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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

253

# of Listings

3

Avg # of Bedrooms

$405

Avg. $ / Sq.Ft.

$830,016

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

253 Properties Found. Page 3 of 17.

An exclusive and rare opportunity could be yours! Welcome to 51 Franklin, consisting of 9 high-end boutique units, developed by John Pilli & constructed by Gate One custom builders in 2020. Located at the intersection of Murray Hill and the city's Historic District, this exquisite condo provides high-end finishes including Legno-Bastone wide-plank hardwood flooring, Caesarstone waterfall counters, Omega cabinetry, Thermador & Wolf appliances, and beautiful designer plumbing and lighting fixtures. California Closets in all bedrooms, pantry and coat closet. Airy ten foot ceilings. Amenities include elevator, rooftop terrace w/luxurious views, secured covered garage parking with 2 assigned spots per unit, extra storage unit 3 steps from condo entry, gas cooking and water usage. Easy walking to Main St, the West St Arts District, and all points Downtown Annapolis...a true lock and leave experience for the next fortunate Owner! SEE VIDEO 'TOURS' FOR IN DEPTH INFO ABOUT THIS SMALL, EXTRAORDINARY HIGH END CONDO BUILDING DESIGNED BY THE ARCHITECTS OF FOURTH STREET DESIGN, AND BUILT BY JOHN PILLI AND GATE ONE BUILDERS

ANNAPOLIS

51 FRANKLIN STREET

2 Beds

2 Baths

2,269 Sq.Ft.

$1,695,000

MLS#: MDAA2127792

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, new tankless water heater, 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.

$1,695,000

MLS#: MDAA2127736

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 20,000 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

Enjoy urban living at 285 West Street #15! This stunning property offers a stylish way to embrace the best of downtown Annapolis in a modern townhome with an elevator and rooftop deck. Step outside and enjoy the city’s energy—shops, restaurants, the waterfront, and cultural attractions are all just a short stroll away—while still savoring the comfort of a private, lock-and-leave retreat.

Built by Bozzuto in 2020, this four-bedroom, four-and-a-half-bath home features an open, light-filled layout designed for both everyday living and entertaining. The open floor plan on the main level includes the living room with spacious seating area and fireplace, a dining area, and a classic all white gourmet kitchen anchored by an island with ample seating, high-end appliances, and a built-in sideboard with beverage center. Upstairs, the primary suite offers two walk-in closets and a spa-like bath with double vanities, and a large tiled shower. An additional bedrooms with ensuite bath and conveniently located laundry room complete the this level. Head upstairs to the top floor via the stairs or elevator to enjoy the inviting family room, guest bedroom and enviable rooftop deck with double sided fireplace and sunshade, an incredible retreat for relaxing and entertaining on a beautiful evening.

The entry level provides a flexible bedroom or office with full bath and boasts heated floors for added comfort. Rounding out the appeal is a two-car garage, plenty of storage and a plethora of upgrades and curated finishes throughout.

Perfectly located within close proximity of everything Annapolis has to offer; walk to the shops and restaurants of West and Main Streets as well as the Historic District, City Dock and the Naval Academy. Traveling or commuting is just as convenient by easily accessing Rt. 50 and 97 which provides direct access to Baltimore, BWI, Ft. Meade/NSA and Washington, DC., or head over the Bay Bridge to the Eastern Shore for a quick beach vacation. Welcome Home!

ANNAPOLIS

285 WEST STREET 15

4 Beds

4 Baths

2,720 Sq.Ft.

$1,595,000

MLS#: MDAA2123570

Thoughtfully updated home, preserving the character and charm of Murray Hill while offering the comfort, efficiency, and style of new construction. | 4 Bed | 3.5 Bath | 2,580 Sf | 3,340 Sf Lot | Large Backyard | 1 Parking Space | Home: Full Gut Renovation, Open Main Living Layout, Custom Tiled Wood Burning Fireplace w/ Mantle, Large Jeld-Wen Windows w/ Lots of Natural Light Throughout, Recessed LED Lighting Throughout, 9 Ft Ceilings, Hard Wired Security System, Klipsch Built-In Speaker System, Dual Zoned High Efficiency Carrier HVAC w/ Ecobee Smart Thermostat, High Efficiency Heat Pump Water Heater, Closets w/ Custom Built-Ins, Elfa Closet System in Primary Suite, Original Heart Pine Hardwood Flooring Throughout First Floor, Laundry Closet w/ Custom Built-Ins & LG Full Size Washer & Dryer, Powder Bath on Main level, Bluestone Entrance Sidewalk & Steps, Rear Property Access from Morris Street | Kitchen: Large Island w/ Storage & Seating for 3, Ample Cabinetry w/ Soft-Close Hardware, Built-In Custom Pantry, Gloss Tile Backsplash, Quartz Countertops, Brushed Brass Finishes, Kitchen Aid Stainless Steel Appliances, French Door Refrigerator, Induction Range w/ Zephyr Exhaust Hood, Full-Size Dishwasher, Built-In Microwave Drawer | Baths: Frameless Glass Enclosed Shower w/ Separate Handheld Shower Head, Built-In Niche, Separate Soaking Tub & Large Double Vanity in Primary Suite, Quartz Topped Vanities w/ Storage, Tiled Shower Walls & Flooring | Basement: Rear Yard Access, Private Backyard Entrance, Family Room w/ Wet Bar, Wine Fridge, & Floating Shelves, Additional Bedroom & En Suite Bathroom w/ Glass Enclosed Shower | Neighborhood: Murray Hill is one of Annapolis’ most sought-after neighborhoods, known for its tree-lined streets, classic architecture, and easy walkability to downtown. With Spa Creek on one side and City Dock just a short stroll away, residents enjoy a perfect blend of historic charm and a waterfront lifestyle.

ANNAPOLIS

48 MURRAY AVENUE

4 Beds

3 Baths

2,580 Sq.Ft.

$1,595,000

MLS#: MDAA2129582

PHOTOS TO BE UPDATED THROUGHOUT BUILDING PROCESS!! This is a rare opportunity to own a newly built, beautifully designed home on a large lot in an established neighborhood-with nature at your doorstep and everything Annapolis has to offer just minutes away. This home is set to be completed by year end, 2025. With a stunning Colonial architectural style, this beautiful home offers 5-bedrooms and 4.5-baths and sits on the last available lot in the Twin Hills neighborhood which is 1.4 acres and borders lush trees and a preservation area. It offers a rare blend of privacy, openness and a connection to nature. Whether you are hosting friends or enjoying a quiet night in, the thoughtful layout makes everyday living feel seamless and relaxed.

As you step inside, you are greeted by an inviting open floor plan with an abundance of light throughout that seamlessly connects the open-concept gourmet kitchen to the family room, creating an ideal space for both entertaining and everyday living. The kitchen features stainless steel appliances, including double wall ovens, cooktop and built-in microwave, complemented by a spacious island and quartz countertops. The Morning Room (Breakfast Room) and Conservatory offers light filled retreats year round. You will also find five generously sized bedrooms, each designed with comfort in mind. The primary suite is a true retreat, with a spacious sitting room and dual walk-in closets in addition to a luxurious en-suite bathroom featuring a soaking tub, walk-in shower, and dual vanities as well as dual water closets! The family room features 10’ ceilings and a relaxing gas fireplace to keep you warm in the cooler nights! The full basement, with an outside entrance, provides extra entertaining spaces with a extensive recreation room, true fifth bedroom and full bath as well as an unfinished area which leaves endless possibilities for customization, whether you envision a home theater, gym, or additional living space. The bedroom floor laundry adds a touch of practicality to daily routines, while the cozy family room off the kitchen serves as the heart of the home, perfect for relaxation and connection. The side-entry garage accommodates three vehicles and a generous amount of storage space, ensuring convenience and ease of access.

This residence is not just a home; it's a lifestyle choice that embodies luxury, comfort, and modern living. Experience the perfect blend of sophistication and warmth in this remarkable new construction home, where every detail has been thoughtfully curated for your enjoyment. All of this with an Annapolis address (and a close proximity to the water and fine restaurants Annapolis has to offer) to add to the joy you will feel from choosing this as your next home. Howmar Homes is a local builder dedicated to treating every house as if it were his own. With no shortcuts taken, each home reflects true care and craftsmanship you can see and feel in every detail. An optional inground pool has already been approved and has been cited on property for future or present consideration. If you act quickly, you can still select final finishings. Don’t miss your chance! Schedule your showing today!

ANNAPOLIS

1907 MACKIEBETH COURT

5 Beds

4 Baths

5,437 Sq.Ft.

$1,575,000

MLS#: MDAA2125858

New Price - Seller wants offer today and a fast close. Incredible value for this Custom-built, Private, Waterfront Retreat on Crab Creek off the South River. Private one acre, deep water Waterfront with incredible views from almost every room and an In Ground Pool. This gorgeous property is an entertainers dream - just minutes from downtown Annapolis as well as Rt 50 and commuter routes making it the ideal resort like residence or weekend getaway As you arrive up the long tree-lined drive and enter the grand entry foyer with the wall of windows and stunning water views you'll immediately take in the multi-level tray ceilings with custom lighting effects, the marble and the hardwood floors and the curved walls and cabinetry. These amazing details are carried throughout as well as the stunning water views from almost every room. This property was custom designed by the original owners who were an Architect and an Interior Designer. Next, head out the side entrance to the gazebo and the private, resort-like in-ground pool surrounded by hardscape and trees. This is the perfect place for outdoor living and entertaining. Finally, head out the back door to the large deck overlooking your waterfront vista and stroll down to the water across the storybook-like bridge and gently slopped path to your private pier with a deep water slip. You won't want to miss this one. Note: 30 day rent back is needed by the Seller after closing.

ANNAPOLIS

2639 GREENBRIAR LANE

3 Beds

2 Baths

3,888 Sq.Ft.

$1,500,000

MLS#: MDAA2129854

Incredible Opportunity in the Heart of Eastport!

Beautifully remodeled Victorian located on the Eastport Peninsula. Features include a welcoming front porch, wood floors, and a chef’s kitchen with Viking appliances, a 6-burner stove, and vented hood. Windows and roof were replaced in 2025; roof includes new gutter guards. Energy-efficient appliances, including a gas on-demand water heater, have earned this home an Energy Star Certificate from BGE.

Flexible heating and cooling options with radiator heat and five mini-split units providing a total of 48,000 BTUs for heating and cooling. Skylights feature solar shades, and the fully encapsulated crawl space enhances year-round comfort and efficiency.

Upper level offers two bedrooms, each with a full bath, plus a full-size washer and dryer.

Enjoy a private, fully fenced backyard (new fence 2020) with mature native trees and landscaping—perfect for relaxing or entertaining. The detached accessory structure offers endless possibilities: office, studio, hobby room, or gym. And don't forget.....there is an off street driveway !!

This property is move-in ready—just bring your personal touch!

ANNAPOLIS

120 CHESAPEAKE AVENUE

2 Beds

2 Baths

2,130 Sq.Ft.

$1,449,000

MLS#: MDAA2130442

Tucked back from the road and surrounded by trees, this contemporary waterfront home offers privacy and a serene connection to nature. Unique original details have been thoughtfully preserved while the interior has been completely renovated for modern living. From the moment you enter, walls of glass draw your eye through the home to the expansive deck that stretches nearly the full length of the house, showcasing tranquil views of Weems Creek through the trees. The open floor plan features a living room with an electric fireplace providing supplemental heat, a beautifully remodeled gourmet kitchen with bar, a dining area, and a conveniently placed mudroom, pantry, and powder room. Upstairs, two ensuite bedrooms include a spacious primary suite with multiple closets and a skylit bath with walk-in shower. The lower level hosts two additional bedrooms and a shared bath with steam shower, while an unfinished basement level provides storage and houses the utilities. Outside, the deck is ideal for entertaining with multiple seating areas and an outdoor TV. While the waterfront is not currently accessible, the property offers potential for private water access and a pier. Whether enjoying the everchanging scenery and waterfowl from indoors or taking in the view from the deck, the setting is captivating. The sought-after Admiral Heights community provides voluntary HOA membership with access to waterfront amenities, a boat club, pool membership, and neighborhood parks. Located within close proximity to restaurants, groceries, shopping and Navy Stadium events, with easy access to all major commuter routes to DC, Baltimore and beyond. Welcome Home!

