Chester Homes with Private Parking features

Welcome to Chester, nestled in the heart of Orange County, New York, where charming landscapes meet a vibrant community. This picturesque area is part of the highly regarded Chester School District, known for its commitment to academic excellence and fostering a nurturing environment for students. Families are drawn to Chester not only for its scenic beauty but also for the district's strong emphasis on education, with dedicated teachers and a wide range of extracurricular activities that encourage personal growth and development.

Living in Chester means enjoying the perfect blend of suburban tranquility and accessibility. The homes here often feature private parking, providing residents with the convenience and security they desire. Imagine coming home after a long day, pulling into your own driveway, and stepping into a warm, inviting space tailored to your lifestyle. These homes offer more than just shelter; they provide a sanctuary where memories are made and cherished.

Chester's community spirit is palpable, with local events and activities that bring neighbors together, fostering friendships and a sense of belonging. The area boasts beautiful parks, recreational facilities, and scenic hiking trails, making it an ideal setting for outdoor enthusiasts. With its friendly atmosphere, excellent schools, and homes that offer the luxury of private parking, Chester is not just a place to live; it's a place to thrive. Explore the opportunities that await you in this delightful corner of New York, where your dream home and a bright future for your family are within reach.

Newest Chester Homes with Private 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

$559,000

4 Beds ⋅ 3 Baths ⋅ 1004369 MLS

Welcome to 24 Walnut Street, Flexibility, Space & Endless Possibility in the Heart of Chester, NY Tucked on a generous half-acre lot in the charming Village of Chester, this versatile 4-bedroom, 2.5-bath home offers a rare mother-daughter layout that delivers the best of both worlds, income potential, or simply more space to grow. Set on a quiet, tree-lined street just minutes from the Orange Heritage Trail, local dining, and easy commuter access, this property is as practical as it is inviting. The main residence spans three spacious bedrooms and 1.5 baths, offering comfortable everyday living with room for the whole family. The private secondary suite features a bright one-bedroom, one-bath layout, ideal for in-laws, extended family, an au pair, or a long-term rental opportunity. Whether you're seeking to offset your mortgage or keep loved ones close while preserving everyone's privacy, this thoughtful configuration checks every box. With a 2,698 sq ft footprint, a full basement, attached garage, hardwood floors, central air, and a sweeping 0.56-acre lot with park views, this home combines classic charm with everyday function. Located in the Chester Union Free School District and just a short drive to Legoland, the Capelli Sports Complex, and Coach USA transit to NYC — 24 Walnut Street isn't just a home. It's a lifestyle. Opportunity like this doesn't last. Schedule your private showing today.

24 Walnut Street, Chester

$749,999

3 Beds ⋅ 3 Baths ⋅ 995624 MLS

Imagine ending every day watching the sun set from your front porch, with breathtaking views that change beautifully through every season. Sunset views, a fenced backyard, brand-new Trex deck, above-ground pool, home office, and the flexibility of **four sleeping spaces** make this property truly stand out. Perched atop the highly sought-after Fieldcrest subdivision, this stunning Colonial is officially listed as a **three-bedroom home** but offers a **spacious bonus room that provides the perfect opportunity for a fourth sleeping space**. Whether you need an additional bedroom, guest room, nursery, home office, or playroom, this versatile space adapts to your lifestyle. Set on 1.3 beautifully landscaped acres, the home blends comfort, functionality, and exceptional outdoor living. The fenced backyard features a newer oversized Trex deck, an above-ground pool, and plenty of room to relax, entertain, and create lasting memories with family and friends. Inside, sun-filled living spaces showcase hardwood floors, recessed lighting, a striking stone fireplace, and an expansive family room with a pellet stove capable of heating the entire home. The spacious kitchen serves as the heart of the home, complete with granite countertops, abundant cabinetry, stainless steel appliances, double ovens, and direct access to the backyard for seamless indoor-outdoor living. Upstairs, you'll find three generously sized bedrooms along with the versatile bonus room that provides valuable additional living and sleeping flexibility. The primary suite offers a private retreat with a Jacuzzi soaking tub and separate shower, while second-floor laundry adds everyday convenience. A walk-up attic, full basement, newer major systems, and exceptional curb appeal complete this impressive property. Offering the versatility of **three official bedrooms plus a bonus room that functions beautifully as a fourth sleeping space**, this home delivers the space, flexibility, and lifestyle today's buyers are searching for in one of the area's most desirable neighborhoods.

58 Nancy Lane, 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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