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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
358
# of Listings
3
Avg # of Bedrooms
$481
Avg. $ / Sq.Ft.
$1,111,442
Med. List Price

Browse Annapolis Real Estate Listings

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358 Properties Found. Page 1 of 24.

THE FRIARY a Trophy property in a league of its own! Set on 23 private acres overlooking a gracious bend of the Severn River with 1,500ft of prime waterfrontage, just minutes from downtown Annapolis and less than an hour from the nation's capital, lies one of the most distinctive estates offered for sale on the East Coast. A true architectural masterpiece, this exquisite 35,000+ sqft residence, is the result of a mammoth and complex renovation that brought it back to its classic Georgian style yet with an acknowledgment of the owner's contemporary tastes and interests. Formerly a Capuchin monastery, this stately brick structure offers modern amenities for comfortable family living yet easily accommodates elegant grand scale entertainment and private events. The attention to detail and emphasis on proportions and craftsmanship are unparalleled. The exterior features spectacular 270 degree river views, nine car garage, roof garden, pool pavilion, 60 feet infinity edge pool, tennis court and direct access by funicular to a 6 slip private dock with 10' MLW and boat lift. Step into the main core of the home, where 18th-century elements, like original heart pine floors & foyer arch moldings, have been flawlessly preserved. A cleverly designed limestone rotunda containing a conservatory & atrium lead to either of the house’s wings: the impeccably appointed guest wing with spacious common room, or the chapel-turned-ballroom with sweeping limestone fireplace, herringbone teak floors, & arched double doors with a picturesque terrace beyond. The extraordinary estate contains a total of seven bedrooms, eight bathrooms and eighteen fireplaces, formal dining room and formal parlor, commercial size gourmet kitchen, over sized ballroom, conservatory, family room, library, music room, indoor spa, game room, wine cellar, catering kitchen, work shop, and a secret vault. Additional structures on the property include a three bedroom, two bath-guest/staff house, an Asian tea house and mechanical facilities. Only minutes from Washington D.C. and multiple international airports, this elegant and opulent property is worlds away from the hustle and bustle of everyday life yet offers an easy commute to several major metropolitan cities. Unmatched opulence and privacy awaits on the Severn River!
#MDAA2102408

ANNAPOLIS

1604 WINCHESTER ROAD

7 Beds

8 Baths

35,435 Sq.Ft.

$19,995,000

MLS#: MDAA2102408

MELVIN ROAD WATERFRONT ESTATE! A winding, tree-canopied drive leads to Silver Maple Manor, a breathtaking waterfront and equestrian estate nestled on nearly eight acres along Little Aberdeen Creek. Designed by the renowned Scarlett Breeding and built with masterful craftsmanship, this European-inspired retreat feels as if it has stood for centuries, its mature landscaping and thoughtful details evoking the grandeur of a bygone era. With 5 bedrooms, 6 full baths and 2 half baths, this home is a masterpiece of custom millwork, rough-sawn oak flooring, and exquisite stonework. The grand foyer welcomes you with soaring 21-foot ceilings, a sweeping curved staircase with a brass handrail, and Venetian plaster walls that glow in the natural light. Every room is designed to embrace the water views, from the elegant living spaces to the chef’s kitchen, where marble countertops and a Thermador cooktop await culinary creations. The finished room above the garage offers a wonderful game room or retreat. The home also features 2 offices and a bonus room with cedar closet that is perfect for a gym. A temperature-controlled wine cellar offers a place to store prized vintages, while the butler’s pantry, complete with a Sub-Zero beverage cooler and Miele double ovens, ensures effortless entertaining. Beyond the home, the estate unfolds into a sanctuary of outdoor luxury. A heated saltwater pool, framed by bluestone pavers and a pergola-shaded terrace, invites both relaxation and celebration. The screened sunporch, with its stacked-stone fireplace and beadboard ceiling, provides a cozy retreat in every season, flowing seamlessly to the flagstone patio, where the water shimmers just beyond. For those drawn to the water, the estate offers four deep-water slips, two boat lifts, and a cedar boathouse, a work of art in itself with handcrafted shutters and masterful carpentry. Whether setting sail for an afternoon on the Chesapeake or simply watching the boats drift by, life here is tied to the rhythm of the water. Equestrians will find a barn thoughtfully designed for both function and beauty, with horse stalls, a conditioned tack room, a traditional hayloft, and its own dedicated driveway for trailers. The rolling pastures provide ample space for grazing, offering a picturesque setting for riding or simply enjoying the serene surroundings. Though it feels like a secluded retreat, Silver Maple Manor is just minutes from Historic Annapolis and an easy commute to Washington, D.C., Baltimore, and major airports. A home of rare beauty and distinction, it is a place where elegance, nature, and craftsmanship intertwine, creating a timeless estate. Welcome Home!
#MDAA2103832

