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

$370,000

3 Beds ⋅ 2 Baths ⋅ 1046996 MLS

Move right in! This beautifully maintained and thoughtfully updated 3-bedroom, 2-full-bath END-UNIT condo offers almost 1,400 square feet of comfortable, easy one-level living in the desirable Whispering Hills community. As soon as you enter the welcoming two-story foyer, you’ll appreciate how bright, open, and impeccably maintained this home is. The spacious open-concept living area features vaulted ceilings and a beautiful Marble & Wood fireplace, creating a warm, inviting atmosphere. Sliding doors lead to your private deck provides easy access to enjoy the peaceful, beautifully landscaped surroundings. The renovated kitchen is both stylish and functional, featuring modern cabinetry, granite countertops, updated backsplash, Stainless appliances and a pantry with plenty of shelving, The spacious primary suite is truly a standout! Enjoy a large walk-in closet with California shelving and a renovated full bath frameless shower. Two additional bedrooms provide plenty of flexibility for guests, a home office, or other needs. Additional updates include sparkling new flooring throughout, new water heater & Washer/Dryer. The attached one-car garage provides convenient direct access to the home along with dedicated storage space. Enjoy all that Whispering Hills has to offer, including a two community pools, tennis court, kids park, dog park, sidewalks, and a peaceful setting—while being just minutes from shopping, restaurants, parks, and major commuter routes. Located in the Chester School District. All this with New York City bus that picks up and drops off right in the complex. Don't miss your opportunity to make it yours. Call today for your private tour. *****Professional Photos Coming Soon****

3211 Whispering Hills, Chester

$380,000

3 Beds ⋅ 3 Baths ⋅ 1038636 MLS

Welcome home to your beautiful, quiet and peaceful oasis. This 3 bed/3bath unit with a spacious 2-car garage has many new recent updates including new flooring, updated kitchen and bathroom, and an elegant hanging chandelier. Have your morning coffee or evening dinner on your lovely private patio and in the winter enjoy your cozy fireplace. The amenities will give you that vacation resort feel including, tennis and basketball courts, pools, a playground, and a clubhouse with a gym. This Whispering Hills home in this wonderful community and scenic views will surely bring you much pleasure and enjoyment for years to come.

4704 Whispering Hills, Chester

$374,900

3 Beds ⋅ 3 Baths ⋅ 1043986 MLS

WHISPERING HILLS! PRIME LOCATION! Largest Unit! Two Story Living! End Unit! 3 Bedrooms! 2 1/2 Bathrooms! 2 Car Garage! Eat In Kitchen! Dining/ Living Room with Fireplace! Master Bedroom Suite with Walk In Closet! Central Air! Country Club Living! Clubhouses! Pools! Tennis! Basketball! Tot Lot! Dog Walk! Perfect Commuter Location! Close to Major Highways, Buses & Shopping! Walk to NYC Bus!

2921 Whispering Hills, Chester

$290,000

2 Beds ⋅ 2 Baths ⋅ 1043197 MLS

Welcome to Whispering Hills! This spacious two-level, 2-bedroom, 1.5-bath condo with a 1-car garage features a great combination of updates and an ideal commuter location. Step inside to a freshly painted interior featuring an updated kitchen and bathrooms. The inviting living room features a fireplace and sliders leading to a private patio, perfect for relaxing and enjoying the outdoors. Additional updates include a newer furnace, central air conditioning and water heater! Enjoy country club-style living with fantastic community amenities including clubhouses, swimming pools, tennis courts, basketball courts, playgrounds, walking areas and a dog run. An excellent commuter location with NYC bus service right in the complex, plus convenient access to major highways, shopping, restaurants and everyday necessities. Comfort, convenience and community amenities all in one—this is one you won’t want to miss!

1005 Whispering Hills, Chester

$550,000

3 Beds ⋅ 2 Baths ⋅ 1042882 MLS

Welcome to this charming ranch style home set on 4 picturesque acres, featuring beautiful flowing hardwood floors and a peaceful, private setting. The inviting kitchen offers gorgeous marble countertops, an abundance of cabinetry, a sink positioned beneath the windows, and stainless-steel appliances. From the living room, double sliding doors open onto the expansive wraparound porch, creating an effortless connection to the serene backyard perfect for relaxing, entertaining, or enjoying the surrounding nature. The spacious primary suite features a huge closet and a private master bath. Two additional bedrooms offer generous closet space, providing plenty of room for family, guests, or a home office. Step outside and cross the charming bridge over the stream to access the enlarged backyard, offering even more space to enjoy the outdoors. A spacious 24' x 28' detached garage with a 10' x 10' garage door provides ample room for large vehicles, ATVs, a workshop, equipment, and storage. Conveniently located just minutes from Route 17, shopping, restaurants, and everyday amenities, this property offers the perfect blend of country tranquility and convenient access to town.

50 Hambletonian Avenue, Chester

$299,000

2 Beds ⋅ 1 Baths ⋅ 1042658 MLS

Welcome to Whispering Hills! This inviting end-unit home offers a comfortable blend of everyday living, privacy, and convenience. Enjoy easy access to major commuter routes and highways, making this an ideal choice for commuters seeking the comfort of home without sacrificing convenience. Come home to a welcoming community and enjoy all that this convenient location has to offer.

2124 Whispering Hills, 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

$360,000

3 Beds ⋅ 3 Baths ⋅ 1032618 MLS

Welcome to this inviting 3 bedroom, 2.5 bath condo nestled in the sought-after Whispering Hills community! Perfectly situated for commuters, this home combines comfort and convenience, with easy access to public transportation and proximity to major highways. Step inside to discover a well-maintained interior with an open-concept living and dining area featuring a wood burning fireplace, providing a welcoming space to relax or entertain with a new HVAC system. The kitchen boasts modern stainless-steel appliances, ample cabinetry, and a functional layout, making it a delight for cooking and meal prep. Living in Whispering Hills comes with a wealth of amenities. Enjoy sunny days by the community pool, play a match on the tennis courts, or hit the gym for your daily workout. There are also handball courts and beautifully landscaped surroundings that make everyday living feel like a getaway. With a prime location, you’re never far from shopping, dining, and recreation options.

3409 Whispering Hills, Chester

$700,000

4 Beds ⋅ 3 Baths ⋅ 1040084 MLS

Gracious Colonial home features the best of the traditional style with the appeal of a contemporary open floor plan in the kitchen - family room area. Meticulously maintenance and stylish updates create easy living spaces that are great for daily relaxation as well as entertainment. The full-length deck, large seating area around the fire pit and expansive yard provide outdoor areas to relax, play or entertain. The cul-de-sac setting allows for low traffic while remaining close to shopping, public transportation, restaurants and shops. This is a must see for the discriminating buyer.

13 Bianca Boulevard, Chester

$475,000

3 Beds ⋅ 2 Baths ⋅ 1030740 MLS

Welcome to this impeccably maintained raised ranch in the highly sought-after Surrey Meadows Community. Upon entering the foyer, you'll find a practical area beneath the stairs, providing convenient storage for coats and shoes. The lower level features a spacious bedroom with access to a full bathroom, complemented by a versatile bonus room perfect for a cozy den or guest accommodation. Ascend the hardwood stairs to the living room, which boasts hardwood flooring and abundant natural light. This level also includes two generously sized bedrooms and an additional bonus room, ideal for a home office. Newly installed pocket doors maximize space. The fully renovated kitchen is a culinary enthusiast's dream, featuring hidden spice cabinets, a copper farmhouse sink, and a glass-door pantry. From the kitchen, step out onto the deck that overlooks a substantial yard. The home includes a convenient garage and a shed, ideal for storage or lawn equipment. Enjoy year-round activities such as Legoland Resort, artisanal eateries and wineries, orchards, and Orange County's recreational lakes. Within walking distance to both the Middle School and High School and approximately an hour's drive from New York City, with public transportation to NYC nearby. This residence is truly a must-see.

21 Trotting Drive, Chester

$290,000

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

$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

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