Pending
Price CutPrice Drop: $25K (09/22)
Sale Pending at 4008 Whispering Hills Dr, Chester Town, NY 10918 | MLS# 1027838 | Listing updated on 2026-09-23
Photo 1 of Sale Pending at 4008 Whispering Hills Dr, Chester Town, NY 10918 | MLS# 1027838 | Listing updated on 2026-09-23
Photo 2 of Sale Pending at 4008 Whispering Hills Dr, Chester Town, NY 10918 | MLS# 1027838 | Listing updated on 2026-09-23
Photo 3 of Sale Pending at 4008 Whispering Hills Dr, Chester Town, NY 10918 | MLS# 1027838 | Listing updated on 2026-09-23
Photo 4 of Sale Pending at 4008 Whispering Hills Dr, Chester Town, NY 10918 | MLS# 1027838 | Listing updated on 2026-09-23
29+
Beds Icon

Street View

$290,000

Monthly Est:$1,443

  • Beds Icon2 Beds
  • Beds Icon
    2 Baths
  • Beds Icon1,072sqft

4008 Whispering Hills Dr, Chester Town, NY 10918

$1,443/moEst:

Get Pre-Approved

  • Condominium

  • Built in 1987

  • $465/mo HOA

  • 435.6 sqft lot

  • $271/sq.ft

Description

Move in ready townhome with a NYC bus stop within the community!! Whispering Hills in Chester is perfectly positioned for commuters being 2 miles to Route 17.
Enjoy a prefect blend of comfort and convenience with a maintenance free lifestyle in this two bedroom townhome. The main floor has brand new flooring, a living room with a wood burning fireplace,and a separate dining area ideal for entertaining.The kitchen has a tile backsplash, and a natural gas range. A convenient half bath and laundry area complete the first floor. Upstairs,the primary bedroom offers vaulted ceilings,a generous walk in closet and a full bath with private access to the hallway. The second bedroom is of ample size with a double door closet. A skylight in the hallways brightens the home. Additional features and highlights include central air, natural gas heating, an attached one car garage with extra storage, building roof replaced in 2022, HVAC 2013, skylight 2013, municipal water and sewer,reasonable hoa fees, snow removal and beautifully maintained grounds. Community amenities feature a dog park, playground, two pools, a gym and more.
Just 5 minutes from the heart of Chester where you'll find local shopping,dining and entertainment all while remaining 70 miles from NYC, 10 minutes to LegoLand and close to Woodbury Common, Resorts Casino and Bethel Woods Concert Venue. Visit our nearby breweries, cafes,farmer market and historic Sugarloaf Village. Come see why everyone wants to live here!

  • Houzeo last checked: 12 hours ago
  • Listing updated: September 23, 2026 at 7:09 am
  • Listing Provided by: Karen R Taphorn (845) 774-6858 | Howard Hanna Rand Realty (845) 928-9691
  • Source: OneKey MLS-NY | MLS#: 1027838 OneKey MLS-NY

Part of

Building
4008 Whispering Hls Dr
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Property Details

  • Status

    Pending

  • Type

    Condominium

  • No. of Stories

    -

  • County

    Orange County

  • City

    Chester Town

  • Neighborhood

    --

  • Year Built

    1987

  • HOA Fees

    $465/mo

  • Finished Area

    1,072 sqft

  • Lot Size

    435.6 sqft lot

  • Basement Area

    - sqft

  • MLS Name

    OneKey MLS

  • MLS Number

    1027838

  • MLS Status

    Pending

  • Days on Market

    66

  • Cumulative Days on Market

    57

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Location

HOA Management

Spinnaker

HOA Fees

$465/ Monthly

Amenities

Amenities and services may be covered by one or multiple associations and service providers.

Club House Club House

Basket Ball Basket Ball

Trash Pickup Trash Pickup

Pool Pool

Snow Removal Snow Removal

Park Playground Park Playground

Gym Gym

Children's Playroom Children's Playroom

Exterior Maintenance Exterior Maintenance

Common Area Maintenance Common Area Maintenance

Grounds Care Grounds Care

Pool Service Pool Service

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 2

    Bathrooms: 2

  • Kitchen

    Level: First

  • Living Room

    Level: First

  • Dining Room

    Level: First

  • Lavatory

    Level: First

  • Laundry

    Level: First

  • Primary Bedroom

    Level: Second

  • Bedroom 2

    Level: Second

  • Bathroom 2

    Level: Second

Interior

  • Flooring

    Carpet, Laminate

  • Appliances

    Dishwasher, Dryer, Gas Oven, Gas Range, Refrigerator, Washer

  • Sewer

    Public Sewer

  • Interior Features

    Cathedral Ceiling(s), Ceiling Fan(s), Formal Dining, High Ceilings, Open Floorplan, Recessed Lighting, Walk In Closet(s)

  • Heating

    Forced Air

  • Cooling

    Central Air

Construction

  • Year Built

    Year Built: 1987

  • Home type

    Condominium

  • Property Condition

    Updated/remodeled

  • Construction Materials

    Frame

Utilities & Energy

  • Parking Features

    Attached, Garage

  • Association Amenities

    Basketball Court, Children's Playroom, Clubhouse, Dog Park, Fitness Center, Pool, Snow Removal

  • Basement

    None

  • Pool Features

    Community

  • Water Source

    Public

  • Utilities

    Cable Connected, Electricity Connected, Natural Gas Connected, Phone Connected, Sewer Connected, Water Connected

  • Fireplace Features

    Wood Burning

Other Features

  • Patio And Porch Features

    Patio

  • Subdivision Name

    Whispering Hills

  • Community Features

    Clubhouse, Fitness Center, Playground, Pool, Sidewalks

Price History

DateEventPrice

09/22/2026

Source: mls_logoOneKey MLS-NY #KEY1027838

Pending

$290,000 -7.94%

$271/sqft

07/27/2026

Source: mls_logoOneKey MLS-NY #KEY1027838

Listed for Sale

$315,000

$294/sqft

Nearby Homes

Based on information from OneKey MLS, through Oct 01, 2026, 02:47PM. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. © 2026 OneKey® MLS. All rights reserved.

Advertising Broker: Derek Greene | The Greene Realty Group