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The United States Naval Academy. Main Street. Historic Annapolis. The Chesapeake Bay. The Severn, West, and South Rivers, to name just a few. Annapolis offers a plethora of treasures to its citizens and millions of visitors each and every year. The “Annapolis lifestyle” means many different things to many different people, but its residents all agree that it is an amazing place to call home. You enjoy sail boating? You’ll love the famous Wednesday night sailboat races! You’re a power boater? Slide into Ego Alley on any warm night and enjoy the sights, sounds, and tastes of historic Annapolis. If you enjoy fine dining, shopping, the fine arts, or really anything, Annapolis has something for you. Are you eager to learn more? Reach out to The Regala Team to help you find the perfect Annapolis home for you!

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Annapolis

2026 Gov Thomas Bladen Way Unit #204, Annapolis image
2026 Gov Thomas Bladen Way Unit #204, Annapolis $340,000

Location, convenience, and peaceful surroundings come together in this well-maintained two-bedroom, two-full-bath condo. This unique end unit offers added privacy and rel...

  • 2 Beds
  • 2 Baths
Courtesy of Taylor Properties

Listing courtesy of Taylor Properties. Contact:

2514 N Haven Cove Unit #102, Annapolis image
2514 N Haven Cove Unit #102, Annapolis — Heritage Harbour $494,000

Welcome to this beautiful 2 Bedroom + Den, 2 Bath condo in N Haven Cove of Heritage Harbour. This inviting home is a popular floor plan with a spacious, updated eat-in k...

  • 2 Beds
  • 2 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

203 Cape St John Rd, Annapolis image
203 Cape St John Rd, Annapolis $3,375,000

Nestled in the serene enclave of Cape St. John, this exquisite coastal residence offers a harmonious blend of luxury and comfort, perfectly designed for an elevated lifes...

  • 5 Beds
  • 7 Baths
Courtesy of Long & Foster Real Estate, Inc.

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

24 Gentry Ct, Annapolis image
24 Gentry Ct, Annapolis $349,000

Located just 5 minutes from Downtown Annapolis in the quiet Gentry subdivision, this contemporary 4-bedroom, 2.5-bath home offers comfortable living across three finished...

  • 4 Beds
  • 3 Baths
Courtesy of Compass

Listing courtesy of Compass. Contact: (410) 886-7342

311 Sloping Woods Ct, Annapolis image
311 Sloping Woods Ct, Annapolis $414,900

Nestled in the serene community of Whispering Woods, this charming townhouse offers a perfect blend of comfort and functionality. Built in 1991, this well-maintained home...

  • 3 Beds
  • 4 Baths
Courtesy of Coldwell Banker Realty

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

4 Ridge Rd, Annapolis image
4 Ridge Rd, Annapolis $2,499,500

There are houses that simply check the boxes—and then there are houses that have a sense of place. Tucked away at the end of a quiet street in the coveted Wardour neighbo...

  • 6 Beds
  • 6 Baths
Courtesy of Cummings & Co Realtors

Listing courtesy of Cummings & Co Realtors. Contact: 4108230033

2691 Claibourne Rd, Annapolis image
2691 Claibourne Rd, Annapolis $825,000

Welcome to 2691 Claibourne Road, beautifully presented and ready to impress in the sought-after water-privileged community of Annapolis Roads. This spacious 4-bedroom, 3....

  • 3 Beds
  • 4 Baths
Courtesy of EXP Realty, LLC

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

20 Greystone Ct Unit #I, Annapolis image
20 Greystone Ct Unit #I, Annapolis $299,900

Discover this charming 2-bedroom, 2-bathroom unit in the desirable Annapolis Overlook community. Spanning 1,229 sq. ft. , this well-maintained garden-style apartment offe...

  • 2 Beds
  • 2 Baths
Courtesy of Compass

Listing courtesy of Compass. Contact: (410) 429-7425

7026 Channel Village Ct Unit #T2, Annapolis image
7026 Channel Village Ct Unit #T2, Annapolis $775,000

There is something special about life on the Chesapeake Bay, and this exceptional end-unit residence captures it beautifully. Ideally positioned where the Channel meets t...

  • 2 Beds
  • 2 Baths
Courtesy of TTR Sotheby's International Realty

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

property image
1017 Hyde Park Dr, Annapolis $534,000

Welcome to 1017 Hyde Park Dr, a charming two-story Dutch Colonial nestled in Annapolis, where classic character meets a convenient location. This 3-bedroom, 2-bath home o...

  • 3 Beds
  • 2 Baths
Courtesy of EXP Realty, LLC

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

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