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SIMULCAST AUCTION. Online pre-bidding begins November 17, 2026 at 10:00 AM ET. Live bidding begins November 19, 2026 at 1:00 PM ET, both on-site at 316 Chester Ave and online through the Ashland Auction Group bidding platform. List price is the suggested opening bid. A 10% buyer’s premium will be added to the high bid. On-site bidders must bring a $10,000 cashier’s check. Online bidders must register and complete the required credit card authorization. Pre-auction offers may be accepted. Built in 1920, this detached Eastport home offers 2 bedrooms and 2 full bathrooms. Inside, the home features a living room, dining room, hardwood floors, and an interior staircase. The outdoor space includes a patio and rear yard on approximately 0.07 acres. Butler’s Marina is nearby on Chester Avenue, and the Annapolis Maritime Museum’s waterfront campus is on Second Street. Eastport’s restaurants and marinas are nearby, with downtown Annapolis and City Dock across the Spa Creek Bridge. The property needs updates and is sold as-is.

316 Chester Ave, Annapolis

Listing courtesy of Ashland Auction Group LLC. Contact:

$315,000

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.

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:

$1,298,000

Skip the renovations and settle right into this Eastport gem. From top to bottom, flawlessly turnkey in every detail, this home invites you to immediately embrace the coveted downtown lifestyle. Custom-built in 2021, this 3200 sq ft home perfectly blends modern luxuries with classic Eastport charm. Fine finishes, 9-foot ceilings, stunning millwork, and gorgeous white oak floors set the tone. The heart is the chef’s kitchen with a show-stopping center island and granite counters. The kitchen is open to the light-filled family room, flanked by a cozy gas fireplace and custom built-ins. A versatile 4th bedroom or office, full bath, and chic beverage center complete the main level. Upstairs features a convenient laundry room, three spacious bedrooms—including a vaulted primary suite—and two beautifully appointed bathrooms with modern tile and granite vanities. The fully finished lower level adds a large recreation area, another full bath and ample storage. For outdoor living, the amazing 300-square-foot screened porch will quickly become a favorite spot. Step off the porch and enjoy the crafted stone patio, firepit and a fully fenced, grassy backyard. Perfectly positioned, you are just moments from Eastport's celebrated restaurants, marinas, and waterfront parks, with an easy stroll across the Spa Creek Bridge to Historic Downtown Annapolis. This exceptional turn-key offering delivers the best of Eastport living in a flawless package. Check out the Interactive Floor Plan!

Skip the renovations and settle right into this Eastport gem. From top to bottom, flawlessly turnkey in every detail, this home invites you to immediately embrace the coveted downtown lifestyle. Custom-built in 2021, this 3200 sq ft home perfectly blends modern luxuries with classic Eastport charm. Fine finishes, 9-foot ceilings, stunning millwork, and gorgeous white oak floors set the tone. The heart is the chef’s kitchen with a show-stopping center island and granite counters. The kitchen is open to the light-filled family room, flanked by a cozy gas fireplace and custom built-ins. A versatile 4th bedroom or office, full bath, and chic beverage center complete the main level. Upstairs features a convenient laundry room, three spacious bedrooms—including a vaulted primary suite—and two beautifully appointed bathrooms with modern tile and granite vanities. The fully finished lower level adds a large recreation area, another full bath and ample storage. For outdoor living, the amazing 300-square-foot screened porch will quickly become a favorite spot. Step off the porch and enjoy the crafted stone patio, firepit and a fully fenced, grassy backyard. Perfectly positioned, you are just moments from Eastport's celebrated restaurants, marinas, and waterfront parks, with an easy stroll across the Spa Creek Bridge to Historic Downtown Annapolis. This exceptional turn-key offering delivers the best of Eastport living in a flawless package. Check out the Interactive Floor Plan!

1010 Park Ave, Annapolis

Listing courtesy of Compass. Contact:

$1,795,000

Priced to Sell! This delightful and updated Eastport beauty embodies the true charm of Eastport! The classic style and curb appeal abound, and the updates are already done for you! Centrally located for easy access to shopping and restaurants in Eastport, as well as a quick trip to downtown Annapolis. Offering 4bedrooms (one on main level), 3.5 baths, a dedicated mudroom with a wet sink, a finished basement with storage, bar, and half bath. Hardwood flooring throughout. The original garage and car port are located on the rear alley. Sellers are offering completed architectural plans for an ADU - ready for submission. The front of the home (new sod) is the original bungalow with all of its charm, and a formal living room with an updated wood burning fireplace (2019). The fourth bedroom and full bath are on the main level. The upper level has a generously sized primary bedroom with a vaulted ceiling, multiple closets, and space for a desk, workout studio or expanded closets. The additional two bedrooms and bath on the upper level are generously sized and have hardwood flooring. Laundry is on the bedroom level. The main-level, hand-scraped white oak floors were re-sanded and given a matte finish in Oct 2026. Central to the rear addition in the gorgeous kitchen and great room with space for dining, two sitting rooms and a gas fireplace. The sizeable, fenced, backyard includes a large patio for entertaining, a detached finished game room/office that could be converted back to 2-car garage, and a car port and driveway with parking for 2-3 cars. Please note that the rear yard has an astro-turf product on it that was professionally installed for wear and proper drainage.

Priced to Sell! This delightful and updated Eastport beauty embodies the true charm of Eastport! The classic style and curb appeal abound, and the updates are already done for you! Centrally located for easy access to shopping and restaurants in Eastport, as well as a quick trip to downtown Annapolis. Offering 4bedrooms (one on main level), 3.5 baths, a dedicated mudroom with a wet sink, a finished basement with storage, bar, and half bath. Hardwood flooring throughout. The original garage and car port are located on the rear alley. Sellers are offering completed architectural plans for an ADU - ready for submission. The front of the home (new sod) is the original bungalow with all of its charm, and a formal living room with an updated wood burning fireplace (2019). The fourth bedroom and full bath are on the main level. The upper level has a generously sized primary bedroom with a vaulted ceiling, multiple closets, and space for a desk, workout studio or expanded closets. The additional two bedrooms and bath on the upper level are generously sized and have hardwood flooring. Laundry is on the bedroom level. The main-level, hand-scraped white oak floors were re-sanded and given a matte finish in Oct 2026. Central to the rear addition in the gorgeous kitchen and great room with space for dining, two sitting rooms and a gas fireplace. The sizeable, fenced, backyard includes a large patio for entertaining, a detached finished game room/office that could be converted back to 2-car garage, and a car port and driveway with parking for 2-3 cars. Please note that the rear yard has an astro-turf product on it that was professionally installed for wear and proper drainage.

