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New Street, Church Hill
$70,000
Finally, an affordable building lot! Come check out this mostly wooded .67 acres on the edge of the historic town of Church Hill. The lot backs to a creek. The owner has a letter from the town saying it should be able to hook into the public sewer. So many fun things to do nearby including theater, marina's, beaches, parks, restaurants and more. Won't last long.

New Street, Church Hill

Listing courtesy of Taylor Properties. Contact:

230 Switchgrass Way Unit 12, Chester
$509,999
2 Beds ⋅ 3 Baths
Move-in ready condo with zero wait! This meticulously maintained, first-floor Magothy shows like new, offering over 2,000 square feet of single-level living in the highly sought-after Four Seasons at Kent Island 55+ active-adult community. Enjoy the rare convenience of direct outdoor patio access and beautiful views from every window. The thoughtfully designed open-concept features two spacious bedrooms, each boasting a full bath and walk-in closet, plus direct patio access from the primary suite. The gourmet kitchen centers around a massive seating island with pendant lighting and a stylish dry bar. French doors open to a dedicated home office, while double sliding doors in the living room provide the entire space with natural light. Quartz countertops and seamless luxury vinyl plank flooring are found throughout the home. Complete with a private guest powder room, laundry room, climate-controlled storage, a one-car garage, and a beautifully appointed community room on the second floor, this condo delivers the low-maintenance lifestyle the community is known for. The award-winning 24,000 square foot Chester House clubhouse is the heart of the community, with indoor and outdoor pools, a fully equipped fitness center, yoga studio, demonstration kitchen, library, billiards and game room, and a grand ballroom. Outside, enjoy lighted tennis, pickleball, and bocce courts, a dog park, gas and wood-burning fire pits, a waterside tiki bar, and miles of walking and biking trails connecting to the Cross Island Trail. The 450-foot community pier on the Chester River, with boat slips plus canoe and kayak launch and storage, is a favorite for anyone who loves the water. Year-round clubs, classes, live entertainment and events can be found at the community clubhouse, and you’ll be minutes from Kent Island, shops, waterfront dining, and Queenstown Premium Outlets, with easy access to the Bay Bridge for Annapolis, Baltimore, and Washington D.C. Schedule your private showing today.

230 Switchgrass Way Unit 12, Chester

Listing courtesy of Real Broker, LLC - Chester. Contact:

205 Anchor Ln, Chester
$500,000
4 Beds ⋅ 3 Baths
SPACE, FLEXIBILITY & VALUE ON KENT ISLAND! Welcome to 205 Anchor Lane, where generous square footage, versatile two-level living and incredible outdoor space come together to create a home that can truly adapt to your needs. With 5 bedrooms, updated bathrooms and living spaces on both levels, the floor plan offers excellent flexibility for multi-generational living, guests, a home office or the potential to create a private in-law suite. The main level features easy-care LVP flooring, while the lower level has been refreshed with brand-new carpet, giving the home a fresh, move-in-ready feel. Multiple living and gathering spaces mean there is room to spread out without sacrificing connection. Outside, the possibilities continue! Enjoy morning coffee on the screened porch, entertain on the spacious deck, or take advantage of the large backyard for play, pets, gardening and gatherings. Car enthusiasts, hobbyists and anyone needing serious storage will LOVE the impressive detached 4-car garage—an increasingly hard-to-find feature on Kent Island. And the best part? NO HOA! Enjoy the freedom to make the property your own without the added monthly community expense. With 5 bedrooms, two levels of flexible living space, updated baths, multiple outdoor living areas, a huge backyard and an exceptional 4-car detached garage, 205 Anchor Lane delivers an incredible amount of home and versatility for the money. If you've been searching for true VALUE on Kent Island, this one deserves a look! With 5 bedrooms and 3 full bathrooms, this home provides room for everyone. The lower level offers excellent potential for multigenerational living, guest accommodations, or a future in-law suite. Fresh carpet, luxury vinyl plank flooring, and updated bathrooms create a move-in ready feel while still leaving opportunities to add your own personal touches and build equity. The functional floor plan offers multiple living spaces, a two-car garage, and abundant storage throughout. Outside, the expansive yard provides plenty of room for entertaining, gardening, pets, or simply enjoying the outdoors. Ideally located within walking distance to local dining, Castle Marina, and the Cross Island Trail, you'll love the convenience of enjoying the Kent Island lifestyle right from your doorstep. Public sewer service and well water add to the property's appeal. Whether you're searching for extra space, a home that can accommodate extended family, or simply a great value in a sought-after location, 205 Anchor Lane delivers endless possibilities.

205 Anchor Ln, Chester

Listing courtesy of Samson Properties. Contact:

116 Prospect Bay Dr W, Grasonville
$749,000
4 Beds ⋅ 3 Baths
PRICED TO SELL - RARE OPPORTUNITY - Beautifully sited on a fabulous 1.03-acre lot in sought-after Prospect Bay Golf and Country Club, this spacious home offers the best of both water and golf course living. Enjoy lovely water views and stunning sunsets from several rooms or while relaxing on the wraparound front porch. From the rear of the home, take in peaceful Golf Course Views overlooking the newly renovated par-five 5th hole. Enjoy these views from the heated and cooled Florida room or from your adjoining deck with a remote controlled awning. Inside, gorgeous hardwood floors flow from the entry through the living and dining rooms. The bright kitchen features Brookhaven cabinets, Profile appliances and opens to the comfortable family room with a gas fireplace and sliders leading to the Florida ( or four seasons) room, creating an ideal layout for everyday living and entertaining. Upstairs, you’ll find four generously sized bedrooms, including a spacious primary suite with tray ceiling, a huge walk-in closet, and a large jetted tub, walk-in shower, and double vanities. The convenient second-level laundry room, two-car garage, storage shed, and oversized parking pad add to the home’s practicality. Select spaces have been refreshed with new interior paint and elegant crown molding (2025), adding a touch of sophistication and style. Recent improvements include Dual-Zone Hybrid HVAC (2024/2026): Customized upstairs/downstairs comfort with two brand-new 2026 Lennox HVAC units with heat pumps and smart thermostats, backed by a Navien tankless combi-boiler Installed in 2024 for ultra-efficient, multi-zone hydronic heating. The crawlspace has been newly encapsulated with an April Aire dehumidifier (2026). Although not a problem in Prospect Bay, you'll never have to worry about losing power as you have a Generac Generator just outside to take care of a power loss! As a Resident of Prospect Bay enjoy exceptional community amenities, including an 18 hole golf course, driving range, a members only restaurant & bar, clubhouse, swimming pool, boat ramp, tennis courts, basketball, pickleball, kayak racks, and a marina. The monthly HOA Fees INCLUDE Golf Membership and Greens Fees. So many activities for all including Book Club, Dine & Cruise, Movie Night for Kids, Garden Club, Line Dancing, etc . This home is just across the street from the boat ramp, marina and open water leading to the Bay! The perfect place to live and play!

116 Prospect Bay Dr W, Grasonville

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact:

315 Bentons Pleasure Rd, Chester
$599,900
3 Beds ⋅ 2 Baths
REDUCED!!! This 3 bedroom 2 full bath brick rancher is located 1.88 for plenty of privacy and plenty of room to expand. Not many large lots left in this community, check with county for very possible sub dividing for 2 additional lots. Home is in need of updating with lots of potential to add your own touch and design. More pictures coming soon. Currently on septic but sewer is available.

315 Bentons Pleasure Rd, Chester

Listing courtesy of Douglas Realty LLC. Contact:

Chester River Drive, Grasonville
$639,000
Big Price Reduction! They aren’t making any more land so come grab this hard-to-find 14+ acres before its gone. Tucked away from the nearby waterfront communities with its rolling landscape & a private serene pond you will fall in love with this gorgeous property. So much room to play, relax, watch the wildlife and build your dream home. There is future subdivision potential for added value and public sewer is on Chester River Rd. This amazing property fronts on Loblolly Rd and Chester River Rd. Wonderful location, just minutes away from local parks, marina’s, cross island trail, hospitals, restaurants, shopping & recreational activities. All reasonable offers considered! For a limited time only, four lots including the cottage, totaling 18 acres (which may have further subdivision potential), is being offered at a discount. Potential investment opportunity.

Chester River Drive, Grasonville

Listing courtesy of Taylor Properties. Contact:

Chester River Drive, Grasonville
$259,000
Huge Price Reduction! Hard to find 3+ acres with pond & just steps from the water. Price to sell in this market. Come build your dream home on this beautiful property then relax & watch the eagles, herons and wildlife that frequent the pond. Wonderful location, just minutes away from local parks, marina’s, cross island trail, hospitals, restaurants, shopping, recreational activities & convenient to route 50. Seller will consider all reasonable offers!

