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Annapolis

One of the most popular communities provided by Maryland Sandbox

Annapolis

About Annapolis

Nestled on the shores of the Chesapeake Bay, Annapolis, Maryland, is a charming and historic community that seamlessly blends waterfront beauty with rich maritime heritage. As the state capital and home to the United States Naval Academy, Annapolis boasts a vibrant downtown area filled with unique shops, gourmet restaurants, and stunning colonial architecture. Residents and visitors alike can enjoy picturesque strolls along the scenic harbor, where sailboats and yachts bob in the water. With its engaging cultural scene, including art galleries, theaters, and annual festivals, Annapolis offers a lively atmosphere for all ages. The community takes pride in its top-rated schools, making it an ideal place for families. Outdoor enthusiasts can explore numerous parks, nature trails, and waterfront activities, while history buffs can immerse themselves in the city's storied past at landmarks such as the Maryland State House. Whether you're seeking a lively urban environment or a peaceful retreat by the bay, Annapolis is a vibrant community that truly has something for everyone.
One of the most popular communities provided by Maryland Sandbox
276
# of Listings
3
Avg # of Bedrooms
$515
Avg. $ / Sq.Ft.
$1,434,627
Med. List Price

Browse Annapolis Real Estate Listings

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Over $5M

14 Properties Found. Page 1 of 1.

Imagine arriving home each day to a place where the pace slows, the views stretch for miles, and every amenity for recreation, relaxation, and entertaining is right outside your door. Tucked away along the Chesapeake Bay, this extraordinary waterfront retreat offers a lifestyle that few properties can match, a private oasis where luxury and nature exist in perfect balance. Originally constructed by the renowned Pyramid Builders and later transformed through an extraordinary $7 million top-to-bottom renovation, also completed by Pyramid Builders, the estate has been reimagined to an uncompromising standard. Every space, finish, and amenity was thoughtfully designed and curated to create a residence that is as functional as it is beautiful, blending timeless craftsmanship with modern luxury. State of the art features include the Crestron Home Automation and integrated Lutron lighting systems while the modern luxuries entail top of the line Miele appliances including a built-in coffee maker, microwave and convection oven, BlueStar range, radiant heated floors in all bedroom bathrooms and much more. Here, days can begin with coffee overlooking the pond and its abundant wildlife, followed by a swim in the heated saltwater pool, a match on the tennis or pickleball court, a workout in the gym, or a stroll down to the sandy beach. Evenings are spent gathered with family and friends around the pool and hot tub, watching the game on the hydraulic television that rises from the landscape, enjoying a glass of wine from the tasting room, or simply taking in the stars above the Bay. The ever-changing waterfront scenery, southern exposure, and remarkable sense of privacy create a backdrop that feels more like a luxury resort than a private residence. Designed for those who believe home should be a destination, the property offers an incredible collection of indoor and outdoor amenities rarely found in a single estate. Tennis, pickleball, basketball, a climbing wall, playground, in-ground trampoline, expansive lawns, sandy beach, pond with fountain, indoor racquetball court with basketball and volleyball capabilities, golf simulator, game room, fitness center, indoor lap pool, infrared sauna, wine tasting and cellar area, and countless spaces to gather ensure there is always something to enjoy for every generation. The residence itself is beautifully designed and thoughtfully appointed, with spacious living and entertaining areas, a wraparound screened porch that embraces the waterfront setting, private ensuite bedrooms throughout, and a dedicated guest or in-law suite that welcomes family and friends in comfort and style. Abundant storage, an attached two-car garage, and a detached garage with additional space for vehicles, golf carts, recreational equipment, and storage provide the functionality expected of a property of this caliber. What makes this estate truly special is not simply the remarkable list of amenities—it is the feeling it creates. The extraordinary combination of peace, beauty, privacy, and convenience is increasingly difficult to find. Just minutes from Annapolis, yet seemingly a world away, this is the kind of property where children spend their days outdoors, guests never want to leave, and every sunset reminds you why you chose to call it home. A rare opportunity to own a true Chesapeake Bay waterfront compound where every day feels like a vacation, every detail has been thoughtfully considered, and the lifestyle is every bit as exceptional as the home itself. Welcome Home!
#MDAA2147500

ANNAPOLIS

2045 MAIDSTONE FARM ROAD

6 Beds

7 Baths

15,859 Sq.Ft.

$12,950,000

MLS#: MDAA2147500

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!
#MDAA2143556

ANNAPOLIS

5 FRANKLIN STREET

5 Beds

6 Baths

5,993 Sq.Ft.

$12,500,000

MLS#: MDAA2143556

Absolutely one of the finest waterfront offerings in the City of Annapolis. Ideally situated on Spa Creek, this exceptional property boasts sweeping water views and showcases the Annapolis skyline, creating a waterfront lifestyle with a myriad of opportunities for boating, kayaking, and entertaining. Enjoy direct water access with the ability to travel by boat to City Dock, local restaurants, and ice cream destinations—an unmatched Annapolis waterfront lifestyle. A prime vantage point for the Blue Angels, fireworks, and the annual boat parade further confirms the setting. Set within an exclusive enclave of three prominent homes, the residence features a waterside heated saltwater pool, deep-water pier, and a spacious Ipe deck designed for outdoor living. The grounds are beautifully landscaped with lush boxwoods and specimen plantings, creating a private and serene setting. Architecturally distinctive and extensively updated, the home showcases high-end renovations by Pyramid Builders. A dramatic marble foyer, floor-to-ceiling windows, and solid wood doors enhance the home’s refined design. The gourmet kitchen is top-of-the-line, featuring Sub-Zero refrigeration, a white 6-burner Viking cooktop, high-gloss Premier cabinetry, Neolith porcelain countertops known for their heat and stain resistance, designer lighting, and a striking floating staircase. A custom bar with a marble countertop is perfectly positioned for entertaining. Offering 4–5 bedrooms, 5 full and 1 half baths, including a desirable first-floor bedroom, the home also features stained black oak flooring throughout. A two-car garage with ample driveway parking provides convenience for residents and guests alike.
#MDAA2143164

ANNAPOLIS

8 SPA VIEW CIRCLE

5 Beds

5 Baths

6,061 Sq.Ft.

$11,500,000

MLS#: MDAA2143164

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!
#MDAA2145202

ANNAPOLIS

3344 HARNESS CREEK ROAD

4 Beds

4 Baths

8,264 Sq.Ft.

$10,850,000

MLS#: MDAA2145202

Located on a private 2.5-acre lot in Wimbledon Farms, this waterfront estate home, designed by Cathy Purple Cherry and constructed by West River Builders, is truly a masterpiece in design and quality. The 3-level home – complete with elevator -- takes full advantage of its waterfront setting that includes 400 ft of shoreline. Facing Quiet Waters Park, the ever-changing view includes brilliant fall foliage, deer by the water’s edge, and osprey circling overhead. Stroll down to the 100 ft private pier with deep-water slips. There’s 7 ft water depth at the dock; Harness Creek is a recognized hurricane hole so this is the perfect spot for boats to ride out a storm. The 20 ft x 40 ft saltwater pool has a spacious ipe deck and two Hanso pergolas provide shade with wonderful water views. Six bedrooms, each with a private ensuite bath, a gourmet kitchen, and wrap-around screen porches and decks provide space for both casual living and grand entertaining. Upon entering, there is a gracious paneled foyer that opens to the living room. With Brazilian cherry floors, a gas fireplace with marble surround, and built-in bookcases, this room has fabulous water views and opens to one of the screened porches on this level that invite outdoor living. To the right is the heart of the home – the great room. It includes a just remodeled chef’s kitchen with multiple work areas, a family room, and the dining area. The kitchen includes Taj Mahal leathered countertops, two wall ovens, two Bosch dishwashers, a warming drawer, instant hot dispenser, Wolf 5-burner gas cooktop, and KitchenAid side-by-side refrigerator. There’s also a wet bar with beverage cooler. The family room has a wood-burning fireplace with raised hearth and stone surround; there’s also a spacious workspace with built-in bookshelves. The dining area overlooks the water, and there’s access to both screened porches. The main level also features a fabulous guest suite: there is a large bedroom with water views, walk-in closet, and a private bath with radiant heated floor. In addition, there are two powder rooms and a mudroom with three closets and an abundance of storage space. The main level has 10 ft ceilings and 8 ft interior doors. Upstairs, the primary suite is an owner’s dream escape. There’s a spacious bedroom with water views, dark cherry floors and a gas fireplace. The study, with wet bar, built-in shelves and file drawers, leads to a small reading room – with water views. The spa-like bathroom, with radiant heated floor, includes a separate water closet room, jetted tub with marble surround, oversized steam shower, and separate vanities. Step onto the private screened porch to enjoy a cup of coffee in the morning. The primary suite also includes two large walk-in closets and a laundry room. There are three additional water view bedrooms on the second floor, each with private bathroom and walk-in closet. The main laundry is in a dedicated room with ample storage. There’s also a walk-in cedar closet. All of the bedrooms and closets that have carpeting were re-carpeted in 2026. The walk-out lower level has a huge game room that includes a big screen TV, wet bar, and full bathroom. From here, you can step out to the bluestone patio that leads up to the pool. There is a half-bath off the patio, accessible for pool visitors. The 6th bedroom with ensuite bathroom also has peaceful views, and multiple closets. The main utility room houses the commercial grade water treatment system. It has a garage door for easy access to boat supplies and equipment servicing. A secondary utility room houses the elevator mechanism and reverse osmosis treatment system. A third unfinished area has the camera and internet systems. This exceptional home offers sophisticated waterfront living just minutes from the heart of Annapolis and the Chesapeake Bay. The year-round beauty of this scenic setting and unrivaled design is truly unsurpassed!
#MDAA2142870

ANNAPOLIS

3285 HARNESS CREEK ROAD

6 Beds

7 Baths

10,745 Sq.Ft.

$10,500,000

MLS#: MDAA2142870

Commanding extraordinary panoramic Chesapeake Bay views from its spectacular south-facing setting, this exceptional waterfront estate offers 210 feet of shoreline on 3.10 private acres in the exclusive Maidstone Farm community. From magnificent sunrises over the water to vivid evening sunsets, the property was thoughtfully designed to maximize its breathtaking waterfront setting, with sweeping, unobstructed water views showcased from nearly every principal room. A private pier on the protected waters of Burley Creek with 6–7 feet MLW measures 34 ft .x 15 ft. with a 10,000 lb lift provides effortless access to the Chesapeake Bay, while the gentle shoreline also offers the ideal setting to launch kayaks and paddleboards directly from the property. The expansive, level lawn creates an exceptional setting for waterfront entertaining, wedding tents, outdoor recreation, or simply enjoying the serenity of the shoreline. Designed by ABS Architects and custom built in 2019, the residence masterfully blends timeless coastal architecture with sophisticated craftsmanship and modern luxury. Encompassing gracious open living spaces with exceptional natural light, the home features five ensuite bedrooms, 6 full and 1 half baths, four fireplaces (including two propane), extensive custom built-ins, and seamless indoor-outdoor flow to covered porches and waterside verandas. Nearly every gathering space was thoughtfully designed to embrace the stunning waterfront backdrop. A dramatic staircase introduces interiors defined by coffered ceilings, crown moldings throughout the first and second floors, 10-foot ceilings on the main level, 9-foot ceilings on the upper and lower levels, 8-foot solid wood doors, 8-inch baseboards, and designer lighting. Framed access for a future elevator provides additional convenience. The gourmet kitchen was designed for both grand entertaining and everyday living, anchored by two oversized islands, opposing Eucalyptus cabinetry and appointed with a La Cornue range and oven, two Sub-Zero refrigerators, Sub-Zero refrigerator drawers, premium hardware, and striking mitered-edge countertops. Open sightlines connect the kitchen to spacious dining and living areas, all enhanced by expansive water views. The luxurious primary suite serves as a private waterfront retreat, complete with a barrel vaulted ceiling, sitting room, oversized walk-in closet, and sweeping Chesapeake Bay vistas. Each additional ensuite bedroom features custom tile work, designer fixtures, and refined finishes. Above the extra-deep four-car garage, a substantial flex space with a full bath and exercise room offers ideal accommodations for guests, a private office, studio, or additional living suite. The unfinished lower level spans approximately 3,664 square feet, presenting endless possibilities for future recreation, wellness, or storage spaces. Additional highlights include a waterside heated, saltwater pool, circular driveway with extensive parking, six-zone HVAC system with gas backup and humidifiers, spray foam insulation, 400-amp electrical service, Kohler propane-powered whole-house generator with a 2,000-gallon tank, comprehensive alarm and security system, and whole-house Control4 audio and lighting automation. Located just moments from downtown Annapolis, City Dock, fine dining, shopping, and cultural attractions, this remarkable property presents a rare opportunity to own a thoughtfully designed luxury waterfront estate offering exceptional privacy, premier boating access, expansive entertaining spaces, and extraordinary Chesapeake Bay views at every turn.
#MDAA2130456

ANNAPOLIS

2035 MAIDSTONE FARM ROAD

5 Beds

6 Baths

7,105 Sq.Ft.

$8,750,000

MLS#: MDAA2130456

Perfectly positioned along the waterfront in the prestigious Murray Hill neighborhood of Annapolis, this extraordinary estate represents a rare opportunity to own a fully reimagined luxury residence where privacy, walkability, boating lifestyle, and architectural sophistication converge in one of the East Coast’s most coveted waterfront settings. RenownedBohan Contracting has been extensively renovating the home since October 2025. The home has not been lived in since completion, offering an exceptionally rare “like-new” experience where every finish, appliance, system, and curated detail remains untouched. Set on an unusually expansive waterfront lot for downtown Annapolis standards, the property delivers a sense of scale and privacy that is nearly impossible to replicate within Murray Hill. Mature landscaping, multiple outdoor living spaces, Brazilian Ipe decking, and panoramic water views create a setting that feels worlds away while remaining just moments from the energy and charm of downtown Annapolis. Designed for the discerning buyer seeking a refined waterfront retreat, the residence effortlessly balances elevated entertaining with relaxed coastal living. Whether arriving by boat after a day on the Chesapeake Bay, hosting sunset gatherings overlooking Spa Creek, or enjoying peaceful mornings watching sailboats drift by, the home was designed around an experience. Inside, timeless design and modern luxury unfold at every turn. The fully reimagined chef’s kitchen rivals those found in premier custom estates, anchored by a complete JennAir Noir appliance suite including a 48-inch dual-fuel range with double ovens, professional refrigeration, dual integrated dishwashers, multiple beverage centers, built-in ice maker, and a butler's pantry designed as both a prep and entertaining space. Custom Schrock “Trademark” maple cabinetry, designer-selected Waterworks fixtures, Calacatta Miraggio Cielo quartz with dramatic waterfall detailing, and layered architectural lighting elevate the space into a true showpiece. Throughout the residence, every finish was intentionally selected to create warmth, sophistication, and understated luxury. Wide-plank white oak flooring, custom white oak ceiling beams, Restoration Hardware lighting, Baldwin hardware, integrated Sonos audio throughout the home, Lutron lighting controls, custom plaster fireplaces, upgraded insulation for sound attenuation, and CAT6 wiring provide the seamless blend of craftsmanship and modern infrastructure expected at this caliber of home. The primary suite serves as a private sanctuary, complete with custom built-ins, boutique-style California Closets systems, integrated laundry, and a bespoke fireplace designed to create an atmosphere reminiscent of a luxury waterfront hotel suite. Every secondary space continues the same level of thoughtful execution and design continuity rarely achieved in residential renovations. Outside, the waterfront experience becomes truly exceptional. A private pier with electric, boat lift, paver stone extended driveway, refinished gates, and oversized outdoor entertaining areas creates a lifestyle tailored for effortless luxury. The property’s unique positioning offers both protected water access and breathtaking views while maintaining an uncommon sense of seclusion in the heart of Annapolis. Located just minutes from Downtown Annapolis, the United States Naval Academy, award-winning restaurants, yacht clubs, boutique shopping, and private aviation access, this home is ideally suited for the executive or entrepreneur seeking an uncompromising second home or primary waterfront residence within easy reach of Washington D.C., Northern Virginia, Philadelphia, and New York. The ability to enjoy a true luxury waterfront lifestyle with boating access, walkability, privacy, and substantial land all within one of Annapolis’ most prestigious neighborhoods is extraordinarily rare.
#MDAA2144478

ANNAPOLIS

11 S ACTON PLACE

4 Beds

3 Baths

3,658 Sq.Ft.

$7,999,000

MLS#: MDAA2144478

This Severn River estate is a rare opportunity to own one of the area’s most spectacular properties. Showcasing a negative-edge pool with beach entry and hot tub, 2 private piers to accommodate a variety of vessel sizes including a 100 ft slip, sprawling yard and sweeping views of the river and Naval Academy Bridge. Imagine waking each morning to the sun sparkling off the Severn, its reflection dancing across the water and spilling into a home designed to embrace the view at every turn. This extraordinary residence is both a private retreat and an entertainer’s dream, with expansive balconies and roof decks on every level, making indoor/outdoor living a breeze. Inside, soaring ceilings and walls of glass frame the ever-changing views like a living masterpiece, while the grand chef’s kitchen, stone-floored sunroom, and elegant dining spaces invite gatherings large and small. The primary suite is an entire level of indulgence, complete with soaring ceilings, a fireplace, spa-like bath, wet bar, expansive dressing room, laundry, and its own private balcony for starlit evenings. Additional ensuite bedrooms and a guest suite with kitchenette ensure comfort for family and friends, while the lower level—with wine cellar, kitchenette, and direct access to the pool—extends the living space to the outdoors. With a sandy beach and two private piers, one tucked into Crouches Cove and the other stretching into the Severn river, this estate offers not just a home but a lifestyle of breathtaking vistas on the water, boating adventures at your doorstep, and the unmatched beauty of Annapolis waterfront living. Located in the Blue-Ribbon Broadneck School district and just 5 miles to downtown Annapolis, convenient to Baltimore, BWI, Ft. Meade/NSA and Washington, DC., the location provides the very best this region has to offer in a 30-mile radius. If you are looking for a truly special property with EPIC water views, resort like amenities and a great private setting, this is the property you have been waiting for. Welcome Home!
#MDAA2132598

ANNAPOLIS

125 S WINCHESTER ROAD

5 Beds

5 Baths

11,269 Sq.Ft.

$7,500,000

MLS#: MDAA2132598

New on site 1 day ago
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.
#MDAA2148092

ANNAPOLIS

3728 RAMSGATE DRIVE

4 Beds

5 Baths

5,771 Sq.Ft.

$6,995,000

MLS#: MDAA2148092

Escape to another world with this striking French modern waterfront estate. Exquisitely sited on a premium and private 4.15 acre lot with 600 feet of impressively rip-rapped water frontage, coveted waterfront pool, tennis court and picturesque views of the serene waters of Whitehall Creek. This ultra-luxe 9,000+ square-foot, 7 bedroom, 5.5 bathroom custom built home has been completely renovated. It is evident from the moment you walk in the front door that no expense was spared with this stunning home. Curated with premium quality, top of the line materials, combined with the tranquil views, exquisite design, and top-tier finishes, 1524 Cedar Lane Farm Road is truly one-of-a-kind and showcases unparalleled craftsmanship. The property both inside and out is an absolute entertainer's dream. The lush lawn and landscaping gracefully extends to the water's edge and leads to the well-appointed multi-slip IPE pier with boat lifts, 2 jet ski lifts, upgraded power, water and great lighting including underwater LED fishing lights. Inside, this stunning home boasts an awe-inspiring Great Room with soaring ceilings, architectural beams, and panoramic water views and features brushed Teak hardwood flooring, renovated high-end gourmet Kitchen with marble counters, 10 burner Wolf range, 5 fireplaces, Restoration Hardware lighting, renovated bathrooms throughout and much more! Fall asleep to captivating, sweeping views from the Primary's suite, enjoy watching the early morning wildlife activity on the water. Located on Whitehall Creek which flows out to Whitehall Bay and beyond to the Chesapeake Bay, you are perfectly located to take advantage of the Bay's best cruising and fishing areas. Attractive destinations such as the Annapolis Harbor, Baltimore's Inner Harbor, St. Michaels, Oxford, and Solomon's Island are only a short cruise away and just minutes from accessing Rt. 50 and 97 which provides direct access to Baltimore, BWI, Ft. Meade/NSA and Washington, DC., or head over the Bay Bridge to the Eastern Shore for a quick beach vacation. Welcome Home!
#MDAA2131054

ANNAPOLIS

1524 CEDAR LANE FARM ROAD

7 Beds

5 Baths

9,024 Sq.Ft.

$6,995,000

MLS#: MDAA2131054

A truly iconic Annapolis offering, this extraordinarily rare waterfront estate is gracefully set on 7.5 remarkably private acres, showcasing what may be the most breathtaking panoramic views in all of Annapolis. With endless, horizon-stretching vistas that evoke the feel of an oceanfront retreat, the Chesapeake Bay unfolds before you with the Bay Bridge creating a dramatic backdrop in the distance, while Annapolis’ beloved summer sailboat races become part of your everyday scenery. A setting of this magnitude—offering serenity, privacy, and commanding water views—is simply irreplaceable. Encompassing more than 9,000 square feet, this grand residence was thoughtfully designed to maximize its extraordinary setting, with jaw-dropping water views greeting you the moment you step through the front door and drawing your eye through the soaring two-story family room straight to the Chesapeake beyond. The architectural footprint and flow are exceptional, creating the perfect canvas for a visionary buyer to elevate this estate into a world-class showpiece. The main level is anchored by an expansive waterfront primary retreat, a sanctuary unto itself featuring dual walk-in closets, a spa-inspired bath with a jetted soaking tub, oversized skylit shower, separate vanities, a bidet, and a private spiral staircase leading directly to the lower-level fitness and hot tub retreat. Two additional generously sized en suite bedrooms with walk-in closets are also conveniently located on the main level, along with a richly appointed study/library, elegant formal dining room, spacious kitchen with island and breakfast area, plus an additional family gathering space designed for effortless everyday living and entertaining. Upstairs, two exceptional en suite bedrooms each offer walk-in closets, fireplaces, private waterfront balconies, and spectacular elevated views that feel suspended above the Bay. The walkout lower level is equally impressive, designed for entertaining and multigenerational flexibility, featuring expansive recreation spaces opening directly to the waterfront patio, plus a fully self-contained in-law or au pair apartment complete with its own kitchen, family room, full bath, separate entrance, and—of course—those same extraordinary views. What sets this offering even further apart is the remarkable future potential already in motion. With public sewer and an extraordinary 7.5-acre footprint, the possibilities are nearly limitless. Seller-approved county plans—transferable to the next owner—dramatically accelerate the vision, including plans for shoreline improvements, tree clearing to further expand views, bank reshaping, revetment enhancements, a new tram and stair access to the pier, a widened driveway with a new entrance feature, a detached guest house with its own private entrance from Lyons Dr, a pickleball court, a gazebo, and additional grounds enhancements. This is more than a home—it is one of Annapolis’ most extraordinary legacy properties, offering a once-in-a-generation opportunity to create an unparalleled waterfront masterpiece.
#MDAA2145908

ANNAPOLIS

2562 CARROLLTON ROAD

7 Beds

8 Baths

9,026 Sq.Ft.

$6,500,000

MLS#: MDAA2145908

Stately French Villa on Spa Creek in downtown Annapolis! This jewel box of a home was designed and built by a renowned local architect as the culmination of an award-winning career. Offered completely turn-key, this exceptional residence conveys fully furnished and thoughtfully appointed—including furniture, fully equipped kitchen, linens, etc —allowing you to arrive with nothing more than a suitcase and begin enjoying the Annapolis waterfront lifestyle from day one. The unrivaled architectural detail, exquisitely curated finishes, and sweeping views across Spa Creek elevate this residence into a class of its own. Privately positioned at the end of a quiet street within one of downtown’s most coveted waterfront enclaves, this 3-bedroom, 3.5-bath retreat is equally suited as an elegant weekend escape or a full-time residence. Dramatic Palladian windows bathe the interiors in natural light while perfectly framing the ever-changing harbor views. At the heart of the home, the gourmet kitchen—appointed with custom cabinetry, premium appliances, and a striking designer hood—flows seamlessly into both the formal living room and inviting family room, each enhanced by a gas fireplace and captivating water vistas. A main-level secondary primary suite offers comfort and flexibility for guests of all generations. Upstairs, the extraordinary waterside primary suite features vaulted ceilings, walls of glass, a gas fireplace, spa-inspired bath with soaking tub, and a custom dressing room with center island. A private balcony provides the ideal perch for sunrise coffee or sunset reflections overlooking Spa Creek, Annapolis Harbor, and Eastport. Designed for effortless waterfront living, two deep-water piers with approximately 9 feet of MLW accommodate substantial vessels, with immediate access to the Severn River, the Chesapeake Bay, and beyond. Walkable to the shops, restaurants, and charm of downtown, this rare offering delivers convenience, privacy, elegance, and ease in one remarkable package. Welcome Home!
#MDAA2132250

ANNAPOLIS

1 SHIPWRIGHT HARBOR

3 Beds

3 Baths

3,108 Sq.Ft.

$5,898,000

MLS#: MDAA2132250

Prime location at the intersection of Route2/Solomons Island Rd and MD-450/West St. 100% Leased! Building was recently fully remodeled to include New Glass, New Facade, New Elevator, New HVAC and New Lobbies. 120 free surface parking spaces (4/1,000 ratio). Easy access to Routes 50 and 97.
#MDAA2131116

ANNAPOLIS

2024 WEST STREET

None Beds

None Baths

34,573 Sq.Ft.

$5,850,000

MLS#: MDAA2131116

Set on 4.5 picturesque acres along the Severn River, this exceptional Tudor–French Country estate blends timeless architecture with refined craftsmanship just minutes from downtown Annapolis. Panoramic river views define the property, complemented by a detached two-car garage with private guest quarters featuring a kitchenette and full bath. Outdoor living is equally compelling, with a fire pit, boathouse for convenient dockside storage, and a private pier equipped with a 20,000 lb boat lift—ideal for embracing true waterfront living. Access the dock via a scenic path and stairs or by private tram. Inside, light-filled interiors capture sweeping water views and flow effortlessly through a thoughtfully designed floor plan suited for both everyday living and elegant entertaining. A dramatic curved staircase anchors the foyer, leading to a main level that includes a gourmet kitchen, living room with a gas fireplace, bar, office, mudroom, two powder rooms, and a formal dining room. The chef’s kitchen is outfitted with a 6+ burner Wolf range, hammered copper sinks, dual dishwashers, expansive prep space, and a generous pantry. The living area opens to a spacious deck, perfect for waterfront gatherings. Upstairs, the primary suite offers a private retreat with its own balcony, wet bar, two walk-in closets, dual vanities, and a walk-in shower. This level also includes flexible bonus space, two additional bedrooms, a full bath, and a laundry room. The lower level expands the living space with two additional bedrooms, two full baths, a family room with fireplace and bar, and a game room—all with easy outdoor access and continued river views. All levels of this home can be accessed by an elevator. Some of the well executed details in this home include wooden beams, arched doorways, curved walls, extensive stone work, intricate iron work, dramatic light fixtures, walnut flooring, dramatic built-ins and the highest level of craftsmanship and execution. A rare opportunity to own a meticulously crafted waterfront retreat that seamlessly combines old-world charm with modern luxury.
#MDAA2139364

ANNAPOLIS

1716 SEVERN FOREST DRIVE

5 Beds

4 Baths

6,573 Sq.Ft.

$5,775,000

MLS#: MDAA2139364

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