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266 Woodland Bayou Dr, Santa Rosa Beach
$3,950,000
5 Beds ⋅ 7 Baths ⋅ 1014311 MLS ⋅ 5,808 SqFt.
Set across 1.5 private acres in Woodland Bayou, 266 Woodland Bayou Drive offers an exceptional blend of architectural sophistication, thoughtful craftsmanship, and waterfront living. This custom residence features approximately 5,808 square feet of heated and cooled living space, expansive entertaining areas, and direct access to the bay. Inside, engineered white oak hardwood floors flow throughout the home, leading into a dramatic two-story living room anchored by a soaring fireplace and custom built-ins. The gourmet kitchen is appointed with Thermador appliances, a 48-inch gas range, under-cabinet lighting, an oversized island, and both a butler's pantry and generous walk-in pantry. A formal dining room, glass-enclosed wine room, and spacious bar with seating for five create an inviting atmosphere for entertaining, while a separate wet bar with a beverage refrigerator and ice maker adds convenience. The thoughtfully designed floor plan features four bedrooms, each with a private ensuite bath, including the primary suite and an additional guest suite on the main level. The primary retreat showcases elegant marble finishes, a soaking tub, walk-in shower, and an expansive custom closet with a center island and built-ins, along with private access to the rear porch. Upstairs, two additional ensuite bedrooms are joined by a versatile flex room with a closet, ideal for a home office or fifth bedroom. A secondary sitting area opens to an outdoor balcony overlooking the surrounding property. Above the three-car garage, a spacious bonus retreat offers a private escape complete with a kitchenette and half bath, with plumbing already in place for a potential conversion to a full bathroom. The garage features a utility sink, additional storage bay, and dedicated storage closet, while three attic spaces, an oversized laundry room, and a whole-house Generac generator further enhance the home's functionality. Designed for seamless indoor-outdoor living, the screened rear porch features a fully equipped summer kitchen with a grill, smoker, and beverage refrigerator. Beyond, the fenced backyard offers a resort-inspired retreat with a heated and cooled saltwater pool, hot tub, expansive lounging areas, and a covered pool pavilion complete with a fireplace and bar. An outdoor shower, dedicated pool half bath, and multiple gated access points to the side yard and dock add to the property's thoughtful design. Along the bayou, a two-level private dock with a boat lift and floating jet ski dock provides effortless access to boating, fishing, and waterfront recreation. Surrounded by lush grounds and offering exceptional privacy, this remarkable property combines custom architectural details, generous living spaces, and an unparalleled outdoor lifestyle. With approximately 8,209 square feet under roof, 266 Woodland Bayou Drive presents a rare opportunity to enjoy refined waterfront living in the heart of Santa Rosa Beach.

266 Woodland Bayou Dr, Santa Rosa Beach
273 Churchill Oaks Dr, Santa Rosa Beach
$3,625,000
5 Beds ⋅ 8 Baths ⋅ 1011437 MLS ⋅ 4,712 SqFt.
Set within the private gates of Churchill Oaks, 273 Churchill Oaks Drive blends thoughtful design, versatile living, and effortless access to the coastal lifestyle. Located in this premier bayfront community, the home offers over 4,000 square feet of refined living space, including four bedrooms, four-and-a-half bathrooms, and a private carriage house--perfect for guests, extended family, or a dedicated home office. The spacious great room, anchored by a gas fireplace and framed by an abundance of windows and doors, sets the tone for the home's mix of traditional elegance with modern touches.

273 Churchill Oaks Dr, Santa Rosa Beach
389 Driftwood Point Rd, Santa Rosa Beach
$3,750,000
6 Beds ⋅ 7 Baths ⋅ 1010759 MLS ⋅ 7,216 SqFt.
Set along the peaceful shores of Choctawhatchee Bay, 389 Driftwood Point Road is a remarkable waterfront estate where architectural character, privacy, and the beauty of bayfront living come together. Set on 1.1 private bayfront acres, this custom estate offers the perfect balance of luxury and the effortless waterfront lifestyle that makes Santa Rosa Beach so desirable. Spanning 7,216 square feet, the property features a 4-bedroom, 3.5-bath main residence and a detached 2-bedroom, 2-bath guest house, creating exceptional flexibility for hosting family, friends, or extended stays. Complete with a private dock and resort-style outdoor living, every space is thoughtfully designed for entertaining and making the most of life on the bay. The residence reflects timeless architectural character and craftsmanship. Blending the charm of New Orleans architecture with the relaxed elegance of the Emerald Coast, the home showcases antique doors, Old Chicago brick, copper gutters, private balconies, and inviting courtyards that give the estate a sense of history, warmth, and authenticity. Inside, you'll find a chef's kitchen with premium appliances, a spacious bayfront primary suite with a beautifully appointed bath that opens directly to a private courtyard for a true retreat, flexible bonus spaces, a separate guest wing complete with its own full kitchen, and the detached guest house offering a private retreat for visitors or multigenerational living. Outside, the estate transforms into a true waterfront oasis. The expansive backyard is centered around a 20-by-40 resort-style pool, while the pool house serves as the ultimate entertaining hub with a summer kitchen, convenient half bath, and relaxed gathering space perfect for cookouts, game days, sunset dinners, or unwinding after a day on the water. Every space is designed to bring family and friends together while embracing the beauty of the waterfront setting. The private dock is equipped with two boat lifts, a boathouse, a jet ski lift, and a kayak launch, providing effortless access to boating, fishing, paddleboarding, and endless days exploring Choctawhatchee Bay. Conveniently located just minutes from Grand Boulevard, Sacred Heart Hospital, top-rated schools, and the sugar-white beaches of 30A, this exceptional bayfront estate delivers a distinctive combination of architectural significance, peaceful waterfront living, privacy, and everyday convenience.

389 Driftwood Point Rd, Santa Rosa Beach
32 Driscoll Dr, Santa Rosa Beach
$3,795,000
4 Beds ⋅ 5 Baths ⋅ 1006021 MLS ⋅ 3,983 SqFt.
The waterfront home you have been waiting for. Tucked away on a private street under mature trees, this beautiful home offers a rare combination of privacy, deep-water boating access, and refined luxury living just minutes from the beach on 30A. Completely renovated down to the concrete block and thoughtfully redesigned, the nearly 4,000-square-foot home offers the peace of mind and insurance advantages of nearly new construction. Timeless finishes include site-finished white oak hardwood floors, Bevolo lanterns, and a top-tier appliance package featuring dual 36-inch Sub-Zero columns, along with Wolf and Bosch appliances. A spacious butler's pantry and extensive custom cabinetry will delight both avid entertainers and serious home chefs. Designed to capitlize on the stunning waterfront setting, the home captures beautiful bayou and bay views from the main living areas and the primary suite. The primary retreat, which occupies its own wing, features a step-free marble shower, cast-iron soaking tub, thoughtfully designed three-level closet system, private laundry, and a secure safe room. Boating enthusiasts will appreciate the newly constructed covered dock with a 12,000-pound lift and access to some of the deepest protected waters in Santa Rosa Beach, accommodating larger vessels than many nearby waterfront properties, and a private slipway ramp makes launching paddleboards and kayaks effortless. The home's western-facing orientation and folding glass wall create... seamless indoor-outdoor living, opening to an expansive pool deck where sunsets become a nightly ritual. The brand new pool and spa are just the icing on the cake. Ideally located on the desirable west end of Santa Rosa Beach, you're less than 10 minutes from 30A's beaches, Grand Boulevard, Publix, and Butler Elementary School.

32 Driscoll Dr, Santa Rosa Beach
295 Churchill Oaks Dr, Santa Rosa Beach
$3,795,000
4 Beds ⋅ 5 Baths ⋅ 1005355 MLS ⋅ 4,124 SqFt.
Home is where the heart is, and you'll quickly fall in love with Churchill Oaks. Nestled along Hogtown Bayou on the scenic Choctawhatchee Bay, this exclusive waterfront community offers over half a mile of shoreline and a private deep-water marina with boat slips. A rare opportunity exists to purchase separately a deeded 35-foot boat slip featuring a boat lift, providing convenient access to Choctawhatchee Bay and the Gulf beyond. This elegantly designed home is nestled among the beautifully landscaped grounds of Churchill Oaks, awaiting your arrival. Upon stepping into the foyer, you'll immediately appreciate the home's exceptional architectural beauty and thoughtful design. From the soaring ceilings and natural stone flooring that extend throughout the first floor to the elegant mirrored wet bar and refined custom finishes, every detail has been carefully curated to create an atmosphere of timeless sophistication and comfort. The seamless flow of the living spaces enhances both everyday living and entertaining, while abundant natural light highlights the home's exquisite craftsmanship. The kitchen is a chef's dream, featuring a Wolf six-burner gas range with griddle, separate refrigerator and freezer, a convenient coffee station, stunning quartzite countertops, and an impressive 12-foot island that serves as the perfect gathering place for family and guests alike. Just off the kitchen, you'll find a spacious butler pantry designed for both convenience and entertaining. This well-appointed space includes a second dishwasher, microwave, warming drawer, additional sink, and beverage refrigerator, making it easy to host large gatherings while keeping the main kitchen beautifully organized and functional. Step into the spacious living room and unwind by the inviting fireplace, beautifully framed by expansive windows that flood the space with natural light and offer tranquil views of the surrounding landscape. Just beyond, the rear porch provides a peaceful retreat for relaxing or entertaining while enjoying the beauty of nature. Take the elevator to the second floor, where wide-plank white oak flooring adds warmth and elegance throughout. This thoughtfully designed level features a spacious sitting area, a convenient breakfast bar, a laundry room, a private office with a fireplace, and three additional bedrooms. The home offers two luxurious primary suites, each highlighted by soaring 12-foot vaulted ceilings, creating a light and airy retreat. An additional guest bedroom provides comfortable accommodations for family and visitors. The main primary suite is a true sanctuary, featuring a spacious walk-in closet and a beautifully appointed ensuite bath with dual vanities, a soaking tub, and a separate walk-in shower, offering the perfect place to relax and unwind at the end of the day. Ideally situated near the community boardwalk, the home offers convenient access to the clubhouse, fitness center, resort-style pool, and private marina, allowing you to fully embrace the exceptional waterfront lifestyle Churchill Oaks offers.

295 Churchill Oaks Dr, Santa Rosa Beach
1239 Driftwood Point Rd, Santa Rosa Beach
$3,199,999
5 Beds ⋅ 5 Baths ⋅ 1001357 MLS ⋅ 4,726 SqFt.
A magnificent custom Mediterranean estate situated on 100 ft of Choctawhatchee Bay. This showpiece's timeless, luxurious appointments; open, airy floor plan; and opulent landscaping are matched in exquisiteness only by the surrounding natural scenery. A large expanse of glass seamlessly merges the interior with the outdoors. A spectacular, fenced-in bayfront oasis features a large pool and covered sitting area. Incredible Sunrise views. This home offers master on the main, 2 master suites on 2nd floor, a study and a separate media room that can easily be turned into a 5th bedroom. Both the 1st floor and 2nd floor master suites offer outdoor access and luxurious en suites. Just 7 minutes north of Sandestin/Grand Blvd and 15mins to 30A. Exterior freshly painted all white. Bank Qual required

1239 Driftwood Point Rd, Santa Rosa Beach
37 Junop Ct, Santa Rosa Beach
$3,325,000
4 Beds ⋅ 5 Baths ⋅ 995561 MLS ⋅ 4,122 SqFt.
Set within the gates of Churchill Oaks, this thoughtfully designed residence captures peaceful bayou views and a level of craftsmanship rarely found. Architectural details such as arched doorways, a vaulted two-car garage, and decorative rain-chain downspouts establish the home's distinctive character, while light oak flooring, Restoration Hardware lighting, and a grand motorized foyer chandelier create a refined, welcoming interior. The well-conceived floor plan balances everyday functionality with elevated design, featuring a butler's pantry, boot room hallway, and a stylish guest bath with designer wallpaper. A first-floor junior suite offers comfort and privacy, complete with an elegant ensuite bath showcasing an oval soaking tub, dual vanities, and a frameless glass shower. At the center of the home, the open-concept kitchen is both striking and highly functional, appointed with floor-to-ceiling cabinetry, quartz countertops, a contrasting wood and white granite island, and premium Wolf and Sub-Zero appliances, including a six-burner gas range. The adjacent dining area with wet bar flows seamlessly into the living room, where wood-beam ceiling details and a gas fireplace create a warm yet sophisticated setting. Expansive sliding glass doors open to a spacious terrace designed for year-round enjoyment, complete with outdoor heating, electric screens, and a plunge pool with a tranquil water feature. Accessible by private elevator, the second level includes two beautifully appointed guest suites and a vaulted primary suite designed as a true retreat. The spa-inspired bath features a frameless glass shower and a custom dressing room with extensive built-in storage, while a private screened porch offers sweeping views of Hogtown Bayou and the surrounding natural landscape. Churchill Oaks is an exclusive 40-acre gated waterfront community with just 87 homesites, offering residents access to a deepwater marina, waterfront clubhouse, three resort-style pools, fitness center, and outdoor gathering spaces. The result is a lifestyle defined by privacy, natural beauty, and effortless access to boating and the best of the Emerald Coast.

37 Junop Ct, Santa Rosa Beach
55 Teal Ct, Santa Rosa Beach
$3,390,000
5 Beds ⋅ 4 Baths ⋅ 980748 MLS ⋅ 3,582 SqFt.
Nestled in the heart of Santa Rosa Beach, this bayfront custom design defines luxury coastal. Multi-level unobstructed bay views create for the unparalleled opportunity of breathtaking sunsets over Choctawhatchee Bay with 30A's white sand beaches just minutes away. The home itself leaves no design stone unturned with multiple spacious indoor-outdoor living spaces, top to bottom coastal-elegant accenting, and more. For boating enthusiasts, the newly built, deepwater dock maintains a 16,000lb boat lift and can accommodate up to 36 in footage. Family Crab Island adventures and the Gulf's ample fishing opportunities are steps from your back door.

55 Teal Ct, Santa Rosa Beach
68 Perrin, Santa Rosa Beach
$3,999,000
5 Beds ⋅ 7 Baths ⋅ 990446 MLS ⋅ 4,298 SqFt.
68 Perrin sits within the gated community of Churchill Oaks and offers a modern coastal design built around clean lines, natural light, and a functional layout that lives comfortably day to day. The home spans roughly 4,298 square feet with five bedrooms, five full baths, and two half baths arranged to balance openness with privacy. The main living area feels refined without being overdone. Tall ceilings, expansive windows, and a marble-accented fireplace create a bright and inviting central space. The living, dining, and kitchen areas connect seamlessly, giving the home a sense of ease and flow. The kitchen features a waterfall-edge island, high-end appliances, and streamlined cabinetry that keeps the space crisp and uncluttered. The primary suite is located on the main level... and is positioned to feel removed from the activity of the home. Vaulted ceilings and large windows bring in soft natural light, and the adjoining bath and custom walk-in closet reinforce a sense of calm and functionality. The remaining bedrooms are each en-suite and placed on separate wings or levels, offering comfort and independence for family or guests. Throughout the home, the layout feels intentional and well measured. Outdoor living centers around a private courtyard that serves as an extension of the interior. A pool, spa, firepit, outdoor kitchen, and exterior half bath give the space structure and utility while maintaining a relaxed coastal feel. Access from multiple points of the home makes the courtyard a natural focal point. Two garages add convenience and storage. Churchill Oaks is one of Santa Rosa Beach's most thoughtfully planned communities, set on more than 40 acres of preserved green space with mature oak canopy and sweeping views along the bay. Residents enjoy access to a private marina with boat slips, a waterfront clubhouse, fitness center, and a resort-style pool. The neighborhood's architectural standards, landscaped streets, and quiet setting create a cohesive environment that complements the design and quality of 68 Perrin.

68 Perrin, Santa Rosa Beach
267 Churchill Oaks Dr, Santa Rosa Beach
$3,195,000
4 Beds ⋅ 5 Baths ⋅ 981260 MLS ⋅ 3,868 SqFt.
Located within the gated waterfront community of Churchill Oaks, this thoughtfully designed residence offers a refined take on coastal living with a focus on effortless indoor-outdoor flow and elevated everyday comfort. Positioned just north of 30A, the home pairs a private setting with access to a bayou front marina, clubhouse, and resort-style infinity pool. Designed for both entertaining and daily living, the home features a private pool, two-car garage, and a flexible layout with two primary suites. The main living area is anchored by soaring 12-foot ceilings and expansive 10-foot Euro-wall sliders that open seamlessly to the outdoor living space, creating a natural extension of the home. Interior finishes blend warmth and sophistication with Venetian plaster walls, white oak flooring, and curated architectural details throughout. The kitchen is designed for both function and presentation, featuring a 48-inch Wolf dual-fuel range with griddle, 48-inch Sub-Zero refrigerator, 6cm honed marble island, butler's pantry, and a wet bar with beverage refrigeration. The main-level primary suite offers vaulted ceilings, a spacious bath with dual vanities and soaking tub, and direct access to the L-shaped plunge pool. Upstairs, a secondary living area with wet bar provides additional space to gather, along with a second primary suite featuring a custom walk-in closet, screened balcony, and a wet-room-style bath with garden tub and shower. Outdoor spaces are designed for low-maintenance enjoyment, complete with an AstroTurf lawn, fire pit, and summer kitchen with built-in grill, sink, and refrigerator. Churchill Oaks residents enjoy gated privacy along with access to a private marina, bayou front clubhouse, and community pool, all within close proximity to the beaches, dining, and shopping of 30A.

267 Churchill Oaks Dr, Santa Rosa Beach

Vendor Member Number : 28166

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