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$2,950,000

This is what Grayton Beach is all about. This charming Old Florida-style cottage captures everything people love about the area, from its relaxed coastal character to its unbeatable location. It features a large private pool--perfect for cooling off after a day at the beach--and is being sold fully furnished for an easy, turnkey experience. Just steps from the beautiful beaches of South Walton and a short walk to ''downtown'' Grayton Beach, home to favorites like The Red Bar and Chiringo, this property offers the ideal blend of convenience and privacy. You're close to all the action, yet tucked away on a peaceful street. The first floor includes a four bunks, two additional bedrooms, and a secondary living space. Upstairs, the main living level features a screened-in porch, updated kitchen, and open living area, along with the primary suite and two additional guest bedrooms. Whether you're gathered on the screened porch, enjoying the heated pool, or walking back from the beach, every moment here is designed for slowing down and truly relaxing in this timeless coastal retreat. Information contained within this listing such as lot dimensions, is deemed to be accurate but is not guaranteed. Buyer to verify.

5 Beds ⋅ 4 Baths ⋅ 1001035 MLS

This is what Grayton Beach is all about. This charming Old Florida-style cottage captures everything people love about the area, from its relaxed coastal character to its unbeatable location. It features a large private pool--perfect for cooling off after a day at the beach--and is being sold fully furnished for an easy, turnkey experience. Just steps from the beautiful beaches of South Walton and a short walk to ''downtown'' Grayton Beach, home to favorites like The Red Bar and Chiringo, this property offers the ideal blend of convenience and privacy. You're close to all the action, yet tucked away on a peaceful street. The first floor includes a four bunks, two additional bedrooms, and a secondary living space. Upstairs, the main living level features a screened-in porch, updated kitchen, and open living area, along with the primary suite and two additional guest bedrooms. Whether you're gathered on the screened porch, enjoying the heated pool, or walking back from the beach, every moment here is designed for slowing down and truly relaxing in this timeless coastal retreat. Information contained within this listing such as lot dimensions, is deemed to be accurate but is not guaranteed. Buyer to verify.

245 Magnolia St, Santa Rosa Beach

$3,440,000

A Grayton Beach rarity: Western Lake views, a private guest cottage, a resort-style pool, and projected rental income of up to $373,000 annually, combine to create a property as versatile as it is unforgettable. Timeless Grayton Beach character meets thoughtful modern renovation in this rare fully-furnished, dual-residence offering just steps from Western Lake, the shoreline, and the heart of one of 30A's most storied beach villages. Originally built in 1970 and extensively reimagined, the property pairs a gracious main home with a fully detached private cottage, creating flexibility for hosting, multigenerational living, or income potential without sacrificing privacy or charm. The main residence spans approximately 2,910 square feet with five bedrooms and four-and-a-half baths across three levels. Recent updates include a fully redesigned kitchen, renovated bathrooms, fresh interior paint, new flooring, updated wiring and plumbing, two HVAC systems, new appliances, and a new roof. From the inviting front porch, morning coffee is enjoyed with tranquil views toward Western Lake. Inside, the first floor opens to a generous living and dining area that flows seamlessly into the kitchen, which offers ample space for an island and connects to a comfortable sitting or game room. A mudroom off the kitchen adds a half bath, a full-sized laundry, and direct access to the side yard for grilling. Two first-floor bedrooms feature updated ensuite baths, while a rear hallway leads directly to the backyard. Upstairs, the second level offers two additional bedrooms and two full baths. The third floor serves as a flexible retreat or bedroom, highlighted by a striking wood A-frame ceiling with access to the large balcony. The detached cottage provides approximately 560 square feet with one bedroom, one full bath, a family room, a full kitchen, a laundry room, an outdoor shower, and a separate entrance. With a new roof and alley access, the cottage allows easy movement to the beach, lake, and dining while remaining discreetly set apart from the main home. Outdoor living is equally compelling, with a spacious backyard ready for relaxed afternoons, a newly added private pool, curated hardscape, and lush landscaping. After a day on the water, rinse off at the outdoor shower or unwind in one of several private seating areas. Parking is generous with a paver driveway, additional front parking, and two rear spaces for a total of seven. Accessibility has been carefully considered with a ramp on the north side and a fully accessible first floor, including the primary bath. Both residences may be rented separately or together, offering exceptional versatility. Positioned moments from Western Lake, two beach accesses, and iconic spots like The Red Bar, Chiringo, and AJ's Grayton Beach, this is a rare opportunity to own a true Grayton Beach classic where coastal history, modern updates, and an unbeatable walkable setting come together with ease.

6 Beds ⋅ 6 Baths ⋅ 992659 MLS

A Grayton Beach rarity: Western Lake views, a private guest cottage, a resort-style pool, and projected rental income of up to $373,000 annually, combine to create a property as versatile as it is unforgettable. Timeless Grayton Beach character meets thoughtful modern renovation in this rare fully-furnished, dual-residence offering just steps from Western Lake, the shoreline, and the heart of one of 30A's most storied beach villages. Originally built in 1970 and extensively reimagined, the property pairs a gracious main home with a fully detached private cottage, creating flexibility for hosting, multigenerational living, or income potential without sacrificing privacy or charm. The main residence spans approximately 2,910 square feet with five bedrooms and four-and-a-half baths across three levels. Recent updates include a fully redesigned kitchen, renovated bathrooms, fresh interior paint, new flooring, updated wiring and plumbing, two HVAC systems, new appliances, and a new roof. From the inviting front porch, morning coffee is enjoyed with tranquil views toward Western Lake. Inside, the first floor opens to a generous living and dining area that flows seamlessly into the kitchen, which offers ample space for an island and connects to a comfortable sitting or game room. A mudroom off the kitchen adds a half bath, a full-sized laundry, and direct access to the side yard for grilling. Two first-floor bedrooms feature updated ensuite baths, while a rear hallway leads directly to the backyard. Upstairs, the second level offers two additional bedrooms and two full baths. The third floor serves as a flexible retreat or bedroom, highlighted by a striking wood A-frame ceiling with access to the large balcony. The detached cottage provides approximately 560 square feet with one bedroom, one full bath, a family room, a full kitchen, a laundry room, an outdoor shower, and a separate entrance. With a new roof and alley access, the cottage allows easy movement to the beach, lake, and dining while remaining discreetly set apart from the main home. Outdoor living is equally compelling, with a spacious backyard ready for relaxed afternoons, a newly added private pool, curated hardscape, and lush landscaping. After a day on the water, rinse off at the outdoor shower or unwind in one of several private seating areas. Parking is generous with a paver driveway, additional front parking, and two rear spaces for a total of seven. Accessibility has been carefully considered with a ramp on the north side and a fully accessible first floor, including the primary bath. Both residences may be rented separately or together, offering exceptional versatility. Positioned moments from Western Lake, two beach accesses, and iconic spots like The Red Bar, Chiringo, and AJ's Grayton Beach, this is a rare opportunity to own a true Grayton Beach classic where coastal history, modern updates, and an unbeatable walkable setting come together with ease.

64 Banfill St, Santa Rosa Beach

$11,499,999

A symphony of elegance in Grayton Beach, Lollygag commands the most coveted location on 30A, where Western Lake meets the Gulf of America in an awe-inspiring convergence of coastal beauty. Positioned at the curve of the Grayton Beach outfall, this home offers a rare and uninterrupted panorama, with forever-protected views of the dune lake, sugar-white sands, and emerald Gulf waters. Its setting is as private as it is breathtaking. Designed with an emphasis on both luxury and resilience, Lollygag is a fortress of coastal design, featuring a bedrock-anchored seawall ensuring lasting protection without compromising the natural beauty that surrounds it. Inside, every element has been thoughtfully curated to create a home that is both extraordinary in design and effortless in function. A commercial-grade elevator provides seamless access across all three levels, while wide hallways enhance flow and accessibility. The first floor is dedicated to comfort and convenience, featuring a steam room (sauna), full laundry, and half bath. The second level hosts two king suites, a queen suite, and a six-bed bunk room, each, except bunkroom, has its own private covered porch to take in the endless views. A handicap-accessible bath serves the bunk room, ensuring comfort for every guest. A swing bed on the second-floor porch provides a tranquil retreat, perfect for soaking in the coastal serenity. The third floor is where Lollygag truly shines. A grand great room, private office, screened-in porch, and an expansive seaward-facing deck with another swing bed create the ultimate indoor-outdoor living experience. Whether gathering in the open concept living space or unwinding as the sun dips below the horizon, every moment in this home is framed by the natural beauty of 30A's most remarkable setting. From its high-end appliances and integrated surround sound to its durable metal roof, hardboard siding, and Trex decking, every element of Lollygag speaks to quality and craftsmanship. Under-home covered parking with custom lighting enhances convenience, while two full outdoor showers offer the perfect way to refresh after a day on the water. With an unrivaled location, timeless design, and a level of craftsmanship rarely found, Lollygag stands as a benchmark of luxury along 30A. Used as a second home and not a rental, its pristine condition and exclusivity remain intact. Private showings by appointment only.

4 Beds ⋅ 6 Baths ⋅ 970654 MLS

A symphony of elegance in Grayton Beach, Lollygag commands the most coveted location on 30A, where Western Lake meets the Gulf of America in an awe-inspiring convergence of coastal beauty. Positioned at the curve of the Grayton Beach outfall, this home offers a rare and uninterrupted panorama, with forever-protected views of the dune lake, sugar-white sands, and emerald Gulf waters. Its setting is as private as it is breathtaking. Designed with an emphasis on both luxury and resilience, Lollygag is a fortress of coastal design, featuring a bedrock-anchored seawall ensuring lasting protection without compromising the natural beauty that surrounds it. Inside, every element has been thoughtfully curated to create a home that is both extraordinary in design and effortless in function. A commercial-grade elevator provides seamless access across all three levels, while wide hallways enhance flow and accessibility. The first floor is dedicated to comfort and convenience, featuring a steam room (sauna), full laundry, and half bath. The second level hosts two king suites, a queen suite, and a six-bed bunk room, each, except bunkroom, has its own private covered porch to take in the endless views. A handicap-accessible bath serves the bunk room, ensuring comfort for every guest. A swing bed on the second-floor porch provides a tranquil retreat, perfect for soaking in the coastal serenity. The third floor is where Lollygag truly shines. A grand great room, private office, screened-in porch, and an expansive seaward-facing deck with another swing bed create the ultimate indoor-outdoor living experience. Whether gathering in the open concept living space or unwinding as the sun dips below the horizon, every moment in this home is framed by the natural beauty of 30A's most remarkable setting. From its high-end appliances and integrated surround sound to its durable metal roof, hardboard siding, and Trex decking, every element of Lollygag speaks to quality and craftsmanship. Under-home covered parking with custom lighting enhances convenience, while two full outdoor showers offer the perfect way to refresh after a day on the water. With an unrivaled location, timeless design, and a level of craftsmanship rarely found, Lollygag stands as a benchmark of luxury along 30A. Used as a second home and not a rental, its pristine condition and exclusivity remain intact. Private showings by appointment only.

186 Banfill St, Santa Rosa Beach