Chester MD Real Estate & Homes for Sale

This is your chance to own a beautiful waterfront home on Kent Island on the scenic Eastern Shore of Maryland. A short drive to the Bay Bridge, Historic Annapolis and the many fabulous restaurants of Kent Narrows. This 2â3-bedroom, 2 full bath home has an idyllic setting overlooking farmland as well as a nostalgic working marina where you can see the Chesapeake crab and oyster boats come and go. The level bulkheaded lot has 90â +/- of water frontage. There is a T-shaped private pier that features water, electric, and two boat lifts (one is new-10,000 lbs. with remote). Mean low water is approximately 6â +/- at end of pier. The home boasts water views from most rooms and has numerous updates including new architectural shingle roof (2023), flooring thru-out, dishwasher, washer and dryer as well as new paint, LVP flooring and demising wall in the garage level family room/recreation room or potential third bedroom. The kitchen has 42â maple cabinets, stainless appliances (gas cooking) and granite counter tops. Waterside primary bedroom has en-suite full bath. Other fine features include: vaulted ceilings, recessed lighting, tank-less hot water heater, 3+ car attached garage and an oversized 1-car detached garage for the water toys. Sit on the large wrap around deck and enjoy the morning sunrise over the water or hop on the boat for a short ride to Crab Alley and Eastern Bay. You will feel like you are on vacation year-round or can be an ideal Airbnb home. BONUS â swim/SUP floating platform conveys and a 26â Sea Ray on lift. (The seller thinks it needs minor repair â as is). GREAT PRICE. WONâT LAST!!

Nestled within the water-privileged enclave of Queen's Landing, along the scenic Chester River off the Chesapeake Bay, this resort-style community unveils a beautiful residence designed for luxurious living. The open concept main level is adorned with a cozy fireplace, neutral color palette, and abundant natural light, creating an inviting ambiance. Multiple outdoor living spaces beckon, each offering captivating water views that amplify the sense of tranquility. Residents of this exclusive community relish an array of amenities, from a private marina and refreshing swimming pool on the Chester River to tennis/pickleball courts and a clubhouse with a social room. Stroll along the waterfront walking path, maintain an active lifestyle in the exercise room, or engage in a friendly match on the racquetball court. Inside, this residence boasts a thoughtfully designed kitchen with upgraded solid surface counters, double oven, and a seamless pass-through to the dining room with a breakfast bar. Custom plantation shutters grace the front door and sidelight window, adding a touch of elegance. The upper level reveals a bedroom with a private balcony and a renovated full hall bath featuring a walk-in shower. Convenience is key with an upper level laundry room. The primary bedroom impresses with a spacious layout, including a versatile space ideal for a sitting room or home office, complemented by a wet bar and a deck with serene water views. A loft bedroom with a full bath completes this exceptional retreat, offering an elevated perspective of the Chester River. In addition, enjoy being minutes from a multitude of shopping, dining, and entertainment options as well as the Cross Island Trail.

Welcome Home to 1409 Queen Anne Drive offering some of the best Eastern Shore Sunsets off of Crab Alley Bay. This Beautifully updated single family home located in the sought after Marling Farms Community on Kent Island with water privileges has the space you need to create a life you desire! Boasting an array of sleek finishes throughout, this 4 bedroom, 2.5 Bathroom home has so much to offer. When you walk inside you're instantly greeted with a spacious open layout featuring a spacious living room, updated kitchen with silestone counters and s/s appliances, family room off of the kitchen and a primary bedroom with updated bath on the first floor. Large maintenance free deck with hot tub is the perfect spot for relaxation, or summer cookouts! Attached 1.5 car garage with lots of driveway parking. This home truly has it all! Book your private showing today before it's gone!!

Embrace serenity on Kent Island with this inviting 3-bedroom, 1-bathroom rancher, offering potential for further enhancements. Newly refreshed with fresh paint, plush carpeting, and modern vinyl plank flooring, this home exudes comfort and style. Nestled on a picturesque corner lot adorned with enchanting mature landscaping, experience a tranquil outdoor haven right at your doorstep. The expansive yard offers ample space for relaxation and outdoor activities, complemented by the convenience of a one-car garage with extra storage for your needs. This charming home boasts the potential for additional features, including the possibility to add another bathroom and create an open layout with dining just off the kitchen, enabling customization to suit your preferences. Located on Kent Island, enjoy the peaceful ambiance of the neighborhood while having effortless access to Rt. 50, making commuting a breeze and providing easy reach to local amenities and attractions. Discover the perfect blend of comfort, convenience, and natural beauty in this delightful rancher â your ideal place to call home.

Waterfront on the Chester River!! This townhouse has been redone from top-to-bottom and it is beautiful!! The walls have been painted a soft off-white, the carpet and the wood-look flooring are easy-care and should be perfect with any color scheme. The kitchen features new cabinetry, stunning quartz counter tops, all new stainless steel appliances, and a huge stainless steel sink! You will enjoy the fabulous views of the river and marina from the kitchen and great room. Step out onto the balcony and you can see the sunrise or watch the sunset! On the next level up, the bedrooms shine with the same soft-white paint on the walls and the same carpeting as on the main level. The contractor opened up "hidden space" to enlarge the closets, as well! Ceiling fans have been added as have Venetian blinds. The bathroom found itself being completely redone ...now it has a quartz counter top, two roomy vessel sinks plus a sturdy shower/tub. The stacked washer/dryer are handily on the bedroom level. The Queens Landing amenities are legion...swimming pool, clubhouse, party room, tennis courts, walking path, indoor courts...more. As far as location goes, Queens Landing is minutes from the Bay Bridge and can be accessed without ever getting on 50/301! This is also a great spot for commuting to Annapolis, Baltimore, D.C. and major and commuter airports. A wonderful place to live! Owners pay the condo fee. For lease application go to the Long and Foster Kent Island website and find the address or MLS number. Click on the rental application button.

Why wait for new construction? Luxurious and Spacious 1st floor condo in highly sought-after Four Seasons at Kent Island-a vibrant, amenity filled 55+ community on the Chester River. This amazing unit has the feel of a private home with a walkout to a yard-like setting, a pond for viewing the resident ducks and heron and offers seasonal water views of Macum Creek. Enjoy luxury plank flooring throughout, warm linear fireplace, a stunning gourmet kitchen with quartz countertops, large center island, stainless steel appliances, recessed lighting, pantry and bonus dry bar. This 2 bedroom(dual master suites) unit also features a bonus office/den with french doors. The 2.5 Bathrooms are beautifully appointed with quartz vanity tops, and tasteful modern tile and fixtures. All located in an elevator building nestled at a quiet corner of the community with a walking trail to the water and kayak racks just steps away. The 24,000 sq. ft Community Clubhouse is sited on the Chester River and features a state-of-the-art fitness center, beach, transient use docks on a private pier, indoor and outdoor pools and spas, an expansive patio area, billiards room, meeting rooms, card and club rooms, walking and biking trails, tennis courts, pickleball courts, basketball and more! A full time lifestyle director ensures a full calendar of fun and active events and classes. Unit includes a private 1 car garage and secure storage room. Very conveniently located just minutes from area amenities, shops, restaurants and 7 minutes to the Bay Bridge.

Ranch style home with cozy front porch located in the waterfront community of Harbor View. Tree lined lot offers backyard privacy. Laminate wood floors throughout. Open floorplan to kitchen, dining room, and living room. Easy access to patio via sunny sliding door. Den could be third bedroom. Special feature of private sunroom off primary bedroom ! Beautiful indoor outdoor living in Harbor View just 2 miles from Bay Bridge. Check out the virtual tour !

