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$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
$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
$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
$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