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An opportunity like this rarely becomes available on Pine Island! Nearly 5.5 acres of mostly cleared, usable land with AG zoning, public water, a private well, irrigation, gated entry, and an existing 3-bedroom, 2-bath home offer a unique opportunity for anyone seeking space, flexibility, and the freedom to pursue an agricultural or homestead lifestyle. Set along Stringfellow Road, this property offers the kind of acreage that is increasingly difficult to find on Pine Island. The land has previously been used for agriculture and includes irrigation that can support the property’s potential nursery or mango operation. Whether your vision is an island homestead, agricultural venture, nursery, growing operation, hobby farm, or simply owning a substantial piece of Pine Island with room to spread out, this property deserves a serious look. The existing home provides a comfortable base while you develop the property around your vision. Recent improvements include a newer HVAC system, impact windows and front door, and luxury vinyl flooring, providing a solid foundation for immediate occupancy or future updates. Soak in the pool after a day of farm work or after coming in off the boat, with a catch of local favorites: Snook, Redfish, and Grouper. The barn also adds value, with a structure already in place to work from or store all the toys you could want on an island farm with quick access to Pine Island Sound. The zoning and potential agricultural exemptions add another important layer of value and flexibility. The gated entrance just off the main road provides privacy while the expansive acreage gives you something increasingly rare in Southwest Florida: room to breathe, room to work, and room to create. And then there is the Pine Island lifestyle. Spend your mornings tending the property, growing your own produce, working with plants, or simply enjoying the privacy of your own acreage. When the day's work is done, you're minutes from Pine Island's legendary boating, fishing, waterfront restaurants, marinas, and the laid-back Old Florida lifestyle that makes this island so special. If you've been looking for a property where you can live, work, grow, and build your own Pine Island vision, you need to see this in person. Properties with this combination of acreage, zoning, infrastructure, and location are truly once-in-a-lifetime.

3 Beds ⋅ 2 Baths ⋅ 2026040187 MLS

An opportunity like this rarely becomes available on Pine Island! Nearly 5.5 acres of mostly cleared, usable land with AG zoning, public water, a private well, irrigation, gated entry, and an existing 3-bedroom, 2-bath home offer a unique opportunity for anyone seeking space, flexibility, and the freedom to pursue an agricultural or homestead lifestyle. Set along Stringfellow Road, this property offers the kind of acreage that is increasingly difficult to find on Pine Island. The land has previously been used for agriculture and includes irrigation that can support the property’s potential nursery or mango operation. Whether your vision is an island homestead, agricultural venture, nursery, growing operation, hobby farm, or simply owning a substantial piece of Pine Island with room to spread out, this property deserves a serious look. The existing home provides a comfortable base while you develop the property around your vision. Recent improvements include a newer HVAC system, impact windows and front door, and luxury vinyl flooring, providing a solid foundation for immediate occupancy or future updates. Soak in the pool after a day of farm work or after coming in off the boat, with a catch of local favorites: Snook, Redfish, and Grouper. The barn also adds value, with a structure already in place to work from or store all the toys you could want on an island farm with quick access to Pine Island Sound. The zoning and potential agricultural exemptions add another important layer of value and flexibility. The gated entrance just off the main road provides privacy while the expansive acreage gives you something increasingly rare in Southwest Florida: room to breathe, room to work, and room to create. And then there is the Pine Island lifestyle. Spend your mornings tending the property, growing your own produce, working with plants, or simply enjoying the privacy of your own acreage. When the day's work is done, you're minutes from Pine Island's legendary boating, fishing, waterfront restaurants, marinas, and the laid-back Old Florida lifestyle that makes this island so special. If you've been looking for a property where you can live, work, grow, and build your own Pine Island vision, you need to see this in person. Properties with this combination of acreage, zoning, infrastructure, and location are truly once-in-a-lifetime.

5228 Stringfellow Road, St James City

2912 Buttonwood Key Court, St James City

$1,175,000

Tucked away in the private waterfront community of Buttonwood Key, this custom-built 2024 home combines privacy, thoughtful design and the ultimate Pine Island boating lifestyle. **Designed with 2 bedrooms plus 2 versatile bonus rooms, the home offers flexible spaces that can easily function as guest quarters, home offices, a den, hobby or craft rooms, or additional sleeping areas—allowing the home to live much larger than a traditional 2-bedroom floor plan.** Set in a serene location with protected preserve views across the front and beautiful water views from the rear, this home was designed to take full advantage of its surroundings. The ground level offers an impressive air-conditioned 4-car garage with workshop area, mudroom and abundant space for vehicles, boating gear and island toys. An additional outdoor storage shed tucked beneath the deck provides even more convenient space for tools, fishing gear and outdoor equipment. Step outside to your own waterfront retreat featuring a composite dock, boat lift, separate sitting dock, built-in fire pit and pergola—an inviting setting to relax by the water after a day of boating. The tropical landscaping adds to the island atmosphere with banana and mango trees along with established aloe plants. Quick access puts you within easy reach of Pine Island Sound, the Gulf, beaches and some of Southwest Florida’s renowned fishing and boating destinations. The main living level features 10’ ceilings, shiplap walls and an open great room designed around expansive water views. The kitchen features white raised-panel cabinetry, granite countertops, stainless steel appliances, a center island and a spacious pantry with built-in shelving and cabinetry. This level also includes a guest bedroom and bath, laundry room with cabinetry and utility sink, sunroom and sitting area, along with the home’s flexible bonus spaces. Front and rear balconies extend the living space outdoors and capture both the peaceful preserve setting and waterfront views. The third level is dedicated to a private primary retreat featuring its own waterfront balcony, two walk-in closets—including one currently utilized as a craft space—and a spacious bath with dual vanities, soaking tub and an impressive walk-in shower with multiple shower heads and rain shower. Smart-home features add everyday convenience with connected lighting, A/C system, appliances and garage doors, while the drinking water system includes reverse osmosis at the tap. With room to add a pool, incredible garage and storage space, flexible bonus rooms, multiple indoor and outdoor living areas, tropical fruit trees and direct access to the water, this is much more than a home—it’s a private island retreat designed for those who want space, serenity and boating right outside their door.

2 Beds ⋅ 2 Baths ⋅ 2026032881 MLS

Tucked away in the private waterfront community of Buttonwood Key, this custom-built 2024 home combines privacy, thoughtful design and the ultimate Pine Island boating lifestyle. **Designed with 2 bedrooms plus 2 versatile bonus rooms, the home offers flexible spaces that can easily function as guest quarters, home offices, a den, hobby or craft rooms, or additional sleeping areas—allowing the home to live much larger than a traditional 2-bedroom floor plan.** Set in a serene location with protected preserve views across the front and beautiful water views from the rear, this home was designed to take full advantage of its surroundings. The ground level offers an impressive air-conditioned 4-car garage with workshop area, mudroom and abundant space for vehicles, boating gear and island toys. An additional outdoor storage shed tucked beneath the deck provides even more convenient space for tools, fishing gear and outdoor equipment. Step outside to your own waterfront retreat featuring a composite dock, boat lift, separate sitting dock, built-in fire pit and pergola—an inviting setting to relax by the water after a day of boating. The tropical landscaping adds to the island atmosphere with banana and mango trees along with established aloe plants. Quick access puts you within easy reach of Pine Island Sound, the Gulf, beaches and some of Southwest Florida’s renowned fishing and boating destinations. The main living level features 10’ ceilings, shiplap walls and an open great room designed around expansive water views. The kitchen features white raised-panel cabinetry, granite countertops, stainless steel appliances, a center island and a spacious pantry with built-in shelving and cabinetry. This level also includes a guest bedroom and bath, laundry room with cabinetry and utility sink, sunroom and sitting area, along with the home’s flexible bonus spaces. Front and rear balconies extend the living space outdoors and capture both the peaceful preserve setting and waterfront views. The third level is dedicated to a private primary retreat featuring its own waterfront balcony, two walk-in closets—including one currently utilized as a craft space—and a spacious bath with dual vanities, soaking tub and an impressive walk-in shower with multiple shower heads and rain shower. Smart-home features add everyday convenience with connected lighting, A/C system, appliances and garage doors, while the drinking water system includes reverse osmosis at the tap. With room to add a pool, incredible garage and storage space, flexible bonus rooms, multiple indoor and outdoor living areas, tropical fruit trees and direct access to the water, this is much more than a home—it’s a private island retreat designed for those who want space, serenity and boating right outside their door.

2912 Buttonwood Key Court, St James City

$4,250,000

Welcome to an extraordinary waterfront estate where 3.4 acres, exceptional boating access and resort-style living come together in one remarkable property. With 1,561 feet of deep-water canal frontage, commanding wide-water views and boating access leading out to the harbor and beyond, this is the kind of Southwest Florida estate that immediately stands apart. On 9/9/26, two parcels were legally combined to create an exceptionally unique waterfront footprint. The consolidation may also provide an opportunity for reduced property taxes. Enter through the private stunning gate and follow a palm tree lined driveway to this custom Stearns-built residence, offered furnished. Inside, the dramatic great room rises 21+ feet, with a floor-to-ceiling stone fireplace, maple ceilings, cherry built-ins and an impressive open staircase. High-end craftsmanship and substantial architectural details carry throughout the home. A dedicated office and separate media room provide rooms for working and relaxing. Open the generous glass doors and the property transforms into a waterfront resort. The expansive lanai overlooks a zero-edge infinity pool and whirlpool, with a full outdoor kitchen, cypress ceilings, fire feature and entertaining areas. Watch manatees move through the canal, dolphins pass the dock and boats cruise by while entertaining poolside. From sunrise coffee by the water to sunset cocktails around the pool, this is a home built for the Florida lifestyle—where weekends feel like vacations and the hardest decision may be whether to take the boat or the golf cart. For boaters and anglers, a custom boathouse features a captain's walk and an 8,000-pound boat lift, while a 90-foot dock provides additional room for larger or visiting vessels. From here, explore Sanibel Island, Captiva, Cayo Costa, Cabbage Key and the Gulf, with world-class fishing, waterfront restaurants and island destinations accessible by boat. The infrastructure behind the lifestyle is equally impressive, with impact windows, a whole-home and pool equipment generator, whole-house dehumidification system, 1,000-gallon buried propane tank, multi-zone air conditioning and ultra-high-speed internet connectivity. Even more impressive, current flood insurance is less than $1,700 annually. Two garages accommodate six vehicles, with high ceilings offering the potential to add lifts—an incredible setup for the car enthusiast, collector or anyone who needs room for the toys. Located just one mile from the heart of Saint James City, you can hop on your golf cart and enjoy local restaurants and the laid-back island atmosphere that makes this community so unique. The real story here can't be duplicated: 3.4 acres, 1,561 feet of waterfront plus an open basin view, serious boating infrastructure, a custom estate and resort-style outdoor living in one of Southwest Florida's most distinctive boating communities. After all, why own any old waterfront home when you can own one that is truly remembered?

