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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

391

# of Listings

3

Avg # of Bedrooms

$455

Avg. $ / Sq.Ft.

$1,131,506

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

391 Properties Found. Page 5 of 27.

Location, location, location! INVESTOR alert for an apartment unit building that can be converted to a single family home in historic Annapolis! This property is steps away from city dock and all that downtown Annapolis has to offer! Enjoy incredible views of historic Annapolis & Spa Creek. The Red Brick Inn is currently being used as a full time Airbnb, but it can easily be converted to a single family home. There are a total of three separate apartments that have all been updated in 2014 and are all separately metered. Floor plans and additional information available upon request! Don’t miss out on this one!

ANNAPOLIS

15 NEWMAN STREET

7 Beds

None Baths

3,509 Sq.Ft.

$1,799,999

MLS#: MDAA2016852

Annapolis four-to-five bedroom waterfront home offers water views from every level! Private dock gives you direct access to the Chesapeake Bay. This stunning custom-built waterfront home is nestled in one of Annapolis’ sought-after neighborhoods. Inviting décor features views of water and a private setting. Casual living room opens to formal dining in a comfortable traditional layout. Stunning kitchen is surrounded by windows and features a large island, gas range, and plentiful cabinets. Kitchen dining area overlooks natural wooded vista. Stone fireplace is the focal point in the bright family room that leads to a large deck and water views. Rich warm wood floors flow from room-to-room throughout! Primary suite features water views, gas fireplace, plantation shutters, and a custom bath with soaking tub, glass shower & separate sinks. Huge walk-in closet features custom shelving. Full laundry on second-level. Two additional bedrooms and baths have been beautifully updated with designer touches. Lower level features a third fireplace, wet bar, and glass sliders to the back yard. Great for a fifth bedroom or an office! New custom steps and walkway lead down a gentle slope to the private dock (4 feet MLW). Your neighbors will include herons and turtles as the headwaters of Lake Ogleton offer a quiet respite for all! Whether you like to kayak or want to power or sail out to the Chesapeake Bay, you will have quick access to all the water activities Annapolis has to offer. Lake Ogleton is a water skier's heaven and the open waters of the Chesapeake are a sailor's paradise. Annapolis Roads has a private community beach and picnic area on a bluff with stunning views of the Severn River and the Chesapeake Bay. This established community is convenient to the restaurants and marinas in Eastport or to major commuter routes. New HVAC 2019, New Hot Water Heater 2020, New HVAC 2022. Annapolis Roads is a Special Tax District; HOA fees included in the annual property owners tax.

ANNAPOLIS

2656 QUEEN ANNE CIRCLE A

4 Beds

4 Baths

3,315 Sq.Ft.

$1,795,000

MLS#: MDAA2111166

FABULOUS PENTHOUSE. Embrace a lifestyle of unparalleled luxury and breathtaking views with this rare opportunity to own an exquisite penthouse at the GrandView in Annapolis Town Center. Perched atop the prestigious 12th floor, this sprawling residence stands as one of the most coveted penthouses, offering panoramic views that stretch for miles, complemented by two expansive balconies that provide front-row seats to the vibrant holiday events and outdoor venues of the Town Center.

Step inside to discover a world of refined elegance, where light cascades through oversized windows, illuminating the dramatic 11-foot ceilings that stretch overhead, creating an atmosphere of open, airy sophistication. This penthouse boasts an expansive layout, featuring three private ensuite bedrooms, each a serene retreat of comfort and luxury. A large den offers flexibility for your lifestyle, whether as a home office, media room, or additional guest space, ensuring this home meets your every need. Newly installed 2-Zone HVAC system and new washer and dryer.

The heart of this home is the open floor plan, seamlessly connecting living spaces with Brazilian cherry hardwood and ceramic tile floors underfoot, exuding warmth and timeless elegance. The gourmet kitchen is a chef's dream, outfitted with high-end appliances, sumptuous granite countertops, and a massive kitchen island, making it perfect for hosting gatherings or savoring quiet moments over coffee.

GrandView isn’t just a residence; it’s a community that offers a true sense of belonging. Residents enjoy exclusive access to a rooftop sky lounge and pool, an outdoor kitchen, a state-of-the-art fitness center, and a club/party room, all designed to foster a lifestyle not just of luxury, but of wellness and social connectivity. The addition of a professionally managed concierge staff ensures every day is lived with ease, convenience, and security.

Situated in the heart of Annapolis, GrandView places you just a stroll away from the finest dining, Whole Foods, Target, Life Time Fitness Club, banking, and boutique shopping. Historic downtown Annapolis, the US Naval Academy, Anne Arundel Medical Center, and Annapolis Mall are mere minutes away, making this a dream location for commuters with quick access to Route 50 and 97.

Seize this unmatched opportunity to indulge in refined urban living at its most sophisticated. Schedule your showing today and take the first step into a life filled with luxury, comfort, and breathtaking beauty in this unparalleled penthouse residence.

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 1210

3 Beds

3 Baths

3,520 Sq.Ft.

$1,750,000

MLS#: MDAA2103424

Coastal elegance meets everyday comfort in this stunning Arundel-on-the-Bay home, perfectly perched to capture peaceful water views of Fishing Creek. From the moment you arrive, this residence promises an elevated lifestyle—whether you're entertaining in the open-concept main living area, savoring a quiet evening on the gracious porch overlooking the water, or launching your next adventure from the oversized garage with room for all your gear.

Inside, rich hardwood floors flow throughout the home, complementing the airy coastal palette and natural light pouring in from every angle. The thoughtfully designed kitchen and dining spaces make hosting effortless, while three spacious bedrooms and two and a half stylish baths offer plenty of space for family and guests alike.

The fully fenced backyard is a private oasis for morning coffee, summer BBQs, or evenings under the stars. And when the day winds down, there’s nothing better than watching the sun reflect off the creek from your own slice of Chesapeake paradise.

Located in the sought-after Arundel-on-the-Bay community—just minutes from downtown Annapolis yet a world away—this home is the perfect blend of charm, function, and waterfront serenity.

ANNAPOLIS

3403 NIAGARA ROAD

4 Beds

3 Baths

3,520 Sq.Ft.

$1,700,000

MLS#: MDAA2116290

Unprecedented opportunity in The Community of Chesapeake Harbour! Gated Chesapeake Harbour offers lavish Chesapeake Bayfront Annapolitan style living. The pinnacle of style and luxurious refinement now available! 4 Levels of spectacular waterfront perfection masterfully done with nothing to do but unpack your toothbrush and head to your marina front deck for happy hour and stunning summer sunsets. Fully renovated and professionally custom designed upgrades from Kitchen Encounters to Baths including Heated Bathroom Floors (all 3 Full), Robern Medicine cabinets, Hansgrohe fixtures, Miele Steam and convection ovens, Thermador Fridge, waterfall island, wine/beverage center, 15K+ of lighting fixtures, Calcutta Italian Marble surround Napolean LED fireplace, new Pella doors, HVAC, all new interior and closet doors with custom closets just to start!!! Please contact listing agent for complete list.
A transformation of over $500,000 in timeless luxe finished renovations to create the space of your dreams. Offering casual elegance and extreme comfort, you will not want to leave your new home but when you do -walk to the private sandy beach to watch the Blue Angels, enjoy sunny days at the Chesapeake Bay waterfront pools, play pickleball/tennis with neighbors and meet new friends for cocktails and sunset dinners at Waterside Beacon Bar and Restaurant. Lots of social events and Beacon has live music on most weekends! Perfection awaits. It doesn’t get better than this in this premiere exclusive resort style Annapolis community. Please see the interactive floorplan under virtual tours for additional photos and information.

ANNAPOLIS

2186 CHESAPEAKE HARBOUR DRIVE

3 Beds

3 Baths

2,719 Sq.Ft.

$1,700,000

MLS#: MDAA2108174

Unprecedented waterfront opportunity in The Community of Chesapeake Harbour! Unduplicatable Gated Chesapeake Harbour offers lavish Chesapeake Bayfront Annapolitan style living. This community could never be built today and this property completes the trifecta with perfect location and luxurious refinements. 4 Levels of spectacular waterfront perfection masterfully done. Fully renovated and professionally custom designed finishes cannot be duplicated and never at this price *Kitchen Encounters to Baths including HEATED Bathroom Floors (all 3 Full), Robern Medicine cabinets, Hansgrohe fixtures, Miele Steam and convection ovens, Thermador Fridge, waterfall island, wine/beverage center, 15K+ of lighting fixtures, Calcutta Italian Marble surround Napolean LED fireplace, new Pella doors, HVAC, all new interior and closet doors with custom closets just to start!!! A transformation of over $500,000+ in timeless luxe finished renovations to create the space of your dreams can be yours! Offering casual elegance and extreme comfort, you will not want to leave your new home but when you do -walk to the private sandy beach to watch the Blue Angels, enjoy sunny days at the Chesapeake Bay waterfront pools, play pickleball/tennis with neighbors and walk with new friends for cocktails and sunset dinners at Waterside Beacon Bar and Restaurant. Lots of social events, groups and Beacon even has live music on most weekends! Perfection awaits. It doesn’t get better than this in this timeless premiere exclusive resort style Annapolis community. Please see the virtual walk through and interactive floorplan under virtual tours for additional photos and information.

ANNAPOLIS

2186 CHESAPEAKE HARBOUR DRIVE E

3 Beds

3 Baths

2,719 Sq.Ft.

$1,700,000

MLS#: MDAA2116414

Custom coastal craftsman home is currently under construction in Eastport - Annapolis, Maryland. This home will feature a perfect blend of classic Eastport and luxury coastal craftsman design. Permitting is complete. This expansive 3600 +/- (approx. 850 unfinished) sq. foot home will offer 4 bedrooms and 3 baths with an open floor plan concept. Truly an entertainer’s dream with hardwood floors, high ceilings, impressive millwork and trim, walk-in closets, beautiful gourmet kitchen, large rooms with multiple dining and gathering areas, and a fully finished basement. The second level of the home offers three bedrooms including the owner’s suite. The suite features a fireplace and master bath with dual vanity, frameless glass shower and soaking tub. The builder did not leave anything out, by placing an office or bedroom on the main level and washer and dryer on the second floor for convenience. The exterior of the home will include a charming front porch, back deck for hosting seasonal barbecues, and ample green space in the rear. A landscaping package is included, as well as 3 off-street parking spaces. Walkability to downtown Annapolis including premier restaurants, shopping, yacht clubs, water activities, and more... Take advantage of this rare opportunity to purchase Eastport new construction. The delivery delivery is summer 2025.

ANNAPOLIS

400 JEFFERSON STREET

4 Beds

3 Baths

3,640 Sq.Ft.

$1,700,000

MLS#: MDAA2032362

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 9,000 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

This modern ('85) 4 bedroom/2 full- 1 half- bath home, sits on the largest lot (1.5 acres) in the coveted Providence community, borders the USNA Golf Course, and is the largest estate lot currently available in Annapolis. The lucky buyer will become a member of the private Providence Club, a $10 million "clubhouse" which includes an 8-year new clubhouse, pool and kids play area all with unparalleled views of the Bay, and its own private marina; which is the closest marina to the Bay on the Severn River. The Providence HOA heavily-subsidizes the marina, so boatowners not only enjoy the best direct Bay access on the Severn, but slip fees (including dry, on-site winter storage) that are a fraction of market marina rates. Enjoy seamless indoor-outdoor living with a screened-in porch—the perfect setting for morning coffee, quiet conversation, or sunset wind-downs. The expansive back deck invites al fresco dining and elevated summer entertaining, framed by the tranquil beauty of this remarkable estate. Inside, the home boasts 4 bedrooms (with potential to expand to 6), 2.5 baths (option to add another full bath), hardwood floors, a modern, light-filled design, and a finished walkout basement. A front-entry garage, extended private driveway, and abundant storage spaces enhance the home's effortless livability. A truly rare opportunity in the prestigious Providence community—without comparison and without compromise. Discover the unmatched elegance, privacy, and lifestyle this estate offers. Schedule your private tour today and experience Annapolis luxury at its finest!

ANNAPOLIS

210 PROVIDENCE ROAD

4 Beds

2 Baths

2,926 Sq.Ft.

$1,650,000

MLS#: MDAA2115356

**SEVERE MOLD THROUGHOUT - MASK & HOLD HARMLESS REQUIRED TO ENTER**

This is a short sale and the property requires a full renovation. Being sold strictly as-is, with no repairs or warranties offered.

Third-party approval required. The list price is not approved by the lender and reflects the amount currently owed, not the property's fair market value. Offers will not be reviewed until the property has been on the market for 7 days, per lender guidelines.

Please note: Property will not be delivered in broom-swept condition, and personal belongings may remain and convey with the sale.

ANNAPOLIS

371 CARRIAGE PARK WAY

4 Beds

3 Baths

6,724 Sq.Ft.

$1,600,000

MLS#: MDAA2118760

Welcome to this exceptional 3-unit property located in the vibrant heart of downtown Annapolis—truly an investor's dream. These turnkey apartments are currently licensed for short term rentals and ready to offer a rewarding investment opportunity.

Situated in the bustling core of Annapolis, this property provides unparalleled access to the city's rich array of dining, shopping, and entertainment. Guests will delight in the diverse dining scene, with popular spots like Iron Rooster, Tsunami, and Osteria 177 offering a range of culinary experiences. Located steps from Gate 1 of the United States Naval Academy makes it one of the most desirable locations for both long and short term guests.

Shopping enthusiasts will find plenty to explore, from charming boutiques and gift shops to unique pottery stores. When the sun sets, Annapolis comes alive with nightlife options, including Dining Under the Stars events, live music at Rams Head Tavern, and a variety of bars and pubs for a perfect evening out.

For those seeking recreation and adventure, the area offers an abundance of activities. Visitors can enjoy the serene beauty of Quiet Waters Park, take sailboat lessons, embark on fishing charters, explore ghost tours, or visit local museums. The proximity to the US Naval Academy, just a block away, adds to the allure of this sought-after tourist destination.

This property not only offers a prime location but also the potential for a lucrative return on investment. Don't miss the chance to own a piece of Annapolis's thriving downtown scene.

ANNAPOLIS

165 KING GEORGE STREET

4 Beds

None Baths

2,595 Sq.Ft.

$1,599,000

MLS#: MDAA2103044

Welcome to this exceptional 3-unit property located in the vibrant heart of downtown Annapolis—truly an investor's dream. These turnkey apartments are currently licensed for short term rentals and ready to offer a rewarding investment opportunity.

Situated in the bustling core of Annapolis, this property provides unparalleled access to the city's rich array of dining, shopping, and entertainment. Guests will delight in the diverse dining scene, with popular spots like Iron Rooster, Tsunami, and Osteria 177 offering a range of culinary experiences. Located steps from Gate 1 of the United States Naval Academy makes it one of the most desirable locations for both long and short term guests.

Shopping enthusiasts will find plenty to explore, from charming boutiques and gift shops to unique pottery stores. When the sun sets, Annapolis comes alive with nightlife options, including Dining Under the Stars events, live music at Rams Head Tavern, and a variety of bars and pubs for a perfect evening out.

For those seeking recreation and adventure, the area offers an abundance of activities. Visitors can enjoy the serene beauty of Quiet Waters Park, take sailboat lessons, embark on fishing charters, explore ghost tours, or visit local museums. The proximity to the US Naval Academy, just a block away, adds to the allure of this sought-after tourist destination.

This property not only offers a prime location but also the potential for a lucrative return on investment. Don't miss the chance to own a piece of Annapolis's thriving downtown scene and the views of the Naval Academy Chapel especially in the evening.

ANNAPOLIS

165 KING GEORGE STREET

4 Beds

3 Baths

2,595 Sq.Ft.

$1,599,000

MLS#: MDAA2103046

Welcome Home to 3529 Chrisland Drive! This beautifully upgraded 5-bedroom, 4-bathroom is located in the highly desired neighborhood of Annapolis Cove, only minutes from downtown Annapolis. Enjoy stunning views of the water from all aspects of your new home. A gourmet open kitchen, family room, formal dining room, formal living room, sunroom, private office and half bath offer amazing living spaces on the first floor. A fully screened in porch off the living room, exterior porch and gazebo off the kitchen offer relaxing views of the water morning and night. The third floor includes a large primary bedroom and updated on suite, three additional bedrooms and a full bathroom. The fully finished walkout basement offers a full bedroom, full bathroom with room for a game room/media room and a home gym. Life in Annapolis Cove offers access to parks, a playground, basketball courts and the option to join the waterfront Bay Ridge Pool and secure a slip in the private community marina. This is a must-see home that won't last, schedule your showing today and don't miss out on the opportunity to own this beautiful home!

ANNAPOLIS

3259 CHRISLAND DRIVE

5 Beds

3 Baths

4,583 Sq.Ft.

$1,550,000

MLS#: MDAA2118272

A Rare Find in the Heart of Eastport! Built in 2006 with timeless Eastport charm, this beautifully maintained home offers the perfect blend of traditional style and modern convenience. Enjoy off-street parking for 2 cars and a host of high-end features throughout. Step inside to discover hardwood flooring on all 3 levels, radiant floor heat, and zoned heating and cooling – including a private AC control in the primary suite. The spacious layout includes three full baths with stone tile details, a whirlpool tub and 2-person shower in the primary bath, and a soaking tub in the guest bath.
The primary bedroom features skylights with rain sensors and remote-controlled shades, as well as his and hers closets. Enjoy a full-size washer & dryer on the second floor. The large 3rd level loft can be used as a 4th bedroom. On the main level there is a pantry/mudroom, separate side entry leads you to step to the unfinished basement with 8' ceilings. Designed with safety and comfort in mind, this home includes ceiling sprinklers on all levels, enhanced fire-rated walls, and a top-rated corner for a wood stove. Outdoor living is just as impressive with rain gardens in the front and back, Leaf Filter gutter guards, outdoor water and electric access, and dimmable lighting on the front porch as well as inside kitchen/dining areas. Additional highlights: Updated interior paint throughout (2024); New refrigerator (2024); dishwasher (2023); and microwave with stove exhaust (2025). Security system with front door camera. Included in the fenced rear yard is a permanent exclusive 5’ rear easement for added privacy.
Enjoy the best of Eastport living in a home designed for comfort, efficiency, and peace of mind.

ANNAPOLIS

541 SECOND STREET

4 Beds

3 Baths

2,341 Sq.Ft.

$1,549,000

MLS#: MDAA2114340

#MDAA2116952

ANNAPOLIS

1028 SANDPIPER LANE

3 Beds

2 Baths

2,552 Sq.Ft.

$1,500,000

MLS#: MDAA2116952

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