Chester Homes with Fitness Center Amenities

Welcome to Chester, New York—a picturesque gem nestled in the heart of Orange County. Known for its stunning landscapes and vibrant community, Chester offers a perfect blend of small-town charm and modern conveniences. With its proximity to the breathtaking Hudson Valley, residents enjoy an array of outdoor activities, from hiking and fishing to exploring local parks and nature trails. The town’s rich history is complemented by a lively arts scene, excellent dining options, and a warm sense of community that makes Chester a wonderful place to call home.

For those seeking a lifestyle that prioritizes health and wellness, Chester’s real estate market features homes equipped with fantastic fitness center amenities. Imagine waking up each day in a beautiful home where your fitness goals can be achieved without ever leaving the comfort of your property. These residences often include state-of-the-art gym facilities, swimming pools, and wellness spaces designed to inspire an active lifestyle. Whether you’re an avid runner, a yoga enthusiast, or someone who simply values the convenience of having a fitness center at your fingertips, Chester’s homes with fitness amenities cater to your needs.

In addition to promoting physical well-being, these homes often come with spacious layouts, modern designs, and access to Chester's serene natural beauty. With a strong sense of community and a commitment to healthy living, Chester, NY is the perfect place for those who want to thrive in both mind and body. Explore the exceptional homes available in this idyllic town and embark on your journey to a healthier, happier lifestyle today!

Newest Chester Homes with Fitness Center Amenities

$379,900

1 Beds ⋅ 2 Baths ⋅ MDQA2018696 MLS

Enjoy waterfront living in the sought-after Queens Landing community! This Mediterranean style 1-bedroom, 1.5-bath end unit condo offers a unique layout with beautiful water views and multiple outdoor spaces designed to make the most of the setting. The first-level primary bedroom and full bath allow for convenient main-level living. The upper-level loft adds valuable flex space with a wood-burning fireplace, skylights, and an abundance of natural light making it the perfect space for a home office, sitting area, guest space, or cozy retreat. Step outside and choose your view, from the garden-style front patio to the waterside patio out back or the upper-level balcony overlooking the water. With inviting indoor spaces, plenty of natural light, and multiple places to relax outdoors, this condo offers an easy, low maintenance, Eastern Shore lifestyle in a beautiful waterfront community.

12 Queen Anne Way Unit #J, Chester

$639,990

2 Beds ⋅ 2 Baths ⋅ MDQA2018602 MLS

Welcome to the Bernstein II, a beautifully designed home offering 2 bedrooms, 2 baths, and a 2-car garage. This home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area offers a spacious and functional space for lounging. A dedicated home office provides a private space for productivity, while the screened patio extends the living area outdoors—perfect for entertaining or relaxing. The kitchen is equipped for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive, elegant finish. Hardwood flooring flows throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, bedrooms 2, the primary suite, loft, and second floor, while tile is featured in all full baths and the laundry room. The primary bath includes a walk-in shower with seat and handheld shower wand and a double-sink vanity for added convenience and luxury. 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. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

641 Warbler Way, Chester

$944,900

3 Beds ⋅ 3 Baths ⋅ MDQA2018566 MLS

Welcome to 275 Warbler Way, a beautifully upgraded Kerr model by K. Hovnanian in the sought-after 55+ Four Seasons at Kent Island community. Less than two years old and already through its one-year builder punch list, this home offers the ease of newer construction without the wait—plus thoughtful upgrades and finishes already in place. Situated on a premium corner lot, this impressive home features 3 bedrooms, a dedicated home office, a spacious second-floor loft and a 3-car garage, including a tandem bay with EV charger. Inside, custom details immediately set it apart, including decorative molding in the foyer and primary bedroom, upgraded chandeliers in the foyer and dining room, custom window shades and a beautiful stone propane fireplace. The kitchen showcases K. Hovnanian's upgraded Looks package with crisp white cabinetry and upgraded Thermador appliances, complemented by reverse osmosis at the kitchen sink and a whole-house water filtration system. Additional features include a Rinnai tankless water heater, two-zone HVAC with propane backup and a whole-home surge protector. Outdoor living is ready to enjoy with a paver patio, propane grill hookup, irrigation system and upgraded landscaping—no waiting for a new yard to grow in or projects to be completed. Best of all, the location puts the Four Seasons lifestyle right outside your door. Enjoy easy access to the community's pickleball courts, clubhouse, indoor and outdoor pools, fitness center, walking trails, pier, kayak launch and more. Why wait to build when you can move right into a nearly new Kerr with the premium lot, upgrades, landscaping and finishing touches already done? 275 Warbler Way delivers exceptional value and an easy, move-in-ready Eastern Shore lifestyle.

275 Warbler Way, 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

$459,000

3 Beds ⋅ 3 Baths ⋅ MDQA2018494 MLS

Welcome to 43-A Queen Neva Court, a pristine 3-bedroom, 2.5-bath contemporary condo in the sought-after Queens Landing community. Offering more than 2,000 square feet of living space, this spacious end unit features an open, sunlit floor plan that is perfect for everyday living and entertaining. The oversized kitchen provides abundant workspace and storage, while the inviting living area is highlighted by a cozy fireplace. The generous primary suite includes a private bath with a soaking tub and separate shower. Step outside to your patio and enjoy peaceful pond views, added privacy, and the benefits of end-unit living. Queens Landing offers an amenity-rich lifestyle with a community pool, clubhouse, fitness center, tennis courts, and much more. This one is truly a 10/10!

