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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
272
# of Listings
3
Avg # of Bedrooms
$428
Avg. $ / Sq.Ft.
$925,284
Med. List Price

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272 Properties Found. Page 3 of 19.

A rare opportunity for a well located worship facility on 23 acres in Cape St. Claire with exceptional frontage on Rt 50. This large complex with extensive acreage allows a congregation an unusual and great opportunity to grow or fund itself. Existing complex can be restored and used with a great opportunity for later expansion for a larger facility on the additional acreage. Selling addition acres for subdivision may be possible. Available preliminary engineering supports subdivision possibilities. This facility's main room is big enough for 175 and building boasts over 4600 total sq ft, includes a kitchen with serving bar, study, multipurpose room, foyer and reception desk, offices, and classrooms. Noteworthy architectural features include palladium windows, exposed brick, beamed ceilings and a custom staircase. The main building will require less updating and the parsonage, once used as offices, will require significant renovation. Property sold as-is, where-is. Zoning is residential and supports some commercial uses. See attached zoning table for R1 uses. All uses will require certificate of use and occupancy.
#MDAA2123582

ANNAPOLIS

1016-1024 E COLLEGE PARKWAY

None Beds

None Baths

4,473 Sq.Ft.

$1,995,000

MLS#: MDAA2123582

23-acre parcel zoned primarily R-1, with some O-S. Preliminary engineering work indicates the property can be subdivided and coul support multiple residential lots. The concept drawing attached.
#MDAA2123584

ANNAPOLIS

1016 E COLLEGE PARKWAY

None Beds

None Baths

23.33 acres

$1,995,000

MLS#: MDAA2123584

Elegant charm meets modern convenience in this one-of-a-kind residence located in the heart of Murray Hill. Offering the very best of the downtown lifestyle, this remarkable property boasts a chef’s kitchen with custom cabinetry, granite counters, and high-end appliances and soaring ceilings. The stunning Living room with gas fireplace and light filled dining area flows seamlessly to the picturesque gardens in the front yard to the elegant fountain in the back. Elevator service to all levels provides ease, while the spacious primary retreat encompassing the entire top floor includes a sitting room/office, private covered porch, and breathtaking views of Spa Creek and the iconic Annapolis skyline. Unmatched in both location and amenities, this residence includes a rare downtown garage, plenty of parking, multiple guest suites for friends and family, and elegant details throughout—from granite foyer floors to a library and breakfast room filled with light and curated finishes. Whether entertaining in style or enjoying a quiet evening watching the boats glide by, this home represents the finest package in the city: an extraordinary blend of history, luxury, and walkable convenience just steps from everything downtown Annapolis has to offer. Welcome Home!
#MDAA2129932

ANNAPOLIS

2 SOUTHGATE AVENUE 10

3 Beds

2 Baths

3,884 Sq.Ft.

$1,975,000

MLS#: MDAA2129932

Embrace the Eastport lifestyle in this charming craftsman just steps from the water and downtown Annapolis. This beautifully maintained home offers 4 bedrooms, 3.5 baths, an elevator, and sitting areas on each level. The reverse floor plan features a gourmet kitchen, dining area, and living room with fireplace and wood floors. The second level primary suite has a private deck and spa-like bath. The entry level includes an en suite bedroom with deck and hot tub access, 2 additional bedrooms and hall bathroom. Enjoy seasonal Back Creek views from the upper balcony and relax in the spacious yard with pergola and hot tub. A rare driveway with 2 car detached garage and finished space above offers endless options. Walk to restaurants, pubs and parks. Perfect blend of Eastport charm and coastal sophistication!
#MDAA2128708

ANNAPOLIS

215 CHESTER AVENUE

4 Beds

3 Baths

3,720 Sq.Ft.

$1,895,000

MLS#: MDAA2128708

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!
#MDAA2116316

ANNAPOLIS

66 FRANKLIN STREET 509

3 Beds

3 Baths

2,477 Sq.Ft.

$1,850,000

MLS#: MDAA2116316

This fantastic property with over 100 feet of waterfrontage is ideally located on a protected cove minutes from the Severn River and the Chesapeake Bay. The .69 acre property boasts lovely views from Lake Ogleton to the Bay Bridge from its perfect perch on a gentle sloping hill. The shoreline is bulkheaded and there is a private pier with good water depth and lots of great dockage for all your watercraft. The original structure was one of the first in the neighborhood and has a two-story addition with a large kitchen and primary suite. The original house features spectacular views, charming living and dining rooms, two main-level bedrooms, and a fabulous sunroom. The expansive kitchen opens to the waterfront family room and has plenty of room for entertaining. On the private 2nd level, there are sweeping waterviews, a huge primary bath, ample closets and a sitting area. The house, safely located outside of flood plains, is currently not in the HOA. The new owner may choose to join the HOA for a reasonable fee. Community offers a marina, waterfront parks and more.
#MDAA2129604

ANNAPOLIS

3137 CATRINA LANE

3 Beds

2 Baths

2,970 Sq.Ft.

