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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

358

# of Listings

3

Avg # of Bedrooms

$480

Avg. $ / Sq.Ft.

$1,098,897

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

358 Properties Found. Page 6 of 24.

Embrace the opportunity to create your dream waterfront retreat on this expansive 10,072 sq ft (0.24-acre) property, strategically located on the tranquil shores of Chesapeake Ave in the coveted Venice Beach area. This combined offering includes Lots 3 & 4 Block C (Tax #020288602739800), providing a unique canvas for your architectural vision.
Whether you choose to renovate the existing structure or start fresh with a custom build, you'll enjoy breathtaking and expansive water views, perfect for soaking up the serene coastal ambiance. This property is a paradise for water enthusiasts, featuring direct access to boating, fishing, and crabbing from your own private pier.
Sold strictly "AS-IS," this property offers an unparalleled chance to invest in prime real estate in a prestigious area, with endless potential to craft a personalized sanctuary tailored to your lifestyle.
Bullets-
*Single-family waterfront home with outstanding views
*Prime waterfront location on Chesapeake Ave in Venice Beach
*Combined lots offer 10,072 sq ft (0.24-acre) of potential
*Ideal for new construction or renovation with expansive water views
*Private pier for boating, fishing, and crabbing
*Sold "AS-IS" for maximum flexibility in development plans
Explore the boundless possibilities of this prime waterfront property and create a legacy home that will be cherished for generations.
SEE SELLER'S Renderings / Drawing for a potential buildout

ANNAPOLIS

1407 CHESAPEAKE AVENUE

3 Beds

1 Baths

964 Sq.Ft.

$1,350,000

MLS#: MDAA2114466

Weekend Escape, Airbnb Gem, or Investment Opportunity in Bay Ridge!

Discover the perfect blend of coastal elegance and craftsman charm in this one-of-a-kind 3-bedroom, 3.5-bath retreat—offered for the very first time. With over 3,500 sq ft of light-filled living space, this home is tucked away in one of Annapolis’s most coveted waterfront communities: Bay Ridge.

Whether you’re searching for a relaxing weekend escape, a high-potential Airbnb, or a long-term investment, this property offers unmatched flexibility and appeal.

Step inside to find gleaming hardwood floors, a chef’s kitchen, and sun-drenched spaces that flow effortlessly onto a balcony ideal for alfresco dining and sunset crab feasts. Each of the three oversized bedrooms boasts private outdoor seating or decks—making every stay feel like a serene getaway.

The spacious lower level includes a private suite with bedroom, full bath, sitting area, and kitchenette—ideal for multigenerational living, a dedicated guest space, or a turnkey short-term rental setup.

Nestled in the heart of Bay Ridge—where the Chesapeake Bay hugs miles of shoreline—you’ll find a vibrant community rich in history, charm, and year-round appeal. From quaint 19th-century cottages to elegant new builds, Bay Ridge is known for its architectural variety, lush landscapes, and true sense of community.

This is more than a home—it’s your chance to own a piece of Annapolis living, whether for weekends, income, or generations to come.

ANNAPOLIS

61 E LAKE DRIVE

3 Beds

3 Baths

3,583 Sq.Ft.

$1,350,000

MLS#: MDAA2110482

Back on the Market!

Escape to your own private Estate. 6100+ sqf of finished space with 2.2 acres of land in the most desirable location of Annapolis. 6 Bedrooms, 4.5 Bathrooms, with > 1000sqf for Master Suite. Two Fireplaces. Move-in condition. Potential for subdivision (check with engineer/county).

A stone's throw to downtown without the city taxes. Across from B&A bike Trail & WWII Memorial. Direct access to Rt50 without any stoplights! BroadneckHS/Severn RiverMS/ArnoldES. Agent Owner.

BRING YOUR OFFERS. All reasonable offers will be considered. Also open to reasonable allowance for prefered cosmetic updates to be completed prior to closing.

Open to Owner Financing or leasing it at $6500/month.

Property is now vacant on combo . Agent Owner.

ANNAPOLIS

1707 RITCHIE HIGHWAY

6 Beds

4 Baths

6,196 Sq.Ft.

$1,325,000

MLS#: MDAA2095284

Stunning single family home in the private enclave of highly sought after Primrose Hill. This six year old custom Craftmark Home checks all the boxes for the discriminating buyer: elevator serving all three floors; spacious kitchen with oversized island; quartz countertops; custom cabinetry; open plan main level with gas fireplace; large first floor office or den; four large bedrooms on second floor, two with ensuite bathrooms; massive private primary suite (19.5’ x 21.5’) with cathedral ceiling plus room-sized primary closet; wonderful primary bath with two vanities, large walk in shower and free standing tub; nine foot ceilings throughout, including basement; full basement with unlimited possibilities: legal fifth bedroom and full bath roughed in; room for large family room, shop, and storage; oversized two car garage and two parking pad spots; energy efficient Certified Green Building; spacious outdoor community spaces, with all grounds maintained by HOA. All of this within walking distance to Pip Moyer Recreation Center, Eastport, downtown Annapolis, shopping, dining, public boat ramp, tennis and pickleball courts.

ANNAPOLIS

57 PRIMROSE HILL LANE

4 Beds

3 Baths

3,841 Sq.Ft.

$1,300,000

MLS#: MDAA2113120

Experience luxury and light in this rare 3-bedroom, 2.5-bath condo in the highly sought-after Park Place community. This corner unit boasts incredible 180° views and is filled with natural light from expansive windows throughout. With three deeded garage parking spaces located right next to each other—an unparalleled convenience in downtown Annapolis—you’ll never have to worry about parking again.

Inside, a spacious open-concept layout welcomes you with upgraded appliances, generous storage, and a stylish design that makes everyday living and entertaining effortless. The sun-drenched living and dining areas flow into a modern kitchen, ideal for both casual meals and special gatherings.

The serene primary suite features an en-suite bath and a peaceful ambiance, while two additional bedrooms offer the perfect setup for guests, a home office, or both.

Park Place offers a true lock-and-leave lifestyle with 24/7 front desk staff, beautifully maintained grounds, a pool, fitness center, party room, and a private outdoor patio with grills and a dog park. And for added convenience, a private shuttle picks up right from the courtyard and takes you anywhere in downtown Annapolis.

Perfectly positioned to enjoy the best of in-town living, this home combines elegance, ease, and vibrant community energy. Welcome to Park Place—your next chapter starts here.

ANNAPOLIS

5 PARK PLACE 428

3 Beds

2 Baths

1,822 Sq.Ft.

$1,299,000

MLS#: MDAA2112582

Welcome to this stunning 2025-renovated Cape Cod nestled in the heart of Eastport at 617 Chesapeake Avenue. With approximately 2,000 finished square feet, this 4-bedroom, 2.5-bath home perfectly blends classic charm with modern luxury.

Step inside to wide plank white oak hardwood floors and an open-concept living space bathed in natural light. The chef’s kitchen is a showstopper, featuring sleek quartz countertops, high-end appliances, and custom cabinetry — ideal for entertaining or quiet evenings at home.

Upstairs, spacious bedrooms and spa-inspired bathrooms provide a serene retreat, while thoughtful design details throughout elevate the home's overall appeal.

Enjoy the convenience of off-street parking and a detached 1-car garage complete with a loft — offering endless potential as a studio, guest space, or accessory dwelling unit (ADU) conversion.

Located just minutes from downtown Annapolis, the waterfront, and all the dining, shopping, and cultural attractions Eastport has to offer, this turnkey property is a rare find in a prime location.

Don’t miss your chance to own a piece of Annapolis living at its finest.

ANNAPOLIS

617 CHESAPEAKE AVENUE

4 Beds

2 Baths

1,969 Sq.Ft.

