luxury waterfront house for sale Wittman, United States

Set on 28 private acres overlooking Plaindealing Creek along the desirable Easton–St. Michaels corridor, this beautifully remodeled waterfront home offers 4 bedrooms, 4 full baths, and breathtaking panoramic views stretching across to Oxford, the Choptank River, and beyond. Positioned on an exceptional point of land, the property enjoys a rare combination of expansive water vistas, privacy, and direct access to some of the Eastern Shore’s finest boating and sporting waters. A scenic, tree-lined drive leads to the residence, where the water immediately takes center stage. Thoughtfully renovated in 2019, with numerous additional upgrades completed in subsequent years, the home is designed for both relaxed everyday living and effortless entertaining. The main level features a waterside primary suite with an exquisite ensuite bath, along with an additional guest bedroom and adjacent full bath(with sauna). The spacious living room is anchored by a brick fireplace with pellet stove insert, custom built-ins, and sliding doors opening to the waterside patio, creating a seamless connection to the remarkable setting. A well-appointed kitchen with stainless steel appliances and granite countertops adjoins the separate dining room, where spectacular water views provide a memorable backdrop for gatherings. Two other main-level rooms offer flexibility for an office, family room, exercise room, or other living needs, while a generous laundry room with built-ins and a secondary staircase adds everyday convenience. Upstairs are two additional guest bedrooms and two en-suite baths along with an adjoining bonus room ideal for guests or hobbies, and a second staircase. A true sportsman’s paradise, the property offers deep water, excellent fishing, private hunting, and endless opportunities for boating and recreation. The private pier, completed in 2023, features three slips, a boat lift, and a jet ski lift. With approximately 7' MLW, a newly riprapped shoreline, sandy beach, new BAT septic system installed in 2019, and a new roof completed in 2026, this exceptional waterfront retreat is perfectly suited for those seeking the very best of Eastern Shore living. *Approximately 24 acres are enrolled in a Forest Stewardship Plan. * Please do not drive in without an appointment-security monitoring.

Welcome to Holly House – A Rare Waterfront Legacy Estate on the Miles River Holly House presents an extraordinary opportunity to own one of the Upper Miles River’s most captivating waterfront estates. Set gracefully on five spectacular, beautifully landscaped acres, this contemporary French-inspired residence offers approximately 150 feet of private shoreline, panoramic water views, and unforgettable sunsets. Designed for effortless one-level living, the impeccably constructed brick home blends timeless architecture with endless potential. The current residence features a gracious living room, formal dining room, inviting den, spacious kitchen, sunroom, private office, study/optional bedroom, an elegant waterfront primary suite with dual bathrooms and separate walk-in closets, two additional en-suite bedrooms, a powder room, unfinished basement, and an attached two-car garage. Outdoor living is equally impressive. A waterside 8-foot-deep swimming pool, expansive terrace overlooking the Miles River, private 150-foot pier, tennis court, and oversized outbuilding create an exceptional setting for entertaining, recreation, and peaceful waterfront living. Whether you choose to thoughtfully refresh the existing home or create a spectacular new estate, Holly House offers an unmatched canvas to realize your vision. The property has also received its long-awaited approval from Talbot County for a new 5-6 bedroom septic system, allowing construction to begin immediately. Fully permitted architectural and structural plans, along with a stunning full-color exterior fly-through video, are included with the sale. For those wishing to personalize the design, the approved plans can be modified to reflect a buyer’s individual style and lifestyle needs. This is more than a home—it’s a once-in-a-generation opportunity to create a landmark waterfront estate in one of the Eastern Shore’s most coveted location See document panel for floor plans for large addition and another for one level living

BY APPOINTMENT ONLY Saturday September 12th 12-3. Rich in history, timeless in character, and unmatched in location, this extraordinary waterfront estate traces its origins to the early 1900s as the historic Girton House Hotel. Perfectly positioned at the tip of Curtis Point, where the West River meets the Chesapeake Bay, the property later became the beloved Danes on the Bay restaurant, a cherished local landmark. Today, this remarkable estate offers an exceptional blend of historic significance, architectural character, and one of the Chesapeake Bay’s most spectacular waterfront settings. Encompassing more than 9,000 square feet of living space, this waterfront estate is gracefully sited on a premier point of land just under one acre, with over 250 feet of protected shoreline and a private deep-water pier with approximately six plus feet of mean low water depth, ideally suited for both elegant sailing vessels and substantial power yachts. Located just 20 miles from historic Annapolis and approximately 45 miles from Washington, D.C., the residence offers an extraordinary balance of secluded waterfront luxury and effortless access to major metropolitan destinations. Commanding sweeping vistas of the Chesapeake Bay and West River, the estate features multiple boat lifts, eight bedrooms, and an array of expansive, thoughtfully designed entertaining spaces. A truly rare offering, it stands among the most compelling values for a luxury waterfront estate in the region.

Set on a spectacular point of land where the South River meets the Chesapeake Bay, this extraordinary waterfront estate captures some of the most breathtaking views in Annapolis. With coveted southern exposure, the property is immersed in sunlight from dawn to dusk, creating an ever-changing backdrop of sparkling water, passing sailboats, and panoramic Chesapeake vistas. Completely reimagined in 2017 by renowned architect Cathy Purple Cherry, this residence was rebuilt and renovated to an exceptional standard, blending timeless coastal architecture with modern luxury and uncompromising construction quality. Spray-foam insulated walls and roof, steel reinforcement, double plywood construction, four-zone HVAC with humidifiers, gas backup heat, tankless propane water heaters, water treatment systems, generator backup, Sonos audio, and Lutron lighting create a home that is as efficient and functional as it is beautiful. Designed for both grand-scale entertaining and comfortable everyday living, the interior offers over-the-top craftsmanship and thoughtful details throughout. Maple hardwood flooring flows through elegant yet inviting spaces including a dramatic waterfront living room with a custom wet bar, an informal gathering room with built-in bookshelves, a private office with custom cabinetry, wet bar, balcony, and commanding views stretching down the Chesapeake Bay, and a state-of-the-art theater room complete with its own wet bar, refrigerator, and ice maker. The chef’s kitchen is a masterpiece featuring double Wolf ovens, Wolf cooktop, Sub-Zero refrigerator, three dishwashers, wine cooler, ice maker, built-in microwave, instant hot water, walk-in pantry with custom built-ins, and a sun-filled breakfast nook overlooking the water. The luxurious primary suite serves as a private waterfront retreat, highlighted by a stunning spa bath finished with Italian water-cut marble. Three additional bedrooms feature ensuite baths, while a full bath on the main level conveniently serves the pool and outdoor entertaining areas. Outdoor living rivals the finest resorts. Expansive Ipe decking surrounds a heated PebbleTec pool and spa, complemented by an outdoor kitchen, fire pit, integrated sound system, and extensive landscape lighting. The private pier is equipped with water, electric, approximately 4 feet of MLW, a 12,000-pound boat lift, an 8,500-pound boat lift, and a 1,500-pound personal watercraft lift, providing immediate access to the Chesapeake Bay and beyond. Offering 4 bedrooms, 5 full baths, 1 half bath, a dedicated office, and a deep four-car garage, this is a rare opportunity to own one of Annapolis’ premier waterfront properties in a setting where extraordinary architecture, unmatched craftsmanship, and world-class outdoor living come together on the shores of the Chesapeake.

EXPANSIVE SOUTHWESTERN VIEWS OF THE TRED AVON AND CHOPTANK RIVERS. A distinguished waterfront residence in Oxford, thoughtfully designed to embrace its extraordinary setting. Exceptional craftsmanship is evident throughout, with exquisite moldings and millwork, Brazilian Cherry hardwood floors, elevated and vaulted ceilings, abundant natural light, and an open floor plan oriented toward the water. The main level is equally suited to gracious entertaining and comfortable everyday living. A formal dining room opens to a refined gourmet kitchen with a generous center island and breakfast bar, premium stainless-steel appliances, wine storage, and a six-burner gas range. The kitchen flows seamlessly into the spacious living room with gas fireplace and continues to a screened porch and adjoining covered porch with outdoor grill, overlooking the pool and river. A well-appointed guest bedroom with ensuite bath and powder room complete the main level. Upstairs, a spacious sitting area with custom built-ins provides a quiet retreat. The waterside primary suite is exceptionally private, with a sitting area and gas fireplace, private balcony overlooking the river, and two cedar-lined walk-in closets with custom cabinetry. A discreetly integrated refreshment bar with wet sink and beverage refrigerator adds an elegant touch. The ensuite bath features a jetted tub, dual-sink vanity, and glass-enclosed walk-in shower. Three additional guest bedrooms include two sharing a Jack-and-Jill bath and a third with an ensuite bath. The waterfront grounds are designed for both relaxation and entertaining, with a pool and hot tub positioned to take full advantage of the expansive river views. A natural shoreline, small sandy beach, and private dock with boat lift and approximately 3' MLW extend the living experience to the water. A large two-car garage provides generous parking and storage. An exceptional Oxford offering with commanding river views, refined interiors, extensive outdoor living, and a private waterfront setting—an elegant retreat with all the elements for sophisticated Eastern Shore living.

Build your own piece of the Chesapeake Bay lifestyle in Turkey Point. This lot offers water views across the Chesapeake Bay, South River, and Ramsey Bay, creating a beautiful setting for a future home. Surrounded by water, Turkey Point offers multiple community beach access points, a community pier, and Cloud Field, a large community play and recreation area. Boating, fishing, crabbing, kayaking, paddleboarding, and days along the shoreline are all part of what makes this peninsula such a special place. This lot is being offered for sale with the adjacent lot at 3725 Ramsey Drive.

Build your own piece of the Chesapeake Bay lifestyle in Turkey Point. This lot offers water views across the Chesapeake Bay, South River, and Ramsey Bay, creating a beautiful setting for a future home. Surrounded by water, Turkey Point offers multiple community beach access points, a community pier, and Cloud Field, a large community play and recreation area. Boating, fishing, crabbing, kayaking, paddleboarding, and days along the shoreline are all part of what makes this peninsula such a special place. This lot is being offered for sale with the adjacent lot at 3727 Ramsey Drive, providing the opportunity to own two neighboring parcels and create a larger footprint.

An extraordinary expression of waterfront luxury, this architecturally significant estate represents a rare convergence of world class design, craftsmanship, and lifestyle. Located within the prestigious enclave of Wimbledon Farms, surrounded by grand estates and moments from local vineyards and equestrian facilities, the residence was masterfully conceived by acclaimed architect Scarlett Breeding and flawlessly built by Pyramid Builders. A complete refit elevated the home to an uncompromising standard where timeless architecture and modern sophistication exist in perfect harmony. An enchanting winding crushed gravel driveway framed by Belgian block curbing sets the tone for the remarkable experience that awaits. Perfectly positioned with western exposure, the property captures breathtaking sunsets as golden light melts into the horizon across the river and the surrounding landscape. Professionally designed landscaping creates a lush resort like setting that enhances the home’s striking architectural presence. Inside, high lacquered woodwork, bespoke millwork, hidden passage doors, attention to detail, and coffered ceilings create an atmosphere of refined sophistication. Ultra luxe Chesneys fireplace surrounds anchor multiple living spaces with warmth and elegance, while expansive walls of glass frame sweeping water views and seamlessly connect the indoors with the surrounding waterfront setting. A richly appointed wood-clad office with custom built ins offers an executive retreat designed for both privacy and inspiration. At the heart of the residence, the extraordinary St. Charles kitchen rivals those found in internationally celebrated estates, featuring Premier custom cabinetry, a statement Le Cornue range and island, exquisite fixtures, and an artisan-crafted focal point range hood, all designed for elevated entertaining and effortless daily living. Outdoor living reaches resort caliber with an elevated spa and a spectacular four sided overflow vanishing edge pool, where the waterline sits flush with the pool edge, creating a seamless visual connection to the river beyond. Exotic Ipe hardwood decking surrounds the pool and expansive rear terrace, while pergolas and a screened porch provide beautifully designed spaces for entertaining and relaxation. A new private pier, private beach, and panoramic river and pond views complete this extraordinary waterfront lifestyle. The upper level offers four luxurious ensuite bedrooms, including a phenomenal primary suite with sweeping water views, barrel ceiling, a fireside sitting room, a boutique inspired dressing gallery, and a spa quality bath with a soaking tub overlooking the water. Integrated Control4 home automation delivers effortless comfort and convenience throughout. Tucked away on the coveted Annapolis Neck peninsula, Wimbledon Farms offers a rare blend of tranquility, exclusivity, and convenience. Just moments from Downtown Annapolis and major commuter routes, the setting feels worlds away, defined by peaceful surroundings and an unmistakable sense of retreat. Encompassing only 19 estate homesites, this intimate waterfront enclave is gracefully bordered by Harness Creek and the South River, creating a breathtaking backdrop for both sunrise and sunset vistas. Residents enjoy a warm yet private community atmosphere, highlighted by occasional neighborhood gatherings and an expansive marina on protected Harness Creek, a prized deep water haven known for its calm, sheltered waters and exceptional boating access. Welcome Home!

