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3 Chester Ave, Annapolis, MD 21403
3 Chester Ave, Annapolis, MD 21403
Sold for $1,660,000
3 Chester Ave, Annapolis, MD 21403
Sold for $1,660,000
3 Chester Ave, Annapolis, MD 21403
3 Chester Ave, Annapolis, MD 21403
3 Chester Ave, Annapolis, MD 21403
3 Chester Ave, Annapolis, MD 21403

3 Chester Ave Annapolis, MD 21403

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$1,660,000

CLOSED
Beds
3
Baths
3
Sqft
2,815
Acres
0.13
Year
1952
Close Date
Feb 12, 2026
Property Type
Residential
Sub Type
Per Square Foot
$590
Date Listed
Nov 22, 2025

Description of 3 Chester Ave, Annapolis, MD 21403

Listing details for 3 Chester Ave, Annapolis, MD 21403 : 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.
Listing Updated : 10-11-2026 at 5:07 AM EDT
Listing Provided By : Victor Pascoe, 3012527771, [email protected], Keller Williams Select Realtors of Annapolis

Properties displayed may be listed or sold by various participants in the MLS

Source :

Bright MLS, MLS#: MDAA2131360

What's this home worth?

National portals guess with an algorithm. We price it from actual closed sales on your street.

Your home value estimate
$1.28M – $2.01M
Exact number$2,845,000

Want an exact number? Use an Agent, not an algorithm.

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What's this home worth?

National portals guess with an algorithm. We price it from actual closed sales on your street.

Your home value estimate
$1.28M – $2.01M
Exact number$2,845,000

Want an exact number? Use an Agent, not an algorithm.

Is this your home?

Claim it to unlock a private owner dashboard, track your equity, and get a free monthly value report.

Property History

DateEventPrice
2/12/2026
Sold
$1,660,000
$590/sqft
Source:Bright MLS #MDAA2131360
11/22/2025
Listed for sale
—
Source:Bright MLS #MDAA2131360
8/8/2025
Sold
$1,715,000
$609/sqft
Source:Bright MLS #MDAA2115396
6/30/2025
Listed for sale
—
Source:Bright MLS #MDAA2115396
3/11/2022
Sold
$1,425,000
$506/sqft
Source:Bright MLS #MDAA2023680
2/9/2022
Listed for sale
—
Source:Bright MLS #MDAA2023680

Location of 3 Chester Ave, Annapolis, MD 21403

Streetview of 3 Chester Ave, Annapolis, MD 21403

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What's this home worth?

National portals guess with an algorithm. We price it from actual closed sales on your street.

Your home value estimate
$1.28M – $2.01M
Exact number$2,845,000

Want an exact number? Use an Agent, not an algorithm.

Is this your home?

Claim it to unlock a private owner dashboard, track your equity, and get a free monthly value report.

Comments

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The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information 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 on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 Bright MLS, Inc.
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