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$899,000
3 Beds 3 Baths
There's golf course frontage and then there's this. Set on a prime corner lot overlooking the 11th green of GlenRiddle's War Admiral Course, this home gives you a front-row seat to one of the community's signature holes. Whether you're sipping your morning coffee in the sunroom or winding down on the porch in the evening, you'll spend your day watching approach shots, birdie putts, and one of the best views GlenRiddle has to offer. Inside, the home is just as impressive. With 3,378 square feet, 3 bedrooms, 2.5 baths, and a first-floor primary suite, the layout is as practical as it is inviting. Best of all, it's being offered completely furnished, making this a true turnkey opportunity. The home has been meticulously maintained and feels virtually brand new. The current owners didn't just maintain it, they upgraded it. The first floor features a dual-fuel heat pump and gas furnace, the sunroom has its own mini-split system, there's a tankless gas water heater, premium window blinds throughout, and yes... three dishwashers, because entertaining should be easy. A brand-new epoxy garage floor is also scheduled to be installed at the end of August. Life in GlenRiddle extends far beyond your front door. Residents enjoy two championship golf courses, an outdoor pool, fitness center, pickleball and tennis courts, a billiard room, marina, Ruth's Chris Steak House, and optional golf memberships, all within one of the area's most sought-after gated communities. Homes with this view don't come along often. Homes that come fully furnished, show like new, and let you move right in are even harder to find. Professional photos coming soon.

10001 Flotilla Ln, Berlin

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

$299,000
3 Beds 3 Baths
Completely Renovated & Turn-Key Home with Pond & Golf Course Views in the Blue Ribbon Delmar School District! Welcome to 9126 Clubhouse Drive, a beautifully updated home nestled in one of the area’s most desirable locations. Currently operating as a successful Airbnb, this property offers an incredible opportunity for homeowners, investors, or anyone looking for a move-in-ready home with breathtaking views. Enjoy peaceful mornings and relaxing evenings overlooking the pond directly behind the home, while also taking in beautiful views of the golf course. This picturesque setting provides the perfect backdrop for everyday living. In January, a sprinkler system malfunction resulted in water damage, creating the opportunity for extensive professional renovations throughout the home. Nearly every affected area has been professionally restored and upgraded, giving this property the feel of a beautifully refreshed home. Recent improvements include: Completely renovated kitchen featuring new cabinetry, granite countertops, tile flooring, refrigerator, faucets, lighting, plumbing repairs, freshly finished walls and ceilings, and new paint. Spacious living and dining areas with new luxury vinyl plank flooring, refinished walls, and freshly painted ceilings throughout. First bedroom with new walls, fresh paint, luxury vinyl plank flooring, and a new ceiling fan. Updated primary suite with freshly painted walls and ceiling. Renovated primary bathroom featuring a new vanity, double sink faucets, new tile flooring, beautifully tiled shower and tub surround, and new shower doors. Updated guest bathroom with a new vanity, sink faucets, and fresh paint. Laundry room improvements include new walls, fresh paint, new tile flooring, and a brand-new washer and dryer. Garage completely refreshed with new insulation, walls, ceilings, and paint. Additional upgrades include: Daikin wall-mounted heating and air conditioning unit (approximately 8 months old). Roof replaced approximately 2 years ago. Sprinkler system professionally repaired and restored. Exterior plumbing to hose faucets replaced with convenient new access panels for future servicing. Located in the highly acclaimed Blue Ribbon Delmar School District, this exceptional home offers the perfect combination of quality craftsmanship, modern upgrades, scenic pond and golf course views, and outstanding value. Whether you’re searching for your next primary residence, a weekend getaway, or an income-producing investment, 9126 Clubhouse Drive is truly move-in ready and ready to impress. This home is a must-see!

9126 Clubhouse Dr, Delmar

Listing courtesy of ERA Martin Associates. Contact: 4107491818

$769,000
3 Beds 2 Baths
Experience the ultimate Ocean City lifestyle at Capri 1911! This stunning oceanfront 3-bedroom, 2-bath condo offers breathtaking views, incredible amenities, and the perfect setting to enjoy everything coastal living has to offer. Step inside and immediately feel the inviting coastal atmosphere, with an open and spacious layout designed to maximize comfort and showcase the spectacular ocean views. The beautifully upgraded kitchen features sleek stainless steel appliances, plenty of workspace, and a seamless flow into the dining and living areas. The breakfast bar and spacious dining area create the perfect gathering space for family and friends, whether you’re enjoying a casual beach breakfast or entertaining after a day in the sun. The living area opens directly to the expansive private oceanfront balcony — the perfect spot to sip your morning coffee while watching the waves roll in, relax with a good book in the afternoon, or enjoy the unforgettable views and ocean breeze at the end of the day. With panoramic views of the Atlantic, every moment feels like a true beach escape. Beyond the condo, Capri offers an impressive array of amenities including an indoor pool, sun deck, fitness room, game room, library, basketball courts, tennis courts, saunas, elevators, and on-site security. Located directly on the oceanfront, this property puts you just seconds from the sand and minutes from Ocean City’s best dining, shopping, and entertainment. Whether you’re searching for a vacation getaway, investment opportunity, or your own private seaside oasis, Capri 1911 offers the perfect blend of luxury, comfort, and the effortless coastal lifestyle that makes Ocean City so special.

11000 Coastal Hwy Unit #1911, Ocean City

Listing courtesy of Keller Williams Realty Delmarva. Contact: 4105246400

$185,000
1 Baths
The perfect beach getaway at an incredible price! Welcome to Jamaica Daybreak 210, a charming second-floor end unit studio condo offering everything you need to enjoy the true Ocean City lifestyle. Located in one of Ocean City’s most desirable areas on 32nd Street, this prime location puts you just seconds from Jolly Roger Amusement Park, the beach, the bay, boat and jet ski rentals, and all the local favorites that make this area such a sought-after destination. Step inside this bright and inviting open-concept studio featuring a comfortable layout, a nice kitchen, and a spacious balcony perfect for soaking in the coastal atmosphere. The end unit location is truly one of the best features of this condo, offering an additional side window that fills the space with extra natural sunlight while providing a beautiful glimpse of the ocean. Start your morning with coffee on the balcony, fill your days with beach adventures and sunshine, and return home to the perfect place to relax, recharge, and enjoy the coastal lifestyle you’ve always wanted. This beach retreat has been lovingly maintained as a personal residence and was not rented. The efficient layout provides all the essentials for easy beach living, whether you’re looking for a weekend escape, a low-maintenance second home, or a place to create lasting Ocean City memories. Recent updates include a new washer and dryer (2025), Amana wall heating and air conditioning unit (2024), new window (2023), new deck screen door (2022), and appliances (2019). Jamaica Daybreak 210 offers the perfect blend of location, comfort, and coastal charm — a place where you can truly embrace the laid-back Ocean City lifestyle from sunrise coffee to sunset relaxation.

202 32nd St Unit #210, Ocean City

Listing courtesy of Keller Williams Realty Delmarva. Contact: 4105246400

$309,900
2 Beds 2 Baths
Welcome to coastal living in this beautifully updated first-floor, end-unit condo, offering the perfect blend of comfort, convenience, and resort-style amenities in one of Kent Island's most sought-after communities. With no stairs to navigate and handicap-accessible features, this home provides effortless everyday living while enjoying the added privacy and abundant natural light that only an end unit can offer. The beautifully updated kitchen features new quartz countertops, backsplash, a breakfast bar, newer stainless steel appliances, and abundant cabinetry, making it as functional as it is stylish. The adjoining dining area flows seamlessly to the private deck through sliding glass doors, bringing the outdoors in and making entertaining a breeze. Fresh paint, carpet, kitchen appliances, HVAC and washer/dryer are all less than 4 years old. The spacious primary suite serves as a relaxing retreat with a large walk-in closet and private ensuite bath. A second generously sized bedroom offers exceptional flexibility for guests, a home office, or family visits, while elegant plantation shutters add timeless charm and character to both bedrooms. Life at Bayside is about much more than the home itself. Residents enjoy a truly maintenance-free lifestyle, with exterior maintenance and community upkeep handled by the condominium association, leaving more time to enjoy everything Kent Island has to offer. Community amenities include a clubhouse, swimming pool, fitness center, tennis courts, beautifully landscaped grounds, and Castle Marina just a short walk away. Outdoor enthusiasts will appreciate being only steps from the Cross Island Trail, offering miles of scenic walking and biking paths showcasing the natural beauty of the Chesapeake Bay. Ideally located near waterfront dining, shopping, and local attractions, this home also provides easy access to Route 50 and the Chesapeake Bay Bridge, international airports and coastal beaches, making commuting and travel exceptionally convenient. Where every day feels like a vacation—and the only thing left to maintain is your schedule.

302 Merganser Ct Unit #A, Chester

Listing courtesy of Keller Williams Flagship. Contact:

$899,900
3 Beds 2 Baths
Experience the best of coastal waterfront living in this charming 3-bedroom, 2-bath home situated on a spacious 7,500-square-foot lot in the desirable Caine Keys community. Just a short stroll to the beach, this exceptional property offers the perfect combination of waterfront living, outdoor recreation, and coastal convenience. Lovingly maintained and never rented, this home has been cherished as a private family retreat and is ready for its next owners to create lasting memories. Inside, you'll find a warm and inviting floor plan designed for comfortable everyday living and entertaining. The lovely kitchen features a convenient breakfast bar and flows seamlessly into the dining area, creating the perfect gathering space for family meals and entertaining friends. The spacious living area is filled with natural light and offers a relaxing atmosphere after a day on the water or at the beach. The primary bedroom is a peaceful retreat complete with a private en suite bath. A generously sized second bedroom provides comfortable accommodations for family and guests, while the hall bath and separate laundry room add convenience. The waterside sunroom/third bedroom, currently being used as a Florida room, overlooks the water and offers breathtaking views, making it the perfect place to enjoy your morning coffee, read a book, or simply relax while watching the boats go by. Step outside to discover your own waterfront oasis. The beautifully designed paver courtyard is ideal for grilling, entertaining, or enjoying warm summer evenings. The expansive deck overlooking the canal is the perfect place to unwind with your morning coffee or evening cocktail while taking in the refreshing ocean and bay breezes. There is a nice awning as well for the hot summer days. Whether you enjoy boating, paddleboarding, kayaking, fishing, or simply watching the sunset over the water, this location offers endless opportunities for waterfront recreation right from your backyard. The attached garage and storage shed provide plenty of room for all of your beach gear, bikes, kayaks, and fishing equipment. Located just moments from Ocean City's beautiful beaches, restaurants, shopping, and entertainment, 131 Old Wharf Road offers the ideal blend of tranquility and convenience. Whether you're searching for a primary residence, a vacation getaway, or an investment opportunity, this rare waterfront gem is ready for you to start enjoying the coastal lifestyle you've always dreamed of.

131 Old Wharf Rd, Ocean City

Listing courtesy of Coldwell Banker Realty. Contact: 4438562211

$365,000
2 Beds 2 Baths
Welcome to easy, one‑level living in The Parke at Ocean Pines—the perfect retirement community for active adults who want comfort, convenience, and a vibrant social lifestyle. This move‑in‑ready home offers everything you need on a single floor, with spacious rooms, natural light, and low‑maintenance living. Step outside to your newly added rear patio, backing to peaceful trees—an ideal spot for morning coffee, afternoon reading, or relaxing outdoors in total privacy. The Parke is known for its friendly, active atmosphere, offering endless opportunities to stay engaged: farmers markets, food trucks, social clubs, fitness classes, and special community events throughout the year. Enjoy resort‑style amenities including an indoor pool, clubhouse, walking trails, and access to all Ocean Pines facilities. Located just minutes from Ocean City’s beaches, golf courses, marinas, and restaurants, this home gives you the best of coastal living with the peace and privacy of a 55+ neighborhood. Perfect as a full‑time residence or a low‑maintenance second home near the shore. Move right in and start enjoying the lifestyle you’ve been waiting for.

13 Hatteras St, Ocean Pines

Listing courtesy of Samson Properties. Contact: 7033788810

$1,650,000
5 Beds 4 Baths
Waterfront on two sides—that's the rare gift waiting at 1069 Shore Acres Rd, where a flat, sun-drenched parcel meets the water along its front and southern edge, just steps from a secluded community beach. This 4-bedroom, 2.5-bath home offers 2,386 square feet of coastal living in one of Arnold's most coveted enclaves. Recent investments make this residence as sound as it is scenic. A cascade of 2022 upgrades—new roof, siding, windows, front door, deck, and a redesigned porch overhang—refreshed the exterior top to bottom. Crawl space waterproofing (2021), a reconditioned iron balcony with spiral stairs (2023), plus a 2025 bulkhead along the riverfront and side and a newly parged foundation give buyers genuine peace of mind. Tucked at the rear sits a detached one-car garage with workshop, ideal for hobbyists and boaters alike. Climb the separate staircase to discover a fully finished second-level retreat, complete with living quarters and a luxurious bath—perfect for guests, extended family, or a private studio escape. From the garage living area, you can look across Lake Placid (the one in Arnold) and out to the Magothy throughout every season. Life in Shore Acres means embracing the rhythm of the water, with quiet mornings on the deck and easy access to the neighborhood beach. When you crave something livelier, downtown Annapolis beckons with fine dining, boutique shopping, and historic charm just minutes away. Route 50 keeps Baltimore and Washington, D.C. comfortably within reach. Homes offering this blend of dual waterfront exposure, modern updates, and flexible living space rarely surface. Come experience it firsthand.

1069 Shore Acres Rd, Arnold

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$749,999
3 Beds 4 Baths
Welcome to this beautifully maintained townhome in Eastport’s sought-after Boucher Place community, where timeless design meets effortless, low-maintenance living. Built in 2013 and offering nearly 1,800 square feet of thoughtfully designed space, this home is tailored for both relaxing everyday comfort and vibrant entertaining. At the center of the main level is a bright, open kitchen anchored by a large island with seating. It seamlessly connects to a living space centered around a cozy gas fireplace, creating a warm, natural gathering spot for guests. Enjoy meals in the adjacent dining area, or step outside into your private outdoor oasis—a freshly landscaped rear patio lit by charming bistro lights, perfect for al fresco dining and evening relaxation. Rich hardwood floors run throughout the main living level, while brand-new carpet (2026) adds plush comfort upstairs. Coupled with fresh neutral interior paint (2026), the entire home delivers a crisp, move-in-ready feel. The upper two levels feature three generously sized bedrooms, highlighted by a serene primary suite complete with a walk-in closet and an en-suite bath featuring a deep soaking tub and separate walk-in shower. A dedicated second-floor laundry room adds essential daily convenience. For a true outdoor highlight, head up to the private rooftop deck- an ideal retreat for morning coffee or sunset drinks. Thoughtful exterior details and community perks make daily life a breeze. Practical highlights include a detached two-car garage with rear entry and a paved driveway, while a spacious community green sits just steps from your front door. The low-maintenance Boucher Place HOA covers lawn care, snow removal, and exterior building insurance for true lock-and-leave ease. Ideally located within walking distance of vibrant downtown shops, dining, and waterfront attractions, this exceptional Eastport property allows you to spend less time on upkeep and more time enjoying coastal living.

21 Boucher Pl, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$274,999
1 Beds 1 Baths
FULLY FURNISHED!!! Welcome to Jamaica IV, where coastal living meets convenience in the heart of Midtown Ocean City! This charming first floor condo at 104 56th Street #106 offers the perfect beach retreat, investment opportunity, or weekend getaway just seconds from both the beach and the bay. Inside, you'll find a bright, thoughtfully designed living space that maximizes comfort and functionality, along with a full bath and an efficient layout that's easy to maintain. The first floor location provides convenient access, making it ideal for owners and guests alike. Jamaica IV is perfectly situated on 56th Street, seconds from Ocean City's beautiful beaches, popular restaurants, nightlife, shopping, mini golf, and local attractions. Whether you're spending the day on the sand, enjoying waterfront dining, or taking in breathtaking bay sunsets, everything you love about Ocean City is just moments away. Whether you're searching for a personal beach escape or a property with strong rental potential, this Midtown gem offers an unbeatable combination of location, convenience, and coastal charm. Don't miss your opportunity to own your place at the beach!

104 56th St Unit #106, Ocean City

Listing courtesy of Coldwell Banker Realty. Contact: 4438562211

$389,000
3 Beds 2 Baths
This beautifully updated 3-bedroom, 2-bath home is tucked away on a quiet cul-de-sac and sits on an oversized lot with a 2-car garage. Enjoy outdoor living at its best with a screened porch, spacious deck, and a fully fenced backyard that's perfect for kids and pets to play safely. Inside, you'll find new luxury vinyl plank flooring throughout, fresh paint, updated light fixtures, and solid surface countertops in both the kitchen and primary bath. The hall bath features a new vanity, while the kitchen is equipped with a brand-new range. The hot water heater is approximately two years old, providing added peace of mind. Storage is plentiful with a coat closet, linen closet, and attic with pull-down stairs. Located in the highly desirable Ocean Pines community, residents enjoy an exceptional lifestyle with amenities that include golf, marinas, parks, swimming pools, pickleball and tennis courts, a yacht club, beach club, farmers market, and miles of scenic walking trails—all just minutes from the beaches, boardwalk, dining, and entertainment of Ocean City.

10 Stonemeadow Ct, Ocean Pines

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

$445,000
2 Beds 2 Baths
Wake up to breathtaking ocean views and experience the best of coastal living at Atlantis 2003! This stunning top-floor oceanfront condo offers the perfect combination of location, comfort, and resort-style amenities in one of Ocean City’s most desirable buildings. Located on the 20th floor of the Atlantis, this spacious 2-bedroom, 2-bath retreat showcases panoramic views of the Atlantic Ocean from nearly every angle. The open-concept layout creates a bright and airy feel, with the ocean serving as the perfect backdrop for everyday living. Enjoy your morning coffee while watching the sunrise from the private oceanfront balcony, relax after a day in the sun, and take in the beauty of Ocean City from your own private escape. The beautifully updated interior features a coastal-inspired design with a comfortable living area, sliding glass doors that open to the balcony, and a modern kitchen complete with granite countertops and stainless steel appliances. The spacious primary suite offers incredible ocean views, while the second bedroom provides additional space for family and guests. Both bathrooms have been thoughtfully renovated with stylish tiled showers, creating the perfect place to refresh after a day at the beach. Beyond the condo itself, Atlantis offers an unmatched oceanfront lifestyle with a seasonal outdoor pool and three elevators. Located just seconds from the sand, restaurants, shopping, and Ocean City’s favorite attractions, you can enjoy everything the area has to offer while leaving the car behind. Whether you’re looking for a vacation retreat, an investment opportunity, or your own piece of Ocean City paradise, Atlantis 2003 delivers the views, amenities, and coastal lifestyle you’ve been searching for.

10300 Coastal Hwy Unit #2003, Ocean City

Listing courtesy of Keller Williams Realty Delmarva. Contact: 4105246400

$450,000
2 Beds 2 Baths
Completely renovated from top to bottom, every detail has been updated with quality finishes and stylish furnishings. From the moment you walk in, you'll feel like you're in your own private coastal retreat. Best of all, the home is being sold fully furnished, making it truly move-in ready. Enjoy your morning coffee on the private balcony, then spend your afternoons relaxing at the community's huge pool and sundeck. Inside, the open dining area offers beautiful bay views and breathtaking sunsets. The unit also features a stacked washer and dryer, making everyday living effortless. Additional highlights include two assigned covered parking spaces, a rare find in Ocean City, and unbeatable access to Coastal Highway. Located directly at a traffic light and just five blocks from Route 90, getting on and off the island is quick and convenient. Unlike many Ocean City condos, this unit has never been a rental. It has been lovingly used by the owners for family weekends a few times each summer, so it has been exceptionally well maintained and remains in outstanding condition. And here's the feature buyers will love the most: NO SPECIAL ASSESSMENT! That's right—this beautiful condo is assessment-free, giving you added peace of mind and value. Whether you're looking for a vacation getaway, a second home, or a year-round residence, this exceptional property checks every box. Don't miss your chance to own one of Midtown Ocean City's finest turnkey condos!

5500 Coastal Hwy Unit #C32903, Ocean City

Listing courtesy of RE/MAX Advantage Realty. Contact:

$1,849,000
4 Beds 4 Baths
Simply Sensational! Sunrise views over Town Creek set the tone for this beautifully designed four-bedroom waterfront home, where contemporary architecture meets the warmth of a waterfront cottage. The main living areas include a formal living room and dining room, each with a fireplace, a bright eat-in kitchen and an inviting family room, where walls of windows frame the water views and fill the home with natural light. Two first-floor bedrooms offer the convenience of main-level living. Upstairs, two ensuite bedrooms open to the second-floor sun deck, including a spacious primary suite with floor-to-ceiling windows overlooking Town Creek.An expansive waterside patio and pool create the perfect setting for relaxing and entertaining. The separate one-bedroom guest house/pool house and detached workshop provide additional space for family, guests, hobbies or a home office. The private pier, complete with a boat lift and floating dock for kayaks and paddleboards, provides easy access to the Tred Avon River and the Chesapeake Bay. Located in the historic waterfront village of Oxford, this exceptional home captures the beauty, charm and relaxed waterfront lifestyle that define Maryland's Eastern Shore. The property is offered with its furniture allowing for an effortless transition.

106 E Division St, Oxford

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$550,000
4 Beds 3 Baths
Showings Begin Friday 7/24 ** Absolute Perfect Entertaining Spot in Marina Village ** Large 4 Bedroom End-Of-Group Townhome with Water Views from Numerous Rooms ** Largest Townhome Lot in the Community with a Southern Exposure & Yard Space on All Sides ** Main Level Primary Suite ** Two-Story Ceilings ** One-Car Attached Garage ** New Roof ** Multiple Outdoor Spaces to Enjoy Including Two Top Level Balconies / Main Level Deck & Screened Porch PLUS Huge Level Side & Back Yards ** All Furniture is Top Notch & Very Gently Used - Only One Owner & Never Been Rented ** Enjoy Walkability Proximity to Both Pines Point Marina & Ocean Pines Yacht Club ** Home is in Excellent Condition & Is One of the Largest in Community ** A++

1014 Baybreeze Ln, Ocean Pines

Listing courtesy of RE/MAX Advantage Realty. Contact:

$499,900
3 Beds 3 Baths
Located in the highly desirable Teal Bay neighborhood, this charming 3-bedroom, 3-bath home has been meticulously loved and maintained. The flexible floor plan features primary suites on both the first and second floors, along with an updated kitchen and bathrooms, a screened in porch, garage, private backyard, and encapsulated crawlspaces. Enjoy a peaceful view of the St. Martin River from the sunroom without the added cost and upkeep that comes with waterfront living. Natural light floods the home, creating a bright and welcoming atmosphere while the spacious upstairs primary suite features two walk-in closets and a private second-floor balcony. Find your serenity in this prime coastal location, just minutes from the beach with all the exceptional amenities Ocean Pines has to offer!

180 Teal Cir, Ocean Pines

Listing courtesy of Coldwell Banker Realty. Contact: 4438562211

$739,900
3 Beds 3 Baths
Rich solid bamboo flooring flows throughout the main living areas, while replacement windows maximize the breathtaking Bay views. The remodeled gourmet kitchen features quartz countertops, stainless steel appliances, and opens to a full-width waterfront deck—perfect for morning coffee, outdoor dining, or simply watching the boats pass by. The spacious family room also opens onto a private waterfront deck, creating seamless indoor and outdoor living. Upstairs, the primary suite becomes your personal waterfront retreat with its own private deck overlooking the Chesapeake Bay, beautifully updated bath, and the convenience of a dedicated washer and dryer. Two additional bedrooms enjoy water views as well, allowing family and guests to wake up to the beauty of the Bay every day. The walk-out lower level offers even more flexibility with a second washer and dryer, access to a stamped concrete waterfront patio, and a covered sitting area just steps from the shoreline—an ideal place to unwind after a day on the water. Residents enjoy exclusive access to a private community pier complete with a boat lift and fishing opportunities. Every Independence Day, neighbors gather to watch the spectacular fireworks display reflected across the Chesapeake Bay, creating a tradition you'll look forward to year after year. Located less than an hour from Washington, D.C., this home offers an exceptional primary residence, weekend escape, or second home without the hassle of Bay Bridge traffic. Enjoy the charm of Chesapeake Beach with its waterfront boardwalk, community beach, farmers markets, local breweries, boutique shopping, restaurants, outdoor concerts, marinas, and year-round events—all just minutes from your door. If you've been searching for true Chesapeake Bay waterfront living with modern updates, unforgettable views, and an unbeatable coastal lifestyle, this is the one.

8337 Bay Crest Ct, Chesapeake Beach

Listing courtesy of RE/MAX United Real Estate. Contact:

$399,000
2 Beds 2 Baths
Waterfront with assigned pier on Thompson Creek – Rare End-Unit Townhome Fantastic opportunity to own an end-unit waterfront townhome with direct views of Thompson Creek, complete with an assigned pier featuring power and water. Inside, gleaming hardwood floors flow through the kitchen and living room. The main level offers a convenient bedroom, while upstairs you'll find a huge loft-style primary suite complete with a spacious primary bathroom featuring an oversized walk-in shower and an equally impressive walk-in closet. A versatile bonus room offers flexibility as a 3rd bedroom or home office. The kitchen offers ample counter space and storage alongside a large dining area, perfect for entertaining. Step outside to a spacious deck to soak in the water views, plus a second private balcony off the primary bedroom. With western exposure, enjoy breathtaking sunsets over the creek every evening. The HOA maintains the pier as well as all exterior upkeep of the home, including the roof and siding, offering true low-maintenance waterfront living. Ideally located on Kent Island, just a half mile to Route 50 and minutes to two shopping centers featuring Food Lion, Target, and a variety of restaurants. Incredible value at $399,000 for waterfront living with a private pier. Furnishings are available for purchase separately, excluding personal items.

101 Marion Quimby Dr, Stevensville

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767

$718,000
2 Beds 2 Baths
Welcome to Unit 503 where resort-style living meets beachfront luxury in Ocean City, MD. This dreamy two-bedroom condo with a den and two bathrooms is perfect for those seeking a blend of vacation life, comfort and convenience. The entire open-concept living area is drenched in natural light, showcasing elegant wood-like flooring and a charming den providing versatile space for work or relaxation. The recently updated kitchen is a chef's delight featuring beautiful granite countertops, stainless steel appliances and an oversized breakfast bar, perfect for casual dining while enjoying panoramic ocean views. The spacious dining area comfortably accommodates family gatherings or an impromptu evening with friends. Step into the inviting family room outfitted with mirror-paneled walls that reflect the beach's beauty. Slide open the floor-to-ceiling glass doors leading to an expansive balcony. This outdoor oasis is ideal for morning coffee, sunset cocktails or simply soaking in the refreshing ocean breeze. Retreat to the oversized primary bedroom complete with picturesque views and direct access to the peaceful balcony. The ensuite bathroom features a glass shower/tub combination and a modern granite vanity. The generously sized second bedroom offers lovely western views of the Assawoman Bay and has plenty of closet space. The in-unit washer/dryer is tucked away in a hallway nook across from the linen closet and full-sized guest bathroom. Beyond your private sanctuary, the Plaza boasts exceptional indoor and outdoor amenities. Adjacent to the lobby you will find a large, heated, indoor space with a pool, hot tub, plunge pool and sauna. The outdoor lap pool and gated baby pool open up to an expansive sunbathing deck and several picnic areas. Enjoy delightful dining experiences at the Jolly Jelly Fish Restaurant and Bar, complete with live music, drink specials, the opportunity to make new friends and meet your new neighbors. Conveniently located off 98th Street and Coastal Highway, you'll have easy access to a variety of restaurants, shops and grocery stores insuring that everything you need is just footsteps away. A coveted, assigned parking space is located in the covered garage just outside the back lobby doors. Sandy beach toys, umbrellas and other beach equipment can be stored in the numbered storage locker which is also located in the garage.  This condo offers a unique opportunity to embrace the beach lifestyle you've always dreamed of. Don't wait, schedule your showing today!

9800 Coastal Hwy Unit #503, Ocean City

Listing courtesy of Century 21 Redwood Realty. Contact:

$1,099,900
5 Beds 2 Baths
A truly one-of-a-kind waterfront estate offering 82+ acres across three parcels in historic Crisfield, Maryland. Known as the legendary "Home of the Terrapin King," this extraordinary property seamlessly blends Chesapeake Bay history with breathtaking waterfront living. Learn more about the property's fascinating story at www.TerrapinKing.org. Built in 1925, this beautifully updated residence offers approximately 2,921 square feet of living space with 5 bedrooms and 2 full bathrooms. Surrounded by water on three sides, nearly every room showcases spectacular panoramic views of the Chesapeake Bay, tidal marshes, and unforgettable sunsets. Extensive recent improvements make this historic home move-in ready while preserving its timeless coastal character. Updates include new luxury vinyl plank flooring throughout, updated lighting, new plumbing, a new water treatment system, new sump pumps and drainage systems with backflow valve preventers, and most mini-split HVAC units replaced within the past few months. The home is being offered fully furnished, making it ideal as a primary residence, vacation home, or turnkey investment property. The spacious primary suite features a pellet stove, double closets, and sweeping waterfront views. One of the home's most iconic spaces, the Captain's Room, features expansive bay windows that create the feeling of standing at the helm of a ship overlooking the Chesapeake. Two screened porches and a second-story balcony provide multiple spaces to relax and enjoy the peaceful waterfront setting. The estate encompasses over 82 acres, including approximately 20 acres of upland, with the balance consisting of pristine waterfront, marshlands, and natural habitat. Private trails offer opportunities for hiking, wildlife observation, hunting, and exploring, while the property's private beach and dock provide direct access to boating, fishing, kayaking, and all that the Chesapeake Bay has to offer. Additional exterior improvements include the removal of all former beach pilings, installation of additional riprap for shoreline stabilization, and backfilling of the yard, further enhancing the property's usability and protecting the shoreline. Beyond its exceptional waterfront lifestyle, this property presents exciting future possibilities. The seller has obtained a conceptual site plan prepared by GMB of Salisbury outlining the potential placement of approximately 3–4 tiny homes within portions of the upland acreage. Buyers should review the listing documents for the proposed layout. Any future development remains subject to all required governmental approvals, permitting, environmental review, and applicable regulations. One of the property's most valuable features is its existing connection to city sewer, an uncommon and highly desirable amenity for a waterfront estate of this size that can significantly reduce future infrastructure costs. Steeped in history as the former headquarters of Albert Tallmadge LaVallette Jr.'s renowned terrapin enterprise, this remarkable estate has become one of Maryland's most recognizable waterfront landmarks. The property currently operates as a successful short-term rental, and the seller reports annual gross short-term rental income approaching $100,000, offering exceptional income potential while serving as a truly unforgettable waterfront retreat. Whether you're searching for a private estate, an income-producing investment, a family compound, or a once-in-a-lifetime Chesapeake Bay property, 1 Lavallette Road delivers unmatched history, privacy, recreation, development potential, and panoramic waterfront beauty. Fireplaces convey As-Is. Total acreage is approximately 82+ acres, including approximately 20 acres of upland. Furnishings included with acceptable terms.

1 Lavallette, Crisfield

Listing courtesy of Worthington Realty Group, LLC. Contact: 8558494663

$1,150,000
3 Beds 3 Baths
Set above the South River on 1.28 acres, 2758 Bon Haven Lane offers the feeling of a private waterfront retreat without sacrificing everyday convenience. Mature trees and over 100 feet of shoreline frame water views and offer the property a wonderfully serene quality. The private pier has approximately five feet of mean low water, two lifts (jet ski and 10,000 lbs), and immediate access to the South River creates an ideal launching point for days on the Chesapeake Bay. The home unfolds across three thoughtfully arranged levels. The main level welcomes you through a central foyer, with a comfortable bedroom set privately to one side. The principal gathering spaces include a generous dining area that flows naturally into the spacious kitchen. The kitchen island offers ample room for everyday dining and the open concept space creates an inviting setting for hosting. Direct access to the attached two-car garage adds convenience. Upstairs, the primary bedroom enjoys generous proportions, a walk-in closet, and a wood-burning fireplace. The ensuite bathroom has a dual sink vanity and a large window for natural light. The second bedroom on this floor, with hardwood floors, is spacious and bright and has a hall bathroom just outside the room. Both bedrooms overlook and have open onto the home’s standout screened porch, a nearly full-width outdoor room with a vaulted wood ceiling and elevated, treehouse-like perspective over the landscape. It makes a wonderful sleeping porch on cooler evenings. The finished walk-out lower level offers a large family room anchored by a second wood-burning fireplace, along with a separate laundry room, half bath, and storage. From here, sliding doors open to a brick, covered patio and an expansive waterside deck, creating an effortless progression from indoor living to outdoor entertaining and the path to the pier. In addition to your private waterfront, the community amenities create opportunities to gather: a sandy beach, picnic areas, boat ramp, community pier and slips. Despite its tremendously private setting, the location is notably convenient. Downtown Annapolis is an easy drive, while nearby Routes 50 and 97 provide straightforward access to Baltimore and Washington, D.C.

