Chester Homes with Attached Parking features

Welcome to Chester, New York – a charming town nestled in the picturesque landscapes of Orange County. Known for its stunning natural beauty and vibrant community spirit, Chester offers a delightful blend of rural tranquility and modern convenience. With its scenic mountain views, lush parks, and proximity to pristine lakes, this area is perfect for those who appreciate the great outdoors. Residents can enjoy hiking, fishing, and exploring the nearby Harriman State Park, making every day an opportunity for adventure.

Chester’s quaint downtown area is filled with unique shops, cozy cafes, and local eateries, creating a warm and inviting atmosphere that fosters a strong sense of community. The town also hosts various events throughout the year, from farmers' markets to seasonal festivals, ensuring there's always something exciting happening.

When it comes to finding your dream home in Chester, you’ll be pleased to discover a range of properties featuring attached parking. This convenient amenity is a significant advantage, providing you with easy access to your vehicle while ensuring you never have to worry about street parking. Whether you’re looking for a charming single-family home or a modern townhouse, the attached parking features add an extra layer of comfort and practicality to your living experience.

Chester is not just a place to live; it’s a lifestyle choice that combines the beauty of nature with the convenience of suburban living. Come explore all that Chester has to offer and discover the perfect home that fits your needs!

Newest Chester Homes with Attached Parking features

$525,000

2 Beds ⋅ 2 Baths ⋅ 1050131 MLS

Welcome to Chester, NY!! Come see this spacious home featuring 2 bedrooms and 2 full baths, with a bonus room. This home has plenty of possibilities and includes a finished basement and finished attic for all your storage needs. Large 2-car garage for all the gadgets. This home has a large open concept for entertaining family and friends. Additional energy saving feature of solar panels and an oversized deck with an above-ground pool for outdoor enjoyment for all. The home boasts charm and beautiful hardwood flooring throughout many areas of the home. This home is conveniently located near shopping, fine dining, and many leisure activities for all age groups. Easy commute to the city and major transportation hubs for commuters. Local highway and interstate access within minutes. This is a property you want to see; come see what Meadow Av has to offer. Welcome Home!!!

19 Meadow Avenue, Chester

$499,000

3 Beds ⋅ 3 Baths ⋅ 1049026 MLS

This beautifully updated Chester home in the Monroe-Woodbury School District sits on 1.5 acres with a level open yard, a creek, and a wooded backdrop. From the moment you arrive, the paver walkway, landscaping, and inviting curb appeal set the tone. Inside, the main level boasts hardwood floors and an open layout with a brand-new kitchen featuring white cabinets, granite counters, and stainless steel appliances, plus a living and dining area with sliding glass doors to the deck and backyard. The first floor also has a full hallway bath and three bedrooms, including a bright primary suite with custom windows, crown molding, and an updated ensuite bath with custom tile and glass shower doors. The lower level offers a large den with a stone fireplace and wood-burning stove insert, a half bath, laundry room, and access to the attached two-car garage. Outdoor spaces include a deck off the kitchen and a covered deck from the den, perfect for relaxing or entertaining. The expansive yard is ideal for recreation, gardening, or gatherings, with the creek and woods adding privacy. Just 57 miles to NYC, this home offers both tranquility and easy access to amenities, including nearby parks with 1,500 acres of trails, playgrounds, and more. Additional perks include central air, newer siding, roof, oversized energy-efficient windows, shed, oil burner, hot water heater, and several updated appliances. Conveniently located near shopping, major highways and public transportation.

264 Bull Mill Road, Chester

$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

$459,000

4 Beds ⋅ 2 Baths ⋅ 1047996 MLS

Welcome to this charming 4-bedroom, 2-bath bilevel, ideally situated on a quiet dead-end street. The inviting open floor plan offers a seamless flow for everyday living and entertaining, with beautiful hardwood floors throughout the main level and a spacious kitchen featuring stainless steel appliances. Enjoy year-round comfort with central air and take advantage of the large deck overlooking a flat, fully fenced backyard, providing the perfect space for outdoor entertaining, relaxing and play. With Monroe-Woodbury Schools, low taxes, and an excellent commuter location, this home offers the ideal combination of comfort, convenience, and value. Don’t miss the opportunity to make this wonderful home your own!

8 Townsend Place, 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

$669,000

3 Beds ⋅ 3 Baths ⋅ 1040801 MLS

Welcome to this charming three bedroom, two and a half bath colonial nestled in a welcoming neighborhood just minutes from the highway and the charming hamlet of Sugar Loaf. This inviting home offers a comfortable layout with plenty of space for everyday living and gathering. Outside, enjoy a flat, level yard that provides space for relaxing, entertaining, gardening, or outdoor activities. Conveniently located near shopping, restaurants, and all that the Hudson Valley has to offer, and located in the Warwick School District. A wonderful opportunity to make this colonial your new home!

173 Creamery Pond Road, 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

$459,000

4 Beds ⋅ 3 Baths ⋅ 1039933 MLS

Welcome Home to 63 Hubshop! This charming colonial boasts 2,100 square feet, 4 Bedrooms, 3 Bathrooms and sits on just under an acre of land. With a spacious kitchen, and both a designated living room and dining room, this home offers an easy-flowing layout, making you feel right at home the moment you walk through the door. Off the kitchen you will find a bonus room that can be transformed into a gym, playroom for the kids, entertainment room for guests or whatever your needs may be. Upstairs, you’ll find four generously sized bedrooms, including a primary suite with its own full bathroom. Last but certainly not least, is the tranquility and calmness this property has to offer. As you venture outside, you will find yourself tucked away on a quiet road with an inviting backyard that has access to Cromline Creek! This offers the perfect setting for those early morning coffees or long days of entertainment . Add easy highway access, an easy commute to NYC, and proximity to shopping destinations like Woodbury Commons, and you've found a location that truly checks all the boxes. Schedule your showing today and make this beautiful home yours before the new school year begins!

63 Hubshop Road, Chester

$749,900

4 Beds ⋅ 4 Baths ⋅ 1037562 MLS

20 Mountainside Drive, Chester, NY offers a spacious Colonial-style single-family home on approximately 1.6 acres with 4 bedrooms, 2 full baths, 2 half baths, 10 total rooms, and approximately 3,080 sq. ft. of above-ground living space. Built in 2021, this Chester residence features central cooling, gas heat, a full basement, fireplace, covered porch, patio, and Attached garage. Located in Orange County within the Chester School District, this home offers space, privacy, and convenient access to shopping, dining, parks, recreation, commuter routes, and Hudson Valley attractions. Some listing photographs have been virtually decluttered and/or virtually staged for visualization purposes. Virtual furnishings shown are not included with the property. Come make it your own.

20 Mountainside Drive, 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

$435,000

3 Beds ⋅ 2 Baths ⋅ 1033721 MLS

Welcome to 66 Whitetail Run – Chester, NY. Tucked back from the road on an ample, tree-lined lot, this charming contemporary colonial offers the perfect blend of privacy and convenience in the Monroe-Woodbury school district. Surrounded by nature and filled with birdsong, this peaceful setting feels like a retreat while still being close to all local amenities. Step inside to a bright, open living room featuring soaring ceilings, a wood-burning fireplace, and oversized windows that flood the space with natural light. Hard floors flow throughout the main level, leading to a spacious eat-in kitchen with granite countertops, plus a formal dining room perfect for hosting gatherings and special occasions. This 3-bedroom, 1.5-bath home also offers both bathrooms newly renovated, along with the convenience of a main-floor laundry room with a new washer and dryer. An attached one-car garage adds everyday practicality, while the back patio invites you to unwind and enjoy the tranquil, wooded surroundings. Don't miss your opportunity to make this move-in ready home yours!

66 Whitetail Run, 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

Start Your Search

© 2026 TReND. All Rights Reserved.
The data relating to real estate for sale on this website appears in part through the TReND Internet Data Exchange (IDX) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Real Broker NY LLC participates, and is provided by TReND through a licensing agreement. Real estate listings held by brokerage firms other than Real Broker NY LLC are marked with the IDX icon and detailed information about each listing includes the name of the listing broker.
All information provided is deemed reliable but is not guaranteed. Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.