Oak Island Homes with Circular Driveway Parking Features

Welcome to Oak Island, North Carolina – a hidden gem nestled in the picturesque Brunswick County. Known for its stunning beaches, tranquil atmosphere, and vibrant community, Oak Island is the perfect destination for those seeking a coastal lifestyle infused with Southern charm. With its miles of sandy shores, lush maritime forests, and scenic marshlands, Oak Island offers a serene escape, whether you’re looking to retire, invest in a vacation home, or raise a family.

One of the standout features of many homes in this delightful coastal town is the availability of circular driveway parking. Imagine arriving home to a beautifully designed property where convenience meets elegance. Homes with circular driveways not only enhance the curb appeal but also provide ample parking space for family and friends. This thoughtful design element allows for easy access and smooth traffic flow, making it perfect for entertaining or simply enjoying the peace of mind that comes with ample parking.

Living in Oak Island means you’ll have access to a plethora of outdoor activities, from fishing and kayaking to exploring the local parks and nature trails. The community is also rich in dining and shopping options, offering a delightful mix of local seafood shacks and quaint boutiques. Whether you’re strolling along the beach at sunset or enjoying a day of fishing, Oak Island is a place where memories are made.

Discover your dream home with a circular driveway in Oak Island, where coastal living meets modern convenience. Let the charm of this coastal paradise welcome you home!

Newest Oak Island Homes with Circular Driveway Parking Features

$799,000

4 Beds ⋅ 4 Baths

You guys, let's talk about the elephant on the island first: this home sits on East Oak Island Drive, one of Oak Island's main routes. Yes, there is traffic out front. But before you scroll past it, this corner-lot setup has a little secret weapon: a circular drive that lets you pull in from either East Oak Island Drive or NE 26th Street and leave facing forward. No awkward backing out onto the main road, no driveway gymnastics. Just easy in, easy out, plus plenty of parking for guests, beach gear, a boat, RV, trailer, or that golf cart you are absolutely going to want. And once you step inside? The road feels a whole lot farther away. The home is quiet inside, and the covered back deck, grilling area, patio, fenced yard, and outdoor shower create a private little retreat out back. This bright, beautifully flexible 4-bedroom, 3.5-bath home is ready to work for the way you want to use it. Need a beach escape? Done. Want a second home that can help offset ownership costs with rental income? Also done. Looking for a roomy primary residence with space for guests, an adult child, aging parent, for multigenerational living? This one has layers. And here is one of the big Oak Island features buyers are always asking about: the home is already set up with an elevator shaft currently being used as owner storage. The electrical is in place, so there is a clear path to adding an elevator in the future, with installation estimated around $20,000. That is a huge plus for a home on pilings and makes this property even more flexible for long-term use. Want to explore it further? I am happy to connect you with an elevator company, help get quotes, and take some of that ''okay, but what would that really cost?'' homework off your plate. This home has been primarily enjoyed by family and friends over the years, but it is now professionally managed and booked through much of the summer, proving it can absolutely perform as a vacation rental when you are not using it. Think of it as your beach getaway that can also help carry its weight. Use it when you want, rent it during prime weeks when you are not here, and let those bookings help offset the mortgage and ownership costs. Upstairs, the open living, dining, and kitchen space is light, spacious, and made for gathering. The kitchen brings the counter space, island seating, and room for a crowd, while the dining area can easily accommodate a larger table for those ''everyone is coming over'' beach weekends. The primary suite offers generous space, a walk-in tile shower, and room for a king-size bed. A second bedroom, third bedroom, and Jack-and-Jill bath keep the upstairs layout easy and functional for family or guests. Downstairs adds a whole second living experience with its own living area, game or dining space, spacious bedroom, full bath, laundry room, and excellent storage. It is ideal for guests who want their own hangout zone, or it could work beautifully for multigenerational living. There is even potential to explore adding a kitchenette downstairs for an even more independent setup. The long tandem garage is another standout. Park a large vehicle, small boat, trailer, and golf cart, use it for beach toys and storage, or keep the current game-room vibe going. There is room to make this space fit your lifestyle, whether that means trucks, golf carts, paddleboards, bikes, a pool table, or all of the above. Outside, the fenced backyard is wonderfully low-maintenance and gives you room to dream a little. It can accommodate a great hot tub or swim spa, and there may also be room to explore a smaller pool option depending on the design and placement. I can help with that legwork too, whether that means connecting you with pool or spa companies, getting ideas on placement, or gathering quotes so you can make decisions with real numbers instead of guessing. Easy peezy. Not on a direct beach-access street? No problem. You can be at the beach in just a few minutes via Yacht Drive by gol the home gives you a great place to store it when you are back. You are also close to the Intracoastal Waterway, Veterans Park, and the public boat ramp at NE 55th Street, making this a fantastic option for boaters and coastal adventurers. The furniture comes with, creating an easy turnkey opportunity, and additional accessories or furnishing options may be negotiable for buyers who want the home ready to enjoy from day one. Bring your own style, keep the current setup, or let's talk about creating the beach home that fits your vision. This is not a cookie-cutter beach house. It is colorful, flexible, rental-ready, full of storage, and designed for real-life coastal living. Come see why this East Oak Island Drive corner might just be the best surprise on your home tour.

2602 E Oak Island Dr, Oak Island

$617,000

3 Beds ⋅ 2 Baths

A RARE gem on the highly sought-after west side of the island! Situated on a spacious DOUBLE LOT with no flood insurance required, this beautifully upgraded 3 bedroom, 2 bath home with circular driveway offers the perfect blend of convenience, privacy, and coastal lifestyle. Enjoy a quick golf cart ride to the beach or boat ramp while being just minutes from grocery stores, restaurants, bars, live music, parks, playgrounds, and the splash pad--close to everything, yet tucked away from the hustle and bustle. Thoughtfully improved throughout, this home features a NEWER roof (2024), fresh interior paint including popcorn ceiling removal, NEW exterior paint, updated light fixtures, NEW toilets, a NEW privacy fence, upgraded landscaping, and a Reverse Osmosis system in the kitchen. Charming shiplap accents add character, while all NEWER appliances--including the washer and dryer--make this home truly move-in ready. The detached, enlarged garage provides exceptional space for vehicles, golf carts, boats, paddle boards, surf boards, hobbies, or storage. Inside the home, you'll find ample storage throughout, including a spacious walk-in laundry room. Whether you're looking for a primary residence, vacation getaway, or investment opportunity, this well-maintained, thoughtfully upgraded, island retreat is a rare find. Furnishings negotiable to enhance turnkey potential.

103 Nw 25th St, Oak Island

$1,100,000

3 Beds ⋅ 3 Baths

Three separate living spaces just a few blocks from the beach! Rarely available on Oak Island, this unique coastal compound sits on a spacious 0.29-acre double lot and spans three separate structures, creating exceptional privacy and endless possibilities for rental income, multi-generational living, or guest accommodations. The property includes a beautifully updated 3-bedroom, 2.5-bath main house, a detached 2-bedroom/1-bath apartment, and a third 1-bedroom/1-bath apartment. With three kitchens and multiple living areas, this versatile property offers a layout seldom found in coastal communities. The main house has been thoughtfully updated throughout, offering an elegant blend of comfort, style, and functionality. A sprawling covered front porch welcomes you inside to a well-designed floor plan featuring vaulted and tray ceilings, a gas log fireplace, spacious sunroom, updated kitchen with an extended peninsula, a pantry, and a first-floor primary suite complete with a two closets and a dual-vanity bathroom with a walk-in shower. The beautifully renovated bedrooms and bathrooms enhance the home's elegant, move-in-ready appeal. Upstairs, two generously sized guest bedrooms and a full bath provide a private retreat for family and guests. Rounding out the second floor are two oversized lighted walk-in storage rooms spanning much of the width of the home, offering abundant space for beach gear, seasonal items, luggage, and hobbies. In addition to the main house, the detached garage structure includes two apartments that provide exceptional flexibility and privacy. The first includes a bedroom, bath, kitchen, and living area. The second features two bedrooms, a full kitchen with island, living room, laundry area, flex room, and private entrance. Together, these additional residences provide excellent options for short-term vacation rentals or long-term rentals, extended family living, guest accommodations, or home office space. The property continues to impress with a circular driveway, abundant parking for multiple vehicles, additional boat and RV parking, mature landscaping, garden areas, and a 6-foot vinyl privacy fence surrounding the backyard. Additional features include DP50 impact-rated windows, a premium metal roof installed by Metal Roofing Experts, tankless water heater, and no HOA. Properties offering this combination of living space, privacy, storage, parking, and proximity to the beach are hardly ever available on Oak Island. Schedule your showing today!

427 Womble St, Oak Island

$415,000

2 Beds ⋅ 2 Baths

Double your pleasure with 2 lots and 2 bedrooms on Oak Island! Popular in the 80's this classic style home gives a nostalgic nod to lazy summers and has circled back around to today's Island living. This home has been a successful rental, but they have now vacated and it is time for you to make it Yours! The huge porch is where you will likely spend most of your time when not on the beach. On the quiet West end and near the public fishing dock on Yacht. Practically priced at land value in today's market. Perfect island home for vacation spot, rental or year round living. The Town of Oak Island offers numerous amenities such as golf, tennis, pickleball, basketball, picnic area, boat launches, public docks, water accesses yet no HOA fees!

102 Nw 20th St, Oak Island

$795,000

3 Beds ⋅ 3 Baths

Amazing custom home on a double lot on the highly desirable west end of Oak Island with a short walk to the beach! Live in the main home and rent out the detached garage apartment however you prefer! Unlimited AIRBNB potential with the spacious apartment! Or rent out both the home and the apartment! The main house hosts a beautiful open floor plan with vaulted ceilings and abundant hardwood floors. Downstairs has a spacious kitchen with granite countertops, large dining area, open living room, powder room, primary bedroom and bathroom and a laundry room. Upstairs includes a flexible loft area, 2 large bedrooms and another full bathroom. Rocking chair covered front porch. Side porch that leads to a brick patio area perfect for grilling and continue up a few stairs to a refreshing swim pool/spa! As mentioned before, this home has a spacious detached garage that offers plenty of room for cars and/or beach toys downstairs and an amazing apartment or 4th bedroom or office upstairs. No restrictions on renting it out so could easily be an income producing home! Outdoor shower. Fenced-in back yard. Crawlspace encapsulated. Not in the flood zone. Circular driveway and plenty of parking. Refrigerator, washer and dryer remain! The town of Oak Island offers great amenities such as golf, tennis, basketball, picnic area, boat launches (close to this house), public docks and tons of water access!

