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$1,595,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 3,106 Sq. Ft.
  • Updated 1 day ago
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Just Listed! Exceptional Lower Eastport property: tastefully updated, semi-detached home with a detached one-bedroom cottage with proven rental income. Enjoy the charm and walkability of Lower Eastport from this 2007-built home on a peaceful, tree-lined street just two blocks from the harbor and close to parks, restaurants, shops and the waterfront. The property offers over 3000 square feet of living space between the main house and the cottage. Two dwellings make up a unique configuration that allows an exceptional degree of flexibility and privacy. Enter the main residence through a classic Eastport front porch, perfect for rocking chairs and enjoying views of the neighborhood. The home features three bedrooms and three-and-a-half baths, a separate dining room, and an open kitchen adjoining a spacious living room. Sliding doors extend the living space to a covered porch overlooking the fenced backyard. Upstairs, the spacious primary suite features a large walk-in closet and adjoining newly renovated bath. A second bedroom with its own hall bath provides privacy for family or guests. Custom plantation shutters throughout the main and top floors add a polished finish and privacy. About 800 square feet of living space on the lower level is currently configured as a family/TV room and third bedroom. Also downstairs are a full bath, laundry, and several storage spaces. This area can be accessed from the interior as well as from its own entrance to the back yard, which allows for added privacy. At the rear of the property is the true standout: a stand-alone 670 square feet, one bedroom, one bath cottage licensed for full-time rental use. Extensively renovated in 2025, the cottage features LVP flooring, kitchen cabinetry, full-size appliances and an updated bathroom. Recently rented for $2,935 per month and garnering more than $35,000 annually, the cottage will be vacant at closing, giving the next owner the flexibility to rent it, use it for family or guests, create a private home office, or accommodate multigenerational living. The current owners have invested more than $100,000 in property upgrades over the past 18 months including new and updated baths; the cottage remodel; extensive electrical, lighting, and hardware upgrades; replacement A/C; interior and exterior painting; and landscaping. Ample street parking, with no parking fees for visitors, is available at this quiet residential end of Eastport. The property's location between First and Second Streets is approximately two blocks from both Horn Point and Spa Creek. This offers the best of the neighborhood's relaxed waterfront lifestyle while also remaining close to some of the best restaurants in Annapolis and just over the bridge from downtown Annapolis. This attractively updated Eastport home, complemented by a rentable cottage, presents a unique and appealing opportunity in one of Annapolis's most popular neighborhoods.

Full Property Details for 123 Chesapeake Ave

General

  • Price: $1,595,000
  • Taxes: $19,532 (2026)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDAA2157850
  • Updated: 9/30/2026
  • Added to Site: 1 day(s) ago

Interior

  • Interior Features: Bathroom - Walk-In Shower, Breakfast Area, Built-Ins, Ceiling Fan(s), Combination Kitchen/Living, Dining Area, Family Room Off Kitchen, Floor Plan - Open, Formal/Separate Dining Room, Kitchen - Island, Primary Bath(s), Upgraded Countertops, Wood Floors
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Corner, Heatilator
  • Appliances: Built-In Microwave, Oven/Range - Gas, Refrigerator, Stainless Steel Appliances
  • Flooring: Wood

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1
  • Upper Floor Baths: 3
  • Upper - Full Baths: 3
  • Main Floor Baths: 1
  • Main - 1/2 Baths: 1
  • Lower Floor Baths: 1
  • Lower - Full Baths: 1

Bedrooms

  • Total Bedrooms: 4
  • Bedrooms Upper: 3
  • Bedrooms Lower: 1

Other Rooms

  • Laundry: Lower Floor

Additional Information

  • Security/Safety: Smoke Detector

Exterior

  • Exterior Features: Extensive Hardscape, Exterior Lighting, Gutter System, Outbuilding(s), Underground Lawn Sprinkler
  • Porch/Patio/Deck: Brick, Deck(s), Patio(s)

Parking

  • Parking Type: On Street

Location

  • Municipality: Annapolis
  • County: ANNE ARUNDEL
  • Subdivision: EASTPORT
  • Cross Streets: Second Street
  • Driving Directions: Chesapeake Avenue between First and Second Streets
  • Location Details: Urban
  • City Limits: Yes