3 Beds ⋅ 4 Baths ⋅ 226030290 MLS

Welcome to an extraordinary waterfront estate where 3.4 acres, exceptional boating access and resort-style living come together in one remarkable property. With 1,561 feet of deep-water canal frontage, commanding wide-water views and boating access leading out to the harbor and beyond, this is the kind of Southwest Florida estate that immediately stands apart. On 9/9/26, two parcels were legally combined to create an exceptionally unique waterfront footprint. The consolidation may also provide an opportunity for reduced property taxes. Enter through the private stunning gate and follow a palm tree lined driveway to this custom Stearns-built residence, offered furnished. Inside, the dramatic great room rises 21+ feet, with a floor-to-ceiling stone fireplace, maple ceilings, cherry built-ins and an impressive open staircase. High-end craftsmanship and substantial architectural details carry throughout the home. A dedicated office and separate media room provide rooms for working and relaxing. Open the generous glass doors and the property transforms into a waterfront resort. The expansive lanai overlooks a zero-edge infinity pool and whirlpool, with a full outdoor kitchen, cypress ceilings, fire feature and entertaining areas. Watch manatees move through the canal, dolphins pass the dock and boats cruise by while entertaining poolside. From sunrise coffee by the water to sunset cocktails around the pool, this is a home built for the Florida lifestyle—where weekends feel like vacations and the hardest decision may be whether to take the boat or the golf cart. For boaters and anglers, a custom boathouse features a captain's walk and an 8,000-pound boat lift, while a 90-foot dock provides additional room for larger or visiting vessels. From here, explore Sanibel Island, Captiva, Cayo Costa, Cabbage Key and the Gulf, with world-class fishing, waterfront restaurants and island destinations accessible by boat. The infrastructure behind the lifestyle is equally impressive, with impact windows, a whole-home and pool equipment generator, whole-house dehumidification system, 1,000-gallon buried propane tank, multi-zone air conditioning and ultra-high-speed internet connectivity. Even more impressive, current flood insurance is less than $1,700 annually. Two garages accommodate six vehicles, with high ceilings offering the potential to add lifts—an incredible setup for the car enthusiast, collector or anyone who needs room for the toys. Located just one mile from the heart of Saint James City, you can hop on your golf cart and enjoy local restaurants and the laid-back island atmosphere that makes this community so unique. The real story here can't be duplicated: 3.4 acres, 1,561 feet of waterfront plus an open basin view, serious boating infrastructure, a custom estate and resort-style outdoor living in one of Southwest Florida's most distinctive boating communities. After all, why own any old waterfront home when you can own one that is truly remembered?

2755 Cussell Drive, St James City

$1,700,000

Welcome to a rare direct Gulf access waterfront estate in the highly sought-after Pine Island Shores community. Perfectly positioned to capture expansive bay views and abundant marine wildlife, this property offers a front-row seat to dolphins playing, manatees gliding by, and unforgettable Southwest Florida sunsets—all from your own backyard. With no bridges to open water, you’ll enjoy effortless access to Pine Island Sound and the Gulf of Mexico. This spacious 2-story coastal retreat features 3 bedrooms + den and 3 bathrooms, designed with a bright open floor plan, cathedral ceilings, and large windows that showcase the stunning waterfront setting throughout the home. The outdoor living experience is truly exceptional. Relax or entertain around your private saltwater pool and spa, expansive patio, gazebo, and multiple balconies are all perfectly oriented to take in the sweeping bay views and coastal breezes. Boating enthusiasts will appreciate the private dock with lift, water, and electric, making it easy to spend your days on the water. Inside, the home offers a well-appointed kitchen with ample cabinetry and eat-in space, a generous primary suite with dual sinks and separate tub and shower, and flexible living areas including a den/home office. Additional highlights include a metal roof, electric storm shutters, fireplace, surround sound wiring, and abundant storage throughout. Located in a gated boating community, this property combines privacy, space, and a true connection to the water. Whether you’re looking for a full-time residence, seasonal retreat, or luxury waterfront escape—this is Pine Island living at its finest.

3 Beds ⋅ 3 Baths ⋅ 2026020265 MLS

Welcome to a rare direct Gulf access waterfront estate in the highly sought-after Pine Island Shores community. Perfectly positioned to capture expansive bay views and abundant marine wildlife, this property offers a front-row seat to dolphins playing, manatees gliding by, and unforgettable Southwest Florida sunsets—all from your own backyard. With no bridges to open water, you’ll enjoy effortless access to Pine Island Sound and the Gulf of Mexico. This spacious 2-story coastal retreat features 3 bedrooms + den and 3 bathrooms, designed with a bright open floor plan, cathedral ceilings, and large windows that showcase the stunning waterfront setting throughout the home. The outdoor living experience is truly exceptional. Relax or entertain around your private saltwater pool and spa, expansive patio, gazebo, and multiple balconies are all perfectly oriented to take in the sweeping bay views and coastal breezes. Boating enthusiasts will appreciate the private dock with lift, water, and electric, making it easy to spend your days on the water. Inside, the home offers a well-appointed kitchen with ample cabinetry and eat-in space, a generous primary suite with dual sinks and separate tub and shower, and flexible living areas including a den/home office. Additional highlights include a metal roof, electric storm shutters, fireplace, surround sound wiring, and abundant storage throughout. Located in a gated boating community, this property combines privacy, space, and a true connection to the water. Whether you’re looking for a full-time residence, seasonal retreat, or luxury waterfront escape—this is Pine Island living at its finest.

2096 Macadamia Street, St James City

$1,999,900

With unobstructed views of the bay, perfectly framed by the tropical landscape, this residence embodies the essence of waterfront living. Upon entering the main level, you will be greeted by an abundance of natural light and vistas complimenting the fireplace in a harmonious blend of coastal and classic design. Entertain family and friends in the formal dining area or the main level balconies overlooking your backyard as dolphins swim in the background. The kitchen boasts views of the bay and offers plenty of cabinet and counterspace, a gas range and a wet bar that connects the kitchen to the family room. The primary quarters offer two walk in closets and a spacious bedroom surrounded by mature landscaping that integrates with the natural beauty of the surroundings. The well appointed guest bedrooms, one on the main level and the other on the first floor, award your guests with privacy. On the first floor you'll find a separate sitting room, a den (which the owners used as an exercise room) and a laundry room with an extra refrigerator and sink. From the office and recreation rooms you can step outside onto the expansive patio, where the beauty of coastal living truly comes to life. Sip cocktails as you watch boats glide across the bay, or indulge in alfresco dining under the pergola covered in blooming flowers. This waterfront setting offers endless opportunities for outdoor recreation, from kayaking and paddleboarding to fishing and birdwatching. The boating community of St. James City is conveniently located a short boat ride away from the Sanibel Causeway and beaches to the south and to the north, through Pine Island Sound, to the world famous Cabbage Key, Useppa Island, and Boca Grande pass. Whether appreciating some of the most pristine natural habitats in SWFL, sport fishing for tarpon or bar hoping by water, the options are endless

3 Beds ⋅ 3 Baths ⋅ 2026002528 MLS

With unobstructed views of the bay, perfectly framed by the tropical landscape, this residence embodies the essence of waterfront living. Upon entering the main level, you will be greeted by an abundance of natural light and vistas complimenting the fireplace in a harmonious blend of coastal and classic design. Entertain family and friends in the formal dining area or the main level balconies overlooking your backyard as dolphins swim in the background. The kitchen boasts views of the bay and offers plenty of cabinet and counterspace, a gas range and a wet bar that connects the kitchen to the family room. The primary quarters offer two walk in closets and a spacious bedroom surrounded by mature landscaping that integrates with the natural beauty of the surroundings. The well appointed guest bedrooms, one on the main level and the other on the first floor, award your guests with privacy. On the first floor you'll find a separate sitting room, a den (which the owners used as an exercise room) and a laundry room with an extra refrigerator and sink. From the office and recreation rooms you can step outside onto the expansive patio, where the beauty of coastal living truly comes to life. Sip cocktails as you watch boats glide across the bay, or indulge in alfresco dining under the pergola covered in blooming flowers. This waterfront setting offers endless opportunities for outdoor recreation, from kayaking and paddleboarding to fishing and birdwatching. The boating community of St. James City is conveniently located a short boat ride away from the Sanibel Causeway and beaches to the south and to the north, through Pine Island Sound, to the world famous Cabbage Key, Useppa Island, and Boca Grande pass. Whether appreciating some of the most pristine natural habitats in SWFL, sport fishing for tarpon or bar hoping by water, the options are endless

3569 San Carlos Drive, St James City