Refine Search
Sort by
$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:

$567,990
3 Beds 2 Baths
THIS IS A TO BE BUILT HOME! Welcome to Sussex, the epitome of modern rancher living! This single-level floor plan has captured the hearts of many, and it's not hard to see why. With stunning curb appeal and thoughtfully designed features and finishes, the Sussex offers versatility to suit any modern lifestyle. Step into an open-concept floor plan that seamlessly connects the Kitchen, Breakfast area, and Great Room, perfect for entertaining or simply enjoying quality time with loved ones. Extend your Breakfast area by adding a Sunroom or enjoy al fresco meals and take your living outdoors with an optional Screened Porch. Just off the Great Room, the Owner's Suite is a true retreat with two walk-in closets that offer ample storage space that extends into a private Owner’s Bath. Plus, you have the option to choose from three upgrade options for the Owner's Bath: the luxurious Venetian-Style with a large shower and bench, the contemporary Roman-style with a walk-in shower, or the indulgent Super with a soaking tub in addition to the shower. In addition to the Owner's Suite, there are two more bedrooms and a hall bath, providing versatility for families of any size. Need extra space? An optional second floor brings added possibilities with a Loft, an additional Bedroom, and a full Bath. Or you can opt for a finished lower level which can provide a Den, Recreation Room, full Bath, and a spacious unfinished Storage area. Experience the joy of single-level living without compromising on style or functionality.

TBD Pine Needle Court, Conowingo

Listing courtesy of Mary Ann Hammel. Contact: (410) 705-2565

$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

$305,000
3 Beds 2 Baths
NEW PRICE! Folk Victorian home, featuring gingerbread trim and over 2000 sq ft., offers a versatile layout ideal for everyday living and entertaining. Spacious kitchen and family rooms with exposed beams provide warmth and character, while the primary suite and laundry on the main level add convenience. The family room bay window overlooks an adjacent lot for sale, presenting exciting opportunities for expansion, gardening, or added privacy. Outdoors, you have a composite deck where you can enjoy beautiful sunsets and a view of the Chesapeake City bridge, front porch, and fenced, sodded rear yard- perfect for gatherings or relaxing. Shed for added storage. While the home has had updates and repairs, it offers the opportunity to refresh finishes and flooring to make it your own.

320 Cecil St, Chesapeake City

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (410) 879-8080

$1,400,000
4 Beds 4 Baths
This waterfront property offers incredible potential and a rare opportunity to create something truly special. The home experienced storm damage several years ago, and while significant improvements have already been completed, the property is still in the process of being renovated and will require additional work to finish. Recent updates include all new windows, new siding, a new roof, a new dishwasher, and a newly built deck. The basement has been completely gutted and is ready to be finished. The home offers a spacious layout with unique features, including a primary bedroom with a loft and sliding glass doors that open to the deck, providing beautiful natural light and a relaxing connection to the outdoors. Another standout feature is the separate above-garage apartment/in-law suite, which includes a bedroom, bathroom, mini-kitchen, and private entrance, offering great potential for guests, extended family, or additional living space. The property also includes both an attached garage and a large detached garage, providing plenty of storage, parking, and workspace. Situated on 3.12 private acres along the water, the setting is truly the highlight—offering peaceful views, privacy, and plenty of space to make this property your own. The seller is unable to complete the remaining renovations, and the property is being sold in its current condition. With vision and finishing touches, this home could be transformed into an exceptional waterfront retreat.

38 Osprey Way, Elkton

Listing courtesy of Iron Valley Real Estate of Central PA. Contact: (717) 344-5950

$549,990
4 Beds 3 Baths
PROPOSED CONSTRUCTION, THIS HOME IS NOT BUILT! COME CHOOSE YOUR LOT, FLOOR PLAN AND OPTIONS! Experience the perfect blend of classic elegance and modern living with the Bristol II. This stunning home features a timeless colonial facade, providing a warm welcome from the moment you arrive. As you step inside, you’ll find a foyer flanked by a formal living room and a formal dining room. These spaces are perfect for hosting gatherings and can be easily transformed into a home office or playroom, allowing you to tailor the floor plan to fit your needs. At the heart of the home, the combined Great Room, Breakfast Room, and Kitchen create an inviting space for gatherings. The cook-friendly kitchen offers abundant cabinet and pantry space, ensuring everything is at your fingertips. You can also add an optional island to enhance storage and functionality. Retreat upstairs to your tranquil Owner’s Bedroom, which features a luxurious ensuite bathroom with double vanity sinks. Enjoy the convenience of a spacious walk-in closet, along with additional linen storage. In addition, three more bedrooms on this level offer flexibility for family or guests, and a conveniently located laundry closet adds to the home’s practicality. Every inch of the Bristol II has been thoughtfully designed for modern living.

TBD White Spruce Way, Conowingo

Listing courtesy of Mary Ann Hammel. Contact: (410) 705-2565

$431,731
4 Beds 2 Baths
TO BE BUILT NEW CONSTRUCTION. Beautiful lot Co- Marketed with a professional builder. This Model is the ----- TRIUMPH --- The Triumph is the perfect ranch-style home for those who desire one-level living, yet still want space for the entire family. With four bedrooms and an open living area, the layout of this home takes advantage of every inch of living space. The center of the home is a large island in the kitchen, perfect for gathering and entertaining. A two-car garage is included, plus many more standard features. --- Buyer may choose any of the builders models that will fit on the lot, prices will vary. Photos are provided by the Builder. Photos and tours may display optional features and upgrades that are not included in the price. Final sq footage are approx. and will be finalized with final options. Upgrade options and custom changes are at an additional cost. Pictures shown are of proposed models and do not reflect the final appearance of the house and yard settings. All prices are subject to change without notice. Purchase price varies by chosen elevations and options. Price shown includes the Base House Price, The Lot and the Estimated Lot Finishing Cost Only. Builder tie-in is non-exclusive Welcome to Chesapeake Haven on Ohio Ave in Earleville, your opportunity to own a slice of paradise in one of the area’s most charming water-access communities. Just moments from the shoreline, this unique offering includes four parcels (Lots 14, 23, 25 & 26) spanning Maryland Ave, Ohio Ave, and New Jersey Ave, totaling approximately .675 acres of prime opportunity. Residents enjoy access to fishing, boating, kayaking, beach days, and breathtaking views from the community waterfront—perfect for relaxing weekends and unforgettable summer memories. Whether you envision building a year-round residence, a vacation retreat, or a weekend escape, the flexibility of multiple lots opens the door to endless possibilities. The seller has already completed substantial groundwork with the township and is in the process of finalizing the attached lot, creating exciting potential for multiple builds (buyer to perform due diligence regarding perc testing and building potential). New construction is already emerging nearby, adding to the momentum and appeal of this peaceful waterfront neighborhood. Tucked away for tranquility yet just a short drive to tax-free Delaware shopping, dining, and entertainment, Chesapeake Haven offers the best of both escape and convenience. Drive by today and start planning your dream by the water. The seller is arranging to have a new survey conducted.

Ohio Ave, Earleville

Listing courtesy of Keller Williams Real Estate - Media. Contact: 6105651995

$59,900
Welcome to Chesapeake Haven on Ohio Ave in Earleville, your opportunity to own a slice of paradise in one of the area’s most charming water-access communities. Builder tie-in is optional. Just moments from the shoreline, this unique offering includes four parcels (Lots 14, 23, 25 & 26) spanning Maryland Ave, Ohio Ave, and New Jersey Ave, totaling approximately .675 acres of prime opportunity. Residents enjoy access to fishing, boating, kayaking, beach days, and breathtaking views from the community waterfront—perfect for relaxing weekends and unforgettable summer memories. Whether you envision building a year-round residence, a vacation retreat, or a weekend escape, the flexibility of multiple lots opens the door to endless possibilities. The seller has already completed substantial groundwork with the township and is in the process of finalizing the attached lot, creating exciting potential for multiple builds (buyer to perform due diligence regarding perc testing and building potential). New construction is already emerging nearby, adding to the momentum and appeal of this peaceful waterfront neighborhood. Neighbors are open to owner financing with a land installment contract as well.

Ohio Ave, Earleville

Listing courtesy of Keller Williams Real Estate - Media. Contact: 6105651995

$514,990
4 Beds 3 Baths
As you walk into the Hamilton there is a Choice Room that's open to the foyer. Use this space as a formal living room or playroom for the kids. Down the hall is the Great Room. Add an optional fireplace to make an inviting space to gather with the whole family. The Great Room opens up to a classically designed Kitchen. A small Mudroom at the entry to the Garage rounds out this flexible first floor. Following the stairs, to the second floor, you find the Owner's Suite and three additional Bedrooms, all with ample closet space, plus a Laundry Room, centrally located at the end of the hallway for convenience and ease. The Owner's Suite with a spacious bedroom offers a walk-in closet brimming with storage space. Designed to be a private haven, the Owner's Bedroom has an ensuite bath with available options of a Super Bath, with soaking tub and shower, or Venetian-style, with a large glass-enclosed shower with seat. Take the Hamilton design even further with a variety of options, extensions, and upgrades to personalize this dream home.

TBD Nell Street, Perryville

Listing courtesy of Mary Ann Hammel. Contact: (410) 705-2565

$492,990
3 Beds 3 Baths
As you walk into the spacious Chaucer II you are greeted by an open concept that includes the Dining area, Kitchen, and Great Room feels as if it is one giant space as you easily move through to the Great Room at the rear of the home. Each room flows effortlessly into the other giving the whole home an open and airy ambiance. The Kitchen has a tremendous amount of space with a plethora of cabinets, a pantry, and a kitchen island; making storage and organization plentiful. The first floor also includes the Owner's Suite with walk-in closet and a private Owner's Bath. Additional Owner's Bath options include a Super Bath, with the added pleasure of a large soaking tub, or a Roman-style bath, which features a deep, walk-in shower with a tiled bench seat. The upper level is accessed by stairs located near the first-floor laundry room. The second level includes two additional bedrooms, a hall bath, and a large loft with additional unfinished storage space. This home design offers a wide variety of options and extensions making it easy to create the home of your dreams.

TBD Nell Street, Perryville

Listing courtesy of Mary Ann Hammel. Contact: (410) 705-2565

$305,000
3 Beds
Come see this beautifully renovated ranch-style home offering over 1,431 sq. ft. of living space, ideally located on a quiet back street in a desirable water-oriented community with beach access. This 3-bedroom, 1 full bath home was completely renovated down to the studs in 2021, allowing the next owner to enjoy the benefits of extensive upgrades throughout. The open floor plan seamlessly connects the living room, dining area, and kitchen, creating a functional and inviting living space. The kitchen features white cabinetry, black granite countertops, and GE stainless steel appliances, while the home is enhanced by ¾-inch thick, 3-inch wide sanded and stained hardwood floors. A spacious family room offers a wood stove and slate flooring, providing additional living and entertaining space. Major improvements include all new plumbing and electrical systems (2021), Andersen Low-E windows, and a Pella sliding door with built-in blinds in the primary bedroom. The updated full bath features a tile surround, and the home is equipped with a high-efficiency Amana heat pump, 50-year architectural shingles, and updated siding. Additional highlights include a stackable washer and dryer, a large front deck, storage shed, and seasonal water views. Residents enjoy access to community amenities including boating, watersports, and beach access. A thoughtfully renovated, move-in-ready home offering comfort, quality, and lifestyle in a waterfront community.

16 Florida Ave, Earleville

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