Chester MD Real Estate & Homes for Sale

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Beds:
5
Baths:
4.00
Sq.Ft.:
2,752
Status:
Active
MLS#:
MDQA2017858
Type:
Single Family-Detached
Subdivision:
HARBOR VIEW
Lot size:
0.55 Acres
Year built:
1986
Courtesy: Samson Properties 703-378-8810
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ADDITIONAL INFORMATION

Discover the extraordinary waterfront oasis of 2702 Sherman Dr. in Chester. This remarkable residence, featuring 5 bedrooms, 2 full bathrooms, and 2 half bathrooms, has undergone a stunning renovation, creating a haven of luxury and serenity on a peaceful street. Every detail of this home has been impeccably updated, from the oversized windows to the modernized bathrooms. However, the true centerpiece is the fully equipped gourmet kitchen, a masterpiece of design. A magnificent 10-foot Quartz center island takes center stage, surrounded by pristine cabinets, state-of-the-art appliances, and exquisite marble countertops. To top it off, the kitchen also boasts its own wet bar with a built-in beverage cooler. The open-concept layout seamlessly connects the kitchen to the living space, with a mesmerizing wall of oversized windows that offer breathtaking views of the expansive waterfront and private pier. Convenience is a priority in this home, with a three-car pull-through garage and a pier equipped with boat lift as well as dual Jetski lift for easy access to the water. Outdoor enjoyment is a given, with two waterfront decks, a screened-in patio, and a private en-suite deck for moments of relaxation. Privacy and the feeling of island-style living are abundant here. Located in the heart of Kent Island, this property provides effortless access to luxury dining options, waterfront restaurants, lively dock bars, and island-style entertainment. All while, being just 2 miles away from the Chesapeake Bay Bridge means seamless travel by land or sea. Welcome to your dream home, here on Kent Island where tranquility and luxury converge with Maryland's Eastern Shore and the Chesapeake Bay.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,602
Status:
Active
MLS#:
MDQA2017940
Type:
Apartment
Subdivision:
FOUR SEASONS AT KENT ISLAND
Year built:
2024
Courtesy: Long & Foster Real Estate, Inc. 410-770-3600
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ADDITIONAL INFORMATION

Welcome to this stunning 4th floor penthouse Severn condominium with serene bay views! This end unit looks out over the walking trails to the water and trees. The fabulous community center /pool / pier is a short 1 mile walk from your backyard.! This unit also has the largest garage space in the the building, plenty of room for one car and storage, a refrigerator etc. There is also an additional inside storage room. This 2600 Sq Ft home is flooded with natural light and has numerous quality upgrades including custom shiplap in most of the rooms, custom ceiling fans and dining room light fixture, custom built his and hers walk in closets. The primary bath has upgraded tile, shelving for more storage, mulitple shower heads and back and front lit vanity mirrors. The gourmet kitchen is designed to impress, featuring elegant quartz countertops,premium appliances and a Wolfe induction cooktop. The island has been upgraded with shiplap as well. Thoughtful upgrades continue throughout the entire home with custom blinds with remote control, a gas fireplace,9 FT ceilings with tray ceilings in the living room and primary suite. A wet bar has also been added to the dining area.The large primary bedroom comes complete with a sitting area/office with exceptional waterviews. It also offers custom designed his -and -her closets that provide both style and storage. This unique residence offers a peaceful setting where you can relax and enjoy the ever-changing waterfront vistas. Whether you are enjoying your morning coffee or entertaining guests, this home offers the perfect blend of sophistication, comfort, and low maintenance waterfront living. Residents enjoy an exceptional resort-style lifestyle with amenities that include indoor and outdoor swimming pools, a fitness center, clubhouse, library, billiards room, hot tub, Bocce Ball, pickleball and tennis courts, picnic areas, tot lots, and a community pier overlooking the Chester River. Ideally located just minutes from shopping, dining, golf, marinas, and the Chesapeake Bay Bridge, this exceptional waterfront residence offers the perfect blend of luxury, convenience, and carefree Eastern Shore living.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,688
Status:
Active
MLS#:
MDQA2017854
Type:
Single Family-Detached
Subdivision:
-0-
Lot size:
1.88 Acres
Year built:
1973
Courtesy: Douglas Realty LLC 866-987-3937
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ADDITIONAL INFORMATION

REDUCED!!! This 3 bedroom 2 full bath brick rancher is located 1.88 for plenty of privacy and plenty of room to expand. Not many large lots left in this community, check with county for very possible sub dividing for 2 additional lots. Home is in need of updating with lots of potential to add your own touch and design. More pictures coming soon. Currently on septic but sewer is available.

