Chester Homes with Pool Amenities

Welcome to Chester, New York—a charming town nestled in the picturesque Orange County, where natural beauty meets modern living. Known for its stunning landscapes and vibrant community, Chester offers a unique blend of rural tranquility and suburban convenience. With its proximity to the Hudson Valley and the breathtaking views of the nearby mountains, residents can enjoy a plethora of outdoor activities, from hiking and biking to fishing and boating.

Chester is not just a haven for nature lovers; it also boasts a welcoming community atmosphere, complete with local shops, delightful eateries, and seasonal events that bring neighbors together. The town’s rich history is reflected in its well-preserved architecture and the scenic beauty of its parks, making it a perfect place to call home.

For those seeking a touch of luxury, Chester’s real estate market features stunning homes with pool amenities that elevate the living experience. Imagine soaking up the sun in your own backyard oasis, with a sparkling pool just steps away. These homes are designed for both relaxation and entertainment, offering spacious outdoor areas perfect for summer gatherings or quiet evenings under the stars. With a variety of styles and sizes available, you can find the perfect residence that fits your lifestyle.

Whether you’re a first-time homebuyer or looking to upgrade, Chester’s homes with pool amenities provide a unique opportunity to embrace the beauty of the outdoors while enjoying the comforts of modern living. Come discover the charm of Chester, where your dream home awaits!

Newest Chester Homes with Pool Amenities

$279,999

2 Beds ⋅ 2 Baths ⋅ 1030827 MLS

Welcome to 2007 Whispering Hills Drive! This 2-bedroom, 1.5-bath condo offers comfortable living in one of Chester’s most desirable communities. The main level features a spacious living room with a real wood-burning fireplace, a dining area, and a kitchen with stainless steel appliances. Luxury vinyl plank flooring adds a modern touch throughout the main living areas. Upstairs, you’ll find two generously sized bedrooms and a full bath, while a convenient first-floor powder room is perfect for guests. Additional features include an attached two-car garage and access to Whispering Hills’ outstanding amenities, including a swimming pool, clubhouse, tennis courts, and basketball courts. Conveniently located close to shopping, restaurants, and major highways, this home offers easy, low-maintenance living with an unbeatable location.

2007 Whispering Hills, Chester

$315,000

2 Beds ⋅ 2 Baths ⋅ 1027838 MLS

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!

4008 Whispering Hills Drive, Chester

$349,999

3 Beds ⋅ 2 Baths ⋅ 974398 MLS

Welcome home to this beautifully updated 3-bedroom, 2-bathroom condominium with a 1-car garage, perfectly situated in the highly sought-after Whispering Hills community. Offering modern upgrades, spacious living, and resort-style amenities, this home is truly move-in ready. Step inside to discover a bright, open floor plan featuring gleaming hardwood floors, an updated chef-inspired kitchen with granite countertops, ample cabinetry, and plenty of prep space for entertaining. The renovated bathrooms offer stylish finishes and a fresh, modern feel with all new windows to help keep the indoor temperature steady. The spacious living room is filled with natural light and features a cozy wood-burning fireplace, creating the perfect place to relax year-round. The living room also opens through a brand-new sliding glass door to a private deck—ideal for morning coffee, outdoor dining, or simply enjoying the peaceful surroundings. The primary suite offers generous closet space and easy access to an updated full bath, while two additional bedrooms provide flexibility for family, guests, or a home office.

3414 Whispering Hills, Chester

$295,000

2 Beds ⋅ 2 Baths ⋅ 1019548 MLS

Step into this gorgeous Townhouse.Upon entering you’ll be welcomed by a perfect floor plan. The inviting living room features wooden floors, a cozy fireplace, and windows. The stylish kitchen has a functional layout and is outfitted with stainless steel appliances and granite countertops. The master-bedroom offers a modern feel and a walk in closet. Enjoy the amenity centers. Stop dreaming and start living, come and take a look today! The Condo charges $475 , HOA $250

2119 Whispering Hills, Chester

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