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7443 Pomegranate Drive, Bokeelia
$355,000
2 Beds ⋅ 2 Baths ⋅ 2026040666 MLS
Peaceful Island Living in Pineland 7443 Pomegranate Drive • Bokeelia, Florida Looking for that Peaceful Easy Island Living? This is it! Tucked away in the charming Pineland area of Pine Island, this beautifully remodeled 2-bedroom, 2-bath island cottage offers the relaxed Old Florida lifestyle people come here looking for. Step inside and you’ll find an updated, move-in-ready home with impact-rated windows and sliders, newer flooring, updated appliances, a 2023 roof and 2020 A/C. Cathedral ceilings add to the open, airy feeling, while the surrounding tropical landscaping creates your own little island retreat. Zillow One of the best parts is the location. You can enjoy the golf-cart-friendly Pineland neighborhood and be close to Tarpon Lodge and nearby marina/water-taxi access for boating and island adventures. Head out for the day to Cayo Costa, Cabbage key or Captiva Island to explore the surrounding islands, or simply come home, relax and enjoy the quiet side of Pine Island. The bike Path will take you from St James City to the Bokeelia Pier. No HOA. Room for your boat or RV on the property with no deed restriction. Island living without all the fuss. Come discover why people fall in love with Pine Island.

7443 Pomegranate Drive, Bokeelia

5191 Marina Drive, Bokeelia
$1,075,000
2 Beds ⋅ 2 Baths ⋅ 2026040340 MLS
Bokeelia Experience the best of waterfront island living at 5161 Marina Drive, an exceptional bayfront retreat in Bokeelia offering expansive water views, outstanding boating access, and a front-row seat to the natural beauty of Southwest Florida. With approximately 150 feet of waterfront, this property offers a setting that is increasingly difficult to find. The outdoor living space is truly the centerpiece. Enjoy a saltwater pool and Jacuzzi overlooking the bay, along with a wraparound dock, two davits/boat lift setup, approximately 90 feet of mangrove boardwalk, and your own private beach and shoreline launch area—an incredibly unique feature providing convenient access for kayaks, paddleboards, jet skis and other watercraft directly from the property. The waterfront tiki hut, rebuilt in 2024, creates the perfect gathering space with an outdoor kitchen, bar area, TV, refrigerator and bathroom. An outdoor shower adds even more convenience after a day spent on the water. From the backyard, dock and pool area, enjoy watching boats pass by and keep an eye out for some of Southwest Florida’s incredible marine life, including dolphins and manatees. The combination of waterfront recreation, tropical surroundings and wildlife viewing also gives the property excellent appeal for those seeking a memorable vacation-rental experience. Numerous recent improvements include a new roof in 2025, new septic system in 2026, new flooring and interior paint in 2025, new front staircase, updated landscaping and plantings, along with an elevator for added convenience. Bamboo fencing and tropical landscaping provide additional privacy, while grapefruit, banana, lemon, orange and mango trees add to the island atmosphere. Whether you’re boating, fishing, kayaking, entertaining poolside, launching directly from your private shoreline or simply relaxing and watching life on the bay, 5161 Marina Drive delivers the kind of waterfront lifestyle people come to Bokeelia to experience.

5191 Marina Drive, Bokeelia

5489 Meadowlark Lane, Bokeelia
$149,000
1 Beds ⋅ 1 Baths ⋅ 2026040203 MLS
Tucked on Meadowlark Lane in Bokeelia, Pine Island, Florida, this +/-0.19 acre property offers an accessible entry point into one of Southwest Florida's more laid-back coastal communities. Lee County Property Appraiser records show the home was built in 1972 on a lot of approximately 8,407 square feet, giving a new owner a manageable, low-maintenance parcel rather than a large yard to keep up. The street itself sees no through traffic, which keeps the immediate area quiet, and the property is close to the center of Pine Island, putting daily errands, local dining, and the town's marinas and waterfront within easy reach rather than a long drive away. Bokeelia sits at the tip of Pine Island, an 18-mile-long island in Charlotte Harbor known for its mangrove shoreline, working marinas, and a slower pace than the more built-up barrier islands nearby. The Greater Pine Island Chamber of Commerce describes the island as a place to enjoy fishing, birdwatching, local art, and waterfront dining, with year-round community events like the Island Market and MangoMania Festival. For anyone who fishes or boats, the Bokeelia Fishing Pier and Boat Ramp is a short drive from the property. The pier has drawn anglers for more than a century targeting snapper, redfish, and snook, and the adjacent boat ramp provides access to Charlotte Harbor and the waters around Cayo Costa State Park. That kind of nearby water access is a draw for both a primary homeowner or a rental tenant looking for a Pine Island base. Beyond the home itself, the property includes a shed or shop structure at the rear of the lot. This kind of bonus building adds real flexibility, whether it is used as a workshop, an art studio, or simply extra storage for boating and fishing gear, tools, or a small business. For a buyer who wants space to work with their hands or pursue a hobby without needing a large parcel, that separate structure is a meaningful asset. The combination of a small, manageable lot, a quiet no-through-traffic location, proximity to town, and a bonus shop building makes this a practical option for two different kinds of buyers. A first-time homebuyer gets an affordable way into homeownership on Pine Island without taking on a large property to maintain. An investor gets a rental-ready asset in a market where vacation and seasonal rental demand on Pine Island stays consistent thanks to the area's fishing, boating, and laid-back island appeal. Bokeelia's location also puts it within a reasonable drive of the broader Fort Myers and Cape Coral area, so residents and renters are not cut off from larger shopping, dining, and services while still enjoying the quieter island setting day to day.

