- Median Sale Price
- # of Homes Sold
- Median Days on Market
Median Sale Price (All Home Types)
$301,836
-26.4% YoY | Jun 2026
- 1 year
- 3 year
- 5 year
Chester, NY homes for sale & real estate
78 homes
Sort:
NEW 17 HRS AGO
$374,900
3 beds1.5 baths1,644 sq ft
260 Gibson Hill Rd, Chester, NY 10918Private access • Countryside retreat • Peaceful setting
Listing by Keller Williams Realty
NEW 22 HRS AGO
$1,685,000
6 beds7.5 baths7,034 sq ft
69 Cedar Pond Ln, Chester, NY 10918Outdoor bar • Outdoor patio • Chef's kitchen
Listing by Prominent Properties Sotheby's
Loading...
$374,900
3 beds2.5 baths1,331 sq ft
2921 Whispering Hls, Chester, NY 10918End unit • Eat in kitchen • Largest unit
Listing by ARC Realty 1 in Sales
FLOOR PLAN
$550,000
3 beds2 baths1,583 sq ft
50 Hambletonian Ave, Chester, NY 10918Marble countertops • Enlarged backyard • Private master bath
Listing by Howard Hanna Rand Realty
OPEN SEP 6, 3PM TO 5PM
$749,000
4 beds2.5 baths2,599 sq ft
121 Conklingtown Rd, Chester, NY 10918High ceiling foyer • Extra living space • Tiled backsplash
Listing by MS Realty Group USA, Inc
13 Bianca Blvd, Chester, NY 10918$700,000
4 beds2.5 baths3,296 sq ft
13 Bianca Blvd, Chester, NY 10918Listing by Keller Williams Realty
38 Shore Dr, Blooming Grove, NY 10914$949,000
3 beds3 baths3,591 sq ft
38 Shore Dr, Blooming Grove, NY 10914Listing by KW Hudson Valley United
1005 Whispering Hls, Chester, NY 10918$290,000
2 beds1.5 baths1,053 sq ft
1005 Whispering Hls, Chester, NY 10918Listing by Century 21 Full Service Realty
2124 Whispering Hls, Chester, NY 10918$299,000
2 beds1 bath1,084 sq ft
2124 Whispering Hls, Chester, NY 10918Listing by Howard Hanna Rand Realty
20 Mountainside Dr, Chester, NY 10918
32 Surrey Rd, Chester, NY 10918
1 Sanford Ave, Chester, NY 10918
65 Oxford Springs Rd, Chester, NY 10918$699,000
5 beds3.5 baths3,463 sq ft
65 Oxford Springs Rd, Chester, NY 10918Listing by HomeSmart Homes & Estates
173 Creamery Pond Rd, Chester, NY 10918$699,000
3 beds2.5 baths2,533 sq ft
173 Creamery Pond Rd, Chester, NY 10918Listing by Keller Williams Realty
176 Beverly Rd, Chester, NY 10918
1 Bell Way, Chester, NY 10918Loading...
166 Bull Mill Rd, Chester, NY 10918$340,000
2 beds1 bath1,004 sq ft
166 Bull Mill Rd, Chester, NY 10918Listing by Keller Williams Valley Realty
63 Hubshop Rd, Chester, NY 10918
241 Meadow Ave, Chester, NY 10918$349,999
4 beds1.5 baths1,560 sq ft
241 Meadow Ave, Chester, NY 10918Listing by Keller Williams Realty
34 Boville Ct, Chester, NY 10918$839,000
4 beds3 baths2,707 sq ft
34 Boville Ct, Chester, NY 10918Listing by Keller Williams Valley Realty
21 Trotting Dr, Chester, NY 10918
3409 Whispering Hls, Chester, NY 10918$360,000
3 beds2.5 baths1,331 sq ft
3409 Whispering Hls, Chester, NY 10918Listing by Howard Hanna Rand Realty
1367 Kings Hwy, Chester, NY 10918
66 Whitetail Run, Chester, NY 10918$449,000
3 beds1.5 baths1,500 sq ft
66 Whitetail Run, Chester, NY 10918Listing by Howard Hanna Rand Realty
3 Garnett Hill Rd, Chester, NY 10918$799,000
4 beds2.5 baths2,516 sq ft
3 Garnett Hill Rd, Chester, NY 10918Listing by Keller Williams Realty
2522 Whispering Hls, Chester, NY 10918$369,000
