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

$879,000

4 Beds ⋅ 4 Baths ⋅ 1048079 MLS

Welcome to 101 Beverly Road, a beautifully renovated 4-bedroom, 2 full and 2 half bath home offering approximately 3,764 square feet of total finished living space on 1.9 private acres in the Warwick Valley School District. Backing to woods for added privacy and a peaceful setting, this move-in-ready home combines generous living space, thoughtful updates and wonderful indoor-outdoor living. The heart of the home is the renovated kitchen, featuring quartz countertops, under-cabinet lighting and a built-in mini wine refrigerator. Wood flooring creates a warm, cohesive feel throughout the living spaces, while built-in speakers in the kitchen and living room are perfect for everyday enjoyment and entertaining. French doors further enhance the home’s inviting atmosphere and connection to the outdoors. The spacious primary suite includes a walk-in closet and beautifully renovated bath with a soaking tub and separate walk-in shower, creating a comfortable private retreat. Three additional bedrooms provide plenty of flexibility for guests or home-office space. A dedicated laundry room adds everyday convenience. Approximately 900 square feet of finished lower-level space expands the home’s possibilities even further. Complete with an added half bath and walk-out access to a stamped-concrete patio, this level is ideal for a recreation room, media space, home gym, playroom, office or additional entertaining area. Outside, enjoy 1.9 acres backing to woods, providing privacy and a beautiful natural backdrop. An aboveground pool and deck create the perfect setting for summer days and gatherings, while stamped-concrete walkways and patio areas extend the outdoor living space. An asphalt driveway leads to the attached two car garage. The home has also been extensively improved with many of the major updates already completed, including a new roof, vinyl siding, vinyl windows, garage doors and a new 200-amp electrical panel. A new ducted high-efficiency heat-pump system provides heating and central air conditioning for year-round comfort. Additional improvements include a Marathon non-metallic electric water heater and a whole-house water filtration and softening system with UV treatment. With its renovated interior, spacious layout, finished walk-out lower level, private wooded setting, pool and extensive major-system improvements, 101 Beverly Road offers the space and amenities to enjoy from day one—all within the Warwick Valley School District.

101 Beverly Road, Chester

$679,000

4 Beds ⋅ 4 Baths ⋅ 1046418 MLS

Custom-built by renowned builder Lou Tedaldi, this one-owner Center Hall Colonial offers nearly 3,000 sq. ft. of exceptionally crafted living space nestled on 6.2 pristine, park-like acres. Set on an exclusive private road shared by only 9 homes, this sanctuary delivers total privacy and tranquility while remaining in the highly sought after Monroe-Woodbury School District and close to all local amenities, major routes, and shopping. Inside, beautiful hardwood floors, custom crown and chair rail moldings, and oversized windows with screens bring continuous natural light throughout. The main level features a welcoming foyer with two coat closets, a formal living room with a cozy brick fireplace, and a family room also featuring its own brick fireplace. The gourmet eat-in kitchen boasts granite countertops, a double electric oven, abundant cabinet space, surplus counters, and Tiffany-style lighting, opening via sliders directly onto the back deck. Enjoy formal meals in the dining room, which features sliders out to a spacious, light-filled screened back porch with ceiling fan, perfect for effortless outdoor entertaining. A major highlight of the main level is a versatile 16x24 bonus addition featuring custom woodworking, a beamed ceiling, a bay window, and an ADA-accessible level including a full bathroom, ideal for a luxurious main floor primary suite, guest wing, or private office. Main floor laundry and a half bath add extra convenience. Upstairs, discover four generously sized bedrooms, including an expansive primary suite with hardwood flooring, a spacious walk-in closet, and an en-suite full bath with double vanity. The second bedroom is exceptionally large, easily serving as an alternate primary, while the remaining bedrooms offer ample closet space and bright, oversized windows.The property continues to impress with incredible functional spaces: Two Basements: Main walk-out basement with shelving, a dedicated workshop area, and a sound-proof room (perfect for a media room or studio). Plus a second insulated basement under the addition with separate exterior access. Property Grounds: Stone-faced concrete foundation, iconic Hudson Valley stone walls, manicured lawn, mature landscaping, storage shed, and surrounding private woods. Modern Comforts & Accessibility: ADA-accessible 2-car garage with ramp entry, full-house propane automatic generator, whole-house alarm system, 4-zone oil heating, attic fan, and 30-year shingle roof. An extraordinary property combining top-tier craftsmanship, flexible living spaces, and unmatched outdoor beauty!

5 Red Fox Run, Chester

$1,685,000

6 Beds ⋅ 8 Baths ⋅ 1043860 MLS

Welcome to 69 Cedar Pond Lane. Perched to capture panoramic mountain views, this expansive Chester estate offers an extraordinary combination of multi generational living, proven Airbnb and rental income potential, and top tier infrastructural upgrades across three fully finished levels. The first floor and its bright living & seamless entertaining sun drenched interiors greet you with soaring skylights and massive picture windows framing panoramic mountain views. The open living and dining layout centers on a wood-burning fireplace, flowing into a chef’s kitchen featuring new countertops, custom tile backsplash, breakfast bar, dining nook, built in wine rack, new refrigerator, dedicated beverage fridge and so much more. This floor features two bedrooms and 2.5 bathrooms, with direct walkout access to an expansive outdoor patio outfitted with an outdoor bar, fireplace, and lounge seating. On the second floor you're greeted to a luxury primary suite & a private in law apartment. The upper level hosts three bedrooms, highlighted by a primary suite with mountain vistas, a walk in closet, and a spa bath with dual vanities, a deep soaking tub, stand up shower, and private water closet. This floor also features a dedicated second kitchen, living room, and private patio access. Thoughtfully updated with new countertops, a built in electric fireplace, and an integrated media center, this wing easily functions as an independent, fully equipped apartment. Downstairs is a guest suite & hidden speakeasy. Designed for recreation and flexible guest accommodations, the walkout lower level features a large open playroom created by opening the main space, complemented by a kitchenette, new carpeting, and updated tile. This level includes an Airbnb ready bedroom, finished laundry room, a newly added half bath, and an additional versatile flex room ideal for a home gym, private office, extra bedroom, or mudroom. Concealed discreetly behind a custom bookshelf lies a finished secret room with an adjacent full bathroom, perfect for a private lounge, speakeasy, or creative studio. Unwind in the private hot tub positioned to the right of the home, gather around the backyard fire pit, or enjoy the upper driveway area landscaped with a dedicated children's playset and seating area. The backyard has already been scoped for a custom in ground pool, with renderings available by seller. Additionally, the lower lot can be subdivided and built on, with electrical infrastructure already set up. The property includes a high efficiency HVAC system, commercial grade well pump, and dual water heaters installed in 2025. The roof was replaced around 2022. Ceiling fans and skylights are installed throughout, and all interior wallpaper is high quality peel and stick for effortless design customization. Whether you are looking for a spacious family home, a turn key rental retreat, or a property with room to build and expand, 69 Cedar Pond Lane has it all. Schedule your private tour today and see everything this one of a kind home has to offer.

69 Cedar Pond Lane, Chester

$750,000

4 Beds ⋅ 3 Baths ⋅ 1041533 MLS

Welcome to 1 Sanford Avenue, a beautifully designed 4-bedroom, 3-bath Bilonial offering over 2,200 square feet of thoughtfully finished living space in Chester. The inviting exterior features a welcoming entry, attached 2-car garage, and attractive curb appeal. Inside, the open-concept layout is enhanced by soaring high ceilings, hardwood floors throughout, and a tiled foyer. The spacious kitchen features custom cabinetry, granite countertops, and a custom wine rack with wine fridge, creating a stylish and functional space for everyday living and entertaining. The main level includes a bedroom and full bath for added flexibility, while the spacious primary bedroom offers a private ensuite full bath. The lower level provides additional finished living space with plenty of flexibility for a recreation room, home office, gym, media area, or other needs. Additional interior features include surround sound and smart thermostats. The attached 2-car garage includes an EV charger, while the property also features solar panels leased through Sunrun and a backup generator. Additional highlights include spray foam insulation, central air, on-demand hot water, and forced-air propane heating. Located in a desirable Chester setting, this home offers convenient access to shopping, dining, parks, major roadways, and commuter routes, providing a comfortable setting with everyday convenience.

1 Sanford Avenue, Chester

$675,000

3 Beds ⋅ 3 Baths ⋅ 1038759 MLS

The search for your DREAM HOME ends when you visit this property, since it will check all your boxes ! LOCATION which is perfect for commuters, just a few feet away from the charming Sugar Loaf Craft Village, situated between Warwick and Chester for your enjoyment and convenience of both town's amenities and activities. Sit on the rocking chair front porch in peace, quiet and tranquility while enjoying the spectacular VIEWS of Sugarloaf Mountain ! Corner lot, vinyl siding, deck overlooking the private backyard with a raised bed garden and large storage shed.The front porch welcomes you into the impressive two story foyer with the living room to the left and formal dining room to the right as you approach the open floor plan space consisting of the large eat in kitchen and family room with a fireplace. This home has hardwood floors , large spacious bedrooms, updated kitchen with granite counters, a walk up attic for lots of easy to get to storage or hobby space, a finished basement with a 1/2 bath and an oversized 2 car garage.

188 Creamery Pond Road, Chester

$359,000

3 Beds ⋅ 3 Baths ⋅ 1027103 MLS

Welcome to Whispering Hills! Discover easy living, comfort and privacy while living within a neighborhood community. Perfect for first time home buyers or if you're downsizing for care free, low maintenance living. Enjoy this spacious 3 bedroom, 3 bath townhouse with lots of storage and your private garage with direct entry into your home. Comfortable and spacious bedroom layouts with baths and ample closet space throughout. Cozy up with your living room fireplace anytime you want to relax. Enjoy morning coffee on your patio directly off the kitchen. This very bright end unit offers extra windows and a large open yard area that affords much outdoor space for your enjoyment. Home features a newer air conditioning conditioner and double patio slider. Location is perfect for commuters and convenient to all major shopping, restaurants and entertainment. The complex offers access to amenities that everyone can enjoy: swimming, handball, tennis, basketball and dog runs too. No need for gym memberships as you have a fully equipped fitness center. Quick access to Route 17 and 94 centered between NYS Thruway and Route 84. Minutes to Legoland, Woodbury Common Outlets, Chester, Sugar Loaf , Warwick and the Heritage Trail. Don't miss this quiet and private inside home off the main road!

2522 Whispering Hills, Chester

$1,195,000

4 Beds ⋅ 4 Baths ⋅ 1010585 MLS

Welcome to a one-of-a-kind Arts and Crafts style sanctuary where timeless craftsmanship meets modern luxury. Tailored for the discerning buyer or avid automotive enthusiast, this exceptional property features an expansive multi-car garage designed to accommodate prized vehicle collections, a workshop, or custom storage needs. Located in the Town of Chester, this 4,281-square-foot estate masterfully blends timeless architectural detail, rich natural textures, and modern sophistication. Exceptional artistry is on display throughout, highlighted by solid wood doors, dual staircases, striking red oak flooring with Mahogany inlays, and radiant-heated floors across the entire main level. Formal living and dining spaces framed by soaring floor-to-ceiling windows flow effortlessly onto a sweeping bluestone patio, while the chef's kitchen and sunken family room with a rustic wood-burning fireplace lead to a covered outdoor patio and private fire pit area. The main-level primary suite offers a peaceful sanctuary with a gas fireplace, wrap-around covered Trex deck, and a spa-inspired bath with a vintage cast iron clawfoot tub. Upstairs, 3 oversized bedrooms—two with private en-suite baths—are complemented by a full walk-up attic and a bonus loft accessed via a spiral staircase. Enjoy the perfect mix of local charm and seamless transit. Located just minutes from the historic Village of Goshen, you’ll have quick access to boutique shopping, famed local dining, craft breweries, local wineries, and the scenic Orange Heritage Trail. Just 10 miles from Woodbury Common Premium Outlets and 60 miles from NYC, with immediate access to Route 17 (I-86), the NYS Thruway, Chester Park & Ride, and Harriman Train Station.

22 Goshen Road, Chester

$749,999

4 Beds ⋅ 3 Baths ⋅ 995624 MLS

Looking for a spacious home that has everything? Look no more! Perched atop the highly sought-after Fieldcrest subdivision, this stunning Colonial offers over 3,300sqft of living space! The property offers four spacious sleeping areas and 2.5 baths. Endless possibilities for additional use continue on the 3rd floor with a 15 x 42 climate-controlled walk-up attic, offering approximately 630 additional square feet of space. Whether envisioned as a media lounge, home gym, creative studio, guest suite, game room, or finished living area, this expansive attic provides an incredible opportunity to customize the home to fit your lifestyle and needs. On the main level 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. Spectacular views, a fenced backyard, brand-new Trex deck, above-ground pool, and potential home office, make this property truly stand out. Abundant living space, flexible rooms, exceptional storage, newer major systems, outstanding outdoor amenities and exceptional curb appeal make this property the rare combination of comfort, functionality, and room to grow.

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

$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. 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

$275,000

2 Beds ⋅ 1 Baths ⋅ 950534 MLS

Welcome Home! 2 Bedrooms 1 Bathroom move in ready end unit. Recently renovated including a new kitchen with granite counter tops and stainless steel appliances, new bathroom, new windows, new laminate flooring, new water heater, new light fixtures and recessed lighting. Nothing to do but move in! Close to supermarket, post office, restaurants, urgent care, highway. Perfect commuter location. Don't wait this one is ready to go!

2113 Whispering Hills, Chester

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