5489 Meadowlark Lane, Bokeelia

15274 Martinique Way, Bokeelia
$1,000,000
4 Beds ⋅ 3 Baths ⋅ 2026039109 MLS
Welcome to your own private tropical oasis in beautiful Bokeelia! Set on 1.5 acres, this unique estate home offers the space, privacy, and laid-back island lifestyle that makes Pine Island so special. The home sits high in Flood Zone X and offers an impressive 2,640 square feet of custom-designed living space on the upper level, plus an additional 2,640 square feet of versatile, flexible living space, garage, and storage on the ground level— for a total of 5,280 square feet. With this much room, the property offers incredible flexibility for multi-generational living, hobbies, storage, entertaining, or creating your own personal space downstairs. If you love being on the water, you’ll appreciate the location just moments from the local boat ramp. From here, you’re only a short, scenic boat ride from some of Southwest Florida’s most beautiful destinations, including Cayo Costa, Captiva, and Boca Grande. Spend the day fishing, exploring the islands, or enjoying the Gulf, then come home to your own private retreat. The grounds are truly something special. The property is surrounded by a mature, organic edible landscape that feels more like a private botanical garden than a typical yard. You’ll find an incredible variety of tropical fruits, herbs, and edible plants, including bananas, turmeric, ginger, mangoes, moringa, papayas, persimmons, avocado, cherimoya, neem, pineapples, guava, blackberries, figs, elderberries, pomegranate, curry leaf, cherries, peaches, sapote, sugar apple, and so much more. It’s a rare opportunity to enjoy your own abundant tropical food garden right outside your door. Adding even more value, the property is not located in a flood zone, which can be a major advantage for peace of mind and insurance costs. With its elevated setting, expansive living and flex space, 1.5 acres of privacy, easy access to the water, and one-of-a-kind tropical landscape, this Bokeelia property offers a lifestyle that is hard to duplicate. If you’ve been looking for a place where you can spread out, enjoy the outdoors, get on the water whenever you want, and truly embrace island living, this one deserves a closer look.

15274 Martinique Way, Bokeelia

5318 Serenity Cove, Bokeelia
$685,000
3 Beds ⋅ 3 Baths ⋅ 226032669 MLS
Seller is offering $15,000 in seller concessions. Set on a quiet private road in Bokeelia's Serenity Cove, this two-story waterfront pool home offers direct Gulf access with no bridges, putting Pine Island Sound, Charlotte Harbor, and the Gulf a short boat ride away. The dock includes a boat lift with canopy, and a shared boat ramp on the east side of the property makes launching easy. The screened, heated pool was recently resurfaced and sits at the front of the home next to a long covered patio. That layout leaves the canal side open for entertaining, with a shaded patio under the upper deck and a built-in brick grill near the water. The home has Hardie board siding, a metal roof installed in 2024, and impact windows. There is plenty of parking in front for trucks, trailers, and guests, and there is no HOA. Stairs lead up to a covered entry deck and the main living level, which has luxury vinyl plank flooring throughout the open kitchen, living, and dining areas. The kitchen features white shaker cabinets, butcher-block countertops, a stone mosaic backsplash, stainless steel appliances, and a large center island. A sliding glass door opens to a screened porch overlooking the canal. The primary suite is large and has a private bath. Two additional bedrooms share a full guest bath. The fully enclosed ground level has tile floors and beadboard wainscoting. It includes a large family room that opens to the pool area, an oversized butcher-block island with bar seating, a home gym, a game room, a full bath, and an unfinished workshop. Mini-split systems cool the ground level, and central AC serves the upstairs.

5318 Serenity Cove, Bokeelia

16340 Buccaneer Street, Bokeelia
$1,225,000
2 Beds ⋅ 2 Baths ⋅ 2026037901 MLS
A BOATER'S DREAM WITH DEEP-WATER SAILBOAT ACCESS, A 30K-POUND LIFT, AND BIG-WATER VIEWS! Completed in 2026 - With views of intersecting canals, Jug Creek, and a deep-water channel, this extensively renovated island residence offers exceptional privacy, boating, and quick access to Charlotte Harbor. Featuring a brand-new 100-foot flow-through dock with a reinforced composite substructure, all-new pilings, freshwater, dual 50-amp shore power, a custom 30K-pound boat lift, and dockage for 40+ foot boat. A 20-foot covered Tiki area at the end of the dock creates an incredible setting for waterfront entertaining, weekend barbecues, or relaxing beside your yacht. Completely rebuilt from the studs, this residence represents one of the island's most extensive whole-home renovations. Offered furnished, it offers more features and quality than most newly completed luxury homes. A dramatic wall of PGT impact windows immediately captures panoramic views of the waterway and boats passing by. New luxury vinyl plank flooring flows throughout the interior, while custom millwork brings warmth and continuity to every room. Shiplap, Synergy cypress accents, custom-crafted room dividers, and an impressive 80-inch fireplace create a refined yet comfortable coastal atmosphere. An approximately 122-inch picture window frames the water and surrounding palms while filling the living areas with natural light. The new kitchen features Samsung Bespoke appliances, custom pull-out cabinetry, Silestone counters, and a walk-in pantry. Designed for everyday living and entertaining. The Master suite features a large walk-in closet with California Closets shelving and a spa-inspired bathroom with a wood ceiling, tilework, and oversized walk-in shower. The generously sized 2nd bedroom can serve as a junior master. The finished garage is climate-controlled and can serve as a 3rd bedroom. Outdoor living continues with a 5-seat HotSpring Envoy saltwater spa. The completely redesigned grounds include custom paver work, retaining walls, new fencing, river rock landscaping, professional regrading, and athletic-field-quality artificial turf installed by Southern Turf. Improvements include a premium Coastal Max aluminum metal roof representing an investment of more than $100,000. Additional upgrades include a new oversized Rheem 3.5-ton HVAC system w/ new ductwork, a HALO whole-home air purification system, a KIND triple-stage whole-home water filtration system, & new plumbing & electrical systems. PGT hurricane impact windows, doors, motorized roll-down shutters, new hurricane/insulated garage door, smart home tech, Lutron lighting, backlit dimmers, 3-zone Sonos audio, & Starlink internet. AI full-property security system. From your private dock, explore the renowned fishing grounds surrounding Boca Grande, cruise to the Gulf of Mexico and nearby barrier islands, or the Florida Keys. Bring your boat, unpack your bags, and start living Island Life!

16340 Buccaneer Street, Bokeelia

7680 Helen Road, Bokeelia
$84,900
2 Beds ⋅ 2 Baths ⋅ 2026037800 MLS
REDUCED! TLC NEEDED for this 1981 manufactured home located in sought-after September Estates 55+ Community on Pine Island. This home as 2 bedrooms and 2 full baths and lives larger than it looks. It did sustain damage to the carport and open lanai but did not flood. It has a very large, enclosed lanai great for outdoor living & entertaining. The other side has a very large open lanai. It did have a canopy roof but was lost during the hurricane. The carport roof was lost as well. All roofing for the home and enclosed lanai remains intact. The inside is dated and does need some floor work for soft spots. It has been a successful annual rental for many years. All information deemed reliable, but not guaranteed, buyers to do due diligence.

7680 Helen Road, Bokeelia

7660 Grande Pine Road, Bokeelia
$449,000
3 Beds ⋅ 3 Baths ⋅ 2026037371 MLS
Paradise awaits in this spacious, beautifully maintained pool home nestled on a private .344-acre lot in desirable Alden Pines, Bokeelia. Built in 1999 with concrete stucco CBS construction, this move-in-ready residence offers 1,981 sq. ft. of living space and 2,422 sq. ft. total area, with an inviting open-concept design, cathedral ceilings, and a desirable split-bedroom floor plan. Enter through the screened porch and double-door entry into a bright, spacious living and dining area. Triple sliding glass doors seamlessly open to the expansive screened lanai and pool, creating the ideal setting for entertaining or relaxing year-round. The generous eat-in kitchen features updated granite countertops, a double sink, abundant cabinetry, and a walk-in pantry with extensive shelving. French doors provide direct access to the lanai and pool, making outdoor dining and entertaining effortless. The private primary suite is a true retreat, complete with French doors opening to the lanai and pool, his-and-hers walk-in closets, and a spacious ensuite bath. The primary bathroom offers a large walk-in shower, dual-sink vanity, window seat, and separate toilet closet. Two additional bedrooms feature large closets and share a full guest bath with a convenient pocket door that can close off the bathroom for added guest privacy. Additional interior storage includes a hallway closet and linen closet. Outdoor living is where this home truly shines. The expansive screened lanai includes a half bath and storage closet, while the large, private backyard borders a peaceful mango orchard. Enjoy the Florida lifestyle with plenty of room to relax, entertain, and enjoy the pool. Additional features include a new metal roof installed in 2023 with Ultra Rib panels and a Four Point Inspection Certificate, storm security shutters, tinted windows throughout, tile flooring in the main living areas, laminate flooring in the primary bedroom, PEX plumbing, and an in-wall pest control system. The oversized two-car garage includes attic storage, a work area, and laundry sink. The separate laundry room offers two spacious storage closets. The pool was resurfaced in 2014. The home is 9' elevation certified and has never flooded. A voluntary HOA provides added flexibility. Enjoy easy access to Pineland Marina and Tarpon Lodge, with dining, boating, and waterfront recreation just a walk or short golf-cart ride away. The newly renovated golf course and clubhouse are scheduled to reopen in late Fall 2026, adding even more appeal to this already exceptional location. This rare turnkey pool home offers the perfect combination of privacy, comfort, outdoor living, and island lifestyle. Come discover your own piece of Florida paradise in Bokeelia!

7660 Grande Pine Road, Bokeelia

5711 Linden Lane, Bokeelia
$870,000
3 Beds ⋅ 2 Baths ⋅ 2026036603 MLS
Welcome to 5711 Linden Lane, a spacious and beautifully upgraded Pine Island home offering the perfect blend of comfort, convenience, and island lifestyle. Ideally located in the center of Pine Island, this two-story property features a private elevator with access from the ground level to the top-floor primary suite. Inside, you'll find a tastefully remodeled kitchen, a brand-new primary bathroom, and a thoughtfully designed layout with generous living space throughout. The private top-level primary suite creates a relaxing retreat, while the elevator adds everyday convenience rarely found in homes like this. Outside, enjoy wraparound composite decking, beautiful landscaping, and a full lawn irrigation system. The property also offers a covered concrete RV/camper area with 50-amp service and water hookups, plus plenty of room for boats, trailers, and recreational toys. Additional features include a heated and cooled garage and access to the community marina and boat ramp, making it easy to enjoy everything Pine Island is known for, from boating and fishing to the laid-back coastal lifestyle. 5711 Linden Lane combines extensive upgrades, exceptional storage, boating access, and a highly desirable central Pine Island location in one truly versatile property.

