Experience the ultimate coastal lifestyle at 7101 Middleton Avenue, a premier short-term rental friendly retreat situated on a rare .70-acre waterfront lot just two blocks from the pristine shores of St. Augustine Beach. This turnkey, fully furnished residence perfectly balances luxury and investment potential, featuring a private dock on the Intracoastal Waterway for breathtaking sunset views and a newly installed, climate-controlled pool with a tanning ledge. Inside, the 2,374 sq. ft. open-concept layout is bathed in natural light, offering three spacious bedrooms plus a versatile office and a dedicated pool table room, all designed for seamless indoor-outdoor entertaining. Whether you're launching a boat from your backyard, taking a sunrise bike ride to the beach, or capitalizing on the high demand for vacation rentals in St. Johns County, this "unicorn" property offers a lifestyle of unparalleled convenience and serenity just minutes from historic downtown St. Augustine.

3 Beds ⋅ 3 Baths ⋅ South Crescent SubDv. ⋅ 32080 Zip Code

Experience the ultimate coastal lifestyle at 7101 Middleton Avenue, a premier short-term rental friendly retreat situated on a rare .70-acre waterfront lot just two blocks from the pristine shores of St. Augustine Beach. This turnkey, fully furnished residence perfectly balances luxury and investment potential, featuring a private dock on the Intracoastal Waterway for breathtaking sunset views and a newly installed, climate-controlled pool with a tanning ledge. Inside, the 2,374 sq. ft. open-concept layout is bathed in natural light, offering three spacious bedrooms plus a versatile office and a dedicated pool table room, all designed for seamless indoor-outdoor entertaining. Whether you're launching a boat from your backyard, taking a sunrise bike ride to the beach, or capitalizing on the high demand for vacation rentals in St. Johns County, this "unicorn" property offers a lifestyle of unparalleled convenience and serenity just minutes from historic downtown St. Augustine.

7101 Middleton Avenue, St Augustine

$1,450,000

Experience the ultimate in coastal living in this stunning 4-bedroom, 3-bath Intracoastal estate, perfectly positioned on a rare double lot at the end of a quiet cul-de-sac within a gated community offering pickleball courts and unobstructed water views. With the Atlantic Ocean and pristine beaches directly across the water, you'll enjoy breathtaking sunrises from the front of the home and spectacular sunsets over the Intracoastal from the rear, creating a setting that feels like a private resort. Inside, soaring ceilings and walls of windows fill the home with natural light, while the open-concept design is ideal for both everyday living and entertaining. Rich oak hardwood floors and tile flow throughout, complementing the inviting living area with its dramatic fireplace and expansive water views. The beautifully designed kitchen is a chef's dream, featuring abundant custom wood cabinetry, granite countertops, stainless steel appliances, a center island, and plenty of workspace for gathering with family and friends. Thoughtfully designed for comfort and flexibility, the home offers a private bedroom suite on the first floor, perfect for guests or multigenerational living. Upstairs, the impressive primary suite overlooks the Intracoastal and captures views of the Atlantic Ocean beyond. Wake each morning to ever-changing water vistas and unwind in the spacious bath with soaking tub and separate shower. Additional bedrooms provide generous space and privacy for family and guests. Outdoor living is where this exceptional property truly shines. The sparkling pool, waterfront fire pit, and multiple covered decks create endless opportunities for relaxation and entertaining. The oversized dock is more than just a place to keep your boat. Designed with gatherings in mind, it offers room for multiple vessels, features a 20,000-pound boat lift, and provides the perfect setting for sunset dinners, celebrations, or simply enjoying life on the water. Watch dolphins play, manatees glide by, and an endless parade of sailboats and cruisers pass along the Intracoastal from your own backyard. Offering privacy, space, and unforgettable views from nearly every room, this extraordinary waterfront retreat combines luxury, boating, and the beauty of Florida's coast in one remarkable property. Whether you're enjoying your morning coffee as the sun rises over the ocean, spending the day on the water, or gathering around the fire pit as the sky glows with sunset colors, every day here feels like a vacation. Minutes to Historic St. Augustine and Charming Flagler Beach.

4 Beds ⋅ 3 Baths ⋅ Summer Island Ph 01 SubDv. ⋅ 32080 Zip Code

Experience the ultimate in coastal living in this stunning 4-bedroom, 3-bath Intracoastal estate, perfectly positioned on a rare double lot at the end of a quiet cul-de-sac within a gated community offering pickleball courts and unobstructed water views. With the Atlantic Ocean and pristine beaches directly across the water, you'll enjoy breathtaking sunrises from the front of the home and spectacular sunsets over the Intracoastal from the rear, creating a setting that feels like a private resort. Inside, soaring ceilings and walls of windows fill the home with natural light, while the open-concept design is ideal for both everyday living and entertaining. Rich oak hardwood floors and tile flow throughout, complementing the inviting living area with its dramatic fireplace and expansive water views. The beautifully designed kitchen is a chef's dream, featuring abundant custom wood cabinetry, granite countertops, stainless steel appliances, a center island, and plenty of workspace for gathering with family and friends. Thoughtfully designed for comfort and flexibility, the home offers a private bedroom suite on the first floor, perfect for guests or multigenerational living. Upstairs, the impressive primary suite overlooks the Intracoastal and captures views of the Atlantic Ocean beyond. Wake each morning to ever-changing water vistas and unwind in the spacious bath with soaking tub and separate shower. Additional bedrooms provide generous space and privacy for family and guests. Outdoor living is where this exceptional property truly shines. The sparkling pool, waterfront fire pit, and multiple covered decks create endless opportunities for relaxation and entertaining. The oversized dock is more than just a place to keep your boat. Designed with gatherings in mind, it offers room for multiple vessels, features a 20,000-pound boat lift, and provides the perfect setting for sunset dinners, celebrations, or simply enjoying life on the water. Watch dolphins play, manatees glide by, and an endless parade of sailboats and cruisers pass along the Intracoastal from your own backyard. Offering privacy, space, and unforgettable views from nearly every room, this extraordinary waterfront retreat combines luxury, boating, and the beauty of Florida's coast in one remarkable property. Whether you're enjoying your morning coffee as the sun rises over the ocean, spending the day on the water, or gathering around the fire pit as the sky glows with sunset colors, every day here feels like a vacation. Minutes to Historic St. Augustine and Charming Flagler Beach.

9277 July Lane, St Augustine

$4,600,000

Experience exceptional waterfront living at 8065 A1A South, a private Intracoastal estate set on more than an acre just minutes from Historic Downtown St. Augustine. Soaring ceilings, designer finishes, statement Visual Comfort lighting, and walls of glass frame breathtaking water views, spectacular sunsets, abundant birdlife, and sailboats gliding by. Designed for effortless indoor-outdoor living, the resort-inspired grounds feature a heated saltwater pool and spa, summer kitchen, pool bath, expansive lawn, and a palm-lined pickleball court with covered pavilion, all surrounded by lush tropical landscaping. The chef’s kitchen is equipped with JennAir column refrigeration, a professional-grade gas range, double ovens, an oversized island, wet bar, and a fully equipped butler’s pantry. The primary suite occupies its own secluded retreat, featuring vaulted ceilings, a waterfront lounge, a spa-inspired bath, a boutique-style dressing room, and private laundry. Beyond the suite, the property boasts a complete luxury one bedroom apartment! Built with comfort and peace of mind, the home includes impact windows, a whole-house Generac, underground sump pump system, irrigation well, and Shellock permeable pavers. Perfectly positioned in Cresent Beach, with easy access to pristine beaches, boating, fishing, kayaking, and paddleboarding, this remarkable estate blends elegant design with the natural beauty of Florida’s coast, creating an extraordinary waterfront lifestyle.

5 Beds ⋅ 7 Baths ⋅ South Crescnt (Icwfr) (850.42) SubDv. ⋅ 32080 Zip Code

Experience exceptional waterfront living at 8065 A1A South, a private Intracoastal estate set on more than an acre just minutes from Historic Downtown St. Augustine. Soaring ceilings, designer finishes, statement Visual Comfort lighting, and walls of glass frame breathtaking water views, spectacular sunsets, abundant birdlife, and sailboats gliding by. Designed for effortless indoor-outdoor living, the resort-inspired grounds feature a heated saltwater pool and spa, summer kitchen, pool bath, expansive lawn, and a palm-lined pickleball court with covered pavilion, all surrounded by lush tropical landscaping. The chef’s kitchen is equipped with JennAir column refrigeration, a professional-grade gas range, double ovens, an oversized island, wet bar, and a fully equipped butler’s pantry. The primary suite occupies its own secluded retreat, featuring vaulted ceilings, a waterfront lounge, a spa-inspired bath, a boutique-style dressing room, and private laundry. Beyond the suite, the property boasts a complete luxury one bedroom apartment! Built with comfort and peace of mind, the home includes impact windows, a whole-house Generac, underground sump pump system, irrigation well, and Shellock permeable pavers. Perfectly positioned in Cresent Beach, with easy access to pristine beaches, boating, fishing, kayaking, and paddleboarding, this remarkable estate blends elegant design with the natural beauty of Florida’s coast, creating an extraordinary waterfront lifestyle.

8065 A1a S, St Augustine

$1,495,000

Embrace the boating lifestyle and enjoy premier waterfront living in the highly sought-after community of Antiqua. This gorgeous dock home sits on a large lot with unobstructed views of the St. Augustine Lighthouse, marsh, and a deep-water canal that leads directly to the intracoastal and to the downtown marina in just five minutes by boat. This is the last home on the cul de sac permitted to have a dock, which means there is no dock to the south of you! Enjoy unlimited access to the deepest water in the canal. The private dock is outfitted with underwater lighting, electrical, and water connections—ready for day and night boating adventures. From the moment you arrive, this home impresses with a paver driveway and a welcoming front porch. Inside, the home is thoughtfully designed with rich wood cabinetry, built-ins throughout and stylish updates that make every room feel inviting! The entry foyer sets the tone with elegance, and a practical drop zone is located right off the garage entrance. A guest bedroom and full bathroom downstairs add extra flexibility for hosting. The spacious family room centers around a custom-built entertainment system with an electric fireplace, offering a cozy space to relax and unwind. The kitchen is a showstopper—perfect for the home chef—with a large quartz island, upgraded vent hood, gas cooktop, wall oven, walk-in pantry, and an abundance of cabinetry for storage. There’s even a charming dining area set in front of the bay windows, offering picture-perfect views of the marsh while you dine. Open the triple sliding glass hideaway doors to create a seamless flow to the outdoor living area, where entertaining is effortless. The covered paver patio includes a fully equipped custom outdoor kitchen, a stunning natural stone fireplace, a center island, outdoor ceiling fan, mounted TV, and upgraded surround sound system—everything you need to enjoy the Florida lifestyle year-round. Upstairs, a surprise bonus family area adds another layer of comfort and charm, complete with custom wood beams, built-ins-ideal for entertaining. The primary suite is spacious and serene, offering custom closet organizers, a walk-out balcony with sweeping views of the landscape and a gorgeous ensuite. Start your mornings with a latte on the balcony, catching the sunrise, or unwind at the end of the day with peaceful sunset views. Two additional bedrooms share a large bathroom upstairs, and a spacious utility/laundry room with plenty of folding space adds to the home's functionality. The home is finished with stunning porcelain wood-like tile on level one and luxury vinyl plank flooring on level two, only 1 room has carpeting. Furniture and boat are both negotiable! Antiqua offers residents access to a community pool, clubhouse and kayak launch, and is just minutes from local restaurants, shopping and 1 mile to St. Augustine Beach! Here, you can fish from your dock, spot wildlife in your backyard, listen to concerts from the amphitheater without ever leaving your home, or drive your boat straight to historic downtown St. Augustine. This is waterfront living at its finest—full of nature, activity, and breathtaking views—all from the comfort of your own home. Locals know the Best fishing in all of St. Augustine happens here!

4 Beds ⋅ 3 Baths ⋅ Antigua Ph Two SubDv. ⋅ 32080 Zip Code

Embrace the boating lifestyle and enjoy premier waterfront living in the highly sought-after community of Antiqua. This gorgeous dock home sits on a large lot with unobstructed views of the St. Augustine Lighthouse, marsh, and a deep-water canal that leads directly to the intracoastal and to the downtown marina in just five minutes by boat. This is the last home on the cul de sac permitted to have a dock, which means there is no dock to the south of you! Enjoy unlimited access to the deepest water in the canal. The private dock is outfitted with underwater lighting, electrical, and water connections—ready for day and night boating adventures. From the moment you arrive, this home impresses with a paver driveway and a welcoming front porch. Inside, the home is thoughtfully designed with rich wood cabinetry, built-ins throughout and stylish updates that make every room feel inviting! The entry foyer sets the tone with elegance, and a practical drop zone is located right off the garage entrance. A guest bedroom and full bathroom downstairs add extra flexibility for hosting. The spacious family room centers around a custom-built entertainment system with an electric fireplace, offering a cozy space to relax and unwind. The kitchen is a showstopper—perfect for the home chef—with a large quartz island, upgraded vent hood, gas cooktop, wall oven, walk-in pantry, and an abundance of cabinetry for storage. There’s even a charming dining area set in front of the bay windows, offering picture-perfect views of the marsh while you dine. Open the triple sliding glass hideaway doors to create a seamless flow to the outdoor living area, where entertaining is effortless. The covered paver patio includes a fully equipped custom outdoor kitchen, a stunning natural stone fireplace, a center island, outdoor ceiling fan, mounted TV, and upgraded surround sound system—everything you need to enjoy the Florida lifestyle year-round. Upstairs, a surprise bonus family area adds another layer of comfort and charm, complete with custom wood beams, built-ins-ideal for entertaining. The primary suite is spacious and serene, offering custom closet organizers, a walk-out balcony with sweeping views of the landscape and a gorgeous ensuite. Start your mornings with a latte on the balcony, catching the sunrise, or unwind at the end of the day with peaceful sunset views. Two additional bedrooms share a large bathroom upstairs, and a spacious utility/laundry room with plenty of folding space adds to the home's functionality. The home is finished with stunning porcelain wood-like tile on level one and luxury vinyl plank flooring on level two, only 1 room has carpeting. Furniture and boat are both negotiable! Antiqua offers residents access to a community pool, clubhouse and kayak launch, and is just minutes from local restaurants, shopping and 1 mile to St. Augustine Beach! Here, you can fish from your dock, spot wildlife in your backyard, listen to concerts from the amphitheater without ever leaving your home, or drive your boat straight to historic downtown St. Augustine. This is waterfront living at its finest—full of nature, activity, and breathtaking views—all from the comfort of your own home. Locals know the Best fishing in all of St. Augustine happens here!

