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$389,900
4 Beds ⋅ 3 Baths ⋅ MDWO2036868 MLS
This stunning 4-bedroom, 2.5-bath contemporary single-family home offers the perfect blend of modern updates, open living spaces, and turnkey convenience in the sought-after community of Ocean Pines. Designed with an inviting open-concept layout, the home features a bright and airy living room with cathedral ceilings, skylights, and large windows that fill the space with natural light, along with an enclosed sunroom ideal for relaxing year-round. The gourmet kitchen features beautiful granite countertops, newer shaker style cabinetry, and Whirlpool stainless steel appliances. The main level also includes a spacious primary suite, a second bedroom, and a convenient powder room, providing flexibility for guests or single-level living. Upstairs, you’ll find two additional bedrooms, a full hall bath, and a large storage area, offering plenty of room for family, guests, or hobbies. This home is truly move-in ready with numerous recent updates, including newer luxury vinyl plank flooring on the first floor, improvements to the crawlspace, fresh interior paint throughout, and a brand-new roof. Meticulously maintained, it presents a rare opportunity to own a like-new home in a well-established coastal community. Whether you’re searching for a primary residence, vacation getaway, or investment property, this exceptional home checks all the boxes. Enjoy everything Ocean Pines has to offer, including pools, golf, marina, parks, trails, and easy access to nearby Ocean City beaches, dining, and entertainment. This is truly a must-see property—schedule your showing today!

37 Watertown Rd, Ocean Pines
$2,250,000
5 Beds ⋅ 7 Baths ⋅ MDWO2036856 MLS
Experience breathtaking water views from this expansive three-level waterfront home designed for comfort, convenience, and entertaining. Featuring a private elevator, two garages, concrete driveway, and a whole-house generator, this property offers exceptional space for everyday living and hosting guests. The home has also undergone a complete exterior overhaul, including the installation of a brand-new metal roof, providing both durability and long-term peace of mind. The main living area showcases a spacious island kitchen with granite countertops, stainless steel appliances, and a breakfast room, along with formal living and dining rooms. Additional spaces include a family room, office, sunroom, exercise room, studio, entertainment room, workshop, and abundant storage. Two impressive primary suites provide luxurious retreats. The main suite features a private deck, walk-in closets, gas fireplace with marble hearth, a spa-style bath with whirlpool tub, marble floors and tile, and a separate powder room. The second suite includes a walk-in whirlpool tub/shower combination. Additional highlights include hardwood floors, surround sound, central vacuum, security system, two washer/dryer sets, two water heaters, and three-zone heating and cooling. Outdoor living is just as impressive with five decks, front and rear paver patios, and exceptional boating amenities, including a 90’ vinyl bulkhead, a 6’ x 33’ dock, and two boat lifts installed in 2020. Prepare to be impressed by the space, views, and waterfront lifestyle this remarkable home offers.

26 Leigh Dr, Ocean Pines
$697,000
3 Beds ⋅ 3 Baths ⋅ MDWO2036636 MLS
Rare opportunity to build your dream home on this homesite with Bay to Beach Builders! Please note: no home is currently built on this property. The list price reflects a proposed construction package and includes the lot, estimated lot preparation/site work, and the featured Bluewater floor plan. The Bluewater offers 1,767 square feet of thoughtfully designed living space with 3 bedrooms, 2.5 bathrooms, a first-floor primary suite, soaring ceilings in the main living area, and timeless coastal-inspired architecture. Designed for comfortable everyday living and effortless entertaining, this home blends modern functionality with classic beach-town charm. The Bluewater is just one of several floor plans that have been reviewed for this lot and meet setback requirements. Additional home designs available through Bay to Beach Builders include The Oxford (1,126 sq. ft.), The Driftwood (1,820 sq. ft.), The Surfside (1,614 sq. ft.), The Fenwick (2,029 sq. ft.), The Chesapeake (2,455 sq. ft.), The Bethany (2,584 sq. ft.), The Rehoboth (2,584 sq. ft.), and The Ocean View (3,424 sq. ft.). The maximum recommended footprint for this homesite is approximately 38' x 66', and these plans have been selected accordingly. Many of these designs are part of Bay to Beach Builders' popular Coastal Collection and Cottage Series, specifically designed to maximize living space on narrower lots. Homes shown on pilings may also be constructed on a traditional foundation depending on buyer preference and site conditions. As a custom builder, Bay to Beach Builders can modify floor plans to better suit your lifestyle, budget, and vision. Buyers are encouraged to explore available floor plans and design options through Bay to Beach Builders and consult directly with the builder regarding pricing, customization opportunities, and included features. Whether you're dreaming of a full-time residence, vacation retreat, or investment property near the coast, this property offers the flexibility to create a home tailored to your needs. The property offers navigable waterfront with the ability to construct a dock and pier. Neighboring owners currently keep a pontoon boat on the creek, demonstrating recreational boating access. Buyers should verify water depths for their specific vessel.

72 Boston, Ocean Pines
$379,900
3 Beds ⋅ 2 Baths ⋅ MDWO2036298 MLS
Spacious and open floor plan designed for easy living and effortless entertaining . This inviting home features 3 generously sized bedrooms and 2 full baths * Sliding glass doors open to a large screened porch * The charming front porch is perfect for enjoying your morning coffee or relaxing in the evenings with your favorite beverage * Roof replaced in 2022 with 50 year warranty * Central Heat /AC for year round comfort * Abundant closet space and storage shed for all of your beach and boating essentials * You'll love being part of a vibrant waterfront community offering exceptional amenities including 5 pools, tennis, pickleball, yacht club, restaurants, Robert Trent Jones, Sr designed championship golf course as well as a beachfront pool, parking and restaurant in Ocean City * EVERYTHING you need to embrace the Coastal Lifestyle to the fullest * Ocean Pines is located just 5 miles inland from Ocean City and blends wooded serenity with Coastal Charm * Fresh paint, new carpeting in bedrooms... Let's make this your home yours *

61 Abbyshire Rd, Ocean Pines
$352,000
3 Beds ⋅ 2 Baths ⋅ MDWO2036314 MLS
Welcome to 26 Castle Drive in Ocean Pines — a beautifully renovated 3-bedroom, 2-bath home originally built in 1984 and thoughtfully updated from top to bottom. This property offers peace of mind with major upgrades already completed, including a new roof, new siding, new windows and doors, new duct work. Inside, you’ll find fresh paint throughout, modern railings, a completely remodeled kitchen, and updated bathrooms designed with today’s style and functionality in mind. The new kitchen features contemporary finishes and a clean, modern aesthetic, making it perfect for everyday living and entertaining. Both bathrooms have been tastefully updated, offering a fresh and cohesive design throughout the home. Located in the sought-after Ocean Pines community, residents enjoy amenities including pools, parks, marina access, golf, and proximity to Ocean City beaches, dining, and shopping. Move-in ready and worry-free — this is the perfect opportunity for a primary residence, second home, or investment property

26 Castle Dr, Ocean Pines
$335,000
3 Beds ⋅ 2 Baths ⋅ MDWO2036184 MLS
3 bedroom, 2 bathroom rancher nestled in a cul de sac in Ocean Pines Community. Gas fireplace, skylight, enclosed rear porch, Laundry room, over sized one car garage. Primary bedroom and primary bathroom. This property is a Fannie Mae Homepath property.

18 Southwind Ct, Ocean Pines
$325,000
4 Beds ⋅ 3 Baths ⋅ MDWO2035840 MLS
BIG PRICE REDUCTION! MOTIVATED SELLER! BRING ALL OFFERS! OVERSIZED FLOOR PLAN! You'll feel like you're in the mountains in this Extra Large Home on an Extra Large lot that backs to Parkland! The second level contains the main living areas, including a tiled backsplash kitchen, a living room with two story ceilings, balcony access, and rustic wooden walls. A large 16x12 Bedroom and 11x8 Bath complete the main floor. Enter the carpeted stairway to a loft area, two additional bedrooms and a full bath on the upper level, overlooking the living room. Accommodate the in-laws / grandparents / large families in the Lower Level living quarters with an additional bedroom, bath, laundry room, kitchen and living area. A one car garage will store all of your beach gear, toys, and tools! Easy access from the South entrance to Ocean Pines. Enjoy top-notch amenities and a short drive to the beaches of Ocean City and Assateague National Seashore. Sold in As-Is condition.

850 Ocean Parkway, Ocean Pines
$824,900
5 Beds ⋅ 4 Baths ⋅ MDWO2035674 MLS
Brand new construction now completed ready for the summer season! This impressive home offers over 3,400 square feet of living space with 5 bedrooms, 3.5 baths, and a bonus room, providing exceptional flexibility for today’s lifestyle. Located on a quiet cul-de-sac in Triple Crown Estates, a community known for its larger lot sizes, this property features a generous 125’ x 100’ homesite. The home offers two primary suites — one on each level. The first-floor primary suite features a beautifully tiled shower, while all full bathrooms are equipped with double-bowl vanities. The stunning kitchen showcases quartz countertops and stainless steel appliances and flows seamlessly into the dining area, which opens to a screened porch and deck, perfect for indoor-outdoor living. The family room is warm and inviting with a linear electric fireplace and a beam-accented vaulted ceiling. Additional highlights include 9’ ceilings on the first floor, LVP flooring throughout the first floor and staircase, a dedicated laundry room, and an 80-gallon hot water heater. The fully insulated, oversized two-car garage features 12’ ceilings, offering excellent potential for additional storage space. The bonus room is separately conditioned with its own split HVAC system, making it ideal for a media room, home office, playroom, or guest retreat. Enjoy all that Ocean Pines has to offer, including multiple pools, golf course, marina, yacht club, beach club in Ocean City, parks, walking trails, and year-round community amenities. Builder Registration #9569.

10 Jockey Ct, Ocean Pines
$315,000
3 Beds ⋅ 3 Baths ⋅ MDWO2035392 MLS ⋅ Pines Point BLDG.
Don't miss this opportunity to own one of the most desirable and move-in-ready properties in Ocean Pines. This bright end-unit offers the perfect blend of convenience, location, and lifestyle with 3 bedrooms, 3 full baths, including a highly sought-after first-floor bedroom and full bath ideal for guests, multi-generational living, or a private home office. Live where every day feels like a vacation—just a short walk to two marinas, two pools, and the Yacht Club, all in the heart of amenity-rich Ocean Pines. Whether you're heading out for a day on the water, enjoying sunset dining, or relaxing poolside, it's all right outside your door. Even better, the path to ownership couldn't be easier. HOA/condo resale documents are complete, title work is finished, and a home inspection has already been completed—removing common hurdles and making a quick, confident closing possible. Recent updates, including a new HVAC system (2025) and refreshed second-floor baths, provide added peace of mind. And for buyers weighing the condo fees, consider the significant value they provide: all exterior maintenance, lawn care, landscaping and grounds maintenance, the master insurance policy, professional management, and parking are included. That means fewer surprise expenses, less weekend upkeep, and more time enjoying everything Ocean Pines has to offer. It's a true lock-and-leave lifestyle that's ideal for full-time residents, second-home owners, and investors alike. Properties offering this combination of 3 bedrooms, 3 full baths, first-floor living flexibility, walkable access to marinas and pools, low-maintenance ownership, and a fast-track closing opportunity are exceptionally rare. Schedule your private tour today and submit your offer before this coastal opportunity is gone.

529 Yacht Club Dr Unit #4, Ocean Pines
$130,000
MDWO2035308 MLS
Build your dream home in the sought-after community of Ocean Pines! This vacant lot offers the perfect opportunity to enjoy all the amenities this premier coastal community has to offer. Ocean Pines features an 18-hole championship golf course, marina and boat ramp, multiple outdoor pools, playgrounds, walking trails, and more. Residents also enjoy a beach club in Ocean City, just minutes away. Conveniently located near shopping, dining, and the beaches of Ocean City, this property is ideal for year-round living or a vacation retreat. Don’t miss your chance to own land in one of Worcester County’s most desirable communities.

92 Ocean Pkwy, Ocean Pines
$2,249,000
8 Beds ⋅ 9 Baths ⋅ MDWO2035268 MLS
Welcome to a rare waterfront masterpiece on a premier point lot in Ocean Pines. Located at 26 W Mallard Drive on a quiet cul-de-sac, this exceptional direct bayfront coastal-style home offers breathtaking, unobstructed views of the Isle of Wight Bay and the Ocean City skyline. Built in 1983 and impeccably maintained, the residence spans just over 5,000 sq. ft. with 8 bedrooms and 8.5 baths, ideal for large gatherings or multi-generational living. Designed to maximize waterfront living, the home features multiple balconies and expansive decks, an outdoor summer kitchen, hot tub, private pier with boat lift, and generous outdoor entertaining spaces perfect for hosting unforgettable bayfront gatherings. Inside, an elevator servicing up to the third level adds convenience and accessibility. The chef’s kitchen is outfitted with 42” cabinetry, granite countertops, stainless steel appliances, multiple ovens, and a GE induction cooktop, complemented by an abundance of storage and prep space. Additional highlights include six refrigerators, a dedicated laundry room, 200-amp whole-house generator, storm shutters, four storage sheds, and an encapsulated crawlspace with dehumidifier and sump pump. Situated within amenity-rich Ocean Pines, residents enjoy access to parks and recreation, aquatics, championship golf, marina, beach club, and more. This extraordinary bayfront property combines space, luxury, and lifestyle—an unparalleled opportunity on Maryland’s Eastern Shore.

26 West Mallard, Ocean Pines
$575,000
MDWO2034876 MLS
The only lot available in highly sought after Terns Landing. The 80 feet of bulkhead was replaced with high quality composite material in 2022 and it even comes with a high end 30,000 lb. boat lift that can accommodate up to a 40 foot vessel. A rare find indeed. Waterfront Lot in Terns Landing on the leeward side of a quiet Cul de Sac is already cleared and ready for your dream home. 80' of waterfrontage offering lovely views and easy access to the open water. Lots of amenities: Restaurant, Basketball Courts, Beach Club, Bike Trail, Boat Dock/Slip, Club House, Community Center, Golf Course, Golf Course Membership Available, Jog/Walk Path, Marina/Marina Club, Picnic Area, Pool - Indoor, Pool - Outdoor, Pool Mem Avail, Recreational Center, Swimming Pool, Tennis Courts, Tot Lots/Playground.

4 Leslie Mews, Ocean Pines
$555,500
5 Beds ⋅ 4 Baths ⋅ MDWO2034472 MLS ⋅ Osprey Point BLDG.
Turnkey and Ready for Summer - Walk to the Yacht Club. Private serene water views all year long, watch birds and wildlife every season throughout the year. Corner lot with plenty of room for entertaining on the side. Discover refined coastal living in this beautifully crafted custom built 5-bedroom, 4-bath home in the sought-after community of Colonial Village at Ocean Pines—just a short stroll from the Yacht Club, community pools and so much more. Custom built with attention to detail. This residence offers over 2,600 sq. ft. of thoughtfully designed living space with top-quality finishes throughout. Main Level Step into a welcoming two-story foyer with 9-foot ceilings and abundant natural light. The main level features a spacious open-concept family room with a cathedral ceiling and a cozy Regency gas fireplace, perfect for relaxing or entertaining. The chef’s kitchen showcases Dacora cabinetry, silestone countertops, porcelain tile flooring, custom backsplash, and high-end Electrolux appliances, including a dual-fuel range. A primary suite on the main level includes dual closets, silestone-topped vanities, a jetted whirlpool tub, and a walk-in silestone shower with special coating on the shower glass to avoid streaking. A second En-suite bedroom offers flexibility for guests or multigenerational living. Access panel under steps in foyer. Upper Level Upstairs, a second primary suite and two additional bedrooms provide comfort and privacy for family and guests. A spacious bonus room above the garage—fully insulated and ideal for storage (providing fitness, or media use—adds to the home’s versatility and an additional 260 sq. feet of space. Middle bedroom has 2 access panels in the dormers 1 for candle lights and other for security system Quality & Efficiency Every detail reflects craftsmanship and care: McLain system - radiant heated floors throughout the main level. 2 high efficiency HVAC systems - Gas Heat, Electric Air. HE Marvin Windows throughout. Tankless Gas Hot Water Heater (2017). Commercial grade de-humidifier in crawl space. Retaining Wall in back was built to prevent pond overflow - the pump was put in back as a precautionary measure - Sellers have moved. Fully insulated attic and garage with dual garage door openers. Automatic window candles with transformer access in upstairs bedroom (access panel). Gas line for outdoor grill on back side of gas fireplace. Architectural 30 year roof. Community & Utilities Ocean Pines HOA $875 per year, Colonial Village $50 per year Average Electric (Choptank Electric) $250 per month. Water (Ocean Pines) $240 per quarter. Lot size .27 acres. View: Pond and wooded views. Very Peaceful. This home offer an unbeatable combination of quality construction, elegant design, and functional living space. This home cannot be built for this price. Whether full time or part time, this home is a place to gather, relax and live the coastal lifestyle to its fullest.

101 Mumfords Landing Rd, Ocean Pines
$879,900
5 Beds ⋅ 4 Baths ⋅ MDWO2034096 MLS
This brand-new 5-bedroom, 3.5-bath coastal farmhouse blends modern luxury with timeless design. Thoughtfully crafted with premium finishes throughout, it features 9-foot ceilings, an 18-foot vaulted great room with a custom fireplace, built-ins, and an open floor plan perfect for entertaining and everyday living. The designer kitchen is truly the heart of the home. It showcases solid wood cabinetry in soft sage and dove tones, Calacatta Prado quartz countertops and backsplash, and a large center island with a built-in microwave, prep sink, and elegant brass chandelier. The kitchen is equipped with high-end GE stainless steel appliances, including a gas range with an air fryer, French door refrigerator, and a quiet dishwasher. A pot filler, brushed brass fixtures, and soft-close cabinetry add to the thoughtful details, while a spacious walk-in pantry provides additional storage and convenience. The first-floor primary suite offers a relaxing retreat with a spa-like bathroom featuring a freestanding soaking tub, double vanity, and tiled shower. Upstairs, you will find additional bedrooms, a versatile loft, and a beautifully appointed bathroom. This home is designed with efficiency and durability in mind, featuring a Bosch dual-zone HVAC system, Rinnai tankless water heater, sound-insulated six-inch exterior walls, and a sprinkler and fire suppression system. Outside, enjoy covered front and rear porches, a finished two-car garage, and a newly paved driveway. Every detail of this home reflects quality, comfort, and thoughtful design, creating an exceptional coastal living experience. Photos are digital renders.

4 Preakness Dr, Ocean Pines
$2,295,000
4 Beds ⋅ 4 Baths ⋅ MDWO2033424 MLS
The opportunity to own the premier property in Ocean Pines comes around only once in a blue moon. Situated on a point lot on Leigh Drive with the most unobstructed views in the Tern’s Landing neighborhood. The 3 level Mediterranean masterpiece has been tastefully curated blending elevated style, design, and architecture. Privately nestled at the end of a cul-de-sac, this 4-bedroom home promotes an indoor-outdoor lifestyle with balconies and decks on every level to admire the panoramic views of Ocean City. Posh customizations including Walker Zanger tiles, Emtek doorknobs, Ralph Lauren pure wool carpet, Kohler faucets, Subzero and Bosch appliances to name a few. Featuring an expansive primary suite with secluded balcony and telescope lookout. Maintenance free exterior with Techo-Bloc pavers and 200 feet of vinyl bulkhead with dock and boat lift. This home radiates coastal luxury and sophistication. Call today for more information!

36 Leigh Dr, Ocean Pines
$120,000
MDWO2033052 MLS
Beautiful, wooded lot with all the peace and tranquility that Whitetail Sanctuary provides. Almost 2500 sq ft of buildable area with plenty of green space surrounding the building envelope for privacy. Close to all the amenities Ocean Pines offers, including marinas, golf club, pools, Yacht Club, and Ocean Club facilities. Build that dream home you always wanted nestled in the woods and watch the wildlife out your windows or from your outdoor oasis.

