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 perfect blend of coastal living and serene woodland surroundings, making it an ideal destination for families, retirees, and nature enthusiasts alike.

Ocean Pines is renowned for its vibrant community spirit, featuring a variety of amenities that cater to an active lifestyle. Residents enjoy access to beautiful parks, scenic walking trails, and a wealth of recreational activities, including boating, fishing, and kayaking on the nearby Assawoman Bay. The community also boasts a stunning golf course, perfect for golf aficionados looking to perfect their swing in a picturesque setting.

Sherwood Forest, a tranquil enclave within Ocean Pines, is characterized by its lush landscapes and friendly atmosphere. The homes here reflect a diverse architectural style, offering everything from cozy cottages to spacious family residences. Many properties are surrounded by mature trees, providing a sense of privacy and connection to nature.

Conveniently located just a short drive from Ocean City, residents can easily indulge in the vibrant beachfront lifestyle, complete with shopping, dining, and entertainment options. Whether you’re looking to relax on the sandy shores or explore the local art scene, Ocean Pines - Sherwood Forest serves as the perfect retreat.

Discover the charm of Ocean Pines - Sherwood Forest and embrace a lifestyle that harmonizes community warmth with the beauty of Maryland's coastal landscape. Your dream home awaits in this idyllic subdivision, where every day feels like a vacation!

Newest Listings in Ocean Pines - Sherwood Forest

$469,900
3 Beds ⋅ 3 Baths
Imagine coming home to your own secluded haven surrounded by nature. This impeccably maintained 3-bedroom, 3-bath home delivers effortless one-level living designed around quality, comfort, and coastal entertainment. Step inside to an airy, open layout bathed in natural light, highlighted by updated LVP flooring throughout and a cozy fireplace serving as the warm focal point of the living space. The gourmet kitchen is a true chef’s delight, featuring an expansive island and stunning quartz countertops—making it an absolute dream for hosting and daily prep. Outdoor living is at its finest; relax on the awning-covered front deck or retreat to the generous screened porch to take in the serene, wooded views. Located in an amenity-rich Ocean Pines community, you'll love having pools, golf, and marinas right at your fingertips —all just a short drive from the beaches and excitement of Ocean City!

39 King Richard Rd, Ocean Pines

Listing courtesy of ERA Martin Associates, Shamrock Division. Contact: 4106415000
$539,900
3 Beds ⋅ 2 Baths
This stunning ranch-style home, set on a beautifully landscaped lot, offers a harmonious blend of luxury and comfort. The interior boasts over 1,500 sq. ft. of thoughtfully designed space, featuring three bedrooms and two full bathrooms. The front bedrooms are perfect for guests or as a private office. The heart of the home is the expansive kitchen, complete with an island, stainless steel appliances, and a cozy breakfast bar, seamlessly flowing into the dining area with recessed lighting, and the house is adorned with crown molding throughout. Major renovations in 2024 have elevated this residence, including new roof, interior paint, doors, fixtures, lighting, and appliances. Enjoy the warmth of the electric fireplace in the living area, enhanced by abundant natural light from skylights and insulated windows. The primary suite features a double door entry, tray ceiling, walk-in closet and a spa-like bathroom with a walk-in shower, lighted faucets, and shiplap walls/ceiling. From the light-filled sunroom, step outside to discover a covered porch, fire pit, extensive hardscaping, pea gravel, a hot tub, and multiple patios perfect for entertaining or relaxing amidst the serene backdrop of trees, vinyl fencing, and gardens. The community offers an array of amenities, including pools, tennis courts, and walking paths, fostering an active lifestyle. Located in a vibrant neighborhood within walking distance to popular restaurants, bars and conveniences. With easy access to recreational facilities and a welcoming community atmosphere, this property is a true gem for those seeking a blend of luxury and lifestyle.

