Regatta Bay Homes with Columns Exterior Features

Regatta Bay Homes with Columns Exterior Features

Welcome to Regatta Bay, a premier subdivision located in Destin, FL, in the picturesque Okaloosa County. This exclusive community offers a luxurious lifestyle with stunning homes and top-notch amenities.

Regatta Bay is known for its beautiful homes with classic Columns Exterior Features that exude elegance and sophistication. These homes are meticulously designed to provide a blend of timeless architecture and modern comforts.

Living in Regatta Bay means enjoying a serene environment surrounded by lush landscapes and scenic views. Residents have access to world-class facilities, including a championship golf course, a marina, tennis courts, swimming pools, and a clubhouse.

The community is conveniently located near top-rated schools, fine dining restaurants, shopping centers, and pristine beaches, offering the perfect balance between tranquility and convenience.

Whether you are looking for a permanent residence or a vacation home, Regatta Bay offers a unique opportunity to experience luxury living at its finest. Don't miss the chance to be part of this exclusive community and enjoy the best that Destin, FL, has to offer.

Newest Regatta Bay Homes with Columns Exterior Features

$2,490,000
4 Beds ⋅ 6 Baths ⋅ 1007912 MLS
Less than a mile from the beach! Finishes and details are stunning! Introducing Tradewinds, the latest gem in Regatta Bay, featuring 54 exquisite homesites inspired by the architectural elegance of the West Indies and Dutch styles. This stunning, brand-new residence embodies modern luxury, seamlessly blending indoor and outdoor living across over 3,600 square feet of climate-controlled space. It boasts 4 bedrooms, 4 full bathrooms, and 2 additional half baths. Upon entry, you are immediately captivated by the design, featuring wood beams on the ceiling and gracefully curved arches. The home presents a sophisticated black-and-white theme, enhanced by tasteful tile selections in the kitchen, butler's pantry, wet bar, and bathrooms. The home boasts an inviting open floor plan, highlighted by a spacious living room featuring a cozy fireplace and a gourmet chef's kitchen equipped with top-of-the-line amenities. On the first floor, the master bedroom provides breathtaking views and direct access to the outdoor living area. The master bath showcases double vanities, elegantly designed lighting fixtures, a custom walk-in tiled shower, and a luxurious soaking tub. Adjacent to the master bedroom, a generous walk-in closet offers custom shelving and his-and-her drawers for added storage. Also located on the first floor is a convenient powder bath for guests, a wet bar, and a guest suite complete with its own private bath. Upstairs, you will discover a generous bonus room, an extra wet bar, two guest suites each featuring private baths, a sizable storage or multipurpose room, and an expansive balcony. The exterior showcases an inviting outdoor area, complete with a summer kitchen and a picturesque Alys Beach-style pool, making this home an ideal retreat for relaxation and entertainment. Built by Legendary Home Builders, utilizing only the finest materials and high end finishes such as: wind and impact resistant windows, wind and impact rated doors, insulated wind and impact rated garage doors, insulation in all interior walls for energy efficiency, sound proofing insulation between floors for sound barrier, stainless steel door hinges, custom wood shelving in all closets, Kohler plumbing throughout, custom solid wood cabinetry throughout with soft close hinges, surround sound, smart home technology customizable for homeowner, led lighting throughout and so much more...

4685 Westwinds Way, Destin
$1,889,000
5 Beds ⋅ 4 Baths ⋅ 1006567 MLS
Welcome to 440 Regatta Bay Blvd, a beautiful single-level home located within the prestigious, gated golf course community of Regatta Bay. Situated on a golf course lot, this extensively renovated residence offers the ideal blend of luxury, functionality and relaxed coastal living. Spanning approximately 3,644 square feet of living space, this thoughtfully designed home features 5 bedrooms, 3.5 bathrooms and an expansive open-concept floor plan. With extensive renovations completed between 2019-2026, this property has been meticulously enhanced with high-end finishes, modern systems and designer touches throughout. From the moment you arrive, the home makes a striking impression with beautiful, updated landscaping, fresh exterior paint and a welcoming entry that reflects the quality found inside. A climate controlled 3-car garage provides multi-functional use, ample parking, plenty of storage and a Level 2 EV charging port. Step through the front door into a light-filled interior where high ceilings, updated finishes and an open layout create a sense of comfort and sophistication. The heart of the home is the chef-inspired, fully updated customized kitchen. This showstopping space features custom cabinetry, an island with a prep sink, leathered granite countertops and a large ceramic farmhouse sink. A professional-grade 48-inch gas range with double ovens anchors the space, making it ideal for entertaining! Adjacent to the kitchen, the spacious living area serves as a central gathering place, enhanced by a newly installed designer fireplace that adds warmth and a modern focal point. The primary suite is a true retreat. The renovated ensuite bath reflects a spa-like aesthetic, featuring a beautifully retiled walk-in shower, a new double vanity and updated finishes. Four additional bedrooms provide exceptional flexibility for family, guests, or work-from-home needs. One bedroom includes its own ensuite bath, offering privacy ideal for guests or multigenerational living. Additional updates to both the ensuite and powder bath ensure consistency in design and quality throughout the home. Step outside to experience one of the property's most compelling features, the private outdoor oasis. A custom heated saltwater pool, completed with a screened enclosure and paver decking, creates the perfect environment for year-round enjoyment. Whether you're hosting poolside gatherings, enjoying quiet evenings under the lanai or soaking in the Florida sunshine, this space is designed for both relaxation and entertainment. The large, fully fenced backyard is a rare find within a golf course setting, offering both privacy and space--ideal for pets, play or future customization. Beyond the fence line, the home enjoys peaceful golf course views. This property has also been significantly upgraded with major system improvements, providing peace of mind for years to come. Highlights include a new HVAC system, a tankless water heater for energy efficiency and endless hot water and updated interior and exterior paint. Regatta Bay is a serene, gated community that seamlessly blends golf and boating, offering a lifestyle that is truly unparalleled! The essence of the Regatta Bay Lifestyle revolves around convenience, allowing residents to easily access numerous enjoyable destinations within minutes via golf cart, including the beach! Within the community, residents can indulge in golf, swimming, tennis, pickleball, parks, playgrounds, the Regatta Bay Clubhouse, Legendary Marine, and Legendary Yacht Club. Furthermore, Regatta Bay features a private road that leads directly to the Destin Commons, where an array of popular retail stores for both men and women awaits, alongside a diverse selection of restaurants, Whole Foods, Bass Pro, Lowes, an AMC movie theater, and Uncle Buck's Bowling-all easily reachable by golf cart. Regatta Bay is centrally located offering easy access to the airport and only a few miles from Northwest Florida's finest hospital. Schedule your private tour today and experience the elegance of Regatta Bay living.

440 Regatta Bay Blvd, Destin
$2,950,000
5 Beds ⋅ 5 Baths ⋅ 1006221 MLS
Custom-Built Pool Home in Regatta Bay Golf & Yacht Club a perfect blend of refined elegance and effortless coastal living. A dramatic 12-foot coffered foyer with reclaimed solid wood accents welcomes you, complemented by custom 8-foot mahogany entry doors. The spacious living area, anchored by a fireplace, flows seamlessly into the chef's kitchen under an impressive open floor plan featuring soaring ceilings, rich hardwood floors, and abundant natural light. Floor-to-ceiling sliders in the living area frame breathtaking views of the outdoor entertainment area, complete with a summer kitchen, heated pool, and hot tub, creating a warm yet sophisticated atmosphere perfect for relaxed living and elegant indoor-outdoor entertaining. The chef's kitchen is a showstopper, featuring quartz countertops, a massive island with seating area, a 48-inch Thermador gas range, Sub-Zero refrigerator, a large walk-in pantry, and a separate wet bar with icemaker. The first-floor primary suite is a true retreat, complete with a sitting area offering serene pool views, dual walk-in closets, and a spa-like bath with double vanities, a deep soaking tub, and a separate tiled walk-in shower. Also on the main level is a guest suite complete with en-suite bath and walk-in closet, a flexible third bedroom/office, and an oversized laundry room with plenty of storage. Upstairs, a second living area with an additional bonus room provides versatile living space, with two additional guest bedrooms each featuring generous walk-in closets and private full bathrooms. A covered balcony overlooking the pool and golf course offers another peaceful vantage point. Plenty of extra storage throughout along with a 3-car garage, spacious attic storage and roomy closets. This energy-efficient home includes a solar power system, whole-house generator, impact-resistant windows and doors, insulated wind-rated garage doors, spray foam roof insulation, superior sound-dampening insulation, custom solid wood cabinetry and shelving, and Schluter waterproofing systems throughout. Built for year-round living and entertaining, this residence delivers luxury and peace of mind in one of Destin's most sought-after communities.

