Annapolis Homes with Colonial Style

Welcome to Annapolis, Maryland, a charming city steeped in history and brimming with character, where the beauty of colonial architecture harmonizes with the vibrant spirit of modern living. Nestled in Anne Arundel County, Annapolis is not only the state capital but also a delightful waterfront community that beckons homebuyers with its picturesque streets and rich heritage.

Annapolis is renowned for its stunning Colonial-style homes, which reflect the elegance and craftsmanship of a bygone era. These stately residences often feature timeless brick facades, large front porches, and intricate woodwork, creating a warm and inviting atmosphere that captivates both residents and visitors alike. Each home tells a story, with many dating back to the 18th century, showcasing the city’s deep-rooted history while offering modern amenities for today’s discerning homeowner.

Living in Annapolis means embracing a lifestyle that balances tranquility with excitement. Enjoy leisurely strolls along the charming downtown area, where boutique shops, gourmet restaurants, and vibrant art galleries await. For outdoor enthusiasts, the scenic waterfront provides ample opportunities for sailing, kayaking, and enjoying breathtaking sunsets over the Chesapeake Bay.

Moreover, Annapolis boasts a strong sense of community, with numerous events and festivals that celebrate its rich maritime heritage. Whether you’re drawn to the historic charm of Colonial architecture or the vibrant lifestyle offered by this coastal gem, Annapolis is a place where you can truly feel at home. Discover your dream Colonial-style residence in this enchanting city and become a part of its storied tapestry today!

Newest Annapolis Homes with Colonial Style

$1,999,999

4 Beds ⋅ 4 Baths

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: (410) 255-3690

$1,950,000

5 Beds ⋅ 3 Baths

Perfectly positioned in the heart of downtown Annapolis, this distinguished historic residence offers a rare opportunity to own a piece of the city’s architectural legacy while enjoying the convenience of two coveted off-street parking spaces. Overlooking the beautifully preserved grounds of St. John’s College, the home captures timeless views that enhance its already exceptional setting. Steeped in history, the property reflects an evolution of craftsmanship spanning centuries, with the original portion dating to the mid 1800s, an expansion in the late 1800s, and a thoughtfully integrated addition in 1921. Sold fully furnished, the interiors are curated with elegant period pieces that complement the home’s character and provide a seamless, move-in-ready experience. Enjoy peace of mind with the updated electrical and plumbing in 1990 , new hot water heater in January of 2024, new shake shingle roof in April 2026 and 2 new heat pumps in March 2025 Inside, classic architectural details unfold across the main level, where two gracious parlors—each anchored by a fireplace—offer inviting spaces for both intimate gatherings and relaxed everyday living. A welcoming entry hall with an open staircase sets the tone, leading to a charming dining room with its own fireplace and a convenient pass-through to the kitchen, blending historic ambiance with functional flow. The upper levels provide flexibility and space, with four bedrooms and two full baths on the second floor, while an additional bedroom occupies the top level—ideal for guests, a private retreat, or creative workspace. Below, the basement offers practical utility space and storage. Just moments from the shops, restaurants, and waterfront attractions of downtown, as well as the United States Naval Academy, this residence invites you to fully immerse yourself in the vibrant Annapolis lifestyle. From morning walks along tree-lined streets to evenings enjoying the energy of the harbor, this is a home where history, location, and livability converge in a truly special way. Welcome Home!

250 Prince George St, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

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