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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

389

# of Listings

3

Avg # of Bedrooms

$475

Avg. $ / Sq.Ft.

$1,078,449

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

389 Properties Found. Page 4 of 26.

Exciting Opportunity in Sherwood Forest – Enjoy breathtaking panoramic water vistas of Brewers Pond and Round Bay on the Severn River. Observe Bald Eagles, Herons, and Osprey soaring amidst the stunning backdrop from your water view deck or spacious living room adorned with floor-to-ceiling windows. This elegantly designed home, nestled in the hillside, seamlessly blends modern amenities with the charm of a traditional cottage. Situated on one of the most secluded homesites in Sherwood Forest, ample parking is available for entertaining family and friends. Sherwood Forest is a prestigious gated community comprising 341 residences. Residents enjoy access to a plethora of amenities including a spacious multi-purpose Club House, General Store, 9-Hole Golf Course, 6 Tennis Courts, Marina, Beaches, Swimming Pool, Basketball Court, Bowling Alley, Pickle Ball Courts, Archery Pit, Nature Lab, and a renowned Children’s Summer Camp Program. Numerous fields throughout the neighborhood cater to various sports such as Lacrosse, Soccer, Football, Softball, Volleyball, and Badminton. The surrounding forest boasts over 5 miles of scenic walking and mountain biking trails, with a picturesque 2-mile waterfront loop offering captivating views of the Severn River and Brewers Pond. Golf carts are the preferred mode of transportation within the community. The vibrant social calendar is filled with events including the 3rd of July Fireworks, 4th of July Parade, Summer Dances, 5K Race, Corn Roast, Clam Bake, Tennis and Golf Tournaments, and much more. Holiday festivities cater to both adults and children alike. A one-time $20,000 membership fee to join the Sherwood Forest Club is required as part of your Real Estate Transaction.

ANNAPOLIS

201 NOTTINGHAM HILL

5 Beds

3 Baths

2,353 Sq.Ft.

$2,200,000

MLS#: MDAA2115758

Wonderful waterfront home located on deep Oyster Creek with direct access to the Chesapeake Bay! Sprawling three levels of waterfront views fronted by large screened in porches, the home provides great areas for entertaining with a blend of coastal living. Custom-built in 2004 by a former midshipman, this energy efficient property is equipped with two separate Geo Thermal HVAC systems that keep the home comfortable year-round with fractional energy costs compared to comparable and even smaller homes on standard systems. Inside, the home boasts hardwood flooring, 9-foot ceilings, and large Anderson windows with views overlooking the water and private pier, which is equipped with water and electricity. Natural light beams into the living areas of the home, which feature wood burning-fireplaces located on two of the three levels. Crown and wall moldings throughout emphasize the custom craftsmanship that was put into the home when built. A modern kitchen with a cooktop and double wall oven are paired with granite countertops. The kitchen leads to the main eating and living area overlooking Oyster Creek with the Chesapeake Bay in the distance. A large master bedroom with a tray ceiling sits atop the third level with two individual decks perfect for enjoying a morning beverage. Two separate walk-in closets in the master provide ample space for all wardrobe needs. Master bath includes a jetted tub, walk in shower and double vanity. Main entrance level is highlighted by a beautiful cherry wood bar complete with accompaniments including a wine fridge, mini fridge, kegerator and highlighted by built in shelving. This area sets the tone for entertaining as guests can walk out onto the two-level screened in porch connected by a spiral staircase. The exterior lawn area is complete with hardscapes, lighting and irrigation systems. The rear patio and large yard along Oyster Creek provides plenty of space for outdoor gatherings, badminton, and volleyball. The waters edge is solidified by rip rap leading to the private pier, with a mean low water depth of 4 feet, ready for your boat. Of note, this home is also NOT in a flood plain, and does NOT require flood insurance.
This incredible home is located just minutes away from downtown Annapolis and Eastport. The Community provides a gated private beach on the Chesapeake Bay complete with a new playground within walking distance, along with community piers for boating and fishing.
Interior pictures COMING SOON!