$1,299,000

MLS#: MDAA2114116

Live the Annapolis lifestyle just close enough to enjoy in-town living, but tucked away in a quiet little enclave avoiding all the noise and parking challenges in town. The current homeowner refers to Primrose Hill as a "serene little gem'. Walk to coffee shops and dining hot spots, launch the boat or hop on the water taxi right up the street. This distinguished Georgian-style home offers the best of both worlds—peaceful, private living with unparalleled access to the city's most desirable amenities. The HOA cares for the lawn and snow removal, just lock and leave and head out of town stress free! Originally the model home for the community, every inch of this residence reflects elevated design and attention to detail a discerning buyer would expect. The timeless Georgian brick front exudes classic charm, while the interior reveals a sophisticated, modern aesthetic. A sleek, designer kitchen with upgraded appliances flows effortlessly into an open-concept main living area—ideal for entertaining or relaxed everyday living. The inviting family room is anchored by custom built-ins and a gas fireplace, adding warmth and architectural interest. This 5-bedroom, 4.5-bath home is designed for comfort and style. The upper level features four spacious bedrooms, including a luxurious owner’s suite with cathedral ceilings, an expansive walk-in closet, and a spa-inspired bathroom retreat. Bedroom two boasts its own private ensuite, offering flexibility for guests or multigenerational living. A conveniently located upstairs laundry enhances everyday functionality. The fully finished lower level includes a generous recreation room and a versatile bonus room—perfect for a home gym, office, or guest bedroom. A rare two-car garage with additional driveway parking adds convenience, especially valuable in this in-town location. Residents enjoy exclusive access to nearby amenities such as the Pip Moyer Recreation Center with tennis and pickleball courts, fitness classes and a swim club. The park like setting and intentional green spaces serve as the perfect backdrop for weekly neighborhood wine nights and social gatherings throughout the year fostering a welcoming and connected sense of community.
This location provides a quick commute to DC and Baltimore. CHECK OUT THE VIRTUAL TOUR;

ANNAPOLIS

52 PRIMROSE HILL LANE

5 Beds

4 Baths

3,978 Sq.Ft.

$1,295,000

MLS#: MDAA2113794

New on site 4 days ago

#MDAA2116712

ANNAPOLIS

1230 CRUMMELL AVENUE

4 Beds

2 Baths

2,555 Sq.Ft.

$1,275,000

MLS#: MDAA2116712

Nestled in the desirable community of The Meadows, this elegant brick-front home offers a perfect balance of space on 2.5 acres with functionality and refined details. Designed for both comfortable living and effortless entertaining, it gives an inviting open-concept layout that seamlessly connects the family room to the gourmet kitchen. The kitchen is a chef’s dream, featuring stainless steel appliances, dual convection ovens, granite countertops, and an oversized island with seating. The Kraftmaid cabinetry includes a double pantry cabinet with pull-out drawers and under-lit glass-front cabinets. A beautifully designed cabinet wet/dry bar with a wine cooler, wine rack, and instant hot water at the oversized sink—perfect for entertaining. Off the kitchen, the formal living and dining area showcases stunning travertine stone flooring, while an immense bay window floods the space with natural light, creating an inviting atmosphere. The main level also includes a spacious laundry and mudroom with a convenient rear door, a huge coat closet, and garage access. Designed shelving maximizes storage and functionality, making daily tasks effortless. Primary Suite Retreat offers a true sanctuary with a sprawling 12x12 walk-in closet, custom-designed by California Closets for optimal organization. The spa-like primary bath features dual sinks, an air-soaking tub, an oversized separate shower, and a private water closet with a bidet, all elegantly accented by marble tile flooring. The finished basement expands the home's living space with multiple outdoor access points leading to an expansive clubroom. Built-in bookshelves and cabinetry make this space ideal for a pool table, media center, or gaming area with surround sound. A flexible bonus room offers versatility as a home gym, craft space, or private office. At the same time, a custom-designed utility and hobby area is outfitted with specialized wiring and a commercial-sized sink—great for pottery enthusiasts or even dog-washing. Additional climate-controlled storage ensures ample space for seasonal items and household essentials.
Stepping outside, you'll find beautifully hardscaped grounds, including a 1,407 sq. ft. multi-level stone paver patio and a Trex deck off the kitchen—perfect for grilling and outdoor gatherings. The professionally landscaped gardens are maintained with an underground sprinkler system, ensuring vibrant greenery year-round. Parking is a breeze with an oversized side-entry two-car garage (613 sq. ft.) featuring a custom organization system and an additional parking pad designed to accommodate guests and oversized vehicles. An owned propane tank fuels the gas fireplace, gas range, and a full-house generator, adding energy efficiency and peace of mind. With a prime location offering easy access to Baltimore, Annapolis, and Washington, D.C., this exceptional home delivers both luxury and convenience. Don’t miss the chance to make 1812 Millridge Ct. your own!

ANNAPOLIS

1812 MILLRIDGE COURT

4 Beds

3 Baths

3,555 Sq.Ft.

$1,250,000

MLS#: MDAA2103154

This one-of-a-kind luxury condo in Historic Downtown Annapolis offers the perfect blend of elegance, convenience, and vibrant city living. Located in the sought-after Acton’s Landing, this 1,921 sq. ft. outside corner unit is just steps from waterfront parks, fine dining, boutique shopping, and iconic landmarks such as the U.S. Naval Academy, the Governor’s Mansion, and the Maryland State House. Residents enjoy front-row access to Annapolis’ world-famous events, including the largest sailboat show in the world (October), the Blue Angels Air Show (May), the Holiday Boat Parade (December), and a summer full of concerts and festivals.

Designed to capture natural light from sunrise to sunset, this bright and airy condo features an open floor plan with expansive windows and sliding glass doors that create a seamless indoor-outdoor connection. The gourmet kitchen boasts a large eat-at island, granite countertops, a gas stove, premium appliances, a touchless faucet, pull-out cabinet drawers and recessed lighting all opening to a spacious dining and living area—ideal for entertaining. The primary suite is a true retreat, with space for a sitting room, featuring a room-size walk-in closet, an additional closet, a ceiling fan, and a spa-inspired en-suite bath with a soaking tub, walk-in shower, dual sinks, ceramic tile, recessed lighting, and a built-in ceiling heater. The second bedroom, with its own en-suite bath and private access to the 27-ft. patio and courtyard via a large sliding glass door , offers an inviting escape. A private home office/den with French doors provides a flexible space. Off the foyer, a third full bathroom with a walk-in shower adds extra convenience for guests, while a full-size front-loading washer and dryer are tucked away in the laundry closet.

Adding to its unmatched value, this unit comes with two parking spaces in the secure underground garage. Building amenities include secure entry, an on-site assistant manager at the front desk in the lobby, as well as an on-site condo property manager, three elevators, wheelchair accessibility, a fitness room, a library, multiple community rooms and a beautifully landscaped courtyard with a central fountain. Experience the best of downtown, historic Annapolis living with unparalleled luxury and convenience. Schedule your private showing today!

Home Warranty included with purchase. NO EV Charger.

ANNAPOLIS

66 FRANKLIN STREET 106

2 Beds

3 Baths

1,921 Sq.Ft.

$1,249,900

MLS#: MDAA2109086

Another $50,000 price improvement!!! Nestled on the banks of Weems Creek off the Severn River, this exceptional waterfront Colonial in Admiral Heights offers 126 feet of private shoreline and deep water access (7-8' MLW) with a newer 80-foot pier perfect for boating enthusiasts. Lovingly maintained by its original owner, this spacious 3-level home features a soaring 2-story living room with a fireplace, a second-floor family room with its own fireplace, and a full walk-out basement ready for your personal touch, complete with a third fireplace and access to a large covered patio, was previously recreation room and fourth bedroom, Enjoy breathtaking water views from the huge main-level deck and second-floor balcony. Located within walking distance of Navy-Marine Corps Stadium and just minutes from downtown Annapolis, this home provides the perfect blend of serene waterfront living and city convenience. Community amenities include a pool, parks, and water access, making this a rare find! Bonus: Room for a 2-car garage. Don’t miss this incredible opportunity—schedule your private tour today! House has so much potential just waiting for your updates!

ANNAPOLIS

322 HALSEY ROAD

3 Beds

3 Baths

2,808 Sq.Ft.

$1,249,900

MLS#: MDAA2111770

All Offers MUST be received by Thursday, April 3rd at 6 pm. Charming 2-Bedroom, 2-Bathroom Cottage in Eastport - A Hidden Gem

Nestled on a peaceful one-way street on the Eastport Peninsula, this
enchanting 2-story cottage offers a serene escape just blocks away from
water on three sides. A coveted destination for vacationers, this property
boasts a proven income-producing rental history—don’t hesitate to inquire
for more details!

Recently renovated by a renowned architect, this unique home seamlessly
blends modern design with cozy charm. The open-concept layout features
2 spacious bedrooms and 2 full bathrooms, perfect for relaxing and
entertaining. The all-seasons room, with its decorative fireplace and The
Frame TV, creates a perfect spot to unwind. The custom-designed
breakfast nook adds a warm touch to the dining area, while the chef-
inspired caterer’s kitchen, complete with high-end appliances and a
spacious double pantry, makes cooking a joy.

Step outside into your own secret garden oasis, where over a dozen rare
Japanese Maples surround the full-size saltwater pool. Sip tea on the upper
deck or entertain guests in your private, landscaped retreat. This garden is
the perfect place to relax in a picturesque, tranquil setting just minutes from
downtown Annapolis.

Key updates and features of the home include:

Bedrooms & Bathrooms: The upstairs features 2 comfortable
bedrooms, including a primary suite with a gas-burning
fireplace and custom California Closet system. Both bedrooms
share a spa-like bathroom with dual vessel sinks, skylights with
remote control closures, natural stone countertops, and a
pebble-floor shower with dual shower heads.

New Features: A beautifully renovated sunroom (2023), new
upper deck (2023), fresh coat of paint (2025), new pool filter
and plaster (2024), and a full fence replacement (2020) make
this home a dream come true.

Additional Amenities: A built-in desk and custom storage
closet in the front bedroom, washer/dryer, attic access, and a
private deck with a glass wall railing offer both style and
practicality.

Enjoy the best of Eastport living in this rare, affordable property—whether
you’re looking for a personal retreat, a primary residence, or an investment
property to add to your portfolio, this home is a perfect choice.

Located just a short 10-minute stroll across the Spa Creek Bridge from
downtown Annapolis, this location is truly unbeatable. Enjoy easy access to
all the charm of Annapolis, with Washington DC just 45 minutes away and
Baltimore only 25 minutes away.

Recent updates:
2020 Electrical panel
2020 new landscaping and full fence replacement
2021 California Closet
2023 Sunroom and upper deck
2024 New pool filter, full pool plaster, cooping, and decorative tile
2025 Fresh Coat of Paint
This is an enchanting piece of real-estate that genuinely represents Eastport living at its finest
without breaking the bank. Make it your own personal retreat, primary residence, or add it to
your investment portfolio!!! ALL ARE EXCELLENT CHOICES!!

Make this your dream home—schedule a tour today!

ANNAPOLIS

421 THIRD STREET

2 Beds

2 Baths

1,315 Sq.Ft.

$1,225,000

MLS#: MDAA2108698

#MDAA2097228

ANNAPOLIS

301 UNITY LANE

5 Beds

5 Baths

7,616 Sq.Ft.

$1,219,000

MLS#: MDAA2097228

Step into a piece of Annapolis history with the Philip Clayton House, a cherished landmark dating back to 1834. Perfectly situated within walking distance to the City Dock, U.S. Naval Academy, and the vibrant shops and restaurants of Downtown Annapolis, this residence blends timeless character with everyday convenience. Over nearly two centuries, the home has undergone thoughtful renovations and expansions, preserving its historic charm while enhancing livability. You'll be captivated by the heart of pine floors,
many original moldings, and multiple fireplaces that reflect its storied past. The spacious family room addition seamlessly opens to a private patio and fenced backyard—ideal for outdoor entertaining or peaceful relaxation. Inside, the home features 4 generously sized bedrooms and 2.5 bathrooms, offering comfortable accommodations for residents and guests alike. The large kitchen, complete with a central island, serves as a natural gathering space—perfect for family meals or entertaining. Currently operating as a successful VRBO, this property offers both residential appeal and investment potential.

Don’t miss your chance to own a piece of Annapolis history!

ANNAPOLIS

160 GREEN STREET

4 Beds

2 Baths

2,322 Sq.Ft.

$1,200,000

MLS#: MDAA2113866

#MDAA2094906

ANNAPOLIS

3536 SARATOGA AVENUE

4 Beds

3 Baths

2,368 Sq.Ft.

$1,196,000

MLS#: MDAA2094906

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