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132 Pennick Dr, Stevensville
$449,000
3 Beds ⋅ 3 Baths
Privacy & serenity you've been searching for on coveted Kent Island in this beautifully maintained ONE-LEVEL rancher, offering over 1,700 square feet of comfortable living on a secluded 0.65-acre homesite. Featuring 3 spacious bedrooms, 2½ baths, an updated kitchen (2025), renovated full bath (2023), Roof (2015), NEW 100' well (2022), this move-in-ready home combines modern updates with everyday convenience. Step outside to your own private retreat with a fenced backyard, sparkling in-ground pool, shady gazebo, and ample room to entertain or simply unwind. A wide concrete driveway provides generous parking, while the rear wheelchair ramp adds accessibility and flexibility. Perfectly positioned just blocks from the Cross Island Trail and Romancoke Pier, with multiple public boat ramps nearby, you'll enjoy the very best of the Kent Island lifestyle. Local shopping, restaurants, waterfront recreation, and an easy commute to both work and play are all just minutes away. Sunporch off kitchen -new windows convey for future install/finishing. Private, updated, and ready for its next lucky owner—this Kent Island gem is one you won't want to miss.

132 Pennick Dr, Stevensville

Listing courtesy of Chaney Homes, LLC. Contact:

300 Woods Point Rd, Chester
$2,625,000
3 Beds ⋅ 2 Baths
Privacy without isolation! - Rare Find - 2 comfy homes on one waterfront property, each served by public sewer.! Both with unobstructed views of the picturesque Cox Creek before it enters the Bay. Discover a captivating traditional charm in this vintage cape cod recently updated in spring 2026 ( 3-bedrooms, 2-bathrooms, with enclosed and screened porches.) The former detached garage converted into a 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.

300 Woods Point Rd, Chester

Listing courtesy of Tidewater Properties. Contact:

705 Carmichael Rd, Queenstown
$474,900
3 Beds ⋅ 2 Baths
Move-In Ready! Modern One-Level Living on a Spacious Half-Acre Lot Completed and move-in ready, this beautifully built 3-bedroom, 2-bath ranch home offers the perfect blend of quality craftsmanship, thoughtful design, and easy living. Situated on a generous half-acre lot in a peaceful country setting, this home features the convenience of one-level living with a slab foundation, providing minimal steps to enter and eliminating the need for stairs inside. Step inside to an inviting open floor plan highlighted by cathedral ceilings that create a bright and spacious living, dining, and kitchen area—ideal for both entertaining and everyday living. The kitchen has been thoughtfully upgraded with granite countertops, soft-close cabinetry and drawers, stainless steel appliances, and plenty of cabinet and countertop space. The well-designed layout offers excellent privacy, with the primary suite separated from the additional bedrooms. The spacious primary bedroom includes a private full bath and a large walk-in closet, while two additional bedrooms provide flexibility for family, guests, or a home office. Outside, you'll enjoy the privacy and room to spread out that comes with a ½-acre lot, offering plenty of space for outdoor entertaining, gardening, play, or simply relaxing and enjoying the peaceful surroundings. Features include: Move-in ready – no waiting to build 3 Bedrooms | 2 Full Bathrooms Spacious ½-acre lot One-level living with minimal steps Open-concept floor plan Cathedral ceilings in the living room and kitchen Granite countertops Upgraded soft-close cabinetry and drawers Stainless steel appliances Luxury vinyl plank flooring Attached 2-car garage Peaceful country setting Whether you're looking to downsize, purchase your first home, or simply enjoy the convenience of one-level living, this home offers modern finishes, an efficient floor plan, and the comfort of a brand-new home that's ready for immediate occupancy. Don't wait months for new construction—this beautiful home is complete, move-in ready, and waiting for its new owners. Schedule your private showing today!

705 Carmichael Rd, Queenstown

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

143 Thicket Ct, Centreville
$899,000
5 Beds ⋅ 4 Baths
$10,000 CREDIT TOWARDS CLOSING COSTS WITH ACCEPTED OFFER BY OCTOBER 10TH! Discover the perfect blend of modern comfort and peaceful Eastern Shore living in this exceptional home nestled at the end of a cup-de-sac in the desirable Willow Branch East community. Built in 2022 and situated on a private 1.25 acre lot backing to mature trees, this exceptional home offers over 4,300 square feet of thoughtfully designed living space in a peaceful Centreville setting. A welcoming front porch and entry foyer with elegant staircase set the tone as you step inside. The open-concept main living area features soaring two-story ceilings, creating a bright and inviting space centered around the beautifully appointed kitchen with quartz countertops, abundant cabinetry, and seamless flow into the spacious living room. The adjoining dining area overlooks the backyard and opens to the rear deck, making indoor and outdoor entertaining effortless. The main-level primary suite provides the convenience of first-floor living and includes a spacious walk-in closet and private bath. Also on the main level are a dedicated home office, a formal living room that can easily serve as a dining room, and a laundry room with convenient access to the side-entry three-car garage. Upstairs, you'll find a private bedroom with an en suite bath, three additional bedrooms, a full hall bath, and a large versatile bonus room ideal for a playroom, home office, fitness room, or guest space. The full unfinished basement with a rough-in for a future bathroom offers endless possibilities for additional finished living space. Additional highlights include a paved driveway, tankless water heater, water treatment system, and an ideal location just minutes from historic Centreville with convenient access to Route 301, Annapolis, Easton, and the Chesapeake Bay Bridge. Combining modern construction, flexible living spaces, and exceptional privacy, this move-in ready home is one you won't want to miss.

