Welcome to Annapolis, Maryland, a city where old streets and pretty waterfront views come together to create a special place to live. Annapolis is one of the oldest cities in the United States, and its history can be seen all around, from brick buildings to charming shops and narrow streets.
But Annapolis isn’t just about the past. Today, it’s also known for its beautiful homes along the Chesapeake Bay. Many people are drawn here for the peaceful views, boating, and the appeal of living near the water.
In this guide, I’ll take you through four of the most luxurious neighborhoods in Annapolis. These are places where you’ll find large, elegant homes, private docks, and amazing views. It’s perfect for anyone dreaming of a waterfront lifestyle.
Eastport: A Waterfront Gem with a Fun, Independent Spirit
Eastport is one of the most loved neighborhoods in Annapolis, and for good reason! It's surrounded by water on three sides, giving it amazing views of the Severn River and Chesapeake Bay. Just across the bridge from downtown Annapolis, Eastport offers the best of both worlds: peaceful waterfront living with easy access to city life.
But what really makes Eastport stand out is its personality. In 1998, when the Spa Creek bridge, connecting Eastport to the rest of Annapolis, closed for repairs, the neighbors decided to have some fun. They jokingly declared Eastport the Maritime Republic of Eastport (MRE) and held their own “secession.” What started as a lighthearted joke turned into a beloved local tradition, with events like the annual Tug of War over Spa Creek and other community celebrations. That playful, independent spirit is still alive today.
It's not just the water that makes this neighborhood special. It’s the feeling you get when you walk the streets. Eastport oozes charm and character, with narrow roads, weathered boat docks, and homes that reflect a classic New England-style maritime look. From the architecture to the salty breeze, you know you’re in a true seafaring town.
Eastport is known as the city’s “maritime district,” filled with marinas, boats, and sailing culture. You’ll also find great spots to eat along Severn Avenue, like Carroll’s Creek Café, Lewes’ Steakhouse, and Boatyard Bar & Grill, where you can enjoy fresh seafood while watching the boats go by.
Key Features:
- Excellent marinas and boat slips
- Horn Point Park with beautiful Spa Creek and Chesapeake Bay views
- Coastal top-notch dining and lively local MRE events
- Walkable to downtown Annapolis
Homes in Eastport range from stylish condos to elegant waterfront estates, many designed to reflect the area’s coastal charm. You’ll find a mix of shingled cottages, modern builds, and historic homes, all nestled in a walkable, welcoming neighborhood. Prices start around $900,000, with larger homes with private docks often going for over $7 million. Whether you’re a lifelong boater or just love that laid-back, salty-air lifestyle, Eastport’s mix of beauty, personality, and maritime magic is hard to beat.
Bay Ridge: A Quiet, Family-Friendly Coastal Retreat
Bay Ridge is a peaceful and upscale neighborhood tucked along the Chesapeake Bay, southeast of downtown Annapolis. It blends a strong sense of community with beautiful natural scenery and easy access to all of Annapolis.
Key Features:
- Private beaches and the Bay Ridge Marina
- Bay Ridge Pool & Tennis Club for fun and social events
- Plenty of trails, playgrounds, and park space for families
- A scenic golf course and conservation areas to explore
Bay Ridge feels like a year-round resort. As you drive into Bay Ridge, you're greeted with stunning views of the Chesapeake Bay, with sailboats dotting the water and sunlight dancing on the waves. The homes range from charming historic cottages from the 1800s to new custom-built estate homes, all with well-kept lawns and coastal-inspired architecture. Many homes include spacious decks, private pools, and inviting outdoor spaces perfect for relaxing or entertaining. With about 460 homes, there’s a nice mix of styles and sizes.
If you love being active outdoors, this is the place. You can walk or bike along shaded paths, play tennis or pickleball, splash in the pool, or relax on your own beach. Families love it here: kids play in safe parks and everyone gathers for community events organized by the Bay Ridge Civic Association. For boaters, the marina offers slips and easy access to the Bay. Quiet Waters Park is just a short drive away for kayaking and hiking. When you want dining or shopping, downtown Annapolis is an easy ride, with restaurants, boutiques, and cultural spots nearby.
Bay Ridge also neighbors a real gem: the Chesapeake Bay Foundation’s (CBF) headquarters, known as the Philip Merrill Environmental Center. Opened in 2001 on what used to be the Bay Ridge Inn property, the Merrill Center was the world’s first LEED Platinum–certified building, showcasing top-tier environmental design. The Merrill Center highlights the neighborhood’s values and commitment to keeping the Chesapeake Bay healthy for future generations.
Homes in Bay Ridge can cost between $1 million and over $7 million, with a median price around $2 million. A low yearly HOA (about $150–$250) helps maintain all the shared spaces while keeping the neighborhood feeling close-knit. Bay Ridge isn’t just a neighborhood, it’s a lifestyle. It’s the kind of place where neighbors know each other, kids ride bikes to the beach, and the sunsets over the Bay never get old. If you're dreaming of a friendly, coastal community with top-notch amenities and natural beauty, Bay Ridge might just be the perfect place to call home.
Downs on the Severn: A Fun Waterside Community
Nestled on a beautiful peninsula between Clements Creek and Brewer Creek, Downs on the Severn is a friendly, waterfront community in Annapolis, MD. At the Downs, neighbors wave hello, kids splash in the pool, and boats slide quietly out to the Chesapeake Bay. The Downs has 225 homes spread across 335 acres, giving everyone plenty of room and shoreline to enjoy.
The community was developed in the 1970s, but the land has a rich past that stretches back much further. Before it became a neighborhood, this area was a mix of farmland and dense forest along the Severn River. As Annapolis grew, Downs on the Severn was carefully planned to blend modern living with the beauty of the natural landscape. That’s why you’ll still find winding roads, mature trees, and stunning water views all around.
Everyone who lives here joins the Downs Property Owners Association, giving them access to fantastic amenities. There are two marinas, the Clements Creek Marina (with 76 boat slips!) and the Brewer Creek Marina. There is an outdoor pool, clubhouse, tennis and pickleball courts, and a playground, all great spots for fun and social gatherings. From Memorial Day through the end of July, the Downs Devilrays swim team, with about 85 swimmers, ages 4 to 18, practice and compete. It’s perfect for kids to make friends and stay active. After meets, families gather for pep rallies, potluck cookouts, and a big Summerfest awards party. There’s even a charitable swim‑a‑thon each year!
Around 830 residents call Downs home, and the median age is 60, with a healthy mix of families and retirees. Most of the homes are spacious and upscale, with beautiful waterfront views and direct access to the river. Properties in the Downs rarely stay on the market long! Current prices range from about $1 million to over $6 million.
Living here feels like being on vacation, but with all the comforts of home. It’s safe, scenic, lively, and calm all at once. Whether you're drifting along the river, cheering on a swim meet, or enjoying a quiet sunset by the marina, Downs on the Severn is the kind of community you’re excited to come home to.
West Annapolis & Wardour: A Historic, High-End Peninsula
West Annapolis and Wardour form one of the most elegant and storied neighborhoods in Annapolis. Just west of downtown and hugging the Severn River, this area blends waterfront luxury, historic charm, and a tight-knit community vibe.
This peninsula was part of large land grants starting in 1658, when John Norwood received 230 acres, later expanded by his son. The land was developed into the planned neighborhood of West Annapolis in the late 1800s. The Wardour section was replotted in the early 1900s. Notably, landscape architect Frederick Law Olmsted Jr., who designed the National Mall and other major sites, was brought in to design Wardour, giving it a refined layout with curving streets and sprawling lots.
This neighborhood pulses with friendly energy. The West Annapolis Civic Association (WACA) has been active since the early 1950s, protecting local history, organizing street-naming projects, and hosting community events like Cinco de Mayo, St. Patrick's Day 5K, and eco-friendly cleanups. But Oktoberfest steals the show in fall! Held every third Sunday in September on Annapolis Street, it’s West Annapolis’s biggest street party. Expect German food, local breweries (like RAR Brewing / Chessie’s Wharf), art vendors, live music, and a real family-friendly community buzz.
One of my personal favorites is a cozy breakfast and brunch spot beloved by locals: Evelyn’s, at 26 Annapolis St. Known for fresh, farm-to-table food (Weems Creek omelette, Cuban sandwich), it’s small (but has recently expanded into the space next door), but full of charm. Park nearby and enjoy the hometown feel and friendly staff. And yes, Evelyn is the owner’s daughter. The Bean Rush Cafe, at 112 Annapolis St, is a boutique coffee shop started by former yacht charter crew who wanted a local gathering spot. They serve excellent coffee, loose-leaf teas, salads, pastries, and sandwiches.
Tree-lined, winding streets, courtesy of Olmsted Jr.'s design, lead to spacious lots and large homes. The homes here range from picturesque Cape Cod and Colonial-style cottages built post-1940 to grand waterfront mansions along the Severn River. In Wardour, you’ll find some of Annapolis’s most prestigious estates, many with private docks and sweeping river views. While they showcase historic charm, most interiors have been refreshed with modern features, blending tradition with comfort.
If you’re drawn to a neighborhood that combines rich history, waterfront luxury, and welcoming community spirit, West Annapolis & Wardour stands out as one of Annapolis’s most prestigious (and warm) places to call home.
Considering a Move? Let Local Expert Jeff Lockard Guide You
With over 25 years of real estate experience, Jeff Lockard is not only a proud Annapolis resident but also a Senior Vice President at TTR Sotheby’s International Realty, having closed over $800 million in sales across the region. Whether you're buying your dream waterfront home, selling for top value, or relocating to the area, Jeff brings strategic insight, design expertise, and a deep knowledge of neighborhoods like Bay Ridge, Downs on the Severn, West Annapolis, Wardour, and Eastport . His clients appreciate his calm confidence, attention to detail, and genuine connection, and many return to him again and again. Are you ready to start your Annapolis journey? Contact Jeff today and experience a smooth, personalized real estate experience in a place he calls home.
