Back to Search
123 Chesapeake Ave, Annapolis, MD 21403
123 Chesapeake Ave, Annapolis, MD 21403
123 Chesapeake Ave, Annapolis, MD 21403
123 Chesapeake Ave, Annapolis, MD 21403
123 Chesapeake Ave, Annapolis, MD 21403
123 Chesapeake Ave, Annapolis, MD 21403
123 Chesapeake Ave, Annapolis, MD 21403

123 Chesapeake Ave Annapolis, MD 21403

1Views
0Saves

$1,595,000

COMING SOON
Beds
4
Baths
5
Sqft
3,020
Acres
0.08
Year
2007
Days on Site
1 Hour
Property Type
Residential
Sub Type
Per Square Foot
$528
Date Listed
Sep 26, 2026

Description of 123 Chesapeake Ave, Annapolis, MD 21403

Listing details for 123 Chesapeake Ave, Annapolis, MD 21403 : COMING SOON - expected on the market September 30th. Enjoy the historic and neighborhood charm of Lower Eastport in this beautifully renovated, turn-key home on a peaceful, tree-lined street just blocks from the water, parks, shops, and restaurants. The property features a three-bedroom, three-and-a-half-bath main house and a one-bedroom cottage at the rear of the property, providing an additional bedroom and full bath along with the privacy and independence of a separate dwelling. The current owners have invested more than $100,000 in renovations since 2024. The main house, built in 2007, is thoughtfully designed for entertaining with an open kitchen, adjoining living room, separate dining space, front and back porches with seating areas, and a fully fenced backyard. Upstairs, the spacious ensuite primary bedroom overlooks the backyard and features a large walk-in closet and adjoining bath. A second bedroom and hallway full bath complete the upper level. The lower level is currently used as a family room and third bedroom and includes a full bath, laundry, additional storage, and a private outside entrance. Custom plantation shutters throughout enhance the aesthetic appeal of the home, offer excellent light control, and provide privacy. At the rear of the property, the cottage is a valuable addition with an upstairs bedroom, full bath, kitchen, living and dining area, and laundry. It is ideal for housing family members or guests or generating rental income. The cottage has its own electric meter and is licensed for rental; current owners have generated nearly $36,000 in rental income over the past 12 months from long-term tenants. With its prime Lower Eastport setting, quality updates, and separate cottage, this property offers exceptional flexibility for family, guests, or rental income. This combination is uncommon in Annapolis and offers a truly distinctive opportunity. Note: Finished square footage and bedroom and bathroom totals reflect the combined main house and cottage. The main house has 2,344 finished square feet plus 86 unfinished square feet; the cottage has 667 finished square feet.
Listing Updated : 09-26-2026 at 2:01 PM EDT
Listing Provided By : Sarah Greenlee Morse, 4103031522, [email protected], TTR Sotheby's International Realty
Source :

Bright MLS, MLS#: MDAA2157850

For more information on this listing contact us at (202) 441-2348

Property History

DateEventPrice
9/26/2026
Coming Soon
$1,595,000
$528/sqft
Source:Bright MLS #MDAA2157850
Home Worth Check

Interested in 123 Chesapeake Ave, Annapolis, MD 21403?

I agree to be contacted by Dell Residential Group via call, email, and text for real estate services. To opt out, you can reply 'stop' at any time or reply 'help' for assistance. You can also click the unsubscribe link in the emails. Message and data rates may apply. Message frequency may vary. For more information, please review our Privacy Policy.

Location of 123 Chesapeake Ave, Annapolis, MD 21403

Streetview of 123 Chesapeake Ave, Annapolis, MD 21403

Mortgage Calculator
Listing Price
Down Payment
Interest Rate

Schools Near 123 Chesapeake Ave, Annapolis, MD 21403

For more information on this listing contact us at (202) 441-2348

Homes Similar to 123 Chesapeake Ave, Annapolis, MD 21403

Recent Blog Post By Category

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement. 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. Copyright 2026 Bright MLS, Inc.
HomeAnnapolisEastport
For more information on this listing contact us at (202) 441-2348