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$660,000
2 Beds 2 Baths
Welcome to Resort-Style Living at Four Seasons at Kent Island! Why wait for new construction when you can move right into this beautifully upgraded Donegal model with the sought-after Great Room extension? Offering exceptional value, this is currently the lowest-priced single-family home in the community, making it an outstanding opportunity to enjoy one of Maryland’s premier 55+ active adult neighborhoods. Designed with both elegance and everyday comfort in mind, this home features a stunning Gourmet Kitchen highlighted by a large Quartz Island, premium Gourmet Appliance Package with Double Oven, and abundant workspace—perfect for everything from casual breakfasts to holiday entertaining. The open-concept Great Room creates an inviting gathering place, centered around a warm Gas Fireplace, while upgraded lighting throughout the home adds a sophisticated touch. The Luxury Spa Bath offers a private retreat after a busy day, and Quartz vanities in every bathroom provide both beauty and durability. The thoughtfully designed floor plan includes first-floor bedrooms, allowing comfortable one-level living. A dedicated home office on the main level provides an ideal workspace, hobby room, or can easily function as a third bedroom for visiting family and friends. Additional premium features include elegant Plantation Shutters, an oversized two-car garage with generous storage space, and an underground irrigation system that helps keep your lawn lush while minimizing maintenance. With approximately $89,000 in builder upgrades and options, this home offers exceptional quality and value that would be costly to duplicate today. Come experience the carefree lifestyle of Four Seasons at Kent Island, where resort-style amenities, beautiful surroundings, and a vibrant social atmosphere make every day feel like a vacation. Life in Four Seasons at Kent Island is about more than the home itself. Residents enjoy resort-style amenities including a stunning clubhouse, indoor and outdoor pools, fitness center, pickleball courts, walking trails, kayak launch, fishing pier, and an active social calendar designed for a vibrant lifestyle.

118 Broadwater Dr, Chester

Listing courtesy of RE/MAX Executive. Contact: 4432741900

$599,000
3 Beds 2 Baths
Welcome home to this beautifully updated contemporary offering water views, flexible living space, and a community pier practically in your backyard! With 3 bedrooms and 2 full baths, this home features a primary bedroom on each level, making the layout ideal for a variety of living arrangements.The heart of the home is the gourmet kitchen, complete with granite countertops, a stylish glass backsplash, stainless steel appliances, a center island, breakfast bar, and plenty of space for a kitchen table. Just beyond, the dramatic two-story living room features a cozy gas fireplace, refinished hardwood floors, and a beautiful stained-glass window that adds character and charm. Enjoy the convenience of a main-level primary bedroom, while upstairs, the entire second floor is dedicated to an expansive primary suite with beautiful views of Greenwood Creek. Outdoor living is just as inviting. Relax on the screened porch, large deck, enjoy the fenced rear yard, or head just steps away to the community pier, where an available boat slip puts days on the water within easy reach. You get the Chesapeake lifestyle and beautiful water views without the waterfront taxes! The entire home has been freshly painted and the hardwood floors beautifully refinished, making it ready for its next owner. Additional features include an encapsulated crawl space and a spacious 2-car garage.Water views, boating access, beautiful updates, and a unique contemporary design—this is Eastern Shore living without the waterfront price tag.

1700 Bennett Point Rd, Queenstown

Listing courtesy of Rosendale Realty. Contact: 4107580333

$1,395,000
4 Beds 5 Baths
Experience elevated waterfront living in one of Kent Narrows' most desirable marina communities. Perfectly positioned as an end-unit in prestigious Wells Cove Townhomes & Marina, this extensively renovated four-level residence captures sweeping Chesapeake Bay and marina views while offering the rare combination of refined finishes, deep-water boating, and a true lock-and-leave lifestyle. Ready for immediate occupancy, this is the turnkey waterfront home you've been waiting for. Spanning approximately 3,500 square feet, the thoughtfully designed floor plan features four bedrooms, four full baths, one half bath, and a private elevator servicing all four levels. Crafted to satisfy even the most discerning buyer, the home reflects an uncompromising commitment to quality, comfort, and timeless design. Rich hardwood flooring, custom millwork, designer lighting, soaring 9-foot ceilings, abundant natural light, and beautifully renovated interiors create an atmosphere that is both sophisticated and inviting. At the heart of the home is a stunning chef's kitchen, completely redesigned in 2019 with custom cabinetry, premium appliances, stone countertops, an oversized center island, and exceptional workspace. Multiple living and entertaining areas, two spacious owner suites, a loft, and a generous recreation room with a wet bar provide remarkable flexibility for family and guests alike. Four private covered waterfront decks seamlessly extend the living space outdoors, creating the perfect setting to enjoy morning coffee, watch boats glide through the marina, or unwind with spectacular Chesapeake Bay sunsets. From nearly every level, the ever-changing waterfront views become part of everyday life. For boating enthusiasts, the deeded deep-water boat slip is one of the marina's most desirable, offering approximately 4 feet of mean low water and the ability to accommodate a substantial vessel. Ideally positioned for convenient access to the Chesapeake Bay, it provides an exceptional home port for everything from an afternoon cruise to a weekend on the water. An oversized two-car garage offers generous storage for vehicles, bicycles, paddleboards, fishing gear, and all the essentials for an active waterfront lifestyle. Located in the heart of Kent Narrows, you're just moments from waterfront restaurants, marinas, boutique shopping, the Cross Island Trail, golf, and Route 50, providing convenient access to Annapolis, Baltimore, Washington, D.C., and the Delaware and Maryland beaches. Beautifully renovated, impeccably maintained, and completely turnkey, this extraordinary residence presents a rare opportunity to own one of Wells Cove's premier waterfront homes. Simply arrive, settle in, and begin enjoying the Chesapeake Bay lifestyle from day one.

314 Channel Marker Way, Grasonville

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$225,000
4 Beds 2 Baths
Extra-wide fenced lot, and just minutes from Chestertown and Chester Harbor. Introducing this spacious 4-bedroom, 2-bath ranch on an extra-wide fenced lot in Chester Harbor, just minutes from historic Chestertown. Offering comfortable single-level living, the home features a large family room, an expansive kitchen with abundant cabinet and counter space, and a functional floor plan that's move-in ready with the opportunity to add your own cosmetic updates. The generous layout includes four bedrooms, two full baths, and flexible space for guests, a home office, or hobbies. Outside, the oversized iron-fenced yard provides plenty of room for gardening, entertaining, pets, or future expansion. Enjoy your morning coffee or evening unwind on the side porch, while the attached one-car garage adds convenient storage. As part of the Chester Harbor community, you'll enjoy access to the community boat ramp and the Chester River, making it easy to spend your days boating, fishing, kayaking, or simply enjoying the waterfront lifestyle. Ideally located near marinas, parks, waterfront dining, and the charm of downtown Chestertown, this property offers the perfect blend of space, convenience, and recreational opportunities.

533 Round Top Rd, Chestertown

Listing courtesy of EXP Realty, LLC. Contact: 8333357433

$775,000
2 Beds 4 Baths
LOCATION! LOCATION! LOCATION! PANAROMIC WATERFRONT VIEWS!!!! One of the best views in Oyster Cove! Eastern shore's best- kept secret is the beautiful, gated community at the Kent Narrows Bridge! VACATION where you live or work from your home office in this tranquil setting. Scenic entrance ponds with fountains. Grill on your spacious deck while entertaining friends & watch boats heading to St. Michaels/Annapolis, etc. This 3-level, interior townhome offers 2 bedrooms + loft & 3.5 baths. It has white pine floors & a FP w/electric insert & built-ins. Updated, eat-in country kitchen features granite counters, beadboard bar & white cabinetry. Large deck with remote-controlled awning & gate. Waterfront primary suite w/balcony, barn doors, W-I shower, W-I closet & jacuzzi. Utility room equipped with newer, front-loading washer/dryer. Boat slips available for rent /sale, along with 5 visitor slips. Enjoy the 1.5 mi. WATERFRONT walking path & the beautiful clubhouse w/state-of-the-art gym, full kitchen, holiday parties & monthly socials, game nights, etc. Saltwater pool opens at 6AM so you can enjoy a swim before the heat of the day. Dock your boat in 1 of the 2 marinas where slips range from 35' - 60'. Use the convenient launch pad for your kayak where there is space for > 100 kayaks or take advantage of the 10 jet ski ports. Enjoy a bike ride on the nearby, paved Cross Island Trail from Oyster Cove to the Chesapeake Bay - great for dog walking, biking, jogging, etc. Walk to 5 restaurants. Only 20 min. to Annapolis. Enjoy a round of golf at Blue Heron executive course or Queenstown championship course. CHANGE YOUR ADDRESS & CHANGE YOUR LIFESTYLE! You will never want to move again!!!

1107 Oyster Cove Dr, Grasonville

Listing courtesy of Star Realty. Contact: (443) 496-1367

$295,000
3 Beds 2 Baths
COMING SOON!! Welcome home...spacious rancher nestled on a beautiful, private 1-acre lot. This home offers 3 bedrooms, 2 full bathrooms, a cozy living room, and an eat-in kitchen perfect for everyday living. The full unfinished basement provides endless possibilities for additional living space, a workshop, or extra storage. Step outside to enjoy the peaceful backyard, featuring a privacy-fenced yard and a paved driveway. The roof, siding, and windows were replaced approximately 10 years ago, offering added value and peace of mind. Stay warm and keep utility costs down during the colder months with both a pellet stove in the living room and a wood-burning stove in the basement. With just a little updating, this home could be everything you've been looking for. Offering privacy, space, and endless potential, it's a great opportunity to make it your own. Located just minutes from the historic waterfront town of Chestertown, you’ll enjoy charming boutiques, local restaurants, seasonal festivals, the popular Farmers Market, and plenty of ways to experience the scenic beauty of the Chester River. The area perfectly captures the charm and lifestyle of Maryland’s Beautiful Eastern Shore.