43 Queen Neva Ct, 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

$749,990

2 Beds ⋅ 3 Baths ⋅ MDQA2018316 MLS

Welcome to the Taylor, a beautifully designed home offering 2 bedrooms, 2 baths, and a 3-car garage. This home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area features a cozy fireplace with mantel and hearth, creating a warm and inviting focal point. A dedicated home office provides a private space for productivity, while the screened patio extends the living area outdoors—perfect for entertaining or relaxing. The kitchen is equipped for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive, elegant finish. Hardwood flooring flows throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, bedrooms 2, the primary suite, loft, and second floor, while tile is featured in all full baths and the laundry room. The primary bath includes a walk-in shower with seat and handheld shower wand and a double-sink vanity for added convenience and luxury. 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. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

536 Warbler Way, 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

$862,750

3 Beds ⋅ 2 Baths ⋅ MDQA2018158 MLS

THE SELLER WILL ACCEPT OFFERS WITH MOST FURNITURE INCLUDED. SOME SMALL DECORATIONS AND A FEW PICTURES ARE RESERVED. THE MOVING VAN IS ALREADY SCHEDULED. Be part of the fastest growing 55+ community on Maryland's Eastern Shore. Bayberry was the first street in Four Seasons Kent Island where construction in 2021 was superior to those today. 320 Bayberry Drive sits on a Premium Lot which abuts lands owned and maintained by the HOA. The developer is charging a Lot Premium of up to $400,000 for the extra space on remaining lots. The seller just completed $80,000 in renovations. Most of the Furniture can be purchased for below half of what it’s value. The optional sunroom area was completely finished as additional living space. There is a massive 256 square foot rear patio with low V lighting and two raised garden beds. Another HOA area is the rear buffer and beautifully landscaped. If they have a dog, the common area next to the home is almost the size of a building lot offering exceptional privacy. FSKI club house offers resort quality from the indoor pool and gym or the outside pool in summer months. FSKI also allows you golf carts! Don’t miss this opportunity to experience resort style living at Four Seasons Kent Island.

320 Bayberry Dr, Chester

$1,100,000

3 Beds ⋅ 4 Baths ⋅ MDQA2018162 MLS

The Franklin Model Home offers a beautifully designed open-concept layout enriched with elevated designer finishes—available now for immediate settlement with a rent-back opportunity. With 3 bedrooms, 3.5 baths, and a 2-car garage, this home provides a refined blend of comfort, versatility, and modern style. Standout features include a dedicated home office, a cozy fireplace, and a screened patio that extends your living space outdoors. Thoughtful design details—such as barn doors, crown molding, and a custom feature wall—add character and craftsmanship throughout. As an added bonus, all model home furniture is included, offering a seamless move-in-ready experience. The beautifully appointed kitchen features a range, single oven, microwave, range hood, dishwasher, French door refrigerator, stylish pendant lighting, and a coordinating tile backsplash. Quartz countertops elevate both the kitchen and the owner’s bath for a fresh, integrated design. LVP flooring extends across the main level for durability and style, with tile in all full baths and carpet in Bedrooms 2 and 3 for added comfort. The owner’s bath offers a spa-inspired shower with a built-in seat, handheld shower wand, and double sinks—creating a relaxing and functional daily retreat. For a full list of included features, please contact our sales representatives. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

117 Flycatcher Way, Chester

$799,900

4 Beds ⋅ 3 Baths ⋅ MDQA2018144 MLS

Welcome to 313 Thomas White Boulevard in the sought-after waterfront community of Gibson's Grant on Kent Island. This beautifully maintained Koch-built home offers more than 3,200 square feet of thoughtfully designed living space with four bedrooms, two-and-a-half baths, and a flexible floor plan tailored to today's lifestyle. The main level features hardwood flooring,crown molding and refined architectural details throughout, a main-level home office, and a spacious family room anchored by a cozy gas fireplace. The gourmet kitchen is designed for both everyday living and entertaining, showcasing granite countertops, rich mahogany cabinetry, stainless steel appliances, double wall ovens, a center island, pantry, and a sunny breakfast area. Upstairs, the spacious primary suite offers a walk-in closet and a luxurious en-suite bath with a soaking tub and separate shower, while three additional bedrooms provide plenty of room for family and guests. Above the garage, an expansive bonus room offers endless possibilities for recreation, work, fitness, or guest accommodations, making it one of the home's most versatile spaces. Relax on the welcoming front porch where you can enjoy the neighborhood's charming streetscape and peaceful surroundings, or unwind in the screened porch overlooking the fenced backyard, an inviting space for morning coffee, outdoor dining, or relaxing. A rear-entry two-car garage adds everyday convenience while preserving the home's classic curb appeal. Located in one of Kent Island's premier waterfront neighborhoods, Gibson's Grant offers exceptional resort-style amenities, including a community pool, clubhouse, fitness center, walking trails, kayak launch, fishing pier, pavilion, playgrounds, picnic areas, and water access to Macum Creek and the Chester River. Just minutes from Route 50 and the Chesapeake Bay Bridge, this home provides an easy commute to Annapolis, Baltimore, Washington, D.C., and Maryland's Eastern Shore while offering the relaxed coastal lifestyle that makes Kent Island so desirable.

313 Thomas White Blvd, 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

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