Ocean Pines - Sherwood Forest Real Estate

Ocean Pines - Sherwood Forest Real Estate

Welcome to Ocean Pines - Sherwood Forest, a hidden gem nestled in the heart of Worcester County, Maryland. This charming subdivision offers a unique blend of coastal living and serene woodland surroundings, making it an ideal destination for families, retirees, and anyone seeking a tranquil lifestyle.

Ocean Pines is renowned for its picturesque landscapes and vibrant community atmosphere. Sherwood Forest, one of its most sought-after neighborhoods, boasts beautifully designed homes that harmonize with the natural beauty of the area. Here, you'll find a variety of architectural styles, from cozy cottages to spacious family residences, all set against the backdrop of lush trees and scenic views.

Residents of Sherwood Forest enjoy exclusive access to a wealth of amenities, including pristine beaches, golf courses, and outdoor recreational facilities. The community features several parks, walking trails, and playgrounds, perfect for afternoon strolls or family picnics. Additionally, the Ocean Pines Association provides a range of social events and activities throughout the year, fostering a strong sense of community among neighbors.

Located just a short drive from the vibrant boardwalk of Ocean City, residents can easily indulge in the area’s rich culture, dining, and entertainment options. Whether you’re looking to enjoy a day at the beach, explore local shops, or savor fresh seafood at waterfront restaurants, Ocean Pines - Sherwood Forest offers the perfect balance of relaxation and adventure.

Discover your dream home in this idyllic community where nature meets convenience, and make Ocean Pines - Sherwood Forest your new haven!

Newest Listings in Ocean Pines - Sherwood Forest

34 Preakness Dr, Berlin
$798,000
4 Beds ⋅ 4 Baths
Welcome to Triple Crown Estates in the South Gate of Ocean Pines. This beautiful new home is a stunning 4‑bedroom, 3.5‑bath custom build by Ultimate Homes, LLC. This coastal‑styled residence offers 2675 sq ft of beautifully designed living space—Crafted with quality and comfort in mind, the home features 2×6 construction, luxury vinyl plank flooring, marble countertops, stainless steel appliances, 60 inch linear fireplace and beautiful finishes throughout. The spacious layout and coastal design elements create a bright, inviting atmosphere perfect for everyday living or relaxing getaways. Ideally located just a few miles from Historic Berlin and the Ocean City beaches and boardwalk, this home offers the best of Eastern Shore living. Weather permitting, you could be settling into your dream property by May! Buy with confidence and peace of mind as the sellers are offering a 2/10 year extended home warranty through Quality Builders Warranty!

34 Preakness Dr, Berlin

Listing courtesy of Sheppard Realty Inc. Contact:

9 Cottonwood Ct, Ocean Pines
$367,500
3 Beds ⋅ 2 Baths
Seller is getting the home ready to see and packing up the personal items that will be sent to the new residence. Custom-built coastal contemporary with a delightful Sun/Florida Room added in 2004 plus an 8x12 rear deck. Vaulted ceiling in the Living Room greets you at your entry from the covered front porch. A gravel walkway from the rear deck to a 9x11 tall shed for all your storage needs. Gutter guards added in 2025 and the bath and shower in 2nd bathroom updated in 2024. New hot water heater in 2022 and crawl space encapsulation in 2020. New roof 2018 and new composite decking on front porch in 2018, also. Walk-in shower done in primary bath in 2014 and new furnace + heat pump in 2012. On a Cul de sac street in the Sherwood Forest section of the wonderful community of Ocean Pines with lots of amenities and recreational opportunities to live or vacation. Lovingly maintained and updated as the need arose.

9 Cottonwood Ct, Ocean Pines

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

1228 Ocean Pkwy, Ocean Pines
$299,900
3 Beds ⋅ 2 Baths
BEST VALUE IN OCEAN PINES! Now’s your chance to be part of the Ocean Pines lifestyle! 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:

2 Cottonwood Ct, Ocean Pines
$117,500
There are very few vacant lots left in the Award-Winning and Amenity-Filled Community of Ocean Pines! Showcase your new home on this beautiful wooded corner lot located in the Sherwood Forest section, with access to public water and sewer. Just a short walk or ride to multiple parks, restaurants, banks, post office, library and much more. Only a few miles to the Ocean City beaches, boardwalk, entertainment and amusements. You may also enjoy nature at Assateague Island National Seashore or antiquing and events in nearby historic Berlin. This destination truly has it all, see why the locals love living here!

2 Cottonwood Ct, Ocean Pines

Listing courtesy of Hileman Real Estate-Berlin. Contact:

1212 Ocean Pkwy, Ocean Pines
$435,000
3 Beds ⋅ 2 Baths
Welcome to Sherwood Forest...in Ocean Pines that is! This contemporary ranch home features 3 bedrooms, 2 full baths, an open living room that flows into the dining area and kitchen, rear sunroom and a walk-up attic which is accessed via the interior of the garage. All of this on a 0.17 +/- acre parcel that backs up to a peaceful wooded area. As part of the 3,000 +/- acre Ocean Pines Community, amenities abound to engage all facets of yourlifestyle! Located approximately 3 miles from Ocean Downs Casino, 8 miles from the boardwalk, beach andAtlantic Ocean in Ocean City, MD and 13 miles from the Assateague Island National Seashore Park. EasternShore living at its finest!Restricted to owner-occupants, non-profits and government agencies through 11/16/2026. HUD Case #241-900265. Seller may contribute up to 3% of the buyer’s closing costs. Equal Housing Opportunity.

1212 Ocean Pkwy, Ocean Pines

Listing courtesy of Brokers Realty Group, LLC. Contact:

110 High Sheriff Trl, Ocean Pines
$379,900
3 Beds ⋅ 2 Baths
South Ocean Pines rancher with a 3 year old roof, attached garage, crown molding throughout, primary en-suite with two closets and a full bath with easy-access shower plus a tub. as well as new LVP flooring in the kitchen, dining area and laundry. The 4-season sunroom offers lots of natural light and opens to the spacious living room. A gas tankless water heater offers efficient on demand hot water.

110 High Sheriff Trl, Ocean Pines

Listing courtesy of Coldwell Banker Realty. Contact:

129 High Sheriff Trl, Ocean Pines
$339,000
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
$300,000
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
$263,150
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:

7 Jockey Ct, Berlin
$785,000
4 Beds ⋅ 3 Baths
BIGGER, BETTER… BUT you better hurry if you want to pick your own colors! Photos are actually pictures of 83 King Richard the beautiful HUNTER I model that sold !! “ The Hunter I” model is the little brother of The Hunter II currently being built at 5 Jockey Court (also pending) and now on 7 Jockey Court with a larger footprint and on a larger lot (see house plans). Crafted by Ultimate Homes, LLC, this masterfully designed 4-bedroom, 2.5-bath with den/office all in this sprawling rancher located in the prestigious new section of Triple Crown Estates in Ocean Pines. Blending timeless craftsmanship with refined modern finishes, this residence offers an elevated lifestyle just moments from the coast. Inspired Design. Exceptional Comfort, From the moment you arrive, the home’s commanding presence and architectural detail set the tone for what lies within. Built with 2x6 construction and topped with 40-year architectural shingles, the quality is evident at every turn. Inside, an expansive open-concept layout creates seamless flow between the living, dining, and kitchen spaces — ideal for both intimate gatherings and grand entertaining. Elegant Luxury Vinyl Plank flooring throughout the main living areas and a striking Electric Linear Fireplace as a contemporary focal point. Designer kitchen featuring Quartz countertops and premium finishes Spacious primary suite designed for rest and rejuvenation Thoughtfully appointed secondary bedrooms for family or guests Every detail reflects a commitment to craftsmanship and livability. Coastal Proximity. Private Serenity, perfectly situated just five miles from the vibrant shoreline of Ocean City and the natural beauty of Assateague Island, this home offers effortless access to beaches, boating, dining, and outdoor adventure — while preserving the tranquility of a refined residential setting. Fall 2026 Delivery. This is more than a home — it is a statement of lifestyle, comfort, and coastal sophistication. Experience “The Hunter II” on a bigger lot and softer than the "The Hunter". Where craftsmanship meets coastal elegance. Buy with confidence and peace of mind as the sellers are offering a 2/10 year extended home warranty through Quality Builders Warranty! Call now to pick your colors and finishes in The Hunter II some photos have been virtually staged

7 Jockey Ct, Berlin

Listing courtesy of Sheppard Realty Inc. Contact:

1142 Ocean Pkwy, Ocean Pines
$349,500
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:

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