240 Round Top Rd, Chestertown

Listing courtesy of Clark & Co Realty, LLC. Contact: 410-490-2183

$315,000
3 Beds 2 Baths
Welcome to 109 Parma Road in family-friendly Chester Harbor. This well-maintained home is located on a quiet street and has three generously sized bedrooms with hardwood flooring and 2 full bathrooms. An upgraded kitchen featuries granite countertops, SS appliances, and solid wood cabinets with quiet-close drawers. Spacious living room off the kitchen and dining room combo. Spacious and private backyard is perfect for dogs and children. Mature oak trees provide lots of cool shade. Recent upgrades include: bathroom vanities, ceilings fans, light fixtures, microwave, interior paint, driveway crushed run. Chester Harbor is a quiet community with water access to the Chester River for just $15 per year and NO HOA. 5 minutes to downtown Historic Chestertown. Founded in 1706, Chestertown sits on the banks of the Chester and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market. Enjoy country living on the Eastern Shore. Less than one hour to Annapolis. Much more info and professional photos coming soon. Stay tuned!

109 Parma Rd, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

$615,000
4 Beds 3 Baths
*Professional pictures should be up by the weekend. In the meantime please enjoy a couple of sneak peak ones!*This is the home for you, if you are ready to experience the Eastern Shore Lifestyle and love coastal vibes!! Welcome to 132 Chesapeake Estates Drive, nestled in the quaint community of Chesapeake Estates. Before pulling into the driveway, you will see a peek-a-boo glimpse of the Chesapeake Bay. If you want to watch the sunset or just enjoy a meal by the water, venture to the waterfront park that is exclusive to the neighborhood. It features a playground and plenty of picnic tables for your enjoyment and convenience. Once you have let your worries melt away by the water, it will be time to head back to your home, to relax and enjoy your brand new construction home! This 4 bedroom, 3 full bath home, has upgrades in every room. It is not your average spec home. One of the highlights of the home, is the open floor plan. The living area, kitchen and dining area are completely open. The living area has a gorgeous, almost 11ft step/trey ceiling with recess lighting throughout, along with crown molding. The kitchen has a classy coastal look, with both white cabinets and a light brown island with room for barstools. The kitchen includes, soft closing cabinets, a farmhouse sink, crown molding, SS Appliances that are Energy Efficient and a subtle, elegant backsplash. If you need extra storage, for food, etc., there is extra space in the pantry, that is conveniently located in the laundry room area, directly off of the garage. Which makes for super easy access after grocery shopping. This lovely home has LVP flooring throughout, making it have a beautiful, seamless flow when touring. Crown molding is included throughout the foyer, dining area, living area, kitchen and hallways. The primary bedroom, includes an ensuite bathroom. The bathroom has a double vanity, a tiled walk in shower with upgraded fixture and a freestanding bathtub. So many other upgrades, that may seem small, but make a huge difference either aesthetically or functionally, some of those include, shiplap tastefully placed throughout the home, cedar shake impressions on the exterior, no wiring shelving in any of the 4 bedroom closets, 2 primary closets, upgraded toilets (to a higher height), etc. The exterior of the home has a nice size front and backyard, landscaping and ample driveway for parking. The attached garage is finished (meaning it has been drywalled and is painted), and includes an electric car charger, remote, keyless entry and a 360 degree camera inside the garage door opener. Which is so convenient when you have a delivery and you will not be home, but want it left in the garage. Of course, the home has a fully conditioned crawlspace (including a sump pump). Lastly, one of my favorite things about this home, is the location! At the beginning of the neighborhood, is access to the South Island Trail (a 7-miled paved trail), that you can enjoy at your convenience, whether you are a walker, runner, biker, etc. You can also be at a beach, park, marina or pier within minutes. (Including the Romancoke Pier and Matapeake Beach). If golf is more your style, you are in luck because again minutes away is the Blue Heron golf course. Don't forget all the amazing restaurants, coffee shops, and other local small businesses that are what make KI special! Call today to schedule your private showing! MHBR: 7172

132 Chesapeake Estates Dr, Stevensville

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

$779,900
4 Beds 3 Baths
Welcome to 354 Claiborne Fields Drive, a beautifully updated home offering over 3,100 square feet of thoughtfully designed living space on a picturesque 1.25-acre lot in Centreville, Maryland. Built in 2000, this exceptional two-story residence combines timeless design with modern updates, creating the perfect setting for everyday living and effortless entertaining. Step inside to a welcoming foyer that opens to spacious, light-filled living areas. The flowing floor plan seamlessly connects the living room, dining room, and recently renovated kitchen, creating an inviting atmosphere for family gatherings and entertaining. A cozy fireplace serves as the focal point of the separate family room, while the updated kitchen features quartz countertops, modern stainless steel appliances, abundant cabinetry, a center island, and ample workspace for the home chef. The home offers generously sized bedrooms and three full bathrooms, including a spacious primary suite, large walk-in closet and an en-suite bath with dual vanities, a soaking tub, and a separate walk-in shower. Throughout the home, you’ll appreciate numerous recent improvements, including new flooring on the main level, an updated bathroom, and a brand-new roof, providing both style and peace of mind for years to come. Step outside to your own private backyard oasis. The beautifully landscaped grounds showcase a spectacular 20’ x 40’ resort-style swimming pool with a waterfall feature, a large lighted pergola perfect for outdoor entertaining, and a separate screened porch for relaxing evenings. The expansive 1.25-acre lot offers exceptional privacy and plenty of space for recreation, gardening, or simply enjoying the outdoors. Additional highlights include a spacious three-car garage and a location that combines country living with convenient access for commuters. This well maintained property offers the perfect blend of comfort, luxury, and outdoor living. With its impressive updates, resort-style backyard, and exceptional setting, 354 Claiborne Fields Drive is truly a place you’ll be proud to call home.

354 Claiborne Fields Dr, Centreville

Listing courtesy of Hawkins Real Estate Company. Contact: 2407932485

$859,500
3 Beds 3 Baths
Welcome to Four Seasons at Kent Island, where luxury waterfront living meets the ease of a premier 55+ lifestyle on the shores of the Chester River. Offering breathtaking, unobstructed water views and exceptional community amenities, this beautifully appointed three-bedroom, two-and-a-half-bath condominium is designed for those who appreciate comfort, elegance, and low-maintenance living. The light-filled, open-concept floor plan showcases luxury vinyl plank flooring throughout, recessed lighting, and expansive windows that capture stunning views of the Chester River from nearly every angle. The spacious living room is anchored by a cozy electric fireplace and flows seamlessly into the dining area and gourmet kitchen, creating the perfect space for entertaining or relaxing. The kitchen features stainless steel appliances, a gas cooktop, white cabinetry, generous countertop space, and an inviting layout that keeps everyone connected. Just beyond the living area, step onto the expansive waterside balcony and enjoy panoramic river views, morning coffee, spectacular sunsets, and endless opportunities to watch boats glide by. The luxurious primary suite is a private waterfront retreat, complete with direct balcony access, a spacious sitting area, two walk-in closets, and an elegant ensuite bath featuring dual vanities and a large walk-in shower. Two additional bedrooms provide comfortable accommodations for guests, a home office, or hobbies. Additional highlights include a beautifully crafted built-in bar, electric blinds, a large laundry room, a dedicated storage room, and an attached one-car garage with new epoxy speckled floor. 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.

201 Switchgrass Way Unit #34, Chester

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

$897,750
3 Beds 2 Baths
Be part of the fastest growing 55+ community on Marylands Eastern Shore. Bayberry was the first street in Four Seasons Kent Island where construction in 2021 was superior to those today. 320 Bayberry Drive sits on a Premium Lot which abuts lands owned and maintained by the HOA. The developer is charging a Lot Premium of up to $400,000 for the extra space on remaining lots. The seller just completed $80,000 in renovations. Most of the Furniture can be purchased for below half of what it’s value. The optional sunroom area was completely finished as additional living space. There is a massive 256 square foot rear patio with low V lighting and two raised garden beds. Another HOA area is the rear buffer and beautifully landscaped. If they have a dog, the common area next to the home is almost the size of a building lot offering exceptional privacy. FSKI club house offers resort quality from the indoor pool and gym or the outside pool in summer months. FSKI also allows you golf carts! Don’t miss this opportunity to experience resort style living at Four Seasons Kent Island.

320 Bayberry Dr, Chester

Listing courtesy of Mr. Lister Realty. Contact: (410) 486-5478

$439,900
3 Beds 2 Baths
First Floor Living at it's BEST! Welcome to Symphony Village at Centreville, a sought after Active Adult Community offering an impressive array of amenities and activities. This beautifully maintained three bedroom, two full bath rancher features stunning cathedral ceilings w/custom accent paint, gleaming hardwood and ceramic tile floors. With an open floor plan that offers a living room/dining room combo, a large kitchen with plenty of granite counterspace, separate beverage area with wine rack and mullion cabinets. Right off of the kitchen is an extensive family room with gas fireplace and tons of natural light. Step outside to the brick patio to enjoy a peaceful and private backyard that backs to trees. Additional highlights include a two car garage with a staircase leading to an unfinished bonus room. Come take a look!

214 Harmony Way, Centreville

Listing courtesy of RE/MAX Executive. Contact:

$300,000
2 Beds 2 Baths
Welcome to your perfect island retreat in the sought-after waterfront community of Bayside! This beautifully positioned end-unit condominium offers the ideal blend of comfort, convenience, and breathtaking scenery. Enjoy tranquil pond views with a charming fountain, along with glimpses of the Chester River and marina—all from the privacy of your own deck. Whether you're sipping your morning coffee or unwinding at sunset, this peaceful setting is one you'll love coming home to. Inside, you'll find a spacious open floor plan enhanced by soaring cathedral ceilings, creating a bright and airy atmosphere. Featuring two generously sized bedrooms and two full bathrooms, this home is designed for easy, comfortable living. The fully equipped kitchen flows seamlessly into the living and dining areas, making it perfect for entertaining or simply enjoying everyday life. Best of all, low-maintenance living means more time to enjoy everything this exceptional community has to offer. Take a leisurely stroll to nearby restaurants, keep your boat at the marina just moments away, or explore scenic bike trails and experience the relaxed charm of island living. Bayside residents also enjoy outstanding amenities, including a clubhouse with a fitness center, party room, two expansive balconies overlooking the resort-style pool, and tennis courts. This is your opportunity to own a piece of paradise on the island. Schedule your private showing today—this exceptional home won't last long!

