luxury properties for sale St. Simons Island, United States

Don’t miss this rare opportunity to own a fully licensed Short-Term Vacation Rental (STVR) in Savannah’s coveted Victorian District—just one block from iconic Forsyth Park. This charming 1BD/1BA first-floor condo combines timeless historic charm with modern upgrades, making it ideal as an income-producing property or personal retreat. Thoughtfully designed, the interior features a sleek kitchen with granite countertops, stainless steel appliances, and custom cabinetry. The inviting living area showcases hardwood floors and decorative fireplace mantles, while the spacious bedroom and luxurious marble walk-in shower provide comfort and style. Step outside to enjoy a large private deck—perfect for entertaining or relaxing. The building offers two off street parking spaces! With an active non-owner STVR license, strong rental history, and a convenient location to SCAD, dining, shopping, and more, this turnkey property offers outstanding investment potential in one of Savannah’s most desirable neighborhoods. All furnishings convey!

Step into timeless charm and modern comfort with this beautifully preserved Victorian freestanding home, originally built in 1892 by John Starr. This 3 bedroom, 2.5 bath residence is located in the Historic District of Savannah, just a short walk to Forsyth Park, boutique shopping, restaurants, a nearby dog park ad the vibrant River Street waterfront. The home seamlessly blends historic character with thoughtful updates, including a renovated kitchen and updated bathrooms designed for today's lifestyle. Inside are rich hardwood floors, soaring high ceilings and an abundance of natural light streaming in from three sides, creating a warm and inviting atmosphere throughout. Original architectural details pair effortlessly with modern finishes, offering both elegance and functionality. Enjoy a private, bricked courtyard oasis with a mature tree, lush bushes and a tranquil fountain - perfect for relaxing or entertaining. Additional highlights include a rare non-owner occupied STVR license, making this property a great opportunity. The John Starr House is a true blend of history, beauty, location and versatility.

Step into the enchanting embrace of the notable Upham Winter Cottage, a captivating Queen Anne Victorian nestled on a quarter-acre lot within the heart of St. Augustine's cherished historic preservation district and listed on the National Register of Historic Places. This world-class historic mansion has recently been renovated from top to bottom to perfection with soft coastal hues in mind, enjoy the well-designed balance of rich historic beauty and modern luxury. With 5800 square feet of living space, five bedrooms and three and a half bathrooms in the main house and a two bedroom, one bath apartment with private entrance, a full kitchen, living and dining rooms - this home is ideal for multigenerational living or additional income. Located on historic St. George Street, the shops, restaurants, landmarks and culture of the Nation's Oldest City are only steps away. The highly active community association provides additional opportunities to socialize and enjoy the buzz of downtown living. Built in 1893 as a winter retreat for John J. Upham, a veteran of the Civil War and Plains Indian War, this remarkable home showcases the graceful blend of Queen Anne Victorian architecture with examples of Moorish Revival in the courtyard arches. With stunning original millwork, wood floors and unique octagonal shape, this home will take you back to the splendor of the Gilded Age. From joyous Flagler Era galas to legendary Mardi Gras celebrations, The Upham Winter Cottage has been a witness to countless extraordinary events throughout the ages. Today, as you step foot within these storied walls, you become a part of the Upham Winter Cottage's narrative and assume the role of its guardian, preserving the heritage of the past while crafting a new chapter in its history. Nothing compares.

This amazing property, aptly named At Journeys End, is a six unit contemporary-styled and designer-inspired bed and breakfast, perfectly located in the heart of Downtown St. Augustine’s Historic District. This unique property features four guest rooms in the main house and two guest suites in the detached carriage house. Below the two carraiage house suites is a large storage area and owners office space. The property offers all the amenities that modern-day travelers enjoy in a fun Victorian fusion style, including a welcoming sitting room, a bright and cheerful dining room, easily-accessible kitchen and laundry room. Each suite is unique and is themed after an explorer. With multiple indoor and outdoor spaces to enjoy, guests can spread out and feel at home during their stay. Situated on a quiet tree-lined street in Lincolnville, guests are just steps away from fabulous restaurants, nightlife, museums, art galleries, shopping, and a picturesque stroll along the bay front. Additional features, such as 6 on-site designated parking spaces, cameras, smart locks and smart thermostats allow for convenience and peace of mind when welcoming guests. It is no wonder that At Journeys End has been consistently ranked as the number 2 St. Augustine Inn by TripAdvisor, with thousands of 5-star reviews. Whether you envision running a traditional bed and breakfast, or renting the home on a short-term vacation rental basis, this charming inn offers a turn-key business for the savvy investor. Or, bring your ideas and imagination for your own business model or St. Augustine residence. Dont wait - opportunities like these do not become available often.

Just steps from historic downtown Saint Augustine, this 1900s southern bungalow in the heart of booming West Augustine is a true unicorn property. The oversized lot offers endless potential to expand or add a pool or ADU, creating the ultimate investment or multiple generational forever home. Enjoy the charm of old Florida with a detached garage, mature trees, and room to grow in one of Saint Augustine's most sought after neighborhoods. Walk to the vibrant west King district filled with local boutiques, cafes, yoga studios, pubs, and a neighborhood brewery, or take a peaceful stroll along Oyster Creek. This is a rare chance to create a mini compound in the nation's oldest city. Bring your craftsmanship and vision to make this family estate your own and capture a piece of historic Saint Augustine charm. Some images are edited, Buyer to verify all information.

A prized island neighborhood tucked beside Anastasia State Park, this is where life slows to the rhythm of the tides, shoes are optional, and biking to the beach becomes part of your everyday routine. Reminiscent of the classic beach bungalows that line the East Coast, 24 Flamingo Drive welcomes you first from its inviting front porch where greeting the sun with coffee in hand is a good start to the morning. Inside, natural light pours through six windows in the expansive gathering room, shifting beautifully throughout the day. Original honey-toned wood floors ground the space with warmth and character, and barefoot living feels perfectly at home. Arrange the space to suit your style and with 420 square feet, living and dining can live happily together. With a nod to keeping the character true to the period, the new kitchen will speak to the person who loves to wield the wooden spoon. Guests can gather at the bar or banquette tucked into the windowed alcove, offering conversation and the occasional helping hand. Abundant cabinetry and generous counter space keep everything organized within easy reach. Just beyond, the screened porch extends living space outdoors for slow breakfasts, afternoon naps in the breeze and cocktails under the evening sky. Three bedrooms line the south side of the home, welcoming morning light, while both bathrooms are conveniently accessible from main living spaces. At the rear of the house, laundry and a wall of storage connect to the side entrance which leads to the carport, workshop and additional parking. Along the sunny southern edge of the property, a four inch wall borders the driveway. It's a terrific canvas for container gardens that thrive in the sunshine. Set on nearly 1/3 of an acre, the property offers an enviable balance of open sun and mature shade. The home sits comfortably centered, with abundant parking to one side and a deliciously private yard to the other. There’s room here for imagination to take shape: am en-suite retreat, a pool for year-round swims, an outdoor kitchen and dining terrace?. This neighborhood has long been treasured for its proximity to both Anastasia State Park and Anastasia Boulevard. The island’s version of Main Street is lined with independent restaurants, shops, markets and local favorites. The park itself feels like a world apart, where protected shoreline, nesting birds and endless shells create a landscape that never loses its magic. Spend your days biking the four mile coastline, paddling through Salt Run, hiking shaded hammock trails or enjoying a picnic beneath windswept oaks while gopher tortoises wander nearby. It’s a lifestyle rooted in nature and simplicity. Also nearby are the St Augustine Lighthouse and Maritime Museum and the St Augustine Amp. Climb the lighthouse for sweeping coastal views, explore the museum or launch your boat into the Intracoastal for a day of fishing. At the Amp, nationally known musicians share the stage year-round, while Saturdays belong to the best farmers market which is replete with local produce, fresh breads, flowers, cheeses and music drifting from the Front Porch stage. If this sounds like the life you’ve been searching for, you’ll likely find us sitting on the front porch at 24 Flamingo Drive.

This one of a kind property captures your attention as soon as you drive through the gate! A truly hidden treasure loaded with unique charm and character. You will see the main home, a log cabin home and the adorable playhouse! Some of their features include custom woodwork finishes throughout, a screened veranda overlooking the lake, beautiful stone fireplace, large family room with stunning lake views, and a covered summer kitchen. There is 168 feet of white sandy beach and a boat dock with a solar powered lift. Crystal Lake is a spring fed lake stocked for fishing. Also included with this waterfront property is 4+/- wooded acreage across the street. Great potential for vacation rentals!

Oak Terrace is a core investment type (aka mailbox money) multifamily complex comprised of 12 total units, consisting of eight (8) townhouse units of 2 bedroom, 1.5 baths and four (4) 2 bedroom 1 bathroom flats, each totaling 900/SF of conditioned space. Centrally located in the heart of one of SW Gainesville's highest growth areas, Butler Plaza and Celebration Point, Oak Terrace is 1.5 miles from the University of Florida, and within short distance to major retailers such as Target, Walmart, Best Buy, Dick's Sporting Goods as well as Publix, Aldi, Total Wine, Sam's Club, and Lowe's. Built in 1981 and 1982 with concrete block construction, Oak Terrace recently experienced full and complete remodels to their units both cosmetically and mechanically, inside and out. The current in-place rents are $1,222/month with 2024 rents already set at $1,350/month across all 12 units. Tenants pay all utilities through individual metering directly to the utility company. All units have washers and dryer hookups. Parking for Tenants is located directly in front of the building.

The Elmore-Henderson House , c. 1821 Some homes were built to impress. This one was built to endure. Established in the early 1820s by U.S. Congressman Franklin Harper Elmore, this historic Federal-style residence remains one of Walterboro's most significant and recognizable estates. Set behind gates on over seven private acres within the Hickory Valley Historic District, the property offers a rare combination of architectural presence, land, and legacy--just over an hour from Charleston. From the moment you enter the property, there is a sense of arrival that cannot be replicated. A long approach framed by mature trees and established plantings gradually reveals the residence, positioned with intention and surrounded by grounds thoughtfully designed to complement both the architecture and the natural landscape. The main residence encompasses approximately 5,800+ square feet, offering 4 bedrooms and 3.5 bathrooms arranged within a traditional central hall floor plan. The home retains the symmetry and proportion characteristic of the Federal period, with 11-foot ceilings, expansive formal and informal living spaces, and original architectural details that reflect the craftsmanship of the early 19th century. Natural light moves easily throughout the home, highlighting the scale of each room and reinforcing the connection between interior and exterior spaces. The wraparound veranda with stately columns serves as a defining architectural feature, offering multiple vantage points to enjoy the surrounding grounds while creating seamless indoor-outdoor living, typical of the Lowcountry. The landscape design is a defining element of the property. Carefully curated by a respected landscape designer, the grounds have been composed to feel both refined and natural. Mature oaks anchor the property, while expansive lawn areas, layered gardens, and seasonal plantings create depth, texture, and year-round visual interest. Brick pathways and garden spaces introduce structure without interrupting the organic flow of the land, resulting in an environment that feels established, balanced, and private. Beyond the main residence, the estate functions as a true compound--an increasingly rare offering. A c. 1880 historic law office remains on the property, a nod to its long-standing role in the community. Additional guest accommodations and outbuildings provide flexibility for extended stays, workspace, or creative use, all while maintaining the integrity and character of the estate. Walterboro itself holds historical significance as a summer refuge for Lowcountry families seeking higher ground and healthier air, and properties of this caliber were reserved for those of influence and means. That legacy is still evident here--not only in the architecture, but also in the way the property has been preserved, respected, and thoughtfully maintained over time. This is not simply a historic home. It is a property defined by continuity--where land, architecture, and landscape come together in a way that cannot be recreated. For the buyer seeking authenticity, scale, and a connection to the Lowcountry's past--while still within reach of Charleston--527 Wichman Street represents a rare and meaningful opportunity.

New co-ownership opportunity by Pacaso: Own one-eighth of Oak House, a professionally managed, turnkey home. Set within Kiawah Island's sought-after Ocean Park community, Oak House offers modern coastal living surrounded by lagoon views and native Lowcountry landscape. The property's main house and guesthouse lie amid native trees, creating a sense of privacy and connection to nature. Built in 2023, the home features an airy, open layout with floor-to-ceiling glass, wide-plank flooring, and vaulted ceilings that draw natural light into every room. Designed for effortless entertaining, the main living spaces open to a private outdoor oasis with a heated saltwater pool and spa, firepit lounge, outdoor fireplace, and a full summer kitchen. Picture yourself beginning the day with coffee overlooking the lagoon or ending evenings gathered around the fire as the sun sets through the oaks. Inside, the chef's kitchen features a waterfall island, Sub-Zero and Wolf appliances, a butler's pantry, and a seamless flow to the dining and living areas. The serene primary suite opens directly to the pool, while additional guest suites and a separate studio space provide space and comfort for hosting. Ownership at Oak House includes access to the Sandcastle, featuring oceanfront pools, fitness facilities, and a curated calendar of owner events. An optional Governor's Club membership is also available, offering access to Kiawah Island's premier golf, dining, wellness, and social experiences. Surrounded by miles of scenic trails and pristine beaches, Oak House embodies the effortless elegance and natural beauty of life on Kiawah Island.