266 Woodland Bayou Drive
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For Sale

266 Woodland Bayou Drive

266 Woodland Bayou Drive, Santa Rosa Beach, FL 32459

$3,950,000
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.

5
beds

7
baths

5,808 Sq.Ft. LIVING AREA

1.49 Acres lot

KENDALL HOOD

KENDALL HOOD

Features & Amenities

Interior

  • total bedrooms5
  • Total bathrooms7
  • full bathrooms4
  • half bathrooms3
  • APPLIANCES Auto Garage Door Opn, Dishwasher, Disposal, Ice Machine, Microwave, Range Hood, Refrigerator W/Ice Mk, Stove/Oven Gas, Water Heater - Gas
  • other interior Features Kitchen Island, Lighting Recessed, Pantry, Shelving, Split Bedroom, Washer/Dryer Hookup, Wet Bar

Area & Lot

  • Status For Sale
  • Living Area5,808 Sq.Ft.
  • Total Area5,808 Sq.Ft.
  • Lot Area1.49 Acres
  • MLS® ID1014311
  • TypeResidential
  • YEAR BUILT2024
  • Architecture StylesContemporary
  • Water FrontageBay, Bayou
  • View DescriptionBayou, Bay
  • Elementary SchoolVan R Butler
  • Middle SchoolBay
  • High SchoolSouth Walton

Exterior

  • STORIES2
  • Garage Space3.0
  • utilitiesGas - Propane
  • PoolPool - Heated, Pool - In-Ground, Pool Type
  • parkingBoat
  • HEAT TYPECentral
  • other exterior FeaturesBalcony, Boatlift, Fenced Back Yard, Hot Tub, Summer Kitchen

Financial

  • Sales Price$3,950,000
  • Real Estate Tax $15,414/yr
  • Zoning Resid Single Family
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Schedule a Showing

We would love to show you our beautiful property. Please select your preferred date and time below. An agent will be in touch shortly to confirm your appointment.
Thank you for your interest in 266 Woodland Bayou Drive, Santa Rosa Beach, FL 32459. We are reviewing your request and will be in touch shortly!

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Kendall Hood, founder and principal of The Kendall Hood Collection

About the founder

The Kendall Hood Collection at Compass

Luxury coastal real estate, 30A and the Emerald Coast

Kendall Hood is the founder and principal of The Kendall Hood Collection, a five-agent luxury real estate team at Compass serving 30A, Santa Rosa Beach, Seagrove Beach, Blue Mountain Beach, Grayton Beach, WaterColor, Rosemary Beach, Inlet Beach, Miramar Beach, Sandestin and Destin. An Alabama native who grew up vacationing on this coastline, she began her career in hospitality at the Waldorf Astoria in New York, spent six years selling new construction at Emerald Grande in Destin, and has spent more than 20 years learning every pocket of the 30A to Destin corridor. A founding agent of Compass 30A, she lives on 30A with her husband, Jim, and their two children. The team has served the Emerald Coast since 2020.

Among the 52 RealTrends Verified teams on 30A, The Kendall Hood Collection ranks number one in four ways: top team in Seagrove Beach, top boutique Compass team of ten agents or fewer, most homes sold among teams averaging $1M to $2M a sale, and most Google reviews on 30A. RealTrends counted $85.16 million and 74 closed sales for the team in 2025.

In the team's own rolling 12 months ending June 30, 2026, it closed 82 transactions and $117 million in volume across five agents, an average of $23.4 million per agent, with a 97.6 percent list-to-sale price ratio. Repeat clients and referrals accounted for 59.2 percent of business. The team holds 103 five-star Google reviews, has represented more than 600 families and has closed more than $540 million in lifetime sales.

Meet the team | 2048 W County Hwy 30A, Suite 107, Santa Rosa Beach, FL 32459 | (850) 974-4556
Rankings: The Closed List, 30A edition, from RealTrends Verified 2025 data.