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$650,000
MDAA2148812 MLS
Welcome to 182 Waldo Road in Pasadena offered at $650,000. An exceptional waterfront redevelopment opportunity on nearly three-quarters of an acre in Pasadena. The existing home is considered a tear-down, creating a rare chance to build a custom waterfront residence tailored to your vision. What sets this property apart is that many of the most expensive waterfront improvements are already in place. The property features a substantial private pier that was constructed in 2022, including multiple slips, providing immediate access to the water and saving a future owner the time, expense, and permitting process associated with new marine construction. In addition, the property includes Anne Arundel County-approved septic plans for a new residence of approximately 2,500 square feet, approved in April 2026. Property Highlights: ✅ .72-acre waterfront homesite ✅ Existing pier built in 2022 featuring: 50' x 6' pier 10' x 20' L-head Multiple finger piers Additional mooring pilings (Originally constructed at a cost of approximately $62,900.) ✅ County-approved septic design for a new 2,500± sq. ft. home ✅ Existing approvals help streamline the path to construction ✅ Rare opportunity to create a custom waterfront retreat in Pasadena Whether you're a builder, investor, or buyer seeking the perfect waterfront homesite, 182 Waldo Road offers the chance to start with valuable infrastructure already in place and focus on designing the home you've always wanted.

182 Waldo Rd, Pasadena

$1,590,000
4 Beds 5 Baths MDAA2148714 MLS
Reduced Price !!!! This idyllic waterfront estate offers a unique blend of luxury and nature, perfect for those seeking a serene retreat. Nestled on two combined lots (Lot 24 and Lot 25), this energy-efficient concrete home combines superior construction with modern elegance. Featuring 4 bedrooms, 3.5 baths, a 2-car garage with an apartment suite, and 360 feet of waterfront with a stunning 270-degree panoramic view of Chesapeake Bay and Bodkin Creek, this property exudes both colonial charm and contemporary design. Upon entering the foyer, you'll be greeted by designer lighting, pocket doors, in-floor heating, European tilt-and-turn windows, tray ceilings, and high-quality hardwood floors. The home is adorned with elegant granite windowsills and includes a laundry room, zoned heating, and central air. The gourmet kitchen is a chef's dream, boasting custom-made cherry cabinets with bird's eye maple inlays, granite countertops, a wine cooler, an oversized glass cooktop stove, a double oven, and a large pantry with a second refrigerator. The open and airy living room features a granite gas fireplace and ample space for gatherings, all with commanding views. The second-floor master suite offers a sitting area with a morning bar, a private balcony, a large spa tub, a glass block shower, marble countertops, and glass sinks. The third floor includes a library or private home office with a custom wrought iron railing, a wood beam ceiling, and wood windowsills. The property is beautifully landscaped with two gardens, expansive grass areas with an automatic watering system, and a charming large oak gazebo illuminated with soft lights and a maintenance-free floor, accessible via a gravel path from the house. The Brazilian oak pier features sturdy pilings with copper protective caps, two boat lifts (7,000 and 8,000 pounds), and slips for boats with up to four feet of draft. Conveniently located between Baltimore and Annapolis, it provides easy access to Alexandria, VA, Washington, D.C., and Potomac, Bethesda…MD—all within an hour's drive. The water is perfect for all kinds of activities, including boating, kayaking, and paddleboarding. This waterfront retreat seamlessly combines comfort, style, and functionality, making it a must-see for those seeking luxury living in a picturesque setting.

2292 Lake Dr, Pasadena

$799,755
4 Beds 2 Baths MDAA2146728 MLS
Stunning Waterfront Home with Deep Water Access & Exceptional Outdoor Living Experience serene, panoramic water views from this beautifully updated waterfront retreat offering 5 ft MLW, a private pier that could be extended, (see plan in the pictures of a proposed 40 ft+ pier), and space for multiple boats. Blending comfort, style, and functionality, this home is perfect for year‑round living or a luxurious weekend escape. Main Level Highlights Open‑concept living — Spacious family room with a gas fireplace and sliders leading to a 24' x 12' screened‑in porch (2022), built with maintenance‑free materials, two skylights, and sweeping water views. Renovated kitchen — Quartz countertops, stylish backsplash, upgraded stainless steel appliances, and durable LVP flooring. Semi‑formal dining room — Perfect for gatherings and entertaining. Main‑level bedroom — Large full bath with a double vanity. Waterfront office — Generous closet; ideal for work, hobbies, or flexible use. Second Level Features Expansive primary suite — Includes a private 16' x 11' screened‑in covered porch overlooking the water. Luxury primary bath — Seamless‑door 4 ft shower, elegant soaking tub, double sinks, and walk‑in closet. Two additional bedrooms — Well‑sized and full of natural light. Large laundry room — 16' x 8' with potential to convert into a third full bath. ⚙️ Exterior & Mechanical Features Oversized 2‑car garage Concrete driveway accommodating 5+ vehicles Two‑zone HVAC, with one system only 3 years old Natural gas already connected Private pier with new decking Deep water suitable for multiple boats. Prime Location and $10,000 in closing help from the seller This home is within walking distance to restaurants, a shopping center, and numerous local conveniences — offering the perfect blend of waterfront tranquility and everyday accessibility.

40 Johnson Rd, Pasadena

$1,350,000
5 Beds 2 Baths MDQA2017588 MLS
The locals called it Keister's Folly. In the mid-1940s, Dr. Keister built a barn on Kent Island overlooking Cox Creek, hoping to raise Black Angus cattle on 25 acres. The acreage was too small for the endeavor — but the barn he built was extraordinary. In the early 1960s, the developer of the Harbor View community converted it into a residence. The current owners' family purchased it in 1965 and has invested over $400,000 in improvements across sixty years of devoted stewardship. This property has never been publicly offered for sale — until now. Situated on 1.65 acres with 205 feet of protected waterfront on Cox Creek, this is one of the largest privately held waterfront parcels remaining in Harbor View. The 75-foot private pier extends into navigable tidal water with approximately 3.5 feet at mean low tide and two boat slips. Shoreline reinforced with professional rip-rap. Maps show Flood Zone X — outside 100-year and 500-year floodplains - buyer and agent should verify. The home offers 3,456 sq ft of living space across two levels including 700+ sq ft of unfinished second and third-level expansion space. Five bedrooms, two full baths. The upper-level primary suite features hardwood floors, panoramic water views, attached full bath, walk-in closet, private coffee bar with refrigerator, and a deck overlooking the creek. Updated kitchen with granite countertops, upgraded cabinetry, and high-end appliances, improvements throughout honor the building's barn heritage. Solid block construction. 200-amp electrical. Well water, public sewer. New Roof will be installed prior to settlement. Ideal for those who are seeking genuine Chesapeake waterfront with privacy, deep water access, and a property unlike anything else on the market. Be sure to download the Home Profile in the documents section for more details on the home including the history of the home.

2513 Cecil Dr, Chester

$1,950,000
4 Beds 3 Baths MDAA2148306 MLS
Stunning offering in gated Epping Forest! This mid-century modern waterfront sanctuary rises above Saltworks Creek on a quiet protected cove all on a .34 Acre lot—where timeless design meets an ethereal, peaceful connection to the water and outside. Originally built in 1978, the almost 3600 sq. ft residence recently underwent a comprehensive renovation inside and out while honoring Mid-Century authenticity and maintaining an effortless flow and contemporary preference. From the street side, the home presents a timeless silhouette with a recent 70K Elevator with ramp that serves as a secondary entrance servicing 2 out of the 3 levels. Waterside, the home is the ultimate expression of blurring the line between nature and interior with floor to ceiling glass walls, 8' sliding glass doors and unobstructed views from the deck. This home wasn't designed to look at the water but rather live with it. A massive stone central fireplace is the heart of the living area creating a cozy architectural retreat. Tasteful modernization but true to its mid-century roots, every element of the home has been considered preserving the architectural integrity while offering the comfort and convenience expected today. More than a home, this is a rare opportunity to own a piece of design history- reimagined for modern waterfront living. Email for list of 925K spent on restoration since purchase including brand new private pier and brand new Kitchen and all 3 Full Baths. Epping Forest is a Gated Waterfront Community on the Severn River with a community beach, waterfront clubhouse with restaurant and bar, tennis/pickleball and marina (new marina is currently under construction) Strong neighborhood connections where neighbors treat each other like family and fun happens weekly! Year around community events codify friendships, 4th of July Fireworks, Oyster & Bull Roast, Boat Club, Summer Volleyball League, community chapel, yoga & summer camps. Come experience the best Chesapeake Bay Maritime Annapolitan Lifestyle around! Epping Forest Inc is a special benefit tax district with bylaws and binding rules and regulations with Non-Riparian Waterfront. Special financing via Pentagon Federal Credit Jumbo 7/6 ARM available to low as 5.50%.

1739 Vineyard Trl, Annapolis

$2,685,000
5 Beds 5 Baths MDAA2148158 MLS
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!

3733 Thomas Point Rd, Annapolis

$25,000
MDAA2148498 MLS
Located on the beautiful Magothy River, Magothy Marina puts you in touch with a water world of cruising, racing, exploring, fishing, crabbing, and enjoyment of the Magothy River and numerous adjoining creeks and the Chesapeake Bay. Situated near the quiet residential area of Manhattan Beach, your marina is less than one mile from four-lane Ritchie Highway (MD Rt. 2) a half-hour away from metropolitan Baltimore, 15 minutes from historic Annapolis, and 45 minutes from Washington, D.C. On the water, within cruising range are many fine day visits and overnights-Annapolis and Baltimore Harbors St. Michaels, Oxford, and the many coves of the eastern and western shores of the Bay. Slip 2G is 32' long and 12' 8"wide. Located on one of the widest fairways in the marina, the slip abuts the main dock of the marina, allowing two points of access to your boat. As a slip owner, you would have access to all the amenities of the marina which include a well-maintained bathhouse, swimming pool, boat ramp, picnic tables, and grills. There is also storage for dinghies, paddleboards, and kayaks, as well as a launching space. Water and electricity are included as part of the quarterly condominium fees.

360 Magothy Rd Unit #2G, Severna Park

$45,000
MDAA2148502 MLS
Located on the beautiful Magothy River, Magothy Marina puts you in touch with a water world of cruising, racing, exploring, fishing, crabbing, and enjoyment of the Magothy River and numerous adjoining creeks and the Chesapeake Bay. Situated near the quiet residential area of Manhattan Beach, your marina is less than one mile from four-lane Ritchie Highway (MD Rt. 2) a half-hour away from metropolitan Baltimore, 15 minutes from historic Annapolis, and 45 minutes from Washington, D.C. On the water, within cruising range are many fine day visits and overnights-Annapolis and Baltimore Harbors St. Michaels, Oxford, and the many coves of the eastern and western shores of the Bay. Slip 1F is 40' long and 14' 3"wide. The slip abuts the main dock of the marina, allowing two points of access to your boat and is located on one of the widest fairways in the marina for ease in docking your boat. As a slip owner, you would have access to all the amenities of the marina which include a well-maintained bathhouse, swimming pool, boat ramp, picnic tables, and grills. There is also storage for dinghies, paddleboards, and kayaks, as well as a launching space. Water and electricity are included as part of the quarterly condominium fees.

360 Magothy Rd Unit #1F, Severna Park

$799,000
4 Beds 3 Baths MDAA2148342 MLS
Buy the home with NO INCOME VERIFICATION!! SAILBOATERS bring your SAILBOATS here with this 15’ water depth! WATERFRONT LIVING AT ITS FINEST! Nestled along Rock Creek & directly across the creek from the Maryland Yacht Club & the famous Mike's North Restaurant, this beautifully UPDATED 4-bedroom, 3-bath home offers the perfect blend of comfort, convenience, and BOATING lifestyle. With over 2,400 square feet of living space and a FULLY FINISHED WALK OUT BASEMENT, there's plenty of room for family, guests, and entertaining! The heart of the home features a stunning renovated kitchen with QUARTZ countertops, DUAL ISLANDS, INDUCTION Cooktop, DOUBLE OVENs, Under-cabinet lighting, Pantry, and WET BAR. Recent improvements throughout include UPDATED FLOORING THRU-OUT, Fresh paint, NEW LIGHTING, Newer WINDOWs, BRAND NEW CARPETING, and Beautifully RENOVATED BATHROOMS. Step outside to enjoy incredible WATER VIEWS from the expansive 600-sqft deck complete with CABLE RAILINGS, PRIVACY SCREEN, UPGRADED ELECTRIC & WATER Service, and plenty of space for gatherings. Follow the path to your private waterfront retreat featuring a 115' PIER with ELECTRIC & WATER, SANDY BEACH AREA at low tide, fire pit, 10,000 lb BOAT LIFT, and Swim Platform. BOATERS will love the easy access to the Chesapeake Bay & the convenience of fueling up just across the creek at the Maryland Yacht Club! Additional features include a new sidewalk and extended driveway accommodating up to SIX VEHICLES, waterproofed lower level, exterior paint, boat storage area, second laundry area in the primary suite, and numerous thoughtful UPGRADES THRU-OUT. This is more than a home—it's a WATERFRONT LIFESTYLE opportunity you won't want to miss- You deserve it!!

222 Bar Harbor Rd, Pasadena

$795,000
3 Beds 2 Baths MDAA2148142 MLS
Waterfront living with a private dock—all for under $800,000! Nestled in the charming Avalon Shores community, this beautifully updated coastal home perfectly blends classic elegance with modern comfort. The open-concept layout features two distinct living areas, ideal for both entertaining and daily relaxation. At the heart of the home is a premium kitchen equipped with granite countertops, stainless steel appliances, a center island with seating, and a sleek range hood. Large bay windows flood the main level with natural light. Enjoy beautifully finished bathrooms, a bedroom on the main living level, and two spacious bedrooms upstairs. Want more room? There’s extra space for an office, playroom, or a bedroom in the loft. Step outside to discover 63 feet of premier waterfront along South Creek. The spacious backyard and private dock with electric & water offer the perfect launchpad for kayaking, paddleboarding, or simply soaking in the tranquil scenery. The primary bedroom has a private balcony to enjoy the creek views. Enjoy peace of mind with new kitchen appliances (dishwasher, fridge - 2025; range hood - 2026), new roof (2025), new HVAC (2026), and sealing work and crawl space encapsulation (2020). Complete with an attached two-car garage offering secure inside access, and the convenience of a personal air-conditioned gym (or open the doors and enjoy the view and sounds of nature!). This turnkey property is a rare opportunity to live the ultimate waterfront lifestyle. Schedule your tour today!

4950 Bonniewood Dr, Shady Side

$999,000
3 Beds 2 Baths MDAA2148344 MLS
Tucked away at the end of a quiet cul-de-sac on over an acre of waterfront property, this beautifully renovated home offers a rare opportunity to enjoy the waterfront lifestyle without the time, expense, and uncertainty of a major renovation. Situated along peaceful Lerch Creek, just off the West River, the property combines privacy, natural beauty, and a truly turnkey living experience in one of Southern Anne Arundel County’s most desirable waterfront communities. Since purchasing the home in 2021, the current owner has completed a comprehensive transformation, thoughtfully updating nearly every aspect of the property. A stunning new kitchen, updated bathrooms, new flooring, fresh paint, new appliances, new siding, and a new roof create a home that feels fresh, modern, and completely move-in ready. The result is a property where the hard work has already been done, allowing the next owner to simply move in and start enjoying life on the water. Inside, natural light pours through oversized windows and a dramatic skylight, creating bright and inviting living spaces throughout. The main level offers an easy, comfortable flow between the living room, dining area, and renovated kitchen, making everyday living and entertaining equally enjoyable. A standout feature of the home is the main-level bedroom and full bathroom, offering exceptional flexibility for guests, multigenerational living, or convenient single-level living. Whether used as a primary suite option, private guest space, or home office with full bath access, this main-floor layout is a rare and valuable feature in a waterfront setting. One of the home’s most inviting spaces is the climate-controlled sunroom, providing year-round enjoyment of the waterfront environment. It serves as a peaceful extension of the living space, ideal for morning coffee, quiet reading, or simply watching wildlife along the creek. From here, step out to the deck and patio areas that overlook the expansive yard as it gently transitions toward the water. Upstairs, two additional bedrooms and a full bath provide comfortable private accommodations, offering separation and space for family or guests. Life in Galesville is centered around the water. From boating and kayaking on Lerch Creek and the West River to waterfront dining and community amenities, the village offers a relaxed Chesapeake Bay lifestyle with a strong sense of place. Residents enjoy nearby parks, pickleball courts, a fishing pier, playground, marinas, sailing opportunities, and several beloved waterfront restaurants, all contributing to the charm and convenience of the area. Beautifully renovated, meticulously maintained, and perfectly positioned on the water, this is the rare waterfront property where buyers can skip the renovation process and immediately begin enjoying everything that makes Chesapeake Bay living so desirable.

4889 Lerch Creek Ct, Galesville

$12,950,000
6 Beds 9 Baths MDAA2147500 MLS
Imagine arriving home each day to a place where the pace slows, the views stretch for miles, and every amenity for recreation, relaxation, and entertaining is right outside your door. Tucked away along the Chesapeake Bay, this extraordinary waterfront retreat offers a lifestyle that few properties can match, a private oasis where luxury and nature exist in perfect balance. Originally constructed by the renowned Pyramid Builders and later transformed through an extraordinary $7 million top-to-bottom renovation, also completed by Pyramid Builders, the estate has been reimagined to an uncompromising standard. Every space, finish, and amenity was thoughtfully designed and curated to create a residence that is as functional as it is beautiful, blending timeless craftsmanship with modern luxury. State of the art features include the Crestron Home Automation and integrated Lutron lighting systems while the modern luxuries entail top of the line Miele appliances including a built-in coffee maker, microwave and convection oven, BlueStar range, radiant heated floors in all bedroom bathrooms and much more. Here, days can begin with coffee overlooking the pond and its abundant wildlife, followed by a swim in the heated saltwater pool, a match on the tennis or pickleball court, a workout in the gym, or a stroll down to the sandy beach. Evenings are spent gathered with family and friends around the pool and hot tub, watching the game on the hydraulic television that rises from the landscape, enjoying a glass of wine from the tasting room, or simply taking in the stars above the Bay. The ever-changing waterfront scenery, southern exposure, and remarkable sense of privacy create a backdrop that feels more like a luxury resort than a private residence. Designed for those who believe home should be a destination, the property offers an incredible collection of indoor and outdoor amenities rarely found in a single estate. Tennis, pickleball, basketball, a climbing wall, playground, in-ground trampoline, expansive lawns, sandy beach, pond with fountain, indoor racquetball court with basketball and volleyball capabilities, golf simulator, game room, fitness center, indoor lap pool, infrared sauna, wine tasting and cellar area, and countless spaces to gather ensure there is always something to enjoy for every generation. The residence itself is beautifully designed and thoughtfully appointed, with spacious living and entertaining areas, a wraparound screened porch that embraces the waterfront setting, private ensuite bedrooms throughout, and a dedicated guest or in-law suite that welcomes family and friends in comfort and style. Abundant storage, an attached two-car garage, and a detached garage with additional space for vehicles, golf carts, recreational equipment, and storage provide the functionality expected of a property of this caliber. What makes this estate truly special is not simply the remarkable list of amenities—it is the feeling it creates. The extraordinary combination of peace, beauty, privacy, and convenience is increasingly difficult to find. Just minutes from Annapolis, yet seemingly a world away, this is the kind of property where children spend their days outdoors, guests never want to leave, and every sunset reminds you why you chose to call it home. A rare opportunity to own a true Chesapeake Bay waterfront compound where every day feels like a vacation, every detail has been thoughtfully considered, and the lifestyle is every bit as exceptional as the home itself. Welcome Home!

2045 Maidstone Farm Rd, Annapolis

$1,450,000
3 Beds 3 Baths MDAA2148278 MLS
** OPEN HOUSE EVERY DAY, CALL FOR TIMES! ** Discover the possibilities of waterfront living on beautiful Beard’s Creek in sought-after Riva. Offering privacy, boating access, and exceptional long-term potential, this spacious property is ready for its next chapter—and the seller welcomes all offers. The ranch-style home provides comfortable one-level living with three bedrooms and two full bathrooms on the main level. The walkout lower level features high ceilings, a full bathroom, fireplace, and expansive glass doors overlooking the water. This bright and versatile space offers excellent potential for an in-law suite, guest quarters, recreation room, home office, or additional living area. Step outside and enjoy the Chesapeake Bay lifestyle from your private pier, complete with two boat lifts and convenient access to Granville Creek, the South River, and the Chesapeake Bay. The generous waterfront setting provides plenty of space for outdoor entertaining, relaxing by the water, and enjoying peaceful views throughout the seasons. Located in a quiet, non-through neighborhood, the property feels tucked away while remaining just minutes from downtown Annapolis, shopping, dining, marinas, major commuter routes, and popular waterfront destinations such as Mike’s Crab House. It is also located within the South River school district with convenient access to Washington, D.C., Baltimore, and the surrounding region. The large waterfront parcel may also offer the potential for subdivision into two waterfront lots, adding another exciting dimension to this unique offering. Buyers should conduct their own due diligence with Anne Arundel County regarding subdivision possibilities, required approvals, and future development options. Whether envisioned as a primary residence, weekend retreat, multigenerational home, renovation opportunity, or long-term investment, this distinctive waterfront property offers flexibility, location, and tremendous potential. Seller welcomes all offers.

3088 Tudor Hall Rd, Riva

$315,000
1 Beds 2 Baths MDAA2147982 MLS
Experience the Baywoods lifestyle from Unit #202, a beautifully located 1BR/1.5BA cooperative residence in the sought-after Baywoods community of Annapolis. Nestled along the beautiful Chesapeake Bay, Baywoods offers residents the perfect blend of waterfront beauty, maintenance-free living, and a vibrant retirement lifestyle. Unit #202 is ideally located in the North Tower, just steps from the elevator and conveniently situated on the same floor as the Bistro, making dining and socializing easily accessible. Relax and enjoy peaceful wooded views from the spacious all-season enclosed patio, offering a private and serene setting year-round. Residents enjoy access to a wide range of amenities, dining venues, wellness programs, social activities, walking paths, and future care services—all within a scenic Annapolis setting. Call the listing agent for details on the cooperative ownership structure, buyer qualifications, monthly fees, and to schedule a private tour. Discover why so many residents choose Baywoods to enjoy the Chesapeake Bay lifestyle while maintaining independence and peace of mind.

7101 Bay Front Dr Unit #202, Annapolis

$4,995,000
5 Beds 4 Baths MDAA2146036 MLS
There are places where you visit the water, and there are places where the water becomes part of your everyday life. Perfectly positioned along the shores of Spa Creek in the heart of Eastport, this exceptional waterfront residence offers a front-row seat to one of Annapolis' most coveted lifestyles. Imagine stepping from your back door onto your private pier, casting off for an evening cruise, a sunset sail, or a waterfront dinner in Annapolis Harbor just minutes away. Paddleboards and kayaks launch effortlessly from the floating dock, while the protected waters of Spa Creek become your backyard playground. Life here unfolds both on and off the water. Mornings begin with coffee on the balcony overlooking the creek as the masts in Annapolis Harbor come to life. Afternoons are spent entertaining friends across multiple waterfront terraces, watching sailboats glide past and city lights reflect across the water. Evenings conclude with a short stroll to Eastport's restaurants, marinas, yacht clubs, and waterfront gathering spots. Thoughtfully rebuilt and extensively updated, the home blends timeless craftsmanship with sophisticated coastal living. Wide-plank white oak flooring, custom millwork, designer finishes, and walls of glass frame breathtaking views from nearly every room. The open-concept living spaces flow seamlessly to the waterfront, creating an ideal setting for both intimate gatherings and large-scale entertaining. With a private 40-foot pier, 12,500-pound boat lift, floating dock, and direct access to the Chesapeake Bay, this is more than a waterfront home—it is an opportunity to embrace the Eastport lifestyle that draws people from around the world to Annapolis, . Properties that combine protected deep-water access, exceptional views, and walkability to Downtown Annapolis rarely become available. This is a home best experienced from the waterfront, where the views, the setting, and the lifestyle speak for themselves.

217 Lockwood Ct, Annapolis

$599,000
3 Beds 2 Baths MDQA2017398 MLS Oyster Cove BLDG.
Enjoy carefree WATERFRONT living in this Beautifully UPDATED Condo in the sought-after Oyster Cove Community! Offering 3 bedrooms and 2 full bathrooms, this light-filled, one-level residence features an open floor plan designed for easy living and entertaining! Stunning wide plank wood flooring flows throughout the main living areas, complemented by newer stone countertops, fresh interior custom paint throughout and NEW carpet in the bedrooms. The spacious living and dining areas open to a Waterfront Deck where you can relax and enjoy breathtaking Sunsets over Eastern Bay and The Narrows. The thoughtfully designed layout offers generous bedroom sizes and two updated baths. Recent exterior improvements include new siding and new windows. Oyster Cove residents enjoy an exceptional Waterfront lifestyle with access to two Marinas, Swimming Pool, two Tennis Courts, a walking/jogging path and a Clubhouse with a fitness room. Conveniently located within walking distance to many restaurants, coffee spots, ice cream parlors, shops and popular dock bars!! Hop on the Kent Island Cross Trail for a bike ride throughout the Island! Just minutes from the Chesapeake Bay Bridge, this is Eastern Shore living at its finest!

116 Oyster Cove Dr Unit #1D, Grasonville

$749,000
4 Beds 3 Baths MDAA2147550 MLS
Discover the ultimate Chesapeake Bay waterfront lifestyle in this beautifully appointed 4-bedroom, 3-bath residence, where breathtaking water views and thoughtful design create an exceptional coastal retreat. Perfectly positioned to capture panoramic bay vistas, this home offers an elegant blend of comfort, sophistication, and year-round waterfront living. The kitchen serves as the centerpiece of the home, featuring seamless flow into the open-concept living spaces. A spacious dining room provides the perfect setting for holiday gatherings, intimate dinner parties, and memorable celebrations with family and friends. The light-filled living room showcases stunning water views and a cozy fireplace for cooler evenings; and opens to an expansive deck, creating a seamless connection between indoor and outdoor living. Designed with convenience in mind, the main level includes a bedroom, full bath, and laundry area, offering the option for first-floor living or comfortable accommodations for guests. Upstairs, the private primary suite serves as a peaceful sanctuary, complete with an en suite bath and direct access to a private waterfront deck where you can enjoy morning coffee, spectacular sunrises, and endless views of the bay. Two additional bedrooms and a full bath provide ample space for family and visitors. The lower level features two garages, ideal for hobbies, projects, storage, or future customization. Outside, multiple deck spaces invite you to relax, entertain, and immerse yourself in the beauty of the Chesapeake Bay. Spend your days boating, fishing, kayaking, paddleboarding, or simply enjoying the tranquil waterfront setting from the comfort of home. Whether you're seeking a luxurious year-round residence or an exceptional waterfront getaway, this remarkable property offers a rare opportunity to experience the very best of Chesapeake Bay living. All set within the stunning town of Churchton with the water front park, a playpark and lovely water front walking paths; this is truly a peaceful and gorgeous place to be!

5523 Ilchester St, Churchton

$997,000
5 Beds 4 Baths MDQA2017028 MLS
WELCOME to the Eastern Shore -- This charming Nantucket style waterfront home offers unique privacy with the advantage of being in a wonderful water privilege community. Rare 1.5-acre lot offers a 5 bedroom, 3.5 bath renovated beauty that offers upgrades to include: true handsome hardwood floors, stunning renovated Coastal kitchen and baths, new windows, siding and doors. There are scenic wrap-around water views from almost every room. The water depth is low and small craft is advised in the creek.... which does exit into the bay.... The community boat ramp is directly across the street for easy boating. There are a couple of garage options available for this property: The garage option is " TO BE BUILT.... County has said OK to pool and garage addition, permit process has started...

101 Beachside Dr, Stevensville

$1,110,000
4 Beds 3 Baths MDAA2147370 MLS
Welcome to 4721 Oak Road, your waterfront paradise on the Chesapeake Bay! Nestled in the sought-after Felicity Cove community of Shady Side, this custom-built 2014 coastal home seamlessly blends modern luxury with effortless waterfront living. Boasting 4 spacious bedrooms, 3 full bathrooms, and 1,868 square feet of pristine living space, this residence shows like new. Step inside to an open-concept main level featuring gleaming hardwood floors and sun-drenched windows that allow sweeping, panoramic water views. The gourmet kitchen is an entertainer’s dream, equipped with premium granite countertops, crisp cabinetry, and stainless steel appliances. Upstairs, the private primary suite serves as a peaceful sanctuary, complete with its own private terrace—the perfect vantage point for watching the sunrise over the Bay with your morning coffee. Outside, your private oasis awaits. The property features a private pier, perfect for crabbing and fishing for Rockfish. Equipped with high-efficiency gas heat, this property offers the ultimate lock-and-leave or year-round coastal lifestyle. Don't miss this rare opportunity to own a modern waterfront gem just minutes from local parks and trails, and an easy commute to Annapolis, DC, and Baltimore.

4721 Oak Rd, Shady Side

$362,500
2 Beds 3 Baths MDQA2017394 MLS Thompson Creek Condos BLDG.
Welcome to 1302 Marion Quimby Dr. Nestled in the serene Thompson Creek community, this charming townhouse with a new HVAC and hot water heater offers a perfect blend of comfort and modern living. With 1,161 square feet of thoughtfully designed space, this home features two spacious bedrooms and two and a half bathrooms, making it an ideal retreat for those seeking tranquility and convenience. Step inside to discover an inviting open floor plan that seamlessly connects the living, dining, and kitchen areas. The contemporary design is enhanced by plush brand new carpeting and elegant ceramic tile flooring, creating a warm and welcoming atmosphere. The living room is anchored by a cozy fireplace, complete with glass doors and a stylish mantel, perfect for those chilly evenings spent at home. The kitchen is a culinary delight, featuring ample table space for casual dining and modern appliances, including a dishwasher, microwave, and electric oven/range. Whether you're preparing a gourmet meal or enjoying a quick breakfast, this kitchen is designed to meet your needs. Retreat to the primary suite, which boasts an en-suite bathroom for added privacy and convenience. Thoughtful window treatments throughout the home allow for natural light while maintaining a sense of intimacy. Step outside to enjoy the beautiful exterior features, including a charming balcony and deck over-looking Thompson Creek and gorgeous water views and sunsets, perfect for sipping your morning coffee or unwinding after a long day. The community amenities are a true highlight, offering access to a refreshing outdoor pool, tennis courts, and scenic jog/walk paths that wind through beautifully landscaped grounds. The property is situated on the banks of Thompson Creek, providing stunning views of the water, lush pastures, and surrounding trees. Imagine relaxing on your deck while listening to the gentle sounds of the creek, creating a peaceful oasis right at your doorstep. With unassigned off-street parking and a well-maintained community that includes exterior building maintenance, management, and trash services, this home offers both convenience and peace of mind. Experience the perfect blend of comfort, community, and natural beauty in this delightful townhouse. Whether you're looking for a weekend getaway or a permanent residence, this property is sure to meet your needs and exceed your expectations.

1302 Marion Quimby Dr, Stevensville

$599,900
3 Beds 4 Baths MDQA2017452 MLS
Experience the best of Kent Island waterfront living in this beautifully appointed home located in the sought-after Bayside community of Chester. Designed for both everyday comfort and effortless entertaining, this residence features an open-concept floor plan with abundant natural light, spacious living areas, and stylish finishes throughout. The gourmet kitchen serves as the heart of the home, offering generous counter space, quality cabinetry, and a seamless flow into the dining and living areas. The expansive primary suite provides a private retreat with a walk-in closet and luxurious ensuite bath. Additional bedrooms and flexible living spaces offer plenty of room for guests, a home office, or recreation. Enjoy outdoor living from the private deck, perfect for relaxing and taking in the peaceful surroundings. An attached garage and ample storage add convenience to everyday life. Residents of Bayside enjoy exceptional community amenities, including a clubhouse, fitness center, swimming pool, tennis courts, walking trails, and marina access. The boat slips at Castle Marina are rented. It can be on a short term up to a yearly basis. There are some slips over on the side where Queens landing condos are that can be for sale. Ideally located near waterfront dining, shopping, golf courses, and major commuter routes, this home offers the perfect blend of Eastern Shore charm and modern convenience. Don't miss this opportunity to enjoy a resort-style lifestyle in one of Chester's premier waterfront communities. Additional parking spaces are located across the street for your convenience.

1012 Auckland Way, Chester

$4,995,000
5 Beds 5 Baths MDQA2017484 MLS
Architect-designed contemporary waterfront home on nearly 18 private acres across two parcels with approximately 1,400 feet of shoreline on Greenwood Creek. Positioned to capture 180-degree western views, the property offers privacy, deep water, and a setting that is increasingly difficult to find on Maryland’s Eastern Shore. A custom pivoting front door creates a striking first impression and sets the tone for the home's thoughtful design. The home was designed to take advantage of the surrounding water and landscape, with floor-to-ceiling windows, open gathering spaces, and strong indoor-outdoor connections throughout. The kitchen opens to the main living areas and features a glass accordion door that connects directly to the screened porch, creating a seamless transition between indoor and outdoor spaces. The layout flows easily between the kitchen, dining areas, family room, porch, and pool area, making the home equally well suited for everyday living and entertaining. The primary suite is set apart from the rest of the home by a glass-enclosed walkway and includes a private office, large dressing room, en-suite bath, and private porch access. In addition to the primary suite, the main level includes three additional bedrooms, each with access to a private bathroom. The finished lower level includes a home theater, billiards room, bar area, workout room, additional bedroom and full bathroom, along with unfinished basement space for storage. Outdoor features include a solar-heated pool, private beach, and deep-water pier with two boat lifts. The protected shoreline and direct access to Eastern Bay make this an ideal property for boating and waterfront living. A three-bay outbuilding with workshop space and additional storage provides room for equipment, hobbies, or car and boat storage. Located just outside Queenstown, the property is convenient to Easton, Annapolis, Washington D.C., Baltimore, and Philadelphia while offering the privacy and pace of the Eastern Shore.

2800 Bennett Point Rd, Queenstown

$1,550,000
4 Beds 4 Baths MDAA2141366 MLS
TO BE BUILT – Exceptional Luxury Home with 1-Acre Waterfront Lot and Private Boat Ramp Experience the rare opportunity to build a custom luxury waterfront home just minutes to the Chesapeake Bay. Nestled on a tranquil wooded lot in West River, this stunning new construction residence offers the perfect blend of refined craftsmanship, modern comfort, and waterfront living. Thoughtfully designed with over 3,500 square feet of finished living space, this 4 bedroom, 3.5 bath home features a highly functional floor plan that lives comfortably for everyday enjoyment while effortlessly accommodating family and guests. The main-level primary suite provides convenience and privacy, while expansive living areas are designed to maximize natural light. Luxury finishes come standard throughout, including 10-foot ceilings, wide-plank White European Oak flooring, furniture-grade custom cabinetry, premium quartz countertops, and a chef's kitchen appointed with Sub-Zero and Wolf appliances. Seamless indoor-outdoor living awaits with a spacious screened porch featuring a cozy outdoor fireplace—perfect for entertaining or relaxing while enjoying the waterfront setting. Enjoy boating, fishing, kayaking, and all that Chesapeake Bay waterfront living has to offer directly from your backyard. Built by the renowned Whitehall Building & Company, buyers are invited to tour the builder's model home by appointment to experience the exceptional craftsmanship, attention to detail, and customization options available. As an added incentive, buyers will receive a $10,000 options credit when using the builder's preferred lender and title company. Qualified buyers may also take advantage of 100% VA financing. A rare opportunity to create your dream waterfront retreat in one of Anne Arundel County's most desirable waterfront communities. Contact LA with any questions or to schedule a tour of the property.

1110 Cherry Point Rd, West River

$1,100,000
2 Beds 2 Baths MDAA2147336 MLS
Welcome to this charming waterfront retreat perfectly positioned along the shores of Browns Cove with breathtaking panoramic water views from nearly every window. Originally built in 1940 and thoughtfully renovated in 2008, this contemporary home seamlessly blends timeless character, modern comfort, and an unparalleled waterfront lifestyle. Offering 2 bedrooms, 2 full bathrooms, and over 2,000 finished square feet, the home features an open-concept main level designed for effortless everyday living and entertaining. The spacious living room flows seamlessly into the kitchen, while a separate dining room provides the perfect setting for gatherings. Walls of windows throughout the home fill the interior with natural light and frame the stunning marina and river views. Beautiful hardwood and carpet flooring, along with two cozy fireplaces, create a warm and inviting atmosphere. The main level includes a comfortable bedroom and full bath, while the entire upper level is dedicated to an exceptional primary suite. This private sanctuary features a spa-inspired bathroom, dual walk-in closets, a sitting area, and a private deck overlooking the water—an ideal place to enjoy your morning coffee or unwind at sunset. An upper-level laundry area adds everyday convenience. Outside, enjoy direct water access from your private dock equipped with an electric boat hoist/lift, along with riparian rights and navigable water access right from your backyard. Whether you're an avid boater or simply appreciate life by the water, this property offers a rare opportunity to embrace the Chesapeake Bay lifestyle. An added bonus rarely found in this section of the neighborhood is the abundant off-street parking. The property offers space for up to five vehicles, with four parking spaces in the driveway and an additional gravel parking space out front—an exceptional convenience where parking is often at a premium. Residents of Palisades on the Severn enjoy an array of community amenities, including beaches, a boat ramp, and playgrounds. Combining serene waterfront living with easy access to shopping and dining, this special property offers the perfect place to call home.

993 Round Bay Rd, Crownsville

$1,150,000
3 Beds 3 Baths MDAA2146926 MLS
Open Friday, July 10th from 4-6:30 PM! Vacation every day in your stunning two-level condo with exceptional views and amazing privacy! Wonderful open floor plan and walls of glass make you feel like you are on a boat and create outstanding views from every room. Exceptional features include smart technology throughout, a wood-burning fireplace, soaring ceilings, GE Cafe appliances (new in 2024), electric blinds, separate dining area with a glass wall that beautifully reflects the water and accentuates the gorgeous natural light. Designer-selected tones throughout the home reflect the changing moods of the outdoors — soft greys and grey blues echo the water and sky, while subtle sunrise-inspired oranges and purples bring warmth and character to the interiors. Cherry wood floors and rich wood accents create a seamless connection between indoor living and the surrounding waterfront setting. The unit has been redesigned to increase the storage, creating ample closet space. Every day is a new opportunity to experience an incredible sunrise over the Chesapeake Bay Bridge and Eastern Shore, follow the tankers and watch the boat races. Chesapeake Harbour is a gated waterfront resort with outstanding water access, including private beaches, boat launch, and great piers for gathering with friends and neighbors to watch the races or cast a fishing line. Choose which of the two waterside community pools suits your mood (one is heated), enjoy a game of tennis on the multiple available courts, or launch your boat or board from the sandy beach and glide across the water. Take one of the many community paths to the marina (slips at Chesapeake Harbour Marina are available for a fee and NOT part of the HOA) or stop in for drinks or dinner at The Beacon harborside restaurant. Better still, stay home where you have the best view in the community and just relax. This amazing haven is located within a few short minutes of fun Eastport, Downtown Annapolis and its many offerings, dozens of scrumptious close-by neighborhood restaurants, 5 minutes from multiple breathtaking parks (Quiet Waters, Thomas Point, EO Moyer, Carr's), and it truly feels like a world away from it all! Bonus-100% turnkey-furniture included! Ask for more details!

2127 Beach Village Ct Unit #202, Annapolis

$344,900
2 Beds 3 Baths MDQA2017440 MLS Thompson Creek Condos BLDG.
Motivated seller! Experience relaxed waterfront living in this beautifully updated townhome condominium overlooking scenic Thompson Creek, where stunning water views, community amenities, and an exceptional coastal lifestyle come together. Thoughtfully renovated and move-in ready, this waterfront retreat blends modern upgrades with inviting indoor and outdoor spaces designed for both everyday comfort and, entertaining.The main level welcomes you with an updated kitchen featuring granite countertops, stainless steel appliances, and abundant cabinetry. Just beyond, the sunken living room creates a warm and inviting atmosphere highlighted by a beautiful brick gas fireplace (ready for propane hookup if desired and easily convertible back to wood-burning), a custom wet bar, and seamless access to the spacious waterfront deck, perfect for enjoying peaceful sunsets over the creek. Recent improvements totaling approximately $20,000 include luxury vinyl plank flooring, new carpet upstairs, fresh interior paint throughout, and new blinds, giving the home a refreshed, modern feel. Upstairs, you'll find two generously sized bedrooms, ample closet space, and 2.5 baths, including a spacious primary suite with a well-appointed ensuite bath. A private balcony off the primary bedroom provides tranquil water views, breathtaking sunsets, and peaceful views of the community walking paths. Outdoor living is truly at the heart of this property. Enjoy boating, fishing, kayaking, swimming, and waterfront recreation just moments from your door. Residents have access to a community pool, clubhouse, tennis courts, scenic walking and jogging paths, nearby marinas, and multiple boat launch options, including Thompson Creek Landing within walking distance and convenient access to Kent Island. Situated along the banks of Thompson Creek, this home offers picturesque views of the water, mature trees, and surrounding natural beauty, creating a peaceful setting perfect for relaxing, entertaining, or simply enjoying the waterfront lifestyle. Additional conveniences include unassigned off-street parking and a well-maintained community offering exterior building maintenance, professional management, and trash service, providing low-maintenance living and added peace of mind. Whether you're searching for a full-time residence, weekend retreat, or investment opportunity, this home offers the perfect blend of comfort, recreation, and coastal charm in an unbeatable waterfront setting.

1102 Marion Quimby Dr, Stevensville

$799,000
4 Beds 4 Baths MDQA2017424 MLS
This boater's paradise demonstrates the perfect blend of luxury and convenience. The property boasts three floors of sweeping waterfront views all easily accessed via your own private elevator. High end finishes can be found throughout and the home has been impeccably maintained. The first floor feels inviting with the fireplace, open kitchen, and guest bedroom with ensuite full bathroom currently being used as an office. The second floors wows you with 3 spacious bedrooms including the primary that has a walkout balcony for quiet evenings staring out over the water. The top floor provides yet another entertaining or living space with a wet bar, full bathroom, and a walk out balcony. Outdoor living in general is a highlight here with each floor allowing for a different perspective of the Eastern Shore landscape. Don't forget about the amenities of the community. Lounge out by the pool, walk to famous waterfront seafood establishments, or navigate the vast waters of the Chesapeake from your deeded 35 foot deep water boat slip just steps away. This luxury Eastern Shore destination is located just an hour from Washington, D.C. or Baltimore and less than two hours from Philadelphia.

110 Channel Marker Way Unit #203, Grasonville