Vintage homes for sale & real estate in Annapolis, MD

Vintage Home for sale in Annapolis, MD:

Live authentically. The Chesapeake Bay is the view, the backdrop and the reason to linger. From the covered bluestone porch, the horizon opens across the Bay with uninterrupted sky and water. Morning coffee, an afternoon breeze through open doors, evenings around the fire—the water sets the pace. Extensively renovated inside and out since 2019, this charming craftsman styled gem in the sought-after Bay Ridge Community offers easy one-floor living and a natural connection to the outdoors. Windows and skylights, French doors and Phantom screens invite the sunshine and bay breeze inside. New Café Elite appliances, induction cooktop, and laundry. Freshly painted, craftsman style tr

Vintage Home for sale in Annapolis, MD:

Welcome to 700 Miller Road. Discover a truly special property tucked away on a private road, yet just minutes away from historic downtown Annapolis. Located less than a 5-minute walk from the Naval Academy Marine Corps Stadium, this beautifully renovated 2026 home offers the rare combination of privacy, convenience and Annapolis charm. Set on a generous . 598-acre tract, the property backs-up to Tawes Gardens, that gives the home a tranquil and private setting. The home has been completely renovated in 2026, both inside and out, offering thoughtful updates while maintaining the integrity of the community. Enjoy the best of Annapolis, all within walking distance or true city living just a sh

Vintage Home for sale in Annapolis, MD:

Experience the best of the Annapolis lifestyle from this beautifully reimagined coastal Craftsman in the heart of Eastport. Ideally located within walking distance of downtown Annapolis, the waterfront, restaurants, shops, yacht clubs, marinas, and the many neighborhood amenities that make Eastport one of the area's most desirable communities, this extensively renovated home offers an exceptional combination of location, character, and modern comfort. Offering approximately 4,099 square feet of finished living space, the home features three bedrooms, a dedicated office, four bathrooms, and a versatile floor plan designed for both everyday living and entertaining. A welcoming front porch set

Vintage Home for sale in Annapolis, MD:

There's history here. In the 1940s, the Meade family built a number of homes on President Street and in Hillsmere — Meade Street bears their name. For the first time, the family will be passing on this home, one of the last one still in family hands, to new owners. Original wood trim, high ceilings, and wood floors pair with a surprisingly open floor plan for its age. The third bedroom and kitchen were added in the 1960's. The daughters' bedroom was the upper level for many years. A detached garage with an attached screened porch is perfectly positioned for outdoor entertaining. The yard is large and fenced. This home only needs the new owner's personal touches to make it once again a