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$779,000

  • For Sale
  • Active
  • Single Family
  • 2 Beds
  • 2 Full Baths
  • 1,176 Sq. Ft.
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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 for 320 Chester Ave

General

  • Price: $779,000
  • Taxes: $9,345 (2024)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDAA2128698
  • Updated: 12/17/2025
  • Added to Site: 80 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.: $662.41
  • 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
  • Tax Total Finished Sq. Ft.: 1176

Disclosures and Reports

  • Ownership: Fee Simple

Listed by Long & Foster Real Estate, Inc., John J Collins

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Listing agent

— 320 Chester Ave —

  • John J Collins

    Long & Foster Real Estate, Inc.

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 320 Chester Ave

School District:Anne Arundel County Public Schools
NameGradesDistance
Eastport Elementary School
420 Fifth Street, Annapolis, MD 21403
PK-50.2 mi
Annapolis Middle School
1399 Forest Drive, Annapolis, MD 21403
6-81.9 mi
Annapolis High School
2700 Riva Road, Annapolis, MD 21401
9-124.6 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 320 Chester Ave Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/27/2025
Listed
$779,000
41.64%
MLS
8/22/2016
Sold
$550,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 320 Chester Ave

Year
Property Taxes
Change
Tax Assessment
Change
2025
$10,345
24%
$721,900
11%
2023
$8,310
—
$650,300
12%
2023
$8,310
3%
$578,700
1%
2022
$8,039
4%
$570,567
1%
2018
$7,710
-1%
$562,433
1%
2021
$7,816
—
$554,300
—
2020
$7,821
1%
$554,300
—
2019
$7,710
5%
$554,300
-1%
2018
$7,316
8%
$560,600
8%
2017
$6,780
9%
$517,967
9%
2016
$6,241
9%
$475,333
10%
2015
$5,733
—
$432,700
—
2014
$5,759
—
$432,700
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 320 Chester Ave

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Listed by Long & Foster Real Estate, Inc., John J Collins

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320 Chester Avenue, Annapolis, MD 21403 (MLS# MDAA2128698) is a Single Family property with 2 bedrooms and 2 full bathrooms. 320 Chester Avenue is currently listed for $779,000 and was received on October 27, 2025. 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.

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