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$549,987

Nestled on a peaceful country setting, this well-maintained colonial offers the perfect blend of privacy and comfort. Featuring 4 bedrooms, 2.5 baths, and soaring cathedral ceilings, the home is filled with natural light and spacious living areas. Enjoy cozy evenings by the fireplace or entertain outdoors in your private backyard oasis complete with a saltwater in-ground pool and a large fenced rear yard. The attached 2-car garage and expansive driveway provide plenty of parking. Conveniently located just a short drive from shopping, dining, schools, and major commuter routes, this home offers the tranquility of country living without sacrificing convenience. Electric solar panels to reduce your monthly energy cost. Don’t miss this exceptional opportunity!

4 Beds ⋅ 3 Baths

Nestled on a peaceful country setting, this well-maintained colonial offers the perfect blend of privacy and comfort. Featuring 4 bedrooms, 2.5 baths, and soaring cathedral ceilings, the home is filled with natural light and spacious living areas. Enjoy cozy evenings by the fireplace or entertain outdoors in your private backyard oasis complete with a saltwater in-ground pool and a large fenced rear yard. The attached 2-car garage and expansive driveway provide plenty of parking. Conveniently located just a short drive from shopping, dining, schools, and major commuter routes, this home offers the tranquility of country living without sacrificing convenience. Electric solar panels to reduce your monthly energy cost. Don’t miss this exceptional opportunity!

611 Clark Corners Rd, Centreville

Listing courtesy of Chaney Homes, LLC. Contact: (410) 739-0242

$699,000

**KENT ISLAND LIVING, THOUGHTFULLY DESIGNED FOR EVERYDAY LIFE!** This beautiful Ellendale home offers the space you need, the flexibility you want, and an unbeatable Kent Island location just minutes from the Chesapeake Bay Bridge. While this is one of the community's larger homes, the thoughtfully designed floor plan keeps the main living areas comfortably centered on the main and upper levels, with the finished English basement providing additional space when you need it. The main level is where everyday life happens, with a beautiful gourmet kitchen featuring granite countertops, stainless steel appliances, an oversized island, and a butler's pantry with cabinetry and a beverage refrigerator. The kitchen opens to the family room and casual dining area, with sliding doors leading to the deck and fenced backyard. A private office and formal dining room add even more functionality without taking away from the open feel of the main living space. Upstairs, you'll find four bedrooms, including an expansive primary suite with dual walk-in closets and a spacious en-suite bath, plus a second primary bedroom/Jr. suite and two additional bedrooms connected by a Jack and Jill bath. The finished English basement adds an entirely separate level of flexibility with two additional bedrooms, both with walk-in closets, a full bath, a second family room, and a recreation/game room. Use it for guests, extended family, hobbies, entertaining, or simply have the extra space available when you need it. With nearly 4,300 square feet, a two-car garage, and six bedrooms total, this home offers plenty of room without requiring every square foot to be part of your everyday routine. And the location is hard to beat. Ellendale is close to Kent Island's schools, shopping, waterfront restaurants, marinas, parks, resorts, and water access, while the Chesapeake Bay Bridge is just minutes away for an easy commute off the island. Community amenities include a pool, tot lot, walking trails, and creek access for kayaking and other water activities. **Come see how this spacious home can give you room to live, room to host, and room to grow, all in the heart of Kent Island.**

