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For Sale

209 Main St

209 Main St, Annapolis, MD 21401

First settled in the 17th Century, Annapolis served as the capital of the United States from 1783 – 1784. It currently serves as the capital of Maryland and is home to the county government seat of Anne Arundel County. Annapolis is located on the Western Shore of the central Chesapeake Bay and is the location of Maryland’s only Bay Bridge. The city is home to 2 major universities including the United States Naval Academy and St. John’s College. With deep historical roots, Annapolis has been a thriving city for over 300 hundred years. Ideally situated east of I-95 and midway between Washington D.C and Baltimore, Annapolis is home to a variety of public and private employers in government, technology, defense, and services industries to name a few. The recent expansion of Class A multifamily housing in Annapolis has transformed the community from a C-Suite bedroom community to an ideal location for attracting employees who value a suburban – urban lifestyle along the banks of the Chesapeake. Main Street in Annapolis stands as the beating heart of the city, a vibrant thoroughfare full of energy. Its allure lies not only in its architectural charm but also in the diverse array of experiences it offers to those who wander its bustling sidewalks. Amidst the historic facades and bustling storefronts, one can embark on a culinary adventure, with an abundance of restaurants catering to every palate, from quaint cafes and ice cream shops to upscale f ine dining. Main Street is not just a haven for food enthusiasts; it is also a shopper’s paradise, boasting an eclectic mix of boutiques, galleries, and specialty stores that beckon with their unique wares and artisanal offerings. Whether in search of a one-of-a-kind piece of artwork or the perfect souvenir to commemorate a visit to Annapolis, Main Street promises to delight even the most discerning of shoppers.One of a kind opportunity to purchase a two-story retail and office building on Main Street in the heart of the Historic District and Downtown Annapolis. Both tenants have several years of lease term remaining, but second floor office tenant has LL exclusive termination option, for a prospective business owner to purchase, exercise, and move to occupy the space.

Key features

  • ±30 ft of Frontage on Main Street
  • One-of-a-kind opportunity to acquire a prominent 2-story building in the heart of Downtown Annapolis
  • Owner user or investment opportunity
  • Thoughtfully designed & well-maintained building once awarded an “Excellence in Architecture” citation by AIA-Chesapeake Bay Chapter
  • Within short walking distance to the new state-of-the-art public parking garage
  • Within steps of numerous restaurants, shops, hotels, US Naval Academy, Maryland State House, Circuit Court, St. John’s College & the beautiful Annapolis Waterfront.
Want more info on this listing?

Reach out to the broker for more info on lease terms and amenities

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Contacts

broker
Cecil Cummins

Hyatt Commercial

Building Details

  • For Sale Subject To Offer
  • Property Type Retail - Street Retail
  • Property Size 6,878 SF
  • Units 3
  • Lot Size 0.05 Acre
  • Property Tenancy Multi-Tenant
  • Building Class C
  • Date Updated May 15, 2026

Getting Around

  • Walk Score ®

    Walker's Paradise (96)
  • Transit Score ®

    Some Transit (44)
  • Bike Score ®

    Bikeable (62)
Powered by Walk Score ®

Location

  • City Annapolis, MD
  • Zip Code 21401
  • Market Baltimore
  • Map
  • Street

Points of Interest

BP

0.31 miles

Shell

0.62 miles

Blink

0.97 miles

Carroll Fuels

1.14 miles

Oceanic

1.18 miles

NEX Gas Station

1.58 miles

Citgo

1.70 miles

Sunoco

1.75 miles

Carroll Motor Fuels

1.81 miles

Gotts Court Parking Facility

0.20 miles

Whitmore Garage

0.27 miles

Marriot Hotel Valet Parking

0.32 miles

Annapolis Yacht Club Parking

0.37 miles

Knighton Parking Garage

0.45 miles

Gold Lot E

0.94 miles

Blue Lot A

0.99 miles

Gold Lot C

0.99 miles

Blue Lot B

1.01 miles

Navy Exchange

1.69 miles

Safeway

1.78 miles

Annapolis International Market

1.92 miles

Giant

2.05 miles

Kohl's

2.43 miles

Lidl

2.47 miles

Whole Foods Market

2.61 miles

Target

2.67 miles

Trader Joe's

2.72 miles

209 Main St Listing Summary

  • What is the asking price at 209 Main St?

    The asking price for 209 Main St is currently available on demand. Contact the listing broker for details.

  • What is the total size of 209 Main St?

    209 Main St has a total of 6,878 square feet.

Contact Listing Broker
broker
Cecil Cummins

Hyatt Commercial

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