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320 Chester Ave, Annapolis, MD 21403
320 Chester Ave, Annapolis, MD 21403
Sold for $725,000
320 Chester Ave, Annapolis, MD 21403
Sold for $725,000
320 Chester Ave, Annapolis, MD 21403
320 Chester Ave, Annapolis, MD 21403
320 Chester Ave, Annapolis, MD 21403
320 Chester Ave, Annapolis, MD 21403

320 Chester Ave Annapolis, MD 21403

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$725,000

CLOSED
Beds
2
Baths
2
Sqft
1,176
Acres
0.08
Year
1920
Close Date
Mar 16, 2026
Property Type
Residential
Sub Type
Per Square Foot
$616
Date Listed
Oct 27, 2025

Description of 320 Chester Ave, Annapolis, MD 21403

Listing details for 320 Chester Ave, Annapolis, MD 21403 : 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.
Listing Updated : 10-11-2026 at 3:34 AM EDT
Listing Provided By : John J Collins, 4106936000, [email protected], Long & Foster Real Estate, Inc.

Properties displayed may be listed or sold by various participants in the MLS

Source :

Bright MLS, MLS#: MDAA2128698

What's this home worth?

National portals guess with an algorithm. We price it from actual closed sales on your street.

Your home value estimate
$559K – $911K
Exact number$2,845,000

Want an exact number? Use an Agent, not an algorithm.

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Claim it to unlock a private owner dashboard, track your equity, and get a free monthly value report.

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What's this home worth?

National portals guess with an algorithm. We price it from actual closed sales on your street.

Your home value estimate
$559K – $911K
Exact number$2,845,000

Want an exact number? Use an Agent, not an algorithm.

Is this your home?

Claim it to unlock a private owner dashboard, track your equity, and get a free monthly value report.

Property History

DateEventPrice
3/16/2026
Sold
$725,000
$616/sqft
Source:Bright MLS #MDAA2128698
10/27/2025
Listed for sale
—
Source:Bright MLS #MDAA2128698
8/22/2016
Sold
$550,000 0%
$468/sqft
Source:Bright MLS #1001298191
8/22/2016
Sold
$550,000
$468/sqft
Source:Bright MLS #1001298945
3/30/2016
Listed for sale
—
Source:Bright MLS #1001298945
3/28/2016
Listed for sale
—
Source:Bright MLS #1001298191

Location of 320 Chester Ave, Annapolis, MD 21403

Streetview of 320 Chester Ave, Annapolis, MD 21403

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What's this home worth?

National portals guess with an algorithm. We price it from actual closed sales on your street.

Your home value estimate
$559K – $911K
Exact number$2,845,000

Want an exact number? Use an Agent, not an algorithm.

Is this your home?

Claim it to unlock a private owner dashboard, track your equity, and get a free monthly value report.

Comments

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No comments yet. Add the first note about this listing.

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The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 Bright MLS, Inc.
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