6 Beds ⋅ 5 Baths

**KENT ISLAND LIVING, THOUGHTFULLY DESIGNED FOR EVERYDAY LIFE!** This beautiful Ellendale home offers the space you need, the flexibility you want, and an unbeatable Kent Island location just minutes from the Chesapeake Bay Bridge. While this is one of the community's larger homes, the thoughtfully designed floor plan keeps the main living areas comfortably centered on the main and upper levels, with the finished English basement providing additional space when you need it. The main level is where everyday life happens, with a beautiful gourmet kitchen featuring granite countertops, stainless steel appliances, an oversized island, and a butler's pantry with cabinetry and a beverage refrigerator. The kitchen opens to the family room and casual dining area, with sliding doors leading to the deck and fenced backyard. A private office and formal dining room add even more functionality without taking away from the open feel of the main living space. Upstairs, you'll find four bedrooms, including an expansive primary suite with dual walk-in closets and a spacious en-suite bath, plus a second primary bedroom/Jr. suite and two additional bedrooms connected by a Jack and Jill bath. The finished English basement adds an entirely separate level of flexibility with two additional bedrooms, both with walk-in closets, a full bath, a second family room, and a recreation/game room. Use it for guests, extended family, hobbies, entertaining, or simply have the extra space available when you need it. With nearly 4,300 square feet, a two-car garage, and six bedrooms total, this home offers plenty of room without requiring every square foot to be part of your everyday routine. And the location is hard to beat. Ellendale is close to Kent Island's schools, shopping, waterfront restaurants, marinas, parks, resorts, and water access, while the Chesapeake Bay Bridge is just minutes away for an easy commute off the island. Community amenities include a pool, tot lot, walking trails, and creek access for kayaking and other water activities. **Come see how this spacious home can give you room to live, room to host, and room to grow, all in the heart of Kent Island.**

247 Breeding Blvd, Stevensville

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

$199,900

Nestled along the water's edge, this waterfront opportunity offers a canvas to create your own Eastern Shore retreat. Whether you choose to renovate the existing 3BR cottage or build on the existing foundation there is plenty of potential. Buyer to confirm building restrictions with the county. This property features a new deep well, new well pump, and new septic holding tanks in 2026. The existing interior of the home has been taken down to the framing and includes 100-amp electrical service, providing a solid starting point for your vision. Outdoor enthusiasts will enjoy everything this property has to offer. Fish for perch, bass, catfish, and snakeheads, or spend the day crabbing from your shoreline. Waterfowl hunters will enjoy the existing duck blind, while everyone will appreciate the stunning sunsets overlooking the water. Whether you're looking for a peaceful weekend escape, a hunting and fishing camp, or the site of your future waterfront cottage, this property offers an opportunity that's becoming increasingly difficult to find.

3 Beds ⋅ 2 Baths

Nestled along the water's edge, this waterfront opportunity offers a canvas to create your own Eastern Shore retreat. Whether you choose to renovate the existing 3BR cottage or build on the existing foundation there is plenty of potential. Buyer to confirm building restrictions with the county. This property features a new deep well, new well pump, and new septic holding tanks in 2026. The existing interior of the home has been taken down to the framing and includes 100-amp electrical service, providing a solid starting point for your vision. Outdoor enthusiasts will enjoy everything this property has to offer. Fish for perch, bass, catfish, and snakeheads, or spend the day crabbing from your shoreline. Waterfowl hunters will enjoy the existing duck blind, while everyone will appreciate the stunning sunsets overlooking the water. Whether you're looking for a peaceful weekend escape, a hunting and fishing camp, or the site of your future waterfront cottage, this property offers an opportunity that's becoming increasingly difficult to find.

220 Kirbys Landing Rd, Millington

Listing courtesy of Select Land & Homes, LLC. Contact: (410) 708-0956

$549,900

TWO LOTS FOR SALE with two different tax Ids/addresses. The home sits on 1.16 arces and the additional adjacent lot sits on 1.10 acres which was graded as a Par 3 golf course. The second lots tax ID is 1805020174, address is 165 Greenwood Creek Rd, Queenstown, MD 21658. This house is ready for your own personal touches and repairs, with four bedrooms and 2.5 baths sitting on 2.16 lush acres of privacy. This homes offers a mature landscaped yard with WATERVIEWS! Hardwood floors throughout just waiting to be brought back to their original beauty. This home also features a full In-law suite / guest house. Located in Queenstown, with easy commutes to Annapolis, Washington, Baltimore, Delaware and the beaches. Come see this home and make it your own today!

4 Beds ⋅ 3 Baths

TWO LOTS FOR SALE with two different tax Ids/addresses. The home sits on 1.16 arces and the additional adjacent lot sits on 1.10 acres which was graded as a Par 3 golf course. The second lots tax ID is 1805020174, address is 165 Greenwood Creek Rd, Queenstown, MD 21658. This house is ready for your own personal touches and repairs, with four bedrooms and 2.5 baths sitting on 2.16 lush acres of privacy. This homes offers a mature landscaped yard with WATERVIEWS! Hardwood floors throughout just waiting to be brought back to their original beauty. This home also features a full In-law suite / guest house. Located in Queenstown, with easy commutes to Annapolis, Washington, Baltimore, Delaware and the beaches. Come see this home and make it your own today!

161 Greenwood Creek Rd, Queenstown

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

$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 St, Church Hill

Listing courtesy of Taylor Properties. Contact:

$525,000

Welcome to resort-style living at K. Hovnanian's Four Seasons at Kent Island — one of the Eastern Shore's premier 55+ waterfront communities on the Chesapeake Bay. This Magothy model condo offers approximately 2003 sq. ft. of thoughtfully designed single-level living, featuring 2 bedrooms — each with its own attached bathroom — plus a powder room for guests, a private home office with French doors, oversized walk-in closets in both bedrooms, a dry bar, and a private deck to unwind and take in the coastal air. A private climate-controlled storage room and a 1-car private garage complete the low-maintenance, lock-and-leave lifestyle this community is known for. Residents enjoy access to a beautifully appointed in-building community room, perfect for relaxing, entertaining, or working from somewhere other than your unit. Your HOA dues unlock access to the award-winning 24,000-sq.-ft. Chester House clubhouse — the true heart of the community — with indoor and outdoor swimming pools, a fully equipped fitness center, yoga studio, demonstration kitchen, library, billiards and game room, and a grand ballroom for private events. Outside, residents enjoy lighted tennis, pickleball, and bocce courts, a dog park, gas and wood-burning fire pits, a waterside tiki bar, and 4.3+ miles of walking and biking trails connecting to the Cross Island Trail. Water lovers will love the 450-foot community pier on the Chester River with boat slips, plus canoe and kayak launch and storage — all just steps from the clubhouse. Live entertainment and community life never stop, with a full-time lifestyle director curating year-round programming: walking club, water aerobics, Zumba, mahjong, kayaking outings, holiday parties, and concerts and movie nights at the community's outdoor waterfront amphitheater. This is more than a home — it's a resort lifestyle every single day. Minutes to Kent Island's shops, waterfront dining, and Queenstown Premium Outlets, with easy access to the Bay Bridge for trips to Annapolis, Baltimore, and Washington D.C. Don't wait to start living the Four Seasons lifestyle — schedule your private showing today.

2 Beds ⋅ 3 Baths

Welcome to resort-style living at K. Hovnanian's Four Seasons at Kent Island — one of the Eastern Shore's premier 55+ waterfront communities on the Chesapeake Bay. This Magothy model condo offers approximately 2003 sq. ft. of thoughtfully designed single-level living, featuring 2 bedrooms — each with its own attached bathroom — plus a powder room for guests, a private home office with French doors, oversized walk-in closets in both bedrooms, a dry bar, and a private deck to unwind and take in the coastal air. A private climate-controlled storage room and a 1-car private garage complete the low-maintenance, lock-and-leave lifestyle this community is known for. Residents enjoy access to a beautifully appointed in-building community room, perfect for relaxing, entertaining, or working from somewhere other than your unit. Your HOA dues unlock access to the award-winning 24,000-sq.-ft. Chester House clubhouse — the true heart of the community — with indoor and outdoor swimming pools, a fully equipped fitness center, yoga studio, demonstration kitchen, library, billiards and game room, and a grand ballroom for private events. Outside, residents enjoy lighted tennis, pickleball, and bocce courts, a dog park, gas and wood-burning fire pits, a waterside tiki bar, and 4.3+ miles of walking and biking trails connecting to the Cross Island Trail. Water lovers will love the 450-foot community pier on the Chester River with boat slips, plus canoe and kayak launch and storage — all just steps from the clubhouse. Live entertainment and community life never stop, with a full-time lifestyle director curating year-round programming: walking club, water aerobics, Zumba, mahjong, kayaking outings, holiday parties, and concerts and movie nights at the community's outdoor waterfront amphitheater. This is more than a home — it's a resort lifestyle every single day. Minutes to Kent Island's shops, waterfront dining, and Queenstown Premium Outlets, with easy access to the Bay Bridge for trips to Annapolis, Baltimore, and Washington D.C. Don't wait to start living the Four Seasons lifestyle — schedule your private showing today.

230 Switchgrass Way Unit #12, Chester

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442

$525,000

Welcome to 205 Anchor Lane, a spacious and versatile home in the desirable Castle Marina community of Chester! Situated on a generous half-acre lot with no HOA, this oversized split foyer offers the flexibility, space, and location that today's buyers are looking for. 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.

5 Beds ⋅ 3 Baths

Welcome to 205 Anchor Lane, a spacious and versatile home in the desirable Castle Marina community of Chester! Situated on a generous half-acre lot with no HOA, this oversized split foyer offers the flexibility, space, and location that today's buyers are looking for. 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: 7033788810

$789,000

New Price Reduction- 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 Profile appliances and opens to the comfortable family room with a gas fireplace and sliders leading to the Florida 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. Recent improvements include two NEW (2026) Lennox HVAC Hybrid units with smart Thermostats. The crawlspace has been newly encapsulated with an April Aire dehumidifier (2026) and there is a tankless Navien hot water heater. 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!

4 Beds ⋅ 3 Baths

New Price Reduction- 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 Profile appliances and opens to the comfortable family room with a gas fireplace and sliders leading to the Florida 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. Recent improvements include two NEW (2026) Lennox HVAC Hybrid units with smart Thermostats. The crawlspace has been newly encapsulated with an April Aire dehumidifier (2026) and there is a tankless Navien hot water heater. 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: 8003833535

$629,900

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.

3 Beds ⋅ 2 Baths

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: (866) 987-3937

$829,000

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. For a limited time only, four lots including the cottage, totaling 18 acres (which may have further subdivision potential), is being offered at $1,650,000. Potential investment opportunity.

Chester River Dr, Grasonville

Listing courtesy of Taylor Properties. Contact:

$349,000

Hard to find 3+ acres with pond & just steps from the water. 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. For a limited time only, four lots including the cottage, totaling 18 acres (which may have further subdivision potential), is being offered at $1,650,000. Great investment opportunity.

Chester River Dr, Grasonville

Listing courtesy of Taylor Properties. Contact:

$199,900

Welcome to the water privileged community of Chester River Beach where you will find this water view lot just waiting to have a new home built on it or save as an investment. Enjoy the added bonus of having a large existing garage or stroll down to the beautiful waterfront park and boat ramp. This lot has public sewer access. Embrace the lifestyle you've always wanted on MDs beautiful eastern shore. Wonderful location, just minutes away from local parks, marina’s, cross island trail, hospitals, restaurants, shopping, recreational activities & convenient to route 50. Sold As Is.

903 Chester River Dr, Grasonville

Listing courtesy of Taylor Properties. Contact:

$299,900

OPEN HOUSE, Sunday Aug 23, 9-12. Huge price drop so come on out & discover this charming water view cottage nestled in the sought after water privileged Chester River Beach community. This remodeled & inviting home offers the perfect balance of comfort, convenience & lifestyle with plenty of room to add on or up & expand to capture water views. This property is on public sewer. You’ll love spending relaxing mornings or evenings on the front patio or watch the sun set from the waterfront park/boat launch just steps away. Wonderful location, just minutes away from local parks, marina’s, cross island trail, hospitals, restaurants, shopping, recreational activities & convenient to route 50. Check out the virtual tour. Sold As Is at this amazing price. For a limited time only, four lots including the cottage, totaling 18 acres (which may have further subdivision potential), is being offered at $1,650,000. Potential investment opportunity.

