For Sale
Single family home for sale at 3 Chester Ave, Annapolis, MD 21403 | MLS# MDAA2131360 | Listing updated on 2026-01-06
Photo 1 of Single family home for sale at 3 Chester Ave, Annapolis, MD 21403 | MLS# MDAA2131360 | Listing updated on 2026-01-06
Photo 2 of Single family home for sale at 3 Chester Ave, Annapolis, MD 21403 | MLS# MDAA2131360 | Listing updated on 2026-01-06
Photo 3 of Single family home for sale at 3 Chester Ave, Annapolis, MD 21403 | MLS# MDAA2131360 | Listing updated on 2026-01-06
Photo 4 of Single family home for sale at 3 Chester Ave, Annapolis, MD 21403 | MLS# MDAA2131360 | Listing updated on 2026-01-06
47+
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Street View

$1,680,000

Monthly Est:$8,362

  • Beds Icon3 Beds
  • Beds Icon
    3 Baths
  • Beds Icon2,815sqft

3 Chester Ave, Annapolis, MD 21403

$8,362/moEst:

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  • Single Family Residence

  • Built in 1952

  • $-- HOA

  • 5,850 sqft lot

  • $597/sq.ft

Description

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.

  • Houzeo last checked: 12 minutes ago
  • Listing updated: January 6, 2026 at 9:03 pm
  • Listing Provided by: Victor Pascoe (301) 252-7771 | Keller Williams Select Realtors of Annapolis (410) 972-4000
  • Source: Bright MLS-NJ | MLS#: MDAA2131360 Bright MLS-NJ

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Anne Arundel Md County

  • City

    Annapolis

  • Neighborhood

    --

  • Year Built

    1952

  • HOA Fees

    -

  • Finished Area

    2,815 sqft

  • Lot Size

    5,850 sqft lot

  • Basement Area

    - sqft

  • MLS Name

    Bright MLS

  • MLS Number

    MDAA2131360

  • MLS Status

    ACTIVE-BRIGHT

  • Days on Market

    46

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Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 3

    Bathrooms: 3

Interior

  • Flooring

    Hardwood, Carpet, Ceramic Tile

  • Appliances

    Dishwasher, Disposal, Dryer, Icemaker, Microwave, Refrigerator, Washer, Oven/range Electric, Water Heater

  • Interior Features

    Family Room Off Kitchen, Breakfast Area, Combination Kitchen/living, Kitchen Island, Kitchen Table Space, Dining Area, Built Ins, Window Treatments, Primary Bath(s), Wood Floors, Upgraded Countertops, Floor Plan Open, Floor Plan Traditional, Carpet, Ceiling Fan(s), Combination Dining/living, Crown Moldings, Pantry, Skylight(s), Spiral Staircase, Walk In Closet(s)

  • Sewer

    Public Sewer

  • Cooling

    Central A/c, Ceiling Fan(s), Zoned

  • Heating

    Forced Air, Heat Pump(s), Zoned, Baseboard Electric

  • Exterior Features

    Exterior Lighting, Extensive Hardscape

Construction

  • Year Built

    Year Built: 1952

  • Home type

    Single Family Residence

  • Architectural Style

    Cape Cod

  • Construction Materials

    Combination

  • Foundation Details

    Other

  • Roof

    Shingle

Utilities & Energy

  • Water Source

    Public

  • Parking Features

    Stone Driveway

  • Fireplace Features

    Mantel(s), Screen

  • Basement

    Connecting Stairway, Interior Access, Unfinished, Water Proofing System

  • Security Features

    Security System, Smoke Detector

Other Features

  • Lot Features

    Landscaping, Level, Rear Yard

  • Patio And Porch Features

    Patio, Porch, Screened, Roof, Balcony

  • Subdivision Name

    Eastport

Price History

DateEventPrice

11/22/2025

Source: mls_logoBright MLS-NJ #MDAA2131360

Listed for Sale

$1,730,000 +2.98%

$706/sqft

11/22/2025

Source: mls_logoBright MLS-NJ #MDAA2131360

Price Decreased

$1,680,000 -2.04%

$685/sqft

08/08/2025

Source: mls_logoBright MLS-NJ #MDAA2115396

Sold

$1,715,000 +2.39%

$700/sqft

06/30/2025

Source: mls_logoBright MLS-NJ #MDAA2115396

Listed for Sale

$1,675,000 +17.54%

$683/sqft

03/11/2022

Source: mls_logoBright MLS-NJ #MDAA2023680

Sold

$1,425,000

$581/sqft

Nearby Homes

Based on information from Bright MLS through Nov 04, 2026, 06:00AM. 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. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. © 2026 Bright MLS, Inc. All Rights Reserved. Click here for more information

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