Chester, NY Real Estate & Homes For Sale

57 homes

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NEW
COMING SOON 5/29
1 ACRE
$779,000
4 Beds
3.5 Baths
2,948 sqft
270 Bull Mill Road,
Chester, NY 10918
Listing by: Keller Williams Realty
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OPEN SAT, 1-2PM
COMING SOON 5/27
1.8 ACRES
$590,000
3 Beds
2.5 Baths
2,083 sqft
94 Booth Road,
Chester, NY 10918
Listing by: Compass Greater NY, LLC
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46 ACRES
$399,000
492 Black Meadow Road,
Chester, NY 10918
Listing by: eXp Realty
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0.3 ACRES
$425,000
3 Beds
2 Baths
1,748 sqft
11 Oxford Depot,
Chester, NY 10918
Listing by: Keller Williams Realty
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10.4 ACRES
$900,000
4 Beds
2.5 Baths
2,588 sqft
60 Whitetail Run,
Chester, NY 10918
Listing by: Realty Blue Corp
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0.36 ACRES
$499,900
3 Beds
2 Baths
1,778 sqft
1 N Hudson Street,
Chester, NY 10918
Listing by: Keller Williams Hudson Valley
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$370,000
3 Beds
2.5 Baths
1,331 sqft
3815 Whispering Hills Drive,
Chester, NY 10918
Listing by: MK Realty Inc
6.3 ACRES
$999,000
3 Beds
3.5 Baths
3,535 sqft
220 Oxford Road,
Chester, NY 10918
Listing by: Blooming Realty
10.9 ACRES
$825,000
4 Beds
2.5 Baths
2,732 sqft
45 Whitetail Run,
Chester, NY 10918
Listing by: Hudson Valley Home Connection
3.6 ACRES
$999,999
5 Beds
2.5 Baths
4,772 sqft
2 Garnett Hill Road,
Chester, NY 10918
Listing by: Platinum Realty Associates
5.4 ACRES
$799,000
5 Beds
5.5 Baths
5,403 sqft
4 Debbie Court,
Chester, NY 10918
Listing by: Flag Realty Group
0.87 ACRES
$529,000
4 Beds
2.5 Baths
2,060 sqft
63 Hubshop Road,
Chester, NY 10918
Listing by: Keller Williams Realty
AUCTION
Est. $298,400
2 Beds
2 Baths
1,086 sqft
1206 Whispering Hls #151,
Chester, NY 10918
1 ACRE
$550,000
5 Beds
2.5 Baths
1,815 sqft
208 Glenmere Road,
Chester, NY 10918
Listing by: MK Realty Inc
FOR SALE BY OWNER
1.9 ACRES
$644,999
4 Beds
2.5 Baths
2,544 sqft
5 Bens Way,
Chester, NY 10918
OPEN SUN, 12-2PM
1.3 ACRES
$799,999
3 Beds
2.5 Baths
2,718 sqft
58 Nancy Lane,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
0.45 ACRES
$450,000
3 Beds
1.5 Baths
1,177 sqft
151 Laroe Road,
Chester, NY 10918
Listing by: Keller Williams Realty
2.8 ACRES
$640,000
3 Beds
1.5 Baths
2,136 sqft
4 Greycourt Road,
Chester, NY 10918
Listing by: MK Realty Inc
2.7 ACRES
$1,195,000
9 Beds
6.5 Baths
4,965 sqft
19 High Street,
Chester, NY 10918
Listing by: Keller Williams Realty
$425,000
3 Beds
2.5 Baths
1,331 sqft
2722 Whispering Hills,
Chester, NY 10918
Listing by: Artisan Realty
$319,900
2 Beds
1.5 Baths
1,072 sqft
2820 Whispering Hills,
Chester, NY 10918
Listing by: R2M Realty Inc.
2.4 ACRES
$899,900
5 Beds
3 Baths
3,846 sqft
2 Heidi Lane,
Chester, NY 10918
Listing by: Cronin & Company Real Estate
18.5 ACRES
$849,900
4 Beds
3 Baths
2,370 sqft
2 Primrose Lane,
Chester, NY 10918
Listing by: Weichert Realtors
0.26 ACRES
$529,900
3 Beds
3 Baths
2,032 sqft
35 Maple Avenue,
Chester, NY 10918
Listing by: RE/MAX Benchmark Realty Group
8.4 ACRES
$3,400,000
4 Beds
4 Baths
7,750 sqft
19 Greentree Lane,
Chester, NY 10918
Listing by: Serhant LLC
1 ACRE
$849,900
3 Beds
3 Baths
2,740 sqft
149 Creamery Pond Road,
Chester, NY 10918
Listing by: Keller Williams Realty
3D VIEW
0.92 ACRES
$695,000
4 Beds
2.5 Baths
2,524 sqft
17 Woodridge Drive,
Chester, NY 10918
Listing by: eXp Realty
NEW CONSTRUCTION
3D VIEW
3.8 ACRES
$1,399,777
4 Beds
4 Baths
4,508 sqft
145 Kings Highway Bypass,
Chester, NY 10918
Listing by: Keller Williams Realty
0.5 ACRES
$875,000
3 Beds
2.5 Baths
2,302 sqft
2 Pine Hill Road,
Chester, NY 10918
Listing by: Ellis Sotheby's Intl Realty
$344,900
3 Beds
2 Baths
1,316 sqft
1311 Whispering Hills,
Chester, NY 10918
Listing by: Keller Williams Realty
1.1 ACRES
$1,159,900
4 Beds
4 Baths
4,624 sqft
16 Lori Lane,
Chester, NY 10918
Listing by: eXp Realty
NEW CONSTRUCTION
0.53 ACRES
$759,900
4 Beds
2.5 Baths
2,250 sqft
90 Pewter Circle,
Chester, NY 10918
Listing by: Keller Williams Realty
0.38 ACRES
$500,000
3 Beds
2 Baths
2,688 sqft
5 N Hudson Street,
Chester, NY 10918
Listing by: Keller Williams Realty
FOR SALE BY OWNER
7.2 ACRES
$899,000
4 Beds
3 Baths
2,700 sqft
91 Glenmere Rd,
Chester, NY 10918
NEW CONSTRUCTION
20.18 ACRES
$849,900
4 Beds
2.5 Baths
2,603 sqft
32 Mountainside Drive,
Chester, NY 10918
Listing by: Our House Real Estate Group
NEW CONSTRUCTION
1.6 ACRES
$869,900
4 Beds
2.5 Baths
3,000 sqft
10 Wells Sweep Lane,
Chester, NY 10918
Listing by: Keller Williams Realty
NEW CONSTRUCTION
4.5 ACRES
$879,900
4 Beds
2.5 Baths
3,200 sqft
1414 Kings Highway,
Chester, NY 10918
Listing by: Keller Williams Realty
5.7 ACRES
$299,000
552 Pine Hill Road,
Chester, NY 10918
Listing by: eRealty Advisors, Inc
1.8 ACRES
$699,000
4 Beds
2.5 Baths
3,120 sqft
558 Pine Hill Road,
Chester, NY 10918
Listing by: eRealty Advisors, Inc
$377,000
3 Beds
2.5 Baths
1,331 sqft
1221 Whispering Hls,
Chester, NY 10918
Listing by: BUY NY REALTY LLC

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 $525,572

Month	Median home value
May 2025	$508k
June 2025	$509k
July 2025	$511k
August 2025	$512k
September 2025	$514k
October 2025	$515k
November 2025	$515k
December 2025	$517k
January 2026	$519k
February 2026	$522k
March 2026	$524k
April 2026	$526k

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 5 new listings in Chester, NY and 57 homes for sale.

Home Size	Home Value*
2 bedrooms (4 homes)	$299,532
3 bedrooms (18 homes)	$477,113
4 bedrooms (20 homes)	$665,960

*Home value over the past month

What Locals Say about Chester

Jenelle Rivera
Visitor
11mo 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
6y 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."
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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 2026-02-06 15:18:24 PST. 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

57 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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