Annapolis, MD Homes for Sale under $2,000,000

Spectacular water-view home nestled at the tip of the Eastport Peninsula in coveted Chesapeake Landing, a premier gated community. Set within the vibrant Maritime Republic of Eastport, deeply rooted in sailboat racing and pleasure-boating traditions. 23 Chesapeake Landing offers an exceptional blend of comfort, convenience and the Annapolis waterfront lifestyle. Residents treasure the

Stephanie Snyder Long & Foster Real Estate, Inc.

Breathtaking 3 BR, 3.5 BA, 3,400 sq. ft. penthouse offering at GrandView in Annapolis Towne Centre--what a value! Bathed in natural light from expansive windows and enhanced by dramatic 11-foot ceilings, this residence offers space and sophistication. Rich hickory hardwood floors, stone counters, and a striking fireplace anchor the beautifully appointed interiors, while dual balconies on either

Yael Beckman Coldwell Banker Realty

Nestled in the heart of Eastport, this stunning Craftsman-style home offers the perfect blend of timeless charm and modern luxury. This was a complete remodel in 2012! Boasting 4 bedrooms and 4 full baths, this thoughtfully designed residence features an open floor plan accented by beautiful bamboo flooring adding warmth and style throughout. The gourmet kitchen is the centerpiece of the home,

John Collins Long & Foster Real Estate, Inc.

Waterfront on the Chesapeake Bay! Welcome to 7017 Bay Front Drive, a charming two-story summer cottage in Annapolis with unobstructed views of the Bay and Bay Bridge. Watch the Blue Angels fly overhead, catch Fourth of July fireworks, or simply enjoy the boats passing by — all from home. Swim, kayak, fish, crab, paddle board, or boat right from your front yard.The main level offers an

Becky King Home Towne Real Estate

** Private first-look appointments are available. Contact the listing agent to schedule for a first-look. **A rare find in Eastport: an oversized attached two-car garage, plus a driveway and additional off-street parking, in a walkable waterfront neighborhood where garages are hard to come by. Beyond the striking exterior is a brand-new, ground-up home spanning three expansive levels,

Shirley Cheung Realty ONE Group Capital

Welcome to 202 Wardour Drive! This classic 1940 Dutch Colonial offers timeless character, generous living space, and an unbeatable Annapolis location. Situated on a quarter acre lot with large front yard, the south facing location ensures sunny days ahead! Located in the elegant Wardour community which reflects the naturalistic style of its designer, Frederick Law Olmstead, Jr, with its mature

David Orso Berkshire Hathaway HomeServices PenFed Realty

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

Rob Carter Douglas Realty, LLC

**Price Improvement! ** Now offered at **$1,600,000**.Take another look at 87 Shipwright Street. In addition to the significant price reduction, several important improvements have recently been completed. The roof has been inspected, and minor repairs have been made. The kitchen floor has been repaired, eliminating the previous sag, and the crawlspace has been professionally remediated,

Catherine Watson - Bye RE/MAX Executive

Experience the best of Annapolis living in the sought-after, amenities-rich community of Fishing Creek Farm. Perfectly positioned to capture beautiful water views and surrounded by lush lawns and mature landscaping, this handsome brick-front Colonial offers a rare combination of timeless architecture, flexible living spaces, and an exceptional neighborhood lifestyle.A gracious foyer

Brad Kappel TTR Sotheby's International Realty

There is something unmistakably special about life in Eastport—and 820 Bay Ridge Ave captures it beautifully. Set within coveted Sailor’s Quay, this exceptional residence offers more than 4,000 square feet of sophisticated living across four beautifully finished levels, combining timeless architecture, thoughtful customization, and an effortless coastal sensibility just moments from the heart of

Wendy Oliver Coldwell Banker Realty

Set back off the road on a quiet cul-de-sac in the coveted Saefern community, this contemporary home offers peaceful water views, a private wooded setting, and endless potential to make it your own. Whether you're looking to move right in and enjoy the home as it is or reimagine the space into your dream retreat, this property presents an incredible opportunity in one of Annapolis' most

Brad Kappel TTR Sotheby's International Realty

** PRICE IMPROVEMENT** GREAT OPPORTUNITY TO OWN A PRIVATE LUXURY ESTATE ON THE BROADNECK PENINSULA!! Built in 2001, this stately brick Koch Colonial offers 4,648 square feet above grade and is nestled on a private 5.73-acre cul-de-sac lot in the highly sought-after Broadneck School District, delivering the perfect blend of luxury, privacy, and timeless elegance. Featuring a stunning 2022 gourmet

Elizabeth DuLaney EXP Realty, LLC

Rarely does a home of this historical significance become available in the heart of Historic Annapolis. Believed to date to the late 17th century, the extraordinary residence is among the city's oldest surviving homes, seamlessly blending centuries of architectural heritage with sophisticated modern living. Perched at the water end of Market St overlooking Spa Creek, this home is instantly

Moe Farley Coldwell Banker Realty

Prepare to be amazed by this rare waterfront opportunity offering 4 bedrooms, 4.5 baths with over 3000 square feet of living space with approximately 270-degree panoramic views of Gingerville Creek. Situated at the end of a quiet cul-de-sac, this exceptional property combines luxury, privacy, and an unbeatable location just minutes from Annapolis. Commuters will love the convenience of being just

Boyd Grainger Pearson Smith Realty, LLC

Nestled along one of the most prestigious streets in Historic Annapolis, 268 King George Street presents a rare opportunity to own a beautifully renovated residence just steps from the U.S. Naval Academy, St. John's College, City Dock, Main Street, Spa Creek, and the Chesapeake Bay. Offering the perfect blend of historic charm and sophisticated modern living, this exceptional home places you at

Carol Snyder Monument Sotheby's International Realty

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

Hanh Pham Samson Properties