62 Guanahani Trail, St Augustine

$2,350,000

178 Avenida Menendez – An Iconic Flagler-Era Residence with Panoramic Bayfront Views Exquisitely restored and meticulously maintained. The Bodley/Bennett residence is a rare Flagler-era treasure, originally built in 1910 and thoughtfully renovated between 2010 and 2012. Perched along the Matanzas River, this historic legal home commands sweeping, panoramic vistas of the St. Augustine Bayfront and the legendary Bridge of Lions, offering a lifestyle defined by elegance, heritage, and unmatched waterfront charm. Boasting 6 bedrooms and 5 full baths, this residence seamlessly blends historic character with modern comforts. Yellow pine flooring, 8” hardwood baseboards, original five-panel doors, and grand staircases evoke timeless craftsmanship while updated systems and finishes ensure contemporary luxury. The First-Floor Residence is an ideal suite for generational living or distinguished guests, featuring 2 bedrooms, 1 full bath, a spacious living room with a period gas fireplace, and a formal dining room. The chef-inspired kitchen includes a Jenn-Air gas range, stainless steel appliances, granite countertops, and espresso-finished cabinetry accented with period hardware—marrying modern convenience with classic detail. The Second-Floor Main Residence is Designed for refined living and entertaining. This level offers 2 bedrooms, 3 full baths, an inviting living room, formal dining, and a beautifully remodeled kitchen with gas range, updated cabinetry, and rich butcher block counters. Thoughtful layouts and elevated finishes create a sense of sophistication and comfort throughout. The Third-Floor Retreat is also the pinnacle of luxury living. This floor provides 2 bedrooms, 1 full bath, and a generous walk-out terrace framing some of the most breathtaking views of the Bayfront and Bridge of Lions—a private sanctuary perfect for morning coffee, sunset entertaining, or simply soaking in St. Augustine’s timeless beauty. A rare convergence of history, architecture, and premier waterfront location, this residence is not just a home—it is a statement. Perfect for collectors of historic properties, lovers of fine craftsmanship, and those who seek an elevated lifestyle in one of Florida’s most cherished cities. Experience St. Augustine living at its finest—where every detail tells a story, every view inspires, and every moment is extraordinary. Optional 1 year home warranty provided by Fidelity National Home Warranty.

6 Beds ⋅ 5 Baths ⋅ City/St Augustine SubDv. ⋅ 32084 Zip Code

178 Avenida Menendez – An Iconic Flagler-Era Residence with Panoramic Bayfront Views Exquisitely restored and meticulously maintained. The Bodley/Bennett residence is a rare Flagler-era treasure, originally built in 1910 and thoughtfully renovated between 2010 and 2012. Perched along the Matanzas River, this historic legal home commands sweeping, panoramic vistas of the St. Augustine Bayfront and the legendary Bridge of Lions, offering a lifestyle defined by elegance, heritage, and unmatched waterfront charm. Boasting 6 bedrooms and 5 full baths, this residence seamlessly blends historic character with modern comforts. Yellow pine flooring, 8” hardwood baseboards, original five-panel doors, and grand staircases evoke timeless craftsmanship while updated systems and finishes ensure contemporary luxury. The First-Floor Residence is an ideal suite for generational living or distinguished guests, featuring 2 bedrooms, 1 full bath, a spacious living room with a period gas fireplace, and a formal dining room. The chef-inspired kitchen includes a Jenn-Air gas range, stainless steel appliances, granite countertops, and espresso-finished cabinetry accented with period hardware—marrying modern convenience with classic detail. The Second-Floor Main Residence is Designed for refined living and entertaining. This level offers 2 bedrooms, 3 full baths, an inviting living room, formal dining, and a beautifully remodeled kitchen with gas range, updated cabinetry, and rich butcher block counters. Thoughtful layouts and elevated finishes create a sense of sophistication and comfort throughout. The Third-Floor Retreat is also the pinnacle of luxury living. This floor provides 2 bedrooms, 1 full bath, and a generous walk-out terrace framing some of the most breathtaking views of the Bayfront and Bridge of Lions—a private sanctuary perfect for morning coffee, sunset entertaining, or simply soaking in St. Augustine’s timeless beauty. A rare convergence of history, architecture, and premier waterfront location, this residence is not just a home—it is a statement. Perfect for collectors of historic properties, lovers of fine craftsmanship, and those who seek an elevated lifestyle in one of Florida’s most cherished cities. Experience St. Augustine living at its finest—where every detail tells a story, every view inspires, and every moment is extraordinary. Optional 1 year home warranty provided by Fidelity National Home Warranty.

178 Avenida Menendez, St Augustine

The Nest Group

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