luxury houses with pool for sale Stevensville, United States

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.

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. 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.

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.

Experience the best of Annapolis living in the sought-after, amenities-rich community of Fishing Creek Farm. Perfectly positioned to capture beautiful water views and surrounded by lush lawns and mature landscaping, this handsome brick-front Colonial offers a rare combination of timeless architecture, flexible living spaces, and an exceptional neighborhood lifestyle. A gracious foyer welcomes you into formal living and dining rooms designed for entertaining. At the heart of the home, the bright white kitchen features quartz countertops, abundant cabinetry, and a sunny breakfast nook that flows seamlessly into the impressive family room with soaring vaulted ceilings, a fireplace, and easy access to the patio and expansive backyard. Whether hosting summer gatherings or enjoying a quiet evening outdoors, the spacious front and rear yards provide room to relax, play, and take in the peaceful surroundings. Designed for both convenience and versatility, the main level includes a spacious primary suite, while a second upper-level primary suite enjoys sweeping water views and creates an ideal retreat for owners or guests. Two additional bedrooms share a well-appointed hall bath, providing ample space for family and friends. The partially finished lower level offers additional living space, generous storage, and easily accessible crawl spaces. Life in Fishing Creek Farm extends far beyond the property itself. Residents enjoy one of Annapolis' most coveted waterfront communities, complete with a community marina, swimming pool, sandy beach, tennis and pickleball courts, and year-round social activities. Located on the Annapolis Neck peninsula between the South River and the Chesapeake Bay, this special neighborhood offers a peaceful waterfront setting just minutes from downtown Annapolis, Eastport, and major commuting routes to Baltimore, BWI Airport, Fort Meade/NSA, Washington, D.C., and the Eastern Shore. A wonderful opportunity to enjoy the Chesapeake lifestyle in one of Annapolis' most desirable communities. Welcome Home!

For the first time in decades, this one of a kind Turkey Point property is being offered for sale by the original owners. With exceptional water views and access to the community’s many waterfront amenities, the home has been meticulously maintained and offers just under 2,800 square feet of finished living space across three levels. The main level offers a kitchen equipped with Bosch stainless steel appliances, dining room, bonus sitting room, an expansive living room with custom built ins, surround sound speakers, and a gas fireplace. Andersen windows are found throughout most of the home, along with hardwood flooring in many of the main living areas. Just off the living room is an incredible screened in porch with water views and opens to the rear deck.  The deck connects directly to the 24 foot round, 52 inch deep above ground pool, with additional water views from the deck and pool area. Additional storage can be found under the deck as well. Upstairs, you’ll find three bedrooms and two full baths. The primary suite includes an enhanced en suite bathroom and additional closet space. The finished walkout lower level provides another spacious gathering area with a family room and propane fireplace, along with a bedroom, full bath with stand up shower, and laundry. Direct walkout access leads to a private patio and backyard.  An oversized attached two-car garage provides significant and surprising additional storage and has been meticulously maintained. The property also includes a covered front porch, backyard shed and rear fenced in yard. The roof was replaced in 2016, the water heater in 2017, and the home is heated by a heat pump with oil backup. Life in Turkey Point is centered around the water. The community offers multiple beaches and water access points, a pier, walking paths, and Cloud Field with its playground and open green space. Boating, kayaking, paddleboarding, fishing, and crabbing are all part of the lifestyle here, with several marinas nearby and additional access to the Chesapeake Bay at Mayo Beach Park and Beverly Triton Nature Park. And while Turkey Point feels tucked away at the end of the peninsula, everyday shopping, restaurants, and the conveniences of Edgewater are still within easy reach, with Annapolis just beyond.  With water views, four bedrooms, three full and one half bathrooms, a finished walkout lower level, pool, and oversized two-car garage, 1117 Wilson Drive offers substantial living space and storage space with access to everything that makes Turkey Point such a distinctive Chesapeake Bay community.