2 Beds ⋅ 1 Baths

OPEN HOUSE, Sunday Aug 23, 9-12. Huge price drop so come on out & discover this charming water view cottage nestled in the sought after water privileged Chester River Beach community. This remodeled & inviting home offers the perfect balance of comfort, convenience & lifestyle with plenty of room to add on or up & expand to capture water views. This property is on public sewer. You’ll love spending relaxing mornings or evenings on the front patio or watch the sun set from the waterfront park/boat launch just steps away. Wonderful location, just minutes away from local parks, marina’s, cross island trail, hospitals, restaurants, shopping, recreational activities & convenient to route 50. Check out the virtual tour. Sold As Is at this amazing price. For a limited time only, four lots including the cottage, totaling 18 acres (which may have further subdivision potential), is being offered at $1,650,000. Potential investment opportunity.

901 Chester River Dr, Grasonville

Listing courtesy of Taylor Properties. Contact:

$459,000

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.

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: (410) 739-0242

$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 Rd, Sudlersville

Listing courtesy of The Land Group. Contact: (410) 934-3478

$724,999

Why wait for new construction when you can move right into this beautiful Simone model in the highly sought-after Four Seasons at Kent Island? This spacious home offers 4 bedrooms, 3 full baths, and the perfect blend of comfort, style, and low-maintenance living.The open floor plan makes everyday living and entertaining easy, with a bright kitchen featuring quartz countertops, stainless steel appliances, a large center island, and plenty of space to gather with family and friends. The cozy gas fireplace adds warmth and charm to the main living area, while the screened patio is the perfect spot to relax with your morning coffee or unwind at the end of the day.The large primary suite offers a peaceful retreat with a spacious walk-in closet, double vanities, and a walk-in shower. Additional bedrooms AND an office provide plenty of room for guests, hobbies, or just about anything you can think of and the convenient mud room adds extra functionality.Living in Four Seasons at Kent Island means enjoying an incredible lifestyle. Residents have access to a stunning 24,000-square-foot clubhouse featuring indoor and outdoor pools, a state-of-the-art fitness center, tennis and pickleball courts, and a full-time lifestyle director who keeps the social calendar full of activities including walking clubs, yoga, mahjong, kayaking, pickleball, and more.Kent Island living is all about making new friends, staying active, and enjoying the lifestyle you've worked hard to achieve. Come see why so many people are proud to call Four Seasons home.

4 Beds ⋅ 3 Baths

Why wait for new construction when you can move right into this beautiful Simone model in the highly sought-after Four Seasons at Kent Island? This spacious home offers 4 bedrooms, 3 full baths, and the perfect blend of comfort, style, and low-maintenance living.The open floor plan makes everyday living and entertaining easy, with a bright kitchen featuring quartz countertops, stainless steel appliances, a large center island, and plenty of space to gather with family and friends. The cozy gas fireplace adds warmth and charm to the main living area, while the screened patio is the perfect spot to relax with your morning coffee or unwind at the end of the day.The large primary suite offers a peaceful retreat with a spacious walk-in closet, double vanities, and a walk-in shower. Additional bedrooms AND an office provide plenty of room for guests, hobbies, or just about anything you can think of and the convenient mud room adds extra functionality.Living in Four Seasons at Kent Island means enjoying an incredible lifestyle. Residents have access to a stunning 24,000-square-foot clubhouse featuring indoor and outdoor pools, a state-of-the-art fitness center, tennis and pickleball courts, and a full-time lifestyle director who keeps the social calendar full of activities including walking clubs, yoga, mahjong, kayaking, pickleball, and more.Kent Island living is all about making new friends, staying active, and enjoying the lifestyle you've worked hard to achieve. Come see why so many people are proud to call Four Seasons home.

233 Peregrine Dr, Chester

Listing courtesy of Rosendale Realty. Contact: 4107580333

$619,900

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.

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: 4107580333

$380,000

You’re invited Open House, Saturday, August 22nd, 9 to 11 AM.. Welcome to this beautifully situated two-story townhome overlooking the tranquil pond in the highly desirable Bridgepointe community on Kent Island. Enjoy an exceptional location with convenient location to Route 50 and just minutes from waterfront dining, Kent Narrows, the Cross Island Trail, public boat ramps, parks, shopping, medical facilities, and more. Experience the perfect blend of comfort, convenience, and the relaxed Eastern Shore lifestyle. Offers Peace of Mind with a brand NEW Roof - Just completed! Designed for easy everyday living, the bright, open floor plan seamlessly connects the kitchen, dining area, and living room, where a cozy gas fireplace creates a warm and relaxing space. The adjoining spacious sunroom showcases tranquil pond views, providing the perfect backdrop for morning coffee, quiet evenings, or entertaining guests. The main level also features a desirable first-floor primary suite with a walk-in closet, private access to the sunroom, and an en-suite bath complete with a relaxing Jacuzzi tub and separate walk-in shower. A flexible bonus room with a laundry area and French door access offers endless possibilities as a home office, den, additional bedroom, craft room, or fitness space. Upstairs, two generously sized bedrooms and a full bath provide comfortable accommodations for family and visitors. Whether you're looking for a full-time residence, a weekend getaway, or a low-maintenance retreat, this exceptional pond front home offers the very best of Kent Island living. Don't miss this rare opportunity—it's more than a home, it's a lifestyle!

3 Beds ⋅ 2 Baths

You’re invited Open House, Saturday, August 22nd, 9 to 11 AM.. Welcome to this beautifully situated two-story townhome overlooking the tranquil pond in the highly desirable Bridgepointe community on Kent Island. Enjoy an exceptional location with convenient location to Route 50 and just minutes from waterfront dining, Kent Narrows, the Cross Island Trail, public boat ramps, parks, shopping, medical facilities, and more. Experience the perfect blend of comfort, convenience, and the relaxed Eastern Shore lifestyle. Offers Peace of Mind with a brand NEW Roof - Just completed! Designed for easy everyday living, the bright, open floor plan seamlessly connects the kitchen, dining area, and living room, where a cozy gas fireplace creates a warm and relaxing space. The adjoining spacious sunroom showcases tranquil pond views, providing the perfect backdrop for morning coffee, quiet evenings, or entertaining guests. The main level also features a desirable first-floor primary suite with a walk-in closet, private access to the sunroom, and an en-suite bath complete with a relaxing Jacuzzi tub and separate walk-in shower. A flexible bonus room with a laundry area and French door access offers endless possibilities as a home office, den, additional bedroom, craft room, or fitness space. Upstairs, two generously sized bedrooms and a full bath provide comfortable accommodations for family and visitors. Whether you're looking for a full-time residence, a weekend getaway, or a low-maintenance retreat, this exceptional pond front home offers the very best of Kent Island living. Don't miss this rare opportunity—it's more than a home, it's a lifestyle!

6010 Bridgepointe Dr, Chester

Listing courtesy of Rosendale Realty. Contact: 4107580333

$899,000

Escape to your own private Eastern Shore sanctuary! Nestled on 15.39 acres in Stevensville, 225 Batts Neck Road offers the ultimate blend of coastal convenience and secluded mountain-getaway. This stunning 3BR/2.5BA post-and-beam cabin welcomes you with a classic wrap-around porch and a cozy interior featuring a wood-burning stove—complete with a second fireplace rough-in for the upstairs lofted primary suite. The expansive layout includes an amazing living room and game area designed for hosting memorable family gatherings. The 15+ acres are an outdoor enthusiast's dream, featuring established walking and ATV trails, along with cleared open areas perfect for camping and firepits. Whether you are looking for a premier hunting retreat, a weekend getaway, or a permanent homestead with the potential to build a second home, this unique acreage delivers. Enjoy the best of the Eastern Shore: less than 2 miles from Matapeake Beach, 2.5 miles from Kentmorr Marina, and 4 miles from Bay Bridge Marina. Best of all, you are just 4 miles from the Bay Bridge for a seamless commute to Annapolis, Baltimore, or DC!

3 Beds ⋅ 3 Baths

Escape to your own private Eastern Shore sanctuary! Nestled on 15.39 acres in Stevensville, 225 Batts Neck Road offers the ultimate blend of coastal convenience and secluded mountain-getaway. This stunning 3BR/2.5BA post-and-beam cabin welcomes you with a classic wrap-around porch and a cozy interior featuring a wood-burning stove—complete with a second fireplace rough-in for the upstairs lofted primary suite. The expansive layout includes an amazing living room and game area designed for hosting memorable family gatherings. The 15+ acres are an outdoor enthusiast's dream, featuring established walking and ATV trails, along with cleared open areas perfect for camping and firepits. Whether you are looking for a premier hunting retreat, a weekend getaway, or a permanent homestead with the potential to build a second home, this unique acreage delivers. Enjoy the best of the Eastern Shore: less than 2 miles from Matapeake Beach, 2.5 miles from Kentmorr Marina, and 4 miles from Bay Bridge Marina. Best of all, you are just 4 miles from the Bay Bridge for a seamless commute to Annapolis, Baltimore, or DC!

225 Batts Neck Rd, Stevensville

Listing courtesy of Real Broker, LLC - Annapolis. Contact: 8554500442

$2,840,000

Privacy without isolation - Rare Find - 2 comfy houses on one waterfront property! Each with unobstructed views of the picturesque Cox Creek before it enters the Bay. Discover a captivating traditional charm in this vintage cape cod ( 3-bedrooms, 2-bathrooms) recently updated in spring 2026. The former detached garage converted into the 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.

3 Beds ⋅ 2 Baths

Privacy without isolation - Rare Find - 2 comfy houses on one waterfront property! Each with unobstructed views of the picturesque Cox Creek before it enters the Bay. Discover a captivating traditional charm in this vintage cape cod ( 3-bedrooms, 2-bathrooms) recently updated in spring 2026. The former detached garage converted into the 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:

$375,000

**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: 4103042011

$499,900

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!

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: (410) 643-5005

$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: 4439818000

$415,000

Just Reduced.... Welcome to 624 Romancoke Road on Kent Island. This beautiful 3 bedroom, 2 full bath Rancher is move in ready and awaiting it's next owner. Situated on a large lot with easy 2 minute access to the Chesapeake Bay Bridge, and easy commute to Annapolis, DC and Baltimore. No worrying about a private well or septic, this home is on public water and sewer. Fully renovated in 2016 with HVAC, appliances and roof in 2017, recent updates include the crawl space encapsulation 2025, additional attic insulation 2025, new windows 2024, front door and rear sliding door 2025 and the rear deck refurbished 2023. 2nd front door leads to possibly a in-law apartment with full bath and bedroom, with door leading into the kitchen. Located in the Bay City community that includes a boat ramp and pavilion, and a 2nd park located on the Chesapeake Bay with a tot lot. The feel of this home is bright and welcoming and the fenced rear yard allows for plenty of room for a future garage or pool. Take a tour of this home that will be available for a quick settlement.

3 Beds ⋅ 2 Baths

Just Reduced.... Welcome to 624 Romancoke Road on Kent Island. This beautiful 3 bedroom, 2 full bath Rancher is move in ready and awaiting it's next owner. Situated on a large lot with easy 2 minute access to the Chesapeake Bay Bridge, and easy commute to Annapolis, DC and Baltimore. No worrying about a private well or septic, this home is on public water and sewer. Fully renovated in 2016 with HVAC, appliances and roof in 2017, recent updates include the crawl space encapsulation 2025, additional attic insulation 2025, new windows 2024, front door and rear sliding door 2025 and the rear deck refurbished 2023. 2nd front door leads to possibly a in-law apartment with full bath and bedroom, with door leading into the kitchen. Located in the Bay City community that includes a boat ramp and pavilion, and a 2nd park located on the Chesapeake Bay with a tot lot. The feel of this home is bright and welcoming and the fenced rear yard allows for plenty of room for a future garage or pool. Take a tour of this home that will be available for a quick settlement.

624 Romancoke Rd, Stevensville

Listing courtesy of RE/MAX Executive. Contact: 4432741900

$915,000

Previous buyer's home sale contingency fell through. Back on the market! 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.

5 Beds ⋅ 4 Baths

Previous buyer's home sale contingency fell through. Back on the market! 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: 4102638686

$1,400,000

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.

5 Beds ⋅ 4 Baths

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: 7033788810

$1,750,000

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.

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: (410) 739-0242

$484,500

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.

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

$389,000

OPEN HOUSE SATURDAY, AUGUST 22ND 11AM - 1PM **USDA eligible financing!** This charming ranch-style home, renovated in 2020, offers a perfect blend of modern comfort and classic appeal. With a thoughtfully designed living space, this residence features three inviting bedrooms and two full bathrooms, including a luxurious primary bath with upgraded countertops and a walk-in tiled shower. The heart of the home is the spacious eat-in kitchen, complete with stainless steel appliances, an island for casual dining, and a family room that flows seamlessly off the kitchen, making it ideal for gatherings. Natural light abounds and the recessed lighting & ceiling fans enhance the warm ambiance throughout. Step outside to enjoy the maintenance-free deck and porch, perfect for relaxing or entertaining while overlooking the level fenced rear yard. Abundant off-street paved parking for numerous boats, RV's & vehicles. Situated in a welcoming community, this home is surrounded by well-maintained parks and recreational areas, providing ample opportunities for outdoor activities including; boating, fishing/crabbing, cook-outs & swimming on the sandy beaches along the scenic Chesapeake Bay. With easy access to restaurants, shops and a friendly neighborhood atmosphere, this property is not just a house; it's a place to create lasting memories. Experience the comfort and community spirit that this lovely Stevensville home and Kent Island lifestyle has to offer!

3 Beds ⋅ 2 Baths

OPEN HOUSE SATURDAY, AUGUST 22ND 11AM - 1PM **USDA eligible financing!** This charming ranch-style home, renovated in 2020, offers a perfect blend of modern comfort and classic appeal. With a thoughtfully designed living space, this residence features three inviting bedrooms and two full bathrooms, including a luxurious primary bath with upgraded countertops and a walk-in tiled shower. The heart of the home is the spacious eat-in kitchen, complete with stainless steel appliances, an island for casual dining, and a family room that flows seamlessly off the kitchen, making it ideal for gatherings. Natural light abounds and the recessed lighting & ceiling fans enhance the warm ambiance throughout. Step outside to enjoy the maintenance-free deck and porch, perfect for relaxing or entertaining while overlooking the level fenced rear yard. Abundant off-street paved parking for numerous boats, RV's & vehicles. Situated in a welcoming community, this home is surrounded by well-maintained parks and recreational areas, providing ample opportunities for outdoor activities including; boating, fishing/crabbing, cook-outs & swimming on the sandy beaches along the scenic Chesapeake Bay. With easy access to restaurants, shops and a friendly neighborhood atmosphere, this property is not just a house; it's a place to create lasting memories. Experience the comfort and community spirit that this lovely Stevensville home and Kent Island lifestyle has to offer!

105 Bobbit Ct, Stevensville

Listing courtesy of Beam Realty Group, Inc.. Contact: 4438656969

$749,000

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.

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