Chester River Drive, Grasonville

Listing courtesy of Taylor Properties. Contact:

132 Pennick Dr, Stevensville
$459,000
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:

Peters Corner Road, Sudlersville
$299,000
The Peters Corner Timber property consists of 32 acres of timber. Timber class can be characterized as an old growth stand of oak species with some hickory and other hardwood species mixed in. The property is improved with electric and a camp site area towards the northern boundary line. No perc test on file with the county. Buyer to perform their own due diligence. A portion of the property is encumbered with an Open Space Easement.

Peters Corner Road, Sudlersville

Listing courtesy of The Land Group. Contact:

324 Web Foot Ln, Stevensville
$619,900
4 Beds ⋅ 3 Baths
Welcome home to this spacious and inviting 4-bedroom, 2.5-bath Colonial located in the sought-after community of Mallard Run, with easy access to the nearby bike trail. With an open floor plan and plenty of room to spread out, this home offers the perfect blend of comfort and convenience. The kitchen is truly the heart of the home, featuring granite countertops, a center island, and new stainless steel appliances, all flowing seamlessly into the main living areas. Just off the kitchen, the large sunroom provides the perfect spot to relax, entertain, or enjoy your morning coffee. Beautiful bamboo flooring adds warmth and character throughout much of the home, while the pellet stove creates a cozy atmosphere during the cooler months. A first-floor laundry room adds everyday convenience. Upstairs, the spacious primary suite offers a walk-in closet and a private bath with double vanities. Three additional bedrooms provide plenty of space for family, guests, or a home office. Step outside to enjoy the composite deck and patio, ideal for summer cookouts and outdoor gatherings. There is even an existing pad for you to bring your hot tub! Additional updates include a roof that's approximately 6 years old and an HVAC system that's approximately 4 years old. If you've been looking for a well-maintained home in a desirable neighborhood with room to live, work, and entertain, this one is not to be missed.

324 Web Foot Ln, Stevensville

Listing courtesy of Rosendale Realty. 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:

715 Winchester Creek Rd, Grasonville
$365,000
**Seller is motivated and ready to move on to the next project—**all offers will be considered! Currently priced significantly below assessed value. This west-facing waterfront lot on Winchester Creek offers over 4 acres of private, NO-HOA living directly off the Chester River. A fully engineered site plan is complete and ready for final submissions—over a year of professional engineering has gone into identifying the ideal build site, saving you time and effort in the permitting process. Enjoy immediate use of the waterfront this season while your new home is under construction. The property features a pier, boat ramp, and partially bulk headed shoreline, providing excellent water access from day one. By boat, you're just minutes from the world-famous Kent Narrows, with Rock Hall and Chestertown nearby. The fishing here is top-notch, with the Chester River producing some of the Eastern Shore’s largest catfish and snakeheads, in addition to excellent salt and brackish water opportunities. Calm and protected, Winchester Creek is ideal for kayaking and paddle boarding. Bring your own builder or use ours—this is a rare opportunity to create your dream waterfront retreat.

715 Winchester Creek Rd, Grasonville

Listing courtesy of Eastern Shore Real Estate, LLC. Contact:

705 Carmichael Rd, Queenstown
$489,900
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:

106 Phyllis Ct, Grasonville
$299,999
Tenant occupied, income producing two unit property in downtown Grasonville now available! The front house (B) rents for $1200 per month to a month to month tenant. The house (B) has 3 bedrooms and 2 baths. The 2 bed 1 bath second floor garage apt rents for $1378 per month to month to month tenants. All tenant spay their own utilities.

106 Phyllis Ct, Grasonville

Listing courtesy of Alberti Realty, LLC. 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:

412 Main St, Stevensville
$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:

103 Opera Ct, Centreville
$489,000
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:

1645 Ruthsburg Rd, Centreville
$375,000
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:

107 2nd St, Crumpton
$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:

136 Long Dr, Queenstown
$425,000
3 Beds ⋅ 3 Baths
Nestled in the prestigious Queenstown Harbor community, this exquisite carriage house-style townhouse offers an unparalleled blend of luxury and comfort. Spanning 1,916 square feet, this meticulously maintained residence is a sanctuary for those who appreciate high-end living and an exclusive lifestyle. Step inside to discover an open floor plan that seamlessly integrates elegance and functionality. The interior boasts stunning hardwood floors, complemented by plush carpeting and ceramic tile, creating a warm and inviting atmosphere. Crown moldings and ceiling fans add a touch of sophistication, while the corner brick fireplace serves as a captivating focal point, perfect for cozy evenings. The gourmet kitchen is a chef's dream, featuring stainless steel appliances, including a built-in microwave, dishwasher, and electric oven/range. Ample cabinetry and counter space ensure that culinary creations can be crafted with ease. Retreat to the luxurious master suite, where tranquility reigns. The thoughtfully designed layout includes two additional bedrooms, providing ample space for guests or a home office. With two full bathrooms and a convenient half bath, morning routines are a breeze. Step outside to your private deck, where you can savor morning coffee or unwind with a glass of wine while overlooking the lush golf course views. The meticulously landscaped exterior features a well-maintained gutter system and sidewalks, enhancing the overall curb appeal. A detached garage and ample driveway parking ensure convenience for you and your guests. For water enthusiasts, this property offers private access to a cove just blocks away, perfect for boating and fishing adventures. The serene surroundings invite you to embrace an active lifestyle, whether it's a leisurely day on the water or a round of golf at the nearby course. This home is not just a residence; it's a lifestyle choice that embodies luxury, comfort, and convenience. Experience the best of Queenstown Harbor living, where every detail has been thoughtfully curated to elevate your everyday life. Don't miss the opportunity to make this exceptional property your own.A Buyers Bonus of $5,000 to an acceptable offer ratified by 10/10/2026.

136 Long Dr, Queenstown

Listing courtesy of Coldwell Banker Realty. 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
$575,000
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:

1000 Herons Nest Way Unit 43, Chester
$595,000
2 Beds ⋅ 3 Baths
Beautiful fourth-floor condo offering nearly 2,000 square feet of living space, featuring two bedrooms, a home office, two full baths, and a half bath. Enjoy morning sun from the oversized porch, a spacious living room, and an open-concept layout designed for comfort and entertainment. Highlights include luxury flooring, a fireplace, and a beautifully appointed kitchen with an oversized center island and quartz countertops stainless steel appliances and much more. This unit also includes a one-car garage and private storage space. The community offers unparalleled amenities and gorgeous water views, creating the perfect Chesapeake Bay lifestyle. Enjoy walking trails, outdoor tennis courts, indoor and outdoor pools, and a 23,000-square-foot clubhouse with outdoor spaces, a ballroom, test kitchen, outdoor bar, and community pier, views of the Chester River.

1000 Herons Nest Way Unit 43, Chester

Listing courtesy of Coldwell Banker Realty. Contact:

420 Duhamel Corner Rd, Marydel
$995,000
4 Beds ⋅ 3 Baths
Farm Compound., with three homes! Each home is independent with separate addresses, all on 48 acres. The lands include woods and a pond. The primary home is 2800 square feet just recently remodeled. Open concept living all the rooms are very spacious with a kitchen with tons of storage and lots of counter space. There is an office space as well so many options to use as additional bedrooms or hobby room. A laundry area that is a room not a closet. The HVAC system was just replaced on the main home, as many other features of this house. Number two house was just put on the property in 2025, Clayton Holmes three bedrooms two baths would make a wonderful in-laws house or a rental. Number three house sits to the back of the property again is its own separate structure, is a remodled single wide. Would make an excellent income, Property or a caretaker residence. This property offers so many options it’s unlimited. It also includes a 30 x 50 insulated pole barn with a concrete floor electric separate meter and pitcher pump. Two pasture areas exist with shelter for live stock they currently have goats. This is a absolutly one of a kind property if you want to have a Equine center lots of room to build a indoor arena or to raise livestock. The entire family can live here and have there own house. Would be an excellent Equine center good pastures building could be converted to stalls. The current owners have greatly improved the property it is now waiting for the next care takers to see what they do with this special property and its new use.

420 Duhamel Corner Rd, Marydel

Listing courtesy of Benson & Mangold, LLC.. 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:

Romancoke Rd, Stevensville
$1,500,000
Great location for your commercial development project! This 3.4 acres property is located across from the Bay Bridge Airport and is less than a mile from Rt.​ 50/301 and the Chesapeake Bay Bridge.​ With 304 ft of frontage on Rt.​ 8/Romancoke Road and over 700 ft along Kent Manor Drive, the property offers exceptional visibility with high traffic counts.​ It’s zoned Urban Commercial with access to public water and sewer service.​

Romancoke Rd, Stevensville

Listing courtesy of Rock Hall Properties Real Estate. Contact: