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9 Shipwright St, Annapolis
$3,495,000
3 Beds ⋅ 3 Baths
Quintessential downtown Annapolis waterfront home on the sparkling waters of Spa Creek! This amazing property combines the best of both worlds; the charming historic feel of a downtown Annapolis home with the premier waterfront lifestyle that every resident is looking for. Nestled on a quiet street, this home is the perfect size for an easy to own, lock up and go property. With 3 bedrooms and 2.5 baths it has all the elements needed to enjoy life to the fullest; either as the perfect weekend retreat or permanent residence. The Annapolis area and the surrounding waterways are sure to entertain in every season. The upper level of the home is dedicated to the spacious Primary suite with unique sitting area and expansive roof deck. Take in panoramic views of Spa Creek, Annapolis Harbor and Eastport. An unparalleled vantage point for sunrise coffee or sunset cocktails. The main level offers multiple cozy gathering areas including a formal living room with fireplace, home office and light filled gourmet kitchen with dining area. The kitchen area flows effortlessly into the dining area and out onto the rear deck overlooking Spa Creek. Perfect for gathers of all sizes and dining al fresco. The lower level provides an ideal retreat for family or guests with 2 spacious bedroom a full bath and a cozy family room with fireplace. Head out to the charming covered patio to read a book or sip your evening cocktail or venture out on the water from the private pier. The amazing location is walkable to everything Annapolis has to offer and Spa Creek provides quick access to the Chesapeake Bay and beyond. Welcome Home!

9 Shipwright St, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

146 Duke Of Gloucester St, Annapolis
$1,950,000
4 Beds ⋅ 4 Baths
Price improvement!!! Welcome to 146 Duke of Gloucester Street! As you approach the home, a welcoming front porch will greet you, offering a place to sit and take in all that Annapolis has to offer. Nestled in the heart of historic Annapolis, this beautifully appointed 4-bedroom, 3.5-bath residence seamlessly blends timeless charm with modern sophistication. Rich in character and thoughtfully updated throughout, this exceptional home offers an inviting open-concept main level designed for both comfortable living and effortless entertaining. Step inside to discover sun-filled living and dining spaces anchored by a stunning exposed brick fireplace that adds warmth and historic appeal. The modern kitchen is a true centerpiece, featuring stylish finishes, ample cabinetry, and a functional layout perfect for everyday living and hosting guests alike. The second level features three spacious bedrooms filled with natural light from oversized windows, generous closet space, and two beautifully appointed full bathrooms, creating comfortable accommodations for family and guests alike. Occupying the entire third floor, the expansive primary suite serves as a private retreat complete with a luxurious spa-inspired bath designed for relaxation and rejuvenation. Outside, enjoy a charming backyard—an ideal setting for outdoor dining, gardening, or simply unwinding in your own private oasis. Perfectly situated just moments from the waterfront, renowned restaurants, boutique shopping, and the rich history of downtown Annapolis, this home offers a rare opportunity to experience historic living with all the comforts of modern design.

146 Duke Of Gloucester St, Annapolis

Listing courtesy of Douglas Realty LLC. Contact:

220 West St, Annapolis
$849,900
Welcome to 220 West Street in Annapolis, Maryland: a rare, fully gut-renovated detached property in the heart of the Downtown Arts District, offered at a row home's price and carrying MX mixed-use zoning that opens the door to residential, commercial, and income-producing use alike. Completed in 2024, the property has been transformed from top to bottom. Every major system and finish has been replaced, delivering a true turnkey opportunity for a buyer seeking a lifestyle home, an investment asset, or a business address in one of the most walkable and desirable areas in Annapolis. Unlike the majority of Downtown Annapolis properties, this is a fully detached building, not a rowhome or townhouse, giving it enhanced privacy, natural light, and a far more versatile footprint for adaptive use. The mixed-use zoning is the story. Under Annapolis MX, the building can serve as a full-time residence, a furnished short-term or corporate rental, or a range of commercial uses including professional and medical office, a personal-care or boutique fitness studio, a gallery or arts studio, or hospitality and food-and-beverage concepts such as a wine bar or cafe, with boutique lodging and inn use available through the City's approval process. The property's own history proves the point: it has previously operated as a furniture store, office space, and a duplex residence. Few Downtown Annapolis addresses offer this much optionality. The extensive renovation includes a brand-new roof, all-new electrical and plumbing, a new high-efficiency mini-split HVAC system, a redesigned floor plan, new flooring throughout, updated lighting, and fully rebuilt kitchen and bathrooms. A modern fire sprinkler system is in place, a meaningful head start for any commercial or lodging adaptation. Outside, the spaces have been completely upgraded with a new deck, brick patio pavers, new fencing, and ambient lighting made for evening entertaining. Inside, a bright two-story entry foyer opens to a professionally curated interior that blends modern comfort with intentional functionality. Three bedrooms and two full bathrooms give the layout the flexibility to support full-time living, guest accommodations, workspace, or commercial conversion. The main-level primary suite opens directly to a private brick patio, while the second bedroom accesses a rear deck overlooking the fully fenced yard: indoor-outdoor connections rarely found downtown. The reimagined kitchen, with new cabinetry, countertops, and appliances, and an open dining area, supports both daily living and gatherings. Step outside into a fully fenced private yard with a brick patio, outdoor dining, lounge seating, and ambient lighting: a genuine urban retreat steps from the energy of Downtown Annapolis. Moments from restaurants, shops, nightlife, City Dock, the Maryland State House, and the U.S. Naval Academy, with easy access to Baltimore, Washington D.C., and BWI, it is equally compelling for owner-users, investors, commuters, and second-home buyers. Adding further value, the property can be sold fully furnished, with every piece professionally selected, so the next owner can move in immediately, operate it as a short-term rental, or transition it into a commercial or mixed-use setup with minimal effort. This is more than a home. It is a rare, fully renovated, detached mixed-use opportunity in Downtown Annapolis where lifestyle, flexibility, and long-term value align.

220 West St, Annapolis

Listing courtesy of Keller Williams Realty Centre. Contact:

220 West St, Annapolis
$849,900
3 Beds ⋅ 2 Baths
Welcome to 220 West Street in Annapolis, Maryland. A rare, fully gut-renovated detached property located in the heart of the Downtown Arts District at a row home's price, offering exceptional flexibility with mixed-use zoning that allows for both residential and commercial use. Completed in 2024, this property has been completely transformed from top to bottom. Every major system and finish has been replaced, delivering a true turnkey opportunity for buyers seeking lifestyle, investment potential, or business use in one of the most walkable and desirable areas in Annapolis. Unlike the majority of Downtown Annapolis properties, this is a fully detached home, not a rowhome or townhouse, providing enhanced privacy, natural light, and a more versatile footprint. The extensive renovation includes a brand new roof, all new electrical and plumbing systems, a new high-efficiency mini-split HVAC system, redesigned floor plan, new flooring throughout, updated lighting, and fully rebuilt kitchen and bathrooms. The outdoor spaces have been completely upgraded with a new deck, new brick patio pavers, new fencing, and ambient lighting that creates a warm and inviting atmosphere for evening entertaining. Inside, the home features a bright two-story entry foyer and a professionally curated interior design that blends modern comfort with intentional functionality. With three bedrooms and two full bathrooms, the layout is flexible enough to support full-time living, guest accommodations, workspace needs, or commercial adaptation. The main-level primary suite opens directly to a private brick patio, while the second bedroom features access to a rear deck overlooking the fully fenced yard. These indoor-outdoor connections are rarely found in Downtown Annapolis and significantly enhance livability. The kitchen has been completely reimagined with new cabinetry, countertops, and appliances, designed to support both daily living and entertaining. The open dining area comfortably accommodates gatherings, reinforcing the home’s versatility. Adding even more value, this property is being sold fully furnished. Every piece has been professionally selected, allowing the next owner to move in immediately, operate as a short-term rental, or transition into a commercial or mixed-use setup with minimal effort. Historically, this property has served multiple purposes, including a furniture store, office space, and duplex residence, highlighting the true flexibility and long-term value of its mixed-use zoning designation. Step outside into a fully fenced private yard featuring a brick patio, outdoor dining area, lounge seating, and ambient lighting, creating a unique urban retreat just steps from the energy of Downtown Annapolis. Located just moments from restaurants, shops, nightlife, City Dock, the Maryland State House, and the U.S. Naval Academy, this property offers unmatched walkability and access. With convenient proximity to Baltimore, Washington D.C., and BWI Airport, it is equally appealing for commuters, investors, and second-home buyers. This is more than a home. It is a rare, fully renovated, detached mixed-use opportunity in Downtown Annapolis where lifestyle, flexibility, and long-term value align.