143 Thicket Ct, Centreville

Listing courtesy of Coldwell Banker Realty. Contact:

952 Chester River Dr, Grasonville
$1,299,000
5 Beds ⋅ 4 Baths
Just reduced $101k! Experience the best of Waterfront living at 952 Chester River Drive, where panoramic water views, spectacular sunsets, and thoughtful custom design come together to create an exceptional waterfront retreat. Offering over 3,500 square feet of living space, this custom-built home is perfectly positioned to capture endless water views from nearly every room. High ceilings and expansive windows fill the home with natural light while framing the ever-changing waterfront backdrop. Designed for both everyday living and effortless entertaining, the main level features an open floor plan that seamlessly connects the living, dining, and kitchen spaces. The gourmet kitchen is equipped with gas cooking, abundant cabinetry, and generous workspace, allowing you to prepare meals while enjoying stunning views of the water. With five bedrooms and three-and-a-half baths, there is plenty of room for family and guests. Thoughtful design elements throughout the home maximize both functionality and comfort while keeping the focus on the incredible waterfront setting. Step outside and discover a boater's dream. The private pier is equipped with electric, water, three boat lifts, including a 20,000-pound lift, 10,000-pound lift, and 2,500-pound lift, offering exceptional flexibility for multiple vessels and watercraft. Spend your days on the water and return home to breathtaking sunsets over the Chester. Additional features include a NEW roof, 2 - 1 year old HVAC systems, tankless hot water heater, attached two-car garage with excellent storage, 50 amp RV hook up, and the quality craftsmanship expected in a custom-built waterfront residence. Whether you're searching for a year-round residence or the ultimate waterfront getaway, 952 Chester Beach Road offers a rare opportunity to enjoy unmatched views, premier boating access, and the relaxed lifestyle that makes Maryland's Eastern Shore so special.

952 Chester River Dr, Grasonville

Listing courtesy of Samson Properties. Contact:

410 Wallman Way, Stevensville
$1,700,000
9 Beds ⋅ 4 Baths
Experience some of the most captivating views the Chesapeake Bay has to offer. Perfectly positioned at the first exit off the Bay Bridge, this waterfront property showcases sweeping water views, stunning sunrises, and a front-row seat to the iconic Chesapeake Bay Bridge. The shoreline is ideal for enjoying the Bay lifestyle-launch a kayak, paddleboard, jet ski, or small skiff right from your backyard, spend the day fishing or crabbing, and unwind while watching the backdrop of the Bay Bridge. Like new construction this home was built just three years ago, this remarkable home offers 9 bedrooms plus a den, this includes a private 4-bedroom in-law suite with its own kitchen/laundry and entry perfect for in-laws, guests or even its own apartment. Public water and public sewer provide added convenience, while the location offers easy access to shopping, dining, and everyday amenities without ever having to navigate Route 50. Whether you're seeking a waterfront family compound, vacation getaway, or year-round residence, this property combines modern living, unmatched convenience, and unforgettable Chesapeake Bay views. Lot next door is included in sale giving home just under 1 acre.

410 Wallman Way, Stevensville

Listing courtesy of Chaney Homes, LLC. Contact:

114 Edenderry Ave, Centreville
$474,500
3 Beds ⋅ 2 Baths
PRICE OPTIMIZED TO $474,500! Enjoy true single-level living with NO HOA FEES in Centreville's desirable North Brook community. This beautifully maintained 3-bedroom, 2-bathroom rancher features a bright, open floor plan that flows seamlessly into a stunning, light-filled sunroom. French doors open to a premium custom brick patio (2023), perfect for outdoor entertaining on the spacious 0.34-acre lot. The upscale eat-in kitchen boasts granite countertops and dual pantries for exceptional storage. Peace-of-mind upgrades are completely done for you: New Roof (2020), Fully Encapsulated Crawl Space (2021), and 6" Gutter Guards with Underground Drainage (2022). Additional features include an attached 2-car garage with newly insulated walls and pull-down attic access. For total buyer convenience, a recent property boundary survey and lot staking have already been completed! Close to historic Centreville's wharf, trails, and dining. Move right in!