$1,750,000

MLS#: MDAA2129604

An exclusive and rare opportunity could be yours! Welcome to 51 Franklin, consisting of 9 high-end boutique units, developed by John Pilli & constructed by Gate One custom builders in 2020. Located at the intersection of Murray Hill and the city's Historic District, this exquisite condo provides high-end finishes including Legno-Bastone wide-plank hardwood flooring, Caesarstone waterfall counters, Omega cabinetry, Thermador & Wolf appliances, and beautiful designer plumbing and lighting fixtures. California Closets in all bedrooms, pantry and coat closet. Airy ten foot ceilings. Amenities include elevator, rooftop terrace w/luxurious views, secured covered garage parking with 2 assigned spots per unit, extra storage unit 3 steps from condo entry, gas cooking and water usage. Easy walking to Main St, the West St Arts District, and all points Downtown Annapolis...a true lock and leave experience for the next fortunate Owner! SEE VIDEO 'TOURS' FOR IN DEPTH INFO ABOUT THIS SMALL, EXTRAORDINARY HIGH END CONDO BUILDING DESIGNED BY THE ARCHITECTS OF FOURTH STREET DESIGN, AND BUILT BY JOHN PILLI AND GATE ONE BUILDERS
#MDAA2127792

ANNAPOLIS

51 FRANKLIN STREET

2 Beds

2 Baths

2,269 Sq.Ft.

$1,749,900

MLS#: MDAA2127792

Step into the heart of Eastport, where charm and convenience meet in this beautifully renovated Cape Cod. Just a short stroll from the water’s edge and downtown Annapolis, this home embodies the Eastport lifestyle — vibrant, nautical, and effortlessly welcoming. From the moment you enter, natural light pours through every window, illuminating three levels of thoughtfully designed living space. Classic details — arched doorways, hardwood floors, custom built-ins, and rich millwork — blend seamlessly with modern updates, creating a home that feels both timeless and fresh. The inviting floor plan offers room for every occasion. A serene primary suite with its own fireplace provides a private retreat, while the main-level office doubles as a guest room or den. Formal living room with fireplace and gorgeous dining room set the stage for elegant entertaining The family room invites casual gatherings with another fireflace and access to the screened porch. The updated kitchen is a true centerpiece, with fresh cabinetry, stylish countertops, and a backsplash that ties it all together. Upstairs, a spiral staircase leads to a sunlit loft with a private balcony — perfect for a creative nook, playroom, or quiet reading space. Outside, the screened porch, fenced yard, and welcoming front porch create effortless indoor-outdoor living, ideal for relaxing or hosting friends. The basement was recently waterproofed. Practical touches like a mudroom with laundry and off-street parking make everyday life easy. Beyond the walls, Eastport beckons. Launch your kayak from Horn Point Park, wander streets lined with art and history, or cross the Spa Creek drawbridge to downtown Annapolis and the Naval Academy. From this location, the Chesapeake Bay is your playground — with cruising and fishing destinations like Baltimore’s Inner Harbor, St. Michael’s, Oxford, and Solomon’s Island all within reach. Annapolis offers the perfect balance of small-town charm and cosmopolitan sophistication, and this Eastport jewel places you right at the center of it all. With quick access to Rt. 50 and 97, Baltimore, BWI, Ft. Meade/NSA, and Washington, DC are just a drive away. This is more than a home — it’s a lifestyle. Welcome to Eastport.
#MDAA2131360

ANNAPOLIS

3 CHESTER AVENUE

3 Beds

3 Baths

3,699 Sq.Ft.

$1,730,000

MLS#: MDAA2131360

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, new tankless water heater, 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.
#MDAA2127736

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 1210

3 Beds

3 Baths

3,520 Sq.Ft.

$1,695,000

MLS#: MDAA2127736

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 20,000 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.
#MDAA2116986

ANNAPOLIS

3300 SHORE DRIVE

4 Beds

4 Baths

2,798 Sq.Ft.

$1,650,000

MLS#: MDAA2116986

Enjoy urban living at 285 West Street #15! This stunning property offers a stylish way to embrace the best of downtown Annapolis in a modern townhome with an elevator and rooftop deck. Step outside and enjoy the city’s energy—shops, restaurants, the waterfront, and cultural attractions are all just a short stroll away—while still savoring the comfort of a private, lock-and-leave retreat. Built by Bozzuto in 2020, this four-bedroom, four-and-a-half-bath home features an open, light-filled layout designed for both everyday living and entertaining. The open floor plan on the main level includes the living room with spacious seating area and fireplace, a dining area, and a classic all white gourmet kitchen anchored by an island with ample seating, high-end appliances, and a built-in sideboard with beverage center. Upstairs, the primary suite offers two walk-in closets and a spa-like bath with double vanities, and a large tiled shower. An additional bedrooms with ensuite bath and conveniently located laundry room complete the this level. Head upstairs to the top floor via the stairs or elevator to enjoy the inviting family room, guest bedroom and enviable rooftop deck with double sided fireplace and sunshade, an incredible retreat for relaxing and entertaining on a beautiful evening. The entry level provides a flexible bedroom or office with full bath and boasts heated floors for added comfort. Rounding out the appeal is a two-car garage, plenty of storage and a plethora of upgrades and curated finishes throughout. Perfectly located within close proximity of everything Annapolis has to offer; walk to the shops and restaurants of West and Main Streets as well as the Historic District, City Dock and the Naval Academy. 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. Welcome Home!
#MDAA2123570

ANNAPOLIS

285 WEST STREET 15

4 Beds

4 Baths

2,720 Sq.Ft.

$1,595,000

MLS#: MDAA2123570

Thoughtfully updated home, preserving the character and charm of Murray Hill while offering the comfort, efficiency, and style of new construction. | 4 Bed | 3.5 Bath | 2,580 Sf | 3,340 Sf Lot | Large Backyard | 1 Parking Space | Home: Full Gut Renovation, Open Main Living Layout, Custom Tiled Wood Burning Fireplace w/ Mantle, Large Jeld-Wen Windows w/ Lots of Natural Light Throughout, Recessed LED Lighting Throughout, 9 Ft Ceilings, Hard Wired Security System, Klipsch Built-In Speaker System, Dual Zoned High Efficiency Carrier HVAC w/ Ecobee Smart Thermostat, High Efficiency Heat Pump Water Heater, Closets w/ Custom Built-Ins, Elfa Closet System in Primary Suite, Original Heart Pine Hardwood Flooring Throughout First Floor, Laundry Closet w/ Custom Built-Ins & LG Full Size Washer & Dryer, Powder Bath on Main level, Bluestone Entrance Sidewalk & Steps, Rear Property Access from Morris Street | Kitchen: Large Island w/ Storage & Seating for 3, Ample Cabinetry w/ Soft-Close Hardware, Built-In Custom Pantry, Gloss Tile Backsplash, Quartz Countertops, Brushed Brass Finishes, Kitchen Aid Stainless Steel Appliances, French Door Refrigerator, Induction Range w/ Zephyr Exhaust Hood, Full-Size Dishwasher, Built-In Microwave Drawer | Baths: Frameless Glass Enclosed Shower w/ Separate Handheld Shower Head, Built-In Niche, Separate Soaking Tub & Large Double Vanity in Primary Suite, Quartz Topped Vanities w/ Storage, Tiled Shower Walls & Flooring | Basement: Rear Yard Access, Private Backyard Entrance, Family Room w/ Wet Bar, Wine Fridge, & Floating Shelves, Additional Bedroom & En Suite Bathroom w/ Glass Enclosed Shower | Neighborhood: Murray Hill is one of Annapolis’ most sought-after neighborhoods, known for its tree-lined streets, classic architecture, and easy walkability to downtown. With Spa Creek on one side and City Dock just a short stroll away, residents enjoy a perfect blend of historic charm and a waterfront lifestyle.
#MDAA2129582

ANNAPOLIS

48 MURRAY AVENUE

4 Beds

3 Baths

2,580 Sq.Ft.

$1,595,000

MLS#: MDAA2129582

PHOTOS TO BE UPDATED THROUGHOUT BUILDING PROCESS!! This is a rare opportunity to own a newly built, beautifully designed home on a large lot in an established neighborhood-with nature at your doorstep and everything Annapolis has to offer just minutes away. This home is set to be completed by year end, 2025. With a stunning Colonial architectural style, this beautiful home offers 5-bedrooms and 4.5-baths and sits on the last available lot in the Twin Hills neighborhood which is 1.4 acres and borders lush trees and a preservation area. It offers a rare blend of privacy, openness and a connection to nature. Whether you are hosting friends or enjoying a quiet night in, the thoughtful layout makes everyday living feel seamless and relaxed. As you step inside, you are greeted by an inviting open floor plan with an abundance of light throughout that seamlessly connects the open-concept gourmet kitchen to the family room, creating an ideal space for both entertaining and everyday living. The kitchen features stainless steel appliances, including double wall ovens, cooktop and built-in microwave, complemented by a spacious island and quartz countertops. The Morning Room (Breakfast Room) and Conservatory offers light filled retreats year round. You will also find five generously sized bedrooms, each designed with comfort in mind. The primary suite is a true retreat, with a spacious sitting room and dual walk-in closets in addition to a luxurious en-suite bathroom featuring a soaking tub, walk-in shower, and dual vanities as well as dual water closets! The family room features 10’ ceilings and a relaxing gas fireplace to keep you warm in the cooler nights! The full basement, with an outside entrance, provides extra entertaining spaces with a extensive recreation room, true fifth bedroom and full bath as well as an unfinished area which leaves endless possibilities for customization, whether you envision a home theater, gym, or additional living space. The bedroom floor laundry adds a touch of practicality to daily routines, while the cozy family room off the kitchen serves as the heart of the home, perfect for relaxation and connection. The side-entry garage accommodates three vehicles and a generous amount of storage space, ensuring convenience and ease of access. This residence is not just a home; it's a lifestyle choice that embodies luxury, comfort, and modern living. Experience the perfect blend of sophistication and warmth in this remarkable new construction home, where every detail has been thoughtfully curated for your enjoyment. All of this with an Annapolis address (and a close proximity to the water and fine restaurants Annapolis has to offer) to add to the joy you will feel from choosing this as your next home. Howmar Homes is a local builder dedicated to treating every house as if it were his own. With no shortcuts taken, each home reflects true care and craftsmanship you can see and feel in every detail. An optional inground pool has already been approved and has been cited on property for future or present consideration. If you act quickly, you can still select final finishings. Don’t miss your chance! Schedule your showing today!
#MDAA2125858

ANNAPOLIS

1907 MACKIEBETH COURT

5 Beds

4 Baths

5,982 Sq.Ft.

$1,575,000

MLS#: MDAA2125858

Incredible Opportunity in the Heart of Eastport! Beautifully remodeled Victorian located on the Eastport Peninsula. Features include a welcoming front porch, wood floors, and a chef’s kitchen with Viking appliances, a 6-burner stove, and vented hood. Windows and roof were replaced in 2025; roof includes new gutter guards. Energy-efficient appliances, including a gas on-demand water heater, have earned this home an Energy Star Certificate from BGE. Flexible heating and cooling options with radiator heat and five mini-split units providing a total of 48,000 BTUs for heating and cooling. Skylights feature solar shades, and the fully encapsulated crawl space enhances year-round comfort and efficiency. Upper level offers two bedrooms, each with a full bath, plus a full-size washer and dryer. Enjoy a private, fully fenced backyard (new fence 2020) with mature native trees and landscaping—perfect for relaxing or entertaining. The detached accessory structure offers endless possibilities: office, studio, hobby room, or gym. And don't forget.....there is an off street driveway !! This property is move-in ready—just bring your personal touch!
#MDAA2130442

ANNAPOLIS

120 CHESAPEAKE AVENUE

2 Beds

2 Baths

2,130 Sq.Ft.

$1,449,000

MLS#: MDAA2130442

Tucked back from the road and surrounded by trees, this contemporary waterfront home offers privacy and a serene connection to nature. Unique original details have been thoughtfully preserved while the interior has been completely renovated for modern living. From the moment you enter, walls of glass draw your eye through the home to the expansive deck that stretches nearly the full length of the house, showcasing tranquil views of Weems Creek through the trees. The open floor plan features a living room with an electric fireplace providing supplemental heat, a beautifully remodeled gourmet kitchen with bar, a dining area, and a conveniently placed mudroom, pantry, and powder room. Upstairs, two ensuite bedrooms include a spacious primary suite with multiple closets and a skylit bath with walk-in shower. The lower level hosts two additional bedrooms and a shared bath with steam shower, while an unfinished basement level provides storage and houses the utilities. Outside, the deck is ideal for entertaining with multiple seating areas and an outdoor TV. While the waterfront is not currently accessible, the property offers potential for private water access and a pier. Whether enjoying the everchanging scenery and waterfowl from indoors or taking in the view from the deck, the setting is captivating. The sought-after Admiral Heights community provides voluntary HOA membership with access to waterfront amenities, a boat club, pool membership, and neighborhood parks. Located within close proximity to restaurants, groceries, shopping and Navy Stadium events, with easy access to all major commuter routes to DC, Baltimore and beyond. Welcome Home!
#MDAA2126690

ANNAPOLIS

173 WILLIAMS DRIVE

4 Beds

3 Baths

2,603 Sq.Ft.

$1,425,000

MLS#: MDAA2126690

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