Chester Homes with Park Amenities

Welcome to Chester, New York – a hidden gem nestled in the heart of Orange County. This picturesque town is renowned for its charming small-town vibe, surrounded by the breathtaking natural beauty of the Hudson Valley. With its rich history, vibrant community, and stunning landscapes, Chester offers an idyllic setting for families, retirees, and nature enthusiasts alike.

One of the standout features of Chester is its commitment to outdoor living. Residents enjoy access to a variety of park amenities, making it easy to embrace the great outdoors. With lush parks, scenic trails, and recreational facilities, Chester provides ample opportunities for hiking, picnicking, and enjoying the beauty of nature. The town’s parks are perfect for family outings, weekend adventures, or simply unwinding after a long day.

When it comes to real estate, Chester offers a delightful array of homes that cater to diverse tastes and lifestyles. Many properties are situated near or within walking distance of the local parks, allowing residents to enjoy the best of both worlds – a tranquil home environment and easy access to outdoor activities. Whether you’re looking for a cozy cottage, a spacious family home, or a modern retreat, Chester has something for everyone.

In addition to its natural beauty, Chester boasts a vibrant community spirit, with local events, farmers' markets, and festivals that bring residents together. With its blend of picturesque landscapes, park amenities, and a welcoming atmosphere, Chester is not just a place to live; it’s a place to thrive. Explore the possibilities of making this charming town your new home!

Newest Chester Homes with Park 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

$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

$1,139,900

4 Beds ⋅ 5 Baths ⋅ 982679 MLS

Welcome to Chester, NY, a resort-style luxury colonial set on a private 1.1-acre cul-de-sac lot in the Monroe-Woodbury area of Orange County. This custom residence delivers the space, craftsmanship, and lifestyle today's relocation and move-up buyers are searching for, with approximately 4,624 square feet, refined architectural detail, mountain views, and seamless indoor-outdoor living. From the bluestone entry and custom foyer to the arched windows, detailed millwork, and stone fireplace, every major room has been designed to make a statement. The chef's granite kitchen, expansive family room, and finished lower level with theater, gym, and additional recreation space create flexibility for entertaining, working from home, and everyday luxury. Outside, the backyard becomes the headline feature: saltwater in-ground pool, firepit, koi pond, extensive pavers, and a 3-season outdoor kitchen that gives this home true vacation-at-home appeal. For buyers looking for a luxury home in Chester NY, a Hudson Valley estate near NYC, or a Monroe-Woodbury area home with pool, privacy, and commuter convenience, This is the kind of property that sells both a residence and a lifestyle.

16 Lori Lane, Chester

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