220 West St, Annapolis

Listing courtesy of Keller Williams Realty Centre. Contact:

202 Bertina A Nick Way, Annapolis
$670,000
4 Beds ⋅ 2 Baths
Coming soon!! Welcome to 202 Bertina A Nick Way, a spacious 4-bedroom townhouse in a convenient Annapolis location. The main level offers a comfortable open-concept layout with generous living and dining areas, durable flooring, and plenty of natural light. The kitchen features stainless steel appliances, ample cabinetry, and direct access to the deck, making it easy to enjoy both everyday living and outdoor entertaining. A generously sized primary bedroom with a private full bath is also located on the main level. Upstairs, three additional bedrooms and another full bathroom provide plenty of room for family, guests, or a home office. The finished lower level offers even more flexibility with a spacious recreation room and additional utility/storage space. Ideally situated near downtown Annapolis, the United States Naval Academy, Chesapeake Bay, shopping, dining, parks, and waterfront activities, this home offers both convenience and access to everything Annapolis has to offer. Major commuter routes to Baltimore and Washington, DC are also easily accessible. Whether you're looking for a primary residence, weekend retreat, or potential airbnb property, this home offers a versatile layout in a desirable location.

202 Bertina A Nick Way, Annapolis

Listing courtesy of EXP Realty, LLC. Contact:

721 Fairway Dr, Annapolis
$567,000
3 Beds ⋅ 3 Baths
Elegant brick and siding split-foyer residence offering 3 bedrooms and 3 renovated full bathrooms on a beautifully sized 0.21-acre lot. The thoughtfully designed upper level features a sun-filled living room, formal dining area, well-appointed brand new kitchen with new appliances, and seamless access to the rear deck—perfect for refined indoor-outdoor living. Two bedrooms and two full baths complete the main level. The lower level is highlighted by a bedroom with a generously renovated full bathroom, providing an ideal owner’s retreat or guest quarters, along with a spacious family/recreation room, laundry area, and mechanical room. Luxury vinyl flooring extends throughout both levels, complemented by windows in excellent condition. Major updates include the roof and new outdoor HVAC system. Serviced by well and public sewer. A well-maintained home offering comfort, privacy, and timeless appeal.

721 Fairway Dr, Annapolis

Listing courtesy of KW Metro Center. Contact:

45 Randall St, Annapolis
$475,000
45 Randall Street presents an extraordinary opportunity to own commercial real estate in the very heart of Downtown Annapolis at a moment when the surrounding waterfront is undergoing a remarkable transformation. Positioned between the U.S. Naval Academy and the Annapolis waterfront, this charming boutique storefront sits along the natural path of tourists, residents, midshipmen, boaters and visitors exploring one of Maryland’s most iconic destinations. And the timing may be just as compelling as the location. Annapolis is making a significant investment in the future of City Dock, creating a reimagined waterfront designed to become an even greater destination for residents and visitors. The improvements include a new City Dock Park, expanded public gathering and programming areas, a Maritime Welcome Center, enhanced pedestrian spaces, significant flood-mitigation infrastructure and a revitalized waterfront experience. The rebuilt Hillman Garage has also increased downtown parking capacity. With Barry Gate anticipated to reopen in December 2026, the Ego Alley boardwalk expected to reopen in March 2027, and City Dock Park and the Maritime Welcome Center targeted to open as early as July 2027, the next chapter of Downtown Annapolis is already taking shape. For an investor or owner-user, 45 Randall Street offers the increasingly rare opportunity to secure a piece of commercial real estate within steps of this major public investment—before the transformation is complete. The property’s highly visible storefront, classic Historic Annapolis character and exceptional walkability create an ideal setting for boutique retail, specialty food or beverage, gallery or studio space, professional use, specialty services, or a long-term investment hold. Surrounded by established restaurants, retailers, attractions and year-round activity, the location benefits from an audience that is exceptionally difficult to replicate. Real estate this close to the Naval Academy, Ego Alley and the Annapolis waterfront simply cannot be recreated. For the buyer who recognizes location, scarcity and the long-term potential created by the transformation occurring just outside the door, 45 Randall Street is more than a storefront—it is an opportunity to own a piece of the future of Downtown Annapolis. Seller financing may be available!

45 Randall St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: