123 CHESAPEAKE AVE, Annapolis, MD 21403
See all 37 photos
123 CHESAPEAKE AVE, Annapolis, MD 21403
123 CHESAPEAKE AVE, Annapolis, MD 21403
123 CHESAPEAKE AVE, Annapolis, MD 21403
123 CHESAPEAKE AVE, Annapolis, MD 21403
REQUEST A TOUR If you would like to see this home without being there in person, select the "Virtual Tour" option and your agent will contact you to discuss available opportunities.
In-PersonVirtual Tour
Listed by Sarah Greenlee Morse • TTR Sotheby's International Realty
$ 1,595,000
Est. payment /mo
Coming Soon

123 CHESAPEAKE AVE Annapolis, MD 21403

4 Beds

5 Baths

3,020 SqFt


UPDATED:

Key Details

Property Type Single Family Home, Townhouse

Sub Type Twin/Semi-Detached

Listing Status Coming Soon

Purchase Type For Sale

Square Footage 3,020 sqft

Price per Sqft $528

Subdivision Eastport

MLS Listing ID MDAA2157850

Style Craftsman

Bedrooms 4

Full Baths 4

Half Baths 1

HOA Y/N N

Abv Grd Liv Area 2,344

Year Built 2007

Available Date 2026-09-30

Annual Tax Amount $19,532

Tax Year 2026

Lot Size 3,526 Sqft

Acres 0.08

Property Sub-Type Twin/Semi-Detached

Source BRIGHT

Property Description

COMING SOON - expected on the market September 30th. Rare Lower Eastport opportunity: spacious townhome with a separately licensed one-bedroom detached cottage and proven rental income.

Enjoy the charm and walkability of Lower Eastport from this thoughtfully updated 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 approximately 2,300 square feet of combined above-grade living space, including the 670-square-foot detached cottage, plus an additional 800 square feet of finished lower-level space in the main residence. This unique configuration combines generous living space with an exceptional degree of flexibility rarely found in Eastport.

Enter the main residence through a charming raised covered porch that overlooks the tree lined street. This home offers three bedrooms and three and a half baths, with a separate dining room, open kitchen flowing into the living room and out onto a covered porch overlooking the fenced-in backyard.

Upstairs, the spacious primary suite overlooks the backyard and features a large walk-in closet and adjoining newly renovated bath. A second bedroom with its own private bath provides comfort and privacy for family or guests. Custom plantation shutters throughout the main and top floors add a polished finish and privacy.

The finished lower level adds approximately 800 square feet of versatile living space and is currently configured as a family/TV room and third bedroom with a full bath, laundry, additional storage and private entrance to the back yard.

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 new LVP flooring, kitchen cabinetry, full-size appliances and an updated bathroom. Most recently rented for $2,935 per month, 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.

Since purchasing the property in January 2025, the current owners have invested more than $100,000 in improvements. A full list of improvements is available from the listing agent.

There is no off-street parking, however, ample street parking is available at this quiet end of Eastport. The property's east of Second St. location is approximately two blocks from 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.

A newer Eastport home, substantial finished living space, and a separate cottage with proven rental income of more than $35,000 annually – an opportunity that is difficult to replicate.

Location

State MD

County Anne Arundel

Zoning RESIDENTIAL

Rooms

Basement Daylight, Partial, Fully Finished, Outside Entrance, Sump Pump, Walkout Stairs, Interior Access

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

Hot Water Electric, Natural Gas

Heating Forced Air, Heat Pump(s)

Cooling Ceiling Fan(s), Central A/C

Flooring Wood

Fireplaces Number 1

Fireplaces Type Corner, Heatilator

Equipment Built-In Microwave, Oven/Range - Gas, Refrigerator, Stainless Steel Appliances

Furnishings No

Fireplace Y

Appliance Built-In Microwave, Oven/Range - Gas, Refrigerator, Stainless Steel Appliances

Heat Source Electric

Laundry Lower Floor

Exterior

Exterior Feature Brick, Deck(s), Patio(s)

Fence Privacy, Rear, Vinyl, Wood

Water Access N

View City

Roof Type Composite,Shingle

Street Surface Black Top

Accessibility None

Porch Brick, Deck(s), Patio(s)

Road Frontage City/County

Garage N

Private Pool No

Building

Lot Description Landscaping, PUD, Rear Yard

Story 3

Foundation Concrete Perimeter

Above Ground Finished SqFt 2344

Sewer Public Sewer

Water Public

Architectural Style Craftsman

Level or Stories 3

Additional Building Above Grade, Below Grade

Structure Type 9'+ Ceilings,Tray Ceilings

New Construction N

Schools

School District Anne Arundel County Public Schools

Others

Pets Allowed Y

Senior Community No

Tax ID 020600003976115

Ownership Fee Simple

SqFt Source 3020

Security Features Smoke Detector

Horse Property N

Special Listing Condition Standard

Pets Allowed Cats OK, Dogs OK

Virtual Tour https://download.dnmq-visuals.com/123_chesapeake_ave-6357/virtual-tour


Bright MLS (BMLS)

NEARBY SCHOOLS & PROPERTIES

Jamila Carr

Jamila Carr

Broker Associate

+1(202) 200-1520

GET MORE INFORMATION

Name
Phone*
Message
Go tour this home

123 CHESAPEAKE AVE