Chester Homes with Garage Door Opener Parking features

Welcome to Chester, New York – a hidden gem nestled in the picturesque Orange County. Known for its stunning natural beauty and vibrant community spirit, Chester offers a delightful blend of serene rural living and modern conveniences. With the majestic backdrop of the Catskill Mountains, this charming town is perfect for nature enthusiasts and families alike, providing ample opportunities for hiking, fishing, and outdoor adventures.

Chester boasts a rich history and a warm, welcoming atmosphere. The town is dotted with quaint shops, local eateries, and community events that foster a strong sense of belonging among its residents. Whether you're exploring the enchanting local parks or enjoying a leisurely stroll through the historic downtown area, Chester is a place where you can truly feel at home.

For those seeking a new residence in this idyllic setting, you'll be pleased to discover a variety of homes equipped with convenient garage door opener parking features. These modern amenities provide ease and security, ensuring that your vehicle is protected from the elements while also offering you quick access when you’re on the go. Imagine coming home after a long day, pulling into your garage, and stepping into your cozy sanctuary without a care in the world.

With its combination of stunning landscapes, friendly community, and modern conveniences, Chester, NY, is the perfect place to find your dream home. Explore the possibilities today and discover why so many are choosing to call Chester their home!

Newest Chester Homes with Garage Door Opener Parking features

$279,999

2 Beds ⋅ 2 Baths ⋅ 1030827 MLS

Welcome to 2007 Whispering Hills Drive! This 2-bedroom, 1.5-bath condo offers comfortable living in one of Chester’s most desirable communities. The main level features a spacious living room with a real wood-burning fireplace, a dining area, and a kitchen with stainless steel appliances. Luxury vinyl plank flooring adds a modern touch throughout the main living areas. Upstairs, you’ll find two generously sized bedrooms and a full bath, while a convenient first-floor powder room is perfect for guests. Additional features include an attached two-car garage and access to Whispering Hills’ outstanding amenities, including a swimming pool, clubhouse, tennis courts, and basketball courts. Conveniently located close to shopping, restaurants, and major highways, this home offers easy, low-maintenance living with an unbeatable location.

2007 Whispering Hills, Chester

$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

$1,195,000

4 Beds ⋅ 4 Baths ⋅ 1010585 MLS

Welcome to an unparalleled expression of luxury living in the Town of Chester. Built in 2003, this custom-built Cape May/Colonial estate designed by award winning architect Larry Belk estate spans 4,281 square feet of meticulously designed living space, masterfully balancing grand entertaining spaces with intimate everyday comfort. From the moment you arrive, exceptional craftsmanship is on display—from the solid wood doors and dual staircases to the premium radiant-heated floors sweeping across the entire main level. The inviting foyer seamlessly transitions into the formal living and dining rooms, both framed by dramatic floor-to-ceiling windows, intricate crown molding, and striking red oak flooring with Mahogany inlays. Both formal spaces open directly to an expansive bluestone patio, offering an effortless indoor-outdoor lifestyle. At the heart of the home is a true culinary enthusiast’s kitchen, outfitted with oversized granite countertops, custom cabinetry, and a table-height center island. Immediately adjacent, a sunken family room anchored by a rustic wood-burning fireplace serves as the perfect gathering hub, featuring French doors that lead to a covered bluestone patio and a private fire pit area. Retreat to the main-level primary suite—a serene sanctuary complete with gas fireplace and French doors opening to a private, wrap around covered Trex deck. The spa-like primary bath boasts a vintage-inspired cast iron clawfoot tub, a walk-in shower, and dual vanities, all complemented by a massive walk-in closet. A dedicated laundry room completes the main level. Upstairs, discover a versatile bonus loft accessed via a spiral staircase, a full walk-up attic, and three generously sized bedrooms—two of which feature private en-suite baths and walk-in closets. The lower level is an enthusiast’s dream. Beyond vast storage capabilities, this floor houses a dedicated wine-making room and provides direct access to an extraordinary, pristine multi-car garage featuring professional epoxy flooring. A true masterpiece of design, utility, and sophistication. Enjoy effortless travel with immediate access to Route 17 (I-86) and the NYS Thruway, while mass transit options like the Chester Park & Ride and the Harriman Train Station make commuting a breeze. Located just 60 miles from NYC, you can enjoy the peace of the suburbs and be in the city in just over an hour. Unbeatable location for entertainment, dining, and shopping! You are 10 miles from the world-famous Woodbury Common Premium Outlets. Explore Chester’s vibrant local food scene, steps from local restaurants, craft breweries, and renowned local wineries. Outdoor enthusiasts will love the proximity to the scenic Orange Heritage Trail. Exceptional location, maximum convenience, and a perfect place to call home!

