Chester Homes with Maintenance Grounds Amenities

Welcome to Chester, New York—a picturesque town nestled in the heart of Orange County, where charming landscapes meet a vibrant community spirit. Known for its stunning natural beauty, Chester is surrounded by lush mountains and serene lakes, making it a haven for outdoor enthusiasts and those seeking a peaceful retreat from the hustle and bustle of city life.

As you explore Chester, you’ll discover a delightful blend of quaint shops, delightful eateries, and a rich history that adds character to this lovely town. The community is known for its friendly atmosphere and hosts various events throughout the year, fostering a strong sense of belonging among residents.

When it comes to housing, Chester offers an array of homes with maintenance grounds amenities, allowing you to enjoy a worry-free lifestyle. These properties are designed for those who appreciate the beauty of well-manicured lawns and gardens without the hassle of upkeep. With maintenance grounds, you can spend more time enjoying the scenic views and less time on chores, making it an ideal choice for busy professionals, families, or retirees.

Whether you’re looking for a cozy cottage or a spacious family home, Chester’s real estate market has something to suit every taste and budget. Living in this enchanting town not only grants you access to nature’s wonders but also places you within a close-knit community that values connection and camaraderie. Discover your dream home in Chester today, where tranquility meets convenience, and every day feels like a getaway!

Newest Chester Homes with Maintenance Grounds Amenities

$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

Start Your Search

© 2026 TReND. All Rights Reserved.
The data relating to real estate for sale on this website appears in part through the TReND Internet Data Exchange (IDX) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Real Broker NY LLC participates, and is provided by TReND through a licensing agreement. Real estate listings held by brokerage firms other than Real Broker NY LLC are marked with the IDX icon and detailed information about each listing includes the name of the listing broker.
All information provided is deemed reliable but is not guaranteed. Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.