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Welcome to 11 Southwind Court, a beautiful custom-designed 4-bedroom, 3-full-bath home offering the perfect blend of comfort, space, and coastal living in the amenity-rich community of Ocean Pines. Tucked away on a quiet cul-de-sac, this spacious home features an inviting open floor plan filled with abundant natural light and plenty of room for family and guests. The heart of the home is the spacious kitchen with a 2nd wall oven which is a electric-convection oven next to the great room, creating a wonderful gathering place for everyday living and entertaining. The open design provides an easy flow between the kitchen, dining, and living areas, while generous room sizes and thoughtful details throughout make this home both comfortable and functional. With four bedrooms, three full baths, and an additional room above the garage, this flexible floor plan offers plenty of options for a primary residence, second home, or coastal retreat. The spacious primary suite provides privacy and comfort, while the additional bedrooms and bonus room offer plenty of space for family, guests, a home office, hobby room, or additional living area. Step outside and discover one of this home's standout features — your own private outdoor pool surrounded by a vinyl-fenced backyard. Whether you're cooling off on a summer afternoon, hosting family and friends, enjoying a crab feast, or simply relaxing after a day at the beach, this private outdoor space is perfect for enjoying the coastal lifestyle and making lasting memories. Located in the award-winning community of Ocean Pines, residents can enjoy an incredible variety of amenities, including indoor and outdoor pools, parks and playgrounds, golf, boating, fishing, crabbing, the Yacht Club, community center, and much more. You're also just a short drive from Ocean City's beaches and boardwalk, historic downtown Berlin, Assateague Island, and everything Maryland's Eastern Shore has to offer.

4 Beds ⋅ 3 Baths

Welcome to 11 Southwind Court, a beautiful custom-designed 4-bedroom, 3-full-bath home offering the perfect blend of comfort, space, and coastal living in the amenity-rich community of Ocean Pines. Tucked away on a quiet cul-de-sac, this spacious home features an inviting open floor plan filled with abundant natural light and plenty of room for family and guests. The heart of the home is the spacious kitchen with a 2nd wall oven which is a electric-convection oven next to the great room, creating a wonderful gathering place for everyday living and entertaining. The open design provides an easy flow between the kitchen, dining, and living areas, while generous room sizes and thoughtful details throughout make this home both comfortable and functional. With four bedrooms, three full baths, and an additional room above the garage, this flexible floor plan offers plenty of options for a primary residence, second home, or coastal retreat. The spacious primary suite provides privacy and comfort, while the additional bedrooms and bonus room offer plenty of space for family, guests, a home office, hobby room, or additional living area. Step outside and discover one of this home's standout features — your own private outdoor pool surrounded by a vinyl-fenced backyard. Whether you're cooling off on a summer afternoon, hosting family and friends, enjoying a crab feast, or simply relaxing after a day at the beach, this private outdoor space is perfect for enjoying the coastal lifestyle and making lasting memories. Located in the award-winning community of Ocean Pines, residents can enjoy an incredible variety of amenities, including indoor and outdoor pools, parks and playgrounds, golf, boating, fishing, crabbing, the Yacht Club, community center, and much more. You're also just a short drive from Ocean City's beaches and boardwalk, historic downtown Berlin, Assateague Island, and everything Maryland's Eastern Shore has to offer.

11 Southwind Ct, Berlin

Listing courtesy of RE/MAX One. Contact:

$415,000

Welcome to 75 Cresthaven Drive, a charming A-frame home located in the desirable Ocean Pines community! This unique 3-bedroom, 2-bath home offers 1,128 square feet of living space and sits on a spacious 10,700-square-foot lot. Whether you're searching for a beach getaway, full-time residence, or investment property, this home offers plenty of possibilities. Currently generating approximately $35,000–$38,000 in annual rental income, it provides an excellent opportunity for buyers looking for a proven vacation rental. The distinctive A-frame design gives the home plenty of coastal character, while the large front deck provides the perfect place to relax and enjoy the outdoors. Out back, you'll find an inviting entertainment area complete with a fire pit—ideal for summer evenings, cookouts, and gathering with family and friends. Ownership in Ocean Pines provides access to an impressive array of community amenities, including indoor and outdoor pools, parks, marina, golf course, restaurant, ball fields, dog park, and more. Best of all, you're just minutes from the beaches and famous Boardwalk of Ocean City, along with fantastic restaurants, shopping, golf, boating, and everything the Maryland coast has to offer. A great combination of character, location, community amenities, and rental potential—75 Cresthaven Drive is ready for its next owner!