5711 Linden Lane, Bokeelia

16385 Boyce Drive Unit 301, Bokeelia
$349,900
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

5831 Samoa Drive, Bokeelia
$335,000
3 Beds ⋅ 2 Baths ⋅ 2026031767 MLS
Discover the charm of Island living in this beautifully maintained 3-bedroom, 2-bath home nestled in the heart of Bokeelia! Offering 1,460 square feet of comfortable living space, 2 car garage, and recent updates, this move-in-ready home combines peace of mind with the relaxed Florida lifestyle you've been dreaming of. The backyard is a gardener's delight, featuring beautifully landscaped grounds with lots of mature fruit trees, 6 banana trees (3 different types), 1 mango, 3 papaya, 1 lemon, 2 sea grapes, 1 shampoo ginger, and a sugar cane, thriving herb gardens and colorful tropical plantings that create peaceful setting to relax, entertain or simply enjoy Florida's natural beauty. There is a lush perimeter of mature shrubs, landscaping that provides natural privacy and enhances the homes' tranquil atmosphere. Inside you'll appreciate the comfortable floor plan and the peace of mind that comes with major improvements, NEW ROOF (2023) ALL NEW PLUMBING THROUGHOUT THE HOME (2025), NEW WATER HEATER (2025), Even more reassuring the home has never flooded during any of the recent hurricanes. Conveniently located within walking distance of the community pool, pickleball courts, shopping, the local museum, and several popular restaurants, you'll love having everyday amenities just minutes from your front door. A short drive brings you to the public boat ramp, offering easy access to world-class fishing, boating, kayaking and all the waters surrounding beautiful Pine Island. Built in 1994 and lovingly care for this home offers the perfect blend of comfort, convenience and the laid-back charm that makes Bokeelia such a desirable place to call home. Whether you're looking for a full-time residence, a seasonal retreat, or an investment opportunity this property is ready to welcome its next owner.

5831 Samoa Drive, Bokeelia

5888 Sea Bass Road, Bokeelia
$288,000
3 Beds ⋅ 2 Baths ⋅ 2026032822 MLS
Back on the market at 'no fault of Seller' -- Buyer's financing fell through. Experience the quintessential Pine Island lifestyle in this beautifully appointed retreat, where tropical serenity & phenomenal flora & fauna meets modern accessibility. This charming island home is ideally positioned moments from local marinas, dining, shopping, and the island's iconic scenic bike path. The upper level radiates warmth, featuring a sun-drenched living area and two comfortable bedrooms. The kitchen serves as a focal point, elevated by exquisite Portuguese porcelain tile countertops and a matching backsplash. For relaxation, the screened lanai offers a seamless transition to the outdoors to unwind, overlooking peaceful views of lush surroundings; perfect for enjoying your morning coffee or evening cocktails. The lower level provides exceptional flexibility with a private-entrance guest suite, including a third bedroom, half bath, and expansive storage—an ideal setup for an art studio or workshop. With a new roof and water heater (2023), a fully fenced yard, and verdant mature landscaping & fruit trees on two lots, this home is a turnkey slice of paradise. Don’t wait---paradise is calling!!

5888 Sea Bass Road, Bokeelia

12303 Cristi Way, Bokeelia
$975,000
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

5419 Avenue E, Bokeelia
$425,000
3 Beds ⋅ 2 Baths ⋅ 2026032008 MLS
Welcome to 5419 Avenue E, Bokeelia, FL, where island living meets peace of mind. The separately strapped lot to the right (5431 Avenue E) is included in the sale, making it a total of .7 acres. This beautifully updated home offers plenty of room to spread out, entertain, or simply enjoy the tropical surroundings. Mature trees and lush landscaping create a private setting that's hard to find. Inside, you'll find a bright, open floor plan featuring a stunning remodeled kitchen with quartz countertops, a large center island, custom cabinetry, stainless steel appliances, and designer finishes throughout. The spacious living areas are filled with natural light, while the updated bathrooms and stylish flooring make this home truly move-in ready. The generously sized bedrooms provide comfortable accommodations, and the flexible floor plan offers space for guests, a home office, or hobbies. Large windows frame beautiful views of the expansive yard, creating a seamless connection between indoor and outdoor living. Step outside to your own private backyard retreat featuring a sparkling swimming pool and an abundance of green space. The oversized lot provides endless possibilities for gardening, RV or boat parking, additional storage, or future expansion. With Pine Island's world-class fishing, boating, and waterfront restaurants just minutes away, every day feels like a vacation. For added confidence, this home is equipped with impact-resistant windows, a new roof installed in 2020, and experienced no hurricane damage or flooding, offering buyers exceptional peace of mind. Whether you're looking for a full-time residence, seasonal getaway, or investment opportunity, 5419 Avenue E delivers the charm of Old Florida with modern updates in one of Pine Island's most desirable locations.