Beds:
4
Baths:
4.00
Sq.Ft.:
2,185
Status:
Active
MLS#:
MDQA2017930
Type:
Single Family-Detached
Subdivision:
GIBSONS GRANT
Lot size:
0.14 Acres
Year built:
2017
Courtesy: Redfin Corp 301-658-6186
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ADDITIONAL INFORMATION

Experience the best of Kent Island living in this beautifully maintained coastal home, ideally situated in the highly desirable Water's Edge section of Gibson's Grant. Built in 2017, this exceptional residence enjoys unobstructed pond views from the welcoming covered front porch, where you can relax while watching blue herons and other native wildlife. Perfectly positioned just one block from the community's exceptional waterfront amenities, including the Chester River, clubhouse, pool, fitness center, kayak launch, fishing pier, and waterfront pavilion, this home offers the perfect blend of luxury, convenience, and the relaxed lifestyle of Maryland's Eastern Shore. Step inside to discover a bright, thoughtfully designed floor plan where beautiful flooring flows throughout the main level and abundant natural light fills every room. Designed for both everyday living and effortless entertaining, the main level offers exceptional versatility with a spacious flex room that is ideal as a home office, den, sitting room, or additional living space, along with a convenient powder room for guests. The heart of the home is the expansive open-concept living area, where the spacious family room, dining area, and beautifully appointed kitchen come together seamlessly. The kitchen features a large center island with abundant seating and workspace, while the family room is highlighted by a beautiful gas fireplace. Just beyond, the brand-new screened porch opens to your own private backyard oasis featuring a beautifully landscaped paver patio, a tranquil ornamental pond with a cascading waterfall, full privacy fencing perfect for pets, and an irrigation system to keep the grounds looking their best. Designed for the ease of first-floor living, the main level features a spacious primary suite privately situated at the rear of the home. The luxurious ensuite bath includes a relaxing Jacuzzi soaking tub, while a second main-level bedroom offers its own private full bath, making it ideal for guests or multigenerational living. The staircase to the upper level is thoughtfully tucked toward the rear of the home, enhancing the home's functional layout. Upstairs, you'll find two generously sized bedrooms and a beautifully appointed full bath, providing comfortable accommodations for family and guests. Completing the home is a spacious rear-entry two-car garage with plenty of room for parking and storage, plus a custom-built workspace perfect for DIY enthusiasts, hobbyists, or woodworking projects. An approximately four-foot-high conditioned crawl space with interior access provides exceptional additional storage. Recent improvements include a brand-new HVAC system, brand-new screened porch, one-year-old oven, and new washer and dryer, allowing you to move in with confidence. Residents of Gibson's Grant enjoy resort-style amenities, including a clubhouse, outdoor pool, fitness center, waterfront pavilion, kayak launch, fishing pier, water access, and direct access to the Cross Island Trail. Tucked behind a peaceful nature preserve just off Route 50, this sought-after waterfront community offers the perfect balance of tranquility and convenience. Located just moments from the Chesapeake Bay Bridge, the home provides an easy commute while placing you minutes from waterfront dining, marinas, shopping, parks, and local entertainment. Beautifully maintained, thoughtfully updated, and ideally located in one of Kent Island's most desirable neighborhoods, this exceptional home offers the perfect opportunity to embrace luxury coastal living on Maryland's Eastern Shore. Schedule your private showing today! Mortgage savings may be available for buyers of this listing.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,900
Status:
Active
MLS#:
MDQA2018010
Type:
Flat
Subdivision:
FOUR SEASONS AT KENT ISLAND
Year built:
2026
Courtesy: Berkshire Hathaway HomeServices PenFed Realty - OP 410-208-3500
View additional info

ADDITIONAL INFORMATION

Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office with lited French doors provides a private and elegant workspace. The kitchen is designed for both everyday living and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with a seat and handheld shower wand, double sinks, and quartz countertops, creating a comfortable and functional retreat. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,900
Status:
Active
MLS#:
MDQA2018008
Type:
Flat
Subdivision:
FOUR SEASONS AT KENT ISLAND
Year built:
2026
Courtesy: Berkshire Hathaway HomeServices PenFed Realty - OP 410-208-3500
View additional info

ADDITIONAL INFORMATION

Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office with lited French doors provides a private and elegant workspace. The kitchen is designed for both everyday living and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with a seat and handheld shower wand, double sinks, and quartz countertops, creating a comfortable and functional retreat. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,524
Status:
Active
MLS#:
MDQA2017932
Type:
Townhouse
Subdivision:
BRIDGE POINTE TOWNHOUSES
Year built:
1990
Courtesy: RE/MAX Executive 443-274-1900
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ADDITIONAL INFORMATION

REDUCED!! Welcome to one of the most desirable Homes in the Bridgepointe Community! ALL NEW Carpet & flooring, fresh custom paint, Granite countertops and Newer Appliances! This beautifully maintained END UNIT home offers added privacy, abundant natural light and a thoughtfully designed floor plan that perfectly blends comfort and convenience. Featuring one of the community's most sought after amenities... an ATTACHED GARAGE with interior access! This exceptional home also offers a MAIN LEVEL Primary bedroom & full bath, first floor laundry, making it ideal for guests, multigenerational living, a home office or anyone seeking the convenience of main level living. Step inside to discover bright, inviting living spaces enhanced by the additional windows that only an end unit can provide. The open concept layout creates an effortless flow for both everyday living and entertaining. The well-appointed kitchen opens to the main living areas while the spacious bedrooms provide flexibility for family, guests, or work-from-home needs. Peace of mind comes with knowing the crawl space is fully encapsulated! Enjoy the best of low maintenance living in the highly desirable Bridgepointe Community, with easy access to shopping, dining, parks, schools, marinas, and the Chesapeake Bay. Commuters will appreciate the close proximity to the Bay Bridge, Route 50, Annapolis, DC, Baltimore and all of Maryland's Eastern Shore! Whether you are searching for a full-time residence, investment or a weekend retreat, this exceptional home offers the perfect combination of location, lifestyle and value!