3 Beds ⋅ 2 Baths

Welcome to 75 Cresthaven Drive, a charming A-frame home located in the desirable Ocean Pines community! This unique 3-bedroom, 2-bath home offers 1,128 square feet of living space and sits on a spacious 10,700-square-foot lot. Whether you're searching for a beach getaway, full-time residence, or investment property, this home offers plenty of possibilities. Currently generating approximately $35,000–$38,000 in annual rental income, it provides an excellent opportunity for buyers looking for a proven vacation rental. The distinctive A-frame design gives the home plenty of coastal character, while the large front deck provides the perfect place to relax and enjoy the outdoors. Out back, you'll find an inviting entertainment area complete with a fire pit—ideal for summer evenings, cookouts, and gathering with family and friends. Ownership in Ocean Pines provides access to an impressive array of community amenities, including indoor and outdoor pools, parks, marina, golf course, restaurant, ball fields, dog park, and more. Best of all, you're just minutes from the beaches and famous Boardwalk of Ocean City, along with fantastic restaurants, shopping, golf, boating, and everything the Maryland coast has to offer. A great combination of character, location, community amenities, and rental potential—75 Cresthaven Drive is ready for its next owner!

75 Cresthaven Dr, Ocean Pines

Listing courtesy of RE/MAX One. Contact:

$349,000

Nestled in a charming and peaceful pocket of Ocean Pines, this inviting one-level rancher offers 3 bedrooms and 2 full baths. The home features beautiful hardwood floors, granite countertops, and an updated primary bathroom with a custom-tiled shower. Step outside onto the back deck overlooking a private backyard that backs to a wooded setting, creating a peaceful retreat for relaxing or entertaining. The convenient single-level layout offers comfortable, easy living with everything you need on one floor. A wonderful opportunity to enjoy all that Ocean Pines has to offer at an attractive price. Schedule your showing today!

3 Beds ⋅ 2 Baths

Nestled in a charming and peaceful pocket of Ocean Pines, this inviting one-level rancher offers 3 bedrooms and 2 full baths. The home features beautiful hardwood floors, granite countertops, and an updated primary bathroom with a custom-tiled shower. Step outside onto the back deck overlooking a private backyard that backs to a wooded setting, creating a peaceful retreat for relaxing or entertaining. The convenient single-level layout offers comfortable, easy living with everything you need on one floor. A wonderful opportunity to enjoy all that Ocean Pines has to offer at an attractive price. Schedule your showing today!

38 Fairway Ln, Berlin

Listing courtesy of Bunting Realty. Contact:

$459,000

Welcome to this inviting 3-bedroom, 2-bath ranch-style home in the desirable Ocean Pines community. Recently refreshed with new carpet and fresh paint throughout, along with a new roof, this home offers a great combination of comfort and functionality. The floor plan connects the living, dining, and kitchen areas, while skylights bring plenty of natural light into the home. A cozy gas fireplace adds warmth and character to the main living space. The spacious primary suite features a walk-in closet and private bath. Step outside to enjoy the screened porch and spacious deck, offering a great spot for relaxing, grilling, or entertaining. An attached two-car garage and concrete driveway provide plenty of parking and additional storage. Enjoy all that Ocean Pines has to offer, including pools, parks, sports courts, walking and biking trails, golf, marinas, and more. With a functional single-level layout, fresh updates, and inviting indoor and outdoor living spaces, this home is ready to welcome its next owners.

3 Beds ⋅ 2 Baths

Welcome to this inviting 3-bedroom, 2-bath ranch-style home in the desirable Ocean Pines community. Recently refreshed with new carpet and fresh paint throughout, along with a new roof, this home offers a great combination of comfort and functionality. The floor plan connects the living, dining, and kitchen areas, while skylights bring plenty of natural light into the home. A cozy gas fireplace adds warmth and character to the main living space. The spacious primary suite features a walk-in closet and private bath. Step outside to enjoy the screened porch and spacious deck, offering a great spot for relaxing, grilling, or entertaining. An attached two-car garage and concrete driveway provide plenty of parking and additional storage. Enjoy all that Ocean Pines has to offer, including pools, parks, sports courts, walking and biking trails, golf, marinas, and more. With a functional single-level layout, fresh updates, and inviting indoor and outdoor living spaces, this home is ready to welcome its next owners.

36 Fairway Ln, Ocean Pines

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

$412,500

Nestled in the charming community of Ocean Pines, this delightful 4-bedroom, 2.5-bathroom home offers a perfect blend of comfort and convenience. With 1,660 square feet of living space, this traditional-style residence is designed for both relaxation and entertaining. The inviting fireplace serves as a cozy focal point, perfect for gathering with loved ones on chilly evenings. The roof 2023 and windows were replaced in 2018; a New water heater in 2025; the living room was remodeled in 2023; the dining and kitchen flooring were replaced in 2026; the stove and dishwasher are newer, and the bathrooms have all been newly renovated. The owner installed Blink security cameras that are ready to be switched over. Ocean Pines is more than just a neighborhood; it's a vibrant community brimming with amenities. Enjoy sunny days at the community beach or take a stroll along the scenic bike trails. For the active lifestyle, the area boasts baseball fields, basketball courts, tennis courts, and pickleball courts, ensuring there's always something to do. The community center and library provide spaces for social gatherings and learning, while the dog park is perfect for furry friends to play. With community pools, both indoor and outdoor, residents can enjoy refreshing swims year-round. The Ocean Pines Golf Club adds an extra touch of leisure, with membership options available for golf enthusiasts. This home is not just a place to live; it's a gateway to a lifestyle filled with community spirit and recreational opportunities. Experience the warmth and charm of Ocean Pines, where every day feels like a vacation.

