luxury real estate for sale 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!

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.

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!

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!

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.

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.

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!

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

Just Listed! 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.

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!

Located 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.

***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.

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.

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!

There is something special about life on the Chesapeake Bay, and this exceptional end-unit residence captures it beautifully. Ideally positioned where the Channel meets the Marina, the home enjoys an unobstructed view up the Channel toward the Chesapeake Bay and Bay Bridge, with expansive water vistas from nearly every room. A waterside wraparound patio, abundant green space, and fabulous interior upgrades further distinguish this unique waterfront setting. Morning begins with the sun rising over the Bay, visible from the primary bedroom and throughout the residence, while the ever-changing waterfront provides a spectacular backdrop to everyday life. From Wednesday night sailing races and Blue Angels flyovers to fireworks, passing boats, and expansive rainbows over the water, there is always something memorable to take in. Inside, the home feels bright, comfortable, and beautifully connected to its waterfront surroundings. The spacious living room is filled with natural light from an abundance of windows framing the incredible views. The electric fireplace provides a warm, relaxing atmosphere for quiet evenings or gathering with friends. Two bedrooms and two full baths provide a comfortable and versatile floor plan, whether used as a full-time residence, weekend retreat, or easy lock-and-leave Annapolis getaway. Just beyond the living room, the covered wraparound patio extends the living space outdoors and overlooks both the water and a large grassy area, an unexpected luxury in condominium living. A second patio off the kitchen offers its own highly sought-after private, no-stair walkway, allowing access to the beautifully appointed kitchen with an immediate view right out to the Bay Bridge. Together with the surrounding green space and multiple outdoor living areas, the residence offers a wonderful sense of privacy and lives much more like a single-family home than a traditional condo. Beyond the front door, Chesapeake Harbor offers a lifestyle centered around the water. Spend summer days at one of two swimming pools, including the waterfront pool, launch a kayak from the community beach, play tennis or pickleball, or follow the walking trails along the shoreline. When the day winds down, stroll to The Beacon for waterfront dining and return home as the evening light settles over the Bay. Ideally located just minutes from Downtown Annapolis, Eastport, the United States Naval Academy, world class dining, shopping, and historic attractions, this exceptional residence also offers convenient access to Washington, DC, Baltimore, and BWI Airport. Whether as a full-time residence or lock-and-leave waterfront retreat, this is a rare opportunity to experience Chesapeake Harbor from a truly special vantage point.

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!

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.

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!

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!

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!

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!

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!

Experience effortless waterfront living at The Point on Spa Creek, where this beautifully appointed entry-level residence combines exceptional convenience with captivating views across Spa Creek toward Historic Annapolis. With no steps required, the spacious condominium offers an easy, lock-and-leave lifestyle just moments from the clubhouse, waterfront pool, docks, and scenic walking paths. The inviting living room is framed by expansive water views and features a thoughtfully designed alcove with built-in shelving that discreetly conceals a Murphy bed, providing flexible accommodations for visiting family and friends. Step outside to the stone waterfront patio, an idyllic setting for entertaining, unwinding, and taking in spectacular sunrises over the water. A second patio off the dining room offers a more intimate retreat surrounded by nature. Inside, hardwood floors flow throughout, complemented by stylish architectural details including a beadboard-accented dining room ceiling. The serene bedroom captures beautiful water views and features a custom built-in closet area and elegantly appointed ensuite bath. A perfectly positioned pocket door allows the bath to serve both the bedroom and guests, providing the convenience of a powder room while maintaining privacy. The Point on Spa Creek offers an impressive collection of amenities designed around the Annapolis waterfront lifestyle. Residents enjoy direct access to Spa Creek with deep-water boat slips and two convenient water-taxi locations providing easy access to Downtown Annapolis. The waterfront pool and expansive deck with hot tub create a resort-like setting, while the clubhouse is available for private gatherings and events. Additional amenities include tennis and pickleball courts, EV charging stations, a kayak and canoe launch with convenient storage racks, and ample parking. Community social gatherings and a monthly newsletter foster a welcoming atmosphere, while pet-friendly policies ensure four-legged family members feel at home as well. A dedicated property maintenance supervisor adds another level of convenience, making life at The Point remarkably seamless. Waterfront views, boating access, and an exceptional array of amenities, all within easy reach of Eastport and downtown Annapolis. Welcome Home!

An exceptional offering in the heart of Eastport, where beautifully considered interiors, generous outdoor space and coveted off-street parking come together in a remarkably peaceful setting. Tucked along a quiet one-way street, this beautifully appointed home offers a rare combination of style, space and convenience. Inside, a light, neutral palette is complemented by wide-plank flooring, crisp millwork and thoughtfully selected finishes. The living spaces flow naturally for everyday living and entertaining, while expansive accordion glass doors create a seamless connection to the covered outdoor living area. The gourmet Kitchen with island features Brighton cabinets, high-end GE Cafe line appliances and stunning black and white mosaic backsplash. The spacious primary suite provides a private retreat with room for a sitting area and a beautifully finished ensuite bath. An additional upper-level flex space with charming architectural lines is ideal for a home office, reading area or creative space. Multiple outdoor spaces extend the living experience, including a covered porch and expansive upper deck with retractable awnings. Beautiful landscaping, mature plantings and lush gardens surround the property, creating a private setting for relaxing and entertaining. The detached two-car garage, private driveway and generous parking area are especially valuable amenities in Eastport. Stroll the artful and nautical streets to five-star restaurants, neighborhood pubs, and hidden street-end parks with community water access for launching kayaks and paddleboards. You'll find yourself just moments from downtown Annapolis and the Naval Academy. Eastport and Annapolis offer the perfect balance of small-town charm and world-class sophistication, with convenient access to Routes 50 and 97 for easy commuting to Baltimore, BWI Airport, Fort Meade, NSA, and Washington, D.C. Welcome Home!