320 Chester Avenue, Annapolis, MD 21403 - Photo 1

1/1

$725,000

Sold
Closed
Single Family
2 Beds
2 Full Baths
1,176 Sq. Ft.
Updated 9 hours ago

1/1

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.

Full Property Details

Full Property Details for 320 Chester Ave

General

Sold For: $725,000
Taxes: $9,345 (2024)
Status: Closed
Type: Single Family
Source: BrightMLSMidAtlantic
MLS ID: MDAA2128698
Added to Site: 142 day(s) ago

Interior

Rooms/Areas: Living Room, Bedroom 2, Kitchen, Bedroom 1, Full Bath
Interior Features: 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
Appliances: Built-In Microwave, Dishwasher, Dryer, Oven/Range - Electric, Refrigerator, Washer
Flooring: Wood, Ceramic Tile

Rooms

Bathrooms

Total Bathrooms: 2
Full Bathrooms: 2
Upper Floor Baths: 1
Upper - Full Baths: 1
Main Floor Baths: 1
Main - Full Baths: 1

Bedrooms

Total Bedrooms: 2
Bedrooms Upper: 1
Bedrooms Main & Up: 1

Other Rooms

Laundry: Washer In Unit, Dryer In Unit, Main Floor, Upper Floor

Exterior

Porch/Patio/Deck: Deck(s)

Parking

Parking Type: On Street

Location

Municipality: Annapolis
County: ANNE ARUNDEL
Subdivision: EASTPORT
Driving Directions: 6th Street to Chester Avenue.
City Limits: Yes

School Information

School District: Anne Arundel County Public Schools
Elementary School: Call School Board
Middle School: Call School Board
High School: Call School Board

Heating & Cooling

Cooling Type: Wall Unit, Ceiling Fan(s)
Cooling Fuel: Electric
Heating Type: Wall Unit
Heating Fuel: Electric
Water Heater: Electric

Utilities

Sewer: Public Sewer
Water: Public

Structural Information

Architectural Style: Colonial
Structure Type: Detached
Construction: Frame
Foundation: Crawl Space
Stories Description: Main, Upper 1
Square Feet: 1,176
Sq. Ft. Source: Assessor
Living Area: 1,176 Sq. Ft.
Finished Above Grnd: 1,176 Sq. Ft.
Year Built: 1920
Year Built Source: Assessor

Lot Features

Lot Size (Acres): 0.08
Lot Size (Sq. Ft.): 3,571
Lot Size Source: Assessor
Zoning: R

Financial Considerations

Price Per Sq. Ft.: $637.76
Assessment Year: 2025
City/TownTax: $4,799
City/TownTax Freq: Annually
County Tax: $4,546
County Tax Freq: Annually
Tax w/Assessment: $721,900
Tax Amount: $9,345
Tax Year: 2024
Terms: Standard Sale
Tax Total Finished Sq. Ft.: 1176

Disclosures and Reports

Ownership: Fee Simple

Listed by Long & Foster Real Estate, Inc., John J Collins
Sold by TTR Sotheby's International Realty, Michele Deckman

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Listing agent

— 320 Chester Ave —

John J Collins

Long & Foster Real Estate, Inc.

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Schools

Schools serving 320 Chester Ave

School District:Anne Arundel County Public Schools

Name	Grades	Distance
Eastport Elementary School 420 Fifth Street, Annapolis, MD 21403	PK-5	0.2 mi
Annapolis Middle School 1399 Forest Drive, Annapolis, MD 21403	6-8	1.9 mi
Annapolis High School 2700 Riva Road, Annapolis, MD 21401	9-12	4.6 mi

Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 320 Chester Ave

Date

Details

Price

Change

Source

3/16/2026

Sold

$725,000

-3.33%

MLS

2/11/2026

Price Reduced

$750,000

-3.72%

MLS

10/27/2025

Listed

$779,000

—

MLS

Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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320 Chester Avenue, Annapolis, MD 21403 (MLS# MDAA2128698) is a Single Family property that was sold at $725,000 on March 16, 2026. Want to learn more about 320 Chester Avenue? Do you have questions about finding other Single Family real estate for sale in Annapolis? You can browse all Annapolis real estate or contact a Coldwell Banker agent to request more information.

320 Chester Ave Annapolis, MD 21403