3 Chester Ave, Annapolis, MD 21403
Local realty services provided by:ERA Byrne Realty
3 Chester Ave,Annapolis, MD 21403
$1,680,000
- 3 Beds
- 3 Baths
- 2,815 sq. ft.
- Single family
- Pending
Listed by: victor pascoe
Office: keller williams select realtors of annapolis
MLS#:MDAA2131360
Source:BRIGHTMLS
Price summary
- Price:$1,680,000
- Price per sq. ft.:$596.8
About this home
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.
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Home facts
- Year built:1952
- Listing ID #:MDAA2131360
- Added:82 day(s) ago
- Updated:February 11, 2026 at 08:32 AM
Rooms and interior
- Bedrooms:3
- Total bathrooms:3
- Full bathrooms:3
- Living area:2,815 sq. ft.
Heating and cooling
- Cooling:Ceiling Fan(s), Central A/C, Zoned
- Heating:Baseboard - Electric, Electric, Forced Air, Heat Pump(s), Oil, Zoned
Structure and exterior
- Roof:Shingle
- Year built:1952
- Building area:2,815 sq. ft.
- Lot area:0.13 Acres
Utilities
- Water:Public
- Sewer:Public Sewer
Finances and disclosures
- Price:$1,680,000
- Price per sq. ft.:$596.8
- Tax amount:$12,991 (2024)
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