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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:

1820 Baltimore Annapolis Blvd, Annapolis

$1,895,000

Welcome to an exceptional private estate in St. Margaret's, where sophisticated living meets effortless indoor-outdoor entertaining. Tucked behind a gated entrance and set on beautifully landscaped grounds, this expansive residence offers an impressive blend of luxury, versatility, and thoughtful design. The main level welcomes you with a grand foyer, solid red oak hardwood floors, and a stunning two-story living room featuring a gas fireplace and custom built-ins. The gourmet kitchen is truly the heart of the home, showcasing Wolf and Sub-Zero appliances, quartz countertops, marble backsplash, Miele dishwasher, beverage refrigerator, walk-in pantry, and abundant custom storage. The adjacent all-seasons room, complete with a wood-burning stove, provides a warm and inviting space to relax year-round. The main-level primary suite is a private retreat with its own gas fireplace, dual custom walk-in closets, built-in safe, and spa-inspired bath featuring a jetted soaking tub, oversized glass shower with dual shower heads and body sprayers, and dual marble vanities. A flexible additional room on the main level offers endless possibilities as an office, guest room, or additional bedroom. Above the oversized two-car garage, a separate bonus suite with full bath and closet provides exceptional flexibility for guests, an au pair, home gym, private office or additional bedroom Upstairs, a spacious loft-style lounge provides additional entertaining space, while three generously sized bedrooms offer walk-in closets and access to private or Jack-and-Jill baths. The lower level is designed for fun and entertaining, featuring a large open recreation area with polished concrete floors, indoor rock-climbing wall, built-in dartboard, beverage refrigerator, and a wood-paneled office/media room with custom built-ins and wet bar. Extensive unfinished storage, multiple utility-floored storage rooms, and a secure storage room with built-in safe and passcode entry provide an abundance of space. Outside, enjoy a custom paver patio with built-in gas grill, dedicated entertaining area, separate stone fire pit, private garden with raised planting beds, expansive side yard, and built-in basketball hoop. The property offers three garage bays, a circular driveway with auto court and five additional parking spaces, plus an attached storage shed. Recent updates include HVAC system improvements to both first and second-floor HVAC systems. A natural gas generator provides backup power for the tankless water heater, primary living spaces, and network/Wi-Fi infrastructure. With its gated privacy, remarkable entertaining spaces, luxury finishes, flexible living arrangements, extensive storage, and exceptional mechanical updates, 1820 Baltimore Annapolis Boulevard offers a truly distinctive lifestyle in sought-after Annapolis.

6 Beds ⋅ 5 Baths

Welcome to an exceptional private estate in St. Margaret's, where sophisticated living meets effortless indoor-outdoor entertaining. Tucked behind a gated entrance and set on beautifully landscaped grounds, this expansive residence offers an impressive blend of luxury, versatility, and thoughtful design. The main level welcomes you with a grand foyer, solid red oak hardwood floors, and a stunning two-story living room featuring a gas fireplace and custom built-ins. The gourmet kitchen is truly the heart of the home, showcasing Wolf and Sub-Zero appliances, quartz countertops, marble backsplash, Miele dishwasher, beverage refrigerator, walk-in pantry, and abundant custom storage. The adjacent all-seasons room, complete with a wood-burning stove, provides a warm and inviting space to relax year-round. The main-level primary suite is a private retreat with its own gas fireplace, dual custom walk-in closets, built-in safe, and spa-inspired bath featuring a jetted soaking tub, oversized glass shower with dual shower heads and body sprayers, and dual marble vanities. A flexible additional room on the main level offers endless possibilities as an office, guest room, or additional bedroom. Above the oversized two-car garage, a separate bonus suite with full bath and closet provides exceptional flexibility for guests, an au pair, home gym, private office or additional bedroom Upstairs, a spacious loft-style lounge provides additional entertaining space, while three generously sized bedrooms offer walk-in closets and access to private or Jack-and-Jill baths. The lower level is designed for fun and entertaining, featuring a large open recreation area with polished concrete floors, indoor rock-climbing wall, built-in dartboard, beverage refrigerator, and a wood-paneled office/media room with custom built-ins and wet bar. Extensive unfinished storage, multiple utility-floored storage rooms, and a secure storage room with built-in safe and passcode entry provide an abundance of space. Outside, enjoy a custom paver patio with built-in gas grill, dedicated entertaining area, separate stone fire pit, private garden with raised planting beds, expansive side yard, and built-in basketball hoop. The property offers three garage bays, a circular driveway with auto court and five additional parking spaces, plus an attached storage shed. Recent updates include HVAC system improvements to both first and second-floor HVAC systems. A natural gas generator provides backup power for the tankless water heater, primary living spaces, and network/Wi-Fi infrastructure. With its gated privacy, remarkable entertaining spaces, luxury finishes, flexible living arrangements, extensive storage, and exceptional mechanical updates, 1820 Baltimore Annapolis Boulevard offers a truly distinctive lifestyle in sought-after Annapolis.

1820 Baltimore Annapolis Blvd, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$1,895,000

** Private first-look appointments are available. Contact the listing agent to schedule for a first-look. ** A rare find in Eastport: an oversized attached two-car garage, plus a driveway and additional off-street parking, in a walkable waterfront neighborhood where garages are hard to come by. Beyond the striking exterior is a brand-new, ground-up home spanning three expansive levels, featuring 6 bedrooms, 4.5 baths, a chef-inspired kitchen with an oversized island and walk-in pantry, a main-level bedroom, an impressive primary suite, upper-level laundry, and a third-floor loft ideal for an office, guest space, or studio. Outside, enjoy a fully fenced yard, patio, and covered front porch — all just a short walk from Eastport’s marinas, restaurants, waterfront lifestyle, and downtown Annapolis.

6 Beds ⋅ 5 Baths

** Private first-look appointments are available. Contact the listing agent to schedule for a first-look. ** A rare find in Eastport: an oversized attached two-car garage, plus a driveway and additional off-street parking, in a walkable waterfront neighborhood where garages are hard to come by. Beyond the striking exterior is a brand-new, ground-up home spanning three expansive levels, featuring 6 bedrooms, 4.5 baths, a chef-inspired kitchen with an oversized island and walk-in pantry, a main-level bedroom, an impressive primary suite, upper-level laundry, and a third-floor loft ideal for an office, guest space, or studio. Outside, enjoy a fully fenced yard, patio, and covered front porch — all just a short walk from Eastport’s marinas, restaurants, waterfront lifestyle, and downtown Annapolis.

914 Van Buren St, Annapolis

Listing courtesy of Realty ONE Group Capital. 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:

$1,850,000

Prepare to be amazed by this rare waterfront opportunity offering 4 bedrooms, 4.5 baths with over 3000 square feet of living space with approximately 270-degree panoramic views of Gingerville Creek. Situated at the end of a quiet cul-de-sac, this exceptional property combines luxury, privacy, and an unbeatable location just minutes from Annapolis. Commuters will love the convenience of being just minutes from Exit 22, approximately 10 minutes to Route 50, and only 15 minutes to historic downtown Annapolis. For boating enthusiasts, this property is truly second to none. The private pier features a 10,000-pound boat lift, water and electric service, including two 220-volt outlets, three boat slips, floating dock and approximately 5+ feet of water at mean low water, making it ideal for larger vessels. A nearby marina and gas dock provide exceptional convenience for fueling, maintenance, and everyday boating adventures. The owners have meticulously maintained and updated the home with major improvements, including a new roof (2021) and upper-level HVAC system (2025). The exterior is equally impressive, featuring an attached two-car garage and driveway parking for up to six additional vehicles. Whether you're hosting family gatherings or waterfront celebrations, there's room for everyone. Step inside and you'll immediately be captivated by breathtaking water views. The welcoming living room features the first of two fireplaces and overlooks the creek, creating the perfect setting to relax year-round. As you continue into the heart of the home, you'll discover an expansive dining area surrounded by panoramic water views that will have you lingering over every meal. Sliding doors lead to a covered brick patio and an incredible backyard designed for entertaining on any scale—from everyday cookouts to milestone celebrations, weddings, corporate events, and unforgettable waterfront parties. Pet owners will appreciate the professionally installed invisible fence, allowing your four-legged family members to safely enjoy the expansive yard. The main level also offers a spacious kitchen, large family room, private office with a convenient half bath, a generously sized bedroom, and a full laundry room. Upstairs, the luxurious owner's suite offers stunning sunrise views over the creek and features an incredible layout with his-and-her bathrooms, a walk-in closet, and a true owner's retreat experience. Two additional bedrooms share a spacious full bath, while the loft provides the perfect second gathering space for movie nights, gaming, reading, or studying. A second laundry room on the upper level adds everyday convenience, and the walk-up attic with pull-down stairs provides abundant storage. Need even more flexibility? A detached waterfront office equipped with its own mini-split heating and cooling system creates the ideal work-from-home environment, art studio, or private retreat—all while enjoying incredible views of Gingerville Creek. Properties offering this combination of panoramic waterfront views, exceptional boating amenities, generous living space, thoughtful updates, and an unbeatable Annapolis-area location are extraordinarily rare. Complete photos, floor plans, and additional details will be available soon. Don't miss your opportunity to own one of the area's premier waterfront homes

Prepare to be amazed by this rare waterfront opportunity offering 4 bedrooms, 4.5 baths with over 3000 square feet of living space with approximately 270-degree panoramic views of Gingerville Creek. Situated at the end of a quiet cul-de-sac, this exceptional property combines luxury, privacy, and an unbeatable location just minutes from Annapolis. Commuters will love the convenience of being just minutes from Exit 22, approximately 10 minutes to Route 50, and only 15 minutes to historic downtown Annapolis. For boating enthusiasts, this property is truly second to none. The private pier features a 10,000-pound boat lift, water and electric service, including two 220-volt outlets, three boat slips, floating dock and approximately 5+ feet of water at mean low water, making it ideal for larger vessels. A nearby marina and gas dock provide exceptional convenience for fueling, maintenance, and everyday boating adventures. The owners have meticulously maintained and updated the home with major improvements, including a new roof (2021) and upper-level HVAC system (2025). The exterior is equally impressive, featuring an attached two-car garage and driveway parking for up to six additional vehicles. Whether you're hosting family gatherings or waterfront celebrations, there's room for everyone. Step inside and you'll immediately be captivated by breathtaking water views. The welcoming living room features the first of two fireplaces and overlooks the creek, creating the perfect setting to relax year-round. As you continue into the heart of the home, you'll discover an expansive dining area surrounded by panoramic water views that will have you lingering over every meal. Sliding doors lead to a covered brick patio and an incredible backyard designed for entertaining on any scale—from everyday cookouts to milestone celebrations, weddings, corporate events, and unforgettable waterfront parties. Pet owners will appreciate the professionally installed invisible fence, allowing your four-legged family members to safely enjoy the expansive yard. The main level also offers a spacious kitchen, large family room, private office with a convenient half bath, a generously sized bedroom, and a full laundry room. Upstairs, the luxurious owner's suite offers stunning sunrise views over the creek and features an incredible layout with his-and-her bathrooms, a walk-in closet, and a true owner's retreat experience. Two additional bedrooms share a spacious full bath, while the loft provides the perfect second gathering space for movie nights, gaming, reading, or studying. A second laundry room on the upper level adds everyday convenience, and the walk-up attic with pull-down stairs provides abundant storage. Need even more flexibility? A detached waterfront office equipped with its own mini-split heating and cooling system creates the ideal work-from-home environment, art studio, or private retreat—all while enjoying incredible views of Gingerville Creek. Properties offering this combination of panoramic waterfront views, exceptional boating amenities, generous living space, thoughtful updates, and an unbeatable Annapolis-area location are extraordinarily rare. Complete photos, floor plans, and additional details will be available soon. Don't miss your opportunity to own one of the area's premier waterfront homes

120 Island View Dr, Annapolis

Listing courtesy of Pearson Smith Realty, LLC. Contact:

$1,850,000

Rare mixed-use opportunity on Annapolis' premier commercial corridor. Positioned directly on West Street (MD Route 450), this versatile, income-producing building pairs a roughly 2,000 SF ground-floor showroom with two legal second-floor apartments and a substantial detached garage with workshop — all on a 12,428 SF lot with private parking for about six vehicles, a genuine premium on this corridor. The ground level is an open, high-visibility showroom with direct West Street frontage, well suited to retail, a gallery or design studio, professional offices, or a service business. Upstairs, two legal apartments (2BR/1BA each, per owner) deliver real live/work flexibility — one is currently configured as offices with a full kitchen. Run your business below and lease or occupy above, lease every component separately, or use the upper level as executive offices. The three-bay detached garage is a true standout: two overhead doors plus a rear man-door, its own heating system, and a wood stove for year-round use — conditioned workshop and storage that's nearly impossible to replicate in this location. Major systems are already addressed, with two newer HVAC units and a newer roof reducing near-term capital needs. Public water and sewer, 200+ amp electric service, and a Flood Zone X location (outside the Special Flood Hazard Area) round out a favorable operating profile. BCE (Business Corridor Enhancement) zoning supports a broad mix of commercial and residential uses, giving owner-operators, investors, and developers exceptional flexibility on one of Annapolis' busiest, highest-visibility corridors. Schedule your private tour today. Information deemed reliable but not guaranteed. Square footage, apartment legality, zoning uses, and systems to be independently verified by buyer.

1977 West St, Annapolis

Listing courtesy of Real Broker, LLC - Chester. 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.

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:

$1,775,000

Waterfront on the Chesapeake Bay! Welcome to 7017 Bay Front Drive, a charming two-story summer cottage in Annapolis with unobstructed views of the Bay and Bay Bridge. Watch the Blue Angels fly overhead, catch Fourth of July fireworks, or simply enjoy the boats passing by — all from home. Swim, kayak, fish, crab, paddle board, or boat right from your front yard. The main level offers an open-concept kitchen, dining area, and family room designed to maximize waterfront views, plus a sleeping area with half bath and closet, a full bath, and laundry. Upstairs, the entire level serves as a private primary suite with sweeping Bay views and its own full bath. Outside features riprap shoreline protection, a storage shed for waterfront gear, and an existing pier and boat slip ready to be restored. More than a cottage — it’s your front-row seat to life on the Chesapeake Bay.

2 Beds ⋅ 3 Baths

Waterfront on the Chesapeake Bay! Welcome to 7017 Bay Front Drive, a charming two-story summer cottage in Annapolis with unobstructed views of the Bay and Bay Bridge. Watch the Blue Angels fly overhead, catch Fourth of July fireworks, or simply enjoy the boats passing by — all from home. Swim, kayak, fish, crab, paddle board, or boat right from your front yard. The main level offers an open-concept kitchen, dining area, and family room designed to maximize waterfront views, plus a sleeping area with half bath and closet, a full bath, and laundry. Upstairs, the entire level serves as a private primary suite with sweeping Bay views and its own full bath. Outside features riprap shoreline protection, a storage shed for waterfront gear, and an existing pier and boat slip ready to be restored. More than a cottage — it’s your front-row seat to life on the Chesapeake Bay.

7017 Bay Front Dr, Annapolis

Listing courtesy of Home Towne Real Estate. Contact:

$1,750,000

Enjoy this large scenic lot w/ fully finished rancher & oversized 2 car garage just outside of downtown Annapolis. Open floor plan, cathedral ceilings, hardwood floors, skylights & more. Bulkheaded waterfront w/ 4 deep water slips. Main floor living, plus a walk out lower level. You will not want to miss this property!! It is truly one of a kind! Call agent for details. Interior photos, floor plan & additional information to follow. Do not enter property without an appointment.

3 Beds ⋅ 3 Baths

Enjoy this large scenic lot w/ fully finished rancher & oversized 2 car garage just outside of downtown Annapolis. Open floor plan, cathedral ceilings, hardwood floors, skylights & more. Bulkheaded waterfront w/ 4 deep water slips. Main floor living, plus a walk out lower level. You will not want to miss this property!! It is truly one of a kind! Call agent for details. Interior photos, floor plan & additional information to follow. Do not enter property without an appointment.

314 Kingsberry Dr, Annapolis

Listing courtesy of RE/MAX One. Contact:

$1,749,000

Stress melts away the moment you pull into the driveway. Set on 1.06 peaceful acres in sought-after Admiral Heights, this mid-century modern home offers expansive views of Weems Creek in both directions, with a resident bald eagle that has called the neighborhood home for more than a decade. The house was fully renovated to the studs in 2022, with new windows, doors, chef's kitchen, design-grade bathrooms, insulation and flooring throughout. Inside are 4 bedrooms and 3.5 baths across 2,382 square feet, with numerous windows designed to take in the water views and the quiet setting. Recent updates continue outside: the exterior was painted in 2025, and the front yard was fully redone and the upper roof replaced in 2026. The work is done, so you can move in and enjoy it. The property includes an approximately 0.2-acre subdivided buildable lot, which offers room for a second home, a guest house for extended household or relatives, or a future investment. This waterfront location is ready to finish, so bring your dock designer/builder and complete the picture. Admiral Heights is a popular water-privileged community with a voluntary improvement association, a neighborhood pool with membership options, several community-owned docks, and a local boat club. You’re minutes from downtown Annapolis and the Navy-Marine Corps Memorial Stadium, with easy access to Route 50 for commuting to DC, Baltimore and beyond. A rare chance to own a renovated, private retreat on Weems Creek, with space to grow.

Stress melts away the moment you pull into the driveway. Set on 1.06 peaceful acres in sought-after Admiral Heights, this mid-century modern home offers expansive views of Weems Creek in both directions, with a resident bald eagle that has called the neighborhood home for more than a decade. The house was fully renovated to the studs in 2022, with new windows, doors, chef's kitchen, design-grade bathrooms, insulation and flooring throughout. Inside are 4 bedrooms and 3.5 baths across 2,382 square feet, with numerous windows designed to take in the water views and the quiet setting. Recent updates continue outside: the exterior was painted in 2025, and the front yard was fully redone and the upper roof replaced in 2026. The work is done, so you can move in and enjoy it. The property includes an approximately 0.2-acre subdivided buildable lot, which offers room for a second home, a guest house for extended household or relatives, or a future investment. This waterfront location is ready to finish, so bring your dock designer/builder and complete the picture. Admiral Heights is a popular water-privileged community with a voluntary improvement association, a neighborhood pool with membership options, several community-owned docks, and a local boat club. You’re minutes from downtown Annapolis and the Navy-Marine Corps Memorial Stadium, with easy access to Route 50 for commuting to DC, Baltimore and beyond. A rare chance to own a renovated, private retreat on Weems Creek, with space to grow.

173 Williams Dr, Annapolis

Listing courtesy of Homecoin.com. Contact:

$1,700,000

Experience the ultimate walkable lifestyle in the heart of Downtown Annapolis with this charming traditional home in the Historic District, where timeless character meets modern comfort. Built in 1900, this inviting residence captures the quintessential charm of Annapolis while offering thoughtful updates and the conveniences of contemporary living. Steps away from the welcoming front porch you'll find boutique shops, waterfront dining, historic landmarks, and the U.S. Naval Academy. Inside, original hardwood floors and classic architectural details create a warm and inviting atmosphere. The layout features three bedrooms, two full bathrooms, and a half bath. The main level offers comfortable living and entertaining spaces along with a welcoming kitchen, while a carefully renovated room addition provides valuable additional living space. The primary bathroom has been beautifully styled with a luxurious spa-like feel, creating a peaceful retreat at the end of the day. Outdoor living is equally inviting, with a private patio and lush turf yard overlooking Cumberland Court—an ideal setting for morning coffee, al fresco dining, summer gatherings, or simply enjoying the charm of downtown living. Surrounded by the history, culture, shops, restaurants, and waterfront that make the Historic District so special, this distinctive home offers an authentic Annapolis lifestyle, blending historic charm, modern comfort, exceptional walkability, and an unusually generous amount of private parking.

3 Beds ⋅ 3 Baths

Experience the ultimate walkable lifestyle in the heart of Downtown Annapolis with this charming traditional home in the Historic District, where timeless character meets modern comfort. Built in 1900, this inviting residence captures the quintessential charm of Annapolis while offering thoughtful updates and the conveniences of contemporary living. Steps away from the welcoming front porch you'll find boutique shops, waterfront dining, historic landmarks, and the U.S. Naval Academy. Inside, original hardwood floors and classic architectural details create a warm and inviting atmosphere. The layout features three bedrooms, two full bathrooms, and a half bath. The main level offers comfortable living and entertaining spaces along with a welcoming kitchen, while a carefully renovated room addition provides valuable additional living space. The primary bathroom has been beautifully styled with a luxurious spa-like feel, creating a peaceful retreat at the end of the day. Outdoor living is equally inviting, with a private patio and lush turf yard overlooking Cumberland Court—an ideal setting for morning coffee, al fresco dining, summer gatherings, or simply enjoying the charm of downtown living. Surrounded by the history, culture, shops, restaurants, and waterfront that make the Historic District so special, this distinctive home offers an authentic Annapolis lifestyle, blending historic charm, modern comfort, exceptional walkability, and an unusually generous amount of private parking.

219 King George St, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$1,700,000

Come see this beautiful one-of-a-kind WATERFRONT property! Complete waterfront view from both levels of this home and every room. True master bedroom and large enough to fit a king-size bedroom suite and private bathroom. Covered patio to enjoy the view in every weather type! Large windows throughout the home brings in natural light while keeping the waterfront setting front and center. There are fireplaces on each level. Swim all year round with this heated indoor pool and hot tub. Dock rental slips are available for owners for a $500 fee for deep water (6ft) or lower water slips for $200 (3ft) with electricity. This property can have a personal pier added not to mention Just steps away from the community beach and docks. Arundel on the Bay also offers a community beach and an established waterfront neighborhood just minutes from everything Annapolis has to offer.

4 Beds ⋅ 3 Baths

Come see this beautiful one-of-a-kind WATERFRONT property! Complete waterfront view from both levels of this home and every room. True master bedroom and large enough to fit a king-size bedroom suite and private bathroom. Covered patio to enjoy the view in every weather type! Large windows throughout the home brings in natural light while keeping the waterfront setting front and center. There are fireplaces on each level. Swim all year round with this heated indoor pool and hot tub. Dock rental slips are available for owners for a $500 fee for deep water (6ft) or lower water slips for $200 (3ft) with electricity. This property can have a personal pier added not to mention Just steps away from the community beach and docks. Arundel on the Bay also offers a community beach and an established waterfront neighborhood just minutes from everything Annapolis has to offer.

1323 Magnolia Ave, Annapolis

Listing courtesy of Keller Williams Select Realtors of Annapolis. Contact:

$1,695,000

Experience the best of Annapolis living in the sought-after, amenities-rich community of Fishing Creek Farm. Perfectly positioned to capture beautiful water views and surrounded by lush lawns and mature landscaping, this handsome brick-front Colonial offers a rare combination of timeless architecture, flexible living spaces, and an exceptional neighborhood lifestyle. A gracious foyer welcomes you into formal living and dining rooms designed for entertaining. At the heart of the home, the bright white kitchen features quartz countertops, abundant cabinetry, and a sunny breakfast nook that flows seamlessly into the impressive family room with soaring vaulted ceilings, a fireplace, and easy access to the patio and expansive backyard. Whether hosting summer gatherings or enjoying a quiet evening outdoors, the spacious front and rear yards provide room to relax, play, and take in the peaceful surroundings. Designed for both convenience and versatility, the main level includes a spacious primary suite, while a second upper-level primary suite enjoys sweeping water views and creates an ideal retreat for owners or guests. Two additional bedrooms share a well-appointed hall bath, providing ample space for family and friends. The partially finished lower level offers additional living space, generous storage, and easily accessible crawl spaces. Life in Fishing Creek Farm extends far beyond the property itself. Residents enjoy one of Annapolis' most coveted waterfront communities, complete with a community marina, swimming pool, sandy beach, tennis and pickleball courts, and year-round social activities. Located on the Annapolis Neck peninsula between the South River and the Chesapeake Bay, this special neighborhood offers a peaceful waterfront setting just minutes from downtown Annapolis, Eastport, and major commuting routes to Baltimore, BWI Airport, Fort Meade/NSA, Washington, D.C., and the Eastern Shore. A wonderful opportunity to enjoy the Chesapeake lifestyle in one of Annapolis' most desirable communities. Welcome Home!

Experience the best of Annapolis living in the sought-after, amenities-rich community of Fishing Creek Farm. Perfectly positioned to capture beautiful water views and surrounded by lush lawns and mature landscaping, this handsome brick-front Colonial offers a rare combination of timeless architecture, flexible living spaces, and an exceptional neighborhood lifestyle. A gracious foyer welcomes you into formal living and dining rooms designed for entertaining. At the heart of the home, the bright white kitchen features quartz countertops, abundant cabinetry, and a sunny breakfast nook that flows seamlessly into the impressive family room with soaring vaulted ceilings, a fireplace, and easy access to the patio and expansive backyard. Whether hosting summer gatherings or enjoying a quiet evening outdoors, the spacious front and rear yards provide room to relax, play, and take in the peaceful surroundings. Designed for both convenience and versatility, the main level includes a spacious primary suite, while a second upper-level primary suite enjoys sweeping water views and creates an ideal retreat for owners or guests. Two additional bedrooms share a well-appointed hall bath, providing ample space for family and friends. The partially finished lower level offers additional living space, generous storage, and easily accessible crawl spaces. Life in Fishing Creek Farm extends far beyond the property itself. Residents enjoy one of Annapolis' most coveted waterfront communities, complete with a community marina, swimming pool, sandy beach, tennis and pickleball courts, and year-round social activities. Located on the Annapolis Neck peninsula between the South River and the Chesapeake Bay, this special neighborhood offers a peaceful waterfront setting just minutes from downtown Annapolis, Eastport, and major commuting routes to Baltimore, BWI Airport, Fort Meade/NSA, Washington, D.C., and the Eastern Shore. A wonderful opportunity to enjoy the Chesapeake lifestyle in one of Annapolis' most desirable communities. Welcome Home!

3403 Hidden River View Rd, Annapolis

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

$1,690,000

A Builder’s Personal Residence | A Signature Annapolis Home A rare opportunity to own the personal residence of a builder and an interior designer, whose expertise and craftsmanship are reflected throughout their exceptional Annapolis home. 3124 Starboard Drive represents their vision of quality, functionality, and enduring design—where no detail was overlooked and every improvement was thoughtfully executed. Known as one of the neighborhood’s exceptional residences, this home offers a level of craftsmanship and attention to detail that is difficult to replicate. From the quality of construction and materials to the thoughtful design choices, the property reflects the discerning standards of a professional who builds and renovates homes for a living. This extraordinary residential real estate transformation is the creation of Mac O’Brien, the owner of Great Eastern Contracting, and his wife Becca O’Brien from Intuitive Design. Together they joined forces and underwent a complete, down-to-the-studs renovation and expansion. They purchased this home in 2015 and over the course of time they turned a 2,000 square foot home into an over 3,700 square feet of luxurious, modern turnkey showpiece with no detail overlooked. This five-bedroom, four-bathroom residence, has an open and elegant floor plan flooded with natural light. The chef kitchen has a stunning 8.9’ x 6.9’ quartz Island countertop offering exceptional workspace and seating for five with striking oversized lantern-style pendant lamps. The Owner’s Suite Spa-inspired primary bath has a custom white double-vanity, luxurious marble countertops, polished brass fixtures, oversized mirrors, elegant glass pendant lighting and heated floors. The expansive walk-in shower is beautifully appointed in veined marble tile with a frameless glass enclosure, multiple shower fixtures and built-in niches, creating a sophisticated, resort-like retreat. The living and family rooms have gas fireplaces and built ins. In addition, the home features a recreation room, fully fenced backyard, a double garage converted into a conditioned and finished Golf simulator room, shed and golf-cart garage. Mechanical systems include a full-house back-up generator, dual zone HVAC systems, tankless water heater, RO water filtration in kitchen and below counter Scotsman Gourmet Ice Maker and water treatment with dual storage tanks, salinator, chlorinator, sediment filter and UV light. This residence was meticulously rebuilt in 2021 - walls, ceilings, floors, fixtures, electrical, and plumbing systems—all removed and replaced with high-end finishes and craftsmanship throughout. The result is a striking blend of contemporary comfort and timeless design. Located in the sought-after waterfront community of Anchorage, this distinctive residence combines sophisticated living with the relaxed character of an established Annapolis neighborhood, offering access to the community’s marina, pool, boat ramp and waterfront amenities.

5 Beds ⋅ 4 Baths

A Builder’s Personal Residence | A Signature Annapolis Home A rare opportunity to own the personal residence of a builder and an interior designer, whose expertise and craftsmanship are reflected throughout their exceptional Annapolis home. 3124 Starboard Drive represents their vision of quality, functionality, and enduring design—where no detail was overlooked and every improvement was thoughtfully executed. Known as one of the neighborhood’s exceptional residences, this home offers a level of craftsmanship and attention to detail that is difficult to replicate. From the quality of construction and materials to the thoughtful design choices, the property reflects the discerning standards of a professional who builds and renovates homes for a living. This extraordinary residential real estate transformation is the creation of Mac O’Brien, the owner of Great Eastern Contracting, and his wife Becca O’Brien from Intuitive Design. Together they joined forces and underwent a complete, down-to-the-studs renovation and expansion. They purchased this home in 2015 and over the course of time they turned a 2,000 square foot home into an over 3,700 square feet of luxurious, modern turnkey showpiece with no detail overlooked. This five-bedroom, four-bathroom residence, has an open and elegant floor plan flooded with natural light. The chef kitchen has a stunning 8.9’ x 6.9’ quartz Island countertop offering exceptional workspace and seating for five with striking oversized lantern-style pendant lamps. The Owner’s Suite Spa-inspired primary bath has a custom white double-vanity, luxurious marble countertops, polished brass fixtures, oversized mirrors, elegant glass pendant lighting and heated floors. The expansive walk-in shower is beautifully appointed in veined marble tile with a frameless glass enclosure, multiple shower fixtures and built-in niches, creating a sophisticated, resort-like retreat. The living and family rooms have gas fireplaces and built ins. In addition, the home features a recreation room, fully fenced backyard, a double garage converted into a conditioned and finished Golf simulator room, shed and golf-cart garage. Mechanical systems include a full-house back-up generator, dual zone HVAC systems, tankless water heater, RO water filtration in kitchen and below counter Scotsman Gourmet Ice Maker and water treatment with dual storage tanks, salinator, chlorinator, sediment filter and UV light. This residence was meticulously rebuilt in 2021 - walls, ceilings, floors, fixtures, electrical, and plumbing systems—all removed and replaced with high-end finishes and craftsmanship throughout. The result is a striking blend of contemporary comfort and timeless design. Located in the sought-after waterfront community of Anchorage, this distinctive residence combines sophisticated living with the relaxed character of an established Annapolis neighborhood, offering access to the community’s marina, pool, boat ramp and waterfront amenities.

3124 Starboard Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$1,675,000

Ideally situated on the corner of Prince George & College Ave(across from St Johns College), this distinguished residence is tucked in the heart of Historic Downtown Annapolis. This exceptional home offers the charm of an Historic home built circa 1800's with modern conveniences. Soaring ceilings and windows create sun-drenched rooms with beautiful views of the grounds at St. Johns College. This home was built for entertaining. It has amazing flow to entertain your guests for a dinner party. Take a short walk to outdoor dining on West Street during "Dinner Under the Stars" or host friends for all the amazing Downtown events like Midnight Madness. This home is in the heart of it all! The electrical and plumbing was updated in 1990, new hot water heater in 2024, 2 heat pumps in 2025 and new Shake Shingle roof in 2026. There are 4 bedrooms and 2 full baths on the second floor with a bonus room on the third floor great for guests or office. All this just 1.5 blocks from the Naval Academy and steps to the shops and amazing restaurants Annapolis has to offer! There is driveway with private parking for 2 cars and plenty of street parking for guests. Walk to City Dock for morning coffee and watch the boats pass by or sit in the morning room and enjoy your coffee looking over the grounds of St. Johns. This is an amazing house in an amazing location with all that Annapolis has to offer.

5 Beds ⋅ 3 Baths

Ideally situated on the corner of Prince George & College Ave(across from St Johns College), this distinguished residence is tucked in the heart of Historic Downtown Annapolis. This exceptional home offers the charm of an Historic home built circa 1800's with modern conveniences. Soaring ceilings and windows create sun-drenched rooms with beautiful views of the grounds at St. Johns College. This home was built for entertaining. It has amazing flow to entertain your guests for a dinner party. Take a short walk to outdoor dining on West Street during "Dinner Under the Stars" or host friends for all the amazing Downtown events like Midnight Madness. This home is in the heart of it all! The electrical and plumbing was updated in 1990, new hot water heater in 2024, 2 heat pumps in 2025 and new Shake Shingle roof in 2026. There are 4 bedrooms and 2 full baths on the second floor with a bonus room on the third floor great for guests or office. All this just 1.5 blocks from the Naval Academy and steps to the shops and amazing restaurants Annapolis has to offer! There is driveway with private parking for 2 cars and plenty of street parking for guests. Walk to City Dock for morning coffee and watch the boats pass by or sit in the morning room and enjoy your coffee looking over the grounds of St. Johns. This is an amazing house in an amazing location with all that Annapolis has to offer.

250 Prince George St, Annapolis

Listing courtesy of Coldwell Banker Realty. 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:

$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 will be vacant at closing, giving the next owner the flexibility to rent it, use it for family or guests, create a private home office, or accommodate multigenerational living. The current owners have invested more than $100,000 in property upgrades over the past 18 months including new and updated baths; the cottage remodel; extensive electrical, lighting, and hardware upgrades; replacement A/C; interior and exterior painting; and landscaping. Ample street parking, with no parking fees for visitors, is available at this quiet residential end of Eastport. The property’s location between First and Second Streets is approximately two blocks from both Horn Point and Spa Creek. This offers the best of the neighborhood’s relaxed waterfront lifestyle while also remaining close to some of the best restaurants in Annapolis and just over the bridge from downtown Annapolis. This attractively updated Eastport home, complemented by a rentable cottage, presents a unique and appealing opportunity in one of Annapolis’s most popular neighborhoods.

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 will be vacant at closing, giving the next owner the flexibility to rent it, use it for family or guests, create a private home office, or accommodate multigenerational living. The current owners have invested more than $100,000 in property upgrades over the past 18 months including new and updated baths; the cottage remodel; extensive electrical, lighting, and hardware upgrades; replacement A/C; interior and exterior painting; and landscaping. Ample street parking, with no parking fees for visitors, is available at this quiet residential end of Eastport. The property’s location between First and Second Streets is approximately two blocks from both Horn Point and Spa Creek. This offers the best of the neighborhood’s relaxed waterfront lifestyle while also remaining close to some of the best restaurants in Annapolis and just over the bridge from downtown Annapolis. This attractively updated Eastport home, complemented by a rentable cottage, presents a unique and appealing opportunity in one of Annapolis’s most popular neighborhoods.

