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$799,000

Escape to the laid-back charm of Old Florida with this elevated island retreat on beautiful North Captiva, located less than 300 feet from the beach—just steps from the sand and Gulf waters. This unique property also includes an adjoining lot, providing exceptional flexibility for a future pool, expansion of the existing home, or construction of an additional residence. The main home features one bedroom, two bathrooms, and a versatile den that can easily serve as a second bedroom, while the ground-level apartment offers an additional bedroom and bathroom—perfect for guests, extended family, or rental use. Multiple outdoor decks provide plenty of space to relax and enjoy the island breeze and partial Gulf views, while several storage buildings offer convenient space for golf carts, beach gear, and island essentials. Accessible only by boat or small plane, North Captiva offers a truly unique car-free lifestyle where golf carts, bicycles, and walking are the preferred ways to get around. Surrounded by nature, pristine beaches, boating, fishing, and strong vacation-rental appeal, this property offers an incredible opportunity to own a versatile piece of island paradise. Schedule your private showing and experience the North Captiva lifestyle for yourself!

2 Beds ⋅ 3 Baths ⋅ 2026037638 MLS

Escape to the laid-back charm of Old Florida with this elevated island retreat on beautiful North Captiva, located less than 300 feet from the beach—just steps from the sand and Gulf waters. This unique property also includes an adjoining lot, providing exceptional flexibility for a future pool, expansion of the existing home, or construction of an additional residence. The main home features one bedroom, two bathrooms, and a versatile den that can easily serve as a second bedroom, while the ground-level apartment offers an additional bedroom and bathroom—perfect for guests, extended family, or rental use. Multiple outdoor decks provide plenty of space to relax and enjoy the island breeze and partial Gulf views, while several storage buildings offer convenient space for golf carts, beach gear, and island essentials. Accessible only by boat or small plane, North Captiva offers a truly unique car-free lifestyle where golf carts, bicycles, and walking are the preferred ways to get around. Surrounded by nature, pristine beaches, boating, fishing, and strong vacation-rental appeal, this property offers an incredible opportunity to own a versatile piece of island paradise. Schedule your private showing and experience the North Captiva lifestyle for yourself!

201 White Pelican Drive, Upper Captiva

$459,000

Some homes are simply well maintained—3742 Tangelo Drive is maintained to an entirely different standard. Its immaculate condition, thoughtful upgrades and unmistakable pride of ownership immediately set it apart. Built in 2016 on an oversized 0.31-acre lot in St. James City’s Tropical Homesites neighborhood, this exceptional 1,553-square-foot home offers 3 bedrooms, 2 bathrooms, a 2-car garage, quality, comfort and authentic island living. Constructed of concrete block with impact-resistant windows and doors, the home is topped with a new standing-seam metal roof. The homesite was also extensively filled and elevated well beyond basic building requirements. This elevated, storm-conscious home is about as well prepared as island living gets—and has no history of flooding. A paver driveway creates a polished first impression. Inside, high ceilings, tall doorways and high-end tile flooring create a bright, open and welcoming atmosphere. Every room feels clean, spacious and thoughtfully finished. The kitchen features granite countertops, stainless-steel appliances and plenty of space for preparing meals and entertaining. Granite surfaces and refined finishes continue into the bathrooms. The spacious primary suite provides a comfortable retreat with two walk-in closets, dual vanities and a large walk-in shower. Both guest bedrooms are generously sized, offering flexibility for visitors, an office or hobbies. The home may also be purchased fully or partially furnished, if desired, making the transition to island living even easier. Florida living truly shines outside. Relax on the screened lanai or entertain around the new custom outdoor kitchen, complete with granite countertops, a built-in gas grill, refrigerator and sink. It is ready for weekend cookouts, evening gatherings and effortless outdoor dining. The large lot offers an uncommon sense of space, while the meticulously maintained exterior perfectly complements the pristine interior. Tropical Point Park and its waterfront beach area are within walking distance, placing kayaking, fishing, picnics and unforgettable sunsets just moments away. Beyond the park is Pine Island’s wonderfully unconventional character—a place where working waterfronts, tropical fruit groves, roadside produce stands, local artists, fishing boats and colorful personalities remain part of everyday life. Days move at their own pace, neighbors wave as they pass and flip-flops are appropriate almost everywhere. It is Old Florida with a little quirk, a lot of personality and none of the polished sameness found elsewhere. This is more than a move-in-ready home—it is an opportunity to own an exceptionally cared-for, thoughtfully constructed property in a lifestyle increasingly difficult to find. With its premium improvements, elevated homesite, storm-conscious construction, outstanding outdoor living spaces and distinctly Pine Island setting, 3742 Tangelo Drive stands apart from the competition.

3 Beds ⋅ 2 Baths ⋅ 2026036307 MLS

Some homes are simply well maintained—3742 Tangelo Drive is maintained to an entirely different standard. Its immaculate condition, thoughtful upgrades and unmistakable pride of ownership immediately set it apart. Built in 2016 on an oversized 0.31-acre lot in St. James City’s Tropical Homesites neighborhood, this exceptional 1,553-square-foot home offers 3 bedrooms, 2 bathrooms, a 2-car garage, quality, comfort and authentic island living. Constructed of concrete block with impact-resistant windows and doors, the home is topped with a new standing-seam metal roof. The homesite was also extensively filled and elevated well beyond basic building requirements. This elevated, storm-conscious home is about as well prepared as island living gets—and has no history of flooding. A paver driveway creates a polished first impression. Inside, high ceilings, tall doorways and high-end tile flooring create a bright, open and welcoming atmosphere. Every room feels clean, spacious and thoughtfully finished. The kitchen features granite countertops, stainless-steel appliances and plenty of space for preparing meals and entertaining. Granite surfaces and refined finishes continue into the bathrooms. The spacious primary suite provides a comfortable retreat with two walk-in closets, dual vanities and a large walk-in shower. Both guest bedrooms are generously sized, offering flexibility for visitors, an office or hobbies. The home may also be purchased fully or partially furnished, if desired, making the transition to island living even easier. Florida living truly shines outside. Relax on the screened lanai or entertain around the new custom outdoor kitchen, complete with granite countertops, a built-in gas grill, refrigerator and sink. It is ready for weekend cookouts, evening gatherings and effortless outdoor dining. The large lot offers an uncommon sense of space, while the meticulously maintained exterior perfectly complements the pristine interior. Tropical Point Park and its waterfront beach area are within walking distance, placing kayaking, fishing, picnics and unforgettable sunsets just moments away. Beyond the park is Pine Island’s wonderfully unconventional character—a place where working waterfronts, tropical fruit groves, roadside produce stands, local artists, fishing boats and colorful personalities remain part of everyday life. Days move at their own pace, neighbors wave as they pass and flip-flops are appropriate almost everywhere. It is Old Florida with a little quirk, a lot of personality and none of the polished sameness found elsewhere. This is more than a move-in-ready home—it is an opportunity to own an exceptionally cared-for, thoughtfully constructed property in a lifestyle increasingly difficult to find. With its premium improvements, elevated homesite, storm-conscious construction, outstanding outdoor living spaces and distinctly Pine Island setting, 3742 Tangelo Drive stands apart from the competition.

3742 Tangelo Drive, St James City

$349,900

Every so often, a property becomes available that simply cannot be duplicated. This beautifully maintained two-bedroom, two-bathroom end-unit condo is one of just 30 residences in Captain’s Cove, an intimate waterfront community in Bokeelia where availability is truly the exception. Inside, the updated kitchen provides a bright, inviting space for everything from a quick breakfast to dinner with friends. The living area opens directly to a screened lanai—an ideal place for morning coffee, an evening cocktail, or the gentle Pine Island breeze. One of the unit’s most valuable improvements may not be immediately visible: the condo has been completely replumbed and thoughtfully equipped with both a master water shutoff and individual shutoffs for each room. This provides exceptional convenience and control for everyday maintenance and is especially valuable for snowbirds and frequent travelers preparing to leave the property for an extended period. Impact windows and doors add storm protection, security, and peace of mind. The desirable end-unit location offers an added sense of privacy, creating a welcoming island retreat where you can settle in and immediately begin enjoying everything that makes Pine Island special. Beneath the residence, an enormous under-building parking area provides enough space for a full-size truck and boat—or as many as four vehicles. It is the kind of protected parking and storage capacity boaters dream about and condo owners almost never find, with room for the vehicles, equipment, and island toys that make life here so enjoyable. At Captain’s Cove, life revolves around the water. The community boat ramp and wet-slip access make spontaneous boating and fishing trips part of your everyday routine. Set out toward Pine Island Sound and Charlotte Harbor, chase the morning bite, cruise to Cayo Costa, Boca Grande, or Cabbage Key for lunch, and return home beneath a sky painted by a Southwest Florida sunset. When the boat is resting, cool off in the community swimming pool or enjoy an afternoon match on the tennis court. Here, an ordinary day can become an island-hopping adventure, a memorable fishing trip, or a quiet afternoon spent savoring the slower rhythm of Bokeelia. Condos in Captain’s Cove are rarely offered—and a two-bedroom end unit with this combination of updates, impact protection, complete replumbing, screened outdoor living, and extraordinary under-building parking is rarer still. This is more than an updated island condo. It is your launch point for a life measured in tides, sunsets, and unforgettable days on the water. There will always be other condos. There may never be another opportunity quite like this one.

2 Beds ⋅ 2 Baths ⋅ 2026034297 MLS

Every so often, a property becomes available that simply cannot be duplicated. This beautifully maintained two-bedroom, two-bathroom end-unit condo is one of just 30 residences in Captain’s Cove, an intimate waterfront community in Bokeelia where availability is truly the exception. Inside, the updated kitchen provides a bright, inviting space for everything from a quick breakfast to dinner with friends. The living area opens directly to a screened lanai—an ideal place for morning coffee, an evening cocktail, or the gentle Pine Island breeze. One of the unit’s most valuable improvements may not be immediately visible: the condo has been completely replumbed and thoughtfully equipped with both a master water shutoff and individual shutoffs for each room. This provides exceptional convenience and control for everyday maintenance and is especially valuable for snowbirds and frequent travelers preparing to leave the property for an extended period. Impact windows and doors add storm protection, security, and peace of mind. The desirable end-unit location offers an added sense of privacy, creating a welcoming island retreat where you can settle in and immediately begin enjoying everything that makes Pine Island special. Beneath the residence, an enormous under-building parking area provides enough space for a full-size truck and boat—or as many as four vehicles. It is the kind of protected parking and storage capacity boaters dream about and condo owners almost never find, with room for the vehicles, equipment, and island toys that make life here so enjoyable. At Captain’s Cove, life revolves around the water. The community boat ramp and wet-slip access make spontaneous boating and fishing trips part of your everyday routine. Set out toward Pine Island Sound and Charlotte Harbor, chase the morning bite, cruise to Cayo Costa, Boca Grande, or Cabbage Key for lunch, and return home beneath a sky painted by a Southwest Florida sunset. When the boat is resting, cool off in the community swimming pool or enjoy an afternoon match on the tennis court. Here, an ordinary day can become an island-hopping adventure, a memorable fishing trip, or a quiet afternoon spent savoring the slower rhythm of Bokeelia. Condos in Captain’s Cove are rarely offered—and a two-bedroom end unit with this combination of updates, impact protection, complete replumbing, screened outdoor living, and extraordinary under-building parking is rarer still. This is more than an updated island condo. It is your launch point for a life measured in tides, sunsets, and unforgettable days on the water. There will always be other condos. There may never be another opportunity quite like this one.

16385 Boyce Drive Unit 301, Bokeelia

$975,000

Set on 2.6 acres in Bokeelia, this fully operational tropical island farm is where mornings begin with fresh eggs and evenings end beside the pool in the island breeze. Part home, part orchard and part working farm, it is ready for its next chapter. Zoned AG-2, the property is ideal for farming, nursery operations or homestead living. The owners currently receive an agricultural tax exemption; the next owner may apply for the same benefit. The home offers 2,283 square feet plus a 573-square-foot air-conditioned attached garage. Mature trees, nursery inventory, chickens, equipment, tools, furnishings and operational assets are included, allowing the next owner to harvest fruit, gather eggs and grow plants without starting from scratch. Upstairs are the main living area, kitchen, dining space and primary bedroom, plus a covered porch overlooking the farm. Downstairs are guest bedrooms, a full bathroom, laundry area and second living room opening to the patio and screened pool—ideal for guests or multigenerational living. Improvements include remodeled kitchen and bathrooms, smart appliances, tile floors, plantation shutters, impact-rated windows and doors, updated A/C, spray-foam insulation, newer water heater and water-treatment systems. A 24-kW generator and 500-gallon underground propane tank add peace of mind. The septic field was replaced, a lift station added, and the roof was resecured in 2022 and inspected annually. The property is not in a designated flood zone. The grounds produce mango, avocado, coconut, citrus, lychee, starfruit, papaya, jackfruit, passion fruit, moringa and more. Over 100 banana plants representing about 22 varieties are established and producing. App-controlled irrigation reaches about 95% of the trees. Farm infrastructure includes perimeter fencing, secure chicken coops, three pole barns, two hurricane-strapped sheds and an air-conditioned tool shed with electric service. Nursery supplies and extensive farm equipment are included for continued operation of the on-site market. Cool off in the screened pool, gather on the lanai or relax on the upper porch in your own tropical oasis. Whether you envision a working farm, nursery, self-sufficient homestead or island retreat with supplemental-income potential, this remarkable property offers room to grow and a lifestyle that feels like a getaway every day.

3 Beds ⋅ 3 Baths ⋅ 2026032475 MLS

Set on 2.6 acres in Bokeelia, this fully operational tropical island farm is where mornings begin with fresh eggs and evenings end beside the pool in the island breeze. Part home, part orchard and part working farm, it is ready for its next chapter. Zoned AG-2, the property is ideal for farming, nursery operations or homestead living. The owners currently receive an agricultural tax exemption; the next owner may apply for the same benefit. The home offers 2,283 square feet plus a 573-square-foot air-conditioned attached garage. Mature trees, nursery inventory, chickens, equipment, tools, furnishings and operational assets are included, allowing the next owner to harvest fruit, gather eggs and grow plants without starting from scratch. Upstairs are the main living area, kitchen, dining space and primary bedroom, plus a covered porch overlooking the farm. Downstairs are guest bedrooms, a full bathroom, laundry area and second living room opening to the patio and screened pool—ideal for guests or multigenerational living. Improvements include remodeled kitchen and bathrooms, smart appliances, tile floors, plantation shutters, impact-rated windows and doors, updated A/C, spray-foam insulation, newer water heater and water-treatment systems. A 24-kW generator and 500-gallon underground propane tank add peace of mind. The septic field was replaced, a lift station added, and the roof was resecured in 2022 and inspected annually. The property is not in a designated flood zone. The grounds produce mango, avocado, coconut, citrus, lychee, starfruit, papaya, jackfruit, passion fruit, moringa and more. Over 100 banana plants representing about 22 varieties are established and producing. App-controlled irrigation reaches about 95% of the trees. Farm infrastructure includes perimeter fencing, secure chicken coops, three pole barns, two hurricane-strapped sheds and an air-conditioned tool shed with electric service. Nursery supplies and extensive farm equipment are included for continued operation of the on-site market. Cool off in the screened pool, gather on the lanai or relax on the upper porch in your own tropical oasis. Whether you envision a working farm, nursery, self-sufficient homestead or island retreat with supplemental-income potential, this remarkable property offers room to grow and a lifestyle that feels like a getaway every day.

12303 Cristi Way, Bokeelia

$240,000

We are proud to present your slice of paradise on Pine Island with this rare gulf-access waterfront lot located in the peaceful boating community of St. James City. This spacious lot offers 110 feet of direct frontage on the Dawson Canal, providing straight-out, unobstructed access to Matlacha Pass and San Carlos Bay—no bridges—just effortless boating to world-class fishing, scenic island hopping, and waterfront dining. The rear of the property is already secured with rip rap shoreline protection along the entire length, providing durability, erosion control, and added peace of mind for your future waterfront build. To make things even easier, the lot has been improved with approximately 100 loads of fill dirt—an estimated $40,000 value—already in place, helping reduce site prep costs and accelerating your timeline to break ground. Tucked near the end of a quiet dead-end road, this homesite enjoys minimal traffic and maximum serenity, surrounded by canal-front homes, tropical palms, and the natural beauty Pine Island is known for. Just minutes away, you'll find local favorites like The Waterfront Restaurant, Low Key Tiki, and Phuzzy's Boat Shack, along with the charming, artsy village of Matlacha, filled with galleries, shops, and island flair. Outdoor enthusiasts will appreciate nearby kayaking trails, birdwatching areas, and nature preserves, while boaters have endless options with direct Gulf access to Sanibel, Captiva, and Cayo Costa. This is a unique opportunity to own a build-ready, rip rap-protected canal lot in one of Southwest Florida’s most laid-back coastal communities. Whether you're planning a full-time residence or a weekend escape, this property offers the perfect gateway to island living at its finest.

