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10 Island Get-Away Houses for Sale

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The return to my home state of Maryland soon after my family’s south Florida adventure has me longing for my next warm get away. I spent much of my down time researching real estate…a hobby of mine. Exploring fascinating property types, jaw dropping features, extraordinary prices, local markets, and unique amenities in different areas. A way to keep my tropical daydreams properly fueled until spring emerges in my own hometown of Calvert County.

Whether you’re longing for an immediate break from this last month of winter, planning your summer holiday, or just want to catch a glimpse of some outrageous current listings, here are some remarkable homes that I came across while visiting the south and more homes that offer an unbelievable setting for escape. So snuggle up with a mug of something warm and check out these 10 daydream-worthy island getaways…

Key West, FL

800 Georgia St, Key West, FL 33040

For sale: $1,999,000

This upscale Key West home combines fun pops of color, such as a coral wall in the foyer and lime green shutter doors, with more classic features like a floating mahogany staircase. The entire back wall of the home features sets of double doors that open directly into the backyard patio, almost creating the illusion that there is no wall dividing the spaces.

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Wailea, HI

18 Ualei Place Makena, HI

For sale: $9,995,000

Word class luxury and comfort are realized in this one- of-a-kind estate in the prestigious Makena gated community of One Palaeua Bay. This home is designed to integrate a natural environment and gracious island style living. Custom designed to fit your contemporary and island lifestyle. Enter through the Porte-Cochere and come inside to experience this magnificent home, offering 5 bedroom suites, 5 baths, a chef’s kitchen dedicated to indoor and outdoor cooking with a full service bar, a large living area, an executive office, media room, 3-car garage, interior-exterior waterfall bar area and a 75 foot infinity edge black lava tiled swimming pool and spa. The property is being sold “As-Is,” with construction to be completed by the buyer. 

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Wilmington, NC

334 Cabbage Inlet Lane, Wilmington, NC

For sale: $3,295,000

This Shingle Style masterpiece is set on a high bluff with over two acres of park-like grounds, and 700 feet of waterfront at the confluence of the ICWW and Whiskey Creek. It is nestled among centuries old live oaks and boasts pier with four boat slips, floating dock and boat lift. Designed by renowned Hamptons architect Alex D Latham III and built by David James, precision craftsmanship can be found in every detail. This coastal home is designed for entertaining and features the main residence with over 7000 square feet and includes five bedrooms and five baths with an open and casual floor plan. The living spaces spill out onto 2400 square feet of wrap-around decking on three levels. After a day of boating, enjoy a dip in the free-formed salt water pool with vanishing edge or gather in the hot tub with family and friends for a relaxing end to your day. Enjoy spectacular sunsets over Whiskey Creek and delight in the dozens of egrets that often come to roost during the summer months in your own private sanctuary. A detached guest house over the three car garage offers an additional 835 square feet and will pamper even the most discriminating guests.

The house can also be seen in the July 2015 issue of Better Living. The property has been featured in the following films; “A Walk to Remember”, “Mary and Martha” (with Hilary Swank), “Tammy” (as Kathy Bates’ lake house), ABC’s “Secrets and Lies”, and the most recent Nicholas Sparks movie “The Choice.” The property was also chosen as the backdrop for L.L. Beans Summer Catalog.


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Marco Island, FL

1440 Caxambas Ct, Marco Island, FL

For sale: $9,450,000

The address is coveted. The legacy is yours forever. Villa Venezia, one of Marco Island’s most notable, treasured, multi award-winning waterfront properties, is the epitome of resort-style magnificence. Its timeless elegance and ceaseless vision, together with resort-style amenities, make this palatial masterpiece awe-inspiring. No expense or time was spared in creating this architectural work of art. Located on the prestigious Caxambas Island on a deep, 1-acre, bayfront lot set against a stunning backdrop of serene bay views and beautiful landscaping sits this romantic estate with gated entry. The grounds set the tone for what this residence offers, which takes you back to the 16th century in Venice where grand Italian villas were built. This seven-bedroom, seven-full and two-half-bath residence with detached one-bed, one-bath guest quarters with fitness center spans over 14,000 air-conditioned square feet. One of the most notable features of this home is the dramatic, expansive lanai with summer kitchen, fire pit, numerous fountains, water features, bridge and a beautiful negative-edge pool. Quick, deep water direct access from your dock. One of the most captivating homes on Marco.

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Houston, TX

27 Mott Lane, Houston, TX

For sale: $35,000,000

The House of Ki – This estate of steel, concrete, zinc and glass is a world-class design by Stern and Bucek with exceptional privacy. The views of the natural beauty of Buffalo Bayou are breathtaking. Interior cabinetry and paneling by Brochsteins of zebra and limba wood. A state-of- the-art Savant Home Automation system allows world-wide monitoring. A media room has meticulously designed acoustics with a retractable wall. A geothermal cooling and heating system. The approx. 8.7-acre property contains a 5+ acre reserve.




Georgetown, SC

223 Pioneer Loop, Georgetown, SC

For sale: $7,450,000

This Direct Oceanfront Fully Furnished Health Wise premiere custom built Oasis is located within the prestigious and highly sought after gated Debordieu Colony. This magnificent estate boasts over 15,000+ total square feet with an open spacious floor plan and has a resort feeling like none other. It comes furnished with beautifully chosen custom furniture, and a catwalk gallery with spectacular artwork crafted by Wyland. This well-appointed 5 bedrooms, 6.2 baths, gives you the full experience of island living with direct ocean access. Impeccable craftsmanship throughout this home with interior features including but not limited to a chef’s gourmet kitchen with all built-in cabinet appliances and center island, easy close drawers, walk in pantry, black walnut hardwood floors, central vacuum system, lighted panel ceilings, hand painted faux finished walls, fitness center, elevator, salt water aquarium with exotic fish from around the world, spiral staircase, all custom solid Alder stained doors, 8 skylights with power close screens and rain sensors, custom door knobs, security system with cameras, whole house sound system, large laundry room with beautiful cabinetry. Presidential, Barrel, Vaulted, Coffered, and Beam ceilings with custom crown molding throughout, 3 fireplaces to keep you warm on a cool summers night, powered chandelier in foyer, with an impressive entry door. Some exterior features include but not limited to grand columns made from imported Brazilian marble as you come up the grand entrance, stucco with brick vaneer, terra cotta roof, high impact windows and doors, professionally landscaped, and spiral staircase to picturesque outdoor living spaces so you can relax and listen to the waves crash on the shore. The massive covered outdoor living space features automatic power screens, fireplace, large seating area, built-in grill, full wet bar with beer taps and kegerators, custom cabinetry, everything you need for a sunny beach day. The geothermal heated salt water pool with hot tub features custom columns and bronze sculpture fountains, with plenty of palm trees for a truly tropical feel. Some mechanical features include Geo-Thermal HVAC units with 7 zones, spray foam insulated throughout, and whole house emergency generator. Community features include 18 hole golf course designed by Pete Dye, private beach access, members only access to beach club, boating with 2 boat storage areas, crabbing, fishing, walking and biking trails, plus lots of other outdoor activity opportunities available. Close to shopping, dining, entertainment, live local music, and medical facilities. 

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Saint Augustine, FL

14 Joiner Street, St Augustine, FL “The Old Mansion”

For sale: $1,750,000

One of the most desirable properties in the heart of Historic St. Augustine, FL, The Old Mansion sits on an entire city block within the The Abbott Tract, an historic district that is on the US Registry of Historic Places. Originally built by Lucy Abbott herself in 1880, The Old Mansion can be enjoyed in many ways, be it a single family residence, a Bed and Breakfast or possibly an event space, this is a very rare and unique opportunity. The main home has four bedrooms and two one bedroom apartments and the coach house has two studio apartments. Just blocks from the oldest masonry fort in the US, Castillo de San Marcos, historic St. George Street and the Fountain of Youth, The Old Mansion is located in the heart of Historic St. Augustine, FL. Purchased and lovingly renovated in 1980 by the current owner, the interior is designed after a Victorian English Manor reminding the owner of her youth. Elaborate plasterwork, wood paneling, stained glass and other features stand out giving the home a feeling of timeless elegance. The spacious gardens are covered by a canopy of old oaks, estimated to be over 225 years old. Garden paths, flowers, fountains and sculptures create the feeling of a secret hidden garden in the heart of the city.

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Miami, FL

14949 SW 184th Ave, Miami, FL

For sale: $4,490,000

Equestrian Estate situated on approximately 5 gates acres. The estate consists of a great house comprised of 6 spacious bedrooms, 7 full baths, gourmet kitchen, with the top of the line finishes with architectural features throughout. Impeccable manicured landscape grounds with a guest house, a carriage house above the garage, pool, two gazebos, an outdoor kitchen complete with barn and stalls. The Estate includes all furniture, fixtures and entertainment systems. Owner financing is available.

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Islamorada, FL

82910 Overseas Highway, Islamorada, FL

For sale: $12,500,000

From the private picturesque setting, this 6.41 acre bay front estate offers over 12,400 square feet of living space including a main residence and two guest cottages. This estate features charming Key West style architecture, intimate garden courtyards, balconies and spacious patios overlooking a bay front pool/spa with cabana. Property also features a rare deep-water boat basin with jetty that can host numerous boats or yachts. Exquisitely crafted, the 2 story main home features 6 bedrooms/5 baths/3 half baths. The guest cottage west features 4 bedrooms/3.5 baths and incredible bay views.The guest cottage east includes 3 bedrooms/3 baths and overlooks the pristine gardens and the tennis court. Other amenities and out buildings include a 4 car garage, lighted tennis court, volley ball court, boat house and staff offices. Property is gated for privacy.

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Santa Barbara, CA

4305 Marina Drive, Santa Barbara, CA

For sale: $25,000,000

Spectacular and newly built contemporary residence in Hope Ranch. Approx. 3.7-acre bluff setting with 204’ ocean frontage. Striking approx. 10,143-sq.ft. home with walls of glass features fabulous living, dining, family/kitchen/bar space. Glass walled rotundas in family and master suite. Amazing home theater, pilates/yoga studio, auxiliary kitchen for large scale entertaining. Three in-wall salt water aquariums, amazing private office, magnificent master with spa-like dressing/bath. Magical third story “lookout” tower with spa that opens to the stars. Three private, over-sized guest bedrooms each with balcony. Expansive grounds and manicured gardens. Wonderful pool and terraces. Cliffside sitting area with fire pit. Private path descends to beach. N/S tennis court, beautiful rose gardens, fruit orchard, Chef’s vegetable garden, approx. 1,700-sq.ft. workshop/art studio. Astonishing attention to detail, fully automated home. Uniquely designed for sophisticated comfort and ease of living.

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