123 Chesapeake Ave, Annapolis

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

$1,549,000

Welcome to 202 Wardour Drive! This classic 1940 Dutch Colonial offers timeless character, generous living space, and an unbeatable Annapolis location. Situated on a quarter acre lot with large front yard, the south facing location ensures sunny days ahead! Located in the elegant Wardour community which reflects the naturalistic style of its designer, Frederick Law Olmstead, Jr, with its mature trees, meandering roads and preserved open spaces that foster community connection. Inside, the home features five bedrooms, two bathrooms, gorgeous oak floors (recently refinished in 2026), fireplace, bright sun-porch and large 12x 32 back deck. The south-facing orientation fills the home with natural light, creating a bright and cheerful atmosphere throughout. Recent improvements include freshly painted interior and exterior spaces, a newer roof approximately four years old, new porch benches, and a beautifully installed brick paver sidewalk that enhances the home’s curb appeal. A long driveway and rear detached garage provide ample parking and storage. Residents benefit from access to seven community beach areas and a shaded walking trail traversing the neighborhood, that provide a tranquil retreat for adults and a natural wonderland to explore. Conveniently located within walking distance of the local elementary school, Navy Stadium, Annapolis Street shopping and dining, Historic Downtown Annapolis and offers easy access to Rt. 50 for commuters. With classic architecture, spacious interiors, abundant natural light, and an exceptional in-town location close to everything Annapolis has to offer, this is a rare opportunity to own in one of the area’s most beloved neighborhoods. Schedule your private tour today!

5 Beds ⋅ 2 Baths

Welcome to 202 Wardour Drive! This classic 1940 Dutch Colonial offers timeless character, generous living space, and an unbeatable Annapolis location. Situated on a quarter acre lot with large front yard, the south facing location ensures sunny days ahead! Located in the elegant Wardour community which reflects the naturalistic style of its designer, Frederick Law Olmstead, Jr, with its mature trees, meandering roads and preserved open spaces that foster community connection. Inside, the home features five bedrooms, two bathrooms, gorgeous oak floors (recently refinished in 2026), fireplace, bright sun-porch and large 12x 32 back deck. The south-facing orientation fills the home with natural light, creating a bright and cheerful atmosphere throughout. Recent improvements include freshly painted interior and exterior spaces, a newer roof approximately four years old, new porch benches, and a beautifully installed brick paver sidewalk that enhances the home’s curb appeal. A long driveway and rear detached garage provide ample parking and storage. Residents benefit from access to seven community beach areas and a shaded walking trail traversing the neighborhood, that provide a tranquil retreat for adults and a natural wonderland to explore. Conveniently located within walking distance of the local elementary school, Navy Stadium, Annapolis Street shopping and dining, Historic Downtown Annapolis and offers easy access to Rt. 50 for commuters. With classic architecture, spacious interiors, abundant natural light, and an exceptional in-town location close to everything Annapolis has to offer, this is a rare opportunity to own in one of the area’s most beloved neighborhoods. Schedule your private tour today!

202 Wardour Dr, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$1,545,000

Rarely does a home of this historical significance become available in the heart of Historic Annapolis. Believed to date to the late 17th century, the extraordinary residence is among the city's oldest surviving homes, seamlessly blending centuries of architectural heritage with sophisticated modern living. Perched at the water end of Market St overlooking Spa Creek and parking on both sides of street, this home is instantly recognizable by its iconic red standing-seam roof and timeless presence. Rich in character, the interior showcases exposed original beams, soaring ceilings, abundant natural light, and thoughtfully designed living spaces that honor the home's remarkable past while embracing contemporary comfort. A nationally recognized renovation in 1977 by Gate One Builders, transformed the residence into a one of a kind masterpiece, preserving its historic integrity while creating an open, light filled floor plan unlike any other in Annapolis. The beautifully appointed Kitchen, inviting living and dining areas, combination gas and wood burning fireplaces and a tranquil large Sunroom addition all flow effortlessly to a private walled courtyard, an intimate outdoor retreat ideal for entertaining or quiet relaxation and completely fenced in. Features 2 ensuite Bedrooms and a 3rd enclosed Bedroom easily adapted into a private home office or gym while still preserving the home's architectural flow. Water Views of Spa Creek, exceptional craftsmanship, and architectural details at every turn make this home as captivating as it is livable. Adding to its rarity are amenities seldom found with the Historic District, including two covered off street parking spaces and an unparalleled waterfront setting just moments from City Dock, the USNA, fine dining, boutiques, galleries and yacht club. Whether enjoyed as a full time residence or an exceptional Annapolis retreat, 100 Market Street represents a once in a generation opportunity to own an irreplaceable piece of the city's history, where more than three centuries of heritage meet the very best of coastal luxury living.

3 Beds ⋅ 3 Baths

Rarely does a home of this historical significance become available in the heart of Historic Annapolis. Believed to date to the late 17th century, the extraordinary residence is among the city's oldest surviving homes, seamlessly blending centuries of architectural heritage with sophisticated modern living. Perched at the water end of Market St overlooking Spa Creek and parking on both sides of street, this home is instantly recognizable by its iconic red standing-seam roof and timeless presence. Rich in character, the interior showcases exposed original beams, soaring ceilings, abundant natural light, and thoughtfully designed living spaces that honor the home's remarkable past while embracing contemporary comfort. A nationally recognized renovation in 1977 by Gate One Builders, transformed the residence into a one of a kind masterpiece, preserving its historic integrity while creating an open, light filled floor plan unlike any other in Annapolis. The beautifully appointed Kitchen, inviting living and dining areas, combination gas and wood burning fireplaces and a tranquil large Sunroom addition all flow effortlessly to a private walled courtyard, an intimate outdoor retreat ideal for entertaining or quiet relaxation and completely fenced in. Features 2 ensuite Bedrooms and a 3rd enclosed Bedroom easily adapted into a private home office or gym while still preserving the home's architectural flow. Water Views of Spa Creek, exceptional craftsmanship, and architectural details at every turn make this home as captivating as it is livable. Adding to its rarity are amenities seldom found with the Historic District, including two covered off street parking spaces and an unparalleled waterfront setting just moments from City Dock, the USNA, fine dining, boutiques, galleries and yacht club. Whether enjoyed as a full time residence or an exceptional Annapolis retreat, 100 Market Street represents a once in a generation opportunity to own an irreplaceable piece of the city's history, where more than three centuries of heritage meet the very best of coastal luxury living.

100 Market St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$1,500,000

First time available in decades! Rare opportunity to own a landmark corner commercial property on highly traveled West Street in Annapolis. Prominently positioned in one of the city’s most established business corridors, this property offers exceptional visibility, strong traffic exposure, and convenient access to US-50 and MD-2. The property features its own private on-site parking lot, a highly desirable amenity in this prime Annapolis location. The spacious commercial kitchen layout provides an excellent foundation for a restaurant or food-service concept, with existing gas connections and multiple plumbing lines already in place to help streamline future renovations and build-out. The flexible floor plan offers outstanding potential for a variety of commercial uses, subject to applicable zoning regulations. Whether you’re an owner-user, investor, or developer, this property presents a unique opportunity to customize the space while capitalizing on its premier location, exceptional visibility, and strong long-term value. Property is being sold As-Is. Buyer is responsible for verifying all zoning, permitted uses, and property information.

1975 West St, Annapolis

Listing courtesy of Taylor Properties. Contact:

$1,499,000

Welcome to 1907 Mackiebeth Court, an exceptional new construction home in the established Twin Hills neighborhood of Annapolis. Offering over 5,000 square feet of finished living space on a private 1.4-acre lot backing to a wooded area, this 5-bedroom, 4.5-bathroom home presents a rare opportunity in the Annapolis market. Built by local builder Howmar Homes, the property showcases craftsmanship, thoughtful design, and premium finishes that go well beyond typical builder-grade construction. The light-filled main level features an open floor plan centered around a gourmet kitchen with quartzite countertops, an oversized island, and premium Samsung & Maytag appliances. The kitchen flows seamlessly into the family room with 10-foot ceilings and a gas fireplace, while the morning room and expansive conservatory provide additional spaces for entertaining and everyday living. Upstairs, the spacious primary suite features a private sitting area, dual walk-in closets, and a luxurious bathroom with a soaking tub, walk-in shower, dual vanities, and separate water closets. Convenient upper-level laundry adds everyday practicality. The finished walkout lower level includes a large recreation room, fifth bedroom, full bathroom, and additional unfinished storage space. Outside, the expansive property offers plenty room to enjoy the outdoors. The approved grading plan includes an optional in-ground pool and patio space, offering exciting opportunities to further enhance the home's outdoor living spaces. Additional features include a side-entry three-car garage and a one-year builder warranty from Howmar Homes. With very few newly constructed homes in the Annapolis area offering this combination of finished square footage, acreage, and elevated craftsmanship, 1907 Mackiebeth Court is a truly unique opportunity. Enjoy the space and privacy of a large property just minutes from downtown Annapolis, waterfront attractions, shopping, and dining.

5 Beds ⋅ 5 Baths

Welcome to 1907 Mackiebeth Court, an exceptional new construction home in the established Twin Hills neighborhood of Annapolis. Offering over 5,000 square feet of finished living space on a private 1.4-acre lot backing to a wooded area, this 5-bedroom, 4.5-bathroom home presents a rare opportunity in the Annapolis market. Built by local builder Howmar Homes, the property showcases craftsmanship, thoughtful design, and premium finishes that go well beyond typical builder-grade construction. The light-filled main level features an open floor plan centered around a gourmet kitchen with quartzite countertops, an oversized island, and premium Samsung & Maytag appliances. The kitchen flows seamlessly into the family room with 10-foot ceilings and a gas fireplace, while the morning room and expansive conservatory provide additional spaces for entertaining and everyday living. Upstairs, the spacious primary suite features a private sitting area, dual walk-in closets, and a luxurious bathroom with a soaking tub, walk-in shower, dual vanities, and separate water closets. Convenient upper-level laundry adds everyday practicality. The finished walkout lower level includes a large recreation room, fifth bedroom, full bathroom, and additional unfinished storage space. Outside, the expansive property offers plenty room to enjoy the outdoors. The approved grading plan includes an optional in-ground pool and patio space, offering exciting opportunities to further enhance the home's outdoor living spaces. Additional features include a side-entry three-car garage and a one-year builder warranty from Howmar Homes. With very few newly constructed homes in the Annapolis area offering this combination of finished square footage, acreage, and elevated craftsmanship, 1907 Mackiebeth Court is a truly unique opportunity. Enjoy the space and privacy of a large property just minutes from downtown Annapolis, waterfront attractions, shopping, and dining.

1907 Mackiebeth Ct, Annapolis

Listing courtesy of Douglas Realty LLC. Contact:

$1,495,000

Nestled along one of the most prestigious streets in Historic Annapolis, 268 King George Street presents a rare opportunity to own a beautifully renovated residence with convenient resident-only parking right out front, just steps from the U.S. Naval Academy, St. John's College, City Dock, Main Street, Spa Creek, and the Chesapeake Bay. Offering the perfect blend of historic charm and sophisticated modern living, this exceptional home places you at the center of everything that makes Downtown Annapolis one of Maryland's most desirable destinations. A welcoming covered front porch sets the tone for the home, providing the perfect place to relax, greet neighbors, or enjoy the charm of one of Annapolis' most iconic streets. Inside, timeless architectural details, including rich heart pine floors, soaring ceilings, elegant moldings, and oversized windows, are beautifully complemented by thoughtful, high-end renovations. Designed for both everyday living and effortless entertaining, the main level features elegant formal spaces, including a gracious dining room anchored by a beautiful fireplace and a spacious living room filled with natural light. The gourmet kitchen is appointed with premium appliances, custom cabinetry, generous workspace, and opens seamlessly to a sun-filled four-seasons room, creating an inviting gathering space for family and friends. Upstairs, the luxurious primary suite offers a peaceful retreat highlighted by two walk-in closets with custom built-in organization systems, providing exceptional storage rarely found in Historic Annapolis homes. The beautifully renovated bathrooms showcase designer-inspired tilework, custom vanities, and sophisticated finishes that blend timeless style with modern comfort. Additional bedrooms offer generous accommodations, while the private third-floor suite provides the ideal space for guests, a home office, fitness studio, or additional living area.Outside, a beautifully landscaped courtyard offers remarkable privacy and a tranquil setting for outdoor dining, entertaining, or quiet evenings in the heart of downtown. From your front door, enjoy easy access to award-winning restaurants, boutique shopping, waterfront parks, marinas, sailing, museums, galleries, and the vibrant energy of City Dock. Whether you're looking for a full-time residence or an exceptional Annapolis retreat, 268 King George Street offers an extraordinary opportunity to experience luxury living in one of Maryland's most treasured historic waterfront communities.

Nestled along one of the most prestigious streets in Historic Annapolis, 268 King George Street presents a rare opportunity to own a beautifully renovated residence with convenient resident-only parking right out front, just steps from the U.S. Naval Academy, St. John's College, City Dock, Main Street, Spa Creek, and the Chesapeake Bay. Offering the perfect blend of historic charm and sophisticated modern living, this exceptional home places you at the center of everything that makes Downtown Annapolis one of Maryland's most desirable destinations. A welcoming covered front porch sets the tone for the home, providing the perfect place to relax, greet neighbors, or enjoy the charm of one of Annapolis' most iconic streets. Inside, timeless architectural details, including rich heart pine floors, soaring ceilings, elegant moldings, and oversized windows, are beautifully complemented by thoughtful, high-end renovations. Designed for both everyday living and effortless entertaining, the main level features elegant formal spaces, including a gracious dining room anchored by a beautiful fireplace and a spacious living room filled with natural light. The gourmet kitchen is appointed with premium appliances, custom cabinetry, generous workspace, and opens seamlessly to a sun-filled four-seasons room, creating an inviting gathering space for family and friends. Upstairs, the luxurious primary suite offers a peaceful retreat highlighted by two walk-in closets with custom built-in organization systems, providing exceptional storage rarely found in Historic Annapolis homes. The beautifully renovated bathrooms showcase designer-inspired tilework, custom vanities, and sophisticated finishes that blend timeless style with modern comfort. Additional bedrooms offer generous accommodations, while the private third-floor suite provides the ideal space for guests, a home office, fitness studio, or additional living area.Outside, a beautifully landscaped courtyard offers remarkable privacy and a tranquil setting for outdoor dining, entertaining, or quiet evenings in the heart of downtown. From your front door, enjoy easy access to award-winning restaurants, boutique shopping, waterfront parks, marinas, sailing, museums, galleries, and the vibrant energy of City Dock. Whether you're looking for a full-time residence or an exceptional Annapolis retreat, 268 King George Street offers an extraordinary opportunity to experience luxury living in one of Maryland's most treasured historic waterfront communities.

268 King George St, Annapolis

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

$1,475,000

Luxury New Construction | A Lifestyle of Walkability, Elegance & Annapolis Charm. Don’t miss this exceptional opportunity to own a stunning new-construction home in the highly desirable Homewood neighborhood of Annapolis! With permits in hand and construction about to begin, there is still time to personalize select finishes and make this beautiful home your own. Offering three finished levels of thoughtfully designed living space, this residence delivers more than luxury living, it offers a lifestyle centered around comfort, connection, and the best of Annapolis right outside your door. Inside, 9-foot ceilings on every level and a bright, open-concept floor plan create an inviting sense of space. The gourmet kitchen is designed to impress, featuring 42-inch custom cabinetry, quartz countertops with a coordinating backsplash, stainless steel appliances, and an oversized island that seamlessly connects the dining area and spacious family room. A cozy gas fireplace creates a warm and welcoming gathering space, while sliding glass doors open to a private deck, perfect for morning coffee, evening cocktails, or entertaining friends. A stylish powder room and convenient mudroom with laundry space complete the main level. Upstairs, the expansive primary suite offers a peaceful retreat, complete with a generous walk-in closet and spa-inspired bath featuring a double vanity, soaking tub, and glass-enclosed shower. Two additional bedrooms and a well-appointed full bath provide comfortable accommodations for family and guests. The finished lower level expands the possibilities with a spacious recreation room, fourth bedroom, and full bath, ideal for hosting overnight guests, accommodating extended family, or creating a flexible space for work and leisure. Set along a charming, tree-lined street, this home captures the character of Homewood while offering the style, comfort, and convenience of modern construction. Here, the lifestyle is just as special as the home itself. Enjoy a leisurely walk to downtown Annapolis for waterfront dining, boutique shopping, coffee with friends, and evenings spent exploring the city’s vibrant historic district. With inviting green spaces, a welcoming neighborhood atmosphere, and convenient access to major commuter routes, you can enjoy the perfect balance of urban convenience and residential charm. With its exceptional design, flexible living spaces, and coveted walkable location, this is more than a place to call home, it’s an opportunity to embrace the Annapolis lifestyle. And with construction just getting underway, you may still have the opportunity to add your own personal touch.

Luxury New Construction | A Lifestyle of Walkability, Elegance & Annapolis Charm. Don’t miss this exceptional opportunity to own a stunning new-construction home in the highly desirable Homewood neighborhood of Annapolis! With permits in hand and construction about to begin, there is still time to personalize select finishes and make this beautiful home your own. Offering three finished levels of thoughtfully designed living space, this residence delivers more than luxury living, it offers a lifestyle centered around comfort, connection, and the best of Annapolis right outside your door. Inside, 9-foot ceilings on every level and a bright, open-concept floor plan create an inviting sense of space. The gourmet kitchen is designed to impress, featuring 42-inch custom cabinetry, quartz countertops with a coordinating backsplash, stainless steel appliances, and an oversized island that seamlessly connects the dining area and spacious family room. A cozy gas fireplace creates a warm and welcoming gathering space, while sliding glass doors open to a private deck, perfect for morning coffee, evening cocktails, or entertaining friends. A stylish powder room and convenient mudroom with laundry space complete the main level. Upstairs, the expansive primary suite offers a peaceful retreat, complete with a generous walk-in closet and spa-inspired bath featuring a double vanity, soaking tub, and glass-enclosed shower. Two additional bedrooms and a well-appointed full bath provide comfortable accommodations for family and guests. The finished lower level expands the possibilities with a spacious recreation room, fourth bedroom, and full bath, ideal for hosting overnight guests, accommodating extended family, or creating a flexible space for work and leisure. Set along a charming, tree-lined street, this home captures the character of Homewood while offering the style, comfort, and convenience of modern construction. Here, the lifestyle is just as special as the home itself. Enjoy a leisurely walk to downtown Annapolis for waterfront dining, boutique shopping, coffee with friends, and evenings spent exploring the city’s vibrant historic district. With inviting green spaces, a welcoming neighborhood atmosphere, and convenient access to major commuter routes, you can enjoy the perfect balance of urban convenience and residential charm. With its exceptional design, flexible living spaces, and coveted walkable location, this is more than a place to call home, it’s an opportunity to embrace the Annapolis lifestyle. And with construction just getting underway, you may still have the opportunity to add your own personal touch.

1207 Mcguckian St, Annapolis

Listing courtesy of EXP Realty, LLC. Contact:

$1,400,000

Welcome to 71 Farragut! This beautiful 4-bedroom; 3 ½ bath home is located in the highly sought-after Bay Ridge Community. The heart of the home features a large eat-in kitchen, with a cozy fireplace in the adjoining family room, and a sun-filled living room with vaulted ceilings. The private professionally designed landscaped yard showcases an in-ground swimming pool that backs to conservation land. Located in one of Annapolis’s premiere waterfront communities, don’t miss your opportunity to call Bay Ridge Home. With the optional community membership, discover a unique chance to experience a coastal lifestyle with private beaches, a marina, walking trails, playgrounds, and year-round neighborhood events. Ideally located just minutes from downtown Annapolis and has convenient access Rt. 50, 97, Washington, Baltimore and BWI Airport.

Welcome to 71 Farragut! This beautiful 4-bedroom; 3 ½ bath home is located in the highly sought-after Bay Ridge Community. The heart of the home features a large eat-in kitchen, with a cozy fireplace in the adjoining family room, and a sun-filled living room with vaulted ceilings. The private professionally designed landscaped yard showcases an in-ground swimming pool that backs to conservation land. Located in one of Annapolis’s premiere waterfront communities, don’t miss your opportunity to call Bay Ridge Home. With the optional community membership, discover a unique chance to experience a coastal lifestyle with private beaches, a marina, walking trails, playgrounds, and year-round neighborhood events. Ideally located just minutes from downtown Annapolis and has convenient access Rt. 50, 97, Washington, Baltimore and BWI Airport.

71 Farragut, Annapolis

Listing courtesy of Douglas Realty LLC. Contact:

$1,399,999

PRICE REDUCED! THIS HOUSE CAN ACCOMODATE A POOL, to ADD to your castle on the hill! Introducing an extraordinary custom-built estate with Brand new roof, not reflected in photos, privately nestled on more than 2+ WOODED ACRES along the B&A Trail in a quiet cul-de-sac setting, just minutes from downtown HISTORIC ANNAPOLIS and convenient to the Rt. 50 corridor. Located in the sought-after Broadneck School District, this exceptional property also includes deeded mooring rights to Cool Spring Cove. Chase Creek Swim Club nearby for summer pool fun! Designed for both elegant entertaining and comfortable everyday living, the home showcases a dramatic two-story great room highlighted by an impressive 18-foot stone fireplace and expansive windows that fill the space with natural light. The OPEN-CONCEPT layout seamlessly connects the living, dining, and gourmet kitchen areas, with quartz countertops and a gas range with double ovens create the perfect culinary setting. Tailored for MAIN-LEVEL LIVING, the spacious primary suite offers a private retreat complete with a spa-inspired bath featuring a walk-in shower/steam room, jacuzzi tub, and oversized walk-in closet. The main floor also includes a flexible guest bedroom or office, a half bath, and an expansive laundry/mudroom adjoining the oversized three-car garage and workshop with custom cabinetry. A stunning curved open staircase leads to the upper level, where a second primary suite provides ideal MULTI-GENERATIONAL LIVING accommodations, accompanied by two additional bedrooms connected by a Jack-and-Jill bath. The FINISHED LOWER LEVEL significantly expands the home’s living space with a large recreation room centered around an 11-foot stone fireplace, along with a custom bar, gaming area, bonus room or optional sixth bedroom, luxury full bath, and extensive storage and wine cellar space. OUTDOOR LIVING is equally exceptional, featuring a sprawling illuminated patio designed for year-round entertaining. The fully equipped outdoor kitchen includes a pizza oven, burners, sink, mini refrigerator, and adjoining firepit area. Thoughtful upgrades throughout — including a whole-house generator — complete this truly one-of-a-kind property. New pricing reflects the Value of a lifetime.

5 Beds ⋅ 5 Baths

PRICE REDUCED! THIS HOUSE CAN ACCOMODATE A POOL, to ADD to your castle on the hill! Introducing an extraordinary custom-built estate with Brand new roof, not reflected in photos, privately nestled on more than 2+ WOODED ACRES along the B&A Trail in a quiet cul-de-sac setting, just minutes from downtown HISTORIC ANNAPOLIS and convenient to the Rt. 50 corridor. Located in the sought-after Broadneck School District, this exceptional property also includes deeded mooring rights to Cool Spring Cove. Chase Creek Swim Club nearby for summer pool fun! Designed for both elegant entertaining and comfortable everyday living, the home showcases a dramatic two-story great room highlighted by an impressive 18-foot stone fireplace and expansive windows that fill the space with natural light. The OPEN-CONCEPT layout seamlessly connects the living, dining, and gourmet kitchen areas, with quartz countertops and a gas range with double ovens create the perfect culinary setting. Tailored for MAIN-LEVEL LIVING, the spacious primary suite offers a private retreat complete with a spa-inspired bath featuring a walk-in shower/steam room, jacuzzi tub, and oversized walk-in closet. The main floor also includes a flexible guest bedroom or office, a half bath, and an expansive laundry/mudroom adjoining the oversized three-car garage and workshop with custom cabinetry. A stunning curved open staircase leads to the upper level, where a second primary suite provides ideal MULTI-GENERATIONAL LIVING accommodations, accompanied by two additional bedrooms connected by a Jack-and-Jill bath. The FINISHED LOWER LEVEL significantly expands the home’s living space with a large recreation room centered around an 11-foot stone fireplace, along with a custom bar, gaming area, bonus room or optional sixth bedroom, luxury full bath, and extensive storage and wine cellar space. OUTDOOR LIVING is equally exceptional, featuring a sprawling illuminated patio designed for year-round entertaining. The fully equipped outdoor kitchen includes a pizza oven, burners, sink, mini refrigerator, and adjoining firepit area. Thoughtful upgrades throughout — including a whole-house generator — complete this truly one-of-a-kind property. New pricing reflects the Value of a lifetime.

1603 Waters Ridge Ct, Annapolis

Listing courtesy of Keller Williams Flagship. Contact:

Discover an exceptional blend of sophisticated design, resort-inspired living, and everyday convenience in this beautifully appointed Annapolis residence. Tucked along a quiet street yet remarkably close to everything that makes Annapolis so desirable, this distinctive home offers the perfect balance of privacy and accessibility. From the vibrant restaurants, boutiques, and waterfront attractions of Historic Downtown Annapolis to the charm of nearby neighborhoods and marinas, the very best of the Annapolis lifestyle is just moments away. Designed with both elegant entertaining and comfortable everyday living in mind, the home welcomes you with striking architectural details, beautifully curated finishes, and thoughtfully designed spaces throughout. The main level features gracious formal living and dining areas, complemented by a butler's pantry that makes hosting effortless. At the heart of the home, a beautifully appointed kitchen opens seamlessly to the casual dining area and inviting family room, where accordion glass doors overlook the backyard retreat with serene pool as the focal point The outdoor living experience is truly exceptional. A stunning private pool serves as the centerpiece of a beautifully designed backyard, framed by lush landscaping and mature greenery that create a wonderful sense of seclusion. An expansive covered patio with comfortable lounging and dining areas, ceiling fans, and a fully equipped outdoor kitchen provides the perfect setting for everything from leisurely summer afternoons to memorable evenings entertaining family and friends. The seamless connection between the interior living spaces and poolside retreat creates an atmosphere reminiscent of a private luxury resort. Upstairs, an open loft with a bar area provides an additional gathering space, ideal for relaxing or entertaining or can easily be transformed into an additional bedroom and bath. The luxurious primary suite offers a peaceful escape, complete with an expansive walk-in closet and beautifully appointed spa-inspired bath featuring a curbless walk-through shower. A private balcony overlooking the pool adds another inviting place to unwind. Two additional bedrooms share a well-appointed full bath, offering comfortable accommodations for family or guests. The finished lower level provides remarkable versatility, with a spacious living room, kitchenette, bedroom, and full bath creating an ideal arrangement for extended family, overnight guests, or multigenerational living. A dedicated wine cellar adds a sophisticated touch, while an additional bonus room, currently utilized as a conference room, offers endless possibilities as a private home theater, media lounge, or recreation space. With its elegant interiors, exceptional outdoor amenities, and peaceful setting just minutes from the energy and excitement of Annapolis, this remarkable residence offers an extraordinary opportunity to experience luxury living without compromising convenience. Welcome Home!

Discover an exceptional blend of sophisticated design, resort-inspired living, and everyday convenience in this beautifully appointed Annapolis residence. Tucked along a quiet street yet remarkably close to everything that makes Annapolis so desirable, this distinctive home offers the perfect balance of privacy and accessibility. From the vibrant restaurants, boutiques, and waterfront attractions of Historic Downtown Annapolis to the charm of nearby neighborhoods and marinas, the very best of the Annapolis lifestyle is just moments away. Designed with both elegant entertaining and comfortable everyday living in mind, the home welcomes you with striking architectural details, beautifully curated finishes, and thoughtfully designed spaces throughout. The main level features gracious formal living and dining areas, complemented by a butler's pantry that makes hosting effortless. At the heart of the home, a beautifully appointed kitchen opens seamlessly to the casual dining area and inviting family room, where accordion glass doors overlook the backyard retreat with serene pool as the focal point The outdoor living experience is truly exceptional. A stunning private pool serves as the centerpiece of a beautifully designed backyard, framed by lush landscaping and mature greenery that create a wonderful sense of seclusion. An expansive covered patio with comfortable lounging and dining areas, ceiling fans, and a fully equipped outdoor kitchen provides the perfect setting for everything from leisurely summer afternoons to memorable evenings entertaining family and friends. The seamless connection between the interior living spaces and poolside retreat creates an atmosphere reminiscent of a private luxury resort. Upstairs, an open loft with a bar area provides an additional gathering space, ideal for relaxing or entertaining or can easily be transformed into an additional bedroom and bath. The luxurious primary suite offers a peaceful escape, complete with an expansive walk-in closet and beautifully appointed spa-inspired bath featuring a curbless walk-through shower. A private balcony overlooking the pool adds another inviting place to unwind. Two additional bedrooms share a well-appointed full bath, offering comfortable accommodations for family or guests. The finished lower level provides remarkable versatility, with a spacious living room, kitchenette, bedroom, and full bath creating an ideal arrangement for extended family, overnight guests, or multigenerational living. A dedicated wine cellar adds a sophisticated touch, while an additional bonus room, currently utilized as a conference room, offers endless possibilities as a private home theater, media lounge, or recreation space. With its elegant interiors, exceptional outdoor amenities, and peaceful setting just minutes from the energy and excitement of Annapolis, this remarkable residence offers an extraordinary opportunity to experience luxury living without compromising convenience. Welcome Home!

204 S Villa Ave, Annapolis

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

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.

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:

Set back off the road on a quiet cul-de-sac in the coveted Saefern community, this contemporary home offers peaceful water views, a private wooded setting, and endless potential to make it your own. Whether you're looking to move right in and enjoy the home as it is or reimagine the space into your dream retreat, this property presents an incredible opportunity in one of Annapolis' most sought-after waterfront communities. Designed to embrace its natural surroundings, the home is filled with light and features soaring ceilings, warm wood architectural details, and expansive windows that bring the outdoors in. The dramatic living room is anchored by a striking brick fireplace and flows into the dining area and kitchen, creating an inviting space for gathering. Three sets of sliding glass doors open to the expansive balcony, seamlessly blending indoor and outdoor living while framing peaceful water and woodland views. Just beyond, the enclosed porch with vaulted ceilings provides a year-round place to relax while taking in the peaceful water and woodland views. The thoughtfully designed main level offers two bedrooms, including a spacious primary suite with a private sitting area and ensuite bath, along with a second bedroom that is served by a full hall bath, ideal for guests, family, or a home office. The walkout lower level expands the living space with a generous family room featuring a second fireplace, a built-in bar area, and access to the adjoining sunroom and patio, creating the perfect setting for entertaining. Two additional bedrooms are located on this level, including one with a private ensuite bath and private patio. An additional bedroom offers flexible accommodations for guests or multigenerational living. Life in Saefern is about much more than the home itself. Membership in the renowned Saefern Saddle & Yacht Club (SSYC) includes a boat slip, marina, swimming pool, tennis and pickleball courts, horse stables, dog park, playground, and an active community lifestyle. Just minutes from Historic Annapolis, the U.S. Naval Academy, shopping, dining, and convenient commuter routes to Washington, D.C. and Baltimore, this is a rare opportunity to invest in a home with outstanding bones, water views, and the chance to create something truly special. Welcome Home!

4 Beds ⋅ 3 Baths

Set back off the road on a quiet cul-de-sac in the coveted Saefern community, this contemporary home offers peaceful water views, a private wooded setting, and endless potential to make it your own. Whether you're looking to move right in and enjoy the home as it is or reimagine the space into your dream retreat, this property presents an incredible opportunity in one of Annapolis' most sought-after waterfront communities. Designed to embrace its natural surroundings, the home is filled with light and features soaring ceilings, warm wood architectural details, and expansive windows that bring the outdoors in. The dramatic living room is anchored by a striking brick fireplace and flows into the dining area and kitchen, creating an inviting space for gathering. Three sets of sliding glass doors open to the expansive balcony, seamlessly blending indoor and outdoor living while framing peaceful water and woodland views. Just beyond, the enclosed porch with vaulted ceilings provides a year-round place to relax while taking in the peaceful water and woodland views. The thoughtfully designed main level offers two bedrooms, including a spacious primary suite with a private sitting area and ensuite bath, along with a second bedroom that is served by a full hall bath, ideal for guests, family, or a home office. The walkout lower level expands the living space with a generous family room featuring a second fireplace, a built-in bar area, and access to the adjoining sunroom and patio, creating the perfect setting for entertaining. Two additional bedrooms are located on this level, including one with a private ensuite bath and private patio. An additional bedroom offers flexible accommodations for guests or multigenerational living. Life in Saefern is about much more than the home itself. Membership in the renowned Saefern Saddle & Yacht Club (SSYC) includes a boat slip, marina, swimming pool, tennis and pickleball courts, horse stables, dog park, playground, and an active community lifestyle. Just minutes from Historic Annapolis, the U.S. Naval Academy, shopping, dining, and convenient commuter routes to Washington, D.C. and Baltimore, this is a rare opportunity to invest in a home with outstanding bones, water views, and the chance to create something truly special. Welcome Home!

500 Sara Dr, Annapolis

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

An exceptional opportunity awaits in coveted West Annapolis—a rare 0.61-acre offering with endless potential. Whether you envision a thoughtful renovation or a custom new build, this expansive lot provides the perfect canvas to create your dream residence in one of the area’s most sought-after neighborhoods. Approved civil engineering plans by Drum, Loyka & Associates, LLC and architectural designs by Custom Designs Unlimited convey with the property (city approvals secured; permits not yet pulled), offering a valuable head start toward bringing your vision to life. The generously sized lot and current AS-IS cottage provides an abundance of outdoor space, inviting a plethora of outdoor gatherings, summer barbecues, and relaxed evenings enjoying the vibrant West Annapolis lifestyle. Just beyond your doorstep, stroll to acclaimed restaurants, local pubs, charming boutiques, and convenient street-end water access. Ideally situated near Downtown Annapolis, Navy Stadium events, and the Naval Academy, the location also provides effortless commuter access to Route 50 and the Bay Bridge for Eastern Shore escapes or travel to Washington, D.C. A truly special setting offered AS-IS, ready for its next chapter. Welcome Home!

4 Beds ⋅ 2 Baths

An exceptional opportunity awaits in coveted West Annapolis—a rare 0.61-acre offering with endless potential. Whether you envision a thoughtful renovation or a custom new build, this expansive lot provides the perfect canvas to create your dream residence in one of the area’s most sought-after neighborhoods. Approved civil engineering plans by Drum, Loyka & Associates, LLC and architectural designs by Custom Designs Unlimited convey with the property (city approvals secured; permits not yet pulled), offering a valuable head start toward bringing your vision to life. The generously sized lot and current AS-IS cottage provides an abundance of outdoor space, inviting a plethora of outdoor gatherings, summer barbecues, and relaxed evenings enjoying the vibrant West Annapolis lifestyle. Just beyond your doorstep, stroll to acclaimed restaurants, local pubs, charming boutiques, and convenient street-end water access. Ideally situated near Downtown Annapolis, Navy Stadium events, and the Naval Academy, the location also provides effortless commuter access to Route 50 and the Bay Bridge for Eastern Shore escapes or travel to Washington, D.C. A truly special setting offered AS-IS, ready for its next chapter. Welcome Home!

4 Shiley St, Annapolis

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