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$309,900
3 Beds 3 Baths
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

Listing courtesy of Island Realty, LLC. Contact:

$589,000
3 Beds 3 Baths
Set on a splendid site backing to open space and woods, this dramatic Gershwin model with a solarium extension and loft will delight you. As you walk through the living and dining room and on to the kitchen and family room, the floor-to-ceiling stone fireplace in the solarium will  draw your eye, with a half round window high on the wall above. Several transom windows add to the natural light flowing into the house. An office opposite the living/dining room could become an additional bedroom, with easy access to the hall bathroom, or a hobby room, music or reading room. Rich hardwood flooring through the formal  area and kitchen, with carpeting in other areas and bedrooms. The gourmet kitchen has granite countertops, cherry cabinets, an electric cooktop and double oven plus microwave, large refrigerator and dishwasher. Several appliances have been replaced. The en suite primary bedroom has two closets, and the bathroom has a soaking tub, double vanity and a large shower with a seat. The guest bedroom is located in a separate hallway with an adjacent bathroom. On the upper floor is a second family room, bathroom and spacious bedroom with a large closet. Over the garage is the sky basement generally used for storage, with attic access. The custom patio overlooks the woods, and a feeling of serenity descends as you enjoy the view and the birdsong. The Symphony Village community is well established, with mature trees throughout, and an impressive clubhouse with many amenities, including a concert hall for the many events organized by the various committees. The main gathering area is bright and welcoming, and is the location for semi-monthly social hours where you bring a dish to share and get to meet your neighbors. Several groups with varied interests meet in the clubhouse on a regular basis, and you might walk through the clubhouse and see folks learning to paint in the craft room, others playing pool, some playing mahjong in the concert hall, or committee meetings to keep things humming along. You can walk outside to the covered patio area and the pool beyond, where residents enjoy holiday picnics, quiet evening time, and fun with the kids during the day. The indoor pool is open every day from early morning until late at night, and you can show up for water aerobics every weekday morning at 9:00A.M. Currently there are Spanish classes offered, in addition to soul line dancing, and at any time you can learn how to play bridge or hand and foot, so there is plenty to keep everyone busy. However, there is no requirement to participate in any activities, and you can live a quiet life in Symphony Village enjoying retirement or still working. There are many areas to walk in around the neighborhood, and in the clubhouse grounds is a pergola to sit and  watch the world go by, a kids' playground, a picnic area, bocce, a putting green (and active league) and a trail leading to Dunkin' Donuts and the shopping center just minutes away.

106 Encore Ct, Centreville

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$485,000
2 Beds 3 Baths
BACK on the MARKET. GREAT OPPORTUNITY at THIS PRICE. This Chester model has scenic, seasonal views of Macum Creek, beautiful sunrises, and an incredible display of wildlife in all seasons. Easy walk to Kayak launch and creek. With nearly 2000 square feet of open living space this home has a great layout for entertaining family and friends. The spacious great room, adjacent to the dining area and kitchen, provide an open area for gatherings. The gourmet kitchen is equipped with upgrades from the stunning kitchen island with quartz counter tops, beautiful upgraded cabinetry to the GE Profile appliances. This kitchen is designed for everyday living as well as hosting the occasional dinner party. The primary bedroom, is a separate self-contained suite complete with two closets and a luxury owners' bath that includes double sinks, and quartz countertops. The bright and airy 2nd bedroom is also a separate suite with a full bath and an oversized walk-in closet. In addition to the two bedrooms, there is a home office with stylish French Doors and a powder room for guests. The separate laundry room is equipped with a GE washer and dryer. This home also has a garage with adjoining driveway/parking space and large personal storage room which is a few short steps from the elevator. This home is just a short walk to resident kayak racks with launch access to the Chester River. KEEP IN MIND THIS CHESTER MODEL, WITH PLENTY OF FEATURES AND UPGRADES INCLUDED, IS MOVE-IN READY AND PRICED TO SELL***** Award-winning 24,000 Square Foot Clubhouse with Stunning Chester River Views! Fantastic amenities include 4.3 miles of walking trails throughout the community, outdoor infinity pool, indoor pool with on-duty lifeguard, fitness center, library, game room, gas and wood burning fire pits, Tiki bar equipped with refrigerators, sinks and television monitors, pier with transient boat slips, walking paths that link to the Cross Island Trail, lighted pickle ball courts, tennis courts, bocce, dog park, and an outdoor amphitheater for live music and movie nights. The community lifestyle director will keep you busy with daily activities such as yoga, a variety of exercise classes and an assortment of clubs including biking, billiards, book club, baking, mahjong, environmental club, trivia night and more. In addition to the weekly and monthly activities, residents can enjoy crab feasts, oyster roasts, and holiday gatherings throughout the year. This development is an unrivaled, amenity-filled, resort-style experience with convenient access to Annapolis, DC, Baltimore, and BWI. Kent Island offers multiple dining and shopping options, a nearby outlet mall, and a 6.5 mile cross-island trail surrounded by views of the Chester River.

1000 Herons Nest Way Unit #22, Chester

Listing courtesy of RE/MAX Executive. Contact: 4432741900

$515,000
2 Beds 3 Baths
WATERFRONT Condo! Open House dates scheduled. Beautifully renovated 2BR/2.5BA waterfront condominium located in the sought-after Queen’s Landing resort-style community on the scenic Chester River, just off the Chesapeake Bay. This move-in-ready home showcases a stunning top-to-bottom remodel, including new luxury vinyl plank flooring, new carpet, fresh paint throughout (ceilings, walls, trim, and doors), new white cabinetry, beautiful quartz countertops with beveled white backsplash, updated bathroom vanities, flooring and modern lighting fixtures. The light-filled open floor plan is designed to highlight the panoramic Chester River views. The spacious family room off the kitchen features an oversized sliding glass door leading to a private balcony with beautiful eastern water views—perfect for morning coffee or relaxing evenings overlooking the river. Upstairs, the primary bedroom suite offers elevated water views and a private full bath. A second large bedroom and additional full bath complete the upper level, with washer and dryer conveniently located between the bedrooms. Residents of Queen’s Landing enjoy exceptional waterfront amenities including a private marina, swimming pool overlooking the Chester River, clubhouse, fitness center, tennis and pickleball courts, and scenic waterfront walking paths. Ideally located just minutes from shopping, dining, entertainment, the Cross Island Trail, and the Chesapeake Bay Bridge, this home is perfect as a full-time residence or weekend waterfront retreat on Maryland’s Eastern Shore. Schedule your private tour today!

34 Queen Anne Way, Chester

Listing courtesy of Taylor Properties. Contact:

$529,000
4 Beds 4 Baths
NEW PRICE ....Welcome to 142 Harmony and this beautiful Beethoven model home featuring 4 bedrooms and 3 and one half bath. Situated on a lot that is just a short walk to the community club house, pools and all amenities, this home is designed with a beautiful brick front. As you enter, the floor inviting floor plan welcomes you with the living and dining area on the front of the home and stairs to the side to the upper level. Moving through you'll enter the very large family room with fireplace and the oversized gourmet kitchen with additional cabinets. The breakfast area off of the kitchen allows for relaxing views of the rear patio. The master suite is also located on the main level with master bath featuring a walk-in shower and a walk-in jetted tub. This suite also has two walk-in closets and additional stairs to the upper level. To complete the main level of the home is a half bath and laundry room with access to the garage which includes a sky basement for storage above. The second level of the home offers a very large additional area that can be utilized in many ways along with a carpeted walk-in storage area that can be utilized as a closet or utility room. To complete the upper level is a sitting room overlooking the family room below along with another bedroom and full bath. This home is move in ready and available for a quick settlement.

142 Harmony Way, Centreville

Listing courtesy of RE/MAX Executive. Contact: 4432741900

$499,000
2 Beds 3 Baths
Four Seasons @ Kent Island - 55+ Community - Reduced! * 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

Listing courtesy of RE/MAX Leading Edge. Contact:

$675,000
3 Beds 5 Baths
Open House July 21, 2026, 4 PM to 7 PM. Welcome to 371 Overture Way, nestled in the serene 55+ active adult community of Symphony Village in Centreville, where comfort, convenience, and connection come together beautifully. This thoughtfully maintained home offers over 6,000 square feet of living and storage space, featuring 3 spacious bedrooms, 4 full baths, and 1 half bath, along with a new roof installed in 2023 for added peace of mind. The attached two-car garage includes a durable epoxy-coated floor and stairs to generous overhead storage, perfect for keeping everything organized without sacrificing living space. Designed with ease and everyday enjoyment in mind, the bright, open main level showcases a gourmet kitchen with extended granite countertops, stainless steel appliances, and a Jenn Air gas stove, ideal for both casual meals and entertaining. The adjoining breakfast nook provides ample cabinetry and prep space, while the flowing layout includes hardwood floors, custom plantation shutters, and inviting living and dining areas. A sun-filled sunroom with wall-to-wall windows offers a tranquil retreat and opens onto a spacious deck, perfect for relaxing or hosting guests while enjoying the private wooded backdrop. The main level primary suite is a true retreat, featuring two walk-in closets, dual vanities, a soaking tub, and a walk-in shower, offering comfort and convenience all in one space. Upstairs, a versatile loft provides the perfect setting for a sitting area or home office, along with a guest bedroom complete with its own full bath and walk-in closet - ideal for visiting family and friends. The fully finished lower level expands your living space even further, with a family room featuring a fireplace, room for a game table, and a walkout to a beautifully paved patio. Two additional bonus rooms, a full bath, and an oversized storage area with a workbench, refrigerator, and freezer make this level both functional and flexible. Life in Symphony Village means more than just a beautiful home, it's a vibrant, welcoming community. Residents enjoy access to a clubhouse with social spaces, indoor and outdoor pools, a fitness center, pickleball and bocce courts, walking and hiking trails, and a full calendar of activities designed to keep you as active and engaged as you would like to be. Conveniently located near Queenstown Premium Outlets and the charming downtown area of Centreville, you will also find yourself just a short drive from the waterfront towns of Chestertown, Easton, St. Michaels, and Annapolis. This is more than a home, it is a lifestyle designed for comfort, connection, and ease. Come experience all that 371 Overture Way has to offer!

371 Overture Way, Centreville

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686