Let's Connect
320 CHESTER AVENUE
320 CHESTER AVENUE
320 CHESTER AVENUE
320 CHESTER AVENUE
320 CHESTER AVENUE
320 CHESTER AVENUE
320 CHESTER AVENUE
320 CHESTER AVENUE
320 CHESTER AVENUE
320 CHESTER AVENUE
320 CHESTER AVENUE
320 CHESTER AVENUE
320 CHESTER AVENUE
320 CHESTER AVENUE
320 CHESTER AVENUE
320 CHESTER AVENUE
320 CHESTER AVENUE
320 CHESTER AVENUE
320 CHESTER AVENUE
320 CHESTER AVENUE
320 CHESTER AVENUE
320 CHESTER AVENUE
320 CHESTER AVENUE
320 CHESTER AVENUE
320 CHESTER AVENUE
320 CHESTER AVENUE
320 CHESTER AVENUE
320 CHESTER AVENUE
320 CHESTER AVENUE
320 CHESTER AVENUE
320 CHESTER AVENUE
320 CHESTER AVENUE
320 CHESTER AVENUE
VIEW PHOTOS
$725,000

320 CHESTER AVENUE

2 Beds 2 Baths 1,176 Sq.Ft. 3,571 Sq.Ft.

Inquire Now

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.

Share Property

Location

320 CHESTER AVENUE, ANNAPOLIS, MD 21403

Status

Sold

Date Sold

March 16, 2026
Michele Deckman in a light blue blazer, posed outdoors against leafy greenery.

Michele Deckman

TITLE

Real Estate Advisor

PHONE

(410) 353-3703

EMAIL

[email protected]

CONTACT AGENT

Property Amenities

Interior
Laundry room Washer In Unit, Dryer In Unit, Main Floor, Upper Floor
Appliances Built-In Microwave, Dishwasher, Dryer, Oven/Range - Electric, Refrigerator, Washer
Flooring Wood, Ceramic Tile
Total Bedrooms: 2
Full Bathrooms: 2
Other 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
Area & Lot
Total area 1,176 Sq.Ft.
Lot Area 3,571 Sq.Ft.
Living area 1,176 Sq.Ft.
MLS® ID MDAA2128698
Year Built 1920
School District ANNE ARUNDEL COUNTY PUBLIC SCHOOLS
High School CALL SCHOOL BOARD
Middle School CALL SCHOOL BOARD
Elementary School CALL SCHOOL BOARD
Architecture Styles Colonial
Type Residential
Status Sold
Exterior
Stories 2
Pool No Pool
Air conditioning Wall Unit, Ceiling Fan(s)
Heat type Wall Unit
Disability Features None
Water Source Public
Sewer Public Sewer
Parking On Street
Finance
Sales Price $725,000
Real Estate Tax $9,345 yearly

360 Virtual Tour

Take a tour of this property

Browse My Active Listings

For Sale

1024 COLLEGE PARKWAY E
$1,000

1024 COLLEGE PARKWAY E, ANNAPOLIS, MD 21409

For Lease

322 NORTH DRIVE
$7,000/mo

322 NORTH DRIVE, SEVERNA PARK, MD 21146

  • 5 BEDS
  • 5 BATHS
  • 4,734 Sq.Ft.
View All

Annapolis

Aerial view of Annapolis Harbor, marinas, waterfront homes, and a sailboat on Chesapeake Bay.
Explore the Area

Your Trusted Agent, Ready to Help

Whether you're buying your first home, searching for your dream property, or preparing to sell, I'm here to guide you every step of the way. With deep local knowledge, a client-first mindset, and proven expertise in the Annapolis luxury market, I’m committed to making your real estate journey smooth, successful, and stress-free.

Let's Connect
Follow Me on Instagram

Get in Touch

White kitchen with a large island, brass fixtures, stainless steel appliances, and warm wood flooring.

Contact Details

Michele Deckman

410.353.3703
[email protected]

209 Main St Annapolis MD 21401