Annapolis, MD 21403 215 Chester Avenue

215 Chester Avenue Annapolis, MD - Image 1215 Chester Avenue Annapolis, MD - Image 2215 Chester Avenue Annapolis, MD - Image 3
50 more
215 Chester Avenue Annapolis, MD - Image 4215 Chester Avenue Annapolis, MD - Image 5215 Chester Avenue Annapolis, MD - Image 6215 Chester Avenue Annapolis, MD - Image 7215 Chester Avenue Annapolis, MD - Image 8215 Chester Avenue Annapolis, MD - Image 9215 Chester Avenue Annapolis, MD - Image 10215 Chester Avenue Annapolis, MD - Image 11215 Chester Avenue Annapolis, MD - Image 12215 Chester Avenue Annapolis, MD - Image 13215 Chester Avenue Annapolis, MD - Image 14215 Chester Avenue Annapolis, MD - Image 15215 Chester Avenue Annapolis, MD - Image 16215 Chester Avenue Annapolis, MD - Image 17215 Chester Avenue Annapolis, MD - Image 18215 Chester Avenue Annapolis, MD - Image 19215 Chester Avenue Annapolis, MD - Image 20215 Chester Avenue Annapolis, MD - Image 21215 Chester Avenue Annapolis, MD - Image 22215 Chester Avenue Annapolis, MD - Image 23215 Chester Avenue Annapolis, MD - Image 24215 Chester Avenue Annapolis, MD - Image 25215 Chester Avenue Annapolis, MD - Image 26215 Chester Avenue Annapolis, MD - Image 27215 Chester Avenue Annapolis, MD - Image 28215 Chester Avenue Annapolis, MD - Image 29215 Chester Avenue Annapolis, MD - Image 30215 Chester Avenue Annapolis, MD - Image 31215 Chester Avenue Annapolis, MD - Image 32215 Chester Avenue Annapolis, MD - Image 33215 Chester Avenue Annapolis, MD - Image 34215 Chester Avenue Annapolis, MD - Image 35215 Chester Avenue Annapolis, MD - Image 36215 Chester Avenue Annapolis, MD - Image 37215 Chester Avenue Annapolis, MD - Image 38215 Chester Avenue Annapolis, MD - Image 39215 Chester Avenue Annapolis, MD - Image 40215 Chester Avenue Annapolis, MD - Image 41215 Chester Avenue Annapolis, MD - Image 42215 Chester Avenue Annapolis, MD - Image 43215 Chester Avenue Annapolis, MD - Image 44215 Chester Avenue Annapolis, MD - Image 45215 Chester Avenue Annapolis, MD - Image 46215 Chester Avenue Annapolis, MD - Image 47215 Chester Avenue Annapolis, MD - Image 48215 Chester Avenue Annapolis, MD - Image 49215 Chester Avenue Annapolis, MD - Image 50215 Chester Avenue Annapolis, MD - Image 51215 Chester Avenue Annapolis, MD - Image 52215 Chester Avenue Annapolis, MD - Image 53215 Chester Avenue Annapolis, MD - Image 54
Presented By: Coldwell Banker Realty
  • MLS# MDAA2128708
  • 10/19/2025
  • Request Tour
  • Request Info
  • Beds • 4
  • Full/Half Baths • 3 / 1
  • SQFT • 3,421
  • Garage • 2

Home Details

EXCITING PRICE IMPROVEMENT! SELLER HAS REDUCED THE PRICE-DON'T MISS THIS GREAT OPPORTUNITY. Embrace the Eastport lifestyle in this charming craftsman just steps from the water and downtown Annapolis. This beautifully maintained home offers 4 bedrooms, 3.5 baths, an elevator, and sitting areas on each level. The reverse floor plan features a gourmet kitchen, dining area, and living room with fireplace and wood floors. The second level primary suite has a private deck and spa-like bath. The entry level includes an en suite bedroom with deck and hot tub access, 2 additional bedrooms and hall bathroom. Enjoy seasonal Back Creek views from the upper balcony and relax in the spacious yard with pergola and hot tub. A rare driveway with 2 car detached garage and finished space above offers endless options. Walk to restaurants, pubs and parks. Perfect blend of Eastport charm and coastal sophistication!
Presented By: Coldwell Banker Realty

Interior Features for 215 Chester Avenue

Bedrooms

Bedrooms Count All Upper Levels1
Bedrooms Count Upper Level 11
Bedrooms Count Upper Level 2
Main Level Bedrooms3
Total Bedrooms4

Bathrooms

Bathrooms Half Upper Level 21
Bathrooms Half All Upper Levels1
Bathrooms Full Upper Level 20
Bathrooms Full Upper Level 11
Bathrooms Full All Upper Levels1
Bathrooms Count Upper Level 21.00
Bathrooms Count Upper Level 11.00
Bathrooms Count All Upper Levels2
Half Baths1
Total Baths4

Other Interior Features

LivingAreaSourceAssessor
Below Grade Unfin Area UnitsSquare Feet
Below Grade Unfin SQFT299
Below Grade Unfin SQFT SourceAssessor
Above Grade Finished Area3122
Above Grade Finished Area SourceAssessor
Above Grade Finished Area Unit TypeSquare Feet
BasementOther
Basement (Y/N)Yes
Below Grade Finished Area299
Below Grade Finished Area SourceAssessor
Below Grade Finished Area Unit TypeSquare Feet
Central Air Y/NYes
Fireplace FeaturesFireplace - Glass Doors, Gas/Propane, Stone, Electric
Fireplace Y/NYes
FlooringHardwood, Ceramic Tile
Heating FuelNatural Gas
Heating Y/NYes
Hot WaterTankless, Natural Gas
Interior AmenitiesBreakfast 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,
Laundry TypeMain Floor
Number of Elevators1
Total Fireplaces2

General for 215 Chester Avenue

AccessibilityElevator
AppliancesBuilt-In Range, Commercial Range, Dishwasher, Disposal, Dryer, Microwave, Oven/Range - Gas, Range Hood, Refrigerator, Six Burner Stove, Stainless Steel Appliances, Washer, Water Heater - Tankless
Architectural StyleCoastal, Craftsman
Bathrooms Count Main Level2.00
Bathrooms Full Main Level2
Body of WaterBack Creek
CityANNAPOLIS
Condo/Coop Association fee Y/NNo
Construction MaterialsFrame
Cool FuelElectric
CoolingCeiling Fan(s), Central A/C, Programmable Thermostat, Zoned
CountyANNE ARUNDEL
DirectionsCompromise St from downtown Annapolis into Eastport. Turn left onto Chester Ave. Home is on your right, next to Turner Park.
Full Baths3
Garage Spaces2.00
Garage Y/NYes
HOANo
HeatingForced Air, Programmable Thermostat, Zoned
Levels3
Living Area3421
Lot Size Square Feet5960.00
Lot Size UnitsSquare Feet
MunicipalityAnnapolis
New ConstructionNo
Other StructuresAbove Grade, Below Grade
OwnershipFee Simple
Patio/Porch FeaturesBalconies- Multiple, Porch(es), Deck(s)
PossessionCoin w/Sell Sett
Price Per Sq Ft Total AG576.23
Property TypeResidential
School DistrictANNE ARUNDEL COUNTY PUBLIC SCHOOLS
Security FeaturesCarbon Monoxide Detector(s), Security System, Smoke Detector, Sprinkler System - Indoor
Senior Community Y/NNo
SewerPublic Sewer
Standard StatusActive
StatusACTIVE
Structure TypeDetached
Subdivision NameEASTPORT
Tax Annual Amount16857.0
Tax Assessed Value1346533.0
Tax Year2024
Total SQFT3720
Vacation Rental Y/NNo
ViewCreek/Stream
Water Access Y/NYes
Year Built2003
Year Built SourceAssessor
ZoningRESIDENTIAL

Exterior for 215 Chester Avenue

# of Detached Garage Spaces2
Builder ModelEastport Craftsman
Exterior AmenitiesExtensive Hardscape, Exterior Lighting, Hot Tub, Street Lights
Foundation DetailsOther
Garage FeaturesAdditional Storage Area, Garage - Front Entry, Garage Door Opener
Land Assessed Value626900.00
Land Use CodeR
Lot FeaturesFront Yard, Landscaping, Level, Premium
Lot Size Acres0.14
Lot Size SourceAssessor
Navigable Water Y/NYes
Parking FeaturesConcrete Driveway
PoolNo Pool
SpaYes
Total Parking Spaces5
Type of ParkingDetached Garage, Driveway
Water Access FeaturesCanoe/Kayak, Fishing Allowed, Public Access, Swimming Allowed
Water Body TypeCreek
Water Oriented Y/NYes
Water SourcePublic
Water View Y/NYes
Waterfront Y/NNo

Additional Details

Price History

Rachel Shepherd

Price $1,799,000
MLS#MDAA2128708
List Date 10/19/2025
Property Type Single Family
Phone 703.929.4729
Request Tour
Request Info
Visit My Website

Similar Properties to 215 Chester Avenue

Skip to content