1036 Ocean Parkway, Ocean Pines

Listing courtesy of Hileman Real Estate-Berlin. Contact: (410) 208-9200
$389,900
3 Beds ⋅ 2 Baths
Welcome to 15 Lord Guy Terrace, a beautifully maintained one-level home in Ocean Pines. Ideally 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 the perfect blend of coastal living and everyday convenience. Situated on an oversized lot with a spacious paved driveway, the property features low-maintenance landscaping with brick-bordered stone beds, a welcoming front porch, and a side porch ideal for outdoor dining and entertaining. Inside, the open-concept layout connects the living room, dining area, and kitchen, creating an inviting space for gathering. The owner's suite is privately positioned at the front of the home, while two guest bedrooms and a full bath are located at the rear. A spacious bonus room off the kitchen provides exceptional flexibility as a second living area, home office, playroom, or potential fourth bedroom with minimal modifications. Ocean Pines offers an impressive selection of resort-style amenities with both free and paid membership options are available. The amenities include 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. This home is an excellent choice for a primary residence, vacation getaway, or investment property. Daily conveniences—including grocery stores, pharmacies, healthcare, banks, and local restaurants—are just minutes away. Enjoy easy access to Ocean City's famous Boardwalk and beaches, Assateague Island National Seashore's wild horses and natural beauty, historic downtown Berlin's boutiques and cafés, numerous nearby golf courses, like Rum Pointe Seaside Golf Links, the Links at Lighthouse Sound, and Glen Riddle Golf Club, boating, fishing, and outdoor recreation, as well as Delaware beach destinations like Lewes, Rehoboth Beach, Bethany Beach, and Fenwick Island all within a 20-50 minute drive.

15 Lord Guy Terrace, Ocean Pines

Listing courtesy of Coldwell Banker Realty. Contact: 3025391777
$369,900
3 Beds ⋅ 3 Baths
A lovely home, a great location, and a great price! Tucked in the serene confines of Sherwood Forest, and yet only a short distance to South Gate of Ocean Pines, this charming 3 Bedroom, 2.5 bath home features 2 FIRST FLOOR bedrooms. One first floor bedroom features an en suite half bath, the full bath is in the hall for both bedrooms to share. Upstairs there is a bedroom, full bath, and a large bonus room with plenty of possibility. Just some of the many features in this home are an open floor plan, updated kitchen with stainless steel appliances, updated bathrooms, gas fireplace, and beautiful LVP floors through the living room, sunroom, and kitchen. Outside there is a deck on the front of the home, a balcony in the rear. Plus a paved driveway and a storage shed. This home is just what you are looking for, schedule a showing today!

7 Royal Oaks Dr, Ocean Pines

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$364,900
3 Beds ⋅ 2 Baths
Home back on the market at no fault of the seller-buyer couldn't get approved for financing. This beautiful 3-bedroom 2-bath home with plenty of natural light and open concept is the home you have been waiting for! Home features LVP flooring throughout which is highly durable and offers the look of natural wood. Newly painted interior, side deck and new flooring in primary bedroom and second bedroom as well as a brand-new water heater completes all the updates needed for a turnkey home. Enjoy your peaceful and relaxing screened in-porch as it is the perfect indoor/outdoor oasis that expands your living space. Living area includes a fireplace for those cool fall or winter evenings, and the kitchen boasts plenty of cabinet space and a pantry. This home also includes an attached storage area for tools, beach chairs, bicycles or whatever you may want to store!

1218 Ocean Pkwy, Ocean Pines

Listing courtesy of Coastal Life Realty Group LLC. Contact: (443) 235-8382
$425,000
3 Beds ⋅ 2 Baths
Welcome to 42 Quarter Staff Place! Conveniently located on South Gate near grocery stores, restaurants, medical services and MORE! This lovely rancher has 3 bedrooms, 2 full baths, beautiful stone front with a welcoming front porch, open floorplan and backs to forestry (yard is half fenced and half undisturbed forestry). This 1200sqft+ home features engineered hardwood, masonry, wood burning, stone fireplace, large primary suite with ensuite bath featuring walk-in tiled shower, soaking tub, granite tops and warm wood cabinets. Modern kitchen with warm wood cabinetry, stainless appliances and granite counter tops! As an added bonus, the home features a 2-car garage and new roof in 2025! Ocean Pines is Worcester County's largest community offering the most extensive amenity package that includes plenty for the outdoor enthusiast! Nature trails, bike trails, boat ramp, marina, basket ball courts, tennis club, several tot lots/playgrounds, skate park, 5 pools (1 year-round indoor, 1 oceanfront), Lake for fishing, community center, oceanfront beach club in Ocean City (48th Street) with snack bar, bathhouse and showers Ocean Pines is located off Racetrack Road (Rt. 589) offering plenty of services, including farmer's market, library, post office, fire dept. police dept., restaurants, grocery options! JUST 8.9 miles to the beach! Better act FAST! This one won't last!

