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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

Browse Annapolis Real Estate Listings

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Under $250,000

$250,000 - $500,000

$500,000 - $1M

$1M - $3M

$3M - $5M

Over $5M

18 Properties Found. Page 1 of 2.

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

"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

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.

$4,450,000

MLS#: MDAA2112550

Commanding panoramic views of the Chesapeake Bay, Bay Bridge, and Eastern Shore, this exceptional waterfront residence offers an unparalleled waterfront lifestyle. The regions finest team was assembled including Purple Cherry Architects and Gate One Builders to create a custom masterpiece of style, design and tranquility. Outside, a private 120’ IPE pier with two Hi-Tide boat lifts—including a 16K heavy-duty lift and a 6K lift for kayaks and jet skis—makes this a boater’s dream. Peaceful waterfront living is elevated with a screened IPE porch featuring breathtaking views of sunrises, sailboat races, and the Blue Angels. Inside, the chef’s kitchen is outfitted with a 55” Lacanche range, dual Bosch dishwashers, leathered marble countertops, Miele appliances, and a walk-in pantry. Reclaimed 150-year-old beams, an award-winning iron and bronze staircase by Maynard Studios and custom built-ins throughout the home reflect true craftsmanship. A main level secondary Primary suite with water views provides flexibility and convenience. Upstairs, the expansive primary suite offers serene bay views, a spa-style bath, dual closets, private library and balcony. Enjoy a glass of wine at the end of the day from the temperature controlled wine cellar in the lower level. An upstairs studio with a bay-facing balcony offers flexible living or guest space. Timeless, thoughtfully designed, and meticulously maintained—2512 Lyon Drive is Chesapeake Bay living at its finest. Welcome Home!
#MDAA2113542

ANNAPOLIS

2512 LYON DRIVE

4 Beds

3 Baths

4,587 Sq.Ft.

$4,200,000

MLS#: MDAA2113542

Coveted West Annapolis Waterfront property with deep water floating dock! Experience elegance and grace in this stunning 4 story home that is sure to captivate. The contemporary architecture and voluminous spaces mixed with traditional finishes and floor plan creates a wonderful combination. Upon entry, the soaring foyer is awe-inspiring and the elegant living room, with built-in bar, sets the tone. With 3 custom bars and multiple gathering areas, this home is perfect for entertaining. The gourmet kitchen is a chef's dream, featuring a large island, top-of-the-line finishes and breakfast nook, which flows seamlessly into the spacious dining room with walls of windows overlooking Weems Creek. With 2 window seat nooks, wet bar, cozy fireplace, and cleverly disguised TV above, this room is equally valued at a lovely Family room. The adjacent library/den boasts mahogany built-ins and flooring, gas fireplace and views; a perfect place to curl up with a book. This home offers three ensuite bedrooms for ultimate comfort and privacy. The master bedroom is a sanctuary with a vaulted ceiling, custom built-ins, enormous walk in closet for 2 and the best views in the house. Wake up every morning and enjoy the activity on the sparkling waters of the creek and the Severn River. The spacious guest room suite with glass breezeway from the main house boasts an elevator directly into the room, creating a truly private oasis for guests and family. This floor also includes an additional bedroom or theater room with adjacent hall bath; providing flexible living options. The fourth floor features a unique bird's nest with elevator access and a wrap-around deck offering panoramic views of Weems Creek and the Severn River. With three elevators throughout the house, accessibility to all four levels is effortless. The exquisite sunroom with folding glass doors epitomizes indoor/outdoor living. Simply open 2 sides of the room to the outdoors and let the party flow onto the sprawling rear deck. The wrap-around IPE deck and multiple level seating areas are ideal for taking in the incredible views from every vista. The lush landscaping and stone stairs lead to the water's edge and the private pier with deep-water floating dock with multiple slips can accommodate a 50ft yacht. Be sure to not miss the stone patio on the way down; ideal for relaxing as the sun sets. This property truly captures the essence of waterfront living by blending luxury and comfort in an unparalleled setting. Welcome Home!
#MDAA2081948

ANNAPOLIS

411 RIDGELY AVENUE

4 Beds

4 Baths

5,950 Sq.Ft.

