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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

357

# of Listings

3

Avg # of Bedrooms

$480

Avg. $ / Sq.Ft.

$1,092,577

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

357 Properties Found. Page 4 of 24.

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

Welcome to 743 Rolling View Drive in the coveted waterfront community of Cape St Claire. This beautifully maintained home offers over 3,800 square feet of finished living space, including 4 bedrooms, 3.5 bathrooms, and a potential 5th bedroom in the basement. Set on over half an acre with expansive views of Deep Creek leading to the Magothy River, this is a rare opportunity for spacious, move-in-ready waterfront living.

The main level features an open-concept layout with large windows framing serene water views. A custom chef’s kitchen anchors the space with Quartz and natural wood countertops, stainless steel appliances—including a double wall oven, induction cooktop, microwave, refrigerator, and dishwasher—and radiant heated floors. The kitchen flows seamlessly into the main living and dining areas, accented by hardwood flooring and wood beam details. A propane fireplace adds warmth to the adjacent library, which also includes built-in shelving and a full bath—ideal for guests or flexible living. A main-level bedroom includes a built-in Murphy bed, offering excellent functionality as an office or guest suite.

Upstairs, the primary suite is a luxurious retreat with two walk-in closets and a spa-like en suite bath featuring radiant heated floors, a clawfoot soaking tub, dual vanities, and a custom mosaic tile shower with artistic tilework, including heron and rockfish detailing. Two additional bedrooms, a full hallway bath, and a convenient top-floor laundry room complete the upper level.

The finished basement provides additional living space with tile flooring, a wet bar with mini fridge and storage, a half bathroom, walk-out access to the backyard, and a flexible space that could serve as a 5th bedroom or office.

The mudroom entry off the detached two-car garage includes custom cubbies, heated flooring, and a built-in commercial-grade ice maker—perfect for stocking coolers or entertaining. Dual-zone HVAC ensures year-round comfort, and the roof and windows have been updated in recent years and remain in excellent condition. A whole-house generator offers added peace of mind.

Outdoor living is just as impressive: a composite wraparound deck with trellis, custom stone patio with built-in fire pit, and mature landscaping create a peaceful backdrop. Follow the custom paver walkway with concrete steps down to a private pier equipped with two boat lifts, a kayak launch, water and electric hookups, and a waterfront storage shed with power. A screened-in porch at the top of the steps with electricity offers the perfect setting to unwind after a day on the water. The home also features a fenced yard, invisible pet fence, and a long driveway with ample parking.

Community amenities include three private beaches, three marinas, multiple parks, a rentable clubhouse, a local shopping center, and seasonal events such as the 4th of July celebration and the Strawberry Festival. Located in the Blue Ribbon Broadneck School District, this home delivers the very best of Annapolis waterfront living.

Special Buyer Incentive! Get a Lower Rate – On Us!
If you choose to work with the seller’s preferred lender, you’ll receive a 1% Temporary Rate Buydown for the First Year that means lower monthly payments for you—at no cost to you as the buyer! Take advantage of this limited-time opportunity to make your new home even more affordable. Ask me for details during your visit today!

ANNAPOLIS

743 ROLLING VIEW DRIVE

4 Beds

3 Baths

3,827 Sq.Ft.

$1,750,000

MLS#: MDAA2109136

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

#MDAA2109866

ANNAPOLIS

146 PRINCE GEORGE STREET

4 Beds

2 Baths

2,550 Sq.Ft.

$1,750,000

MLS#: MDAA2109866

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.

$1,750,000

MLS#: MDAA2115356

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.

ANNAPOLIS

400 JEFFERSON STREET

4 Beds

3 Baths

3,640 Sq.Ft.

$1,700,000

MLS#: MDAA2032362

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

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

Custom Luxury in Downtown Annapolis — Over 2,100 Sq Ft of High-End Living at West141

Welcome to Unit 304, the premier residence in the boutique West141 building and the only unit created by combining two original floor plans into one expansive home. With over 2,100 square feet of thoughtfully designed space, this is downtown Annapolis condo living at its most refined.

Originally configured as a 3-bedroom, 3-bath layout, this home has been expertly redesigned to enhance both style and function. The spacious primary suite features its own private balcony, a seating area, a spa-inspired bath with double vanity, soaking tub, and oversized walk-in shower, and a large walk-in closet with custom California Closet built-ins. The second bedroom includes a private ensuite bath, perfect for guests. The third bedroom has been transformed into a high-end office with over $17,000 in custom cabinetry, shelving, and a built-in desk.

Off the main living area, a flexible bonus space provides the perfect zone for a home gym, reading lounge, or guest accommodations with a sleeper sofa or Murphy bed. And for any additional guests, the luxury Graduate Hotel is located directly across the street.

The kitchen is a showstopper—featuring an oversized quartz island with bar seating, stainless steel appliances, crisp white cabinetry, and designer lighting—all opening to a sunlit living and dining area accented by shiplap walls and custom built-ins.

Stylish and functional upgrades include: over 2,100 sq ft of interior space • custom-built office • three California Closet systems • remote-controlled motorized shades • two private balconies (one off kitchen/dining, one off primary suite) • spacious primary suite with spa-like bath and seating area • shiplap accent walls • oversized kitchen island with quartz counters and bar seating • stainless appliances and shaker cabinetry • flexible bonus space for gym, guest, or den • second bedroom with private ensuite bath • separate laundry room with storage cabinetry • two secure garage parking spaces with a private storage unit • elevator building with controlled access • short-term rentals allowed • steps to dining, shopping, Naval Academy, and Navy Stadium • easy access to Route 50 for D.C., Baltimore, and weekend getaways.

Unit 304 is truly one of a kind—offering the space and feel of a home with the convenience of low-maintenance condo living, all in the heart of Annapolis. Whether you’re looking for a primary residence, a stylish weekend escape, or a flexible investment property, West141 delivers it all.

Welcome home.

ANNAPOLIS

141 WEST STREET 304

3 Beds

3 Baths

2,012 Sq.Ft.

$1,599,000

MLS#: MDAA2112000

Welcome to 15 Chesapeake Landing, a beautifully updated townhome in one of Eastport’s premier gated waterfront communities. With Severn River views from two decks and an unbeatable location just a short walk to Downtown Annapolis, the U.S. Naval Academy, and some of the city's best restaurants, this home offers the ideal blend of luxury, lifestyle, and low-maintenance living.
This four-level residence includes three bedrooms, two full baths, and one half bath, offering a flexible floor plan that lives large and adapts to your needs. The main level features a completely renovated kitchen with a 10-foot island, stainless steel appliances, and space for four to dine comfortably at the counter. Acacia hardwood floors span the upper levels, while the lower level is finished with durable luxury vinyl plank flooring.
The primary suite is a true retreat, complete with two walk-in closets and a fully remodeled bathroom (2023) with high-end finishes. Outdoor living is maximized with a lower-level flagstone patio and three upgraded decks—including a newly completed railing system designed to enhance both space and views.
Additional highlights include a one-car garage with extra parking, attic storage, and updated systems such as a new hot water heater (2023), new HVAC and 12 updated windows and sliding doors, most replaced within the last two years.
Residents enjoy the security of a gated community and have the option to join the adjacent Annapolis Maryland Capital Yacht Club, which offers a pool, marina, clubhouse, and year-round social events. HOA dues cover landscaping, snow removal, and common area maintenance, providing a lock-and-leave lifestyle in the heart of Eastport.

ANNAPOLIS

15 CHESAPEAKE LANDING

3 Beds

2 Baths

2,153 Sq.Ft.

$1,595,000

MLS#: MDAA2109404

Experience Historic Charm & Modern Elegance in the Heart of Annapolis.

Nestled in the heart of downtown Annapolis, this stunning historic Federal-style home offers the perfect blend of timeless character and modern sophistication. Located on the iconic Duke of Gloucester Street, this residence places you just steps away from the waterfront, top-tier dining, boutique shopping, and the rich history that defines Annapolis.

From the moment you step inside, you’re welcomed by pristine hardwood floors, soaring ceilings, and an abundance of natural light that fills every room. The spacious and thoughtfully updated interior seamlessly combines historic charm with contemporary convenience, featuring custom millwork, built-ins, and an elegant fireplace that creates an inviting atmosphere.

The gourmet kitchen is a chef’s dream—offering premium appliances, custom cabinetry, and a layout designed for both entertaining and daily living. Enjoy your morning coffee in the sun-drenched breakfast nook or step outside to the private courtyard, a peaceful retreat perfect for al fresco dining or evening gatherings.

The primary suite is a sanctuary of its own, offering ample closet space and a spa-inspired ensuite bath. Additional bedrooms provide comfort and flexibility for guests, a home office, or creative spaces.

Beyond its breathtaking interiors, the true magic of this home lies in its location—walk to the U.S. Naval Academy, Maryland State House, and City Dock, or simply enjoy the vibrant energy of downtown life.

This is more than a home; it’s an opportunity to own a piece of Annapolis's history with all the conveniences of modern luxury. Don’t miss your chance to experience it firsthand—schedule your private showing today!

Short term rental numbers are remarkable.Seller willing to share upon request.

ANNAPOLIS

146 DUKE OF GLOUCESTER STREET

4 Beds

3 Baths

3,042 Sq.Ft.

$1,549,000

MLS#: MDAA2108604

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

Welcome to 816 Bay Ridge Avenue, a beautifully maintained 4-bedroom, 4.5-bath home located in Eastport’s coveted Sailor’s Quay community. Offering over 3,300 square feet of refined living space, this home blends modern coastal style with everyday convenience—just minutes from downtown Annapolis, marinas, and top-rated restaurants. Built in 2012, the home features an open-concept layout with hardwood floors throughout, fresh paint, premium trim, and a gourmet kitchen with granite countertops, stainless steel appliances, and a gas cooktop. The spacious main level is ideal for both casual living and entertaining. One of only a few homes in the community with a full-size ELEVATOR servicing all three levels, this residence is ideal for those seeking long-term comfort and accessibility. The oversized primary suite includes two large walk-in closets and a spa-like bath. A second en suite bedroom on the upper level—located next to the elevator—offers a convenient option for guests or multi-generational living. The finished lower level includes a full bath and is pre-plumbed for a future beverage center. An adjacent unfinished area is ready for a 5th bedroom, home gym, or office. Additional features include a 2-car garage, extra parking, Hardie plank siding, multiple decks, excellent storage, and great natural light throughout. Low-maintenance living with a $150/month HOA—this is Eastport living at its finest.

ANNAPOLIS

816 BAY RIDGE AVENUE

4 Beds

4 Baths

3,374 Sq.Ft.

$1,510,000

MLS#: MDAA2114914

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