42 Quarter Staff Pl, Ocean Pines

Listing courtesy of Keller Williams Realty Delmarva. Contact: 4105246400
$399,000
3 Beds ⋅ 2 Baths
This 3 bedroom 2 bath home is designed for easy living. Just off the great room is a 3 season room and deck that overlooks a private back yard...providing an outdoor entertainment area or an area for quiet mornings with your coffee or tea. Great room with its bright and airy feel is accented by a cathedral ceiling. First floor main bedroom with bath ...second floor has two bedrooms and a bath. Oodles of floored storage space in attic eaves with doored access. Detached shed for lawn care items, tools, bikes and/or beach toys. Over sized one car garage and a paved driveway. This home is perfect for living, relaxing, entertaining, or enjoying the coastal lifestyle. Conveniently located near Ocean Pines' many amenities, including pools, parks, marina facilities, yacht club, golf course, walking trails, and more. Whether you're searching for a primary residence, vacation getaway, or investment property, this home is ready for its next owner.

1348 Ocean Pkwy, Berlin

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$391,000
It's a rare gem to have a fully buildable .28 acre lot in the highly desired Sherwood Forest section of Ocean Pines -- and with some amazing views you have to see to believe! Public water and sewer access are ready for your new construction, and while awaiting move-in day, take time to familiarize yourself with the abundant amenities Ocean Pines offers. Plan your dream home today and take advantage of starting from the ground up...customize YOUR own paradise and be settled and ready for next year's beach season!

100 Robin Hood Trl, Ocean Pines

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$374,900
3 Beds ⋅ 2 Baths
Motivated sellers just made a price reduction! All spruced up and ready to go! Fresh paint and new carpet throughout this 1 level contemporary coastal custom-built 3-bedroom 2 bath home in the community of Ocean Pines. Delightful 14 x 12 screened porch plus a 12 x 12 deck for enjoying the good life here at the beach. Spacious Primary bedroom with a vaulted ceiling has a walk-in-closet and access to the primary bath with a walk-in shower. 8x7 attached shed for all you bike, lawn equipment and beach toys. Gutter guards installed. Asphalt paved driveway for plenty of parking for you, family and friends. 5 x7 laundry room with washer and dryer. The complete package is easy to see and ready for your immediate enjoyment.

31 Footbridge, Ocean Pines

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$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 just sold in 06/26!!“ The Hunter I” model is the little brother of The Hunter II currently being built at 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 more soft 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: 4437830299
$475,000
5 Beds ⋅ 4 Baths
NEW PRICE! This gracious Tudor styled home is waiting for you to enjoy now at a reduced price. The open living, dining and kitchen greet you as you enter the home. 3 bedrooms, including the Primary one, are on the first level along with 2 full baths. Wonderful Sunroom off the dining room plus a screened porch overlooking the private rear yard. Large rear deck for more outside enjoyment. Large 2 car garage has some extra space of tools and storage. Second floor has an open loft with lots of shelves for books or collectables. One more bedroom is the next room and has a full bath plus skylights and a nice size closet. Private office is the next room with separate rear access to the rear stairs. It has a skylight and a small closet and could be another bedroom. Roof is only 2 or 3 years old. Almost all of the furniture in the home will remain. Vacant and easy to see.

127 Nottingham Ln, Ocean Pines

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$875,000
4 Beds ⋅ 3 Baths
Welcome to Triple Crown Estates in the South Gate of Ocean Pines. The Harper Model is a stunning 4‑bedroom, 2.5‑bath custom build by Ultimate Homes, LLC. This coastal‑styled residence offers just over 3,100 sq ft of beautifully designed living space—including a 19 x17 primary bedroom with tray ceilings, a first-floor office for working remotely or opt to make it a first floor 5th bedroom, and plenty of room to entertain friends and family. 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!

85 King Richard Rd, Berlin

Listing courtesy of Sheppard Realty Inc. Contact: 4437830299
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