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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

300

# of Listings

3

Avg # of Bedrooms

$467

Avg. $ / Sq.Ft.

$1,062,130

Med. List Price

Browse Annapolis Real Estate Listings

$250,000 - $500,000

$3M - $5M

12 Properties Found. Page 1 of 1.

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!

ANNAPOLIS

1632A WINCHESTER ROAD

5 Beds

4 Baths

5,000 Sq.Ft.

$4,950,000

MLS#: MDAA2110220

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.

ANNAPOLIS

54 RIVER DRIVE

4 Beds

4 Baths

3,250 Sq.Ft.

$3,995,000

MLS#: MDAA2100338

Life will never be the same. This slick and sleek coastal contemporary is beautifully designed for optimal waterfront living. With six bedrooms (FIVE ensuites), six full baths and one half bath, waterviews are visible from nearly all living spaces and bedrooms (and three bathrooms, to be fair). Witness the walls of windows on the first level, facing the Chesapeake Bay to the East and Severn River to the Northwest; one will never be bored with the marvelously incessant theatre of watercraft and nature. Enjoy morning coffee out on the open air patio, down at the pier, or in the large, screened porch. If weather is uncooperative, stretch out in the massive open living area, or retreat to one of two second floor water-facing rooms (one perfect for sitting room/office) to take in a new perspective. This home was fully renovated in 2017, sporting gorgeous custom light cherry 5" wood floors on the first and second level and showcasing unique custom, open staircases with black cable handrail system. There are two primary bedroom ensuites; one on the first floor featuring concrete shower floor, bathroom floor and cast concrete countertop. With generous, custom closets and oversized windows featured in each room, both residents and guests are guaranteed to render a five star rating for their stay and experience. This property is one block from 70 acres of walking trails and two blocks from the community beach, playground, picnic pavilion and firepit.

ANNAPOLIS

2514 LYON DRIVE

6 Beds

6 Baths

6,776 Sq.Ft.

$3,850,000

MLS#: MDAA2115858

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!

ANNAPOLIS

1741 HOLLY BEACH FARM ROAD

5 Beds

3 Baths

2,775 Sq.Ft.

$3,800,000

MLS#: MDAA2112080

A picture perfect piece of waterfront in Eastport with views across Back Creek out to the Bay bridge. This impeccable coastal craftsman style home is beautifully appointed making it turn-key for either a forever home or a fabulous weekend escape. A rare find to be nestled in the heart of Eastport located on a serene protected creek with pier and still have expansive views up the Chesapeake Bay all the way to the Bay Bridge. The highly sought-after Eastport location is conveniently walkable to everything Eastport and Annapolis has to offer. Tucked away in a small enclave of homes, this magnificent custom home with 2 car garage was custom built to the highest standards and boasts the perfect floor plan for enjoying the water views. The community pier services the 10 homes (5 single family and 5 townhomes) in the community and your deeded boat slip is located right in your backyard with 20,000lb boat lift and 8' MLW. Inside, the thoughtful floorplan combines an open floor plan with cozy spaces for easy entertaining for small or large gatherings. Featuring beautiful hardwood floors, extensive millwork, gourmet Kitchen, 2 fireplaces, high ceilings and walls of windows that expertly capture the water views. The soaring ceilings, magnificent views, adjoining office, sitting area, fireplace, multiple balconies and spa-like bath makes the Primary's suite a relaxing private retreat to begin and end every day. The main level bedroom suite provides flexibility for one level living and with 5 bedroom, 4 full baths, 2 half baths there is plenty of room for family and friends. Outside the waterside deck and patio across the back of the home is great for dining al fresco on cool summer nights and the lush backyard is perfect for entertaining. Stroll the artful and nautical streets of Eastport to amenities like: restaurants, pubs and street-end parks. Not to mention you are merely steps away from downtown Annapolis and Naval Academy attractions. From this location, just a short cruise on Back Creek and you can venture off to some of the Bay's best cruising and fishing areas or take a turn up Spa Creek and cruise into downtown Annapolis. The historic 18th-century seaport town of Annapolis, Maryland is America's sailing capital. Annapolis offers the perfect balance of small-town charm and big world sophistication. Welcome Home!

ANNAPOLIS

4 LITTLE HARBOR WAY

5 Beds

4 Baths

5,186 Sq.Ft.

$3,800,000

MLS#: MDAA2123802

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!

ANNAPOLIS

9 SHIPWRIGHT STREET

3 Beds

2 Baths

2,621 Sq.Ft.

$3,495,000

MLS#: MDAA2109630

Boating season is here! Incredible opportunity - Seller will hold a 10% second mortgage at 5.87% for five years if you are putting a minimum of 20% down! 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.

ANNAPOLIS

1576 BAY HEAD ROAD

6 Beds

5 Baths

6,732 Sq.Ft.

$3,475,000

MLS#: MDAA2109848

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.

ANNAPOLIS

48A E LAKE DRIVE

4 Beds

3 Baths

4,150 Sq.Ft.

$3,395,000

MLS#: MDAA2124834

#MDAA2119714

ANNAPOLIS

1486 DOWNHAM MARKET

5 Beds

4 Baths

5,260 Sq.Ft.

$3,250,000

MLS#: MDAA2119714

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.

ANNAPOLIS

3015 FRIENDS ROAD

6 Beds

6 Baths

4,900 Sq.Ft.

$3,250,000

MLS#: MDAA2114190

Welcome to 3307 Harness Creek Road-- a Nantucket style, coastal home with spectacular water views, a private backyard oasis and two deep-water piers on protected Harness Creek. This waterside gem, with 190 ft of waterfrontage, is situated directly across from Quiet Waters Park and offers quick access to the South River and the Chesapeake Bay.
Inside, you’re greeted by the natural warmth pouring in from the numerous floor-to-ceiling windows on the main level. The foyer starts a seamless transition to the living room on one side and the kitchen on the other. A central island draped by granite countertops centers the kitchen. Casual and formal dining options make the home great for entertaining. Adjacent to the kitchen is a walk-in pantry with quartz counters, sink and additional storage. The washer and dryer are also conveniently located here.
A cozy sitting area surrounded by bay windows shifts into the main living area. This space features many special details: a wood-burning fireplace, a window seat, and immediate access to the waterside ipe decks. Gorgeous hardwood floors are throughout the house. Closets and a powder room complete the main floor layout.
As you approach the staircase to go upstairs, you’ll notice the beautiful ribbon striped Sapele treads and one-of-a-kind detailing in the railing construction that add another creative touch to this special home. The two-story sitting area brings the natural light into the stairwell. The primary suite includes a spacious bedroom with fabulous Harness Creek and Quiet Waters Park views. The ensuite bathroom has a double-bowl vanity, soaking tub, and oversized shower with glass tile accent. There are two additional water view bedrooms upstairs and an updated hall bath.
On a coveted street close to downtown and providing easy access to Routes 97 and 50, a short walk to the local winery, or a paddle to hiking trails in Quiet Waters Park, this home’s prime location and modern interior make it the perfect combination of boater’s heaven and entertainer’s dream.
One of the best features of this property is the privacy in the lush, waterside yard. Adjacent to the main level living room, there is a spacious ipe wood deck with standing seam metal roof. Relax here and watch the paddlers on Harness Creek and the parade of boats and wildlife. With beautiful landscaping and hardscape, the sumptuous yard adds to the serenity of the waterfront scenery. The two private piers complete with water and electric offer tons of options for the serious boater. One pier is 46 ft and includes a 20,000 lb boat lift, 30/50 amp. electric, fresh water supply and has 5+ ft water depth. The second pier, with fresh water supply, is 76 ft long and can accommodate a sizable sailboat; here, the water is 8 ft at mean low tide. The outdoor spaces and interior detailing work in tandem to create a polished encapsulation of coastal living in Annapolis.
Major system updates include: new two zone high-efficiency 21 SEER Bosch HVAC systems (2024, 2023), treated water for irrigation, sprayed foam insulation in crawl space, new refrigerator, Dacor dual fuel range with propane cooktop, exterior landscape lighting, alarm system, freshly painted interior, new window treatments, and a new roof in 2022.

ANNAPOLIS

3307 HARNESS CREEK ROAD

3 Beds

2 Baths

2,236 Sq.Ft.

$3,195,000

MLS#: MDAA2120606

**Open House Saturday 8/16, 11-1 pm** Welcome to 856 St Edmonds Place! Have it all with stunning views from nearly every room, deep water, privacy, and a spacious floorplan for multi generational living! Spectacular custom built waterfront home in the sought after Downs community of Annapolis! Breathtaking views await you from every corner of this updated and well conceived home. Dramatic details throughout highlight the open floorplan and entertaining is a dream! Gourmet Kitchen with high end appliances, light filled formal dining room, soaring ceilings and imposing stone fireplace highlight the gathering room, cozy waterside family room off the kitchen, amazing primary suite with floor to ceiling windows and luxurious bath and oversized closet, two additional bedrooms and a full bath complete the upper level, bright and airy lower level with family room, theater, two additional bedrooms with en suite baths and plenty of storage, enjoy the flexibility of an enormous maintenance free deck and a stunning screened porch, attached two car garage and additional detached one car garage with amazing 1 BR/1Bath updated in law suite/caretaker space, whole house generator, new tram and steps for convenient access to your pier with covered slip, two new boat lifts and jet ski lift nestled perfectly on Brewer Creek with quick access to the Severn River and the Chesapeake Bay! Located close to the community pool and sports courts with an an easy commute to Washington DC, BWI and Baltimore!

ANNAPOLIS

856 ST EDMONDS PLACE

5 Beds

4 Baths

6,595 Sq.Ft.

$3,100,000

MLS#: MDAA2105068

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