Chester Condos for Sale

Welcome to Chester, New York – a hidden gem nestled in the heart of Orange County, where picturesque landscapes meet a vibrant community spirit. Known for its stunning natural beauty, Chester offers residents a unique blend of serene country living and modern conveniences. With the majestic backdrop of the Hudson Valley and the nearby Catskill Mountains, outdoor enthusiasts will find plenty of opportunities for hiking, fishing, and exploring the great outdoors.

Chester boasts a charming downtown area filled with delightful shops, cozy cafes, and local eateries that reflect the town's warm, welcoming atmosphere. Whether you’re strolling through the quaint streets or enjoying a local festival, you’ll quickly discover why Chester is beloved by its residents.

For those considering a move to this enchanting area, our selection of condos for sale in Chester presents an incredible opportunity. These modern residences offer a perfect balance of comfort and style, featuring spacious layouts, contemporary finishes, and stunning views of the surrounding landscape. Many condos provide convenient amenities such as fitness centers, pools, and outdoor spaces, making them ideal for both relaxation and entertainment.

Living in Chester means embracing a lifestyle filled with community events, excellent schools, and easy access to nearby attractions. Plus, with its close proximity to major highways, commuting to neighboring cities for work or leisure is a breeze.

Don’t miss your chance to be a part of this vibrant community. Explore our available condos for sale in Chester today and discover your new home in this idyllic corner of New York!

Newest Chester Condos for Sale

$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

$719,990

2 Beds ⋅ 3 Baths ⋅ MDQA2018548 MLS

Welcome to Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in May 2027, this home combines comfort, functionality, and stylish finishes for modern living. The main living area features an electric fireplace, creating a warm and inviting focal point, while a dry bar adds the perfect touch for entertaining. A dedicated home office with French doors provides a private and polished space for working from home, studying, or pursuing hobbies. The kitchen is designed for both everyday living and entertaining, featuring a single oven, microwave, gas cooktop, range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Laminate flooring flows throughout the home, with tile flooring in both full baths for added durability and style. The primary bath offers a relaxing retreat with a spacious shower featuring a built-in seat and handheld shower wand, along with a double-sink vanity and quartz countertops. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

736 Warbler Way Unit #2733, 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

$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

$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

$835,000

3 Beds ⋅ 3 Baths ⋅ MDQA2018120 MLS

Welcome to Four Seasons at Kent Island, where luxury waterfront living meets the ease of a premier 55+ lifestyle on the shores of the Chester River. Offering breathtaking, unobstructed water views and exceptional community amenities, this beautifully appointed three-bedroom, two-and-a-half-bath condominium is designed for those who appreciate comfort, elegance, and low-maintenance living. The light-filled, open-concept floor plan showcases luxury vinyl plank flooring throughout, recessed lighting, and expansive windows that capture stunning views of the Chester River from nearly every angle. The spacious living room is anchored by a cozy electric fireplace and flows seamlessly into the dining area and gourmet kitchen, creating the perfect space for entertaining or relaxing. The kitchen features stainless steel appliances, a gas cooktop, white cabinetry, generous countertop space, and an inviting layout that keeps everyone connected. Just beyond the living area, step onto the expansive waterside balcony and enjoy panoramic river views, morning coffee, spectacular sunsets, and endless opportunities to watch boats glide by. The luxurious primary suite is a private waterfront retreat, complete with direct balcony access, a spacious sitting area, two walk-in closets, and an elegant ensuite bath featuring dual vanities and a large walk-in shower. Two additional bedrooms provide comfortable accommodations for guests, a home office, or hobbies. Additional highlights include a beautifully crafted built-in bar, electric blinds, a large laundry room, a dedicated storage room, and an attached one-car garage with new epoxy speckled floor. Residents enjoy an exceptional resort-style lifestyle with amenities that include indoor and outdoor swimming pools, a fitness center, clubhouse, library, billiards room, hot tub, Bocce Ball, pickleball and tennis courts, picnic areas, tot lots, and a community pier overlooking the Chester River. Ideally located just minutes from shopping, dining, golf, marinas, and the Chesapeake Bay Bridge, this exceptional waterfront residence offers the perfect blend of luxury, convenience, and carefree Eastern Shore living.

201 Switchgrass Way Unit #34, 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

$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

$998,000

3 Beds ⋅ 3 Baths ⋅ MDQA2017940 MLS

Welcome to this stunning 4th floor penthouse Severn condominium with serene bay views! This end unit looks out over the walking trails to the water and trees. The fabulous community center /pool / pier is a short 1 mile walk from your backyard.! This unit also has the largest garage space in the the building, plenty of room for one car and storage, a refrigerator etc. There is also an additional inside storage room. This 2600 Sq Ft home is flooded with natural light and has numerous quality upgrades including custom shiplap in most of the rooms, custom ceiling fans and dining room light fixture, custom built his and hers walk in closets. The primary bath has upgraded tile, shelving for more storage, mulitple shower heads and back and front lit vanity mirrors. The gourmet kitchen is designed to impress, featuring elegant quartz countertops,premium appliances and a Wolfe induction cooktop. The island has been upgraded with shiplap as well. Thoughtful upgrades continue throughout the entire home with custom blinds with remote control, a gas fireplace,9 FT ceilings with tray ceilings in the living room and primary suite. A wet bar has also been added to the dining area.The large primary bedroom comes complete with a sitting area/office with exceptional waterviews. It also offers custom designed his -and -her closets that provide both style and storage. This unique residence offers a peaceful setting where you can relax and enjoy the ever-changing waterfront vistas. Whether you are enjoying your morning coffee or entertaining guests, this home offers the perfect blend of sophistication, comfort, and low maintenance waterfront living. Residents enjoy an exceptional resort-style lifestyle with amenities that include indoor and outdoor swimming pools, a fitness center, clubhouse, library, billiards room, hot tub, Bocce Ball, pickleball and tennis courts, picnic areas, tot lots, and a community pier overlooking the Chester River. Ideally located just minutes from shopping, dining, golf, marinas, and the Chesapeake Bay Bridge, this exceptional waterfront residence offers the perfect blend of luxury, convenience, and carefree Eastern Shore living.

111 Marshgrass Way Unit #41, Chester

$919,990

2 Beds ⋅ 3 Baths ⋅ MDQA2018010 MLS

Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office with lited French doors provides a private and elegant workspace. The kitchen is designed for both everyday living and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with a seat and handheld shower wand, double sinks, and quartz countertops, creating a comfortable and functional retreat. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

102 Boatswain Way Unit #2943, Chester

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