Chester, NY Real Estate & Homes For Sale

59 homes

Use arrow keys to navigate
NEW - 17 MIN AGO
$725,000
3 Beds
2.5 Baths
2,677 sqft
1 Arborvitae Court,
Chester, NY 10918
Listing by: MK Realty Inc
Use arrow keys to navigate
NEW - 1 HR AGO
$740,000
5 Beds
2.5 Baths
2,700 sqft
7 Hilltop Lane,
Chester, NY 10918
Listing by: MK Realty Inc
Use arrow keys to navigate
NEW
OPEN SAT, 11-1PM
3D VIEW
$349,999
3 Beds
2 Baths
1,316 sqft
3414 Whispering Hills,
Chester, NY 10918
Listing by: KW Hudson Valley United
Use arrow keys to navigate
NEW
OPEN SAT, 12-2PM
0.35 ACRES
$489,900
3 Beds
2 Baths
1,912 sqft
76 Surrey Road,
Chester, NY 10918
Listing by: eXp Realty
Use arrow keys to navigate
OPEN SAT, 11-1PM
$329,000
2 Beds
1.5 Baths
1,294 sqft
4118 Whispering Hills Drive,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
Use arrow keys to navigate
OPEN SUN, 1-3PM
0.46 ACRES
$615,000
3 Beds
2.5 Baths
1,908 sqft
11 Chandler Drive,
Chester, NY 10918
Listing by: Coldwell Banker Realty
Use arrow keys to navigate
$850,000
5 Beds
2.5 Baths
3,200 sqft
5 Hilltop Lane,
Chester, NY 10918
Listing by: MK Realty Inc
$750,000
5 Beds
2.5 Baths
2,700 sqft
3 Hemlock Court,
Chester, NY 10918
Listing by: MK Realty Inc
OPEN SAT, 12-2PM
3D VIEW
3 ACRES
$800,000
4 Beds
3.5 Baths
3,100 sqft
985 Craigville Road,
Chester, NY 10918
Listing by: Serhant LLC
$295,000
2 Beds
1.5 Baths
1,086 sqft
2119 Whispering Hills,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
OPEN SUN, 1-3PM
2.5 ACRES
$799,900
4 Beds
2.5 Baths
2,715 sqft
176 Beverly Rd,
Chester, NY 10918
Listing by: BLUESTONE SIGNATURE REALTY LLC
OPEN SAT, 12-2PM
2.5 ACRES
$649,999
4 Beds
3 Baths
2,316 sqft
424 Laroe Road,
Chester, NY 10918
Listing by: Epique Realty
0.69 ACRES
$440,800
3 Beds
1 Bath
2,016 sqft
815 Craigville Road,
Chester, NY 10918
Listing by: Ellis Sotheby's Intl Realty
3D VIEW
0.42 ACRES
$789,900
5 Beds
4 Baths
4,697 sqft
19 Grand View Terrace,
Chester, NY 10918
Listing by: eXp Realty
3.7 ACRES
$849,999
4 Beds
2.5 Baths
2,236 sqft
24 Boville Court,
Chester, NY 10918
Listing by: KW Hudson Valley United
FORECLOSURE
BANK OWNED
0.37 ACRES
$390,000
3 Beds
1 Bath
1,561 sqft
33 Meadow Avenue,
Chester, NY 10918
Listing by: River Realty Services, Inc.
3D VIEW
2.3 ACRES
$1,195,000
4 Beds
3.5 Baths
4,281 sqft
22 Goshen Road,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
7.1 ACRES
$875,000
4 Beds
2.5 Baths
3,656 sqft
49 Stone Mountain Trail,
Chester, NY 10918
Listing by: eRealty Advisors, Inc
0.39 ACRES
$685,000
4 Beds
2.5 Baths
1,718 sqft
26 Bridle Lane,
Chester, NY 10918
Listing by: Owner Entry.com
6 ACRES
$1,200,000
4 Beds
2.5 Baths
2,711 sqft
63 Whitetail Run,
Chester, NY 10918
Listing by: SPIRAL NY Real Estate LLC
3D VIEW
6.8 ACRES
$1,000,000
4 Beds
2.5 Baths
3,955 sqft
1 Oakland Avenue,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
3D VIEW
2.3 ACRES
$949,000
4 Beds
2.5 Baths
3,332 sqft
19 Bull Mine Road,
Chester, NY 10918
Listing by: BHG Real Estate Green Team
0.45 ACRES
$549,900
3 Beds
2 Baths
2,138 sqft
3318 State Route 94,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
3.2 ACRES
$675,000
4 Beds
2.5 Baths
2,784 sqft
335 Laroe Road,
Chester, NY 10918
Listing by: Coldwell Banker Choice Prop.
3.2 ACRES
$999,900
Studio
4,032 sqft
206 Greycourt Road,
Chester, NY 10918
Listing by: Cronin & Company Real Estate
3D VIEW
2.3 ACRES
$1,090,000
4 Beds
3.5 Baths
4,130 sqft
102 Beverly Road,
Chester, NY 10918
Listing by: Keller Williams Realty
3D VIEW
5.2 ACRES
$899,000