Beds:
2
Baths:
3.00
Sq.Ft.:
2,003
Status:
Active
MLS#:
MDQA2017860
Type:
Flat
Subdivision:
FOUR SEASONS AT KENT ISLAND
Year built:
2025
Courtesy: Real Broker, LLC 855-450-0442
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ADDITIONAL INFORMATION

Move-in ready condo with zero wait! This meticulously maintained, first-floor Magothy shows like new, offering over 2,000 square feet of single-level living in the highly sought-after Four Seasons at Kent Island 55+ active-adult community. Enjoy the rare convenience of direct outdoor patio access and beautiful views from every window. The thoughtfully designed open-concept features two spacious bedrooms, each boasting a full bath and walk-in closet, plus direct patio access from the primary suite. The gourmet kitchen centers around a massive seating island with pendant lighting and a stylish dry bar. French doors open to a dedicated home office, while double sliding doors in the living room provide the entire space with natural light. Quartz countertops and seamless luxury vinyl plank flooring are found throughout the home. Complete with a private guest powder room, laundry room, climate-controlled storage, a one-car garage, and a beautifully appointed community room on the second floor, this condo delivers the low-maintenance lifestyle the community is known for. The award-winning 24,000 square foot Chester House clubhouse is the heart of the community, with indoor and outdoor pools, a fully equipped fitness center, yoga studio, demonstration kitchen, library, billiards and game room, and a grand ballroom. Outside, enjoy lighted tennis, pickleball, and bocce courts, a dog park, gas and wood-burning fire pits, a waterside tiki bar, and miles of walking and biking trails connecting to the Cross Island Trail. The 450-foot community pier on the Chester River, with boat slips plus canoe and kayak launch and storage, is a favorite for anyone who loves the water. Year-round clubs, classes, live entertainment and events can be found at the community clubhouse, and you’ll be minutes from Kent Island, shops, waterfront dining, and Queenstown Premium Outlets, with easy access to the Bay Bridge for Annapolis, Baltimore, and Washington D.C. Schedule your private showing today.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,000
Status:
Active
MLS#:
MDQA2017820
Type:
Single Family-Detached
Subdivision:
NONE AVAILABLE
Lot size:
4.01 Acres
Year built:
1928
Courtesy: Tidewater Properties 410-827-8877
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ADDITIONAL INFORMATION

Privacy without isolation - Rare Find - 2 comfy houses on one waterfront property! Each with unobstructed views of the picturesque Cox Creek before it enters the Bay. Discover a captivating traditional charm in this vintage cape cod ( 3-bedrooms, 2-bathrooms, with an enclosed plus a screened porch) recently updated in spring 2026. The former detached garage converted into the 2 story guest cottage (2BR, 1.5 BA) has a fabulous screened porch you'll spend endless hours on. A separate building provides versatile storage for equipment or hobbies. Nestled in a serene rural setting, this home boasts picturesque views along the banks of Cox Creek, offering panoramic western vistas that will take your breath away, especially as the sun sets on the horizon. Step inside to find a thoughtfully designed interior featuring rich wood floors in most rooms. Upgraded countertops and new appliances elevate the kitchen, convenient to the screened porch perfect for gatherings. The living room, complete with a brick fireplace, invites warmth and relaxation. Enjoy the convenience of an entry-level bedroom, or home office, in this traditional floor plan that flows seamlessly throughout. The exterior amenities are equally impressive, featuring a private shoreline and a circular gravel driveway that accommodates ample parking. With 548 feet of waterfrontage, indulge in fishing, boating, or simply soaking in the tranquil surroundings. The property includes a private dock with electric hoist and ramp, making water access effortless. . The secluded parcel offers year-round access, ensuring your retreat is always within reach. This home is not just a residence; it's a lifestyle waiting to be embraced. Don't miss the opportunity to make this serene haven your own! Less than 30 minutes to Annapolis, 50 minutes to Baltimore or DC.. Convenient to area restaurants and points of interest. Not under subdivision restrictions. Perfect for multi-generational living, private guest quarters, or possible rental income. Room for expansion of living spaces, outdoor sports court, horseshoes, bocci, or gardens.. Former waterside pool could be revitalized, subject to county approval.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,772
Status:
Active
MLS#:
MDQA2017958
Type:
Single Family-Detached
Subdivision:
FOUR SEASONS AT KENT ISLAND
Lot size:
0.16 Acres
Year built:
2026
Courtesy: Berkshire Hathaway HomeServices PenFed Realty - OP 410-208-3500
View additional info

