Bokeelia Homes under $500,000

Bokeelia Homes under $500,000

Welcome to Bokeelia, a hidden gem nestled on the northern tip of Pine Island in Lee County, Florida. This picturesque community offers a unique blend of serene island living and vibrant local culture, making it an ideal place for those seeking tranquility without sacrificing convenience. With its stunning waterfront views, lush landscapes, and friendly atmosphere, Bokeelia is perfect for families, retirees, and anyone looking to embrace the Florida lifestyle.

One of the most appealing aspects of Bokeelia is its diverse real estate market, particularly for those seeking homes under $500,000. Here, you’ll find charming single-family homes, cozy cottages, and spacious properties that provide ample space for relaxation and recreation. Many of these homes boast beautiful gardens, proximity to the water, and easy access to local amenities, ensuring you can enjoy the best of island living without breaking the bank.

Bokeelia is not just about beautiful homes; it’s also a haven for outdoor enthusiasts. With numerous parks, nature trails, and opportunities for boating, fishing, and kayaking, you’ll find plenty of ways to enjoy the stunning natural surroundings. The community also hosts various events throughout the year, fostering a strong sense of camaraderie among residents.

Whether you’re looking for a seasonal retreat or a permanent residence, Bokeelia offers an inviting atmosphere and affordable housing options that make it a perfect choice for your next home. Come explore the charm of this delightful island community and discover the possibilities that await you in Bokeelia, Florida!

Newest Bokeelia Homes under $500,000

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
5486 Avenue E, Bokeelia
$299,000
4 Beds ⋅ 2 Baths ⋅ 2026040711 MLS
Island life, income potential, and a location that puts Bokeelia right outside your door. Check out this great opportunity to own a duplex on Pine Island! Tucked into the heart of “The Center”, this duplex offers the kind of laid-back Florida lifestyle people come to Pine Island looking for. Walk to local restaurants, shopping, the library, park, public pool, and nearby nature trails, then come home and enjoy the slower pace that makes island living so special. For Families, the school is just down the street! One side has been updated with a fresh, comfortable feel, while the other offers an opportunity to add your own style and create additional value. Whether you choose to live in one side and rent the other, keep both as income-producing residences, or create space for family and friends, the flexibility here is a big part of the appeal. Each unit offers a spacious layout and an oversized screened in patio in the back. This is the kind of place where mornings can start with a walk or bike ride, afternoons can be spent exploring the island, and dinner is just minutes away at a favorite local spot. Easygoing, convenient, and full of possibilities — this is Bokeelia living with options. Explore the great potential of this unique property today! Photos marked “enhanced” have been digitally optimized to show ideas for upgrades!)

5486 Avenue E, 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
10899 Russell Road, Bokeelia
$275,000
3 Beds ⋅ 2 Baths ⋅ 2026039878 MLS
Enjoy the laid-back Pine Island lifestyle in this 3-bedroom, 2-bath home situated on over half an acre in Bokeelia. The home offers an open great-room layout with vaulted ceilings, impact-resistant windows, and a newer roof. A separate attached living area with its own entrance and full bath provides additional flexibility for guests, extended family, a home office, or additional living space. Step outside to the large screened lanai overlooking a spacious backyard with mature landscaping and plenty of room for a pool, garden, boat, RV, or outdoor entertaining. With no HOA, you have the freedom to make the property your own. Located near the heart of Bokeelia, you're convenient to public boat ramps, the Bokeelia Fishing Pier, waterfront dining, and access to Pine Island Sound, Charlotte Harbor, and some of Southwest Florida's best boating and fishing. Property is being sold AS-IS. Potential short sale; sale price and terms are subject to third-party/lender approval.

10899 Russell Road, Bokeelia
10925 Russell Road, Bokeelia
$274,500
3 Beds ⋅ 3 Baths ⋅ 2026039973 MLS
Best value on Pine Island- Updated two story home. @ bedroom 2 bathrooms upstairs and a 1 bedroom 1 bathroom area on the first level. Excellent property for vacation or winter home. Even a possible AirBnB with two living areas. Updated home in the last year all permitted improvements. Close to all the parks and stores on Pine island. Beautiful Florida retreat!

10925 Russell Road, 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
11311 Stringfellow Road, Bokeelia
$189,000
3 Beds ⋅ 2 Baths ⋅ 2026037732 MLS
This 3-bedroom, 2-bath mobile home is a wonderful opportunity for a small family, retired couple, or anyone looking to enjoy the relaxed Pine Island lifestyle while owning a home of their own. Step into the fenced backyard oasis, where peace and privacy await. The patio and fire pit create the perfect setting for evening relaxation, entertaining friends, or simply unwinding after a day on the island. Conveniently located near Pine Island Center, you’ll be just minutes from the Pine Island Public Library, Pine Island Community Pool, Phillips Park, the new pickleball courts, shopping, and local restaurants. The island’s bike path is right across the street, making it easy to get out and enjoy the beautiful surroundings. For boating enthusiasts, some of Pine Island’s best marinas are only a few miles away in either direction, giving you easy access to everything the island has to offer. Priced to sell quickly, this is an opportunity you won’t want to miss! Come see why this could be the perfect place to call home and own your own little slice of paradise.

11311 Stringfellow Road, 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
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
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