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3 Chester Avenue

Annapolis, MD 21403

3 beds
3 baths
2,815 sqft
5,850 sqft lot
$595 per sqft
1952 build

Celebrate the Eastport lifestyle in this charming jewel box of a home just steps from everything Eastport/Annapolis has to offer. Enjoy three levels of well maintained and impeccable living space that includes 3 bedrooms and 3 baths. This beautifully renovated Cape Cod is flooded with natural sunlight and exudes timeless character while offering modern comforts in every corner. Thoughtful updates and classic design elements—arched doorways, hardwood floors, custom built-ins, and rich millwork come together to create a home that is as charming as it is functional. The inviting floor plan features three generously sized bedrooms, including a serene primary suite with its own fireplace, and a main-level office that easily doubles as a guest room or den. The formal living and dining rooms provide elegant spaces for entertaining, while the expansive great room offers a more casual retreat. The newly updated kitchen is a standout, boasting all-new cabinetry, stylish countertops, and a fresh backsplash that blends beautifully with the home’s character. A spiral staircase leads to a sunlit loft with private balcony—perfect for a creative nook, playroom, or tranquil reading space. Enjoy seamless indoor-outdoor living with a screened porch, private fenced yard, patio and welcoming front porch, ideal for relaxing or hosting gatherings. The unfinished lower level has just been professionally waterproofed and presents endless potential for additional living space, a home gym, studio, or workshop. Additional features include a mudroom with conveniently located laundry and coveted off-street parking. This home is a rare blend of historic charm, modern updates, and unbeatable lifestyle. Grab your kayaks and launch from multiple locations including Horn Point Park just a block from the front door. Stroll the artful and nautical streets to amenities like; five-star restaurants, pubs and street-end parks with hidden treasures. Not to mention you are merely steps away from downtown Annapolis and Naval Academy by either walking across the Spa Creek drawbridge or motoring in the water taxi. From this location, you are also close to some of the Bay's best cruising and fishing areas. Attractive destinations such as Baltimore's Inner Harbor, St. Michael's, Oxford, and Solomon's Island are only a short cruise away. Annapolis offers the perfect balance of small-town charm and big world sophistication. Located just 5 miles to Rt. 50 and 97 which provides direct access to Baltimore, BWI, Ft.Meade/NSA and Washington, DC. Welcome Home!

Listing courtesy of BRIGHT / TTR Sotheby's International Realty

Last checked: Checking… • Last updated Jun 30, 2025 •

MLS# MDAA2115396 —

The Building

Year Built:

1952
Year Built Source:

Assessor
Year Major Reno/Remodel:

1998
Roof:

Shingle
New Construction:

No
Construction Materials:

Combination
Builder Model:

Charming Eastport Cape Cod
Structure Type:

Detached
Architectural Style:

Cape Cod
Levels:

3.5
Security Features:

Security System, Smoke Detector
Accessibility Features:

None
Foundation Details:

Other
Basement:

Yes
Basement Type:

Connecting Stairway, Interior Access, Unfinished, Water Proofing System
Total SqFt Source:

Assessor
Total Below Grade SqFt:

884
Total Below Grade SqFt Source:

Assessor
Above Grade Finished Area Units:

Square Feet
Above Grade Unfinished Area Units:

Square Feet
Above Grade Finished SqFt:

2815
Above Grade Finished SqFt Source:

Assessor
Below Grade Unfinished Area Units:

Square Feet
Below Grade Unfinished SqFt:

884
Below Grade Unfinished SqFt Source:

Assessor
Tax Total Finished SqFt:

2815

Interior

Interior Features:

Family Room Off Kitchen, Breakfast Area, Combination Kitchen/Living, Kitchen - Island, Kitchen - Table Space, Dining Area, Built-Ins, Window Treatments, Primary Bath(s), Wood Floors, Upgraded Countertops, Floor Plan - Open, Floor Plan - Traditional, Carpet, Ceiling Fan(s), Combination Dining/Living, Crown Moldings, Pantry, Skylight(s), Spiral Staircase, Walk-in Closet(s)
Flooring Type:

Hardwood, Carpet, Ceramic Tile
Fireplace:

Yes
Fireplaces:

3
Fireplace Features:

Equipment, Fireplace - Glass Doors, Mantel(s), Screen
Wall & Ceilings:

Plaster Walls, 9'+ Ceilings, Vaulted Ceilings
Living Area SqFt Source:

Assessor

Room Dimensions

Total SqFt:

3699
Living Area SqFt:

2,815 Sqft

Financial & Terms

Sale Type:

Standard
Acceptable Financing:

Cash, Conventional
Possession:

Settlement

Location

Directions:

From Downtown Annapolis take the Spa Creek Bridge into Eastport. Turn left onto Chesapeake Ave. Turn right onto First St. Turn left onto Chester Avenue, home is on your right. Welcome Home!
Latitude:

38.97164751
Longitude:

-76.47546533

The Property

Property Type:

Residential
Property Condition:

Very Good
Lot Size Units:

Square Feet
Lot Size Acres:

0.13
Lot Size Source:

Assessor
Lot Features:

Landscaping, Level, Rear Yard
Lot SqFt:

5,850 Sqft
Inclusions:

See Documents for Inclusions/Exclusions
Additional Parcels:

No
Zoning:

R2
View:

Garden/Lawn
In City Limits:

Yes
Outdoor Living Structures:

Patio(s), Porch(es), Screened, Roof, Balcony
Other Structures:

Above Grade
Waterview:

No
Fencing:

Rear
Waterfront:

No
Water Oriented:

Yes
Water Access:

Yes
Water Access Features:

Canoe/Kayak, Fishing Allowed, Public Access
Distance To Water:

Blocks
Distance To Body Of Water:

1
Water Body Name:

Back Creek/Severn River
Water Body Type:

Creek/Stream
Navigable Water:

Yes
Tidal Water:

No
Land Use Code:

R
Ground Rent Exists:

No
Riparian Rights:

No

Listing Agent

Contact info:

Taxes

Tax ID Number:

020600004881800
Tax Year:

2024
Tax Lot:

26
Tax Annual Amount:

$12,991
Tax Assessed Value:

$992,633
Year Assessed:

2025
County Tax:

6319.00
City/Town Tax:

6672.00
Total Taxes Payment Frequency:

Annually

Beds

Bedrooms:

3
Upper Level Bedrooms:

3
Upper Level 1 Bedrooms:

3

Baths

Total Baths:

3
Full Baths:

3
Main Level Baths:

1.00
Main Level Full Baths:

1
Upper Level Full Baths:

2
Upper Level Total Baths:

2
Upper Level Total Baths:

2.00
Upper Level Full Baths:

2

The Listing

Virtual Tour

Heating & Cooling

Cooling Type:

Central A/C, Ceiling Fan(s), Programmable Thermostat, Zoned
Central Air:

Yes
Cooling Fuel:

Electric
Heating:

Yes
Heating Type:

Forced Air, Heat Pump(s), Zoned, Programmable Thermostat
Heating Fuel:

Electric, Oil

Utilities

Sewer/Septic:

Public Sewer
Hot Water:

Electric
Water Source:

Public

Appliances

Appliances:

Dishwasher, Disposal, Dryer, Icemaker, Microwave, Refrigerator, Washer, Oven/Range - Electric, Water Heater
Laundry Type:

Main Floor

Schools

School District Name:

Anne Arundel County Public Schools
School District Source:

Listing Agent

The Community

Subdivision Name:

Eastport
Senior Community:

No
Exterior Features:

Exterior Lighting, Extensive Hardscape
Pool:

No Pool
HOA:

No
Condo/Coop Association:

No

Parking

Total Garage and Parking Spaces:

2
Garage:

No
Type of Parking:

Driveway, On Street
Parking Features:

Stone Driveway
Driveway - # of Spaces:

2

Extra Units

Vacation Rental:

No

Monthly cost estimate

Asking price

$1,675,000

Expense	Monthly cost
Mortgage	$8,969
Taxes	$1,082
Insurance	$460
Utilities	$263 See report
Total	$10,774/mo.^*
	^*This is an estimate

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Sale history

Date	Event	Source	Price	% Change
6/30/25 Jun 30, 2025	Listed / Active	BRIGHT	$1,675,000

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This house located in Annapolis, MD 21403 is currently for sale for $1,675,000. 3 Chester Avenue is a 2,815 square foot house with 3 beds and 3 baths. This house is in the attendance area of Annapolis High School, Eastport Elementary School, and Annapolis Middle School.

Listing Courtesy of: BRIGHT and TTR Sotheby's International Realty.

The information included in this listing is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information on each listing is furnished by the owner and deemed reliable to the best of his/her knowledge, but should be verified by the purchaser. BRIGHT MLS and Estately assume no responsibility for typographical errors, misprints or misinformation. This property is offered without respect to any protected classes in accordance with the law. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller.