Chester MD Real Estate & Homes for Sale

**Island Living Awaits You - Immediate Move-In Available!**Seize the Summer - Your Dream Condo Awaits!** Escape to the idyllic island life this summer and make your move now â no need to wait until 2024! Discover this stunning and meticulously maintained condo nestled in the prestigious "Four Seasons at Kent Island," a vibrant 55+ community located in picturesque Chester, Maryland. **Luxurious Space** This exceptional corner unit offers three generously proportioned bedrooms and 2.5 bathrooms, providing the space you've always dreamed of. **Gourmet Kitchen** The heart of this home is its top-of-the-line kitchen, boasting upgraded cabinetry, exquisite granite countertops, and high-end GE Profile stainless steel appliances. Delight in the convenience of a propane-powered cooktop and revel in the elegance of Moen faucets and fixtures throughout. **Unwind on Your Private Balcony** Step out onto your expansive 16 x 12 private balcony accessible from both the living room and the owner's suite. Here, you'll be treated to breathtaking vistas of the tranquil nature preserve, Macum Creek, and seasonal glimpses of the majestic Chester River. **Owner's Suite Oasis** The luxurious owner's suite features a spacious sitting area, not one but two walk-in closets, and an en-suite bathroom. Meanwhile, the opposite "wing" offers two more well-appointed bedrooms, complete with jack-and-jill bathrooms and their own walk-in closets. **Modern Comforts** Additional highlights of this exquisite condo include a sizable laundry room, a convenient powder room, an electric fireplace, and Low-E windows fitted with custom Hunter-Douglas blinds, ensuring ample natural light filters through. Luxury Vinyl planks make for easy cleaning and allergen-friendly living. **Resort-Style Amenities** Beyond your doorstep, the award-winning waterfront clubhouse and its amenities beckon. Enjoy a 450' pier extending into the Chester River, a state-of-the-art fitness center, indoor and outdoor swimming pools, a canoe and kayak launch, scenic hiking and biking trails, and more! **Ideal Location** The central location is perfect for exploring nearby towns and cities, including Annapolis, Baltimore, Washington D.C., Easton, Delaware, and Ocean City. Savor delectable meals at multiple award-winning restaurants, indulge in prime shopping, and relish easy access to the renowned Chesapeake Bay. Your Island Lifestyle Awaits! Don't miss your chance to own a piece of this waterfront story. Arrange your personal viewing of 4000 Heron's Nest Way #34. Let's turn this property into the next chapter of your life.

Welcome to this stunning property that seamlessly combines modern upgrades and convenience in a desirable location. This thoughtfully renovated 3-bedroom, 2-full bath home provides a comfortable and stylish living experience. With numerous updates completed in 2018, including the HVAC system, kitchen, roof, and the addition of a new septic system in 2019, this home is move-in ready and sure to impress. Upon entering, you'll be greeted by a well-designed floor plan that caters to easy living. The spacious and inviting kitchen is truly a showstopper, boasting modern appliances, beautiful countertops, and ample cabinetry. Whether you're a culinary enthusiast or simply enjoy gathering with loved ones, this gorgeous kitchen is sure to be the heart of the home. Parking will never be an issue here, as the property offers plenty of space for multiple vehicles. Additionally, the expansive yard provides a delightful oasis for outdoor activities, gardening, or simply unwinding in nature. Situated just 2 miles off Route 50, this home offers a convenient commute to the vibrant cities of Annapolis, Easton, Baltimore, and Washington, D.C. Whether you're heading to work or looking for entertainment options, you'll appreciate the easy access to these bustling destinations. The living room is both cozy and modern, featuring an electric fireplace that adds warmth and charm to the space. The vinyl plank floors not only enhance the room's aesthetics but also provide durability and easy maintenance, making your everyday living a breeze.

