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$789,000

Waterfront living doesn't get much better than this. Welcome to 280 Lake Caroline Drive—a beautifully updated lakefront retreat where every day feels like a vacation. Rare Deep-Water Lakefront Living—Turnkey, Updated, and Ready for Your Next Chapter at Lake Caroline.” Welcome to 280 Lake Caroline Drive, a private waterfront retreat where thoughtful updates, wide lake views, and true move-in readiness come together on one of Lake Caroline’s most desirable lots. Set on more than half an acre with breathtaking 180-degree lake views and deep-water access, this beautifully maintained home delivers the feel of a year-round resort with the comfort and practicality of everyday living. A long paved driveway leads to the attached two-car garage, with generous additional parking for guests, boats, and recreational vehicles. Professionally landscaped grounds, extensive irrigation, and a fully fenced backyard create a setting designed for privacy, ease, and outdoor enjoyment. Inside, the home has been extensively updated across both levels. Highlights include remodeled bathrooms, updated flooring, newer kitchen appliances, a 2024 HVAC system, 2022 water heater, and a whole-house water filtration system installed in 2025. Four large bay windows fill the home with natural light and frame spectacular water views from multiple rooms. The main level offers comfortable living spaces and direct access to an elevated three-season porch overlooking the lake. The primary suite includes its own private balcony, an ideal spot for morning coffee, sunrise views, and quiet evenings by the water. Two gas fireplaces add warmth and character on both levels. The finished lower level offers excellent flexibility for guests, extended stays, multigenerational living, remote work, hobbies, or entertaining. This level features a spacious family room, large bedroom, full bath, kitchenette, two bonus rooms, one currently used as a fourth bedroom, and additional storage space. Outdoor living is where this property truly shines. Enjoy an oversized lakeside deck, expansive lawn, attached storage shed, and private deep-water dock ready for boating, fishing, swimming, kayaking, paddleboarding, and quiet days on the water. Active lawn care and HVAC service contracts convey to the new owner, adding convenience from day one. Lake Caroline offers an outstanding waterfront lifestyle with a 277-acre full-service lake, two sandy beaches, swimming pool with lifeguards, clubhouse, playgrounds, tennis courts, pickleball courts, basketball courts, fishing, boating, water skiing, wakeboarding, jet skiing, kayaking, paddleboarding, and year-round community events. This is an exceptional fit for a full-time residence, relocation to the area, second home, weekend retreat, or move-up waterfront purchase. Located within a gated, amenity-rich community just minutes from I-95, shopping, dining, and schools, 280 Lake Caroline Drive is a rare opportunity to own one of Lake Caroline’s standout waterfront properties. Nothing left to do except move in and start enjoying lakefront living.

3 Beds ⋅ 3 Baths

Waterfront living doesn't get much better than this. Welcome to 280 Lake Caroline Drive—a beautifully updated lakefront retreat where every day feels like a vacation. Rare Deep-Water Lakefront Living—Turnkey, Updated, and Ready for Your Next Chapter at Lake Caroline.” Welcome to 280 Lake Caroline Drive, a private waterfront retreat where thoughtful updates, wide lake views, and true move-in readiness come together on one of Lake Caroline’s most desirable lots. Set on more than half an acre with breathtaking 180-degree lake views and deep-water access, this beautifully maintained home delivers the feel of a year-round resort with the comfort and practicality of everyday living. A long paved driveway leads to the attached two-car garage, with generous additional parking for guests, boats, and recreational vehicles. Professionally landscaped grounds, extensive irrigation, and a fully fenced backyard create a setting designed for privacy, ease, and outdoor enjoyment. Inside, the home has been extensively updated across both levels. Highlights include remodeled bathrooms, updated flooring, newer kitchen appliances, a 2024 HVAC system, 2022 water heater, and a whole-house water filtration system installed in 2025. Four large bay windows fill the home with natural light and frame spectacular water views from multiple rooms. The main level offers comfortable living spaces and direct access to an elevated three-season porch overlooking the lake. The primary suite includes its own private balcony, an ideal spot for morning coffee, sunrise views, and quiet evenings by the water. Two gas fireplaces add warmth and character on both levels. The finished lower level offers excellent flexibility for guests, extended stays, multigenerational living, remote work, hobbies, or entertaining. This level features a spacious family room, large bedroom, full bath, kitchenette, two bonus rooms, one currently used as a fourth bedroom, and additional storage space. Outdoor living is where this property truly shines. Enjoy an oversized lakeside deck, expansive lawn, attached storage shed, and private deep-water dock ready for boating, fishing, swimming, kayaking, paddleboarding, and quiet days on the water. Active lawn care and HVAC service contracts convey to the new owner, adding convenience from day one. Lake Caroline offers an outstanding waterfront lifestyle with a 277-acre full-service lake, two sandy beaches, swimming pool with lifeguards, clubhouse, playgrounds, tennis courts, pickleball courts, basketball courts, fishing, boating, water skiing, wakeboarding, jet skiing, kayaking, paddleboarding, and year-round community events. This is an exceptional fit for a full-time residence, relocation to the area, second home, weekend retreat, or move-up waterfront purchase. Located within a gated, amenity-rich community just minutes from I-95, shopping, dining, and schools, 280 Lake Caroline Drive is a rare opportunity to own one of Lake Caroline’s standout waterfront properties. Nothing left to do except move in and start enjoying lakefront living.

280 Lake Caroline Dr, Ruther Glen

Listing courtesy of Metro Premier Homes. Contact: 703606-4156

$479,000

Custom Brick Rancher with 2500 sq ft of living space sitting on over half an acre just outside of downtown Federalsburg overlooking Chambers Park is waiting for you to come see to appreciate. Owners have done many improvements and upgrades to the property, but left some of it's timeless charm. New carpet has been installed on the porch, breakfast nook, and family room July 2026, new windows 2026, New refrigerator July 2026, new HVAC 2021, 3yr old whole house water treatment with R/O system, and a 40 breaker 4D electrical panel is new, too! With a mix of formal rooms and recreation areas all off the kitchen, but split from the generously sized Bedrooms, you will have no problem entertaining all year round. 2 Sheds, both with electric, one with garage door and workbenches help with all those indoor and outdoor projects. 3rd full bath is off the enclosed sunporch for ease of use from multiple areas and outside. In addition to Chambers Park the Federalsburg Park and Marina is just down the road for added recreation, along with shopping and restaurants in Federalsburg, Easton, Preston, or just over into Delaware not to mention multiple Beaches in both MD and DE that are close enough to spend the day and come back home. Don't miss your opportunity to see this one and call it yours!

3 Beds ⋅ 3 Baths

Custom Brick Rancher with 2500 sq ft of living space sitting on over half an acre just outside of downtown Federalsburg overlooking Chambers Park is waiting for you to come see to appreciate. Owners have done many improvements and upgrades to the property, but left some of it's timeless charm. New carpet has been installed on the porch, breakfast nook, and family room July 2026, new windows 2026, New refrigerator July 2026, new HVAC 2021, 3yr old whole house water treatment with R/O system, and a 40 breaker 4D electrical panel is new, too! With a mix of formal rooms and recreation areas all off the kitchen, but split from the generously sized Bedrooms, you will have no problem entertaining all year round. 2 Sheds, both with electric, one with garage door and workbenches help with all those indoor and outdoor projects. 3rd full bath is off the enclosed sunporch for ease of use from multiple areas and outside. In addition to Chambers Park the Federalsburg Park and Marina is just down the road for added recreation, along with shopping and restaurants in Federalsburg, Easton, Preston, or just over into Delaware not to mention multiple Beaches in both MD and DE that are close enough to spend the day and come back home. Don't miss your opportunity to see this one and call it yours!

104 Charlotte Ave, Federalsburg

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255

$330,000

Ready to own without the stress? Move in and start your life, not your renovation. This fully renovated home is one your friends will be drooling over. The kitchen steals the show: soft-close navy cabinets with gold hardware and quartz countertops, stainless steel appliances, a deep kitchen sink, stylish floating shelves, and a crisp white tile backsplash. It's the kind of space that makes cooking and gathering feel effortless. The first-floor primary bedroom is your sanctuary—walk-in closet, walk-in tile shower that feels like a spa, beautiful quartz vanity. Wide plank LVP flooring keeps the whole home feeling fresh and connected. The two-car detached garage is insulated, has electric, and includes a storage room—practical space that actually works. The 0.325-acre lot sits across from Chambers Park, where you can enjoy a ball game, walking path, or tennis courts. Paved driveway, plenty of parking, and a home that's honestly ready for you. This is what move-in ready feels like: fully updated, thoughtfully finished, and zero projects waiting. Just unpack and live.

3 Beds ⋅ 3 Baths

Ready to own without the stress? Move in and start your life, not your renovation. This fully renovated home is one your friends will be drooling over. The kitchen steals the show: soft-close navy cabinets with gold hardware and quartz countertops, stainless steel appliances, a deep kitchen sink, stylish floating shelves, and a crisp white tile backsplash. It's the kind of space that makes cooking and gathering feel effortless. The first-floor primary bedroom is your sanctuary—walk-in closet, walk-in tile shower that feels like a spa, beautiful quartz vanity. Wide plank LVP flooring keeps the whole home feeling fresh and connected. The two-car detached garage is insulated, has electric, and includes a storage room—practical space that actually works. The 0.325-acre lot sits across from Chambers Park, where you can enjoy a ball game, walking path, or tennis courts. Paved driveway, plenty of parking, and a home that's honestly ready for you. This is what move-in ready feels like: fully updated, thoughtfully finished, and zero projects waiting. Just unpack and live.

104 Chambers St, Federalsburg

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

$395,000

Updated + Upgraded - Turn-key 4BR/2.5BA contemporary 2-story home on a culdesac lot backing to trees, near historic downtown Denton - a true gem of an Eastern Shore town, perched on the banks of the Choptank River - but tucked away on a residential court. New flooring + paint throughout, new granite counters, new kitchen appliances, new fixtures. Wide open floorplan boasts tall ceilings, spacious rooms throughout, and lots of great light. Great room with new LVP flooring offers living, dining, breakfast, and kitchen spaces. Bright + cheery kitchen - light gray cabinetry, new stainless steel appliances, gorgeous granite counters, new custom tile backsplash. Sliders out to the expansive deck overlooking your roomy yard. Separate flex room - perfect for a home office, study - whatever you like. A half bath completes the 1st floor. Upstairs, primary bedroom with vaulted ceiling, new carpet, walk-in closet, full, en-suite bath - new tile floors, step-in shower, double-sink vanity. 3 additional bedrooms - all with new carpet. 2nd full bath with tub/shower combo, tile flooring. Laundry room with new tile floors completes the home's interior. Attached 2-car garage with extra space for storage, concrete driveway, nice-sized storage shed. Minutes to the best that Denton and Caroline County offers - great local restaurants, boutique and big-box store shopping, arts + culture, history galore, plenty of public launches and marinas, boating, world-class fishing, crabbing, hunting, wildlife estuaries, incredible state parks - a true paradise for nature lovers, photographers, boaters, fishermen and anyone who wants to enjoy the more relaxed pace on the Eastern Shore - from the beaches to the bays and beyond! Great central location on the Delmarva Peninsula -- 15mi to Easton, 30mi to the Bay Bridge or Cambridge, 40mi to Annapolis's Downtown, about an hour to the Delaware Beaches or Newark, half hour more to Ocean City's Boardwalk. This home is ready for its new owner to just move in and enjoy. Sizes, taxes, distances approximate.

4 Beds ⋅ 3 Baths

Updated + Upgraded - Turn-key 4BR/2.5BA contemporary 2-story home on a culdesac lot backing to trees, near historic downtown Denton - a true gem of an Eastern Shore town, perched on the banks of the Choptank River - but tucked away on a residential court. New flooring + paint throughout, new granite counters, new kitchen appliances, new fixtures. Wide open floorplan boasts tall ceilings, spacious rooms throughout, and lots of great light. Great room with new LVP flooring offers living, dining, breakfast, and kitchen spaces. Bright + cheery kitchen - light gray cabinetry, new stainless steel appliances, gorgeous granite counters, new custom tile backsplash. Sliders out to the expansive deck overlooking your roomy yard. Separate flex room - perfect for a home office, study - whatever you like. A half bath completes the 1st floor. Upstairs, primary bedroom with vaulted ceiling, new carpet, walk-in closet, full, en-suite bath - new tile floors, step-in shower, double-sink vanity. 3 additional bedrooms - all with new carpet. 2nd full bath with tub/shower combo, tile flooring. Laundry room with new tile floors completes the home's interior. Attached 2-car garage with extra space for storage, concrete driveway, nice-sized storage shed. Minutes to the best that Denton and Caroline County offers - great local restaurants, boutique and big-box store shopping, arts + culture, history galore, plenty of public launches and marinas, boating, world-class fishing, crabbing, hunting, wildlife estuaries, incredible state parks - a true paradise for nature lovers, photographers, boaters, fishermen and anyone who wants to enjoy the more relaxed pace on the Eastern Shore - from the beaches to the bays and beyond! Great central location on the Delmarva Peninsula -- 15mi to Easton, 30mi to the Bay Bridge or Cambridge, 40mi to Annapolis's Downtown, about an hour to the Delaware Beaches or Newark, half hour more to Ocean City's Boardwalk. This home is ready for its new owner to just move in and enjoy. Sizes, taxes, distances approximate.

502 Kathryn Ct, Denton

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$1,550,000

Wake up to sunrise on the Choptank River and wind down with some of the most stunning sunsets on the Eastern Shore — with Ospreys, Eagles, Herons, and an abundance of wildlife as your daily backdrop. This stunning 4,853 sq ft waterfront estate sits on 2.44 acres with 268 feet of private river frontage, putting you right on the water and just steps from the best of historic downtown Denton. Built in 2006 and extensively renovated in 2016, this 5-bed, 4.5-bath home has been meticulously maintained — nothing to do but move in. Two private primary suites on the main level each offer a serene river view retreat, ideal for multi-generational living or hosting guests in style. Three additional bedrooms upstairs provide room to spread out. Soaring 9-ft ceilings, hardwood floors with a dark walnut finish, maple paneling, and a custom Hagerstown Kitchens kitchen set the tone for quality throughout. Entertain on the brand-new Trex deck (2025) or unwind on the screened porch with spectacular western sunsets — and those views are yours forever. The land across the river is a protected Resource Conservation Area. All major systems are in excellent condition and maintained on yearly service contracts: three Carrier variable-speed HVAC units, dual Rinnai tankless water heaters, closed-cell foam insulation, and Hardie Board siding. The private dock features 8 ft MLW, a boat lift, and dedicated kayak dock with water, 240V power, and security cameras — accessed via hand-laid stone steps. Ospreys, Eagles, Herons, and Owls are regular visitors. A dedicated wellness room with river view includes a voice-command sauna, cold plunge, full shower, and workout space. The 3-bay epoxy-floored garage with LED lighting offers abundant storage for all your gear. A short walk to historic downtown Denton — an Eastern Shore best-kept secret with Eden Town Brewery, award-winning Caroline's Restaurant, Clayton Farms, and Shore Gourmet and the Chesapeake Culinary Center. Easton, St. Michaels, and Oxford are less than 30 minutes away, while Annapolis, Ocean City, Rehoboth Beach, Assateague, and Chincoteague are all within roughly an hour. You're already in the heart of it all.

5 Beds ⋅ 5 Baths

Wake up to sunrise on the Choptank River and wind down with some of the most stunning sunsets on the Eastern Shore — with Ospreys, Eagles, Herons, and an abundance of wildlife as your daily backdrop. This stunning 4,853 sq ft waterfront estate sits on 2.44 acres with 268 feet of private river frontage, putting you right on the water and just steps from the best of historic downtown Denton. Built in 2006 and extensively renovated in 2016, this 5-bed, 4.5-bath home has been meticulously maintained — nothing to do but move in. Two private primary suites on the main level each offer a serene river view retreat, ideal for multi-generational living or hosting guests in style. Three additional bedrooms upstairs provide room to spread out. Soaring 9-ft ceilings, hardwood floors with a dark walnut finish, maple paneling, and a custom Hagerstown Kitchens kitchen set the tone for quality throughout. Entertain on the brand-new Trex deck (2025) or unwind on the screened porch with spectacular western sunsets — and those views are yours forever. The land across the river is a protected Resource Conservation Area. All major systems are in excellent condition and maintained on yearly service contracts: three Carrier variable-speed HVAC units, dual Rinnai tankless water heaters, closed-cell foam insulation, and Hardie Board siding. The private dock features 8 ft MLW, a boat lift, and dedicated kayak dock with water, 240V power, and security cameras — accessed via hand-laid stone steps. Ospreys, Eagles, Herons, and Owls are regular visitors. A dedicated wellness room with river view includes a voice-command sauna, cold plunge, full shower, and workout space. The 3-bay epoxy-floored garage with LED lighting offers abundant storage for all your gear. A short walk to historic downtown Denton — an Eastern Shore best-kept secret with Eden Town Brewery, award-winning Caroline's Restaurant, Clayton Farms, and Shore Gourmet and the Chesapeake Culinary Center. Easton, St. Michaels, and Oxford are less than 30 minutes away, while Annapolis, Ocean City, Rehoboth Beach, Assateague, and Chincoteague are all within roughly an hour. You're already in the heart of it all.

322 S 2nd St, Denton

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$190,000

3-Story Townhome Ready for Its New Owners! Home offers 3 bedrooms and 2.5 baths with a functional layout and comfortable living spaces. The spacious first floor features an open living area and convenient half bath for guests. The second floor includes two bedrooms, a full bath, and laundry area, providing everyday convenience. The third-floor primary suite offers a private retreat with a separate shower, soaking tub, and double-sink vanity. HOA includes lawn care, snow removal, trash service, and access to a community pool and clubhouse. Ideally located close to downtown, shopping, grocery stores, and the public boat ramp with access to the Choptank River, as well as nearby Martinek Park. Easy access to the main highway makes commuting simple while still enjoying the charm of the area. Schedule your showing today!

3 Beds ⋅ 3 Baths

3-Story Townhome Ready for Its New Owners! Home offers 3 bedrooms and 2.5 baths with a functional layout and comfortable living spaces. The spacious first floor features an open living area and convenient half bath for guests. The second floor includes two bedrooms, a full bath, and laundry area, providing everyday convenience. The third-floor primary suite offers a private retreat with a separate shower, soaking tub, and double-sink vanity. HOA includes lawn care, snow removal, trash service, and access to a community pool and clubhouse. Ideally located close to downtown, shopping, grocery stores, and the public boat ramp with access to the Choptank River, as well as nearby Martinek Park. Easy access to the main highway makes commuting simple while still enjoying the charm of the area. Schedule your showing today!

1507 Blue Heron Dr, Denton

Listing courtesy of Keller Williams Select Realtors of Cambridge. Contact: 4102711265

$609,000

Nestled in the shadows of the Choptank River is a meticulously maintained home in the water-privileged neighborhood of Asbury. Beautiful Expansive lot size gives you the privacy needed within a walkable neighborhood. The flat level lot opens up future pool and other amenity possibilities. Sit in your rocker with a cocktail while enjoying the dream turned into a reality of a wrap-around porch. A large rear screened-in porch to watch the local wildlife opens onto extensive hardscaping, perfect for an outdoor fire pit to enjoy those cool evenings with family and friends. Large open kitchen into the family room is the heart of the home that features a wood stove. 4 substantial bedrooms upstairs. Main floor features an office that could be a wide range of things, including a main floor bedroom. Steps from the Asbury Nature Trail that brings you to your community dock and water access with Huge views of the Choptank River.

5 Beds ⋅ 3 Baths

Nestled in the shadows of the Choptank River is a meticulously maintained home in the water-privileged neighborhood of Asbury. Beautiful Expansive lot size gives you the privacy needed within a walkable neighborhood. The flat level lot opens up future pool and other amenity possibilities. Sit in your rocker with a cocktail while enjoying the dream turned into a reality of a wrap-around porch. A large rear screened-in porch to watch the local wildlife opens onto extensive hardscaping, perfect for an outdoor fire pit to enjoy those cool evenings with family and friends. Large open kitchen into the family room is the heart of the home that features a wood stove. 4 substantial bedrooms upstairs. Main floor features an office that could be a wide range of things, including a main floor bedroom. Steps from the Asbury Nature Trail that brings you to your community dock and water access with Huge views of the Choptank River.

24276 Asbury Dr, Denton

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