$3,950,000

MLS#: MDAA2081948

Once-in-a-Lifetime Opportunity to Build Your Dream Waterfront Home in Bay Ridge. Don't miss your chance to own the last remaining waterfront lot and be in your new home by next boating season in the prestigious and highly sought-after Bay Ridge community. This is a rare opportunity to work with the builder to design and build your dream home on a premium lot offering 57 feet of serene waterfront on protected Lake Ogleton. Also listed as just a lot without a house package. Enjoy breathtaking, unobstructed views and the peaceful lifestyle that only true waterfront living can offer. Whether you're envisioning a luxurious modern retreat or a timeless coastal home, this lot is the perfect canvas. Contact the listing agent for insight and inspiration on potential home designs tailored to this exceptional property. Bay Ridge is renowned for its rich history, vibrant community, and unmatched amenities, including a bayfront community pool and newly renovated clubhouse, sandy beaches and scenic waterfront , a large community marina, basketball and pickleball courts, a children's playground, and year-round community events. Located just minutes from downtown Annapolis and Eastport, Bay Ridge offers the charm of a tight-knit neighborhood with the convenience of city access. Experience the perfect blend of tranquility and community in one of the most desirable waterfront enclaves on the Chesapeake Bay. This is more than just a lot—it's the beginning of your dream lifestyle and opportunity to customize the perfect paradise.
#MDAA2115330

ANNAPOLIS

48A E LAKE DRIVE

5 Beds

4 Baths

4,000 Sq.Ft.

$3,950,000

MLS#: MDAA2115330

Once-in-a-Lifetime Opportunity to Build Your Dream Waterfront Home in Bay Ridge. Don't miss your chance to own the last remaining waterfront lot and be in your new home by next boating season in the prestigious and highly sought-after Bay Ridge community. This is a rare opportunity to work with the builder to design and build your dream home on a premium lot offering 57 feet of serene waterfront on protected Lake Ogleton. Also listed as just a lot without a house package. Enjoy breathtaking, unobstructed views and the peaceful lifestyle that only true waterfront living can offer. Whether you're envisioning a luxurious modern retreat or a timeless coastal home, this lot is the perfect canvas. Contact the listing agent for insight and inspiration on potential home designs tailored to this exceptional property. Bay Ridge is renowned for its rich history, vibrant community, and unmatched amenities, including a bayfront community pool and newly renovated clubhouse, sandy beaches and scenic waterfront , a large community marina, basketball and pickleball courts, a children's playground, and year-round community events. Located just minutes from downtown Annapolis and Eastport, Bay Ridge offers the charm of a tight-knit neighborhood with the convenience of city access. Experience the perfect blend of tranquility and community in one of the most desirable waterfront enclaves on the Chesapeake Bay. This is more than just a lot—it's the beginning of your dream lifestyle and opportunity to customize the perfect paradise.
#MDAA2115352

ANNAPOLIS

48 A E LAKE DRIVE

5 Beds

4 Baths

4,000 Sq.Ft.

$3,950,000

MLS#: MDAA2115352

Rare Waterfront Opportunity! Escape to your waterfront farmhouse retreat. Nestled on 3.5 picturesque acres overlooking the tranquil waters of protected Moss Pond, this charming historic property offers big views of and direct access to the Chesapeake Bay. Originally part of a working thoroughbred racehorse farm, this home is surrounded by parkland and privacy while still close to the city. Imagine peaceful mornings, stunning sunsets, and the joys of waterfront living. Your dream of a serene coastal lifestyle awaits. Enjoy boating, fishing, birdwatching, and the peace and quiet of coastal living all just a short drive from all the history, charm and convenience Annapolis has to offer. A peaceful meandering drive leads you to this one of a kind property. Enjoy breathtaking water views from each of the 5 bedrooms or entertain family & friends in one of the many sitting rooms that have retained their original character and charm. Custom built ins, heart pine flooring and dual staircases to the upper level, this home is steeped in history. Ample waterside living with an enclosed porch with screens or glass offering year round use flowing perfectly to the patio overlooking your 287 feet of water frontage, the perfect place for summer cocktails and dinner parties! The property features three outbuildings, an enclosed barn that can accommodate 4 cars, a storage barn with horse stalls and a detached man cave that would make a perfect home office or studio! With a private pier, dock, boat and jetski lifts, you can enjoy all that the Chesapeake Bay has to offer. Whether you're looking for a peaceful retreat or a place to entertain family and friends, this farmhouse is the perfect place. Welcome Home!
#MDAA2112080

ANNAPOLIS

1741 HOLLY BEACH FARM ROAD

5 Beds

3 Baths

2,775 Sq.Ft.

