Chester Homes with Garage Parking features

Welcome to Chester, New York – a charming town nestled in the heart of Orange County, where picturesque landscapes meet a vibrant community spirit. Known for its friendly atmosphere and small-town charm, Chester is not only a great place to live but also a wonderful place to raise a family. One of the standout features of this area is its highly regarded school district, which is dedicated to fostering a supportive learning environment for students of all ages.

The Chester School District prides itself on its commitment to academic excellence, offering a wide range of programs designed to meet the diverse needs of its students. With experienced educators and a curriculum that emphasizes critical thinking and creativity, children in Chester are equipped with the skills they need to succeed. The district also boasts a variety of extracurricular activities, from sports to the arts, ensuring that every student can find their passion and thrive both in and out of the classroom.

For those considering making Chester their home, you’ll be delighted to discover a selection of beautiful properties that feature garage parking – a true convenience in today’s busy world. These homes not only provide ample space for your vehicles but also offer additional storage options for your outdoor gear or seasonal decorations. Whether you’re looking for a cozy cottage or a spacious family home, Chester’s real estate market has something for everyone.

Come explore Chester, where quality education and charming homes with garage parking await you!

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

$629,000

4 Beds ⋅ 2 Baths ⋅ 1030227 MLS

Gorgeous corner fully fenced in Bi-Level house for sale in Town of Goshen. State of the art heating system, central air, beautiful sunroom, modern kitchen and bathrooms. House was fully remodeled in 2014. The main level features three bedrooms, master bathroom has walk in closet with access to the bathroom, spacious living room, dinning room, kitchen and sunroom. The lower level offers additional living space with a fully finished basement, 4th bedroom, modern bathroom, additional storage space and laundry room. Extra large deck, above ground pool with paver patio. House is conveniently located to major highways, shopping, dinning and bus stations. Move in ready! Must come and see!

14 Larchwood Drive, Goshen

$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

$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

$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

$549,900

3 Beds ⋅ 2 Baths ⋅ 1008703 MLS

This beautifully updated homes features wood floors throughout, three spacious bedrooms, two den/office spaces, formal dining room, and two full baths. The expansive primary suite has an additional 10 X 10-ft. sitting room, generous walk-in closet, an en-suite with linen closet, walk-in shower and Venetian soaking tub. The main floor bathroom is equally large with a jetted bathtub. Both the living room ams the Primary have soaring cathedral ceilings and the dining room has a 10-ft. tray ceiling. Light pours into this homemaking the oversized living area bright and cherry. The inviting eat in kitchen features stainless appliances, and for extra storage a basement pantry features floor to ceiling shelves. There is also a basement laundry with included, oversized washer and dryer. An Additional laundry hook up is also available right outside the Primary suite. The living room has a fireplace clad in beautiful cultured stone with a wood burning insert for extra heat. Outside, mature landscaping frames this beautiful house. Enjoy relaxing on a two-tiered ,massive, low maintenance Trex deck surrounded by colorful perennial flowers that bloom every spring and summer. A stone fire pit sits center stage on the lower deck, and a large shed will hold all your gardening tool. In front a quaint porch provides more outside seating. There ia a garage and plenty of additional outdoor parking. The house has upgraded Hardie plank siding and stone. Enjoy country living and pace while still only being minutes from shopping, dining and the highway.

3318 State Route 94, 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

$3,200,000

5 Beds ⋅ 4 Baths ⋅ 956598 MLS

Set on 1.6 private acres overlooking Greenwood Lake and directly bordering the Appalachian Trail and protected state parkland, this nearly 5,920 SF modern residence feels suspended between civilization and nature. You’re not just buying a home. You’re securing protected views, mountain air, and lasting privacy. The architecture sets the tone immediately. Clean lines. A refined blend of metal and wood. Intentional design. Enter through a private mudroom and the scale unfolds. The main living space rises to ceilings nearing 30 feet, anchored by a dramatic double-height living and dining area framed by large-format, high-performance Wythe windows that capture the lake and mountain backdrop. Natural light floods the interior. European White Oak floors warm up the primary living areas, balancing the modern aesthetic. The open kitchen was designed for gathering, with a Bosch appliance package, exterior-vented hood, Sandy Shaker-style cabinetry by RTA, natural stone countertops and backsplashes, and contemporary Kohler fixtures flowing seamlessly into the entertaining spaces. An open loft overlooks the main level, complemented by a dedicated home office and a separate library or reading room, creating quiet retreats within an expansive layout. The primary suite feels restorative. A spa-inspired bath features large-format tile, a Kohler freestanding soaking tub, and a walk-in rain shower with ceiling-mounted head and linear drain. Natural stone counters, custom vanity cabinetry, integrated mirrored medicine cabinets, and layered lighting complete the space. Secondary baths carry the same elevated, durable finishes. The finished lower level offers flexible space for a gym, media room, bar, or lounge. Outside, nearly 2,000 square feet of decks and terraces extend the living areas outward, framing lake and parkland views with complete privacy. Built using Passive House principles, the home features a high-performance envelope and net-positive energy strategy supported by on-site solar. Advanced insulation, Passive House–certified windows, smart power monitoring, EV charging, and LED lighting throughout ensure exceptional efficiency and air quality. A fully integrated Savant system controls lighting, HVAC, sound, security, and energy management from your phone, delivering intuitive, connected living. A private two-car garage, dedicated laundry area, and thoughtful storage complete the functionality. What defines 95 Jersey Ave isn’t just its size or finishes. It’s the experience of living in architecture that respects its setting, opening to Greenwood Lake on one side and permanently protected land on the other. Modern mountain-lake living, executed at the highest level.

95 Jersey Avenue, Greenwood Lake

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