5419 Avenue E, Bokeelia

5748 Linden Lane, Bokeelia
$444,000
3 Beds ⋅ 2 Baths ⋅ 2026031812 MLS
Comfortable, updated and designed to make the most of the Pine Island lifestyle. This 3-bedroom, 2-bath island home has a bright, open feel with high ceilings, an updated kitchen and baths, and sliding doors that open the living area to a covered lanai and screened pool surrounded by tropical landscaping. The entire home features individually zoned heating and cooling, giving you the freedom to keep each space exactly as comfortable as you like while using energy where you need it. Even the two-car garage is finished, floored and climate controlled, making it a great flex space that can easily be returned to vehicle use and perfect for an electric vehicle. One of the perks for this home is the private community marina access which includes a boat ramp, boat slips for easy water access and a fish-cleaning station, making it easy to enjoy everything Pine Island has to offer on the water. The home can be sold fully furnished, and one full year of professional pool service is included, making it that much easier to settle in and simply enjoy the home from day one.

5748 Linden Lane, Bokeelia

5791 Porpoise Road, Bokeelia
$429,900
3 Beds ⋅ 2 Baths ⋅ 2026031193 MLS
Rarely does a property like this become available in Bokeelia's highly sought-after Fish Streets! Set on an impressive 0.88-acre homesite—nearly four times the size of a typical neighborhood lot—this exceptional property offers the privacy, space, and flexibility that are becoming increasingly rare on Pine Island. This well-maintained home features 4 bedrooms (or 3 bedrooms plus a den/home office) and 2 bathrooms, with a spacious, functional layout designed for comfortable everyday living. Accessibility has been thoughtfully incorporated, with wheelchair access throughout the main living areas and the primary bathroom, making the home suitable for a variety of lifestyles and abilities. Major improvements provide peace of mind, including a new roof (2023), new kitchen appliances (2023/2024), and a new water heater (2022). Original terrazzo floors extend throughout much of the home, offering the opportunity to restore a timeless Florida design element that perfectly complements the island lifestyle. Step outside and experience what truly sets this property apart. The oversized homesite offers endless possibilities, with ample space for a custom pool, a detached garage, a workshop, RV and boat storage, additional outbuildings, or lush tropical gardens. Mature, fruit-producing mango trees enhance the landscape, creating your own private island retreat. Best of all, there's no HOA, giving you the freedom to enjoy and improve your property without restrictive rules or fees. Large residential parcels of this size are increasingly difficult to find, making this property not only a wonderful place to call home but also an outstanding long-term investment with exceptional land value and appreciation potential. Conveniently located just minutes from marinas, public boat ramps, world-class fishing, waterfront restaurants, parks, and Pine Island's renowned natural beauty, this property offers the best of Southwest Florida living. Whether you're looking for a full-time residence, a seasonal escape, or an investment opportunity, this one-of-a-kind property delivers the space, privacy, and lifestyle today's buyers are seeking. Don't miss your opportunity to own one of the largest and most desirable home sites in the Fish Streets!

5791 Porpoise Road, Bokeelia

16191 Porto Bello Street, Bokeelia
$539,999
2 Beds ⋅ 2 Baths ⋅ 2026031016 MLS
Whether you're searching for a waterfront investment opportunity, a seasonal retreat, or your future retirement home, this charming concrete block residence offers exceptional value and coastal appeal. Recent upgrades include a newer air conditioning system and a durable metal roof, tankless water heater, boat lift canopy, full kitchen and bathroom updating, providing comfort and peace of mind for years to come. Inside, you'll find warm, character-filled walls and ceilings paired with crisp white finishes that create a bright, relaxed coastal atmosphere. This elegant, classic layout paired with Bahama shutters outside (and metal shutters for hurricane season) add both style and island-inspired charm. Step outdoors to enjoy the oversized screened lanai—an ideal space for entertaining, relaxing, or dining while taking in the waterfront setting. The fully fenced backyard features a wide double gate, making it easy to store a boat, trailer, golf cart, or other recreational equipment securely on the property, this space has plenty of room to accommodate a future pool or hotub. Boaters and anglers will especially appreciate the private boat lift with direct access to open water. Spend your days fishing, cruising, or exploring some of Southwest Florida's most sought-after destinations, including North Captiva Island, Boca Grande/Gasparilla Island, Cabbage Key, Cayo Costa, and the area's stunning Gulf beaches. Whether you're looking for a full-time residence, vacation getaway, or income-producing property, this waterfront gem offers the perfect combination of comfort, convenience, and the Florida lifestyle.

16191 Porto Bello Street, Bokeelia

15474 Pembrooke Road, Bokeelia
$325,000
2 Beds ⋅ 2 Baths ⋅ 2026030550 MLS
Now Offered at $325,000. Come experience the relaxing privacy of this beautiful pool home. Electric bill is under $30!!! This budget friendly home has fully paid off solar panels and a new shingled roof in 2023. This home has NEVER flooded and features hurricane impact windows on the front and sides of the house and sliding hurricane shutters on the back lanai for peace of mind. This beautifully maintained 1/2-acre property tucked away in a quiet area of Bokeelia on Pine Island. Inside and out, no detail was overlooked - enjoy a tankless on demand hot water heater, lush landscaping, and a sparkling pool set on a spacious fenced in (6' high fence) half acre lot. Unwind on the oversized lanai that spans the entire length of the home. Perfect for entertaining or simply soaking in the Florida lifestyle. The lanai is insulated and under truss...which means you could easily extend your indoor living to include the lanai area. Located just minutes from Pine Island's best restaurants, marinas, a community pool, pickleball courts, a local museum, and scenic bike trails, this property offers the perfect blend of privacy and island charm. Directions: Go North on Stringfellow Rd to Tropical Lane and turn right. Go about a 1/4 mile and turn right on Bahama Way. Go left on Howard Road. Turn right on Bimini Way and a quick left on Rockaway Dr. Go to the end of Rockaway and home is straight ahead. Please protect the tortoises in the area and drive with caution.

15474 Pembrooke Road, Bokeelia

15976 Bellflower Street, Bokeelia
$399,000
2 Beds ⋅ 2 Baths ⋅ 2026029179 MLS
Calling all boaters and fishermen. If you are looking for a home with easy access to the waters of Charlotte Harbor, Pine Island Sound and the Gulf of Mexico, then this unique Bokeelia home is just what the doctor ordered. This property is located on the north end of Pine Island, just a stones throw from Lavender Landing which is a Lee County owned marina and boat launch ramp. The home is older but very well built with CBS construction and a metal roof. The air conditioning is one year old. The interior has Terrazzo flooring in like new condition and tongue and groove cypress wall coverings There are two lanai's , one in the rear of the house and one in the front. The oversized lot is fenced with chain link fencing and there is a 10' X 20' storage building with water and electric. There is ample room for boat and RV parking.

15976 Bellflower Street, Bokeelia

5375 Serenity Cove, Bokeelia
$579,900
2 Beds ⋅ 2 Baths ⋅ 2026029862 MLS
PRICE IMPROVEMENT! Live the Pine Island Waterfront Lifestyle! Escape to this beautifully remodeled gulf-access stilt home where every upgrade is already done and every day feels like vacation. This turnkey retreat blends modern comfort with the laid-back charm of island living—just bring your clothes and a toothbrush and start enjoying the water. A Boater’s Paradise as you step outside onto your 2024 captain’s-walk dock, complete with a 13,000 lb. boat lift and a convenient fish cleaning station. Launch straight into Matlacha Pass with no bridges—just open water, world-class fishing, and endless boating adventures right from your backyard. Fresh, Modern, and Move-In Ready Inside, the home shines with a full 2023 remodel to include: New kitchen and appliances, new laminate flooring installed over an added ¾" plywood reinforcement for a solid floor. New roof, hot water heater, replumb, and updated electric panel. Clean, bright spaces designed for comfort and easy coastal Island living at its best! Sip your morning coffee with the breeze on the balcony, spend afternoons on the water, and unwind with sunset views only Pine Island can offer. Whether you’re seeking a seasonal escape or a full-time waterfront lifestyle, this home delivers effortless living in one of Southwest Florida’s most peaceful boating communities.

5375 Serenity Cove, Bokeelia

14281 Pacosin Court, Bokeelia
$459,000
3 Beds ⋅ 2 Baths ⋅ 2026029237 MLS
Elevated two Story piling home with over 1,700 sq ft under air and large 4 car enclosed garage on 1st level. Huge workshop area. Pine Island and Bokeelia offer small-town charm, art galleries, local markets, Tree Nurseries and some of Southwest Florida’s best fishing and boating. Whether you’re seeking a primary residence or vacation home. Home offers 3 bedrooms and 2 baths with large living area. Large back (screened) deck and outside grilling entertaining deck with stairs. Very private backyard with pathway around the golf course. Newer air, galvanized roof, most windows are hurricane proof, new hot water heater, new soffit and rain gutters. New flooring throughout the home. You can walk to Pineland Marina which offers full Marina Service, dine at the well-known Tarpon Lodge. Private setting. You will love this Island and community.

14281 Pacosin Court, Bokeelia

16276 Nautical Way Unit 1404, Bokeelia
$349,000
2 Beds ⋅ 2 Baths ⋅ 2026028844 MLS
Welcome to this beautifully maintained 2-bedroom, 2-bathroom end-unit condo in the sought-after Captains Harbor community. Sold turnkey furnished, this move-in-ready home is perfect as a full-time residence, seasonal getaway, or investment property. Step inside to find 18" tile flooring throughout, creating a clean, cohesive, and low-maintenance living space. The beautiful kitchen is a chef's delight, offering plenty of cabinet storage, gorgeous granite countertops, and a convenient breakfast bar — perfect for casual dining or entertaining. Both bedrooms are generously sized with walk-in closets, and an in-unit laundry room adds everyday convenience. As an end unit, you'll enjoy extra privacy and natural light, along with a quiet, tranquil setting overlooking the community's tennis and pickleball courts. Boaters will love the included dock with water and electric — just a short boat ride to Charlotte Harbor and the beautiful outer islands. A private two-car garage provides ample storage and parking. Community amenities include a sparkling pool and scenic walking paths, all just minutes from great restaurants and shopping. Don't miss this rare opportunity to own a turnkey, boater's-paradise condo in one of the area's most desirable communities!

16276 Nautical Way Unit 1404, Bokeelia

16600 Bocilla Island Club Drive Unit 35, Bokeelia
$455,000
2 Beds ⋅ 3 Baths ⋅ 2026028343 MLS
Experience SPECTACULAR WATER VIEWS from this beautifully positioned corner residence in the highly desirable Bocilla Island Club. This is widely considered the premier building in the community, offering panoramic water vistas from both levels and an abundance of natural light through additional side windows unique to this END UNIT. For boaters and anglers, this property is truly a rare find. Included is a PRIVATE BOAT SLIP with a 10,000-pound lift, accommodating boats up to 24 feet, providing quick access to Charlotte Harbor, Boca Grande Pass, Cayo Costa, North Captiva, world-class tarpon fishing, backwater flats, and some of Southwest Florida’s most pristine beaches. Ask almost any local fishing charter captain and they’ll tell you these are among the finest fishing grounds in all of Lee County. Anglers can achieve the coveted Grand Slam of fishing right in the vicinity. Abundant Snook, Redfish, Sea trout, and Tarpon are just a few of many prized local catches Relax on your screened lanai while watching dolphins, manatees, and boats cruise by, all with peaceful waterfront views as your backdrop. IMPACT WINDOWS AND DOORS provide peace of mind, while the floor plan offers a first-floor living area with a convenient half bath. Upstairs features a generous primary suite with breathtaking views, a walk-in closet, updated bath, private waterfront lanai, plus a guest bedroom with its own private bath. Additionally there is a convenient full sized laundry room. Additional highlights include a private storage room adjacent to the covered parking space. The oversized assigned under building parking space has plenty of room for both your vehicle and golf cart. Seasonal rentals are permitted, making this an outstanding investment opportunity with an established rental history. Bocilla Island Club offers a true resort lifestyle with two heated pools, tennis and pickleball courts, shuffleboard, beautifully landscaped grounds, scenic waterfront walking paths, a private fishing pier on Charlotte Harbor, and a kayak launch. Walk to nearby restaurants and Four Winds Marina, a full-service marina just minutes away. Flood insurance is included through the HOA. Whether you’re searching for the ultimate winter escape, year-round waterfront residence, or income-producing vacation property, this exceptional home combines breathtaking water views, unmatched fishing and boating, and the laid-back island lifestyle that makes Bokeelia so special.

16600 Bocilla Island Club Drive Unit 35, Bokeelia

8161 Moyer Lane, Bokeelia
$599,000
3 Beds ⋅ 3 Baths ⋅ 2026028932 MLS
Live the coastal dream in this charming 3-bedroom, 2.5-bathroom stilt home nestled along a peaceful canal with direct access to Jug Creek and Back Bay. With 120 feet of canal frontage, this property is a boater’s paradise, complete with a 10,000-pound boat lift and ample space to enjoy waterfront living. Upstairs, the open-concept layout is filled with natural light and offers scenic water views. The living and dining areas flow seamlessly into the kitchen, creating an inviting space for relaxation. Both bedrooms are well-sized, and the bathrooms are tastefully appointed. Downstairs, you’ll find a bonus bedroom and bathroom, ideal for guests or extra space. Plus, under the home is a covered area great for relaxing, entertaining, or parking, including a dedicated storage room perfect for tools, gear, and outdoor essentials. For anglers and boaters, the location is unbeatable! You’ll have access to world-class backcountry flats fishing, and it’s only a five-mile boat ride to Boca Grande Pass—home to the best Tarpon fishing in the world. Plus, enjoy manatees and dolphins as they visit you in the canal! Whether you’re looking for a weekend getaway or a full-time residence, this home offers the ultimate in laid-back, waterfront living with quick access to some of the best boating and fishing waters in the area. Don’t miss your chance to own a piece of paradise!

8161 Moyer Lane, Bokeelia

11940 Oakland Drive, Bokeelia
$898,000
3 Beds ⋅ 2 Baths ⋅ 2026027483 MLS
Stunning Waterfront Estate in Bokeelia. Experience exceptional waterfront living in this beautifully crafted freshwater-front estate offering approximately 2,129 square feet under air. Built with durability, efficiency, and comfort in mind. The home offers 3 spacious bedrooms, 2 elegantly appointed bathrooms, and a versatile bonus room ideal for a home office, fitness studio, media room, or additional guest accommodations. The thoughtfully designed primary suite serves as a private retreat, featuring separate custom closets, including a walk-in closet with wood ventilated shelving and additional custom cabinetry. The luxurious en-suite bath showcases dual quartz vanities, custom cabinetry, and a stunning solid quartz walk-in shower. Guest bedrooms are generously sized and offer ample closet storage. Designed for both everyday comfort and effortless entertaining, the home boasts two expansive covered porches with composite decking, complemented by paver patios on both sides of the property. The outdoor living area is truly resort-inspired, centered around a free-form Gunite saltwater pool with elegant travertine decking. A large structural cabana creates the perfect outdoor living room, while no-see-um screening surrounds the entire pool area for year-round enjoyment. Completing this private oasis is a Hot Spring saltwater spa. The chef-inspired kitchen is equally impressive, offering approximately 68 square feet of quartz countertop space with a matching quartz backsplash. Premium features include a farmhouse sink, built-in exhaust system, drawer microwave, Bosch induction range, Bosch dishwasher, and an LG refrigerator that produces four types of ice. Additional highlights include: • Oversized garage with an 18’ x 8’ door, ideal for larger vehicles, boats, and storage • Extended concrete driveway with abundant parking • 2023 Galvalume standing seam metal roof • Freshwater frontage offering privacy and serene water views A rare opportunity to enjoy luxury, sustainability, privacy, and waterfront living in the heart of beautiful Bokeelia. This exceptional property seamlessly blends high-performance construction with resort-style amenities, creating a home that is as efficient as it is beautiful.

11940 Oakland Drive, Bokeelia

7660 Bocilla Lane, Bokeelia
$4,799,000
6 Beds ⋅ 8 Baths ⋅ 2026025336 MLS
Luxury coastal estate overlooking Charlotte Harbor. Commanding one of the most spectacular waterfront settings in Southwest Florida, this extraordinary one-acre coastal estate offers an unrivaled lifestyle on the shores of Charlotte Harbor. In the charming island community of Bokeelia, this remarkable property is a boater's paradise with direct Gulf access and immediate proximity to world-renowned fishing waters. Encompassing 227 feet of pristine waterfrontage, the estate features a 300-foot private dock extending into Charlotte Harbor, as well as an additional deeded dock with a boatlift across the street. Together, these exceptional amenities provide rare flexibility for multiple vessels and effortless access to some of Florida's sought-after boating destinations. Completely rebuilt and masterfully renovated in 2021, the residence showcases timeless coastal architecture blended with modern luxury and cutting-edge technology. Walls of glass frame breathtaking panoramic harbor views that stretch for miles. The expansive great room serves as the heart of the home, featuring soaring wood-paneled ceilings, custom shiplap detailing, two striking Hellfire 360 fireplaces, and seamless indoor-outdoor living spaces designed for entertaining on any scale. A chef's kitchen of exceptional quality offers premium Thermador appliances, a gas range, custom cabinetry, a workstation sink, dedicated prep station with dual faucets and a beautifully appointed built-in bar, creating an ideal setting for intimate dinners and grand celebrations. Designed to accommodate family and guests in absolute comfort, the residence features six bedroom suites, each with its private en-suite bath. The luxurious primary suite is a private sanctuary, offering a gas fireplace, spa-inspired bath with freestanding soaking tub and oversized walk-in shower, a private office and an expansive waterfront balcony with sweeping views across Charlotte Harbor. Providing tremendous versatility, the property includes an air-conditioned space on the ground level, complete with a pool bath and kitchenette. This flexible area is ideally suited for a fitness studio, game room, home theater, entertaining lounge or additional guest accommodations. Resort-inspired outdoor living takes center stage with the pool and spa overlooking the harbor, a fully equipped tiki bar and lush tropical landscaping. Whether enjoying morning coffee as the sun rises over the water or gathering with friends for unforgettable sunsets, every outdoor space has been designed to maximize the property's extraordinary setting. Additional features include a gated entrance, private elevator, dual laundry rooms and whole-home smart automation with customizable controls on each level. Offering a combination of luxury, privacy, boating access and breathtaking natural beauty, this is a rare opportunity to own one of Charlotte Harbor's exceptional waterfront estates.

7660 Bocilla Lane, Bokeelia

7380 Barrancas Avenue, Bokeelia
$1,150,000
5 Beds ⋅ 3 Baths ⋅ 2026024358 MLS
Discover an exceptional waterfront investment opportunity in beautiful Bokeelia! Situated on an almost half-acre lot with direct Gulf access, this professionally decorated, turnkey vacation rental offers the perfect blend of island living, luxury, and income-producing potential. Nestled at the head of a deep-water canal, this stunning property provides quick access to Charlotte Harbor and the Gulf of Mexico, making it a dream destination for boaters, anglers, and nature lovers alike. Step outside and experience true island life, where manatees and dolphins are frequent visitors right in your backyard, creating an unforgettable experience for guests year-round. Designed to accommodate large groups, the home features 5 spacious bedrooms plus a bonus Murphy bed on the upstairs patio, comfortably sleeping 16+ guests. The expansive dock offers room for multiple boats, allowing easy access to world-class fishing, shelling, island hopping, and waterfront adventures. The outdoor living spaces are equally impressive, featuring a beautiful tiki hut, fire pit, kayaks, paddleboards, bicycles, and more—everything guests need to explore the surrounding waterways and embrace the laid-back island lifestyle. Whether you’re seeking a personal waterfront retreat, a highly successful vacation rental, or both, this turnkey property delivers. With breathtaking views, abundant wildlife, direct Gulf access, and proven rental appeal, this is a rare opportunity to own a slice of paradise. Schedule your private showing today and see why this remarkable island getaway continues to captivate guests and generate exceptional returns.

7380 Barrancas Avenue, Bokeelia

7257 Victory Road, Bokeelia
$439,000
2 Beds ⋅ 1 Baths ⋅ 2026023300 MLS
Welcome to your dream island retreat at 7257 Victory Rd in charming Bokeelia, FL! This beautifully remodeled 2-bedroom, 1-bathroom home is nestled in the serene enclave of Pineland, at the north end of Pine Island. Situated on a.42 acre lot, this home boasts modern upgrades including stainless steel appliances, tile floors, impact windows and doors, and a newer central A/C system. Enjoy peace of mind with updated electric panels and a durable metal roof. The spacious 24' x 38' garage with a newer shingle roof offers endless possibilities while the large screened porch invites you to unwind. Explore nearby marinas and boat ramps, or savor the delightful local dining. Perfect for nature lovers and boating enthusiasts! Don’t miss this gem! THIS. HOME HAS NOT FLOODED.

7257 Victory Road, Bokeelia