ANNAPOLIS

948 MELVIN ROAD

5 Beds

6 Baths

10,505 Sq.Ft.

$12,500,000

MLS#: MDAA2103832

Rare opportunity for a true legacy property on the Severn River! Built by Pilli Custom Homes, this home is a masterpiece of craftsmanship. Wake up every morning to the everchanging scenery out your windows, step out onto your private balcony with a freshly brewed coffee from your in-room coffee bar, feeling the gentle river breeze as you watch sailboats drift by. Make your way down via the elevator or stairs to the heart of the home —a gourmet kitchen designed for both function and beauty. A commercial-grade stove, oversized island, high end appliances and butler’s pantry set the stage for memorable meals, whether it’s a casual breakfast in the sunlit dining area or a feast prepared for guests. The open floor plan ensures that no moment is spent away from the home’s most stunning feature—its endless panoramic water views. Mid-morning calls for a stroll down to your private beach, toes in the sand, as the water laps gently at the shore. Perhaps it’s time for a boat ride. Your commercial-sized pier, equipped with multiple lifts and slips, makes it effortless to set out for an afternoon on the water. The land lovers can take an easy stroll into Annapolis or stay closer to home and lounge by the heated saltwater pool, where the sound of the waves blends with the laughter of loved ones. A distinguished home office showcases exquisite woodwork, built-ins, and a double-sided fireplace; a great place to catch up on some work if you can take your eyes off the mesmerizing views. As the day winds down, retreat to one of the many cozy sitting rooms including the stunning sitting room with walls of windows, a perfect hideaway overlooking the pool and river, ideal for a quiet moment with a book or a glass of wine. In the cooler months, the home's fireplaces—found in the living room, family room, office, and even the primary bath—offer warmth and ambiance. Evening entertainment takes shape in the lower-level London pub bar, where friends gather for a game of billiards or a lively conversation. A family movie night in the spacious den, a midnight swim under the stars. The possibilities are endless in a home designed for both grand entertaining and peaceful retreat. As night falls, retreat to the primary suite, a true sanctuary with a private balcony, a fireplace flickering in the background, and a spa-like bath where a deep soaking tub and towel-warming drawers create the perfect end to a perfect day. At 1900 Carrollton Road, every day feels like a dream—a life immersed in luxury, comfort, and the beauty of the Severn River. This is more than a home; it’s a legacy. Welcome Home!
#MDAA2105526

ANNAPOLIS

1900 CARROLLTON ROAD

7 Beds

6 Baths

12,200 Sq.Ft.

$8,995,000

MLS#: MDAA2105526

Welcome to your luxury waterfront sanctuary on the Severn River, located in the highly coveted Downs on the Severn community of Annapolis. This extraordinary estate offers unmatched amenities including a private sport court, heated saltwater pool, and private pier with a tram to easily transport you and your guests to the water’s edge for unforgettable days on the Bay. Inside, the craftsmanship is unparalleled and the curated finishes reflect that no expensive was spared to create a home of distinction. The main level flows from the stately foyer, the soaring rotunda that serves as a formal dining room and meticulously constructed office to the beautifully appointed Living room, wet bar, Gourmet Kitchen and Family room all with stunning views of the river below. The attention to detail throughout is designed to impress while creating a warm and inviting home for day to day waterfront living. The bonus dog room with shower, laundry, and refrigerator with access to the dog run is perfect for animal lovers! A fully finished lower level invites relaxation and entertainment with a game room, steam room, home gym, and guest quarters. The bar area and possible wine tasting room/wine cellar adjacent to the elevator are ready for your personal touches to make it your own. Upstairs, the stunning primary suite is a true retreat with private balcony overlooking the pool and waterfront, dual bathrooms, custom vanities, 2 expansive closets, a private massage room, and a second-level laundry suite with an in-home salon for discreet hair and makeup sessions. An oversized, glass-enclosed luxury shower connects the two spa baths, offering breathtaking views of the river below. The 3 additional ensuite bedrooms provides ample room and privacy for guests and family. Outside, the heated saltwater pool with deep end diving board boasts unobstructed water views and expansive pool deck area including fully equipped outdoor kitchen, a pavilion to enjoy the shade, stunning fire bowls and easy access to the water below. The deep water private pier features multiple slips and 40,000lb boat lift; creating an effortless and fun atmosphere while cruising down the Severn River to the Chesapeake Bay and beyond. Experience a life of privacy, resort-style amenities, and timeless beauty in this one-of-a-kind waterfront masterpiece. Welcome Home!
#MDAA2109888

ANNAPOLIS

806 COACHWAY

5 Beds

5 Baths

12,635 Sq.Ft.

$7,850,000

MLS#: MDAA2109888

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!
#MDAA2103890

ANNAPOLIS

1524 CEDAR LANE FARM ROAD

7 Beds

5 Baths

9,024 Sq.Ft.

$6,995,000

MLS#: MDAA2103890

This Severn River Waterfront Estate is a rare and breathtaking Annapolis retreat. Experience the ultimate in waterfront living in this exquisite residence, a true masterpiece offering unparalleled panoramic water views. Nestled on a pristine one-acre site in the prestigious Point of The Downs, this custom-built legacy home has been meticulously updated to perfection, creating the ideal setting for unforgettable family gatherings, holidays, and retreats. Spanning four levels of immaculate living space, this residence boasts designer finishes throughout. The grand chef’s kitchen is a showstopper, featuring elegant white cabinetry, a Sub-Zero refrigerator, a custom bar area, and multiple dining spaces. The luxurious primary suite is a private sanctuary, offering breathtaking water views. Two home offices provide the perfect work-from-home setup, while an elevator ensures seamless access to all levels. Indulge in exceptional amenities designed for both relaxation and entertainment. Six gas fireplaces create warmth and ambiance, while the in-home theater offers the ultimate cinematic experience. A private gym, sauna, and steam room provide a space for wellness and rejuvenation. Outside, the PebbleTec waterside pool, hot tub and outdoor fireplace create a resort-style atmosphere perfect for entertaining or unwinding. For boating enthusiasts, the private deep-water pier features an eight-foot mean low water depth, three slips, and two lifts with 12,000- and 20,000-pound capacities. A three-car garage with 2 electric charging stations and circular driveway provide ample parking for residents and guests alike. This is more than just a home—it’s a lifestyle. Don’t miss this rare opportunity to own one of Annapolis’ finest waterfront estates on the Severn River.
#MDAA2105620

ANNAPOLIS

803 COACHWAY

6 Beds

8 Baths

11,045 Sq.Ft.

$6,750,000

MLS#: MDAA2105620

Winchester-on-the-Severn Waterfront! This modern home is only surpassed by the all encompassing, elevated views of the Severn River. Exquisite finishes are the hallmark of this elegant 5 bedroom 5.5 bath brick home where no details were compromised in presenting a home of distinction. Floor to ceiling sliding LaCantina glass doors blur the line of indoor and outdoor living and showcase the water beyond. If you can look away from the view, the marble slab fireplace, beamed ceiling and wet bar truly elevate the scene in the spacious great room. The chef's gourmet kitchen is sure to impress with Wolf and Sub-Zero ultra premium appliances and is well-equipped for large parties or intimate dinners at home. With more walls of glass and expansive waterside IPE deck, the dining room and family room are thoughtfully located to take in the view and create a wonderful atmosphere for entertaining. The opposite wing of the home is dedicated to an executive level office space with built-ins and the glorious ultra-luxe primary suite which features soaring ceilings, endless views, coffee/wet bar, 2 custom walk-in closets and the most luxurious bathroom with heated porcelain floors, soaking tub, glass enclosed walk-in shower and 2 vanities. Completing the main level is the guest room with full bath, laundry room, mudroom and powder room. Upstairs enjoy framed views of the water from light-filled seating nooks, 3 bedrooms, 3 baths and multiple bonus rooms, perfect for a play room, gym or teen hang-out space. The unobstructed sweeping panoramic south facing views abound which embodies the quintessential Annapolis waterfront lifestyle. Sit back and watch the ships navigate the local waterways from the expansive IPE deck with glass railings or head out yourself from your private deep water pier with tram access. Voyage out under the Severn River bridge to Annapolis and beyond. This magnificent property stands proudly in the coveted Winchester-on-the Severn community which boasts THE best beach on the Severn River plus tons of community amenities including a boat ramp, (4) piers, marina, beach pavilion, playground, and dog beach, plus the Chase Creek swim club and the B&A Trail is right up the street. Located in the Blue-Ribbon Broadneck School district and just 5 miles to downtown Annapolis and Severna Park. 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 and a great neighborhood setting, this is one opportunity you don't want to miss!
#MDAA2097756

ANNAPOLIS

205 WINCHESTER BEACH DRIVE

5 Beds

5 Baths

6,911 Sq.Ft.

$6,498,000

MLS#: MDAA2097756

South Annapolis Yacht Center is located on Spa Creek overlooking the beautiful skyline of Historic Annapolis. This award winning residence features an elegant interior design that brings the feel of the adjoining waterway into the living area. Patrick Sutton thoughtfully did the interior design and Bret Anderson of Pyramid Builders constructed this magical 3 bedroom, 3 bath waterfront residence. A bright open floor plan, perfect for entertaining, connects to the wrap around deck overlooking the water. The kitchen features a six burner La Cornue range with matching hood, Sub-Zero refrigerator with custom freezer draws, wine cooler and a large luxe marble center island all overlooking the water. The Primary Suite enjoys beautiful views of Spa Creek & Annapolis, a large dressing room with rosewood cabinets and a luxurious spa like bath. The Primary suite walls are fully upholstered with a wool herringbone material and braided leather trim giving the space a warm comfortable feel. There are 2 additional ensuite bedrooms with one doubling as a den/in home office. There are 2 gas fireplaces, one in the main living area and one on the waterfront deck. There is a rented 1 car garage (across the street, $700/mo) and a storage unit in the lower level of the building. Access to this fabulous residence is via an elevator that opens directly into the unit. Enjoy watching the Christmas Boat Parade, Commissioning Week Blue Angels Show and the 4th of July Fireworks from the waterfront deck. The adjoining world class marina not only is a perfect spot to keep your boat but a great view to watch some of the most beautiful yachts on the East Coast. The prime Spa Creek location, the quality of construction and the award winning interior design puts this property in a league of its own. CHECK OUT THE 3D FLOOR PLAN.
#MDAA2102850

ANNAPOLIS

287 STATE STREET 2

3 Beds

3 Baths

2,949 Sq.Ft.

$6,350,000

MLS#: MDAA2102850

Price is for a total of 10 buildable lots. Lots are permit ready, all SWM are already completed by Reliable Contracting under original grading permit that is already bonded by Chesapeake Realty Group, only requiring all of the permits that are required by the city of Annapolis. No permits are required by The Anne Arundel County Department of permits. Builder just needs to submit house plan, pay building permit based on the square footage, whatever impact fees that are required and install #2 stone over construction entrance where the driveway openings are for each house and they are ready to build! Construction entrances need fabric cloth underneath the stone, no Storm Water Management is required on these 10 Lots! No HOA, there is a front foot fee of $950/year to Sturbridge Parkeside LLC with a $25 account setup fee.
#MDAA2092632

ANNAPOLIS

117 STILLY WAY

None Beds

None Baths

0.22 acres

$6,000,000

MLS#: MDAA2092632

Stately French Villa on Spa Creek in downtown Annapolis! This jewel box of a home was designed and built by renowned local architect as the culmination of an award winning career. The unsurpassed attention to architectural details, exquisitely curated finishes and breathtaking views of Spa Creek places this trophy home in a league of its own. Tucked away at the end of a quiet street in a premier residential enclave on the banks of Spa creek, this 3 bedroom 3.5 bath is the perfect weekend getaway or forever home. Awe- inspiring palladian windows flood the rooms with natural light and frame the ever-changing water and harbor views. Enjoy entertaining from the gourmet kitchen with custom cabinetry, high end appliances, and beautiful range hood; located in the center of the home the kitchen flows easily into the formal living room and family room both with gas fireplaces and water views. The main level secondary primary suite provides options for friends and family of all ages. Upstairs the spectacular waterside Primary suite boasts vaulted ceilings, floor to ceiling windows, gas fireplace, spa-like bath with soaking tub and custom closet with center island. Relax every morning and evening from the private balcony while enjoying the panoramic views of Spa Creek, Annapolis Harbor, and Eastport. The 2 deep water piers with 9ft MLW can accommodate boats of all sizes and the location provides quick access from Spa Creek out to the Severn River, Chesapeake Bay and beyond. Walkable to everything Annapolis has to offer this truly unique property offers the complete package: convenience, security, beauty and comfort. Welcome Home!
#MDAA2100630

ANNAPOLIS

1 SHIPWRIGHT HARBOR

3 Beds

3 Baths

3,108 Sq.Ft.

$5,898,000

MLS#: MDAA2100630

Gorgeous coastal style home in the coveted Bay Ridge community with stunning and thoughtful renovations that highlight the expansive Chesapeake and Bay Bridge views! The extensive renovation by M Homes elevated the appeal and functionality of the home by adding 2 additional ensuite bedrooms and laundry room on the 2nd level and much more. No expense was spared to make this a home of distinction, from the on trend wide plank white oak floors, to the stunning primary bedroom and bath, every detail was thought out and expertly executed. The open floor plan allows water views from almost every room, the gourmet kitchen is perfect for entertaining and the main level bedroom with full bath provides options for one level living. Envision idyllic days filled with family and friends gathering in the perfectly perched screen porch to watch the endless activity on the Bay. Head upstairs and enjoy the amazing recent addition that boasts a convenient and expansive laundry room and 3 ensuite bedrooms, including the spectacular Primary suite. Savor the breathtaking panoramic Bay views from sunrise to sunset from the comfort of your bed! The renovation of the 2 car detached garage ensures shelter for your vehicles and delivers additional living space with the upper level bonus room/office space. Beach access to the Bay right out your front door ensures endless opportunities to relax at the water's edge, watch the waves and sailboats, cool off on summer days and enjoy the waterfront lifestyle! The sought-after Bay Ridge Community features a plethora of amenities including community pool with a clubhouse that overlooks the beautiful waters of the Bay, community beaches on both the River and the Bay and a community Marina with a newly renovated clubhouse. Off-the-water activities include enjoying the basketball court, playground, ball fields, pickleball courts, common areas and year-round community activities. Walk or ride your bike for miles along the water and enjoy all the benefits of the Bay Ridge lifestyle, there is no other place like it! Located just minutes from downtown Annapolis and Eastport which offer the perfect balance of small-town charm and big world sophistication. Traveling or commuting is just as convenient by easily 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.
#MDAA2100338

ANNAPOLIS

54 RIVER DRIVE

4 Beds

4 Baths

3,250 Sq.Ft.

$4,995,000

MLS#: MDAA2100338

Don't miss this incredible opportunity to build your dream luxury estate home on this amazing private 3.3 acre homesite with amazing waterviews and privacy. Tucked away back off of your 1/4 mile private driveway which sets the tone as you approach your very own oasis. Come witness our vision and be a part of creating a generational estate that Annapolis rarely sees. The main level boasts soaring 10-foot ceilings, exposed beams, and wide plank floors, creating a spacious and inviting atmosphere. The gourmet kitchen is a chef’s dream, featuring built-in cabinetry, sleek quartz countertops and backsplash, a generous island, double ovens, a gas cooktop, and a walk-in pantry. The kitchen seamlessly flows into the dining area, with large windows and glass doors that frame stunning views of the creek. Step outside to a covered patio, perfect for outdoor entertaining, located just off the dining and family room. Upstairs, the expansive primary suite offers panoramic water views through large windows. The spa-like primary bathroom includes a freestanding tub, oversized shower, water closet, and a walk-in closet. This level also features three additional spacious bedrooms, two full bathrooms, and a convenient laundry room. The finished lower level includes a fifth bedroom, a full bathroom, and a large recreation room, providing plenty of space for guests or family activities. Situated on a private 3.3 acre lot with pristine waterfrontage, this property has the ideal depth for a private pier to accommodate your boat. Experience ultimate privacy, luxury, and waterfront living all in one. Appointments are required for a private showing—please contact the listing agent for details and don’t miss out on this once-in-a-lifetime opportunity!
#MDAA2110220

ANNAPOLIS

1632A WINCHESTER ROAD

5 Beds

4 Baths

5,000 Sq.Ft.

$4,950,000

MLS#: MDAA2110220

Welcome to 3054 Rundelac Road, a quintessential Annapolis waterfront estate located on Aberdeen Creek. Nestled on nearly 4 acres in a quiet neighborhood, this extraordinary home offers thoughtful luxury and amenities ensuring the ultimate experience in waterfront living. The landscaped gardens include a welcoming front yard and a private backyard. Off the extensive swimming pool patio, the lawn flows down to waterfront framed, but not obscured, with mature hardwood trees. The barn is ready to host a flock of chickens or a fleet of kayaks. Exterior features include a private pier with boat lift, a heated swimming pool with gazebo and hot tub, a two stall horse barn, multiple garages, a large storage shed, and a dedicated mooring. The house itself is a timeless beauty. Exceptionally well designed with recent expansions and updates, the interior boasts a stunning two story great room with dramatic vaulted ceiling and skylights, allowing in tons of natural light. Other features include a chef’s kitchen with state of the art appliances, a movie theater, a gym, multiple game rooms, generous bedrooms with ensuite bathrooms, a large office, two living rooms and a formal dining space. A separate two-bedroom apartment with a private entrance as well as a second staircase leading to the kitchen is located above the garage. Seamlessly blending indoor and outdoor living, the property offers endless opportunities for family gatherings and fabulous parties. And just a fifteen minute boat ride to downtown Annapolis!
#MDAA2109490

ANNAPOLIS

3054 RUNDELAC ROAD

6 Beds

6 Baths

13,495 Sq.Ft.

$4,850,000

MLS#: MDAA2109490

One-of-a-kind Waterfront Luxury in Annapolis, Maryland! Secluded on 2.59 lush, park-like acres along the shores of one of the Chesapeake Bay’s most serene and protected tributaries, this exceptional estate offers an unparalleled blend of privacy, elegance, and premier waterfront living rarely found in Annapolis. From the moment you arrive down the tree-lined drive, a sense of calm and sophistication sets in. With 185 feet of pristine shoreline, deep water, and a private pier with boat lift, this is more than a home, it’s a relaxing destination where every day feels like a retreat. Spanning over 12,000 square feet, this custom-built estate (main floor finished in 2014 by Pyramid Builders, lower level in 2019 by Bayview Builders) is crafted with the highest-quality materials and top-of-the-line features. Every detail has been curated with uncompromising quality to deliver a life of luxury, comfort, and effortless entertaining. This resort-like home is built to host—from elegant galas with ample onsite parking to relaxed family weekends. Inside, sunlit spaces and radiant-heated floors create a warm, welcoming atmosphere throughout the year. The grand two-story foyer with custom millwork ceiling opens to formal living and dining rooms, while the heart of the home—a soaring great room with fireplace—anchors the space with timeless beauty and comfort. A chef’s dream kitchen is equipped for both daily living and high-end entertaining, featuring Sub Zero refrigerators and wine cooler, Wolf stove/griddle and double ovens, dual dishwashers, warming drawers, catering entrance, ample custom cabinetry, and expansive granite countertops. Whether preparing an intimate dinner or a large event, this space delivers excellence. For gathering and unwinding, the custom mahogany bar with private balcony overlooking the waterfront and pool is located on the main floor and connects to the kitchen by the great room–perfect for serving pre-dinner cocktails or spreading out larger gatherings. A comfortable family room and sunroom off the kitchen overlook the waterfront and pool providing relaxing sunset views. A main-level guest suite with private balcony ensures both comfort and privacy for visitors while a sun-filled custom wood paneled office with fireplace provides an impressive and inspiring executive workspace at home. Ascend the stunning curved staircase to the primary suite for a serene escape with water views and attention to all your needs with sitting room, fireplace, dual dressing rooms, a private balcony, and a spa-like en-suite bath. Three additional en-suite bedrooms, a laundry room and an upper-level library offer generous, luxurious accommodations for family and guests. The newly finished walkout lower level feels like its own private coastal escape: game room, kitchenette, home gym, a 2nd laundry room, pool bath, sauna, and guest quarters with private entry—perfect for an au pair, in-laws, or long-term visitors. Step outside and discover a resort caliber setting: a heated saltwater pool and hot tub surrounded by travertine patios, Ipe decks, and outdoor dining areas that invite celebration and quiet reflection alike. Cruise effortlessly from your backyard to the Chesapeake Bay, South River, Annapolis Harbor and St. Michaels for waterfront dining or explore the many nearby creeks and coves. Whether you're boating, catching crabs off the dock, taking in the bald eagles during sunset, or paddling into calm morning waters, the connection to nature and the water here is effortless. Conveniently located just minutes from downtown Annapolis and within easy reach of commuter routes to Washington, D.C. and Baltimore, this extraordinary estate defines luxury living. This is more than a home—it’s an estate that offers a luxurious lifestyle immersed in nature, rooted in comfort, and ready to be shared. Embrace this rare opportunity to own an exclusive piece of Annapolis where luxury meets tranquility!
#MDAA2112550

ANNAPOLIS

840 CHILDS POINT ROAD

6 Beds

7 Baths

12,374 Sq.Ft.

$4,650,000

MLS#: MDAA2112550

"First time publicly offered". The owner/operator is now ready to retire and pass the Baton, after 55 years of service, So, you won't want to miss out on this wonderful opportunity to own this thriving business along with its prime commercial real estate. Under his stewardship and dedication, the owner built this business to become an Annapolis Icon. Being offered is a multiple-faceted business opportunity i.e. in addition to its copious gasoline sales the, business operates a 7-bay service area for automobile repairs (equipped with lifts), it is an Authorized Maryland Inspection Station, a Towing Service with a fleet of tow trucks with varied capabilities, and to complement the towing business there is a secured (income producing) commodious fenced storage /tow yard with approval for 125 automobiles. The real estate portion consists of 2.0 acres +/- of commercially zoned land with a road frontage of 270' +/- AADT count of 46,000+/-. The zoning is split between AA County( C-4) and the City of Annapolis (B-2). The site is served by public utilities i.e. public water, public sewer, and natural gas. A 3,800 sq. ft. building serves as the operational hub which consists of 7 service bays, 2 integrated offices, a lobby (vending & ATM), a service write-up areas, a cashier window, and 3 restrooms (1 is handicapped accessible), 8 security cameras. UST tanks with 30,000-gallon capacity, including diesel fuel (tanks recently underwent state inspection). The apron was recently blacktopped. Currently, the operational level is open 6 days per week and closed on Sundays and all major holidays, thus creating an immense opportunity to increase the sales volume by simply revising the operational schedule. There is potential for a "C" store conversion on this site. The grounds and workstations are exceptionally well kept. The pride shows. The 2.0 acres is a composite of 5 parcels, with individual account numbers assigned by the SDAT. The lead account shown only covers the main building and a portion of the land and does not reflect the site's overall size. The owner has obtained a permit and has cleared and gravelled an addition area and erected new fencing thus increasing the storage area. The buyer is to do their own Due Diligence. PREQUALIFIED BUYERS ONLY! NO TIRE KICKERS! This site can only be shown by appointment. A Confidentiality Agreement will be required before any showings. A video accompanying this listing is attached.
#MDAA2087840

ANNAPOLIS

1321 FOREST DRIVE

None Beds

None Baths

N/A

$4,500,000

MLS#: MDAA2087840

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