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

$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

$840,000

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

$620,000

3 Beds ⋅ 3 Baths ⋅ MDQA2017258 MLS

Welcome to 265 Evelyne Street in the sought-after waterfront community of Gibsons Grant! Offering nearly 2,200 square feet of living space, this beautifully maintained home combines coastal charm with modern comfort. Inside, you’ll find engineered hardwood floors, a spacious open-concept layout, and a beautifully appointed kitchen featuring a large island, gas stove, double oven, and plenty of space for gathering and entertaining. The flexible floor plan includes a spacious family room above the two-car garage — perfect for a media room, playroom, home office, or guest retreat. The primary suite offers a relaxing escape with a double vanity, soaking tub, and walk-in shower. Additional highlights include a Rinnai tankless hot water heater, welcoming front porch, and thoughtful upgrades throughout. Enjoy all that Gibsons Grant has to offer, including a community pool, clubhouse, fitness center, kayak launch, walking trails, playgrounds, waterfront access, and scenic open spaces — all conveniently located just minutes from the Bay Bridge, shopping, dining, and everything Kent Island has to offer. Coastal living at its best!

265 Evelyne St, Chester

$359,900

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

$319,900

3 Beds ⋅ 3 Baths ⋅ MDQA2017146 MLS

Priced to Sell! 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

$399,000

3 Beds ⋅ 4 Baths ⋅ MDQA2016002 MLS

REDUCED! Just like NEW! Welcome Home to this beautifully upgraded 4BR END UNIT Townhome with 2 full and 2 half baths, thoughtfully renovated from top to bottom! Step inside to find the main level that boasts NEW carpet and new LVP flooring, a NEW half bath, NEW paint, a spacious laundry room and a large bedroom that could be used as another family room, toy/game room, den space, home office and more! Get ready to be wowed by the rich walnut NEWLY stained hardwood flooring throughout the 2nd level where the living room, gas fireplace, NEW half bath and kitchen are located. The BRAND-NEW Kitchen finishes are sure to please with NEW white quartz counter tops, NEW SS Appliances, fresh neutral paint and white cabinetry! Upstairs hosts the huge Primary En-Suite, 2 more bedrooms all with NEW Carpet and another full bathroom with NEWLY Tiled shower, NEW toilet and NEW quartz sink! With three generous levels, a deck overlooking the pond, a cozy patio and a charming front porch, there’s space for everyone to relax and have their own space! Pull right into your own garage and your own driveway which makes life easy not to have to look for parking! The community offers fantastic amenities to enjoy like the inground and life-guarded pool, volleyball & tennis courts, fitness gym and direct access to the Cross Island Trail! Very close to the Castle Harbor Marina, many Beaches, Parks & Playgrounds and just a short stroll to local restaurants along the waters edge of the CHESTER RIVER! Condo living made easy with the Bayside fee covering major exterior maintenance including the roof, deck rails, siding, exterior structural upkeep, landscaping, snow removal, road maintenance, trash, master insurance policy, professional property management, long term reserve funding and the list goes on! Truly turn‑key living in an unbeatable location on the desired Eastern Shore of Maryland! Come see what Kent Island living is all about! SUMMER is here!

208 Blenny Ln, Chester

$765,000

2 Beds ⋅ 3 Baths ⋅ MDQA2016724 MLS

Penthouse Unit! Seller offering closing cost assistance to qualified buyers! Rare top floor unit with year-round water views perfectly positioned to capture stunning sunrises every morning. This home has been owned and meticulously maintained by the original owner who spared no expense and opted for every builder upgrade that was offered, over $60,000.00 in options. The open concept design seamlessly connects the living room, dining area, and kitchen areas, all enhanced by expansive windows letting in an abundant amount of natural light. Experience resort style living in the highly sought after Four Seasons at Kent Island, a premier 55+ waterfront community. Residents enjoy access to world class amenities, including indoor and outdoor pools, walking trails, a Chester River pier. Ideally located just minutes from waterfront dining, shopping, and the Chesapeake Bay Bridge, this home offers the perfect blend of relaxation, convenience and low maintenance living at its finest.

111 Marshgrass Way Unit #43, Chester

$1,049,500

5 Beds ⋅ 5 Baths ⋅ MDQA2016702 MLS

Price Reduced $50K – Check out the Virtual Tour! Exceptional Value in Four Seasons at Kent Island Why wait to build? This less-than-one-year-old Tuscaloosa model on sought-after Kingfisher Lane delivers the upgrades, location, and efficiency buyers are chasing—without the timeline or added expense. Positioned just across from the Chester River, enjoy peekaboo water views from the covered front porch and even a sightline to the clubhouse. Inside, the home is bright, open, and thoughtfully designed with 5 bedrooms and 4.5 baths, offering flexibility for guests, work-from-home space, or multigenerational living. It shows like new—but lives better—because everything has already been elevated beyond builder grade. Over $70,000 in post-builder upgrades, including: • Owned solar system (10kW+) providing substantial energy savings • Custom closet systems throughout the home • Custom window treatments already installed • Premium Café Series appliances • Tankless water heater • Upgraded lighting and fixtures • Additional high-end finishes and improvements throughout The spacious floor plan offers room for everyone, while the oversized garage provides ample storage for vehicles, golf carts, and all the gear that comes with Eastern Shore living. Life in Four Seasons at Kent Island is about more than the home itself. Residents enjoy resort-style amenities including a stunning clubhouse, indoor and outdoor pools, fitness center, pickleball courts, walking trails, kayak launch, fishing pier, and an active social calendar designed for a vibrant lifestyle. With immediate availability, extensive upgrades already completed, and one of the community's most desirable locations, this home represents an opportunity that's becoming increasingly difficult to find. Add in the recent $50,000 price reduction, and this is one of the best values currently available in Four Seasons at Kent Island. Don't miss your chance to enjoy nearly new construction, energy-efficient living, and the Chesapeake Bay lifestyle you've been waiting for.

215 Kingfisher Ln, Chester

$530,000

2 Beds ⋅ 3 Baths ⋅ MDQA2015800 MLS

Four Seasons @ Kent Island - 55+ Community - Price Improvement + Seller to Credit $4000 towards Capital Contribution Fee * Turn-key & Lovely 2nd Floor Condo in Elevator Building with 1 Car Garage plus 1 Car Outdoor Parking and Private, Secure Indoor Storage Area. This Chester Model offers 1900 sf with pond view and winter water views of Macum Creek. Enter to find an expansive, open floor plan featuring a beautiful white Kitchen with quartz counters, propane gas cooktop with range hood, wall oven + microwave combo and a huge Island that accommodates plenty of bar seating. Spacious Bedroom suites each with private full baths and generous closet spaces. The Primary bath has His 'n Her's double sinks with Moen fixtures, comfort height vanities, large vanity mirrors, medicine cabinets and a walk-in tiled shower with seat. The Primary bedroom features 2 closets; one walk-in-closet and one generous wall closet, a ceiling fan and a single French door to access the balcony. The 2nd Bedroom is large enough to hold a traditional sized bedroom set and features a tub/shower combo in the bath. The open Great Room is large, bright and has serene pond views and winter water views of Macum Creek with oversized sliders to a covered balcony. You will love the convenient laundry room located off the foyer area that accommodates the included full-sized GE washer and dryer. Elevator down to the Lobby level to your private garage and a just a few steps down the corridor is your private, keyed storage closet. This condo building features a secure lobby entrance and is impeccably decorated and maintained. Additionally, the 2nd floor has a common Club Room/Meeting Room great for socializing with your neighbors or as additional entertainment space. It features Public Water, Public Sewer, individually metered propane gas heat and cooking. All residents have access to the community amenities which include a huge 20,000 sf Club House with Billiards Room, Casual Lounge Area, Fitness Center, Party and Meeting rooms, and fabulous Indoor Heated Pool & Spa. Outside awaits a resort-like Pool, Cabana House, Private Beach Area, Outdoor Concert Space, Pier for Fishing and taking in the magnificent Chester River views & Kayak launch and Walking Trails. Pickle Ball enthusiasts you are in luck as there are Tennis Courts and Pickle Ball Courts for all, and grand kids can be entertained at a small Playground Area. Come tour today and see why this is THE place to be in Kent Island for 55+ living!

4000 Herons Nest Way Unit #22, Chester

$329,000

2 Beds ⋅ 3 Baths ⋅ MDQA2015236 MLS

DON"T MISS OUT on this super deal!! Owners have lowered the price by $10,000 and are willing to look at offers! Nothing to do but move in! Be in this spring to enjoy all that summer offers on the shore!! This roomy 2 bedroom, 2.5 bathroom end unit has been completely painted in a beautiful neutral shade and has new carpet throughout the living areas and new vinyl flooring in the kitchen. A propane fireplace highlights the great room turning chilly nights into cozy nights! On warm days, enjoy relaxing in the enclosed patio/porch or just being outside. Being an end-unit it offers lots of privacy. Any and all assessments have been paid by the owner, so you are ready to go and enjoy all the amenities that Queens Landing is known for...beautiful waterside pool, the club house with a party room, racquet ball court, exercise room, tennis courts, jogging trail, and more! Close to the cross-island trail, the Matapeake Dog Park, restaurants, schools, library...it is a wonderful place to live! Whether you are looking for a place to use as a vacation or weekend home, or as a year-round residence, this will suit both needs. It's situated in a great location...minutes to the Bay Bridge for any commuters to the western shore, and many airports, and an easy drive to the MD and DE beaches! Note: 4 pictures have been Virtually Enhanced!

54 Queen Caroline Ct, 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.