ADDITIONAL INFORMATION

Welcome to the Kerr, a beautifully designed home offering 3 bedrooms, 3 baths, and a 3-car garage. This home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area features a cozy fireplace with mantel and hearth, creating a warm and inviting focal point. A dedicated home office provides a private space for productivity, while the screened patio extends the living area outdoors—perfect for entertaining or relaxing. The kitchen is equipped for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive, elegant finish. Hardwood flooring flows throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, bedrooms 2, the primary suite, loft, and second floor, while tile is featured in all full baths and the laundry room. The primary bath includes a walk-in shower with seat and handheld shower wand and a double-sink vanity for added convenience and luxury. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. 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.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,900
Status:
Active
MLS#:
MDQA2017956
Type:
Flat
Subdivision:
FOUR SEASONS AT KENT ISLAND
Year built:
2026
Courtesy: Berkshire Hathaway HomeServices PenFed Realty - OP 410-208-3500
View additional info

ADDITIONAL INFORMATION

Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office with lited French doors provides a private and elegant workspace. The kitchen is designed for both everyday living and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with a seat and handheld shower wand, double sinks, and quartz countertops, creating a comfortable and functional retreat. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

Beds:
2
Baths:
2.00
Sq.Ft.:
2,118
Status:
Active
MLS#:
MDQA2017900
Type:
Single Family-Detached
Subdivision:
FOUR SEASONS AT KENT ISLAND
Lot size:
0.14 Acres
Year built:
2023
Courtesy: Coldwell Banker Realty 410-263-8686
View additional info

ADDITIONAL INFORMATION

Assumable VA Loan available w/interest rate in 5's to qualified buyers! Experience the ease of elegant one-level living in this exceptional home, located in one of Maryland's premier 55+ active adult communities on the Chesapeake Bay. Designed for both comfort and style, this beautifully appointed residence features a three-car tandem garage with an EV charger, a spacious screened porch, a cozy gas fireplace, upgraded trim and designer feature walls. Thoughtful enhancements include Hunter Douglas plantation shutters, custom California Closets in the owner's suite and second bedroom, modern ceiling fans throughout, reverse osmosis water filtration, and professionally treated energy-efficient windows that reduce UV rays and heat for year-round comfort. Beyond your front door, enjoy a true resort-style lifestyle just 45 miles from both Washington, D.C. and Baltimore. The impressive 24,000-square-foot clubhouse offers indoor and outdoor pools, a state-of-the-art fitness center, tennis and pickleball courts, and an active social calendar led by a full-time lifestyle director. From kayaking, yoga, and walking clubs to mahjong, pickleball, and countless social events, there is something for everyone. Located just steps from the waterfront and minutes from historic Annapolis, this vibrant Kent Island community combines small-town charm with exceptional convenience. Enjoy easy access to Route 50, along with nearby shopping, dining, and everything that makes Chesapeake Bay living so special.

Beds:
5
Baths:
3.00
Sq.Ft.:
3,000
Status:
Active
MLS#:
MDQA2017856
Type:
Single Family-Detached
Subdivision:
CASTLE MARINA
Lot size:
0.5 Acres
Year built:
1977
Courtesy: Samson Properties 703-378-8810
View additional info

ADDITIONAL INFORMATION

SPACE, FLEXIBILITY & VALUE ON KENT ISLAND! Welcome to 205 Anchor Lane, where generous square footage, versatile two-level living and incredible outdoor space come together to create a home that can truly adapt to your needs. With 5 bedrooms, updated bathrooms and living spaces on both levels, the floor plan offers excellent flexibility for multi-generational living, guests, a home office or the potential to create a private in-law suite. The main level features easy-care LVP flooring, while the lower level has been refreshed with brand-new carpet, giving the home a fresh, move-in-ready feel. Multiple living and gathering spaces mean there is room to spread out without sacrificing connection. Outside, the possibilities continue! Enjoy morning coffee on the screened porch, entertain on the spacious deck, or take advantage of the large backyard for play, pets, gardening and gatherings. Car enthusiasts, hobbyists and anyone needing serious storage will LOVE the impressive detached 4-car garage—an increasingly hard-to-find feature on Kent Island. And the best part? NO HOA! Enjoy the freedom to make the property your own without the added monthly community expense. With 5 bedrooms, two levels of flexible living space, updated baths, multiple outdoor living areas, a huge backyard and an exceptional 4-car detached garage, 205 Anchor Lane delivers an incredible amount of home and versatility for the money. If you've been searching for true VALUE on Kent Island, this one deserves a look! With 5 bedrooms and 3 full bathrooms, this home provides room for everyone. The lower level offers excellent potential for multigenerational living, guest accommodations, or a future in-law suite. Fresh carpet, luxury vinyl plank flooring, and updated bathrooms create a move-in ready feel while still leaving opportunities to add your own personal touches and build equity. The functional floor plan offers multiple living spaces, a two-car garage, and abundant storage throughout. Outside, the expansive yard provides plenty of room for entertaining, gardening, pets, or simply enjoying the outdoors. Ideally located within walking distance to local dining, Castle Marina, and the Cross Island Trail, you'll love the convenience of enjoying the Kent Island lifestyle right from your doorstep. Public sewer service and well water add to the property's appeal. Whether you're searching for extra space, a home that can accommodate extended family, or simply a great value in a sought-after location, 205 Anchor Lane delivers endless possibilities.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,900
Status:
Active
MLS#:
MDQA2017928
Type:
Flat
Subdivision:
FOUR SEASONS AT KENT ISLAND
Year built:
2026
Courtesy: Berkshire Hathaway HomeServices PenFed Realty - OP 410-208-3500
View additional info