ANNAPOLIS

173 WILLIAMS DRIVE

4 Beds

3 Baths

2,382 Sq.Ft.

$1,425,000

MLS#: MDAA2126690

#MDAA2131598

ANNAPOLIS

133 LAKE VIEW DRIVE

5 Beds

5 Baths

4,308 Sq.Ft.

$1,400,000

MLS#: MDAA2131598

Don’t miss this stunning new construction in the highly desirable Homewood neighborhood of Annapolis. Perfectly situated within walking distance to downtown, this thoughtfully designed luxury residence offers the ideal blend of sophistication, comfort, and convenience. Step inside to soaring 9-foot ceilings on every level and a light-filled open floor plan. The gourmet kitchen is a chef’s dream, featuring 42-inch custom cabinetry, quartz countertops with coordinating backsplash, stainless steel appliances, and an oversized island that flows seamlessly into the dining area and spacious family room with a cozy gas fireplace. Sliding doors extend the living space to a private deck, creating the perfect setting for entertaining. A stylish powder room and functional mudroom with laundry space complete the main level. Upstairs, the expansive primary suite offers a large walk-in closet and a spa-inspired bath with double vanity, soaking tub, and glass-enclosed shower. Two additional bedrooms and a well-appointed guest bath provide both comfort and practicality. The finished lower level offers even more living space with a generous recreation room, a fourth bedroom, and a full bath—ideal for guests or extended family. Set on a charming tree-lined street, this home captures the unique character of Homewood with the benefits of modern construction. Residents enjoy a vibrant, walkable community with abundant green spaces and easy access to major routes, while remaining just steps from the energy of downtown Annapolis. This home offers the rare opportunity to experience the best of luxury living in one of the city’s most coveted neighborhoods.

ANNAPOLIS

1207 MCGUCKIAN STREET

4 Beds

3 Baths

3,150 Sq.Ft.

$1,395,000

MLS#: MDAA2127608

There are so many option available for this property in the heart of Historic Annapolis. You may want to convert the entire home back to one living unit. You may want to live in one, long-term rent the other two or short term rent one. You may choose that it be be used for a couple/single person to live in one apt and rent out 2 or have a multigenerational combined family living in 1, 2 (while renting 1) or all 3. There are so many possibilities to enjoy this amazing property. This is 3 fully finished levels and units above grade. The basement level houses the storage area, HVAC and shared laundry area. All of the units are fully furnished with kitchen appliances, items, dishware, glassware, beds, linens, furniture, you name it, it is there and conveys. This is steps away from the Naval Academy. The main level entry has a hallway with stairwell to the upper level units and access to the man level unit Apt 1 and the basement. Apt 1 offers a foyer, eat-in kitchen, full bath, living room, bedroom and access to the rear patio fenced in area. The 2nd level has Apt 2 with a living room, kitchen, bath, 2 bedrooms and access to the rear patio area. The third upper level offers a full bath, galley kitchen, bedroom and large living area with space for a table, couch and mor furnishings. All units have the old time charm with modern components. All three units offer high ceilings. This is a very popular property so bear with us as we want to accommodate all showing requests. The most advance notice you can give the better. There may be times when all 3 may not be able to be seen on the same day. There is a virtual tour where you can walk through the entire property, zoom in and out and see the whole house from your phone or computer. This is also listed as Residential MLS# MDAA2132242. Parking info is loaded in the documents section.

ANNAPOLIS

165 KING GEORGE STREET

4 Beds

None Baths

2,649 Sq.Ft.

$1,375,000

MLS#: MDAA2132270

There are so many option available for this property in the heart of Historic Annapolis. You may want to convert the entire home back to one living unit. You may want to live in one, long-term rent the other two or short term rent one. You may choose that it be be used for a couple/single person to live in one apt and rent out 2 or have a multigenerational combined family living in 1, 2 (while renting 1) or all 3. There are so many possibilities to enjoy this amazing property. This is 3 fully finished levels and units above grade. The basement level houses the storage area, HVAC and shared laundry area. All of the units are fully furnished with kitchen appliances, items, dishware, glassware, beds, linens, furniture, you name it, it is there and conveys. This is steps away from the Naval Academy. The main level entry has a hallway with stairwell to the upper level units and access to the man level unit Apt 1 and the basement. Apt 1 offers a foyer, eat-in kitchen, full bath, living room, bedroom and access to the rear patio fenced in area. The 2nd level has Apt 2 with a living room, kitchen, bath, 2 bedrooms and access to the rear patio area. The third upper level offers a full bath, galley kitchen, bedroom and large living area with space for a table, couch and mor furnishings. All units have the old time charm with modern components. All three units offer high ceilings. This is a very popular property so bear with us as we want to accommodate all showing requests. The most advance notice you can give the better. There may be times when all 3 may not be able to be seen on the same day. There is a virtual tour where you can walk through the entire property, zoom in and out and see the whole house from your phone or computer. This is also listed as Multi-Family MLS# MDAA2132270. Parking info is loaded in the documents section.

ANNAPOLIS

165 KING GEORGE STREET

4 Beds

3 Baths

2,649 Sq.Ft.

$1,375,000

MLS#: MDAA2132242

OPEN HOUSE LOCATION on 11/23 is 9 Rusty Red Dr. in Annapolis. At our show home. Or make an appointment to visit our show home! This listing is for an End Unit at the standard price, however, Sturbridge Homes is offering a generous pre-construction incentive package for early buyers, including: $40,000 in closing cost credit, $30,000 in options and upgrades, including a hot tub installed on the rooftop terrace, No upcharge for end units (-$25,000), a one-year membership to Lifetime Fitness. Submit your deposit now to lock in current pricing and have the ability to customize your home! Sales Center appointments are available now. A sample of the builder's work nearby is available to tour.
Welcome to Towne Row - A community of 18 Luxury Townhomes in the Annapolis Town Center Corridor.
A Towne Row home is superior in every way. The craftsmanship and expansive spaces are apparent immediately. Notice the contemporary exterior, rooftop terrace for entertaining and stargazing, and two-car garage. Savor the spacious kitchen and luxurious owner's suite, privately situated on its own level, and the high-end materials and fixtures throughout. Live graciously and vertically on four generous levels, whisked up and down by your private elevator. This is Towne Row, your haven, your showplace, your new home. It's like none other in Annapolis. Features include: 3,100 Square Feet of Living Space, 3 Bedrooms + Den, 3 Full Baths, 2 Half Baths, Expansive Gourmet Kitchen With Walk-out Deck, Private Elevator, Elegant, Spacious Owner's Suite on Its Own Level, Quartz Countertops Throughout, Four Levels of Finished Living Space, Rooftop Deck With Space for Hot Tub, Two-car Garage, Energy Star & LEED Gold Certified

Location, location, location. Living at Towne Row puts you in the heart of the bustling Annapolis Town Center corridor. You have instant access to an array of upscale and casual restaurants, boutiques and shops, favorite grocery stores, sophisticated fashion and home goods retailers, fitness clubs, movie theaters, and essential services. Plus, you'll be minutes from the Annapolis historic district, endless waterways, nearby marinas, and a short drive to Baltimore and Washington, D.C. It's luxury living and convenience beyond compare.

Lot dimensions, floor plans, and square footage figures are approximate. Architectural renderings are samples only and may not reflect the exact product. Sellew Rd. has not been built and may not appear on some mapping apps.

ANNAPOLIS

208 SELLEW ROAD

3 Beds

3 Baths

3,100 Sq.Ft.

$1,375,000

MLS#: MDAA2119308

This is a stunning home in one of Annapolis’s hottest in-town neighborhoods --- offering generous living spaces, an entertainer's kitchen, and the perfect layout to suit many lifestyles. Eateries, coffee shops, boutiques, breweries, schools, churches, a grocery store, pharmacy, veterinarian, and more are just minutes from the front door—creating an effortless, walkable way of living. Easy commute to USNA, Fort Meade, NASA Goddard, D.C., and Baltimore. An excellent opportunity to own in coveted West Annapolis.

ANNAPOLIS

112 MELVIN AVENUE

4 Beds

2 Baths

3,462 Sq.Ft.

$1,350,000

MLS#: MDAA2132602

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