116 Nw 8th St, Oak Island

$1,975,000

4 Beds ⋅ 3 Baths

The soft swish and sway of sea oats atop the dune as you sit in your favorite rocker, a cool ocean breeze caressing your shirt, and all the stars in the sky winking at you over the Atlantic Ocean. This is what memories are made of. That's what welcomes you at 645 Caswell Beach Road, Memory Maker, an OCEANFRONT retreat perfectly situated between historic Southport and Oak Island on one of North Carolina's most prestigious coastal addresses, reimagined from the walls in with thoughtful 2025/26 renovations. Step inside, and the Atlantic greets you. Four giant picture windows have looked out over the wide sand turtle sanctuary beach for decades. Vaulted beamed ceilings, soft sea-glass walls, and wide-plank flooring, wainscoting set on a diagonal, set the stage. Imagine a game table anchoring the loft overlooking the living area below, the kind of space where long afternoons turn into longer evenings, where acquaintances become best friends. Furniture is included. The chef's kiss kitchen is the home's quiet showpiece. A hand-laid mother-of-pearl hexagon shell backsplash catches the morning light above all-new GE appliances, including a double wall oven, glass cooktop, and French-door refrigerator. Two beautifully reimagined bathrooms, one with marble hex tile and brushed gold, another with veined quartz and a glass-enclosed marble shower, feel more boutique hotel than beach house. Every surface is new: raised seam metal roof, HVAC, water heater, floors, kitchen, baths. Beyond the kitchen, a private boardwalk leads to your stretch of sand. After a full day with the ones you love, rinse off in the outdoor shower enclosure, then settle onto the oceanfront deck as the sun slips lower. Step up to the loft's deck, pull up a rocking chair, and take in the Independence Day fireworks painting the sky above Southport's Harbor. From the front of the home, expansive decks and windows capture sweeping views of Southport Harbor and the Intracoastal Waterway, a rare double-water vantage few Caswell homes can offer. Four separate decks and a long covered porch wrap the home, with a dedicated storage room below that keeps beach gear tucked away until the next sunrise. The .42-acre parcel leaves room to grill, gather, and play. A round porthole window overlooks the dunes. A shell-shaped sconce's warm glow lights the stairwell. Small moments, carefully chosen. This is North Carolina beach life at its best, a home built for experiences and the stories that come with them. Come for the sunrises. Stay for the memories.

645 Caswell Beach Rd, Oak Island

$598,000

3 Beds ⋅ 2 Baths

OWNER FINANCING OWNER FINANCING TELL FRIENDS AND FAMILY THAT WANT TO COME TO ISLAND LIFE IT WANT GET BETTER THAN THIS OPPORTUNITY Island Life with the Benefits of a Double Lot! Welcome to 108 NW 29th St, where space, comfort, and modern updates come together in this beautifully upgraded 3-bedroom, 2-bath home with over 1,600 sq ft of living space. From the moment you arrive, you'll appreciate the ample parking--perfect for your camper, boat, and multiple vehicles. The circular driveway makes coming and going a breeze, and there's a secondary drive that leads to a 20x24 insulated building with electricity--ready to become your workshop, studio, gym, or anything else you envision. In addition, the property features, a second building, approximately 10x12 with a lean-to and electric, 16x16 screened detached building with electricity--ideal for entertaining or relaxing, just steps from your slider door, backyard patio with seating, privacy wood fence and planter beds for added charm and tranquility. The front of the home boasts a welcoming porch that leads to the screened-in lanai and into the spacious living room via a sliding glass door. Inside, no detail was overlooked: all-new flooring throughout, fully renovated bathrooms and kitchen, new appliances: Refrigerator, microwave, oven/range, and dishwasher, New Stackable Washer and Dryer, new cabinetry with stylish butcher block countertops, Carolina room perfect for lounging or entertaining, can lights throughout for a warm, modern glow. This home offers flexibility, comfort, and upgraded living--all on an expansive double lot. Don't miss your chance to enjoy island life with room to live, play, and grow.

108 Nw 29th St, Oak Island

Start Your Search

Copyright 2026 NCRMLS. All rights reserved. North Carolina Regional Multiple Listing Service, (NCRMLS), provides content displayed here (“provided content”) on an “as is” basis and makes no representations or warranties regarding the provided content, including, but not limited to those of non-infringement, timeliness, accuracy, or completeness. Individuals and companies using information presented are responsible for verification and validation of information they utilize and present to their customers and clients. NCRMLS will not be liable for any damage or loss resulting from use of the provided content or the products available through Portals, IDX, VOW, and/or Syndication. Recipients of this information shall not resell, redistribute, reproduce, modify, or otherwise copy any portion thereof without the expressed written consent of NCRMLS.