Chester Homes with Garage Parking features

Welcome to Chester, New York—a hidden gem nestled in the picturesque Orange County, where the charm of small-town living meets the beauty of nature. Known for its stunning landscapes, Chester is surrounded by the breathtaking backdrop of the Hudson Valley, making it a perfect retreat for those seeking tranquility without sacrificing convenience. The town is rich in history, with quaint shops, delightful eateries, and vibrant community events that foster a welcoming atmosphere.

Chester boasts a variety of outdoor activities, from hiking the scenic trails of the nearby Sterling Forest State Park to enjoying a leisurely day at the local lakes. Families and outdoor enthusiasts will appreciate the abundance of parks and recreational facilities available, making it easy to embrace an active lifestyle. The town’s close-knit community is ideal for raising children, with excellent schools and numerous family-friendly activities throughout the year.

When it comes to finding your dream home in Chester, you’ll be pleased to discover a selection of properties featuring the coveted garage parking option. Whether you’re looking for a cozy cottage or a spacious family home, many residences in this charming area come equipped with garage parking, providing you with the convenience and security you desire. Imagine coming home after a long day to a warm and welcoming space, with the added benefit of easily accessible parking.

Explore the endless possibilities that Chester, NY has to offer. With its stunning surroundings, vibrant community spirit, and homes with garage parking, Chester is not just a place to live but a place to thrive. Come and experience the magic of Chester—your new home awaits!

Newest Chester Homes with Garage 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

$315,000

2 Beds ⋅ 2 Baths ⋅ 1027838 MLS

Move in ready townhome with a NYC bus stop within the community!! Whispering Hills in Chester is perfectly positioned for commuters being 2 miles to Route 17. Enjoy a prefect blend of comfort and convenience with a maintenance free lifestyle in this two bedroom townhome. The main floor has brand new flooring, a living room with a wood burning fireplace,and a separate dining area ideal for entertaining.The kitchen has a tile backsplash, and a natural gas range. A convenient half bath and laundry area complete the first floor. Upstairs,the primary bedroom offers vaulted ceilings,a generous walk in closet and a full bath with private access to the hallway. The second bedroom is of ample size with a double door closet. A skylight in the hallways brightens the home. Additional features and highlights include central air, natural gas heating, an attached one car garage with extra storage, building roof replaced in 2022, HVAC 2013, skylight 2013, municipal water and sewer,reasonable hoa fees, snow removal and beautifully maintained grounds. Community amenities feature a dog park, playground, two pools, a gym and more. Just 5 minutes from the heart of Chester where you'll find local shopping,dining and entertainment all while remaining 70 miles from NYC, 10 minutes to LegoLand and close to Woodbury Common, Resorts Casino and Bethel Woods Concert Venue. Visit our nearby breweries, cafes,farmer market and historic Sugarloaf Village. Come see why everyone wants to live here!

4008 Whispering Hills Drive, 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

$650,000

3 Beds ⋅ 4 Baths ⋅ 1027353 MLS

Welcome to a contemporary retreat where refined design, exceptional craftsmanship, and a seamless connection to nature come together in one of Chester’s most desirable settings. Thoughtfully designed for both everyday living and effortless entertaining, this light-filled residence offers three bedrooms, two full bathrooms, and two half baths with an open, flowing floor plan that balances sophistication with comfort. The main level is defined by soaring ceilings, expansive windows, and an abundance of natural light that fills every corner of the home. The dramatic living room serves as the heart of the residence, centered around a wood-burning fireplace and overlooking a beautifully landscaped backyard complete with a custom-built pond and tranquil gardens that create a truly peaceful backdrop. The custom-designed white kitchen is a true showpiece, crafted for those who love to entertain. A large center island with an integrated cooktop allows the chef to remain part of every conversation, while generous workspace, custom cabinetry, and views of the surrounding landscape make the space as functional as it is beautiful. Sliding doors extend the living space to a private patio, creating a natural indoor-outdoor flow for dining and gatherings. Upstairs, the spacious primary suite and additional bedrooms are thoughtfully appointed with custom-built closet systems that maximize both style and organization. Three generously sized bedrooms and two beautifully finished full bathrooms provide comfortable accommodations designed for modern living. The finished lower level offers exceptional flexibility, featuring a spacious recreation or living area, a convenient half bath, and a dedicated storage room—ideal for a media room, home office, gym, guest retreat, or extended living space. Perfectly positioned just minutes from Walton Lake, Goosepond Mountain State Park, and the world-class shopping and dining of Woodbury Common Premium Outlets, this home offers the best of Hudson Valley living with convenient access to New York City in approximately 90 minutes. Combining contemporary architecture, designer finishes, and an idyllic natural setting, this exceptional residence delivers a lifestyle defined by comfort, elegance, and effortless luxury.

29 Murray Drive, Chester

$389,900

3 Beds ⋅ 2 Baths ⋅ 1027245 MLS

WOW! Move right into this 3 Bedroom 2 Full bath "all on one level" (almost 1400 sq.ft.) beautifully maintained and updated END UNIT condo style home! You'll love the bright and open concept layout featuring the living room with vaulted ceilings and a gorgeous floor to ceiling fireplace as the focal point of the space. Within this area is easy access to the private deck (with new slider door) perfect for outdoor enjoyment and relaxation overlooking the pretty landscape. The kitchen has been thoughtfully renovated with new modern cabinetry, quartz countertops, updated backsplash, newer appliances (dishwasher, gas range and microwave), dedicated pantry with roll outs and ample shelving, new sink and pull out garbage drawer. Through the main entry level you have immediate access to the 1 car garage, which also has a dedicated storage space. This home has its own private entrance and the two story foyer offers a warm welcome to the unit. Notice how well maintained this home is as you tour. The primary bedroom is spectacular. This room is spacious and it has a large walk in closet and a gorgeous newly designed on suite full bathroom that feels like a "spa". Throughout the home, new flooring and window blinds have been installed, along with recessed lighting and a modern dining room chandelier. An added perk is that the entire condo was freshly painted in 2023. Further, additional significant updates offering peace of mind for years to come include: New furnace (2022) and new air conditioning unit (2023). There is also a smart thermostat system. This property is located in the Chester school district. Whispering Hills is an in-demand location - just minutes from shopping, restaurants, parks and more. Also, you'll love the easy access to main routes while enjoying the peaceful setting this development has to offer! Within Whispering Hills is the community pool for Summer fun, tennis court and sidewalks. Call for your private tour. Welcome home! *Special features sheet with more details and a floor-plan are available*

4114 Whispering Hills, 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

$329,000

2 Beds ⋅ 2 Baths ⋅ 1018748 MLS

Beautifully maintained two bedroom condo with a two car garage in an excellent location within the highly desirable Whispering Hills community. Updated kitchen and newer flooring on the main level. Wood burning fireplace in the spacious living room. Sliding door from the dining area to the patio. The primary bedroom with tall vaulted ceilings has a large walk-in closet with custom California-closets style design features floor-to-ceiling shelves and cabinetry. Bedroom #2 also has custom closets. The outdoor patio with privacy fence overlooks the green area. Laundry area with storage shelves and full sized washer and dryer included. Central air conditioning and forced air heating. Natural gas and municipal water and sewer services. This home is in a fantastic location within Whispering Hills - tucked in the rear side of the community alongside the green area near the tennis courts, clubhouse, pool area, playground and dog run. Included with monthly HOA fee: Water, garbage and recycling, snow removal, landscaping, pool pass to two separate pool areas, use of tennis courts, basketball court, playground and clubhouse. Low taxes!!! Excellent commuter location. Bus stop to NYC/NJ in the complex. Close to the highway, supermarket, and shopping. Minutes from Woodbury Common, LegoLand NY, Garnet Health Medical Center, Chester Mall Shopping Center.

