Ocean Pines Homes for Sale

Ocean Pines Homes for Sale

Welcome to Ocean Pines, Maryland—a charming coastal community nestled in the heart of Worcester County. Just a stone's throw away from the vibrant beaches of Ocean City, this picturesque town offers the perfect blend of tranquility and adventure. With its stunning waterfront views, lush green spaces, and a welcoming atmosphere, Ocean Pines is an ideal place to call home.

Ocean Pines is renowned for its beautiful homes, ranging from cozy beach cottages to spacious family residences, making it a perfect fit for first-time buyers, retirees, and everyone in between. The real estate market here is thriving, with a variety of homes for sale that cater to diverse tastes and budgets. Whether you’re looking for a serene retreat or a vibrant community lifestyle, you’ll find it all in Ocean Pines.

In addition to its stunning properties, Ocean Pines boasts an array of amenities that enhance the quality of life for its residents. Enjoy leisurely afternoons at one of the community’s parks, take a dip in the pool, or explore the scenic walking trails. The area also features a variety of shops, restaurants, and recreational activities, ensuring there’s always something to do.

With its friendly community spirit and a wealth of natural beauty, Ocean Pines is more than just a place to live; it’s a lifestyle waiting to be embraced. If you’re ready to find your dream home in this idyllic setting, explore the homes for sale in Ocean Pines today and start your journey towards a vibrant coastal life!

Newest Ocean Pines Homes for Sale

$449,900
3 Beds ⋅ 3 Baths
Beautifully maintained home, offering a blend of comfort, style, and community, making this an exceptional choice for anyone seeking a serene living environment. One of only three standalone Blue Teal models, it sits on a prime lot, nestled in a 55+ community within Ocean Pines, with easy access to the community clubhouse and amenities. This 3- bedroom, 3-bath model has an additional loft area for extra versatility. Over 1800 sq. ft. thanks to a year-round sunroom addition. Welcoming entry with 16-foot ceilings that enhance the sense of space, abundant windows throughout, especially in the sunroom connecting you to the scenic wooded backyard. Luxury vinyl wood plank floors throughout the living areas offer durability and aesthetic appeal. An updated kitchen with stainless steel appliances and quartz countertops provides the modern touch. HVAC and roof were replaced 7 years ago, ensuring peace of mind. This home is not just a residence; it’s a haven that combines modern amenities with a warm community atmosphere. The stunning sunroom and thoughtful updates make it a standout choice for those looking to enjoy a comfortable lifestyle in a vibrant community.

30 Chatham Ct, Ocean Pines

Listing courtesy of Coldwell Banker Realty. Contact: 4438562211
$499,000
3 Beds ⋅ 3 Baths
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

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty-WOC. Contact: 4105202600
$474,900
3 Beds ⋅ 2 Baths
This charming Salt Box-style home, built in 1989, offers a perfect blend of comfort and modern living. With 1,539 sq. ft. Step inside to discover a warm ambiance highlighted by beautiful wood floors and cozy carpeting. The traditional floor plan seamlessly connects the kitchen and dining areas, making it perfect for entertaining. The kitchen is equipped with energy-efficient appliances, including a self-cleaning oven and built-in microwave, ensuring both convenience and sustainability. The exterior boasts extensive hardscaping, a hot tub for unwinding, a fire pit for relaxing evenings and a community pool that invites you to enjoy sunny days. The property sits on a generous 0.24-acre lot, providing ample outdoor space for activities and gardening. Parking is a breeze with a detached garage and a spacious driveway. Located in a vibrant community, this home is surrounded by parks, walking trails, and recreational facilities, perfect for outdoor enthusiasts. The neighborhood is known for its friendly atmosphere and convenient access to local amenities, including shops and dining options. This residence is not just a house; it's a place to create lasting memories. Experience the warmth and comfort of this delightful home today!

11 Seafarer Ln, Ocean Pines

Listing courtesy of Keller Williams Realty. Contact: 3023600300
$875,000
3 Beds ⋅ 3 Baths
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

Listing courtesy of Keller Williams Realty Delmarva. Contact: 4105246400
$369,900
3 Beds ⋅ 2 Baths
Check out this inviting getaway with peaceful and happy vibes! Located on a quaint street within a short walking distance to 6.6 acre Huntington Park, featuring playground equipment and open space. You will find engineered hardwood floors and vaulted ceilings throughout the main living areas. The split bedroom floor plan places the primary suite on one side of the house and the extra bedrooms on the opposite side, with the central living areas acting as a noise buffer and privacy wall. Beautiful granite countertops, a large center island and two separate breakfast bars are featured in the spacious and bright kitchen, but the showcase of this lovely home is definitely the huge rear screened porch that measures 20 x 14, the perfect setting for crab feasts or gathering with friends and family. A double door welcomes you into the primary suite, while one of the guest bedrooms is brightened by an arched window with a window seat and vaulted ceilings, which could double as a home office. A large capacity washer and dryer takes care of loads of beach towels and bedding. The heat pump was replaced in 2018. Furnishings are negotiable. Ocean Pines is an award-winning, amenity-filled community, located just a short drive to the nearby beaches of Ocean City, Assateague Island National Seashore, and downtown historic Berlin!

43 Birdnest Dr, Ocean Pines

Listing courtesy of Hileman Real Estate-Berlin. Contact: (410) 208-9200
$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
$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
$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
$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
$388,000
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
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