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

274

# of Listings

3

Avg # of Bedrooms

$510

Avg. $ / Sq.Ft.

$1,357,507

Med. List Price

Browse Annapolis Real Estate Listings

$250,000 - $500,000

$1M - $3M

74 Properties Found. Page 5 of 5.

#MDAA2143526

ANNAPOLIS

377 BROADVIEW LANE

4 Beds

3 Baths

3,111 Sq.Ft.

$1,169,000

MLS#: MDAA2143526

Discover luxurious living in this exceptional 5-bedroom, 4-bathroom home nestled on a full acre in an exclusive WATER ACCESS community. This meticulously crafted residence seamlessly blends elegant design with modern comfort, offering the perfect retreat for those seeking both tranquility and sophistication. The expansive one-acre lot offers endless possibilities for outdoor enjoyment, including gardening, relaxing on the rooftop deck, or sitting under the ceiling fans on the large front porch. Each of the five spacious bedrooms offers comfort and style, while four full bathrooms feature premium tile work, modern vanities, and spa-like amenities. All the while, enjoying the water access community amenities that offer boating, fishing, and waterfront recreation just moments from your doorstep. Easy access to local restaurants, shopping, and major roadways.

ANNAPOLIS

767 BON HAVEN DRIVE

5 Beds

4 Baths

3,255 Sq.Ft.

$1,150,000

MLS#: MDAA2140440

Waterfront home nestled in the serene enclave of Kitty Creek; located right off the South River with easy access to the Chesapeake Bay. This recently updated home offers the perfect blend of luxury, comfort, and waterfront living. Inside, you’re welcomed by refinished hardwood floors and abundant natural light. The updated kitchen features new GE stainless steel appliances and opens to a cozy living room with a wood-burning fireplace and direct access to the deck; ideal for dining under the stars overlooking the peaceful backyard and creek. A main-level laundry/mudroom with side entrance and ramp adds everyday convenience.The primary suite is a true retreat, featuring a waterfront-facing design with a private balcony and updated en-suite bath. Three additional bedrooms with new carpet offer flexibility for guests, a home office, or growing needs. The fully finished walkout lower level provides a private in-law suite with its own entrance, full kitchen, large updated bath, and laundry hookup; perfect for extended stays or entertaining. Outside, enjoy 50 feet of waterfront with a private dock slip, kayak rack, and a spacious .41-acre lot offering plenty of room to relax, garden, or play. Ideally located with easy access to Annapolis, BWI, and DC, this home offers the best of peaceful waterfront living in Annapolis and everyday convenience.

ANNAPOLIS

996 HEADWATER ROAD

4 Beds

3 Baths

2,288 Sq.Ft.

$1,150,000

MLS#: MDAA2143898

Nestled on a tranquil private drive in the highly sought-after water access neighborhood, The Downs on the Severn. This stunning stone-front Colonial offers the perfect blend of luxury, privacy, and modern convenience. Situated on 1.43 acres surrounded by nature, this beautifully remodeled 4-bedroom, 2.5-bath home has been thoughtfully updated from top to bottom with exceptional attention to detail.

Step inside to discover gorgeous new hardwood floors throughout and an open-concept layout designed for effortless entertaining and everyday living. The fully updated gourmet kitchen features warm, high-end cabinetry, elegant Calacatta Storm Gold Quartz countertops, and premium stainless steel appliances. The entire home features Mirage Harwood Flooring. Extensive upgrades include gas installation for the range and fireplace connections, a newer water heater, newer HVAC system, dual-tank water softener, sprinkler system, UV water filtration system, replacement first-floor doors, and updated roof and gutter systems. There is also a recently remodeled lower level with modern doors, LVP flooring, entertainment room, workout room, additional office space, and plenty of storage!

The luxurious primary suite has been completely transformed with a modern spa-inspired bathroom and expanded his-and-her closet space, creating the perfect private retreat.

Outdoor living is equally impressive with beautifully designed patios and fire pit areas ideal for entertaining or relaxing on peaceful summer evenings surrounded by nature.

Residents of The Downs on the Severn enjoy an unmatched lifestyle with exceptional community amenities, including two marinas with slip availability, an outdoor pool with summer swim team, clubhouse, tot lot, little library, and scenic walkable streets throughout this private waterfront neighborhood. Conveniently located near BWI Airport, Baltimore, Washington D.C., and Maryland’s Eastern Shore beaches, with easy access to Routes 97 and 50.

This exceptional home offers the perfect combination of privacy, luxury, location, and community amenities — a rare opportunity that will not last long. Privacy and a modern home that is a must see!

ANNAPOLIS

1718 WESTMINSTER WAY

4 Beds

2 Baths

3,500 Sq.Ft.

$1,149,000

MLS#: MDAA2143876

Striking modern craftsman located in Eastport! This beautifully constructed home boasts 3 levels of living space including the finished basement with great room, bonus room and full bath. The community of Green Acres is a private, water privileged neighborhood with a waterfront park just steps from the home. Located on Back Creek the residents enjoy boat slips, canoe/kayak storage and vibrant community gatherings.

The inviting front porch with balcony above welcomes you as you step onto the property. The high ceilings, plethora of windows for natural light and wide open floor plan set the tone for this wonderful home. The main level features a thoughtful layout and elegant details including a formal living room and dining room which flows to the stunning 2 story Family room with coffered ceiling. The adjacent breakfast nook and gourmet kitchen boasts a massive island; perfect for entertaining. The sunroom off the kitchen is an ideal location to relax or entertain and offers a smooth transition to access the outdoor patio; perfect for alfresco dining. Head upstairs to enjoy the spacious Primary bedroom ensuite with coved ceiling, walk-in closet and luxurious spa-like bathroom. 3 additional bedrooms on this level, one with a spacious balcony overlooking the front yard, provides plenty of space for family and friends. The quaint community of Green Acres provides a community waterfront common area to gather, swim, fish, launch a kayak or tie up a small vessel. The close proximity to downtown Eastport encourages you to stroll the artful and nautical streets to amenities like; five-star restaurants, pubs and shopping. Not to mention you are merely steps away from downtown Annapolis and Naval Academy by either walking across the Spa Creek drawbridge or motoring in the water taxi. From this location, you are also close to some of the Bay's best cruising and fishing areas. Attractive destinations such as Baltimore's Inner Harbor, St. Michael's, Oxford, and Solomon's Island are only a short cruise away. Annapolis offers the perfect balance of small-town charm and big world sophistication. Located just 5 miles to Rt. 50 and 97 which provides direct access to Baltimore, BWI, Ft.Meade/NSA and Washington, DC. Welcome Home!

ANNAPOLIS

819 JANICE DRIVE

4 Beds

3 Baths

4,043 Sq.Ft.

$1,125,000

MLS#: MDAA2136882

This exquisite 5-bedroom, 5 full bath stone-front traditional residence blends timeless sophistication with modern luxury. A grand marble entry foyer introduces the beautifully appointed formal living and dining rooms, adorned with classic picture frame moldings and elegant tray ceilings. At the heart of the home, a gourmet kitchen showcases a custom marble center cooking island and a sun-drenched breakfast room, opening seamlessly to a stunning family room anchored by a dramatic stacked stone two-story gas fireplace. Custom hickory handscape wood floors by Beers flooring. A luminous sunroom and a custom deck off the main level provide refined spaces for both intimate indoor gatherings and gracious outdoor entertaining. The home’s thoughtfully designed bedroom arrangement is truly exceptional, highlighted by a sumptuous primary suite featuring a see-through natural gas fireplace, an expansive sitting room, private deck access, and a spa-inspired bath with a dual walk-in shower, custom travertine floor, marble-topped vanities, a jetted tub, and an oversized walk-in closet. Two generously proportioned bedrooms share a beautifully appointed Jack and Jill bath, while an additional en suite bedroom with its own walk-in closet offers comfort and privacy. New carpet in all of the bedrooms. Laundry on both the main and upper levels enhance everyday ease. The lower level is an entertainer’s dream, offering an expansive family room with new carpet and an impressive 10x10 bar area complete with a built-in granite-topped bar, double drawer dishwasher, and a refrigerator with ice maker. A professionally installed home theater with a 90-inch screen delivers a true cinematic experience, while an additional bedroom with walk-in closet and access to a full bath provides ideal guest accommodations. A substantial storage area and immersive 4-zone surround sound system complete this remarkable level. Outdoors, the home continues to impress with a custom deck, a serene patio with a fountain feature, an inground sprinkler system, and bespoke landscape lighting. Complementing this exceptional offering are community amenities including a gated pool, pavilion, play area, and dog park—creating a lifestyle defined by elegance, comfort, and distinction.

ANNAPOLIS

905 CORNELL AVENUE

5 Beds

5 Baths

6,414 Sq.Ft.

$1,125,000

MLS#: MDAA2143546

Back on the market through no fault of the Sellers. Buyer's home sale contingency was not met, creating a new oppotunity for interested buyers. This gorgeous townhome nestled in the sought-after community of Uptown at Murray Hill, in the heart of downtown Annapolis' West Street Arts District and just steps away from restaurants, pubs, galleries and boutiques. A classic brick façade and covered front porch overlook a charming city garden. Inside, the home is professionally decorated with elegant Pottery Barn furnishings and thoughtfully curated finishes throughout. The entry level features a flex space with French doors—ideal for guests, a home office, or bedroom—along with a convenient powder room. Upstairs, the main living level showcases rich hardwood flooring and an open, light-filled layout perfect for everyday living and entertaining. The bright kitchen is a true centerpiece, complete with granite countertops, stainless steel appliances, a pantry, and a breakfast counter with seating beneath stylish pendant lighting. A sliding glass door opens to the balcony, extending your living space outdoors for grilling. The kitchen flows seamlessly into the dining area highlighted by a designer chandelier, and onward to the inviting living room with a cozy gas fireplace. The primary suite offers a peaceful retreat with luxury vinyl plank flooring, a spacious California-style walk-in closet, and a beautifully appointed ensuite bath featuring dual vanities, generous counter and cabinet space, and a glass-enclosed step-in shower with built-in bench. A large guest bedroom and a hall bath with tub/shower provide comfortable accommodations for family or visitors. The top floor adds exceptional versatility with a game room and lounge area, complete with a wet/dry bar, powder room, and direct access to a private deck—perfect for entertaining or relaxing evenings at home. Additional highlights include a garage and off-street parking. Ideally located with easy access to Rt. 50, Navy–Marine Corps Memorial Stadium, the United States Naval Academy, the Severn River, and all the shops, dining, and waterfront charm of Annapolis, this exceptional home offers the very best of Annapolis living.

ANNAPOLIS

219 WEST STREET

3 Beds

2 Baths

2,080 Sq.Ft.

$1,125,000

MLS#: MDAA2136426

Tucked within the gated waterfront community of Epping Forest, this charming Craftsman bungalow captures the ease and appeal of Annapolis waterfront living with the rare advantage of true one-level living. Perfectly positioned on one of the community’s largest and flattest lots, the property offers a difficult-to-find combination of privacy, outdoor space, and low-maintenance comfort just moments from the Severn River and downtown Annapolis.

Inside, the three-bedroom, two-bath residence is filled with warmth and character. Heated floors provide year-round comfort, while dual fireplaces, including one gas and one wood-burning, create inviting gathering spaces throughout the home. The sun-filled great room features transom windows, abundant natural light, and French doors that open seamlessly to the outdoor living areas, creating an effortless connection between indoors and out.

The surrounding grounds have been thoughtfully designed to embrace every season of Chesapeake Bay living. Mature landscaping, a dedicated vegetable garden, outdoor fireplace, cedar outdoor shower, and expansive patio create a setting equally suited for quiet mornings or entertaining after a day on the water. Seasonal winter views of the Severn River further enhance the property’s appeal and reinforce its connection to the waterfront lifestyle that defines Annapolis and Anne Arundel County.

Life in Epping Forest extends far beyond the home itself. Residents enjoy access to one of Annapolis’ most established and sought-after waterfront communities, complete with a private clubhouse with waterfront dining, deep-water marina, sandy beach, boat ramp, tennis courts, scenic walking trails, and a vibrant calendar of neighborhood events and clubs. The location also offers convenient access to downtown Annapolis, the U.S. Naval Academy, Washington, D.C., Baltimore, and major commuter routes.

This is a rare opportunity to own a turnkey home in one of Annapolis’ premier gated waterfront communities, where the Chesapeake Bay lifestyle is part of everyday living.

Epping Forest is a Special Tax District. Annual tax: $1,583.64. Community is governed by binding Rules and Regulations.

ANNAPOLIS

310 EPPING WAY

3 Beds

2 Baths

2,036 Sq.Ft.

$1,100,000

MLS#: MDAA2145574

Backs to Quiet Waters Park! This spacious and elegant home offers 4 bedrooms, 3.5 bathrooms and approximately 4,400 sq. ft. of living space, with the option to expand to 5,300 sq. ft. by adding a fourth level. The gourmet kitchen features double wall ovens (with the upper oven including an air-fry option), a 36-inch gas cooktop and the choice of a cabinetry hood or stainless-steel chimney hood. Additional highlights include a sunroom. These are to-be-built homes, allowing buyers to make all selections and personalize their finishes.

ANNAPOLIS

116 STILLY WAY

4 Beds

3 Baths

4,400 Sq.Ft.

$1,099,990

MLS#: MDAA2138688

Spacious and elegant, this 4-bedroom, 4.5-bath home offers approximately 4,400 sq. ft., with the option to expand to 5,300 sq. ft. with a fourth level. The gourmet kitchen features double wall ovens (upper with air-fry), a 36" gas cooktop, and choice of cabinetry or stainless steel hood. Enjoy a sunroom, cozy fireplace, 9-foot ceilings on all levels, and a finished basement with full bath. Energy-efficient upgrades include a tankless water heater and two-zone HVAC. Private setting near Quiet Waters Park. Fully furnished model available. Estimated move-in July/August.

ANNAPOLIS

113 STILLY WAY

4 Beds

4 Baths

4,700 Sq.Ft.

$1,079,990

MLS#: MDAA2134880

Welcome to 704 Caleb Lane, a beautifully maintained home in the highly sought-after, amenity-rich Kingsport community of Annapolis. Situated on nearly a quarter-acre lot and just two short blocks from the community pool, clubhouse, playgrounds, water access for kayaking and fishing, and scenic walking and biking trails, this exceptional property offers the perfect blend of comfort, elegance, and convenience.

Located only 10 minutes from Downtown Annapolis, this home provides the tranquility of private community living without sacrificing easy access to shopping, dining, and waterfront attractions.

Inside, you’ll find spectacular natural light throughout all three finished levels, including a fully finished basement suite complete with its own kitchen, laundry room, 1.5 baths, and two spacious bedrooms — ideal for guests, multigenerational living, or extended entertaining space.

The stunning main-level kitchen is designed to impress, featuring sparkling granite countertops, a massive center island, custom cabinetry, and convenient access via a secondary staircase. The kitchen opens seamlessly to the dramatic two-story Great Room, highlighted by a cozy gas fireplace, soaring windows, and elegant custom wood blinds.

Beautifully maintained hardwood floors run throughout the home, adding warmth and timeless appeal. Outside, the pristine driveway and oversized two-car garage provide ample parking and storage space for gardening, landscaping, and recreational needs.

Additional recent updates include:
* Roof
* HVAC system
* Water heater

This elegant home truly checks every box — offering exceptional space, thoughtful upgrades, outstanding community amenities, and an unbeatable Annapolis location.

ANNAPOLIS

704 CALEB LANE

6 Beds

4 Baths

4,166 Sq.Ft.

$1,050,000

MLS#: MDAA2145044

Welcome to 903 Scupper Ct. Luxury living at its finest. Located close to Annapolis in the community of Broad Creek Landing. This magnificent home features almost 4300 sq. ft on the upper two levels with an additional 1500 sq. ft. of finished area in the lower level. This home was built for the executive lifestyle.
The main level includes a foyer, formal living room and dining room, large family room, gourmet kitchen with breakfast area and a separate office/library. All opening to a fabulous maintenance free deck. The upper level includes 3 large bedrooms for children and guests and 2 baths. The main bedroom/suite is comprised of a large bedroom area and sitting room. His and her closets. The main bath is absolutely beautiful. Soaking tub, large shower, his and her vanities and marble floor. The lower level is finished as a large room. This can be used for multiple adventures, as well as a full bath and access to the exterior.
The home has a brick front with maintenance free vinyl siding and aluminum facia and soffit. The roof was replaced in 2019. The upper two levels were repainted in 2024. New water heater. Everything you can ask for is in this magnificent. It is close to Annapolis, Baltimore, Washington, Rt.97 and Rt. 50. Level back yard with blooming trees and new shed!
Livability, convenience, luxury, they are all present in this home. Come and view this spectacular home!

ANNAPOLIS

903 SCUPPER COURT

4 Beds

4 Baths

5,766 Sq.Ft.

$1,050,000

MLS#: MDAA2141286

She’s one and a half years young. She’s flawless. And she’s exactly the kind of home buyers spend months hoping will hit the market—but almost never does. Welcome to 141 Stilly Way, a fully upgraded, privately owned resale in Parkside Preserve where every premium finish, every design decision, and every upgrade has already been completed for you. This is not a builder sale. There are no construction delays, no upgrade meetings, no added expenses, and no waiting. This is the finished product—refined, elevated, and completely move-in ready. From the moment you step inside, the home delivers a level of warmth, sophistication, and functionality that instantly stands apart. Sunlight pours through the expansive open-concept layout, highlighting wide-plank flooring, elevated finishes, and spaces designed for the way people truly live today. At the center of the home is a stunning designer kitchen featuring premium cabinetry, quartz countertops, tiled backsplash, under-cabinet lighting, double wall ovens, a gas cooktop, stainless hood, and an oversized island that effortlessly anchors everyday living and entertaining alike. The kitchen opens seamlessly to the inviting family room with a gas fireplace and peaceful wooded backdrop, creating a setting that feels both luxurious and comfortable. Upstairs, the primary suite feels like a private retreat with a spa-inspired bath and oversized walk-in closet, while the additional bedrooms provide generous space and flexibility for family, guests, office needs, or lifestyle changes. The fully finished lower level extends the home beautifully, offering the ideal space for entertaining, movie nights, a gym, guest accommodations, or a second living area. But what truly elevates this property is the lifestyle that comes with it. Parkside Preserve has quickly become one of Annapolis’ most desirable newer communities because it offers something buyers desperately want but rarely find—modern luxury living paired with genuine neighborhood connection. Sidewalk-lined streets, walking paths, a community playground, and a welcoming neighborhood atmosphere create the kind of everyday environment people instantly fall in love with. And the location is exceptional. One of the biggest lifestyle advantages of living here is the ability to walk or bike directly to Quiet Waters Park—one of Annapolis’ most beloved waterfront destinations offering miles of scenic trails, kayaking, dog parks, picnic areas, outdoor concerts, and year-round community events. Imagine evening walks through the park, morning runs along the water, or weekends spent enjoying the Chesapeake lifestyle just moments from your front door. Equally impressive is the home’s proximity and walkability to local restaurants, coffee spots, waterfront dining, marinas, and the charm of Annapolis. Dinner out, drinks with friends, coffee runs, waterfront sunsets, and spontaneous nights in town become part of your everyday routine instead of a special occasion. This location perfectly blends the peaceful feel of a newer community with the vibrant lifestyle Annapolis buyers are truly searching for. Morning coffee on the deck. Walks to Quiet Waters Park. Dinner nearby. Sunset evenings by the water. Weekends on the Chesapeake Bay. This is more than just a beautiful home—it’s the lifestyle people move to Annapolis hoping to find. And the reality is simple: homes like this—this upgraded, this turnkey, this perfectly located—without the builder process attached, simply do not last.

ANNAPOLIS

141 STILLY WAY

5 Beds

4 Baths

5,140 Sq.Ft.

$1,049,000

MLS#: MDAA2139818

VIRTUAL TOUR: https://my.matterport.com/show/?m=FRKRayZVZEv&mls=

Buyer may keep all furnishings if desired, all items in garage will be removed prior to sale.

Welcome to 3249 Arundel on the Bay Road — where coastal charm meets timeless character in one of Annapolis’ most sought-after waterfront communities.

Nestled in the heart of Arundel on the Bay, this beautifully positioned home offers the rare opportunity to enjoy true Chesapeake Bay living with a blend of tranquility, charm, and convenience. Surrounded by water and embraced by a tight-knit community known for its private beaches, boat ramps, and breathtaking sunsets, this property delivers a lifestyle—not just a home.

Step inside to discover a residence filled with natural light, warm finishes, and an inviting layout designed for both everyday living and effortless entertaining. The home features spacious living areas, well-appointed bedrooms, and thoughtful touches throughout that create a sense of comfort and functionality.

Outside, enjoy serene outdoor living with space to relax, entertain, or simply take in the coastal breeze via backyard and 2nd floor deck. Whether you’re hosting gatherings, unwinding after a long day, or heading out for a walk along the water, this home offers the perfect backdrop.

Living in Arundel on the Bay means access to exclusive community amenities, including private beaches, a boat ramp, fishing piers, playgrounds, and kayak storage—making it a dream for water enthusiasts and nature lovers alike. All of this, just minutes from historic downtown Annapolis, dining, shopping, and major commuter routes.

Whether you’re seeking a full-time residence, a weekend retreat, or an investment opportunity in a highly desirable waterfront enclave, 3249 Arundel on the Bay Road is a rare find that captures the essence of coastal Maryland living.

Don’t miss your chance to own a piece of the Bay lifestyle.

ANNAPOLIS

3249 ARUNDEL ON THE BAY ROAD

4 Beds

3 Baths

2,800 Sq.Ft.

$1,025,000

MLS#: MDAA2139224

1 ... 3 4 5

Buyers resources

7 Reasons to Work with a Realtor

7 Principles For Home Buying Success

Getting a Mortgage To Buy a Home

Home Hazards Awareness

Key Items For Home Inspection

Questions When Buying a Condo

Questions When Choosing a Realtor

Sellers resources

8 reasons to work with a realtor

Calculating Capital Gains

Checklist for Better Showing

Cleaning Home For Sale

Improving Odds Of an Offer

Preparing Home for photoshoot

Selling Your Home for More $$

Buyers resources

BUYERS RESOURCES

Sellers resources

SELLERS RESOURCES

properties found. properties found. Page of .

- property

Send a message

Message successfully sent.

First Name

Last Name

Email

Phone

MLS Property Number

Your message

What is 3 + 4 ?

Reason for contacting?

Buying a home

Selling a home

Other

I agree to receive email communication and understand I can unsubscribe at any time.

I agree to be contacted by Maryland Sandbox via call, email, and text for real estate services. To opt out, you can reply 'stop' at any time or reply 'help' for assistance. You can also click the unsubscribe link in the emails. Message and data rates may apply. Message frequency may vary. Privacy Policy

Update Your Temporary Password

Accessibility Menu

Personalize your search

Enter your email and we'll notify you immediately when new listings match what you're looking for.

or enter email address

Email address (Must be valid)

Already have an account ? Login here

Continue your home search

Email address

First name First Name

Last name Last Name

Phone number (Optional)

Password

I agree to receive communications and understand I can unsubscribe at any time.

I agree to be contacted by Maryland Sandbox via call, email, and text for real estate services. To opt out, you can reply 'stop' at any time or reply 'help' for assistance. You can also click the unsubscribe link in the emails. Message and data rates may apply. Message frequency may vary. Privacy Policy

Already have an account ? Login here

We use cookies

We use cookies primarily for analytics to enhance your experience. By accepting, you agree to our use of these cookies. You can manage your preferences or learn more about our cookies policy.

Privacy Policy Terms of Service