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
300
# of Listings
3
Avg # of Bedrooms
$467
Avg. $ / Sq.Ft.
$1,062,130
Med. List Price

Browse Annapolis Real Estate Listings

All listings

Under $250,000

$250,000 - $500,000

$500,000 - $1M

$1M - $3M

$3M - $5M

Over $5M

54 Properties Found. Page 1 of 4.

ONLINE REAL ESTATE AUCTION!! Online Bidding Opens - Monday, September 1, 2025. Online Bidding Closes - Wednesday, September 3, 2025 at 11:00 AM. List price is opening bid only. 199 Prince George Street is situated in the Downtown Annapolis Historic District, one block east of State Circle, and one block northwest of the City Dock. The home is within a short walk of Maryland State government offices, the State House, legislative houses, the US Naval Academy, restaurants, hotels, shops, historic sites and Annapolis Harbor. Prince George Street is a picturesque one-way street, lined with detached homes and townhomes often exceeding 100 years of age.
#MDAA2122376

ANNAPOLIS

199 PRINCE GEORGE STREET

3 Beds

3 Baths

2,134 Sq.Ft.

$500,000

MLS#: MDAA2122376

Enjoy a fantastic lifestyle in this beautiful and pristine 2BR/2BA condo in the very desirable and vibrant 55+ community of Four Seasons at St Margarets! Enter the very well-kept secure building and access your second floor home by stairs or elevator ...OR use your garage door remote and enter the building through your private, over-sized garage. The dramatic open floor plan is ideal with kitchen island overlooking the huge living room with gorgeous hardwood floors and plantation shutters. The living room leads to a large, private balcony. The primary bedroom is massive with a large bay window and an over-sized walk-in closet. The attached bathroom has a walk-in shower and separate soaking tub. The second bedroom has a bay window, two double closets and is served by a hall bath. A large laundry room and multiple closets complete this side of the condo. Nothing to do but move in and enjoy the incredible amenities - stunning community center has several beautifully furnished party areas to entertain your guests and meet with neighbors. There is a kitchen, bar, billiards room, library, fitness center and inviting outdoor pool with many tables and chairs to enjoy the beautiful weather and wooded surroundings. The location is ideal - tucked away, but very close to shopping, public library, hiking and bike trail, and easy access to downtown Annapolis! Smoking Restricted Community
#MDAA2114444

ANNAPOLIS

1509 FERAL DAE LANE 204

2 Beds

2 Baths

1,442 Sq.Ft.

$500,000

MLS#: MDAA2114444

Model Home Now For Sale! Bright, spacious unit at second floor elevation showcasing stylish design upgrades throughout! Start an exciting new chapter in this amenity-rich 55+ community conveniently located mere minutes to downtown Annapolis, retail shopping, waterfront dining and Bay Bridge. Reserved parking included. Turnkey luxury includes window treatments, full-size washer and dryer and more! Building One nearly sold out - tour this gorgeous staged model home today!!
#MDAA2110762

ANNAPOLIS

78 OLD MILL BOTTOM ROAD N 107

2 Beds

2 Baths

1,318 Sq.Ft.

$499,900

MLS#: MDAA2110762

Welcome to easy living in the highly sought-after 55+ community of Heritage Harbour where the amenities rival the finest resorts! This charming one-level home offers a perfect blend of comfort, style, and convenience, plus a private and serene back setting surrounded by trees for an added peaceful feeling. Featuring 2 spacious bedrooms, 2 full bathrooms, a den, and an updated kitchen, this residence is designed for modern living. You'll love the new flooring, fresh paint, and the private back patio—ideal for leisurely mornings or relaxing evenings. Enjoy the ease of a one-car garage and low-maintenance living while taking advantage of everything Heritage Harbour has to offer. Residents enjoy access to indoor and outdoor pools, a fully equipped fitness center, tennis and sport courts, a community library, performance hall, scenic walking trails, and water access for kayaking or boating. All this, plus convenient proximity to shopping, dining, and major commuter routes. Don't miss your chance to live in one of the area's premier active adult communities—where lifestyle meets location!
#MDAA2118638

ANNAPOLIS

2601 COMPASS DRIVE

2 Beds

2 Baths

1,514 Sq.Ft.

$496,500

MLS#: MDAA2118638

Step into an unparalleled opportunity to own a piece of Cape St. John — all for under $500,000! This rare gem offers the perfect blend of coastal charm, modern upgrades, and an enviable location in one of the area’s most beloved waterfront communities. Welcome to your dream retreat! Just a short stroll from your door, you’ll find one of the community’s best private beaches, complete with a sandy shoreline, kayak storage, boat ramp, designated swimming area, and dock along the majestic South River. This home packs a big punch for its price, featuring numerous upgrades on a beautifully maintained and usable .34-acre lot with seasonal water views. Imagine sipping your favorite beverage on the inviting front porch, surrounded by mature trees that provide privacy and a serene landscape setting. Location couldn’t be better — just minutes from Mike’s Crab House, Routes 50 and 97, and only 15 minutes from historic Annapolis, while shopping and everyday conveniences are just a short drive away. Why settle for a townhouse when you can have a private lot and single-family home, with multi-million-dollar waterfront estates just a few houses down? Don’t let this rare opportunity slip away — Cape St. John living awaits!
#MDAA2124512

ANNAPOLIS

251 CAPE SAINT JOHN ROAD

2 Beds

1 Baths

1,002 Sq.Ft.

$495,000

MLS#: MDAA2124512

Charming Condo for sale in Heritage Harbour's 55+ Community. Step into a lifestyle of ease and sophistication in this beautiful condo, nestled within the vibrant 55+ community of Heritage Harbour in Annapolis. Perfect for active adults, this sought after neighborhood offers a host of amenities tailored to enhance your daily living. Enjoy access to a state-of-the-art clubhouse, indoor and outdoor swimming pools, tennis courts, a fitness center, scenic walking trails, and even a golf course and dock for your boat and kayaks. Socialize with friends through the community, grab a meal at the private community restaurant Wilder Fresh Kitchen, or simply unwind in the serene surroundings.
#MDAA2119226

ANNAPOLIS

940 ASTERN WAY 112

2 Beds

2 Baths

1,588 Sq.Ft.

$495,000

MLS#: MDAA2119226

Exceptionally beautiful 1 BR/1 Bath with stunning sunset views in like-new condition. The only unit available in this Luxurious Condo Building still priced below $500K. Many upgrades: New Bosch HVAC Heat Pump costing $10K, New designer walk-in shower costing $12 K , New carpeting in Bedroom., Hardwood floors, granite counters. Many amenities : 24/7 live person at the Lobby Front Desk, very secure building, One owned/ assigned underground garage parking space with remote opener, Fitness Center, Outdoor Pool and Hot Tub, Two Outdoor Gourmet BBQ kitchens, Gardening Area, Library, Party Room , TV Lounge , Free Shuttle Service to downtown, just blocks to City Dock attractions: restaurants, entertainment venues, shopping. The most luxurious condo residence in this county.
#MDAA2121784

ANNAPOLIS

5 PARK PLACE 431

1 Beds

1 Baths

839 Sq.Ft.

$489,900

MLS#: MDAA2121784

An incredible find; Welcome home to 577 Francis Nicholson Way, a rarely available end unit townhome residence in the highly desirable Tidewater Community! With fresh carpet on the main & upper floors along with new roof (1 year old), newer HVAC (under 2 years old), and newer hot water heater, move in complete peace of mind! Past the hardwood laden foyer, the kitchen flows with hardwoods, granite countertops, stainless steel appliances, and a breakfast nook perfect for morning coffee. The hardwoods continue through the dining room which flows to a fresh-carpet laden family room complete with gas fireplace and sliding door to the deck & backyard. Upstairs the primary bedroom shines with natural light on the vaulted ceiling, and it's ample size compliments the walk-in closet. An en-suite primary bathroom is ready for your personalized touches. The second bedroom, also with new carpet, is past the hallway second-full bathroom. A fully finished basement has a sizable living room and graciously spaced third bedroom equipped with full bathroom. To round out this incredible offering is Tidewater Colony's incredible community amenities complete with pool, tennis courts, club house, community center, and so much more!
#MDAA2118986

ANNAPOLIS

577 FRANCIS NICHOLSON WAY

3 Beds

3 Baths

2,092 Sq.Ft.

$489,000

MLS#: MDAA2118986

Welcome to a home that checks all the right boxes: space, convenience, and location. With four generously sized bedrooms and two full bathrooms, this townhouse offers room to grow, work from home, or host weekend guests who end up staying just a bit longer than planned. The living space features a bright, open layout with plenty of natural light—perfect for morning coffee, afternoon naps, or an impromptu dance party (no judgment). The kitchen and dining flow smoothly into the main living area, making entertaining easy and cleanup even easier. Step outside and enjoy a private outdoor space, great for grilling in the summer or sipping something warm in the fall. There's even an attached garage—a rare find in townhouse living—for convenient parking and additional storage. If you're into fresh air and weekend strolls, you're in luck. A scenic walking trail is just around the corner, while nearby parks offer playgrounds and green spaces. Thinking about school options? One of the area’s top-rated high schools is only a short distance away. When it's time to stock the fridge or grab takeout, local grocery stores and a variety of dining spots are close at hand. And if your weekdays involve commuting, you'll enjoy easy access to major routes connecting you to Annapolis, Baltimore, and Washington. Whether you're a first-time buyer or simply looking to simplify life without giving up comfort, this home offers the lifestyle you've been looking for—no compromising required.
#MDAA2120130

ANNAPOLIS

633 BAYSTONE COURT

4 Beds

2 Baths

1,868 Sq.Ft.

$484,995

MLS#: MDAA2120130

Beautifully Updated 2-Bedroom Condo in Heritage Harbour Welcome to this bright and spacious first-floor corner condo in the highly desirable 55+ Heritage Harbour community. This updated 2-bedroom, 2-bath home features hardwood floors throughout and an abundance of natural sunlight. Enter through your private side entrance off the walk-up patio into an open-concept living room, complete with custom built-in bookshelves and plenty of space for entertaining. The kitchen flows seamlessly from the living area, making it perfect for gatherings. The large primary suite includes an updated bathroom, while the second bedroom has been thoughtfully designed as a custom home office with excellent storage options. This unit also comes with its own underground garage parking space for added convenience. What makes this building truly special is that it is the only building in Heritage Harbour with its own indoor and outdoor pool and fitness center on-site—meaning you can enjoy swimming or working out just steps from your door without having to go to the Lodge. Beyond your building, Heritage Harbour offers resort-style amenities, including golf, tennis, dining, water access, walking trails, and so much more—all designed for an active and vibrant lifestyle.
#MDAA2123520

ANNAPOLIS

930 ASTERN WAY 105

2 Beds

2 Baths

1,578 Sq.Ft.

$477,000

MLS#: MDAA2123520

Annapolis One-Level Living with Endless Potential! Discover over 2,300 sq. ft. of spacious one-level living on a large ¼-acre lot in a quiet, sought-after neighborhood. This home offers an upgraded kitchen with Oak cabinets, Corian countertops, and newer appliances—perfect for culinary enthusiasts. Beneath the carpet in the living room and bedrooms, beautiful hardwood floors await your personal touch. Enjoy the bright sunroom off the kitchen, ideal as a dining area or family room, which leads to a new deck with steps and a handicapped-accessible ramp. The full, unfinished basement provides limitless possibilities—create a home gym, theater room, office, additional bedrooms, or media space. Additional highlights include an attached oversized one-car garage with room for a workbench, a fenced backyard perfect for kids, pets, and entertaining, and freshly painted interiors throughout. Conveniently located close to Annapolis, major commuter routes, shopping, and all amenities, this home blends comfort, function, and location perfectly.
#MDAA2123640

ANNAPOLIS

114 2ND STREET

3 Beds

2 Baths

2,370 Sq.Ft.

$475,000

MLS#: MDAA2123640

Popular Hunt Meadow townhome model ONE-LEVEL living-2 BDRM/2 BA - with basement! Wood floors throughout- tile in kitchen, vaulted ceilings, gas fireplace. Remodeled main Bathroom. Recent new roof and deck. Reasonable HOA fees of $250/mo. covers pool/tennis/jog-bike trails, prof off-site mgmt.; lawn maintenance; trash; snow shoveling to your front door!
#MDAA2119470

ANNAPOLIS

7 ASHFORD COURT

2 Beds

2 Baths

1,740 Sq.Ft.