This property is so relaxing, you can sit on the deck and think of nothing, listening to the sound of the fountain in the lake and look out over the water, it is what everyone needs. This beauty has been completely updated and features Stainless Appliances with Granite Counters, Life Proof Flooring, Fresh Paint , HVAC in 2016 and a climate controlled One Car Garage with a floor you could eat off of. You literally have views from every room, from the upper deck AND the Walk out lower level patio. All this in sought after Bayside Community, near the Pool, Hot Tub, Fitness Room and Tennis Courts. The location can't be beat !!!

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.

This is the waterfront dream home youâve been waiting for! Are you looking for expansive bay views from your forever home or second home on the Eastern Shore? This 5 BR, 2.5 BA property with 110 feet of rip rapped waterfront delivers with 2.9 manicured acres (one of the largest lots in the community!) in the serene upscale community of Southwind. You will enjoy this secluded setting with wide sweeping water views surrounded by Crab Alley and Eastern Bay. Just steps down the back yard is the six-foot wide pier with both boat and jet ski lifts and a gorgeous custom salt-water pool surrounded by a pristine paver patio and walkways. Enjoy boating, jet skiing, fishing, crabbing or just relax on the pier and enjoy your morning coffee as you soak in the sunrise! The backyard oasis includes screened porch, two-level Timber Tech decks and waterside fire pits set up for bay view entertaining and fun, fun, fun! This gem has been lovingly cared for every step of the way and is in pristine condition with a major remodel in 2015. This is a rare opportunity and the first time this property has been on the market. Marvel as you enter into gleaming blonde hardwoods throughout the first floor and upstairs hallway of this 3,718 finished square foot home. Seven rooms on the water side have wide open views of the bay! The foyer features an 18-foot ceiling and 9-foot ceilings throughout the first floor including living, dining, breakfast room, kitchen, bathroom, and office/bedroom. There is a wood burning masonry fireplace flanked by custom built-in bookshelves to enjoy in the chilly winter months. The 1.6-acre communal easement immediately adjacent to the left of the home insures you will have no neighbor to the left adding to the secluded setting. The community of Southwind also offers a boat launch, boat storage, waterside tennis or pickle ball courts, basketball court, waterfront club house for events and year round activity calendar, walking trail with a pair of nesting bald eagles and much more! Close to prime shopping and dining, yet privacy abounds in this upscale neighborhood. Want to go to restaurants by boat? This location is a short boat ride to the Narrows and St. Michaels! Kent Islandâs expansive Cross Island Trail with miles of biking, running, and walking trails provides endless opportunities for locals to enjoy all the island has to offer! This is a MUST SEE!

This 3-bedroom, 2-bathroom water-oriented rancher is a fantastic property with plenty of desirable features. Situated in Marling Farms with direct access to Crab Alley Bay and Eastern Bay, it offers a great waterfront community location with boat ramps, 4 beaches, fishing pier, baseball fields, basketball court, common grounds, picnic areas, boat ramps, kayak racks, a pier/dock, and a playground, making it an ideal place for an Eastern Shore lifestyle. With 2,120 square feet of living space, there's plenty of room to enjoy. The spacious living room with gas fireplace and the sunroom, which is filled with natural light, are perfect places to relax and unwind. The primary bedroom's direct access to the outdoor deck with a retractable awning is a wonderful feature for enjoying the outdoors. Freshly updated flooring throughout the house adds to the appeal. The fenced-in spacious backyard with a paver patio is ideal for outdoor activities and gatherings. With wheelchair-accessible features, including ramps at every entry/exit and a roll-in shower in the primary bath, make the home inclusive and accommodating. This property offers a comfortable and enjoyable living experience, with both indoor and outdoor spaces designed for relaxation and recreation. It's a great opportunity for those seeking a water access home with a sense of community and accessibility features.

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.

Bridgepointe Townhome - this desirable Kent Island Community is located just off Rt. 50. Fabulous Two Story Townhome is ready for YOU! Inviting Front Porch and Foyer opens to Beautiful Kitchen with Breakfast Nook, Large Dining and Living Room includes Brilliant Hardwood Flooring. Bright Open Floor Plan. Sliding Door - opens to Large Deck w/built in storage shed and Electronic Awning. Relax and enjoy the peaceful views. Second Floor includes Master Suite with Private Bathroom, Second Bedroom and Den (could be 3rd Bedroom) and Full Bath in Hall. NEW in 2023 Hot Water Heater, Dehumidifier in Crawl Space, Washer and Dryer. The Garage was converted into step down Family Room with French Doors and lots of overhead storage. Bridgepointe Community has a Storage Area for Boats/RV's (see HOA Docs). Stroll beside the Beautiful Community Pond with Fountain and Cross Bridge. Make your move today - Close to Waterfront Dining, Kent Narrows, Cross Island Trail, Shopping, Medical and more!

Welcome to 2015 Stevens Drive!! Tucked away right off Route 50, this beautiful 3-bedroom, 3-bathroom split foyer home in Chester, Maryland, is a wonderful opportunity to enjoy comfortable living in a peaceful and welcoming community. Arriving to the property, you are greeted by a well-maintained front yard with lush greenery and raised flower beds, the split foyer design gives the home a distinctive look, with a welcoming front entrance. As you enter the home, in true split foyer style, you are greeted by stairs leading to the main level, as well as the lower level. Upstairs on the main level, you will find yourself greeted by a beautiful spacious, living room featuring large windows and a sliding glass door that leads to the outside deck, that allows plenty of natural light to stream in. The open floor plan seamlessly connects the living area to the dining space and kitchen, making it an ideal space for entertaining family and friends. The kitchen is equipped with modern stainless steel appliances, ample cabinet space, and a convenient breakfast bar perfect for morning coffee. The dining room features another siding glass door that provides access to the deck that has perfect views over the back yard and is the perfect spot to BBQ and relax. The large owners suite boast tons of living space and large ensuite with walk in shower, making it the perfect peaceful retreat. A second bedroom and full bathroom finishes off the upstairs living area. Heading downstairs to the lower level, you will discover a versatile and cozy family room, ideal for movie nights or just relaxing. This level also features the third bedroom, perfect for a home office, guest room, or a growing family. A third full bathroom on this level adds to the convenience. A laundry room and storage room are also located on the lower level, as well as the mechanical closet. Stepping outside through the sliding glass door into the backyard, onto the raised patio, unwind in the hot tub after a long day or sit inside the screened-in area an excellent space for outdoor dining, barbecues, or simply enjoying the serene surroundings. The backyard offers ample space for gardening, play, and relaxation. Don't miss this perfect opportunity.

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. Closet on balcony is mechanical only, not for tenant use. Total of 8 units, 6 with slightly smaller, 725 Sq Ft at $1750.00 and 2 larger units 802 Sq Ft at $1800 on upper floor only #202 & 203

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.

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.

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.

Lovely 2nd floor condo with private deck on lake. 2 bedroom / 2 new full bath, unit with ALL NEW appliances, new carpet, freshly painted.

This one-level Rambler, located in a waterfront community, sits on .739 acres and has a water view of Crab Alley Creek. This home has no HOA and offers 3/ bedrooms, 2/ full baths, a living room, a family room with a wood-burning fireplace, an eat-in kitchen, and an oversized attached garage. The primary bedroom offers luxury vinyl plank flooring and a closet organizer system. The primary bedroom has tile flooring with a tile surround shower and a deep jetted tub. The hall full bath has new vinyl flooring and houses the washer and dryer. The other 2/ bedrooms offer large space and nice-sized closets with carpet flooring. The living room has plank flooring with recessed lights and is a nice open space. The kitchen offers all-new stainless steel appliances, as well as new granite countertops with a breakfast bar. The family room offers a large open space to entertain with a wood-burning fireplace, recessed lights, a ceiling fan, and a side entrance. Saving the best for last, the garage! This garage edition was built in 2019 and is 32 x 40, with a 14' ceiling. The garage features (2) 10 x 10 separate doors,100 amp sub panel, is pre-wired for A/C and a car lift, 20amp receptacles throughout, and has (3) welding outlets. This is perfect for a mechanic, car enthusiast, or for storing your boat!! A private deep well, septic system was installed in 2018 with the new MD environment-compliant Norweco nitrogen-reducing system. A new roof and siding was completed in 2019. The central A/C is a 2.5-ton Goodman dual-fuel heat pump with a propane furnace and insulated ducting installed in 2011. Kent Island Heritage Society preserved farmland surrounds the neighborhood. This property is 1 mile from 2 public boat landings. By boat, you will be minutes to Kent Narrows, 30 minutes to St. Michaels, and only 45 minutes to Annapolis. This home will not disappoint, add it to the top of your list and come see for yourself!

2 Bedroom 2 1/2 bath townhouse in Queens Landing. Rear patio and Balcony overlook the lake and fountain. Hardwood floors on first level, wall to wall carpet on upper levels. Laundry closet on second floor. Community features pool, walking paths, tennis courts, gym, and clubhouse on the Chester River. Storage closets off balcony and patio. Enjoy numerous community amenities including a marina, swimming pool on the Chester River, tennis/pickle ball courts, clubhouse with social room, waterfront walking path, exercise room, and racquetball. New roof installed in 9/2020. New hot water heater, newer windows and doors. All assessments have been paid and no poly-pipes are present.

The Jenkins II model is a show stopper! This home showcases a Loft look. This home also features a screened patio and fireplace as well as upgraded shower. 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 Bernstein II model is a show stopper! This home includes a fireplace as well as an upgraded shower. This home features the Classic Look. 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 Bernstein II model is a show stopper! This home features a fireplace as well as a screened patio. 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 Kelly model is first floor living at its finest. This home features a screened patio, fireplace, upgraded shower and detailed trim in the foyer and primary bedroom. . For a full list of included features please consult 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.

Live in the resort-style community of Queenâs Landing! This WATER privileged end-unit home offers three bedrooms and two full baths on the main level, a loft, and multiple outdoor living opportunities to view the marina and watch spectacular sunsets. Enjoy numerous community amenities including a marina, swimming pool on the Chester River, tennis/pickle ball courts, clubhouse with social room, waterfront walking path, exercise room, and racquetball. The welcoming interior is introduced by beautiful glass panel doors with flanking windows illuminating the neutral color palette and hardwood floors. The spacious open concept living, dining, and kitchen provides unparalleled convenience combined with casual comfort and elegance from a soaring vaulted ceiling and skylights. Prepare your favorite recipes in the kitchen appointed with warm toned shaker cabinetry, recessed lighting, and solid surface counters with iridescent flecks evoking feelings of sand and sea. Retreat to the primary bedroom highlighting a walk-in closet, access to the full bath, and a sliding glass door to the patio. Two additional generously sized bedrooms and a full bath conclude the interior. The upper level loft is a cozy haven featuring a wood-burning fireplace, built-in bookcase, and balcony overlooking the marina. Enjoy being minutes from a multitude of shopping, dining, and entertainment options as well as the Cross Island Trail.

KENT ISLAND - Hurry to Harbor View. This move in ready home features over 2,200 sq ft of well maintained space for you and your family. From the front covered porch you are welcomed into the spacious central foyer, which flows into the spacious kitchen and dining area filled with lots of natural light, upgrades galore, new appliances, and an exit to the fully fenced backyard oasis. Relax by the fire in the living room or hang out in the newly added family room which leads to the backyard with paver patio, large deck, shaded lawn, mature landscaping, vegetable garden, storage shed and garage/workshop. The upstairs offers 3 large bedrooms, 2 full baths and private office. Owners have made many upgrades, Roof is 5 years old, fireplace converted to gas, new water heater in 2019, kitchen floors tiled and exterior vinyl fence installed in 2020, backyard drainage system, LVP flooring installed downstairs and old screened porch converted to 270 sf of interior living space in 2021, new Samsung appliance package added just 8 months ago. This home is located central to KI shopping, restaurants, schools, activities.