4118 Whispering Hills Drive, Chester

$575,000

3 Beds ⋅ 3 Baths ⋅ 1018371 MLS

Welcome to this beautifully maintained raised ranch, perfectly situated on a desirable corner lot in Chester. This inviting 3-bedroom, 2 full and 1 half bath home blends comfort, style, and modern convenience in a location you'll love. Filled with natural light, the home features spacious living areas and a well-appointed kitchen with stainless steel appliances. The finished basement offers flexible space for a family room, home office, gym, or guest retreat. Thoughtful upgrades, including a Nest thermostat, Ring security camera with window sensors, and a reverse osmosis water filtration system, enhance both comfort and convenience. In addition to the home's primary boiler heating system, the central HVAC system provides air conditioning and electric auxiliary heat, offering added comfort and flexibility throughout the seasons. Step outside to your own private backyard oasis featuring a spacious deck, above-ground pool, and newly installed white vinyl privacy fence—perfect for relaxing or entertaining. Conveniently located just 12 minutes from Woodbury Common Premium Outlets with easy access to major highways, this home offers the perfect blend of peaceful suburban living and everyday convenience. Don't miss the opportunity to make it yours!

11 Chandler Drive, Chester

$295,000

2 Beds ⋅ 2 Baths ⋅ 1019548 MLS

Step into this gorgeous Townhouse.Upon entering you’ll be welcomed by a perfect floor plan. The inviting living room features wooden floors, a cozy fireplace, and windows. The stylish kitchen has a functional layout and is outfitted with stainless steel appliances and granite countertops. The master-bedroom offers a modern feel and a walk in closet. Enjoy the amenity centers. Stop dreaming and start living, come and take a look today! The Condo charges $475 , HOA $250

2119 Whispering Hills, Chester

$649,999

4 Beds ⋅ 3 Baths ⋅ 1013375 MLS

Private 2.5-Acre Contemporary Retreat with Expansive Deck – Chester, NY Welcome to 424 Laroe Road — a rare opportunity to own 2.5 private acres in sought-after Chester. This solid 1974 contemporary home offers 2,316 square feet of flexible living space with 4 bedrooms and 3 bathrooms, perfectly positioned to take full advantage of its peaceful, tree-lined setting. Step outside onto the expansive multi-level deck and immediately feel the difference that true privacy and land can make. Ideal for entertaining, morning coffee, or simply enjoying the quiet, the outdoor living space is a standout feature rarely found at this price point. The generous lot offers room to expand, garden, play, or create your own outdoor oasis. Inside, the home provides a comfortable layout with bright living areas, multiple bedrooms, and the potential to personalize to your style. Ample garage and parking space add everyday convenience. Located in Orange County with easy access to major routes, this property delivers the space and privacy so many buyers are searching for — without sacrificing convenience. Whether you’re looking for a primary residence with room to grow or a peaceful retreat, 424 Laroe Road offers a strong foundation and exceptional land value. Key Features: 4 bedrooms | 3 bathrooms 2,316 sq ft 2.5 private acres Expansive deck for outdoor living Built 1974 – solid bones with modern potential Convenient Chester location Schedule your private showing today and experience the space, privacy, and potential for yourself.

424 Laroe Road, 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

$875,000

4 Beds ⋅ 3 Baths ⋅ 1011165 MLS

Escape to your own private retreat at 49 Stone Mountain Trail. Tucked away on more than 7 acres with mountain views, this contemporary home delivers the perfect balance of comfort, space, and outdoor enjoyment. Imagine mornings filled with sunlight streaming through oversized windows, evenings gathered around the stone fireplace, and summers spent relaxing by the in-ground pool surrounded by nature. The soaring great room creates a dramatic first impression, while the beautifully updated kitchen serves as the heart of the home with its oversized island and bright, modern finishes. Outside, the expansive grounds provide endless possibilities—from entertaining and recreation to simply enjoying the peaceful surroundings. With 4 bedrooms, 2.5 baths, and over 3,600 square feet of living space, this property offers room to spread out while enjoying the privacy and beauty of its remarkable setting.

49 Stone Mountain Trail, Chester

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