Ocean Pines Real Estate Search

Ocean Pines, MD Real Estate & Community Guide

Located just minutes inland from the beaches of Ocean City, Maryland, Ocean Pines is a premier 3,000-acre master-planned residential resort community in Worcester County. Known for its heavily wooded lots, deep-water canals, top-tier amenities, and strong sense of community, Ocean Pines provides the ideal setting for year-round residents, retirees, and vacation homeowners.

With over 8,400 platted lots, Ocean Pines combines quiet coastal woodland living with immediate access to golf, boating, swimming, and private beach parking in Ocean City.

Why Buyers Choose Ocean Pines, MD 

 Ocean Pines offers one of the most comprehensive amenity packages on the Delmarva Peninsula, making it a standout choice for single-family living near the beach.

Unrivaled Resort Amenities

  • Ocean Pines Beach Club: A private oceanfront beach club located at 49th Street in Ocean City, featuring a private pool, restaurant, bar, and beach access exclusively for community residents and guests.

  • Golf & Racquet Sports: Home to a 18-hole championship golf course designed by Robert Trent Jones Sr., complete with a clubhouse, pro shop, and driving range, alongside extensive tennis and pickleball courts.

  • Aquatics & Parks: Five community swimming pools (including an indoor heated pool), multiple playgrounds, walking trails, a dog park, and a community marina with boat slips.

Diverse Property Styles & Waterfront Access

  • Waterfront & Canal Homes: Hundreds of homes feature private boat docks, lifts, and direct navigable access to St. Martin River and Isle of Wight Bay.

  • Golf Course & Wooded Lots: Enjoy private views overlooking fairway greens or quiet pine-forested lots.

  • Single-Family & Low-Maintenance Living: Choose between detached single-family homes, single-level ranch style layouts, or low-maintenance townhomes and condominiums.

Frequently Asked Questions About Ocean Pines, MD Real Estate

Where is Ocean Pines located in relation to Ocean City, MD?

Ocean Pines is situated in Worcester County directly across the Isle of Wight Bay, accessible via the Route 90 bridge. Residents are typically just a 10 to 15-minute drive from the beaches and boardwalk of Ocean City.

What does the Ocean Pines HOA fee cover?

The Ocean Pines Association (OPA) annual assessment covers the maintenance of community infrastructure, roads, drainage systems, parks, 24/7 private police department protection, fire/EMS facilities, and common grounds. Specific amenity memberships (golf, pool passes, boat slips) can be added based on resident preference.

What school district serves Ocean Pines?

Ocean Pines is served by the acclaimed Worcester County Public Schools district. Students typically attend Showell Elementary School, Stephen Decatur Middle School, and Stephen Decatur High School.

Local Resources & Helpful Links

Ocean Pines Newest Listings

$899,900
4 Beds 3 Baths MDWO2033692 MLS
Set on a premier golf course lot overlooking the 8th fairway, this exceptional, nearly 3,900-square-foot home offers 4 bedrooms, 3 full baths of quality construction, thoughtful design, and extensive upgrades. Nine-foot ceilings, four skylights, cathedral ceilings in both the living room and the sunroom, numerous pocket doors, and abundant natural light create an inviting feel throughout. The main level features a spacious primary suite with en-suite bath, bamboo hardwood flooring, and a living room highlighted by a dramatic two-story natural stone fireplace matching the home's exterior stonework. The fireplace features an old-wood mantel reclaimed from a Pennsylvania barn, gas insert with heat blower, remote operation, and annual maintenance. Plantation shutters adorn the upper-level windows in the living room. Most lighting throughout the home is on dimmers, and all TVs are wall-mounted with wiring concealed. The beautifully appointed kitchen features tall-to-ceiling Omega cabinetry with dovetail construction, soft-close doors/drawers, granite counters, under-mount lighting, pull-out shelving, lazy Susan corner cabinet, baker's pan cabinet, separate prep sink, and double ovens with the top oven being convection and the recessed light above doubles as an additional exhaust fan. The cooktop has an exterior-vented exhaust system and there's a dedicated 20-amp outlet next to the cooktop for those serious chefs. Underneath the cooktop are two large pot/pan drawers flanked by two spice rack pullout cabinets! Also noteworthy is the wine refrigerator and dishwasher new in 2026. A walk-in pantry offers both wood and wire shelving.. The formal dining space off the kitchen features bay windows and a farmhouse chandelier. The cathedral-ceiling sunroom features a high sunburst window, while the adjoining recreation room includes skylights and opens to the rear deck. Upstairs, the primary bedroom features a tray ceiling and luxurious en-suite bath with walk-in Roman shower and multiple body sprays. Off the primary bedroom is a home office that leads to the 3rd floor walk-up attic, which provides extensive floored storage plus a finished, conditioned storage room (the green room in the photos). Bedrooms 2 and 3 share a Jack-and-Jill bath, and both bedrooms offer walk-in closets featuring built-in drawer systems. The second-floor hallway offers a huge storage closet, and the 2nd floor laundry room includes a utility sink. One bedroom upstairs is even insulated from top-to-bottom for sound reduction (you'll note the drum set in the photos) and features a cathedral ceiling. Outdoor living is exceptional, with 8th fairway views, extensive rear pavers, elevated composite decking, covered grilling area with bluestone flooring and remote/light-sensor string lighting, outdoor gas fireplace with custom dome cover, 7-person Hot Spring Grande hot tub on poured slab, landscaped 10x12 shed on slab, concrete side walkway, and multi-zone irrigation with rain sensor. Natural gas serves the fireplace, Rinnai systems, and fire pit. The home is foam insulated throughout and features an upgraded ZIP System beneath the siding. The geothermal HVAC includes two 3-ton water-source units, one for each level, a 6-ton dual-zone system, and six wells, serviced twice annually by A&A Services Co. Two tankless Rinnai systems provide efficient hot water. A 16kW Generac generator provides peace of mind, while an upgraded 1-inch water supply line improves water pressure. Back downstairs, a large mudroom with cabinetry connects the home to the two-car attached garage, which features an insulated door, mini-split heating/air, utility sink, and epoxy flooring. This remarkable property combines golf course views, exceptional indoor and outdoor living, abundant storage, energy-efficient systems, and a level of thoughtful detail rarely found in one home.

38 Battersea Rd, Ocean Pines

$499,000
3 Beds 3 Baths MDWO2039622 MLS
MUST-SEE beach-style home in the highly-acclaimed community of Ocean Pines! This 3-bedroom/2.5-bathroom, fully-furnished, turnkey house, with select items excluded, situated on a 0.20-acre serene, natural setting, with both an indoor and outdoor staircase to access inside. Within the main door, a foyer entrance allows for beach gear and other storage, before heading up the stairs to the elegant, open living-space. Here, LVP flooring guides you between the amply-sized modern kitchen, complete with quartz countertops and stainless-steel appliances, the cozy living-room, and the spacious dining-area. From here, the living and entertainment space continues, with sliding-glass doors giving the invitation to enjoy the MASSIVE screened-in porch (also accessed by a separate door from the kitchen). Family and friends can then transition into a full nature-immersion, as the opposite screen-door gives way to the large deck, easily serving as the party center, or a peaceful spot for coffee and bird-watching. The main level is also served by a powder room, exhibiting convenience for all. The LVP flooring ventures upstairs, locating the 2nd and 3rd bedrooms, adjoined by a Jack and Jill bathroom, offering privacy and comfort to family and guests. The showstopper on this level, though, is the primary ensuite, boasting a generous size, with a sleek, contemporary bathroom. But that's not all, as entry to a private balcony can be gained from the other side of the ensuite, adding to the ambiance of the primary sleeping-quarters. And if that weren't enough, the theme just keeps extending, as the primary balcony merges into a spiral staircase that elevates you to the birds-eye view from the SUNDECK, where a glimpse of the canal can be caught through the trees. The aforementioned canal, an easy walk across the street, also has an adjoining nature area called Pintail Park, which is an 11-acre space, featuring a scenic covered-gazebo, walking trail, crabbing and fishing pier, picnic tables, and an ADA-accessible kayak/boat launch for residents to use. This is just one of seemingly-countless amenities that community members have access to, including dining and entertainment options, many other parks, a premier golf course, five swimming pools, a yacht club, two marinas, and a 1st-class racquet-sports complex. Ocean Pines is truly a resort community with only 5 miles separating it from the beach and Ocean City. Whether you're searching for the perfect forever home, a coastal retreat, or an investment opportunity, this property offers exceptional potential. The home generated over $40,000 in rental income in 2023 under previous management. More recent rental performance reflects changes in rental management and marketing exposure, while the home's desirable location, amenities, and appeal continue to position it for excellent rental potential. (Rental income is provided for informational purposes only and is not a guarantee of future rental performance.) DO NOT hesitate on this phenomenal opportunity while it lasts!

