Ocean Pines Homes with Pool

Ocean Pines Homes with Pool

Welcome to Ocean Pines, Maryland – a hidden gem nestled in Worcester County that beautifully marries coastal charm with suburban tranquility. Just a stone's throw from the Atlantic Ocean, this vibrant community offers a perfect retreat for families, retirees, and anyone seeking a serene lifestyle amidst nature’s wonders. With its lush landscapes, picturesque waterways, and a plethora of recreational activities, Ocean Pines is not just a place to live, but a lifestyle to embrace.

One of the standout features of homes in Ocean Pines is the abundance of properties boasting private pools. Imagine stepping into your backyard oasis on a warm summer day, where you can unwind and soak up the sun in your very own swimming pool. These homes offer the ideal blend of luxury and comfort, perfect for entertaining friends and family or enjoying a peaceful afternoon with a good book by the water.

Beyond the allure of private pools, Ocean Pines is home to a wealth of amenities, including scenic parks, hiking trails, and community events that foster a strong sense of belonging. Residents enjoy access to beautiful beaches, golf courses, and a variety of dining and shopping options just a short drive away. Whether you’re looking for a full-time residence or a vacation getaway, Ocean Pines provides an exceptional quality of life with homes that cater to your every need.

Explore the delightful offerings of Ocean Pines and discover your dream home with a pool today – where every day feels like a vacation!

Newest Ocean Pines Homes with Pool

$399,000
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
$545,000
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
$1,749,900
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
$479,900
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
$589,900
3 Beds ⋅ 3 Baths
Stunning Coastal Townhome with Spectacular Water Views Enjoy coastal living at its finest in this beautifully updated 3-bedroom, 2½-bath townhome offering gorgeous water views and a move-in-ready interior. Ideally located, this home is just steps from the Yacht Club, where you can enjoy waterfront dining, a pool bar, and a vibrant marina lifestyle. Relax on one of two private balconies, including one off the spacious primary suite, and take in the beautiful views. Nearby amenities include Pines Point Marina, Mumfords Landing pool, and the Yacht Club pool, all just down the street. Whether you’re looking for a primary residence, vacation getaway, or investment property, this exceptional townhome combines modern updates, an unbeatable location, and the best of coastal living. See list of upgrades in disclosure information.

941 Yacht Club Dr, Ocean Pines

Listing courtesy of ERA Martin Associates, Shamrock Division. Contact: 4106415000
$469,900
3 Beds ⋅ 3 Baths
Imagine coming home to your own secluded haven surrounded by nature. This impeccably maintained 3-bedroom, 3-bath home delivers effortless one-level living designed around quality, comfort, and coastal entertainment. Step inside to an airy, open layout bathed in natural light, highlighted by updated LVP flooring throughout and a cozy fireplace serving as the warm focal point of the living space. The gourmet kitchen is a true chef’s delight, featuring an expansive island and stunning quartz countertops—making it an absolute dream for hosting and daily prep. Outdoor living is at its finest; relax on the awning-covered front deck or retreat to the generous screened porch to take in the serene, wooded views. Located in an amenity-rich Ocean Pines community, you'll love having pools, golf, and marinas right at your fingertips —all just a short drive from the beaches and excitement of Ocean City!

39 King Richard Rd, Ocean Pines

Listing courtesy of ERA Martin Associates, Shamrock Division. Contact: 4106415000
$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
$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
$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
$390,000
3 Beds ⋅ 2 Baths
Welcome to coastal living at its finest in sought-after Ocean Pines, Maryland! Discover this beautifully updated 3-bedroom, 2-bath home that has been completely renovated from top to bottom. Every detail has been thoughtfully refreshed, offering a true move-in-ready experience just minutes from the beaches of Ocean City. Interior Highlights Totally renovated kitchen — modern finishes, perfect for everyday living or entertaining Fully renovated bathrooms with contemporary updates New vinyl plank flooring throughout the main living areas for durability and style New carpet in the bedrooms for added comfort Inviting gas fireplace ideal for cozy evenings year-round Outdoor Living Step outside to your brand-new wrap-around deck — the perfect spot for morning coffee, evening relaxation, or entertaining friends and family while enjoying the wooded, coastal surroundings of Ocean Pines. Ocean Pines Lifestyle & Amenities As a resident of Ocean Pines, you’ll enjoy access to one of the premier residential communities on Maryland’s Eastern Shore (amenities available via optional a-la-carte memberships): Five swimming pools (including indoor and outdoor options, plus the Ocean Pines Beach Club in Ocean City) Robert Trent Jones Sr.–designed championship 18-hole golf course Premier racquet sports complex with tennis, pickleball, and platform tennis Two marinas and the scenic Yacht Club with bayfront dining Private Beach Club oceanfront facility in Ocean City (with resident parking privileges) Multiple parks, walking & biking trails, community center, farmers market, and year-round recreation programs Own police and fire departments for added peace of mind Located just a short 10–15 minute drive to Ocean City’s beaches, boardwalk, dining, and entertainment, yet nestled in a quieter, wooded community with over 3,000 acres and more than nine miles of waterfront property. Ocean Pines offers the ideal balance of resort-style amenities and relaxed Eastern Shore living.This renovated home is ready for its next owners to enjoy the best of coastal Maryland living. Don’t miss this opportunity!

6 Weeping Willow Ct, Ocean Pines

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$559,900
3 Beds ⋅ 2 Baths
This new construction property is a customized version of the popular Wahoo model, with groundbreaking scheduled to start in approximately 30 days. Buyers who secure this home early have a rare window of opportunity to select the custom interior finishes and make this home uniquely theirs. Core Property Overview, Floor Plan: Customized Wahoo/3 Model , Bedrooms: 3 spacious bedrooms , Bathrooms: 2 full bathrooms, Garage: Attached 2-car garage , Premium Interior & Gourmet Kitchen Custom Upscale Kitchen: Outfitted with high-end stainless steel appliances. Gas Cooking: Features a premium gas range for culinary precision. Gas Fireplace: Serves as a cozy, ambient centerpiece in the main living area. Primary Suite: Features an expansive, large primary bath with detailed custom showers. Outdoor Living Spaces Screened Porch: Built for bug-free relaxation and comfortable outdoor lounging. Outside Deck: Perfect for grilling, entertaining, and enjoying the backyard views. High-Efficiency & Structural Systems Hybrid HVAC: Dual-fuel heating and cooling system maximizes energy efficiency and cost savings. On-Demand Hot Water: A tankless water heater system delivers endless hot water instantly while lowering utility costs. Encapsulated Crawl Space: Offers premium moisture control, protects the subfloor, improves indoor air quality, and adds superior insulation.

108 Nottingham Ln, Ocean Pines

Listing courtesy of Coldwell Banker Realty. Contact: 4438562211
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