Historic District Homes with Paved Parking features

Welcome to the Historic District of Annapolis, Maryland—a charming enclave where the past beautifully intertwines with modern living. Nestled in the heart of Anne Arundel County, this vibrant community is renowned for its rich history, picturesque streets, and stunning architecture. As you stroll through the Historic District, you’ll be captivated by the well-preserved colonial homes, each telling a story of yesteryears while offering the comforts of contemporary life.

One of the standout features of homes in this area is the availability of paved parking, a rare gem in such a sought-after location. Imagine the convenience of returning home to your own designated parking space, freeing you from the hassle of street parking. Many residences boast beautifully landscaped driveways, ensuring that your vehicles are not only secure but also add to the overall charm of your property.

Living in the Historic District means you’re just steps away from Annapolis’ vibrant waterfront, eclectic shops, and delectable dining options. Enjoy leisurely walks along the cobblestone streets, explore the local art scene, or take in the breathtaking views of the Chesapeake Bay. This community is not just a place to live; it’s a lifestyle enriched by culture, history, and a strong sense of community.

Whether you’re a history buff, a nature lover, or someone who appreciates the finer things in life, the Historic District offers a unique blend of all that Annapolis has to offer. Discover your dream home in this enchanting neighborhood and experience the perfect harmony of history and modernity.

Newest Historic District Homes with Paved Parking features

$1,675,000

5 Beds ⋅ 3 Baths

Ideally situated on the corner of Prince George & College Ave(across from St Johns College), this distinguished residence is tucked in the heart of Historic Downtown Annapolis. This exceptional home offers the charm of an Historic home built circa 1800's with modern conveniences. Soaring ceilings and windows create sun-drenched rooms with beautiful views of the grounds at St. Johns College. This home was built for entertaining. It has amazing flow to entertain your guests for a dinner party. Take a short walk to outdoor dining on West Street during "Dinner Under the Stars" or host friends for all the amazing Downtown events like Midnight Madness. This home is in the heart of it all! The electrical and plumbing was updated in 1990, new hot water heater in 2024, 2 heat pumps in 2025 and new Shake Shingle roof in 2026. There are 4 bedrooms and 2 full baths on the second floor with a bonus room on the third floor great for guests or office. All this just 1.5 blocks from the Naval Academy and steps to the shops and amazing restaurants Annapolis has to offer! There is driveway with private parking for 2 cars and plenty of street parking for guests. Walk to City Dock for morning coffee and watch the boats pass by or sit in the morning room and enjoy your coffee looking over the grounds of St. Johns. This is an amazing house in an amazing location with all that Annapolis has to offer.

250 Prince George St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$1,950,000

6 Beds ⋅ 4 Baths

Welcome to the Thomas Hyde House – a rare opportunity to own a piece of Annapolis history in the heart of downtown. Built in 1769, this impeccably restored Federal- style property blends 18th-century charm with modern luxury. Perfectly situated on sought- after Duke of Gloucester Street, this vibrant and colorful home offers stunning views of the Maryland State House and extremely rare off-street parking for 6+ vehicles. Originally configured as office space, the residence has been reimagined into six spacious bedrooms and four full baths across two beautifully fully remodeled levels, with the potential for third floor updating plus a large basement with ample storage and updating space. The first floor offers true single level living with a primary suite and second bedroom, while the second level features four additional bedrooms and a convenient laundry area. No detail has been overlooked – from new appliances, countertops, and cabinetry to frameless glass showers, ceramics, extensive trim and molding, recessed lighting, fresh interior and exterior paint, new plumbing/electric and sprinkler system, updated flooring, freshly painted standing seam roof/front dormers and more. The result is a turnkey home where historic character meets modern sophistication & luxury. The property is offered with negotiable furnishings, electronics and art, The Thomas Hyde House is as versatile as it is fun and captivating. Just steps from downtown Annapolis shopping, dining, yacht clubs, local marinas & major commuter routes. Whether as a primary residence, investment property, or distinctive downtown retreat. schedule your showing today.

192 Duke Of Gloucester, Annapolis

Listing courtesy of Samson Properties. Contact:

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