$3,800,000

MLS#: MDAA2112080

As you make your way down the quarter-mile private road, passing one of the area's last working farms and historic tobacco barns, you arrive at 1576 Bay Head Road—a breathtaking waterfront sanctuary in the historic enclave of Podickory Point. Set on over an acre of beautifully landscaped grounds and boasting 250 feet of unobstructed water frontage along the Little Magothy River, this stunning estate offers an unmatched lifestyle of luxury, tranquility, and effortless connection to the Chesapeake Bay. Built in 2015 with meticulous attention to detail, this 7,000 sq. ft. home invites you to immerse yourself in a world where everyday living feels like a vacation. Imagine spending the day out on the bay, crabbing, fishing, or exploring the waterways, and returning to your private 60-foot pier, where two boat slips and a spacious landing make docking a breeze. Fully equipped with water and electric, the pier becomes the heart of your waterfront living, whether you’re unloading the day’s catch or hosting friends for an impromptu evening of sunsets and cocktails by the water. Outdoor entertaining reaches new heights with two expansive decks that capture the beauty of the river. One deck is covered for a shaded, serene retreat, while the other features a retractable awning, giving you the freedom to bask in the sun or relax under the shade. These spaces are ideal for summer barbecues, holiday gatherings, or quiet evenings watching the changing colors of the sky reflect on the water. Step inside, and the home’s sophistication and warmth envelop you. Sunlight pours through walls of windows, illuminating a thoughtfully designed open floor plan that maximizes both comfort and function. The two-story family room, with its soaring ceilings and breathtaking water views, is a showstopper and the perfect backdrop for cozy evenings by the fire or lively family celebrations. The gourmet kitchen is a chef’s dream, featuring top-of-the-line stainless steel appliances, a six-burner stove, and an oversized island that’s perfect for preparing meals or gathering with guests over wine and laughter. Adjacent to the kitchen, the breakfast area offers a front-row seat to the river’s serene beauty, making casual meals feel extraordinary. The main-level primary suite is your private haven, where you can wake up to the soft glow of the sunrise over the water. Crown molding, a romantic coffered ceiling, and a spa-like en suite bath with a soaking tub and walk-in shower create a space that is as elegant as it is restful. Upstairs, three additional bedrooms and beautifully appointed baths provide ample space for family and guests, ensuring everyone feels at home. Downstairs, the fully finished basement is an entertainer’s paradise. Host movie nights in the private theater room, mix drinks at the wet bar, or let guests unwind in the recreation area while you enjoy a workout in the home gym. The seamless flow of this home makes it just as suited for grand celebrations as it is for intimate gatherings, with every detail designed to bring people together while still allowing for peaceful retreats. This property offers more than a home—it’s a lifestyle. Whether you’re crabbing from your dock, kayaking along the shoreline, or enjoying the simple pleasure of sitting on your deck as the water laps against the shore, life here feels unhurried, peaceful, and deeply connected to nature. Despite its serene setting, the home is ideally located just minutes from major commuter routes, including Route 50, I-97, and Route 2, and a short drive to downtown Annapolis, where you can enjoy dining, shopping, and cultural landmarks. Perfectly blending timeless elegance, modern convenience, and the unmatched beauty of the Chesapeake Bay, 1576 Bay Head Road is more than just a place to live—it’s a place to create memories, build traditions, and embrace the best of waterfront living. Don’t miss your chance to call this extraordinary property home.
#MDAA2101866

ANNAPOLIS

1576 BAY HEAD ROAD

5 Beds

5 Baths

7,000 Sq.Ft.

$3,625,000

MLS#: MDAA2101866

Boating season is here! Welcome to 1576 Bay Head Road, an exceptional waterfront estate where luxury living meets the ultimate Chesapeake Bay lifestyle. Perfectly situated on a private one-acre lot along the calm, protected waters of the Little Magothy River, this 6,700+ sq. ft. custom home offers the rare opportunity to be out on the Bay in under five minutes—just in time for boating season. Whether it’s a morning fishing run, an afternoon cruise, or a sunset sail with friends, this property was designed for those who live life on the water. Built in 2017 with meticulous attention to detail, this residence delivers refined design and modern comfort across three spacious levels. Step outside to your private 60-foot pier, fully equipped with water and electric, two boat slips, and a generous landing space perfect for docking, fishing, or simply soaking in the sunrise. The easy access to the open Bay makes this home a dream for boaters, water sports enthusiasts, or anyone craving the rhythm of coastal living. The outdoor spaces are designed to maximize the stunning waterfront setting. Two expansive rear decks—one covered, the other with a retractable awning—offer incredible versatility for lounging in the shade or basking in the sun. Whether you're hosting summer crab feasts, sipping cocktails at sunset, or enjoying quiet mornings with a cup of coffee, these spaces become an extension of your lifestyle on the water. Inside, soaring ceilings and walls of windows frame endless water views and flood the home with natural light. The two-story family room is a striking focal point, with dramatic volume and an open layout that seamlessly connects living, dining, and entertaining spaces. The gourmet kitchen is a chef’s dream, complete with top-of-the-line stainless appliances, a six-burner gas stove, oversized island, and breakfast area overlooking the river. The main-level primary suite is a private sanctuary, offering sweeping water views, a spa-like en suite bath, and exquisite details like a coffered ceiling, recessed lighting, and elegant crown molding. Upstairs, additional bedrooms are generously sized and beautifully appointed, offering comfort and privacy for family or guests. The fully finished lower level is built for entertainment and relaxation, featuring a private theater room, wet bar, home gym, office, and multiple recreation spaces—ideal for hosting gatherings or enjoying a quiet night in. Additional features include dual staircases, two fireplaces, hardwood and luxury vinyl plank flooring, energy-efficient windows, and a carefully designed flow that blurs the line between indoor comfort and outdoor beauty. At 1576 Bay Head Road, you're not just buying a home—you’re embracing a lifestyle where boating, nature, and refined living go hand in hand. The location offers the tranquility of a private riverfront retreat with the convenience of being minutes from Annapolis, major commuter routes, and everything the Chesapeake Bay has to offer. This is your season. This is your waterfront. Come experience it for yourself.
#MDAA2109848

ANNAPOLIS

1576 BAY HEAD ROAD

6 Beds

5 Baths

6,732 Sq.Ft.

$3,500,000

MLS#: MDAA2109848

An extraordinary opportunity to own a premier property in The Downs has arrived. This expansive contemporary on almost 2 acres offers over 5,000sqft of open living with direct views of Clements Creek from seven rooms and a 180ft pier. This home has some serious wow factors including; a hexagonal dining room... double entry doors...an enclosed hot tub area with river views...an exquisitely renovated primary bathroom and dressing room suite with radiant heat flooring...new water treatment system with reverse osmosis and UV filtering...a concrete reinforced wine cellar or panic room...a cozy, sunken seating area claims one side of the double-sided gas stone fireplace while the other side of the room offers panoramic views through a huge architectural picture window and sliding glass doors...the list goes on and on. A 3-level spiral staircase with additional views is tucked to one side of the home and accesses the gym, family room and primary bedroom which just adds to its overall uniqueness. Relax at night or wake up in your owners suite with yet another large picture window from the homes highest vantage point with jaw-dropping views of the water and your long, private pier. The pier has been outfitted with reinforced pilings to accommodate a 40,000lb boat lift which has already been permitted and electric has been run to the the end of the pier, one of the longest in the Downs community. Your new home comes with an abundant list of community amenities including a pool, clubhouse, tennis & pickleball courts, a playground and two marinas. Enjoy the perfect mingling of privacy, indoor/outdoor space, water views and an overall sense of a permanent vacation while still being close to Annapolis and with easy access to Baltimore and Washington DC. It truly is a DREAM!
#MDAA2105838

ANNAPOLIS

1486 DOWNHAM MARKET

6 Beds

4 Baths

5,020 Sq.Ft.

