Chester, NY Real Estate & Homes For Sale

73 homes

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NEW
COMING SOON 8/28
3D VIEW
$299,000
2 Beds
1 Bath
1,084 sqft
2124 Whispering Hills,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
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NEW
COMING SOON 8/28
2 ACRES
$649,999
3 Beds
3 Baths
2,902 sqft
3561 Rte 94,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
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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
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OPEN SUN, 11-1PM
3D VIEW
0.37 ACRES
$699,000
3 Beds
2.5 Baths
2,533 sqft
173 Creamery Pond Road,
Chester, NY 10918
Listing by: Keller Williams Realty
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$750,000
4 Beds
3 Baths
2,280 sqft
1 Sanford Avenue,
Chester, NY 10918
Listing by: Redfin Real Estate
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COMING SOON 9/1
$360,000
3 Beds
2.5 Baths
1,331 sqft
3409 Whispering Hills,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
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0.37 ACRES
$489,000
4 Beds
1.5 Baths
1,820 sqft
32 Surrey Road,
Chester, NY 10918
Listing by: eXp Realty
3D VIEW
1.8 ACRES
$839,000
4 Beds
3 Baths
2,707 sqft
34 Boville Court,
Chester, NY 10918
Listing by: Keller Williams Valley Realty
0.87 ACRES
$459,000
4 Beds
2.5 Baths
2,060 sqft
63 Hubshop Road,
Chester, NY 10918
Listing by: Keller Williams Realty
1 ACRE
$700,000
4 Beds
2.5 Baths
3,296 sqft
13 Bianca Boulevard,
Chester, NY 10918
Listing by: Keller Williams Realty
3D VIEW
0.34 ACRES
$565,000
3 Beds
2 Baths
1,724 sqft
1 Bell Way,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
COMING SOON 8/28
0.37 ACRES
$675,000
3 Beds
2.5 Baths
3,202 sqft
188 Creamery Pond Road,
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
$749,900
4 Beds
3 Baths
3,080 sqft
20 Mountainside Drive,
Chester, NY 10918
Listing by: eXp Realty
3 ACRES
$799,000
4 Beds
2.5 Baths
2,516 sqft
3 Garnett Hill Road,
Chester, NY 10918
Listing by: Keller Williams Realty
1.8 ACRES
$340,000
2 Beds
1 Bath
1,004 sqft
166 Bull Mill Road,
Chester, NY 10918
Listing by: Keller Williams Valley Realty
OPEN SAT, 1-3PM
3D VIEW
2.4 ACRES
$615,000
3 Beds
2 Baths
1,848 sqft
412 Laroe Road,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
$295,000
2 Beds
1 Bath
1,084 sqft
2113 Whispering Hills,
Chester, NY 10918
Listing by: Keller Williams Realty
3D VIEW
0.39 ACRES
$475,000
3 Beds
2 Baths
1,624 sqft
21 Trotting Drive,
Chester, NY 10918
Listing by: Keller Williams Realty
0.76 ACRES
$469,000
3 Beds
2 Baths
1,357 sqft
70 Main Street,
Chester, NY 10918
Listing by: Curasi Realty, Inc.
2.5 ACRES
$699,900
4 Beds
2.5 Baths
2,715 sqft
176 Beverly Road,
Chester, NY 10918
Listing by: Owner Entry.com
3.5 ACRES
$724,000
4 Beds
2.5 Baths
2,547 sqft
11 Old Dominion Road,
Blooming Grove, NY 10914
Listing by: Mount Realty
$369,000
3 Beds
2.5 Baths
1,331 sqft
2522 Whispering Hills,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
0.92 ACRES
$449,000
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
$325,000
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
$290,000
2 Beds
1.5 Baths
1,072 sqft
4008 Whispering Hills Drive,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
1 ACRE
$549,999
4 Beds
2.5 Baths
2,098 sqft
7 Lakeview Drive,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
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
1.9 ACRES
$650,000
3 Beds
3 Baths
2,520 sqft
29 Murray Drive,
Chester, NY 10918
Listing by: eXp Realty
$389,900
3 Beds
2 Baths
1,393 sqft
4114 Whispering Hills,
Chester, NY 10918
Listing by: Coldwell Banker Realty
FOR SALE BY OWNER
4 ACRES
$550,000
3 Beds
2 Baths
1,583 sqft
50 Hambletonian Ave,
Chester, NY 10918
$750,000
5 Beds
2.5 Baths
2,700 sqft
2 Hemlock Court,
Chester, NY 10918
Listing by: MK Realty Inc
FORECLOSURE
NOTICE OF DEFAULT
3D VIEW
0.94 ACRES
4 Beds
1.5 Baths
1,560 sqft
241 Meadow Avenue,
Chester, NY 10918
Listing by: Keller Williams Realty
0.95 ACRES
$389,000
3 Beds
1 Bath
1,062 sqft
185 Oxford Road,
Chester, NY 10918
Listing by: Keller Williams Hudson Valley
$725,000
3 Beds
2.5 Baths
2,677 sqft
1 Arborvitae Court,
Chester, NY 10918
Listing by: MK Realty Inc
OPEN SUN, 1-3PM
0.46 ACRES
$545,000
3 Beds
2.5 Baths
1,908 sqft
11 Chandler Drive,
Chester, NY 10918
Listing by: Coldwell Banker Realty

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 $539,985

Month	Median home value
August 2025	$523k
September 2025	$525k
October 2025	$526k
November 2025	$526k
December 2025	$528k
January 2026	$530k
February 2026	$533k
March 2026	$535k
April 2026	$537k
May 2026	$538k
June 2026	$539k
July 2026	$540k

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 9 new listings in Chester, NY and 73 homes for sale.

Home Size	Home Value*
2 bedrooms (6 homes)	$306,992
3 bedrooms (24 homes)	$489,499
4 bedrooms (28 homes)	$683,413

*Home value over the past month

What Locals Say about Chester

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
1y 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
5y 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
6y 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
6y 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
7y 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
7y 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. "
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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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inwalker
11y ago
"Easy commute to work in New York City via route 17M (2 miles) or bus via Short Line (2 miles) yet no congested roads to deal with. Great neighbors. Park within walking distance (football, soccer, baseball and children's recreation area). Large variety of Restaurants to satisfy your all your cravings. Orange Regional Medical center 5 miles via 17M."
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Based on information submitted to the MLS GRID as of 2026-08-25 08:18:10 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

73 homes

Chester, NY Real Estate Trends

Affordability of Living in Chester, NY

Average Home Value in Chester, NY, by Home Size

What Locals Say about Chester

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