Chester Homes with Detached Parking features

Welcome to Chester, New York—a picturesque gem nestled in the heart of Orange County. Known for its charming small-town atmosphere and beautiful natural surroundings, Chester is not just a place to live; it’s a community that fosters growth, education, and connection.

One of the standout features of Chester is its highly regarded school district, which prides itself on providing a nurturing and enriching environment for students. The Chester School District offers a comprehensive curriculum that emphasizes academic excellence while fostering creativity and critical thinking skills. With dedicated teachers and a variety of extracurricular activities, students are encouraged to explore their passions and develop into well-rounded individuals. Families can feel confident that their children are receiving a quality education that prepares them for future success.

In addition to its educational offerings, Chester presents a variety of real estate options, including homes with detached parking—a coveted feature that adds convenience and value to your property. Imagine coming home to your own private parking space after a long day, providing easy access to your home and enhancing your outdoor living experience. Whether you’re entertaining guests or simply enjoying the tranquility of your surroundings, detached parking allows for extra space and flexibility.

Chester is not just a place to live; it’s a community where families can thrive, children can learn, and memories can be made. Explore the beauty of Chester, NY, and discover your dream home in this idyllic setting today!

Newest Chester Homes with Detached Parking features

$599,900

3 Beds ⋅ 2 Baths ⋅ 1029645 MLS

Located in the heart of the Village of Chester, this beautifully updated home offers the rare combination of modern comfort, privacy, and convenience. Just steps from Chester Academy and the Heritage Trail, this property provides easy access to walking, biking, running, local events, and community amenities while offering the peaceful retreat of your own private acreage. Set on 4 private acres, this home is a nature lover’s dream. The expansive property offers the perfect balance of open space and natural beauty, providing endless opportunities for outdoor enjoyment, family adventures, gardening, recreation, and creating your own private oasis. The large yard gives children plenty of room to play, explore, and connect with nature, while offering the space and flexibility for a hobby farm, gardens, chickens, outdoor activities, or other homesteading dreams. The entire home has been thoughtfully renovated within recent years, offering a fresh, updated feel throughout. A new HVAC system provides added comfort, efficiency, and peace of mind. The home also offers excellent future expansion potential with a full walk-out basement ready to be finished—perfect for a recreation room, guest suite, home gym, office, playroom, or media area. A standout feature is the oversized garage, providing exceptional space for vehicles, storage, hobbies, a workshop, or additional workspace. Step outside and enjoy the wrap-around back porch, the perfect place to relax, entertain, and take in the peaceful surroundings of your expansive yard. Whether enjoying morning coffee, hosting friends and family, or watching kids explore the outdoors, this space truly embraces the best of country-style living with village convenience. Property Highlights • Beautifully renovated home with modern updates • Just steps from Chester Academy and the Heritage Trail • Prime Village of Chester location close to schools, shops, and amenities • 4 private acres with beautiful natural surroundings • Perfect property for nature lovers and outdoor enthusiasts • Large yard ideal for kids to play, explore, and create memories • Endless possibilities for gardens, recreation, and hobby farming • New HVAC system • New roof • Full walk-out basement with finishing potential • Oversized garage with ample storage and workspace • Wrap-around back porch overlooking the property A rare opportunity to own a move-in ready home with land, updates, and endless possibilities—all in one of Chester’s most convenient locations. Whether you’re looking for space to grow, room for your family to explore, or the opportunity to create your own private retreat, 50 Hambletonian Ave offers the lifestyle you’ve been searching for.

50 Hambletonian Avenue, Chester

$575,000

6 Beds ⋅ 2 Baths ⋅ 992189 MLS

Rare opportunity. Come in and see this multi-family property in Chester, NY, and very close to main highways. This features 2 separate structures with their own utilities and natural gas. The main house presents 4 bedrooms, a kitchen, a dining room, and a living room with 1 full bath. main house is fully professional painted recently and now floors and roof on this house is 2 years old. The Second beautiful structure offers hardwood floors, as seen, 2 bedrooms, a kitchen, a living room, and 1 full bath. In addition, there is a garage about 750 sq that can be rented out for another few hundred dollars a month. Enjoy the beautiful 1.1-acre property. This unique property has multiple opportunities!

68 Conklingtown Road Unit #1&2, Chester

$1,145,000

9 Beds ⋅ 7 Baths ⋅ 995148 MLS

Own One of America's Great Equestrian Landmarks Steeped in history and unlike anything else on the market, The Hambletonian House is a magnificent Victorian estate built in the 19th century by William Rysdyk, owner of the legendary Hambletonian 10—the foundation sire of nearly every modern Standardbred racehorse. More than a remarkable home, this is an opportunity to become the next steward of one of the most significant equestrian properties in history. Gracefully set atop a scenic knoll on nearly three private acres in the heart of Chester, New York, the estate offers exceptional privacy while remaining just 40 miles from Manhattan. From the moment you arrive, the home's commanding presence, timeless architecture, and beautifully maintained grounds create an unforgettable first impression. The stately main residence features seven bedrooms and four-and-a-half bathrooms, where authentic Victorian craftsmanship has been meticulously preserved. Soaring ceilings, original hardwood floors, intricate millwork, marble fireplaces, elegant pocket doors, and exquisite architectural details reflect the grandeur of a bygone era, while thoughtful modern updates provide today's expected comforts. Designed for both elegant entertainment and everyday living, the home's expansive gathering spaces flow effortlessly to the surrounding grounds, creating an ideal setting for celebrations, family gatherings, or quiet evenings enjoying the beauty of the property. Adding to the estate's resort-style appeal is a separate pool house, complete with a full bathroom and private sauna, offering the perfect retreat for relaxation, wellness, or entertaining guests throughout the seasons. One of the property's most compelling features is its detached second residence, offering a beautifully appointed two-bedroom apartment with exceptional flexibility. Beyond providing luxurious accommodation for guests or extended family, this separate living space creates an outstanding opportunity for additional income. Whether utilized as a premium long-term rental, short-term vacation rental, executive housing, caretaker's residence, or owner's quarters while operating the main home as a hospitality property, it provides the versatility today's buyers are seeking. Beyond its architectural beauty, the property presents an exceptional opportunity to offset ownership costs through multiple revenue streams. This rare combination of a landmark residence and an income-producing secondary dwelling makes the estate equally attractive to homeowners, investors, and entrepreneurs. With its iconic history, breathtaking setting, and expansive layout, The Hambletonian House is ideally suited as a luxury bed and breakfast, boutique inn, private event venue, executive retreat, or premier destination rental—offering limitless possibilities for both lifestyle and investment. The current owner has invested extensively in preserving the estate's historic integrity while making significant improvements to major mechanical systems and the roof, ensuring modern reliability without compromising its timeless character. This careful stewardship allows the next owner to enjoy the confidence of updated infrastructure while preserving a truly irreplaceable piece of history. Ideally located near the shops, restaurants, and conveniences of the Village of Chester, with easy access to major highways and the best of the Hudson Valley, the property offers the perfect balance of peaceful country living and metropolitan accessibility. Properties of this significance rarely become available. Combining rich history, exceptional architecture, income-producing potential, and an irreplaceable legacy, The Hambletonian House represents a once-in-a-generation opportunity to own one of the most celebrated equestrian landmarks. Some homes are purchased. Others become part of history. This is one of them.

19 High Street, Chester

$500,000

3 Beds ⋅ 2 Baths ⋅ 976521 MLS

3 bedroom 2 bath contemporary home tucked away on a quiet street. Modern renovation already started, put your finishing touches on it. Home sold as is. Open concept living, spacious kitchen, private primary suite on 2nd floor with 2 additional bedrooms on 1st floor. Peaceful setting and still close to all amenities. 1,000 sq ft 2 car detached garage.

5 N Hudson Street, Chester

$379,900

2 Beds ⋅ 1 Baths ⋅ 964090 MLS

Great new price! Come take a look at this 2 bedroom charmer with additional room offers potential 3+ bedrooms. Larger than it looks - need to see. Discover the timeless charm and surprising spaciousness of this delightful carriage house, set on a property rich with character and possibility. Step inside to a generous living room where a wood burning fireplace, hardwood floors, and a large bay window create a bright, welcoming atmosphere. Wall sconces add a soft glow, and a wall A/C unit ensures comfort throughout the warmer months. The eat in kitchen blends practicality with charm, offering tile floors, a newer refrigerator, a handy island, abundant cabinetry, and a pantry for extra storage. Another bay window brings in natural light and enhances the home’s cozy appeal. A full bathroom with a classic pedestal sink and tub completes the main living space. The primary bedroom features hardwood floors, newer windows, two closets, and its own wall A/C unit. A second bedroom—equally charming—also offers hardwood floors and plenty of natural light. Throughout the home, you’ll find generous storage options, including ample closets and a pull down attic. The property is thoughtfully equipped with a natural gas generator, a paved driveway, and multiple outbuildings that expand its functionality. The main house includes an attached two car garage, while a separate two car detached garage showcases original carriage house doors that add a touch of historic character. A small shed provides additional storage, and an oversized outbuilding—with an 8' garage door, separate electric and gas meter, and gas boiler heat—offers exceptional versatility. Above it sits a caretaker’s apartment, ideal for guests, extended family, or workspace needs. All structures are being sold as is. An additional parcel with a storage barn is also available, offering even more room to grow, store, or create. This property blends charm, practicality, and potential in a way that’s increasingly rare—inviting you to imagine the many ways it can fit your lifestyle.

7 Hambletonian Avenue, Chester

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