5 Beds
3.5 Baths
3,764 sqft
86 Long Vista Lane,
Chester, NY 10918
Listing by: RE/MAX Town & Country
0.56 ACRES
$559,000
4 Beds
2.5 Baths
2,698 sqft
24 Walnut Street,
Chester, NY 10918
Listing by: Keller Williams Village Sq Rlt
1.8 ACRES
$550,000
3 Beds
2.5 Baths
2,083 sqft
94 Booth Road,
Chester, NY 10918
Listing by: Compass Greater NY, LLC
46 ACRES
$399,000
492 Black Meadow Road,
Chester, NY 10918
Listing by: eXp Realty
10.4 ACRES
$900,000
4 Beds
2.5 Baths
2,588 sqft
60 Whitetail Run,
Chester, NY 10918
Listing by: Realty Blue Corp
6.3 ACRES
$894,000
3 Beds
3.5 Baths
3,535 sqft
220 Oxford Road,
Chester, NY 10918
Listing by: Blooming Realty
3D VIEW
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
3D VIEW
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
$785,000
5 Beds
5.5 Baths
5,403 sqft
4 Debbie Court,
Chester, NY 10918
Listing by: Flag Realty Group
0.87 ACRES
$499,000
4 Beds
2.5 Baths
2,060 sqft
63 Hubshop Road,
Chester, NY 10918
Listing by: Keller Williams Realty
FOR SALE BY OWNER
1.9 ACRES
$644,999
4 Beds
2.5 Baths
2,544 sqft
5 Bens Way,
Chester, NY 10918
OPEN SAT, 12-2PM
1.3 ACRES
$749,999
3 Beds
2.5 Baths
2,718 sqft
58 Nancy Lane,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
3D VIEW
2.7 ACRES
$1,145,000
9 Beds
6.5 Baths
4,965 sqft
19 High Street,
Chester, NY 10918
Listing by: Keller Williams Realty
18.5 ACRES
$849,900
4 Beds
3 Baths
2,370 sqft
2 Primrose Lane,
Chester, NY 10918
Listing by: Weichert Realtors

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 $533,037

Month	Median home value
June 2025	$515k
July 2025	$517k
August 2025	$519k
September 2025	$520k
October 2025	$521k
November 2025	$522k
December 2025	$523k
January 2026	$525k
February 2026	$528k
March 2026	$530k
April 2026	$532k
May 2026	$533k

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 6 new listings in Chester, NY and 59 homes for sale.

Home Size	Home Value*
2 bedrooms (3 homes)	$302,432
3 bedrooms (14 homes)	$484,591
4 bedrooms (27 homes)	$674,146

*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"
0
Flag
Jenelle Rivera
Resident
1y ago
"Very close to major highways and traffic is always minimal. Shopping Centers and major supermarkets are within walking distance "
0
Flag
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 😅"
0
Flag
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 "
0
Flag
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."
0
Flag
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
Flag
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
Flag
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
Flag
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
Flag
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
Flag
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
Flag
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"
0
Flag
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
Flag
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
Flag
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
Flag
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
Flag
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."
0
Flag

Based on information submitted to the MLS GRID as of 2026-07-09 17:58:18 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

59 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

Nearby Real Estate

Nearby Zip Codes

Popular Cities in New York

Chester Neighborhoods

Chester Property Types

Real Estate Guides

Find Rental Properties