Downtown Annapolis

Bridging the gap between heritage and modernity, Downtown Annapolis is perfect for homebuyers who are looking for a captivating coastal environment, a multi-faceted lifestyle, and a connected community. Before you embark on your home buying journey, here’s your complete guide to buying Downtown Annapolis real estate.

About Downtown Annapolis, MD

Annapolis is a city that shows the fruits of the nation’s centuries-long history and development. Situated at the mouth of the Severn River on the Chesapeake Bay, the city is just 25 miles south of Baltimore and 30 miles east of Washington, D.C., placing residents and businesses at the heart of activity in the Mid-Atlantic region. 

Downtown Annapolis, located between Church Circle and the City Dock, serves as the city’s epicenter. From its electrifying nightlife to its awe-inspiring art galleries and museums, this neighborhood is considered the ideal launching point to explore all the best that the city has to offer. 

A cradle of American history

Founded in 1649, Annapolis holds a significant place in American history as the seat of the Confederation Congress, formerly known as the Second Continental Congress. It also briefly served as the capital of the United States from 1783 to 1784, where General George Washington made his landmark resignation as commander of the Continental Army. 

The city also played a pivotal role in the 1786 Annapolis Convention, issuing a historic call for states to send delegates to the Constitutional Convention held the following year in Philadelphia. And, more recently, the Annapolis Peace Conference in 2007 added another layer to its storied legacy.

The Sailing Capital of the U.S.

Because of its prime location along the Chesapeake Bay, Annapolis was a strategic port and economic center early in its history. Today, it remains a popular destination for sailors and boating enthusiasts, housing a number of world-class facilities and institutions such as the Annapolis Yacht Club, the Annapolis Waterfront and Sailing Center, and the U.S. Naval Academy Sailing Center. It also hosts a number of major sailing events and competitions each year.

Even if you’re not a sailor, Downtown Annapolis offers a wealth of fun activities. You can stroll along its waterfront promenade, watch sailboats parade down Ego Alley, or walk across Spa Creek bridge to Eastport, where you can find additional art galleries, waterfront dining destinations, and captivating views of Downtown Annapolis.

The Downtown Annapolis real estate market

Thanks to its coastal-urban and historic character, Downtown Annapolis is home to some of the most desirable properties in the region. Here’s what you can expect as a homebuyer:

A lively bayfront neighborhood

Given its coastal location, walkability, and proximity to the water, Downtown Annapolis exudes a distinctive nautical atmosphere where residents can immerse themselves in picturesque seaside views and the sounds of the harbor. Its proximity to higher educational institutions like United States Naval Academy (USNA) and St. John’s College also makes it a popular neighborhood for college students.

Versatile property types and unique architecture

Downtown Annapolis real estate primarily consists of small to medium-sized properties, such as studio to two-bedroom apartments, townhomes, and larger three to four-bedroom homes. Whether you’re a young professional, a couple, or a parent with a growing family, this neighborhood has the right kind of home for you. 

Moreover, most of Downtown Annapolis is part of the Colonial Annapolis Historic District. So, you’ll find that many residential properties typically date back to 1939 or earlier. Its rich history is reflected in its architecture as well, from Eastport Bungalows and Cape Cod homes to Arts & Crafts, English Cottage, Dutch Colonial, Federal, and Georgian-style properties. Greek Revival architecture can also be seen in public buildings like The Maryland State House.

High investment potential

The Annapolis real estate market consistently experiences strong demand. Property values in the city have appreciated by an impressive 157.75% since 2000, with an annual average rate of 4.16%.

This means that when you buy a home in Downtown Annapolis, you are not only securing a home; you’re also making a smart investment for the future. With property values steadily rising, you can expect your investment to gain equity over time. Moreover, the robust demand for homes in this downtown area ensures that your property will remain highly sought after, offering lucrative opportunities for resale or rental income.

Life in Downtown Annapolis

From stellar educational options to colorful events and festivals, there are many reasons why living in Downtown Annapolis is an exceptional choice for young professionals, families, and retirees. Here’s what you can expect in this dynamic neighborhood: 

Getting around

Annapolis is less than an hour from Washington, D.C. and Baltimore, and only about two hours from Philadelphia, which is perfect for those who want convenient access to major metropolitan areas. The Baltimore-Washington International Thurgood Marshall Airport (BWI) – a 35-minute drive away from Downtown Annapolis – offers convenient domestic and international flights, while Washington National and Dulles International Airports are both within an hour’s reach, ensuring hassle-free air travel options for residents.

Going around within the city is easy as well, whether it’s by bus, car, bike, or even on foot. Main Street and West Street, Annapolis’ busiest thoroughfares, are lined with various boutiques, restaurants, bars, and historic sites. Downtown Annapolis is known for being pedestrian-friendly, so it’s great for those who appreciate a walkable lifestyle, with charming streets designed for leisurely strolls. 

Top-quality education

Annapolis is served by the Anne Arundel County Public Schools system, which boasts a remarkable track record with 18 National Blue Ribbons, 21 Maryland Blue Ribbons, and several nationally acclaimed programs. The district ranked as the third-best school district in the Baltimore area in 2023, according to Niche.com.

Downtown Annapolis also offers a range of exceptional private schools catering to various educational preferences. These include St. Anne’s School of Annapolis, Aleph Bet Jewish Day School, Annapolis Area Christian School, St. Martins Lutheran School, Severn School, St. Mary’s High School, and Indian Creek School. 

For those pursuing higher education, Downtown Annapolis is home to two distinguished universities:

• United States Naval Academy (USNA). This federal service academy educates and trains officers for the United States Navy and Marine Corps. Established in 1845, this historic campus sits right on the banks of the Severn River. Its comprehensive academic programs ensure that graduates are commissioned as officers in the Navy or Marine Corps, and many achieve some of the highest starting salaries in the country.
• St. John’s College. This private liberal arts college is located within the historic district of Annapolis. With its unique Great Books curriculum – which involves an interdisciplinary exploration of books pning millennia – St. John’s prepares students for diverse fields, including law, government, research, STEM, media, and education. It is the third-oldest college in the United States and is hailed as one of the most forward-thinking institutions in America.

Numerous shopping and dining options

Downtown Annapolis offers the ultimate live, play, work lifestyle with its plethora of shopping and entertainment options.

• Shopping at Main Street. This lively street is home to an enticing array of shops, restaurants, and bars. Locally-owned boutiques like Lilac Bijoux and Local By Design Downtown offer a delightful shopping experience, while cafés and ice cream parlors like the

  Annapolis Ice Cream Company ensure that your taste buds are in for a treat.

• Meet with friends at the Annapolis Town Center. This entertainment-focused, mixed-use destination seamlessly blends retail, dining, residential, and office spaces. Designed to foster a sense of community, this central gathering place offers abundant opportunities to unwind and engage, whether it’s going for a wine tasting session at Cooper’s Hawk Restaurant or a girls’ night out at Muse Paintbar. 
• Go on a food trip along West Street. Stretching 2.5 miles from Church Circle to Solomons Island Road, this stretch includes not only national fast food chains but also over a dozen unique local restaurants. From Italian dishes at Luna Blu to Thai cuisine at Lemongrass, West Street offers a diverse range of culinary treasures.
• Explore Eastport. Take a scenic water taxi ride from City Dock or stroll across the Spa Creek Bridge to experience the laid-back charm of Eastport, Annapolis’ maritime district. Here, you can explore street-end parks by the water or immerse yourself in the watermen’s heritage at the Annapolis Maritime Museum. Eastport is also renowned for its “Restaurant Row,” which houses the best seafood restaurants and steakhouses in the area.

Various outdoor recreational activities

For those who love to bask in the beauty of the outdoors, Downtown Annapolis offers a plethora of parks and recreational areas:

• The Annapolis City Dock is where the city connects with the Chesapeake Bay, offering its residents a variety of water-related activities. Here you can watch boats parade around the turning basin of Ego Alley, go on a tour with the Harbor Queen, or take the helm of the Schooner Woodwind. It is also home to a range of excellent waterfront establishments. City Dock hosts major events throughout the year as well, making it a hub of activity and entertainment.
• The People’s Park. Open from dawn to dusk, this beautiful park is a peaceful place to enjoy the outdoors and reflect on its rich history. It is best known for housing the Dr. Martin Luther King Foot Soldiers Memorial, a tribute to the attendees of the historic March on Washington in 1963. 
• Truxtun Park is the crown jewel of Annapolis’ city parks, pning over 80 lush acres with  hiking trails, a skate park, picnic areas, and two playgrounds for children. Sports lovers will find plenty to do with 12 tennis courts, three baseball fields, and five basketball courts. If you’re a boating enthusiast, you’ll appreciate the public boat ramp. The park is also home to the Roger W. Pip Moyer Recreation Center, where you can enjoy indoor rock climbing, an indoor Ballocity™ playground for kids, playing courts, and a four-lane walking/jogging track.
• South Annapolis Yacht Centre (SAYC) is an exclusive in-town destination marina that offers 74 annual and transient slips. Nestled along Spa Creek in the historic Eastport neighborhood, SAYC can house yachts and vessels up to 135 feet. A short walk or water taxi ride from here takes you to downtown Annapolis, City Dock, and the Annapolis Harbor. 
• Jonas and Anne Catherine Green Park, located at the southern terminus of the Baltimore & Annapolis Trail, offers a serene location on the Severn River. It features a sandy beach for cartop boat launching, a 288-foot fishing pier, picnic tables, and restrooms. The park is also handicap accessible, making it an ideal spot for fishing, picnicking, and soaking up the river’s beauty for people of diverse needs.
• The Greenbury Point Conservation Area is a Navy-managed conservation area that has become a popular destination for nature lovers, runners, and hikers. While it’s open to the public when safe, please note that it can close without prior notification due to its critical role in NSA Annapolis’ mission. When military or navy training is not ongoing, you can enjoy scenic hikes and peaceful strolls, taking in the natural beauty that surrounds you.

A rich history and culture

Whether you’re an art enthusiast or a history buff, Downtown Annapolis boasts an array of museums, galleries, and historical sites that will captivate your imagination. Here’s a glimpse into the neighborhood’s vibrant arts and culture scene:

• Mitchell Art Museum at St. John’s College. Located within the St. John’s College campus, the Elizabeth Myers Mitchell Art Museum offers changing exhibitions that encourage deep engagement and open-ended conversations about the human experience through art. As one of only five nationally accredited visual arts museums in Maryland, it’s a hidden gem that welcomes over 10,000 visitors each year.
• Banneker-Douglass Museum, named after Benjamin Banneker and Frederick Douglass, this museum is a testament to Annapolis’ rich African American heritage. Housed in the historic Mount Moriah African Methodist Episcopal Church, which dates back to 1874, this community-based museum focuses on building collections, exhibitions, and public programs rooted in community contributions. 
• The Maryland Federation of Art (MFA) has been creating connections in the community for decades. Founded in 1963, MFA is Maryland’s oldest artist-run organization. It established the iconic Circle Gallery located along the State Circle (which houses 12 exhibitions a year), and utilizes various alternate sites to provide the public with opportunities to appreciate and learn from artists of all backgrounds at all stages of their careers. 
• Maryland State House allows you to step back in time to America’s first peacetime capitol. Completed in 1779, the Maryland State House is the oldest state house still in legislative use. It has witnessed many pivotal moments in American history, including George Washington’s resignation as commander-in-chief and the ratification of the Treaty of Paris. Today, it serves as the home of the Maryland General Assembly and is open to the public everyday. 

Year-round events and festivals

When you call Downtown Annapolis home, you become part of a vibrant community that knows how to celebrate life. From historical reenactments to soul-stirring music festivals, here are some of the exhilarating events that await you:

• Kunta Kinte Heritage Festival. Named after Kunta Kinte, who arrived in Annapolis in 1767, this festival is a testament to the enduring spirit and cultural heritage of Africans, African Americans, and Caribbean people of African descent. The festival features live music, African art and jewelry, dance performances, a comedy show, and even a fashion show. There is also a Remembrance ceremony and enlightening lectures on genealogy, gardening, and more. 
• Annapolis Boat Shows. Every October, the Annapolis City Dock undergoes a maritime transformation for the Powerboat and Sailboat Shows. Here thousands of boaters and enthusiasts gather to explore the latest boat models, maritime tech, and boating products, as well as showcase some of the world’s most impressive sailboats, motor yachts, trawlers, fishing vessels, and more
• Annapolis Jazz & Roots Festival. This two-weekends-long celebration of jazz, blues, and more features an impressive lineup of world-class international and regional artists. Set against the charming backdrop of Eastport, the festival offers the best of Flamenco Jazz, Pop, Rock, and Chesapeake Bay Songs & Sea Chanteys, as well as various lectures and workshops for music lovers, history enthusiasts, and anyone interested in Annapolis’s rich musical heritage.
• Spring Sailboat Show. Serving as a prologue to the US Boat Shows in October, the Spring Sailboat Show – held every April – showcases catamarans, monohulls, racing boats, and more than 100 new and brokerage yachts. It’s the perfect opportunity to explore vessels and shop for the latest boating gear, from electronics to clothing. The show also offers hands-on workshops at Cruisers University, providing insights into boat maintenance, navigation, and more.
• May Day in Annapolis. Every first day of May, the city transforms into a colorful tapestry of blossoms and blooms. It is a tradition that goes all the way back to 1956, in which local businesses and homes adorn their front doors and gates with fresh-cut flowers, with some even joining in a friendly May basket competition. This annual beautification, sponsored by the Garden Club of Old Annapolis Towne, brings joy and beauty to the city, welcoming springtime with open arms.

Discover Downtown Annapolis real estate today!

Explore the heart of Annapolis with Jen Schaub, your dedicated real estate partner. With years of experience and a deep-rooted connection to this remarkable area, Jen is more than just a Realtor – she’s your local guide, trusted advisor, and your advocate in this competitive  real estate market.

Ready to take that first step towards your dream home in Downtown Annapolis? Get in touch with Jen by calling 720.244.5945 or by sending her an email. You can also reach out to her by sending a message here!