School Information

  • School District: Anne Arundel County Public Schools

Community

  • Pets Allowed: Yes
  • Pets: Cats OK, Dogs OK

Heating & Cooling

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

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Dist. to Water: 3 Blocks

Structural Information

  • Architectural Style: Craftsman
  • Structure Type: Twin/Semi-Detached
  • Construction: Vinyl Siding
  • Basement: Yes
  • Basement Entrance: Yes
  • Basement Desc.: Daylight, Partial, Fully Finished, Outside Entrance, Sump Pump, Walkout Stairs, Interior Access
  • Foundation: Concrete Perimeter
  • Roof: Composite, Shingle
  • Walls/Ceilings: 9'+ Ceilings, Tray Ceilings
  • Entry Floor Number: 2
  • Stories Description: Lower 1, Main, Upper 1
  • Square Feet: 3,106
  • Sq. Ft. Source: Estimated
  • Living Area: 3,020 Sq. Ft.
  • Finished Above Grnd: 2,344 Sq. Ft.
  • Finished Below Grnd: 676 Sq. Ft.
  • Year Built: 2007
  • Year Built Source: Assessor
  • Property Condition: Excellent

Unit Information

  • Unit Floor in Bldg.: 3

Unit 1

  • Bathrooms-Lower: 1
  • Bedrooms-Lower: 1

Lot Features

  • Property View: City
  • Lot Size (Acres): 0.08
  • Lot Size (Sq. Ft.): 3,526
  • Lot Size Source: Assessor
  • Street/Road Desc.: Black Top
  • Zoning: RESIDENTIAL
  • Lot Description: Landscaping, PUD, Rear Yard
  • Fencing (Description): Privacy, Rear, Vinyl, Wood

Water Features

  • Water Front Type: Bay
  • Water Front Name: Spa Creek, Back Creek, Chesapeake Bay

Financial Considerations

  • Price Per Sq. Ft.: $680.46
  • Assessment Year: 2026
  • City/TownTax: $10,101
  • City/TownTax Freq: Annually
  • County Tax: $9,431
  • County Tax Freq: Annually
  • Tax w/Assessment: $1,368,800
  • Tax Amount: $19,532
  • Tax Year: 2026
  • Tax Total Finished Sq. Ft.: 2965

Disclosures and Reports

  • Ownership: Fee Simple

Listed by TTR Sotheby's International Realty, Sarah Greenlee Morse

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Listing agent

— 123 Chesapeake Ave —

  • Sarah Greenlee Morse

    TTR Sotheby's International Realty

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 123 Chesapeake Ave

School District:Anne Arundel County Public Schools
NameGradesDistance
Eastport Elementary School
420 Fifth Street, Annapolis, MD 21403
PK-50.3 mi
Annapolis Middle School
1399 Forest Drive, Annapolis, MD 21403
6-82 mi
Annapolis High School
2700 Riva Road, Annapolis, MD 21401
9-124.7 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 123 Chesapeake Ave Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/30/2026
Listed
$1,595,000
10%
MLS
1/15/2025
Sold
$1,450,000
—
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 123 Chesapeake Ave

Year
Property Taxes
Change
Tax Assessment
Change
2025
$16,499
—
$1,368,800
19%
2025
$16,499
60%
$1,151,333
23%
2023
$10,288
—
$933,867
30%
2023
$10,288
2%
$716,400
—
2022
$10,094
2%
$716,400
—
2018
$9,915
-6%
$716,400
-4%
2021
$10,545
2%
$747,900
2%
2020
$10,305
4%
$730,333
2%
2019
$9,915
9%
$712,767
3%
2018
$9,072
—
$695,200
—
2017
$9,100
—
$695,200
—
2016
$9,128
-2%
$695,200
-2%
2015
$9,362
—
$706,600
—
2014
$9,405
—
$706,600
—
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.

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NMLS#: 1598647

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Listed by TTR Sotheby's International Realty, Sarah Greenlee Morse

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123 Chesapeake Avenue, Annapolis, MD 21403 (MLS# MDAA2157850) is a Single Family property with 4 bedrooms, 4 full bathrooms and 1 partial bathroom. 123 Chesapeake Avenue is currently listed for $1,595,000 and was received on September 30, 2026. Want to learn more about 123 Chesapeake 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.

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