114 Edenderry Ave, Centreville

Listing courtesy of Benson & Mangold, LLC. Contact:

104 Port Ct, Grasonville
$1,200,000
4 Beds ⋅ 3 Baths
WATERFRONT LIVING ON WINCHESTER CREEK! Welcome to this incredible 4-bedroom, 2.5-bath Grasonville estate offering the ultimate Eastern Shore lifestyle. The home is fully refreshed with a freshly painted neutral interior, gleaming hardwoods, and plush new carpet. A grand 2-story foyer with a Palladian window welcomes you inside to a main level featuring soaring 11' ceilings, a great room with a gas fireplace, and a striking bank of windows framing gorgeous water views. The main-floor primary suite boasts a walk-in closet and a zero-threshold shower. Two additional generously sized bedrooms, a full hall bath, and a guest powder room complete the main-level living spaces. Entertaining is a breeze in the bright breakfast room and fabulous kitchen, which features newer appliances, a separate pantry, and a center island. The separate dining room, with its soaring ceiling and wall of windows, is the absolute chef's kiss. Upstairs, a versatile bonus space with custom built-ins serves as a perfect home office or media room. Your outdoor resort awaits! A Trex deck with built-in benches and a retractable awning leads to a custom paver patio and a sparkling 18’ x 37’ saltwater pool with a tranquil waterfall feature. Boaters will love the convenience of their own deeded boat slip (#10), mooring pile, and private boat lift on Winchester Creek just a short walk away, offering protected deep-water access directly to the Chester River and Kent Narrows. Experience the legendary Eastern Shore dock-and-dine lifestyle by boat or car, with regional favorites like The Narrows, Bridges, and the brand-new Dock House just minutes away. Enjoy close proximity to trails at CBEC, shopping, top-tier healthcare at , and highly regarded . This estate beautifully pairs absolute waterfront tranquility with everyday convenience! Mechanics & Storage: Main-level laundry with sink, oversized 2-car garage with multiple storage rooms, HVAC (2018), buried 500-gallon propane tank, and a fully serviced water conditioning system with reverse osmosis.

104 Port Ct, Grasonville

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

103 Opera Ct, Centreville
$489,000
3 Beds ⋅ 2 Baths
FANTASTIC value for a 3-BR home on a prime lot! Welcome to 103 Opera Court in the sought-after, active 55+ community of Symphony Village at Centerville. This expanded Vivaldi model features three bedrooms and two full bathrooms on an oversized corner lot across from parklands and with no home behind the paver patio. Pull up to your side loading garage and take the short path to the front door, with a quaint covered porch for slow evenings and watching nature go by. Once inside, the spacious foyer offers a dry bar with mini-fridge and architectural pillars lead to an open concept living space. You’re invited in by unobstructed views from the dining area through the living area into the family room extension with a vaulted ceiling and fireplace with marble surround. There is beautiful, engineered hardwood flooring throughout the public spaces. Unmatched natural light drenches the entire space which centers on the cozy gas fireplace for ease of use on the few chilly winter nights. The gourmet, open style kitchen features gorgeous cabinetry, granite countertops, stainless steel appliances, including double wall ovens that are sure to please any chef. The primary bedroom suite has brand new carpeting, a sitting area with vaulted ceiling, a tray ceiling above the bed for added drama, and double walk-in closets. The primary bath features separate vanities, a jetted soaking tub and a custom, walk-in tub. The second bedroom is down the hall from the entry and is adjacent to the second well-appointed full bath. The third bedroom, at the front of the home, is a perfect flex space and could be a bedroom, office, or studio. It also has wood floors and plenty of natural light. Tucked away at the center of the home is the laundry which is on the way to the two-car garage. The garage features a “sky basement” above, which is partially finished and can be used for storage. Outside the French doors in the family room is a paver patio, perfect for entertaining, dining alfresco or taking your morning coffee. For peace of mind and low utilities, this home also has solar panels and a whole house generator. The community takes care of the grounds, leaving you more time to relax and enjoy the peace and quiet and the many amenities! There are paths for walking or biking, including one leading to the local shopping center, pickleball and tennis courts, putting green, bocce ball courts and a resort style outdoor pool. The clubhouse features a concert hall, billiards room, fitness room, bar, party rooms, dining room, and an indoor heated pool open every day. Activities include classes to learn a variety of skills, social hour, arts and crafts, game and card nights, an artist guild with quarterly art shows and much more for the low HOA fee. The historic and charming town of Centerville is minutes away with wonderful restaurants and shops, and a wharf for boating, paddling or a picnic. Enjoy the slower pace of the eastern shore while remaining close to the ocean beaches and the city life across the Chesapeake Bay. This home has SO MANY UPGRADES and beautiful views – it’s a very special property.

