How to Choose the Right Neighborhood in Annapolis
Your Hyperlocal Guide to Annapolis Neighborhoods
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Your Hyperlocal Guide to Annapolis Neighborhoods 〰️
Finding Your Fit Beyond the House Itself
One of the biggest lessons I’ve learned as a REALTOR and as a mom raising my boys here in Annapolis is this: the neighborhood you choose shapes the rhythm of your life just as much as the house itself.
It’s the morning walks before work, school pickup lines, grocery trips to Graul’s, sunsets over the rivers off of the Chesapeake Bay, the laughter from kids riding bikes after dinner, and the neighbors who wave as you pull into the driveway.
Choosing where to live in Annapolis isn’t just a real estate decision.
It’s a lifestyle decision. It’s about how you want to feel when you come home.
If you’re exploring a move to Annapolis, this guide will help you identify the communities that best fit your values, your habits, and your next chapter.
Step One: What Matters Most to Your Family?
Before we zoom into specific neighborhoods, take a moment to reflect on what matters most to you. This is where clarity starts.
You may be considering:
• Walkability to downtown Annapolis or bike-friendly streets
• Access to marinas, beaches, or the Bay
• Neighborhood connection and community events
• Strong school district
• Proximity to the USNA, D.C., Baltimore, or Fort Meade
• Local parks, pools, and trails
• A calm, peaceful environment at the end of the day
When you’re clear on these, everything else falls into place.
Step Two: Understanding the Annapolis Area Landscape
The Annapolis area offers an incredible variety of communities — historic, coastal, family-focused, wooded, walkable, and water-privileged. There is truly something for everyone. Much of the feel of a particular neighborhood is guided by which of the five rivers that the neighborhood is located near or between: The Magothy River, The Severn River, The South River, The West River, and the Rhodes River.
Here’s a hyperlocal breakdown of the neighborhoods my clients ask about most often:
Annapolis Communities
West Annapolis & Homewood
Walkable, charming, village-like
West Annapolis has that small-town charm people fall in love with immediately. Boutique shops, leafy sidewalks, beloved local cafés, and a tight-knit community feel. It’s also incredibly convenient to downtown and the Naval Academy (especially the Stadium and its events).
Best for: Walkers, Navy-connected families, those who love historic character and neighborly energy.
Historic Downtown Annapolis & Murray Hill
Cobblestones, water views, and postcard-perfect charm
Downtown living means walking to dinner, watching boats in Ego Alley, and experiencing Annapolis traditions steps from your front door.
Best for: Those who want walkability, nightlife, and nonstop charm. Popular with retirees and second-home buyers.
Eastport
Laid-back, coastal, artsy, and spirited
Eastport marches to the beat of its own drum in the best way. Marinas everywhere, quirky personality, waterfront dining, and a true coastal lifestyle.
Best for: Boaters (sailors in particular), foodies, creatives, and anyone who wants a relaxed-but-lively vibe.
Bay Ridge
Waterfront living with resort-style community amenities
Bay Ridge is one of Annapolis’s most sought-after waterfront communities. With a marina, private beaches, a pool, clubhouse, walking paths, and year-round traditions, Bay Ridge offers that rare blend of luxury and laid-back Chesapeake lifestyle. Many of the original cottages have been renovated or replaced with stunning custom homes.
Best for: Water lovers, active families, anyone who dreams of a tight-knit community with stunning views.
Annapolis Cove
Serene, wooded, and water-privileged
Located right next to Bay Ridge, Annapolis Cove offers private marina access, quiet streets, beautiful homes, and a strong community feel. Residents love the balance of nature, privacy, and access to all the Bay Ridge amenities next door.
Best for: Families and professionals who want water access and tranquility in a social neighborhood
Fishing Creek Farm
Upscale, private, and beautifully situated on the water
A premier Annapolis neighborhood with sweeping water views from non-riparian (read: lower maintenance) waterfront lots, a community clubhouse, pool, kayak launch, and marina. The homes are spacious, refined, and designed for luxury living with nature at your doorstep.
Best for: Those wanting elegance, privacy, and high-end waterfront amenities with a custom feel. The marina is located in a convenient location at the mouth of the South River and offers a low-maintenance option for those that desire waterfront with the ability to lock-and-leave a vacation home.
Broadneck Peninsula Communities
Pleasant Plains
Water-privileged and almost rural
Pleasant Plains is a quiet, established neighborhood with deep-rooted Annapolis charm. Set among former farmland, the properties are large and estate-like. Residents enjoy water access on Broad Creek, Mill Creek, and Whitehall Creek, peaceful streets, and a friendly, down-to-earth community among some of the quietest large homes in the area.
Best for: Buyers seeking a private Annapolis lifestyle with water privileges and true Southern Charm
Arnold
Tree-lined, peaceful, and incredibly convenient
Arnold offers quick access to the B&A Trail, Broadneck Park, marinas, and top-rated schools. It’s central to everything while still feeling quiet and residential. Water privileged neighborhoods such as Ulmstead Estates and Shore Acres are coveted for their large lots and social activities, along with quick access to the Magothy River.
Best for: Families, commuters, and anyone who wants calm and convenience, with access to some of the best bike trails and water access in the area.
Cape St. Claire
Active, beachy, and full of personality
The Cape started as a weekend retreat for vacationers from Baltimore and DC and has turned into a wonderful community rich in year-round traditions. Original ranchers stand beside newer homes, and the neighborhood has several beaches, marinas, a pier, clubhouse, playgrounds, and community events traditions. It’s lively, engaged, and full of pride. There is a neighborhood shopping center that has everything you need from Graul’s Market to Ace Hardware, Bella’s Liquors and several restaurants. Many Capers are very loyal to their local small businesses and take pride in The Broadneck Peninsula.
Best for: Active families, beach-goers, and community-driven buyers looking for a combination of top-rated Broadneck schools and a variety of housing price-points.
Bay Hills, Deep Creek Village & Surrounding Communities
Accessible, scenic, and active
These neighborhoods offer quiet streets, neighborhood amenities , and strong community identity. Bay Hills offers a community pool, 18-hole Golf Club, and neighborhood shopping center (including popular O’Loughlin’s Pub and Restaurant). Homes are set on scenic lots, often backing up to the golf course. Deep Creek Village is a newer neighborhood comprised of both single-family homes and luxury townhomes, with walking paths and a vibrant community who hosts many annual events.
Best for: Buyers who want mature neighborhoods with nature and amenities, families looking to be in the Broadneck School District
Step Three: How Do You Want Your Days to Feel?
Choosing a neighborhood is choosing a lifestyle. Ask yourself:
Do I want to walk to the water?
Do I want kids biking through the neighborhood after school?
Do quiet evenings matter or do I love an active weekend vibe?
Do I want marinas, trails, or restaurants nearby?
Is a larger home or a larger lot more important to me?
Do I picture a historic home or something newer?
Step Four: Touring With Intention
When we explore neighborhoods together, I always encourage clients to look beyond the listings and trust what they feel.
Pay attention to:
• The vibe of the streets
• How well homes and yards are cared for
• Traffic patterns
• Walkability and community activity
• Noise levels
• Proximity to parks, water access, and local favorites
• The view from your future front porch
These details matter just as much as square footage.
Step Five: Let Local Insight Guide You
After raising my family here – football games, lacrosse practices, boat days on The Chesapeake Bay and Magothy River, trivia nights at the local pub, holiday markets, Christmas Lights on the Broadneck Peninsula — I can share the nuances that don’t show up on Google Maps.
Like:
• Which streets are quietest in each neighborhood
• Where traffic builds on school mornings
• Which communities have the best events
• Which marinas are easiest to get into
• Where kids gather after school
• Which neighborhoods are most walkable
• Where to find the best sunrise or sunset
This kind of insight helps buyers feel grounded and confident in their choice.
Ready to Explore Annapolis or Arnold?
If you're dreaming about a move, I would love to walk this journey with you. Neighborhood tours are one of my favorite ways to help clients feel informed, excited, and completely supported.