luxury houses with pool for sale Annapolis, United States (page 2)

This extraordinary gated 20-acre waterfront estate, featuring a French-inspired stone residence, sits prominently along the banks of the Severn River just minutes from downtown Annapolis and under an hour from Washington, DC. With coveted western exposure, the property offers breathtaking, year-round sunsets and over 23,000 square feet of combined living space across the main house, guest house, and carriage house-all set amid rolling lawns, formal gardens, mature trees, and natural surroundings. The main residence is designed for both grand entertaining and comfortable living, with ten sets of French doors opening to terraces and gardens. A dramatic two-story foyer with limestone and marble inlays leads to a soaring great room anchored by an 18th-century French carved limestone mantel. Additional main-level spaces include a formal dining room, library, and music room-each with its own fireplace-and a gourmet kitchen featuring dual marble-topped islands. Upstairs, an open gallery overlooks the great room and grounds, while the expansive primary suite offers a fireplace, private sitting room, and waterside balcony with sweeping river views. The lower level is equally impressive, with a family room, billiards room and bar, a striking stone wine cellar with tasting room, media room, full gym with bath and sauna, and an additional bedroom suite. A separate wing provides a dedicated art studio or craft space, complemented by a motor court and two three-car garages. Outdoor living is equally refined, with manicured lawns and gardens, an expansive patio, outdoor kitchen, hot tub, and charming details including a gardening shed, chicken coop, and raised beds. The approximately 6,000-square-foot guest house is ideal for hosting, centered around a pool with a covered veranda, outdoor fireplace, bar, and gazebo-all with water views. Inside, it offers spacious living and dining areas with a shared stone fireplace, three bedrooms, two full and two half baths, and a full catering kitchen with Viking appliances. A breezeway connects to the carriage house with an additional three-car garage. The estate's 900 feet of shoreline is complemented by a 350-foot deep-water pier (8-9' MLW) with four slips, including two accommodating 60-foot vessels, and two boat lifts-perfect for boating, sailing, and enjoying life on the Severn River and Chesapeake Bay.

Experience the best of the Severna Park waterfront lifestyle from this exceptional home, privately positioned at the end of a cul-de-sac and elevated above Yantz Creek to capture sweeping views toward the Severn River. With a heated waterside pool, expansive outdoor living spaces, and a private pier with boat lift, this is a home designed for days spent on the water and evenings relaxing poolside. Open and spacious interiors keep the water views at the forefront. Formal living and dining spaces flow around the double sided fireplace into the waterside gourmet kitchen and family room, where sliding glass doors open to a rear balcony overlooking the pool and creek. Whether gathering with friends, dining outdoors, or enjoying a quiet morning above the water, indoor and outdoor living blend effortlessly. The main-level primary suite offers beautiful privacy with two walk-in closets and a spacious ensuite bath with dual vanity areas, jetted tub, and walk-in shower. An additional bedroom, full bath, and powder room provide flexibility for family and guests. The expansive lower level was made for entertaining, featuring a second double-sided fireplace, wet bar, full kitchen, and generous recreation and gathering spaces. Three additional bedrooms and two full baths offer plenty of room for overnight guests or extended family, while a separate entrance from the driveway adds even greater versatility. Just outside, a large covered brick patio leads to the heated in-ground pool and expansive pool deck, all overlooking the waterfront with a conveniently located pool bath nearby. Beyond the pool, a distinctive brick bulkhead and private pier with boat lift make it easy to head out for a day on the Severn or simply settle in and enjoy the ever-changing views. All of this is tucked into sought-after West Severna Park, close to shops, restaurants, award winning schools, and convenient commuter routes. Welcome Home!