Simultaneously Listed and SOLD

A true Chesapeake treasure! Set within the historic Camp Roosevelt community, once home to one of the nation’s earliest permanent Boy Scout camps, this extraordinary 20-acre estate offers approximately 500 feet of private Chesapeake Bay shoreline - and a beach where fossilized shark teeth and other prehistoric treasures are routinely discovered. It is a rare opportunity to own a property where history, nature, and exceptional waterfront living converge. As you approach the home, you are greeted by a spectacular tree-lined private drive culminating in a grand circular arrival court. The stately Georgian Colonial residence is as welcoming as it is impressive. Built in 1999 and thoughtfully designed for a large family, the home offers 5 bedrooms, 5 full and 1 half baths, with an effortless flow between grand entertaining spaces and comfortable everyday living. A dramatic foyer with sweeping circular staircase opens to a gallery and handsome library with two gas fireplaces, billiards, and views toward the water. Above, the second-level library is open to the room below, creating an extraordinary architectural focal point. The two-story great room anchors the rear of the home, where soaring ceilings, a magnificent chandelier, and walls of windows frame expansive views of the grounds and Chesapeake Bay. Four fireplaces throughout the residence add warmth and character to its gracious living spaces. The heart of the home is its exceptional kitchen, designed for gathering and entertaining with a substantial island, Sub-Zero refrigerator, professional propane range, two dishwashers, walk-in pantry, and adjoining wet bar. The adjacent family room/dining area features vaulted, beamed ceilings and remarkable details that pay homage to the property's storied past, including a historic canoe and a one-of-a-kind custom fireplace hearth carved with the Maryland State Seal. The main-level primary suite is a private retreat, complete with two large walk-in closets and two separate spa-like bathrooms, each with its own vanity, shower, soaking tub, and private water closet. Upstairs are three additional bedrooms, including a private waterside ensuite, two bedrooms connected by a shared bath, a gym, generous storage, and access to the open second-level library. An additional bedroom and full bath above the garage provide exceptional flexibility for guests or extended family. Outside, established gardens, extensive hardscape, custom landscape lighting, built-in firepit, spa and a heated in-ground pool with auto-cover create an extraordinary setting for Chesapeake summers and year-round gatherings. From the pool and grounds, hardscape steps with continuous railing lead down to the private beach and 500 feet of shoreline. The unfinished lower level, with bath rough-in, offers additional potential for the next generation to make their own. More than a grand waterfront estate, this is a home designed for living - gathering family, entertaining friends, celebrating milestones, and creating a lifetime of memories. A truly singular Chesapeake Bay property where timeless architecture, remarkable acreage, living history, and one of Maryland's most extraordinary natural settings come together. Yet remarkably convenient, the property is approximately 45 minutes from Washington, DC and just minutes from the restaurants, shops, and waterfront amenities of Chesapeake Beach. Welcome Home!