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215 Chester Avenue

ANNAPOLIS, MD 21403
  • $1,799,000
  • STATUS: Active Under Contract
  • ON SITE: 93 Days
  • ID#: MDAA2128708
Under Contract
UPDATED: 62 min ago
$1,799,000
  • 4
    BEDS
  • 0.14
    ACRES
  • 3
    BATHS
  • 1
    1/2 BATHS
  • 3,421
    SQFT
  • $526
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
2003
County:

School Ratings & Info

Description

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 feel—making 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 pergola—ideal 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 Annapolis’s most sought-after neighborhoods. Buyer should check current licensing regulations for Annapolis. Enjoy leisurely strolls through Eastport’s 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, you’re also close to premier cruising and fishing waters, with easy access to destinations like Baltimore’s Inner Harbor, St. Michaels, Oxford, and Solomon’s 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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©2026 Bright MLS, All Rights Reserved. IDX information 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. Some properties which appear for sale may no longer be available because they are for instance, under contract, sold, or are no longer being offered for sale. Information is deemed reliable but is not guaranteed accurate by the MLS or Nomis Group International | eXp Realty. 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. Data last updated: 2026-01-21T21:52:36.863.
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215 Chester Avenue ANNAPOLIS, MD 21403

  • Price: $1,799,000
  • Status: Active Under Contract
  • On Site: 93 Days
  • Updated: 62 min ago
  • ID#: MDAA2128708
4
Beds
3
Baths
1
½ Baths
0.14
Acres
3,421
SQFT
$526
$/SQFT
2003
Built
Neighborhood:
Eastport
County:
Anne Arundel
School District:
Anne Arundel County Public Schools
Property Description
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 feel—making 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 pergola—ideal 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 Annapolis’s most sought-after neighborhoods. Buyer should check current licensing regulations for Annapolis. Enjoy leisurely strolls through Eastport’s 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, you’re also close to premier cruising and fishing waters, with easy access to destinations like Baltimore’s Inner Harbor, St. Michaels, Oxford, and Solomon’s 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.
Exterior Features

Architectural Style CoastalCraftsman Construction Materials Frame Distance To Body Of Water 1 Exterior Features Extensive HardscapeExterior LightingHot TubStreet Lights Garage Spaces 2.00 Garage Type Additional Storage AreaGarage - Front EntryGarage Door Opener Garage YN Yes Lot Features Front YardLandscapingLevelPremium Parking Features Concrete Driveway Parking Types Detached GarageDriveway Patio And Porch Features Balconies- MultiplePorch(es)Deck(s) Pool No Pool View Creek/Stream Water Access Features Canoe/KayakFishing AllowedPublic AccessSwimming Allowed Water Access YN Yes Water Body Name Back Creek Water Body Type Creek Water View YN Yes Waterfront YN No

Interior Features

Above Grade Fin SQFT 3122 Appliances Built-In RangeCommercial RangeDishwasherDisposalDryerMicrowaveOven/Range - GasRange HoodRefrigeratorSix Burner StoveStainless Steel AppliancesWasherWater Heater - Tankless Basement Other Basement YN Yes Below Grade Finished Area 299 Below Grade Unfinished Area 299 Cooling Ceiling Fan(s)Central A/CProgrammable ThermostatZoned Fireplace Features Fireplace - Glass DoorsGas/PropaneStoneElectric Fireplace YN Yes Fireplaces Total 2 Flooring HardwoodCeramic Tile Heating Forced AirProgrammable ThermostatZoned Heating YN Yes Interior Features Breakfast AreaBuilt-InsCeiling Fan(s)Combination Dining/LivingCombination Kitchen/DiningCombination Kitchen/LivingDining AreaElevatorEntry Level BedroomExposed BeamsFamily Room Off KitchenFloor Plan - OpenKitchen - Eat-InKitchen - GourmetPrimary Bath(s)Recessed LightingSprinkler SystemUpgraded CountertopsWindow TreatmentsWood Floors Laundry Type Main Floor Levels 3 Main Level Bedrooms 3 Security Features Carbon Monoxide Detector(s)Security SystemSmoke DetectorSprinkler System - Indoor Spa YN Yes Upper Level1 Bedrooms 1 Walls Ceilings Beamed CeilingsVaulted CeilingsWood Ceilings

Property Features

Accessibility Features Elevator Association YN No Builder Model Eastport Craftsman Central Air YN Yes Condo YN No Cooling Fuel Electric Elevators 1 Foundation Details Other Ground Rent Payment Frequency Annually Heating Fuel Natural Gas Hot Water TanklessNatural Gas Municipality Annapolis Navigable Water YN Y New Construction YN No Original MLSNumber 804242360162 Ownership Interest Fee Simple Sale Type Standard Senior Community YN No Sewer Public Sewer Structure Design Type Detached Tax Annual Amount 16857.00 Vacation Rental YN No Water Source Public Zoning RESIDENTIAL

Listing courtesy of Coldwell Banker Realty: .


©2026 Bright MLS, All Rights Reserved. IDX information 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. Some properties which appear for sale may no longer be available because they are for instance, under contract, sold, or are no longer being offered for sale. Information is deemed reliable but is not guaranteed accurate by the MLS or Nomis Group International | eXp Realty. 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. Data last updated: 2026-01-21T21:52:36.863.
 
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