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luxury houses for sale Annapolis, United States

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50

House with pool and garden Annapolis (United States)

Open Sunday, November 1st! Experience the best of the Annapolis lifestyle at 1610 Ridout Road, where beautifully updated interiors, exceptional outdoor living, and coveted water access come together in one inviting home. Inside, an open and comfortable floor plan is designed for the way people actually live. The kitchen opens to a sun-filled bar and dining area, where a sliding door provides direct access to the backyard and creates an easy connection between indoor and outdoor living. Two gas fireplaces, one in the living room and another in the family room, bring warmth and character to the main level, while the finished lower level provides additional flexible living space and storage. Upstairs, the spacious primary suite with an ensuite bath and three additional bedrooms sharing a full hall bath, offer comfortable space for family and guests. An attached two-car garage completes the home’s practical conveniences. Outside is where this property truly distinguishes itself. Framed by lush landscaping, the expansive, fully fenced backyard unfolds as a series of thoughtfully created outdoor living spaces. The in-ground pool, hot tub, generous patio space, and pergola-covered dining area area designed for long summer days and effortless entertaining, while the broad lawn offers plenty of room to play, garden, or simply unwind. And the lifestyle extends well beyond the property line. Amberley is one of the Broadneck Peninsula’s sought-after water-privileged communities, with three private community piers along Whitehall and Ridout Creeks and 45 slips accommodating both power and sailboats. Residents also enjoy a boat ramp, kayak and paddleboard storage, and a launch pier for smaller watercraft. More than 15 acres of community forest and open space, along with over 3 miles of paved roads and walking trails, contribute to Amberley’s peaceful, established character. Just minutes from Downtown Annapolis, Broadneck schools, and convenient routes to Washington, D.C., Baltimore, and the Eastern Shore, this private oasis offers something increasingly difficult to find: space to spread out, a backyard built for living, and easy access to the Chesapeake Bay lifestyle.

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$1,195,000
4bedrooms
3bathrooms
land 0.3ha

By Ttr Sotheby's International Realty

30
3D visit

House with garden and terrace Annapolis (United States)

An extraordinary opportunity to own one of Annapolis' most distinctive waterfront properties, offering some of the finest views on Spa Creek and the rare privilege of owning your own private marina in your backyard with dockside parking. Perfectly positioned to capture breathtaking panoramic vistas, this elegant Nantucket-inspired residence is filled with natural light, featuring walls of glass that showcase the ever-changing waterfront from nearly every room. Multiple balconies and an expansive waterside terrace invite effortless indoor-outdoor living, creating exceptional spaces for entertaining or simply enjoying the beauty of life on the water. A dockside workshop is a great opportunity to work and enjoy waterfront living. The thoughtfully designed floor plan includes spacious living areas, a versatile 1800 square feet (approximate) lower level with an in-law suite or private guest accommodations, and endless opportunities to personalize the home to suit your lifestyle. This home even has a koi pond in the front yard. Whether you're an avid yachtsman, seeking a multigenerational waterfront retreat, or searching for a truly one-of-a-kind Annapolis property, this exceptional offering combines luxury, privacy, and an unmatched boating lifestyle in one remarkable setting.

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$4,600,000
473m²
5bedrooms
3bathrooms

By Annonceur International

38
Video

Property with pool Annapolis (United States)

Welcome to Dreams Landing, one of Annapolis's most desirable water-privileged condominium communities. Offering beautiful views of the Severn River, this charming two-bedroom, one-bath residence combines the tranquility of waterside living with an exceptional collection of community amenities. Move-in ready and thoughtfully updated, the residence features hardwood flooring throughout, an updated kitchen with upgraded countertops, cabinetry, and stainless steel appliances, and a beautifully renovated bathroom with a walk-in shower. The primary bedroom offers comfortable space, while the versatile second bedroom is perfect for guests, a home office, or both. Perched along a hillside overlooking the Severn River, Dreams Landing offers a picturesque setting of the Severn River. At the heart of the community, a sparkling swimming pool is surrounded by two expansive decks with breathtaking, elevated views of the river. These inviting spaces provide the perfect backdrop for relaxing afternoons, entertaining friends, and enjoying the community's cherished social gatherings. Boating enthusiasts will appreciate the community marina, which offers slips for vessels of various sizes and convenient access to the Chesapeake Bay. Additional amenities include a fitness center, a woodworking shop, and a private storage unit included with the residence. Beyond its exceptional amenities, Dreams Landing is known for its welcoming atmosphere and strong sense of community. Whether spending the day on the water, relaxing poolside, or simply watching the boats pass along the Severn River, residents enjoy a lifestyle that captures the very best of Annapolis living. Experience the charm, convenience, and exceptional water privileges of Dreams Landing. Schedule your private showing today!

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$415,000
2bedrooms
1bathroom
land 0ha

By Ttr Sotheby's International Realty

25

House with terrace Annapolis (United States)

Beautiful 2-Bed, 2-Bath Condo with Water Access in Annapolis! Welcome home to this beautifully updated 2-bedroom, 2-bathroom condo in the sought-after Riva Trace! Step inside to discover a bright and airy open floor plan with fresh neutral paint, luxury vinyl plank flooring, and modern fixtures throughout. The spacious living room features a cozy fireplace and direct access to light-filled sunroom, perfect for morning coffee or evening relaxation. The renovated kitchen is a chef's dream with white shaker cabinets, quartz countertops, stainless steel appliances, and a breakfast bar overlooking the dining area—ideal for entertaining. The primary suite boasts a large walk-in closet, a beautifully updated ensuite bath with a dual vanity, and access to the balcony. A second generously sized bedroom and a stylishly renovated full bath complete the home. Enjoy low-maintenance living with fantastic community amenities, including water access, tennis courts, a playground, and walking trails. Conveniently located just minutes from downtown Annapolis, the Naval Academy, shopping, dining, and major commuter routes, this condo is a rare find!

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$380,000
2bedrooms
2bathrooms

By Monument Sotheby's International Realty

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50
Video

House with garden and terrace Annapolis (United States)

Experience the timeless charm of waterfront living along the protected waters of Burley Creek, where beautifully landscaped grounds, a distinctive boathouse and exceptional boating amenities create an idyllic Chesapeake Bay retreat. Located in the sought-after Beechwood on the Burley community, this captivating Cape Cod combines classic architectural character with thoughtful modern improvements, offering a wonderful balance of everyday comfort and effortless waterfront entertaining. The waterfront is truly the heart of this remarkable property. Approximately 75 feet of shoreline, a private pier, boathouse with upgraded boat lift, and kayak launch invite endless opportunities to embrace life on the water. Exceptional docking accommodations include two deep-water slips capable of accommodating vessels up to 70 and 50 feet, a rare and desirable feature for the avid boating enthusiast. Extensive improvements include a reconfigured pier with new pilings, decking, and electrical service, along with a relocated boat lift beneath the boathouse. Whether setting out for a day on the Chesapeake Bay, enjoying a peaceful morning paddle, or gathering with friends along the shoreline, every day offers an extraordinary connection to the water. Inside, inviting living spaces blend traditional craftsmanship with modern conveniences. Rich hardwood flooring, architectural details, and impressive stone fireplaces create warmth and character throughout. The spacious family room opens to a screened porch, extending the living space outdoors, while the distinctive dining room and family room features vaulted ceilings, exposed beams, wet bar and a charming reading nook. The beautifully appointed kitchen offers granite countertops, and updated appliances. The main-level primary suite provides comfort and convenience with custom built-in cabinetry and an updated ensuite bath. Upstairs, two additional bedrooms, full bath and a bonus room feature vaulted ceilings and dormer windows offer welcoming accommodations for family and guests. The finished lower level features a second stone fireplace in the great room and multi-purpose room, creating another inviting destination for entertaining and relaxation. Outdoor living continues with a beautiful new stone patio, landscaped grounds, and multiple spaces to appreciate the peaceful waterfront setting. Additional improvements include updated HVAC systems, water treatment, fencing, and expanded parking. A detached two-car garage adds convenience. Residents of Beechwood on the Burley have access through the voluntary community association to a waterfront park, community pier, playground, and kayak storage. Located in the Blue-Ribbon Broadneck School district and just 5 miles to downtown Annapolis and Severna Park. Convenient to Baltimore, BWI, Ft. Meade/NSA and Washington, DC., the location provides the very best this region has to offer in a 30-mile radius. Welcome Home!

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$1,895,000
3bedrooms
3bathrooms
land 0.2ha

By Ttr Sotheby's International Realty

50
Video

House with pool and terrace Annapolis (United States)

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!

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$1,395,000
4bedrooms
4bathrooms
land 0.1ha

By Ttr Sotheby's International Realty

40
Video

House with terrace Annapolis (United States)

***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.

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$1,875,000
4bedrooms
4bathrooms
land 0.1ha

By Ttr Sotheby's International Realty

35

House with garden and terrace Annapolis (United States)

Price Improvement Incredibly maintained home in the sought-after water-privileged community of Beechwood on the Burley. This two-level home offers comfortable living, a spacious outdoor setting, and an ideal Broadneck Peninsula location just minutes from downtown Annapolis and with easy access to Route 50. The established community offers water access, a marina, playground, and peaceful neighborhood setting, with convenient back-road access to downtown Annapolis. Inside, the home has been well maintained and thoughtfully updated with refinished hardwood floors, fresh paint, updated lighting, and new carpet. The upper level features a comfortable open-concept layout with a living room that flows into the dining area and kitchen. Granite countertops, beautiful cabinetry, and a center island with seating create a welcoming kitchen with plenty of workspace. Sliding glass doors open to a composite deck overlooking the flat, fully fenced backyard, where mature landscaping provides privacy and a lovely backdrop for outdoor living. The primary suite features a private ensuite bath, accompanied by two additional bedrooms and a full hall bath. The lower level adds valuable living space with a family room centered around a propane gas fireplace, an office/fourth bedroom, laundry room, and access to the attached garage. Ample storage throughout adds to the home's everyday functionality. Beechwood on the Burley is a voluntary HOA community with access to a waterfront park, community dock with slips, playground, and picnic area along the water. The neighborhood's quiet roads and surrounding farmland create a peaceful setting for walking, running, and cycling, while the home's location provides easy access to Annapolis, Broadneck schools, shopping, dining, and major commuter routes.

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$574,900
4bedrooms
2bathrooms
land 0.1ha

By Monument Sotheby's International Realty

44
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House with terrace Annapolis (United States)

Refined city living meets effortless Annapolis charm in this exceptional end-unit townhome, perfectly positioned in the heart of the Arts District. From this coveted location, some of Downtown Annapolis’ best restaurants, boutiques, Maryland Hall for the Creative Arts, Spa Creek waterfront, scenic trails, playgrounds, and Navy Stadium are all just moments away. The complimentary City Circulator makes exploring the waterfront and City Dock remarkably easy, while convenient access to Route 50 keeps commuting a breeze. Spanning approximately 3,400 square feet over four beautifully finished levels, this sophisticated residence offers an exceptional combination of space, versatility, and custom character. Fresh interior paint creates a crisp, inviting backdrop, while upgraded lighting and carefully selected wallpaper accents in the primary suite and powder room bring an elevated designer aesthetic to the home. The main level is designed for both everyday living and entertaining, with an open-concept floor plan, dramatic ceilings, and an abundance of natural light. The gracious living room centers around a gas fireplace, creating a warm and inviting gathering space. The adjoining kitchen features granite countertops, stainless steel appliances, a substantial center island with seating and storage, and effortless connection to the dining area. Upstairs, the private primary suite offers a serene retreat complete with a generous walk-in closet and beautifully appointed en suite bath featuring a soaking tub, dual vanity, and separate shower. Two additional bedrooms, a full bath, and conveniently located laundry complete the second level. The extraordinary top-floor loft expands the possibilities even further, featuring vaulted ceilings, exceptional storage, a full bath, and a dedicated brand new heating and cooling mini-split system. Equally suited for a second primary suite, guest quarters, home office, creative studio, or comfortable lounge, this versatile space adapts beautifully to a variety of lifestyles. The fully finished lower level adds another dimension to the home with an additional bedroom, full bath, and egress window, offering an ideal private retreat for guests, a home office, recreation space, or extended-stay accommodations. The property also includes two assigned parking spaces, complemented by additional community parking. With its distinctive end-unit setting, impressive scale, thoughtful custom finishes, and enviable proximity to the very best of Downtown Annapolis, this is a home that delivers the quintessential Annapolis lifestyle - with room to live, work, entertain, and enjoy it all. Welcome Home!

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$659,000
5bedrooms
5bathrooms
land 0ha

By Ttr Sotheby's International Realty

50

House with terrace Annapolis (United States)

Why wait to build when you can move right in? Welcome to 126 Stilly Way, a beautifully finished, nearly new home in Annapolis’ Parkside Preserve. Built in 2024 and offering more than 4,400 square feet of finished living space across three levels, this home combines the appeal of newer construction with the convenience of having the finishing touches already in place. The bright, open main level features a beautifully appointed kitchen with white cabinetry, quartz countertops, stainless steel appliances, gas cooking, double wall ovens, tiled backsplash, and an oversized center island. The kitchen flows seamlessly into the spacious family room, anchored by a gas fireplace with custom built-ins. A separate dining room provides additional space for entertaining. Upstairs, the primary suite features a tray ceiling, walk-in closets, and private bath with dual vanities, soaking tub, and oversized glass-enclosed shower. Three additional bedrooms each with their own walk-in closets and well-appointed baths complete the upper level. The finished lower level adds exceptional flexibility, with an expansive recreation area, wet bar with beverage refrigerator, full bath, and the potential to create a true fifth bedroom while still maintaining plenty of additional living and entertaining space. What truly sets this home apart is how much has already been done. Window treatments are installed, the lower level is finished, the yard is established, and the home is ready to enjoy from day one. Enjoy the benefits of a newer home without waiting on a construction timeline or tackling the many finishing touches that often come after settlement. A covered front porch, HardiePlank and brick exterior, level backyard, and attached two-car garage complete the property. Located just moments from Quiet Waters Park and convenient to Downtown Annapolis, shopping, dining, and major commuter routes, 126 Stilly Way offers the opportunity to enjoy newer construction with the added benefit of a home that is already finished, established, and truly move-in ready.

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$1,160,000
4bedrooms
5bathrooms
land 0.1ha

By Ttr Sotheby's International Realty

35
Video

House with pool and terrace Annapolis (United States)

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!

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$1,395,000
4bedrooms
3bathrooms
land 0.6ha

By Ttr Sotheby's International Realty

45
Video

House with pool and garden Annapolis (United States)

Located in the coveted Wardour community, this stately home combines timeless architecture with an enviable walkable location near West Annapolis’ shops and restaurants and just minutes from downtown. With stunning curb appeal, spacious 0.55 acre lot, expansive front yard and water views from nearly every room in the home, this property offers a rare combination of privacy and community, where every day feels like a retreat yet conveniences are just minutes away. The main level welcomes with a gracious foyer flanked by formal living and dining rooms, highlighted by custom millwork, crown molding, wainscoting, and hardwood floors. The formal living room features a classic gas fireplace, while the private office with built-ins and the inviting family room with a coffered ceiling provide versatile spaces for work and relaxation. The gourmet kitchen impresses with high-end appliances, a large center island, casual dining area overlooking the backyard, and wet bar adjoining the dining room. A well-designed mudroom off the two-car garage and side entry enhances everyday function. Upstairs, three spacious ensuite bedrooms complement the luxurious primary suite, which offers a serene sitting room with gas fireplace, private balcony, and spa-like bath. The top floor is a flexible open space with full bath, perfect as an office, playroom, studio, or lounge. The lower level is an entertainer’s retreat with a full bar, open gathering space anchored by a wood-burning fireplace, and a room prepped to become a wine cellar. A full bath and additional bedroom complete this versatile level. Conveniently located to access Downtown Annapolis, head over the Bay Bridge to the Eastern shore or jump on Rt. 50 to get back to Washington, DC and just a few short blocks to West Annapolis' charming commercial district's restaurants & shops. Welcome Home!

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$3,495,000
5bedrooms
7bathrooms
land 0.2ha

By Ttr Sotheby's International Realty

46
Video

House with pool and terrace Annapolis (United States)

Welcome to this exceptional custom-built estate set on 3.1 acres in Wyatts Hill community. Offering three finished levels of thoughtfully designed living space, this five-bedroom, seven-bathroom home combines timeless architecture, modern updates, and resort-inspired outdoor living. A grand two-story foyer welcomes you with a sweeping curved staircase and soaring ceilings. The main level is designed for both everyday living and entertaining, featuring a formal dining room, private office, dramatic two-story family room with a fireplace, and a sunroom connected by French doors that fills the home with natural light. The gourmet kitchen serves as the heart of the home with an oversized center island, custom cabinetry, granite countertops, a spacious breakfast area, and a butler’s pantry, creating an ideal space for gatherings large and small. The main level also features a spacious primary suite with an en-suite bath, providing flexibility for a variety of living arrangements. An additional office, laundry room, and powder room complete the main level. Upstairs, a second primary suite offers a private retreat with a sitting area and en-suite bath. Three additional bedrooms each feature their own private en-suite bathrooms, providing comfort and privacy throughout the upper level. The walkout lower level expands the home’s living and entertaining space with a large recreation room, second kitchen, half bath, and abundant storage. Completed in 2023, the backyard was transformed into an exceptional outdoor living space featuring a heated saltwater pool, expansive patio, outdoor fireplace, and a fully equipped outdoor kitchen designed for entertaining and enjoying an outdoor lifestyle. Recent improvements include a new roof (2025), two new HVAC systems (2022), new wood front and garage doors, a Tesla EV charger, and a lawn irrigation system. Located in the desirable Wyatts Hill community with no HOA, this home offers convenient access to Historic Annapolis, BWI Airport, Fort Meade, Baltimore, Washington, D.C., and major commuter routes including I-97 and Route 50.

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$1,998,000
5bedrooms
7bathrooms
land 1.3ha

By Ttr Sotheby's International Realty

34

House with garden Annapolis (United States)

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.

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$1,495,000
4bedrooms
4bathrooms
land 0ha

By Monument Sotheby's International Realty

50

House with pool and garden Annapolis (United States)

This spacious split-level home set on over a third of an acre features three main-floor bedrooms, two full baths (one of which is ensuite to the primary bedroom), and hardwood flooring. The vaulted living/dining room opens to a big deck overlooking a fully-fenced back yard. Downstairs, the fourth bedroom can be used as a TV room, office, or home gym. The lower-level includes a spacious family room with wood-burning fireplace, half bath, bonus room, laundry room, and plenty of storage space. The family room opens to the back yard. Numerous property improvements include a newer HVAC (2024), kitchen appliances (2022), replacement windows and sliding doors, and fresh paint throughout. The roof and gutters are less than five years old. Admiral Heights is a popular water-privileged community close to the Navy Marine Corps Stadium and just a mile and a half from downtown Annapolis. The neighborhood consists of more than 600 homes and features community amenities including a pool, a swim club, docks, parks, and kayak/canoe storage on Weems Creek. NOTE: Home is empty - many photos show virtual staging. Also, seller conducted a thorough home inspection in September 2026; a copy of this report is available upon request.

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$725,000
4bedrooms
3bathrooms
land 0.2ha

By Ttr Sotheby's International Realty

36
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Seaside house with pool and terrace Annapolis (United States)

Celebrate the Eastport lifestyle in this beautifully crafted home, ideally positioned on the coveted Eastport Peninsula. Built in 2015 and thoughtfully designed for easy, low-maintenance living, the home blends classic Craftsman character with beautifully appointed spaces and modern amenities, making this home equally suited for a full-time residence or an Annapolis retreat. Thoughtful details are found throughout, including two spacious primary suites with ensuite baths and walk-in closets and a versatile loft level offering additional living/guest space with full bath. Natural light fills the interiors, while glimpses of Back Creek from various vantage points offer a subtle reminder of the home's maritime surroundings. The true highlight awaits above on the coveted roof deck, where elevated views open across Back Creek and create an incredible outdoor living space. Whether gathering with friends, unwinding at the end of the day, or simply watching the activity on the water, this private perch captures the essence of life in Eastport. Outside, professional landscaping with irrigation and uplighting creates an inviting setting while keeping maintenance to a minimum. HardiePlank siding and timeless architectural details complement the home's Craftsman style and make it as appealing outside as it is within. Located in the heart of Eastport's maritime district, this home puts the best of Annapolis just outside your door. Stroll to neighborhood favorites including Davis' Pub, Leeward Market, the Annapolis Maritime Museum, waterfront parks, marinas, and restaurants, or make your way across the bridge to Historic Downtown Annapolis. Morning walks along the water, afternoons on the Bay, and evenings spent enjoying Eastport's restaurants and neighborhood gathering spots are all part of everyday life here. Welcome Home!

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$1,150,000
2bedrooms
4bathrooms
land 0ha

By Ttr Sotheby's International Realty

34
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House with garden and terrace Annapolis (United States)

Experience the Annapolis waterfront lifestyle from this charming A-frame cottage, where days on the water begin just steps from your door. Designed for relaxed coastal living, the 2-bedroom, 2-bath home features a light-filled, open interior with soaring vaulted ceilings and an inviting sense of space. Outside, the property becomes your private gateway to the South River. A private pier offers two deep-water slips, including one with a boat lift, while a dedicated kayak launch makes it effortless to explore the surrounding waterways. Bulkheaded shoreline, a storage shed, and ample outdoor space complete a setting designed for life along the Annapolis waterfront. Spend mornings enjoying coffee overlooking the water, afternoons boating, kayaking, or paddleboarding, and evenings unwinding on the South River as the sun sets across the waterfront. Whether you're searching for a full-time residence, weekend retreat, or Annapolis boating getaway, this is an opportunity to embrace a lifestyle centered around the Chesapeake Bay

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$1,195,000
2bedrooms
2bathrooms
land 0.2ha

By Ttr Sotheby's International Realty

42
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House with terrace Annapolis (United States)

A rare waterfront setting just off the Severn River, 1800 River Watch Lane is positioned on a private peninsula with more than 450 feet of shoreline along Luce Creek, offering exceptional privacy, sweeping water views and approximately 8 feet of protected deep water at the pier. From here, the Severn River is moments away and downtown Annapolis is an easy boat ride, an extraordinary setting for anyone who wants to make the Chesapeake Bay lifestyle part of everyday life. Approached by a long private drive and circular pea-stone courtyard, the extensively renovated residence sits high above the water, surrounded by mature trees and landscaping. Designed primarily on one level, the home takes full advantage of its elevated setting, with water views filling nearly every room and expansive outdoor living spaces overlooking the creek. At the center of the home, the dramatic living room pairs a wood-paneled cathedral ceiling with a floor-to-ceiling stone fireplace and an entire wall of glass facing the water. Doors open to a broad Ipe deck spanning the waterside of the home, creating a natural extension of the living space. Morning coffee overlooking the creek, dinner outside with friends or an evening in the hot tub all unfold against the backdrop of the water. The open layout continues into the dining and family areas, where cathedral ceilings, a gas fireplace and panoramic views create relaxed spaces equally suited to entertaining and everyday living. The adjoining chef's kitchen features marbled Silestone countertops, an extensive suite of Miele appliances, including double wall ovens, warming drawer and induction cooktop, along with a large walk-in pantry. The home's private spaces are equally thoughtful. A dedicated office with built-ins and an adjoining den or bedroom offer flexibility for working from home or accommodating guests. An architecturally distinctive, skylit hexagon hall leads to the bedroom wing and the waterside primary suite, a serene retreat with a gas fireplace, tray ceiling and oversized walk-in closet. The spa-inspired primary bath features a soaking tub positioned toward the view, large walk-in shower, double vanity and private sauna. Two additional bedrooms, including one ensuite, another full bath, separate laundry room and powder room complete the living spaces. Hardwood flooring, generous windows and clean contemporary finishes carry throughout the home, while a well-appointed mudroom connects to the oversized two-car garage. Outside is where the property becomes truly exceptional. The elevated homesite provides privacy and long views across Luce Creek, while a private funicular makes the trip from the house to the shoreline effortless. At the water, a substantial private pier with two boat lifts and approximately 8 feet MLW provides the kind of deep-water access that is increasingly difficult to find. The protected waters of Luce Creek offer an ideal home base for your boat, with the Severn River just beyond and the Chesapeake Bay easily accessible. Spend the morning on the water, cruise into downtown Annapolis for lunch or dinner, or simply enjoy the activity along the creek from the deck above. Despite its remarkably private setting, 1800 River Watch Lane remains convenient to downtown Annapolis as well as major routes to Baltimore, BWI, Washington, D.C. and the Eastern Shore. With its combination of substantial shoreline, protected deep water, immediate Severn River access, privacy and proximity to Annapolis, 1800 River Watch Lane offers a waterfront lifestyle that is increasingly hard to replicate.

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$2,995,000
3bedrooms
4bathrooms
land 0.7ha

By Ttr Sotheby's International Realty

50
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House with pool and garden Annapolis (United States)

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!

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$1,695,000
4bedrooms
5bathrooms
land 0.2ha

By Ttr Sotheby's International Realty

50

House with pool and terrace Annapolis (United States)

Outstanding luxury living in this 3-story townhouse with so many extras! 10 Enclave has the best floor plan with a superior kitchen layout, bump-outs on three levels allowing office space on the main level and double walk-in closets in the primary suite. Natural light fills the great room and the soaring ceilings, 8-foot entry and French doors and banks of windows create volume and an unmatched sense of open space. The kitchen features fabulous, pretty and timeless finishes with light cabinets and counters, gorgeous lighting, a pantry, ample counter space, an eat-at counter and gas cooking, and double ovens. The top level has wood floors in all bedrooms and a truly elegant primary suite features coffered 9+ ft. ceilings and enough closet space where even a "clothes horse" will enjoy space! The bedroom level also has a large laundry room with storage for your easy lifestyle. The walkout level is the perfect "plus" space for a family room, a fantastic hobby area or extra guests and is complete with a powder room. All three levels have outside access (two decks and an amazing hardspace patio) complete even the most particular buyer's wishlist. Two-car garage and driveway parking! This special community is the perfect Annapolis location, minutes to Downtown and Eastport, all commuter routes, shopping, and marinas!

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$688,000
3bedrooms
4bathrooms
land 0ha

By Ttr Sotheby's International Realty

40
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House with pool and terrace Annapolis (United States)

A rare opportunity to own a fully metered triplex in the heart of Downtown Annapolis where historic charm, prime location, and remarkable versatility come together. Steeped in character and offering exceptional flexibility, this distinctive property presents an array of possibilities for both lifestyle and investment. With separately metered electricity, the property can be enjoyed as a multigenerational residence, with each family member having their own private space; an owner-occupied home with additional rental income from the remaining units; or a pure investment property with multiple income producing residences. For those envisioning something truly extraordinary, the entire building could be transformed back into a stunning single-family home. With original architecture and showcasing hardwood floors throughout, this property strikes the perfect balance between historic character and modern livability. The first floor features two bedrooms, each with an en-suite bath, kitchen, and living room, ideal for an owner-occupant or long-term tenant. The second floor offers one bedroom, a full bath, kitchen, living room, and access to a private balcony. The third floor impresses with two bedrooms, a full bath, kitchen, and living room, plus its own private balcony. An unfinished basement provides excellent storage space. A fenced backyard complete with a paver patio, provides an outdoor retreat ideal for relaxing or entertaining. Add to that the coveted off-street parking, a true rarity in Downtown Annapolis, and this property is as practical as it is beautiful. Whether you're an investor seeking immediate income potential, a buyer looking to offset your mortgage, or a multigenerational family wanting separate yet connected living spaces, this home checks every box. All of this just steps from the vibrant shops, restaurants, waterfront, and history that make Downtown Annapolis truly one of a kind.

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$1,300,000
5bedrooms
4bathrooms
land 0ha

By Ttr Sotheby's International Realty

15
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Property with garden Annapolis (United States)

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!

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$1,395,000
4bedrooms
2bathrooms
land 0.3ha

By Ttr Sotheby's International Realty

46
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House Annapolis (United States)

Life takes on a different pace in Oakwood, where the calm waters of Fishing Creek and the South River provide an idyllic backdrop and effortless access to the Chesapeake Bay. With 93 feet of shoreline, a private pier with multiple slips, and a substantial 25,000-pound boat lift, this property is perfectly suited for boating enthusiasts and those who appreciate the beauty and tranquility of the Chesapeake lifestyle. Designed for both everyday comfort and effortless entertaining, the home offers an inviting open floor plan with seamless flow between the gourmet kitchen with center island, sunroom, soaring two-story living room, and adjacent family room. Walls of windows frame picturesque water views and fill the home with natural light. A versatile main-level room with an adjoining full bath provides ideal space for guests, a private office, or flexible living needs. Upstairs, the spacious primary suite serves as a peaceful retreat with abundant windows capturing the ever-changing waterfront scenery, a walk-in closet, and an ensuite bath featuring dual vanities, a large shower, and a relaxing soaking tub. Two additional bedrooms share an ensuite bath and a fourth bedroom provides plenty of space for family and friends. The expansive space above the garage has been transformed into a fun Margaritaville-inspired bar and game room complete with a full bath. This exceptional area offers endless possibilities and could easily become a second primary suite, private guest quarters, or an in-law suite. Outside, multiple entertaining spaces invite gatherings with family and friends while the lush lawn gently transitions to the water's edge. Whether hosting summer celebrations, launching a boat for a day on the Bay, or simply unwinding as the sun reflects across Fishing Creek, this property offers a lifestyle that feels like a vacation every day. A side-entry two-car garage and spacious driveway complete this exceptional waterfront offering in one of Annapolis Neck's most desirable communities. Welcome Home!

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$2,495,000
5bedrooms
5bathrooms
land 0.1ha

By Ttr Sotheby's International Realty

37

House with terrace Annapolis (United States)

Tucked into Homewood, just beyond the brick sidewalks of Historic Downtown Annapolis, 16 Woodlawn Avenue is a residence taken down to the studs and rebuilt in 2019, blending all the comforts of modern design with the historic charm of Homewood. A traditional front porch, turned white columns and soft buttery siding announce the home from the street while a long driveway offers the rare luxury of off street parking in one of Annapolis's most walkable in-town pockets. Inside, tall ceilings and recessed lighting set an airy tone against gorgeous oak flooring on the main level and the beautifully refinished original pine flooring on the stairs and level two. The classic period moldings that run throughout remind you that this home has been here for a time as the updates make it seem like a much newer build. The kitchen anchors the main level: white shaker cabinetry, stainless appliances, and granite countertops surround a center island with room for a kitchen table, while a separate formal dining room sits just off the living room for more considered entertaining. A main level powder room, a rare find in homes of this era, provides ease buyers rarely expect from an in-town address. A mudroom tucked off the kitchen doubles as an office also providing space for the pantry, a laundry closet and access to the unfinished basement and backyard. Upstairs, three bedrooms include a primary suite that is bright, generously scaled, and appointed with an ensuite bath and stall shower. The hall bath is an ode to the age of the home with a refurbished black and white clawfoot tub (with shower) set beneath classic wainscoting. A third floor of floored attic space stands ready as flexible storage today, or a defining feature tomorrow for an owner who wants to finish it into additional living space. Outside, the large, flat, fully fenced yard is anchored by a side patio off the mudroom for grilling and framed by fig trees, with a gate to a rear fenced area and a large storage shed beyond. The location is a defining feature in its own right. Walk to Navy games, boat shows, Wednesday night's "Dinner Under the Stars, and pickup pickleball on West Street, or take a short drive to the boat ramps at Amos Garrett Park or West Annapolis to launch your paddle board or kayak. 16 Woodlawn Avenue isn't just a renovated in-town home. It stands as a premier expression of Chesapeake Bay living at its most walkable and most alive. Be sure to check out the virtual walk through tour!

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$799,000
3bedrooms
3bathrooms
land 0.1ha

By Ttr Sotheby's International Realty

42

House with garden and terrace Annapolis (United States)

Celebrate the Eastport lifestyle in this beautifully crafted home, where classic Craftsman character meets the comfort and ease of newer construction. Built in 2016 and lightly lived in, the home captures everything that makes Eastport so desirable, from its welcoming front porch, charming architectural details, and beautifully curated landscaping to a location just steps from marinas, restaurants, waterfront parks, and the vibrant streets of Downtown Eastport and Annapolis. Lush, thoughtfully designed landscaping brings the property to life, framing the home with color, texture, and greenery and creating an inviting sense of arrival. A gracious front porch sets the tone for the warm and welcoming interiors. Just inside, a dedicated office provides a quiet workspace, while hardwood floors, shiplap accents, custom millwork, and thoughtful details lend character throughout. The open floor plan unfolds into the heart of the home, where a spectacular kitchen features GE Monogram appliances, an expansive island, abundant cabinetry, and generous workspace. The adjoining dining area flows seamlessly into the living room, anchored by a fireplace framed with custom built-ins. Doors extend the living space to a large rear patio surrounded by beautiful landscaping, creating a private and inviting setting for outdoor dining, entertaining, and relaxed evenings at home. The main-level primary suite offers the convenience of one-level living with a beautifully appointed ensuite bath and conveniently located laundry room. A thoughtfully designed mudroom with built-in cubbies provides everyday functionality and an organized transition into the home. Additionally, the home features advanced technology throughout, including a Tesla Powerwall 3 for backup power, Tesla EV charger, and professionally installed Control4 home automation. The integrated system provides centralized control of lighting, climate, security, electronic locks, TVs, and built-in ceiling speakers throughout the home. Upstairs, two spacious bedrooms share a hall bath, while a large finished attic adds a wonderfully flexible dimension to the floor plan. Currently ideal as a bunk room, this charming bonus space can easily adapt as a playroom, additional sleeping quarters, creative studio, or whatever best suits your lifestyle. The finished lower level takes entertaining and recreation to another level with a spacious family room, game area, wet bar, full bath, and golf simulator. A separate bonus room currently serves as a home gym, while an expansive storage area provides the practical space that is often difficult to find in Eastport. Beyond the front door, the best of Annapolis is within easy reach. Launch a kayak from nearby Horn Point Park, stroll to Eastport's celebrated restaurants, pubs, marinas, and street-end parks, or cross the Spa Creek Bridge into Downtown Annapolis and the U.S. Naval Academy. Boaters will appreciate immediate proximity to the Chesapeake Bay and some of the region's most sought-after cruising destinations. Membership at the nearby Annapolis Capital Yacht Club marina also provides permission to enjoy the Chesapeake Landing community swimming pool, adding yet another way to embrace the waterfront lifestyle just steps from home. Offering the charm and personality of an Eastport Craftsman with the advantages of newer construction, beautiful landscaping, a main-level primary suite, exceptional entertaining spaces, and an enviable walkable location, this is a rare opportunity to experience one of Annapolis' most beloved neighborhoods with comfort, style, and ease. Welcome Home!

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$2,695,000
4bedrooms
4bathrooms
land 0.1ha

By Ttr Sotheby's International Realty

49
Video

House with pool and garden Annapolis (United States)

Bay Ridge Waterfront! Built by Pilli Custom Homes and beautifully curated by Erin Paige Pitts Interiors, this exceptional waterfront residence blends timeless architecture, impeccable craftsmanship, and extraordinary attention to detail. Rich custom millwork, extensive crown molding, elegant wainscoting, and coffered ceilings create an atmosphere of refined luxury throughout. A welcoming bluestone walkway and front porch opens to the foyer, while a dramatic circular foyer at the foot of the staircase serves as the heart of the home, seamlessly connecting the formal dining room, elegant club room, and expansive kitchen and family room. Designed for effortless entertaining and everyday living, the chef's kitchen opens to the spacious family room featuring coffered ceilings and a striking fireplace. Just beyond, the waterside deck expands the living space with a swim spa, outdoor kitchen, and an exterior half bath, thoughtfully positioned so guests coming from boating, swimming, or relaxing by the water never need to enter the home. These exceptional amenities create the perfect setting for entertaining while embracing the waterfront lifestyle. Off the 2-car garage, the thoughtfully designed mudroom offers a built-in workspace, abundant storage, and a convenient powder room. A private main-level guest suite with an ensuite bath provides ideal accommodations for guests or multigenerational living. The upper level offers four spacious bedrooms, including two with private ensuite baths, while two additional bedrooms share a beautifully appointed bath. One bedroom has been transformed into a custom dressing room and can easily be converted back if desired. A large bonus room above the garage, complete with its own powder room, provides endless flexibility as a media room, playroom, home gym, or studio. The luxurious primary suite is a true retreat, featuring sweeping Lake Ogleton views from its wraparound balcony, a private office, spacious walk-in closet, and a spa-inspired bath with heated floors, soaking tub, oversized walk-in shower with built-in bench, and designer finishes. The top level is designed for entertaining with an expansive recreation room and a dramatic spiral staircase leading to one of the home's most remarkable features, a private rooftop deck perched among the highest elevations in Bay Ridge, offering breathtaking panoramic views and the perfect setting for morning coffee, sunset cocktails, or evening stargazing. Outside, the waterfront experience is equally impressive with a newly constructed pier featuring upgraded electrical service, LED lighting, three boat lifts, including an impressive 40,000-pound lift, and convenient waterside shed, providing exceptional accommodations for a variety of vessels and effortless access to the Chesapeake Bay. Bay Ridge offers an unmatched waterfront lifestyle with a community pool and clubhouse overlooking the Chesapeake Bay, sandy beaches on both the Bay and the river, a marina with a newly renovated clubhouse, playgrounds, basketball courts, ball fields, and miles of scenic waterfront roads for walking and biking. An active social calendar and year-round events make Bay Ridge one of Annapolis' most sought-after communities. Just minutes from Historic Downtown Annapolis and Eastport, enjoy award-winning restaurants, boutique shopping, marinas, and waterfront parks, with convenient access to Routes 50 and 97 for commuting to Baltimore, BWI Airport, Fort Meade/NSA, Washington, D.C., or Maryland's Eastern Shore. Welcome Home!

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$3,997,000
5bedrooms
7bathrooms
land 0.2ha

By Ttr Sotheby's International Realty

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