ADDITIONAL INFORMATION

Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in October 2026, this home combines modern comfort with functional living spaces. The heart of the home features a dry bar and an electric fireplace, creating a warm and inviting atmosphere. A dedicated home office with lited French doors provides a stylish and private workspace. The kitchen is designed for both everyday living and entertaining, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with seat and handheld shower wand, double sinks, and quartz countertops for added convenience and style. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,524
Status:
Active
MLS#:
MDQA2017690
Type:
Single Family-Detached
Subdivision:
NONE AVAILABLE
Lot size:
0.41 Acres
Year built:
1974
Courtesy: Engel & Volkers Annapolis 443-292-6767
View additional info

ADDITIONAL INFORMATION

Coastal cottage charm meets waterfront living on picturesque Crab Alley Creek. Offering 120 feet of shoreline and direct access to the Eastern Bay, this beautifully maintained home combines privacy, convenience, and the very best of the Chesapeake lifestyle. A pier permit already in hand provides an exciting opportunity for the next owner to further enhance their waterfront experience. This move-in-ready residence features 3 bedrooms, 2 full baths, and a versatile bonus room that can serve as a home office, guest room, or potential 4th bedroom. Meticulously updated and lovingly maintained throughout, pride of ownership is evident at every turn. Thoughtful upgrades create a warm and inviting atmosphere, including under-cabinet lighting and dimmer switches throughout the home, allowing you to create the perfect ambiance for any occasion. The kitchen is both stylish and functional, featuring an additional beverage refrigerator, making entertaining family and friends a breeze. The bathrooms offer a touch of luxury with heated floors and built-in Bluetooth speakers, creating a spa-like retreat within your own home. Situated on a large, level waterfront lot, the property is designed for both relaxation and recreation. Across the creek, protected conservation land provides a peaceful, natural backdrop and exceptional privacy rarely found on the water. Raised garden beds offer the opportunity to grow your own herbs and vegetables, while the detached garage, two storage sheds, and attic provide ample space for tools, equipment, seasonal items, and all your waterfront essentials. Spend your evenings gathered around the fire pit overlooking the water, launch a kayak from your backyard, or cruise to one of the many waterfront restaurants accessible from the Eastern Bay. Whether you're entertaining guests or enjoying a quiet sunset, this property embraces the laid-back charm of coastal living. Conveniently located just 10 minutes from the Bay Bridge, 20 minutes from Annapolis, and approximately 90 minutes from the beach, you'll enjoy easy access to everything while feeling worlds away. A rare opportunity to own a turnkey waterfront retreat in one of Kent Island's most desirable locations, where every detail has been thoughtfully curated for comfort, convenience, and enjoyment.

Beds:
4
Baths:
3.00
Sq.Ft.:
1,979
Status:
Active
MLS#:
MDQA2017718
Type:
Single Family-Detached
Subdivision:
NONE AVAILABLE
Lot size:
0.17 Acres
Year built:
2020
Courtesy: Douglas Realty LLC 866-987-3937
View additional info

ADDITIONAL INFORMATION

NEW PRICE—An Unbelievable Value on Kent Island! Built in 2020, this gorgeous, like-new home offers approximately 1,974 square feet of beautifully maintained living space, a spacious yard backing to trees, and a desirable Kent Island location. An assumable VA loan at an attractive 2.75% interest rate may be available to qualified buyers, subject to lender and VA approval. Fresh interior paint and new carpeting throughout make this home truly move-in ready. The spacious living and dining areas provide plenty of room for everyday living and entertaining, while the inviting fireplace adds warmth and character. The kitchen features a breakfast bar, granite, pantry, abundant cabinetry, and generous storage. The spacious owner’s suite offers two walk-in closets and a private en-suite bath, creating a comfortable retreat. Step outside to enjoy the private backyard backing to trees, ideal for relaxing, entertaining, or enjoying peaceful evenings outdoors. Ccnvenient access to nearby boat ramps. Ideally located near shopping, dining, golf, pickleball, waterfront parks, walking trails, beaches, a dog beach, marinas, boat storage, Queenstown Premium Outlets, and popular local restaurants and entertainment. Experience the best of Kent Island living in this beautifully updated home. Some rooms have been virtually staged, including the owner’s suite, living room, and dining room.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,832
Status:
Active
MLS#:
MDQA2017608
Type:
Flat
Subdivision:
FOUR SEASONS AT KENT ISLAND
Year built:
2020
Courtesy: Coldwell Banker Realty 410-224-2200
View additional info

ADDITIONAL INFORMATION

Beautiful fourth-floor condo offering nearly 2,000 square feet of living space, featuring two bedrooms, a home office, two full baths, and a half bath. Enjoy morning sun from the oversized porch, a spacious living room, and an open-concept layout designed for comfort and entertainment. Highlights include luxury flooring, a fireplace, and a beautifully appointed kitchen with an oversized center island and quartz countertops stainless steel appliances and much more. This unit also includes a one-car garage and private storage space. The community offers unparalleled amenities and gorgeous water views, creating the perfect Chesapeake Bay lifestyle. Enjoy walking trails, outdoor tennis courts, indoor and outdoor pools, and a 23,000-square-foot clubhouse with outdoor spaces, a ballroom, test kitchen, outdoor bar, and community pier, views of the Chester River.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,602
Status:
Active
MLS#:
MDQA2017542
Type:
Flat
Subdivision:
FOUR SEASONS AT KENT ISLAND
Lot size:
0.06 Acres
Year built:
2020
Courtesy: Real Broker, LLC 855-450-0442
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ADDITIONAL INFORMATION

Newly adjusted price. Rarely available, this luxurious Severn penthouse in Four Seasons at Kent Island offers the perfect blend of waterfront beauty, comfort, and resort-style living. Built in 2020 and meticulously maintained, the home features an open-concept design filled with natural light and stunning views of Macum Creek and the Chester River. The gourmet kitchen is the heart of the home, showcasing a large island, premium appliances, and picturesque water views. Three spacious bedrooms, two-and-a-half baths, and inviting living spaces provide comfort and flexibility for everyday living and entertaining. Enjoy spectacular sunrises, abundant wildlife, and peaceful water views from your private balcony. Just steps away, you'll find creekside trails, kayak launches, picnic areas, and direct access to the natural beauty that makes Kent Island so special. Located in desirable Phase One, this penthouse offers enhanced privacy, mature surroundings, and freedom from nearby construction. Additional features include an oversized attached garage with interior access and a secure storage room. Residents enjoy access to Four Seasons' exceptional amenities, including a 24,000-square-foot clubhouse, indoor and outdoor pools, fitness center, pickleball and tennis courts, fishing pier, kayak launches, dog parks, walking trails, tiki bar, and more.

Beds:
3
Baths:
4.00
Sq.Ft.:
2,100
Status:
Active
MLS#:
MDQA2017442
Type:
Townhouse
Subdivision:
BAYSIDE
Year built:
2000
Courtesy: Real Broker, LLC 855-450-0442
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ADDITIONAL INFORMATION

Seller is offering up to $9,000 toward the buyer's interest rate buydown or closing costs. That's real money applied at settlement, and on a home already carrying over $50,000 in owner improvements, it's the kind of combination that doesn't sit long. This is a renovated end-unit townhome with three bedrooms and three and a half baths in Bayside, an established waterfront community along the Chester River. Hardwood runs the main and upper levels — no carpet — beginning at a slate tile entry that opens into rooms filled with natural light. The renovated kitchen is the centerpiece: Thermador induction cooktop, GE Monogram wall oven, Bosch dishwasher, granite counters, updated cabinetry, and recessed lighting, all opening directly to the living area so the space works as one. That living area centers on a gas fireplace framed by built-in bookshelves. Just off it, a private deck with a retractable awning looks out to seasonal water views of the Chester River. Upstairs, the primary suite includes a walk-in closet, an ensuite bath with jetted soaking tub and separate shower, and a private deck of its own. The second upper-level bedroom has its own attached full bath. Above that, the top-floor space adds two walk-in closets and a third full bath, with the flexibility to serve as a guest room, home office, or studio. Recently updated HVAC. High-efficiency washer and dryer convey. Attached one-car garage for protected parking and storage. End-unit positioning means no neighbor on one side. The monthly fee covers lawn maintenance, snow removal, pool access, and recreation facilities — the maintenance is handled, the amenities are there, and the weekends are yours. Route 50/301 is minutes away, with shopping and dining close by. Nothing here needs doing. Ask about the $9,000 buyer credit and current availability.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,312
Status:
Active
MLS#:
MDQA2017378
Type:
Single Family-Detached
Subdivision:
GIBSONS GRANT
Lot size:
0.22 Acres
Year built:
2012
Courtesy: TTR Sotheby's International Realty 410-673-3344
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ADDITIONAL INFORMATION

Situated on one of the largest lots in sought-after Gibson’s Grant, this 4-bedroom, 3.5-bath home offers space, flexibility, and room to grow. High ceilings and an open layout create an airy feel, with an oversized kitchen flowing seamlessly into the family room and a separate main-level office for work or quiet retreat. The main level also features a formal dining room and living room. Upstairs, the spacious primary suite features a sitting area, two walk-in closets, and en-suite bath, alongside three additional bedrooms and two full bathrooms. The unfinished walkout basement includes a rough-in for a future bath. Outside, enjoy a fenced backyard complete with a patio and built-in fire pit—perfect for gathering year-round. Community amenities include swimming pool, clubhouse, fitness center, walking trails, community pier, picnic area, and kayak launch. Centrally located on Kent Island. Only 5 minutes to the Bay Bridge.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,595
Status:
Active
MLS#:
MDQA2017432
Type:
Townhouse
Subdivision:
BAYSIDE
Year built:
1992
Courtesy: Realty Navigator 410-643-3404
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ADDITIONAL INFORMATION

Marina views, waterfront surroundings, and the Bayside lifestyle—all at a new price of $429,900! Welcome to 106 Bodys Neck Road in Chester, where everyday living comes with a view. This 3-bedroom, 2.5-bath home offers upper and lower decks overlooking the marina, creating inviting spaces to enjoy your morning coffee, unwind at the end of the day, or simply watch the activity along the water. Inside, you'll find a comfortable and functional layout featuring a gas fireplace, spacious living areas, and an attached 1-car garage. New carpet in the lower level adds a fresh touch, while a new roof installed in 2023 offers an important recent update. The front foot fee was paid in full in 2024, and the seller is also providing a one-year home warranty for added peace of mind. Bayside offers a resort-style setting with amenities that include a clubhouse, outdoor pool, fitness center, tennis and volleyball courts, and scenic walking and jogging trails. Marina and water access add to the Chesapeake Bay lifestyle that makes this community so appealing. Conveniently located on Kent Island with easy access to Route 50, the Bay Bridge, dining, shopping, and nearby waterfront destinations. Now offered at $429,900. Come experience the marina view and see what life at Bayside could look like for you.

Beds:
2
Baths:
3.00
Sq.Ft.:
2,003
Status:
Active
MLS#:
MDQA2017364
Type:
Flat
Subdivision:
FOUR SEASONS AT KENT ISLAND
Year built:
2023
Courtesy: Real Broker, LLC 855-450-0442
View additional info

ADDITIONAL INFORMATION

Priced to sell at just $700,000, this is an exceptional opportunity. With a $160,000 lot premium and over $60,000 in builder upgrades, this home is offered below its replacement value. Experience everything Four Seasons has to offer without the wait. This meticulously maintained home shows like new and is located just steps from the community amenities and vibrant social spaces that make Four Seasons so desirable. 132 Wheelhouse Way offers one of the most desirable locations in the community, with exceptional water views, ground-level access, and an easy walk to the resort-style amenities. Inside, you'll find a gourmet kitchen with quartz countertops, GE Café double wall ovens, upgraded stainless steel appliances, luxury vinyl plank flooring, and an open-concept living space with an electric fireplace and beautiful water views. The primary suite features patio access, a walk-in closet, and a luxurious bath, while the second bedroom suite and private office provide comfort and flexibility. Residents enjoy the Chester House Clubhouse, indoor and outdoor pools, a fitness center, pickleball and tennis courts, walking trails, a kayak launch, fishing pier, dog park, tiki bar, and more. Perfectly located on Kent Island, this home offers an exceptional blend of luxury, convenience, and the Chesapeake Bay lifestyle.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,302
Status:
Active
MLS#:
MDQA2017274
Type:
Townhouse
Subdivision:
BRIDGE POINTE
Year built:
1995
Courtesy: Keller Williams Realty Centre 410-312-0000
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ADDITIONAL INFORMATION

Nestled in the heart of Kent Island, this charming 3 Bedroom, 2 Full Bathroom townhome with Bonus Room, offers the perfect blend of comfort, convenience, and peaceful surroundings. Located in the desirable Bridgepointe community, this home features major updates including a newer roof, HVAC system, and water heater providing peace of mind for years to come. Enjoy a private backyard setting that backs to mature trees, creating a serene outdoor retreat, while being just steps from the community lake, walking paths, and boat parking lot! Inside, the functional layout offers spacious living areas, comfortable bedrooms, and plenty of natural light throughout. Whether you're looking for a primary residence, weekend getaway, or low-maintenance lifestyle near the Chesapeake Bay, this Kent Island gem is ideally situated close to shopping, dining, marinas, and commuter routes. Schedule your tour today! Home sold as-is.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,440
Status:
Active
MLS#:
MDQA2017146
Type:
Townhouse
Subdivision:
QUEENS LANDING
Year built:
1998
Courtesy: Island Realty, LLC 410-643-4131
View additional info

ADDITIONAL INFORMATION

Motivated Seller now offering $5,000 closing help! This home is move in ready. Discover refined waterfront community living in this beautifully updated and rarely available 3-bedroom, 2.5-bath condo in the highly desirable Queen’s Landing community. Thoughtfully designed with both comfort and style in mind, this spacious home offers fresh interior paint, an inviting open layout, and a beautifully updated kitchen featuring elegant quartz countertops—perfect for everyday living, relaxing weekends, and entertaining family and friends. Natural light fills the living spaces, while the seamless flow between the kitchen, dining, and living areas creates a warm and welcoming atmosphere throughout the home. Step outside to enjoy your private screened porch—ideal for morning coffee or evening unwinding—or host summer gatherings on the private patio designed for grilling and outdoor entertaining. Rare opportunities like this don’t come along often in Queen’s Landing, especially with the combination of three bedrooms, modern updates, and exceptional outdoor living spaces. Enjoy a true resort-style lifestyle with community amenities that include a swimming pool, fitness center, pickleball and tennis courts, and a private marina. Whether you’re looking for a full-time residence, weekend retreat, or low-maintenance coastal lifestyle, this home offers the perfect balance of relaxation and convenience. Ideally located in the heart of Chester, you are just minutes from waterfront dining, shopping, entertainment, and major commuter routes—making it easy to enjoy everything the Eastern Shore has to offer while staying connected to Annapolis, Baltimore, and Washington, D.C. Some photos are for illustrative purposes only.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,312
Status:
Active
MLS#:
MDQA2017164
Type:
Other
Subdivision:
QUEENS LANDING
Year built:
1995
Courtesy: Coldwell Banker Realty 410-263-8686
View additional info

ADDITIONAL INFORMATION

Price Improvement! Seller is offering closing cost assistance for qualified buyers! This charming townhouse in Queens Landing offers a perfect blend of comfort and community amenities. Step inside to discover a traditional floor plan featuring a cozy living room off the eat-in kitchen, with a separate family room ideal for gatherings. The home boasts two spacious bedrooms and 2.5 baths, including a primary bath for added convenience. Updates include new flooring throughout; LED lighting, granite counters, newer windows and HVAC system. Enjoy modern amenities with a suite of appliances, including a built-in microwave, dishwasher, electric range, washer and dryer. Outside, the community shines with well-maintained sidewalks, streetlights, and a variety of recreational facilities. Take advantage of the clubhouse, outdoor pool, tennis courts, and scenic waterfront jogging paths. The nearby Chester River provides a serene backdrop for leisurely strolls and outdoor activities, with access to the Cross Island Trail connecting waterfront features at Terrapin Park and The Narrows. Located within a vibrant neighborhood, residents benefit from access to parks and essential public services. This home is not just a place to live; it's a gateway to a fulfilling lifestyle in a welcoming community. Some photos displayed used AI and may not be 100% accurate. Please schedule an in-person tour to view this beautiful property.

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Andrea Conner, Maryland License 667140, Xome Inc., License 667140, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, D.C. License BR200200783, Xome Inc., License CO98372739, [email protected], 844-400- 9663, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, PA License # RM425337, Xome Inc., PA License #RB067821, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, NJ License # 1758875, Xome Inc. NJ License # 2326449, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

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Chester 21619 Real Estate

Chester is located in Maryland. Chester, Maryland 21619has a population of 4,371. Chester 21619 is less family-centric than the surrounding county with 23.42% of the households containing married families with children. The county average for households married with children is 31.88%.

The median household income in Chester, Maryland 21619 is $84,835. The median household income for the surrounding county is $99,597 compared to the national median of $69,021. The median age of people living in Chester 21619 is 43.9 years.

Chester Weather

The average high temperature in July is 87 degrees, with an average low temperature in January of 28.3 degrees. The average rainfall is approximately 46.2 inches per year, with 12.7 inches of snow per year.

Chester Map

Chester Real Estate Market Conditions

  • Median sales price

    N/A
  • # Active listings

    94
    30-day change

Chester Schools and Demographics

Education near Chester, MD

City County
High School Graduates 92.01 92.87
College Degree - 2 year 9.35 7.89
College Degree - 4 year 31.36 36.96
Graduate Degree 8.55 10.55
Expenditures per Student 15,198 15,198
Students per Teacher 14.4 14.4

Elementary Schools near Chester, MD

Grades Students P/T Ratio ZIP
Bayside Elementary School 03 - 05 402 16.1 21666
Cape St. Claire Elementary KG - 05 646 15.9 21409
Grasonville Elementary School PK - 05 494 15.9 21638
Kent Island Elementary School PK - 02 469 16.2 21666
Matapeake Elementary School PK - 05 493 15.4 21666
Rock Hall Elementary School PK - 05 187 14.3 21661
Windsor Farm Elementary School KG - 05 608 17 21409

Middle Schools near Chester, MD

Grades Students P/T Ratio ZIP
Matapeake Middle School 06 - 08 416 15.4 21666
Stevensville Middle School 06 - 08 474 13.5 21666

High Schools near Chester, MD

Grades Students P/T Ratio ZIP
Broadneck High School 09 - 12 2,104 18.4 21409
Kent Island High School 09 - 12 1,194 15.5 21666

Demographics near Chester, MD 21619

Zip Code City
Neighborhood Type Small town
Population 4,371 49,702
Population Density 835 134
Median Age 43.9 44.7
People per Household 2.4 2.6
Median Household Income 84,835 99,597
Average Income per Capita 53,406 49,178

Real estate near Chester