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.
Sold for $725,000
$725,000
320 Chester Ave, Annapolis, MD 21403
2beds
1,176sqft
Single Family Residence
Built in 1920
3,571 Square Feet Lot
$730,300 Zestimate®
$616/sqft
$2,965 Estimated rent
Home value
$730,300
$679,000 - $781,000
$2,965/mo
Zestimate® history
Owner options
List your home for rent
$2,965/mo
Rent Zestimate®
Find your next renter with Zillow Rental Manager. Plus, with online applications, you can quickly screen prospective tenants – for free.
$2,965/mo
Rent Zestimate®
Refinance and save
$4,291/mo
Est. payment
Refinancing to a lower rate could help reduce your monthly payments and save thousands over the life of the loan.
$4,291/mo
Est. payment
Explore your selling options
Work with a Zillow partner agent
Leverage their expertise and Zillow's premium Showcase listings to get your home seen by more buyers.
Get startedList with your own agent
Get your home in front of millions of buyers by listing it on Zillow.
Learn how to do itSell it yourself
Take full control of how buyers see your home on Zillow by listing For Sale by Owner (FSBO).
List your homeWhat's special
Private entranceConvenient in-unit laundryFull kitchenWater viewsSpacious bedroom
Zillow last checked:
Listing updated:
Listed by:
John Collins 410-693-6000,
Long & Foster Real Estate, Inc.
Bought with:
Michele Deckman, 669296
TTR Sotheby's International Realty
Source: Bright MLS,MLS#: MDAA2128698
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 2
- Full bathrooms: 2
- Main level bathrooms: 1
- Main level bedrooms: 1
Bedroom 1
- Level: Main
- Area: 132 Square Feet
- Dimensions: 11 X 12
Bedroom 2
- Level: Upper
- Area: 135 Square Feet
- Dimensions: 9 X 15
Other
- Level: Main
Other
- Level: Upper
Kitchen
- Level: Main
- Area: 48 Square Feet
- Dimensions: 6 X 8
Kitchen
- Level: Upper
- Area: 88 Square Feet
- Dimensions: 8 X 11
Living room
- Level: Main
- Area: 165 Square Feet
- Dimensions: 11 X 15
Living room
- Level: Upper
- Area: 168 Square Feet
- Dimensions: 12 X 14
Heating
- Wall Unit, Electric
Cooling
- Wall Unit(s), Ceiling Fan(s), Electric
Appliances
- Included: Microwave, Dishwasher, Dryer, Oven/Range - Electric, Refrigerator, Washer, Electric Water Heater
- Laundry: Washer In Unit, Dryer In Unit, Main Level, Upper Level
Features
- Bathroom - Walk-In Shower, Ceiling Fan(s), Combination Dining/Living, Combination Kitchen/Dining, Combination Kitchen/Living, Entry Level Bedroom, Floor Plan - Traditional, 2nd Kitchen
- Flooring: Wood, Ceramic Tile
- Has basement: No
- Has fireplace: No
Interior area
- Total structure area: 1,176
- Total interior livable area: 1,176 sqft
- Finished area above ground: 1,176
- Finished area below ground: 0
Property
Parking
- Parking features: On Street
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: None
Features
- Levels: Two
- Stories: 2
- Patio & porch: Deck
- Pool features: None
Lot
- Size: 3,571 sqft
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 020600003976108
- Zoning: R
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Frame
- Foundation: Crawl Space
Condition
- New construction: No
- Year built: 1920
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & neighborhood
Location
- Region: Annapolis
- Subdivision: Eastport
- Municipality: Annapolis
Other
Other facts
- Listing agreement: Exclusive Right To Sell
- Ownership: Fee Simple
Price history
| Date | Event | Price |
|---|---|---|
| 3/16/2026 | Sold | $725,000-3.3%$616/sqft |
Source:  Bright MLS #MDAA2128698 Report a problem | ||
| 2/16/2026 | Contingent | $750,000$638/sqft |
Source: Bright MLS #MDAA2128698 Report a problem | ||
| 2/11/2026 | Price change | $750,000-3.7%$638/sqft |
Source: Bright MLS #MDAA2128698 Report a problem | ||
| 10/27/2025 | Listed for sale | $779,000+41.6%$662/sqft |
Source: Bright MLS #MDAA2128698 Report a problem | ||
| 8/22/2016 | Sold | $550,000-8.2%$468/sqft |
Source: Public Record Report a problem | ||
| 7/15/2016 | Pending sale | $599,000$509/sqft |
Source: Keller Williams - Annapolis #AA9610080 Report a problem | ||
| 5/28/2016 | Price change | $599,000-1.6%$509/sqft |
Source: Keller Williams - Annapolis #AA9610080 Report a problem | ||
| 4/25/2016 | Price change | $609,000-2.5%$518/sqft |
Source: Keller Williams - Annapolis #AA9610080 Report a problem | ||
| 3/29/2016 | Listed for sale | $624,900+68.9%$531/sqft |
Source: Keller Williams - Annapolis #AA9610080 Report a problem | ||
| 1/16/2015 | Sold | $370,000-17.8%$315/sqft |
Source: Public Record Report a problem | ||
| 8/19/2014 | Listing removed | $450,000$383/sqft |
Source: Coldwell Banker Residential Brokerage - Annapolis Church #AA8386688 Report a problem | ||
| 6/25/2014 | Listed for sale | $450,000-18%$383/sqft |
Source: Coldwell Banker Residential Brokerage - Annapolis Church #AA8386688 Report a problem | ||
| 10/3/2009 | Listing removed | $549,000$467/sqft |
Source: Long & Foster Real Estate, Inc. #AA6027033 Report a problem | ||
| 8/6/2008 | Price change | $549,000-18.7%$467/sqft |
Source: Long and Foster Real Estate #AA6027033 Report a problem | ||
| 5/27/2008 | Listed for sale | $675,000$574/sqft |
Source: Long and Foster Real Estate #AA6027033 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $10,345 +10.7% | $721,900 +11% |
| 2024 | $9,345 +12.5% | $650,300 +12.4% |
| 2023 | $8,310 +3.4% | $578,700 +1.4% |
| 2022 | $8,039 +1.4% | $570,567 +1.4% |
| 2021 | $7,925 +1.4% | $562,433 +1.5% |
| 2020 | $7,816 -0.1% | $554,300 |
| 2019 | $7,821 +1.4% | $554,300 |
| 2018 | $7,710 +5.4% | $554,300 -1.1% |
| 2017 | $7,316 | $560,600 +8.2% |
| 2016 | -- | $517,967 +9% |
| 2015 | -- | $475,333 +9.9% |
| 2014 | -- | $432,700 |
| 2013 | -- | $432,700 |
| 2012 | -- | $432,700 -15.1% |
| 2011 | -- | $509,830 |
| 2010 | -- | $509,830 |
| 2009 | -- | $509,830 -15.2% |
| 2008 | -- | $601,160 +20.5% |
| 2007 | -- | $498,696 +25.9% |
| 2006 | -- | $396,233 +34.9% |
| 2005 | -- | $293,770 +22.6% |
| 2004 | -- | $239,640 +29.2% |
| 2003 | -- | $185,510 +41.2% |
| 2002 | -- | $131,380 +3.1% |
| 2001 | -- | $127,382 |
Find assessor info on the county website
Neighborhood: 21403
Nearby schools
GreatSchools rating
- 6/10Eastport Elementary SchoolGrades: PK-5Distance: 0.2 mi
- 4/10Annapolis Middle SchoolGrades: 6-8Distance: 1.9 mi
- 5/10Annapolis High SchoolGrades: 9-12Distance: 4.6 mi
Schools provided by the listing agent
- District: Anne Arundel County Public Schools
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$730,300
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$730,300
- Maryland
- Anne Arundel County
- Annapolis
- 21403
- 320 Chester Ave
Nearby cities
Nearby zip codes
Other Annapolis Topics