$3,500,000

MLS#: MDAA2105838

Quintessential downtown Annapolis waterfront home on the sparkling waters of Spa Creek! This amazing property combines the best of both worlds; the charming historic feel of a downtown Annapolis home with the premier waterfront lifestyle that every resident is looking for. Nestled on a quiet street, this home is the perfect size for an easy to own, lock up and go property. With 3 bedrooms and 2.5 baths it has all the elements needed to enjoy life to the fullest; either as the perfect weekend retreat or permanent residence. The Annapolis area and the surrounding waterways are sure to entertain in every season. The upper level of the home is dedicated to the spacious Primary suite with unique sitting area and expansive roof deck. Take in panoramic views of Spa Creek, Annapolis Harbor and Eastport. An unparalleled vantage point for sunrise coffee or sunset cocktails. The main level offers multiple cozy gathering areas including a formal living room with fireplace, home office and light filled gourmet kitchen with dining area. The kitchen area flows effortlessly into the dining area and out onto the rear deck overlooking Spa Creek. Perfect for gathers of all sizes and dining al fresco. The lower level provides an ideal retreat for family or guests with 2 spacious bedroom a full bath and a cozy family room with fireplace. Head out to the charming covered patio to read a book or sip your evening cocktail or venture out on the water from the private pier. The amazing location is walkable to everything Annapolis has to offer and Spa Creek provides quick access to the Chesapeake Bay and beyond. Welcome Home!
#MDAA2109630

ANNAPOLIS

9 SHIPWRIGHT STREET

3 Beds

2 Baths

2,621 Sq.Ft.

$3,495,000

MLS#: MDAA2109630

3015 Friends Road is perched on a stunning point of land where the South River meets the protected waters of Boyds Cove. The views down the South River towards the Chesapeake Bay are truly endless! This custom-built home with 456 ft of waterfrontage is everything you’d hope for in a modern waterfront retreat. Built in 2021, it blends contemporary design with the relaxed elegance of coastal living and every detail has been thoughtfully crafted to make life feel effortless. From the moment you walk in, you're welcomed by a soaring two-story foyer anchored by a dramatic light fixture — a striking first impression that sets the tone for the rest of the home. From there, the wall of glass overlooking the South River takes center stage and immediately lures you to the waterside. The heart of the main level is an open-concept great room featuring the kitchen with quartz waterfall, dining area, and family room with a stylish raised gas fireplace. The spaces flow easily in a bright, airy layout designed for both easy living and entertaining. The gorgeous, oversized island is perfect for casual meals, conversations, or hosting with ease. A walk-in pantry adds function, while beautiful light fixtures lend a contemporary, curated feel throughout the space. Step onto the spacious composite waterside deck, through 8 ft doors, which offers impeccable views, al fresco dining and comfortable seating areas. The layout is as flexible as it is beautiful. There’s a main-level water view bedroom (currently set up as an office) with a full bathroom. Upstairs, the primary suite is a peaceful escape, featuring a private office or sitting room that overlooks the water. The walk-in closet has been perfectly designed to handle an extensive wardrobe. The bathroom truly feels like a spa with deep soaking tub, custom tiled shower, WC and dual sink vanity. Two more bedrooms, each with their own bathroom, provide space and privacy for everyone. The finished, walk-out basement is a great place to hang out with friends, with its’ custom bar and space for a home theater. There’s also another bedroom, with sliding glass door to a waterside patio, and full bathroom. From the main level, there is access to an upstairs guest suite, thoughtfully designed to have a separate entrance and lots of closet space to provide guests with privacy and comfort. Outside, enjoy everything that makes living on the South River so special: a private pier tucked into a protected cove, multiple vantage points for soaking in the river views, an outdoor shower, and lush, thoughtful landscaping that frames the home beautifully. Around the corner by boat are multiple restaurants and fuel docks. This property offers the rare combination of a new home in pristine condition, panoramic views and protected pier, public water and sewer, and easy access to downtown Annapolis and Route 50.
#MDAA2114190

ANNAPOLIS

3015 FRIENDS ROAD

6 Beds

6 Baths

4,750 Sq.Ft.

$3,250,000

MLS#: MDAA2114190

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