luxury real estate for sale Galesville, United States

Welcome to 4909 Olive Street, a newer construction three bedroom, two and a half bath home. Offering a functional layout, contemporary finishes, open living spaces, a fully fenced in backyard, and a private driveway. Enjoy access to a community beach, pier, kayak launch, waterfront park, playground, and picnic areas. Conveniently located near local marinas, waterfront dining, parks, and Chesapeake Bay attractions, with easy access to Annapolis, Edgewater, Washington, D.C., and Baltimore. A great opportunity to enjoy a water oriented lifestyle in one of Southern Anne Arundel County's popular waterfront communities.

Now is the time to take a fresh look at this beautifully designed 2022-built home, where modern style, thoughtful details, and a peaceful wooded setting come together. Move-in ready and filled with natural light, this home offers the space and flexibility buyers are looking for—without the wait or expense of new construction. Step inside to an open two-story foyer and into the inviting main living area with vaulted ceilings. Nine-foot ceilings throughout the home, charming cottage-style windows, and an open layout create an airy, comfortable feel. LVP flooring flows throughout the living room, kitchen, and wide hallway, making everyday living and entertaining effortless. The kitchen is a standout, featuring granite countertops, soft-close cabinetry, oil-rubbed bronze fixtures, and a center island with seating. There’s plenty of room for a dining table, creating an easy gathering space for family and friends. The main level offers three bedrooms including a spacious owner’s suite with two closets providing excellent storage, while the distinctive en-suite bath features dual sinks, granite countertops, a walk-in shower, custom wall trim. The two additional bedrooms feature custom molding, decorative wall treatments, and stylish finishes. The hall bath includes a granite vanity and shower/tub combination. And there’s even more living space downstairs! The lower level features a large recreation room with sliding glass doors to the backyard, a flexible fourth bedroom perfect for guests, a home office, gym, or hobby room, plus another full bath. This versatile lower level gives you room to spread out, work from home, entertain, or accommodate overnight guests. Outside, raised garden beds are ready for your favorite flowers, herbs, and vegetables. The mature, wooded backdrop provides a peaceful sense of privacy and a beautiful setting to enjoy year-round.

OPEN HOUSE Saturday 10/24 from 1-3PM. Historic Portland Manor – Allendale is privately set on 4.5 acres off sought-after Brooks Woods Road, surrounded by mature trees, neighboring acreage, and pastoral surroundings. A heritage tree-lined drive leads to the residence, framed by established landscaping, gorgeous brick walkways surrounding the home, landscape lighting, covered porches, and a renovated in-ground pool. Dating back to the late 1700s, with additions completed in the early 1800s, the home has been thoughtfully restored and updated while preserving its historic integrity and original craftsmanship. Offering an estimated 5,060 square feet, the property includes six bedrooms and four and a half baths across the main residence and separate in-law suite. Interior features include original heart pine flooring, restored historic windows, six fireplaces, a traditional central hall layout, three staircases, multiple gathering spaces, and extensive custom built-ins and storage throughout. The main level includes a formal dining room with marble fireplace and adjoining butler’s pantry, family room with restored marble fireplace, living room with fireplace and custom built-ins, greenhouse room, powder room, and multiple access points to the home’s covered porches and outdoor living spaces. The custom kitchen features extensive handmade cabinetry and tile work, custom shelving and pantry storage, soapstone and butcher block countertops, commercial-grade gas cooking with a double gas range, vent hood, griddle, separate service sink, and generous preparation space designed for entertaining and everyday functionality. A storage closet beneath the main staircase and extensive built-in cabinetry throughout the connecting gallery to the in-law suite provide exceptional functional storage rarely found in historic homes. The second level includes the primary suite with a large walk-in closet, private kitchenette, fireplace, and ensuite bath. Two additional bedrooms are located on this level, each featuring fireplaces, with one offering an ensuite bathroom. The third floor offers two additional bedrooms, a full bathroom, a large finished storage closet, and expansive attic storage space. The separate in-law suite, originally constructed in 1785, includes a living and dining area, kitchenette, full bathroom with private laundry, and an upper-level bedroom with vaulted A-frame ceiling. The residence includes eight exterior doors leading to approximately 1,000 square feet of covered brick porches, landscaped walkways, pool areas, and outdoor gathering spaces, creating a seamless connection between the home and grounds. Additional upgrades include fresh exterior paint on the entire home (2026), high-efficiency foam insulation in the attic, roof space, and crawlspace, and a comprehensive exterior restoration. The siding was removed and rebuilt with new Rockwool sidewall insulation, plywood sheathing, and infiltration fabric. Outdoor features include a fully renovated 20’ x 40’ pool (2025), pool house, custom fire pit patio with built-in seating, large deck with new decking (2025), fenced areas, extensive landscape lighting, and a custom Williamsburg-style chicken coop. Major system updates include two high-efficiency HVAC systems, plumbing system replaced in 2013, electrical systems and new 400-amp electric service was redone (2025). The exterior was fully repainted in 2026. A rare offering combining historic character, extensive restoration, privacy, acreage, and modern livability, conveniently located near The Cannon Club, local farmers markets, waterfront dining, and commuter routes. Two Tax IDs convey.

Build your own piece of the Chesapeake Bay lifestyle in Turkey Point. This lot offers water views across the Chesapeake Bay, South River, and Ramsey Bay, creating a beautiful setting for a future home. Surrounded by water, Turkey Point offers multiple community beach access points, a community pier, and Cloud Field, a large community play and recreation area. Boating, fishing, crabbing, kayaking, paddleboarding, and days along the shoreline are all part of what makes this peninsula such a special place. This lot is being offered for sale with the adjacent lot at 3727 Ramsey Drive, providing the opportunity to own two neighboring parcels and create a larger footprint.

Build your own piece of the Chesapeake Bay lifestyle in Turkey Point. This lot offers water views across the Chesapeake Bay, South River, and Ramsey Bay, creating a beautiful setting for a future home. Surrounded by water, Turkey Point offers multiple community beach access points, a community pier, and Cloud Field, a large community play and recreation area. Boating, fishing, crabbing, kayaking, paddleboarding, and days along the shoreline are all part of what makes this peninsula such a special place. This lot is being offered for sale with the adjacent lot at 3725 Ramsey Drive.

For the first time in decades, this one of a kind property on Turkey Point Island is being offered for sale by the original owners. With exceptional water views and access to the community’s many waterfront amenities, the home has been meticulously maintained and offers just over 2,900 square feet of finished living space across three levels. The main level offers a kitchen equipped with Bosch stainless steel appliances, dining room, bonus sitting room, an expansive living room with custom built ins, surround sound system, and a gas fireplace. Andersen windows are found throughout most of the home, along with hardwood flooring in many of the main living areas. Just off the living room is an incredible screened in porch with water views and opens to the rear deck.  The deck (with fiberon composite deck boards) connects directly to the 24 foot round, 52 inch deep above ground pool, with additional water views from the deck and pool area. Additional storage can be found under the deck as well. Upstairs, you’ll find three bedrooms and two full baths. The primary suite includes an enhanced en suite bathroom and additional closet space. The finished walkout lower level provides another spacious gathering area with a family room and propane fireplace, along with a bedroom, full bath with stand up shower, and laundry. Direct walkout access leads to a private patio and backyard.  An oversized attached two-car garage with roughly 9' wide x 8' high garage doors provides significant and surprising additional storage and has been meticulously maintained. The property also includes a covered front porch, backyard shed and rear fenced in yard. The roof was replaced in 2016, the water heater in 2017, and the home is heated by a heat pump with oil backup. Life in Turkey Point is centered around the water. The community offers multiple beaches and water access points, a pier, walking paths, and Cloud Field with its playground and open green space. Boating, kayaking, paddleboarding, fishing, and crabbing are all part of the lifestyle here, with several marinas nearby and additional access to the Chesapeake Bay at Mayo Beach Park and Beverly Triton Nature Park. And while Turkey Point feels tucked away at the end of the peninsula, everyday shopping, restaurants, and the conveniences of Edgewater are still within easy reach, with Annapolis just beyond.  With water views, four bedrooms, three full and one half bathrooms, a finished walkout lower level, pool, and oversized two-car garage, 1117 Wilson Drive offers substantial living space and storage space with access to everything that makes Turkey Point such a distinctive Chesapeake Bay community. Island living at its best!

Set on a spectacular point of land where the South River meets the Chesapeake Bay, this extraordinary waterfront estate captures some of the most breathtaking views in Annapolis. With coveted southern exposure, the property is immersed in sunlight from dawn to dusk, creating an ever-changing backdrop of sparkling water, passing sailboats, and panoramic Chesapeake vistas. Completely reimagined in 2017 by renowned architect Cathy Purple Cherry, this residence was rebuilt and renovated to an exceptional standard, blending timeless coastal architecture with modern luxury and uncompromising construction quality. Spray-foam insulated walls and roof, steel reinforcement, double plywood construction, four-zone HVAC with humidifiers, gas backup heat, tankless propane water heaters, water treatment systems, generator backup, Sonos audio, and Lutron lighting create a home that is as efficient and functional as it is beautiful. Designed for both grand-scale entertaining and comfortable everyday living, the interior offers over-the-top craftsmanship and thoughtful details throughout. Maple hardwood flooring flows through elegant yet inviting spaces including a dramatic waterfront living room with a custom wet bar, an informal gathering room with built-in bookshelves, a private office with custom cabinetry, wet bar, balcony, and commanding views stretching down the Chesapeake Bay, and a state-of-the-art theater room complete with its own wet bar, refrigerator, and ice maker. The chef’s kitchen is a masterpiece featuring double Wolf ovens, Wolf cooktop, Sub-Zero refrigerator, three dishwashers, wine cooler, ice maker, built-in microwave, instant hot water, walk-in pantry with custom built-ins, and a sun-filled breakfast nook overlooking the water. The luxurious primary suite serves as a private waterfront retreat, highlighted by a stunning spa bath finished with Italian water-cut marble. Three additional bedrooms feature ensuite baths, while a full bath on the main level conveniently serves the pool and outdoor entertaining areas. Outdoor living rivals the finest resorts. Expansive Ipe decking surrounds a heated PebbleTec pool and spa, complemented by an outdoor kitchen, fire pit, integrated sound system, and extensive landscape lighting. The private pier is equipped with water, electric, approximately 4 feet of MLW, a 12,000-pound boat lift, an 8,500-pound boat lift, and a 1,500-pound personal watercraft lift, providing immediate access to the Chesapeake Bay and beyond. Offering 4 bedrooms, 5 full baths, 1 half bath, a dedicated office, and a deep four-car garage, this is a rare opportunity to own one of Annapolis’ premier waterfront properties in a setting where extraordinary architecture, unmatched craftsmanship, and world-class outdoor living come together on the shores of the Chesapeake.

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!

An extraordinary expression of waterfront luxury, this architecturally significant estate represents a rare convergence of world class design, craftsmanship, and lifestyle. Located within the prestigious enclave of Wimbledon Farms, surrounded by grand estates and moments from local vineyards and equestrian facilities, the residence was masterfully conceived by acclaimed architect Scarlett Breeding and flawlessly built by Pyramid Builders. A complete refit elevated the home to an uncompromising standard where timeless architecture and modern sophistication exist in perfect harmony. An enchanting winding crushed gravel driveway framed by Belgian block curbing sets the tone for the remarkable experience that awaits. Perfectly positioned with western exposure, the property captures breathtaking sunsets as golden light melts into the horizon across the river and the surrounding landscape. Professionally designed landscaping creates a lush resort like setting that enhances the home’s striking architectural presence. Inside, high lacquered woodwork, bespoke millwork, hidden passage doors, attention to detail, and coffered ceilings create an atmosphere of refined sophistication. Ultra luxe Chesneys fireplace surrounds anchor multiple living spaces with warmth and elegance, while expansive walls of glass frame sweeping water views and seamlessly connect the indoors with the surrounding waterfront setting. A richly appointed wood-clad office with custom built ins offers an executive retreat designed for both privacy and inspiration. At the heart of the residence, the extraordinary St. Charles kitchen rivals those found in internationally celebrated estates, featuring Premier custom cabinetry, a statement Le Cornue range and island, exquisite fixtures, and an artisan-crafted focal point range hood, all designed for elevated entertaining and effortless daily living. Outdoor living reaches resort caliber with an elevated spa and a spectacular four sided overflow vanishing edge pool, where the waterline sits flush with the pool edge, creating a seamless visual connection to the river beyond. Exotic Ipe hardwood decking surrounds the pool and expansive rear terrace, while pergolas and a screened porch provide beautifully designed spaces for entertaining and relaxation. A new private pier, private beach, and panoramic river and pond views complete this extraordinary waterfront lifestyle. The upper level offers four luxurious ensuite bedrooms, including a phenomenal primary suite with sweeping water views, barrel ceiling, a fireside sitting room, a boutique inspired dressing gallery, and a spa quality bath with a soaking tub overlooking the water. Integrated Control4 home automation delivers effortless comfort and convenience throughout. Tucked away on the coveted Annapolis Neck peninsula, Wimbledon Farms offers a rare blend of tranquility, exclusivity, and convenience. Just moments from Downtown Annapolis and major commuter routes, the setting feels worlds away, defined by peaceful surroundings and an unmistakable sense of retreat. Encompassing only 19 estate homesites, this intimate waterfront enclave is gracefully bordered by Harness Creek and the South River, creating a breathtaking backdrop for both sunrise and sunset vistas. Residents enjoy a warm yet private community atmosphere, highlighted by occasional neighborhood gatherings and an expansive marina on protected Harness Creek, a prized deep water haven known for its calm, sheltered waters and exceptional boating access. Welcome Home!

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

Welcome to the coveted South River Landing waterfront community, where sweeping views across the South River and a deeded boat slip at the community's deep-water marina offer an exceptional opportunity to embrace the Annapolis waterfront lifestyle. From spontaneous afternoons exploring the Chesapeake Bay to leisurely cruises along the river, life on the water becomes an effortless part of everyday living. Beautifully constructed, this impressive all-brick residence offers three finished levels, expansive outdoor living spaces, and walls of windows that capture the ever-changing waterfront scenery, creating a remarkable setting for both relaxation and entertaining. A grand entrance with an elegant curved staircase and impressive custom front door sets the tone for the spacious interiors. The main level is thoughtfully designed around the water views, with a beautifully appointed kitchen flowing seamlessly into the living room with fireplace and casual dining area. Whether gathering around the kitchen, hosting memorable dinners in the formal dining room with custom built-ins, or stepping outside to the sprawling waterside balcony, the South River provides a spectacular backdrop. Enjoy morning coffee as boats make their way along the river, spend the afternoon cruising from your own deeded slip, and return home to unwind as the evening light settles over the water. Two ensuite bedrooms and a powder room provide additional comfort and flexibility on this level. Upstairs, a spacious multi-purpose living area with fireplace and built-in entertainment center creates an inviting destination of its own. A full second kitchen makes entertaining effortless and offers wonderful flexibility for extended family or guests. A full bath with soaking tub and separate shower, powder room, and finished bonus room above the garage provide additional options for relaxing, working, or accommodating visitors. With generous spaces designed for gathering or retreating, the home easily adapts to everything from quiet weekends to extended stays with family and friends. The finished lower level offers another exceptional setting for entertaining and relaxation, with a recreation area centered around a fireplace, wet bar, beautifully designed wine cellar, and dedicated theater room. After a day spent boating, swimming, or exploring the waterways, return home for an evening of movies, conversation, and time together. An additional ensuite bedroom provides private guest accommodations, while an elevator connecting all three levels and laundry facilities on each floor add exceptional convenience to everyday living. Beyond the residence, the gated South River Landing community offers a lifestyle reminiscent of a private waterfront resort. Residents enjoy 24-hour staffed security, a waterfront swimming pool, deep-water marina, kayak launch, tennis courts, playground, basketball court, private beach, and scenic walking trails. The deeded boat slip is a particularly desirable feature, providing a dedicated place for your boat and convenient access to the South River, Chesapeake Bay, and the countless waterfront destinations that make this region so special. Whether heading out for a morning cruise, meeting friends at a favorite waterside restaurant, spending an afternoon kayaking, or simply relaxing by the community pool, every day presents another opportunity to appreciate life along the water. Combining the privacy and security of an established gated community with the freedom of having your boat just moments from home, this extraordinary property offers far more than beautiful waterfront views. It is an invitation to embrace a lifestyle defined by effortless boating, gracious entertaining, and the natural beauty of the Chesapeake Bay region. All just minutes from historic Annapolis, with convenient access to Washington, D.C. and Baltimore. Welcome Home!

Coastal charm and thoughtful craftsmanship come together in this beautifully renovated cottage in the sought-after Edgewater Beach community. Surrounded by mature trees, perfectly sited on a double lot and filled with natural light, the home offers a peaceful, private setting with seasonal glimpses of Beards Creek and conveniently located access path leading to the water’s edge. Inside, an open floor plan creates an inviting sense of space, enhanced by skylights and a classic brick fireplace with glass doors that adds warmth and character to the main living area. The beautifully renovated kitchen is both stylish and exceptionally functional, showcasing quality craftsmanship and thoughtful details throughout. A distinctive 12' long Bubinga wood live-edge countertop anchors the generous island with abundant seating, while two wall ovens, a built-in pantry, microwave, and ample storage make the space equally suited for everyday living and entertaining. Just outside the main living space, an expansive deck extends the home outdoors, creating a natural setting for dining, entertaining, or simply relaxing beneath the surrounding tree canopy. The seamless connection between indoors and out adds to the home’s relaxed feel and provides a peaceful backdrop throughout the seasons. Two bedrooms are located on the main level, one currently styled as an office, and share a beautifully renovated hall bath. Upstairs, the entire level is dedicated to a spacious and private primary suite. Tucked away from the main living spaces, this serene retreat features a walk-in closet and spa-like ensuite bath with a freestanding jetted tub and separate walk-in shower, creating a wonderful sense of privacy and escape. Located right at the edge of the property a serene path winds through the trees to the shoreline providing a wonderful spot to sit at the water's edge or launch a kayak. The Edgewater Beach community offers a boat ramp, boat slips, kayak storage, pavilion, playground, and additional amenities that make enjoying the South River lifestyle easy. Charming, beautifully updated, and rich with character, this special cottage combines thoughtful renovations, inviting indoor/outdoor living, privacy, and community water access in a peaceful coastal setting. 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.

South River Waterfront! Discover an exceptional waterfront lifestyle in Port Isle, where beautiful water views, a private pier, and thoughtfully designed indoor and outdoor spaces come together in a setting made for boating, entertaining, and relaxed everyday living. A cart path through the backyard leads to the private pier, complete with low-maintenance composite decking, a 24,000-lb. boat lift, and floating dock offering effortless access for kayaks and paddleboards. A long driveway creates a sense of arrival and leads to the two-car garage. Inside, the light-filled foyer with vaulted ceiling opens to a comfortable living area before flowing into the heart of the home. The expansive kitchen is designed for gathering, with two generous islands, abundant cabinetry, and extensive counter space providing exceptional room for cooking and entertaining. An adjoining dining area connects seamlessly to the family room, where a fireplace anchors the space and doors open to the waterfront deck. Here, elevated views across the backyard toward the South River create a natural extension of the living space and an inviting backdrop for dining, entertaining, or simply unwinding at the end of the day. Upstairs, all three bedrooms feature vaulted ceilings and water views. The primary suite is a peaceful retreat with a private waterfront balcony and ensuite bath featuring dual sinks and a spacious walk-in shower with bench. Two additional bedrooms share a well-appointed hall bath with dual sinks. A conveniently located laundry room completes this level. The walk-out lower level expands the home's versatility with a spacious recreation room, fourth bedroom, full bath, and generous storage. The living area opens to an extensive screened porch overlooking the backyard and water, creating another exceptional space for entertaining and relaxing. Seasonal coverings allow the porch to be enjoyed well into the cooler months. With multiple outdoor living spaces, a private pier, boat lift, kayak launch, and direct access to the South River, every element invites you to embrace life on the water. A golf cart conveys with the property, making it easy to travel through the neighborhood and down to the water's edge. Whether heading out for a day of boating, launching a kayak, entertaining on the deck, or relaxing on the private balcony, this Port Isle waterfront retreat captures the ease and beauty of the waterfront lifestyle. 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

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!

Set on a spacious corner lot in the water access community of Wilelinor Estates, this four bedroom home offers three finished levels, a bonus room in the basement, a fully fenced backyard, and access to the water, all just minutes from Annapolis. The main level features hardwood flooring throughout much of the home, with a dedicated dining room, eat in kitchen with access to the back patio, spacious living room and a sun filled family room with a walkout to the back yard. The kitchen is finished with granite countertops, stainless steel appliances, and a butcher block island over looking a wood burning fireplace, while a barn door leads to the main level laundry and attached two-car garage. Upstairs offers four bedrooms, including the primary suite with a walk-in closet and private bathroom. The finished walkout lower level offers even more living space with a large recreation room, bonus room, half bathroom, and additional storage. Outside, the fully fenced backyard is surrounded by established landscaping and complemented by hardscaping, creating plenty of space for entertaining and time outdoors. Recent improvements include a newer HVAC system and BAT septic system. Beyond the home, Wilelinor Estates offers a setting that is increasingly hard to find this close to Annapolis. Wide streets and mature trees lead to community amenities including a waterfront clubhouse, boat slips, kayak and paddleboard launch and storage racks, and trails along several ponds, including trails just across the street from the property. With access to Church Creek, the South River, and beyond, life in Wilelinor is closely connected to the water. Convenient to Annapolis, Edgewater, shopping, dining, and major commuter routes,

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!

Enjoy resort-style waterfront living with harbor and Chesapeake Bay views in the gated community of Chesapeake Harbour. This beautifully updated two-level residence offers the ideal blend of comfort, natural light, and low-maintenance coastal living. Freshly painted throughout with new carpet, the home features a thoughtfully designed floor plan with over 1,900 square feet of living space, an attached 2 car garage with interior access and additional parking out front, a rare and coveted amenity in the neighborhood. The entry level features an eat-in kitchen with white cabinets and counters, powder room and laundry room with a few steps up to the living room. The thoughtfully designed split-level layout creates a natural separation between the home’s functional spaces and its main entertaining areas, allowing gatherings to flow effortlessly while keeping day-to-day tasks discreetly tucked away. The dramatic living area where soaring ceilings, gas fireplace with custom built-ins, and walls of windows fill the space with natural light while framing the harbor views. Step outside to the expansive full-width waterside deck, the perfect setting for morning coffee, evening cocktails, or simply enjoying the marina activity and views stretching toward the Chesapeake Bay. Upstairs, the spacious primary suite offers a balcony, an ensuite bath with new cabinet and drawer fronts, and a peaceful retreat for relaxing after a long day. A loft-style flex space overlooks the living room below and can easily function as a second bedroom, home office, or additional lounge area, complemented by a full hall bath. Life in Chesapeake Harbour feels like a year-round vacation with an unmatched collection of resort-style amenities, including two waterfront pools, a private sandy beach, exclusive fitness center for a small enclave of residents, tennis and pickleball courts, fishing piers, walking and jogging paths, picnic areas with grills, scenic Chase Pond, and the security of a 24-hour attended gatehouse. The newly opened waterfront marina restaurant adds to the vibrant atmosphere with outdoor dining and live music on weekends. Ideally located just minutes from Downtown Annapolis, Eastport, the United States Naval Academy, waterfront dining, shopping, and historic attractions, this exceptional residence also offers easy access to Washington, DC, Baltimore, and Baltimore/Washington International Thurgood Marshall Airport. Whether you are searching for a full-time residence or a lock-and-leave waterfront retreat, this home offers the very best of the Annapolis waterfront lifestyle. Welcome Home!

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!

NEW PRICE * MOTIVATED SELLER * LAST CALL BEFORE THIS PROPERTY IS TAKEN OFF MARKET AND RENOVATED. Virtually staged photos of the living room. Seller converting the fireplace to electric and adding a new washer/dryer. With the leaves falling the view to the bay is improving. Quiet tranquil setting for this 2 bedroom 2 bath unit with a view of the Bay in the distance, Windows in second bedroom replaced in 2024. To be sold in As-is condition. Enjoy the community amenities - 24 hour security, swimming pools, tennis courts, a beach and walking trails. Bay Ridge Rd. to Route 50 and 97 to DC and Baltimore. Easy to show, just call Showings to log in.

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.

***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.

Enjoy the Chesapeake Bay lifestyle from this charming 2-bedroom, 3-bath cottage offering beautiful Bay views and direct access to the water just across the street. Situated on more than .6 acres, the property combines a relaxed coastal setting with a spacious, private backyard that is flat and ideal for outdoor living and entertaining. After a day on the water, unwind in the hot tub, rinse off in the outdoor shower, or simply enjoy the privacy of the backyard. A storage shed provides convenient space for kayaks, paddleboards, bikes, and other outdoor gear. Just across the street, direct access to the Chesapeake Bay and a sandy beach makes it easy to launch a kayak or paddleboard, spend the day along the shoreline, or simply take in the Bay. While the property is non-waterfront, the combination of water views and convenient Bay access offers an exceptional opportunity to enjoy the Eastern Shore lifestyle. Whether you're looking for a weekend getaway or a full-time Shore home, 101 Chesapeake Bay Drive offers an inviting retreat with space, privacy, water views, and the Chesapeake Bay just steps away.