Chester Homes with Swimming Pool Amenities

Welcome to Chester, Maryland, a hidden gem nestled in the heart of Queen Anne's County. This charming town offers a unique blend of picturesque landscapes, a tight-knit community, and a tranquil lifestyle, making it an ideal place for families and individuals alike. Known for its stunning waterfront views along the Chester River, residents enjoy the perfect backdrop for outdoor activities, from boating to fishing, and everything in between.

One of the standout features of homes in Chester is the availability of properties with swimming pool amenities. Imagine coming home after a long day to your own private oasis, where you can relax by the poolside or host summer barbecues with friends and family. These homes not only provide a refreshing escape during the warmer months but also enhance your lifestyle with luxurious outdoor living spaces. Whether you’re looking for a cozy retreat or a spacious family home, Chester boasts a variety of options that cater to your needs.

In addition to the serene environment, Chester offers convenient access to major highways, making commuting to nearby cities a breeze. With a rich history and a vibrant community spirit, Chester is also home to local shops, restaurants, and recreational parks, ensuring that you have everything you need right at your fingertips.

If you're considering a move to Chester, Maryland, you’ll find a welcoming community and beautiful homes that come with the added luxury of swimming pool amenities. Dive into the lifestyle you've always dreamed of in this charming town!

Newest Chester Homes with Swimming Pool Amenities

$550,000

2 Beds ⋅ 3 Baths ⋅ MDQA2018626 MLS

Set directly along the Chester River in desirable Queen’s Landing, this waterfront home puts the water at the center of everyday living, with incredible views from the main level, sunroom, patio, and both upstairs bedrooms. The shoreline feels remarkably close, creating a peaceful backdrop that can be enjoyed from nearly every principal living space. Renovations and upgrades throughout complement the setting, including wide-plank luxury vinyl plank flooring and an open-concept floor plan designed to keep the water in view. The remodeled kitchen, completed in 2022, features soft-close white cabinetry, quartz countertops, stainless steel appliances, a pantry, and a stainless steel sink and faucet positioned to overlook the entire main level and the Chester River beyond. Open to the living and dining combination, the kitchen creates an easy flow for everyday living and entertaining. A fireplace, added in 2025, brings a cozy focal point to the spacious gathering area while the water remains part of the view. Further along, a finished sunroom, unique to this home, extends the living space toward the water, with oversized sliding glass doors opening directly to the patio. Added in 2023, the patio provides an inviting place to sit outdoors and take in the ever-changing river scenery. Upstairs, both bedrooms enjoy water views, with the waterfront primary bedroom offering windows that act as artwork overlooking the serene Chester River. The remodeled primary bath features a convenient barn door, new shower with floor-to-ceiling tile, frameless glass door, and luxury vinyl plank flooring. The generous second bedroom also has an en-suite bath with luxury vinyl plank flooring. Additional improvements include a new front door, whole-house paint and electrical upgrades, second-floor carpet, a 2025 HVAC system, and first-floor luxury vinyl plank flooring added in 2026. The Queen’s Landing community offers a true waterfront lifestyle with a heated waterfront pool, clubhouse, fitness center, indoor racquetball court, tennis and pickleball courts, walking paths, kayak storage and launch areas, and a resident-only 62-slip marina. A kayak launch is conveniently located at the end of the street, while a deeded 25-foot boat slip is also available for purchase, adding even more opportunity to enjoy life on the Chester River. With water views woven throughout the home and direct access to the community’s waterfront amenities, this is a special opportunity to embrace the Chesapeake lifestyle from the comfort of home.

47-F Queen Anne Way, Chester

$815,000

4 Beds ⋅ 3 Baths ⋅ MDQA2018740 MLS

This beautiful coastal Colonial home in Gibsons Grant offers a perfect blend of comfort and style. With 4 spacious bedrooms and 2.5 bathrooms, the open floor plan invites warmth and connection. Enjoy cooking up your favorite feast in the upgraded kitchen featuring an island, built-in appliances, and endless countertops. The family room, complete with a propane fireplace, is perfect for gatherings and gamed. Step outside to discover beautifully maintained common grounds, a community center, and a inground swimming pool. The neighborhood boasts walking paths, tennis courts, and picnic areas, ideal for outdoor enthusiasts. Located near the Chester River, residents can enjoy serene views and water access. With excellent schools and parks nearby, this community is perfect for those seeking an active lifestyle. Additional conveniences include lawn maintenance, snow removal, and trash services, ensuring a low-maintenance lifestyle. Experience the charm and vibrancy of this welcoming community-your new home awaits!