3 beds2.5 baths1,331 sq ft
2522 Whispering Hls, Chester, NY 10918Listing by Howard Hanna Rand Realty
33 Meadow Ave, Chester, NY 10918$370,000
3 beds1 bath1,561 sq ft
33 Meadow Ave, Chester, NY 10918Listing by River Realty Services, Inc.
412 Laroe Rd, Chester, NY 10918
4008 Whispering Hills Dr, Chester, NY 10918$290,000
2 beds1.5 baths1,072 sq ft
4008 Whispering Hills Dr, Chester, NY 10918Listing by Howard Hanna Rand Realty
4 Debbie Ct, Chester, NY 10918
151 Main St, Chester, NY 10918
11 Old Dominion Rd, Blooming Grove, NY 10914$724,000
4 beds2.5 baths2,547 sq ft
11 Old Dominion Rd, Blooming Grove, NY 10914Listing by Mount Realty
11 Chandler Dr, Chester, NY 10918$545,000
3 beds2.5 baths1,908 sq ft
11 Chandler Dr, Chester, NY 10918Listing by Coldwell Banker Realty
424 Laroe Rd, Chester, NY 10918
70 Main St, Chester, NY 10918
7 Lakeview Dr, Chester, NY 10918$549,999
4 beds2.5 baths2,098 sq ft
7 Lakeview Dr, Chester, NY 10918Listing by Howard Hanna Rand Realty
44 Sayer Rd, Blooming Grove, NY 10914$540,000
3 beds1.5 baths2,332 sq ft
44 Sayer Rd, Blooming Grove, NY 10914Listing by Sage Realty Center LLC
985 Craigville Rd, Chester, NY 10918
185 Oxford Rd, Chester, NY 10918$389,000
3 beds1 bath1,062 sq ft
185 Oxford Rd, Chester, NY 10918Listing by Keller Williams Hudson Valley
197 Oxford Rd, Chester, NY 10918$799,000
4 beds2.5 baths3,070 sq ft
197 Oxford Rd, Chester, NY 10918Listing by Howard Hanna Rand Realty
68 Conklingtown Rd Unit 1&2, Chester, NY 10918$575,000
6 beds2 baths— sq ft
68 Conklingtown Rd Unit 1&2, Chester, NY 10918Listing by MS Realty Group USA, Inc
Viewing page 1 of 2 (Download top 78)
Based on information submitted to the MLS GRID as of Sat Aug 29 2026. 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$427,000
- Woodbury homes for sale$649,999
- New City homes for sale$854,000
- Goshen homes for sale$737,450
- Beacon homes for sale$722,450
- Warwick homes for sale$699,000
Zip Codes
- 10924 homes for sale$799,900
- 10981 homes for sale
- 10918 homes for sale$699,000
- 10950 homes for sale$586,500
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
Jun 2026
Growth
% YoY
Chester, NY
$301,836
-26.4%
More to explore in Chester, NY
- Featured
- Price
- Bedroom
Popular Markets in New York
- New York homes for sale$899,000
- Manhattan homes for sale$1,389,500
- Rochester homes for sale$130,000
- Buffalo homes for sale$198,000
- Yonkers homes for sale$379,000
- White Plains homes for sale$449,000
Find us
Subsidiaries
Affiliated Business
United States
CanadaCopyright: © 2026 Redfin. All rights reserved.
Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.
Do not sell or share my personal information.
REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.
California DRE #01521930
Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures
New Mexico Real Estate Licenses
TREC: Info About Brokerage Services, Consumer Protection Notice
All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.
Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.
If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.
REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.