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320 Chester Avenue, Annapolis, MD 21403

$750,000
  • 320 Chester Avenue, Annapolis, MD 21403 Main Photo

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Contingent Price Reduced $29,000 on February 11th, 2026
BEDS2 BATHS2 full SQUARE FEET1,176 MLS#MDAA2128698
STATUSACTIVE UNDER CONTRACT PROPERTY TYPEResidential - Single Family SUBDIVISIONEASTPORT SCHOOLANNE ARUNDEL COUNTY PUBLIC SCHOOLS

Property Description

Rare opportunity to own a charming 2-unit building in the heart of Eastport, offering water views from both units. Each residence features its own private entrance and deck, perfect for enjoying the sights and sounds of small town living and serene surroundings. Thoughtfully designed, both units include a comfortable living area, full kitchen, spacious bedroom, full bath, and convenient in-unit laundry. Just a short walk to Historic Downtown Annapolis, this property is ideal for investors or enjoying one unit while renting the other. Experience the best of Eastport living—steps from restaurants, marinas, and the waterfront lifestyle. The downstairs is a licensed short-term rental, and the upstairs is a licensed long-term rental. May be subject to all future rentals.

320 Chester Avenue | MLS# MDAA2128698

This single family home located at 320 Chester Avenue, Annapolis, MD 21403 is currently listed for sale with an asking price of $750,000. This property was built in 1920 and has 2 bedrooms and 2 full baths with 1176 sq. ft. Chester Avenue is located in the EASTPORT subdivision within the ANNE ARUNDEL COUNTY PUBLIC SCHOOLS school district. Search EASTPORT real estate on www.countonrick.com today.

Property Features

Property Type: Residential - Single Family
Cooling: Wall Unit, Ceiling Fan(s)
Fuel Type: Electric
Heating: Wall Unit
Home Style: Colonial
Lot Size: 0.08 Acres
Stories: 2.0
Taxes: $9,345
Year Built: 1920

Feature Descriptions

Additional Structures: Above Grade, Below Grade
Appliances: Built-In Microwave, Dishwasher, Dryer, Oven/Range - Electric, Refrigerator, Washer
Exterior: Frame
Flooring: Wood, Ceramic Tile
Interior: Bathroom - Walk-In Shower, Ceiling Fan(s), Combination Dining/Living, Combination Kitchen/Dining, Combination Kitchen/Living, Entry Level Bedroom, Floor Plan - Traditional, Wood Floors,2nd Kitchen
Lot Dimensions: 0.08 Acre(S)
Municipality: Annapolis
Rooms: Living Room, Bedroom 2,Kitchen, Bedroom 1,Full Bath
Sewer: Public Sewer
SQFT Above Finished: 1176
SQFT Total Finished: 1176
Structure Type: Detached
Water: Public

Room Sizes

Living Room: 15 x 11 Level - Main
Kitchen: 8 x 6 Level - Main
Bedroom 1: 12 x 11 Level - Main
Living Room: 14 x 12 Level - Upper 1
Kitchen: 11 x 8 Level - Upper 1
Bedroom 2: 15 x 9 Level - Upper 1

Local Schools

School District: ANNE ARUNDEL COUNTY PUBLIC SCHOOLS

Listed By / Shown By

Listed By

Agency Name: Long & Foster Real Estate, Inc.
Agency Phone: 4102244999

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Estimated Payment

$ 2,666.67 per month $1,669.17 Principal & Interest $778.75 Property Tax $218.75 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 03/04/2026. The listing information on this page last changed on 03/04/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Wed 03/04/2026 12:04:59 AM EST) or Bright MLS (last updated Tue 03/03/2026 11:58:15 PM EST). Real estate listings held by brokerage firms other than Berkshire Hathaway HomeServices Homesale Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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