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$559,900
3 Beds ⋅ 3 Baths
Could it be possible that the home you've been searching for isn't another typical floor plan — but one thoughtfully designed around the way you actually live? Welcome to an exceptional custom home on 1.4 private acres in Woodcrest Shores, one of Elkton's most sought-after communities near the Elk River and Chesapeake Bay. With over 3,200 square feet of finished living space, this is a home designed to bring people together while giving everyone room to spread out. Just imagine coming home to an inviting front porch, a dramatic great room with soaring ceilings, abundant natural light, and a beautifully appointed kitchen at the heart of it all. The main level is where everyone naturally gathers — equally suited to quiet everyday living or effortless entertaining. Then there's the flexibility. The thoughtfully designed split-level floor plan provides genuine separation between living spaces. The upper level features the primary suite, an additional bedroom, and a full bath. The lower level offers a private guest suite with a spacious bedroom, private full bath, and additional living area — an ideal space for guests, extended family, a home office, hobbies, or simply someone who appreciates having a place of their own. Outside, the experience continues with an impeccably maintained pool, hot tub, expansive yard, and peaceful surroundings on a 1.4-acre corner homesite. Whether you're enjoying a quiet afternoon poolside or gathering with family and friends, this is outdoor living designed to be enjoyed. And when you're ready to venture out, you're just minutes from marina access, the Elk River, Chesapeake Bay, shopping, dining, and major commuter routes. I'm not sure if it's for you or not, but if you've been searching for something beyond the ordinary — a home with character, exceptional living spaces, privacy, and the flexibility to fit the way you live — this one deserves a closer look.

7 Cynthia Ct, Elkton

Listing courtesy of Real Broker LLC. Contact: 8554500442
$499,900
4 Beds ⋅ 3 Baths
Better than new: Built in 2022, this upgraded home is packed with features that truly stand out. Situated on a quiet street with protected trees behind, this home is located in the sought-after Chesapeake Bay Golf Club community. From the moment you arrive, you’ll notice the inviting covered front porch, two-car garage, and a level backyard complete with a maintenance-free deck and privacy fence backing to trees. Inside, luxury vinyl plank flooring flows throughout the main living areas. The kitchen has stainless steel appliances, quartz countertops, a breakfast bar/island, under-cabinet lighting, stylish backsplash, hood vent, and a charming barn door accent for the pantry. Custom shelving adds both function and personality. The recently finished lower level offers a spacious family room, recessed lighting, and a rough-in for a future bathroom. Upstairs, you’ll find a versatile loft, convenient upper-level laundry, and a spacious primary suite featuring a walk-in closet, custom blackout shades, and a beautifully tiled en-suite bath. Two additional bedrooms include carpet, ceiling fans, and ample space, along with a full hall bathroom. The lower level is also finished with a new rec room (new sofa included), framing for a bedroom and rough-in for a full bathroom. Located near the headwaters of the Chesapeake Bay, this community offers easy access to outdoor recreation including walking trails, open spaces, golf courses, downtown North East and Elk Neck State Forest. Commuting is a breeze with quick access to I-95 and proximity to Wilmington, Philadelphia, and Baltimore. SEE UPGRADE LIST.

336 Bay Club Pkwy, North East

Listing courtesy of American Premier Realty, LLC. Contact: 4435120090
$699,000
8 Beds ⋅ 6 Baths
Nestled on 3.6 private acres in the sought-after Pearce Creek community, this exceptional 8-bedroom residence offers an impressive combination of space, comfort, and timeless charm. Thoughtfully designed and meticulously maintained, the home features 4 full bathrooms, 2 half bathrooms, and a 2-car garage, with versatile living spaces ideal for a variety of lifestyles. The main level is anchored by a luxurious owner’s retreat featuring a private sitting room with a wood-burning stove, two walk-in closets, and an elegant en-suite bath complete with a soaking tub. Three additional bedrooms, two full bathrooms, and two half bathrooms provide ample accommodations on this level. Designed for both entertaining and everyday living, the home also offers a formal dining room, welcoming living room, and a spacious eat-in kitchen. A sun-filled four-season room overlooks the wooded backyard, creating a tranquil space to enjoy the beauty of every season. Practical features such as a walk-in pantry, expansive laundry room with abundant storage, and beautiful tongue-and-groove hardwood flooring throughout enhance both function and character. Upstairs, a private suite with a large bedroom, walk-in closet, and full bath provides the perfect setup for guests or multigenerational living. Three additional bedrooms, a kitchenette, and a dramatic open-concept family room with custom built-in bookshelves and a wood-burning stove complete the upper level, offering endless flexibility for gathering, relaxing, or entertaining. The unfinished basement presents a blank canvas for future expansion, whether you envision additional living space, a recreation area, workshop, or home gym. Combining generous living space, distinctive architectural details, and a peaceful natural setting, this one-of-a-kind property presents a rare opportunity to enjoy country living without compromise. Surrounded by mature Leyland cypress and Southern pine trees, the property offers a remarkable sense of privacy and seclusion while remaining conveniently located within the Cecil County School District.

143 Clemencia Rd, Earleville

Listing courtesy of Samson Properties. Contact: 4433437660
$10,000,000
14 Beds ⋅ 14 Baths
This offering marks an extraordinary opportunity to acquire one of North America’s most prestigious properties. While the 437.5 acre farm is globally celebrated for its history of breeding, training, and raising excellence and many world-class sport horse champions, the focus now turns to the sale of the physical estate, a masterpiece of equestrian infrastructure and natural beauty now available for its next chapter. The property is defined by its remarkable landscape, featuring 200 wooded acres of mature trees, 220 acres of pastureland, and 15 acres of impervious structures across the gently rolling terrain of Cecil County. Bordered by 1.3 miles of tranquil waters of the Octoraro Creek, the land offers a rare combination of high-performance utility and serene privacy. The sale includes comprehensive, established equestrian infrastructure, highlighted by a 36-stall main barn, 2 outdoor arenas, 12 fields, 31 paddocks, 14 dwellings, 2 additional barns, and numerous equine facilities that have served as the benchmark for elite sport horse development for decades. The true value of Hilltop Farm’s footprint lies in its versatility; it is a canvas limited only by the scale of one’s imagination. While its equestrian pedigree is unrivaled, the estate invites a bold repurposing as a world-class Agri-Tourism Destination or a Private Legacy Compound. The riverfront and woodlands are perfectly suited for a Luxury Wellness Retreat, with riparian trails just a stone's throw from the urban corridors of Philadelphia, Baltimore, and DC. As this historic operational chapter concludes, the property is now positioned for a new curator to inherit a landscape of immense function and beauty. This is a rare chance to own a sanctuary that has been both a stage for international sport and a community standard-bearer. This property includes multiple parcels and should be referenced in conjunction with MLS# MDCC2020402 (Tax ID: 0806025811) and MLS# MDCC2020404 (Tax ID: 0806012450). Photos #6, #9, #13, #18, #28, #33, #39, #51, #58, and #61 are AI-generated conceptual images depicting potential improvements and/or uses for the Conference Center, Tenant House, and Lodge. These images are for illustrative purposes only and do not represent existing conditions.

1089 Nesbitt Rd, Colora

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767
$10,000,000
14 Beds ⋅ 14 Baths
This offering marks an extraordinary opportunity to acquire one of North America’s most prestigious properties. While the 437.5 acre farm is globally celebrated for its history of breeding, training, and raising excellence and many world-class sport horse champions, the focus now turns to the sale of the physical estate, a masterpiece of equestrian infrastructure and natural beauty now available for its next chapter. The property is defined by its remarkable landscape, featuring 200 wooded acres of mature trees, 220 acres of pastureland, and 15 acres of impervious structures across the gently rolling terrain of Cecil County. Bordered by 1.3 miles of tranquil waters of the Octoraro Creek, the land offers a rare combination of high-performance utility and serene privacy. The sale includes comprehensive, established equestrian infrastructure, highlighted by a 36-stall main barn, 2 outdoor arenas, 12 fields, 31 paddocks, 14 dwellings, 2 additional barns, and numerous equine facilities that have served as the benchmark for elite sport horse development for decades. The true value of Hilltop Farm’s footprint lies in its versatility; it is a canvas limited only by the scale of one’s imagination. While its equestrian pedigree is unrivaled, the estate invites a bold repurposing as a world-class Agri-Tourism Destination or a Private Legacy Compound. The riverfront and woodlands are perfectly suited for a Luxury Wellness Retreat, with riparian trails just a stone's throw from the urban corridors of Philadelphia, Baltimore, and DC. As this historic operational chapter concludes, the property is now positioned for a new curator to inherit a landscape of immense function and beauty. This is a rare chance to own a sanctuary that has been both a stage for international sport and a community standard-bearer. This listing includes multiple parcels and should be referenced in conjunction with MLS# MDCC2020400 and MLS# MDCC2020404. Photos #6, #9, #12, #18, #30, #32, #40, #52, #59, #63, #68, #70, and #83 are AI-generated concept images of the Conference Center, Tenant House, and Lodge and are intended for illustrative purposes only.

1089 Nesbitt Rd, Colora

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767
$495,000
2 Beds ⋅ 2 Baths
Absolutely adorable beach home being offered fully furnished and ready for your summer fun. Lots of upgrades throughout make this a worry free property offering wonderful beach and community amenities. There is a civic association with annual dues of $300. Community boat ramp and swim beach. Lots of neighborhood activities including a golf cart parade, picnic and much more. There is also a 10kw back up generator to keep you up and running in the event the power does not! Get a head start on the summer season and come see this charming property today!

112 Midway Dr, Earleville

Listing courtesy of L. C. Parker Real Estate. Contact:

$8,995,000
6 Beds ⋅ 5 Baths
Set on 93 private acres with 6,100 feet of shoreline along the picturesque Sassafras River and Cox Creek. The estate includes a main house, guest house, pool house and riverside pavilion, offering ample delightful space for large groups to gather, unwind and experience the activities and natural beauty of the upper Chesapeake. Showcasing exceptional design, materials, craftsmanship, the living spaces are framed by expansive views of the Sassafras River. The main residence includes six spacious bedrooms and four and a half baths. The heart of the home is a gourmet kitchen and adjacent generous breakfast room wrapped in 180-degree river views, a setting that enhances every meal. The home flows naturally into multiple large gathering spaces built for entertaining, and into quieter, more intimate rooms designed for reflection and rest. The guest house ensures that you can accommodate family and friends. With three generously sized bedrooms and one and a half baths, full kitchen, fireplace and brick patio, it offers a self-contained retreat that gives guests their own space while keeping everyone together on the estate. The pool complex redefines what a backyard amenity can be. At its center is a 52,000-gallon swimming pool with a retractable electric cover, positioned to frame sweeping panoramic river views. An adjoining heated spa and a oversized pool deck complete a setting that invites long, unhurried afternoons in the sun. Elevating the experience further, it offers a full bath, generous living and dining areas, and amenities more commonly found at a high-end resort - a large, well-equipped gym and an eight-person steam room -providing the perfect end to an active day. Perched at the water's edge, the recently constructed two-story pavilion is the social and recreational heart of the estate's waterfront. It's a front-row seat to everything that makes the Sassafras River so beloved: working crab boats in the early morning, sailboats gliding past at midday, and the sky turning gold over the water at dusk. Spend a lazy afternoon on the pavilion's upper level as the river life unfolds below, then head down to launch your own boat from the private boat lift or boat ramp. The Sassafras and Cox Creek offer boundless activities including boating, water skiing, tubing, wakeboarding, sailing, paddleboarding, and kayaking, all awaiting just steps away. After fun on the water, return to the pavilion for lunch, dinner, or simply a seat with one of the best views on the upper Bay. Adjacent to the grassy wharf, the nearly 1,000-foot private sandy beach is a rare and remarkable amenity ideal for an afternoon stroll with friends or a quiet moment watching the sunset or moon rise over the river. Other improvements along the waterfront include a 1000+ stone revetment protecting the shoreline, a 13,000lb boat lift, and a boat ramp. The grounds reflect a thoughtful balance of beauty, privacy, and long-term stewardship, with carefully planned enhancements designed to complement the natural setting while supporting comfortable estate living. Mature trees and established landscaping create a sense of arrival and continuity across the property, while curated sightlines and open lawn areas transition naturally into wooded edges and surrounding countryside. A network of trails invites exploration through the woods, offering quiet vantage points and seasonal changes that reinforce the property’s connection to the Eastern Shore landscape. The property's blend of fields, woods and waterfront habitats, complemented by offshore hunting rights offers productive hunting. The land supports healthy populations of deer, wild turkey, ducks & geese, creating a sportsman's haven throughout the seasons. Enjoy fishing and crabbing from the dock ideally located on the edge of the deep water channel. Major mid-Atlantic cities, international airports & train stations are within easy reach, making the estate accessible for full-time residents and weekend escapes.

750 Cassidy Wharf Rd, Earleville

Listing courtesy of Gunther-McClary Real Estate. Contact:

$549,900
4 Beds ⋅ 4 Baths
Welcome to this exceptional Waterford model offering over 4,800 square feet of total living space on a beautifully landscaped 0.32-acre lot backing to protected woods for outstanding privacy and peaceful views. This impressive 4-bedroom, 3.5-bath Colonial with a 2-car attached garage combines spacious living, elegant architectural details, and endless possibilities for future expansion. Step inside to a welcoming 2 story foyer highlighted by beautiful hardwood flooring that flows throughout much of the main level. The thoughtfully designed floor plan features formal living and dining rooms, a private home office, and an expansive family room accented by architectural columns, a cozy gas fireplace, and a spacious bump-out that creates the perfect gathering space for family and friends. The gourmet kitchen is designed for both everyday living and entertaining, offering abundant cabinetry, generous counter space, and a bright breakfast area and sunroom that opens seamlessly onto a rear deck overlooking the large, level backyard and tranquil wooded backdrop. An ideal setting for outdoor dining, relaxing, or entertaining. Upstairs, the luxurious primary suite serves as a private retreat featuring a spacious sitting room, elegant tray ceiling, oversized walk-in closet, and a spa-inspired bath. Three additional generously sized bedrooms, a full hall bath, and the convenience of an upper-level laundry room complete the second floor. The walk-out lower level provides incredible flexibility with a finished recreation room, full bath, abundant storage, and multiple framed rooms with windows already in place, offering outstanding potential to create up to two additional bedrooms, a media room, fitness area, hobby space, or multi-generational living. Additional highlights include a brick-front exterior, owned propane tank (no lease), zoned heating and cooling, public water and sewer, and an attached two-car garage. Located in the desirable Chesapeake Club Fairway Links community, residents enjoy a quiet neighborhood setting with easy access to Chesapeake Bay marinas, golf, waterfront dining, shopping, and major commuter routes, making travel to Delaware, Pennsylvania, and the Baltimore metropolitan area convenient. Combining exceptional space, quality construction, and a private wooded setting, this remarkable home offers an outstanding opportunity to enjoy comfortable everyday living with room to grow for years to come.

128 Bay Club Pkwy, North East

Listing courtesy of Winning Edge. Contact: 4434636009
$19,900,000
4 Beds ⋅ 5 Baths
Rarely… does such a unique, well-designed, constructed, and maintained world-class equestrian facility grace the international real estate market. Spanning 510 preserved acres, this iconic equestrian estate boasts a rich legacy and unparalleled amenities, including a state-of-the-art equestrian training facility built by B&D Builders, a nationally renowned custom builder. RiverEdge Farm is synonymous with world-class equestrian training, ideally suited to any discipline. The farm has previously housed numerous Olympic dressage and three-day event horses, operated as a top-class private thoroughbred breeding facility, and most recently served as a training mecca for world-class dressage. At the heart of the property is a spectacular 31-stall, 45,000-square-foot indoor dressage show barn. Built with unmatched craftsmanship and old-world charm second to none. Visitors are welcomed through a charming, covered porch and elegant, glass-paneled double doors into a grand reception area featuring a central stone fireplace and a private meeting room, all adorned with custom millwork throughout. Overlooking the 100’ x 200’ indoor dressage arena are stunning glass-enclosed observation areas on both the first and second floors, that are brilliantly filled with natural light and character. This impressive space includes twin service bars, a conveniently located commercial-grade kitchen, and a spacious area ideal for entertaining. An ornate wide-plank staircase leads to a lofted second level with private office suites, an exercise room, and a lounge area. The barn itself is thoughtfully designed, featuring barreled ceilings, six grooming/wash stalls, two well-appointed tack rooms, a central eat-in kitchen/break area, a laundry room, and a three-season sitting room offering panoramic views through grand window walls on two sides. The barn’s layout seamlessly flows through a bank of 31 spacious (mostly 14’ x 14’) stalls, curving into an additional wing with even more accommodations. Complementing the equestrian facilities is a beautifully appointed 9,000-square-foot brick manor home of Georgian architectural style, offering four bedrooms and 3 full & 2 half bathrooms. This wonderful home features an updated kitchen, brick and antique wood flooring, beamed ceilings, a sunken living room, multiple fireplaces, a spacious game room, and a detached three-car garage. The extensive grounds are thoughtfully and professionally landscaped. It artfully blends traditional character with modern conveniences—perfectly suited for today’s lifestyle. Also included within this breathtaking property is a luxurious guest home featuring a chef’s kitchen and an enclosed timber-framed pavilion over a heated indoor pool. Additionally, there is a 15-stall center-aisle block barn with a six-horse Kraft Eurocizer, as well as numerous ancillary operational buildings, including a fully functional brick office building—and numerous double-fenced fields and paddocks with approximately 10 miles of four-rail post-and-board fencing offering unparalleled views throughout the farm. RiverEdge is set within one of Maryland’s largest agricultural preservation areas and is protected by a conservation easement, ensuring its beauty and legacy for generations to come. The property includes 4 parcels: 0802016206 - 109.4 acres, 0802019078 - 186.7 acres, 0802029049 - 106 acres, and 0802029537 - 109.4 acres.

1455 Cayots Corner Rd, Chesapeake City

Listing courtesy of Monument Sotheby's International Realty. Contact: 3026546500
$19,900,000
4 Beds ⋅ 5 Baths
Rarely… does such a unique, well-designed, constructed, and maintained world-class equestrian facility grace the international real estate market. Spanning 510 preserved acres, this iconic equestrian estate boasts a rich legacy and unparalleled amenities, including a state-of-the-art equestrian training facility built by B&D Builders, a nationally renowned custom builder. RiverEdge Farm is synonymous with world-class equestrian training, ideally suited to any discipline. The farm has previously housed numerous Olympic dressage and three-day event horses, operated as a top-class private thoroughbred breeding facility, and most recently served as a training mecca for world-class dressage. At the heart of the property is a spectacular 31-stall, 45,000-square-foot indoor dressage show barn. Built with unmatched craftsmanship and old-world charm second to none. Visitors are welcomed through a charming, covered porch and elegant, glass-paneled double doors into a grand reception area featuring a central stone fireplace and a private meeting room, all adorned with custom millwork throughout. Overlooking the 100’ x 200’ indoor dressage arena are stunning glass-enclosed observation areas on both the first and second floors, that are brilliantly filled with natural light and character. This impressive space includes twin service bars, a conveniently located commercial-grade kitchen, and a spacious area ideal for entertaining. An ornate wide-plank staircase leads to a lofted second level with private office suites, an exercise room, and a lounge area. The barn itself is thoughtfully designed, featuring barreled ceilings, six grooming/wash stalls, two well-appointed tack rooms, a central eat-in kitchen/break area, a laundry room, and a three-season sitting room offering panoramic views through grand window walls on two sides. The barn’s layout seamlessly flows through a bank of 31 spacious (mostly 14’ x 14’) stalls, curving into an additional wing with even more accommodations. Complementing the equestrian facilities is a beautifully appointed 9,000-square-foot brick manor home of Georgian architectural style, offering four bedrooms and 3 full & 2 half bathrooms. This wonderful home features an updated kitchen, brick and antique wood flooring, beamed ceilings, a sunken living room, multiple fireplaces, a spacious game room, and a detached three-car garage. The extensive grounds are thoughtfully and professionally landscaped. It artfully blends traditional character with modern conveniences—perfectly suited for today’s lifestyle. Also included within this breathtaking property is a luxurious guest home featuring a chef’s kitchen and an enclosed timber-framed pavilion over a heated indoor pool. Additionally, there is a 15-stall center-aisle block barn with a six-horse Kraft Eurocizer, as well as numerous ancillary operational buildings, including a fully functional brick office building—and numerous double-fenced fields and paddocks with approximately 10 miles of four-rail post-and-board fencing offering unparalleled views throughout the farm. RiverEdge is set within one of Maryland’s largest agricultural preservation areas and is protected by a conservation easement, ensuring its beauty and legacy for generations to come. The property includes 4 parcels: 0802016206 - 109.4 acres, 0802019078 - 186.7 acres, 0802029049 - 106 acres, and 0802029537 - 109.4 acres.

1455 Cayots Corner Rd, Chesapeake City

Listing courtesy of Monument Sotheby's International Realty. Contact: 3026546500