22 Goshen Road, Chester

$675,000

4 Beds ⋅ 3 Baths ⋅ 1009848 MLS

Set on 3.2 acres within the Monroe-Woodbury School District, 335 Laroe Road offers a rare combination of space, functionality, and a convenient Chester location. Step inside to the welcoming two-story foyer featuring an open staircase and you'll immediately appreciate the size of the home. The main level offers a functional layout with multiple living spaces, including a living room, formal dining room, and family room anchored by a floor-to-ceiling stone fireplace. Large windows throughout the main level bring in an abundance of natural light, creating a bright and open feel throughout the home. The eat-in kitchen is designed for both everyday use and entertaining, offering generous cabinet and counter space, a center island, and an open layout that connects well with the rest of the home. French doors lead directly from the kitchen to the rear deck, which was updated within the last two years and provides plenty of room to enjoy the outdoor setting. The first floor also features a large pantry and laundry area with an impressive amount of cabinetry and storage, along with a full bathroom for added convenience. Upstairs, you'll find four bedrooms and two full bathrooms, including a spacious primary suite. The basement offers an incredible amount of additional space and storage that truly needs to be seen in person to be appreciated. Throughout the home, there is no shortage of storage or usable living space. Outside, the property provides a mix of open yard and mature trees across 3.2 acres, offering plenty of room to enjoy the outdoors. An existing in-ground pool is also located on the property and is being sold as-is. Located right next door, the Orange County Recreation Area at Laroe Road features walking and hiking trails, picnic areas, fishing ponds, and additional green space for all to enjoy. Call today to schedule your private showing. **Home is being sold AS-IS**

335 Laroe Road, Chester

$529,000

3 Beds ⋅ 3 Baths ⋅ 898870 MLS

Some lots just have good bones. This one has it's own private nature trail, stocked pond rights, and a cul-de-sac that dead-ends into miles of nature trails anchored by a solid, spacious raised ranch on 1.8 acres. Inside, the home has been partially updated and offers solid bones with room to add your own touch over time. The house delivers where it counts. Three bedrooms, two and a half baths, large kitchen, a two-car garage, and a three-season room and deck that make the most of a property this beautiful. The woodburning stove in the basement helps the winter months stay cozy while saving on fuel oil bills. Multiple outbuildings including a shed and a playhouse that will get more use than you'd expect. The lawn and mature landscaping are genuinely impressive — the kind that takes years to establish and shows the moment you pull in the driveway. Then there's everything else. When not playing on the impeccable lawn, the kids could be kids catching frogs and fish, climbing trees and building forts in the woods.. All without leaving the property. When they do, the trail into Goosepond Mountain State Park is just a few doors down, at the end of the Cul de Sac.. The street itself is unhurried and unpretentious — picture dads teaching kids to ride bikes in the road, strollers, joggers, dogs on leashes and kids swarming ice cream trucks. With easy access to amenities and a realistic commute to NYC, Booth Rd means you don't have to choose between the life you want and the job that funds it. Come feel it. The land speaks for itself.

94 Booth Road, Chester

$825,000

4 Beds ⋅ 3 Baths ⋅ 999741 MLS

Set on over 10 private acres in the rolling hills of Orange County, this exceptional custom colonial offers the rare combination of luxury, privacy, and convenience AND just minutes from the heart of Chester and major commuter routes. Built in 2017 and thoughtfully designed with over 2,700 square feet of living space, 45 Whitetail Run delivers the kind of lifestyle buyers dream about but rarely find. From the moment you enter, soaring ceilings, natural woodwork, and an open-concept layout create a warm yet sophisticated atmosphere. The heart of the home is the stunning chef’s kitchen featuring granite countertops, a leathered granite kitchen island with storage, breakfast bar, 2 pantry's, and seamless flow into the dining and living spaces; perfect for entertaining or everyday living. A dramatic wood-burning fireplace anchors the living room, while oversized UV tinted windows frame peaceful mountain and wooded views in every direction. The flexible floor plan includes a highly sought-after first-floor bedroom with tray ceilings, spa-like finishes in the bath, whirlpool tub, double vanity, oversized walk-in closets, laundry and balcony. That kind of retreat style feel that makes home hard to leave. Outside, the property truly shines. Enjoy morning coffee on the covered porch, host summer gatherings on the expansive deck and patio, or unwind beneath the pergola surrounded by nature and professionally maintained grounds and gardens. The 10.9-acre setting provides exceptional privacy while still keeping you close to shopping, dining, schools, and commuter access. Additional highlights include central air, smart thermostat, walk-out basement with endless potential, oversized two-car garage, new windows, security system, drilled well, septic, propane heat, and multiple outdoor structures for storage or hobby use. A property like this doesn’t just offer a home, it offers space, serenity, and a lifestyle upgrade. Welcome home to 45 Whitetail Run.

45 Whitetail Run, 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

$849,900

4 Beds ⋅ 3 Baths ⋅ 991517 MLS

Welcome to this stunning Colonial, perfectly blending comfort, style, and functionality. Offering 2,370 sq ft plus full walkout basement, this beautifully designed home features 4 spacious bedrooms and 3 full bathrooms, creating an inviting layout ideal for everyday living and entertaining. Step inside to a grand, sun-filled foyer with soaring ceilings that set the tone for the home’s warm and elegant feel. The thoughtfully designed kitchen is perfect for cooking, gathering, and hosting. Outdoors, enjoy your own private retreat with an above-ground pool, play area, and a beautiful, wooded setting. With over 18 acres, the land offers exceptional privacy, natural beauty, and a peaceful buffer around the home. A rare opportunity to own a spacious Colonial with room to live, relax, and entertain—inside and out. Schedule your private showing today!

2 Primrose Lane, Chester

$1,139,900

4 Beds ⋅ 5 Baths ⋅ 982679 MLS

Welcome to Chester, NY, a resort-style luxury colonial set on a private 1.1-acre cul-de-sac lot in the Monroe-Woodbury area of Orange County. This custom residence delivers the space, craftsmanship, and lifestyle today's relocation and move-up buyers are searching for, with approximately 4,624 square feet, refined architectural detail, mountain views, and seamless indoor-outdoor living. From the bluestone entry and custom foyer to the arched windows, detailed millwork, and stone fireplace, every major room has been designed to make a statement. The chef's granite kitchen, expansive family room, and finished lower level with theater, gym, and additional recreation space create flexibility for entertaining, working from home, and everyday luxury. Outside, the backyard becomes the headline feature: saltwater in-ground pool, firepit, koi pond, extensive pavers, and a 3-season outdoor kitchen that gives this home true vacation-at-home appeal. For buyers looking for a luxury home in Chester NY, a Hudson Valley estate near NYC, or a Monroe-Woodbury area home with pool, privacy, and commuter convenience, This is the kind of property that sells both a residence and a lifestyle.

16 Lori Lane, 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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