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$1,750,000
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 full 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: (410) 739-0242
$484,500
3 Beds ⋅ 2 Baths
New List Price for this beautifully maintained and truly move in ready, this spacious home offers comfortable single level living with thoughtful upgrades throughout. Featuring 3 bedrooms and 2 full baths, the property showcases luxury vinyl plank flooring in the spacious living room, dining area and kitchen. The home is filled with natural sunlight, enhanced by new Andersen tilt in windows in the bedrooms and kitchen, plus an oversized Andersen French door leading from the sunroom to the rear patio. The sunroom features a tiled floor, creating a bright and relaxing space year round. The kitchen provides ample cabinet storage, two pantries, granite countertops, an eat in area, and a built in desk. The spacious master suite includes a walk in closet and private bath with granite counters. A large living room flows seamlessly into the adjoining dining area, offering an open and inviting layout. Major improvements include: Encapsulated crawl space (2021),New roof (2020),New 6" gutter guard system with underground drainage (2022),New brick patio and steps off the sunroom (2023),Recent property survey and staking for buyer convenience Additional features include a 2 car garage with pull down attic access and newly insulated side walls. Attractive, neutral color schemes run throughout the home, creating a warm and welcoming atmosphere. Best of all—NO HOA dues. Note virtual staging. This well cared for property offers comfort, quality, and convenience in the desirable North Brook community. Enjoy the amenities that Historic Centreville has to offer, the wharf, trail, parks, resturants and more.

114 Edenderry Ave, Centreville

Listing courtesy of Benson & Mangold, LLC. Contact: (443) 988-0483
$749,000
3 Beds ⋅ 2 Baths
Coastal cottage charm meets waterfront living on picturesque Crab Alley Creek. Offering 120 feet of shoreline and direct access to the Eastern Bay, this beautifully maintained home combines privacy, convenience, and the very best of the Chesapeake lifestyle. A pier permit already in hand provides an exciting opportunity for the next owner to further enhance their waterfront experience. This move-in-ready residence features 3 bedrooms, 2 full baths, and a versatile bonus room that can serve as a home office, guest room, or potential 4th bedroom. Meticulously updated and lovingly maintained throughout, pride of ownership is evident at every turn. Thoughtful upgrades create a warm and inviting atmosphere, including under-cabinet lighting and dimmer switches throughout the home, allowing you to create the perfect ambiance for any occasion. The kitchen is both stylish and functional, featuring an additional beverage refrigerator, making entertaining family and friends a breeze. The bathrooms offer a touch of luxury with heated floors and built-in Bluetooth speakers, creating a spa-like retreat within your own home. Situated on a large, level waterfront lot, the property is designed for both relaxation and recreation. Across the creek, protected conservation land provides a peaceful, natural backdrop and exceptional privacy rarely found on the water. Raised garden beds offer the opportunity to grow your own herbs and vegetables, while the detached garage, two storage sheds, and attic provide ample space for tools, equipment, seasonal items, and all your waterfront essentials. Spend your evenings gathered around the fire pit overlooking the water, launch a kayak from your backyard, or cruise to one of the many waterfront restaurants accessible from the Eastern Bay. Whether you're entertaining guests or enjoying a quiet sunset, this property embraces the laid-back charm of coastal living. Conveniently located just 10 minutes from the Bay Bridge, 20 minutes from Annapolis, and approximately 90 minutes from the beach, you'll enjoy easy access to everything while feeling worlds away. A rare opportunity to own a turnkey waterfront retreat in one of Kent Island's most desirable locations, where every detail has been thoughtfully curated for comfort, convenience, and enjoyment.

205 Riverside Dr, Chester

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767
$414,000
3 Beds ⋅ 2 Baths
Welcome to one of the most impeccably updated homes in Cloverfields, where thoughtful design, quality craftsmanship, and attention to detail are evident at every turn. Situated on a desirable corner lot, this move-in-ready home offers an impressive list of upgrades, allowing you to simply unpack and enjoy the Kent Island lifestyle. The stunning kitchen serves as the centerpiece of the home, featuring beautiful granite countertops, solid wood 46-inch cabinetry, matching stainless steel appliances, and a spacious center island that doubles as a bar-top dining area. A built-in dual-zone wine refrigerator adds both convenience and style, while the custom tile backsplash serves as one of the home’s defining design features, seamlessly tying together the cabinetry, countertops, and flooring to create a cohesive and sophisticated space. Luxury vinyl plank flooring extends throughout the main living areas, complemented by recessed lighting, fresh paint throughout, updated six-panel doors, and modern finishes that give the entire home a fresh, inviting feel. Every detail has been carefully considered to maximize both functionality and style. The bathrooms have been beautifully renovated with ceramic tile flooring, solid wood vanities topped with granite, updated fixtures, and comfort-height toilets. The primary bath showcases a ceramic tile shower with a glass enclosure, creating a clean and timeless look. Spacious bedrooms feature new carpeting, including the primary suite complete with a walk-in closet and private bath. Major system updates provide peace of mind, including a newer roof, HVAC system, water heater, updated windows, washer and dryer, vinyl siding, and updated exterior doors featuring built-in blinds between the glass. Ample storage can be found throughout the home, making excellent use of every square foot. Step outside to enjoy the rear patio, perfect for grilling, relaxing, or entertaining guests, with convenient access to the driveway and backyard. As a resident of Cloverfields, you’ll enjoy access to exceptional community amenities including a private sandy beach, community pool, marina, boat ramp, fishing pier, playground, and clubhouse. Conveniently located near shopping, waterfront dining, entertainment, and the Bay Bridge, this home offers the perfect combination of updated living and Eastern Shore charm. Rarely does a home of this size offer this level of renovation, quality, and attention to detail. Every major improvement has already been completed, creating a truly turnkey opportunity in one of Kent Island’s most sought-after communities.

601 Davol Rd, Stevensville

Listing courtesy of Samson Properties. Contact: 7033788810
$1,350,000
4 Beds ⋅ 3 Baths
WATERFRONT LIVING on Winchester Creek! This wonderful 4 bedroom, 2.5 bath Grasonville estate offers the ultimate Eastern Shore lifestyle, fully refreshed with a newly painted neutral interior, gleaming refinished hardwoods, and carpet. A grand 2-story foyer with a palladium window, transom accents, and elegant French doors welcomes you inside. The main level features 11' ceilings, a great room with fireplace and a bank of windows with water views, a separate dining room, bright breakfast room, and a fabulous kitchen with an island, pantry, and reverse osmosis water filtration. The main floor primary suite boasts a walk-in closet and a no-threshold shower, complemented by a full, hall bath and convenient half bath. Upstairs, a versatile bonus space features custom built-ins— perfect for an office and media space. Your outdoor resort awaits: a Trex deck with built-in benches and 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 deeded boat slip (#10), mooring pile, and private boat lift. Rounding out this incredible home is an oversized 2-car garage with storage space, HVAC (2018), buried 500-gallon propane tank, and full water conditioning system and lush landscaping.

104 Port Ct, Grasonville

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

$699,000
4 Beds ⋅ 2 Baths
This two home listing in historic Stevensville is in walkable distance to Kent Island Elementary School, Stevensville Middle and Kent Island High School. The front house was built in 1932 and the back house was built in 1980 as a garage and is now a solid home with perfect bones. This property is being sold as-is and not a traditional listing. There will only be two open houses on two different weekends that have not been determined yet. Please do not drive on the to property because there are two different tenants that live there. This property is zoned residential and commercial.

412 Main St, Stevensville

Listing courtesy of Cottage Street Realty LLC. Contact:

$569,900
4 Beds ⋅ 3 Baths
PRICE IMPROVEMENT! $10K REDUCTION! Why wait for new construction when this barely lived-in home in the desirable community of Perry’s Retreat is available now? Welcome to 128 Perry’s Retreat Boulevard, offering a bright, open-concept main level with LVP flooring throughout and a layout designed for everyday living and easy entertaining. The spacious kitchen features an oversized island, stainless steel appliances, pantry, quartz countertops, soft-close cabinetry, and plenty of room to gather. The main level also includes a convenient half bathroom, office space, garage access, an oversized coat closet, and a walkout to the spacious backyard. Upstairs, you’ll find four carpeted bedrooms, two full bathrooms, and a conveniently located laundry area. The beautiful primary suite features a tray ceiling, spacious walk-in closet with natural light, and an upgraded en-suite bathroom with LVP flooring, a dual vanity, and a shower with built-in seating and dual showerheads. Outside, enjoy a covered front porch with space for seating, a spacious backyard, and a maintenance-free vinyl privacy fence. Perry’s Retreat offers sidewalks throughout the community, playgrounds, and additional parking for boats, RVs, and extra vehicles. The location is another major bonus, with quick access to Route 50 and close proximity to Kent Island, the Narrows, Annapolis, Easton, St. Michaels, local dining, shopping, golf, boat launches, and Chesapeake Bay favorites. This move-in ready home offers the benefits of newer construction, a convenient Eastern Shore location, and no wait!

128 Perrys Retreat Blvd, Grasonville

Listing courtesy of RE/MAX Executive. Contact:

$510,000
3 Beds ⋅ 2 Baths
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:

$400,000
3 Beds ⋅ 2 Baths
Opportunity meets location at this charming 1891 farmhouse situated on a spacious ¾-acre lot just a few short miles off 301 . Located within the Village Center District, this unique property offers the flexibility and visibility that entrepreneurs, tradespeople, hobbyists, and investors have been searching for. And NO TOWN TAXES. The home features 3 bedrooms and 2 full baths, blending historic character with thoughtful updates including granite countertops and stainless steel appliances. Outside, the standout feature is the impressive 32' x 24' detached garage with two 10' x 10' doors, providing ample space for a workshop, storage, equipment, vehicles, or business operations. Whether you're looking for a place to call home, a property with room to grow your business, or a combination of both, the possibilities here are hard to find. Enjoy the convenience of being just minutes from downtown Centreville, schools, shopping, dining, and major commuter routes while maintaining the space and flexibility that only a property like this can provide. Bring your vision and explore the potential of this rare Village Center opportunity. Buyers to complete their own due diligence for permitted use of the property and fees.

1645 Ruthsburg Rd, Centreville

Listing courtesy of Samson Properties. Contact: 7033788810
$200,000
3 Beds ⋅ 2 Baths
Oversized, three-story home located close to the Chester River. Investor-Special, in need of repairs and priced accordingly. The property offers a great opportunity for the right buyer. There is a covered porch and balcony. Tons of character throughout with original hardwood floors. Sold in As-Is condition, priced below assessed value!

107 2nd St, Crumpton

Listing courtesy of Marathon Real Estate. Contact:

$499,000
4 Beds ⋅ 3 Baths
NEW PRICE—An Unbelievable Value on Kent Island! Built in 2020, this gorgeous, like-new home offers approximately 1,974 square feet of beautifully maintained living space, a spacious yard backing to trees, and a desirable Kent Island location. An assumable VA loan at an attractive 2.75% interest rate may be available to qualified buyers, subject to lender and VA approval. Fresh interior paint and new carpeting throughout make this home truly move-in ready. The spacious living and dining areas provide plenty of room for everyday living and entertaining, while the inviting fireplace adds warmth and character. The kitchen features a breakfast bar, granite, pantry, abundant cabinetry, and generous storage. The spacious owner’s suite offers two walk-in closets and a private en-suite bath, creating a comfortable retreat. Step outside to enjoy the private backyard backing to trees, ideal for relaxing, entertaining, or enjoying peaceful evenings outdoors. Ccnvenient access to nearby boat ramps. Ideally located near shopping, dining, golf, pickleball, waterfront parks, walking trails, beaches, a dog beach, marinas, boat storage, Queenstown Premium Outlets, and popular local restaurants and entertainment. Experience the best of Kent Island living in this beautifully updated home. Some rooms have been virtually staged, including the owner’s suite, living room, and dining room.

124 Riverside Dr, Chester

Listing courtesy of Douglas Realty LLC. Contact: (866) 987-3937
$669,900
3 Beds ⋅ 2 Baths
Welcome to your private Eastern Shore oasis at 116 Mallard Drive, Stevensville, MD 21666! This beautifully maintained and recently updated Cape Cod home sits on a rare 1.1-acre lot in a quiet, private neighborhood on Kent Island — one of the hardest-to-find lot sizes in this desirable area. Enjoy serene, protected views of Mallard Pond, where you can watch ducks glide across the water, sip morning coffee on the screened porch, and truly experience peaceful Kent Island living at its finest. Boasting 1,976 square feet of above-grade living space (built in 2000), this 3-bedroom, 2-bath home features thoughtful updates throughout. Enjoy new LVP flooring and carpet, a bright open-concept main level perfect for everyday living and entertaining, and a stunning kitchen with granite countertops and all new appliances. The spacious primary suite includes a luxurious soaking tub and walk-in closet, while two additional bedrooms and a full bath complete the main level. A 2-car garage and newer furnace add convenience and peace of mind. The standout feature is the large unfinished attic with electrical wiring and HVAC already extended — substantial, flexible space ready for your vision. Easily finish into additional bedrooms, a home office, playroom, or family suite. Outside, the expansive 1.1-acre lot delivers exceptional privacy and natural beauty, bordered by community-owned preserved woodlands and Mallard Pond that ensure your views remain undisturbed for years to come. Enjoy the screened porch overlooking the pond, low-maintenance exterior, low HOA fees of only $17 per month, and the incredible location on Kent Island — walk or bike to the public golf course, Kent Island Trail, waterfront parks, piers, and just minutes from Chesapeake Bay adventures, shopping, and dining. This updated home combines solid construction, modern finishes, low monthly costs, and a truly rare 1.1-acre private setting. Whether you’re looking for a peaceful full-time residence or a lifestyle property with room to grow, 116 Mallard Drive is a standout opportunity on Kent Island. Don’t miss it!

116 Mallard Dr, Stevensville

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

$299,900
3 Beds ⋅ 1 Baths
An exceptional opportunity to own this Single Level 3 bedroom 1 full bathrooms Ranch Style Home at a GREAT price nestled on an adorable lot. No need to worry about climbing stairs, everything is located on one floor. the interior showcases contemporary finishes and a thoughtful layout that maximizes both style and functionality. The bathroom has been tastefully refreshed, the home has been freshly painted with LPV flooring and carpet throughout. This home offers the ultimate in conveniences local public and private golf courses outlets Close Proximity to the Chester River, fine dining and easy access to major highways. Don't miss out on the chance to create your dream space in this prime Chestertown location! NEW HVAC SYSTEM TO BE INSTALLED

517 Round Top Rd, Chestertown

Listing courtesy of Keller Williams Flagship. Contact:

$525,000
5 Beds ⋅ 3 Baths
Welcome to 101 Edenderry Avenue in North Brook! Some homes simply stand out, and this former model home is one of them. Perfectly positioned on a desirable corner lot in the sought-after North Brook community, this spacious 5-bedroom home combines thoughtful design, modern updates, and the flexible living space today's buyers are searching for. Step inside and you'll immediately appreciate the bright, open floor plan that effortlessly connects the beautifully updated kitchen with the surrounding living and entertaining spaces. Featuring abundant cabinetry, generous counter space, and a large center island, the kitchen serves as the heart of the home—perfect for everything from weeknight dinners to holiday gatherings. Fresh new carpet adds a clean, move-in ready feel throughout, while oversized windows fill the home with natural light, creating a warm and welcoming atmosphere in every room. With five true bedrooms, there's room for everyone, whether you need space for family, guests, a home office, fitness room, or playroom. The spacious primary suite offers a relaxing retreat complete with a private bath and walk-in closet. Outside, you'll love the large backyard, offering endless opportunities for entertaining, backyard games, gardening, or simply relaxing after a long day. The premium corner lot provides additional outdoor space, enhanced curb appeal, and extra privacy. Located in the highly desirable North Brook community, you'll enjoy sidewalks, neighborhood amenities, and convenient access to shopping, dining, schools, and major commuter routes. Move-in ready, beautifully maintained, and offering the space today's buyers need, 101 Edenderry Avenue is the one you've been waiting for. Schedule your private tour before someone else calls it home.

101 Edenderry Ave, Centreville

Listing courtesy of RE/MAX Executive. Contact: 4432741900
$575,555
4 Beds ⋅ 3 Baths
*Some images have been digitally enhanced / virtually staged for illustrative purposes only* Discover the perfect blend of coastal living and everyday comfort in this spacious 4-bedroom, 3-bath single-family home located in the lovely area of Stevensville. Set on a generous 0.39-acre private fully fenced in lot. Ideal for those who enjoy entertaining, recreation, gardening or simply rest and relaxation with the Chesapeake Bay in your own backyard. Inside, you’ll find a bright and welcoming flexible floorplan layout featuring multiple living areas, a well-appointed kitchen, a beautifully decorated, spacious and bright morning room and much more. A home suited for families or multi-generational living. Recent updates include energy-efficient windows, a french drain around the home, modern appliances, improved insulation, upgraded water systems, and refreshed finishes, providing peace of mind and added comfort. The spacious backyard offers endless possibilities—gardening, play areas, or outdoor gatherings—while the property’s ample parking, carport/garage, and room for boat storage make it a standout for those who love life on the water. Just a short distance from your own neighborhood private beach, nearby marinas and restaurants. This home delivers coastal charm on the Eastern Shore. Conveniently located near Route 50...Come and visit us! A rare opportunity you don't want to miss to own in one of Kent Island’s most sought out water-access neighborhoods.

511 Chesapeake Ave, Stevensville

Listing courtesy of RE/MAX Realty Centre, Inc.. Contact:

$559,000
4 Beds ⋅ 3 Baths
Welcome to Symphony Village in Centreville a 55+ Active Adult Community that HAS IT ALL! DON'T MISS THIS OPPORTUNITY! This thoughtfully maintained home offers over 3,190 square feet of living space as well a Sky Basement w/ 520 (approx.) square feet of additional storage space, Featuring 4 Bedrooms, 3 full baths, Roof 2019, Water Heater 2026, Washer/Dryer 2023, New Front Porch, Sidewalk plus drainage 2023, HVAC Units 2012, The Bright open main level includes Kitchen with extended granite countertops, stainless steel appliances, while the flowing layout includes hardwood floors, custom Blinds & Shades, and inviting living and dining areas. A GLORIOUS sunroom with wall-to-wall windows offers a tranquil retreat and opens onto a spacious Professionally Landscaped Patio, perfect for relaxing or hosting guests! The main level primary suite is a true retreat, featuring two walk-in closets, dual vanities, a soaking tub, and a walk-in shower Plus a fabulous Sitting Room/Office, Upstairs, a versatile loft provides the perfect setting for a Sports Bar area Etc., along with a guest bedroom complete with its own full bath and walk-in closet, Life in Symphony Village means more than just a beautiful home, it's a vibrant, welcoming community. Residents enjoy access to a clubhouse with social spaces, indoor and outdoor pools, a fitness center, pickleball and bocce courts, walking and hiking trails, and a full calendar of activities designed to keep you as active and engaged as you would like to be. Community HOA fee includes Partial Sprinkler system on your property! Conveniently located near Queenstown Premium Outlets and the charming downtown area of Centreville, you will also find yourself just a short drive from the waterfront towns of Chestertown, Easton, St. Michaels, Oxford and Annapolis. also, UMMS and UM Shore Regional Health are building a state-of-the-art medical center in Easton, set to open in 2028, This is more than a home, it is a LIFESTYLE .

510 Symphony Way, Centreville

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

$345,000
3 Beds ⋅ 2 Baths
Step into timeless charm with this beautifully maintained Colonial in the heart of Centreville. Built in 1901, this character-filled home offers the perfect blend of historic appeal and everyday comfort. Featuring three spacious bedrooms, one and a half bathrooms, and nearly 1,800 square feet of living space, you'll appreciate the generous room sizes, abundant natural light, and flexible floor plan designed for modern living. Situated on a large, level lot, the property provides plenty of space for gardening, entertaining, or simply relaxing outdoors. The inviting front porch welcomes you home, while the backyard offers endless possibilities for outdoor enjoyment. Conveniently located just minutes from downtown Centreville's shops, restaurants, parks, and schools, this home combines small-town charm with an easy commute to Annapolis, Easton, and the Chesapeake Bay. Whether you're looking for your first home, room to grow, or simply appreciate the character that only an historic home can offer, 430 Railroad Avenue is ready to welcome you home.

430 Railroad Ave, Centreville

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767
$1,990,000
6 Beds ⋅ 5 Baths
The location of this property is fabulous! One of the most beautiful spots on the bay, it features a panoramic view across the bay to Annapolis! Watch the ships going in and out of Baltimore, magnificent sunsets, and the Blue Angels, when they perform! In a small neighborhood, just minutes from the Bay Bridge, the property has all you need for a year-round home or for a week-end or vacation retreat! The cement, heated in-ground pool adjoins the deck and porch areas . A small kitchen and full bath are poolside for coming in from the pool, cleaning your "catch of the day" or steaming crabs! The private pier accommodates a boat lift and two jet-ski lifts. There is rip-rap and bulk heading, and depending on the tide, there is a beach! This uniquely-designed home offers multiple living and dining areas, as well as main and second level bedrooms and a separate office. With its many three-season and screened-in porch areas and outside decks, you can entertain rain or shine! And, by the way, the golfers in the family, need not leave the neighborhood as it abuts the Blue Heron Golf Course! Instead of commuting from your primary home to a vacation home, save yourself the trip...this house has it all! There is a video security system at the property.

206 Queen Anne Club Dr, Stevensville

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

$599,000
4 Beds ⋅ 3 Baths
Welcome to 130 Opera Court in the sought after community of Symphony Village at Centreville. If you've been waiting for that home resting on an exceptional lot backing to an open area and woods, then this is the home you've been waiting for. The beautiful 4 bedroom, 3 full bath home is exceptional, move in ready and just waiting for you. As you enter the home, your eyes will be drawn to the bright open floorplan and the rear windows overlooking the large deck that expands across the entire rear of the home. On the right, you'll find the front guest bedroom/office, a second guest bedroom, full bath, laundry room and access to the garage and lower level of the home. Moving through the home, you'll pass through the large living area with double sided propane fireplace, mounted TV that conveys with the home and the relaxing area and dining area on the rear overlooking the large lot backing to beautiful woods. To the right is the gourmet kitchen with granite counters, appliances including a gas stove and under cabinet lighting. The expansive primary suite is a must see with French Doors leading to the balcony, his and her walk-in closets and the primary bath with a large walk-in corner shower. Moving to the lower level, you'll find a large family area, another guest bedroom, full bath, a massive amount of storage area and a workshop leading to the rear exterior of the home. This home rests on a premium wooded lot for your relaxation while enjoying the wildlife that the area has to offer.

130 Opera Ct, Centreville

Listing courtesy of RE/MAX Executive. Contact: 4432741900
$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. 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:

$650,000
3 Beds ⋅ 3 Baths
Contemporary home in Prospect Bay offering approximately 2,850 square feet of living space and available for the first time since 1999. Features 3 bedrooms, including 2 on the main level, and 2.5 baths. The family room includes a fireplace and triple sliders leading to the deck. Spacious primary suite. Loft overlooking the family room, ideal for a home office, sitting area, or additional living space. Separate dining room and dedicated mudroom with laundry. Complete with a 2-car garage and deck overlooking the backyard. Located in Prospect Bay Golf and Country Club. Club amenities include: golf, a swimming pool, boat ramp, tennis courts and a clubhouse with restaurant.

24 Fairway Is, Grasonville

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

$7,995,000
8 Beds ⋅ 10 Baths
Set on 20 private waterfront acres with over 800 feet of shoreline along the Chesapeake Bay, this extraordinary estate offers a rare opportunity to own one of Maryland’s most impressive legacy properties. Behind a gated entrance and winding tree-lined drive, the residence combines timeless architecture, exceptional craftsmanship, and resort-inspired amenities designed for both grand entertaining and everyday enjoyment. The shoreline is simply remarkable, featuring riprap protection, a private pier with lifts, sandy beach areas, water and electric service, and panoramic Bay views that deliver spectacular sunsets year-round. Whether enjoying a quiet morning by the water, setting out for a day on the Bay, or gathering with family and friends for an evening by the fire, every aspect of the property has been thoughtfully designed to embrace the waterfront lifestyle. Inside, over 15,000 square feet of finished living space showcases Brazilian cherry flooring, handcrafted millwork, coffered ceilings, custom paneling, seven fireplaces, and beautifully curated living spaces throughout. The gourmet kitchen serves as the heart of the home, featuring premium appliances, an oversized island, sunlit breakfast room, and a fully equipped butler’s pantry designed for seamless entertaining. The residence offers two luxurious primary suites, including a main-level retreat with fireplace, spa-inspired bath, private office, and direct access to the waterfront. Multiple ensuite guest bedrooms, a theater room, game room, exercise suite, expansive third-floor recreation space, and a private apartment above the garage provide exceptional flexibility for hosting family and guests. Outdoor amenities rival those of a private resort. Enjoy a saltwater pool and spa, covered poolside entertaining pavilion with outdoor kitchen and fireplace, regulation tennis and pickleball court, expansive patios and terraces, fire pit, pond with fountain, playground, and extensive professional landscaping that creates a setting of complete privacy and tranquility. This is more than a home—it is a Chesapeake Bay estate designed for generations to gather, celebrate, and create lasting memories. A rare offering where luxury, privacy, recreation, and waterfront living come together on an extraordinary scale.

7328 Kent Point Rd, Stevensville

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$399,500
3 Beds ⋅ 2 Baths
Welcome to 2645 Cox Neck Road, a move-in ready home in the desirable Harbor View Community of Chester. Offering 3 bedrooms, 1.5 baths, and situated on a spacious .34-acre lot, this well-maintained property combines comfort, convenience, and exceptional value at $399,500. Inside, you'll find a bright and inviting floor plan featuring a kitchen with a stylish tile backsplash, ample cabinetry, and luxury vinyl plank flooring. Thoughtfully maintained and updated over the years, this home offers peace of mind with a roof replaced within the last five years, replacement windows, siding, storm doors, and sliding glass door, as well as a recently replaced well pressure tank. Fresh interior paint and included appliances, including the washer and dryer, make moving in easy. Outdoor living is equally appealing with a charming front patio perfect for morning coffee and a large rear patio ideal for entertaining, grilling, or relaxing with family and friends. The beautifully maintained yard offers plenty of space for gardening, outdoor activities, or simply enjoying the outdoors. Two storage sheds provide ample room for tools, lawn equipment, and recreational gear. Located just minutes from Kent Island's popular restaurants, shopping, marinas, parks, and the Cross Island Trail, this home offers convenient access to everything the Eastern Shore lifestyle has to offer. Commuters will appreciate being less than 10 minutes from the Chesapeake Bay Bridge, while Harbor View residents enjoy a strong sense of community with neighborhood gatherings, holiday celebrations, yard sales, and other neighborhood events throughout the year. Whether you're searching for your first home, looking to downsize, or seeking a move-in ready property in a convenient Kent Island location, 2645 Cox Neck Road is an opportunity you won't want to miss.

2645 Cox Neck Rd, Chester

Listing courtesy of Compass. Contact: (410) 429-7425
$1,350,000
5 Beds ⋅ 2 Baths
The locals called it Keister's Folly. In the mid-1940s, Dr. Keister built a barn on Kent Island overlooking Cox Creek, hoping to raise Black Angus cattle on 25 acres. The acreage was too small for the endeavor — but the barn he built was extraordinary. In the early 1960s, the developer of the Harbor View community converted it into a residence. The current owners' family purchased it in 1965 and has invested over $400,000 in improvements across sixty years of devoted stewardship. This property has never been publicly offered for sale — until now. Situated on 1.65 acres with 205 feet of protected waterfront on Cox Creek, this is one of the largest privately held waterfront parcels remaining in Harbor View. The 75-foot private pier extends into navigable tidal water with approximately 3.5 feet at mean low tide and two boat slips. Shoreline reinforced with professional rip-rap. Maps show Flood Zone X — outside 100-year and 500-year floodplains - buyer and agent should verify. The home offers 3,456 sq ft of living space across two levels including 700+ sq ft of unfinished second and third-level expansion space. Five bedrooms, two full baths. The upper-level primary suite features hardwood floors, panoramic water views, attached full bath, walk-in closet, private coffee bar with refrigerator, and a deck overlooking the creek. Updated kitchen with granite countertops, upgraded cabinetry, and high-end appliances, improvements throughout honor the building's barn heritage. Solid block construction. 200-amp electrical. Well water, public sewer. New Roof will be installed prior to settlement. Ideal for those who are seeking genuine Chesapeake waterfront with privacy, deep water access, and a property unlike anything else on the market. Be sure to download the Home Profile in the documents section for more details on the home including the history of the home.

2513 Cecil Dr, Chester

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442
$699,500
5 Beds ⋅ 4 Baths
Welcome to 216 Brix Dr. — Where Modern Luxury Meets Eastern Shore Charm Prepare to be impressed by this beautifully renovated 5-bedroom, 3.5-bath home in the sought-after community of Church Hill. Thoughtfully updated from top to bottom, this exceptional residence offers generous living space, stylish finishes, and the peaceful lifestyle the Eastern Shore is known for. Step inside to discover a bright, open interior featuring brand-new luxury vinyl plank flooring throughout the main level, plush new carpeting upstairs, and fresh paint throughout, creating a crisp, contemporary feel that's completely move-in ready. At the heart of the home, the stunning gourmet kitchen is designed to impress, boasting brand-new stainless steel appliances, an oversized center island, abundant cabinetry, and expansive counter space—perfect for entertaining, hosting holidays, or everyday living. A rare and highly desirable feature, this home offers two spacious primary suites—one on the main level and another upstairs—providing incredible flexibility for multi-generational living, extended guests, or a private owner's retreat. Outside, enjoy the convenience of an oversized three-car garage, a blacktop driveway, and a peaceful backyard backing to mature woods, creating a private setting for relaxing evenings, outdoor gatherings, or simply enjoying nature. Beyond the home itself, residents enjoy access to community walking trails and water access, allowing you to fully embrace the outdoor lifestyle and scenic beauty that make the Eastern Shore so desirable. Ideally located, this home is approximately 10 minutes from the historic waterfront towns of Centreville and Chestertown, where you'll enjoy charming boutiques, locally owned restaurants, marinas, waterfront parks, and year-round community events. Combining modern updates, spacious living, desirable community amenities, and an unbeatable location, this exceptional property offers the very best of Eastern Shore living. Don't miss your opportunity to make this stunning home your own—schedule your private tour today!

216 Brix Dr, Church Hill

Listing courtesy of CR Realty. Contact: 4104900460
$569,000
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: (410) 255-3690
$335,000
4 Beds ⋅ 2 Baths
Some homes simply have a feeling you can't recreate, and this is one of them. Rich in character and timeless craftsmanship, this beautifully maintained home blends historic charm with thoughtful updates, creating a warm and inviting place you'll love coming home to. Original hardwood floors, glass doorknobs, skeleton keys, classic swinging doors, and elegant architectural details tell the story of a home built to stand the test of time, while an updated bathroom and refreshed kitchen provide the comforts of everyday living. Designed with both gathering and quiet moments in mind, the spacious layout offers generously sized rooms filled with natural light. The oversized screened porch is the perfect extension of the home, inviting you to enjoy morning coffee, evening conversations, or simply unwind while overlooking the expansive backyard with plenty of room for gardening, entertaining, pets, or play. A full unfinished basement offers abundant storage and room for future possibilities. Located in the heart of Church Hill, this is more than just a house. It's an opportunity to own a home filled with warmth, history, and character that's becoming increasingly difficult to find.

104 Walnut St, Church Hill

Listing courtesy of RE/MAX Executive. Contact: 4432741900
$649,000
3 Beds ⋅ 1 Baths
Welcome to your dream coastal retreat in the highly sought-after Chester River Beach community of Grasonville, Maryland. This beautiful, luxurious bayside property is a single-story rancher that offers the perfect blend of modern upgrades, breathtaking views of the Bay and relaxed coastal living in a vibrant and lively neighborhood that is perfect for boating enthusiasts, crabbing, and fishing. This fully remodeled three bedroom, one full bath home sits on one of the largest corner lots and has been thoughtfully updated from top to bottom with high end finishes and brand new systems throughout. Enjoy peace of mind with newly installed roof, vinyl siding, flooring, central air conditioning system with heat pump, new well tank, and water heater. Next on the list is a completely renovated bathroom featuring a state of the art smart bidet toilet with heated seat, and automated micro bubble cleansing technology bringing spa like comfort to your everyday routine. After enjoying the beach, boating, fishing or swimming, relax in the spacious brand new shower. Gorgeous coastal style kitchen designed with two spacious islands, providing ample prep space, including breakfast bar seating perfect for entertaining family and guests. Amenties showcasing high end cabinetry, ceramic tile backsplash, wall mounted retractable pot filler, smart appliances including flat top range, stainless double door refrigerator, double oven, and farm sink sink as well as other highend features! The home also includes convenient laundry with a new washer and dryer, offering everyday ease and functionality. Enjoy breathtaking water views filling the space with natural light and creating a serene coastal atmosphere through two newly installed bay windows. Additional features include a cozy working fireplace, sliding patio door leading to a newly constructed deck with additional views of the bay, off-street parking, and a spacious detached garage equipped with electrical service. The home also includes a full, easily accessible attic, providing plenty of storage and potential to include additional living space! The property includes access to private boat docks, boat ramps, and private managed beach just a few steps away. Residents also enjoy a community park, entertainment pavilion with stunning waterfront views, along with convenient access to nearby shopping malls, restaurants, and grocery stores. Boat directly to many waterfront bars and boating restaurants making every day feel like a vacation. Whether you're looking for a full-time residence or a weekend getaway, this move-in-ready Chester River Beach home delivers the very best of Eastern Shore bay-front living.

801 Chester River Dr, Grasonville

Listing courtesy of HomeZu by Simple Choice. Contact: (855) 885-4663
$609,900
4 Beds ⋅ 3 Baths
**Price Improvement** 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. To make this opportunity even more appealing, sellers are offering a 2-YEAR HOME WARRANTY (up to $2,000) with an acceptable offer—adding extra peace of mind to a property that already offers space, flexibility, and freedom.

913 Clark Corners Rd, Centreville

Listing courtesy of Coldwell Banker Waterman Realty. Contact: (410) 643-5005
$589,000
1 Beds ⋅ 2 Baths
The luxury of living here is not in the square footage. It is in the untouched beauty of the river and constant exposure to nature. A charming oasis on the Chester River with 3 outbuildings all with the most amazing view. Magnificent plantings around the property. A duck blind for hunting. Private dock with lift. Historical ferry road is yours! The house was completely renovated in 2011. It's all so charming and extremely well kept. Roughly a quarter mile of waterfront. BAT septic system only approved for 1 bedroom. You cannot expand the house.

114 Front St, Crumpton

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