830 Chester Ave, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$1,250,000

A Serene Retreat with Unforgettable Scenery... Enjoy breathtaking, unobstructed water views from every window in this inviting condominium, where peaceful surroundings meet comfortable living. Thoughtfully designed for relaxation and everyday convenience, this home offers a wonderful opportunity to wake up to beautiful scenery and unwind beside the water at the end of the day. Front-row balcony viewing of Blue Angels practice and show dates in May for Commissioning Week; Parade of Lights; Fireworks on 4th July and New Year’s Eve. Daily activity in the Annapolis Harbor. • Overlooking Spa Creek, Ego Alley, U.S. Naval Academy, Eastport Bridge, Severn River, Annapolis skyline. • Elevator • Secured Condo and Garage Building • The open-plan living, dining, and kitchen area is flooded with natural light. • A chef’s kitchen flanks the 10 ft island, maximized with new cabinet storage. • Appliances: Sub-Zero, Miele, Bertazzoni, Whirlpool • Kitchen and bath cabinets: natural Hickory and off-white flat-panel • The large walk-in closet and in-unit laundry connect the bedroom to the Kohler spa-like bath and separate vanity area. • Built-in cabinet for TV and electric fireplace • Walking distance to shops, pubs, and restaurants. • Water taxi 1 block away. • Local marinas, shopping, restaurants, pubs, and cafes within walking distance Whether you are looking for a full-time residence, a weekend getaway, or an investment opportunity, this condominium offers an exceptional setting and a lifestyle centered on the view. Come experience tranquility and charm for yourself.

1 Beds ⋅ 1 Baths

A Serene Retreat with Unforgettable Scenery... Enjoy breathtaking, unobstructed water views from every window in this inviting condominium, where peaceful surroundings meet comfortable living. Thoughtfully designed for relaxation and everyday convenience, this home offers a wonderful opportunity to wake up to beautiful scenery and unwind beside the water at the end of the day. Front-row balcony viewing of Blue Angels practice and show dates in May for Commissioning Week; Parade of Lights; Fireworks on 4th July and New Year’s Eve. Daily activity in the Annapolis Harbor. • Overlooking Spa Creek, Ego Alley, U.S. Naval Academy, Eastport Bridge, Severn River, Annapolis skyline. • Elevator • Secured Condo and Garage Building • The open-plan living, dining, and kitchen area is flooded with natural light. • A chef’s kitchen flanks the 10 ft island, maximized with new cabinet storage. • Appliances: Sub-Zero, Miele, Bertazzoni, Whirlpool • Kitchen and bath cabinets: natural Hickory and off-white flat-panel • The large walk-in closet and in-unit laundry connect the bedroom to the Kohler spa-like bath and separate vanity area. • Built-in cabinet for TV and electric fireplace • Walking distance to shops, pubs, and restaurants. • Water taxi 1 block away. • Local marinas, shopping, restaurants, pubs, and cafes within walking distance Whether you are looking for a full-time residence, a weekend getaway, or an investment opportunity, this condominium offers an exceptional setting and a lifestyle centered on the view. Come experience tranquility and charm for yourself.

100 Severn Ave Unit 507, Annapolis

Listing courtesy of Coastal Realty Maryland. 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:

$869,000

Enjoy the convenience and charm of Eastport living at 827 Bay Ridge, just a short walk to local restaurants, shops, marinas, parks, and downtown Annapolis. This updated and well-maintained 3-bedroom, 3-full-bath home offers comfortable, flexible living space. The main level features two bedrooms and two full baths, inviting living areas, hardwood floors, and an updated kitchen with white cabinetry, granite countertops, and stainless steel appliances. Just off the living and dining areas, the screened porch overlooks the private backyard, creating the perfect spot to relax or entertain. The lower level provides additional living space with a third bedroom and full bath, ideal for guests, a private retreat, or a home office. Outdoor features include a welcoming front porch, rear patio, private backyard, and a driveway conveniently located behind the home, along with a storage shed. Whether you’re looking for a full-time residence or a weekend getaway, this turnkey home has everything that makes coastal living so desirable!

Enjoy the convenience and charm of Eastport living at 827 Bay Ridge, just a short walk to local restaurants, shops, marinas, parks, and downtown Annapolis. This updated and well-maintained 3-bedroom, 3-full-bath home offers comfortable, flexible living space. The main level features two bedrooms and two full baths, inviting living areas, hardwood floors, and an updated kitchen with white cabinetry, granite countertops, and stainless steel appliances. Just off the living and dining areas, the screened porch overlooks the private backyard, creating the perfect spot to relax or entertain. The lower level provides additional living space with a third bedroom and full bath, ideal for guests, a private retreat, or a home office. Outdoor features include a welcoming front porch, rear patio, private backyard, and a driveway conveniently located behind the home, along with a storage shed. Whether you’re looking for a full-time residence or a weekend getaway, this turnkey home has everything that makes coastal living so desirable!

827 Bay Ridge Ave, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. 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:

$765,000

Welcome to 312 Severn Avenue, Unit W308—a rarely available two-story, two-bedroom, two-bath condominium at The Tecumseh, one of Eastport’s most distinctive waterfront communities. Located on the third floor, this approximately 1,390-square-foot residence offers a unique two-level layout with plenty of opportunity to make it your own. The entry level features a welcoming foyer and a spacious bedroom with an en-suite bath. The lower level includes a second bedroom and full bath, kitchen, and a generous living and dining area with a wood-burning fireplace and access to a private balcony with beautiful views of downtown Annapolis, Spa Creek, and portion of the Naval Academy campus. While there is currently no washer and dryer within the unit, one can easily be added, and a community laundry room is conveniently located just down the hall. Set directly along Spa Creek, The Tecumseh offers a 72-slip private marina, waterfront swimming pool and deck, gated private parking, lobby, mailroom, conference room, and an on-site property manager. For the boater, ownership of W308 also includes an entitlement to a 29-foot boat slip. What truly sets this property apart is the lifestyle. Step outside and you’re moments from the water, just steps from Eastport’s Restaurant Row, and an easy walk across the bridge to downtown Annapolis. Rarely available, W308 presents a special opportunity to create your own home within a waterfront community cherished for its location, boating lifestyle, and enduring connection to Annapolis’s maritime heritage. The Tecumseh Condominium has a 15-day first right of refusal.

Welcome to 312 Severn Avenue, Unit W308—a rarely available two-story, two-bedroom, two-bath condominium at The Tecumseh, one of Eastport’s most distinctive waterfront communities. Located on the third floor, this approximately 1,390-square-foot residence offers a unique two-level layout with plenty of opportunity to make it your own. The entry level features a welcoming foyer and a spacious bedroom with an en-suite bath. The lower level includes a second bedroom and full bath, kitchen, and a generous living and dining area with a wood-burning fireplace and access to a private balcony with beautiful views of downtown Annapolis, Spa Creek, and portion of the Naval Academy campus. While there is currently no washer and dryer within the unit, one can easily be added, and a community laundry room is conveniently located just down the hall. Set directly along Spa Creek, The Tecumseh offers a 72-slip private marina, waterfront swimming pool and deck, gated private parking, lobby, mailroom, conference room, and an on-site property manager. For the boater, ownership of W308 also includes an entitlement to a 29-foot boat slip. What truly sets this property apart is the lifestyle. Step outside and you’re moments from the water, just steps from Eastport’s Restaurant Row, and an easy walk across the bridge to downtown Annapolis. Rarely available, W308 presents a special opportunity to create your own home within a waterfront community cherished for its location, boating lifestyle, and enduring connection to Annapolis’s maritime heritage. The Tecumseh Condominium has a 15-day first right of refusal.

312 Severn Unit W308, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$895,000

Nestled within the serene embrace of nature, enjoy fabulous waterfront views of Hawkins Cove and Spa Creek from this stunning 2-bedroom, 2.5-bathroom penthouse condominium in the highly sought-after community of Shearwater in Eastport. With a contemporary coastal architectural style, this home is a perfect blend of sophistication and warmth. Step inside to discover an open floor plan that seamlessly integrates the living and dining areas, enhanced by a stunning spiral staircase that adds a touch of architectural flair. The living area is accentuated by cathedral ceilings. Natural light floods the space through skylights, creating an inviting atmosphere throughout. The flat was entirely upgraded by an interior design firm in 2024, featuring gleaming living room floors, new windows and a gourmet kitchen designed to elevate your culinary creations. This penthouse features an abundance of chic finishes including Spa-inspired luxury bathrooms. Of particular note is the upper level Master suite artfully designed and fashioned from what was a large open balcony. It features a private and cozy retreat with a luxurious ensuite bathroom. A home office has been thoughtfully designed with elegant built ins on the upper level. The main floor bedroom also offers ample space and privacy, making it ideal for guests. The exterior of the property is equally impressive, boasting a private balcony that overlooks the lush landscaping and the waterfront, providing a peaceful escape right from your terrace. This truly is a nature watchers’ paradise. In December, celebrate the famous Eastport Yacht Club annual Parade of Lights in style by your cozy wood-burning fireplace. In Spring/Summer enjoy the easy breeze with family and friends with your favorite libation. For water enthusiasts, the property offers direct access to Hawkins Cove and Spa Creek, complete with a private dock site and multiple slips for boating, fishing, and kayaking adventures. Surrounded by partly wooded areas and mature trees, the lot features a harmonious blend of nature and luxury, creating a serene environment for relaxation and recreation. It offers seamless access to the Chesapeake Bay and beyond. Your luxury lifestyle features the choice to relax poolside, play tennis/pickleball on the courts, or take a water taxi from the docks to enjoy the stunning array of restaurants, events, the arts and much more. Welcome home, your Annapolis dream has come true!

2 Beds ⋅ 3 Baths

Nestled within the serene embrace of nature, enjoy fabulous waterfront views of Hawkins Cove and Spa Creek from this stunning 2-bedroom, 2.5-bathroom penthouse condominium in the highly sought-after community of Shearwater in Eastport. With a contemporary coastal architectural style, this home is a perfect blend of sophistication and warmth. Step inside to discover an open floor plan that seamlessly integrates the living and dining areas, enhanced by a stunning spiral staircase that adds a touch of architectural flair. The living area is accentuated by cathedral ceilings. Natural light floods the space through skylights, creating an inviting atmosphere throughout. The flat was entirely upgraded by an interior design firm in 2024, featuring gleaming living room floors, new windows and a gourmet kitchen designed to elevate your culinary creations. This penthouse features an abundance of chic finishes including Spa-inspired luxury bathrooms. Of particular note is the upper level Master suite artfully designed and fashioned from what was a large open balcony. It features a private and cozy retreat with a luxurious ensuite bathroom. A home office has been thoughtfully designed with elegant built ins on the upper level. The main floor bedroom also offers ample space and privacy, making it ideal for guests. The exterior of the property is equally impressive, boasting a private balcony that overlooks the lush landscaping and the waterfront, providing a peaceful escape right from your terrace. This truly is a nature watchers’ paradise. In December, celebrate the famous Eastport Yacht Club annual Parade of Lights in style by your cozy wood-burning fireplace. In Spring/Summer enjoy the easy breeze with family and friends with your favorite libation. For water enthusiasts, the property offers direct access to Hawkins Cove and Spa Creek, complete with a private dock site and multiple slips for boating, fishing, and kayaking adventures. Surrounded by partly wooded areas and mature trees, the lot features a harmonious blend of nature and luxury, creating a serene environment for relaxation and recreation. It offers seamless access to the Chesapeake Bay and beyond. Your luxury lifestyle features the choice to relax poolside, play tennis/pickleball on the courts, or take a water taxi from the docks to enjoy the stunning array of restaurants, events, the arts and much more. Welcome home, your Annapolis dream has come true!

8 Spa Creek Lndg Unit A3, Annapolis

Listing courtesy of Curtis Real Estate Company. Contact:

$506,000

Nestled within the serene embrace of nature, enjoy fabulous waterfront views of Hawkins Cove and Spa Creek from this stunning 1-bedroom, 1.5-bathroom second floor condominium in the highly sought-after community of Shearwater in Eastport. With a contemporary coastal architectural style, this home is a perfect blend of sophistication and warmth. Step inside to discover an open floor plan that seamlessly integrates the living and dining areas. Natural morning light floods the space through the kitchen creating an inviting atmosphere throughout. The flat has an upgraded refrigerator, new microwave, new washer&dryer, HVAC, heat pump and air handler all in aprox 2024. The home features gleaming living room floors, and a gourmet kitchen designed to elevate your culinary creations. The bedroom suite is a private and cozy retreat with a luxurious ensuite bathroom. The exterior of the property is equally impressive, boasting a private balcony that overlooks the lush landscaping and the waterfront, providing a peaceful escape right from your terrace. This truly is a nature watchers’ paradise. In December, celebrate the famous Eastport Yacht Club annual Parade of Lights in style by your cozy wood-burning fireplace. In Spring/Summer enjoy the easy breeze with family and friends with your favorite libation. For water enthusiasts, the community offers direct access to Hawkins Cove and Spa Creek, complete with a private dock site and multiple slips for boating, fishing, and kayaking adventures. Surrounded by partly wooded areas and mature trees, the lot features a harmonious blend of nature and luxury, creating a serene environment for relaxation and recreation. It offers seamless access to the Chesapeake Bay and beyond. Your luxury lifestyle features the choice to relax poolside, play tennis/pickleball on the courts, or take a water taxi from the docks to enjoy the stunning array of restaurants, events, the arts and much more. Welcome home, your Annapolis dream has come true!

1 Beds ⋅ 2 Baths

Nestled within the serene embrace of nature, enjoy fabulous waterfront views of Hawkins Cove and Spa Creek from this stunning 1-bedroom, 1.5-bathroom second floor condominium in the highly sought-after community of Shearwater in Eastport. With a contemporary coastal architectural style, this home is a perfect blend of sophistication and warmth. Step inside to discover an open floor plan that seamlessly integrates the living and dining areas. Natural morning light floods the space through the kitchen creating an inviting atmosphere throughout. The flat has an upgraded refrigerator, new microwave, new washer&dryer, HVAC, heat pump and air handler all in aprox 2024. The home features gleaming living room floors, and a gourmet kitchen designed to elevate your culinary creations. The bedroom suite is a private and cozy retreat with a luxurious ensuite bathroom. The exterior of the property is equally impressive, boasting a private balcony that overlooks the lush landscaping and the waterfront, providing a peaceful escape right from your terrace. This truly is a nature watchers’ paradise. In December, celebrate the famous Eastport Yacht Club annual Parade of Lights in style by your cozy wood-burning fireplace. In Spring/Summer enjoy the easy breeze with family and friends with your favorite libation. For water enthusiasts, the community offers direct access to Hawkins Cove and Spa Creek, complete with a private dock site and multiple slips for boating, fishing, and kayaking adventures. Surrounded by partly wooded areas and mature trees, the lot features a harmonious blend of nature and luxury, creating a serene environment for relaxation and recreation. It offers seamless access to the Chesapeake Bay and beyond. Your luxury lifestyle features the choice to relax poolside, play tennis/pickleball on the courts, or take a water taxi from the docks to enjoy the stunning array of restaurants, events, the arts and much more. Welcome home, your Annapolis dream has come true!

13 Spa Creek Lndg Unit A2, Annapolis

Listing courtesy of Curtis Real Estate Company. Contact:

$1,395,000

Highly desirable Eastport location just a short walk to Historic Annapolis, the U.S. Naval Academy, vibrant restaurants, boutique shops, and multiple marinas. This rare offering features essentially two separate homes on one property, creating an exceptional opportunity for multi‑generational living, guest accommodations, potential rental income, or a private studio/office retreat. The beautifully updated three‑level Cape Cod has been thoughtfully expanded and modernized. It features a gourmet kitchen, hardwood floors, two generous bedrooms, and 2.5 bathrooms. The main level office provides flexibility and can easily function as an additional bedroom. Every level blends comfort with style, offering bright spaces and quality finishes throughout. At the rear of the property sits an eclectic secondary structure with two cozy bedrooms and two full baths. Its lower level includes garage space and abundant storage ideal for bikes, paddleboards, tools, or seasonal items. Outdoor living shines here: a spacious deck and stone patio create inviting spaces for entertaining, grilling, or unwinding in a peaceful setting. With numerous exterior upgrades and a location that captures the best of Eastport living, this property is truly one of a kind.

4 Beds ⋅ 5 Baths

Highly desirable Eastport location just a short walk to Historic Annapolis, the U.S. Naval Academy, vibrant restaurants, boutique shops, and multiple marinas. This rare offering features essentially two separate homes on one property, creating an exceptional opportunity for multi‑generational living, guest accommodations, potential rental income, or a private studio/office retreat. The beautifully updated three‑level Cape Cod has been thoughtfully expanded and modernized. It features a gourmet kitchen, hardwood floors, two generous bedrooms, and 2.5 bathrooms. The main level office provides flexibility and can easily function as an additional bedroom. Every level blends comfort with style, offering bright spaces and quality finishes throughout. At the rear of the property sits an eclectic secondary structure with two cozy bedrooms and two full baths. Its lower level includes garage space and abundant storage ideal for bikes, paddleboards, tools, or seasonal items. Outdoor living shines here: a spacious deck and stone patio create inviting spaces for entertaining, grilling, or unwinding in a peaceful setting. With numerous exterior upgrades and a location that captures the best of Eastport living, this property is truly one of a kind.

1030 Boucher Ave, Annapolis

Listing courtesy of Curtis Real Estate Company. Contact:

$1,875,000

***Owner financing available at 6%*** Experience the best of the Annapolis lifestyle from this beautifully reimagined coastal Craftsman in the heart of Eastport. Ideally located within walking distance of downtown Annapolis, the waterfront, restaurants, shops, yacht clubs, marinas, and the many neighborhood amenities that make Eastport one of the area's most desirable communities, this extensively renovated home offers an exceptional combination of location, character, and modern comfort. Offering approximately 4,099 square feet of finished living space, the home features three bedrooms, a dedicated office, four bathrooms, and a versatile floor plan designed for both everyday living and entertaining. A welcoming front porch sets the tone, while James Hardie siding, Andersen 400 Series windows, low-maintenance exterior materials, and extensive improvements provide the benefits of a thoughtfully updated home while preserving its classic Eastport character. Inside, hardwood floors, high ceilings, substantial trim work, a fireplace creates warmth and architectural interest. Generous living and dining spaces flow naturally into the kitchen and family room, creating an inviting setting for entertaining or relaxed everyday living. Dual staircases provide access from both the front and rear portions of the home and add a distinctive architectural element to the floor plan. Upstairs, the spacious primary suite serves as a private retreat with a spa-inspired bath featuring a soaking tub, frameless glass shower, and dual vanity. Two additional bedrooms provide comfortable accommodations, while a separate office offers an ideal space for working from home. Convenient second-floor laundry completes the upper level. The fully finished lower level significantly expands the home's versatility, offering generous space for a recreation room, home gym, media room, or potential fourth bedroom. Full egress provides added flexibility for buyers who need additional sleeping accommodations, while ample storage enhances the functionality of the space. Outside, a large rear deck overlooks the generously sized yard, providing plenty of room for outdoor dining, entertaining, gardening, or simply relaxing at home. Three off-street parking spaces are an exceptional convenience in Eastport, while the property also offers potential for a future garage, accessory dwelling unit, and/or pool, subject to applicable approvals. Beyond the property itself is the lifestyle that makes this location so special. Leave the car at home and explore Eastport's restaurants, marinas, yacht clubs, and waterfront destinations, or stroll across the Spa Creek Bridge into historic downtown Annapolis and City Dock. Spend the morning on the water, meet friends for dinner in Eastport, or walk downtown for an evening along the harbor—all just minutes from your front door. 400 Jefferson Street offers the space and amenities of a substantially renovated home paired with the walkability, waterfront culture, and unmistakable character of Eastport. This is Annapolis living at its best.

***Owner financing available at 6%*** Experience the best of the Annapolis lifestyle from this beautifully reimagined coastal Craftsman in the heart of Eastport. Ideally located within walking distance of downtown Annapolis, the waterfront, restaurants, shops, yacht clubs, marinas, and the many neighborhood amenities that make Eastport one of the area's most desirable communities, this extensively renovated home offers an exceptional combination of location, character, and modern comfort. Offering approximately 4,099 square feet of finished living space, the home features three bedrooms, a dedicated office, four bathrooms, and a versatile floor plan designed for both everyday living and entertaining. A welcoming front porch sets the tone, while James Hardie siding, Andersen 400 Series windows, low-maintenance exterior materials, and extensive improvements provide the benefits of a thoughtfully updated home while preserving its classic Eastport character. Inside, hardwood floors, high ceilings, substantial trim work, a fireplace creates warmth and architectural interest. Generous living and dining spaces flow naturally into the kitchen and family room, creating an inviting setting for entertaining or relaxed everyday living. Dual staircases provide access from both the front and rear portions of the home and add a distinctive architectural element to the floor plan. Upstairs, the spacious primary suite serves as a private retreat with a spa-inspired bath featuring a soaking tub, frameless glass shower, and dual vanity. Two additional bedrooms provide comfortable accommodations, while a separate office offers an ideal space for working from home. Convenient second-floor laundry completes the upper level. The fully finished lower level significantly expands the home's versatility, offering generous space for a recreation room, home gym, media room, or potential fourth bedroom. Full egress provides added flexibility for buyers who need additional sleeping accommodations, while ample storage enhances the functionality of the space. Outside, a large rear deck overlooks the generously sized yard, providing plenty of room for outdoor dining, entertaining, gardening, or simply relaxing at home. Three off-street parking spaces are an exceptional convenience in Eastport, while the property also offers potential for a future garage, accessory dwelling unit, and/or pool, subject to applicable approvals. Beyond the property itself is the lifestyle that makes this location so special. Leave the car at home and explore Eastport's restaurants, marinas, yacht clubs, and waterfront destinations, or stroll across the Spa Creek Bridge into historic downtown Annapolis and City Dock. Spend the morning on the water, meet friends for dinner in Eastport, or walk downtown for an evening along the harbor—all just minutes from your front door. 400 Jefferson Street offers the space and amenities of a substantially renovated home paired with the walkability, waterfront culture, and unmistakable character of Eastport. This is Annapolis living at its best.

400 Jefferson St, Annapolis

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

$650,000

RARE OPPORTUNITY! TWO HOMES ON ONE LOT IN EASTPORT! This versatile property offers an exceptional combination of character, functionality, and flexibility with a renovated 2-bedroom, 1.5-bath main home PLUS a separate 1-bedroom, 1-bath guest house. The main residence features gleaming hardwood floors, a cozy fireplace, and a spacious kitchen with abundant counter space, a large peninsula, and stainless-steel appliances. The inviting layout provides comfortable living spaces while retaining the charm and character buyers love. The detached guest house is a standout feature, offering a private bedroom, full bath, living room, washer/dryer, and separate utilities. Ideal for guests, extended family, a private home office, or other flexible living arrangements. Enjoy the outdoors in the pleasant, tree-lined backyard, enclosed by a privacy fence. A 1+ car garage and shed provide plenty of room for parking, storage, hobbies, and outdoor equipment. Located conveniently to the restaurants, shops, waterfront, and attractions of Eastport and Downtown Annapolis, this property puts you close to everything while offering the flexibility of two separate living spaces. Notable recent improvements include: New roof and skylights (2023) New driveway (2022) Guest house electrical wiring (2022) New dishwasher (2024) Two homes. One lot. Endless possibilities. A unique opportunity in a highly desirable Annapolis location!

RARE OPPORTUNITY! TWO HOMES ON ONE LOT IN EASTPORT! This versatile property offers an exceptional combination of character, functionality, and flexibility with a renovated 2-bedroom, 1.5-bath main home PLUS a separate 1-bedroom, 1-bath guest house. The main residence features gleaming hardwood floors, a cozy fireplace, and a spacious kitchen with abundant counter space, a large peninsula, and stainless-steel appliances. The inviting layout provides comfortable living spaces while retaining the charm and character buyers love. The detached guest house is a standout feature, offering a private bedroom, full bath, living room, washer/dryer, and separate utilities. Ideal for guests, extended family, a private home office, or other flexible living arrangements. Enjoy the outdoors in the pleasant, tree-lined backyard, enclosed by a privacy fence. A 1+ car garage and shed provide plenty of room for parking, storage, hobbies, and outdoor equipment. Located conveniently to the restaurants, shops, waterfront, and attractions of Eastport and Downtown Annapolis, this property puts you close to everything while offering the flexibility of two separate living spaces. Notable recent improvements include: New roof and skylights (2023) New driveway (2022) Guest house electrical wiring (2022) New dishwasher (2024) Two homes. One lot. Endless possibilities. A unique opportunity in a highly desirable Annapolis location!

906 Jackson St, Annapolis

Listing courtesy of EXP Realty, LLC. Contact:

$1,799,000

Ooh la la, Eastport. There is something unmistakably special about life here—and 820 Bay Ridge Avenue captures it beautifully. Set within coveted Sailor’s Quay, this exceptional residence delivers the rare combination of space, sophistication, outdoor living, and walkability, all just moments from the heart of Annapolis. Behind the white picket fence, manicured landscaping and a gracious brick front porch create a picture-perfect welcome. Step inside to more than 4,000 square feet of beautifully finished living across FOUR levels, where rich hardwood floors, 9-foot ceilings, elegant millwork, tray ceilings, and plantation shutters create a home that feels polished without ever feeling fussy. Thoughtfully customized during construction, the residence includes numerous builder upgrades, enhanced electrical features, and details designed to make everyday living as effortless as the home is beautiful. At its heart is a fabulous kitchen with honed granite countertops, premium appliances, abundant cabinetry, and a generous center island opening seamlessly to the family room and upgraded gas fireplace. The formal dining room is ready for holidays, celebrations, and memorable dinners, while the adjoining sitting room or study is perfect for working from home, curling up with a favorite book, or ending the evening with a bourbon. And then there is the outdoor living. Morning coffee on the front porch overlooking the flower garden. Dinner in your private English courtyard. Cocktails under the stars on the second-floor terrace. Professionally enhanced landscaping creates an intimate retreat, while ceiling fans, a dedicated natural gas line for grilling, and the opportunity for a future fire feature make these spaces as functional as they are beautiful. Upstairs, the primary suite feels like a private escape, with a custom walk-in closet, spa-inspired bath, and expansive sitting room. A generous junior suite with its own bath offers wonderful privacy for family or guests, while two additional vaulted-ceiling bedrooms share a beautifully appointed full bath. The finished third-floor loft brings even more possibilities—a home office, fitness studio, media room, guest retreat, or whatever life calls for next. The finished lower level adds a spacious family room and full bath, providing even more flexibility for entertaining, extended stays, or multigenerational living. And in a feature rarely found, the home was designed with the future in mind with a framed elevator shaft, allowing an elevator to be added without compromising the architecture or thoughtful floor plan. But perhaps the greatest luxury of 820 Bay Ridge Avenue is everything waiting just outside your front door. Walk to St. Mary’s. Walk to dinner. Walk to neighborhood cafés and marinas. Walk to the Annapolis Yacht Club and Eastport Yacht Club. Cross the Spa Creek Drawbridge into Historic Downtown Annapolis and City Dock. Spend the afternoon on the Chesapeake, meet friends for dinner on the water, browse the shops and galleries downtown, or take the water taxi home after an evening out. Morning coffee around the corner. An afternoon on the water. Dinner in Eastport. Ice cream at City Dock. School, sailing, restaurants, shopping, marinas, yacht clubs, and downtown Annapolis—all without having to get in the car. And somehow, you still come home to more than 4,000 square feet, four finished levels, beautiful outdoor spaces, exceptional privacy, extensive custom upgrades, and future elevator capability. No need to choose between space, sophistication, and walkability. Here, you get all three. Polished. Coastal. Effortlessly Annapolis. Ooh la la, indeed.

4 Beds ⋅ 5 Baths

Ooh la la, Eastport. There is something unmistakably special about life here—and 820 Bay Ridge Avenue captures it beautifully. Set within coveted Sailor’s Quay, this exceptional residence delivers the rare combination of space, sophistication, outdoor living, and walkability, all just moments from the heart of Annapolis. Behind the white picket fence, manicured landscaping and a gracious brick front porch create a picture-perfect welcome. Step inside to more than 4,000 square feet of beautifully finished living across FOUR levels, where rich hardwood floors, 9-foot ceilings, elegant millwork, tray ceilings, and plantation shutters create a home that feels polished without ever feeling fussy. Thoughtfully customized during construction, the residence includes numerous builder upgrades, enhanced electrical features, and details designed to make everyday living as effortless as the home is beautiful. At its heart is a fabulous kitchen with honed granite countertops, premium appliances, abundant cabinetry, and a generous center island opening seamlessly to the family room and upgraded gas fireplace. The formal dining room is ready for holidays, celebrations, and memorable dinners, while the adjoining sitting room or study is perfect for working from home, curling up with a favorite book, or ending the evening with a bourbon. And then there is the outdoor living. Morning coffee on the front porch overlooking the flower garden. Dinner in your private English courtyard. Cocktails under the stars on the second-floor terrace. Professionally enhanced landscaping creates an intimate retreat, while ceiling fans, a dedicated natural gas line for grilling, and the opportunity for a future fire feature make these spaces as functional as they are beautiful. Upstairs, the primary suite feels like a private escape, with a custom walk-in closet, spa-inspired bath, and expansive sitting room. A generous junior suite with its own bath offers wonderful privacy for family or guests, while two additional vaulted-ceiling bedrooms share a beautifully appointed full bath. The finished third-floor loft brings even more possibilities—a home office, fitness studio, media room, guest retreat, or whatever life calls for next. The finished lower level adds a spacious family room and full bath, providing even more flexibility for entertaining, extended stays, or multigenerational living. And in a feature rarely found, the home was designed with the future in mind with a framed elevator shaft, allowing an elevator to be added without compromising the architecture or thoughtful floor plan. But perhaps the greatest luxury of 820 Bay Ridge Avenue is everything waiting just outside your front door. Walk to St. Mary’s. Walk to dinner. Walk to neighborhood cafés and marinas. Walk to the Annapolis Yacht Club and Eastport Yacht Club. Cross the Spa Creek Drawbridge into Historic Downtown Annapolis and City Dock. Spend the afternoon on the Chesapeake, meet friends for dinner on the water, browse the shops and galleries downtown, or take the water taxi home after an evening out. Morning coffee around the corner. An afternoon on the water. Dinner in Eastport. Ice cream at City Dock. School, sailing, restaurants, shopping, marinas, yacht clubs, and downtown Annapolis—all without having to get in the car. And somehow, you still come home to more than 4,000 square feet, four finished levels, beautiful outdoor spaces, exceptional privacy, extensive custom upgrades, and future elevator capability. No need to choose between space, sophistication, and walkability. Here, you get all three. Polished. Coastal. Effortlessly Annapolis. Ooh la la, indeed.

820 Bay Ridge Ave, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$540,000

Price adjusted to reflect market response. AND it's open 10/31 & 11/1 ! There's history here. In the 1940s, the Meade family built a number of homes on President Street and in Hillsmere — Meade Street bears their name. For the first time, the family will be passing on this home, one of the last one still in family hands, to new owners. Original wood trim, high ceilings, and wood floors pair with a surprisingly open floor plan for its age. The third bedroom and kitchen were added in the 1960's. The daughters' bedroom was the upper level for many years. A detached garage with an attached screened porch is perfectly positioned for outdoor entertaining. The yard is large and fenced. This home only needs the new owner's personal touches to make it once again a forever home!

3 Beds ⋅ 2 Baths

Price adjusted to reflect market response. AND it's open 10/31 & 11/1 ! There's history here. In the 1940s, the Meade family built a number of homes on President Street and in Hillsmere — Meade Street bears their name. For the first time, the family will be passing on this home, one of the last one still in family hands, to new owners. Original wood trim, high ceilings, and wood floors pair with a surprisingly open floor plan for its age. The third bedroom and kitchen were added in the 1960's. The daughters' bedroom was the upper level for many years. A detached garage with an attached screened porch is perfectly positioned for outdoor entertaining. The yard is large and fenced. This home only needs the new owner's personal touches to make it once again a forever home!

1309 President St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$550,000

Eastport! Eastport! Eastport! Corner lot that consists of 9,240 square feet. Off street parking and street parking. Stainless steel refrigerator, washer and dryer, and storage in lower level off the kitchen and in the upper level. New 10 foot by 15 foot shed. Separate dining room. Back porch 21 feet by 7 feet. Partially fenced back yard. Upstairs bedroom has unique wood ceiling. Freshly painted living room, 2 bedrooms, and dining room. Lot has room for expansion. Close to downtown, Quiet Waters Park, and Eastport Shopping Center. Easy access to main streets.

3 Beds ⋅ 1 Baths

Eastport! Eastport! Eastport! Corner lot that consists of 9,240 square feet. Off street parking and street parking. Stainless steel refrigerator, washer and dryer, and storage in lower level off the kitchen and in the upper level. New 10 foot by 15 foot shed. Separate dining room. Back porch 21 feet by 7 feet. Partially fenced back yard. Upstairs bedroom has unique wood ceiling. Freshly painted living room, 2 bedrooms, and dining room. Lot has room for expansion. Close to downtown, Quiet Waters Park, and Eastport Shopping Center. Easy access to main streets.

1311 President St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$700,000

Welcome to 1025 Hanson Street, offering nearly 2,880 sq. ft. of exceptionally flexible living space across three finished levels in the heart of Annapolis! Perfect for a multi-generational family. Thoughtfully improved and meticulously maintained, this turn-key home provides a rare combination of space, versatility, parking and major system upgrades. The main and upper levels feature 4 bedrooms, a full bath, a bright and open living area, an updated kitchen with granite countertops and tile backsplash, and dedicated laundry with front-loading washer and dryer, utility sink and additional storage. The fully finished ground level creates an incredible second living space featuring 2 additional bedrooms, a den/office, full bath, stunning secondary kitchen (minus stove/oven) with granite countertops, stainless steel appliances and tile backsplash, a second laundry setup with utility sink, and new LVP flooring throughout. A private side entrance, new fencing, paver walkway and patio access provide tremendous flexibility for multi-generational living, extended guests, a home office setup or simply additional space to spread out. Outside, you'll find features that are especially hard to come by in Annapolis—including dual driveways with parking for 6+ vehicles and/or boats, along with a two-story detached shed offering excellent storage and convenient yard and street access. Extensive improvements provide peace of mind, including a NEW 2025 roof on both the home and shed with transferable warranty, updated HVAC including heat pump and indoor coil, 60-gallon hybrid high-efficiency water heater, 200-amp electrical service, Tesla EV charger, French drain and stormwater management system, sump pump, updated attic insulation with spray foam, Nest thermostats, updated siding, additional ground-level egress, ceiling fans, fresh paint and much more. With three finished levels, two distinct living areas, exceptional parking and storage, and numerous major capital improvements already completed, 1025 Hanson Street offers the kind of versatility that's difficult to find in Annapolis. Whether you're looking for room for a growing household, multi-generational living, extended guests, midshipman sponsor hosting, or simply a home that provides plenty of space to live, work and entertain—this one is a 10/10!

6 Beds ⋅ 3 Baths

Welcome to 1025 Hanson Street, offering nearly 2,880 sq. ft. of exceptionally flexible living space across three finished levels in the heart of Annapolis! Perfect for a multi-generational family. Thoughtfully improved and meticulously maintained, this turn-key home provides a rare combination of space, versatility, parking and major system upgrades. The main and upper levels feature 4 bedrooms, a full bath, a bright and open living area, an updated kitchen with granite countertops and tile backsplash, and dedicated laundry with front-loading washer and dryer, utility sink and additional storage. The fully finished ground level creates an incredible second living space featuring 2 additional bedrooms, a den/office, full bath, stunning secondary kitchen (minus stove/oven) with granite countertops, stainless steel appliances and tile backsplash, a second laundry setup with utility sink, and new LVP flooring throughout. A private side entrance, new fencing, paver walkway and patio access provide tremendous flexibility for multi-generational living, extended guests, a home office setup or simply additional space to spread out. Outside, you'll find features that are especially hard to come by in Annapolis—including dual driveways with parking for 6+ vehicles and/or boats, along with a two-story detached shed offering excellent storage and convenient yard and street access. Extensive improvements provide peace of mind, including a NEW 2025 roof on both the home and shed with transferable warranty, updated HVAC including heat pump and indoor coil, 60-gallon hybrid high-efficiency water heater, 200-amp electrical service, Tesla EV charger, French drain and stormwater management system, sump pump, updated attic insulation with spray foam, Nest thermostats, updated siding, additional ground-level egress, ceiling fans, fresh paint and much more. With three finished levels, two distinct living areas, exceptional parking and storage, and numerous major capital improvements already completed, 1025 Hanson Street offers the kind of versatility that's difficult to find in Annapolis. Whether you're looking for room for a growing household, multi-generational living, extended guests, midshipman sponsor hosting, or simply a home that provides plenty of space to live, work and entertain—this one is a 10/10!

1025 Hanson St, Annapolis

Listing courtesy of Anne Arundel Properties, Inc.. Contact:

$674,000

Enjoy show-stopping sunsets and fabulous waterfront views of Spa Creek from this stunning condominium in the highly sought-after Shearwater complex in Eastport. This contemporary 2 bedroom condo is located on the second floor of building 6. From your private balcony, witness herons, egrets, ducks, and even the bald eagle in this bird and nature watchers’ paradise. Your view will feature a green valley that ends at the lagoon that leads directly to Spa Creek. In December, celebrate the famous EYC annual Parade of Lights in style by your wood-burning fireplace and in Spring/Summer enjoy the easy breeze with family and friends . The private community marina just steps away from your home, is the perfect place to dock your boat and store your kayak . It offers seamless access to Spa Creek, the Chesapeake Bay and beyond. Your luxury lifestyle also includes the choice to relax poolside, play tennis/pickleball on the courts, walk to town or take a water taxi from the docks to enjoy the stunning array of restaurants, events, the arts and much more. Welcome home, your Annapolis waterfront dream has come true!

Enjoy show-stopping sunsets and fabulous waterfront views of Spa Creek from this stunning condominium in the highly sought-after Shearwater complex in Eastport. This contemporary 2 bedroom condo is located on the second floor of building 6. From your private balcony, witness herons, egrets, ducks, and even the bald eagle in this bird and nature watchers’ paradise. Your view will feature a green valley that ends at the lagoon that leads directly to Spa Creek. In December, celebrate the famous EYC annual Parade of Lights in style by your wood-burning fireplace and in Spring/Summer enjoy the easy breeze with family and friends . The private community marina just steps away from your home, is the perfect place to dock your boat and store your kayak . It offers seamless access to Spa Creek, the Chesapeake Bay and beyond. Your luxury lifestyle also includes the choice to relax poolside, play tennis/pickleball on the courts, walk to town or take a water taxi from the docks to enjoy the stunning array of restaurants, events, the arts and much more. Welcome home, your Annapolis waterfront dream has come true!

6 Spa Creek Lndg Unit B2, Annapolis

Listing courtesy of Curtis Real Estate Company. Contact:

$1,250,000

Nestled in the heart of Eastport, this thoughtfully designed 3-bedroom, 2.5-bath home offers the perfect combination of comfortable living, modern updates, and one of Annapolis' most sought-after walkable locations. Complete with a rare detached two-car garage, this is an exceptional opportunity to enjoy the Eastport lifestyle in an established neighborhood that continues to attract significant investment and enduring demand. The main level features hardwood flooring throughout, a spacious living room, separate dining room, and an inviting family room with a wood-burning fireplace that opens directly to the kitchen—creating an ideal space for everyday living and entertaining. The kitchen is equipped with stainless steel appliances, a gas cooktop, and a separate main-level laundry/mudroom for added convenience. A spacious three-season porch extends the living space and creates a wonderful transition to the beautifully landscaped backyard, complete with a flagstone patio, attractive stone retaining wall, and detached two-car garage—ideal for relaxing or entertaining. Upstairs, the spacious primary suite offers a walk-in closet and private bath, along with two additional bedrooms and a full bathroom. The unfinished lower level provides abundant storage, a dedicated workshop area, and exterior access to the rear yard. Recent improvements include a new HVAC system (2024), newer garage doors, and a low-maintenance composite front porch. Step outside and enjoy everything that makes Eastport one of the most desirable waterfront communities in the region. Walk or bike to neighborhood restaurants, coffee shops, marinas, the Annapolis Athletic Club, Spa Creek, multiple yacht clubs, and Historic Downtown Annapolis via the Eastport Bridge. Hop aboard the Water Taxi, spend afternoons on the waterfront, or simply enjoy the vibrant coastal lifestyle that surrounds you. Opportunities to purchase in established Eastport neighborhoods continue to become more limited as significant investment and redevelopment enhance the surrounding area. Whether you're looking for a wonderful place to call home or a long-term investment in one of Annapolis' most coveted communities, 1105 Boucher Avenue offers both lifestyle and lasting value.

Nestled in the heart of Eastport, this thoughtfully designed 3-bedroom, 2.5-bath home offers the perfect combination of comfortable living, modern updates, and one of Annapolis' most sought-after walkable locations. Complete with a rare detached two-car garage, this is an exceptional opportunity to enjoy the Eastport lifestyle in an established neighborhood that continues to attract significant investment and enduring demand. The main level features hardwood flooring throughout, a spacious living room, separate dining room, and an inviting family room with a wood-burning fireplace that opens directly to the kitchen—creating an ideal space for everyday living and entertaining. The kitchen is equipped with stainless steel appliances, a gas cooktop, and a separate main-level laundry/mudroom for added convenience. A spacious three-season porch extends the living space and creates a wonderful transition to the beautifully landscaped backyard, complete with a flagstone patio, attractive stone retaining wall, and detached two-car garage—ideal for relaxing or entertaining. Upstairs, the spacious primary suite offers a walk-in closet and private bath, along with two additional bedrooms and a full bathroom. The unfinished lower level provides abundant storage, a dedicated workshop area, and exterior access to the rear yard. Recent improvements include a new HVAC system (2024), newer garage doors, and a low-maintenance composite front porch. Step outside and enjoy everything that makes Eastport one of the most desirable waterfront communities in the region. Walk or bike to neighborhood restaurants, coffee shops, marinas, the Annapolis Athletic Club, Spa Creek, multiple yacht clubs, and Historic Downtown Annapolis via the Eastport Bridge. Hop aboard the Water Taxi, spend afternoons on the waterfront, or simply enjoy the vibrant coastal lifestyle that surrounds you. Opportunities to purchase in established Eastport neighborhoods continue to become more limited as significant investment and redevelopment enhance the surrounding area. Whether you're looking for a wonderful place to call home or a long-term investment in one of Annapolis' most coveted communities, 1105 Boucher Avenue offers both lifestyle and lasting value.

1105 Boucher Ave, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$1,650,000

Nestled in the heart of Eastport, this stunning Craftsman-style home offers the perfect blend of timeless charm and modern luxury. This was a complete remodel in 2012! Boasting 4 bedrooms and 4 full baths, this thoughtfully designed residence features an open floor plan accented by beautiful bamboo flooring adding warmth and style throughout. The gourmet kitchen is the centerpiece of the home, complete with a striking marble center island, black granite countertops, stainless steel appliances, a pantry, and an expansive dining area that seamlessly flows into the inviting living room. The main-level primary suite is a true retreat with a spa-inspired bath featuring a soaking tub, walk-in shower, and generous walk-in closet. Upstairs, you'll find two large bedrooms, that share a full bath and an additional bedroom with its own private full bath, and a versatile sun-drenched sitting area with a dramatic vaulted ceiling. The walk-out lower level includes a full bath and versatile space to suit your lifestyle. Outside, a private rear deck perfect for relaxing or entertaining and charming stone walkways and welcoming front porch add historic like charm. A private driveway is for convenient off-street parking, and a storage shed is perfect to house all of your outdoor needs. Ideally located within walking distance of historic downtown Annapolis, you'll enjoy easy access to waterfront dining, boutique shopping, historic landmarks, entertainment, and all the vibrant attractions this sought-after area has to offer. The Eastport lifestyle truly one of a kind!

Nestled in the heart of Eastport, this stunning Craftsman-style home offers the perfect blend of timeless charm and modern luxury. This was a complete remodel in 2012! Boasting 4 bedrooms and 4 full baths, this thoughtfully designed residence features an open floor plan accented by beautiful bamboo flooring adding warmth and style throughout. The gourmet kitchen is the centerpiece of the home, complete with a striking marble center island, black granite countertops, stainless steel appliances, a pantry, and an expansive dining area that seamlessly flows into the inviting living room. The main-level primary suite is a true retreat with a spa-inspired bath featuring a soaking tub, walk-in shower, and generous walk-in closet. Upstairs, you'll find two large bedrooms, that share a full bath and an additional bedroom with its own private full bath, and a versatile sun-drenched sitting area with a dramatic vaulted ceiling. The walk-out lower level includes a full bath and versatile space to suit your lifestyle. Outside, a private rear deck perfect for relaxing or entertaining and charming stone walkways and welcoming front porch add historic like charm. A private driveway is for convenient off-street parking, and a storage shed is perfect to house all of your outdoor needs. Ideally located within walking distance of historic downtown Annapolis, you'll enjoy easy access to waterfront dining, boutique shopping, historic landmarks, entertainment, and all the vibrant attractions this sought-after area has to offer. The Eastport lifestyle truly one of a kind!

219 Lockwood Ct, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$524,999

Welcome home to this thoughtfully redesigned home in Eastport just blocks from Spa Creek and minutes to downtown Annapolis. This beautifully updated 3-bedroom, 3-bath residence offers approximately 1,600 finished square feet across two levels, combining a functional layout with quality finishes and extensive upgrades throughout. The main level features a bright living room and an updated kitchen with quartz countertops, shaker cabinetry, stainless steel appliances, and a dining area. A main-level bedroom and full bath provide flexibility for guests or a home office. A dedicated laundry and utility space leads to the rear addition, where the private primary suite includes vaulted ceilings, a walk-in closet, and an en-suite bath with double vanities, custom tile, and a walk-in shower. The upper level offers a finished attic suite with a third bedroom, full bath, and bonus flex space suitable for an office or additional living area. Interior features include durable flooring, recessed lighting, and a cohesive, modern design. Exterior highlights include a fully fenced backyard with new sod and a concrete patio, ideal for outdoor enjoyment. The property also features professional landscaping, a new asphalt driveway for off-street parking, and durable exterior materials including Hardie Plank siding, Andersen 200 Series windows, and a new architectural shingle roof. Major system upgrades include 200-amp electric service, new plumbing, dual-zone HVAC, and a whole-house sprinkler system. Conveniently located near restaurants, marinas, parks, downtown Annapolis, and Truxton Park.

Welcome home to this thoughtfully redesigned home in Eastport just blocks from Spa Creek and minutes to downtown Annapolis. This beautifully updated 3-bedroom, 3-bath residence offers approximately 1,600 finished square feet across two levels, combining a functional layout with quality finishes and extensive upgrades throughout. The main level features a bright living room and an updated kitchen with quartz countertops, shaker cabinetry, stainless steel appliances, and a dining area. A main-level bedroom and full bath provide flexibility for guests or a home office. A dedicated laundry and utility space leads to the rear addition, where the private primary suite includes vaulted ceilings, a walk-in closet, and an en-suite bath with double vanities, custom tile, and a walk-in shower. The upper level offers a finished attic suite with a third bedroom, full bath, and bonus flex space suitable for an office or additional living area. Interior features include durable flooring, recessed lighting, and a cohesive, modern design. Exterior highlights include a fully fenced backyard with new sod and a concrete patio, ideal for outdoor enjoyment. The property also features professional landscaping, a new asphalt driveway for off-street parking, and durable exterior materials including Hardie Plank siding, Andersen 200 Series windows, and a new architectural shingle roof. Major system upgrades include 200-amp electric service, new plumbing, dual-zone HVAC, and a whole-house sprinkler system. Conveniently located near restaurants, marinas, parks, downtown Annapolis, and Truxton Park.

1210 President St, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$995,000

Welcome to Eastport Estates at Griscom Square, a brand-new construction community of just 11 luxury single-family homes, located within one mile of downtown Eastport! Each residence showcases high-end finishes, spacious open-concept layouts, 9-foot ceilings, 4-5 Bedrooms, gourmet kitchen, modern baths, 2-car garages with private parking, and quality craftsmanship throughout, creating a truly well-built home. Inspired by its coastal setting, each home incorporates light-filled spaces and design elements that reflect Eastport’s nautical character. Enjoy effortless access to Eastport’s vibrant waterfront dining, live music, local marinas, yacht clubs, and scenic sunset views - or bike to or take the water taxi to City Dock, downtown Annapolis, and the United States Naval Academy. Luxury, lifestyle, and location - together in one place. This is a rare opportunity to build your own home this close to town. Lot and model options available!