Chester, NY · Condominiums

Whispering Hills Condos in Chester, NY

Whispering Hills is a condominium community in Chester, NY with two- and three-bedroom units built in the mid-1980s to early 1990s. Over the last three years, 85 units sold through OneKey® MLS at a median price of $324,900. I'm Ammar Iqbal, a Real Estate Salesperson with eXp Realty, and I've handled 11 Whispering Hills sales since 2021.

Whispering Hills at a Glance

Location

Chester, Orange County, NY (Chester mailing address)

Home type

Condominium units, 2 and 3 bedrooms

Typical size

About 1,050 to 1,355 sq ft in recent sales

Built

Mid-1980s to early 1990s, per MLS records

Median sale, last 12 months

$320,000 across 25 sales

Local agent

Ammar Iqbal, eXp Realty · (845) 837-9577

What Whispering Hills Units Have Sold For

These numbers cover every Whispering Hills sale in Chester recorded in OneKey MLS from October 1, 2023 through September 30, 2026. They include sales by all agents, not just mine.

Source: OneKey MLS closed sales, street name Whispering Hills, Chester, checked October 2, 2026. Sale-to-list is total closing prices divided by total final list prices, so earlier price cuts aren't reflected. Off-market sales are not included. 56 of the 85 units sold at or above their final list price.

Buying in Whispering Hills

• Compare like for like. Two-bedroom and three-bedroom units sell in different price bands, so compare a unit to recent sales of the same type and size.
• Read the condo documents. Before you commit, review the HOA fee, what it covers, the budget, any special assessments and the rules on rentals and pets. Your attorney and lender will ask for these.
• Check the unit's systems. Most buildings date from the 1980s, so ask about the age of the heating, cooling, water heater and windows inside the unit.
• Know your full monthly cost. Add the mortgage, property taxes and HOA fee together. That total is what matters for your budget and your loan approval.

See Chester homes for sale, read the Chester, NY guide, or learn how buying works.

Selling Your Whispering Hills Unit

Buyers can compare many similar units, so condition, price and presentation matter. Recent sales give a clear price range for each unit type, and units priced right have sold quickly: the median time on market over the last year was 27 days.

• Price from recent sales of the same unit type, adjusted for updates, location in the complex and condition.
• Gather the condo documents and HOA contact early so the buyer's attorney and lender aren't waiting on them.
• Fix small items before photos. Paint, lighting and flooring updates stand out when buyers compare similar layouts.

Start with a free home value estimate or read about pricing a home in Chester and selling a home in Chester.

Whispering Hills FAQ