2026025640 MLS

We are proud to present your slice of paradise on Pine Island with this rare gulf-access waterfront lot located in the peaceful boating community of St. James City. This spacious lot offers 110 feet of direct frontage on the Dawson Canal, providing straight-out, unobstructed access to Matlacha Pass and San Carlos Bay—no bridges—just effortless boating to world-class fishing, scenic island hopping, and waterfront dining. The rear of the property is already secured with rip rap shoreline protection along the entire length, providing durability, erosion control, and added peace of mind for your future waterfront build. To make things even easier, the lot has been improved with approximately 100 loads of fill dirt—an estimated $40,000 value—already in place, helping reduce site prep costs and accelerating your timeline to break ground. Tucked near the end of a quiet dead-end road, this homesite enjoys minimal traffic and maximum serenity, surrounded by canal-front homes, tropical palms, and the natural beauty Pine Island is known for. Just minutes away, you'll find local favorites like The Waterfront Restaurant, Low Key Tiki, and Phuzzy's Boat Shack, along with the charming, artsy village of Matlacha, filled with galleries, shops, and island flair. Outdoor enthusiasts will appreciate nearby kayaking trails, birdwatching areas, and nature preserves, while boaters have endless options with direct Gulf access to Sanibel, Captiva, and Cayo Costa. This is a unique opportunity to own a build-ready, rip rap-protected canal lot in one of Southwest Florida’s most laid-back coastal communities. Whether you're planning a full-time residence or a weekend escape, this property offers the perfect gateway to island living at its finest.

2807 Cussell Drive, St James City

$399,000

Exceptional opportunity to own a turnkey, income-producing duplex in the heart of Bokeelia. Built in 2005 and featuring a new roof installed in 2023, this well-maintained property offers two spacious units, each with 3 bedrooms, 2 bathrooms, and 1,117 square feet of living space. Both units feature modern finishes, private rear decks, and separate backyard areas, providing tenants with the comfort and privacy of a single-family home. Long-term tenants are already in place, creating immediate and reliable cash flow for investors. Whether you're looking to expand your investment portfolio or take advantage of a house-hacking opportunity by living in one unit and renting the other to offset your housing expenses, this versatile property is ready to perform from day one. With stable income, recent capital improvements, and strong rental appeal, this duplex is a rare opportunity on beautiful Pine Island.

6 Beds ⋅ 4 Baths ⋅ 2026024876 MLS

Exceptional opportunity to own a turnkey, income-producing duplex in the heart of Bokeelia. Built in 2005 and featuring a new roof installed in 2023, this well-maintained property offers two spacious units, each with 3 bedrooms, 2 bathrooms, and 1,117 square feet of living space. Both units feature modern finishes, private rear decks, and separate backyard areas, providing tenants with the comfort and privacy of a single-family home. Long-term tenants are already in place, creating immediate and reliable cash flow for investors. Whether you're looking to expand your investment portfolio or take advantage of a house-hacking opportunity by living in one unit and renting the other to offset your housing expenses, this versatile property is ready to perform from day one. With stable income, recent capital improvements, and strong rental appeal, this duplex is a rare opportunity on beautiful Pine Island.

5527 Judith Road, Bokeelia

$999,000

Exceptional opportunity to acquire a fully renovated commercial property located on the highly visible corner of Fowler Street and Katherine Street in Fort Myers. The property consists of a 6,200± square foot commercial building situated on approximately 0.46 acres and zoned CI (Commercial Intensive), allowing for a broad range of commercial uses including retail, office, medical, showroom, professional services, contractor operations, and warehouse/storage uses. Originally constructed in 1955, the building underwent a complete top-to-bottom renovation in 2023, offering modernized interiors, updated finishes, and excellent functionality throughout. The property is currently owner occupied and configured into three potential units, creating flexibility for an owner-user, investor, or future multi-tenant occupancy. One suite includes approximately 1,140± square feet ideally suited for warehouse, storage, or light operational use with convenient rear access. The site offers exceptional visibility and accessibility with approximately 163 feet of frontage on Fowler Street and 125 feet of frontage on Katherine Street. Positioned along a major commercial corridor with traffic counts exceeding 20,000 vehicles per day, the property benefits from outstanding signage exposure and strong daily traffic flow. Additional site features include ample on-site parking, multiple ingress and egress points, and a large fenced rear lot ideal for storage, fleet parking, outdoor operations, or additional functionality. Conveniently located near Downtown Fort Myers, US-41, Colonial Boulevard, and Interstate 75, the property provides excellent connectivity throughout Southwest Florida and is surrounded by established residential neighborhoods, retail centers, office users, and commercial businesses. This move-in ready asset presents a rare opportunity to acquire a flexible-use commercial property in one of Fort Myers’ active commercial corridors.

2026022904 MLS

Exceptional opportunity to acquire a fully renovated commercial property located on the highly visible corner of Fowler Street and Katherine Street in Fort Myers. The property consists of a 6,200± square foot commercial building situated on approximately 0.46 acres and zoned CI (Commercial Intensive), allowing for a broad range of commercial uses including retail, office, medical, showroom, professional services, contractor operations, and warehouse/storage uses. Originally constructed in 1955, the building underwent a complete top-to-bottom renovation in 2023, offering modernized interiors, updated finishes, and excellent functionality throughout. The property is currently owner occupied and configured into three potential units, creating flexibility for an owner-user, investor, or future multi-tenant occupancy. One suite includes approximately 1,140± square feet ideally suited for warehouse, storage, or light operational use with convenient rear access. The site offers exceptional visibility and accessibility with approximately 163 feet of frontage on Fowler Street and 125 feet of frontage on Katherine Street. Positioned along a major commercial corridor with traffic counts exceeding 20,000 vehicles per day, the property benefits from outstanding signage exposure and strong daily traffic flow. Additional site features include ample on-site parking, multiple ingress and egress points, and a large fenced rear lot ideal for storage, fleet parking, outdoor operations, or additional functionality. Conveniently located near Downtown Fort Myers, US-41, Colonial Boulevard, and Interstate 75, the property provides excellent connectivity throughout Southwest Florida and is surrounded by established residential neighborhoods, retail centers, office users, and commercial businesses. This move-in ready asset presents a rare opportunity to acquire a flexible-use commercial property in one of Fort Myers’ active commercial corridors.

2730 Fowler Street, Fort Myers

$1,500,000

Set within the historic heart of Pineland, this extraordinary 9.5-acre AG-2 zoned estate offers a rare opportunity to own a true piece of Old Florida heritage. Held within the same family for five generations, the property carries a legacy that stretches back more than a century, blending agricultural utility, historic character, and deep cultural significance into one irreplaceable offering. Surrounded by mature trees and peaceful rural landscapes, the property is currently configured with two established horse paddocks, stables, multiple outbuildings, and expansive usable acreage suited for equestrian, agricultural, recreational, or private estate use. The AG-2 zoning allows for flexibility while preserving the property’s timeless country setting. Positioned near the center of the property is a home originally constructed in 1926, now officially 100 years old. The residence remains occupied and functional, offering the next owner the option to restore and preserve a historic Pine Island homeplace or reimagine the property entirely according to their own vision. While the home itself is not considered the primary contributory value of the estate, it adds an unmistakable sense of authenticity and history rarely found in today’s market. What truly distinguishes this property is its location within one of the most historically significant areas in Southwest Florida. Located near the ancient Calusa Canal system and just moments from the renowned Pineland archaeological district, the property sits within a landscape once occupied and engineered by the powerful Calusa civilization — one of the most advanced indigenous societies in North America. These hand-built canals connected fisheries, inland waterways, ceremonial sites, and shell mound complexes throughout the region and remain among the most remarkable examples of prehistoric engineering in the United States. Historians recognize Pineland as one of the most important Calusa settlements ever discovered, historically associated with the settlement known as “Tanpa,” believed to have contributed to the modern namesake of Tampa. The nearby shell mounds, waterways, and preserved archaeological features stand today as enduring reminders of the area’s immense cultural importance. Whether envisioned as a private family compound, equestrian retreat, agricultural homestead, restoration project, or long-term legacy holding, this property offers a combination of acreage, history, and generational significance that is becoming increasingly impossible to find. Properties can be replicated. History cannot.

2026022571 MLS

Set within the historic heart of Pineland, this extraordinary 9.5-acre AG-2 zoned estate offers a rare opportunity to own a true piece of Old Florida heritage. Held within the same family for five generations, the property carries a legacy that stretches back more than a century, blending agricultural utility, historic character, and deep cultural significance into one irreplaceable offering. Surrounded by mature trees and peaceful rural landscapes, the property is currently configured with two established horse paddocks, stables, multiple outbuildings, and expansive usable acreage suited for equestrian, agricultural, recreational, or private estate use. The AG-2 zoning allows for flexibility while preserving the property’s timeless country setting. Positioned near the center of the property is a home originally constructed in 1926, now officially 100 years old. The residence remains occupied and functional, offering the next owner the option to restore and preserve a historic Pine Island homeplace or reimagine the property entirely according to their own vision. While the home itself is not considered the primary contributory value of the estate, it adds an unmistakable sense of authenticity and history rarely found in today’s market. What truly distinguishes this property is its location within one of the most historically significant areas in Southwest Florida. Located near the ancient Calusa Canal system and just moments from the renowned Pineland archaeological district, the property sits within a landscape once occupied and engineered by the powerful Calusa civilization — one of the most advanced indigenous societies in North America. These hand-built canals connected fisheries, inland waterways, ceremonial sites, and shell mound complexes throughout the region and remain among the most remarkable examples of prehistoric engineering in the United States. Historians recognize Pineland as one of the most important Calusa settlements ever discovered, historically associated with the settlement known as “Tanpa,” believed to have contributed to the modern namesake of Tampa. The nearby shell mounds, waterways, and preserved archaeological features stand today as enduring reminders of the area’s immense cultural importance. Whether envisioned as a private family compound, equestrian retreat, agricultural homestead, restoration project, or long-term legacy holding, this property offers a combination of acreage, history, and generational significance that is becoming increasingly impossible to find. Properties can be replicated. History cannot.