103 Opera Ct, Centreville

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

121 Eareckson Ln, Stevensville
$850,000
4 Beds ⋅ 3 Baths
Nestled within the serene enclave of Goose Point Estates, this exquisite one level living home offers a harmonious blend of luxury and comfort, perfect for those seeking an elevated lifestyle. This residence boasts a modern aesthetic while retaining its timeless charm. Step inside to discover a spacious 2,141 square feet of meticulously designed living space. The interior features a warm palette complemented by rich hardwood flooring and plush carpeting, creating an inviting atmosphere throughout. Crown moldings and chair railings add a touch of elegance, while recessed lighting and skylights bathe the space in natural light. The heart of the home is undoubtedly the gourmet kitchen, equipped with upgraded countertops and ample table space for casual dining. High-end appliances, including a self-cleaning oven, built-in microwave, and energy-efficient dishwasher, make cooking a delight. The adjacent family room, complete with a charming wood-burning fireplace, provides a perfect retreat for relaxation. This residence features four generously sized bedrooms, including a main-level bedroom for convenience. The luxurious master suite offers a walk-in closet and a spa-like bathroom with a stall shower included with a hot tub, ensuring a private oasis for unwinding after a long day. Outside, the property is equally impressive, set on a sprawling 2.4-acre lot surrounded by lush trees and serene woods, providing a tranquil backdrop for outdoor living. Enjoy evenings under the stars in the hot tub or host gatherings with friends in the beautifully landscaped yard. The exterior is adorned with thoughtful features such as bump-outs, exterior lighting, and flood lights, enhancing both functionality and aesthetics. Additional highlights include a spacious attached garage with extra storage, main-floor laundry for added convenience, and a water treatment system for peace of mind. This home is not just a residence; it's a lifestyle choice, offering a perfect blend of luxury, comfort, and nature. Experience the best of both worlds in this exceptional property, where modern amenities meet the tranquility of nature, creating a perfect sanctuary to call home. Roof is 10 years old. Goose Point Estates is just minutes away from route 50 and the Chesapeake Bay Bridge but far enough away from all the traffic.

121 Eareckson Ln, Stevensville

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

24 Fairway Is, Grasonville
$559,000
3 Beds ⋅ 3 Baths
NEW PRICE — A GREAT OPPORTUNITY IN PROSPECT BAY! Offering approximately 2,850 square feet of living space, this contemporary presents an opportunity to enjoy the Prospect Bay lifestyle at an attractive price point. Available for the first time since 1999, this well-loved home is ready for its next chapter. The spacious family room features a brick fireplace, cathedral ceiling and triple sliders opening to the deck and backyard. The kitchen offers lovely cabinetry, generous counter and storage space, and plenty of room for casual dining. Two bedrooms are conveniently located on the main level, along with a separate dining room and dedicated mudroom with laundry. Upstairs, the spacious primary suite offers privacy, while a loft overlooking the family room provides flexible space for a home office, sitting area, or additional living area. Oversized 2-car garage, plus deck overlooking the backyard. Located in Prospect Bay Golf & Country Club, where residents enjoy golf, swimming pool, tennis courts, boat ramp, and clubhouse with restaurant. Bring your ideas and make this home your own while enjoying all that Prospect Bay has to offer.

24 Fairway Is, Grasonville

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

205 Bryantown Lndg, Queenstown
$324,900
4 Beds ⋅ 2 Baths
MAJOR PRICE IMPROVEMENT! Discover this updated home that blends classic architecture with modern living, offering 1,783 sq. ft. of versatile space. Venture inside to find a welcoming traditional floor plan with new luxury vinyl plank flooring and fresh interior paint that flows from the living room to dining room and well-appointed bedrooms. The upgraded kitchen, equipped with white shaker cabinetry, stainless-steel appliances and granite countertops, is a perfect place for culinary enthusiasts. The three bedrooms and full bathroom equipped with a stall shower and whirlpool tub, ensures comfort and relaxation after a long day. The finished 2nd level with new carpet flooring can be converted or used into a 4th bedroom while the main level sunroom with its bright airy ambience is a perfect spot for entertaining. Outside, enjoy the tranquility of your front and rear yards, great for gardening or outdoor activities.

205 Bryantown Lndg, Queenstown

Listing courtesy of Century 21 Downtown. Contact:

223 Overlook Dr, Queenstown
$550,000
4 Beds ⋅ 3 Baths
Absolutely Charming Eastern Shore Home with Beautiful Farm Views! Experience the peaceful charm of Queenstown living in this beautifully updated home situated on a gorgeous .83 acre lot surrounded by the natural beauty of Maryland’s Eastern Shore. Enjoy the slower pace of life with open farmland views, plenty of outdoor space, and a setting that feels away from the congestion while still being convenient to nearby shopping, restaurants, waterfront areas, and commuter routes. The welcoming front porch is the perfect place to relax and take in the scenic farm views, while the screened porch overlooking the backyard provides another wonderful space to enjoy the outdoors. Inside, this home is full of warmth and character with luxury vinyl plank flooring throughout the main level and thoughtful updates throughout. The upgraded kitchen features white cabinetry, stainless steel appliances, and a convenient laundry room nearby. The inviting family room offers a cozy wood burning fireplace, creating a comfortable gathering space. A main level office with a beautiful French door entry offers flexibility and could also serve as an additional bedroom, guest space, or hobby room. Upstairs, you will find three spacious bedrooms with fresh carpeting, including the impressive primary suite featuring a large ensuite bathroom, walk-in shower, dual sink vanity, and generous closet space. The additional bathrooms have also been beautifully updated. With abundant parking, nearly an acre of land, peaceful surroundings, and views that capture the best of Eastern Shore living, this Queenstown charmer is truly a special place to call home.

223 Overlook Dr, Queenstown

Listing courtesy of Douglas Realty LLC. Contact:

913 Clark Corners Rd, Centreville
$585,000
4 Beds ⋅ 3 Baths
OVER 5 ACRES. NO HOA. JUST MINUTES FROM US301. That’s a combination that’s becoming increasingly difficult to find. Welcome to 913 Clark Corners Rd, where 5.42 ACRES of partially wooded land offer the freedom to live your way! Whether you’re dreaming of horses, chickens, gardening, recreational activities, frequent sightings of deer, birds, owls, and other wildlife, or simply room to breathe, this property delivers the space and flexibility today’s buyers are searching for. Inside, you’ll find a thoughtfully updated home featuring a fully renovated kitchen with quartz countertops, 42” soft-close white cabinetry, stainless steel appliances, recessed lighting, a large center island with seating, and luxury vinyl plank flooring that flows seamlessly into the spacious family room with a gas fireplace. The main level also boasts engineered hardwood floors and offers formal living and dining rooms, an updated powder room, and a renovated laundry/mud room with additional cabinetry, countertop workspace, and valuable pantry storage. Upstairs, the spacious primary suite includes a walk-in closet and private bath, while three additional bedrooms and a full hall bath provide room for family, guests, hobbies, or a home office. Outside, enjoy a welcoming wraparound front porch that’s perfect for relaxing and taking in the peaceful surroundings, along with a rear deck, partially fenced backyard, large storage shed, mature landscaping, permanent Govee front exterior lighting, and a blend of open yard and wooded acreage that creates a setting rarely found at this price point. Above the garage, the unfinished attic space provides exceptional storage and potential future possibilities, subject to buyer verification of county requirements and approvals. Whether you’re looking for room to grow, room to roam, or simply room to breathe, this property delivers!

913 Clark Corners Rd, Centreville

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

Baltimore Drive, Stevensville
$549,900
3 Beds ⋅ 2 Baths
Coming soon — brand new construction opportunity! This thoughtfully designed ranch-style home will be breaking ground soon and offers the chance to secure a brand-new home before construction begins. Featuring convenient one-level living, this home will include an open floor plan with vaulted ceilings and quality finishes throughout. The kitchen is planned to feature quartz countertops, stainless steel appliances, a center island, and ample cabinet space, opening to the spacious living and dining areas—ideal for everyday living and entertaining. The primary suite is designed as a private retreat with a spacious bedroom, walk-in closet, and ensuite bath featuring a double vanity and oversized shower. Additional bedrooms provide flexibility for guests, family, or a home office. Other highlights include a dedicated laundry room, generous storage, and an attached 2-car garage. Situated on a spacious lot, buyers may have the opportunity to make selections depending on the stage of construction. Get in early and make this upcoming new construction home yours before it’s built!

Baltimore Drive, Stevensville

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

335 S Carolina Rd, Stevensville
$734,500
4 Beds ⋅ 4 Baths
335 S. Carolina Rd is ready for its 2nd owner! Potential income producing property, would make an amazing short term rental vacation property! Enjoy sprawling views of the Chesapeake Bay from every level. Only 3 years young, this home is beautifully appointed and move in ready. As you enter, the first floor opens to a living space with a slider that leads to your lush green back yard. There is also a full bathroom and bedroom. The second floor is where the magic is. Your living room with fireplace, kitchen and dining space are open for you to enjoy the spectacular water views from all angles. The third floor boasts 3 bedrooms and 2 full bathrooms including the waterside primary suite with its own private deck. Some special features include a bright open floor plan, balconies with water views, a gorgeous fire pit, and walkable to the Bay and beach. Also enjoy a widened driveway for extra parking spaces, a water softener system and storage shed. This home features 3 decks and a 2 car garage. Move in time to enjoy all that a beautiful Kent Island summer has to offer.

335 S Carolina Rd, Stevensville

Listing courtesy of Coldwell Banker Realty. Contact:

128 Allison Jane Dr, Stevensville
$650,000
3 Beds ⋅ 3 Baths
Welcome to Ellendale—where modern comfort meets Eastern Shore charm. This beautifully maintained 3-bedroom, 2 full and 1 half bath home, built in 2018 by Baldwin Homes, offers the feel of new construction with a spacious, light-filled layout, a desirable first-floor primary suite, and a 2-car garage. Designed for both everyday living and effortless entertaining, the home features stylish finishes throughout, along with two added Mitsubishi mini-split systems for enhanced comfort and energy efficiency. Step outside to enjoy the fully fenced backyard and stone patio, creating the ideal setting for outdoor dining, gatherings, or quiet mornings with a cup of coffee. An in-ground lawn sprinkler system helps keep the yard lush and beautifully maintained with ease throughout the seasons. Nestled in the sought-after Ellendale community in Stevensville on Kent Island, you're just minutes from waterfront dining, boutique shopping, and the attractions of Kent Narrows. With convenient access to Route 50 and an easy commute to Annapolis, this home offers the perfect blend of comfort, convenience, and coastal living.

128 Allison Jane Dr, Stevensville

Listing courtesy of Mr. Lister Realty. Contact:

2800 Bennett Point Rd, Queenstown
$4,695,000
5 Beds ⋅ 5 Baths
Architect-designed contemporary waterfront home on nearly 18 private acres across two parcels with approximately 1,400 feet of shoreline on Greenwood Creek. Positioned to capture 180-degree western views, the property offers privacy, deep water, and a setting that is increasingly difficult to find on Maryland’s Eastern Shore. A custom pivoting front door creates a striking first impression and sets the tone for the home's thoughtful design. The home was designed to take advantage of the surrounding water and landscape, with floor-to-ceiling windows, open gathering spaces, and strong indoor-outdoor connections throughout. The kitchen opens to the main living areas and features a glass accordion door that connects directly to the screened porch, creating a seamless transition between indoor and outdoor spaces. The layout flows easily between the kitchen, dining areas, family room, porch, and pool area, making the home equally well suited for everyday living and entertaining. The primary suite is set apart from the rest of the home by a glass-enclosed walkway and includes a private office, large dressing room, en-suite bath, and private porch access. In addition to the primary suite, the main level includes three additional bedrooms, each with access to a private bathroom. The finished lower level includes a home theater, billiards room, bar area, workout room, additional bedroom and full bathroom, along with unfinished basement space for storage. Outdoor features include a solar-heated pool, private beach, and deep-water pier with two boat lifts. The protected shoreline and direct access to Eastern Bay make this an ideal property for boating and waterfront living. A three-bay outbuilding with workshop space and additional storage provides room for equipment, hobbies, or car and boat storage. Located just outside Queenstown, the property is convenient to Easton, Annapolis, Washington D.C., Baltimore, and Philadelphia while offering the privacy and pace of the Eastern Shore.

2800 Bennett Point Rd, Queenstown

Listing courtesy of TTR Sotheby's International Realty. Contact:

420 Five Farms Dr, Stevensville
$624,900
3 Beds ⋅ 2 Baths
Welcome to 420 Five Farms Drive in the sought-after Queen Anne Colony community on Kent Island, where the Chesapeake Bay lifestyle is right outside your door. Nestled in a water-oriented neighborhood featuring a community marina, waterfront park, and endless opportunities to enjoy boating, fishing, kayaking, and stunning sunsets, this home offers the perfect blend of coastal living and modern updates. From the moment you arrive, you’ll appreciate the peace of mind that comes with a brand-new roof and brand-new siding, creating incredible curb appeal and low-maintenance living. Inside, you’ll find a light-filled, airy interior accented by beautiful hardwood floors and a stunning renovated kitchen that serves as the heart of the home. Designed for both everyday living and entertaining, the kitchen flows seamlessly into the main living spaces while offering stylish finishes and ample workspace. The home features three spacious bedrooms and beautifully updated bathrooms, providing comfort and functionality for family and guests alike. Step outside to your private backyard retreat where summer memories are waiting to be made. Relax with your morning coffee in the screened porch, host gatherings around the in-ground pool, or enjoy the privacy and security of the fully fenced backyard. Whether you’re looking for a full-time residence or the ultimate Kent Island getaway, 420 Five Farms Drive delivers the lifestyle buyers dream about, updated, move-in ready, and located in one of Stevensville’s most desirable waterfront communities. Brand-new roof. Brand-new siding. Gorgeous kitchen. Inground pool. Marina community. Chesapeake Bay lifestyle. This is the one you’ve been waiting for.

420 Five Farms Dr, Stevensville

Listing courtesy of RE/MAX Executive. Contact:

1024 Avalon Ct, Stevensville
$579,900
3 Beds ⋅ 3 Baths
Recently Reduced and Ready for Its New Owner! Experience the best of Eastern Shore living at 1024 Avalon Court, where spacious design, natural light, and a peaceful setting come together beautifully. Perfectly positioned on a desirable lot with views of the community pond area and protected woodlands, this exceptional residence offers a wonderful blend of privacy, comfort, and everyday convenience. From the inviting exterior with stone accents and a two car garage to the open interior layout and exceptional outdoor living spaces, this home is designed for easy living and effortless entertaining. Step inside to a welcoming foyer with neutral paint and a bright, airy feel that continues throughout the main level. The thoughtfully designed floor plan offers excellent flexibility with formal living and dining areas, generous open gathering spaces, and seamless flow between rooms. Expansive windows bring in beautiful natural light while framing peaceful rear views, creating a warm and inviting atmosphere throughout the home. The heart of the home is the open concept kitchen and family room area, ideal for both everyday living and entertaining. The kitchen features abundant cabinetry, granite counters, stainless steel appliances, recessed lighting, a center island cooktop, and direct connection to the surrounding living spaces. The spacious family room offers a cozy fireplace and easy access to the private screened porch and large raised concrete patio, two standout features rarely found in this community. Both outdoor spaces overlook the community pond area and protected woodlands, creating a private and peaceful backdrop for relaxing, dining, and entertaining. The home continues with spacious bedrooms, including a large main level owner’s suite with generous closet space and a private bath featuring dual vanities, a soaking tub, and separate shower. This main level suite offers excellent flexibility for multigenerational living, guests, or those seeking everyday convenience. Additional bedrooms on the upper level provide comfortable space for family, guests, home office needs, hobbies, or recreation. Outdoor living is truly a highlight, with multiple areas to enjoy the serene wooded setting. The private screened porch is perfect for morning coffee, quiet evenings, or relaxing without the elements, while the oversized raised concrete patio offers wonderful space for grilling, entertaining, or simply enjoying the peaceful rear views. Additional highlights include flexible living spaces, a heated and air conditioned two car garage with amazing storage, and a peaceful rear setting rarely found in such a convenient location. Ideally positioned with easy access to major commuter routes including Routes 50 and 301, this exceptional residence offers convenient access to Downtown Annapolis, Washington, D.C., Baltimore, Kent Island, the Bay Bridge, Middletown, Dover, NSA, Fort Meade and Dover Air Force Base. Enjoy great local amenities including restaurants, shopping, recreation, and all the lifestyle conveniences that make the Eastern Shore so desirable. Don’t miss out on this incredible opportunity!

1024 Avalon Ct, Stevensville

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

232 Evelyne St, Chester
$825,000
4 Beds ⋅ 4 Baths
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.

232 Evelyne St, Chester

Listing courtesy of TTR Sotheby's International Realty. Contact:

108 Prospect Bay Dr W, Grasonville
$819,000
4 Beds ⋅ 3 Baths
Located in the waterfront community of Prospect Bay, residents enjoy golf, swimming pool, boat ramp, tennis courts, and a clubhouse with restaurant. Welcome to this much-loved home, beautifully situated on 1.03 acres with sunset water views on one side and golf course views on the other. Quality built with 2x6 construction, the home features hardwood flooring, Andersen windows, and abundant natural light. The kitchen offers maple cabinetry, a center island, table space, and an open layout connecting to the family room with fireplace and efficient wood-burning insert. Separate living and dining rooms feature bow windows showcasing the water views. A main-level fourth bedroom with built-ins currently serves as a home office. Upstairs, the spacious primary suite features water views, a large bath, and generous walk-in closet, along with two additional bedrooms and a full bath. Enjoy a screened porch overlooking the golf course, a 16' x 12' Amish-built shed, and an oversized two-car garage with workshop space and extensive storage. The large driveway and parking pad accommodate up to six vehicles. Additional storage is available in the walk-in attic. Recent updates include a washer, dryer, refrigerator, microwave, dishwasher, and Trane heat pumps less than two years old.

108 Prospect Bay Dr W, Grasonville

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

Price Station Rd, Centreville
$649,500
4 Beds ⋅ 2 Baths
Discover the exceptional craftsmanship of Lomaxx Custom Homes with this thoughtfully designed modern farmhouse rancher! This to-be-built home offers 4 spacious bedrooms, 2 full bathrooms, and an inviting open-concept floor plan perfect for everyday living and entertaining. Unlike many new construction homes, this property comes loaded with premium upgrades already included—without the hefty upgrade costs! Standard features include a fully encapsulated and conditioned crawl space, luxury vinyl plank flooring throughout, custom trim work and built-ins, stunning faux wood beams, black windows, stainless steel appliances, quartz countertops, and high-end finishes that truly set this home apart. Situated on just over 2 acres, there’s plenty of room for whatever hobbies, recreation, or outdoor lifestyle you can imagine. The breathtaking rural views create the perfect peaceful setting while still offering convenient access to nearby destinations—approximately 5 minutes to the Town of Centreville, 20 minutes to the Bay Bridge, and just 30 minutes to Middletown, Delaware. The lot offers a beautiful natural slope away from the homesite, adding to both the setting and functionality of the property. Enjoy peaceful mornings on the covered front porch and unwind in the evenings on the rear patio while taking in the surrounding countryside. The bright and airy living spaces are complemented by a stunning kitchen and a private owner’s suite designed for comfort and relaxation. Additional floor plans and layouts are also available and can be discussed to fit your needs and vision. The builder is also open to constructing a pole barn for an additional cost, creating endless possibilities for storage, hobbies, workshop space, or recreational use. Photos shown are of a previously built model.

Price Station Rd, Centreville

Listing courtesy of CR Realty. Contact:

Clark Corner Rd, Centreville
$575,000
3 Beds ⋅ 2 Baths
Discover the exceptional craftsmanship of Lomaxx Custom Homes with this thoughtfully designed modern farmhouse rancher! This to-be-built home offers 3 spacious bedrooms, 2 full bathrooms, and an inviting open-concept floor plan perfect for everyday living and entertaining. Unlike many new construction homes, this property comes loaded with premium upgrades already included—without the hefty upgrade costs! Standard features include a fully encapsulated and conditioned crawl space, luxury vinyl plank flooring throughout, custom trim work and built-ins, stunning faux wood beams, black windows, stainless steel appliances, quartz countertops, and high-end finishes that truly set this home apart. Situated on just over 2 acres, there’s plenty of room for whatever hobbies, recreation, or outdoor lifestyle you can imagine. The breathtaking rural views create the perfect peaceful setting while still offering convenient access to nearby destinations—approximately 5 minutes to the Town of Centreville, 20 minutes to the Bay Bridge, and just 30 minutes to Middletown, Delaware. Enjoy peaceful mornings on the covered front porch and unwind in the evenings on the back deck while taking in the surrounding countryside. The bright and airy living spaces are complemented by a stunning kitchen and a private owner’s suite designed for comfort and relaxation. Additional floor plans and layouts are also available and can be discussed to fit your needs and vision. The builder is also open to constructing a pole barn for an additional cost, which would fit perfectly on the right side of the property beyond the hedge row and ditch. A culvert is being installed by the builder to provide easy access to this area, creating endless possibilities for storage, hobbies, workshop space, or recreational use. Photos shown are of a previously built model.

Clark Corner Rd, Centreville

Listing courtesy of CR Realty. Contact:

319 Twin Meadows Farm Ln, Centreville
$679,900
3 Beds ⋅ 2 Baths
Welcome to Meadow Creek. Estate homes on acre plus homesites with plenty of room for a pool and a separate garage.. In the country but close to downtown Centreville. Centreville offers restaurants, grocery stores, parks and schools. This one level home features a formal dining area flanked by columns as well as three nicely sized bedrooms and a large living area with gourmet-appointed island kitchen, breakfast room and optional morning room on one level. Your owner’s bath includes a separate soaking tub and shower or you may choose to install the large enclosed spa shower and closet for linens. Plan features a main level washer/dryer laundry/mud room and a lower level which can be customized to meet your needs. **Special offer Construction financing** Models shown with options

319 Twin Meadows Farm Ln, Centreville

Listing courtesy of Keller Williams Flagship. Contact:

218 Upland Ln, Centreville
$925,000
5 Beds ⋅ 5 Baths
WOW! This one is an absolute 11 on a scale of 1–10! Thoughtfully updated with stylish, on-trend finishes throughout, this property is truly exceptional from top to bottom. From the moment you step onto the covered front porch and into the dramatic two-story foyer, you’ll feel the difference. A private dining room sits to one side while two spacious main-level offices on the other make balancing work and home life effortless. And YES—high-speed internet is available through Talkie Fiber! At the heart of the home is a bright and beautiful gourmet kitchen featuring stainless steel appliances, a full refrigerator and full freezer, center island seating, and the kind of layout that naturally becomes the gathering place for everyone. The adjoining living room is warm and inviting, anchored by a fireplace and framed by oversized windows that flood the space with natural light while overlooking the picturesque backyard. Upstairs, you’ll find a magazine-worthy laundry room along with three spacious bedrooms and two beautifully updated full baths. The primary suite was designed to feel like a true personal retreat—complete with vaulted ceilings, a private deck overlooking the grounds, and plenty of natural light. Start your mornings with coffee in the fresh air or unwind at the end of the day under the stars. The luxurious ensuite bath features a soaking tub, separate shower, double vanity, and soaring ceilings that make the space feel spa-like. And just when you think it can’t get any better… there’s approximately 1,800 additional square feet of finished living space in the lower level! Complete with a private movie theater with seating for eight, bedroom, full bath, family room, kitchenette, and private entrance, the lower level offers incredible flexibility for guests, multi-generational living, or an in-law suite. Situated on nearly 1.5 acres surrounded by mature trees, this property offers the peaceful privacy of your own backyard oasis. The in-ground pool with landscaping, fire pit, multiple lounging areas, and glowing string lights create the perfect setting for entertaining family and friends all summer long. And tucked beyond it all? A beach volleyball court and horseshoe pit that make this property feel like your own private resort. PLUS: (As if all that wasn't enough) There is a whole house Generac to ensure you never lose power AND a 46,000 Enphase Solar (owned--no lease takeover!!) that saves BIG on electric and also returns Solar Renewable Energy Credits (SREC). Brand New Roof, too! Sound too good to be true? It’s not… unless you wait too long. This GEM is guaranteed to turn heads the moment it hits the market—so be ready!

218 Upland Ln, Centreville

Listing courtesy of Wilson Realty & Staging LLC. Contact:

Tenneessee, Stevensville
$525,000
3 Beds ⋅ 2 Baths
House is up, trimmed, drywalled, sided and kitchen is being installed. Ready to move in 45 days. Brand new construction opportunity! This thoughtfully designed ranch-style home will be breaking ground soon and offers the chance to secure a brand-new home before construction begins. Featuring convenient one-level living, this home will include an open floor plan with vaulted ceilings and quality finishes throughout. The kitchen is planned to feature quartz countertops, stainless steel appliances, a center island, and ample cabinet space, opening to the spacious living and dining areas—ideal for everyday living and entertaining. The primary suite is designed as a private retreat with a spacious bedroom, walk-in closet, and ensuite bath featuring a double vanity and oversized shower. Additional bedrooms provide flexibility for guests, family, or a home office. Other highlights include a dedicated laundry room, generous storage, and an attached 2-car garage. Situated on a spacious lot, buyers may have the opportunity to make selections depending on the stage of construction.

Tenneessee, Stevensville

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

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