Pine Island Real Estate

Pine Island Real Estate

Welcome to Pine Island, a hidden gem nestled in the heart of Lee County, Florida. This enchanting island is renowned for its stunning natural beauty, vibrant wildlife, and laid-back island lifestyle. Surrounded by the sparkling waters of the Gulf of Mexico, Pine Island offers a unique blend of tranquility and adventure, making it the perfect destination for those seeking a serene escape or an active outdoor lifestyle.

As you explore Pine Island, you’ll discover charming waterfront homes, lush landscapes, and a strong sense of community. The island is home to a variety of residential options, from cozy cottages to luxurious waterfront estates, all designed to capture the essence of Florida living. With its rich history and artistic flair, Pine Island boasts an array of local galleries, shops, and dining establishments that showcase the best of island culture.

Outdoor enthusiasts will revel in the abundance of recreational activities available. Kayaking through the mangroves, fishing in the bountiful waters, or simply lounging on the pristine beaches are just a few of the ways to soak in the natural splendor. The island is also a haven for birdwatchers and nature lovers, with numerous parks and wildlife preserves that provide a glimpse into Florida’s diverse ecosystems.

Whether you are looking to invest in a vacation home, retire in paradise, or simply enjoy the idyllic lifestyle, Pine Island offers an unparalleled experience. Discover the charm and beauty of this coastal paradise, where every day feels like a vacation. Welcome home to Pine Island, where your dream lifestyle awaits!

Newest Listings in Pine Island

5476 Avenue D, Bokeelia
$239,000
3 Beds ⋅ 2 Baths ⋅ 226035741 MLS ⋅ Pine Island BLDG.
3 bedroom and 2 bath POOL HOME! Newer roof already installed. Pavers in the outdoor pool area and fenced yard. 1 car garage. Located close to the heart of Pine Island with easy access to Matlacha and Cape Coral. Very easy to show! Best value for money in all of Bokeelia currently. Modern PVC laminate floor throughout. Block home! Priced below appraisal value. Currently vacant! Good investment for Airbnb or long term rental or for home owners looking for the best value on the island! All appliances included.

5476 Avenue D, Bokeelia
10899 Russell Rd, Bokeelia
$275,000
3 Beds ⋅ 2 Baths ⋅ 2026039878 MLS ⋅ Pine Island BLDG.
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 Rd, Bokeelia
10925 Russell Rd, Bokeelia
$274,500
3 Beds ⋅ 3 Baths ⋅ 2026039973 MLS ⋅ Pine Island BLDG.
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 Rd, Bokeelia
2471 Avocado St, St. James City
$599,000
3 Beds ⋅ 2 Baths ⋅ 2026037929 MLS ⋅ Pine Island BLDG.
Experience owning a slice of paradise in this fully and tastefully remodeled home. Each room has been extensively updated to enjoy comfortable island living within its light filled spaces. The new kitchen and baths with walk-in showers are amazing. A metal roof was installed three years ago, and recently a water heater. This area of the island is golf cart friendly so you may ride it to local restaurants, bars, shopping or simply cruise around the entire neighborhood. Whether used as a full-time residence, seasonal, or an investment property, this home would easily fulfill your desires. Pine Island is a nature lover's paradise in addition to offering access to world class fishing. It has several county parks and a bike path almost the entire length of the island. Are you a baseball fan? Southwest Florida has many MLB spring training locations all within an easy drive. If you enjoy sun, salt, fishing, boating, baseball or great fresh seafood, Pine Island is the right place for you and your family. Start living on "Island Time."

2471 Avocado St, St. James City
12180-12212 Stringfellow Rd, Bokeelia
$300,000
226031653 MLS ⋅ Pine Island BLDG.
1.8 miles north of Pine Island Rd, across from 40+ acre Diocese of Venice church and just north of Pelletier Rickert Physical Therapy. Assemblage of ten 25'X155' lots, creating a whole block between Trout Rd and Kingfish Rd on Stringfellow Rd with rear access from Redfish Ln, totaling 0.89 acres with 250’ frontage on Stringfellow Rd in Bokeelia of Pine Island. Zoned C-1, which allows variety of Commercial as well as Residential Ues. STRAPS: 12212 Stringfellow Rd=16-44-22-02-00000.049B; 12208 Stringfellow Rd=16-44-22-02-00000.050B; 12204 Stringfellow Rd=16-44-22-02-00000.051B 12200 Stringfellow Rd=16-44-22-02-00000.052B; 12196 Stringfellow Rd=16-44-22-02-00000.053B; 12192 Stringfellow Rd=16-44-22-02-00000.054B; 12188 Stringfellow Rd=16-44-22-02-00000.055B; 12184 Stringfellow Rd=16-44-22-02-00000.056B; 12182 Stringfellow Rd=16-44-22-02-00000.057B; 12180 Stringfellow Rd=16-44-22-02-00000.058B;

12180-12212 Stringfellow Rd, Bokeelia
5127 Curlew Dr, St. James City
$240,000
2026035960 MLS ⋅ Pine Island BLDG.
Build your ideal Pine Island retreat on this oversized 80x180 clear lot located on quiet Flamingo Drive in Saint James City. This property is ready for your new manufactured home. Enjoy direct water access, the lot sits high and open offering easy build ability and ample space for parking, outdoor living and storage. The HOA is voluntary that includes use of the pool & boat ramp if you chose to join. It is close to marinas, waterfront dinning and all the charm of Pine Island living. This homesite offers exceptional value for a seasonal get away or full time Florida lifestyle. Just minutes out to great fishing or visiting the Cayo Costa Beach.

5127 Curlew Dr, St. James City
5831 Samoa Dr, Bokeelia
$335,000
3 Beds ⋅ 2 Baths ⋅ 2026031767 MLS ⋅ Pine Island BLDG.
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 Dr, Bokeelia
12303 Cristi Way, Bokeelia
$975,000
3 Beds ⋅ 2.5 Baths ⋅ 2026032475 MLS ⋅ Pine Island BLDG.
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
TBD Masters Landing Dr, St. James City
$325,198
2026031044 MLS ⋅ Pine Island BLDG.
Create your private retreat area. Attention, Nature conservators, Land Bankers, Land mitigation asset comptrollers. Almost 10 acres of Pristine Virgin Pine Island acres near open water on offer for your consideration.(in the Master's Landing vicinity) Address not yet determined Approximate measurement is as follows:328' x 1369' x 328' x1368'

TBD Masters Landing Dr, St. James City
5375 Serenity Cv, Bokeelia
$579,900
2 Beds ⋅ 2 Baths ⋅ 2026029862 MLS ⋅ Pine Island BLDG.
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 Cv, Bokeelia
TBD Masters Landing Dr, St. James City
$342,423
2026027336 MLS ⋅ Pine Island BLDG.
Treasure Hunt! 10+ Pristine Virgin Pine Island acres near open water on offer for your consideration in the Master's Landing vicinity. The address is not yet determined. The approximate measurement is as follows: 332' X 1367 (10+acres)'. Walk past the corner of Masters Landing Dr. Go east of Pirate Landing Ln there is a paper road once at the corner of those two roads you walk about 573 feet and you will be at the SW corner of this unamed parcel which is situated to the east of mls#2026025968 and shares a property line with it. Together these contigous parcels comprise a 27+ acre opportunity. Attention, Nature conservators, Land Bankers, Land mitigation asset comptrollers anyone looking to build a unique estate.

TBD Masters Landing Dr, St. James City
TBD Pirate Landing Ln, St. James City
$501,790
2026025968 MLS ⋅ Pine Island BLDG.
Imagine your private santuary! Attention, Nature conservators, Land Bankers, Land mitigation asset comptrollers. 17+ Pristine Virgin Pine Island acres near open water on offer for your consideration.(in the Master's Landing vicinity) Address not yet determined Approximate measurement is as follows: 1357x573x1367x573

TBD Pirate Landing Ln, St. James City
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