luxury house with terrace for sale Chesapeake Beach, United States

Welcome to 4909 Olive Street, a newer construction three bedroom, two and a half bath home. Offering a functional layout, contemporary finishes, open living spaces, a fully fenced in backyard, and a private driveway. Enjoy access to a community beach, pier, kayak launch, waterfront park, playground, and picnic areas. Conveniently located near local marinas, waterfront dining, parks, and Chesapeake Bay attractions, with easy access to Annapolis, Edgewater, Washington, D.C., and Baltimore. A great opportunity to enjoy a water oriented lifestyle in one of Southern Anne Arundel County's popular waterfront communities.

Price reduced SIGNIFICANTLY!! Beautiful views of Harris Creek and the Choptank River beyond provide a stunning backdrop for this beautifully maintained home in the established community of Tilghman on Chesapeake. A welcoming front porch framed by mature landscaping and colorful gardens leads into a bright, light-filled interior featuring soaring two-story ceilings, hardwood floors, crown moldings, and abundant natural light. Designed for both everyday living and entertaining, the gourmet kitchen opens to a spacious family room with a gas fireplace, breakfast area, and inviting sunroom. The adjoining rear deck, complete with a hot tub, provides a wonderful setting for outdoor entertaining while overlooking the beautifully landscaped grounds and tranquil water views. The main level also includes gracious formal living and dining rooms, as well as a private office. The upper level overlooks the family room below and features a spacious primary suite with a private balcony and luxurious ensuite bath with a jetted tub and walk-in shower. Three additional bedrooms—one currently used as a library—share a full hall bath. An attached two-car garage provides convenient parking and storage. Residents of Tilghman on Chesapeake enjoy an exceptional array of amenities, including a waterfront clubhouse, swimming pool, picnic area, community pier, and private boat slips available for lease, offering residents an ideal opportunity to enjoy the waterfront lifestyle of Maryland’s Eastern Shore.

Enjoy the Chesapeake Bay lifestyle from this charming 2-bedroom, 3-bath cottage offering beautiful Bay views and direct access to the water just across the street. Situated on more than .6 acres, the property combines a relaxed coastal setting with a spacious, private backyard that is flat and ideal for outdoor living and entertaining. After a day on the water, unwind in the hot tub, rinse off in the outdoor shower, or simply enjoy the privacy of the backyard. A storage shed provides convenient space for kayaks, paddleboards, bikes, and other outdoor gear. Just across the street, direct access to the Chesapeake Bay and a sandy beach makes it easy to launch a kayak or paddleboard, spend the day along the shoreline, or simply take in the Bay. While the property is non-waterfront, the combination of water views and convenient Bay access offers an exceptional opportunity to enjoy the Eastern Shore lifestyle. Whether you're looking for a weekend getaway or a full-time Shore home, 101 Chesapeake Bay Drive offers an inviting retreat with space, privacy, water views, and the Chesapeake Bay just steps away.

For the first time in decades, this one of a kind property on Turkey Point Island 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 over 2,900 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 system, 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 (with fiberon composite deck boards) 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 with roughly 9' wide x 8' high garage doors 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. Island living at its best!

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!

Adorable waterfront cottage nestled along the peaceful shores of Hudson Creek., This charming 2-bedroom, 1-bath home features an open-concept kitchen, dining, and living area designed to maximize comfort and showcase beautiful waterfront views and amazing sunsets. Additional features include front and back porches, firepit, fresh paint throughout and a detached storage shed for all your outdoor gear, Experience Eastern Shore waterfront living and spend your days fishing or crabbing from your private pier, launch your kayaks for an afternoon on the creek, or simply unwind on the deck while taking in the spectacular sunsets. This low-maintenance property has been successfully operated as an income generating vacation rental, making it an excellent opportunity as a personal getaway, investment property, or both. The home is being sold fully furnished, including two kayaks, a BBQ grill and deck furniture

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

*OPEN HOUSE SAT & SUN with PRICE ADJUSTMENT TO SELL!* Come Take a look at this One Of A Kind property in the heart of the it All! Grab a Large Plot of Waterfront Land in Annapolis/Edgewater area! Incredible value on this newly updated 10.77-acre waterfront estate,with Picturesque Winter Water views, perfectly nestled on its own private peninsula on Beards Creek in Scotts Cove. Offering over 7,700 sq ft of finished living space, this unique 7-BR, 5-BA home is surrounded by 9.12 acres of wooded conservation easement, delivering extraordinary privacy with no HOA and flexible R-2 zoning.The expansive, versatile floor plan is optimized for multi-generational living or a high-yielding short-term rental-ideal for Navy families and students. Separate living zones include a main-floor bedroom with a full bath and a private side entrance, plus a flexible bonus wing (previously a media room/office) leading to a massive private deck.Premium Spring 2026 updates feature new CertainTeed Cedar Impressions siding in Coastal Grey, fresh Behr Cotton White interior paint, updated deck railings, and new sod/landscaping. Move-in ready with high-end mechanicals: private elevator (2022), 4 geothermal heat pumps (5 zones), tankless water heater, 3 steam showers, whole-house generator, and owned solar panels.Waterfront amenities include 665 ft of creek frontage, a private pier, and 2 boat lifts-perfect for kayaks and smaller watercraft. Unbeatable, secluded location just off Route 2 South with quick access to shopping, dining, Lee Airport, Route 50, Route 97, Annapolis, BWI, and Washington, D.C!

Welcome to the coveted South River Landing waterfront community, where sweeping views across the South River and a deeded boat slip at the community's deep-water marina offer an exceptional opportunity to embrace the Annapolis waterfront lifestyle. From spontaneous afternoons exploring the Chesapeake Bay to leisurely cruises along the river, life on the water becomes an effortless part of everyday living. Beautifully constructed, this impressive all-brick residence offers three finished levels, expansive outdoor living spaces, and walls of windows that capture the ever-changing waterfront scenery, creating a remarkable setting for both relaxation and entertaining. A grand entrance with an elegant curved staircase and impressive custom front door sets the tone for the spacious interiors. The main level is thoughtfully designed around the water views, with a beautifully appointed kitchen flowing seamlessly into the living room with fireplace and casual dining area. Whether gathering around the kitchen, hosting memorable dinners in the formal dining room with custom built-ins, or stepping outside to the sprawling waterside balcony, the South River provides a spectacular backdrop. Enjoy morning coffee as boats make their way along the river, spend the afternoon cruising from your own deeded slip, and return home to unwind as the evening light settles over the water. Two ensuite bedrooms and a powder room provide additional comfort and flexibility on this level. Upstairs, a spacious multi-purpose living area with fireplace and built-in entertainment center creates an inviting destination of its own. A full second kitchen makes entertaining effortless and offers wonderful flexibility for extended family or guests. A full bath with soaking tub and separate shower, powder room, and finished bonus room above the garage provide additional options for relaxing, working, or accommodating visitors. With generous spaces designed for gathering or retreating, the home easily adapts to everything from quiet weekends to extended stays with family and friends. The finished lower level offers another exceptional setting for entertaining and relaxation, with a recreation area centered around a fireplace, wet bar, beautifully designed wine cellar, and dedicated theater room. After a day spent boating, swimming, or exploring the waterways, return home for an evening of movies, conversation, and time together. An additional ensuite bedroom provides private guest accommodations, while an elevator connecting all three levels and laundry facilities on each floor add exceptional convenience to everyday living. Beyond the residence, the gated South River Landing community offers a lifestyle reminiscent of a private waterfront resort. Residents enjoy 24-hour staffed security, a waterfront swimming pool, deep-water marina, kayak launch, tennis courts, playground, basketball court, private beach, and scenic walking trails. The deeded boat slip is a particularly desirable feature, providing a dedicated place for your boat and convenient access to the South River, Chesapeake Bay, and the countless waterfront destinations that make this region so special. Whether heading out for a morning cruise, meeting friends at a favorite waterside restaurant, spending an afternoon kayaking, or simply relaxing by the community pool, every day presents another opportunity to appreciate life along the water. Combining the privacy and security of an established gated community with the freedom of having your boat just moments from home, this extraordinary property offers far more than beautiful waterfront views. It is an invitation to embrace a lifestyle defined by effortless boating, gracious entertaining, and the natural beauty of the Chesapeake Bay region. All just minutes from historic Annapolis, with convenient access to Washington, D.C. and Baltimore. Welcome Home!

Coastal charm and thoughtful craftsmanship come together in this beautifully renovated cottage in the sought-after Edgewater Beach community. Surrounded by mature trees, perfectly sited on a double lot and filled with natural light, the home offers a peaceful, private setting with seasonal glimpses of Beards Creek and conveniently located access path leading to the water’s edge. Inside, an open floor plan creates an inviting sense of space, enhanced by skylights and a classic brick fireplace with glass doors that adds warmth and character to the main living area. The beautifully renovated kitchen is both stylish and exceptionally functional, showcasing quality craftsmanship and thoughtful details throughout. A distinctive 12' long Bubinga wood live-edge countertop anchors the generous island with abundant seating, while two wall ovens, a built-in pantry, microwave, and ample storage make the space equally suited for everyday living and entertaining. Just outside the main living space, an expansive deck extends the home outdoors, creating a natural setting for dining, entertaining, or simply relaxing beneath the surrounding tree canopy. The seamless connection between indoors and out adds to the home’s relaxed feel and provides a peaceful backdrop throughout the seasons. Two bedrooms are located on the main level, one currently styled as an office, and share a beautifully renovated hall bath. Upstairs, the entire level is dedicated to a spacious and private primary suite. Tucked away from the main living spaces, this serene retreat features a walk-in closet and spa-like ensuite bath with a freestanding jetted tub and separate walk-in shower, creating a wonderful sense of privacy and escape. Located right at the edge of the property a serene path winds through the trees to the shoreline providing a wonderful spot to sit at the water's edge or launch a kayak. The Edgewater Beach community offers a boat ramp, boat slips, kayak storage, pavilion, playground, and additional amenities that make enjoying the South River lifestyle easy. Charming, beautifully updated, and rich with character, this special cottage combines thoughtful renovations, inviting indoor/outdoor living, privacy, and community water access in a peaceful coastal setting. Welcome Home!

Why wait to build when you can move right in? Welcome to 126 Stilly Way, a beautifully finished, nearly new home in Annapolis’ Parkside Preserve. Built in 2024 and offering more than 4,400 square feet of finished living space across three levels, this home combines the appeal of newer construction with the convenience of having the finishing touches already in place. The bright, open main level features a beautifully appointed kitchen with white cabinetry, quartz countertops, stainless steel appliances, gas cooking, double wall ovens, tiled backsplash, and an oversized center island. The kitchen flows seamlessly into the spacious family room, anchored by a gas fireplace with custom built-ins. A separate dining room provides additional space for entertaining. Upstairs, the primary suite features a tray ceiling, walk-in closets, and private bath with dual vanities, soaking tub, and oversized glass-enclosed shower. Three additional bedrooms each with their own walk-in closets and well-appointed baths complete the upper level. The finished lower level adds exceptional flexibility, with an expansive recreation area, wet bar with beverage refrigerator, full bath, and the potential to create a true fifth bedroom while still maintaining plenty of additional living and entertaining space. What truly sets this home apart is how much has already been done. Window treatments are installed, the lower level is finished, the yard is established, and the home is ready to enjoy from day one. Enjoy the benefits of a newer home without waiting on a construction timeline or tackling the many finishing touches that often come after settlement. A covered front porch, HardiePlank and brick exterior, level backyard, and attached two-car garage complete the property. Located just moments from Quiet Waters Park and convenient to Downtown Annapolis, shopping, dining, and major commuter routes, 126 Stilly Way offers the opportunity to enjoy newer construction with the added benefit of a home that is already finished, established, and truly move-in ready.

This over 5000 finished sq. ft. (public records is incorrect in Sq. Ft. listed) Dutch Craftsman with gorgeous front porch (10x43) welcomes you to this private 2 acre lot that is an entertainers dream. It has so many custom features and amenities you will be blown away. The main level is very open concept with bright kitchen with new leather granite and black stainless appliances, soaring ceilings in the huge great room with fireplace and oversized windows and the formal dining room is perfect for those huge dinner parties. The main level also offers a large owners suite and large private deck. New hardwood floors throughout kitchen, great room, foyer and dining room. The upper level has a very cool loft area overlooking great room, three large bedrooms and 2 full baths and a very large 2nd family room over the garage that is perfect for a huge home office or extra living space. But just wait until you see this lower level. Only one word describes it, WOW! It has tons of entertaining space with a custom wet bar, billiards area, theater room, cozy sitting area with pellet stove, guest room, full bath and workout/storage room. This lower level leads to my absolute favorite part, a custom patio/hot tub/ sauna and party space. This area even has its own full bath. It's really quite spectacular. Freshly painted throughout most of the home it is so fresh and ready for its new owners. The private lot at the end of a long driveway is rolling and beautiful with several flowering weeping willows, magnolias, dogwoods, rose bushes and more. This home also features a 2 car side entry garage and oversized driveway for many cars. Easy access to Rt. 50 but feels like you are in the country. 25min to BWI, DCA and 10 min to Annapolis.

NEW PRICE! Don't miss this opportunity to live on the water in a beautiful neighborhood! Tucked between the tranquil waters of Long Creek and Shipping Creek, this approximately 2,100 square-foot waterfront retreat offers a rare blend of mid-century charm and modern comfort. With two bedrooms, an office and three full bathrooms, there's plenty of space to live, relax, and host with ease. Originally built in 1977 and thoughtfully renovated in 2019, the home showcases timeless mid-century design - clean lines, an inviting flow, and character you can't replicate in new construction. A brand-new well pump (2025) adds peace of mind, ensuring reliable, efficient water service for years to come. The primary bedroom offers a true private retreat, while the additional bedrooms and full baths provide comfort and flexibility for family or guests. Throughout the home, updated finishes and smart design touches create a space that feels both stylish and easy to live in. Step outside and the real magic begins: your own private dock on Long Creek, with a mean depth of approximately 6 feet, ideal for kayaking, paddleboarding, fishing, or simply pulling up the boat after a day on the water. Enjoy the birds, sea life and mature landscaping from morning to night! This is more than a house - it's a lifestyle. Mid-century character, recent upgrades, and an unbeatable waterfront setting come together to create a truly special place to call home.

South River Waterfront! Discover an exceptional waterfront lifestyle in Port Isle, where beautiful water views, a private pier, and thoughtfully designed indoor and outdoor spaces come together in a setting made for boating, entertaining, and relaxed everyday living. A cart path through the backyard leads to the private pier, complete with low-maintenance composite decking, a 24,000-lb. boat lift, and floating dock offering effortless access for kayaks and paddleboards. A long driveway creates a sense of arrival and leads to the two-car garage. Inside, the light-filled foyer with vaulted ceiling opens to a comfortable living area before flowing into the heart of the home. The expansive kitchen is designed for gathering, with two generous islands, abundant cabinetry, and extensive counter space providing exceptional room for cooking and entertaining. An adjoining dining area connects seamlessly to the family room, where a fireplace anchors the space and doors open to the waterfront deck. Here, elevated views across the backyard toward the South River create a natural extension of the living space and an inviting backdrop for dining, entertaining, or simply unwinding at the end of the day. Upstairs, all three bedrooms feature vaulted ceilings and water views. The primary suite is a peaceful retreat with a private waterfront balcony and ensuite bath featuring dual sinks and a spacious walk-in shower with bench. Two additional bedrooms share a well-appointed hall bath with dual sinks. A conveniently located laundry room completes this level. The walk-out lower level expands the home's versatility with a spacious recreation room, fourth bedroom, full bath, and generous storage. The living area opens to an extensive screened porch overlooking the backyard and water, creating another exceptional space for entertaining and relaxing. Seasonal coverings allow the porch to be enjoyed well into the cooler months. With multiple outdoor living spaces, a private pier, boat lift, kayak launch, and direct access to the South River, every element invites you to embrace life on the water. A golf cart conveys with the property, making it easy to travel through the neighborhood and down to the water's edge. Whether heading out for a day of boating, launching a kayak, entertaining on the deck, or relaxing on the private balcony, this Port Isle waterfront retreat captures the ease and beauty of the waterfront lifestyle. Welcome Home!

Experience the Annapolis waterfront lifestyle from this charming A-frame cottage, where days on the water begin just steps from your door. Designed for relaxed coastal living, the 2-bedroom, 2-bath home features a light-filled, open interior with soaring vaulted ceilings and an inviting sense of space. Outside, the property becomes your private gateway to the South River. A private pier offers two deep-water slips, including one with a boat lift, while a dedicated kayak launch makes it effortless to explore the surrounding waterways. Bulkheaded shoreline, a storage shed, and ample outdoor space complete a setting designed for life along the Annapolis waterfront. Spend mornings enjoying coffee overlooking the water, afternoons boating, kayaking, or paddleboarding, and evenings unwinding on the South River as the sun sets across the waterfront. Whether you're searching for a full-time residence, weekend retreat, or Annapolis boating getaway, this is an opportunity to embrace a lifestyle centered around the Chesapeake Bay