509 Teal Ct Unit #E, Chester

Listing courtesy of RE/MAX Executive. Contact: 4432741900

$615,000
3 Beds 3 Baths
Coming Soon. Welcome to the Country - this beautifully maintained custom-built 3-bedroom, 2.5-bath home, perfectly situated on 3.34 picturesque acres with mature landscaping and plenty of room to relax, entertain, or operate a home-based business. Enjoy peaceful mornings on the inviting front porch or unwind on the cozy screened rear porch while taking in the beauty of nature. Inside, you'll find a warm and welcoming interior featuring a completely renovated kitchen with white cabinetry, quartz countertops, top-of-the-line stainless steel appliances, and stunning new luxury vinyl plank flooring throughout the house. The entire interior has new paint in Sherwin-Williams Agreeable Gray, creating a fresh, timeless feel. The spacious primary suite has an oversized walk-in closet and a luxurious private bath with a spa tub and separate shower. The partially finished basement offers additional heated and air-conditioned living space, perfect for a recreation room, home gym, additional bedroom or office. Recent updates and improvements include: Newer 3.5-ton HVAC system, new Lifetime Luxury Vinyl Plank flooring throughout, new, well pump with continuous pressure system, the tankless water heater professionally serviced, and the chimney professionally cleaned and serviced, Additional attic insulation has been added for improved energy efficiency. Outside, the property continues to impress with two exceptional outbuildings. A detached two-car garage is connected to the home by a convenient breezeway. The impressive 30' x 60' detached building offers endless possibilities with a workshop, 220-volt electric service, storage loft, office, and an expansive gathering/party room—ideal for entertaining, hobbies, car enthusiasts, or a small business. Conveniently located just 18 miles from Chestertown, Centreville, Dover, and Middletown, this one-of-a-kind property offers the perfect blend of country living and accessibility. If you've been searching for privacy, quality, and versatility, this exceptional property is one you won't want to miss! Professional interior pictures to come in about two weeks.

620 Baxter Rd, Sudlersville

Listing courtesy of Taylor Properties. Contact:

$1,100,000
3 Beds 3 Baths
The Kerr Model Home offers a beautifully crafted layout enhanced with elevated designer finishes throughout—available now for immediate settlement with a rent-back opportunity. Thoughtfully designed with 3 bedrooms, 3 baths, and a 3-car garage, this home blends spacious living, refined styling, and everyday functionality. Standout features include a dedicated home office, an inviting fireplace, and professionally designed details such as a feature wall, crown molding, and sliding barn doors that add custom character to each space. As an added benefit, all model home furniture is included, providing a fully move-in-ready experience. The gourmet kitchen is equipped with a Profile range, single oven, microwave, range hood, dishwasher, side-by-side refrigerator, elegant pendant lighting, and a designer tile backsplash. Quartz countertops elevate both the kitchen and the owner’s bath for a clean, cohesive finish. Hardwood flooring extends across the main level, with tile in all full baths and carpet in Bedroom 2 and the loft for added comfort. The owner’s bath features a shower with seat, handheld shower wand, and double sinks, creating a spa-inspired retreat designed for everyday ease. For a full list of included features, please contact our sales representatives. 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.

123 Flycatcher Way, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

$1,200,000
3 Beds 4 Baths
The Franklin Model Home offers a beautifully designed open-concept layout enriched with elevated designer finishes—available now for immediate settlement with a rent-back opportunity. With 3 bedrooms, 3.5 baths, and a 2-car garage, this home provides a refined blend of comfort, versatility, and modern style. Standout features include a dedicated home office, a cozy fireplace, and a screened patio that extends your living space outdoors. Thoughtful design details—such as barn doors, crown molding, and a custom feature wall—add character and craftsmanship throughout. As an added bonus, all model home furniture is included, offering a seamless move-in-ready experience. The beautifully appointed kitchen features a range, single oven, microwave, range hood, dishwasher, French door refrigerator, stylish pendant lighting, and a coordinating tile backsplash. Quartz countertops elevate both the kitchen and the owner’s bath for a fresh, integrated design. LVP flooring extends across the main level for durability and style, with tile in all full baths and carpet in Bedrooms 2 and 3 for added comfort. The owner’s bath offers a spa-inspired shower with a built-in seat, handheld shower wand, and double sinks—creating a relaxing and functional daily retreat. For a full list of included features, please contact our sales representatives. 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.