2758 Bon Haven Ln, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$469,900
2 Beds 2 Baths
Wake up every day to panoramic views of the Chesapeake Bay and live the vacation lifestyle you’ve always imagined, surrounded by Osprey, sailboats, and endless waterfront activity. Inside, the light-filled floor plan features beautiful hardwood floors throughout the living room, a well-appointed kitchen with breakfast bar, maple cabinetry, and stainless steel appliances, plus a spacious balcony overlooking the Bay accessible from both the living room and the owner’s suite. The owner’s suite offers a walk-in closet and an updated bathroom with an upgraded double-sink vanity, soaking tub, and separate shower, creating the perfect blend of comfort, convenience, and coastal living. Horizon on the Bay enhances this lifestyle with resort-style amenities including a fitness center, rooftop pool with lounge area, library, picnic area with grills and a firepit, secure fenced parking with private spaces, a package delivery room, and a private pier with fishing access and a cleaning station. Residents enjoy a vibrant community with happy hours, potluck dinners, art shows, talent fundraisers, and more. This unit provides easy access to the lobby and rooftop pool, and is super conveient to Annapolis, Solomon's, Washington, D.C., and only a few blocks from downtown North Beach’s boardwalk, farmers market, concerts, and restaurants.

8501 Bayside Rd Unit #606, Chesapeake Beach

Listing courtesy of RE/MAX United Real Estate. Contact:

$309,900
2 Beds 2 Baths
Professional pictures coming August 5th after tenant has completely moved out. Nestled in the serene community of Caine Woods, this exquisite 2-bedroom, 2-bathroom unit at Sea Pine Villas offers a coastal lifestyle that seamlessly blends comfort and elegance. With a thoughtful renovation completed in 2024, this residence is a true gem, showcasing high-end finishes and modern conveniences. Step inside to discover an inviting open floor plan that effortlessly connects the living, dining, and kitchen areas. The spacious family room featuring new laminate flooring and ceiling fans, creates a warm atmosphere perfect for relaxation or entertaining. The gourmet kitchen is a dream, featuring new stainless steel appliances, including a self-cleaning oven, built-in microwave, and dishwasher, all complemented by a stylish pantry for added convenience. Just off the kitchen is a brand new stack washer and dryer for your convenience. Retreat to the primary suite, where tranquility reigns. The luxurious primary bath boasts a soaking tub, walk-in shower, and elegant fixtures, providing a spa-like experience right at home. The second bedroom is equally inviting, with ample space and natural light, making it perfect for guests or a home office. The outdoor features of this property are equally impressive. Enjoy the community's beautifully maintained grounds, complete with a fenced, in-ground pool that invites you to unwind on warm days. The unit itself offers a private deck and patio, ideal for morning coffee or evening gatherings, all while surrounded by lush landscaping and the soothing sounds of nature, as the property backs to trees. Additional highlights include all new windows, sliders, door and storm door. In addition there is a new hotwater heater and the crawlspace has been recently encapsulated. There is ample parking with two unassigned spaces in a lighted, paved lot, and a comprehensive association that covers common area maintenance, lawn care, and more, ensuring a low-maintenance lifestyle. Located in a bayside community, this residence is just a short distance from local amenities and a bus stop, making it easy to explore the vibrant surroundings. The architectural style reflects a coastal charm, with a combination of stucco and vinyl siding that enhances its curb appeal. This property is not just a home; it's a lifestyle choice that offers the perfect blend of luxury, comfort, and convenience. The private outdoor pool makes for a nice retreat after a day at the beach. Experience the best of coastal living in this exceptional Sea Pine Villas unit, where every detail has been meticulously crafted for your enjoyment. The courtyard is also great for your furry friends to relax and enjoy the outdoors.

404 141st Unit #6, Ocean City

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

$989,800
5 Beds 4 Baths
Coastal luxury living by Laine Street Homes, this exceptional waterfront home offers over 3,000 square feet on 3 levels with 5 bedrooms, 3.5 bathrooms, and stunning water views. Perfectly positioned and thoughtfully designed to capture beautiful sunrises over the water, the home is filled with natural light and showcases panoramic water views from the main living areas and the luxurious primary suite. Designed for both luxury living and entertaining, the open floor plan features 7-inch wide plank flooring, a gas fireplace, entry-level guest suite, and high-end finishes throughout. The gourmet kitchen is the heart of the home, complete with shaker-style cabinetry, quartz countertops, an oversized island, premium ZLINE stainless steel appliances, upgraded custom lighting, and expansive water views. Upstairs, the spacious primary suite offers a peaceful waterfront retreat with a spa-inspired bath featuring a 6-foot tiled walk-in shower with dual shower heads, a built-in bench, double vanities, and generous closet space. Bedroom-level laundry and beautifully finished bathrooms with tile flooring add everyday convenience. Outdoor living is just as impressive, with an expansive rear deck and covered patio overlooking the creek—perfect for enjoying sunrises over the water or relaxing while watching local wildlife. Adding to the sense of privacy, approximately 181 acres of rural land zoned "Countryside District" stretch across the shoreline on the opposite side, preserving the natural views with protected land. For those who enjoy life on the water, this location is hard to beat. Launch a kayak, paddleboard, or small boat from your backyard and reach the Chester River in approximately one mile, with the Chesapeake Bay just 5 to 6 water miles beyond. Enjoy quick access to bay boating while returning home to the calm waters, privacy, and natural beauty of a protected creek. Combining quality craftsmanship, upscale finishes, and an exceptional waterfront setting, this newly completed home offers a rare opportunity to enjoy the best of Maryland's Eastern Shore lifestyle!

203 Riverside Dr, Chester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 3019459010

$875,000
3 Beds 2 Baths
Luxury Bayfront Living with Spectacular Sunset Views Experience coastal living at its finest in this beautifully updated 3-bedroom, 2-bath bayfront residence offering 1,735 square feet in an exclusive 12-unit boutique building in the heart of Midtown Ocean City. Perfectly positioned with southern exposure, this exceptional home offers breathtaking panoramic views of the bay and protected wetlands. This meticulously maintained residence has been extensively updated with fresh paint throughout, upgraded recessed lighting in every room, new ceiling fans, all new electrical outlets and switches, new gas fireplace logs, Levolor® motorized shades, and heated distressed wide-plank tile flooring with 11 individually controlled heating zones. The Levolor® motorized shades feature room-darkening blinds in the primary suite and light-filtering blinds in the living room, while the gas fireplace creates the perfect place to relax on cooler evenings. The spacious kitchen is designed for entertaining and offers an abundance of cabinetry, quartz countertops, a coastal blue tile backsplash, stainless steel appliances, and a wine refrigerator a rare find for a beach home. The primary suite features a custom Elfa® Closet System by The Container Store and a stunning en-suite bath with upgraded fixtures and a spacious walk-in shower. A second Elfa® Closet System adds exceptional organization to one of the additional bedrooms. The second bathroom has also been beautifully updated with a spacious walk-in shower and seamless glass doors. The spacious laundry room has also been recently enhanced with the addition of a utility sink and custom cabinetry, providing exceptional storage and functionality. Step onto the expansive waterfront deck and enjoy spectacular sunsets, outdoor dining, or simply relax while overlooking the bay and protected wetlands. Amenities include a south-facing outdoor pool, barbecue area, covered parking, ground-level storage, secure lobby with elevator, and a kayak/paddleboard launch and storage area. Located in a well-maintained boutique building, this home offers a peaceful waterfront lifestyle just moments from Ocean City’s beaches, dining, shopping, and entertainment. Don’t wait on this one! Opportunities like this are rare. Schedule your private showing today and experience the very best of bayfront living in Ocean City!

124 75th St Unit #402, Ocean City

Listing courtesy of Sheppard Realty Inc. Contact: (410) 723-7070

$799,900
3 Beds 4 Baths
Experience the beauty of waterfront living without the waterfront expense at 233 Circle Road! Built in 2003 and lovingly maintained by the original owners, the home is thoughtfully designed to showcase the water views. Surrounded by water and overlooking one of the widest stretches of the Magothy River, this remarkable 3-bedroom, 3.5-bath home offers breathtaking panoramic views and a true water-oriented lifestyle. Please note that the property is not waterfront and conveys no private riparian rights; however, the community beach and water access are conveniently located directly across the street. The community boat ramp is located nearby off Long Point Road on Cornfield Creek. The elevated main level welcomes you into a space designed to showcase breathtaking views of the Magothy River. A covered porch connects to the wraparound deck, allowing you to walk around the home, enjoy multiple outdoor living areas and take in views of the entire property. Hardwood floors flow throughout the main level, connecting the spacious living room, family room, dining area and kitchen. Two sliding glass doors lead directly to the deck and fill the space with natural light and water views. The kitchen features butcher-block countertops, stainless steel appliances, a farmhouse sink and pantry, along with peaceful views of the pool and the wooded creek that curves around the back of the property. A conveniently located half bath completes this level. Upstairs, the primary suite is an owner’s oasis featuring panoramic river views, two closets, including a walk-in. An ensuite bath with a soaking tub, separate shower and double vanity. Two additional bedrooms share a convenient Jack-and-Jill bath, and the upper-level laundry room makes everyday living easier. You can enter the home on the ground level as well through the side garage door. The garage features a durable epoxy floor and oversized sliding doors that open directly to the outdoor in-ground pool, seamlessly expanding the entertaining space and supporting the home’s relaxed, water-oriented lifestyle. This level features a spacious family room, full bath and versatile bonus room with access to its own private patio, creating an ideal retreat for overnight guests, a home office or additional living space. Nestled in a quiet, tucked-away setting within the Long Point community, this .40-acre property offers added privacy, no through traffic, breathtaking water views, and an abundance of natural beauty—all within the sought-after Chesapeake School District. Community amenities include community beaches, a community hall and a community boat ramp that launches into Cornfield Creek. The voluntary HOA is $65/year , with an additional annual fee of $75 for boat-ramp privileges. Don’t miss this rare opportunity to enjoy spectacular Magothy River views, community water access, an in-ground pool and your own private piece of paradise!

233 Circle Rd, Pasadena

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (410) 544-4000