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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
359
# of Listings
3
Avg # of Bedrooms
$482
Avg. $ / Sq.Ft.
$1,111,217
Med. List Price

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10 Properties Found. Page 1 of 1.

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

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