582 Ocean Pkwy, Ocean Pines

$514,900
3 Beds 2 Baths MDWO2040412 MLS Points Reach BLDG.
Welcome to 3208 Points Reach, where waterfront living and the relaxed Ocean Pines lifestyle come together in a spacious, light-filled condominium overlooking the bay. From the main living area, large glass doors draw your attention straight toward the water, while gleaming hardwood floors, crown molding, and a corner gas fireplace create a warm and inviting space for both everyday living and entertaining. The generously sized kitchen opens to the main living area and features an abundance of wood cabinetry, granite countertops, stainless steel appliances, recessed lighting, and plenty of workspace for cooking and gathering. The open layout keeps the kitchen connected to the living space and the waterfront setting beyond. Step outside to what may be the highlight of the home: an expansive covered waterfront balcony with plenty of room to relax, dine, and entertain. A built-in gas grill makes outdoor cooking easy, while the sweeping views across the water and surrounding natural landscape provide a beautiful backdrop for morning coffee, evening cocktails, and everything in between. Inside, spacious bedrooms offer comfortable accommodations, with details including crown molding, ceiling fans, plantation-style shutters, and generous closet space. Set within the desirable Points Reach community in Ocean Pines, this residence offers the combination buyers come to the Eastern Shore looking for: beautiful water views, comfortable living, inviting indoor and outdoor spaces, and a setting surrounded by coastal scenery. Whether enjoyed as a full-time residence or an Eastern Shore getaway, 3208 Points Reach is ready for its next owner to make it their own.

3208 Points Reach Unit #3208, Ocean Pines

$875,000
3 Beds 3 Baths MDWO2040246 MLS
We're going to call this canal-front because technically, that's what it is. Just don't expect it to look like most canal-front homes in Ocean Pines!! Walk out back and you'll understand the difference. Instead of staring across a narrow canal at another row of homes, the water (and views) open up considerably.... with no homes blocking your view, you're given a stunning view of the Ocean Pines Golf Course, and beyond. Plus, you get the boating access you're looking for in a waterfront home. Let's move on to the house itself.... At approximately 2,500 square feet, this 3-bedroom, 3-full-bath home gives you something else that's surprisingly difficult to find on the waterfront in Ocean Pines: SPACE. There's a true two-car garage, generous living areas, a three-season room overlooking the water, and a large first-floor deck that turns the backyard into a pretty compelling reason to spend more time outside. Plus, the interior has been extensively renovated with a new kitchen, new bathrooms, new flooring, new central HVAC, and fresh paint throughout. The result, when you walk in the front door into a vaulted 2-story living room, is impressive! This is an established waterfront home that's already had the major interior updating that you don't want to have to do yourself. Out back is where everything starts coming together. The property includes a bulkhead and private dock with water suitable for boats, paddle-boarding, and kayaks....giving you the ability to keep the boat (and water toys) in your back yard. The three-season room provides another place to enjoy the waterfront when the weather doesn't cooperate... because this is Maryland and apparently we're required to experience all four seasons in the same week (you know I'm right)!. There's no 'one thing' that separates this home from other waterfront homes in the area.... It's "all the things" that make it stand out. The lot size, the quiet street, the attached garage, the renovations, the vaulted ceilings, the waterfront location, the views, and the price point! That's what makes this home at 84 Newport so interesting. Ocean Pines has grown into one of the area's most complete residential communities, with miles of waterfront, parks and recreation, pools, racquet sports, boat ramps and kayak launches, the Ocean Pines Golf Club, Yacht Club, and even its own Beach Club in Ocean City. You're positioned within an easy drive of Berlin, Ocean City, Assateague Island, shopping, restaurants, healthcare, and everything else that makes northern Worcester County such a desirable place to live. At $875,000, we're offering a waterfront home that 'offers' more than most. And we'd love to help make this your home.

84 Newport Dr, Ocean Pines

$399,000
2 Beds 2 Baths MDWO2040242 MLS
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

$545,000
5 Beds 2 Baths MDWO2040224 MLS
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

$1,749,900
4 Beds 5 Baths MDWO2040086 MLS
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

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