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Own your own land in the Eastport area with no condo fee, no HOA, and no pet restrictions. This single-level, two-bedroom, two-full-bath home has a new roof, central air, and a private patio and backyard just outside the sliding glass doors of the primary bedroom. The kitchen is bright from two sides plus a skylight, with a pass-through and eat-in counter for coffee or casual meals. Wood floors, ceiling fans, and a main-floor laundry make daily life easy, and an off-street parking pad and a shed for bikes, tools, and seasonal gear add storage and convenience. At 800 square feet, it’s a manageable, low-upkeep step from a condo or rental into homeownership, about 10 minutes from downtown Annapolis. Photos have been virtually staged.

2 Beds ⋅ 2 Baths

Own your own land in the Eastport area with no condo fee, no HOA, and no pet restrictions. This single-level, two-bedroom, two-full-bath home has a new roof, central air, and a private patio and backyard just outside the sliding glass doors of the primary bedroom. The kitchen is bright from two sides plus a skylight, with a pass-through and eat-in counter for coffee or casual meals. Wood floors, ceiling fans, and a main-floor laundry make daily life easy, and an off-street parking pad and a shed for bikes, tools, and seasonal gear add storage and convenience. At 800 square feet, it’s a manageable, low-upkeep step from a condo or rental into homeownership, about 10 minutes from downtown Annapolis. Photos have been virtually staged.

1136 Tyler Ave, Annapolis

Listing courtesy of Engel & Volkers Washington, DC. Contact:

$1,199,000

This charming historic Eastport home was built in the early 1900s and moved to Second Street in 1937. David Fogle, renowned preservationist architect and professor, purchased the home in 1970s and designed the light-filled addition featuring Palladium windows and architectural angles. The home bridges the integrity of the past to the present with its original Heart Pine floors on the main level. The current owners did a full kitchen renovation to include custom-built Heartwood cherry cabinets, dry/wet bar, and granite countertops with plenty of room for food prep and entertaining! The combined living room/dining room area is spacious and open while the comfortable family room opens to the front porch and overlooks a lovely flower garden. The family room opens to a brick patio and a large partially- fenced backyard that is ideal for warm weather entertaining. Lots of custom bookshelves throughout, and there are two gas fireplaces on the main level for added charm and ambiance in the cold weather! Full bathroom on the first floor. The spacious bright primary bedroom on the second floor features skylights and windows that offer views of the private backyard. Second bedroom is perfect for an office/guest room with Murphy bed. The coveted off-street parking accommodates four cars. The house is located in the heart of Eastport's historic maritime neighborhoods where watermen made a living from fishing, crabbing, and oystering. The front porch on this friendly street is the perfect spot for impromptu gatherings with neighbors and friends. Easy walk to marinas on Back and Spa Creeks, the Maritime Museum, yacht clubs, restaurants, pubs and shops; access to seasonal water taxi transport to downtown Annapolis. Eastport charm at its best!

2 Beds ⋅ 3 Baths

This charming historic Eastport home was built in the early 1900s and moved to Second Street in 1937. David Fogle, renowned preservationist architect and professor, purchased the home in 1970s and designed the light-filled addition featuring Palladium windows and architectural angles. The home bridges the integrity of the past to the present with its original Heart Pine floors on the main level. The current owners did a full kitchen renovation to include custom-built Heartwood cherry cabinets, dry/wet bar, and granite countertops with plenty of room for food prep and entertaining! The combined living room/dining room area is spacious and open while the comfortable family room opens to the front porch and overlooks a lovely flower garden. The family room opens to a brick patio and a large partially- fenced backyard that is ideal for warm weather entertaining. Lots of custom bookshelves throughout, and there are two gas fireplaces on the main level for added charm and ambiance in the cold weather! Full bathroom on the first floor. The spacious bright primary bedroom on the second floor features skylights and windows that offer views of the private backyard. Second bedroom is perfect for an office/guest room with Murphy bed. The coveted off-street parking accommodates four cars. The house is located in the heart of Eastport's historic maritime neighborhoods where watermen made a living from fishing, crabbing, and oystering. The front porch on this friendly street is the perfect spot for impromptu gatherings with neighbors and friends. Easy walk to marinas on Back and Spa Creeks, the Maritime Museum, yacht clubs, restaurants, pubs and shops; access to seasonal water taxi transport to downtown Annapolis. Eastport charm at its best!

531 Second St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$1,595,000

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 is now vacant, 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.

4 Beds ⋅ 5 Baths

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 is now vacant, 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.

123 Chesapeake Ave, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

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