Ocean Pines - Sherwood Forest Homes under $500,000

Ocean Pines - Sherwood Forest Homes under $500,000

Welcome to Ocean Pines - Sherwood Forest, a charming subdivision nestled in the heart of Worcester County, Maryland. This delightful community is just a stone's throw away from the stunning Atlantic coastline, offering residents a perfect blend of serene living and vibrant coastal activities. With its lush landscapes and picturesque surroundings, Ocean Pines - Sherwood Forest is an ideal place for families, retirees, and anyone seeking a peaceful retreat.

One of the standout features of this subdivision is the availability of beautiful homes priced under $500,000. This makes Ocean Pines - Sherwood Forest not only an attractive option for first-time homebuyers but also for those looking to downsize without compromising on quality or comfort. The homes in this community range from cozy single-family residences to spacious townhouses, each offering unique architectural styles and modern amenities.

Residents enjoy access to a wealth of community features, including parks, walking trails, and recreational facilities. The Ocean Pines Association provides a plethora of activities and events throughout the year, ensuring there's always something to do. Whether you prefer a leisurely day at the beach, exploring local shops, or indulging in delicious dining options, Ocean Pines has it all.

Living in Ocean Pines - Sherwood Forest means embracing a lifestyle that celebrates both relaxation and adventure. With its affordable housing options, stunning natural beauty, and a strong sense of community, this subdivision is truly a hidden gem in Maryland. Come discover your dream home in Ocean Pines today!

Newest Ocean Pines - Sherwood Forest Homes under $500,000

129 High Sheriff Trl, Ocean Pines
$349,990
3 Beds ⋅ 2 Baths
Discover the perfect blend of comfort, space, and coastal living in this inviting home tucked away just off the parkway in desirable Ocean Pines, a short drive from the beautiful beaches of Ocean City!Step inside to a spacious living room featuring upgraded flooring and an inviting atmosphere perfect for relaxing or entertaining. The upgraded kitchen offers functionality and style, while the adjoining open sunroom provides endless possibilities. Imagine using this versatile space as a dining room, a second living area, a home office, or the perfect spot to enjoy your morning coffee.Just beyond the sunroom, step outside to a large deck featuring a charming arbor—an ideal setting for summer barbecues, outdoor dining, and gathering with family and friends. With three bedrooms and two-and-a-half baths, this home offers plenty of room to spread out and enjoy everything coastal living has to offer.Ocean Pines is known for its exceptional community amenities, including indoor and outdoor swimming pools, a yacht club, pickleball courts, scenic walking and biking trails, and a golf course. Residents also enjoy access to a private beach club in Ocean City, offering a convenient place to spend sunny days at the beach along with free parking. Whether you're looking for a full-time residence, a relaxing second home, or the perfect vacation getaway, this home offers the opportunity to embrace the laid-back coastal lifestyle you've been dreaming of. Enjoy the best of Ocean Pines living, with the beautiful beaches of Ocean City and the natural beauty of Assateague Island just a short drive away!

129 High Sheriff Trl, Ocean Pines

Listing courtesy of Atlantic Shores Sotheby's International Realty. Contact:

59 Castle Dr, Ocean Pines
$320,000
3 Beds ⋅ 2 Baths
Welcome to this charming single-level home nestled among mature trees in the highly desirable Ocean Pines community! Situated on a spacious, wooded, corner lot, this property offers a peaceful setting with plenty of outdoor space to enjoy. Inside, you'll find a comfortable and functional layout featuring a combination of luxury vinyl plank flooring and carpeting, generously sized windows that bring in natural light, and a wood-burning-style stove that serves as a cozy focal point. Additional highlights include a dedicated laundry room, an exterior ramp leading to the front entrance, and a paved driveway providing convenient off-street parking. Outside, the property offers a detached storage shed, an additional rear structure, and plenty of room to create your ideal outdoor retreat. Ocean Pines is known for its incredible selection of amenities and recreational opportunities. Residents can enjoy multiple outdoor swimming pools, an indoor aquatic center, the Ocean Pines Golf Club featuring an 18-hole championship course, tennis courts, pickleball courts, basketball courts, playgrounds, parks, walking trails, and the Ocean Pines Yacht Club overlooking the Isle of Wight Bay. The community also offers marinas, boat ramps, fishing and crabbing opportunities, a community center, and the Ocean Pines Beach Club located directly on the beach in Ocean City. With numerous community events and activities throughout the year, there is always something to enjoy! Conveniently located just a short drive from the beaches, boardwalk, restaurants, shopping, and entertainment of Ocean City, as well as the charming downtown of Berlin, this property offers the perfect combination of a quiet residential setting and easy access to everything the Eastern Shore has to offer. Whether you're searching for a primary residence, vacation getaway, or investment opportunity, this Ocean Pines property is full of potential. Come explore the possibilities and enjoy all that this wonderful coastal community has to offer!

59 Castle Dr, Ocean Pines

Listing courtesy of Coastal Life Realty Group LLC. Contact:

141 Nottingham Ln, Ocean Pines
$277,000
2 Beds ⋅ 2 Baths
This Ranch style home in Ocean Pines, Maryland offers two bedrooms, bonus room or office, split floorplan and an attached rear storage area. The home sits close to the Ocean City Boardwalk and close to Assateague Island National Seashore, both within a short drive for beach days and time outdoors. Contact me to schedule a showing and see how this Ocean Pines ranch could work for you.

141 Nottingham Ln, Ocean Pines

Listing courtesy of Sheppard Realty Inc. Contact:

66 Robin Hood Trl, Ocean Pines
$375,000
3 Beds ⋅ 2 Baths
Welcome to this beautiful charming updated home located in the Sherwood Forest section of Ocean Pines! This home features 3 bedrooms with neutral color carpeting The main bedroom offers an en-suite with double sinks, beautiful laminate flooring.There is a 2nd bath with same beautiful laminate flooring The vaulted ceiling in the living room creates an open airy feeling along with a gas fireplace for those cozy evenings. The spacious kitchen has gorgeous laminate flooring,white cabinetry with lots of storage You'll also find a walk- in pantry which adds additional storage The kitchen flows into the dining area giving lots of space for family gatherings.Off the dining area is another room with a sliding door which could be used as an office or perhaps another quiet space to enjoy the peaceful surroundings. Step outside from there to a private yard that backs to woods. You can create a place for entertaining or a place to simply relax and take in all the beautiful nature that abounds. Whether you're searching for a year-round residence or a coastal getaway, this home offers the opportunity to enjoy the many amenities Ocean Pines has to offer!

66 Robin Hood Trl, Ocean Pines

Listing courtesy of EXP Realty, LLC. Contact:

1142 Ocean Pkwy, Ocean Pines
$353,000
3 Beds ⋅ 2 Baths
Looking for a permanent home or a vacation get away? This is it! Offering both convenience and relaxation this home has one level living with an open floor plan, vaulted ceilings, a combined dining and kitchen area, a gas fireplace for cozy evenings and a screen porch to enjoy through all the seasons. This coastal contemporary has three bedrooms and two full baths. The luxury vinyl plank flooring, vanity lights, fixtures, ceiling fans and appliances are only about a year old. Ocean Pines has all the amenities you could ever hope for: volleyball, parks, a marina, a golf course, both indoor and outdoor pools, walking trails and a variety of clubs and activities. Easy access to nearby beaches and attractions come fall in love with the magic of Ocean Pines living.

1142 Ocean Pkwy, Ocean Pines

Listing courtesy of ERA Martin Associates. Contact:

1228 Ocean Pkwy, Ocean Pines
$329,900
3 Beds ⋅ 2 Baths
Now’s your time to be part of life in Ocean Pines! You’ll love the convenience of one-level living in this updated 3 bedroom 1.5 bath rancher in Sherwood Forest. Relax or entertain in your spacious sun-drenched family room that leads into an eat-in kitchen with updated appliances and enclosed laundry room. From the kitchen, step into the spacious screened-in porch and large partially fenced back yard overlooking trees. Ocean Pines offers an exceptional array of amenities including multiple pools, boat ramps, playgrounds, walking trails, a community center, and much more. All of this is only a few miles from Ocean City where you’ll find the Ocean Pines beach club with a pool, restaurant, locker rooms and other activities. Ocean Pines isn���t just a neighborhood it’s a vibrant community with something for everyone. If you’re looking for an investment, this property has been partially rented generating a steady income.

1228 Ocean Pkwy, Ocean Pines

Listing courtesy of The KW Collective. Contact:

13 Catalpa Ln, Ocean Pines
$475,000
3 Beds ⋅ 2 Baths
This well maintained home on a quiet cul de sac in the south gate of Ocean Pines features an open floor plan. The main level is bright with cathedral ceilings in the living room, a dining area off of the large kitchen with updated appliances and a 2nd sitting area, a first floor primary suite with high ceilings and walk in closet. You will also find on the first floor a laundry room with utility sink, a half bath, access to the attached garage with bonus storage area and a large 4 seasons room with a gas fireplace that leads to the back deck. The second level features 2 additional bedrooms, a full bathroom and a small bonus room along with storage area. Roof and skylight were replaced in 2022.

13 Catalpa Ln, Ocean Pines

Listing courtesy of Coastal Life Realty Group LLC. Contact:

14 Willow Way, Ocean Pines
$394,500
3 Beds ⋅ 2 Baths
Welcome to 14 Willow Way in Ocean Pines! Situated on a peaceful cul-de-sac, this beautifully updated 3-bedroom, 2-bath home offers inviting living spaces and an impressive list of recent upgrades. The main level features LVP flooring throughout, a spacious living area with a beautiful cathedral ceiling, and an updated kitchen showcasing quartz countertops, newer appliances, and a stunning glass tile backsplash. Enjoy seamless indoor-outdoor living from the screened porch, which overlooks the fully fenced backyard and large concrete patio—ideal for entertaining, relaxing, or enjoying warm summer evenings. Two storage sheds provide plenty of space for bikes, tools, beach gear, and more. A brand-new roof adds peace of mind, while the home's thoughtful updates and desirable cul-de-sac setting make it an excellent opportunity to enjoy the Ocean Pines lifestyle. Don't miss your chance to make this beautifully maintained home your own!

14 Willow Way, Ocean Pines

Listing courtesy of Hileman Real Estate-Berlin. Contact:

25 Royal Oaks Dr, Ocean Pines
$399,900
4 Beds ⋅ 3 Baths
Welcome to 25 Royal Oaks Drive, a beautifully updated Ocean Pines home offering the perfect blend of comfort, flexibility, and coastal living. This spacious 4-bedroom, 3-full-bath residence offers 1,728 square feet of thoughtfully designed living space and is situated on a 7,500-square-foot lot. Step inside to find a bright and inviting interior with a versatile layout designed for everyday living and entertaining. The main level features a comfortable living area, well-appointed kitchen and dining space, and a sliding door leading to the rear deck—an ideal spot for morning coffee, outdoor dining, or relaxing with friends and family. The upper level offers private bedroom accommodations, including a spacious primary suite, while the lower level provides exceptional flexibility with a large bonus room, full bath, laundry area, and walk-out access to the backyard. Use the lower-level space as a fourth bedroom, guest suite, home office, recreation room, or second living area—the possibilities are yours. Numerous updates over the years include the roof, windows, flooring, doors, and appliances, providing a move-in-ready opportunity for the next owner. The outdoor space adds even more appeal, with a rear deck and backyard offering room to enjoy the relaxed Eastern Shore lifestyle. Located in desirable Ocean Pines, this home provides access to an impressive array of community amenities, including pools, beach areas, golf, tennis, pickleball, walking paths, marina facilities, playgrounds, recreation areas, and more. Enjoy the best of coastal Maryland living while remaining just minutes from Ocean City, beaches, dining, shopping, and entertainment. Whether you're looking for a year-round residence, vacation getaway, or investment opportunity, 25 Royal Oaks Drive offers the space, flexibility, and location to make your Eastern Shore lifestyle a reality.

25 Royal Oaks Dr, Ocean Pines

Listing courtesy of Coldwell Banker Realty. Contact:

17 King Richard Rd, Ocean Pines
$374,900
3 Beds ⋅ 2 Baths
Welcome to this well‑maintained contemporary home tucked away in the heart of Sherwood Forest in Ocean Pines. This 3BR, 2BA home with a loft comes partially furnished and features numerous upgrades, including a new heat pump, electric hot water heater, newer roof, new siding, and a front deck with an electric awning. Inside, enjoy Corian countertops, new cabinets, tile backsplash, SS apps, plus a beautifully updated bathroom with a walk‑in shower, vanity & LVP flooring. Outside, you’ll find an enclosed outdoor shower, paved driveway, and a shed with electric—perfect for storage or projects. Make this your next home in Ocean Pines!

17 King Richard Rd, Ocean Pines

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

15 Lord Guy Ter, Ocean Pines
$359,900
3 Beds ⋅ 2 Baths
Welcome to 15 Lord Guy Terrace, a BEAUTIFULLY MAINTAINED one level home in the sought after community of Ocean Pines. Located just minutes from the beaches of Ocean City and Assateague Island, charming downtown Berlin, championship golf courses, marinas, shopping, dining, and year round entertainment, this home offers an ideal combination of coastal lifestyle and everyday convenience. Set on an OVERSIZED LOT with a spacious paved driveway, the property welcomes you with low maintenance landscaping, brick bordered stone beds, a charming front porch, and a convenient side porch that is perfect for outdoor dining, entertaining, or simply enjoying the coastal setting. Inside, the OPEN CONCEPT floor plan creates an easy flow between the living room, dining area, and kitchen, providing a comfortable space for both everyday living and gatherings. The owners suite is privately situated at the front of the home, while two additional bedrooms and a full bath are located toward the rear. Just off the kitchen, the SPACIOUS BONUS ROOM adds valuable flexibility and can easily serve as a second living area, home office, playroom, or potential fourth bedroom with minimal modifications. Living in Ocean Pines provides access to an impressive collection of RESORT STYLE AMENITIES, with both free and paid membership options available. Residents can enjoy swimming pools, parks, playgrounds, walking trails, a championship golf course, marina, yacht club, pickleball and tennis courts, a community garden, and a vibrant community center. Whether you are looking for a full time residence, vacation getaway, or investment property, this home offers the flexibility to fit a variety of lifestyles. Everyday essentials are conveniently close, including grocery stores, pharmacies, healthcare, banks, and local restaurants. Spend the day enjoying Ocean Citys famous Boardwalk and beaches, explore the wild horses and natural beauty of Assateague Island National Seashore, or visit historic downtown Berlin for its boutiques and cafes. Golf enthusiasts will appreciate the nearby selection of courses, including Rum Pointe Seaside Golf Links, the Links at Lighthouse Sound, and Glen Riddle Golf Club. Boating, fishing, and outdoor recreation are also close at hand, while popular Delaware beach destinations including Lewes, Rehoboth Beach, Bethany Beach, and Fenwick Island are all within an approximately 20 to 50 minute drive. With its convenient location, flexible floor plan, oversized lot, and access to the many amenities of Ocean Pines, 15 Lord Guy Terrace is ready to welcome you to the coastal lifestyle!

15 Lord Guy Ter, Ocean Pines

Listing courtesy of Coldwell Banker Realty. Contact:

31 Nottingham Ln, Berlin
$359,000
4 Beds ⋅ 2 Baths
The perfect vacation home or short term rental investments property! Positioned on spacious corner lot in the amenity-rich Ocean Pines community, this inviting cottage-style home offers 4 bedrooms and 2 baths, making it an ideal vacation retreat or investment opportunity. Recent updates include a brand-new HVAC system, brand new conditioned crawl space, new luxury vinyl plank flooring in the bedrooms, and fresh decking for outdoor enjoyment. The extended driveway provides parking for up to 8 vehicles, perfect for hosting guests. Backyard shed is ideal for storing your beach gear! Conveniently located within walking distance to grocery stores, restaurants, and local shopping, this home is also just a short drive to Ocean City, where residents can enjoy exclusive access to the Ocean Pines Beach Club. Ocean Pines offers an abundance of community amenities, including indoor and outdoor pools, several parks and walking trails, tennis and pickleball courts, a championship golf course, and a full-service yacht club. Whether for year-round living or a weekend getaway, this home places coastal living and recreation at your fingertips.

31 Nottingham Ln, Berlin

Listing courtesy of Northrop Realty. Contact:

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