YOUR NEIGHBORHOOD GUIDE · CHESTER, NY
Get to know
Whispering Hills.
Explore Whispering Hills in Chester, NY: nearby homes, schools and everyday places.
LIFE IN WHISPERING HILLS
Get a feel for Whispering Hills.
Whispering Hills is a neighborhood in Chester, NY. This guide brings together a housing snapshot and places to explore in and around the community.
LOCAL KNOWLEDGE MAKES A DIFFERENCE
Work with Top Real Estate Agents in Whispering Hills
Explore top real estate agents in Chester who serve the Whispering Hills neighborhood. Compare their experience, verified reviews, and profiles. A neighborhood-specific rating for Whispering Hills is not currently available.
A LOOK AT THE MARKET
Whispering Hills Housing Market
Asking prices come from active listings. Recorded sales cover to . A dash means that figure was not available.
What kinds of homes are here?
40 residential property records give a broader picture of Whispering Hills, including homes that aren’t for sale.
Updated 2026-10-08. These are property classifications, not a census of individual homes.
THE CITY AROUND YOU
Chester demographics & households
Citywide context for a move to Whispering Hills. These figures describe Chester as a whole.
From FastExpert’s existing Chester city-data source, retrieved 2026-10-08; source year was not supplied. Explore all Chester city data →
FIND YOUR PLACE HERE
Homes for sale in Whispering Hills
No properties are currently available in Whispering Hills. Explore homes for sale in nearby neighborhoods.
For sale0 beds · 0 baths · 0 sq ft
206 Greycourt Rd #190
Chester, NY
For sale4 beds · 2 baths · 2,156 sq ft
50 Kingsley Ln
Chestertown, NY
For sale0 beds · 0 baths · 0 sq ft
61 Snowshoe Rdg
Chestertown, NY
For sale0 beds · 0 baths · 0 sq ft
L31 Clarkson Rd
Chestertown, NY
For sale2 beds · 1 baths · 976 sq ft
213 3rd Street
Wallkill, NY
For sale2 beds · 2 baths · 1,110 sq ft
7 Sycamore Drive
Middletown, NY
For sale0 beds · 0 baths · 1,705 sq ft
22 Sullivan Street
Wurtsboro, NY
For sale0 beds · 0 baths · 0 sq ft
1337,1339,1341,1343,1357 Lincoln Terrace
Peekskill, NY
For sale3 beds · 2 baths · 2,000 sq ft
350 Old Homestead Drive, Highland Lakes
Vernon Township, NJ
For sale6 beds · 5 baths · 0 sq ft
112 Ramapo Valley Road
Mahwah, NJ
For sale6 beds · 2 baths · 1,912 sq ft
112 Wawayanda Avenue
Middletown, NY
For sale6 beds · 2 baths · 2,324 sq ft
36 Spring Street
Middletown, NY
KEEP EXPLORING
Get to know Chester.
Explore the broader area’s housing and demographic context.
Frequently Asked Questions
Frequently Asked Questions About Whispering Hills
Common questions about homes, the housing market, and daily life in Whispering Hills, Chester.
What types of homes are in Whispering Hills?
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How Competitive Is the Whispering Hills Housing Market?
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Is Whispering Hills, Chester a good neighborhood to live in?
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Pros and cons of living in Whispering Hills, Chester?
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Cost of living in Whispering Hills, Chester?
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How can I find a real estate agent serving Whispering Hills?
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When is the best time to sell real estate in Whispering Hills?
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When is the best time to buy real estate in Whispering Hills?
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Sources, dates & how we calculate estimates
Nearby places and photos come from an approved snapshot. Viewing this page does not call Google Places. A controlled refresh can still search within 5 km of the center. Recreation combines park, lake, trail and club searches, removes duplicates and keeps results within 5 miles. Restaurant ranking balances star ratings with review counts; fast-food, convenience stores and places marked as not offering dine-in are excluded.
Housing mix uses residential property records, including homes that are not for sale. Market prices use the most recent recorded qualifying sale per property within 2025-10-08 to 2026-10-08. Transfers identified as non-market transactions and records without a positive sale amount are excluded. Medians appear with at least 10 sales; price per square foot also requires a recorded home size. Property classifications and neighborhood definitions may differ from local usage. These are dated snapshots, not a complete transaction history or live inventory feed.
School grades are FastExpert estimates based on the mean available ratings for unique public schools found across 4 Whispering Hills property samples: A = 8–10, B = 6–under 8, C = 4–under 6, D = 2–under 4, F = 1–under 2. Unrated schools are excluded. Grades do not confirm attendance eligibility.
Chester demographics come from the existing FastExpert city-data source. The city’s source year was not supplied. Top agents use FastExpert’s existing Chester ranking; a Whispering Hills-specific ranking is not available yet.