502 Regatta Bay Blvd, Destin
$2,379,000
4 Beds ⋅ 5 Baths ⋅ 1002898 MLS
Less than a mile from the beach, this breathtaking new construction home delivers exceptional luxury and striking attention to detail. Welcome to Tradewinds--the newest enclave within Regatta Bay--featuring 54 exclusive homesites inspired by refined West Indies and Dutch-Caribbean architecture. This exquisite residence offers over 3400 square feet of climate-controlled living space with 4 bedrooms, 4 full baths, and 1 half bath. Designed for seamless indoor-outdoor enjoyment, the home centers around a private outdoor oasis complete with a summer kitchen, hot tub and an Alys Beach-inspired pool, creating an ideal setting for both relaxation and entertaining. Inside, the open-concept layout immediately impresses. The expansive living room is anchored by a custom fireplace and flows effortlessly into a chef's kitchen featuring quartzite countertops, a large island, premium appliances, and a spacious pantry with custom shelving. The first-floor primary suite offers serene views and direct access to the outdoor living area. Its spa-like bathroom includes dual vanities, designer lighting, a custom-tiled walk-in shower, and a luxurious soaking tub. A generously sized walk-in closet features custom shelving and built-in his and her storage. Also on the main level is a stylish powder room and a private guest suite with its own bath. The second floor features a large bonus room with a wet bar, laundry room, two guest suites with private baths and a large balcony perfect for enjoying evening breezes. Built by Legendary Home Builders, utilizing only the finest materials and high end finishes such as: wind and impact resistant windows, wind and impact rated doors, insulated wind and impact rated garage doors, insulation in all interior walls for energy efficiency, sound proofing insulation between floors for sound barrier, stainless steel door hinges, custom wood shelving in all closets, Kohler plumbing throughout, custom solid wood cabinetry throughout with soft close hinges, surround sound, smart home technology customizable for homeowner, led lighting throughout and so much more! This extraordinary home captures the essence of modern coastal luxury beautiful, functional, and just moments from the beach. Regatta Bay is a serene, gated community that seamlessly blends golf and boating, offering a lifestyle that is truly unparalleled! The essence of the Regatta Bay Lifestyle revolves around convenience, allowing residents to easily access numerous enjoyable destinations within minutes via golf cart, including the beach! Within the community, residents can indulge in golf, swimming, tennis, pickleball, parks, playgrounds, the Regatta Bay Clubhouse, Legendary Marine, and Legendary Yacht Club. Furthermore, Regatta Bay features a private road that leads directly to the Destin Commons, where an array of popular retail stores for both men and women awaits, alongside a diverse selection of restaurants, Whole Foods, Bass Pro, Lowes, an AMC movie theater, and Uncle Buck's Bowling-all easily reachable by golf cart. Regatta Bay is centrally located offering easy access to the airport and only a few miles from Northwest Florida's finest hospital. Schedule your private tour today and experience the elegance of Regatta Bay living.

4564 Leeward Ln, Destin
$3,490,000
4 Beds ⋅ 6 Baths ⋅ 995363 MLS
Less than a mile from the beach! Welcome to Tradewinds, the newest community in Regatta Bay consisting of 54 homesites with a West Indies/Dutch architectural influence. This beautiful home was built in 2023 and offers modern luxury indoor/outdoor living w/ 4797 sq. ft. of heated/cooled space, 4 beds, + study, 4 full baths and 2 half baths. Exterior features include an outdoor living space overlooking the golf course and lake with covered and uncovered space for entertaining and lounging, summer kitchen, pool/jacuzzi and fire pits. This home features lush landscaping that is maintained by the association, paver driveway and a 3-car garage plus golf cart garage. The home was finished with designer chosen selections throughout including shiplap, Venetian Plaster, tumbled travertine & wood flooring, quartzite & marble countertops and solid wood custom cabinetry just to name a few. The 1st floor offers a split floor plan and includes a family room w/gas fireplace, dining area, gourmet kitchen with all the bells and whistles, scullery with additional kitchen appliances, butler's pantry, wet bar, study, powder bath for guests, laundry room and a guest suite with private bath. The master suite is also located on the 1st floor and features a custom cathedral ceiling with painted wood beams, sitting area and a showstopping master bath which includes separate his and her walk-in closets, separate his and her vanities, separate his and her water closets, a large custom marble tile shower, soaking tub and last but not least a master laundry room! The 2nd floor offers a large entertainment space with wet bar, powder bath for guests, 2 guest suites with private baths and a laundry room. Built by Legendary Home Builders utilizing the most current technology for each build using only the finest materials and high-end finishes such as: wind and impact resistant windows, wind and impact rated doors, insulated, wind and impact rated garage doors, foam spray insulation in roof for superior energy efficiency, insulation in all interior walls for energy efficiency and sound proofing, insulation between floors for sound barrier, stucco homes equipped with Enviro-dry liquid waterproofing house wrap, gas lanterns, stainless steel door hinges, custom wood shelving in all closets, Kohler plumbing throughout, all showers have KBRS waterproofing systems specifically designed to maintain integrity & durability, air conditioning zones for maximum efficiency, Rinnai tankless water heaters, custom solid wood cabinets throughout with soft close hinges, smart home technology customizable for homeowner, LED lighting throughout. Regatta Bay is a quiet, gated, golf & boating community that offers a LIFESTYLE unlike no other! The Regatta Bay Lifestyle is about convenience! You can golf cart to so many fun places in minutes, including the Beach! Within Regatta Bay, there is golf, swimming, tennis, pickle ball, park, playground, Regatta Bay Clubhouse, Legendary Marine & Legendary Yacht Club. Regatta Bay offers a private road that takes residents to the Destin Commons, where you'll find an array of popular men's and women's retail stores, a variety of restaurants, Whole Foods, Bass Pro, Lowes, AMC movie theater and Uncle Buck's Bowling! ALL ACCESSIBLE BY GOLF CART.

4548 Sailmaker Ln, Destin
$2,150,000
4 Beds ⋅ 6 Baths ⋅ 994546 MLS
PRICED BELOW MARKET VALUE!!! The entire exterior of the home has been recently painted with a fresh coat of elastomeric paint! Located in Regatta Bay's newest community, Tradewinds, this exceptional luxury coastal home showcases refined craftsmanship and timeless design. Built in 2022 by Legendary Home Builders, the home features West Indies architecture with Dutch influence, thoughtfully curated for elegant coastal living. Offering 4 bedrooms, 4 full baths, 2 half baths and a 3-car garage, this smart home spans 3,078 sq. ft. of heated/ cooled living space and is filled with hand-selected designer finishes throughout. Hardwood floors flow seamlessly through the home, complemented by quartzite countertops, custom tiled showers and elevated details at every turn. The master bedroom is a true retreat, featuring a large walk-in closet, a spa-inspired bath with a soaking tub, and separate walk-in shower. A first-floor guest bedroom with private bath, powder room and spacious laundry room with sink provide both comfort and convenience. Designed for entertaining, the large gourmet kitchen is equipped with top-of-the-line features and opens to the expansive living area. Step outside to the screened outdoor living space with summer kitchen, private pool and spa and spectacular views of the lake and golf course the perfect setting for year-round enjoyment. Upstairs, a versatile bonus/flex space is joined by two additional bedrooms, each with private en-suite baths, offering privacy and flexibility for family or guests. Last but certainly not least the home offers and whole house generator. Built by Legendary Home Builders, utilizing only the finest materials and high end finishes such as: wind and impact resistant windows, wind and impact rated doors, insulated wind and impact rated garage doors, insulation in all interior walls for energy efficiency, sound proofing insulation between floors for sound barrier, stainless steel door hinges, custom wood shelving in all closets, Kohler plumbing throughout, custom solid wood cabinetry throughout with soft close hinges, surround sound, smart home technology, led lighting throughout and so much more...This remarkable home combines luxury, location, and lifestyle in one of Destin's most desirable gated communities. Regatta Bay is a serene, gated community that seamlessly blends golf and boating, offering a lifestyle that is truly unparalleled! The essence of the Regatta Bay Lifestyle revolves around convenience, allowing residents to easily access numerous enjoyable destinations within minutes via golf cart, including the beach! Within the community, residents can indulge in golf, swimming, tennis, pickleball, parks, playgrounds, the Regatta Bay Clubhouse, Legendary Marine, and Legendary Yacht Club. Furthermore, Regatta Bay features a private road that leads directly to the Destin Commons and Paradise Key, where an array of popular retail stores for both men and women await, alongside a diverse selection of restaurants, Whole Foods, Publix, Wine World, Nail Salons, Sephora, Bass Pro, Lowes, AMC movie theater, and Uncle Buck's Bowling-all easily reachable by golf cart. Regatta Bay is centrally located offering easy access to the airport and only a few miles from Northwest Florida's finest hospital. Schedule your private tour today and experience the elegance of Regatta Bay living.