Welcome to this fabulous waterfront estate historically known as The POD. Set behind the gates of an extraordinary 7+ acre waterfront compound, The POD offers a rare blend of privacy, scale, and resort-caliber living along Forked Creek and the Severn River. Beautifully constructed and thoughtfully curated, the property unfolds as a true lifestyle destination, where every detail has been designed to elevate both everyday living and grand entertaining. A long, illuminated drive framed by mature crape myrtles leads to expansive, meticulously landscaped grounds. Outdoor living takes center stage with sweeping wraparound decks, multiple gathering spaces, and a heated saltwater pool surrounded by travertine stone, gazebo, and fire features. An outdoor kitchen, complete with EVO grill, gas burners, refrigeration, and bar seating, creates the perfect setting for waterfront entertaining, while the year-round spa and low-maintenance turf with putting green enhance the ease of ownership. The private pier is a standout, offering multiple slips, lifts, floating dock access, and approximately 10 feet of water depth. An exceptional experience that is ideal for boating enthusiasts seeking effortless access to the Severn River and beyond. Inside, the main residence spans approximately 8,000 square feet, where refined finishes and architectural details are complemented by a light-filled, flowing layout. A grand foyer introduces the home, leading to elegant living and dining spaces, a chef’s kitchen equipped with premium appliances, and a welcoming sunroom overlooking the pool and waterfront. The main level Primary suite with private balcony, fireplace and spa-like bath is the perfect retreat after a day in the pool or on the water. A conveniently located elevator provides seamless access to all 3 levels. Designed for both relaxation and recreation, the lower level transforms into a true entertainment hub, featuring a nightclub-inspired lounge with full bar, a state-of-the-art theater, and dedicated fitness and recreation spaces. Head upstairs where an additional 3 bedrooms, 2 baths and an awe-inspiring office with wrap around deck offer comfort and flexibility for family and guests. A separate guest house offers additional accommodations with its own kitchen, living spaces, 3 bedrooms 2 baths and private comforts, an ideal retreat for extended stays or hosting with ease. Advanced infrastructure and smart home technology, including whole-house automation, security, generator, and climate systems, ensure modern convenience is fully integrated into this exceptional offering. The POD is more than a home, it is a private waterfront retreat designed for those who value space, privacy, and a seamless connection to the water. A truly resort-inspired setting, this property offers an unparalleled opportunity to experience the waterfront lifestyle in its most complete and effortless form. Welcome Home!

Easy living and a convenient Kent Island location come together at 233 Keenan Way, an end-unit townhome in the sought-after Ellendale community. Offering three finished levels, 1,884 square feet of living space and a two-car garage, this light-filled home features a flexible floor plan designed for everyday living. The main level is bright and open, with abundant natural light enhanced by the additional windows of an end-unit location. The spacious kitchen features tile flooring, ample cabinetry and counter space, and a large center island with seating. Open to the dining area and adjacent living room with LVP flooring, the layout creates an easy flow for everyday living and entertaining. Step outside to the rear deck for grilling, dining al fresco or simply relaxing at the end of the day. Upstairs, two generously sized bedrooms each feature a private ensuite bath, offering the flexibility of dual primary suites. New carpet adds a fresh update to the upper level. The entry level provides an additional bedroom or flexible bonus space ideal for guests, a home office, fitness room or second living area. Life at Ellendale extends beyond the home, with community amenities including an outdoor pool, clubhouse, tot lot, fishing pier, kayak storage, boat storage and walking paths, with sidewalks and streetlights throughout the neighborhood. Located just minutes from the Bay Bridge and convenient to shopping, dining and everyday necessities at Kent Landing, 233 Keenan Way offers a great combination of space, community amenities and easy access to Annapolis, Baltimore, Washington, D.C. and the Eastern Shore.

An extraordinary opportunity to reimagine one of Kent Island's most substantial waterfront estates. Set on approximately 20 private acres with 883 feet of shoreline along Cox Creek and views extending toward Eastern Bay, 450 Seascape offers the scale, privacy and waterfront setting to create something truly exceptional. The property is significant in every sense. The main residence encompasses over 12,000 square feet with seven bedrooms, multiple living and entertaining spaces, two offices and a private theater. A separate approximately 3,200 sq. ft. resort building features an indoor pool and expansive entertaining space, while more than 2,200 square feet of garage space provides exceptional room for vehicles, boats, equipment and storage. For the next owner, however, the real opportunity is the chance to take this remarkable collection of land, waterfront and improvements and make it entirely their own. The main residence was designed on a grand scale, with generous rooms, extensive glass and numerous spaces oriented toward the water. Multiple bedroom suites provide flexibility for family and guests. A large private office above the garage has its own entrance, abundant built-in storage and peaceful views across the property. Created for entertaining, the home also features a dedicated private theater with tiered seating, a 172 inch screen, surround sound, custom millwork and its own HVAC system. Throughout the residence, the sheer size and variety of spaces provide an exceptional canvas for a new owner to update, redesign and create a waterfront home tailored to the way they want to live. Separate from the main house, the resort building offers another dimension entirely. At its center is an indoor Gunite saltwater pool designed for year-round enjoyment, complemented by a large entertainment area with an extensive Viking equipped bar and kitchen, fireplace, full bath and laundry. A mezzanine overlooks the pool and opens to elevated outdoor entertaining areas with panoramic views across the property and water. Beyond the improvements, the setting is what makes 450 Seascape difficult to replicate. Approximately 20 acres provide remarkable privacy and room to create a waterfront compound, while 883 feet of shoreline establishes an extraordinary connection to the Chesapeake Bay landscape. A private pier puts Eastern Bay and some of the Chesapeake's most desirable destinations within easy reach. Cruise from your own backyard toward St. Michaels, Tilghman Island, Oxford and the Kent Narrows, or continue out onto the open waters of the Chesapeake Bay. 450 Seascape is not simply an opportunity to purchase a large waterfront home. It is an opportunity to take an estate of unusual scale; 20 acres, extensive shoreline, substantial existing improvements and exceptional boating access; and reinvent it for its next chapter. For the buyer with vision, the foundation is already here.

Steeped in history and surrounded by the timeless beauty of Maryland's Eastern Shore, 1130 Old Love Point Road presents a once-in-a-generation opportunity to own an extraordinary family farm in the heart of Kent Island. Spanning approximately 36.73 acres, this remarkable property blends agricultural heritage, historic character, and exceptional future potential in one of the Shore's most storied locations. At the center of the property sits an historic Victorian farmhouse dating to circa 1896, recognized by the Maryland Historical Trust as a historically contributing structure representative of the classic 19th-century Delmarva farmhouse. The home and grounds reflect generations of stewardship and offers tremendous opportunity for its next generation renovation, rehabilitation and future development prior to occupancy. Old Love Point Road itself carries a rich and fascinating history. Before the Chesapeake Bay Bridge connected Maryland to the Eastern Shore, Love Point served as one of the principal gateways to the Shore. Ferries, steamships, and rail lines once brought travelers from Baltimore and Annapolis to Kent Island, where they continued eastward across Maryland and Delaware. Love Point became known as a romantic waterfront destination and transportation hub, welcoming visitors arriving by ferry and the historic Queen Anne's Railroad. The property's location captures the spirit of that history while offering exceptional convenience to today's modern traveler. Situated just minutes from Route 50 and the Chesapeake Bay Bridge, the farm offers easy access to Annapolis, Washington D.C., Baltimore, and the Delaware beaches while maintaining the peaceful charm of Eastern Shore living. Currently farmed and designated as prime farmland, the property is ideally suited for a gentleman's farm, equestrian estate, vineyard, winery, agritourism venue, or luxury country retreat. The Development Analysis Report identifies a winery as one of the site's most favorable and viable uses, noting that agritourism operations such as vineyards and wineries are specifically encouraged within Queen Anne's County's future agricultural economy plans. In addition to its agricultural and lifestyle appeal, the property, perhaps most importantly, offers substantial long-term development potential. Located within the County's Suburban Estate zoning district and designated growth area, the site may support future residential subdivision opportunities, including large-lot estate development, clustered single-family communities, multifamily concepts, or additional residential lots under current moratorium guidelines. Whether envisioned as a private family compound, vineyard and winery destination, legacy investment, or future development opportunity, 1130 Old Love Point Road represents a rare chance to own a meaningful piece of Maryland's Eastern Shore history — where the past, present, and future converge along one of Kent Island's most iconic roads.