Bay Ridge Waterfront! Built by Pilli Custom Homes and beautifully curated by Erin Paige Pitts Interiors, this exceptional waterfront residence blends timeless architecture, impeccable craftsmanship, and extraordinary attention to detail. Rich custom millwork, extensive crown molding, elegant wainscoting, and coffered ceilings create an atmosphere of refined luxury throughout. A welcoming bluestone walkway and front porch opens to the foyer, while a dramatic circular foyer at the foot of the staircase serves as the heart of the home, seamlessly connecting the formal dining room, elegant club room, and expansive kitchen and family room. Designed for effortless entertaining and everyday living, the chef's kitchen opens to the spacious family room featuring coffered ceilings and a striking fireplace. Just beyond, the waterside deck expands the living space with a swim spa, outdoor kitchen, and an exterior half bath, thoughtfully positioned so guests coming from boating, swimming, or relaxing by the water never need to enter the home. These exceptional amenities create the perfect setting for entertaining while embracing the waterfront lifestyle. Off the 2-car garage, the thoughtfully designed mudroom offers a built-in workspace, abundant storage, and a convenient powder room. A private main-level guest suite with an ensuite bath provides ideal accommodations for guests or multigenerational living. The upper level offers four spacious bedrooms, including two with private ensuite baths, while two additional bedrooms share a beautifully appointed bath. One bedroom has been transformed into a custom dressing room and can easily be converted back if desired. A large bonus room above the garage, complete with its own powder room, provides endless flexibility as a media room, playroom, home gym, or studio. The luxurious primary suite is a true retreat, featuring sweeping Lake Ogleton views from its wraparound balcony, a private office, spacious walk-in closet, and a spa-inspired bath with heated floors, soaking tub, oversized walk-in shower with built-in bench, and designer finishes. The top level is designed for entertaining with an expansive recreation room and a dramatic spiral staircase leading to one of the home's most remarkable features, a private rooftop deck perched among the highest elevations in Bay Ridge, offering breathtaking panoramic views and the perfect setting for morning coffee, sunset cocktails, or evening stargazing. Outside, the waterfront experience is equally impressive with a newly constructed pier featuring upgraded electrical service, LED lighting, three boat lifts, including an impressive 40,000-pound lift, and convenient waterside shed, providing exceptional accommodations for a variety of vessels and effortless access to the Chesapeake Bay. Bay Ridge offers an unmatched waterfront lifestyle with a community pool and clubhouse overlooking the Chesapeake Bay, sandy beaches on both the Bay and the river, a marina with a newly renovated clubhouse, playgrounds, basketball courts, ball fields, and miles of scenic waterfront roads for walking and biking. An active social calendar and year-round events make Bay Ridge one of Annapolis' most sought-after communities. Just minutes from Historic Downtown Annapolis and Eastport, enjoy award-winning restaurants, boutique shopping, marinas, and waterfront parks, with convenient access to Routes 50 and 97 for commuting to Baltimore, BWI Airport, Fort Meade/NSA, Washington, D.C., or Maryland's Eastern Shore. Welcome Home!

Welcome to this extraordinary waterfront estate, gracefully sited on 6.92 lush, landscaped acres with sweeping views of Leadenham Creek. Designed by architect Alan Meyers, constructed by Ilex Construction, and masterfully styled by interior designer Skip Sroka, this 10,000+/-sq. ft. residence is a showcase of timeless craftsmanship and elevated design. The custom brick exterior is crowned by a new cedar shake roof with copper caps and bands, creating a refined profile that blends seamlessly into the natural surroundings. Double mahogany doors with full-view, artistically designed leaded glass open to a luminous foyer with immediate, breathtaking views of the water. Inside, riff-sawn red oak floors flow through expansive formal and informal living areas. Vaulted ceilings add architectural drama, while curated lighting provides warmth and sophistication throughout. The main level features formal living and dining rooms, a stunning gourmet kitchen, and multiple spaces designed for both relaxation and entertaining. The kitchen is a chef’s dream—equipped with top-tier appliances, a large center island, sitting area with fireplace, and an eat-in dining space. Just off the kitchen, a beautifully crafted screened porch with an octagonal ceiling offers a peaceful, year-round retreat. A walk-in pantry and custom-designed bar enhance both function and hospitality. Also on the main level is a striking private office wrapped in Anigre wood paneling, featuring custom built-ins and a circular backlit ceiling. A separate guest wing includes a spacious family/recreation room with spectacular river views and two guest suites with ensuite baths. The primary suite enjoys its own private wing, with serene water views, a cozy sitting area and fireplace, dual walk-in closets, and an elegant dressing hall. The luxurious, spa-inspired bath includes a soaking tub and glass-enclosed shower, creating a true sanctuary of comfort and privacy. Upstairs, dual wings on opposite sides of the home offer two additional guest suites with ensuite baths, a bonus/music room, and a dedicated fitness room. Five fireplaces handcrafted by Collecio Brothers Stone Masons bring warmth and timeless character throughout the home. Modern systems include geothermal heating and cooling, a new Honeywell HVAC control system, Vantage lighting automation, a fully encapsulated crawlspace, and a Generac generator. In addition to the oversized 3+ car attached garage, a separate detached two-bay garage offers equipment storage, a workshop, and a half bath. Outdoors, the estate is designed for both grand entertaining and quiet waterfront living. Features include an extended waterside patio, beautiful pool house with a fully equipped outdoor kitchen, two dressing rooms, an outdoor shower, and an in-ground pool with heated spa. Over 1,000 feet of riprapped shoreline and a 210-foot private dock with two slips, a floating dock, and 7-foot MLW offer direct access to the Chesapeake Bay. This remarkable estate was built for luxurious living, effortless entertaining, and a deep connection to the natural beauty of Maryland’s Eastern Shore. *Current taxes are based on homestead credit.

Experience the quintessential coastal lifestyle in this historic gem, situated on one of the most sought-after streets in the St. Michaels historic district. Featuring timeless charm and character, this stately property perfectly blends classic architectural details (such as multiple built-ins and four working fireplaces) with modern convenience, all just a stone's throw from the town's vibrant harbor, boutique shops, and award-winning restaurants. Enter from the wide, covered front porch - ideal for morning coffee or greeting neighbors - into a grand, elongated foyer that sets a welcoming tone. The interior features gorgeous hardwood floors throughout, seamlessly connecting the bright living spaces. This home offers four spacious bedrooms, generously sized bathrooms, and ample storage, providing comfort for family and guests alike. The rear yard is a private retreat designed for both relaxation and entertaining. Tucked into the lush landscaping (which includes an in-ground irrigation system) is a fully finished, detached accessory building. This versatile, light-filled structure is perfect for a dedicated craft studio, hobby workshop, private home office, or fitness room. This property also includes rare, highly coveted off-street parking. Situated just steps from San Domingo creek and less than a block from Talbot Street, the house provides quick access to the waterfront park/kayak launch and the nature trail as well to the town's maritime attractions, local ice cream parlors, and fine dining. An 1850 historic treasure in a premier in-town location doesn't come along often-schedule your private tour today and make the magic of the Eastern Shore your reality.

PRICE IMPROVEMENT.... PRIVATE Estate Living Minutes from Historic St. Michaels... Escape to nearly twenty acres of unspoiled countryside just moments from the charm and waterfront allure of historic St. Michaels. This 4,492-square-foot home offers refined comfort with four bedrooms, two and a half baths, and a gourmet kitchen designed for both everyday living and effortless entertaining. A dedicated space for a future elevator adds thoughtful flexibility for years to come. Outside, the possibilities are as expansive as the land itself- 19.5 private acres with pastures suited for up to eleven Horses, plus a car barn for storage, hobbies, or collections. Agricultural and livestock production also permitted (buyers should confirm specifics with Easton P&Z). Notably, 5.75 wooded acres are enrolled in the DNR's Forest Stewardship Plan, preserving the agricultural tax discount without the requirement to grow crops or house livestock.

Waterfront Living Reimagined in San Domingo Cove! Coastal influences, exceptional craftsmanship and meticulous attention to detail define this immaculate custom waterfront home. Dramatic two-story family room, soaring ceilings, walls of windows and an open staircase with stainless steel cable railings create a striking architectural statement. The second-story catwalk and loft overlook the main living area, while expansive windows frame the pool and water views beyond. Designed for both everyday living and entertaining, the chef's kitchen features quartz countertops, stainless steel appliances and extensive soft-close cabinetry. An oversized island provides generous prep space and seating, while the bright eat-in dining area and separate beverage station offer exceptional space for casual dining and entertaining. Bamboo flooring extends throughout the living spaces, adding warmth and continuity to the home's contemporary coastal design. The thoughtfully designed floor plan includes a first-floor primary suite overlooking the pool and San Domingo Creek, two additional ensuite bedrooms and a spacious bonus room with a full bath, ideal as a guest suite, home office, studio, media room or fourth bedroom. Outside, beautifully landscaped grounds frame the waterside pool and expansive patio, while the shared private pier with a boat lift and floating dock provides easy access for boating, kayaking and paddleboarding. An oversized three-car garage offers ample space for vehicles, storage and recreational equipment. Located in desirable San Domingo Cove, the community enjoys protected natural open space, beautiful water features and immediate access to the St. Michaels Nature Trail. This distinctive property combines waterfront privacy with convenient access to the shops, restaurants, marinas and waterfront attractions of St. Michaels.

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.

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.

A truly exceptional waterfront offering, this is one of the finest opportunities to come to market on Glebe Bay. Set on a spectacular 1.71-acre point lot with more than 400 feet of pristine shoreline, this private estate enjoys panoramic water views, gentle topography, and an unparalleled setting at the end of a quiet cul-de-sac. Whether you're seeking an elegant waterfront home to enjoy immediately or envision transforming it into a custom luxury estate, this remarkable property offers endless possibilities. Lovingly maintained over the years, the residence is comfortable and full of character today, while also presenting an outstanding opportunity to renovate, update, or create a custom showcase that takes full advantage of its extraordinary setting. Designed for an exceptional waterfront lifestyle, the property features a private pier with boat and jet ski lifts, a waterside in-ground pool, and a screened porch that invites relaxed entertaining while overlooking Glebe Bay, a premier tributary of the South River. The existing home offers over three finished levels, including a desirable main-level primary suite, luxurious hardwood floors, four spacious bedrooms upstairs, and a fully finished walkout lower level with a full bath, ideal for guests, an au pair, or extended family. While the interiors reflect the current owner's distinctive style, the home's generous footprint provides an outstanding foundation for reimagining the space to today's luxury standards. A detached three-car garage with a full stand-up attic adds tremendous flexibility for storage, a studio, guest quarters, or future expansion. Properties with this combination of acreage, shoreline, privacy, and protected water are increasingly rare. This is a remarkable opportunity to create a legacy waterfront estate in one of Anne Arundel County's most coveted locations. Great value lies in this extraordinary homesite.

Experience one of the few Annapolis waterfront estates where you can leave your private dock and arrive at City Dock in minutes. Ideally situated on Spa Creek, this exceptional property captures the essence of Annapolis waterfront living with panoramic water views, unobstructed views of the Annapolis skyline, and endless opportunities for boating, kayaking, paddleboarding, and entertaining. Cruise by boat to downtown Annapolis, waterfront restaurants, ice cream shops, and the historic City Dock, or enjoy spectacular views of the Blue Angels, fireworks, and the annual boat parade from your own private retreat. Set within an exclusive enclave of only three prominent waterfront residences, this property offers a rare combination of privacy, convenience, and lifestyle. The waterside heated saltwater pool, expansive Ipe deck, and beautifully landscaped grounds create the perfect setting for entertaining family and friends. Host sunset dinners, summer gatherings, or relaxed afternoons outdoors while enjoying the water views and the sparkling lights of the Annapolis skyline. Surrounded by lush boxwoods and specimen plantings, the grounds provide a peaceful escape just minutes from downtown. Architecturally distinctive and thoughtfully updated, the residence combines refined design with comfortable waterfront living. Extensive renovations by Pyramid Builders showcase exceptional craftsmanship, including a dramatic marble foyer, floor-to-ceiling windows, solid wood doors, and rich stained black oak flooring. The gourmet kitchen features Sub-Zero refrigeration, a white six-burner Viking cooktop, high-gloss Premier cabinetry, Neolith porcelain countertops, designer lighting, and a striking floating staircase. A custom marble-topped bar provides an ideal space for entertaining. Offering 4-5 bedrooms, 5 full baths, and 1 half bath, including a desirable first-floor bedroom suite, the home provides flexibility for family and guests. A two-car garage, generous parking, and deep-water pier complete this exceptional Annapolis waterfront offering. This is more than a home-it is a rare opportunity to experience the very best of Annapolis living, where boating, entertaining, and downtown charm come together in one extraordinary setting.

A rare opportunity to own a fully metered triplex in the heart of Downtown Annapolis where historic charm, prime location, and remarkable versatility come together. Steeped in character and offering exceptional flexibility, this distinctive property presents an array of possibilities for both lifestyle and investment. With separately metered electricity, the property can be enjoyed as a multigenerational residence, with each family member having their own private space; an owner-occupied home with additional rental income from the remaining units; or a pure investment property with multiple income producing residences. For those envisioning something truly extraordinary, the entire building could be transformed back into a stunning single-family home. With original architecture and showcasing hardwood floors throughout, this property strikes the perfect balance between historic character and modern livability. The first floor features two bedrooms, each with an en-suite bath, kitchen, and living room, ideal for an owner-occupant or long-term tenant. The second floor offers one bedroom, a full bath, kitchen, living room, and access to a private balcony. The third floor impresses with two bedrooms, a full bath, kitchen, and living room, plus its own private balcony. An unfinished basement provides excellent storage space. A fenced backyard complete with a paver patio, provides an outdoor retreat ideal for relaxing or entertaining. Add to that the coveted off-street parking, a true rarity in Downtown Annapolis, and this property is as practical as it is beautiful. Whether you're an investor seeking immediate income potential, a buyer looking to offset your mortgage, or a multigenerational family wanting separate yet connected living spaces, this home checks every box. All of this just steps from the vibrant shops, restaurants, waterfront, and history that make Downtown Annapolis truly one of a kind.

A rare opportunity on Spa Creek, this fully reimagined Murray Hill residence offers an extraordinary waterfront lifestyle just moments from downtown Annapolis. Completed in late 2023 after a full ground-up rebuild, the home spans 5,900+ sq. ft. of impeccably crafted living space, where natural materials, refined architectural details, and top-tier systems create a seamless blend of comfort and sophistication. Set on just under a half acre of level waterfront, the property showcases one of the most complete private pier systems in the area: a heavily built main pier, two floating docks, and three boat lifts (16,000lb, 8,000lb, and 2,500lb), plus lighting, water, 30/50-amp shore power, Tide Slide moorings, and 6' MLW at the 70' T-head. A charming boathouse and waterside deck capture the magic of Spa Creek from morning to sunset. Outdoor living is exceptional. A stunning 40' x 20' PebbleTec saltwater pool—rebuilt in 2024—anchors a series of Ipe decks and natural stone patios and decks designed for effortless entertaining. The outdoor kitchen with piped natural gas grill, refrigerator, and sink extends gatherings well into the warm months, while covered and uncovered spaces offer year-round enjoyment. The exterior speaks to enduring quality with Carderock stone foundations, mahogany trim and ceilings, Loewen windows, Canadian cedar siding, copper gutters and flashings, and custom mahogany entry doors. A detached heated and cooled two-car garage includes a beautifully finished upper level with kitchenette, laundry, living/sleeping area, and private bath—ideal for guests or an au pair. Inside, the home is defined by warm natural luxury featuring a stunning barrel vaulted mahogany ceiling with cove lighting. Additional curated details include: mahogany doors, black bronze hardware, 5" Cumaru flooring, custom cabinetry, and extensive millwork throughout. The chef’s kitchen features Sub-Zero and Wolf appliances with granite and soapstone surfaces. The main level Primary suite with inspiring view of pool and waterfront provides convenience and options for aging in place. The lower-level recreation spaces provide a relaxed retreat with a private bedroom suite, family room, wet bar, gym and full laundry room. An abundance of thoughtful design is presented throughout the home with multiple wet bars, radiant heated tile floors in five bathrooms and the main-level bar, and four separate laundry areas. Less than half a mile from Church Circle, this residence delivers the rare ability to live on the water while enjoying the full walk-everywhere lifestyle of historic Annapolis. This is Spa Creek living at its finest: sophisticated, effortless, and undeniably special. Welcome Home!

Experience the best of the Annapolis lifestyle at 1610 Ridout Road, where beautifully updated interiors, exceptional outdoor living, and coveted water access come together in one inviting home. Inside, an open and comfortable floor plan is designed for the way people actually live. The kitchen opens to a sun-filled bar and dining area, where a sliding door provides direct access to the backyard and creates an easy connection between indoor and outdoor living. Two gas fireplaces, one in the living room and another in the family room, bring warmth and character to the main level, while the finished lower level provides additional flexible living space and storage. Upstairs, the spacious primary suite with an ensuite bath and three additional bedrooms sharing a full hall bath, offer comfortable space for family and guests. An attached two-car garage completes the home’s practical conveniences. Outside is where this property truly distinguishes itself. Framed by lush landscaping, the expansive, fully fenced backyard unfolds as a series of thoughtfully created outdoor living spaces. The heated in-ground pool, hot tub, generous patio space, and pergola-covered dining area area designed for long summer days and effortless entertaining, while the broad lawn offers plenty of room to play, garden, or simply unwind. And the lifestyle extends well beyond the property line. Amberley is one of the Broadneck Peninsula’s sought-after water-privileged communities, with three private community piers along Whitehall and Ridout Creeks and 45 slips accommodating both power and sailboats. Residents also enjoy a boat ramp, kayak and paddleboard storage, and a launch pier for smaller watercraft. More than 15 acres of community forest and open space, along with over 3 miles of paved roads and walking trails, contribute to Amberley’s peaceful, established character. Just minutes from Downtown Annapolis, Broadneck schools, and convenient routes to Washington, D.C., Baltimore, and the Eastern Shore, this private oasis offers something increasingly difficult to find: space to spread out, a backyard built for living, and easy access to the Chesapeake Bay lifestyle.

This move in ready five bedroom, two and a half bath home sits on a private lot in southern Anne Arundel County, with the space, updates, and outdoor living that today's buyers are prioritizing. Inside, the kitchen, bathrooms, living areas, and bedrooms have all been enhanced in 2026 with fresh paint, flooring, cabinetry, countertops, and more. The primary suite includes a walk-in closet and an en suite bath with a soaking tub, stand up shower, and double sink vanity, all overlooking the in ground pool below. The finished walkout basement adds a large family room and a bonus room with a window, well suited to a home office, gym, or guest space. Outside is where the property earns its keep: a covered front porch, a screened in back porch, extensive hardscaping, an in-ground pool with a storage shed, and private walking trails through the wooded backyard. It's a layout built for entertaining as much as for quiet mornings with coffee. The driveway offers ample parking for guests connecting to a two car garage. Tracys Landing puts you minutes from marinas, waterfront dining, and Chesapeake Bay access, with Annapolis, Washington, D.C., and Northern Virginia all within reach.

Discover the pinnacle of contemporary waterfront living in this extraordinary new construction residence by Cypress Homes, perfectly sited on a spectacular peninsula along the picturesque Little Magothy River. Surrounded by water on two sides and offering a rare 525 feet of waterfrontage, this remarkable property captures sweeping panoramic views extending across the Magothy River to the Chesapeake Bay beyond. This custom crafted luxury home offers an exceptional blend of refined craftsmanship, timeless elegance, and an unparalleled waterfront lifestyle. Located within the highly acclaimed Blue Ribbon Broadneck School District and just minutes from downtown Annapolis, Severna Park, Baltimore, Washington, D.C., and BWI Airport, this residence offers the perfect balance of peaceful waterfront living and everyday convenience. Designed with meticulous attention to detail, every space has been thoughtfully curated to capture the spectacular water views while offering exceptional comfort for everyday living and entertaining. The dramatic foyer immediately impresses with a stunning floor to ceiling glass wine cellar before opening to expansive living spaces where walls of glass frame the shimmering waters of the river and pool beyond. The open concept design seamlessly connects the living room with fireplace and wet bar, an elegant dining area, and a gourmet chef's kitchen featuring premium appliances, custom cabinetry, and sleek designer finishes. A private main level bedroom with an ensuite bath provides ideal accommodations for guests, extended family, or a dedicated home office. An architectural open tread staircase leads to the upper level, where four additional bedrooms and three beautifully appointed baths await. The primary suite is a true waterfront sanctuary, offering breathtaking views, a private balcony overlooking the heated saltwater pool, a spa style bath, and generous walk in closets. An additional ensuite bedroom and two spacious bedrooms connected by a shared bath provide flexibility for family and guests, while the expansive bonus room above the garage is ideal as a media room, playroom, fitness studio, or additional guest retreat. Step outside to experience a waterfront setting few can rival. Whether relaxing beside the heated saltwater pool, entertaining along the water's edge, or enjoying the serenity afforded by this rare peninsula setting, the connection to the water is ever present. Launch a kayak or paddleboard from your private pier, spend the day crabbing and fishing, or cruise the protected waters of the Little Magothy River before venturing out for endless boating adventures. Offering the rare combination of new construction, 525 feet of waterfrontage, a peninsula setting with water on two sides, luxurious finishes, panoramic water views, and an unbeatable location, this is a home designed to be enjoyed for generations. A truly remarkable opportunity to experience one of Annapolis' most extraordinary waterfront estates. Welcome home!

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

A masterpiece of Eastern Shore living, this Tidewater colonial estate is set against sweeping, panoramic views where the Choptank River, Chesapeake Bay, and three creeks converge. Showcasing breathtaking sunsets, the private oasis features a waterside pool, a main floor primary suite built in 2023, rich hardwood floors, and a detached 3-car garage. Tucked away in the desirable Ferry Neck enclave of Royal Oak, this estate offers the ultimate waterfront lifestyle. As you approach via tree-lined W. Ferry Neck Road, you enter Tranquility and are greeted by a circular driveway, mature landscaping, and a profound sense of privacy. Designed for classic Eastern Shore comfort, Tranquility offers impressive water perspectives from every room. The Main Level features gleaming hardwood floors, formal living room and dining room, gourmet kitchen with walk-in pantry, screened porch, sunroom, two wood-burning fireplaces, and two convenient powder rooms. The spectacular first-floor primary suite offers an exceptional private sanctuary. The Second Level boasts three well-appointed, ensuite bedrooms, ensuring privacy and comfort for family and guests. Structural Updates: The home also features a brand-new roof installed in 2023. Beyond the main residence, the 3-car detached garage ideal for car enthusiasts has an upper level that presently serves as an office and a substantial storage room. Tranquility truly provides the best of both worlds. For just under three acres, the property's privacy is unmatched. The endless water views , the close proximity to the sandy bottom shore, the pier with water, electric, and boat lift, all contribute to the perfect retreat. Furthermore, the convenience to Oxford by boat or the Bellevue Ferry, as well as a 15-minute car ride to both Easton and St. Michaels, define the perfect Talbot County location.