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3 Beds
3 Baths
2,815 sqft

$1,660,000

3 CHESTER AVENUE, ANNAPOLIS MD, 21403

Price per sqft$589.70
Built in1952
Property size2,815 sqft
Property typeResidential

Overview

Sold

Closed-bright

Listed Feb 12, 2026

Updated 5 days ago

Step into the heart of Eastport, where charm and convenience meet in this beautifully renovated Cape Cod. Just a short stroll from the water’s edge and downtown Annapolis, this home embodies the Eastport lifestyle — vibrant, nautical, and effortlessly welcoming. From the moment you enter, natural light pours through every window, illuminating three levels of thoughtfully designed living space. Classic details — arched doorways, hardwood floors, custom built-ins, and rich millwork — blend seamlessly with modern updates, creating a home that feels both timeless and fresh. The inviting floor plan offers room for every occasion. A serene primary suite with its own fireplace provides a private retreat, while the main-level office doubles as a guest room or den. Formal living room with fireplace and gorgeous dining room set the stage for elegant entertaining The family room invites casual gatherings with another fireflace and access to the screened porch. The updated kitchen is a true centerpiece, with fresh cabinetry, stylish countertops, and a backsplash that ties it all together. Upstairs, a spiral staircase leads to a sunlit loft with a private balcony — perfect for a creative nook, playroom, or quiet reading space. Outside, the screened porch, fenced yard, and welcoming front porch create effortless indoor-outdoor living, ideal for relaxing or hosting friends. The basement was recently waterproofed. Practical touches like a mudroom with laundry and off-street parking make everyday life easy. Beyond the walls, Eastport beckons. Launch your kayak from Horn Point Park, wander streets lined with art and history, or cross the Spa Creek drawbridge to downtown Annapolis and the Naval Academy. From this location, the Chesapeake Bay is your playground — with cruising and fishing destinations like Baltimore’s Inner Harbor, St. Michael’s, Oxford, and Solomon’s Island all within reach. Annapolis offers the perfect balance of small-town charm and cosmopolitan sophistication, and this Eastport jewel places you right at the center of it all. With quick access to Rt. 50 and 97, Baltimore, BWI, Ft. Meade/NSA, and Washington, DC are just a drive away. This is more than a home — it’s a lifestyle. Welcome to Eastport.

Additional information

MLS® ID
MDAA2131360

Interior Features

Bedrooms
3
Bathrooms
3
Fireplace
Yes
Cooling
Yes
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
0.13 Acres

Other Property Details

Taxes
$12,991
Tax Frequency
Annually
View
Yes
55+/Senior Community
No
MLS provider logo

Listed by Keller Williams Select Realtors of Annapolis
Listing Contact: 3012527771 

The IDX display contains information sourced from the Bright MLS, Inc. as of 9/15/2026. This data is intended solely for personal, non-commercial use and is not to be utilized for any other purposes except to identify potential properties for purchase. Although the MLS data displayed is typically considered reliable, it is not guaranteed to be accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and are advised to conduct their own investigations or seek professional assistance. Other sources besides the Listing Agent may have contributed to the MLS data presented. Unless expressly specified in writing, the Broker/Agent has not confirmed any information obtained from external sources. The Broker/Agent may or may not have acted as the Listing and/or Selling Agent and cannot guarantee the accuracy of property locations displayed on any map. Any compensation offers are solely made to participants of the MLS where the listing is registered.

©2026 Bright MLS, Inc. all rights reserved.

Data last updated on 9/15/2026 at 11:02 PM UTC

 

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