7535 Caloosa Drive, Bokeelia

$749,900

Welcome to paradise in the highly sought-after Alden Pines neighborhood of Bokeelia! Perfectly positioned on an oversized double homesite totaling 0.67 acres, this extraordinary coastal retreat offers the ultimate Pine Island lifestyle with an unbeatable location just a short walk to the clubhouse at the newly revitalized Alden Pines “The Gator in the Rough” golf course, Pineland Marina, Tarpon Lodge, and the historic Randell Research Center. With the golf course renovation nearing completion and reopening this fall, the future of this area has never looked brighter. Encompassing an impressive 2,732 square feet of living space, this spacious residence features 4 bedrooms, 3 bathrooms, and an incredible 6-car garage with 3 tandem spaces — perfect for car collectors, golf carts, boats, kayaks, or all your island toys. Outdoor living is where this home truly shines. The massive 35’ x 15’ resort-style pool and spa are surrounded by an expansive paver patio designed for entertaining, complete with a covered outdoor dining area, full outdoor kitchen, and convenient pool bath. Whether hosting family and friends or simply relaxing in your private tropical oasis, every inch of this property embraces the Florida lifestyle. The luxurious primary suite feels more like a private resort retreat, featuring a screened wraparound balcony, dual walk-in closets, and an extraordinary dual-bathroom design connected by an oversized walk-through shower unlike anything you’ve seen before. The shower even opens to its own private outdoor balcony, creating a spa-like experience immersed in nature. Designed for both comfort and peace of mind, the property also features an elevated Generac whole-home backup generator with a buried fuel tank, providing reliable protection and convenience year-round. Lush tropical landscaping with mature palms, native vegetation, and vibrant greenery surrounds the property, enhancing the serene coastal atmosphere and providing exceptional privacy. This is a rare opportunity to own a truly unique island estate in one of Pine Island’s most desirable communities.

4 Beds ⋅ 3 Baths ⋅ 2026021268 MLS

Welcome to paradise in the highly sought-after Alden Pines neighborhood of Bokeelia! Perfectly positioned on an oversized double homesite totaling 0.67 acres, this extraordinary coastal retreat offers the ultimate Pine Island lifestyle with an unbeatable location just a short walk to the clubhouse at the newly revitalized Alden Pines “The Gator in the Rough” golf course, Pineland Marina, Tarpon Lodge, and the historic Randell Research Center. With the golf course renovation nearing completion and reopening this fall, the future of this area has never looked brighter. Encompassing an impressive 2,732 square feet of living space, this spacious residence features 4 bedrooms, 3 bathrooms, and an incredible 6-car garage with 3 tandem spaces — perfect for car collectors, golf carts, boats, kayaks, or all your island toys. Outdoor living is where this home truly shines. The massive 35’ x 15’ resort-style pool and spa are surrounded by an expansive paver patio designed for entertaining, complete with a covered outdoor dining area, full outdoor kitchen, and convenient pool bath. Whether hosting family and friends or simply relaxing in your private tropical oasis, every inch of this property embraces the Florida lifestyle. The luxurious primary suite feels more like a private resort retreat, featuring a screened wraparound balcony, dual walk-in closets, and an extraordinary dual-bathroom design connected by an oversized walk-through shower unlike anything you’ve seen before. The shower even opens to its own private outdoor balcony, creating a spa-like experience immersed in nature. Designed for both comfort and peace of mind, the property also features an elevated Generac whole-home backup generator with a buried fuel tank, providing reliable protection and convenience year-round. Lush tropical landscaping with mature palms, native vegetation, and vibrant greenery surrounds the property, enhancing the serene coastal atmosphere and providing exceptional privacy. This is a rare opportunity to own a truly unique island estate in one of Pine Island’s most desirable communities.

14221 Clubhouse Drive, Bokeelia

$249,900

Looking for a charming cottage with personality? Welcome to this recently renovated 3-bedroom, 1-bath single-family home in Bokeelia’s beloved “Fish Streets”—a local favorite known for its laid-back island vibe. This move-in ready home has all the updates you want without losing its charm. Inside, you’ll find a clean, refreshed space that’s ready for your furniture (and whatever style you’re currently into—we’re not here to judge). Step outside and you’ll really see the value—this oversized lot offers plenty of room for outdoor living, hobbies, or finally having space for your boat, trailer, or weekend projects. There’s even a large shed out back for storage, a workshop, or your next big idea. If you’ve been searching for a home with space, character, and a location locals love, this one checks all the boxes. Opportunities like this don’t last—schedule your showing today!

3 Beds ⋅ 1 Baths ⋅ 2026013549 MLS

Looking for a charming cottage with personality? Welcome to this recently renovated 3-bedroom, 1-bath single-family home in Bokeelia’s beloved “Fish Streets”—a local favorite known for its laid-back island vibe. This move-in ready home has all the updates you want without losing its charm. Inside, you’ll find a clean, refreshed space that’s ready for your furniture (and whatever style you’re currently into—we’re not here to judge). Step outside and you’ll really see the value—this oversized lot offers plenty of room for outdoor living, hobbies, or finally having space for your boat, trailer, or weekend projects. There’s even a large shed out back for storage, a workshop, or your next big idea. If you’ve been searching for a home with space, character, and a location locals love, this one checks all the boxes. Opportunities like this don’t last—schedule your showing today!

5935 Sea Bass Road, Bokeelia

$475,000

This 2024-built 3-bedroom, 2-bath stilt home offers 1,518 square feet of modern coastal living and is built like it plans to be here a while. The oversized pilings are driven approximately 25 feet into the ground, providing serious structural confidence and peace of mind. Elevated, well-built, and thoughtfully designed, this home checks both the practical and aesthetic boxes. It has never been lived in full time, and yes—it still has that unmistakable “new home smell” you don’t usually get in resale homes. Inside, you’ll find a bright, open-concept floor plan with a spacious great room and a stylish kitchen featuring stainless steel appliances, ample cabinetry, and a large island perfect for entertaining, meal prepping, or pretending you’re on a cooking show. The split-bedroom layout offers privacy, with three generously sized bedrooms and two modern bathrooms finished with clean, contemporary touches. Natural light fills the home, and the elevated setting adds both airflow and charm. Downstairs, the covered area provides flexible space currently set up with a spa and seating—ideal for post-fishing relaxation, evening cocktails, or just enjoying the fact that you don’t live in a snowstorm. Parking is conveniently located in front of the home, and the stilt design makes excellent use of space while enhancing the coastal lifestyle. Situated near the highly desirable Henley Canal—one of the most active canals in St. James City—the home offers a front-row seat to daily boat traffic, island vibes, and authentic Pine Island living. You’re within walking distance to restaurants, waterfront bars, fishing spots, and all the local flavor that makes this area special. The home is currently set up for and actively operating as a vacation rental and can continue as such with new ownership, making it a rare find that works just as well as an investment as it does a personal retreat. Whether you’re looking for a primary residence, a seasonal escape, or a property that pays for itself while you’re not using it, this one delivers—with a little personality to match.

3 Beds ⋅ 2 Baths ⋅ 2026001749 MLS

This 2024-built 3-bedroom, 2-bath stilt home offers 1,518 square feet of modern coastal living and is built like it plans to be here a while. The oversized pilings are driven approximately 25 feet into the ground, providing serious structural confidence and peace of mind. Elevated, well-built, and thoughtfully designed, this home checks both the practical and aesthetic boxes. It has never been lived in full time, and yes—it still has that unmistakable “new home smell” you don’t usually get in resale homes. Inside, you’ll find a bright, open-concept floor plan with a spacious great room and a stylish kitchen featuring stainless steel appliances, ample cabinetry, and a large island perfect for entertaining, meal prepping, or pretending you’re on a cooking show. The split-bedroom layout offers privacy, with three generously sized bedrooms and two modern bathrooms finished with clean, contemporary touches. Natural light fills the home, and the elevated setting adds both airflow and charm. Downstairs, the covered area provides flexible space currently set up with a spa and seating—ideal for post-fishing relaxation, evening cocktails, or just enjoying the fact that you don’t live in a snowstorm. Parking is conveniently located in front of the home, and the stilt design makes excellent use of space while enhancing the coastal lifestyle. Situated near the highly desirable Henley Canal—one of the most active canals in St. James City—the home offers a front-row seat to daily boat traffic, island vibes, and authentic Pine Island living. You’re within walking distance to restaurants, waterfront bars, fishing spots, and all the local flavor that makes this area special. The home is currently set up for and actively operating as a vacation rental and can continue as such with new ownership, making it a rare find that works just as well as an investment as it does a personal retreat. Whether you’re looking for a primary residence, a seasonal escape, or a property that pays for itself while you’re not using it, this one delivers—with a little personality to match.

3524 5th Avenue, St James City

$1,970,000

Rare Opportunity to Purchase Luxurious Gulf Front Estate on North Captiva Island A rare opportunity has arisen to purchase a luxurious gulf front estate located within the prestigious community of Safety Harbor Club on North Captiva Island. This stunning coastal property boasts beach frontage with breathtaking sunsets and panoramic views of the Gulf. Recently renovated and remodeled with the highest quality craftsmanship and attention to detail, this estate is truly one-of-a-kind. The interior of the property features a striking custom staircase, quartz countertops, and custom solid wood cabinetry in the kitchen. Beautiful oak and porcelain floors run throughout the home, creating a sense of elegance and luxury. The estate includes two guest bedrooms. One ensuite. The highlight of the property is the exquisite Master Bedroom, located on the second floor with private decks offering stunning views of the Gulf. The Master Bedroom also features a fireplace and a large bathroom with a jet tub and separate shower. The spacious kitchen is equipped with an island cooktop, downdraft ventilation, Subzero refrigerator/freezer, microwave with convection, wall oven, and dishwasher. The property offers gorgeous views of the beach from the Master Bedroom, kitchen, dining area, and great room. This custom home is truly a gem and must be seen to be fully appreciated. Schedule an appointment today to view this beautiful estate and make it your own.

3 Beds ⋅ 3 Baths ⋅ 2025000843 MLS

Rare Opportunity to Purchase Luxurious Gulf Front Estate on North Captiva Island A rare opportunity has arisen to purchase a luxurious gulf front estate located within the prestigious community of Safety Harbor Club on North Captiva Island. This stunning coastal property boasts beach frontage with breathtaking sunsets and panoramic views of the Gulf. Recently renovated and remodeled with the highest quality craftsmanship and attention to detail, this estate is truly one-of-a-kind. The interior of the property features a striking custom staircase, quartz countertops, and custom solid wood cabinetry in the kitchen. Beautiful oak and porcelain floors run throughout the home, creating a sense of elegance and luxury. The estate includes two guest bedrooms. One ensuite. The highlight of the property is the exquisite Master Bedroom, located on the second floor with private decks offering stunning views of the Gulf. The Master Bedroom also features a fireplace and a large bathroom with a jet tub and separate shower. The spacious kitchen is equipped with an island cooktop, downdraft ventilation, Subzero refrigerator/freezer, microwave with convection, wall oven, and dishwasher. The property offers gorgeous views of the beach from the Master Bedroom, kitchen, dining area, and great room. This custom home is truly a gem and must be seen to be fully appreciated. Schedule an appointment today to view this beautiful estate and make it your own.

406 Gulf Bend Drive, Captiva

$26,900

Great homesite in an area of nice homes. Ready to build your dream home in Southwest Florida. Close to transportation, I-75, shopping, restaurants, golf, and sports venues. Less than 10 Minutes to Downtown Punta Gorda, 10 Minutes to Cape Coral. Financing available.

223080067 MLS

Great homesite in an area of nice homes. Ready to build your dream home in Southwest Florida. Close to transportation, I-75, shopping, restaurants, golf, and sports venues. Less than 10 Minutes to Downtown Punta Gorda, 10 Minutes to Cape Coral. Financing available.

26448 Deer Road, Punta Gorda

$16,900

Good Standard size lot in area of nice homes. Ready to build your dream home in Southwest Florida. Close to transportation I-75 shopping , restaurants, golf, and sports venues. High and dry, not in a flood zone. Financing available.

223079156 MLS

Good Standard size lot in area of nice homes. Ready to build your dream home in Southwest Florida. Close to transportation I-75 shopping , restaurants, golf, and sports venues. High and dry, not in a flood zone. Financing available.

6300 Russell Street, Punta Gorda

$54,900

We are proud to bring you a slice of tropical paradise! This 80x100 vacant homesite at 3651 Crestwell Cr, nestled in Saint James City's sought-after St. Jude Harbors, is a true gem awaiting your dream abode. Surrounded by lush preserve land, this waterfront haven on a freshwater canal offers an idyllic blend of tranquility and convenience. Immerse yourself in the vibrant ambiance of Pine Island, as you revel in the gentle caress of the balmy breeze and the mesmerizing melody of the nearby canal. Indulge in the sheer delight of strolling to the array of delightful eateries, casting your line at nearby prime fishing spots, or exploring the enchanting walking trails. With city water and electricity readily available, seize the opportunity to craft your own tropical oasis. Come, envision your ideal sanctuary amidst this captivating natural haven!

223078692 MLS

We are proud to bring you a slice of tropical paradise! This 80x100 vacant homesite at 3651 Crestwell Cr, nestled in Saint James City's sought-after St. Jude Harbors, is a true gem awaiting your dream abode. Surrounded by lush preserve land, this waterfront haven on a freshwater canal offers an idyllic blend of tranquility and convenience. Immerse yourself in the vibrant ambiance of Pine Island, as you revel in the gentle caress of the balmy breeze and the mesmerizing melody of the nearby canal. Indulge in the sheer delight of strolling to the array of delightful eateries, casting your line at nearby prime fishing spots, or exploring the enchanting walking trails. With city water and electricity readily available, seize the opportunity to craft your own tropical oasis. Come, envision your ideal sanctuary amidst this captivating natural haven!

3651 Crestwell Court, St James City

$199,900

We are proud to bring you your slice of tropical paradise in Pine Island Cove, one of St. James City’s most desirable 55+ communities! This brand-new 2 bedroom, 2 bathroom manufactured home has just been installed and is elevated to meet current flood zone elevation requirements, providing peace of mind and potential insurance savings. With an open-concept floor plan, a split-bedroom layout, and a dedicated laundry room, this home is both functional and filled with natural light. Outside, enjoy the convenience of a new covered carport and matching storage shed—ideal for your tools, beach gear, or golf cart. Best of all, the home is located just three homes away from the community center and an easy walk to the heated community pool and other amenities. The interior and exterior comes as a blank slate—fresh, neutral, and ready for your personal touches to make it truly your own. Add your preferred finishes, furnishings, landscaping, and décor to create your perfect Florida retreat. Pine Island Cove offers direct Gulf access via a private community boat ramp, along with RV/boat storage, an active clubhouse, and a full calendar of social events. The HOA is low and the island lifestyle is unmatched. Pine Island is known for its laid-back atmosphere, tropical surroundings, excellent fishing, art galleries, and waterfront dining—a true escape from the mainland grind. Don’t miss this opportunity to own a brand-new, elevated home in a welcoming waterfront community. Schedule your private showing today and make this island gem your own!

2 Beds ⋅ 2 Baths ⋅ 225056362 MLS

We are proud to bring you your slice of tropical paradise in Pine Island Cove, one of St. James City’s most desirable 55+ communities! This brand-new 2 bedroom, 2 bathroom manufactured home has just been installed and is elevated to meet current flood zone elevation requirements, providing peace of mind and potential insurance savings. With an open-concept floor plan, a split-bedroom layout, and a dedicated laundry room, this home is both functional and filled with natural light. Outside, enjoy the convenience of a new covered carport and matching storage shed—ideal for your tools, beach gear, or golf cart. Best of all, the home is located just three homes away from the community center and an easy walk to the heated community pool and other amenities. The interior and exterior comes as a blank slate—fresh, neutral, and ready for your personal touches to make it truly your own. Add your preferred finishes, furnishings, landscaping, and décor to create your perfect Florida retreat. Pine Island Cove offers direct Gulf access via a private community boat ramp, along with RV/boat storage, an active clubhouse, and a full calendar of social events. The HOA is low and the island lifestyle is unmatched. Pine Island is known for its laid-back atmosphere, tropical surroundings, excellent fishing, art galleries, and waterfront dining—a true escape from the mainland grind. Don’t miss this opportunity to own a brand-new, elevated home in a welcoming waterfront community. Schedule your private showing today and make this island gem your own!

4944 Porky Lane, St James City

$15,400

TROPICAL GULF ACRES! JUST OFF RT 41 AND JUST NORTH OF FT MYERS AND SOUTH OF THE CITY OF PUNTA GORDA. SUPER CONVENIENT LOCATION.

223080024 MLS

TROPICAL GULF ACRES! JUST OFF RT 41 AND JUST NORTH OF FT MYERS AND SOUTH OF THE CITY OF PUNTA GORDA. SUPER CONVENIENT LOCATION.

27180 Earthnut Drive, Punta Gorda

$24,200

Great homesite in an area of nice homes. Ready to build your dream home in Southwest Florida. Close to transportation, I-75, shopping, restaurants, golf, and sports venues. Less than 10 Minutes to Downtown Punta Gorda, 10 Minutes to Cape Coral. Financing available.

223080036 MLS

Great homesite in an area of nice homes. Ready to build your dream home in Southwest Florida. Close to transportation, I-75, shopping, restaurants, golf, and sports venues. Less than 10 Minutes to Downtown Punta Gorda, 10 Minutes to Cape Coral. Financing available.

27412 Chrysalis Drive, Punta Gorda