WELCOME HOME TO OUR 55+ Four Seasons Community at Kent Island! This Exquisite and Spacious Condominium combines Luxury, Comfort, and Convenience with an Elevator, Attached Garage for easy access keeping you warm and dry from the elements, all in one Stunning Package. This Home could be The Model! Gorgeous 2 bedroom, 2.5 bath Residence Boasts an array of Impressive Community Features with Indoor Heated Pool, Negative Edge/Infinity Outdoor Pool, Indoor/Outdoor Hot Tubs, Clubhouse, Fitness Center, Game Room, Billiard Room, Meeting Room, Pier/Dock, Bike/Walk/Jog Path, Tot Lot and So Much More! Step inside and be Greeted by the Sleek Elegance that Permeates Every Corner, starting with the Gourmet Kitchen with Moen Fixtures! The Large Island, Adorned with a Gorgeous Quartz Countertop, 30" Cooktop and Canopy Hood, also Includes a Built-In Wall Oven/ Microwave Combo, GE Enabled Wi-Fi and Bluetooth capabilities, Top of the Line GE Stainless Steel Appliances and More, serves as the Heart of this Space! Perfect for Gatherings and Entertaining guests! The Pantry provides Ample Storage Space, allowing you to keep your kitchen organized and clutter-free. The Luxurious vibes continue throughout the condo, with each room designed to provide comfort and style. This Spacious Living area is Bathed in Natural Light, Inset Ceiling Lights and offers a Cozy Atmosphere for relaxation. The Primary Bedroom is complete with an Ensuite Bathroom, provides a Tranquil Haven after a long day. The Second Bedroom is Generously Sized and is perfect for Accommodating Guests or family member. As you enter your home you'll see Lovely French Doors that leads you to this Extra Space, Great for a Home Office! This IS a Prime Location! With All the Modern Conveniences and Amenities which Includes a Storage Area, Secure Entry and an Elevator! You Will Not Be disappointed! You would be Sure To Enjoy All What this Area Offers! A Vibrant Community with Fine Restaurants, Shops and Entertainment Options, all in just a Stone's Throw Away! Please do not hesitate! This Affordable Luxury Condominium Will Not Last! Sale is contingent on sellers finding home of choice. Right now they have their eye on a home that they are very interested in. Sellers are very motivated.

The Windermere combines all of the home design elements our purchasers love the most. On the main level is an open plan design with a huge kitchen, breakfast/sunroom and family room! Formal living and dining rooms, and two-story foyer complete the space. Upstairs you will find 4 spacious bedrooms to include an owner's suite with spacious walk-in closet or choose the optional super bath and get two walk-in closets! A lower level offers numerous options for expanding your living space to suit your lifestyle.

This gorgeous Santorini with Loft is Move In Ready and located in the amenity rich 55+ community of Four Seasons. Built in 2019, this home provides a spacious floor plan offering approximately 3200' of living space. The Awesome Gourmet Kitchen provides an oversized island with plenty of seating and Quartz Countertops, lots of cabinet space with under cabinet lighting, lovely walk-in pantry, top of the line appliances including a 5-burner gas cooktop, a counter depth refrigerator and double (His & Her?) ovens. Generously sized family room is crowned by an elegant gas fireplace that is not just a pretty focal point but an effective heat source with blower to keep you toasty warm. This Santorini Loft model features dual primary bedrooms on the main floor. Both with private baths and large walk-in closets. There is a 3rd full bath on the main level with a jetted walk-in tub! Upstairs the loft area provides a 3rd bedroom, a 4th full bath plus a 2nd Family room that could be the optional space you seek. Glass French doors give privacy to the downstairs office. There is also a separate formal dining room and the Laundry is on the main level too. Love the screened porch and Trex deck. Both are great options for relaxing or entertaining. An oversized garage will park 2 cars with space to spare. This community offers a Resort-style, amenity rich experience. Residents @ Four Seasons can take advantage of the community's spectacular 24,000' clubhouse. There are 2 pools, one inside and one outside, a state-of-the-art fitness center, multiple tennis and pickleball courts, a reading room, a party room, a Billiards room plus more. A full-time lifestyle director is on site. The Kent Island Four Seasons also features a well-maintained calendar of activities and has a full-time lifestyle director on site. Located steps from the water and has quick access to Rt. 50.

Located in the water privileged community of Queens Landing, this end unit is a rare find and provides a main level owners bedroom with full upgraded bath complete with walk-in shower. Must see to appreciate. The living area with gas fireplace is open to the updated kitchen with custom backsplash, stainless appliances and lots of storage space. Double sliders lead to patio with water view. Gorgeous LTV flooring in living area, main level laundry and pantry are enhanced with gorgeous custom barn doors. Upstairs are two additional bedrooms, a full bath and a large walk-in storage closet* Roof new in 2020* Water heater new 2020* Washer/Dryer new 2021*. In addition, the water privileged community of Queens landing provides many amenities: Waterfront Clubhouse* Large water side pool* Tennis courts* Pickleball* Kayak rack* Walking path and more. Convenient location only 2 minutes to highway 50 and Bay Bridge*