117 Flycatcher Way, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

$1,200,000
5 Beds 5 Baths
The Tuscaloosa Model Home offers an exceptional open-concept design enriched with high-end finishes and thoughtful upgrades throughout. Available for immediate settlement with a rent-back opportunity, this expansive home features 5 bedrooms, 4.5 baths, and a 3-car garage, delivering both space and sophistication. Standout features include a dedicated home office, an inviting fireplace, and a screened patio perfect for indoor–outdoor living. Custom design elements—such as barn doors, ceiling beams, and a striking feature wall—bring warmth, character, and craftsmanship to every corner. As a premium bonus, all model home furniture is included, providing a fully move-in-ready lifestyle. The chef-inspired kitchen showcases a Profile range, single oven, microwave, range hood, dishwasher, French door refrigerator, elegant pendant lighting, and a stylish tile backsplash. Quartz countertops elevate both the kitchen and the owner’s bath for a clean, cohesive look. Hardwood flooring spans the main level for timeless appeal, with tile in all full baths and carpet in Bedroom 2, the loft, and Bedrooms 4 and 5 for added comfort. The owner’s bath features a luxurious shower with a built-in seat, handheld shower wand, and double sinks—creating a serene, spa-like retreat. For a full list of included features, please contact our sales representatives. 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.

111 Flycatcher Way, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

$825,000
4 Beds 3 Baths
Welcome to 313 Thomas White Boulevard in the sought-after waterfront community of Gibson's Grant on Kent Island. This beautifully maintained Koch-built home offers more than 3,200 square feet of thoughtfully designed living space with four bedrooms, two-and-a-half baths, and a flexible floor plan tailored to today's lifestyle. The main level features hardwood flooring,crown molding and refined architectural details throughout, a main-level home office, and a spacious family room anchored by a cozy gas fireplace. The gourmet kitchen is designed for both everyday living and entertaining, showcasing granite countertops, rich mahogany cabinetry, stainless steel appliances, double wall ovens, a center island, pantry, and a sunny breakfast area. Upstairs, the spacious primary suite offers a walk-in closet and a luxurious en-suite bath with a soaking tub and separate shower, while three additional bedrooms provide plenty of room for family and guests. Above the garage, an expansive bonus room offers endless possibilities for recreation, work, fitness, or guest accommodations, making it one of the home's most versatile spaces. Relax on the welcoming front porch where you can enjoy the neighborhood's charming streetscape and peaceful surroundings, or unwind in the screened porch overlooking the fenced backyard, an inviting space for morning coffee, outdoor dining, or relaxing. A rear-entry two-car garage adds everyday convenience while preserving the home's classic curb appeal. Located in one of Kent Island's premier waterfront neighborhoods, Gibson's Grant offers exceptional resort-style amenities, including a community pool, clubhouse, fitness center, walking trails, kayak launch, fishing pier, pavilion, playgrounds, picnic areas, and water access to Macum Creek and the Chester River. Just minutes from Route 50 and the Chesapeake Bay Bridge, this home provides an easy commute to Annapolis, Baltimore, Washington, D.C., and Maryland's Eastern Shore while offering the relaxed coastal lifestyle that makes Kent Island so desirable.

313 Thomas White Blvd, Chester

Listing courtesy of Monument Sotheby's International Realty. Contact: (443) 906-3848

$475,000
4 Beds 3 Baths
Everything has been done—just move in and start enjoying the Eastern Shore lifestyle! This beautifully renovated 4-bedroom, 3 full bath home blends modern finishes with functional living spaces, offering room to spread out both inside and out. ✨ Completely renovated throughout ✨ Gorgeous new kitchen with center island, butcher block countertops & high-end stainless steel appliances ✨ New flooring throughout ✨ Beautifully updated bathrooms ✨ Finished walk-out lower level featuring a spacious rec room with fireplace, fourth bedroom & full bath—perfect for guests, a home office or multi-generational living ✨ Large deck overlooking an expansive, fenced backyard ✨ Oversized driveway with room for multiple vehicles, your boat, RV and more Located in the desirable Kent Island Estates community, you'll enjoy the option to join the voluntary civic association with access to community beaches, all while being just minutes from shopping, dining, marinas and the Chesapeake Bay Bridge for an easy commute. This is the kind of turnkey home buyers have been waiting for—updated, spacious, and perfectly positioned to enjoy everything Kent Island has to offer.

231 Wicomico Rd, Stevensville

Listing courtesy of Samson Properties. Contact: 7033788810

$525,000
3 Beds 2 Baths
Welcome to this much loved 19-acre property that offers pastures, trees and about 50+' feet of shoreline on the Chester River.  Launch your kayak, johnboat or fish from your shoreline!  This charming home was built in 1920 and provides 3-bedrooms and 2-baths.  Versatile floor plan, currently set up as 2 living spaces to accommodate generational living.  The spacious family room is filled with natural light and overlooks the pastures and trees.  The main kitchen is open to the family room.  The spare room off the kitchen could be perfect for a dining room.  Take a moment to relax on the welcoming front porch before exploring the second living area, complete with its own family/living room, kitchen, two bedrooms, and a full bath.  Also, this home has a huge walk-up attic and the roof is New 2026!    Don't miss the large outbuilding with electricity. It has excellent space for a workshop, storage, etc. This private country residence offers acreage, water access, and flexibility in one peaceful setting.  Providing endless opportunities for recreation, gardening, horses, livestock, or simply relaxing.. No HOA. Close to Chestertown, Centreville and Middletown Delaware.

204 Groff Rd, Millington

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$747,900
4 Beds 3 Baths
Welcome Home! JUST LISTED & OPEN Saturday 8/8 11am-1pm and Sunday 8/9 9am-11am OR by APPT DAILY! Barely lived in, this home still looks like new, offering all the benefits of new construction without the wait. The thoughtfully designed floor plan of the Simone model offers exceptional flexibility. The main level features a stunning gourmet kitchen with crisp white cabinetry, a large center island, stainless steel appliances, a wall oven/microwave combination, a propane gas range, all within an open-concept layout that flows into the light-filled dining room. The lovely living room is anchored by a cozy stone fireplace, while the screened porch provides the perfect place to relax and unwind. The main-level primary suite features tray ceilings and offers a spa-inspired bath with an expansive walk-in closet, dual vanities, and a large walk-in shower. One additional bedroom and a private office/den (or optional 5th bedroom), as well as a full bath and laundry room, are all located on the main level. Upstairs, you'll find a loft/family room, perfect for entertaining. Two additional bedrooms and a full bath accommodate family and guests. The attached garage provides added convenience and storage. Beyond the home, you'll enjoy an unmatched resort-style lifestyle with incredible community amenities, including a 23,000-square-foot clubhouse, gym, indoor and outdoor pools, billiard room, tennis and pickleball courts, a community pier, outdoor bar, fire pit, and a full calendar of social events. The nearby Cross Island Trail is perfect for walking, running, or biking, and you're just minutes from shopping, dining, and everything Kent Island has to offer. If you're looking for a home that combines luxury, space, and an exceptional lifestyle, 209 Harrier is one you won't want to miss.

209 Harrier Way, Chester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$1,995,000
5 Beds 5 Baths
Welcome to 92 Long Creek Drive, an extraordinary Kent Island waterfront estate where luxury living meets exceptional investment potential. Perfectly positioned on more than 2.5 private acres with approximately 250 feet of shoreline, this remarkable property offers the opportunity to enjoy a waterfront retreat while benefiting from an established, successful short-term vacation rental with proven income history. Profit and loss statements are available upon request, and the home is available fully furnished for a truly turnkey experience. Spanning nearly 4,000 square feet across four finished levels, the home features five bedrooms, four full baths, multiple living and entertaining spaces, and sweeping water views from nearly every room. The beautifully renovated kitchen is the heart of the home, offering white cabinetry, granite countertops, a commercial-grade refrigerator, custom pantry, shiplap accents, generous dining space, and stunning waterfront vistas. The primary suite is a peaceful retreat with panoramic water views and a luxurious bath featuring a soaking tub and tiled shower. Multiple living areas—including a lower-level recreation room with a full bar and full bath—provide abundant space for entertaining family and guests. Outside, every detail has been designed to embrace the Chesapeake Bay lifestyle. Enjoy the in-ground pool, outdoor kitchen and pavilion, expansive waterside deck and patio, beautifully landscaped grounds, and a private pier with boat lift and new electric service for enjoying boating, fishing, crabbing, paddleboarding, and kayaking. The property also includes an attached garage and a heated detached three-car garage, providing exceptional storage for vehicles, boats, water toys, and recreational equipment. Whether you're searching for a full-time waterfront residence, an unforgettable family retreat, or an investment property with an established rental history, 92 Long Creek Drive delivers an exceptional lifestyle just minutes from the Bay Bridge, Annapolis, and the rest of Maryland's Eastern Shore.

92 Long Creek Dr, Stevensville

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$868,000
4 Beds 3 Baths
A must see home! Super floor plan! Wonderful hardwood floors! Custom fixtures and finishes throughout! The best Family/Great room ever with floor to ceiling fireplace with vaulted ceilings plus outside access to stone patio w/hot tub. Wonderful kitchen featuring oak cabinetry, upgraded appliances, crown moldings, tile & granite backsplash & countertops and eat in breakfast area. Formal Dining room, main level fourth bedroom or office with half bath and exterior entrance, perfect for occasional client or guest. Large 17x13 1st level Living Rm with hardwoods & display center. Inside entrance to the four car garage with additional built-in storage & shelving! Upper level primary bedroom suite featuring 2 walk in closets, gorgeous primary bath with double vanity, huge walk in shower, quartz counters and trim, jetted soaking tub and wainscoting & chair rail finishes. Bedroom #2 w/walk in closet & double entry full bath. Bedroom #3 w/walk in closet, ceiling fan and upper deck access. Upper level laundry area with washer, dryer, shelving and deep sink. Exterior features include 1 Acre lot, beautiful pool with adjoining deck, screen porch, patio w/hot tub and garden shed. Front porch with covered sitting area. Oversized driveway w/side parking area perfect for boat or RV storage. Exterior audio & video system currently in use but not included in the sale. Your super opportunity for a wonderful home!

113 Bentons Pleasure Rd, Chester

Listing courtesy of Cummings & Co. Realtors. Contact: (410) 823-0033

$285,000
3 Beds 2 Baths
Enjoy comfort, convenience, and scenic surroundings in this lovely3‑bedroom, 2‑bath condo located in the desirable Thompson Creek community. This inviting home features a cozy living room fireplace and a peaceful pond view, creating a warm and relaxing atmosphere year‑round. Residents benefit from outstanding community amenities, including a walking trail, outdoor pool, and fitness center. Perfectly situated for easy access to the Bay Bridge, local shopping, dining, and commuter routes, this location offers both practicality and lifestyle appeal. A wonderful opportunity to enjoy low‑maintenance Eastern Shore living in a beautifully maintained community. Pictures are vitural

1403 Marion Quimby Dr, Stevensville

Listing courtesy of Benson & Mangold, LLC. Contact: (443) 988-0483

$856,000
3 Beds 3 Baths
Welcome to Your Dream Home at Four Seasons on Kent Island. Step into refined elegance and low-maintenance, luxury main-level living with this stunning Lille Loft model. This single family home with 10 foot ceilings blends style, comfort, and functionality, in Kent Island's premier 55+ resort-style community. Enjoy the convenience of a thoughtfully designed main level home featuring a spacious primary suite, guest bedroom, and a private home office - perfect for working from home or hosting visitors. A chef's dream, the Gourmet Kitchen is the heart of the home, boasting upgraded appliances, expansive quartz counter tops, custom cabinetry, double wall ovens, stainless steel refrigerator with French doors, and a large island ideal for entertaining, and a separate beverage center! Your primary suite includes a spa style bathroom complete with walk-in shower. The upper level of the home offers a spacious loft, a flexible area perfect for a second family room, hobby space, and an additional bedroom and bathroom for overnight guests. Also, the large above attic storage room is fully finished. More storage is available in the oversized fully finished two car garage with extra room for a golf cart. Off the dining area is a screened-in porch and patio, and the community run irrigation system to keep your lawn lush and green! You will certainly enjoy the 24,000 square foot Clubhouse located directly on the Chester River. Fantastic amenities include an outdoor infinity pool, indoor pool with on-duty lifeguard, fitness center, library, game room, gas and wood burning fire pits, Tiki bar equipped with refrigerators, sinks and television monitors, pier with transient boat slips, walking paths that link to the Cross Island Trail, pickle ball & tennis courts, bocce, dog park, and an outdoor amphitheater for live music and movie nights. The community lifestyle director will keep you busy with daily activities such as yoga and an assortment of clubs including biking, billiards, book club, baking, mahjong, environmental club, trivia night and more. This development is an unrivaled, amenity-filled, resort-style experience with convenient access to Annapolis (17 miles), DC (45 miles), Baltimore (45 miles), and BWI (30 miles). Kent Island offers multiple dining and shopping options, a nearby outlet mall, and a 6.5 mile cross-island trail surrounded by endless views of the Chester River.

193 Spinnaker Way, Chester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$599,900
5 Beds 3 Baths
Please remove shoes or use shoe covers provided! Welcome to the rarely-available upgraded Hudson model at Perry's Retreat located at 106 Pixie Court. This beautiful unit offers the perfect blend of space, comfort, and modern design on a PREMIUM LOT. This home presents a rare opportunity to own one of the community's most desirable models in a cud-de-sac. The main level features an open concept design that seamlessly connects the kitchen, dining, and living areas, creating an ideal layout for both everyday living and entertaining. A private office with French doors provides the perfect work from home space, while an additional ensuite bedroom on this level offers endless possibilities as a guest room, or hobby space. The upgraded kitchen serves as the heart of the home, showcasing quartz countertops, stainless steel appliances, upgraded backsplash, additional wall oven, and a large island overlooking the spacious living room. Luxury vinyl plank flooring in most of the main level adds both style and durability. Upstairs, the spacious primary suite offers a relaxing retreat with a tray ceiling, two oversized walk-in closets, and a beautifully appointed en-suite bathroom featuring dual vanities, private water closet, and linen closet. Three additional bedrooms, a full bathroom with double sinks, and a convenient upper-level laundry room complete the second floor. Outside, enjoy a backyard that creates a setting for relaxation and entertaining. Community amenities include a playground, open green space for neighborhood events. Conveniently located just minutes from Route 50, residents enjoy easy access to Kent Island, Annapolis, Easton, St. Michaels, Oxford, Tilghman Island, Baltimore, and Washington, D.C. Directly across from the community, the Chesapeake Bay Environmental Center offers hiking trails, kayaking, wildlife viewing, educational programs, and summer camps, allowing you to fully embrace the Eastern Shore lifestyle. Professional photos coming soon!

106 Pixie Ct, Grasonville

Listing courtesy of HomeSmart. Contact: 3013524065

$555,000
4 Beds 3 Baths
Eastern Shore living begins here! Welcome to 532 Cross Creek Court in the desirable Claybourne Woods community of Chester. This beautifully maintained 4-bedroom, 2.5-bath home offers plenty of space to gather, relax, and create lasting memories. Whether you're hosting gatherings, enjoying quiet evenings at home, or entertaining friends, this home provides the perfect setting. Located on Kent Island, you'll enjoy the best of both worlds peaceful neighborhood living with convenient access to waterfront dining, marinas, shopping, recreation, and major commuter routes. Just minutes from the Bay Bridge, this home is ideal for those seeking the charm of the Eastern Shore without sacrificing convenience.

532 Cross Creek Ct, Chester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: