215 CHESTER AVENUE, ANNAPOLIS, MD 21403

$1,799,000

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… Read More 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. Read Less

Courtesy of Janet L Craig, Coldwell Banker Realty 410-263-8686

Listing Snapshot

Days Online

Last Updated

Jan 4, 2026

Property Type

Single Family Residential

Beds

Full Baths

Partial Baths

Square Ft.

3,421

Lot Size

0.14 Acres

Year Built

2003

MLS Number

MDAA2128708

Additional Details

Appliances & Equipment

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

Building

Built in 2003, Living area: 3421, Levels: 3, Construction Materials: Frame

Cooling

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

Accessibility Features

Elevator

Exterior Features

Patio/Porch Features: Balconies- Multiple, Porch(es), Deck(s), Extensive Hardscape, Exterior Lighting, Hot Tub, Street Lights

Fireplaces

2 fireplaces, Fireplace - Glass Doors, Gas/Propane, Stone, Electric

Floors

Hardwood, Ceramic Tile

Garage

2 spaces

Heating

Forced Air, Programmable Thermostat, Zoned

Interior Features

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, Floor Plan - Open, Kitchen - Eat-In, Kitchen - Gourmet, Primary Bath(s), Recessed Lighting, Sprinkler System, Upgraded Countertops, Window Treatments, Wood Floors

Lot

0.14 acres, Front Yard, Landscaping, Level, Premium

Parking

Concrete Driveway

Property

Other structures: Above Grade, Below Grade, Creek/Stream

Security Features

Carbon Monoxide Detector(s), Security System, Smoke Detector, Sprinkler System - Indoor

Sewer

Public Sewer

Taxes

Annual Amount: $16,857, Year: 2024, Zoning: RESIDENTIAL

Utilities

Water Source: Public

Water Features

Water Body Name: Back Creek

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