Annapolis Real Estate

Annapolis Real Estate

Welcome to Annapolis, Maryland—a charming city that beautifully blends rich history with modern living. Nestled in Anne Arundel County, Annapolis is renowned for its stunning waterfront views, vibrant culture, and an array of recreational activities that cater to every lifestyle.

Annapolis, the state capital of Maryland, is steeped in history, boasting colonial architecture and cobblestone streets that transport you back in time. The city is home to the United States Naval Academy, where visitors can explore its impressive grounds and learn about the naval heritage that shapes this vibrant community.

As a subdivision, Annapolis offers a diverse range of housing options, from historic homes with character to contemporary developments that provide modern conveniences. Families, young professionals, and retirees alike find their perfect abode here, with neighborhoods that foster a sense of community and belonging.

The local amenities are abundant, with boutique shops, gourmet restaurants, and lively entertainment options just a stone's throw away. Outdoor enthusiasts will delight in the numerous parks, marinas, and scenic waterfronts that invite leisurely strolls, boating, and fishing.

Education is a priority in Annapolis, with top-rated schools and proximity to esteemed institutions. The city’s strategic location also makes it easy to access major urban centers, including Baltimore and Washington, D.C., while still enjoying the tranquility of suburban living.

Whether you are looking to buy your first home, retire in comfort, or invest in a vibrant community, Annapolis stands out as a remarkable place to call home. Embrace a lifestyle filled with history, beauty, and endless opportunities in Annapolis, Maryland!

Newest Listings in Annapolis

2638 Greenbriar Ln, Annapolis
$550,000
4 Beds ⋅ 2 Baths
DIAMOND IN THE ROUGH! 1.90 Acres • Solid Brick Ranch Home • Exceptional Location • Possible Subdivision Potential Location, land, and possibilities! An outstanding opportunity to renovate, reimagine, or potentially redevelop an unusually large residential property consisting of nearly two acres of land in one of the Annapolis area's most desirable and established residential locations. Situated toward the end of Greenbriar Lane, just off Forest Drive and literally minutes from Routes 665, 50, and 97, this spacious brick ranch home offers something increasingly difficult to find in the Annapolis area: a substantial parcel of land, a convenient location, and the flexibility to create something truly special. Built in 1955, the residence has served as a rental property for many years and is ready for a comprehensive cosmetic renovation and modernization. The home also features a substantial 20-by-30-foot addition constructed in the late 1980s, incorporating a large primary bedroom with cathedral ceilings, a small side porch, and a primary bathroom with his-and-hers vanities and closets. According to Anne Arundel County GIS records, the property contains approximately 2,500 square feet across the main level and approximately 1,300 square feet of unfinished space in the lower level. The existing floor plan includes four bedrooms, two full bathrooms, living and dining areas, a family room, kitchen, laundry room, and an enclosed sunroom or three-season room. The house presents an excellent opportunity for someone looking to transform an older, solid residence into an attractive modern home without sacrificing the character and space of an established property. THE LAND The property encompasses approximately 1.90 acres, with an unusually generous amount of frontage along Greenbriar Lane. Previous county mapping information indicates approximately 370 feet of road frontage and a rear property boundary of approximately 360 feet adjoining land owned by the City of Annapolis. Mature trees, established landscaping, and the property's substantial dimensions provide an attractive setting with considerable possibilities for landscaping, outdoor recreation, expansion, or potential additional residential development. The property is zoned R2 Residential, which may offer subdivision or additional building opportunities, subject to applicable zoning, minimum lot sizes, access requirements, utility availability, and county approvals. For a builder, investor, or homeowner interested in maximizing the value of a nearly two-acre parcel, this represents an especially intriguing opportunity. A LOCATION THAT IS HARD TO DUPLICATE Greenbriar Lane is an established residential street conveniently located off Forest Drive, with excellent access to shopping, restaurants, grocery stores, and the many amenities of the Annapolis area. The property is situated across the street from Crab Creek, a tributary of the South River, and is surrounded by neighborhoods featuring attractive custom-built homes, generously sized properties, and numerous waterfront residences. Historic downtown Annapolis, City Dock, the United States Naval Academy, and the city's renowned waterfront restaurants and attractions are approximately four miles away. The surrounding area offers a combination of suburban privacy and convenient access to everything Annapolis has to offer. AN OPPORTUNITY WITH MULTIPLE POSSIBILITIES. Properties offering this combination of acreage, location, road frontage, and potential are increasingly difficult to find in the Annapolis market.The home needs renovation. The location and land are the attractions. The possibilities are what make this property special. The property is offered in its present condition. Acreage, square footage, lot dimensions, zoning, permitted uses, and subdivision potential should be independently verified by prospective purchasers with Anne Arundel County and other applicable authorities.

2638 Greenbriar Ln, Annapolis

Listing courtesy of Cottage Street Realty LLC. Contact:

220 West St, Annapolis
$824,899
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:

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
$824,899
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:

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:

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