4572 Sailmaker Ln, Destin
$1,499,000
4 Beds ⋅ 5 Baths ⋅ 993361 MLS
259 Moonlit Way is an exceptional Southern-inspired residence tucked within The Preserve at Regatta Bay, an exclusive 21-home enclave known for privacy, elegance and refined coastal living. Built in 2019, this thoughtfully designed home blends timeless architectural character with modern luxury finishes throughout. Step inside to soaring natural light, designer selections and wood flooring that flows seamlessly across the home. The gourmet kitchen is a statement of craftsmanship--featuring quartz countertops, custom cabinetry, a Sub-Zero refrigerator, Wolf gas range and a spacious walk-in pantry. A stylish wet bar just off the kitchen adds the perfect touch for entertaining. Click ''more'' to continue... Offering 4 bedrooms and 4.5 baths, each bedroom is generously sized with large walk-in closets, creating a comfortable and private retreat for family and guests. The home's open layout extends effortlessly to the outdoors, where a sparkling pool provides the ultimate place to unwind. The hallmark of this residence is its expansive wrap-around porch, offering abundant space to relax, dine or host gatherings while enjoying the peaceful, boutique setting of Regatta Bay Preserve. The oversized 2.5 car garage provides exceptional storage and functionality. This is a rare opportunity to own a newer construction luxury home in one of Regatta Bay's most sought-after neighborhoods where charm, craftsmanship and coastal elegance come together seamlessly. Built by Legendary Home Builders, utilizing only the finest materials and high end finishes such as: wind and impact resistant windows, wind and impact rated doors, insulated wind and impact rated garage doors, insulation in all interior walls for energy efficiency, sound proofing insulation between floors for sound barrier, stainless steel door hinges, custom wood shelving in all closets, Kohler plumbing throughout, custom solid wood cabinetry throughout with soft close hinges, surround sound, smart home technology customizable for homeowner, led lighting throughout and so much more! Regatta Bay is a quiet, gated, golf & boating community that offers a LIFESTYLE unlike no other! The Regatta Bay Lifestyle is about convenience! You can golf cart to so many fun places in minutes, including the Beach! Within Regatta Bay, there is golf, swimming, tennis, pickle ball, park, playground, Regatta Bay Clubhouse, Legendary Marine & Legendary Yacht Club. Regatta Bay offers a private road that takes residents to the Destin Commons, where you'll find an array of popular men's and women's retail stores, a variety of restaurants, Whole Foods, Bass Pro, Lowes, AMC movie theater and Uncle Buck's Bowling! ALL ACCESSIBLE BY GOLF CART.

259 Moonlit Way, Destin
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