Worcester Homes with Pool

Worcester Homes with Pool

Welcome to Worcester County, Maryland – a hidden gem on the Eastern Shore that beautifully combines the charm of small-town living with the allure of coastal recreation. Nestled between the Atlantic Ocean and the serene waters of the Chesapeake Bay, this vibrant county is renowned for its stunning natural landscapes, rich history, and welcoming communities. With picturesque beaches, lush parks, and a myriad of outdoor activities, Worcester County is a haven for nature lovers and adventure seekers alike.

For those seeking a home that embodies relaxation and leisure, our selection of properties with pools is sure to captivate you. Imagine stepping out of your beautifully designed home and into your own private oasis. Whether you’re hosting summer barbecues, enjoying a tranquil evening swim, or simply soaking up the sun with a good book, a home with a pool in Worcester County offers the perfect backdrop for your ideal lifestyle.

Worcester County is also home to charming towns like Ocean City, where you can enjoy vibrant boardwalks, fine dining, and entertainment options. The county boasts excellent schools, ample shopping, and a strong sense of community, making it an ideal place for families and retirees alike.

With a diverse range of homes available, from quaint cottages to luxurious waterfront estates, you’re sure to find the perfect residence that matches your vision of home. Let Worcester County be the backdrop for your next chapter, where every day feels like a vacation, and your poolside dreams become a reality. Explore our listings today and dive into the serene lifestyle that awaits you!

Newest Worcester Homes with Pool

3 Beds ⋅ 3 Baths

Discover the perfect blend of luxury, comfort, and convenience in this pristine three-bedroom, three-bath condominium with over 1,600 Sq Ft. in the highly desirable Coral Seas building in midtown Ocean City. Original hand-painted art murals adorn the walls to elevate your living experience and enjoyment. Rarely does an opportunity arise to own a spacious residence offering three generously sized bedrooms, each paired with its own convenient bathroom. The Primary bedroom enjoys private access to the large balcony. This residence has it all making it ideal for full-time residence, a luxurious vacation retreat, or an exceptional investment property. Designed for effortless coastal living, the expansive open floor plan features a large living room with a cozy fireplace, that flows seamlessly into the dining area and well-appointed kitchen, creating the perfect space for entertaining loved ones and friends. Step outside onto the oversized private balcony and unwind while enjoying limited views of the beautiful bay and refreshing coastal breezes. Additional highlights include a dedicated laundry room, tasteful finishes throughout, and meticulous care that makes this home truly move-in ready. Located in the heart of midtown Ocean City, Coral Seas places you just moments from the beach, the bay, outstanding restaurants, shopping, entertainment, and everything the resort lifestyle has to offer. Residents also enjoy access to an on-site outdoor pool, adding even more appeal to this exceptional coastal property. Whether you’re searching for your dream beach home, a spacious year-round residence, or a strong investment opportunity, this rare offering checks every box.

7601 Coastal Hwy Unit #201, Ocean City

Listing courtesy of Coldwell Banker Realty. Contact: 4438562211

2 Beds ⋅ 2 Baths

Welcome home to this lovingly cared-for, one-owner home, designed by an interior decorator. This retreat nestled among the towering trees in the desirable North Gate of Ocean Pines one of the safest places to live in Maryland and just minutes from the beautiful beaches, dining, and entertainment of Ocean City, Maryland, Assateague and Rehoboth beaches. Medical facilities, schools, yacht club, and golf course nearby. Situated on a serene, private lot backs to Briarcrest Park, this charming 2-bedroom, 2-bath home also features a spacious loft that can easily be converted into a third bedroom, home office, or flex space to suit your needs. Filled with warmth and character, the great room showcases soaring cathedral ceilings accented by stunning exposed wood beams, unique moon-shaped architectural openings, and a cozy wood-burning stove that creates the perfect gathering place. The wood stove provides ambiance and warmth on cold winter nights as well as peace of mind with possible energy loss! Laminate hardwood flooring flows throughout the main living areas, while the tiled kitchen is equipped with a stainless-steel refrigerator and offers both functionality and style. The first-floor bedroom features sliding glass doors leading to a vinyl-tech enclosed screened porch, providing a peaceful spot to relax and enjoy the surrounding nature. Double sliders from the great room open to an expansive wraparound deck, seamlessly blending indoor and outdoor living and offering the perfect setting for entertaining or simply enjoying the tranquil wooded backdrop. Outside, you'll find an outdoor shower, storage shed, and convenient U-shaped driveway. Major updates include a roof and HVAC system that are approximately five old. Home is complete with pull down attic stairs and encapsulated crawl space. This wooded retreat can be yours now to enjoy year-round. Call for your private showing!

6 Briarcrest Dr, Ocean Pines

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

2 Beds ⋅ 2 Baths

Spacious 2-bedroom, 2-bath direct oceanfront condominium offering breathtaking panoramic views of the Atlantic Ocean. The open floor plan is designed to maximize natural light and showcases spectacular ocean views from nearly every room, with seamless access to your private oceanfront balcony. Beautifully renovated, the kitchen features coastal white cabinetry, tile backsplash, granite countertops, and stainless-steel appliances. The oceanfront primary suite features a large picture window and sliding glass doors leading to your private balcony - the perfect spot to enjoy your morning coffee while watching the sunrise over the ocean. The bayside guest bedroom provides comfort and privacy for family and guests. Ideally positioned on the 2nd floor and open to the bayside to capture refreshing coastal breezes, abundant sunshine, and endless ocean views, this exceptional residence is located in The Plaza at 98th Street, one of Ocean City's premier oceanfront communities. Resort-style amenities include a half-acre oceanfront sun deck, Heated Outdoor Pool, Kiddie pool, Tiki Bar/Grill, Year-round Indoor Pool, 5-star restaurant, Hot Tub, saunas, 24/7 Security, Private Beach storage, and 2 parking spaces (one covered). The Plaza is professionally managed with extensive building improvements already completed and No New Assessments. Don't miss this outstanding opportunity to own your piece of the beach!

9800 Coastal Hwy Unit #210, Ocean City

Listing courtesy of Mary McCracken Realty, Inc. Contact: 4107231895

2 Beds ⋅ 2 Baths

Discover the best of beach living in this 2-bedroom, 2-bath ocean block condo in Ocean City, Maryland, offering beautiful bay views and just steps to the beach. This well-maintained condo features an updated kitchen, spacious living areas, and a comfortable floor plan designed for relaxing and entertaining. Enjoy the convenience of an elevator, community pool, and covered parking, making every visit easy and enjoyable. Whether you’re searching for a vacation home, a full-time residence, or an investment property, this condo is an outstanding opportunity with its proven rental history and sought-after location. Spend your days on the beach and your evenings taking in stunning bay sunsets, all while being close to Ocean City’s restaurants, shopping, dining, entertainment, and all the attractions the area has to offer. Whether you’re looking to create lasting family memories or generate rental income, this property offers the perfect blend of lifestyle and value. Don’t miss your chance to own your own piece of Ocean City in a prime ocean block location with the bonus of beautiful bay views. This is beach living at its best!

7604 Coastal Hwy Unit #2C, Ocean City

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

5 Beds ⋅ 2 Baths

Waterfront investment opportunity in Ocean Pines! 2 Windjammer Rd represents an incredible chance to buy into a premier coastal location at a low waterfront price point and build instant equity through your own improvements. Please note: This is an trustee sale. The property is being sold strictly AS-IS and is priced accordingly. Bring your vision and tools to this classic handyman special! The spacious main house features 2,258 square feet of potential, boasting a side porch with vinyl tech windows, and a rear deck perfect for entertaining. The unique layout offers incredible versatility with an open floor plan for the living/dining/kitchen areas. There are a total of 5 bedrooms and 2 full baths in the main house- 2 beds and 1 bath on entry level, 3 beds and 1 bath on upper level. The second-floor balcony provides private access (with additional steps from the ground level) to a separate room over the garage. This bonus area includes finished, climate-controlled guest quarters (approx 600 sq feet) complete with its own full bathroom, kitchenette, and stairs to loft area. The over-sized 2 car garage is attached to the main home by a deck/breezeway and offers space for covered parking plus workshop area and additional storage. Boaters and water lovers take note: the true highlight of this property is its prime waterfront location. Enjoy your own private dock with direct access out of the canal and into Assawoman Bay. There is a long list of amenities in Ocean Pines, including: championship golf course, five swimming pools (including an indoor pool and the oceanfront Beach Club in Ocean City), two marinas, racquet sports, a yacht club, and multiple parks and trails. Positioned in an ideal coastal hub, you are just a short drive from the historic charm of downtown Berlin, the legendary beaches and boardwalk of Ocean City, MD, and the pristine, natural beauty of Assateague National and State Beaches. Don't miss this rare waterfront flip, rental asset, or dream coastal project!

2 Windjammer Rd, Ocean Pines

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

1 Beds ⋅ 1 Baths

Your Ocean City getaway is ready! This fully furnished first floor condo offers easy one level living just three blocks from the beach and boardwalk. The spacious layout provides plenty of room to cook, dine, relax, and entertain after a day in the sun. The bedroom features two queen beds, and the living room includes a sleeper sofa, giving you flexible sleeping space for family, friends, or vacation guests. The location is hard to beat. The new 4th Street Park is only half a block away and offers basketball, tennis, pickleball, a skate park, and a playground. For days when you want a break from the sand, the community pool is conveniently located right across the street. The bay is also just three houses away, making evening sunset walks an easy part of the Ocean City lifestyle. Parking options include on-site parking, street parking, and an additional lot across the street. Whether you are searching for a personal beach retreat, a vacation rental, or a property that can do both, this condo checks the boxes. It generated more than $27,000 in rental income last year and is being sold fully furnished, making it easy to start enjoying or renting right away.

409 Saint Louis Ave Unit #48, Ocean City

Listing courtesy of Keller Williams Realty Delmarva. Contact: 4105246400

2 Beds ⋅ 2 Baths

Nicely updated direct oceanfront condo in the ever-popular Sandpiper Dunes building. This condo offers two bedrooms, two full-bathrooms, an open living area and prime views of the beach and ocean from its optimal third floor location. The living area features a comfortably furnished living room, dining area, fully-equipped kitchen with a convenient breakfast-counter and a utility/storage room. There is a good-sized, private balcony with storm-shutters located off of the living area and master bedroom. This is a great place to relax, unwind and enjoy the beautiful views after a long day on the beach. The oceanfront master bedroom features a large picture window that maximizes the views, an updated ensuite full-bathroom and balcony access. The guest bedroom is generously sized, offering a variety of configuration options. The second full-bathroom is centrally located and easily accessible from throughout the condo. Condo improvements include vinyl plank flooring in the living area and bedrooms, tile flooring in the kitchen and bathrooms, updated windows and doors, updated kitchen, new full-size washer and dryer, updated bathrooms and some new furniture pieces. Building amenities include assigned parking for two vehicles, an outdoor pool, multiple elevators and direct beach access. Good restaurants, shopping, amusements, water-sports, nightlife and more are all within walking distance. The property conveys fully-furnished and equipped for turn-key enjoyment. This is a great oceanfront condo in one of Ocean City’s best managed buildings. Schedule your private showing today.

5801 Atlantic Ave Unit #305, Ocean City

Listing courtesy of Coastal Life Realty Group LLC. Contact: (443) 235-8382

4 Beds ⋅ 6 Baths

Experience the best of coastal living in this exceptional four-story luxury townhome, perfectly positioned in an upscale community just two blocks from the beach in North Ocean City. With an established and proven rental history, this beautifully appointed property presents an outstanding opportunity as both an investment and a personal beach retreat. Offering thoughtfully designed living space, the home features three spacious bedrooms, three full baths, two half baths, and a fourth floor loft area. High end finishes, modern coastal style, and expansive living areas create an inviting atmosphere ideal for entertaining or relaxing after a day by the ocean. This home is sold fully furnished and ready for your enjoyment. The entry level welcomes you with a private two car garage, while the first living level offers a comfortable family room with a queen sleeper sofa, large Smart TV, and convenient half bath, creating the perfect space for guests or additional gathering space. The main living level is the heart of the home, showcasing an open concept design filled with natural light. The gourmet kitchen is equipped with premium finishes, abundant cabinetry, bar seating, and flows seamlessly into the dining area and spacious living room, where comfortable seating and a large Smart TV provide an ideal setting for everyday living or entertaining. Private balconies extend the living space outdoors, allowing you to enjoy the refreshing coastal breeze. The upper levels are dedicated to comfortable bedroom suites, including two generously sized bedrooms with beautifully appointed en suite baths and a luxurious top floor primary retreat featuring its own private bath. A versatile loft provides additional living space perfect for a media room, game room, or guest lounge, while a conveniently located laundry room adds everyday practicality. Residents of Lighthouse Bay enjoy exclusive master-planned amenities, including a resort-style swimming pool, picnic area, and BBQ area, perfect for outdoor gatherings. Ideally located on 143rd Street, this home places you within walking distance of the beach, restaurants, shopping, and entertainment. Fenwick Island is less than a mile away, while miniature golf, go karts, waterfront dining, and countless coastal attractions are just minutes from your door. Whether you're seeking a luxury vacation home, a year round coastal residence, or a turnkey investment property with excellent rental potential, this exceptional townhome offers the perfect combination of location, style, and lifestyle in one of North Ocean City's most desirable beach communities. Don’t miss out on this rare opportunity!

14303 Coastal Hwy Unit #14303C, Ocean City

Listing courtesy of Northrop Realty. Contact: (302) 539-0800

4 Beds ⋅ 5 Baths

Situated on a private, serene half-acre waterfront lot in the desirable Colonial Village section of Ocean Pines, this spectacular 4-bedroom, 3 full bath, 2 half bath home offers over 4,289 square feet of beautifully designed living space with exceptional indoor and outdoor amenities. The home is strategically positioned via view-oriented architecture to guarantee water views. Just a short stroll to the Ocean Pines Yacht Club, two community pools, the Pines Point Provisions restaurant, and the Pines Point Marina; this is coastal living at its finest. From the moment you step inside, you'll appreciate the thoughtfully designed floor plan that perfectly balances comfort and functionality. The spacious living room, casual dining room, and inviting family room to provide the perfect setting for entertaining family and friends or simply relaxing. The chef's kitchen is sure to impress with upgraded quartz countertops, premium Viking appliances, and abundant workspace. The luxurious first-floor primary suite is a peaceful waterfront retreat featuring breathtaking water views, a beautifully updated spa-inspired bath, and an oversized walk-in closet with plenty of space for two. The inviting family room, complete with a cozy fireplace, opens to a covered waterfront deck—the perfect place to enjoy your morning coffee or unwind with an evening drink while taking in the tranquil surroundings. A charming four-season gazebo creates the ideal setting for crab feasts, outdoor dining, and relaxing while enjoying the refreshing coastal breezes. The first floor also features a convenient laundry room and two half baths. Upstairs, you'll find three spacious guest bedrooms, two full baths, a dedicated exercise room, and a second covered waterfront deck where you can enjoy spectacular water views and seasonal fireworks. Step outside to your own private waterfront oasis. The expansive backyard offers plenty of room for children and pets to play, while boating enthusiasts will appreciate 105 feet of waterfront with a bulkhead replaced in 2025, a 16,000-pound boat lift, and dockage that can accommodate boats up to approximately 70 feet with easy access to the open bay. The protected canal is perfect for kayaking and paddleboarding, and dolphins are often spotted swimming by, making every day feel like a vacation. Additional improvements include two HVAC systems replaced in 2025 and 2026, a tankless water heater approximately seven years old, an encapsulated crawl space, a spacious 2.5-car garage, and ample driveway parking. This smart home is equipped with security cameras and an alarm system for added peace of mind. Best of all, this exceptional waterfront home is being sold fully furnished, making it truly move-in ready. Simply bring your suitcase and start creating unforgettable memories with family and friends in one of Ocean Pines' most sought-after waterfront communities. Flood Zone X no flood insurance required. Water depth in low tide is 5Ft 6".

538 Yacht Club Dr, Ocean Pines

Listing courtesy of Coldwell Banker Realty. Contact: 4438562211

3 Beds ⋅ 3 Baths

Beautiful Townhome in Marina Village at Ocean Pines Welcome to this charming 3-bedroom, 2.5-bath townhome located in the desirable Marina Village Townhomes section of the Ocean Pines community. Offering comfort, style, and an unbeatable location, this home is perfect for year-round living or a coastal getaway. The home features a one-car garage, durable hard-surface flooring on the stairs, hallway, and guest bedroom, and a bright sunroom that provides the perfect space to relax and unwind. Step outside to enjoy the freshly updated rear deck, overlooking a peaceful wooded backdrop. The spacious primary suite is a true retreat, featuring an ensuite bath, a unique double-sided fireplace, and a private deck where you can enjoy your morning coffee while taking in the tranquil wooded views. On the main level, you'll find a warm and inviting family room with a fireplace, a separate dining area, and an eat-in kitchen designed for comfortable everyday living and entertaining. Ideally situated within walking distance to the Ocean Pines Yacht Club, Mumford's Landing Pool, and Pines Point Provisions, this home allows you to enjoy some of the community's most popular amenities right at your doorstep.Don't miss the opportunity to own this wonderful Marina Village townhome that perfectly blends convenience, comfort, and coastal charm.

953 Yacht Club Dr, Ocean Pines

Listing courtesy of Coldwell Banker Realty. Contact: 4438562211

2 Beds ⋅ 2 Baths

This unit has direct Bayfront views and gorgeous sunsets from the balcony. The interior has been freshly painted, new appliances. Cabinets with soft close drawers. Both bedrooms have their own private bath and walk-in closets. All new plank floor throughout. 4 remote ceiling fans with light.

4709 Coastal Hwy Unit #364, Ocean City

Listing courtesy of ERA Martin Associates. Contact: 4107491818

3 Beds ⋅ 4 Baths

Welcome to the prestigious gated community of Harbour Island, home to the world-famous White Marlin Open Fishing Tournament! This beautifully 3-bedroom townhouse with a spacious bonus room and 3.5 baths offers an unbeatable waterfront lifestyle with breathtaking, unobstructed views of the bay from both the main living area and the expansive deck. Boating enthusiasts will appreciate the private double boat slip with two new boat lifts, perfectly suited for a 25-foot center console boat on one side and two personal watercraft on the other—making it easy to enjoy everything Ocean City has to offer by water. Inside, the home features gorgeous hardwood floors and an updated kitchen complete with modern cabinetry, countertops, and flooring. Offered fully furnished, this property is truly move-in ready, whether you're looking for a primary residence, vacation getaway, or investment opportunity. Additional updates include a 2019 HVAC system and a new hot water heater, providing peace of mind for years to come. Located just minutes from Ocean City's beaches, Boardwalk, restaurants, shopping, and entertainment, this is a rare opportunity to own one of Harbour Island's most desirable waterfront townhomes. Schedule your private showing today and experience the coastal lifestyle you've been dreaming of!

419 14th St Unit #71, Ocean City

Listing courtesy of RE/MAX One. Contact: 4105356291

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