Chester Homes with Off Street Parking features

Welcome to Chester, New York—a charming town nestled in the heart of Orange County, where community spirit and natural beauty converge. Known for its picturesque landscapes and friendly atmosphere, Chester is an ideal place for families seeking a vibrant and nurturing environment. One of the standout features of this delightful area is its highly regarded school district, which prioritizes academic excellence and holistic development for students.

The Chester School District is dedicated to fostering a love for learning, offering a range of programs that cater to diverse interests and talents. With small class sizes and a commitment to personalized education, teachers in Chester are able to provide individual attention, ensuring that every child can thrive. The district boasts a variety of extracurricular activities, from athletics to arts, allowing students to explore their passions and develop essential life skills. Parents can rest easy knowing that their children are receiving a quality education in a supportive community.

In addition to its excellent schools, Chester offers a variety of homes that feature off-street parking—an essential convenience for busy families. Imagine returning home after a long day, pulling into your own driveway, and stepping into your cozy abode without the hassle of street parking. These homes provide not just comfort, but also peace of mind, making them perfect for those who value both accessibility and tranquility.

Explore the enchanting community of Chester, where exceptional education and convenient living come together to create a truly delightful place to call home.

Newest Chester Homes with Off Street Parking features

$399,999

4 Beds ⋅ 2 Baths ⋅ 1024779 MLS

Discover the timeless charm and endless potential of this classic Colonial farmhouse, ideally situated on just under one level acre in the heart of Chester, NY. Offering approximately 1,560 square feet of living space, this 4 bedroom, 2 bath home is filled with character and craftsmanship. Step inside to find original hardwood floors, a cozy wood-burning stove, and an artistic, welcoming atmosphere that highlights the home's authentic farmhouse appeal. Rich with historic charm and original details, this property is ready for its next owner to restore and make it their own. Enjoy peaceful, scenic views of the surrounding greenery while benefiting from a highly convenient commuter friendly location. Just minutes from the highway, downtown Chester, Goshen, Monroe, and Warwick, you'll have easy access to local shops, restaurants, parks, wineries, farmers markets, and everything the Hudson Valley has to offer. Priced with the home's restoration needs in mind, this is a rare opportunity to invest in a property with incredible potential, generous outdoor space, and an unbeatable location. Whether you're searching for a primary residence, weekend retreat, or renovation project, this farmhouse is ready to be brought back to life. Schedule your private tour today and imagine the possibilities!

241 Meadow Avenue, 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

$3,400,000

4 Beds ⋅ 4 Baths ⋅ 988789 MLS

Set behind a gated entrance with a private guard house and unfolding across 8.4 private acres, The Retreat at Greentree is a true estate in every sense, engineered for privacy, designed for lifestyle, and positioned as one of the most unique offerings in the Hudson Valley. A cascading waterfall greets you on arrival, establishing a sense of calm and separation from the outside world. From that moment forward, every detail reinforces the same idea. This property was built intentionally, without compromise. Originally designed by renowned architect Paul Rudolph, the residence carries a level of architectural pedigree rarely available. Spanning over 7,750 square feet, the home blends that design legacy with modern performance, including radiant heated floors, geothermal systems, and thoughtfully curated living spaces that feel both refined and highly functional. What truly sets this property apart is the lifestyle it delivers. A private helipad offers direct access to Manhattan in approximately 14 minutes, redefining convenience at the highest level. The grounds unfold as a resort-caliber setting, anchored by a heated saltwater pool, three private cabanas, and a fully equipped outdoor kitchen with a dedicated dining space designed for effortless indoor outdoor living. A rare white sand beach introduces an unexpected element, creating a setting that feels more like a destination resort than a private residence. Inside, the home takes on a spa-like atmosphere, with wellness-driven features including a private sauna and spaces designed to restore and recharge. The primary suite is its own retreat, complete with a three-season room that extends the experience outdoors while maintaining complete privacy. A fully built-out home theater adds another layer to the lifestyle, bringing a true cinematic environment into the comfort of your own home. Beyond the property itself, the location adds another dimension. This is the perfect getaway for winter weekends, fall retreats, or summer escapes, surrounded by some of the Hudson Valley’s most sought-after destinations. Just minutes from LEGOLAND New York Resort, Woodbury Common Premium Outlets, Warwick Valley Winery & Distillery, local apple orchards throughout Warwick, Bear Mountain State Park for skiing and outdoor recreation, and the five-star Glenmere Mansion, the area offers a rare blend of recreation, luxury, and accessibility. Hiking, camping, fishing, skiing, biking, horseback riding, fine dining, and shopping are all within reach, creating a year-round lifestyle that is both active and refined. This is more than a residence. It is a fully realized compound, private, efficient, and architecturally significant, built for someone who values time, discretion, and a level of living that cannot be replicated.

19 Greentree Lane, Chester

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