4 Beds ⋅ 3 Baths

Nestled in the charming community of Ocean Pines, this delightful 4-bedroom, 2.5-bathroom home offers a perfect blend of comfort and convenience. With 1,660 square feet of living space, this traditional-style residence is designed for both relaxation and entertaining. The inviting fireplace serves as a cozy focal point, perfect for gathering with loved ones on chilly evenings. The roof 2023 and windows were replaced in 2018; a New water heater in 2025; the living room was remodeled in 2023; the dining and kitchen flooring were replaced in 2026; the stove and dishwasher are newer, and the bathrooms have all been newly renovated. The owner installed Blink security cameras that are ready to be switched over. Ocean Pines is more than just a neighborhood; it's a vibrant community brimming with amenities. Enjoy sunny days at the community beach or take a stroll along the scenic bike trails. For the active lifestyle, the area boasts baseball fields, basketball courts, tennis courts, and pickleball courts, ensuring there's always something to do. The community center and library provide spaces for social gatherings and learning, while the dog park is perfect for furry friends to play. With community pools, both indoor and outdoor, residents can enjoy refreshing swims year-round. The Ocean Pines Golf Club adds an extra touch of leisure, with membership options available for golf enthusiasts. This home is not just a place to live; it's a gateway to a lifestyle filled with community spirit and recreational opportunities. Experience the warmth and charm of Ocean Pines, where every day feels like a vacation.

63 Newport Dr, Ocean Pines

Listing courtesy of ERA Martin Associates. Contact:

$410,000

MOTIVATED SELLER, BRING ALL OFFERS!! $10,000.00 CLOSING COST/RATE BUY-DOWN CREDIT!! Move-In Ready & Furnished in Ocean Pines! NEW ROOF, VAPOR BARRIER AND DEHUMIDIFIER INSTALLED 09/08/26! Welcome to 150 Sandyhook Road, a beautifully situated 3-bedroom, 2-bath home on a generous .47-acre lot in desirable Ocean Pines. Offered fully furnished and move-in ready, this home makes it easy to start enjoying the Eastern Shore lifestyle from day one. Relax and entertain from the inviting screened-in porch, perfect for morning coffee, afternoon drinks, or gathering with friends and family. The property also features an oversized insulated garage with built-in storage cabinets, providing plenty of room for vehicles, bikes, beach gear, tools, and recreational equipment. Major peace-of-mind update- A new roof was installed September 8, 2026 as well as a new vapor barrier and dehumidifier in the crawl space. This home also features on-demand hot water, adding efficiency and convenience. With three bedrooms, two full bathrooms, a spacious lot, ample garage storage, and furnishings included, this property is an ideal choice for a year-round residence, second home, or coastal getaway. And then there's Ocean Pines! The community offers an impressive array of amenities, including multiple pools, golf, tennis, pickleball, marinas, parks, trails, and access to the Ocean Pines Beach Club in Ocean City. Just bring your suitcase and start enjoying everything Ocean Pines and the Eastern Shore have to offer!

3 Beds ⋅ 2 Baths

MOTIVATED SELLER, BRING ALL OFFERS!! $10,000.00 CLOSING COST/RATE BUY-DOWN CREDIT!! Move-In Ready & Furnished in Ocean Pines! NEW ROOF, VAPOR BARRIER AND DEHUMIDIFIER INSTALLED 09/08/26! Welcome to 150 Sandyhook Road, a beautifully situated 3-bedroom, 2-bath home on a generous .47-acre lot in desirable Ocean Pines. Offered fully furnished and move-in ready, this home makes it easy to start enjoying the Eastern Shore lifestyle from day one. Relax and entertain from the inviting screened-in porch, perfect for morning coffee, afternoon drinks, or gathering with friends and family. The property also features an oversized insulated garage with built-in storage cabinets, providing plenty of room for vehicles, bikes, beach gear, tools, and recreational equipment. Major peace-of-mind update- A new roof was installed September 8, 2026 as well as a new vapor barrier and dehumidifier in the crawl space. This home also features on-demand hot water, adding efficiency and convenience. With three bedrooms, two full bathrooms, a spacious lot, ample garage storage, and furnishings included, this property is an ideal choice for a year-round residence, second home, or coastal getaway. And then there's Ocean Pines! The community offers an impressive array of amenities, including multiple pools, golf, tennis, pickleball, marinas, parks, trails, and access to the Ocean Pines Beach Club in Ocean City. Just bring your suitcase and start enjoying everything Ocean Pines and the Eastern Shore have to offer!

150 Sandyhook Rd, Ocean Pines

Listing courtesy of Coldwell Banker Realty. Contact:

$559,900

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.

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: