$139,999 Island Life at Its Finest! Welcome to this charming 1-bedroom, 1-bath condo located just minutes from the center of town, offering convenient access to shopping, dining, and everything island living has to offer. Whether you're looking for an affordable island getaway, a full-time residence, or an income-producing rental investment, this property checks all the boxes. Inside, you'll find a bright and inviting living space featuring wood plank tile flooring throughout the main living areas, cozy carpet in the bedroom, and an abundance of natural light. What truly sets this property apart is its location on one of the higher elevations on the island. The property has never flooded and sustained zero damage during the last three major hurricanes, offering exceptional peace of mind and making it a rare find for island living. The real value extends beyond the unit itself. For just $150 per year HOA fee, owners enjoy access to 8 community boat slips and a direct Gulf access boat ramp—perfect for boating and fishing enthusiasts. Just down the street, you'll also find a marina, park, pickleball and tennis courts, baseball fields, and a community pool, creating endless opportunities for recreation and relaxation. Don't miss this rare opportunity to own an affordable piece of paradise and enjoy the island lifestyle you've always dreamed of! 1 Beds ⋅ 1 Baths ⋅ 2026025178 MLS Island Life at Its Finest! Welcome to this charming 1-bedroom, 1-bath condo located just minutes from the center of town, offering convenient access to shopping, dining, and everything island living has to offer. Whether you're looking for an affordable island getaway, a full-time residence, or an income-producing rental investment, this property checks all the boxes. Inside, you'll find a bright and inviting living space featuring wood plank tile flooring throughout the main living areas, cozy carpet in the bedroom, and an abundance of natural light. What truly sets this property apart is its location on one of the higher elevations on the island. The property has never flooded and sustained zero damage during the last three major hurricanes, offering exceptional peace of mind and making it a rare find for island living. The real value extends beyond the unit itself. For just $150 per year HOA fee, owners enjoy access to 8 community boat slips and a direct Gulf access boat ramp—perfect for boating and fishing enthusiasts. Just down the street, you'll also find a marina, park, pickleball and tennis courts, baseball fields, and a community pool, creating endless opportunities for recreation and relaxation. Don't miss this rare opportunity to own an affordable piece of paradise and enjoy the island lifestyle you've always dreamed of! 5725 Genesee Parkway Unit 10, Bokeelia
$225,000 Your Worry-Free Island Escape: Pristine Condo with Low Maintenance: The low monthly fee covers the heavy lifting of home ownership, providing pest control, insurance, and lawn care—allowing for a "lock and leave" lifestyle or just relaxing on Pine Island Time. Step into the heart of THE 'Island Center' with this exceptional condo near the Phillips Park, Tennis Courts, Library and Community Pool; as well as some of the Best Local Eats! Since Pine Island is long and spread out, being at "the Center" is a major perk and perfectly positioned for those who crave the "Old Florida" lifestyle while still being just minutes from local art galleries, fresh seafood markets, and the charming shops of Matlacha, and surrounding resort islands. Whether you're looking for a seasonal retreat, a high-potential rental, or a permanent slice of paradise, this unit offers the ultimate island home base. This condo's Flexible Layout features 2BR/2BA, attached garage, with plenty of natural light and coastal breezes under cathedral ceilings. The front dining room serves as a perfect "flex space" for a home office or den and with its Spacious & Bright flow through the kitchen and Florida Great Room; ceramic tile throughout. Enjoy peaceful front and backyard views, a screened-in lanai with views to a fenced-in, private backyard surrounded by shade trees and beautifully landscaped grounds that feel like a private sanctuary. This condo sounds like the quintessential "Old Florida" retreat, especially for someone who wants the perks of island living without the typical maintenance headaches; and with a quiet neighborhood setting, you'll have the perfect balance of convenience and tranquility while enjoying the best at an affordable price. Don't miss out on this incredible opportunity to live on an island in Paradise. 2 Beds ⋅ 2 Baths ⋅ 2026016275 MLS Your Worry-Free Island Escape: Pristine Condo with Low Maintenance: The low monthly fee covers the heavy lifting of home ownership, providing pest control, insurance, and lawn care—allowing for a "lock and leave" lifestyle or just relaxing on Pine Island Time. Step into the heart of THE 'Island Center' with this exceptional condo near the Phillips Park, Tennis Courts, Library and Community Pool; as well as some of the Best Local Eats! Since Pine Island is long and spread out, being at "the Center" is a major perk and perfectly positioned for those who crave the "Old Florida" lifestyle while still being just minutes from local art galleries, fresh seafood markets, and the charming shops of Matlacha, and surrounding resort islands. Whether you're looking for a seasonal retreat, a high-potential rental, or a permanent slice of paradise, this unit offers the ultimate island home base. This condo's Flexible Layout features 2BR/2BA, attached garage, with plenty of natural light and coastal breezes under cathedral ceilings. The front dining room serves as a perfect "flex space" for a home office or den and with its Spacious & Bright flow through the kitchen and Florida Great Room; ceramic tile throughout. Enjoy peaceful front and backyard views, a screened-in lanai with views to a fenced-in, private backyard surrounded by shade trees and beautifully landscaped grounds that feel like a private sanctuary. This condo sounds like the quintessential "Old Florida" retreat, especially for someone who wants the perks of island living without the typical maintenance headaches; and with a quiet neighborhood setting, you'll have the perfect balance of convenience and tranquility while enjoying the best at an affordable price. Don't miss out on this incredible opportunity to live on an island in Paradise. 5520 Phillips Street, Bokeelia
$449,000 If you are searching for a waterfront getaway, a seasonal snowbird retreat or an incoming-producing investment property, this condo offers exceptional versatility. Bright, inviting interiors and an open layout create a relaxed coastal atmosphere, while the seamless connection to the lanais encourages effortless indoor-outdoor enjoyment. Enjoy beautiful water views,move in ready and low-maintenance lifestyle in a highly desirable location. two pools and spas,clubhouse, tennis and pickle ball courts.There are three plus bedrooms and 3 1/2 baths. Plenty of storage for your boats-bikes etc. There is a boat launch to take you to the best fishing and island hopping.This condo could be a good rental investment or just enjoy for yourself. Take advantage of this property. 3 Beds ⋅ 6 Baths ⋅ 2026009356 MLS If you are searching for a waterfront getaway, a seasonal snowbird retreat or an incoming-producing investment property, this condo offers exceptional versatility. Bright, inviting interiors and an open layout create a relaxed coastal atmosphere, while the seamless connection to the lanais encourages effortless indoor-outdoor enjoyment. Enjoy beautiful water views,move in ready and low-maintenance lifestyle in a highly desirable location. two pools and spas,clubhouse, tennis and pickle ball courts.There are three plus bedrooms and 3 1/2 baths. Plenty of storage for your boats-bikes etc. There is a boat launch to take you to the best fishing and island hopping.This condo could be a good rental investment or just enjoy for yourself. Take advantage of this property. 5411 Blue Crab Circle Unit 4, Bokeelia
$450,000 Experience effortless coastal living in this modern and sleek 2-bedroom, 2-bath turnkey penthouse end-unit condo, ideally located in the highly desirable Four Winds Marina community. Soaring vaulted ceilings enhance the open, light-filled layout, while impact-resistant doors and windows provide peace of mind. Enjoy tile and luxury vinyl plank flooring throughout, complemented by beautifully designed, contemporary kitchens and bathrooms. The spacious wraparound screened lanai offers coveted southeast exposure—perfect for relaxing in afternoon shade while still capturing glimpses of stunning sunsets and shimmering water reflections. Just steps away, you’ll find the popular Lazy Flamingo restaurant and world-class fishing charters. Also located a short distance away is Jug Creek Marina & Fish House, where you can enjoy more tasty island food and cath the ferry for amazing tours and adventures. Surrounded by abundant wildlife including dolphins, manatees, wild birds, and schools of fish, this prime waterfront location provides quick boating access to Sanibel, Pine Island, Captiva, Boca Grande, Cayo Costa, and beyond. The solid, secure building features concrete pillars and walls, a durable metal roof installed in 2022, and is complemented by a beautifully updated community with new brick paver driveways, ample parking, and fresh landscaping throughout. Schedule your private showing today and start living the waterfront lifestyle you’ve been dreaming of. 2 Beds ⋅ 2 Baths ⋅ 2026004594 MLS Experience effortless coastal living in this modern and sleek 2-bedroom, 2-bath turnkey penthouse end-unit condo, ideally located in the highly desirable Four Winds Marina community. Soaring vaulted ceilings enhance the open, light-filled layout, while impact-resistant doors and windows provide peace of mind. Enjoy tile and luxury vinyl plank flooring throughout, complemented by beautifully designed, contemporary kitchens and bathrooms. The spacious wraparound screened lanai offers coveted southeast exposure—perfect for relaxing in afternoon shade while still capturing glimpses of stunning sunsets and shimmering water reflections. Just steps away, you’ll find the popular Lazy Flamingo restaurant and world-class fishing charters. Also located a short distance away is Jug Creek Marina & Fish House, where you can enjoy more tasty island food and cath the ferry for amazing tours and adventures. Surrounded by abundant wildlife including dolphins, manatees, wild birds, and schools of fish, this prime waterfront location provides quick boating access to Sanibel, Pine Island, Captiva, Boca Grande, Cayo Costa, and beyond. The solid, secure building features concrete pillars and walls, a durable metal roof installed in 2022, and is complemented by a beautifully updated community with new brick paver driveways, ample parking, and fresh landscaping throughout. Schedule your private showing today and start living the waterfront lifestyle you’ve been dreaming of. 16641 Stringfellow Road Unit 506, Bokeelia
$328,000 This is one of Pine Islands most unique, well-maintained, sought after developments. As you drive up and over the bridge into Blue Crab Key, the peaceful, close-knit feel of this tropical island community is immediately apparent. Enjoy quiet evenings relaxing on your lanai or front deck. Spend time socializing at one of the two pools areas with whirlpool spas, or the pickleball courts. This unit for sale offers a gorgeous view overlooking the mangroves and canal. With Matlacha Pass in the background you’re just minutes from some of the best fishing in the world as you head out to Charlotte Harbor. The lanai is fully glassed in for comfortable air-conditioning year-round. The high-impact windows and doors are a wonderful bonus. Inside you have two spacious bedrooms, with en-suite bathrooms, and an open floor plan. Another standout feature is the extended storage unit on the first level, perfect for kayaks, fishing poles, bikes, boat equipment, and more, with all shelving included. The excellent amenities include two pools, two whirlpools, pickleball as well as tennis courts, and a putting green, clubhouse and an observation deck. Boaters have everything you need with boat and kayak storage, a community boat ramp, and docks available on a first-come, first-serve basis. With the canal and docks right outside the back door you can easily view your boat and enjoy access for loading, unloading, and rinsing after a day on the water. To top it all off, the HOA fees are the lowest on the island! Blue Crab Key is centrally located to make it much faster and easier to get on and off island. This home is being sold furnished, making it truly move-in ready. 2 Beds ⋅ 3 Baths ⋅ 2025026107 MLS This is one of Pine Islands most unique, well-maintained, sought after developments. As you drive up and over the bridge into Blue Crab Key, the peaceful, close-knit feel of this tropical island community is immediately apparent. Enjoy quiet evenings relaxing on your lanai or front deck. Spend time socializing at one of the two pools areas with whirlpool spas, or the pickleball courts. This unit for sale offers a gorgeous view overlooking the mangroves and canal. With Matlacha Pass in the background you’re just minutes from some of the best fishing in the world as you head out to Charlotte Harbor. The lanai is fully glassed in for comfortable air-conditioning year-round. The high-impact windows and doors are a wonderful bonus. Inside you have two spacious bedrooms, with en-suite bathrooms, and an open floor plan. Another standout feature is the extended storage unit on the first level, perfect for kayaks, fishing poles, bikes, boat equipment, and more, with all shelving included. The excellent amenities include two pools, two whirlpools, pickleball as well as tennis courts, and a putting green, clubhouse and an observation deck. Boaters have everything you need with boat and kayak storage, a community boat ramp, and docks available on a first-come, first-serve basis. With the canal and docks right outside the back door you can easily view your boat and enjoy access for loading, unloading, and rinsing after a day on the water. To top it all off, the HOA fees are the lowest on the island! Blue Crab Key is centrally located to make it much faster and easier to get on and off island. This home is being sold furnished, making it truly move-in ready. 5301 Blue Crab Circle Unit 4, Bokeelia