The median home value in Chester, MD is $472,500.
This is
higher than
the county median home value of $395,500.
The national median home value is $308,980.
The average price of homes sold in Chester, MD is $472,500.
Approximately 71% of Chester homes are owned,
compared to 19% rented, while
10% are vacant.
Chester real estate listings include condos, townhomes, and single family homes for sale.
Commercial properties are also available.
If you like to see a property, contact Chester real estate agent to arrange a tour
today! Learn more about Chester Real Estate.
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.
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!
Welcome to your dream home in Chester, Maryland, located on Kent Island! This charming rancher offers the perfect blend of comfort and convenience with its one-level living design. The highlight of this home is the spacious bonus room off the kitchen, complete with a cozy pellet stove and electric heating elements for those cooler evenings. The recently remodeled kitchen boasts stainless steel appliances, giving it a modern and sleek touch. Natural light floods through the windows, creating a warm and inviting atmosphere throughout the house. The generously-sized driveway provides ample space for parking your camper or boat, making it a breeze to enjoy outdoor adventures. Additionally, the property features a beautiful, landscaped yard and a two-car detached garage, adding both functionality and curb appeal to this lovely home. Best of all, there are no homeowner association fees to worry about. Welcome to island living at its finest, and don't forget to indulge in the island's famous ice cream at Island Ice!
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!
***Sellers have found their home of choice! Bring us an Offer!*** Welcome to Queens Landing in charming Chester, MD! This wonderful 3-level townhome boasts elegant Spanish-style architecture and is one of the most spacious models within the community. **Key Features** **Brava Model with expansive 12x26 Loft: Enjoy the luxury of an expansive loft space, perfect for a home office, entertainment area, or additional living space. This unique feature adds versatility and ample room to tailor to your lifestyle. **Remodeled Kitchen: The heart of this home features a thoughtfully remodeled kitchen with a pantry, Corian countertops, and wainscot detailing. Functionality meets aesthetics for an ideal culinary experience. **Freshly Painted (2023): Step into a home that feels 'new' with a fresh coat of paint that enhances the ambiance and offers a blank canvas for your personal touch. **Plantation Shutters, High and Vaulted Ceilings: Adorning the windows, plantation shutters add a touch of sophistication while allowing you to control natural light. The vaulted ceiling in the Primary Bedroom creates an airy and open atmosphere. **Modern Upgrades: Benefit from recent upgrades including HVAC replacement in 2019, washer/dryer replacement in 2022, and a roof replacement in 2019. These essential updates ensure your comfort and peace of mind. **Flooring: Aesthetic meets functionality with stone, ceramic tile, laminate, and carpet flooring throughout the home. **Ample Storage: Discover convenience in the form of four built-in outdoor storage closets, as well as well-designed storage spaces within the condo. Organize with ease. **Views: Partial river views grace the main level's covered and tiled patio, as well as the inviting deck connected to the Primary Bedroom. Serenity and natural beauty are just outside your doorstep. **Large Loft area doubles as a 3rd Bedroom! **Convenience and Proximity to the Surrounding Areas: Approx. 3 miles and the Bay Bridge opens up seamless opportunities for travel, shopping and exploration. **Community Amenities: Experience waterfront-style living with access to a range of amenities including a clubhouse, pool, gym, tennis courts, marina, boat slips, and a picturesque jogging/walking path along the serene Chester River. Every day is an opportunity to indulge in a variety of recreational activities without leaving the comfort of your community. This condo in Queens Landing offers not just a home, but a lifestyle enriched by modern comforts, scenic beauty, and a thriving community. Don't miss your chance to be a part of this remarkable living experience.
Price Adjustment of $10,000! Welcome to 1808 Chester Drive located in the Harbor View community on beautiful Kent Island. Step inside and you will fall in love with this One Level Living home located boasting approximately 1700 sq ft of living space and offering 3 Bedrooms + Den and 1.5 Bathrooms. The split floor plan offers privacy and generously sized bedrooms. The garage was converted to host the primary bedroom, plus a conditioned workshop/studio. The kitchen offers newer appliances, a breakfast bar, and slider to the HUGE backyard! In the - there are currently two sheds (1 with electric perfect for a man cave, she shed, office or gym), an above ground pool, firepit area, patio, and plenty of room for swing sets, garden and more! HVAC installed 2022 Harbor View HOA is $25/year Public Sewer & Well Water - with owned filter system. Don't wait, call to schedule your showing today!
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.