231 Evelyne St, Chester

$329,000

2 Beds ⋅ 3 Baths ⋅ MDQA2018730 MLS

Nestled in the community of Queens Landing, this townhome offers a blend of coastal charm and contemporary elegance with carefree living. Boat slips with provisioned boats when available through marina along with Kayaking and storage. With 1,440 square feet of thoughtfully designed living space, this home is a sanctuary of comfort and style. Step inside to discover an inviting open floor plan that seamlessly connects the living and dining areas, creating an ideal space for entertaining or quiet evenings at home. The family room, conveniently located off the kitchen, features an electric fireplace, providing a cozy ambiance for gatherings. On the second level, are two bedrooms both with their private full bath. The most recent upgrades include; New HVAC, new electric fireplace, new kitchen appliances (GE Profile), updated bathroom, new shower, new carpeting and painted throughout. The community amenities include access to an outdoor swimming pool, tennis courts, and pickleball courts, all designed for an active and social lifestyle. The clubhouse and fitness center provide additional opportunities for relaxation and recreation. This home is conveniently located off of 301/50 and minutes from the Bay Bridge for an easy commute. to Annapolis/DC or Baltimore. NOTE; Community upgrade for Fios internet in process

53 Queen Caroline Ct, Chester

$789,000

3 Beds ⋅ 3 Baths ⋅ MDQA2018418 MLS

Welcome to 402 Macum Creek Drive, ideally situated along Macum Creek in the beautiful waterfront community of Gibson’s Grant. This thoughtfully designed Hartley model by Koch Homes offers three bedrooms, two-and-a-half baths, and an open floor plan perfect for everyday living and entertaining. A beautiful stone propane fireplace creates a warm and inviting focal point in the main living area. Double porches provide the perfect place to relax and take in breathtaking sunset views over the creek. Positioned on a desirable corner lot, the home also features a fenced backyard, spacious deck, and hardscape patio—ideal for outdoor dining, entertaining, or simply enjoying the peaceful surroundings. A rear-entry two-car garage with a large parking pad provides ample space for residents and guests. Gibson’s Grant is conveniently located near waterfront dining, shopping, and the Cross Island Trail, with easy access to the Bay Bridge for commuting or exploring all that the Eastern Shore has to offer. Experience the perfect blend of waterfront community living, everyday convenience, and the relaxed Shore lifestyle.

402 Macum Creek Dr, Chester

$930,000

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

$439,000

3 Beds ⋅ 4 Baths ⋅ MDQA2018508 MLS

Set along scenic Lake Amletto in the waterfront resort-style community of Queen’s Landing, this three-level garage townhome pairs updated interiors with relaxing water views and an impressive collection of community amenities. Neutral paint, wide-plank luxury vinyl plank flooring, new carpeting, and updates to the kitchen and bathrooms create a fresh, cohesive feel throughout. Step inside to a spacious living and dining room combination designed for easy everyday living and entertaining. The dining area flows into the updated kitchen, with a breakfast bar providing a natural transition between the spaces. Quartz countertops, stainless steel appliances, and a subway tile backsplash give the kitchen a polished look, while its open connection to the adjacent family room keeps the layout inviting and functional. A sliding glass door leads from the family room to the deck, where views of Lake Amletto create a peaceful backdrop for dining or unwinding outdoors. Upstairs, all three bedrooms feature vaulted ceilings that enhance the sense of space. The primary bedroom includes two closets and a stylish vanity area, along with a private water closet featuring a tiled tub and shower surround with a soaking tub. Two additional bedrooms share the hall bath, where a vaulted ceiling and statement light fixture lend an elevated feel. The lower level adds valuable flexibility with a recreation room and sliding glass door opening to the backyard. A separate laundry room is also located on this level, along with interior access to the attached one-car garage. Just inside the garage, a convenient drop zone helps keep everyday essentials organized, while the painted garage offers additional storage space. Beyond the home, Queen’s Landing delivers a true waterfront lifestyle along the Chester River on Kent Island. Residents enjoy a heated waterfront pool, clubhouse, fitness center, indoor racquetball court, tennis and pickleball courts, walking paths, kayak storage and launch areas, and a resident-only 62-slip marina. With Lake Amletto just outside and access to Kent Narrows, Eastern Bay, and the Chesapeake Bay nearby, this inviting home offers an ideal blend of updated comfort, water views, and resort-style living. Please note: photos depicting furniture have utilized virtual staging.

41 Queen Catherine Ct, Chester

$389,900

3 Beds ⋅ 3 Baths ⋅ MDQA2018242 MLS

Bayside In Kent Island Located in the Popular Community of Bayside just minutes from the Bay Bridge and all Kent Island has to offer! This lovely End Unit Townhome with Garage is very well maintained and in move in condition. It features 3 levels above ground. Enter at ground level which includes Garage, Foyer, Laundry and a bright and sunny 1st floor Family Room with Sliding Glass Doors to a Concrete Patio. The next level up opens to an Expansive Living Room/Dining Room combo with gleaming hardwood floors, propane gas Fireplace w mantle and sliding glass doors to a rear facing Deck. The Half Bath & L-Shaped Kitchen with pass thru are located in the front of the home, and the Kitchen is nicely updated to include stainless steel appliances, white cabinets, quartz counters, modern oversized sink with single lever faucet and wonderful wall of built-in storage/pantry space.

108 Blenny Ln, 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

$595,000

2 Beds ⋅ 3 Baths ⋅ MDQA2017608 MLS

Beautiful fourth-floor condo offering nearly 2,000 square feet of living space, featuring two bedrooms, a home office, two full baths, and a half bath. Enjoy morning sun from the oversized porch, a spacious living room, and an open-concept layout designed for comfort and entertainment. Highlights include luxury flooring, a fireplace, and a beautifully appointed kitchen with an oversized center island and quartz countertops stainless steel appliances and much more. This unit also includes a one-car garage and private storage space. The community offers unparalleled amenities and gorgeous water views, creating the perfect Chesapeake Bay lifestyle. Enjoy walking trails, outdoor tennis courts, indoor and outdoor pools, and a 23,000-square-foot clubhouse with outdoor spaces, a ballroom, test kitchen, outdoor bar, and community pier, views of the Chester River.

1000 Herons Nest Way Unit #43, Chester

$825,000

4 Beds ⋅ 4 Baths ⋅ MDQA2017378 MLS

Situated on one of the largest lots in sought-after Gibson’s Grant, this 4-bedroom, 3.5-bath home offers space, flexibility, and room to grow. High ceilings and an open layout create an airy feel, with an oversized kitchen flowing seamlessly into the family room and a separate main-level office for work or quiet retreat. The main level also features a formal dining room and living room. Upstairs, the spacious primary suite features a sitting area, two walk-in closets, and en-suite bath, alongside three additional bedrooms and two full bathrooms. The unfinished walkout basement includes a rough-in for a future bath. Outside, enjoy a fenced backyard complete with a patio and built-in fire pit—perfect for gathering year-round. Community amenities include swimming pool, clubhouse, fitness center, walking trails, community pier, picnic area, and kayak launch. Centrally located on Kent Island. Only 5 minutes to the Bay Bridge.

232 Evelyne St, Chester

$349,900

3 Beds ⋅ 3 Baths ⋅ MDQA2017082 MLS ⋅ Queens Landing BLDG.

Completely remodeled in 2026 with a new kitchen to include new appliances, quartz counters, and backsplash, 3 new bathrooms, all new flooring throughout, new washer and dryer and freshly painted. Nestled in the serene enclave of Queens Landing, this exquisite remodeled in 2026 Colonial townhouse offers a harmonious blend of luxury and comfort. Spanning 1,440 square feet, the open floor plan invites you to experience a seamless flow between the combination dining and living areas, perfect for both intimate gatherings and entertaining. The family room, conveniently located off the kitchen, creates a warm atmosphere where cherished memories are made. Indulge in the elegance of three spacious bedrooms all on the same level and two and a half beautifully recently remodeled bathrooms, designed for relaxation and rejuvenation. The inviting ambiance is enhanced by the cozy fireplace, providing a perfect backdrop for cozy evenings at home. Step outside to discover the community's stunning outdoor pool, where you can unwind under the sun or enjoy leisurely afternoons by the water. With direct access to the Chester River, water enthusiasts will appreciate the navigable waters, ideal for kayaking or simply soaking in the tranquil views. Queens Landing boasts an array of amenities, including a clubhouse, exercise room, and scenic bike trails, fostering an active and vibrant lifestyle. The meticulously maintained common grounds offer a picturesque setting for leisurely strolls or social gatherings. This property is not just a home; it's a lifestyle choice that embodies luxury, comfort, and community. Experience the best of waterfront living in this exceptional residence, where every detail has been thoughtfully curated for your enjoyment. Schedule your tour today!!

54F Queen Caroline Ct, Chester

$299,900

3 Beds ⋅ 3 Baths ⋅ MDQA2017146 MLS

Motivated Seller! This home is move in ready. Discover refined waterfront community living in this beautifully updated and rarely available 3-bedroom, 2.5-bath condo in the highly desirable Queen’s Landing community. Thoughtfully designed with both comfort and style in mind, this spacious home offers fresh interior paint, an inviting open layout, and a beautifully updated kitchen featuring elegant quartz countertops—perfect for everyday living, relaxing weekends, and entertaining family and friends. Natural light fills the living spaces, while the seamless flow between the kitchen, dining, and living areas creates a warm and welcoming atmosphere throughout the home. Step outside to enjoy your private screened porch—ideal for morning coffee or evening unwinding—or host summer gatherings on the private patio designed for grilling and outdoor entertaining. Rare opportunities like this don’t come along often in Queen’s Landing, especially with the combination of three bedrooms, modern updates, and exceptional outdoor living spaces. Enjoy a true resort-style lifestyle with community amenities that include a swimming pool, fitness center, pickleball and tennis courts, and a private marina. Whether you’re looking for a full-time residence, weekend retreat, or low-maintenance coastal lifestyle, this home offers the perfect balance of relaxation and convenience. Ideally located in the heart of Chester, you are just minutes from waterfront dining, shopping, entertainment, and major commuter routes—making it easy to enjoy everything the Eastern Shore has to offer while staying connected to Annapolis, Baltimore, and Washington, D.C.

54 Queen Caroline Ct, Chester

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