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$2,300,000

Perfectly positioned in the heart of Seagrove Beach, 107 Cypress Hill Road offers the ideal blend of luxury, location, and investment potential. Situated in a short-term rental-friendly area, it's an exceptional opportunity as a primary residence, second home, or vacation rental Just steps from the sugar-white sand and a short walk or bike ride to Seaside's iconic town center, you'll enjoy effortless access to local favorites including Bud & Alley's, Great Southern Café, Modica Market, Sundog Books, boutique shopping, the Seaside Amphitheater, and the vibrant restaurants and shops that have made 30A a nationally recognized destination. Spanning approximately 2,607 square feet, the home offers multiple gathering spaces thoughtfully arranged across three levels. An in-home elevator provides effortless access to every floor, where the upper levels open to sweeping Gulf views from multiple balconies--creating the perfect backdrop for morning coffee, afternoon breezes, and unforgettable Emerald Coast sunsets. Designed for both entertaining and relaxation, the private backyard serves as your own resort-style escape with a heated in-ground pool, spa, outdoor shower, grilling area, and plenty of space to unwind after a day at the beach. The third floor is the heart of the home, where an open-concept living, dining, and gourmet kitchen is framed by expansive windows and balconies that showcase sparkling Gulf waters. The flexible floor plan features five bedrooms, five full bathrooms, and and half bath, including multiple king suites, a spacious primary retreat with a private balcony, and bunk accommodations ideal for family and guests. Combining Gulf views, thoughtful design, and an unbeatable location, this home offers the flexibility today's buyers are looking for while capturing the very best of the 30A lifestyle. With beach access just moments away, ample parking, and Seagrove Beach's vibrant lifestyle right outside your door, 107 Cypress Hill Road delivers the complete coastal experience.

5 Beds ⋅ 6 Baths ⋅ 1009402 MLS

Perfectly positioned in the heart of Seagrove Beach, 107 Cypress Hill Road offers the ideal blend of luxury, location, and investment potential. Situated in a short-term rental-friendly area, it's an exceptional opportunity as a primary residence, second home, or vacation rental Just steps from the sugar-white sand and a short walk or bike ride to Seaside's iconic town center, you'll enjoy effortless access to local favorites including Bud & Alley's, Great Southern Café, Modica Market, Sundog Books, boutique shopping, the Seaside Amphitheater, and the vibrant restaurants and shops that have made 30A a nationally recognized destination. Spanning approximately 2,607 square feet, the home offers multiple gathering spaces thoughtfully arranged across three levels. An in-home elevator provides effortless access to every floor, where the upper levels open to sweeping Gulf views from multiple balconies--creating the perfect backdrop for morning coffee, afternoon breezes, and unforgettable Emerald Coast sunsets. Designed for both entertaining and relaxation, the private backyard serves as your own resort-style escape with a heated in-ground pool, spa, outdoor shower, grilling area, and plenty of space to unwind after a day at the beach. The third floor is the heart of the home, where an open-concept living, dining, and gourmet kitchen is framed by expansive windows and balconies that showcase sparkling Gulf waters. The flexible floor plan features five bedrooms, five full bathrooms, and and half bath, including multiple king suites, a spacious primary retreat with a private balcony, and bunk accommodations ideal for family and guests. Combining Gulf views, thoughtful design, and an unbeatable location, this home offers the flexibility today's buyers are looking for while capturing the very best of the 30A lifestyle. With beach access just moments away, ample parking, and Seagrove Beach's vibrant lifestyle right outside your door, 107 Cypress Hill Road delivers the complete coastal experience.

107 Cypress Hill Rd, Santa Rosa Beach

$4,950,000

Defined by a clean coastal exterior of white brick, Hardie plank siding, and a metal roof, 69 Live Oak Street presents a timeless architectural profile across four thoughtfully designed levels, the result of a collaboration between architects Leslie Schwartz and Rob Bounds of 30A North Design and builder Timothy O'Hara of Coastal Custom Builders. Seamlessly set among the old growth oaks of Old Seagrove, and ideally positioned just 200 yards from the Live Oak Street beach access, the home offers convenient proximity to the Gulf while maintaining a sense of privacy. A dedicated game room anchors the ground floor, where soaring 12-foot ceilings frame a relaxed gathering space with ample seating, shuffleboard, and pinball. Just beyond, the outdoor living area extends the experience with a private pool, spa, and fully equipped summer kitchen--designed for seamless indoor-outdoor entertaining. Two king guest suites offer privacy and comfort, setting the tone for the home's ability to comfortably accommodate guests from the moment you enter. A half bath, full laundry room with dual washers and dryers, owner's storage, mudroom, and garage complete the level, all connected by elevator service to the upper floors. The main living level unfolds with an open layout designed for hosting at scale. A spacious den and secondary sitting area flow into a dining space that comfortably accommodates large gatherings, all centered around a chef's kitchen featuring a 6-by-14-foot quartz island, 48" dual fuel Wolf range, and integrated Sub-Zero refrigeration. A secondary prep area provides additional workspace and storage, supporting effortless entertaining. This level also includes a private king suite and a bunk room with custom queen-over-queen accommodations, further expanding the home's flexible sleeping capacity. Upstairs, the primary suite offers a quiet retreat, complete with a spa-like bath featuring dual vanities, a soaking tub, and a separate shower, along with direct access to a spacious balcony overlooking the backyard. Additional king guest suites and dual bunk configurations create a layout designed to comfortably host large groups while maintaining a sense of privacy throughout. The fourth level is dedicated entirely to an open-air rooftop deck, where treetop views of Old Seagrove and expansive skies create a setting equally suited for morning coffee or evening gatherings. Designed with both lifestyle and performance in mind, the home accommodates up to 28 guests and presents an opportunity meaningful annual rental income.

7 Beds ⋅ 9 Baths ⋅ 1002002 MLS

Defined by a clean coastal exterior of white brick, Hardie plank siding, and a metal roof, 69 Live Oak Street presents a timeless architectural profile across four thoughtfully designed levels, the result of a collaboration between architects Leslie Schwartz and Rob Bounds of 30A North Design and builder Timothy O'Hara of Coastal Custom Builders. Seamlessly set among the old growth oaks of Old Seagrove, and ideally positioned just 200 yards from the Live Oak Street beach access, the home offers convenient proximity to the Gulf while maintaining a sense of privacy. A dedicated game room anchors the ground floor, where soaring 12-foot ceilings frame a relaxed gathering space with ample seating, shuffleboard, and pinball. Just beyond, the outdoor living area extends the experience with a private pool, spa, and fully equipped summer kitchen--designed for seamless indoor-outdoor entertaining. Two king guest suites offer privacy and comfort, setting the tone for the home's ability to comfortably accommodate guests from the moment you enter. A half bath, full laundry room with dual washers and dryers, owner's storage, mudroom, and garage complete the level, all connected by elevator service to the upper floors. The main living level unfolds with an open layout designed for hosting at scale. A spacious den and secondary sitting area flow into a dining space that comfortably accommodates large gatherings, all centered around a chef's kitchen featuring a 6-by-14-foot quartz island, 48" dual fuel Wolf range, and integrated Sub-Zero refrigeration. A secondary prep area provides additional workspace and storage, supporting effortless entertaining. This level also includes a private king suite and a bunk room with custom queen-over-queen accommodations, further expanding the home's flexible sleeping capacity. Upstairs, the primary suite offers a quiet retreat, complete with a spa-like bath featuring dual vanities, a soaking tub, and a separate shower, along with direct access to a spacious balcony overlooking the backyard. Additional king guest suites and dual bunk configurations create a layout designed to comfortably host large groups while maintaining a sense of privacy throughout. The fourth level is dedicated entirely to an open-air rooftop deck, where treetop views of Old Seagrove and expansive skies create a setting equally suited for morning coffee or evening gatherings. Designed with both lifestyle and performance in mind, the home accommodates up to 28 guests and presents an opportunity meaningful annual rental income.

69 Live Oak St, Santa Rosa Beach

$2,750,000

Steps from the iconic sugar-white sands of 30A, 39 Thyme blends coastal charm & effortless livability in one of Seagrove's most coveted locations. Tucked beneath a canopy of magnolias & oaks, this spacious retreat sits just 100 yards to both the Dogwood & Hickory beach accesses and a short stroll to Seaside's shops, dining & entertainment. The 5 bedroom home (plus bunk room) features wraparound balconies on the 2nd & 3rd floors, offering Gulf glimpses & multiple outdoor living spaces. The fenced backyard includes a sparkling pool, paver sundeck, grilling area, and covered patio with ping-pong & outdoor shower. Inside, the main living level is located on the 2nd floor, complete with a full kitchen, large dining area, and an inviting family room filled with natural light. A 3rd-floor den offers an additional gathering space with a wet bar & balcony access. With a bathroom for every bedroom, generous storage, plenty of driveway parking, the home lives large & comfortably. Perfectly positioned in Old Seagrove, this property is an exceptional opportunity for buyers seeking a primary residence, second home, or investment on the east side of 30A.

5 Beds ⋅ 6 Baths ⋅ 994889 MLS

Steps from the iconic sugar-white sands of 30A, 39 Thyme blends coastal charm & effortless livability in one of Seagrove's most coveted locations. Tucked beneath a canopy of magnolias & oaks, this spacious retreat sits just 100 yards to both the Dogwood & Hickory beach accesses and a short stroll to Seaside's shops, dining & entertainment. The 5 bedroom home (plus bunk room) features wraparound balconies on the 2nd & 3rd floors, offering Gulf glimpses & multiple outdoor living spaces. The fenced backyard includes a sparkling pool, paver sundeck, grilling area, and covered patio with ping-pong & outdoor shower. Inside, the main living level is located on the 2nd floor, complete with a full kitchen, large dining area, and an inviting family room filled with natural light. A 3rd-floor den offers an additional gathering space with a wet bar & balcony access. With a bathroom for every bedroom, generous storage, plenty of driveway parking, the home lives large & comfortably. Perfectly positioned in Old Seagrove, this property is an exceptional opportunity for buyers seeking a primary residence, second home, or investment on the east side of 30A.

39 Thyme St, Santa Rosa Beach