Tupelo Road Homes with Two Story Style

Welcome to Tupelo Road, a charming subdivision nestled in the heart of Hilton Head Island, South Carolina. Known for its serene landscapes and vibrant community spirit, Tupelo Road offers a unique blend of coastal living and modern convenience. This idyllic neighborhood is perfect for families, retirees, and anyone looking to embrace the laid-back lifestyle that the Lowcountry is famous for.

One of the standout features of homes in Tupelo Road is their stunning two-story designs. These spacious residences provide ample room for both relaxation and entertainment, with open floor plans that seamlessly connect living, dining, and kitchen areas. Imagine waking up to the gentle sounds of nature and enjoying your morning coffee on a private balcony, soaking in the breathtaking views of the lush surroundings. The two-story style not only enhances the aesthetic appeal of each home but also offers the opportunity for versatile living spaces, with bedrooms and additional rooms thoughtfully spread across both levels.

Residents of Tupelo Road enjoy easy access to Hilton Head Island’s pristine beaches, world-class golf courses, and a variety of dining and shopping options. The community is also known for its friendly neighbors and active lifestyle, with numerous parks and recreational areas nearby. Whether you’re taking a leisurely stroll or biking along the scenic paths, Tupelo Road is the perfect place to call home. Experience the beauty and charm of Hilton Head Island living in this delightful subdivision—where your dream home awaits!

Newest Tupelo Road Homes with Two Story Style

$3,875,000

7 Beds ⋅ 7 Baths ⋅ 4,400 SqFt. ⋅ HILTONHEAD-504560 MLS

7 Bedrooms | Brand New Construction | Close Proximity to the Beach | Sea Pines - Set along the fairways of Heron Point Golf Course in the heart of Sea Pines, 34 Tupelo is a newly constructed luxury residence designed for gracious living, gathering, and effortless Lowcountry style. With seven bedrooms and beautifully curated spaces throughout, this home offers both scale and intimacy. Inside, soaring ceilings and abundant natural light frame an open-concept layout that feels both elevated and welcoming. The chef's kitchen anchors the home with high-end appliances including a gas range, dual dishwashers and refrigerators, a butler's pantry, designed for entertaining with ease. Multiple living areas, including a recreation room, reading nook, and private in-law suite with its own staircase, provide flexibility and privacy for every lifestyle. A private pool overlooks the golf course, while the patio and built-in outdoor kitchen create an ideal setting for morning coffee, relaxed afternoons, or evenings spent under the stars. The home's location within Sea Pines Resort places you minutes from the beach, Harbour Town Marina, the iconic lighthouse, Lawton Stables, world-class golf and tennis, and miles of leisure trails. Whether biking to the beach, or exploring everything Sea Pines has to offer, the lifestyle here is both convenient and exceptional. 34 Tupelo is a rare opportunity to own a brand-new luxury home in one of Hilton Head Island's most sought-after resort communities. This is where refined design, thoughtful spaces, and an unmatched setting come together seamlessly.

34 Tupelo Road, Hilton Head Island

Listing courtesy of COAST PROFESSIONALS Brokered by EXP 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.