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

266

# of Listings

3

Avg # of Bedrooms

$480

Avg. $ / Sq.Ft.

$1,289,299

Med. List Price

Browse Annapolis Real Estate Listings

$250,000 - $500,000

$1M - $3M

68 Properties Found. Page 5 of 5.

Tucked within the sought-after gated waterfront community of Epping Forest, this charming Craftsman-style home pairs a serene, elevated setting with exceptional water access at the mouth of Clements Creek and the Severn River. The private sandy beach and deep-water pier with 12,000-lb boat lift create an ideal launching point for boating, paddleboarding, and exploring Annapolis waterways while embracing the quintessential Annapolitan lifestyle.

Situated on a peaceful 0.39-acre homesite surrounded by trees, woods, and water views, the beautifully renovated residence offers over 3,000 square feet across three finished levels with 4 bedrooms and 4 full baths. A welcoming stone stairway and thoughtfully designed landscaping lead to an interior filled with natural light, open living spaces, and timeless craftsmanship. The kitchen, dining area, and living room with fireplace flow seamlessly to a screened porch and deck—perfect for alfresco dining and relaxing among the treetops.

The main level features a spacious bedroom with sitting area and hall bath, ideal for convenient single-level living. Upstairs, a dramatic landing with soaring ceilings and private balcony connects two ensuite bedrooms, including the primary suite showcasing treetop views and glimpses of the water, complemented by dual vanities and a custom tiled walk-in shower.

The walk-out lower level expands the home’s versatility with a family room with fireplace, additional bedroom, full bath, home office or flex space, generous storage, and private patio—providing comfortable accommodations for guests and everyday living alike.

Exclusive Epping Forest Gated Community offers fabulous amenities including the clubhouse with waterside bar and grill, deep-water marina, sandy beach, boat ramp, tennis courts, hiking paths plus year-round activities including: July 4th fireworks, Labor and Memorial Day festivities, oyster roast and summer camps. There's so much fun to be had in Epping Forest, great social clubs include the boat club, volleyball leagues, swim team and garden club. Come and enjoy all that Epping has to offer! Conveniently located to access Downtown Annapolis, head over the Bay Bridge to the Eastern shore or jump on Rt. 50 to get back to Washington, D.C. Annapolis living at its best! Epping Forest is a Special Tax District, ($1964.86/yr.) with binding Rules & Regulations. Welcome Home!

ANNAPOLIS

357 OVERLOOK TRAIL

4 Beds

4 Baths

3,070 Sq.Ft.

$1,100,000

MLS#: MDAA2136590

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

She’s one and a half years young. She’s flawless. And she’s the one buyers keep hoping hits the market—but almost never does. Welcome to 141 Stilly Way, a fully upgraded, privately owned resale in Parkside Preserve where the work is already done, the upgrades are already in place, and the wait is completely eliminated. This is not a builder sale. This is the finished product—refined, elevated, and move-in ready without the stress, delays, or added expense of building. From the moment you walk in, the home delivers—light-filled, expansive, and intentionally designed for the way people actually want to live today. The main level flows effortlessly, anchored by a stunning designer kitchen with premium cabinetry, quartz countertops, tiled backsplash, under-cabinet lighting, and a chef’s appliance package with double wall ovens, gas cooktop, and stainless hood, all opening to a warm and inviting family room with a gas fireplace and peaceful wooded backdrop. Upstairs, the primary suite feels like a true retreat with a spa-inspired bath and oversized walk-in closet, while the additional bedrooms offer space, comfort, and flexibility. The fully finished lower level creates the perfect extension of the home—ideal for entertaining, guests, a gym, or movie nights. And beyond the home itself, the lifestyle is exactly what today’s buyers are chasing—a newer community filled with friendly neighbors, sidewalks, and a true sense of connection, paired with resort-style amenities including a pool, clubhouse, fitness center, playgrounds, and walking trails. Step outside your door and you’re minutes to Quiet Waters Park with its waterfront trails, dog park, and outdoor concerts, as well as the charm of Annapolis—from historic streets and boutique shopping to waterfront dining, marinas, and endless Chesapeake Bay adventures. Morning coffee on your deck, evening walks through the neighborhood, weekends on the water, and nights out in town—this is the lifestyle people move here for. And here’s the reality—homes like this, in this condition, in this location, without the builder process, do not sit. If you’ve been waiting for the right one, this is it.

ANNAPOLIS

141 STILLY WAY

5 Beds

4 Baths

5,140 Sq.Ft.

$1,095,000

MLS#: MDAA2139818

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

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.

$1,050,000

MLS#: MDAA2139224

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

New on site 4 days ago

Stunning brick front colonial with over 6,000 total square feet featuring 4/5 bedrooms and 4½ baths across 3 finished levels on a premium lot. This home offers a sunroom, an updated eat-in kitchen with a recently installed oversized white stone island and a new refrigerator and dishwaher offering perfect space for family meals and entertaining. Enjoy a 2-story great room with a wall of windows and gas fireplace, plus a main-level office, a formal living and dining room- all with hardwood floors. The primary suite boasts hardwood floors, tray ceiling, and peaceful views of the woods. The lower level has a full bath, a recreation room, an exercise room with special rubber flooring and a potential 5th bedroom with outside entrance. The rear fenced yard backs to open space with walking paths and woods, including a patio and spacious lawn. Additional highlights include a 2-car garage with finished flooring, recent carpet and paint throughout. Located in the sought-after, community of Kingsport, offering easy access to downtown Annapolis and community routes to BWI and Washington, D.C. Community amenities include a pool, community pier, tot lot, kayak storage, and walking paths. A perfect blend of comfort, style, and outdoor enjoyment!

ANNAPOLIS

732 PEARSON POINT PLACE

5 Beds

4 Baths

5,333 Sq.Ft.

$1,025,000

MLS#: MDAA2143452

Rare waterfront redevelopment opportunity in Annapolis. The existing structure is a complete shell and requires a full renovation or rebuild. Ideal for investors, builders, or buyers looking to design and construct a custom waterfront home from the ground up.

Located along the protected waters of Oyster Cove, the property includes a deep-water pier and boat house. The existing footprint and favorable waterside placement offer strong potential to maximize views and overall design.

Convenient access to the Chesapeake Bay and close proximity to Historic Downtown Annapolis by both land and water. Enjoy boating, sailing, and easy access to surrounding waterfront destinations throughout the region.

Property is being sold strictly as-is. A unique opportunity for those ready to take on a full redevelopment project in a prime waterfront setting.

ANNAPOLIS

1254 WASHINGTON DRIVE

5 Beds

4 Baths

9,960 Sq.Ft.

$1,000,000

MLS#: MDAA2143700

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.

Sign Out

Virtual Assistant

Would you like to take the next step with this property? We can help you schedule a showing or virtual tour, or send you more details.

Yes, I would like more information.

Thank You for Your Reply, One of Our Agents will contact you as soon as possible

No, maybe later.

Thank you, you can always contact me via email, phone number or through the contact form.

Realhub AI

Lucy - Your AI-Powered Realtor

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.

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