ANNAPOLIS

1242 WASHINGTON DRIVE

5 Beds

4 Baths

3,687 Sq.Ft.

$2,100,000

MLS#: MDAA2105588

Seller has obtained Approval to construct an on-site sewage disposal system. System to be installed by and at cost of buyer. See approval in online documents with approval to construct and approved septic site plan. Limited Home Addition has been granted with conditions set forth in documents and agreement that can be shared to interested parties. Don't miss your opportunity to build on one of the most scenic waterfront properties with magnificent views of the South River that was once the site of a part of Annapolis' ferry boat history, Boasting 1.15 acres and approximately 200' of frontage, property has existing pier (in need of repair or replacement). Tax card reflects the previously existing boat house so may have potential to rebuild boathouse (Buyer's responsibility to verify).

ANNAPOLIS

400 FERRY POINT ROAD

4 Beds

2 Baths

5,814 Sq.Ft.

$1,900,000

MLS#: MDAA2053852

GET READY FOR YOUR BEST SUMMER EVER! This waterfront home is nestled in one of Annapolis’ sought-after neighborhoods. Inviting and beautiful décor punctuates views of water and private setting. Tons of windows and flooded with light! Conversational style living room opens to formal dining in a comfortable traditional layout. Stunning kitchen is surrounded by windows and features a large island, gas range, and plentiful cabinets. Kitchen dining area overlooks natural wooded vista. Stone-faced fireplace is the focal point in the bright family room that leads to a large deck and features waterviews. Rich warm wood floors flow from room-to-room throughout! Primary suite features water views, gas fireplace, plantation shutters, and a stunning bath with soaking tub, glass shower & separate sinks. Large walk-in closet has custom shelving. Full laundry on second-level. Two additional bedrooms and baths have been beautifully updated with designer touches. Lower level features a third fireplace, wet bar, and glass sliders to the back yard. Great for a fifth bedroom or an office! New custom steps and walkway lead down a gentle slope to the private dock (4 feet MLW). Your neighbors will include herons and turtles as the headwaters of Lake Ogleton offer a quiet respite for all! Whether you like to kayak or want to power or sail out to the Chesapeake Bay, you will have quick access to all the water activities Annapolis has to offer. Lake Ogleton is a water skier's heaven and the open waters of the Chesapeake are a sailor's paradise. Annapolis Roads has a private community beach and picnic area on a bluff with stunning views of the Severn River and the Chesapeake Bay. This established community is convenient to the restaurants and marinas in Eastport or to major commuter routes. New HVAC 2019, New Hot Water Heater 2020, New HVAC 2022. Annapolis Roads is a Special Tax District, and the HOA is included in the annual property owners tax.

ANNAPOLIS

2656 QUEEN ANNE CIRCLE A

4 Beds

4 Baths

3,315 Sq.Ft.

$1,850,000

MLS#: MDAA2111166

New on site 1 day ago

Gorgeous, One-of-a-Kind Luxury Penthouse in Downtown Annapolis!
Welcome to this stunning 3-bedroom, 3.5-bathroom penthouse condo in the exclusive Acton’s Landing community—offering an unparalleled blend of historic charm and sophisticated modern living. With private elevator access, deeded use of two garage parking spaces, and two expansive balconies with breathtaking skyline views, this residence is truly exceptional.
Thoughtfully designed to capture natural light from sunrise to sunset, the open floor plan features a gourmet kitchen boasting Silestone countertops, custom tile backsplash, custom cabinetry, new refrigerator, new dishwasher, gas cooking, wine fridge, under cabinet lighting, and updated fixtures.
Recent upgrades include new HVAC system, new hardwood flooring, and new high-end wall to wall carpet in the 3 bedrooms, new dining room chandelier. The powder room and main level ensuite bath has been updated. The laundry room has custom built-in cabinetry, new flooring, new washer, dryer, and 2 refrigerated beverage drawers. Entire unit freshly painted for a crisp, modern feel.
Residents of Acton’s Landing enjoy first-class amenities: secure entry, on-site property management and assistant, a fitness center, recreation and meeting rooms, library, and a beautifully landscaped courtyard with a central fountain.
Steps from Acton’s Cove waterfront park, boutique shopping, fine dining, the U.S. Naval Academy, Maryland State House, and the Governor’s Mansion—this is the perfect fusion of urban convenience and tranquil retreat.
Don’t miss this rare opportunity to live in one of Annapolis’ most coveted locations!

ANNAPOLIS

66 FRANKLIN STREET 509

3 Beds

3 Baths

2,477 Sq.Ft.

$1,850,000

MLS#: MDAA2116316

Location, location, location! INVESTOR alert for an apartment unit building that can be converted to a single family home in historic Annapolis! This property is steps away from city dock and all that downtown Annapolis has to offer! Enjoy incredible views of historic Annapolis & Spa Creek. The Red Brick Inn is currently being used as a full time Airbnb, but it can easily be converted to a single family home. There are a total of three separate apartments that have all been updated in 2014 and are all separately metered. Floor plans and additional information available upon request! Don’t miss out on this one!

ANNAPOLIS

15 NEWMAN STREET

7 Beds

None Baths

3,509 Sq.Ft.

$1,799,999

MLS#: MDAA2016852

FABULOUS PENTHOUSE. Embrace a lifestyle of unparalleled luxury and breathtaking views with this rare opportunity to own an exquisite penthouse at the GrandView in Annapolis Town Center. Perched atop the prestigious 12th floor, this sprawling residence stands as one of the most coveted penthouses, offering panoramic views that stretch for miles, complemented by two expansive balconies that provide front-row seats to the vibrant holiday events and outdoor venues of the Town Center.

Step inside to discover a world of refined elegance, where light cascades through oversized windows, illuminating the dramatic 11-foot ceilings that stretch overhead, creating an atmosphere of open, airy sophistication. This penthouse boasts an expansive layout, featuring three private ensuite bedrooms, each a serene retreat of comfort and luxury. A large den offers flexibility for your lifestyle, whether as a home office, media room, or additional guest space, ensuring this home meets your every need. Newly installed 2-Zone HVAC system and new washer and dryer.

The heart of this home is the open floor plan, seamlessly connecting living spaces with Brazilian cherry hardwood and ceramic tile floors underfoot, exuding warmth and timeless elegance. The gourmet kitchen is a chef's dream, outfitted with high-end appliances, sumptuous granite countertops, and a massive kitchen island, making it perfect for hosting gatherings or savoring quiet moments over coffee.

GrandView isn’t just a residence; it’s a community that offers a true sense of belonging. Residents enjoy exclusive access to a rooftop sky lounge and pool, an outdoor kitchen, a state-of-the-art fitness center, and a club/party room, all designed to foster a lifestyle not just of luxury, but of wellness and social connectivity. The addition of a professionally managed concierge staff ensures every day is lived with ease, convenience, and security.

Situated in the heart of Annapolis, GrandView places you just a stroll away from the finest dining, Whole Foods, Target, Life Time Fitness Club, banking, and boutique shopping. Historic downtown Annapolis, the US Naval Academy, Anne Arundel Medical Center, and Annapolis Mall are mere minutes away, making this a dream location for commuters with quick access to Route 50 and 97.

Seize this unmatched opportunity to indulge in refined urban living at its most sophisticated. Schedule your showing today and take the first step into a life filled with luxury, comfort, and breathtaking beauty in this unparalleled penthouse residence.

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 1210

3 Beds

3 Baths

3,520 Sq.Ft.

$1,750,000

MLS#: MDAA2103424

#MDAA2109866

ANNAPOLIS

146 PRINCE GEORGE STREET

4 Beds

2 Baths

2,550 Sq.Ft.

$1,750,000

MLS#: MDAA2109866

Custom coastal craftsman home is currently under construction in Eastport - Annapolis, Maryland. This home will feature a perfect blend of classic Eastport and luxury coastal craftsman design. Permitting is complete. This expansive 3600 +/- (approx. 850 unfinished) sq. foot home will offer 4 bedrooms and 3 baths with an open floor plan concept. Truly an entertainer’s dream with hardwood floors, high ceilings, impressive millwork and trim, walk-in closets, beautiful gourmet kitchen, large rooms with multiple dining and gathering areas, and a fully finished basement. The second level of the home offers three bedrooms including the owner’s suite. The suite features a fireplace and master bath with dual vanity, frameless glass shower and soaking tub. The builder did not leave anything out, by placing an office or bedroom on the main level and washer and dryer on the second floor for convenience. The exterior of the home will include a charming front porch, back deck for hosting seasonal barbecues, and ample green space in the rear. A landscaping package is included, as well as 3 off-street parking spaces. Walkability to downtown Annapolis including premier restaurants, shopping, yacht clubs, water activities, and more... Take advantage of this rare opportunity to purchase Eastport new construction.

ANNAPOLIS

400 JEFFERSON STREET

4 Beds

3 Baths

3,640 Sq.Ft.

$1,700,000

MLS#: MDAA2032362

Unprecedented opportunity in The Community of Chesapeake Harbour! Gated Chesapeake Harbour offers lavish Chesapeake Bayfront Annapolitan style living. The pinnacle of style and luxurious refinement now available! 4 Levels of spectacular waterfront perfection masterfully done with nothing to do but unpack your toothbrush and head to your marina front deck for happy hour and stunning summer sunsets. Fully renovated and professionally custom designed upgrades from Kitchen Encounters to Baths including Heated Bathroom Floors (all 3 Full), Robern Medicine cabinets, Hansgrohe fixtures, Miele Steam and convection ovens, Thermador Fridge, waterfall island, wine/beverage center, 15K+ of lighting fixtures, Calcutta Italian Marble surround Napolean LED fireplace, new Pella doors, HVAC, all new interior and closet doors with custom closets just to start!!! Please contact listing agent for complete list.
A transformation of over $500,000 in timeless luxe finished renovations to create the space of your dreams. Offering casual elegance and extreme comfort, you will not want to leave your new home but when you do -walk to the private sandy beach to watch the Blue Angels, enjoy sunny days at the Chesapeake Bay waterfront pools, play pickleball/tennis with neighbors and meet new friends for cocktails and sunset dinners at Waterside Beacon Bar and Restaurant. Lots of social events and Beacon has live music on most weekends! Perfection awaits. It doesn’t get better than this in this premiere exclusive resort style Annapolis community. Please see the interactive floorplan under virtual tours for additional photos and information.

ANNAPOLIS

2186 CHESAPEAKE HARBOUR DRIVE

3 Beds

3 Baths

2,719 Sq.Ft.

$1,700,000

MLS#: MDAA2108174

Unprecedented waterfront opportunity in The Community of Chesapeake Harbour! Unduplicatable Gated Chesapeake Harbour offers lavish Chesapeake Bayfront Annapolitan style living. This community could never be built today and this property completes the trifecta with perfect location and luxurious refinements. 4 Levels of spectacular waterfront perfection masterfully done. Fully renovated and professionally custom designed finishes cannot be duplicated and never at this price *Kitchen Encounters to Baths including HEATED Bathroom Floors (all 3 Full), Robern Medicine cabinets, Hansgrohe fixtures, Miele Steam and convection ovens, Thermador Fridge, waterfall island, wine/beverage center, 15K+ of lighting fixtures, Calcutta Italian Marble surround Napolean LED fireplace, new Pella doors, HVAC, all new interior and closet doors with custom closets just to start!!! A transformation of over $500,000+ in timeless luxe finished renovations to create the space of your dreams can be yours! Offering casual elegance and extreme comfort, you will not want to leave your new home but when you do -walk to the private sandy beach to watch the Blue Angels, enjoy sunny days at the Chesapeake Bay waterfront pools, play pickleball/tennis with neighbors and walk with new friends for cocktails and sunset dinners at Waterside Beacon Bar and Restaurant. Lots of social events, groups and Beacon even has live music on most weekends! Perfection awaits. It doesn’t get better than this in this timeless premiere exclusive resort style Annapolis community. Please see the virtual walk through and interactive floorplan under virtual tours for additional photos and information.

ANNAPOLIS

2186 CHESAPEAKE HARBOUR DRIVE E

3 Beds

3 Baths

2,719 Sq.Ft.

$1,700,000

MLS#: MDAA2116414

Welcome to 743 Rolling View Drive in the coveted waterfront community of Cape St Claire. This beautifully maintained home offers over 3,800 square feet of finished living space, including 4 bedrooms, 3.5 bathrooms, and a potential 5th bedroom in the basement. Set on over half an acre with expansive views of Deep Creek leading to the Magothy River, this is a rare opportunity for spacious, move-in-ready waterfront living.

The main level features an open-concept layout with large windows framing serene water views. A custom chef’s kitchen anchors the space with Quartz and natural wood countertops, stainless steel appliances—including a double wall oven, induction cooktop, microwave, refrigerator, and dishwasher—and radiant heated floors. The kitchen flows seamlessly into the main living and dining areas, accented by hardwood flooring and wood beam details. A propane fireplace adds warmth to the adjacent library, which also includes built-in shelving and a full bath—ideal for guests or flexible living. A main-level bedroom includes a built-in Murphy bed, offering excellent functionality as an office or guest suite.

Upstairs, the primary suite is a luxurious retreat with two walk-in closets and a spa-like en suite bath featuring radiant heated floors, a clawfoot soaking tub, dual vanities, and a custom mosaic tile shower with artistic tilework, including heron and rockfish detailing. Two additional bedrooms, a full hallway bath, and a convenient top-floor laundry room complete the upper level.

The finished basement provides additional living space with tile flooring, a wet bar with mini fridge and storage, a half bathroom, walk-out access to the backyard, and a flexible space that could serve as a 5th bedroom or office.

The mudroom entry off the detached two-car garage includes custom cubbies, heated flooring, and a built-in commercial-grade ice maker—perfect for stocking coolers or entertaining. Dual-zone HVAC ensures year-round comfort, and the roof and windows have been updated in recent years and remain in excellent condition. A whole-house generator offers added peace of mind.

Outdoor living is just as impressive: a composite wraparound deck with trellis, custom stone patio with built-in fire pit, and mature landscaping create a peaceful backdrop. Follow the custom paver walkway with concrete steps down to a private pier equipped with two boat lifts, a kayak launch, water and electric hookups, and a waterfront storage shed with power. A screened-in porch at the top of the steps with electricity offers the perfect setting to unwind after a day on the water. The home also features a fenced yard, invisible pet fence, and a long driveway with ample parking.

Community amenities include three private beaches, three marinas, multiple parks, a rentable clubhouse, a local shopping center, and seasonal events such as the 4th of July celebration and the Strawberry Festival. Located in the Blue Ribbon Broadneck School District, this home delivers the very best of Annapolis waterfront living.

Special Buyer Incentive! Get a Lower Rate – On Us!
If you choose to work with the seller’s preferred lender, you’ll receive a 1% Temporary Rate Buydown for the First Year that means lower monthly payments for you—at no cost to you as the buyer! Take advantage of this limited-time opportunity to make your new home even more affordable. Ask me for details during your visit today!

ANNAPOLIS

743 ROLLING VIEW DRIVE

4 Beds

3 Baths

3,827 Sq.Ft.

$1,650,000

MLS#: MDAA2109136

New on site today

Stunning Waterfront Coastal Retreat on Oyster Creek with Breathtaking Sunsets! This exceptional 4-bedroom, 4-bathroom home is perfectly situated on the shores offering unique views of the Chesapeake Bay and Oyster Creek from nearly every room. Step inside to discover the open design, highlighting a gourmet kitchen designed for both beauty and function, featuring granite countertops, stainless steel appliances, and breakfast bar. The open-concept living and dining areas flow easily out to the multi-level waterfront decking, ideal for entertaining or simply enjoying the peaceful surroundings. The luxury primary suite is a true sanctuary, complete with a private waterfront deck, spa-like bathroom featuring a walk-in shower, soaking tub, and a generous walk-in closet. The third-level living space includes a full bath and offers endless possibilities—perfect as a media room, guest suite, or home office with elevated views.
Outside, a private pier with a 9,000 lb boat lift invites you to explore the water with ease. Whether you're boating, fishing, or just soaking in the serene creekfront setting, this property offers the ultimate coastal lifestyle. Don’t miss this rare opportunity to own a slice of waterfront paradise on Oyster Creek. Property is in a Special Tax District. - $2,274.75 annually.

ANNAPOLIS

3300 SHORE DRIVE

4 Beds

4 Baths

2,798 Sq.Ft.

$1,650,000

MLS#: MDAA2116986

This modern ('85) 4 bedroom/2 full- 1 half- bath home, sits on the largest lot (1.5 acres) in the coveted Providence community, borders the USNA Golf Course, and is the largest estate lot currently available in Annapolis. The lucky buyer will become a member of the private Providence Club, a $10 million "clubhouse" which includes an 8-year new clubhouse, pool and kids play area all with unparalleled views of the Bay, and its own private marina; which is the closest marina to the Bay on the Severn River. The Providence HOA heavily-subsidizes the marina, so boatowners not only enjoy the best direct Bay access on the Severn, but slip fees (including dry, on-site winter storage) that are a fraction of market marina rates. Enjoy seamless indoor-outdoor living with a screened-in porch—the perfect setting for morning coffee, quiet conversation, or sunset wind-downs. The expansive back deck invites al fresco dining and elevated summer entertaining, framed by the tranquil beauty of this remarkable estate. Inside, the home boasts 4 bedrooms (with potential to expand to 6), 2.5 baths (option to add another full bath), hardwood floors, a modern, light-filled design, and a finished walkout basement. A front-entry garage, extended private driveway, and abundant storage spaces enhance the home's effortless livability. A truly rare opportunity in the prestigious Providence community—without comparison and without compromise. Discover the unmatched elegance, privacy, and lifestyle this estate offers. Schedule your private tour today and experience Annapolis luxury at its finest!

ANNAPOLIS

210 PROVIDENCE ROAD

4 Beds

2 Baths

2,926 Sq.Ft.

$1,650,000

MLS#: MDAA2115356

Welcome to this exceptional 3-unit property located in the vibrant heart of downtown Annapolis—truly an investor's dream. These turnkey apartments are currently licensed for short term rentals and ready to offer a rewarding investment opportunity.

Situated in the bustling core of Annapolis, this property provides unparalleled access to the city's rich array of dining, shopping, and entertainment. Guests will delight in the diverse dining scene, with popular spots like Iron Rooster, Tsunami, and Osteria 177 offering a range of culinary experiences. Located steps from Gate 1 of the United States Naval Academy makes it one of the most desirable locations for both long and short term guests.

Shopping enthusiasts will find plenty to explore, from charming boutiques and gift shops to unique pottery stores. When the sun sets, Annapolis comes alive with nightlife options, including Dining Under the Stars events, live music at Rams Head Tavern, and a variety of bars and pubs for a perfect evening out.

For those seeking recreation and adventure, the area offers an abundance of activities. Visitors can enjoy the serene beauty of Quiet Waters Park, take sailboat lessons, embark on fishing charters, explore ghost tours, or visit local museums. The proximity to the US Naval Academy, just a block away, adds to the allure of this sought-after tourist destination.

This property not only offers a prime location but also the potential for a lucrative return on investment. Don't miss the chance to own a piece of Annapolis's thriving downtown scene.

ANNAPOLIS

165 KING GEORGE STREET

4 Beds

None Baths

2,595 Sq.Ft.

$1,599,000

MLS#: MDAA2103044

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