Listing by: Greene Realty Group
AUCTION
3D VIEW
0.38 ACRES
$459,000
4 Beds
2 Baths
1,832 sqft
8 Townsend Place,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
OPEN SUN, 12-2PM
6.2 ACRES
$679,000
4 Beds
3.5 Baths
2,960 sqft
5 Red Fox Run,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
$370,000
3 Beds
2.5 Baths
1,331 sqft
4704 Whispering Hills,
Chester, NY 10918
Listing by: Sahagian Realty LLC
10.7 ACRES
$1,599,999
6 Beds
7.5 Baths
7,034 sqft
69 Cedar Pond Lane,
Chester, NY 10918
Listing by: Prominent Properties Sotheby's
3D VIEW
1.1 ACRES
$949,000
3 Beds
3 Baths
3,591 sqft
38 Shore Drive,
Blooming Grove, NY 10914
Listing by: KW Hudson Valley United
$364,900
3 Beds
2.5 Baths
1,331 sqft
2921 Whispering Hills,
Chester, NY 10918
Listing by: ARC Realty 1 in Sales
3D VIEW
1.3 ACRES
$425,000
4 Beds
1.5 Baths
2,116 sqft
6 Old Dominion Road,
Blooming Grove, NY 10914
Listing by: RE/MAX Prime Properties
3D VIEW
$290,000
2 Beds
1.5 Baths
1,053 sqft
1005 Whispering Hills,
Chester, NY 10918
Listing by: Century 21 Full Service Realty
1.4 ACRES
$749,000
4 Beds
2.5 Baths
2,599 sqft
121 Conklingtown Road,
Chester, NY 10918
Listing by: MS Realty Group USA, Inc
3D VIEW
$289,000
2 Beds
1 Bath
1,084 sqft
2124 Whispering Hills,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
3D VIEW
2 ACRES
$619,999
3 Beds
3 Baths
2,902 sqft
3561 Rte 94,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
3D VIEW
2.3 ACRES
$699,000
5 Beds
3.5 Baths
3,463 sqft
65 Oxford Springs Road,
Chester, NY 10918
Listing by: HomeSmart Homes & Estates
$750,000
4 Beds
3 Baths
2,280 sqft
1 Sanford Avenue,
Chester, NY 10918
Listing by: Redfin Real Estate
1 ACRE
$700,000
4 Beds
2.5 Baths
3,296 sqft
13 Bianca Boulevard,
Chester, NY 10918
Listing by: Keller Williams Realty
0.37 ACRES
$440,000
3 Beds
1.5 Baths
1,728 sqft
1367 Kings Highway,
Chester, NY 10918
Listing by: Greene Realty Group
1.6 ACRES
$739,900
4 Beds
3 Baths
3,080 sqft
20 Mountainside Drive,
Chester, NY 10918
Listing by: eXp Realty
3D VIEW
2.4 ACRES
$605,000
3 Beds
2 Baths
1,848 sqft
412 Laroe Road,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
$275,000
2 Beds
1 Bath
1,084 sqft
2113 Whispering Hills,
Chester, NY 10918
Listing by: Keller Williams Realty
0.76 ACRES
$419,000
3 Beds
2 Baths
1,357 sqft
70 Main Street,
Chester, NY 10918
Listing by: Curasi Realty, Inc.
$355,000
3 Beds
2.5 Baths
1,331 sqft
2522 Whispering Hills,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
0.92 ACRES
$435,000
3 Beds
1.5 Baths
1,500 sqft
66 Whitetail Run,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
FORECLOSURE
BANK OWNED
0.37 ACRES
$370,000
3 Beds
1 Bath
1,561 sqft
33 Meadow Avenue,
Chester, NY 10918
Listing by: River Realty Services, Inc.
$750,000
5 Beds
2.5 Baths
2,700 sqft
3 Hilltop Lane,
Chester, NY 10918
Listing by: MK Realty Inc
$299,000
4 Beds
1 Bath
1,504 sqft
151 Main Street,
Chester, NY 10918
Listing by: Hudson Valley Griffith
$750,000
5 Beds
2.5 Baths
2,700 sqft
1 Hilltop Lane,
Chester, NY 10918
Listing by: MK Realty Inc
3D VIEW
1.7 ACRES
$799,000
4 Beds
2.5 Baths
3,070 sqft
197 Oxford Road,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
1 ACRE
$575,000
6 Beds
2 Baths
68 Conklingtown Road #1&2,
Chester, NY 10918
Listing by: MS Realty Group USA, Inc
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Chester, NY Real Estate Trends

Learn about the Chester, NY housing market through trends and averages.

Affordability
Home Value
What Locals Say

Affordability of Living in Chester, NY

The median home value is $537,879

Month	Median home value
September 2025	$522k
October 2025	$523k
November 2025	$523k
December 2025	$525k
January 2026	$527k
February 2026	$529k
March 2026	$532k
April 2026	$534k
May 2026	$535k
June 2026	$536k
July 2026	$537k
August 2026	$538k

View as a graph

Trends and affordability stats are provided by third party data sources.

Average Home Value in Chester, NY, by Home Size

Currently, there are 65 homes for sale in Chester.

Home Size	Home Value*
2 bedrooms (8 homes)	$303,403
3 bedrooms (16 homes)	$487,958
4 bedrooms (27 homes)	$678,464

*Home value over the past month

What Locals Say about Chester

Araceli Santiago
Resident
3w ago
"Quiet and peaceful area to live in Children safely play outside with neighbors also friendly neighborhood "
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Jenelle Rivera
Visitor
1y ago
"Quiet and pretty family oriented very clean feels safe and there’s sufficient parking for the residents"
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Jenelle Rivera
Resident
1y ago
"Very close to major highways and traffic is always minimal. Shopping Centers and major supermarkets are within walking distance "
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Araceli Santiago
Resident
2y ago
"Im new in this neighborhood i barely like to live very quiet place to lived with family Only bad is higher tax 😅"
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Trulia User
Resident
6y ago
"There's plenty of areas with sidewalks to walk your dog throughout most of town. My apartment complex has a dog park "
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Jennifer G.
Resident
6y ago
"I have two years living here. Great place to raise a family. Friendly and safe neighborhood. The kids love it as well."
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Kcouponsdeals
Resident
7y ago
"this is a great village, and neighborhood to live in lots of community involvement, family activities, close to transportation and shopping."
1
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Kcouponsdeals
Resident
7y ago
"this is a great family neighborhood. You can walk to store and NYC bus stop. it's great for kids sports, trick or treating ,etc. there are also arts and theater programs in the area."
2
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DEIRDRE B.
Resident
7y ago
"I take the Shortline bus to NYC. 1 hour and 15 minutes more or less plus train from Port. It’s about $450/month including Metrocard. Shortline has become less reliable recently. "
3
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Missmtrejo
Resident
7y ago
"It’s a safe community and our neighbors have become friends! We have lived here for 20 years. It’s a great place for children to make friends and feel safe in their environment when they are outside playing. "
1
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Melissa Kyles
Resident
7y ago
"I lived in Chester when I was a children to adulthood. Great place to live. Outstanding school district. Wish I never moved away."
4
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Dianerene
Resident
7y ago
"Street fairs, community parades, concerts and so much more. The location is awesome and neighbors aren’t overly nosy yet friendly."
2
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Dawnstephenson42
Resident
7y ago
"fireworks night football h.s small town feel community garage sales schools mom and pop shops nearby wineries holiday parades farmers market"
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Suzzzzzzz64
Resident
8y ago
"I live in this area for 11 years my neighborhood is great and the people around here are really nice "
5
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Dianerene
Resident
8y ago
"My commute is excellent. I have a 3 minute commute to the park and ride bus and local stores. Easy to get around by foot if needed."
1
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Ebobec18
Resident
8y ago
"Safety its a neighborhood very secure the police its annoying but make sense because that its part of what make this place so safe. I can go out at 3pm or 3am and i will fill safe any time. "
1
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Tara R.
Resident
8y ago
"i love chester unfortunately there arent many houses for purchase in my range for a single mom. wanted my kids to stay in there school there on sports teams."
5
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Browse Chester, NY homes by type

Based on information submitted to the MLS GRID as of 2026-10-08 20:23:13 PDT 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. Some IDX listings have been excluded from this website. Click here for more information

Chester, NY Real Estate & Homes For Sale