226 Charleston Rd, Ocean Pines
$250,000
MDWO2031912 MLS
HUGE PRICE REDUCTION!!! Design and build your custom coastal retreat on this rare 0.18-acre waterfront lot offering expansive views of peaceful Manklin Creek. Nestled on Boston Drive in the sought-after Ocean Pines community, this homesite promises privacy and tranquility with unspoiled nature views and minimal development across the creek, a true luxury along the coast. Enjoy the best of coastal living with Ocean Pines’ premier amenities at your doorstep: marinas, yacht club, golf, pools, parks, and Ocean City’s beaches just minutes away. Boundary survey, wetland determination report, and MDE letter of authorization are already on file, making it easy to bring your vision, your builder, and then watch it come to life. Opportunities like this are incredibly limited, secure your waterfront slice of the Eastern Shore while you still can. Sellers have already taken time to get MDE permit and have paid the mitigation, this saves buyers tons of time and thousands of dollars. The property offers navigable waterfront with the ability to construct a dock and pier. Neighboring owners currently keep a pontoon boat on the creek, demonstrating recreational boating access. Buyers should verify water depths for their specific vessel.

72 Boston Dr, Ocean Pines
$425,000
4 Beds ⋅ 2 Baths ⋅ MDWO2031478 MLS
Don't miss out on this incredible opportunity to own a piece of Ocean Pines paradise. With its unbeatable location, stunning design, and endless possibilities, this remodeled 4 bedroom, 2 bath home is the perfect haven for anyone looking to experience the best of coastal living. Brand new 2.5 ton Rheem heat pump system and Honeywell thermostat just installed June 2026. This home in 2022 went under major rehab with new architectural roof, new siding and shutters, high efficiency tilt in windows, new flooring throughout, vanities and a beautiful gourmet kitchen with a large granite breakfast bar that seats 6. One of the larger lots in the Pines with the home situated to easily add a two-car garage. South gate living at its best and just a few houses over from the bay. Schedule a showing today and make your dreams a reality!

120 Robin Hood, Ocean Pines
$335,000
MDWO2030022 MLS
Welcome to this beautiful waterfront lot in Ocean Pines Teal Bay Community. This pristine lot is available to Build your dream home on .21 acres with a bullhead. Cleared and ready for you to invest in the beach life and the great community of Ocean Pines. The community offers so many amenities for all ages and interests. You have the option to enjoy multiple pools, trails, parks, restaurants, golf and activities. Don’t miss out on this rare opportunity to have the beach and water lifestyle. There is a survey available and great pictures to view this lovely lot. Call Today to set up your tour !

392 Ocean Pkwy, Ocean Pines
$140,000
MDWO2023118 MLS
Welcome to 21 Alden Ct, a serene 0.15-acre lot tucked at the end of a peaceful cul-de-sac in the sought-after Ocean Pines community. This prime lot offers the rare benefit of waterfront access, providing the perfect backdrop to design and build your custom home. Situated within the vibrant Ocean Pines, this property grants you access to a wealth of top-notch amenities, including the Ocean Pines Golf Club, outdoor pools, tennis and pickleball courts, basketball courts, and soccer fields. For boating and water enthusiasts, take advantage of the fishing marina with boat slips, and enjoy exclusive access to the Ocean Pines Beach Club on 49th St. in Ocean City. The community also boasts kids' play areas, walking and jogging trails, and numerous parks that cater to families and outdoor lovers alike. Savor a meal at the Yacht Club, overlooking the marina, or partake in the many social events such as ice cream socials, bingo, and community yard sales. Conveniently located just minutes from the beach, golf courses, dining, and shopping, this property offers the perfect blend of coastal living and everyday convenience. Across the street, a walkway leads you directly to a bustling farmers market, craft shows, live music under the pavilion, and a large playground. Don’t miss this fantastic opportunity to build your waterfront retreat in the heart of Ocean Pines!

21 Alden Ct, Ocean Pines