Chester Homes with Dog Park Amenities

Chester Homes with Dog Park Amenities

Welcome to Chester, New York—a charming town nestled in the picturesque Orange County, where community spirit meets breathtaking natural beauty. Chester boasts a highly regarded school district that prioritizes academic excellence and holistic development. Families are drawn to the Chester School District for its commitment to fostering a nurturing environment, where students are encouraged to explore their passions and excel in their studies. With dedicated teachers, innovative programs, and a range of extracurricular activities, children in Chester are provided with a well-rounded education that prepares them for future success.

Beyond its educational offerings, Chester is a haven for dog lovers, featuring homes that come with delightful dog park amenities. Imagine stepping outside your front door and finding a spacious, well-maintained dog park just a short stroll away. These parks provide a safe and inviting space for your furry friends to socialize, exercise, and enjoy the great outdoors. Whether you're a proud owner of a playful pup or a serene senior dog, these pet-friendly homes in Chester ensure that your four-legged family members have the room to roam and play.

In addition to the wonderful school district and dog park amenities, Chester offers a vibrant community filled with local shops, restaurants, and recreational opportunities. With its blend of quality education, pet-friendly living, and a warm, welcoming atmosphere, Chester is not just a place to live; it’s a place to thrive. Discover your dream home in this idyllic town today!

Newest Chester Homes with Dog Park Amenities

$370,000
3 Beds 2 Baths 1046996 MLS
Move right in! This beautifully maintained and thoughtfully updated 3-bedroom, 2-full-bath END-UNIT condo offers almost 1,400 square feet of comfortable, easy one-level living in the desirable Whispering Hills community. As soon as you enter the welcoming two-story foyer, you’ll appreciate how bright, open, and impeccably maintained this home is. The spacious open-concept living area features vaulted ceilings and a beautiful Marble & Wood fireplace, creating a warm, inviting atmosphere. Sliding doors lead to your private deck provides easy access to enjoy the peaceful, beautifully landscaped surroundings. The renovated kitchen is both stylish and functional, featuring modern cabinetry, granite countertops, updated backsplash, Stainless appliances and a pantry with plenty of shelving, The spacious primary suite is truly a standout! Enjoy a large walk-in closet with California shelving and a renovated full bath frameless shower. Two additional bedrooms provide plenty of flexibility for guests, a home office, or other needs. Additional updates include sparkling new flooring throughout, new water heater & Washer/Dryer. The attached one-car garage provides convenient direct access to the home along with dedicated storage space. Enjoy all that Whispering Hills has to offer, including a two community pools, tennis court, kids park, dog park, sidewalks, and a peaceful setting—while being just minutes from shopping, restaurants, parks, and major commuter routes. Located in the Chester School District. All this with New York City bus that picks up and drops off right in the complex. Don't miss your opportunity to make it yours. Call today for your private tour. *****Professional Photos Coming Soon****

3211 Whispering Hills, Chester

$290,000
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

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