$465,000

MLS#: MDAA2119470

Price Adjustment! Welcome to 8 Ashford Ct — Modern Living in the Heart of Annapolis! Now offered at a new, more attractive price, this beautifully updated 2-bedroom, 1.5-bath contemporary townhouse is move-in ready and full of upgrades. Enjoy a spacious open floor plan featuring gleaming hardwood floors and a modern kitchen with stainless steel appliances. Located in the highly desirable Hunt Meadow community, residents have access to amenities including a pool, tennis courts, and scenic walking paths. All just minutes from downtown Annapolis, shopping, dining, and commuter routes — don’t miss this fantastic opportunity!
#MDAA2115574

ANNAPOLIS

8 ASHFORD COURT

2 Beds

1 Baths

1,248 Sq.Ft.

$465,000

MLS#: MDAA2115574

Beautiful Condo on Spa Creek! PRICE IMPROVEMENT TO $460K. Great investment property, second home or live in downtown Annapolis! Located in the heart of desirable Eastport, this inviting condo offers the best of Annapolis nautically inspired living. 316 Burnside Street has big water views of the serene waters of Spa Creek! This home offers an ideal retreat for those seeking both tranquility in the city of Annapolis! Updated kitchen offers rich cherry cabinetry, gleaming granite countertops, and stainless steel appliances. The kitchen is both functional and stylish. Modern, nautical ash and cherry wood floors flow seamlessly throughout, adding warmth and style to this comfortable space. Recent upgrades includes all new HVAC 2022 of 2 units, freshly painted, and recessed lighting. The Burnside Condominium offers a unique blend of urban living and waterfront charm, featuring a rooftop pool and deck with panoramic views of Spa Creek, downtown Annapolis, and the U.S. Naval Academy. These amenities provide residents with a serene retreat to enjoy sunsets, watch events like the Blue Angels' flyovers, NAVY commissioning week, and parade of lights. Partake in kayaking, and paddle boarding with private dock space. and water taxis. Deep water boat slips available for a rental fee. Entertain your friends and watch the Annapolis fireworks from your deck without fighting the crowds. The Burnside Condominiums in Annapolis offers a unique blend of urban living and waterfront charm, featuring a rooftop pool and deck with panoramic views of Spa Creek, downtown Annapolis, and the U.S. Naval Academy. Take an easy stroll to some of the best waterside restaurants, yacht clubs, shopping, grocery store, and all the charm Annapolis has to offer! This is a secured building, with keyed entry, intercom system, and elevator access. There is laundry use on all condo levels and main floor storage unit for your condo space. Off street parking for residents on lot, and guest parking available. This a beautiful home and you will not want to miss a viewing! Move right in and enjoy Annapolis living at its very best!
#MDAA2114264

ANNAPOLIS

316 BURNSIDE STREET 304

1 Beds

1 Baths

526 Sq.Ft.

$460,000

MLS#: MDAA2114264

It’s rare to find a home that checks all the boxes—peaceful neighborhood, functional space, and a location that keeps you connected. This one does just that. Nestled on a quiet cul-de-sac in Whispering Woods, the setting feels tucked away while still offering easy access to everything Annapolis has to offer. Step outside and you’re just minutes from Broadneck parks, local shops, and waterfront dining—yet the neighborhood itself feels like a retreat, with wooded walking paths, a community playground, and neighbors who take pride in their surroundings. The fully fenced backyard backs to trees, offering privacy and room to enjoy the outdoors. Inside, the home’s layout is made for everyday living. Defined spaces flow naturally from one level to the next, with a cozy fireplace downstairs and extra room for whatever life throws your way—whether that’s working from home, hosting guests, or simply needing a bit more space. For anyone looking to put down roots in a neighborhood that feels established, welcoming, and close to it all—this is the kind of place where the next chapter can begin.
#MDAA2116680

ANNAPOLIS

414 BLOSSOM TREE COURT

3 Beds

1 Baths

1,560 Sq.Ft.

$444,900

MLS#: MDAA2116680

1 2 3 4
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 $$

properties found. properties found. Page of .

- property

Send a message

Message successfully sent.

Your message

Reason for contacting?

Sign Out

Virtual Assistant

Would you like to receive some additional information on this specific property or similar properties?

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

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

Already have an account ? Login here

Continue your home search

Already have an account ? Login here