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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
318
# of Listings
3
Avg # of Bedrooms
$463
Avg. $ / Sq.Ft.
$1,069,668
Med. List Price

Browse Annapolis Real Estate Listings

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Over $5M

103 Properties Found. Page 3 of 7.

Welcome home to completely renovated 529 Tayman Drive, an impeccably renovated residence blending modern luxury with prime Hillsmere convenience. Situated on a large/spacious, fenced-in corner lot, this 3-bedroom 2.5-bathroom with a finished basement offers a lifestyle of comfort and ease. Step inside and be captivated by the two-story vaulted living room, a sun-drenched space designed for both relaxation and grand entertaining. The gourmet kitchen is a chef’s dream, featuring sleek quartz countertops and all-new appliances. The primary bedroom is a true retreat, offering a spa-like en-suite bathroom for ultimate relaxation. The finished basement provides ample flexible space for a media room, home gym, or play area. With no detail overlooked, this home is entirely move-in ready. Upgrades include a new roof, new siding, a new composite deck and porch, a new HVAC system, a new water heater, and a new French drain waterproofing system. The backyard has a pour concrete pad with electrical service for a large shed or hot tub! As if the home itself weren't enough, the location is unbeatable—just one block from the Key School and a short walk from the community beach. Discover the best of Hillsmere living.
#MDAA2127754

ANNAPOLIS

529 TAYMAN DRIVE

3 Beds

2 Baths

3,400 Sq.Ft.

$750,000

MLS#: MDAA2127754

Chic Street-Level Condo in the Heart of Annapolis. Welcome to this spacious 1-bedroom, 1.5-bath condo in the sought-after Acton's Landing community. Perfectly situated on the street level for effortless access, this unit combines convenience with luxury. The open-concept layout features a generous living space, a large kitchen with a center island, breakfast bar, and plenty of storage—ideal for a weekend getaway or everyday living. The separate den offers a perfect work-from-home setup or cozy retreat. The primary suite is a true haven, complete with a spa-inspired bath featuring a soaking tub, walk-in shower, and ample closet space. Enjoy easy access to the building’s parking garage just steps from your door. Community amenities include a fitness center, gym, party room, library, and more. Located just a short stroll from the water taxi and the vibrant shops, dining, and charm of historic downtown Annapolis—this is city living at its best. Don’t miss your chance to own in one of Annapolis’ most desirable communities!
#MDAA2120238

ANNAPOLIS

66 FRANKLIN STREET 20

1 Beds

1 Baths

1,342 Sq.Ft.

$750,000

MLS#: MDAA2120238

Professional Photos Coming Soon! A thoughtfully designed residence offering a blend of historic character and modern comfort in the heart of Downtown Annapolis. Nestled amongst the city's best dining, shopping, and waterfront attractions, this home provides convenience and style, along with designated PARKING. This stylish residence blends sleek modern updates and design along with nautical-inspired details throughout! Inside the home features high ceilings, beautiful custom built-ins with integrated spotlighting, warm hardwood floors, an abundance of bright natural light, and exposed brick accent walls that set an authentic city vibe! The home includes Two bedrooms, two full and one half bathrooms. Fabulous balcony located off the primary bedroom suite to enjoy morning coffee or a relaxing evening/ ! With designated parking, thoughtful updates, and in-town walkability, this home embodies Annapolis charm with a modern costal twist. You will love living here!
#MDAA2128240

ANNAPOLIS

222 WEST STREET A

2 Beds

2 Baths

1,434 Sq.Ft.

$749,000

MLS#: MDAA2128240

Welcome to your dream home nestled in a park-like setting! The beautifully updated home boasts fresh new paint and flooring throughout. The spacious main level includes a living room, dining room, family room, and half bath. The heart of the home features a brand new kitchen, equipped with state-of-the-art appliances, sleek countertops, and abundant cabinetry with undermount lighting. Cooking and entertaining have never been easier or more enjoyable! The composite deck is just steps away and the perfect spot to grill. The upper level encompasses a primary suite with vaulted ceiling and attached bath. There are two guest bedrooms and a hall bath, providing ample space for family and guests. The lower level is a hidden gem, boasting a comfortable 4th bedroom and a full 3rd bath, perfect for an in-law or au pair suite. This private space offers flexibility and convenience for multigenerational living or guests. In addition there is a room that could be a game room or home theater. Set on a generous .86-acre lot, this property is a nature lover's paradise! Enjoy your own orchard with fruit trees, including pear and plum, as well as a bounty of blackberries, blueberries, and raspberries. The lush landscape invites outdoor gatherings, playtime, or simply moments of tranquility. A standout feature is the expansive 50-foot carport, ideal for storing your boat or RV. Enjoy the freedom to explore the great outdoors without worrying about where to park your toys! Located in the highly desirable water privileged community of Bon Haven. The voluntary community association members have access to a pier, slips, and a boat ramp, making waterfront activities easily accessible. Imagine spending weekends on the water, fishing, or simply soaking in the sun! Currently, boat slips are available starting at just $300 per year. Despite its secluded feel, this home is perfectly positioned for an easy commute to Washington D.C., Ft. Meade, Baltimore, or the Naval Academy. Enjoy the tranquility of suburban living with all the conveniences of city life just minutes away!
#MDAA2127224

ANNAPOLIS

701 SONNE DRIVE

4 Beds

3 Baths

2,704 Sq.Ft.

$740,000

MLS#: MDAA2127224

Commercially zoned C-1 pad site available adjacent to McDonald's and Wendy's. Just shy of 1 acre. Public Utilities. Great visibility from Rt. 50. Build your office building, a restaurant, retail center, mixed use building, residential apts or condos over ground floor commercial, etc. See documents section for more information.
#MDAA2018250

ANNAPOLIS

1440 WHITEHALL ROAD

None Beds

None Baths

0.92 acres

$739,900

MLS#: MDAA2018250

1.485 acre RLD zoned parcel/ lot available adjacent to McDonald's, Wendy's. Potential uses include daycare, veterinarian, assisted living, club, group home, kennel, plant nursery, produce stand, etc. All utilities are available. Easy access on and off of Rt. 50. Refer to documents section.
#MDAA2018258

ANNAPOLIS

1444 WHITEHALL ROAD

None Beds

None Baths

1.49 acres

$739,900

MLS#: MDAA2018258

Water View !!! New Construction in Arundel on the Bay come see this Amazing new home with beautiful quartz counter tops and brass fixtures and handles . Don't miss these large custom bathrooms all the final touches are almost done hurry and finish with your own ideas home will be done in next couple weeks
#MDAA2124030

ANNAPOLIS

3449 ROCKWAY AVENUE

3 Beds

2 Baths

1,700 Sq.Ft.

$725,000

MLS#: MDAA2124030

New on site today
Welcome home! This private Annapolis retreat blends comfort and elegance, with dramatic high ceilings and main level living that feels both relaxed for everyday life and sophisticated for entertaining. Inside, discover an open floorplan with fresh paint, stunning vaulted wood ceilings, gleaming hardwood floors, and wide windows flooding the home with abundant natural light. The spacious and bright living room features a large picture window and recessed lighting, and is anchored by a striking double-sided stone gas fireplace flanked by built-in cabinets. Pass through the classic archway into the gorgeously updated kitchen (2021) featuring sleek marble countertops, new tile flooring, modern recessed lighting, and stainless steel appliances, including a high-end dual-fuel GE Café range with double oven (2021). With a central island breakfast bar and additional bank of cabinet storage, this spacious layout keeps the chef connected to the living and dining areas. Continue through the lovely glass pocket doors into the open dining and family room and be impressed by the custom vaulted wood ceiling, large windows and welcoming finishes. Down the hall, the rare main-level primary bedroom boasts a rich cathedral wood ceiling, newer plush carpeting, a cozy wood-burning fireplace that can easily convert to gas, and a unique two-level walk-in closet. Enjoy a beautifully appointed custom en suite bathroom with a luxurious oversized shower and a handsome vanity with a new countertop, sink, and faucet (2025). The second bedroom includes new soft carpeted flooring, ample closet space, and access to the second tastefully updated bathroom in the hallway. Downstairs, the lower level offers a versatile recreation room with brand new carpeting (2025) and a generously-sized storage room with built-in shelving. Two additional bedrooms and a third full bathroom with a step-in shower provide further flexibility for a private guest space, home office, or gym. Outside, enjoy an expansive wraparound and recently repainted wooden deck with built-in grill, and relax by the firepit in the privacy of nearly half an acre of fenced yard, surrounded by mature trees for a tranquil, scenic view. On the front of the home, the refinished driveway (2024) offers plenty of room for your boat or trailer. Recent major home updates include a newer roof (2022), geothermal energy-efficient HVAC (2019), upgraded Anderson doors and windows, whole-house water filtration with UV filters and a point-of-use reverse osmosis filtering sytsem, a 50-amp hookup for a potential hot tub, a gas line roughed for a future whole-house generator, replaced BAT septic system. Conveniently located just minutes to Giant, Annapolis Mall, Downtown Historic Annapolis, and Quiet Waters Park. Easy access to Route 50 and nearby commuter routes puts Annapolis, Baltimore, and the region within easy reach. Schedule a private showing to see everything this special home has to offer!
#MDAA2129480

