320 Chester Ave

Annapolis, MD 21403

$779,000
Price
2
Beds
1,176 Sq. Ft.
$662 / Sq. Ft.
1,176
Sq. Ft.
$662
per Sq. Ft.
Virtual Tour
Virtual Tour
front view of a house
a front view of a house with a garden
a view of a patio with a chairs and table in a patio
a view of a living room and a window
a workspace with furniture and wooden floor
a kitchen with a sink and a window
a kitchen with a refrigerator a stove a sink and white cabinets
a kitchen with a sink a refrigerator a washer and dryer
a kitchen with a stove and a microwave
a utility room with dryer washer and a view of living room
a bathroom with a sink toilet and shower
a bedroom with a bed desk and a window
a bedroom with a bed and wooden floor
a view of a brick house with a yard and plants
a view of an house with backyard and swimming pool
a view of a house with backyard
a view of a house with wooden floor
a view of balcony with wooden fence and trees
an empty room with wooden floor and windows
a view of an empty room with wooden floor and kitchen
a kitchen with granite countertop white cabinets and a window
a kitchen with kitchen island a refrigerator stove and sink
a kitchen with stainless steel appliances granite countertop a sink and a refrigerator
a kitchen with granite countertop a sink and a stove
a kitchen with granite countertop white cabinets and white appliances
a bathroom with a sink toilet and shower
a view of a hallway with washer and dryer
an empty room with windows
a view of an empty room with wooden floor
a view of a backyard with garden
a view of a house with a yard and swimming pool
a car parked in front of the building

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...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.
  1. Listed by John J Collins • Long & Foster Real Estate, Inc.
    P: (410)-693-6000 john@johncollinsgroup.com

Property Details for 320 Chester Avenue

Tax ID Number
020600003976108
Ownership
Fee Simple
Condo Coop Association
No
HOA
No
Structure Type
Detached
Style
Colonial
Levels/Stories
2
Waterfront
No
LISTING UPDATED: 12/01/2025 10:32 PM

Property Details for 320 Chester Avenue

StatusActive
MLS #MDAA2128698
Days on Market46
Taxes$9,345 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Fee Simple
Year Built1920
Lot Size0.08 AC / 3,571 SF
CountyAnne Arundel County

Location

Listing Courtesy of Long & Foster Real Estate, Inc.
Add your commute

Virtual Tour

Building Information for 320 Chester Avenue

Stories2Year Built1920Building Size-Lot Size0.08 AC / 3,571 SF

Payment Calculator

$4,628 per month

30 year fixed, 6.28% Interest

Principal and Interest

$3,849

Property Taxes

$779

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 320 Chester Avenue

Location
Location
  • In City Limits: Yes
  • School District Name: ANNE ARUNDEL COUNTY PUBLIC SCHOOLS
  • School District County ID: 121140671932
  • SchoolDistrictSource: Listing Agent
  • Elementary School: CALL SCHOOL BOARD (ANNE ARUNDEL MD)
  • ElementarySchoolSource: Listing Agent
  • Middle Or Junior School: CALL SCHOOL BOARD (ANNE ARUNDEL MD)
  • MiddleSchoolSource: Listing Agent
  • High School: CALL SCHOOL BOARD (ANNE ARUNDEL MD)
  • HighSchoolSource: Listing Agent
  • County: ANNE ARUNDEL
Waterfront / Water Access
Waterfront / Water Access
  • Water View: No
  • Water Access: No
  • Water Oriented: No
  • Navigable Water: No
  • Tidal Water: No
  • Riparian Rights Y/N: No
Association / Community Info
Association / Community Info
  • Senior Community: No
Taxes and Assessment
Taxes and Assessment
  • Tax Year: 2024
  • Tax Assessed Value: $721,900
  • Year Assessed: 2025
  • County Tax: $4,546
  • Improvement Assessed Value: $118,500
  • City Town Tax: $4,799
  • Land Assessed Value: $675,000
  • Clean Green Assessed: No
  • Land Use Code: R
  • Zoning: R
  • School Tax: $0
  • Automatically Update Tax Values Y/N: Yes
Rooms
Main
  • # Bedrooms Count Main Level: 1
  • # Bathrooms Count Main Level: 1
  • # Bathrooms Full Main Level: 1
All Upper Levels
  • # Bedrooms Count All Upper Levels: 1
  • # Bathrooms Count All Upper Levels: 1
  • # Bathrooms Full All Upper Levels: 1
Upper Level 1
  • # Bedrooms Count Upper Level: 1
  • # Bathrooms Count Upper Level: 1
  • # Bathrooms Full Upper Level: 1
Rooms
  • Room List: Living Room, Bedroom 2, Kitchen, Bedroom 1, Full Bath
  • Stories: Main, Upper 1
Rooms Information
Room 1
  • Room Type: Living Room
  • Room Length: 15.0
  • Room Width: 11.0
  • Room Level: Main
  • Room Exists: Yes
Room 2
  • Room Type: Kitchen
  • Room Length: 8.0
  • Room Width: 6.0
  • Room Level: Main
  • Room Exists: Yes
Room 3
  • Room Type: Bedroom 1
  • Room Length: 12.0
  • Room Width: 11.0
  • Room Level: Main
  • Room Exists: Yes
Room 4
  • Room Type: Full Bath
  • Room Level: Main
  • Room Exists: Yes
Room 5
  • Room Type: Living Room
  • Room Length: 14.0
  • Room Width: 12.0
  • Room Level: Upper 1
  • Room Exists: Yes
Room 6
  • Room Type: Kitchen
  • Room Length: 11.0
  • Room Width: 8.0
  • Room Level: Upper 1
  • Room Exists: Yes
Room 7
  • Room Type: Bedroom 2
  • Room Length: 15.0
  • Room Width: 9.0
  • Room Level: Upper 1
  • Room Exists: Yes
Room 8
  • Room Type: Full Bath
  • Room Level: Upper 1
  • Room Exists: Yes
Building Info
Building Info
  • Total Finished SQFT: 1,176.00
  • Total Finished SQFT Source: Assessor
Lot / Land Information
Lot / Land Information
  • Lot Size Source: Assessor
  • Parcel ID: 15314615
Parking
Parking
  • Type Of Parking: On Street
Interior Features
Interior Features
  • 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
  • Fireplace: No
Exterior Features
Exterior Features
  • Outdoor Living Structures: Deck(s)
  • Pool: No Pool
Utilities
Utilities
  • Heating: Yes
  • Cooling Type: Wall Unit, Ceiling Fan(s)
  • Cooling Fuel: Electric
  • Heating Type: Wall Unit
  • Heating Fuel: Electric
  • Hot Water: Electric
  • Water Source: Public
  • Sewer Septic: Public Sewer
Confidential Data
Listing Office
  • List Agent AOR: Anne Arundel County Association of REALTORS
  • List Agent URL: www.johncollinsgroup.com

Property History for 320 Chester Avenue

DateEvent & SourcePriceAppreciation
Oct 27, 2025

Listed (Active)

BRIGHT #MDAA2128698

$779,000—
Aug 22, 2016

Closed (Public Record)

Public Record #579924997

$550,000—
Aug 22, 2016

Closed (Public Record)

Public Record #579924997

$550,000

+27.8% / yr

Aug 22, 2016

Closed

BRIGHT #1001298945

$550,000—
Aug 22, 2016

Closed

BRIGHT #1001298191

$550,000—
Jul 14, 2016

Pending

BRIGHT #1001298945

—
Jul 14, 2016

Pending

BRIGHT #1001298191

—
Mar 30, 2016

Listed (Active)

BRIGHT #1001298945

$624,900—
Mar 28, 2016

Listed (Active)

BRIGHT #1001298191

$624,900—
Jan 9, 2015

Closed (Public Record)

Public Record #487064238

$370,000—
Nov 13, 2014

Withdrawn

BRIGHT #1007687088

$420,000—
Nov 13, 2014

Withdrawn

BRIGHT #1007687088

—
Jun 24, 2014

Listed (Active)

BRIGHT #1007687088

$450,000—
Oct 1, 2009

Expired

BRIGHT #MDAA320588

$549,000—
Apr 25, 2006

Listed (Active)

BRIGHT #MDAA320588

$675,000—
Mar 16, 2006

Expired

BRIGHT #MDAA319258

$675,000—
Sep 16, 2005

Listed (Active)

BRIGHT #MDAA319258

$795,000—
DateEvent & SourcePrice
10/27/2025

Listed (Active)

BRIGHT #MDAA2128698

$779,000
08/22/2016

Closed (Public Record)

Public Record #579924997

$550,000
08/22/2016

Closed (Public Record)

Public Record #579924997

$550,000

+27.8% / yr

08/22/2016

Closed

BRIGHT #1001298945

$550,000
08/22/2016

Closed

BRIGHT #1001298191

$550,000
07/14/2016

Pending

BRIGHT #1001298945

—
07/14/2016

Pending

BRIGHT #1001298191

—
03/30/2016

Listed (Active)

BRIGHT #1001298945

$624,900
03/28/2016

Listed (Active)

BRIGHT #1001298191

$624,900
01/09/2015

Closed (Public Record)

Public Record #487064238

$370,000
11/13/2014

Withdrawn

BRIGHT #1007687088

$420,000
11/13/2014

Withdrawn

BRIGHT #1007687088

—
06/24/2014

Listed (Active)

BRIGHT #1007687088

$450,000
10/01/2009

Expired

BRIGHT #MDAA320588

$549,000
04/25/2006

Listed (Active)

BRIGHT #MDAA320588

$675,000
03/16/2006

Expired

BRIGHT #MDAA319258

$675,000
09/16/2005

Listed (Active)

BRIGHT #MDAA319258

$795,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 320 Chester Avenue

Taxable ValueLand-Additions-Total-
Tax Record2025$10,345 ($862 / month)
Home Facts
Beds0Baths2Total Finished SqFt1,176 SqFtAbove Grade Finished SqFt1,176 SqFtStories2Lot Size3,571 SqFtStyleSingle Family ResidenceYear Built1920CountyANNE ARUNDELAPN06-000-03976108Fireplace TypeHas Fireplace

Schools near 320 Chester Avenue

This home is within Anne Arundel County Public Schools.
Rating
School
Type
Grades
Distance
Eastport Elementary School
Public - PK to 5
Annapolis Middle School
Public - 6 to 8
Annapolis High School
Public - 9 to 12
Mary Moss at Adams Academy
Public - 6 to 9
Rating
School
Distance
Eastport Elementary School
PublicPK to 5

Annapolis Middle School
Public6 to 8

Annapolis High School
Public9 to 12

Mary Moss at Adams Academy
Public6 to 9

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

Similar Sold Homes

Explore Nearby Homes

More information about 320 Chester Avenue, Annapolis, MD 21403

320 Chester Avenue is a single family home for sale in Annapolis, MD 21403. This property was listed for sale on October 27, 2025 by Long & Foster Real Estate, Inc., it's currently listed at $779,000. It has been on the market for a total of 46 days and was last sold on August 22, 2016. This listing's school district is Anne Arundel County Public Schools. Nearby schools include Eastport Elementary School, Annapolis Middle School and Annapolis High School. 320 Chester Avenue is a 2-bed, 2-bath, 1,176 sqft single family home built in 1920.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Long & Foster Real Estate, Inc.

© 2025 Bright MLS. All rights reserved. All information is deemed reliable, but accuracy is not guaranteed. Listing information is from various brokers who participate in IDX and not all listings may be visible on the site. The property information being provided is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated on 12/01/2025 10:32 PM