Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$1,680,000

  • For Sale
  • Under Contract
  • Single Family
  • 3 Beds
  • 3 Full Baths
  • 3,699 Sq. Ft.
  • Updated 7 days ago
See This Home
Save This Home
See This Home
Save 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.

Full Property Details for 3 Chester Ave

General

  • Price: $1,680,000
  • Taxes: $12,991 (2024)
  • Status: Under Contract
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDAA2131360
  • Updated: 1/12/2026
  • Added to Site: 59 day(s) ago

Interior

  • 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)
  • Fireplace: Yes
  • Number of Fireplaces: 3
  • Fireplace(s): Mantel(s), Screen
  • Appliances: Dishwasher, Disposal, Dryer, Icemaker, Microwave, Refrigerator, Washer, Oven/Range - Electric, Water Heater
  • Flooring: Hardwood, Carpet, Ceramic Tile

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3
  • Upper Floor Baths: 2
  • Upper - Full Baths: 2
  • Main Floor Baths: 1
  • Main - Full Baths: 1

Bedrooms

  • Total Bedrooms: 3
  • Bedrooms Upper: 3

Other Rooms

  • Laundry: Main Floor

Additional Information

  • Security/Safety: Security System, Smoke Detector

Exterior

  • Exterior Features: Exterior Lighting, Extensive Hardscape
  • Porch/Patio/Deck: Patio(s), Porch(es), Screened, Roof, Balcony

Parking

  • Parking Features: Stone Driveway
  • Parking Type: Driveway, On Street

Location

  • Municipality: Annapolis
  • County: ANNE ARUNDEL
  • Subdivision: EASTPORT
  • Driving Directions: From downtown Annapolis go over Spa Creek bridge turn left on Chester follow to the end of the peninsula. House is on right.
  • City Limits: Yes

School Information

  • School District: Anne Arundel County Public Schools

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C, Ceiling Fan(s), Zoned
  • Cooling Fuel: Electric
  • Heating Type: Forced Air, Heat Pump(s), Zoned, Baseboard - Electric
  • Heating Fuel: Electric, Oil
  • Water Heater: Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Dist. to Water: 1 Blocks

Structural Information

  • Architectural Style: Cape Cod
  • Structure Type: Detached
  • Model: Charming Eastport Cape Cod
  • Construction: Combination
  • Basement: Yes
  • Basement Desc.: Connecting Stairway, Interior Access, Unfinished, Water Proofing System
  • Foundation: Other
  • Roof: Shingle
  • Walls/Ceilings: Plaster Walls, 9'+ Ceilings, Vaulted Ceilings
  • Stories Description: Lower 1, Main, Upper 1, Upper 2
  • Square Feet: 3,699
  • Sq. Ft. Source: Estimated
  • Living Area: 2,815 Sq. Ft.
  • Finished Above Grnd: 2,815 Sq. Ft.
  • Year Built: 1952
  • Year Built Source: Estimated

Additional Structures

  • Other Structures: Shed

Lot Features

  • Property View: Garden/Lawn
  • Lot Size (Acres): 0.13
  • Lot Size (Sq. Ft.): 5,850
  • Lot Size Source: Estimated
  • Zoning: R2NC
  • Lot Description: Landscaping, Level, Rear Yard
  • Fencing (Description): Rear

Water Features

  • Navigable Water: Yes
  • Water Access: Yes
  • Water Access Desc: Canoe/Kayak, Fishing Allowed, Public Access
  • Water Front Type: Creek/Stream
  • Water Front Name: Back Creek/Severn River

Financial Considerations

  • Price Per Sq. Ft.: $596.8
  • Assessment Year: 2025
  • City/TownTax: $6,672
  • City/TownTax Freq: Annually
  • County Tax: $6,319
  • County Tax Freq: Annually
  • Tax w/Assessment: $992,633
  • Tax Amount: $12,991
  • Tax Year: 2024

Disclosures and Reports

  • Ownership: Fee Simple
  • Lot Number: 26

Listed by Keller Williams Select Realtors of Annapolis, Victor Pascoe

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 3 Chester Ave —

  • Victor Pascoe

    Keller Williams Select Realtors of Annapolis

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 3 Chester Ave

School District:Anne Arundel County Public Schools
NameGradesDistance
Eastport Elementary School
420 Fifth Street, Annapolis, MD 21403
PK-50.4 mi
Annapolis Middle School
1399 Forest Drive, Annapolis, MD 21403
6-82.1 mi
Annapolis High School
2700 Riva Road, Annapolis, MD 21401
9-124.9 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 3 Chester Ave Get Price Alerts and Save Property

Date
Details
Price
Change
Source
1/02/2026
Price Reduced
$1,680,000
-2.89%
MLS
11/22/2025
Listed
$1,730,000
0.87%
MLS
8/08/2025
Sold
$1,715,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 3 Chester Ave

Year
Property Taxes
Change
Tax Assessment
Change
2025
$14,224
21%
$992,633
10%
2023
$11,711
—
$904,067
11%
2023
$11,711
3%
$815,500
1%
2022
$11,409
3%
$809,700
1%
2018
$11,102
-1%
$803,900
1%
2021
$11,253
—
$798,100
—
2020
$11,261
1%
$798,100
—
2019
$11,102
4%
$798,100
-2%
2018
$10,667
1%
$817,400
2%
2017
$10,520
1%
$803,633
2%
2016
$10,371
1%
$789,867
2%
2015
$10,283
11%
$776,100
—
2014
$9,261
—
$776,100
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 3 Chester Ave

$
Down Payment
%
$
%

$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Keller Williams Select Realtors of Annapolis, Victor Pascoe

Similar Properties near 3 Chester Ave

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

1836 Burley Ln, Annapolis, MD 21409 - Photo 1
$1,695,000

1836 Burley Ln  Annapolis, MD 21409

  • Single Family
  • Active
  • Updated 2 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,240
    Sq. Ft.
Listed by Long & Foster Real Estate, Inc., Jacquelyn K Reinauer
315 Cove Rd, Riva, MD 21140 - Photo 1 Just Listed
$1,695,000

315 Cove Rd  Riva, MD 21140

  • Single Family
  • Active
  • Updated 4 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 3,568
    Sq. Ft.
Listed by Long & Foster Real Estate, Inc., Reid Buckley
3300 Shore Dr, Annapolis, MD 21403 - Photo 1
$1,650,000

3300 Shore Dr  Annapolis, MD 21403

  • Single Family
  • Active
  • 4
    Beds
  • 4
    Total Baths
  • 2,798
    Sq. Ft.
Listed by Long & Foster Real Estate, Inc., John J Collins
394 North Dr, Severna Park, MD 21146 - Photo 1
$1,675,000

394 North Dr  Severna Park, MD 21146

  • Single Family
  • Active
  • 2
    Beds
  • 3
    Total Baths
  • 3,242
    Sq. Ft.
Listed by Synergy Realty, Kathleen A May

Just Listed near 3 Chester Ave

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

208 Admirals Ct, Arnold, MD 21012 - Photo 1 Just Listed
$680,000

208 Admirals Ct  Arnold, MD 21012

  • Townhouse
  • Active
  • Updated 5 days ago
  • 4
    Beds
  • 4
    Total Baths
  • 2,919
    Sq. Ft.
Listed by Long & Foster Real Estate, Inc., DeAnna W Miller
559 Melissa Ct, Arnold, MD 21012 - Photo 1 Just Listed
$408,950

559 Melissa Ct  Arnold, MD 21012

  • Townhouse
  • Active
  • Updated 1 day ago
  • 3
    Beds
  • 4
    Total Baths
  • 1,680
    Sq. Ft.
Listed by EXP Realty, LLC, Rachel Gontkovic
923 Whitstable Blvd, Arnold, MD 21012 - Photo 1 Just Listed
$685,000

923 Whitstable Blvd  Arnold, MD 21012

  • Townhouse
  • Active
  • Updated 2 days ago
  • 4
    Beds
  • 4
    Total Baths
  • 2,880
    Sq. Ft.
Listed by Long & Foster Real Estate, Inc., Kara Chaffin Donofrio and Long & Foster Real Estate, Inc., Kayla Stephens
276 Southdale Ct, Dunkirk, MD 20754 - Photo 1 Just Listed
$625,000

276 Southdale Ct  Dunkirk, MD 20754

  • Single Family
  • Active
  • Updated 4 hours ago
  • 4
    Beds
  • 3
    Total Baths
  • 3,258
    Sq. Ft.
Listed by Long & Foster Real Estate, Inc., Rita A Ilg

Price Reduced near 3 Chester Ave

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

1078 Bright Leaf Ct, Arnold, MD 21012 - Photo 1 Price Reduced
-$11,000 (-2.12%)
$509,000

1078 Bright Leaf Ct  Arnold, MD 21012

  • Single Family
  • Active
  • Updated 5 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 1,780
    Sq. Ft.
Listed by Michelle Boretti (410) 980-5906
795 Match Point Dr, Arnold, MD 21012 - Photo 1 Price Reduced
-$5,000 (-1.36%)
$363,000

795 Match Point Dr  Arnold, MD 21012

  • Single Family
  • Active
  • Updated 4 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,368
    Sq. Ft.
Listed by Samson Properties, Robert J Chew and Samson Properties, Betty Ban
1241 Tamarack Trail, Arnold, MD 21012 - Photo 1 Price Reduced
-$15,000 (-2.61%)
$560,000

1241 Tamarack Trail  Arnold, MD 21012

  • Single Family
  • Active
  • Updated 4 days ago
  • 4
    Beds
  • 2
    Total Baths
  • 1,944
    Sq. Ft.
Listed by Compass, Jennifer K Melvin
99 Hummingbird Ct, Dunkirk, MD 20754 - Photo 1 Price Reduced
-$20,000 (-2.37%)
$825,000

99 Hummingbird Ct  Dunkirk, MD 20754

  • Single Family
  • Active
  • Updated 4 days ago
  • 4
    Beds
  • 5
    Total Baths
  • 5,899
    Sq. Ft.
Listed by EXP Realty, LLC, Kimberlee Randall

Recent Sales near 3 Chester Ave

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

3 Chester Ave, Annapolis, MD 21403 - Photo 1 Sold
$1,715,000

3 Chester Ave  Annapolis, MD 21403

  • Single Family
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 3,699
    Sq. Ft.
Listed by TTR Sotheby's International Realty, Bradley R Kappel and TTR Sotheby's International Realty, Alex M Clark
Sold by Keller Williams Select Realtors of Annapolis, Victor Pascoe
11 Chesapeake Landing, Annapolis, MD 21403 - Photo 1 Sold
$1,595,000

11 Chesapeake Landing  Annapolis, MD 21403

  • Townhouse
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 2,153
    Sq. Ft.
Listed by Connie Cadwell
Sold by Long & Foster Real Estate, Inc., Stephanie M Snyder
15 Chesapeake Landing, Annapolis, MD 21403 - Photo 1 Sold
$1,500,000

15 Chesapeake Landing  Annapolis, MD 21403

  • Townhouse
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 2,153
    Sq. Ft.
Listed by Compass, Shane C Hall
Sold by Keller Williams Select Realtors of Annapolis, Victor Pascoe
541 Second St, Annapolis, MD 21403 - Photo 1 Sold
$1,470,000

541 Second St  Annapolis, MD 21403

  • Single Family
  • Closed
  • 4
    Beds
  • 3
    Total Baths
  • 2,341
    Sq. Ft.
Listed by Berkshire Hathaway HomeServices PenFed Realty, Betty W Jans
Sold by Long & Foster Real Estate, Inc., Jacquelyn K Reinauer

3 Chester Avenue, Annapolis, MD 21403 (MLS# MDAA2131360) is a Single Family property with 3 bedrooms and 3 full bathrooms. 3 Chester Avenue is currently listed for $1,680,000 and was received on November 22, 2025. Want to learn more about 3 Chester Avenue? Do you have questions about finding other Single Family real estate for sale in Annapolis? You can browse all Annapolis real estate or contact a Coldwell Banker agent to request more information.

Tour this property