ANNAPOLIS

1114 BAY RIDGE ROAD

4 Beds

3 Baths

3,120 Sq.Ft.

$725,000

MLS#: MDAA2129480

**OPEN HOUSE - SUNDAY, October 19 from 12-2pm** MUST SEE! ** Pristine/Move-in-Ready 4-Level, End of Row Townhome in the Community of Parkeside Preserve in Annapolis, MD *****The True Definition of Luxury Living with all the Bells & Whistles! This Incredible Home Features 4 Finished Levels with 4 Bedrooms, 3 Full & 1 Half Bathrooms, 2 Car Garage, which features High Grade Epoxy Flooring, Custom bi-level Stone Accent Walls; Ample Storage, and a convenient TESLA Charger! *****Enter on the Main Level either from the Front Door or Garage and Enjoy Entertaining in Your Spacious Family Room with Lots of Natural Light and the Convenience of a Full Bathroom and additional Storage area! *****The 2nd Level features a Spacious Open Floor Plan - Also Great for Entertaining! The Gourmet Kitchen provides Unparalleled Convenience Combined with Casual Comfort and Elegance. Plenty of Counter space with a Kitchen Island and Breakfast Bar; Sep Coffee/Bar Nook, Huge Walk-in Pantry and Half Bath! *****Stainless Steel Appliances; Refrigerator with Water Filtration system; Soft Close Cabinetry. *****Ascend to the Owner's Suite for Ultimate Convenience of your daily routine. Deluxe Bathroom, Sep Water Closet, and a Huge Walk-in Closet; *****Two (2) additional well-appointed Bedrooms and a Shared Hall Bathroom offering Comfort and Privacy. Both rooms feature 9' Ceilings. *****Sep Laundry area and Hallway Linen Closet. *****Venture to the 4th level (use as a 4th Bedroom, Home Office/Flex Area, Serene Retreat) and Enjoy Evenings Under the Stars! Watch the Blue Angels Fly Over as well as July 4th Fireworks! *****Back to the Main Level for a little down time and Enjoy Sitting under your Covered Front Porch and Soak in the Peaceful Surroundings! *****Added Perks: In addition to a TESLA Charger, there's a 'Flo by Moen' device which monitors the Water pressure, Temperature, Flow rate in real-time, and offers Leak Detection and alerts. *****BEST OF ALL ... Enjoy the Benefits of a ‘Flash Heater System’ that provides UNLIMITED Hot Water for the Shower! *****Energy Star Certified Appliances; and Custom Window Blinds; and a Ring System *****Call Me for Details about available GRANT/down Payment Funds; ZERO down payment with NO Mortgage Insurance Loan; FHLB Money for a LIMITED TIME with Higher Amounts to HELP Buyers! *****Click the MOVIE Icon Next to the Photos to Navigate through each Level of this Gorgeous Home! **OPEN HOUSE - SUNDAY, October 19 from 12-2pm**
#MDAA2118974

ANNAPOLIS

113 TREBLIS WAY

4 Beds

3 Baths

2,348 Sq.Ft.

$724,999

MLS#: MDAA2118974

This five-bedroom, three full-bath colonial is situated on a corner lot in the desirable Cape St. Claire neighborhood of Annapolis. This home boasts a charming front porch and relaxing side patio, along with ample off-street parking including a two-car garage and four-car driveway. Step inside to find a home that is truly move-in ready, featuring fresh paint throughout, gleaming hardwood floors, new carpet, crown molding and recessed lighting. The updated kitchen showcases new cabinets and new stainless-steel appliances. The living room features a cozy wood-burning fireplace, adding warmth and character to the heart of the home. A bright and spacious great room, with sunroom area, provides a versatile space perfect for entertaining or relaxing. The main level offers flexible living options with two bedrooms featuring new carpet and an updated full hall bath. Upstairs, the primary suite is a true retreat, featuring cathedral ceilings and an upgraded en-suite bathroom with soaking tub and separate shower. Two additional bedrooms and another updated full hall bath complete the upper level. The lower level includes convenient garage access, rec room with new carpet, laundry closet with a new washer and dryer and a tiled storage room. Nestled in a charming, well-established community known for its welcoming atmosphere and excellent amenities, this move-in ready colonial offers the perfect setting for enjoying the Annapolis lifestyle.
#MDAA2120586

ANNAPOLIS

1014 ST CHARLES DRIVE

5 Beds

3 Baths

3,680 Sq.Ft.

$719,900

MLS#: MDAA2120586

Tucked away on a peaceful cul-de-sac in the desirable Georgetown Grove community, this beautifully maintained three-level waterfront home offers the perfect blend of privacy, comfort and convenience. Set on the largest lot in the neighborhood, the property abuts onto the headwaters of Back Creek. A picturesque, wooded lot surrounds the home and provides a blanket of greenery during the summer season. Stunning views of Back Creek and its boats are enjoyed the rest of the year. A protected wetland bird sanctuary is situated just behind the home, attracting blue herons, hawks, and an abundance of wildlife. The community also provides kayak and paddleboard access to the creek, affording you incredible views of boats and marinas, and the Chesapeake Bay. The home features an open concept living and dining area, a dramatic two-story vaulted ceiling, and a wall of feature windows that frame lush landscaping and provide abundant natural light. The kitchen features white cabinetry, granite countertops, pantry storage, and a sunlit table area overlooking the deck, trees and creek. Just beyond, the family room offers a cozy retreat with a fireplace and a triple-panel sliding glass door that leads to the multi-tiered entertainment deck, ideal for outdoor gatherings and peaceful relaxation. Upstairs, the primary suite includes two closets, a separate vanity area, and a spacious en suite bath with double vanity, soaking tub, and separate shower. Two additional bedrooms, one with a cathedral ceiling, share an updated full bath. The spacious, finished lower-level walkout provides a functional space that includes a large cedar closet, full bath with steam shower, and walk-out access to a stone patio surrounded by trees and a water view. If needed, this large space could serve as an in-law suite or rental unit. The property also offers a rare opportunity to experience the waterfront while living in the heart of Annapolis. Downtown historic Annapolis, the Naval Academy, Eastport, marinas, restaurants, grocery shopping and commuter routes to Washington DC are all just minutes away. Quiet Waters Park is a short walking/biking distance, providing family recreation, summer concert series, educational events, and watercraft rentals. A local marina, grocery store and restaurants are all within walking distance. Enjoy gracious living in this private Georgetown Grove home, along with a vibrant lifestyle that comes with living in the heart of Annapolis.
#MDAA2114986

ANNAPOLIS

39 WINDWHISPER LANE

3 Beds

3 Baths

3,193 Sq.Ft.

$700,000

MLS#: MDAA2114986

The recent price adjustment makes this condo an exceptional value in the heart of historic Annapolis! Welcome to luxury living in the highly sought-after Residence at Park Place! This beautifully maintained 2-bedroom, 2-full bath condo offers comfort, convenience, and top-tier amenities — all in a secure, resort-style building. Step inside to find generously sized bedrooms, gorgeous hardwood floors, and an open-concept layout filled with natural light. The chef’s kitchen has granite countertops, stainless steel appliances, and plenty of cabinet space — perfect for entertaining. Relax by the cozy fireplace or enjoy your morning coffee in the peaceful setting. The open-concept living area features gleaming hardwood floors, a gas fireplace with a nice white mantle and large windows that fill the space with natural light. This home has been freshly painted, professionally cleaned, and the floors have been buffed and waxed, making it move-in ready. The primary suite includes a spacious walk-in closet, a spa-like bathroom with a separate tub and walk-in shower, and a double vanity with ample counter space. The second bedroom also has its own private full bath with a stand-up shower, offering ideal comfort and privacy for guests. The second bedroom could also be used as a remote-home office. There are 2 deeded and assigned parking spaces in the gated, secure garage with access to secure interior elevators. This upscale building has many unique benefits including a 24-hour front desk concierge in the lobby. The first-class amenities include an outdoor pool, hot tub, fitness center, pool table, meeting rooms, full-kitchen in the common area and several places to gather with your family, friends and neighbors, inside and outside in the courtyard and patio and also has garden plots for the residents. The free Circular Trolley can pick you up right out front and take you to the Annapolis waterfront. This is a pet friendly building and even has its own dog park called Bark Place Dog Park! This exceptional condo combines modern luxury with timeless charm in one of Annapolis’s most sought-after communities. Whether you're looking for a full-time residence, weekend getaway, or investment property, this condo offers the ideal blend of comfort, security, and location. Just steps from the Annapolis waterfront, award-winning restaurants, boutique shopping, and historical landmarks – everything you love about Annapolis is right outside your door! Reasonable commute to Baltimore and Washington DC. Just a few blocks to the Navy-Marine Corps Stadium and not far from the U. S. Naval Academy, Maryland State Capital and is just a few blocks to Maryland Hall, which the center of the culture in this region. Live the Annapolis life in a way few others can. Call today to schedule an appointment!
#MDAA2121090

ANNAPOLIS

5 PARK PLACE 217

2 Beds

2 Baths

1,343 Sq.Ft.

$699,900

MLS#: MDAA2121090

This 2 bedroom, 2 bath condo is move-in ready! Freshly painted, and brand new carpet in bedrooms. Park Place boasts numerous amenities that make it one of the best places to live in Annapolis. With an ideal location, you can walk everywhere in town to restaurants and shopping. When you enter the lobby, you will be greeted by the 24/7 staff at the front desk. The party room is perfect for larger gatherings and meetings with friends and neighbors. The Social Committee organizes plenty of events to join in and have fun with your neighbors if you feel like it. s. Grab a book from the library and relax on the back patio. The pool is fabulous, and there is a lifeguard on duty during the season. The dog park is perfect for your pet. Grills for your convenience are also located on the back patio! Walk to the Naval Academy Stadium minutes away and enjoy the lively Football season. Come and see why Park Place is the perfect place to call home!
#MDAA2122622

ANNAPOLIS

5 PARK PLACE 626

2 Beds

2 Baths

1,314 Sq.Ft.

$699,000

MLS#: MDAA2122622

Welcome to 228 Dubois Road in Annapolis Maryland** Updated Cape Cod on .81 Acres in Annapolis! Private Yard and Private Street**Every Level of this Home has been Updated**Main Level has Living Room & Kitchen**Also on Main Level are Two Bedrooms and a Full Bath**Sunroom on Side of Main Level**Upper Level has Private Main Bedroom w/Full Bath**There is a Smaller Room off of the Primary Bedroom that could be used to a Office/Den/Nursery**Lower Level has Family Room, Laundry, Full Bath and Another Bedroom**Large Spacious Yard has been Professional Landscaped**Roof and Gutters are 2024**HVAC is 2025** Close to ALL Annapolis has to Offer along with Major Routes to DC and Baltimore**
#MDAA2127442

ANNAPOLIS

228 DUBOIS ROAD

4 Beds

3 Baths

2,900 Sq.Ft.

$699,000

MLS#: MDAA2127442

Experience elevated living in this stunning 10th-floor residence at Towne Centre, Annapolis’ premier luxury condominium community. This spacious 2-bedroom, 2.5-bath unit features a separate study with French doors—perfect for a home office or library. High end finishes adorn this unit with unique pendant lighting and brilliant chandeliers. The living and dining area are open and bright with walls of windows with a private balcony and panoramic views. The gourmet kitchen features upgraded appliances, granite counters and a separate laundry room. Unwind in the expansive primary suite complete with a walk-in closet and spa-inspired bath. The second bedroom also offers a large en-suite bath and walk-in closet, ideal for guests or family. Brand new HVAC, Hot Water Heater and Refrigerator. This unit conveys 2 covered parking spaces and a storage unit. This secure building offers exceptional amenities including a fitness room, eating and living areas, a rooftop pool, BBQ area, and a gathering room showcasing sweeping views of Annapolis. Enjoy the top-rated restaurants, Whole Foods, boutique shops and Target right outside your front door. Upscale living meets unmatched convenience at Towne Centre.
#MDAA2126676

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 1001

2 Beds

2 Baths

1,648 Sq.Ft.

$699,000

MLS#: MDAA2126676

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