123 Chesapeake Avenue, ANNAPOLIS, Maryland image 1

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MLS: #MDAA2157850, Listed By: Sarah Greenlee Morse, TTR Sotheby's International Realty, Source:Bright MLS

123 Chesapeake Avenue

ANNAPOLIS, MD 21403

$1,595,000 $6,724/Mo

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Overview

Bed

Bath

3,020

Sqft

0.08

Acre(Lot)

Description

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 adjo ining 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.

Property Details

Property Type : Residential

Price : $1,595,000

AD Id : 91537417

MLS Id : MDAA2157850

Beds : 4

Lot Size : 0.08 Acre

Living Area Size : 3,020 Sq. Ft

Tax Amount : $19,532

Year Built : 2007

County : ANNE ARUNDEL

Subdivision: Eastport

Map

What's Nearby

Nearby Areas

Features

Bedroom Information

Total beds: 4

Bathroom Information

Total Baths: 5 Full Baths: 4 Half Baths: 1

Room Information

Has Basement: Yes Basement: Finished, Exterior Entry, Walk-Out Access, Daylight, Partial, Sump Pump, Interior Entry
Flooring Information

Wood
Roofing Information

Composition, Shingle
Interior Features

Ceiling Fan(s), Kitchen Island, High Ceilings, Tray Ceiling(s), Built-in Features, Open Floorplan Roof: Composition, Shingle Appliances: Gas Range, Gas Oven, Electric Water Heater, Gas Water Heater, Refrigerator, Stainless Steel Appliance(s), Microwave Laundry Features: Lower Level
Heating & Cooling

Has Heating: Yes Heating: Electric, Forced Air, Heat Pump Has Cooling: Yes Cooling: Central Air, Ceiling Fan(s), Electric

Building Information

Year Built: 2007 Building Area Total: 3106 Construction Materials: Vinyl Siding Patio And Porch Features: Deck, Patio Pool Features: None Private Pool: No View: City
Exterior Features

Exterior Features: Lighting, Rain Gutters

Lot Information

Lot Size Acres: 0.08 Lot Size Source: Assessor Lot Size Square Feet: 3526 Lot Description: Back Yard

Property Information

Subdivision: EASTPORT Source Property Type: Residential Postal Code Plus 4: 4147 Property SubType: Townhouse Levels: Three Or More Property Age: 19

Listing Price Information

Listing Price: $1595000

Tax Information

Parcel Number: 020600003976115 Tax Year: 2026 Annual Tax: $19532

Parking Information

On Street

Garage Information

Pets Allowed: Cats OK, Dogs OK, Yes

Location Information

Direction: Chesapeake Avenue between First and Second Streets WaterSource: Public Security Features: Smoke Detector(s)

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1045 Cedar Ridge Court, Annapolis, MD, 21403	$399,900	3	3	1,320	0.04 Acre
19 Boucher Place, Annapolis, MD, 21403	$799,000	3	4	1,800	0.05 Acre
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ByOwner last updated this listing 10/01/2026 @ 09:24

MLS: MDAA2157850 LISTED BY: Sarah Greenlee Morse, TTR Sotheby's International Realty 410-280-5600 SOURCE: Bright MLS