Be the first to see this beautiful 2 story house that has been tastefully renovated & upgraded. You will love open concept of living and dining area with a charming electric fireplace that lights up the room in a beautiful way and gets you warm and cozy; lots of natural lights, vaulted ceiling, beautifully refinished and stained wood floor, maintenance free deck with a lounge area and a firepit, private backyard with a spacious and comfortable lounge area. The kitchen is furnished with stainless steel appliances, 42â wood cabinets, and a new stainless-steel sink with accessories. Quality filtered water. The house was built in 2012. Recent (2022-2023) renovations and upgrades include: added 6ââ bump wall with a built in electric 60â Touchstone fireplace (dual mode â flame and heat) and a high-quality Denon sound system; fully remodeled bathrooms; installed water filtration system (Charger Iron Breaker III) that supplies the whole house; refinished and stained oak wood floor, NEW - wood stairs treads, asphalt driveway, pavestone patio, LED light fixtures, ceiling fans with LED lights and remote/wall control, door hardware, light switches, vent grilles, stainless sink in the kitchen, Samsung laundry machine, window covering (curtains and blinds), paint - garage & all doors, wall paper and painted accent walls in bedrooms; built half wall (1st floor), added shelves in bedroom closets; LVP floor in the utility room; sum pump; outdoor entrance lights; landscaping (planted evergreen trees and sod). The air duct system was repaired and cleaned in December 2022. The house features 4 bedrooms and 2 ½ bathrooms. The primary bedroom is on the second level and features an ensuite bath. The second and third bedrooms are on the second level and share a hall full bath. There is a main living area, dining, and kitchen on the second level. On the first level, there is fourth bedroom/living area with an ensuite half bath, and the utility room with oversized washer and dryer (Samsung). The attached 2 car garage. Shed in the backyard. House is very clean and well maintained. Pet and smoking free. Great central location. No HOA fees. Move in ready. The house is sold strictly furnished at no additional cost for the furniture.

Elegance abounds in this fabulous 3 bedroom, 3 full bath home. Coastal inspired vibes resonate throughout the home with many upgrades that include but are not limited to; quartz countertops in kitchen and baths, 9' sliding glass door at the dining area, screened porch/lanai area, gourmet kitchen layout, upgraded cabinetry, pendant and under counter lighting, upgraded carpet and padding throughout the loft area. Four Seasons Community offers resort style living right here in Maryland. Clubhouse, party rooms, fitness center, pool, pickle ball, tennis, bocce courts, marina and much more. clubhouse is open for tour 9-5 pm daily. Please see movie camera icon for video and please see the paper icon for documents inclusive of floor plan, cable and internet upgrades and upgraded features of this home.

The Simone model is a show stopper! This home includes a screened patio, fireplace, upgraded primary bath shower and more. For a full list of features please see a sales representative. 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. *pictures are representative of a similar home.

The Kerr model is a show stopper! This home includes a covered patio, fireplace, upgraded primary bath shower and more. For a full list of features please see a sales representative. 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. *pictures are representative of a similar home.

The Taylor model is a show stopper! This home includes a covered patio, fireplace, upgraded primary bath shower and more. For a full list of features please see a sales representative. 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. *pictures are representative of a similar home.

Coastal Colonial with pond views. Many recent updates and upgrades. Open kitchen design with large island and gourmet stainless appliances. Adjacent to the kitchen is the breakfast nook and family room with propane fireplace. Sunlit dining room with adjacent butler pantry and open foyer. The primary bedroom has a walk-in closet and designer primary bath with soaking tub, double bowl sink, walk-in shower and water closet. Three other bedrooms, a full bath and laundry will also be found on the upper level. The rear brick patio and fenced yard can be accessed from the kitchen. The garage has pull down storage, a foldable work bench and charging port for an electric vehicle. The community has many amenities including a pool and fishing pier. This home is truly a must to see!

2 bedroom end unit townhouse located in beautiful bridgepointe neighborhood. There is a den that could be used as a 3rd room. This townhouse comes fully furnished.

Brand new 1 bedroom 1 bath apartments in Chester. Close to everything Kent Island. Secure building, keyless entry, 1 parking space per unit with plenty of overflow for one additional per unit. Large kitchens, full size washer & dryers in each unit. Water & sewer included. This is a NO SMOKING, NO PET building. 3 Apartments on 2nd floor, office space on first floor.

Brand new 1 bedroom 1 bath apartments in Chester. Close to everything Kent Island. Secure building, keyless entry, 1 parking space per unit with plenty of overflow for one additional per unit. Large kitchens, full size washer & dryers in each unit. Water & sewer included. This is a NO SMOKING, NO PET building. 3 units over top office space.

This beautiful townhouse in Bayside is ready for its new owners! Featuring 3 spacious bedrooms, 2 full bathrooms and 2 half baths (on first and second level), attached garage and driveway with paver patio addition for convenience, gas fireplace and oversized deck; this home won't last long! The kitchen has been beautifully updated including quartz countertops, hardwood floors gleam throughout living areas, and brand new carpet makes this home turn key and ready to go! Enjoy pond views from your back deck that has just been rebuilt to the largest size allowed. All appliances are new and bathrooms have been updated as well as a brand new wooden insulated garage door. Bayside Marina features some of the best amenities on the island including a community pool, gym, clubhouse w/ kitchen that can be rented for parties, tennis courts, volleyball courts and access to the Cross Island Trail! It's also located right next to two great restaurants and a marina, all in walking distance. Island life doesn't get much better than this!

Kent Island Waterfront on Cox Creek!! Public Sewer available, road frontage is 45ft. This is a flag lot with opening on the waterfront of 108 ft. This property does not have a pier, so please do not go on pier. This is the perfect lot to build your dream home. The natural environment has wildlife and waterfowl and as well as good fishing and crabbing. If you want a piece of the shore-life this is the property you have been looking for.

Welcome to Eastern Shore living at Bayside! This meticulously cared for three level water-view townhome overlooks Northeast Bay and the Chester River. Amazing open-concept floorplan allows for plenty of room to entertain indoors or outdoors. Main level boasts wood floors, rich paint, custom moldings, plantation shutters, gas fireplace, recessed lighting, and more. Bright and airy kitchen to include white cabinets, sleek appliances, granite counter-tops, paint, and lighting/fixtures. Enormous Primary Bedroom with private deck/balcony, large walk-in closet, and spa-like bathroom. Second bedroom suite with private bathroom and large closet. Third bedroom/loft has views of the Bay, vaulted ceiling, walk-in closet and private bathroom. Two tiered deck to take advantage of the magnificent views. Both HVAC systems replaced in 2017. Amazing community amenities that include, Clubhouse, tennis courts and outdoor pool! Walking distance to two local restaurants marina. Your boat can be just steps away! Close to area bike and walking trails. This is the place to enjoy all that Kent Island Living has to offer! Five miles away from waterfront restaurants such as: Libbeyâs, The Narrows, Bridges and the Jetty, among others. Do not miss the opportunity to purchase a vacation style home located only 17-miles from Annapolis, 46-miles from Washington DC and 60-miles from Baltimore. Condo fees cover full time on-site management, reserve funds, master insurance policy, exterior building maintenance (roof, siding, crawl spaces), amenities, all landscaping, trash, snow removal, road/parking lot maintenance. ***Seller is offering $5,000 credit toward buyer closing costs, interest rate buy-down, or pre-paid condo fees with an acceptable offer***

Brand new 1 bedroom 1 bath apartments in Chester. Close to everything Kent Island. Secure building, keyless entry, 1 parking space per unit with plenty of overflow for one additional per unit. Large kitchens, full size washer & dryers in each unit. Water & sewer included. This is a NO SMOKING building. Pets under 35lbs welcome with a pet deposit. Total of 8 units, 6 with this floor plan and price, 2 larger units at $1800 on upper floor.

Brand new 1 bedroom 1 bath apartments in Chester. Close to everything Kent Island. Secure building, keyless entry, 1 parking space per unit with plenty of overflow for one additional per unit. Large kitchens, full size washer & dryers in each unit. Water & sewer included. This is a NO SMOKING building. Pets under 35lbs welcome with a pet deposit. Total of 8 units, 6 with this floor plan and price, 2 larger units at $1800 on upper floor.