Welcome to 313 Thomas White Boulevard in the sought-after waterfront community of Gibson's Grant on Kent Island. This beautifully maintained Koch-built home offers more than 3,200 square feet of thoughtfully designed living space with four bedrooms, two-and-a-half baths, and a flexible floor plan tailored to today's lifestyle. The main level features hardwood flooring,crown molding and refined architectural details throughout, a main-level home office, and a spacious family room anchored by a cozy gas fireplace. The gourmet kitchen is designed for both everyday living and entertaining, showcasing granite countertops, rich mahogany cabinetry, stainless steel appliances, double wall ovens, a center island, pantry, and a sunny breakfast area. Upstairs, the spacious primary suite offers a walk-in closet and a luxurious en-suite bath with a soaking tub and separate shower, while three additional bedrooms provide plenty of room for family and guests. Above the garage, an expansive bonus room offers endless possibilities for recreation, work, fitness, or guest accommodations, making it one of the home's most versatile spaces. Relax on the welcoming front porch where you can enjoy the neighborhood's charming streetscape and peaceful surroundings, or unwind in the screened porch overlooking the fenced backyard, an inviting space for morning coffee, outdoor dining, or relaxing. A rear-entry two-car garage adds everyday convenience while preserving the home's classic curb appeal. Located in one of Kent Island's premier waterfront neighborhoods, Gibson's Grant offers exceptional resort-style amenities, including a community pool, clubhouse, fitness center, walking trails, kayak launch, fishing pier, pavilion, playgrounds, picnic areas, and water access to Macum Creek and the Chester River. Just minutes from Route 50 and the Chesapeake Bay Bridge, this home provides an easy commute to Annapolis, Baltimore, Washington, D.C., and Maryland's Eastern Shore while offering the relaxed coastal lifestyle that makes Kent Island so desirable.

Situated on one of the largest lots in sought-after Gibson’s Grant, this 4-bedroom, 3.5-bath home offers space, flexibility, and room to grow. High ceilings and an open layout create an airy feel, with an oversized kitchen flowing seamlessly into the family room and a separate main-level office for work or quiet retreat. The main level also features a formal dining room and living room. Upstairs, the spacious primary suite features a sitting area, two walk-in closets, and en-suite bath, alongside three additional bedrooms and two full bathrooms. The unfinished walkout basement includes a rough-in for a future bath. Outside, enjoy a fenced backyard complete with a patio and built-in fire pit—perfect for gathering year-round. Community amenities include swimming pool, clubhouse, fitness center, walking trails, community pier, picnic area, and kayak launch. Centrally located on Kent Island. Only 5 minutes to the Bay Bridge.

Historic Portland Manor – Allendale is privately set on 4.5 acres off sought-after Brooks Woods Road, surrounded by mature trees, neighboring acreage, and pastoral surroundings. A heritage tree-lined drive leads to the residence, framed by established landscaping, gorgeous brick walkways surrounding the home, landscape lighting, covered porches, and a renovated in-ground pool. Dating back to the late 1700s, with additions completed in the early 1800s, the home has been thoughtfully restored and updated while preserving its historic integrity and original craftsmanship. Offering an estimated 5,060 square feet, the property includes six bedrooms and four and a half baths across the main residence and separate in-law suite. Interior features include original heart pine flooring, restored historic windows, six fireplaces, a traditional central hall layout, three staircases, multiple gathering spaces, and extensive custom built-ins and storage throughout. The main level includes a formal dining room with marble fireplace and adjoining butler’s pantry, family room with restored marble fireplace, living room with fireplace and custom built-ins, greenhouse room, powder room, and multiple access points to the home’s covered porches and outdoor living spaces. The custom kitchen features extensive handmade cabinetry and tile work, custom shelving and pantry storage, soapstone and butcher block countertops, commercial-grade gas cooking with a double gas range, vent hood, griddle, separate service sink, and generous preparation space designed for entertaining and everyday functionality. A storage closet beneath the main staircase and extensive built-in cabinetry throughout the connecting gallery to the in-law suite provide exceptional functional storage rarely found in historic homes. The second level includes the primary suite with a large walk-in closet, private kitchenette, fireplace, and ensuite bath. Two additional bedrooms are located on this level, each featuring fireplaces, with one offering an ensuite bathroom. The third floor offers two additional bedrooms, a full bathroom, a large finished storage closet, and expansive attic storage space. The separate in-law suite, originally constructed in 1785, includes a living and dining area, kitchenette, full bathroom with private laundry, and an upper-level bedroom with vaulted A-frame ceiling. The residence includes eight exterior doors leading to approximately 1,000 square feet of covered brick porches, landscaped walkways, pool areas, and outdoor gathering spaces, creating a seamless connection between the home and grounds. Additional upgrades include fresh exterior paint on the entire home (2026), high-efficiency foam insulation in the attic, roof space, and crawlspace, and a comprehensive exterior restoration. The siding was removed and rebuilt with new Rockwool sidewall insulation, plywood sheathing, and infiltration fabric. Outdoor features include a fully renovated 20’ x 40’ pool (2025), pool house, custom fire pit patio with built-in seating, large deck with new decking (2025), fenced areas, extensive landscape lighting, and a custom Williamsburg-style chicken coop. Major system updates include two high-efficiency HVAC systems, plumbing system replaced in 2013, electrical systems and new 400-amp electric service was redone (2025). The exterior was fully repainted in 2026. A rare offering combining historic character, extensive restoration, privacy, acreage, and modern livability, conveniently located near The Cannon Club, local farmers markets, waterfront dining, and commuter routes. Two Tax IDs convey.

See listing MDTA2012146 which includes an adjacent 37+-acre waterfront parcel which has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. "Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 76+-acre waterfront estate has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

"Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 114+-acre waterfront estate with two deeded lots has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. The adjacent 37+-acre waterfront parcel (included in the total acreage) has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

"Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 114+-acre waterfront estate with two deeded lots has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. An adjacent 37+-acre waterfront parcel (included in the total acreage) has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

See listing MDTA2012146 which includes an adjacent 37+-acre waterfront parcel which has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. "Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 76+-acre waterfront estate has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

Architect-designed contemporary waterfront home on nearly 18 private acres across two parcels with approximately 1,400 feet of shoreline on Greenwood Creek. Positioned to capture 180-degree western views, the property offers privacy, deep water, and a setting that is increasingly difficult to find on Maryland’s Eastern Shore. A custom pivoting front door creates a striking first impression and sets the tone for the home's thoughtful design. The home was designed to take advantage of the surrounding water and landscape, with floor-to-ceiling windows, open gathering spaces, and strong indoor-outdoor connections throughout. The kitchen opens to the main living areas and features a glass accordion door that connects directly to the screened porch, creating a seamless transition between indoor and outdoor spaces. The layout flows easily between the kitchen, dining areas, family room, porch, and pool area, making the home equally well suited for everyday living and entertaining. The primary suite is set apart from the rest of the home by a glass-enclosed walkway and includes a private office, large dressing room, en-suite bath, and private porch access. In addition to the primary suite, the main level includes three additional bedrooms, each with access to a private bathroom. The finished lower level includes a home theater, billiards room, bar area, workout room, additional bedroom and full bathroom, along with unfinished basement space for storage. Outdoor features include a solar-heated pool, private beach, and deep-water pier with two boat lifts. The protected shoreline and direct access to Eastern Bay make this an ideal property for boating and waterfront living. A three-bay outbuilding with workshop space and additional storage provides room for equipment, hobbies, or car and boat storage. Located just outside Queenstown, the property is convenient to Easton, Annapolis, Washington D.C., Baltimore, and Philadelphia while offering the privacy and pace of the Eastern Shore.

New construction opportunity in Rock Hall with time to make it your own. The current plans feature a 1,650-square-foot ranch-style home with 3 bedrooms, 2 bathrooms, a front porch, and rear deck, all situated on a .79-acre lot within town limits. The open living areas include a large kitchen with white cabinetry, quartz countertops, stainless steel appliances, and upgraded LVP flooring that continues through the living and dining rooms. The primary bedroom features a walk-in closet and en-suite bathroom with dual vanity and shower. Two additional bedrooms have upgraded carpet and share a guest bathroom with a tub/shower. Additional features include an energy efficiency heat pump, a conditioned crawl space and public water and sewer. There is still time to select finishes and add your own personal touches. Buyers may also have the option to make changes to the current plans or choose a different style of home, subject to new permit approval. Located just two blocks from Rock Hall Harbor and close to Haven Harbour and Swan Creek, the property puts boating, marinas, restaurants, shops, and the waterfront all within easy reach. It’s a convenient in-town location for enjoying the laid-back, waterfront lifestyle that makes Rock Hall such a popular Eastern Shore destination.

This is more than a waterfront estate - it is an invitation to experience one of Maryland's Eastern Shore's most treasured lifestyles. Step from your private dock onto your boat, and within minutes, you will be cruising the scenic waters of the Wye River and Eastern Bay. Renowned for exceptional crabbing and fishing, the Wye River offers endless opportunities to pull crab pots, teach the kids to fish, or spend memorable days exploring the waterways. At home, your private beach provides the perfect setting for swimming, kayaking, relaxing along the shoreline, and gathering with family and friends to watch spectacular sunsets over the bay. The property's private lighthouse - a truly distinctive feature that conveys with the home - creates an unforgettable backdrop for entertaining, peaceful evenings, and panoramic water views. When it is time for dinner, shopping, or a change of scenery, historic St. Michaels is just a 10-minute boat ride away. One of the Eastern Shore's most beloved waterfront towns, it is known for award-winning restaurants, charming boutiques, picturesque marinas, and year-round events. Whether you are boating across the Wye River and Eastern Bay, enjoying world-class crabbing, fishing with the family, or ending the day with a sunset from your private beach or lighthouse, this property captures waterfront living at its finest - a rare Eastern Shore experience few homes can offer.

Welcome to 200 Wye Road, an exceptional waterfront estate set on over two private acres along the Wye River, directly across from the protected natural beauty of Wye Island. Here, scale, setting, and thoughtful design converge to create a truly elevated Eastern Shore lifestyle. Spanning more than 8,100 square feet across three finished levels, the residence offers a refined yet highly livable floor plan designed to capture water views from nearly every room. Expansive living spaces, a formal dining room with handpainted custom wallpaper from the U.K., and a reimagined gourmet kitchen create an environment equally suited for everyday living and large-scale entertaining. The kitchen has been thoughtfully redesigned with updated cabinetry, statement lighting, and a full suite of premium appliances, including Wolf, Sub-Zero, and Bosch. The home offers exceptional flexibility, including an optional first-floor primary suite, a dedicated home gym, two laundry rooms, and an oversized mudroom designed for seamless day-to-day living. Two wood-burning fireplaces add warmth and character, enhancing the home’s sense of comfort and timeless appeal. The primary suite serves as a private retreat, complete with two walk-in closets and a fully renovated, spa-inspired bath featuring heated flooring, a soaking tub, a glass-enclosed shower, and its own gas fireplace, delivering a level of comfort and detail rarely found. Since 2024, the property has undergone extensive upgrades that enhance both performance and long-term value, including a new Owens Corning roof with a transferable warranty, three fully replaced Trane HVAC systems, a whole-home water filtration system, and comprehensive renovations throughout the bathrooms and interior spaces. Outdoor living is where the property truly distinguishes itself. A newly renovated 20x40 waterfront pool with a pebble finish and automatic cover anchors the setting, complemented by expansive hardscaping, manicured grounds, and multiple areas designed for entertaining or quiet relaxation. The shoreline has been improved with 250 feet of stone rip rap, and the deep-water dock is outfitted with new electrical service and lighting, featuring a new 25,000 lb boat lift and a 12,000 lb one along with two additional slips, providing effortless access to the Wye River and beyond. Whether enjoying sunrise coffee on the screened porch, hosting summer gatherings by the pool, or heading out by boat to St. Michaels or the Kent Narrows, this property offers a lifestyle defined by ease, privacy, and connection to the water. Conveniently located in Queenstown, just minutes from shopping, dining, and Route 50, with easy access to Annapolis and Easton, 200 Wye Road represents a rare opportunity to own a turnkey waterfront estate in one of the Eastern Shore’s most sought-after settings.