Chester MD Real Estate & Homes for Sale

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.

You little slice of Cox Creek heaven! This 3/4+ acre lot will support a narrow design up to 28' in width. The Seller reports a 6' water depth at 170' from the shoreline. The sewer tap fee has been PAID and the lot is ready for you to file grading and building permits. Sellers are working to remove the phragmites.

This beautiful 3/4+ acre waterfront lot is READY to ROLL for you to secure a grading permit and building permit. The sewer tap fee is PAID. The Sellers are working to remove the phragmites to get back that beautiful Cox Creek view back. Out on the creek is 6'...yes, SIX FEET of water 170' from shore according to the Sellers. This is a rare and beautiful home site in a terrific neighborhood. Don't miss it!

A deep-water Cox Creek fixer with great "bones" isn't a home that comes up very often, but here it is! Do a little, or do a lot, as this is a true 1968 time AS-IS time capsule that feels solid under its beautiful hardwood floors. With 5+' water depth and a beautiful view of the creek, your investment will be solid either way. The home is connected to the original septic system, but a sewer tap with a PAID-FOR tap fee is available on-site. Don't miss this one as it is sure not to last long! Note that there is a plotted view lane on the property designed to protect the view of 310 Benton's Pleasure Rd that is included in the documents available to the Buyer. Two adjacent building lots to the right are also for sale.

FOR RENT! Single, private 10x11 office space located within Kent Island Chiropractic business. Perfect space for those that "work from home" but still want a private office setting close to home. Flat monthly fee, NO CAM fees. If tenant needs 2 office spaces, an additional 10x11 office is available for $775/mo total.

Welcome to 201 Gibson Circle in Chester, MD! This Stunning End unit townhome is COMING SOON in the Desired Community of Gibsons Grant on the Chester River and Macum Creek! Boasting a Contemporary Coastal design and immaculate condition, this property is a Perfect fit for anyone seeking a Stylish, Spacious Home to move right in and not have to do a thing! Abundant windows with Tons of Natural light offer a Bright and inviting atmosphere throughout. The surrounding plush Green Space creates a Peaceful setting, especially when enjoyed from the maintenance free, private side deck. Bring your rockers to enjoy the sprawling covered front porch... AND it is ALL about the decor on the porches here in Gibsons Grant! Newer brick paver walkway and flagstone patio add a touch of elegance to the outdoor space. Situated on the corner lot, this property features copious amounts of mature landscaping, ensuring a Serene and Picturesque environment with the birds and the butterflies all around. Storage will never be a problem thanks to the poured concrete floor crawl space, the large pantry area and all of the storage racks in the OVERSIZED 2 Car Garage! Inside, you will find three Spacious Bedrooms, along with an Office space that can easily serve as a FOURTH Bedroom! The super-sized Primary Bedroom is a true retreat, offering a private sanctuary with its own ensuite bathroom and 2 WALK-IN Closets! In total, there are 2.5 Bathrooms in this home, all beautifully designed and ready to cater to your needs. OPEN CONCEPT with Gourmet Kitchen and HUGE Island to enjoy daily meals! The Kitchen has New Glass Tile Backsplash, 42" Cabinets with New hardware, lots of counter space, Stainless Appliances, new Sink Faucet, beautiful Pendant Lighting & more! Eating area with table space and the Living Room off the kitchen creates ease when Entertaining! True Full-Size Laundry ROOM with Stainless Steel sink, countertops for folding or crafting and a walk-in Pantry! With a sizable 2,650 square feet of living space, this Home provides more room than many single-family homes in the Community. The fully upgraded interior is a testament to the Meticulous attention to detail that has been put into this property. Community Amenities are plentiful on the Fifty-Five Acre Waterfront development to include, Ponds, Open Space, Life-Guarded Pool, Party Room, Gym (with NEW equipment), Meeting Room, Kayak Storage, Waterfront Pavilion, Grilling Area, Fire-Pit in the Happy Hour Space, Walking Trails, Dog Stations and a Private Fishing & Crabbing Pier! Don't miss out on the opportunity to own this Remarkable Home...come witness the allure of 201 Gibson Circle for yourself!!

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 !!!

Gorgeous 5 Bedroom 3 Full Bath single family home with a water view! Completely renovated and situated on a large .87 acre lot. Open concept kitchen with White Shaker cabinets, granite counters, stainless steel appliances, peninsula with additional seating and LVP floors. Upper level with 3 generous bedrooms and primary bedroom with separate bath and luxury shower. Lower level with 2 bedrooms and large family room with plenty of natural light. Roof- 3 years new. Oversized driveway for multiple cars/RV parking and separate detached garage with electric. A Must See!

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 home is under construction and is estimating to be move in ready by October 2023! This particular home comes included with a fireplace and a dry bar. 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. *Photos are of similar home as this home is to be built.

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 2 bedroom 2.5 bath renovated townhome located in the community of Queens Landing. Large living room with corner fireplace, newer flooring throughout. Second level features 2 spacious bedrooms, each with their own full bath and laundry conveniently located in hall. Private patio with beautiful water views. New HVAC, roof, and appliances. Amazing community amenities including outdoor pool, tennis & racquetball courts, fitness center and more! Close to restaurants, shopping and the Kent Island walking trail.

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

The stunning 109 John Dabb Court, nestled within the highly sought-after waterfront community of Gibson's Grant and just a block away from the Chester River! Step onto the inviting porch and immediately embrace a sense of tranquility. This thoughtfully designed, newly built home (Koch Kingston 2019) seamlessly guides you through the living areas on the first floor, including a family room accompanied by a cozy fireplace, dining space, to an upgraded kitchen featuring premium appliances. Adding to the ease of living, a convenient first-floor bedroom and a full bathroom awaits. On the second level, discover 3 bedrooms and 2 bathrooms tailored for modern comfort. Through French doors, the primary bedroom leads to a private balcony, offering a serene retreat. Don't forget about the attached garage and expanded driveway pad, perfect for everyday convenience. Gibson's Grant is a resort style community with amenities including outdoor pool, clubhouse with fitness center, pavilions, fishing pier and all just minutes from shopping, dining and the Chesapeake Bay Bridge. Schedule a showing today!