3 Chester Ave, Annapolis, MD 21403
Local realty services provided by:Better Homes and Gardens Real Estate Valley Partners
3 Chester Ave,Annapolis, MD 21403
$1,680,000
- 3 Beds
- 3 Baths
- 2,815 sq. ft.
- Single family
- Active
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.
Contact an agent
Home facts
- Year built:1952
- Listing ID #:MDAA2131360
- Added:50 day(s) ago
- Updated:January 11, 2026 at 02:42 PM
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)
New listings near 3 Chester Ave
- New
$519,930Active2 beds 2 baths1,318 sq. ft.78 Old Mill Bottom Rd N #307, ANNAPOLIS, MD 21409
MLS# MDAA2134478Listed by: MCWILLIAMS/BALLARD, INC. - Open Sun, 10am to 12pmNew
$485,000Active3 beds 2 baths1,880 sq. ft.108 Conley Dr, ANNAPOLIS, MD 21403
MLS# MDAA2133422Listed by: KELLER WILLIAMS SELECT REALTORS OF ANNAPOLIS - Coming Soon
$1,150,000Coming Soon4 beds 2 baths2762 Bon Haven Ln, ANNAPOLIS, MD 21401
MLS# MDAA2134402Listed by: RE/MAX EXECUTIVE - Coming Soon
$419,000Coming Soon2 beds 4 baths21 Muir Woods Ct, ANNAPOLIS, MD 21403
MLS# MDAA2134442Listed by: COLDWELL BANKER REALTY - Coming Soon
$899,000Coming Soon4 beds 4 baths1009 Old Bay Ridge Rd, ANNAPOLIS, MD 21403
MLS# MDAA2132254Listed by: COLDWELL BANKER REALTY - New
$3,250,000Active3 beds 3 baths2,043 sq. ft.45 E Lake Dr, ANNAPOLIS, MD 21403
MLS# MDAA2134186Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY - Coming Soon
$625,000Coming Soon4 beds 3 baths1091 Skyway Dr, ANNAPOLIS, MD 21409
MLS# MDAA2133076Listed by: NORTHROP REALTY - Open Sun, 11am to 1pmNew
$925,000Active4 beds 3 baths1,960 sq. ft.1403 Corey Ln, ANNAPOLIS, MD 21401
MLS# MDAA2134282Listed by: COLDWELL BANKER REALTY - Coming Soon
$1,100,000Coming Soon3 beds 4 baths1753 Ebling Trl, ANNAPOLIS, MD 21401
MLS# MDAA2134304Listed by: NORTHROP REALTY - New
$690,000Active3 beds 2 baths1,994 sq. ft.2572 Golfers Ridge Rd, ANNAPOLIS, MD 21401
MLS# MDAA2134084Listed by: DOUGLAS REALTY LLC