Crooked Pond Real Estate

Welcome to Crooked Pond, a hidden gem nestled in the heart of Hilton Head Island, South Carolina. This enchanting subdivision offers a perfect blend of natural beauty and modern convenience, making it an ideal destination for families, retirees, and anyone seeking a tranquil lifestyle by the coast.

Crooked Pond is characterized by its picturesque surroundings, featuring serene ponds, lush greenery, and a variety of wildlife that call this area home. Residents can often be seen enjoying leisurely walks along the scenic pathways, where the soothing sounds of nature provide a peaceful backdrop. The community is designed with an emphasis on outdoor living, encouraging an active lifestyle with opportunities for biking, jogging, and enjoying the stunning South Carolina weather.

Convenience is at your fingertips in Crooked Pond, with easy access to Hilton Head’s renowned beaches, golf courses, and a plethora of dining and shopping options. The vibrant community is just a short drive from the island's bustling center, where you can explore local boutiques, savor fresh seafood at waterfront restaurants, or indulge in a round of golf at one of the award-winning courses.

Families will appreciate the proximity to top-rated schools and recreational facilities, making Crooked Pond a desirable location for those looking to settle down. With its charming homes and inviting atmosphere, Crooked Pond is more than just a subdivision; it's a community where neighbors become friends and lifelong memories are made. Discover the allure of Crooked Pond, where your dream home awaits in beautiful Hilton Head Island!

Newest Listings in Crooked Pond

$1,150,000

3 Beds ⋅ 5 Baths ⋅ HILTONHEAD-511807 MLS

Excellent value on updated, superbly maintained lifestyle home with private pool/spa and panoramic lagoon views on quiet cul de sac street in popular Hilton Head Plantation. Features include soaring, smooth vaulted & tray ceilings, wood & tile flooring, granite & composite counters, high end appliances (Forno 8 burner gas range & double Ovens, etc.), custom cabinetry/vanities/built-ins, plantation shutters, skylights, recessed lighting, ceiling fans, walls of windows to pool & lagoon views, 17 SEER high efficiency HVAC system, newer roof (2022) & mechanicals, etc. Very livable floor plan offers Chef's dream kitchen (large island, coffee/wet bar, butlers pantry, max cabinet & counter space), open to casual and formal dining, expansive great room, bonus/media room, much desired screened porch, 3 BR suites including well-appointed primary suite w/private courtyard, 2 ample guest BR's with updated baths (glass & tile surround showers, new vanities, counters, lighting), secluded den/study, 2 powder rooms, 2nd floor loft, walk-in attic space, 2 car garage and ample closet/storage space. All with charming curb appeal, circular drive, specimen live oaks, palms, azaleas, etc. and proximity to Crooked Pond Pool/Tennis, front gate & shopping/dining/entertainment + HHP's Spring Lake Pool Complex, Dolphin Head Recreational Area and newly refurbished Pine Island Beach Park!

3 Twisted Cay Lane, Hilton Head Island

Courtesy of Charter One Realty

$845,000

3 Beds ⋅ 3 Baths ⋅ HILTONHEAD-509823 MLS

Welcome to classic Lowcountry living in Hilton Head Plantation, one of the Island's most sought-after gated communities. Tucked away on a quiet cul-de-sac and backing to tranquil woods, this beautifully and impeccably maintained 3-bedroom, 2.5-bath home offers 2,454 square feet of charm, privacy, and inviting living space. The recently renovated showstopper kitchen is truly the heart of the home and an unforgettable showpiece. Anchored by an enormous picture window overlooking the lush landscaped yard and protected wooded backdrop, the space is immersed in nature. The view is so expansive and serene that it creates the illusion the property extends endlessly into the protected woods beyond. Framed by towering greenery and filled with natural light throughout the day, this incredible window transforms the kitchen into a warm, calming gathering space unlike anything you typically find on Hilton Head Island. Spectacular!!! All bedrooms are conveniently located upstairs, while the main level offers an ideal flow for entertaining and everyday living. Downstairs you'll find a spacious living room, sunroom, formal dining room, and a versatile den - a truly coveted flex space perfect for a home office, media room, fitness, or even guest overflow. The home's exterior captures timeless Southern charm with a welcoming front porch, attached one-car garage (with additional storage space as it's extended in length). Mature landscaping surrounds the property with towering specimen trees, native azaleas, and even a blooming pomegranate tree, creating a lush and unforgettable setting. This is the {famous} good juju house! Residents of Hilton Head Plantation enjoy an unmatched lifestyle with two guarded entrances, private beach access (Dolphin Head), miles of leisure trails (including my favorite - The Bluff Walk), and some of the island's most desirable amenities - including an incredible community pool complex complete with a lazy river, area for lap swimming, and kiddo splash pad, too. This is a rare and special opportunity to enjoy privacy, nature, and resort-style living in one of Hilton Head's premier communities.

54 Edgewood Drive, Hilton Head Island

Courtesy of RE/MAX Island Realty

Start Your Search

We do not attempt to independently verify the currency, completeness, accuracy or authenticity of the data contained herein. It may be subject to transcription and transmission errors. Accordingly, the data is provided on an “as is” “as available” basis only and may not reflect all real estate activity in the market. © 2026 REsides, Inc. All rights reserved. Certain information contained herein is derived from information, which is the licensed property of, and copyrighted by, REsides, Inc.

This information is deemed reliable, but not guaranteed. Neither the Lowcountry Regional MLS, nor the listing broker, nor their agents or subagents are responsible for the accuracy of the information. The buyer is responsible for verifying all information. This information is provided by the Lowcountry Regional MLS for use by its members and is not intended for use for any other purpose.