One of the most popular communities provided by {{page_data.agentName}}

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

207

# of Listings

3

Avg # of Bedrooms

$516

Avg. $ / Sq.Ft.

$1,086,221

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

207 Properties Found. Page 3 of 14.

Nestled in the heart of historic Eastport Annapolis, this coastal craftsman has been extensively remodeled, offering a perfect blend of classic charm and contemporary elegance. The home is set on a generously sized lot, providing abundant green space, with new sod and landscaping coming soon. Premium exterior finishes include an inviting front porch, James Hardi siding and Anderson 400 windows. Inside, the home features a modern sprinkler system, two fireplaces, and all new plumbing and electrical systems.

As you step inside, the open and versatile floor plan begins with a multi-use room to the left ideal for an office or sitting area- while a spacious area to the right offers flexibility for living and dining. The layout then flows seamlessly into the kitchen and into a comfortable family room, creating an ideal setup for both everyday living and entertaining. Hardwood floors, high ceilings, and impressive millwork carry throughout.

Upstairs, the second floor hosts all four bedrooms, including the luxurious master’s suite. The master’s suite features a spa-like bath complete with a dual vanity, frameless glass shower, and soaking tub. A conveniently located washer and dryer are also on this level. A large, fully finished basement provides ample storage, especially in the sizable utility area, offering flexible space for a home gym, recreation, or more. Notably, the home features a double staircase one in the front portion of the home and another in the rear, leading directly into the kitchen and family room adding a unique and functional design element. Additional upgrades include all new plumbing and electrical systems. A generous rear deck is perfect for entertaining, and there are three off street parking spaces, plus the potential for a future garage with an accessory dwelling unit above. All of this is just steps from restaurants, shopping, yacht clubs and everything Eastport and downtown Annapolis have to offer. Days on market reflect the extensive permitting period to begin the remodel and addition.

ANNAPOLIS

400 JEFFERSON STREET

4 Beds

3 Baths

3,640 Sq.Ft.

$1,990,000

MLS#: MDAA2131396

Last available opportunity for a buildable Waterfront lot on Lake Ogleton in the coveted community of Bay Ridge in Annapolis! This .22 acre lot has been in the same family for the past 58 years and is coming to market for the first time. With 57 feet of waterfrontage on the sparkling shores of Lake Ogleton, the possibilities are endless for building the waterfront home of your dreams! This property is priced to sell quickly, at $361,000 below the tax assessed value! Contact your architect and take the first step toward bringing your vision of the ideal Annapolis lifestyle on the water! The sought-after Bay Ridge Community features a plethora of amenities, including a 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

48 E LAKE DRIVE

None Beds

None Baths

0.22 acres

$1,895,000

MLS#: MDAA2137314

An exceptional opportunity awaits in coveted West Annapolis—a rare 0.61-acre offering with endless potential. Whether you envision a thoughtful renovation or a custom new build, this expansive lot provides the perfect canvas to create your dream residence in one of the area’s most sought-after neighborhoods. Approved civil engineering plans by Drum, Loyka & Associates, LLC and architectural designs by Custom Designs Unlimited convey with the property (city approvals secured; permits not yet pulled), offering a valuable head start toward bringing your vision to life.

The generously sized lot and current AS-IS cottage provides an abundance of outdoor space, inviting a plethora of outdoor gatherings, summer barbecues, and relaxed evenings enjoying the vibrant West Annapolis lifestyle. Just beyond your doorstep, stroll to acclaimed restaurants, local pubs, charming boutiques, and convenient street-end water access. Ideally situated near Downtown Annapolis, Navy Stadium events, and the Naval Academy, the location also provides effortless commuter access to Route 50 and the Bay Bridge for Eastern Shore escapes or travel to Washington, D.C.

A truly special setting offered AS-IS, ready for its next chapter. Welcome Home!

ANNAPOLIS

4 SHILEY STREET

None Beds

None Baths

0.61 acres

$1,875,000

MLS#: MDAA2136908

An exceptional opportunity awaits in coveted West Annapolis—a rare 0.61-acre offering with endless potential. Whether you envision a thoughtful renovation or a custom new build, this expansive lot provides the perfect canvas to create your dream residence in one of the area’s most sought-after neighborhoods. Approved civil engineering plans by Drum, Loyka & Associates, LLC and architectural designs by Custom Designs Unlimited convey with the property (city approvals secured; permits not yet pulled), offering a valuable head start toward bringing your vision to life.

The generously sized lot and current AS-IS cottage provides an abundance of outdoor space, inviting a plethora of outdoor gatherings, summer barbecues, and relaxed evenings enjoying the vibrant West Annapolis lifestyle. Just beyond your doorstep, stroll to acclaimed restaurants, local pubs, charming boutiques, and convenient street-end water access. Ideally situated near Downtown Annapolis, Navy Stadium events, and the Naval Academy, the location also provides effortless commuter access to Route 50 and the Bay Bridge for Eastern Shore escapes or travel to Washington, D.C.

A truly special setting offered AS-IS, ready for its next chapter. Welcome Home!

ANNAPOLIS

4 SHILEY STREET

4 Beds

2 Baths

1,557 Sq.Ft.

$1,875,000

MLS#: MDAA2137186

Welcome to 310 Giddings Avenue, a stunningly re-imagined Craftsman-style home on an expansive corner lot in the heart of West Annapolis. This property offers three levels of custom-finished living space, perfectly blending modern luxury with classic architectural charm. This 3-bedroom, 3-full-bath home boasts a main-level Owners' Suite complete with a deluxe full bath and a spacious walk-in closet.

An entertainer’s dream, the sun-filled main level features a wide-open floor plan anchored by a dramatic double-sided fireplace and a soaring two-story vaulted ceiling. This creates an airy, sophisticated atmosphere that flows seamlessly from the living room to the gourmet kitchen and dining area. Upstairs, you will find two oversized bedrooms accompanied by an extra-large full bathroom.

The finished lower level serves as a dedicated wing for work and play, boasting a private home office and a sprawling recreation room with its own fireplace and walk-out access to the backyard. If you enjoy outdoor entertaining, you'll love the screened-in porch and stone patio that lead to a fully fenced backyard that is both private and welcoming. The connected two-car garage provides ample storage and includes a finished loft above.

Located in one of Annapolis’s most sought-after communities, you are just a short stroll from West Annapolis Elementary and the vibrant shops on Annapolis Street. Plus, enjoy easy access to Weems Creek for paddling or boating via the nearby city-maintained boat launch.

Join us for an Open House Saturday, March 7th from 11am-2pm.

ANNAPOLIS

310 GIDDINGS AVENUE

3 Beds

3 Baths

3,218 Sq.Ft.

$1,750,000

MLS#: MDAA2137866

Rare penthouse opportunity in downtown Annapolis. This 3-bedroom, 3.5-bath condo in the exclusive Acton’s Landing community offers over 2,500 square feet of mint-condition living space, private elevator access, two deeded tandem garage parking spaces, and two large balconies with skyline views of Annapolis.
The layout is bright, open and functional, with natural light throughout the day. The white kitchen features Silestone countertops, custom cabinetry and tile backsplash, gas cooking, a wine refrigerator, under-cabinet lighting, and new refrigerator and dishwasher.

Recent updates include a new HVAC system, new hardwood flooring, new wall-to-wall carpet in all three bedrooms, and a new dining room chandelier. The powder room and main-level en-suite bath have been updated. The combined laundry room and pantry offers custom built-ins, new flooring, a new washer and dryer, and two refrigerated beverage drawers. The entire unit has been freshly painted.

Residents at Acton’s Landing enjoy secure entry, on-site management, a fitness center, meeting and recreation rooms, a library, and a landscaped courtyard with a fountain.

Located just steps from Acton’s Cove Waterfront Park, boutique shops, restaurants, the United States Naval Academy, the Maryland State House, and the Maryland Governor’s Mansion, this is a well-appointed home in one of Annapolis’ most desirable locations. Don't miss this lock and leave opportunity!

ANNAPOLIS

66 FRANKLIN STREET 509

3 Beds

3 Baths

2,665 Sq.Ft.

$1,725,000

MLS#: MDAA2136156

With the ability to dock 5 boats on a beautifully protected cove on Burley Creek, with 10' MLW, potable water and electricity at the dock, with 30 AMP hook-up, you essentially have a private marina that happens to have a lovely home included. Exceptional features rarely found in Annapolis at the price point.

Tucked into a lovely setting yet just minutes from downtown Annapolis, this refreshed three-bedroom, three-bath contemporary offers one bedroom on each level, creating ideal separation and flexibility for guests, multi-generational living, or weekend retreats. The interior has been thoughtfully updated throughout, including fresh paint on every level and new LVP flooring that adds a soft, modern touch while enhancing the warm architectural lines of the home. Expansive windows and sliding doors draw in natural light and frame sweeping views of the creek, bringing the outdoors in and making every room feel connected to the water.

The main level is the heart of the home, where the dramatic stone fireplace rises to meet the vaulted ceiling and creates a gathering space that feels both elevated and deeply comfortable. The dining area and living room flow seamlessly onto the outdoor decks, offering multiple places to enjoy morning coffee, read a book, or simply breathe in the calm that surrounds the property. The kitchen and breakfast area provide direct access to the outdoors and enjoy tile flooring that complements the clean, modern updates found throughout the rest of the home.

Each floor offers its own bedroom and full bath. The lower level is bright and welcoming with a renovated full bathroom and a walkout directly to the waterfront lawn, ideal for guests, a studio, or a home office. The main level bedroom sits near a beautifully updated full bath featuring new flooring, vanity, and lighting. The upper-level primary suite feels like a private retreat of its own. A spacious walk-in closet provides ample storage, while the ensuite bath, complete with an elevated soaking tub that feels like something out of Old Hollywood adds a touch of whimsy and charm. The open dual-vanity area and tucked-away water closet function beautifully while keeping the suite’s retreat-like feel intact.

Whether you're hosting waterfront gatherings, relaxing by one of the two stunning stacked-stone fireplaces, or unwinding on one of the many peaceful outdoor spaces, this home offers a lifestyle that balances luxury, comfort, and natural beauty. Warm, inviting, architecturally unique, and designed to embrace the water from every angle, this property offers a one-of-a-kind opportunity to enjoy deep-water living in a setting that feels like a year-round retreat.

A truly exceptional Annapolis offering where luxury design, cozy chalet ambiance, and premier boating features meet in perfect harmony.

ANNAPOLIS

1836 BURLEY LANE

3 Beds

3 Baths

2,016 Sq.Ft.

$1,695,000

MLS#: MDAA2132644

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.

ANNAPOLIS

3300 SHORE DRIVE

4 Beds

4 Baths

2,798 Sq.Ft.

$1,650,000

MLS#: MDAA2116986

New on site 1 day ago

Old-world elegance is masterfully expressed in this exceptional Villa, a true work of art set on a lush and private 1.26-acre homesite just one block from the Chesapeake Bay. A rare offering that seamlessly blends timeless European craftsmanship with modern luxury, the residence is defined by hand-chiseled stone, classic stucco, and a striking terracotta tile roof, creating a presence that is both refined and enduring.

Inside, exquisite finishes and thoughtful design unfold at every turn. The gourmet kitchen is appointed with honed granite surfaces and chef-grade stainless steel appliances, while reclaimed hardwood flooring and imported Italian tile add warmth and authenticity throughout. Custom doors, windows, and plantation shutters further elevate the home’s character. The spacious primary suite offers a serene retreat with soaring 10-foot ceilings and a spa-inspired bath, while three additional bedrooms and well-appointed baths provide comfort for family and guests alike. A versatile bonus suite above the two-car garage, complete with a half bath, offers ideal flexibility for an in-law suite, guest quarters, or private office.

Outdoor living is equally captivating. A grand loggia invites year-round enjoyment, centered around a stunning wood-burning fireplace set within a handcrafted stone façade, the perfect ambiance for quiet evenings or entertaining under the stars. The resort-style backyard features a heated 40' x 18' PebbleTec saltwater pool with an elegant fountain feature, all surrounded by an expansive, level lawn framed by mature trees, creating a sense of total privacy and tranquility. The bucolic setting just minutes from shopping, dining, and major routes, this property offers a rare blend of peaceful countryside living with everyday convenience. The grounds feature a charming pasture with shed currently home to sheep, a thoughtfully designed chicken coop, and a solar panel field beyond, adding both character and efficiency. Flexible in nature, the land invites a range of uses, perfectly balancing rural charm with modern-day versatility.

Just moments away, Safe Harbor Marina provides the waterfront lifestyle with a full-service, resort-like atmosphere. Thoughtfully designed for both convenience and enjoyment, the marina offers a seamless boating experience complemented by beautifully maintained grounds, gathering spaces, and amenities that make it easy to spend entire days on the water. From relaxed afternoons by the pool to effortless dockside access, it serves as an extension of the home, providing a vibrant yet refined setting for both recreation and connection.

Ideally located within the sought-after Broadneck School District, the property also provides easy access to the natural beauty of Sandy Point State Park, seamless travel across the Bay Bridge to the Eastern Shore, and a direct route to Washington, D.C. via Route 50. Welcome Home!

ANNAPOLIS

1344 TYDINGS ROAD

4 Beds

4 Baths

5,536 Sq.Ft.

$1,599,000

MLS#: MDAA2139876

PHOTOS TO BE UPDATED BY THE END OF MARCH! 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 estimated to be completed by the end of April, 2026. 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!

ANNAPOLIS

1907 MACKIEBETH COURT

5 Beds

4 Baths

5,437 Sq.Ft.

$1,575,000

MLS#: MDAA2125858

Greet neighbors from the front porch or entertain them on the private, fenced rear patio. This classically designed home offers high ceilings, two gas fireplaces, updated kitchen and baths and a floor plan that allows for intimate gatherings or lavish dinner parties. Light floods all the rooms including the 4 upper level(3 ensuite) bedrooms, one with a balcony. The lower level offers a cozy fireplace, full bath and separate entry. There is a two car garage (with electric car charger)off a rear driveway that can accommodate 3-4 additional vehicles. And you will be awed by the professionally designed gardens and outdoor living spaces.
All this within walking/biking distance to local shops, restaurants and events.
Downsizing? There is ample storage! Moving up? The flexible floorplan can accommodate your changing lifestyle. Come see for yourself.

ANNAPOLIS

1109 BOUCHER AVENUE

4 Beds

4 Baths

3,779 Sq.Ft.

$1,529,000

MLS#: MDAA2136296

Historic charm and everyday comfort come together beautifully in this spacious Victorian in the heart of downtown Annapolis. From the wide front porch—perfect for slow morning coffee or unwinding at the end of the day—to the sun-filled interior, this home offers the rare combination of character, scale, and convenience.

With four finished levels, 4 bedrooms, 3 full baths, 2 half baths, and a finished walkout lower level, there is room here to spread out, gather, and live with ease. Thoughtfully updated living spaces are paired with a modern kitchen designed for real life and easy entertaining—imagine hosting dinner parties in the formal dining room, serving appetizers around the oversized island, or enjoying a quiet weeknight meal at home. Modern bathrooms throughout bring a fresh, polished feel that complements the home’s historic appeal.
The layout is especially compelling for buyers who value flexibility. Separate living and bedroom spaces across multiple levels create options for guests, work-from-home needs, hobbies, or extended stays. For buyers thinking strategically, the generous footprint also offers valuable versatility for future rental opportunities, subject to local regulations.

Outside, the lifestyle is just as appealing. Enjoy a private patio for outdoor dining or relaxing after a day in town, plus the rare advantage of parking for 2 vehicles directly behind the building—an exceptional amenity in downtown Annapolis.

Set in one of Annapolis’ most desirable locations, this home offers the best of city living without the pace or feel of a major city: close to dining, shopping, and waterfront charm, yet with the welcoming neighborhood feel that makes Annapolis so special. Schedule your private showing today and experience the space, style, and lifestyle this exceptional downtown home has to offer.

ANNAPOLIS

190 DUKE OF GLOUCESTER STREET

4 Beds

3 Baths

3,393 Sq.Ft.

$1,500,000

MLS#: MDAA2136464

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!
Seller will consider all offers !!!

ANNAPOLIS

120 CHESAPEAKE AVENUE

2 Beds

2 Baths

2,130 Sq.Ft.

$1,449,000

MLS#: MDAA2130442

Located on one of the most charming and desirable streets in Historic Annapolis, this beautifully updated home offers a rare combination of timeless character, thoughtful improvements, and an exceptional sense of space and privacy. With no direct neighbors in front or behind, the home enjoys an open, airy setting that is hard to find in such a prime downtown location.
Inside, historic details are thoughtfully complemented by modern updates throughout. The welcoming living room features a gas fireplace and sets the tone for the home’s warm and inviting feel. The kitchen and dining area flow effortlessly into a comfortable family room with a built-in bar—ideal for both everyday living and entertaining.
Upstairs, three well-appointed bedrooms provide peaceful retreats, including a spacious primary suite with a private foyer, en suite bath, and access to a deck overlooking the backyard. From here, enjoy views of the Maryland State Capitol dome—an iconic Annapolis backdrop, especially when illuminated in the evening. A fully floored attic, accessible from the primary bedroom, offers generous storage across the entire footprint.
The outdoor space is equally impressive, featuring an expanded brick patio, new fencing, and landscaping that create a private and inviting setting for relaxing or entertaining. The roof has been replaced within the past six years, adding to the home’s overall upkeep and value.
Ideally located just steps from the waterfront, Ego Alley, the U.S. Naval Academy, Maryland Avenue, and Main Street, this home offers the very best of Annapolis living—historic charm, modern comfort, and an unbeatable walkable lifestyle. Its proximity to the City Dock Resiliency Project further enhances long-term appeal, reflecting the City’s investment in preserving and improving this treasured waterfront area for years to come.

ANNAPOLIS

163 PRINCE GEORGE STREET

3 Beds

2 Baths

2,434 Sq.Ft.

$1,425,000

MLS#: MDAA2137556

#MDAA2138416

ANNAPOLIS

2644 CLAIBOURNE ROAD

6 Beds

4 Baths

3,702 Sq.Ft.

$1,384,000

MLS#: MDAA2138416

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