$1,500,000 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: Selling Office: L C Parker Real Estate.
$1,200,000 Right out of HGTV! Custom Built in 2020, this 3,350+/- sq ft one-level home offers an abundance of amenities including high ceilings, 4 bedrooms, 3.5 Baths, large open floorplan with huge gourmet kitchen with quartz/ss appliances, separate pantry, family room with stacked stone gas fireplace. The Primary Bedroom is located at one end of the house and includes a large bath with double vanity, separate tub, tiled shower with multiple jets, large closet with custom built-in’s. There are three separate bedrooms and 2 full baths. The main living areas feature wall of glass sliding doors lead you to the concrete patio overlooking the pool. Property is improved with incredible pool with Travertine decking, rock features, a water slide and more! Other features include a paved driveway, located at the end of a cul-de-sac, complete privacy, 18.6+/- acres, room to hunt, have horses/animals or ride the ATV’s. Convenient to boat ramps, state parks, MD & DE Beaches. An incredible house/property package. 4 Beds ⋅ 4 Baths Right out of HGTV! Custom Built in 2020, this 3,350+/- sq ft one-level home offers an abundance of amenities including high ceilings, 4 bedrooms, 3.5 Baths, large open floorplan with huge gourmet kitchen with quartz/ss appliances, separate pantry, family room with stacked stone gas fireplace. The Primary Bedroom is located at one end of the house and includes a large bath with double vanity, separate tub, tiled shower with multiple jets, large closet with custom built-in’s. There are three separate bedrooms and 2 full baths. The main living areas feature wall of glass sliding doors lead you to the concrete patio overlooking the pool. Property is improved with incredible pool with Travertine decking, rock features, a water slide and more! Other features include a paved driveway, located at the end of a cul-de-sac, complete privacy, 18.6+/- acres, room to hunt, have horses/animals or ride the ATV’s. Convenient to boat ramps, state parks, MD & DE Beaches. An incredible house/property package. 23296 Wilder Way, Denton Listing courtesy of Benson & Mangold, LLC. Contact: Selling Office: RE/MAX United Real Estate.
$1,150,000 Experience timeless elegance and Eastern Shore charm at this beautifully restored 4-bedroom, 3.5-bath colonial retreat set on 7 acres along the Choptank River. Once known as “Hazelwood,” this historic Governor’s Mansion is one you don’t want to miss! Inside, you’ll find expansive formal and informal rooms flow seamlessly for entertaining and family living alike. This estate features refinished wood floors (2023), freshly replastered / painted walls (2023), updated marble bathrooms, brand new gas stove (2025), HVAC split systems (2019), roof (2016), septic (2009), well (2013), pool liner (2020), and a new propane tank and pool heater (2022) for the in-ground pool. Additional outlets, recessed lighting, and ceiling fans have also been added for modern convenience (2022). Outdoors, enjoy the best of Eastern Shore living—fishing, boating, kayaking, or swimming right from your backyard dock on the scenic Choptank River. Relax poolside, gather around the firepit, or simply take in the tranquil water views. With a strong history as an income-generating Airbnb, this property offers exceptional versatility as a private retreat, family estate, or investment opportunity. And to top it off, enjoy a day of golf right next door at Caroline Country Club! Don’t miss your chance to own a piece of Maryland history—and let the riverfront veranda echo with history while you sip your morning coffee. 4 Beds ⋅ 4 Baths Experience timeless elegance and Eastern Shore charm at this beautifully restored 4-bedroom, 3.5-bath colonial retreat set on 7 acres along the Choptank River. Once known as “Hazelwood,” this historic Governor’s Mansion is one you don’t want to miss! Inside, you’ll find expansive formal and informal rooms flow seamlessly for entertaining and family living alike. This estate features refinished wood floors (2023), freshly replastered / painted walls (2023), updated marble bathrooms, brand new gas stove (2025), HVAC split systems (2019), roof (2016), septic (2009), well (2013), pool liner (2020), and a new propane tank and pool heater (2022) for the in-ground pool. Additional outlets, recessed lighting, and ceiling fans have also been added for modern convenience (2022). Outdoors, enjoy the best of Eastern Shore living—fishing, boating, kayaking, or swimming right from your backyard dock on the scenic Choptank River. Relax poolside, gather around the firepit, or simply take in the tranquil water views. With a strong history as an income-generating Airbnb, this property offers exceptional versatility as a private retreat, family estate, or investment opportunity. And to top it off, enjoy a day of golf right next door at Caroline Country Club! Don’t miss your chance to own a piece of Maryland history—and let the riverfront veranda echo with history while you sip your morning coffee. 24800 Pealiquor Rd, Denton Listing courtesy of Fathom Realty LLC. Contact: Selling Office: Wright Real Estate.
$1,099,999 This ±45-acre previously certified organic farm is located just south of Denton and offers a well-rounded combination of productive farmland, agricultural infrastructure, and residential living. The property includes approximately ±41 acres of tillable ground equipped with a subsurface irrigation system fed by six on-site wells, providing efficient and reliable water delivery for a wide range of crop operations. Agricultural improvements include a ±22,500 square foot greenhouse with an integrated loading dock, historically used for produce and flower production, as well as a 30’ x 72’ high tunnel to support extended growing seasons. A dedicated generator shed houses a 60-kW generator that supplies power to pasture fencing,well pumps, and greenhouse (including all componets) adding reliability and operational security. Additional improvements include a 30’ x 60’ pole barn with a partial concrete floor, suitable for equipment storage or farm operations. The residential component consists of a well-maintained 3,242 square foot home built in 1998, featuring central air conditioning, a central vacuum system, and generous closet space throughout. The home includes a large third-floor family room that can serve as a game room, office, or flexible living space. Powering the residence is a solar energy system that generates surplus electricity annually, providing long-term energy efficiency and reduced operating costs. With its advanced irrigation infrastructure, established agricultural improvements, and history of organic production, this property is well suited for continued farming operations, specialty crop production, or an ag-focused investment opportunity in a desirable Caroline County location just south of Denton. 4 Beds ⋅ 3 Baths This ±45-acre previously certified organic farm is located just south of Denton and offers a well-rounded combination of productive farmland, agricultural infrastructure, and residential living. The property includes approximately ±41 acres of tillable ground equipped with a subsurface irrigation system fed by six on-site wells, providing efficient and reliable water delivery for a wide range of crop operations. Agricultural improvements include a ±22,500 square foot greenhouse with an integrated loading dock, historically used for produce and flower production, as well as a 30’ x 72’ high tunnel to support extended growing seasons. A dedicated generator shed houses a 60-kW generator that supplies power to pasture fencing,well pumps, and greenhouse (including all componets) adding reliability and operational security. Additional improvements include a 30’ x 60’ pole barn with a partial concrete floor, suitable for equipment storage or farm operations. The residential component consists of a well-maintained 3,242 square foot home built in 1998, featuring central air conditioning, a central vacuum system, and generous closet space throughout. The home includes a large third-floor family room that can serve as a game room, office, or flexible living space. Powering the residence is a solar energy system that generates surplus electricity annually, providing long-term energy efficiency and reduced operating costs. With its advanced irrigation infrastructure, established agricultural improvements, and history of organic production, this property is well suited for continued farming operations, specialty crop production, or an ag-focused investment opportunity in a desirable Caroline County location just south of Denton. 7904 Clark Rd, Denton Listing courtesy of The Land Group. Contact: Selling Office: The Land Group.
$1,099,999 This ±45-acre previously certified organic farm is located just south of Denton and offers a well-rounded combination of productive farmland, agricultural infrastructure, and residential living. The property includes approximately ±41 acres of tillable ground equipped with a subsurface irrigation system fed by six on-site wells, providing efficient and reliable water delivery for a wide range of crop operations. Agricultural improvements include a ±22,500 square foot greenhouse with an integrated loading dock, historically used for produce and flower production, as well as a 30’ x 72’ high tunnel to support extended growing seasons. A dedicated generator shed houses a 60-kW generator that supplies power to pasture fencing,well pumps, and greenhouse (including all componets) adding reliability and operational security. Additional improvements include a 30’ x 60’ pole barn with a partial concrete floor, suitable for equipment storage or farm operations. The residential component consists of a well-maintained 3,242 square foot home built in 1998, featuring central air conditioning, a central vacuum system, and generous closet space throughout. The home includes a large third-floor family room that can serve as a game room, office, or flexible living space. Powering the residence is a solar energy system that generates surplus electricity annually, providing long-term energy efficiency and reduced operating costs. With its advanced irrigation infrastructure, established agricultural improvements, and history of organic production, this property is well suited for continued farming operations, specialty crop production, or an ag-focused investment opportunity in a desirable Caroline County location just south of Denton. 4 Beds ⋅ 3 Baths This ±45-acre previously certified organic farm is located just south of Denton and offers a well-rounded combination of productive farmland, agricultural infrastructure, and residential living. The property includes approximately ±41 acres of tillable ground equipped with a subsurface irrigation system fed by six on-site wells, providing efficient and reliable water delivery for a wide range of crop operations. Agricultural improvements include a ±22,500 square foot greenhouse with an integrated loading dock, historically used for produce and flower production, as well as a 30’ x 72’ high tunnel to support extended growing seasons. A dedicated generator shed houses a 60-kW generator that supplies power to pasture fencing,well pumps, and greenhouse (including all componets) adding reliability and operational security. Additional improvements include a 30’ x 60’ pole barn with a partial concrete floor, suitable for equipment storage or farm operations. The residential component consists of a well-maintained 3,242 square foot home built in 1998, featuring central air conditioning, a central vacuum system, and generous closet space throughout. The home includes a large third-floor family room that can serve as a game room, office, or flexible living space. Powering the residence is a solar energy system that generates surplus electricity annually, providing long-term energy efficiency and reduced operating costs. With its advanced irrigation infrastructure, established agricultural improvements, and history of organic production, this property is well suited for continued farming operations, specialty crop production, or an ag-focused investment opportunity in a desirable Caroline County location just south of Denton. 7904 Clark Rd, Denton Listing courtesy of The Land Group. Contact: Selling Office: The Land Group.
$950,000 Experience the perfect harmony of modern luxury and timeless countryside living with this exceptional 3 bedroom 2.5 bath farmhouse, built in 2022, gracefully set on approximately 62 acres in the heart of Denton, Maryland. Surrounded by a serene, bucolic landscape, this remarkable property offers a rare opportunity to embrace refined rural living without sacrificing contemporary comfort. From the moment you arrive, the home’s striking farmhouse aesthetic makes a lasting impression, featuring a durable metal roof and siding, and a welcoming covered front porch supported by handcrafted timber posts. Inside, a sun-drenched open floor plan unfolds with effortless flow, enhanced by seamless luxury vinyl plank flooring and a neutral palette throughout. The spacious family room transitions beautifully into an expansive kitchen designed for both everyday living and entertaining. Thoughtfully appointed with quartz countertops, stainless steel appliances, subway tile backsplash, recessed lighting, and a large center island with breakfast bar and an additional cooktop, this space is as functional as it is beautiful. A generous dining area completes the kitchen. In the main living area, behind charming natural wood barn doors a versatile bonus room is ideal as a private den, study, or reading retreat. The primary bedroom is a true sanctuary, offering abundant natural light and a thoughtfully designed ensuite behind double doors, creating a private dressing and bathing suite complete with double vanity, shower, jetted soaking tub, and a spacious walk-in closet. Two additional well-sized bedrooms feature plush neutral carpeting and share a well appointed full hall bath. An additional flexible living space, in the bedroom area provides endless possibilities for a home office, hobby space, or guest overflow. A convenient main-level powder room and dedicated laundry area further enhance everyday convenience. Outdoors, the property transforms into an unparalleled retreat. Spanning three parcels, the expansive acreage is highlighted by a beautifully managed forest under a Forest Conservation Management Plan, creating a park-like setting rich with natural beauty. A tranquil pond, open lawn space for recreation, and abundant wildlife make this an outdoorsman’s dream, perfect for hunting, exploring, or simply enjoying the peace of nature. Multiple outbuildings with electric and a separate agricultural well, including a machine shed and storage structures, add exceptional functionality for rural living. This is more than a home, it is a lifestyle. A rare blend of modern farmhouse design and unspoiled countryside, offering space, privacy, and endless opportunity. There are 2 additional parcels to be conveyed with this sale. Tax ID: 0608006709 (56.76 Acres) & Tax ID: 060801422 (3.4 Acres). Both Parcels are Perc tested and buildable. 3 Beds ⋅ 3 Baths Experience the perfect harmony of modern luxury and timeless countryside living with this exceptional 3 bedroom 2.5 bath farmhouse, built in 2022, gracefully set on approximately 62 acres in the heart of Denton, Maryland. Surrounded by a serene, bucolic landscape, this remarkable property offers a rare opportunity to embrace refined rural living without sacrificing contemporary comfort. From the moment you arrive, the home’s striking farmhouse aesthetic makes a lasting impression, featuring a durable metal roof and siding, and a welcoming covered front porch supported by handcrafted timber posts. Inside, a sun-drenched open floor plan unfolds with effortless flow, enhanced by seamless luxury vinyl plank flooring and a neutral palette throughout. The spacious family room transitions beautifully into an expansive kitchen designed for both everyday living and entertaining. Thoughtfully appointed with quartz countertops, stainless steel appliances, subway tile backsplash, recessed lighting, and a large center island with breakfast bar and an additional cooktop, this space is as functional as it is beautiful. A generous dining area completes the kitchen. In the main living area, behind charming natural wood barn doors a versatile bonus room is ideal as a private den, study, or reading retreat. The primary bedroom is a true sanctuary, offering abundant natural light and a thoughtfully designed ensuite behind double doors, creating a private dressing and bathing suite complete with double vanity, shower, jetted soaking tub, and a spacious walk-in closet. Two additional well-sized bedrooms feature plush neutral carpeting and share a well appointed full hall bath. An additional flexible living space, in the bedroom area provides endless possibilities for a home office, hobby space, or guest overflow. A convenient main-level powder room and dedicated laundry area further enhance everyday convenience. Outdoors, the property transforms into an unparalleled retreat. Spanning three parcels, the expansive acreage is highlighted by a beautifully managed forest under a Forest Conservation Management Plan, creating a park-like setting rich with natural beauty. A tranquil pond, open lawn space for recreation, and abundant wildlife make this an outdoorsman’s dream, perfect for hunting, exploring, or simply enjoying the peace of nature. Multiple outbuildings with electric and a separate agricultural well, including a machine shed and storage structures, add exceptional functionality for rural living. This is more than a home, it is a lifestyle. A rare blend of modern farmhouse design and unspoiled countryside, offering space, privacy, and endless opportunity. There are 2 additional parcels to be conveyed with this sale. Tax ID: 0608006709 (56.76 Acres) & Tax ID: 060801422 (3.4 Acres). Both Parcels are Perc tested and buildable. 7805 Dyer Rd, Denton Listing courtesy of Northrop Realty. Contact: Selling Office: Coldwell Banker Realty.
$940,000 Nestled on over six acres of pristine land with direct access to the Choptank River, this contemporary waterfront estate offers the ultimate in Eastern Shore luxury living. Designed to impress, the home features four spacious bedrooms, three and a half baths, and soaring cathedral ceilings that crown a dramatic two-story living room with floor-to-ceiling windows—flooding the home with natural light and showcasing stunning views of the surrounding landscape. Perfect for both relaxation and entertaining, the open-concept main living area flows seamlessly into the dining room and a gourmet kitchen equipped with a large center island, custom cabinetry, abundant storage, and a bright breakfast area. Four fireplaces—including one in the cozy family room—add warmth and character throughout the home. A dedicated billiard room with direct outdoor access offers a versatile space that could also serve as an art studio, media room, or more. The expansive primary suite is a true retreat, featuring a private marble bath, separate workout and tanning rooms, and peaceful garden views. Bedroom flexibility, built-in features, and an upstairs suite with en suite bath offer options for multi-generational living or hosting guests with ease. Outdoors, enjoy your private, fenced backyard oasis complete with a sparkling in-ground pool and a deep-water dock—ideal for boating, kayaking, or simply soaking in the tranquil beauty of the riverfront setting. Additional amenities include a detached garage with a second-floor loft perfect for storage, studio space, or a workshop, and a separate shed for tools and equipment. Located just outside the town of Denton, you’re only minutes from charming shops, dining, and state parks, all while enjoying the privacy and serenity of a secluded waterfront lifestyle. This is a rare opportunity to own a truly remarkable Eastern Shore property where luxury meets nature. 4 Beds ⋅ 4 Baths Nestled on over six acres of pristine land with direct access to the Choptank River, this contemporary waterfront estate offers the ultimate in Eastern Shore luxury living. Designed to impress, the home features four spacious bedrooms, three and a half baths, and soaring cathedral ceilings that crown a dramatic two-story living room with floor-to-ceiling windows—flooding the home with natural light and showcasing stunning views of the surrounding landscape. Perfect for both relaxation and entertaining, the open-concept main living area flows seamlessly into the dining room and a gourmet kitchen equipped with a large center island, custom cabinetry, abundant storage, and a bright breakfast area. Four fireplaces—including one in the cozy family room—add warmth and character throughout the home. A dedicated billiard room with direct outdoor access offers a versatile space that could also serve as an art studio, media room, or more. The expansive primary suite is a true retreat, featuring a private marble bath, separate workout and tanning rooms, and peaceful garden views. Bedroom flexibility, built-in features, and an upstairs suite with en suite bath offer options for multi-generational living or hosting guests with ease. Outdoors, enjoy your private, fenced backyard oasis complete with a sparkling in-ground pool and a deep-water dock—ideal for boating, kayaking, or simply soaking in the tranquil beauty of the riverfront setting. Additional amenities include a detached garage with a second-floor loft perfect for storage, studio space, or a workshop, and a separate shed for tools and equipment. Located just outside the town of Denton, you’re only minutes from charming shops, dining, and state parks, all while enjoying the privacy and serenity of a secluded waterfront lifestyle. This is a rare opportunity to own a truly remarkable Eastern Shore property where luxury meets nature. 8816 Dorothy Ln, Denton Listing courtesy of The Parker Group. Contact: Selling Office: Benson & Mangold, LLC.
$905,000 Private Waterfront Retreat on the Choptank River. Experience the best of Eastern Shore waterfront living in this exceptional home built in 2021, where modern luxury, privacy, and serene views come together on one remarkable property. Situated on 8.15± private acres with approximately 600 feet of Choptank River frontage and deep water access, this stunning retreat offers the perfect balance of refined living and peaceful seclusion. Featuring 2,376± square feet of beautifully designed living space with modern finishes throughout, this home was thoughtfully crafted for effortless entertaining and everyday comfort. The open concept design seamlessly connects the kitchen, dining, and living areas, including a spacious sunroom with expansive windows for a bird's eye view of the river frontage. The main floor also includes an easily accessible large primary suite. Two additional bedrooms, full bath, and a dedicated pocket office or potential walk in closet can be found on the second level. Over the large garage, a full staircase provides access to a spacious bonus room, providing storage space currently, though could potentially serve as flexible space for guests, a media room, home gym, or playroom, per county approval. Step outside to discover a true waterfront oasis. Fresh landscaping complements the natural beauty of the property, while three acres of manicured lawn blend seamlessly into five acres of mature woods, creating ideal privacy and a picturesque setting. Whether hosting gatherings with family or friends, enjoying dinner or cocktails on the patio or dock, or relaxing with your morning coffee overlooking the peaceful scenery, every moment is enhanced by the tranquil surroundings. A new private pier with approximately 12 feet of water depth offers outstanding access to the Choptank River, making it easy to spend your days boating, fishing, kayaking, paddleboarding, or simply taking in spectacular sun painted skies from your own backyard. Ideally located near the town of Denton with lovely shops and restaurants, the location of this sanctuary is just a short drive to the Eastern Shore's most desirable destinations where there is convenient access to the boutique shopping, award winning restaurants, galleries, and downtown charm of Easton, the historic waterfront town of St. Michaels, and even excellent ocean beaches only one hour away. This property provides the perfect blend of privacy while keeping you close to everything that makes Maryland's Eastern Shore so special. More than just a home, this is a lifestyle where every day feels like a getaway and every season brings new opportunities to relax, entertain, and enjoy the beauty of private waterfront living. 3 Beds ⋅ 3 Baths Private Waterfront Retreat on the Choptank River. Experience the best of Eastern Shore waterfront living in this exceptional home built in 2021, where modern luxury, privacy, and serene views come together on one remarkable property. Situated on 8.15± private acres with approximately 600 feet of Choptank River frontage and deep water access, this stunning retreat offers the perfect balance of refined living and peaceful seclusion. Featuring 2,376± square feet of beautifully designed living space with modern finishes throughout, this home was thoughtfully crafted for effortless entertaining and everyday comfort. The open concept design seamlessly connects the kitchen, dining, and living areas, including a spacious sunroom with expansive windows for a bird's eye view of the river frontage. The main floor also includes an easily accessible large primary suite. Two additional bedrooms, full bath, and a dedicated pocket office or potential walk in closet can be found on the second level. Over the large garage, a full staircase provides access to a spacious bonus room, providing storage space currently, though could potentially serve as flexible space for guests, a media room, home gym, or playroom, per county approval. Step outside to discover a true waterfront oasis. Fresh landscaping complements the natural beauty of the property, while three acres of manicured lawn blend seamlessly into five acres of mature woods, creating ideal privacy and a picturesque setting. Whether hosting gatherings with family or friends, enjoying dinner or cocktails on the patio or dock, or relaxing with your morning coffee overlooking the peaceful scenery, every moment is enhanced by the tranquil surroundings. A new private pier with approximately 12 feet of water depth offers outstanding access to the Choptank River, making it easy to spend your days boating, fishing, kayaking, paddleboarding, or simply taking in spectacular sun painted skies from your own backyard. Ideally located near the town of Denton with lovely shops and restaurants, the location of this sanctuary is just a short drive to the Eastern Shore's most desirable destinations where there is convenient access to the boutique shopping, award winning restaurants, galleries, and downtown charm of Easton, the historic waterfront town of St. Michaels, and even excellent ocean beaches only one hour away. This property provides the perfect blend of privacy while keeping you close to everything that makes Maryland's Eastern Shore so special. More than just a home, this is a lifestyle where every day feels like a getaway and every season brings new opportunities to relax, entertain, and enjoy the beauty of private waterfront living. 8851 New Bridge Rd, Denton Listing courtesy of Meredith Fine Properties. Contact: Selling Office: Benson & Mangold, LLC.
$740,000 " Diamond in the Rough" This property is being sold to settle an estate and no repairs will be made. Offering considerable upside potential, this well built, private, 5 bedroom, 5 bath home is tucked away on the Choptank River in the community of Asbury. Featuring a large, open kitchen/living area with fireplace, first floor primary suite, inground pool and private pier. 5 Beds ⋅ 5 Baths " Diamond in the Rough" This property is being sold to settle an estate and no repairs will be made. Offering considerable upside potential, this well built, private, 5 bedroom, 5 bath home is tucked away on the Choptank River in the community of Asbury. Featuring a large, open kitchen/living area with fireplace, first floor primary suite, inground pool and private pier. 8821 Dorothy Ln, Denton Listing courtesy of Wright Real Estate. Contact: Selling Office: Wright Real Estate.
$700,000 Stunning waterfront property on the Choptank River featuring a private dock, boat lift and deep water access. This spacious home offers 4 bedrooms and 2 bathrooms, an inviting sunroom, hardwood flooring throughout, and a cozy fireplace. The unfinished basement provides potential for customization. Additional amenities include a 2 car attached garage on a 1 acre lot with no covenants or restrictions. NOTE: New roof, septic, and many more improvements throughout! Perfect property for enjoying serene river views and outdoor living! 4 Beds ⋅ 2 Baths Stunning waterfront property on the Choptank River featuring a private dock, boat lift and deep water access. This spacious home offers 4 bedrooms and 2 bathrooms, an inviting sunroom, hardwood flooring throughout, and a cozy fireplace. The unfinished basement provides potential for customization. Additional amenities include a 2 car attached garage on a 1 acre lot with no covenants or restrictions. NOTE: New roof, septic, and many more improvements throughout! Perfect property for enjoying serene river views and outdoor living! 25211 Adams Landing Rd, Denton Listing courtesy of Long & Foster Real Estate, Inc.. Contact: Selling Office: Unrepresented Buyer Office.
$619,000 Lovely grand colonial with covered front porch located on almost 4 acres. The first floor offers a huge primary suite with walk in closet and bath with soaking tub, dual headed shower and double vanity. Dining room has gleaming hardwood floors with enough space to seat 20 people, lovely overhead chandelier and warming propane fireplace . Kitchen has all stainless appliances, plenty of workspace, under cabinet lightning. tile backsplash and pantry. Kitchen also has a separate eating area that offers a more informal setting. Family room offers another propane fireplace plus plenty of room for your family gatherings. Laundry room has a separate pantry area with tons of storage and room for second fridge and freezer plus a laundry tub and hanging area. A great office with hardwood floors for the person who works from home. The second floor has three bedrooms( one converted to kitchenette) plus two large bonus rooms and full bath. The outside space is a private oasis with a 30 x 12 screened porch and a 67 x 40 deck for family gatherings . Recent upgrades include Geo thermal heating and air conditioning system(2017) and new roof (2023). 12x24 shed with electric for plenty of storage. Come visit and make this your new home. 4 Beds ⋅ 4 Baths Lovely grand colonial with covered front porch located on almost 4 acres. The first floor offers a huge primary suite with walk in closet and bath with soaking tub, dual headed shower and double vanity. Dining room has gleaming hardwood floors with enough space to seat 20 people, lovely overhead chandelier and warming propane fireplace . Kitchen has all stainless appliances, plenty of workspace, under cabinet lightning. tile backsplash and pantry. Kitchen also has a separate eating area that offers a more informal setting. Family room offers another propane fireplace plus plenty of room for your family gatherings. Laundry room has a separate pantry area with tons of storage and room for second fridge and freezer plus a laundry tub and hanging area. A great office with hardwood floors for the person who works from home. The second floor has three bedrooms( one converted to kitchenette) plus two large bonus rooms and full bath. The outside space is a private oasis with a 30 x 12 screened porch and a 67 x 40 deck for family gatherings . Recent upgrades include Geo thermal heating and air conditioning system(2017) and new roof (2023). 12x24 shed with electric for plenty of storage. Come visit and make this your new home. 24324 Asbury Dr, Denton Listing courtesy of Keller Williams Realty. Contact: Selling Office: Berkshire Hathaway Homeservice Homesale Realty.
$590,000 Hunters Paradise: 3 Br, 3 Baths, 3 car garage all on 16.60 acres with very large machine shop /workshop. Acreage is mostly wooded with a stream running through the back of the property. Great deer and turkey hunting. Room for horses, chickens, goats or whatever your heart's desire. The 2,565 sq ft home offers Living room w/ fireplace (wood stove insert), Country kitchen w/attached breakfast area and island, separate dining room, first floor primary w/hot tub in primary bath, open staircase leads to 2 bedrooms, 1 full bath and bonus room on second floor. Also, there's a bonus room over garage w/exterior entry that can be used for studio, office, game room or man cave. Enjoy watching the wildlife on the rear screened porch. Located just 30 minutes from the Bay Bridge and 30 minutes to the Delaware and Maryland beaches. Home is being sold as is. 3 Beds ⋅ 3 Baths Hunters Paradise: 3 Br, 3 Baths, 3 car garage all on 16.60 acres with very large machine shop /workshop. Acreage is mostly wooded with a stream running through the back of the property. Great deer and turkey hunting. Room for horses, chickens, goats or whatever your heart's desire. The 2,565 sq ft home offers Living room w/ fireplace (wood stove insert), Country kitchen w/attached breakfast area and island, separate dining room, first floor primary w/hot tub in primary bath, open staircase leads to 2 bedrooms, 1 full bath and bonus room on second floor. Also, there's a bonus room over garage w/exterior entry that can be used for studio, office, game room or man cave. Enjoy watching the wildlife on the rear screened porch. Located just 30 minutes from the Bay Bridge and 30 minutes to the Delaware and Maryland beaches. Home is being sold as is. 8197 Detour Rd, Denton Listing courtesy of Benson & Mangold, LLC. Contact: Selling Office: Unrepresented Buyer Office.
$550,000 This home is anything but ordinary. Thoughtfully built by the current owners in 1982, the property showcases true craftsmanship with structural beams hewn from timber sourced right from the land itself. The main living space is situated on the second floor, offering a bright, airy layout and sweeping views across 13 picturesque acres. The first floor provides incredible flexibility—ideal for finishing into additional living space, creating a private guest suite, or establishing a home-based business. A spacious 1,100-square-foot garage with four overhead doors and dedicated workspace makes this property perfect for hobbyists, entrepreneurs, or anyone needing room to create and store. Meticulously maintained and filled with character, this cheerful home is complemented by four additional lots that were subdivided when the property was originally platted—offering future potential, investment opportunities, or added privacy. A rare opportunity to own a truly distinctive property with space, versatility, and endless possibilities. The back boundary line abuts Denton Elementary School and Trice Meadows. Martinak State Park is a mile down the road. This is 13 acres of country but close to everything. 2 Beds ⋅ 2 Baths This home is anything but ordinary. Thoughtfully built by the current owners in 1982, the property showcases true craftsmanship with structural beams hewn from timber sourced right from the land itself. The main living space is situated on the second floor, offering a bright, airy layout and sweeping views across 13 picturesque acres. The first floor provides incredible flexibility—ideal for finishing into additional living space, creating a private guest suite, or establishing a home-based business. A spacious 1,100-square-foot garage with four overhead doors and dedicated workspace makes this property perfect for hobbyists, entrepreneurs, or anyone needing room to create and store. Meticulously maintained and filled with character, this cheerful home is complemented by four additional lots that were subdivided when the property was originally platted—offering future potential, investment opportunities, or added privacy. A rare opportunity to own a truly distinctive property with space, versatility, and endless possibilities. The back boundary line abuts Denton Elementary School and Trice Meadows. Martinak State Park is a mile down the road. This is 13 acres of country but close to everything. 322 Deep Shore Rd, Denton Listing courtesy of Benson & Mangold, LLC. Contact: Selling Office: Chesapeake Real Estate Associates, LLC.
$527,000 Enjoy the space and privacy of this beautiful home situated on over 2 acres just outside of Denton. The main level features a formal dining room, a spacious primary suite with separate his-and-her closets, and a private bath with a walk-in shower. The kitchen opens to the family room, creating an inviting space for everyday living and entertaining. Custom window treatments enhance both the living room and primary bedroom. A standout feature is the enclosed sunroom, complete with a fireplace and stunning floor-to-ceiling stone surround—perfect for family gatherings and year-round enjoyment. The main floor also includes a convenient laundry area and half bath. Upstairs, you'll find three additional bedrooms, a loft area, and a huge bonus room that offers abundant storage space or flexibility for hobbies, recreation, or a home office. Outdoor features include a composite deck and a fully fenced backyard lined with privacy trees. The insulated two-car garage provides ample room for vehicles, storage, or a workshop. Additional updates and features include: Encapsulated crawl space with dehumidifier HVAC replaced in 2020 and Water heater replaced in 2018. HOME WARRANTY PROVIDED AT CLOSING. 4 Beds ⋅ 3 Baths Enjoy the space and privacy of this beautiful home situated on over 2 acres just outside of Denton. The main level features a formal dining room, a spacious primary suite with separate his-and-her closets, and a private bath with a walk-in shower. The kitchen opens to the family room, creating an inviting space for everyday living and entertaining. Custom window treatments enhance both the living room and primary bedroom. A standout feature is the enclosed sunroom, complete with a fireplace and stunning floor-to-ceiling stone surround—perfect for family gatherings and year-round enjoyment. The main floor also includes a convenient laundry area and half bath. Upstairs, you'll find three additional bedrooms, a loft area, and a huge bonus room that offers abundant storage space or flexibility for hobbies, recreation, or a home office. Outdoor features include a composite deck and a fully fenced backyard lined with privacy trees. The insulated two-car garage provides ample room for vehicles, storage, or a workshop. Additional updates and features include: Encapsulated crawl space with dehumidifier HVAC replaced in 2020 and Water heater replaced in 2018. HOME WARRANTY PROVIDED AT CLOSING. 8590 Briar Patch Dr, Denton Listing courtesy of Long & Foster Real Estate, Inc.. Contact: Selling Office: Taylor Properties.
$520,000 Welcome to 8047 Laurel Lane in Denton, Md. First time ever offered on the market! Tucked away on 1.4 private, wooded acres in Denton’s sought-after Forest Landing community, this custom-built 3BR/2BA home features a pristine inground pool, a brand-new roof, and water-privileged community access just minutes from the Tuckahoe Creek, leading into the Choptank River. Property Highlights: Move-In Ready Ease: Buy with total confidence—a brand-new roof has just been installed. The Layout: Features a bright, open floor plan with 3 comfortable bedrooms and 2 full bathrooms. Backyard Paradise: Your own private sanctuary featuring a beautiful inground pool surrounded by mature trees. Premium Location: Enjoy ultimate privacy while staying just minutes from downtown Easton, historic downtown Denton, and the scenic Tuckahoe River. Community Perks: Forest Landing offers residents an established, mature neighborhood feel with private beach access, picnic areas, and a community launch spot for canoes, kayaks, and fishing. Opportunities like this do not last long in this neighborhood. Grab your kayak, pack your swimsuits, and come see this beautiful custom property before it is gone! 3 Beds ⋅ 2 Baths Welcome to 8047 Laurel Lane in Denton, Md. First time ever offered on the market! Tucked away on 1.4 private, wooded acres in Denton’s sought-after Forest Landing community, this custom-built 3BR/2BA home features a pristine inground pool, a brand-new roof, and water-privileged community access just minutes from the Tuckahoe Creek, leading into the Choptank River. Property Highlights: Move-In Ready Ease: Buy with total confidence—a brand-new roof has just been installed. The Layout: Features a bright, open floor plan with 3 comfortable bedrooms and 2 full bathrooms. Backyard Paradise: Your own private sanctuary featuring a beautiful inground pool surrounded by mature trees. Premium Location: Enjoy ultimate privacy while staying just minutes from downtown Easton, historic downtown Denton, and the scenic Tuckahoe River. Community Perks: Forest Landing offers residents an established, mature neighborhood feel with private beach access, picnic areas, and a community launch spot for canoes, kayaks, and fishing. Opportunities like this do not last long in this neighborhood. Grab your kayak, pack your swimsuits, and come see this beautiful custom property before it is gone! 8047 Laurel Ln, Denton Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact: Selling Office: Rosendale Realty.
$500,000 Nestled on a serene 5.64-acre lot, this charming ranch-style home offers a perfect blend of comfort and modern living in a tranquil rural setting. Built in 2003, (New Roof in January 2026!) this well-maintained residence boasts 2,100 square feet of thoughtfully designed space, featuring three spacious bedrooms and two full bathrooms, ideal for relaxation and everyday living. Step inside to discover a warm and inviting interior adorned with a mix of hardwood, carpet, and vinyl flooring. The heart of the home is the eat-in kitchen, complete with upgraded countertops, stainless steel appliances, and an island with additional storage. The formal dining room provides an comfortable space for gatherings, while the cozy living areas are enhanced by recessed lighting and ceiling fans, ensuring a comfortable atmosphere year-round. The exterior of the property is equally impressive, featuring a deck perfect for outdoor entertaining and a hot tub for unwinding under the stars. The beautifully landscaped front and rear yards are surrounded by mature trees, offering privacy and a picturesque view of the woods. Additional structures include a detached garage providing ample storage and workspace. Located in a peaceful rural community, this home offers the best of both worlds-seclusion and accessibility. Enjoy the benefits of nearby parks and recreational areas, perfect for outdoor enthusiasts. Public services are readily available, ensuring convenience and peace of mind. With a private, no-thru street, this property offers a safe and quiet retreat while still being within reach of essential amenities. Whether you're looking to enjoy the tranquility of nature or engage with the community, this home is a perfect choice for those seeking comfort and connection. Come experience the warmth and charm of this delightful property. 3 Beds ⋅ 2 Baths Nestled on a serene 5.64-acre lot, this charming ranch-style home offers a perfect blend of comfort and modern living in a tranquil rural setting. Built in 2003, (New Roof in January 2026!) this well-maintained residence boasts 2,100 square feet of thoughtfully designed space, featuring three spacious bedrooms and two full bathrooms, ideal for relaxation and everyday living. Step inside to discover a warm and inviting interior adorned with a mix of hardwood, carpet, and vinyl flooring. The heart of the home is the eat-in kitchen, complete with upgraded countertops, stainless steel appliances, and an island with additional storage. The formal dining room provides an comfortable space for gatherings, while the cozy living areas are enhanced by recessed lighting and ceiling fans, ensuring a comfortable atmosphere year-round. The exterior of the property is equally impressive, featuring a deck perfect for outdoor entertaining and a hot tub for unwinding under the stars. The beautifully landscaped front and rear yards are surrounded by mature trees, offering privacy and a picturesque view of the woods. Additional structures include a detached garage providing ample storage and workspace. Located in a peaceful rural community, this home offers the best of both worlds-seclusion and accessibility. Enjoy the benefits of nearby parks and recreational areas, perfect for outdoor enthusiasts. Public services are readily available, ensuring convenience and peace of mind. With a private, no-thru street, this property offers a safe and quiet retreat while still being within reach of essential amenities. Whether you're looking to enjoy the tranquility of nature or engage with the community, this home is a perfect choice for those seeking comfort and connection. Come experience the warmth and charm of this delightful property. 8664 Mitchell Rd, Denton Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact: Selling Office: Whitetail Properties Real Estate, LLC.
$500,000 Peaceful Living on the Choptank River!!! One level Living! Brand New Roof! Offering 3 Bed and 1.5 Bath. Home features an open Floor Plan with Large Living Room w/ Gas Burning Stove., Spacious Kitchen with Tons of Storage, Breakfast Bar, and plenty of space for your Table and Chairs! Primary Bedroom facing the Water with Great Waterfront Views. Home also features a paved driveway with 2 door garage and a full set of stairs leading to the attic. Relax on your Enclosed Patio OR your Outside Deck and watch the boats go by! Enjoy fishing from your own Private Pier! Don't let this Ship Sail! Make an appointment today! 3 Beds ⋅ 2 Baths Peaceful Living on the Choptank River!!! One level Living! Brand New Roof! Offering 3 Bed and 1.5 Bath. Home features an open Floor Plan with Large Living Room w/ Gas Burning Stove., Spacious Kitchen with Tons of Storage, Breakfast Bar, and plenty of space for your Table and Chairs! Primary Bedroom facing the Water with Great Waterfront Views. Home also features a paved driveway with 2 door garage and a full set of stairs leading to the attic. Relax on your Enclosed Patio OR your Outside Deck and watch the boats go by! Enjoy fishing from your own Private Pier! Don't let this Ship Sail! Make an appointment today! 300 S 1st St, Denton Listing courtesy of Brenton Realty Group. Contact: Selling Office: Long & Foster Real Estate, Inc..
$480,000 Welcome to Willow Pond Road. This property rests on 5 acres, including much open field ready for horses, goats, chickens, or plenty of space for large gardens or more. Home offers updates throughout including new roof, also has been freshly painted, and new LVP flooring throughout, new Mini split on 2nd floor. updated bathrooms and all new appliances. Enjoy the park-like setting of the back deck for entertaining. Need more space? Detached 2-car garage offers an apartment above it with a kitchen/ living room combo, bedroom, and full bathroom, excellent for extra family or income-producing. Professional photos 9/6 3 Beds ⋅ 2 Baths Welcome to Willow Pond Road. This property rests on 5 acres, including much open field ready for horses, goats, chickens, or plenty of space for large gardens or more. Home offers updates throughout including new roof, also has been freshly painted, and new LVP flooring throughout, new Mini split on 2nd floor. updated bathrooms and all new appliances. Enjoy the park-like setting of the back deck for entertaining. Need more space? Detached 2-car garage offers an apartment above it with a kitchen/ living room combo, bedroom, and full bathroom, excellent for extra family or income-producing. Professional photos 9/6 23678 Willow Pond Rd, Denton Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact: Selling Office: Berkshire Hathaway HomeServices PenFed Realty.
$479,000 Beautiful Colonial Farmhouse nestled on a wooded lot at the end of a cul-de-sac private lane. This 4 bedroom, 2.5 bath home has been meticulously maintained and features a traditional floor plan with a large kitchen/breakfast area, large family room with vaulted ceilings and a gas fireplace, separate dining room, living room/office. Second floor includes a primary suite with large bathroom with a jacuzzi tub, 3 additional bedrooms and a upstairs laundry room (new washer and dryer). There is an attached 2-car garage, 2 composite decks, 2 sheds all on a 1.35+/- acre lot. 4 Beds ⋅ 3 Baths Beautiful Colonial Farmhouse nestled on a wooded lot at the end of a cul-de-sac private lane. This 4 bedroom, 2.5 bath home has been meticulously maintained and features a traditional floor plan with a large kitchen/breakfast area, large family room with vaulted ceilings and a gas fireplace, separate dining room, living room/office. Second floor includes a primary suite with large bathroom with a jacuzzi tub, 3 additional bedrooms and a upstairs laundry room (new washer and dryer). There is an attached 2-car garage, 2 composite decks, 2 sheds all on a 1.35+/- acre lot. 8605 Hickory Pl, Denton Listing courtesy of Benson & Mangold, LLC. Contact: Selling Office: Samson Properties.
$469,000 Beautiful 3 bedroom 2 bathroom rancher sitting on just over 3 acres. Quiet, friendly neighborhood with plenty of space for your animals too! There are Brazilian hardwoods running through most of the home. Both bathrooms have been remodeled. Generous sized bedrooms with large closets, primary bedroom has two with his and her closets. Tankless instant hot water. Oversized two car garage. It’s also close to shopping and Martinak State Park! 3 Beds ⋅ 2 Baths Beautiful 3 bedroom 2 bathroom rancher sitting on just over 3 acres. Quiet, friendly neighborhood with plenty of space for your animals too! There are Brazilian hardwoods running through most of the home. Both bathrooms have been remodeled. Generous sized bedrooms with large closets, primary bedroom has two with his and her closets. Tankless instant hot water. Oversized two car garage. It’s also close to shopping and Martinak State Park! 25790 Herring Ln, Denton Listing courtesy of Meredith Fine Properties. Contact: Selling Office: Long & Foster Real Estate, Inc..
$465,000 Beautifully maintained 4 bedroom, 2.5 bath Colonial set on a spacious lot just minutes from Denton and the newly opened Caroline Country Club. This inviting home features a comfortable, flowing layout featuring a gas fireplace, perfect for relaxing evenings or gatherings. The kitchen is conveniently located right off the main living area. The space showcases granite counter tops, stainless steel appliances, and a gas range. Upstairs, the large primary bedroom features trace ceilings and an attached primary bathroom with jacuzzi soaking tub. 3 additional bedrooms offer ample closet space and plenty of natural light. Enjoy the outdoors on the large screened-in porch overlooking the private backyard. A 2-car attached garage and separate storage shed provide plenty of space for tools, equipment, and hobbies. Major updates, including a newer roof and upgraded HVAC system featuring 2 separate heat pumps and a gas furnace. Move-in ready and ideally located this one will not last long! 4 Beds ⋅ 3 Baths Beautifully maintained 4 bedroom, 2.5 bath Colonial set on a spacious lot just minutes from Denton and the newly opened Caroline Country Club. This inviting home features a comfortable, flowing layout featuring a gas fireplace, perfect for relaxing evenings or gatherings. The kitchen is conveniently located right off the main living area. The space showcases granite counter tops, stainless steel appliances, and a gas range. Upstairs, the large primary bedroom features trace ceilings and an attached primary bathroom with jacuzzi soaking tub. 3 additional bedrooms offer ample closet space and plenty of natural light. Enjoy the outdoors on the large screened-in porch overlooking the private backyard. A 2-car attached garage and separate storage shed provide plenty of space for tools, equipment, and hobbies. Major updates, including a newer roof and upgraded HVAC system featuring 2 separate heat pumps and a gas furnace. Move-in ready and ideally located this one will not last long! 24749 Woods Dr, Denton Listing courtesy of Benson & Mangold, LLC. Contact: Selling Office: Bayside Realty.
$448,050 Set amid wide-open countryside in Denton, MD (Caroline County 21629), this single-level home is in immaculate, move-in ready condition. A covered front porch opens to a bright entry with hardwood floors and a flexible dining area that connects to the kitchen. Cook and gather with warm wood cabinetry, peninsula bar seating, under-cabinet lighting, and a sink window framing rural views. The living room offers soft neutral tones and recessed lighting for relaxed evenings. Three bedrooms include a light-filled primary suite with dual-vanity bath and soaking tub; a hall bath and a convenient half bath serve guests. Step outside to an expansive composite deck overlooking open fields—ideal for al-fresco dining, morning coffee, or stargazing under Eastern Shore skies. An oversized two-car garage with high ceilings adds storage and workshop flexibility. Designed for low-maintenance living, quality details include 2×6 exterior walls, insulated garage, concrete-slab ( 5') crawl space, Cedar Impressions shingle siding, GAF roof (2020), and central vacuum. Finished area 2,105 sq ft per iGUIDE/ANSI (buyer to verify); floor plan available. Pre-wired for cable/fiber internet supports work-from-home. Enjoy quiet rural living minutes to Denton conveniences, parks, and commuter routes—carefully maintained, maintenance-friendly materials, and truly move-in ready. 3 Beds ⋅ 3 Baths Set amid wide-open countryside in Denton, MD (Caroline County 21629), this single-level home is in immaculate, move-in ready condition. A covered front porch opens to a bright entry with hardwood floors and a flexible dining area that connects to the kitchen. Cook and gather with warm wood cabinetry, peninsula bar seating, under-cabinet lighting, and a sink window framing rural views. The living room offers soft neutral tones and recessed lighting for relaxed evenings. Three bedrooms include a light-filled primary suite with dual-vanity bath and soaking tub; a hall bath and a convenient half bath serve guests. Step outside to an expansive composite deck overlooking open fields—ideal for al-fresco dining, morning coffee, or stargazing under Eastern Shore skies. An oversized two-car garage with high ceilings adds storage and workshop flexibility. Designed for low-maintenance living, quality details include 2×6 exterior walls, insulated garage, concrete-slab ( 5') crawl space, Cedar Impressions shingle siding, GAF roof (2020), and central vacuum. Finished area 2,105 sq ft per iGUIDE/ANSI (buyer to verify); floor plan available. Pre-wired for cable/fiber internet supports work-from-home. Enjoy quiet rural living minutes to Denton conveniences, parks, and commuter routes—carefully maintained, maintenance-friendly materials, and truly move-in ready. 25946 Garey Rd, Denton Listing courtesy of Shore Living Real Estate. Contact: Selling Office: Keller Williams Realty.
$435,000 This charming ranch-style home in the desirable Magnolia Hill community offers a perfect blend of comfort and modern living. With 3 spacious bedrooms and 2 full bathrooms, the open floor plan with cathedral ceilings invites natural light, creating a warm and welcoming atmosphere. The eat-in kitchen features an island, ideal for casual meals, while the adjoining dining area is perfect for entertaining. With so much space in the kitchen the sellers chose to use the dining room as their home office. Set on a generous 1-acre lot, the property boasts a lovely garden view, providing a peaceful backdrop for relaxation. The community is known for its friendly neighbors and well-maintained surroundings. Local parks and recreational areas are just a short stroll away, offering ample opportunities for outdoor activities. This home is not just a place to live; it's a place to thrive. Experience the warmth and community spirit that Magnolia Hill has to offer! 3 Beds ⋅ 2 Baths This charming ranch-style home in the desirable Magnolia Hill community offers a perfect blend of comfort and modern living. With 3 spacious bedrooms and 2 full bathrooms, the open floor plan with cathedral ceilings invites natural light, creating a warm and welcoming atmosphere. The eat-in kitchen features an island, ideal for casual meals, while the adjoining dining area is perfect for entertaining. With so much space in the kitchen the sellers chose to use the dining room as their home office. Set on a generous 1-acre lot, the property boasts a lovely garden view, providing a peaceful backdrop for relaxation. The community is known for its friendly neighbors and well-maintained surroundings. Local parks and recreational areas are just a short stroll away, offering ample opportunities for outdoor activities. This home is not just a place to live; it's a place to thrive. Experience the warmth and community spirit that Magnolia Hill has to offer! 23283 Magnolia Hills Rd, Denton Listing courtesy of Wilson Realty & Staging LLC. Contact: Selling Office: Wilson Realty & Staging LLC.
$435,000 Welcome to this spacious beautiful family home in a desirable subdivision. This 5 bedroom 3.5 bathroom home is inviting the inut you walk through the door. This home boats a first and second floor primary suite tha is perfect for in laws or guests. If closet space is essential to you than you will love the closet space in the 2nd floor primary suite. It's a dream space for anyone with an expansive wardrobe because there is more than enough room for every thing. This stunning home is the largest in the community and provides over 4000 sq feet in addition to a three car garage. This beautiful home is overloaded with so much character as well as a commodious entertainment/recreation room. There's a patio that overlooks the mature trees for a peaceful and serene setting for entertaining, grilling. or just relaxing outside. 5 Beds ⋅ 4 Baths Welcome to this spacious beautiful family home in a desirable subdivision. This 5 bedroom 3.5 bathroom home is inviting the inut you walk through the door. This home boats a first and second floor primary suite tha is perfect for in laws or guests. If closet space is essential to you than you will love the closet space in the 2nd floor primary suite. It's a dream space for anyone with an expansive wardrobe because there is more than enough room for every thing. This stunning home is the largest in the community and provides over 4000 sq feet in addition to a three car garage. This beautiful home is overloaded with so much character as well as a commodious entertainment/recreation room. There's a patio that overlooks the mature trees for a peaceful and serene setting for entertaining, grilling. or just relaxing outside. 1233 Painted Fern Rd, Denton Listing courtesy of EXIT Sunshine Realty. Contact: Selling Office: Long & Foster Real Estate, Inc..
$430,000 Motivated seller, Rare opportunity to purchase 19.1 acres with 2 dwellings, included property identified as 11285 Gregg Rd. Endless options to either rent one or have an in-law suite. It is said to have three septic systems, three electric services all on one property. Then main house which has the basement is in need of some remodeling, has 4 bedrooms and 1.1/4 baths, the remodling process has been started. The little house 2 bedrooms 1 bath, which was a rental is cute and ready for a tenant. Large utility building which was a shop in the past, has a wood stove and electric. The property is in a voluntary forest management program, for tax purpose. Two slabs are still present if someone wanted to rebuild the chicken houses. Bring your dreams and imagination to this beautiful and peaceful property. 4 Beds ⋅ 2 Baths Motivated seller, Rare opportunity to purchase 19.1 acres with 2 dwellings, included property identified as 11285 Gregg Rd. Endless options to either rent one or have an in-law suite. It is said to have three septic systems, three electric services all on one property. Then main house which has the basement is in need of some remodeling, has 4 bedrooms and 1.1/4 baths, the remodling process has been started. The little house 2 bedrooms 1 bath, which was a rental is cute and ready for a tenant. Large utility building which was a shop in the past, has a wood stove and electric. The property is in a voluntary forest management program, for tax purpose. Two slabs are still present if someone wanted to rebuild the chicken houses. Bring your dreams and imagination to this beautiful and peaceful property. 11289 Gregg Rd, Denton Listing courtesy of Benson & Mangold, LLC.. Contact: Selling Office: RE/MAX Executive.
$410,000 Welcome to one of Denton's most charming historic homes, where timeless Victorian architecture, thoughtful updates, and small-town living come together beautifully. Situated on a picturesque corner lot in Denton's historic district, this lovingly maintained five-bedroom home offers more than 2,300 square feet of character-filled living space, abundant natural light, original architectural details, and inviting indoor and outdoor gathering spaces. The gracious covered front portico, mature landscaping, fenced yard, covered side deck, and expansive rear deck create wonderful spaces for relaxing, entertaining, gardening, and enjoying Eastern Shore living. Located within walking distance of downtown Denton's shops, restaurants, community events, and everyday conveniences, the home offers both charm and convenience. The third floor provides flexible bonus space ideal for a home office, studio, reading retreat, playroom, guest overflow, or additional storage. Surrounded by views of a beautiful mature oak tree, the space has a cozy treehouse feel that makes it especially appealing as a creative workspace or remote-work retreat. While the third floor is not connected to the home's central HVAC system, it has been comfortably used year-round with supplemental heating and cooling units. Thoughtful updates help provide peace of mind while preserving the home's historic character, including a 2018 roof, updated electrical panel, Whirlpool range (2019), refrigerator (2017), microwave (2025), Frigidaire Gallery dishwasher with new plumbing and electrical installation (2025), HVAC air handler (2012), and water heater (2011). Perfectly positioned to enjoy the best of the Eastern Shore, the home is approximately 20 minutes to Easton, 50 minutes to Annapolis, 1 hour to Rehoboth Beach, and 90 minutes to Ocean City. This is more than a house—it is a home with warmth, history, character, and heart, offering a lifestyle that blends historic beauty with everyday livability. 5 Beds ⋅ 3 Baths Welcome to one of Denton's most charming historic homes, where timeless Victorian architecture, thoughtful updates, and small-town living come together beautifully. Situated on a picturesque corner lot in Denton's historic district, this lovingly maintained five-bedroom home offers more than 2,300 square feet of character-filled living space, abundant natural light, original architectural details, and inviting indoor and outdoor gathering spaces. The gracious covered front portico, mature landscaping, fenced yard, covered side deck, and expansive rear deck create wonderful spaces for relaxing, entertaining, gardening, and enjoying Eastern Shore living. Located within walking distance of downtown Denton's shops, restaurants, community events, and everyday conveniences, the home offers both charm and convenience. The third floor provides flexible bonus space ideal for a home office, studio, reading retreat, playroom, guest overflow, or additional storage. Surrounded by views of a beautiful mature oak tree, the space has a cozy treehouse feel that makes it especially appealing as a creative workspace or remote-work retreat. While the third floor is not connected to the home's central HVAC system, it has been comfortably used year-round with supplemental heating and cooling units. Thoughtful updates help provide peace of mind while preserving the home's historic character, including a 2018 roof, updated electrical panel, Whirlpool range (2019), refrigerator (2017), microwave (2025), Frigidaire Gallery dishwasher with new plumbing and electrical installation (2025), HVAC air handler (2012), and water heater (2011). Perfectly positioned to enjoy the best of the Eastern Shore, the home is approximately 20 minutes to Easton, 50 minutes to Annapolis, 1 hour to Rehoboth Beach, and 90 minutes to Ocean City. This is more than a house—it is a home with warmth, history, character, and heart, offering a lifestyle that blends historic beauty with everyday livability. 225 S 2nd St, Denton Listing courtesy of Redfin Corp. Contact: Selling Office: Rosendale Realty.
$410,000 Welcome to 109 Briarwood Cir in the sought-after Sandy Meadows community of Denton, offering an impressive blend of space, comfort, and flexibility with over 3,300 finished square feet plus an additional 1,525 sq ft unfinished walkout basement ready for your future vision. With its stately two-story presence, beautiful architectural windows, mature landscaping, and inviting curb appeal, this home makes a memorable first impression before you even step inside. From the moment you enter, natural light pours through the front entry and oversized windows into the sun-filled two-story foyer accented with decorative molding and elegant details. Fresh paint, new carpet, and hardwood flooring create a warm, move-in ready feel throughout. Designed with both everyday living and entertaining in mind, the open floor plan features a spacious family room with a cozy fireplace and a beautifully appointed kitchen complete with granite countertops, stainless steel appliances, center island, and generous gathering space. A main-level office with a charming bay window offers the perfect work-from-home setup. Upstairs, the expansive primary suite is a true retreat featuring vaulted ceilings, two walk-in closets, and a spa-inspired bath with double vanities, jetted soaking tub, oversized walk-in shower, and private water closet. A standout feature of this home is the second oversized bedroom with its own private full bath, creating an ideal guest suite, multigenerational setup, or private retreat. Step outside to enjoy morning coffee on the deck or evenings entertaining as the deck flows seamlessly to the patio and spacious fully fenced backyard — a flat, private setting designed for gatherings, play, and everyday enjoyment. A shed adds even more storage and convenience. Recent updates include a new roof (2023), dual HVAC systems, fresh paint, and new carpet for added peace of mind. Located just minutes from downtown Denton, enjoy small-town charm with local shops, restaurants, parks, and community events nearby. Outdoor enthusiasts will love being close to the Choptank River, Martinak State Park, Tuckahoe State Park, and Adkins Arboretum. Commuters will appreciate convenient access routes, while weekend adventures await with the Chesapeake Bay Bridge approximately 30 minutes away and Delaware beaches within easy reach. This exceptional home offers the perfect blend of space, lifestyle, and Eastern Shore charm. 4 Beds ⋅ 4 Baths Welcome to 109 Briarwood Cir in the sought-after Sandy Meadows community of Denton, offering an impressive blend of space, comfort, and flexibility with over 3,300 finished square feet plus an additional 1,525 sq ft unfinished walkout basement ready for your future vision. With its stately two-story presence, beautiful architectural windows, mature landscaping, and inviting curb appeal, this home makes a memorable first impression before you even step inside. From the moment you enter, natural light pours through the front entry and oversized windows into the sun-filled two-story foyer accented with decorative molding and elegant details. Fresh paint, new carpet, and hardwood flooring create a warm, move-in ready feel throughout. Designed with both everyday living and entertaining in mind, the open floor plan features a spacious family room with a cozy fireplace and a beautifully appointed kitchen complete with granite countertops, stainless steel appliances, center island, and generous gathering space. A main-level office with a charming bay window offers the perfect work-from-home setup. Upstairs, the expansive primary suite is a true retreat featuring vaulted ceilings, two walk-in closets, and a spa-inspired bath with double vanities, jetted soaking tub, oversized walk-in shower, and private water closet. A standout feature of this home is the second oversized bedroom with its own private full bath, creating an ideal guest suite, multigenerational setup, or private retreat. Step outside to enjoy morning coffee on the deck or evenings entertaining as the deck flows seamlessly to the patio and spacious fully fenced backyard — a flat, private setting designed for gatherings, play, and everyday enjoyment. A shed adds even more storage and convenience. Recent updates include a new roof (2023), dual HVAC systems, fresh paint, and new carpet for added peace of mind. Located just minutes from downtown Denton, enjoy small-town charm with local shops, restaurants, parks, and community events nearby. Outdoor enthusiasts will love being close to the Choptank River, Martinak State Park, Tuckahoe State Park, and Adkins Arboretum. Commuters will appreciate convenient access routes, while weekend adventures await with the Chesapeake Bay Bridge approximately 30 minutes away and Delaware beaches within easy reach. This exceptional home offers the perfect blend of space, lifestyle, and Eastern Shore charm. 109 Briarwood Cir, Denton Listing courtesy of Keller Williams Flagship. Contact: Selling Office: Keller Williams Legacy.
$405,000 Waterfront parcel on the Choptank River! 3 (possibly 4) bedroom, 2 full bath 2-story home on a 3.15 +/- acre fee simple parcel. Numerous shade trees and perennial plantings surround the home. Two (2) outbuildings await your vision. Located approximately 15 miles from the Harrington Raceway & Casino, 30 miles from the Bay Bridge and 50 miles from local beach resorts. Owner say to bring offers.Restricted to owner-occupants, non-profits and government agencies through 7/29/2026, with first review of offers on 07/27/2026. Seller may contribute up to 3% of the buyer’s closing costs. Equal Housing Opportunity. HUD Case #241-857485. 3 Beds ⋅ 2 Baths Waterfront parcel on the Choptank River! 3 (possibly 4) bedroom, 2 full bath 2-story home on a 3.15 +/- acre fee simple parcel. Numerous shade trees and perennial plantings surround the home. Two (2) outbuildings await your vision. Located approximately 15 miles from the Harrington Raceway & Casino, 30 miles from the Bay Bridge and 50 miles from local beach resorts. Owner say to bring offers.Restricted to owner-occupants, non-profits and government agencies through 7/29/2026, with first review of offers on 07/27/2026. Seller may contribute up to 3% of the buyer’s closing costs. Equal Housing Opportunity. HUD Case #241-857485. 25214 Smith Landing Rd, Denton Listing courtesy of Brokers Realty Group, LLC. Contact: Selling Office: Long & Foster Real Estate, Inc..
$402,000 Some homes just have that “stop everything and take a closer look” vibe and this is one of them. Discover a home that blends space, comfort, and small-town charm on Maryland’s beloved Eastern Shore. This 4-bedroom, 2.5-bath beauty offers thoughtful design, oversized rooms, and a backyard retreat you’ll never want to leave. Step inside through the soaring two-story foyer and you’re greeted by hardwood floors that flow through the kitchen, breakfast area, and entryway. The kitchen is the heart of the home—complete with an expansive center island, coffee bar, abundant prep space, and a pantry large enough to hold everything you need and then some!. A spacious laundry room doubles as additional storage, while a versatile main-level flex room is perfect for a home office, guest suite, or in-law living space. Upstairs, the open loft fills the home with natural light and connects four oversized bedrooms—each with its own walk-in closet. The primary suite is a true retreat, featuring a spa-like bath with soaking tub, separate shower, an enormous walk-in closet, and even room for a cozy sitting area. Out back, you’ll find your private sanctuary: a vinyl-fenced yard with specialty trees, shrubs, and plants, a patio with built-in BBQ, and plenty of room for entertaining or relaxing outdoors. The rare three-car garage offers unparalleled convenience and storage. Tucked away on a quiet street yet minutes from everything, this home gives you the best of both worlds: peaceful surroundings with easy access to nearby parks, Martinak State Park, Tuckahoe State Park, and Adkins Arboretum. Enjoy the charm of Denton’s historic downtown, or take a short drive to the beaches of Ocean City and Delaware. Here, you’ll experience small-town living with a strong sense of community, surrounded by nature, recreation, and all the beauty of the Eastern Shore. 4 Beds ⋅ 3 Baths Some homes just have that “stop everything and take a closer look” vibe and this is one of them. Discover a home that blends space, comfort, and small-town charm on Maryland’s beloved Eastern Shore. This 4-bedroom, 2.5-bath beauty offers thoughtful design, oversized rooms, and a backyard retreat you’ll never want to leave. Step inside through the soaring two-story foyer and you’re greeted by hardwood floors that flow through the kitchen, breakfast area, and entryway. The kitchen is the heart of the home—complete with an expansive center island, coffee bar, abundant prep space, and a pantry large enough to hold everything you need and then some!. A spacious laundry room doubles as additional storage, while a versatile main-level flex room is perfect for a home office, guest suite, or in-law living space. Upstairs, the open loft fills the home with natural light and connects four oversized bedrooms—each with its own walk-in closet. The primary suite is a true retreat, featuring a spa-like bath with soaking tub, separate shower, an enormous walk-in closet, and even room for a cozy sitting area. Out back, you’ll find your private sanctuary: a vinyl-fenced yard with specialty trees, shrubs, and plants, a patio with built-in BBQ, and plenty of room for entertaining or relaxing outdoors. The rare three-car garage offers unparalleled convenience and storage. Tucked away on a quiet street yet minutes from everything, this home gives you the best of both worlds: peaceful surroundings with easy access to nearby parks, Martinak State Park, Tuckahoe State Park, and Adkins Arboretum. Enjoy the charm of Denton’s historic downtown, or take a short drive to the beaches of Ocean City and Delaware. Here, you’ll experience small-town living with a strong sense of community, surrounded by nature, recreation, and all the beauty of the Eastern Shore. 1111 Daylily Ln, Denton Listing courtesy of RE/MAX Executive. Contact: Selling Office: Samson Properties.
$400,000 New Construction Feel—Without the Wait! Welcome to the highly sought-after Sandy Meadows community, where this beautifully maintained home—just 4 years young—is move-in ready and waiting for its next owners. Offering over 2,500 sq. ft. of living space, this property is designed for comfort, functionality, and effortless entertaining. Step inside to a spacious open-concept living room and kitchen, featuring a double oven, ample cabinetry, and an oversized dining room perfect for hosting gatherings. An additional sitting room and a bright bumped-out sunroom provide even more space for relaxation or entertaining. Double sided fireplace in the living areas make for a cozy and comfortable space. A convenient half bath completes the main level. Upstairs, retreat to the massive primary suite, showcasing a luxurious bathroom with a double-headed shower, soaking tub, and a large double vanity. You’ll also love the his-and-hers walk-in closets. Two additional bedrooms and a second full bathroom offer plenty of room for family or guests. The home also includes a large 2-car garage with high ceilings, ideal for extra storage or oversized vehicles. This property has the modern feel of new construction—without the wait. Come see why this is the perfect place to call home! 3 Beds ⋅ 3 Baths New Construction Feel—Without the Wait! Welcome to the highly sought-after Sandy Meadows community, where this beautifully maintained home—just 4 years young—is move-in ready and waiting for its next owners. Offering over 2,500 sq. ft. of living space, this property is designed for comfort, functionality, and effortless entertaining. Step inside to a spacious open-concept living room and kitchen, featuring a double oven, ample cabinetry, and an oversized dining room perfect for hosting gatherings. An additional sitting room and a bright bumped-out sunroom provide even more space for relaxation or entertaining. Double sided fireplace in the living areas make for a cozy and comfortable space. A convenient half bath completes the main level. Upstairs, retreat to the massive primary suite, showcasing a luxurious bathroom with a double-headed shower, soaking tub, and a large double vanity. You’ll also love the his-and-hers walk-in closets. Two additional bedrooms and a second full bathroom offer plenty of room for family or guests. The home also includes a large 2-car garage with high ceilings, ideal for extra storage or oversized vehicles. This property has the modern feel of new construction—without the wait. Come see why this is the perfect place to call home! 106 Briarwood Cir, Denton Listing courtesy of Douglas Realty LLC. Contact: Selling Office: Samson Properties.