215 Chester Avenue
Annapolis, MD, 21403 $ 1,799,000
Bedrooms4 Baths3.1 Sq 3,421 Monthly Estimate*
$ 11,223
for $1,799,000 with 4 bedrooms and 3 full baths, 1 half bath. This 3,421 square foot home was built in 2003 on a lot size of 0.14.
EXCITING PRICE IMPROVEMENT! SELLER HAS REDUCED THE PRICE-DON'T MISS THIS GREAT OPPORTUNITY. Immerse yourself in the quintessential Eastport lifestyle with this inviting Craftsman-style residence, ideally located just moments from the water access at Davis Park and the vibrant offerings of Eastport and downtown Annapolis. This beautifully maintained home spans three thoughtfully designed levels and features four bedrooms, three and a half baths, an elevator, and comfortable sitting areas on every floor. Highlights include a gourmet kitchen, warm living spaces with a fireplace, rich wood flooring, a generous dining area, and a reverse floor plan that captures light, views, and a relaxed coastal feelmaking every day feel like a getaway. The entry level is perfect for hosting family and friends, offering three bedrooms, including a private ensuite with direct access to the deck and hot tub, plus two additional bedrooms served by a hall bath. The second level is devoted to the primary retreat, featuring an open sitting area overlooking the level below, a spacious bedroom, a private deck with peaceful backyard views, and a luxurious spa-inspired bath. The top level serves as the heart of the home, complete with an expansive partially covered balcony where you can enjoy seasonal glimpses of Back Creek from an exceptionally private setting. Outdoor spaces are equally impressive, with a welcoming front porch and a large, fenced rear yard featuring a deck, hot tub, and pergolaideal for entertaining, grilling, or simply soaking in the Eastport vibe. A detached garage with driveway provides rare and valuable off-street parking for multiple vehicles. Above the garage, a finished space with a separate entrance offers endless flexibility for guests, a home office, studio, or rental opportunity. This property also presents excellent potential as a VRBO or Airbnb, offering year-round income possibilities in one of Annapoliss most sought-after neighborhoods. Buyer should check current licensing regulations for Annapolis. Enjoy leisurely strolls through Eastports artistic, maritime streets to acclaimed restaurants, pubs, and charming street-end parks, one is right next door. Downtown Annapolis and the Naval Academy are just steps away via the Spa Creek drawbridge or a quick ride on the water taxi. From here, youre also close to premier cruising and fishing waters, with easy access to destinations like Baltimores Inner Harbor, St. Michaels, Oxford, and Solomons Island. Conveniently located approximately five miles from Routes 50 and 97, with direct access to Baltimore, BWI, Fort Meade/NSA, and Washington, DC, this home offers the perfect blend of coastal charm, walkable convenience, and sophisticated living. Welcome to Eastport living at its best.
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FeaturesGeneralLiving Area 3421
Sewer Public Sewer
Heating Forced Air Programmable Thermostat Zoned
Cooling Ceiling Fan(s) Central A/C Programmable Thermostat Zoned
Possession Coin w/Sell Sett
Appliances Built-In Range Commercial Range Dishwasher Disposal Dryer Microwave Oven/Range - Gas Range Hood Refrigerator Six Burner Stove Stainless Steel Appliances Washer Water Heater - Tankless
Zoning RESIDENTIAL
Garage Spaces 2.00
Patio/Porch Features Balconies- Multiple Porch(es) Deck(s)
Architectural Style Coastal Craftsman
Security Features Carbon Monoxide Detector(s) Security System Smoke Detector Sprinkler System - Indoor
Construction Materials Frame
School District ANNE ARUNDEL COUNTY PUBLIC SCHOOLS
Year Built 2003
View Creek/Stream
Levels 3
Tax Year 2024
Ownership Fee Simple
Cool Fuel Electric
Municipality Annapolis
Accessibility Elevator
County ANNE ARUNDEL
New Construction N
Property Type Residential
HOA N
Subdivision Name EASTPORT
Garage Y/N Y
Water Access Y/N Y
Other Structures Above Grade Below Grade
Full Baths 3
Status ACTIVE
Directions Compromise St from downtown Annapolis into Eastport. Turn left onto Chester Ave. Home is on your right next to Turner Park.
City ANNAPOLIS
Body of Water Back Creek
Senior Community Y/N N
Lot Size Units Square Feet
Lot Size Square Feet 5960.00
Tax Annual Amount 16857.0
Structure Type Detached
Condo/Coop Association fee Y/N N
Bathrooms Full Main Level 2
Bathrooms Count Main Level 2.00
Price Per Sq Ft Total AG 576.23
Vacation Rental Y/N N
Standard Status Active
Year Built Source Assessor
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InteriorInterior Amenities Breakfast Area Built-Ins Ceiling Fan(s) Combination Dining/Living Combination Kitchen/Dining Combination Kitchen/Living Dining Area Elevator Entry Level Bedroom Exposed Beams Family Room Off Kitchen
Heating Fuel Natural Gas
Basement Other
Flooring Hardwood Ceramic Tile
Total Fireplaces 2
Fireplace Features Fireplace - Glass Doors Gas/Propane Stone Electric
Hot Water Tankless Natural Gas
Basement (Y/N) Y
Heating Y/N Y
Fireplace Y/N Y
Above Grade Finished Area 3122
Half Baths 1
Central Air Y/N Y
Total Bedrooms 4
Below Grade Finished Area 299
Main Level Bedrooms 3
Below Grade Finished Area Unit Type Square Feet
Laundry Type Main Floor
Below Grade Finished Area Source Assessor
Above Grade Finished Area Source Assessor
Above Grade Finished Area Unit Type Square Feet
Total Baths 4
Number of Elevators 1
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ExteriorExterior Amenities Extensive Hardscape Exterior Lighting Hot Tub Street Lights
Pool No Pool
Parking Features Concrete Driveway
Lot Features Front Yard Landscaping Level Premium
Water Source Public
Garage Features Additional Storage Area Garage - Front Entry Garage Door Opener
Type of Parking Detached Garage Driveway
Foundation Details Other
Spa Y
Water View Y/N Y
Lot Size Acres 0.14
Water Body Type Creek
Lot Size Source Assessor
Waterfront Y/N N
Builder Model Eastport Craftsman
Water Access Features Canoe/Kayak Fishing Allowed Public Access Swimming Allowed
Land Assessed Value 626900.00
Navigable Water Y/N Y
Water Oriented Y/N Y
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* Excluded FeaturesList ByColdwell Banker RealtyBroker
janet.craig@cbrealty.comEmail
Affordability Calculator
- Monthly Principal & Interest
- $11,223
- Monthly Property Taxes
- $1,405
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Annapolis, MD
Average List Price $1,476,115
Percent of Sale Price 18%
About Annapolis, MD 40,323 Population
12% Since 2002
$ 79,580 Median Income
38.67 Median Age
24% Households with Children
Trends Information provided by ATTOM Data Solutions.
3533405 Elementary School
3533185 Middle School
Unknown High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 12/13/2025 | $1,799,000 | -5.07% | Price Down |
| 11/14/2025 | $1,895,000 | -2.82% | Price Down |
| 10/19/2025 | $1,950,000 | | Listed Price |