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8550 Ebbtide Way, Bokeelia
$1,324,500
5 Beds ⋅ 3 Baths ⋅ 2026029600 MLS ⋅ Pine Island BLDG.
Experience the very best of Pine Island waterfront living in this exceptional harbor front estate, where panoramic Charlotte Harbor views, unmatched boating access, and breathtaking sunrises and sunsets create a lifestyle few properties can offer. Tucked away behind a private gated entrance, this custom waterfront retreat features an impressive 400-foot private dock with two 10,000-pound boat lifts, water and electric service, and direct, no-bridge access to some of Southwest Florida's most sought-after destinations, including Boca Grande, Cayo Costa, North Captiva, Cabbage Key, and world-class fishing waters. Designed to capture spectacular water views from nearly every angle, the main living level is easily accessed by either the staircase or your private elevator. Inside, soaring cathedral ceilings and an open-concept great room frame spectacular Charlotte Harbor views, creating a bright and inviting space designed for entertaining. The updated kitchen is beautifully appointed with premium stainless-steel appliances, a Viking range hood, gas cooktop, beverage cooler, trash compactor, abundant cabinetry, and generous workspace, making it ideal for both everyday living and entertaining. The spacious primary suite offers a zero-entry walk-in shower, and handicap accessibility. Three additional guest bedrooms on the main level provide plenty of room for family and friends. The lower level offers exceptional flexibility with a fully equipped private guest suite featuring its own kitchen, living room, bedroom, full bathroom, den, and screened lanai with above ground hot tub. Whether used for multigenerational living, extended guests, a home office, or as a potential income-producing rental, this separate living space adds tremendous value and versatility. Outside, the waterfront lifestyle truly comes to life. Spend your mornings enjoying coffee from the end of your private dock as the sun rises over Charlotte Harbor, then return in the evening to watch unforgettable sunsets over Boca Grande Pass. Launch your boat from one of two lifts and be cruising to secluded beaches, waterfront restaurants, or some of Florida's finest fishing grounds within minutes. Dolphins, manatees, and spectacular coastal wildlife are frequent visitors, making every day feel like a vacation. Built with peace of mind in mind, the home also features a durable metal roof, impact-resistant windows, electric hurricane shutters, propane service, and a private elevator, combining comfort, accessibility, and storm-ready construction. Properties offering this level of privacy, protected harbor frontage, boating convenience, and flexible living space are exceptionally rare. Whether you're searching for a full-time residence, seasonal retreat, or waterfront legacy property, this remarkable home offers an unparalleled opportunity to embrace the very best of the Pine Island lifestyle.

8550 Ebbtide Way, Bokeelia

7940 Lobean Ln, Bokeelia
$780,000
4 Beds ⋅ 3 Baths ⋅ 225033377 MLS ⋅ Pine Island BLDG.
Nestled in the tranquil fishing community of Bokeelia on Pine Island, Florida, this home offers a private retreat with close proximity to local amenities. This 3 story, pool home is located at the end of a quiet road, has a private gate to access almost 1/2 an acre of waterfront property! Downstairs you will find the entry way which leads you to an air conditioned room, that would make an excellent tackle room, along with 1 bedroom and 1 bathroom. The 2nd floor has a nice open living space with a cozy fireplace and functional kitchen with ample space. You will find a wrap around, screened in porch overlooking the mangroves AND a small outdoor elevator. The 2nd and 3rd bedroom, along with a bathroom are on the 2nd floor as well. The 3rd floor has an extremely large master suite, surrounded by wall-to-wall windows. The in ground, heated pool, can be enjoyed all year long. Best of all- this property is located on a deep water, Gulf Access canal, with TWO boat lifts, composite deck and an additional set of davits. You are just minutes away from Boca Grande, Cayo Costa, Cabbage Key and North Captiva. Time to start living the island life!

7940 Lobean Ln, Bokeelia

2291 Palm Ave, St. James City
$700,000
3 Beds ⋅ 2 Baths ⋅ 2025019210 MLS ⋅ Pine Island BLDG.
NEW METAL ROOF APRIL 2026 Spectacular canalfront living awaits in this fully furnished 3-bedroom, 2-bathroom pool home—ready to enjoy immediately or continue as a successful Airbnb/VRBO. Situated on the highly desirable Monroe Canal, one of Saint James City's widest and deepest waterways, this property is a true boater's paradise. Boating enthusiasts will enjoy the utmost in maritime convenience with unobstructed, deep-water access that accommodates sailboats and motorboats with no height or depth restrictions. From your dock, you have quick, direct access to San Carlos Bay, Pine Island Sound, the Gulf of Mexico, and world-class destinations like Sanibel, Captiva, Ft. Myers Beach, and Cayo Costa! With no HOA and stunning views from every window, this home is bright, airy, and designed for comfort, convenience, and entertaining. The main living area features a spacious combined living and dining space, perfect for gatherings. The kitchen includes a gas stove top on the island with hood, all new appliances, and ample storage, including loft storage in the guest room and cedar-lined window seat storage. The primary suite is a private retreat with balcony access, an ensuite bathroom with tub/shower combo, and access to an enormous attic with a finished floor, 10-foot ceilings, ventilation, and walk-around space. One guest bedroom has private access to the pool and deck, while the other shares the full guest bathroom, recently updated with a new vanity. The ground floor is fully enclosed and air-conditioned, renovated with waterproof PVC wall panels, and plumbing is already installed to add an additional bathroom if desired. Outdoor living is exceptional, with a two-story deck, heated saltwater pool (renovated 2023 with new heater and saltwater system), fenced for safety, and privacy enhanced by mature landscaping. The waterside beckons you to unwind by the pool or head down to the dock, where playful dolphins are frequent visitors. Relax on your lanai, listen to the rolling tarpon, and enjoy bird watching right from your backyard. The 10,000-lb boat lift has a new motor, and the dock offers water, electric, and new decking. The outdoor AC unit is elevated to the first floor to remain unaffected by hurricanes. The septic tank was pumped in 2023. Located just yards from the marina, the home offers easy pedestrian access to waterfront restaurants and the local fish market. The St. James community allows golf carts on the roads and hosts lively events such as boat parades, family weekends, and live music. Just minutes to open water and a ½-hour boat ride to Sanibel, this custom-built 1998 home with impact-resistant doors and windows perfectly blends indoor/outdoor living, waterfront amenities, and the Florida lifestyle—ideal as a full-time residence, vacation retreat, or income-producing Airbnb/VRBO.

2291 Palm Ave, St. James City

2311 Sycamore St, St. James City
$500,000
3 Beds ⋅ 2 Baths ⋅ 2026040191 MLS ⋅ Pine Island BLDG.
Experience the ultimate Florida waterfront lifestyle in this beautiful, well maintained 3-bedroom, 2-bathroom, 2-car garage home located on the highly desirable Pine Island. No flooding here and only one owner! Built for water recreation enthusiasts, this property offers direct Gulf access with no bridges, making it a true boater’s paradise. Stepping inside, you are greeted by a neutral color palette that provides a perfect canvas for your creative interior ideas. This home features nice-sized, spacious rooms adorned with durable tile flooring throughout and upgraded laminate plank flooring in the bedrooms. The kitchen is a chef's delight, boasting ample cabinets, countertop space and a large breakfast island that serves as the perfect hub for morning coffee or casual entertaining. Through the triple sliding glass doors, the living area opens seamlessly to a comfortable lanai overlooking the wide gulf-access canal. Step down to your private captain’s walk, complete with a boat lift, ready to launch your next saltwater adventure. This home also offers peace of mind with numerous high-value updates, including Laminate flooring (2024), New roof (2022), New hot water heater (2022), Re-enforced seawall (2021), AC system (2019) and new electric panel. Don’t miss this rare opportunity to own a piece of Pine Island paradise where your boat is docked right in your backyard! All information deemed reliable but not guaranteed. Buyers to do due diligence.

2311 Sycamore St, St. James City

12242 Eagles Nest Dr, Bokeelia
$497,500
2026020078 MLS ⋅ Pine Island BLDG.
SELLER FINANCING AVAILABLE!!! Your shortcut to island living starts here. Welcome to your private slice of paradise on Pine Island. Set on 2.5 acres, this property is already prepped and packed with opportunity the clearing and elevation is done, so you can skip the heavy lifting and jump straight into bringing your vision to life. Tucked away at the very end of a quiet dirt road, this peaceful setting is surrounded by other large parcels, offering both privacy and room to grow. A serene salt water pond borders the west side, adding a natural focal point and tranquil views. Zoned agricultural, this land is incredibly versatile design your dream homestead, start that boutique farm or nursery, or create a private retreat complete with a custom home, pool, and barn. With approximately 200 palm trees already on the ground included in the sale (standing palms do not convey), you’ve got a head start on landscaping or business potential. What truly sets this property apart are two brand-new wooden covered structures beautifully built and perfect for hosting gatherings, parties, family reunions, or even creating a unique event space. Whether you're entertaining under the island breeze or planning something bigger, the setup is already here. Utilities are already in place, with electric on site and a well. fed irrigation system covering the entire property ideal for maintaining lush greenery year round. Life on Pine Island is all about slowing down and soaking it in. Known for its laid-back charm, the island offers scenic bike paths, a local K–5 school, fresh-caught seafood, and endless kayaking opportunities. Surrounded by Gulf waters, you’ll also have access to some of the best shallow water fishing in the world. Whether you're looking to build, invest, or create something truly unique this property delivers the space, setting, and flexibility to make it happen.

12242 Eagles Nest Dr, Bokeelia

5228 Stringfellow Rd, St. James City
$490,000
3 Beds ⋅ 2 Baths ⋅ 2026040187 MLS ⋅ Pine Island BLDG.
An opportunity like this rarely becomes available on Pine Island! Nearly 5.5 acres of mostly cleared, usable land with AG zoning, public water, a private well, irrigation, gated entry, and an existing 3-bedroom, 2-bath home offer a unique opportunity for anyone seeking space, flexibility, and the freedom to pursue an agricultural or homestead lifestyle. Set along Stringfellow Road, this property offers the kind of acreage that is increasingly difficult to find on Pine Island. The land has previously been used for agriculture and includes irrigation that can support the property’s potential nursery or mango operation. Whether your vision is an island homestead, agricultural venture, nursery, growing operation, hobby farm, or simply owning a substantial piece of Pine Island with room to spread out, this property deserves a serious look. The existing home provides a comfortable base while you develop the property around your vision. Recent improvements include a newer HVAC system, impact windows and front door, and luxury vinyl flooring, providing a solid foundation for immediate occupancy or future updates. Soak in the pool after a day of farm work or after coming in off the boat, with a catch of local favorites: Snook, Redfish, and Grouper. The barn also adds value, with a structure already in place to work from or store all the toys you could want on an island farm with quick access to Pine Island Sound. The zoning and potential agricultural exemptions add another important layer of value and flexibility. The gated entrance just off the main road provides privacy while the expansive acreage gives you something increasingly rare in Southwest Florida: room to breathe, room to work, and room to create. And then there is the Pine Island lifestyle. Spend your mornings tending the property, growing your own produce, working with plants, or simply enjoying the privacy of your own acreage. When the day's work is done, you're minutes from Pine Island's legendary boating, fishing, waterfront restaurants, marinas, and the laid-back Old Florida lifestyle that makes this island so special. If you've been looking for a property where you can live, work, grow, and build your own Pine Island vision, you need to see this in person. Properties with this combination of acreage, zoning, infrastructure, and location are truly once-in-a-lifetime.

5228 Stringfellow Rd, St. James City

7655 Myrsine Cir, Bokeelia
$475,000
3 Beds ⋅ 3 Baths ⋅ 226014250 MLS ⋅ Pine Island BLDG.
Welcome to this beautifully maintained and move-in-ready home that perfectly blends comfort, style, and convenience. Nestled in the private community of Isle of Pines, this property offers an inviting open-concept layout filled with natural light, ideal for both everyday living and entertaining. The spacious kitchen features modern appliances, a gas stove, ample cabinetry, two pantries and a generous island that flows seamlessly into the living and dining areas. The oversized primary suite provides a relaxing retreat with a well-appointed en-suite complete with soaking tub, a large tiled shower, his and hers walk-in closets and sliding doors to a private lanai. Two additional bedrooms are perfect for guests, each with their own en suite and large closets. Step outside to enjoy the heated pool and private clubhouse with pool table, and a bonus guest apartment for overflow company. This community has a private waste water system, so you’ll never have to worry about a septic. With thoughtful upgrades throughout, and pride of ownership evident in every detail, this home truly stands out. Walk to nearby Pineland Marina and Alden Pines Golf Course, or enjoy a five star dinner at the world renowned Tarpon Lodge, right in your back yard! A brand new outdoor lift and maintenance free landscaping complete this beautiful property .This home sustained no damage or flooding from any of the recent storms. Don’t miss your opportunity to make this exceptional island home your own—schedule your showing today! Motivated Seller!! New asking price Now $524500

7655 Myrsine Cir, Bokeelia

3932 Phoenix Dr, St. James City
$300,000
2 Beds ⋅ 2 Baths ⋅ 2026012849 MLS ⋅ Pine Island BLDG.
Welcome to your island getaway located in Saint James. This home is perfectly designed for the ultimate waterfront enthusiast. Situated on an oversized direct Gulf access lot, this property offers ample dock space for multiple boats and includes a covered 10,000 lb boat lift. Inside, you’ll find a well-appointed layout featuring 2 bedrooms, 2 bathrooms, and a spacious 2 car garage. Recent upgrades provide peace of mind and modern comfort, including a new AC (2024), water heater (2025), and kitchen appliances (2023). Luxury vinyl plank flooring was installed throughout in 2023, adding both style and durability, while hurricane shutters added in 2024 enhance storm protection. A partially fenced yard offers the perfect space for pets to roam, completing this move-in-ready coastal retreat.

3932 Phoenix Dr, St. James City

15869 Missouri St, Bokeelia
$300,000
2 Beds ⋅ 2 Baths ⋅ 226011517 MLS ⋅ Pine Island BLDG.
This charming 2-bedroom, 2-bathroom home is the perfect island getaway, offering a beautiful and comfortable space both inside and out. The interior features high cathedral ceilings that create an open, airy feel throughout the main living areas. You will love cooking in the modern kitchen, which comes complete with granite countertops, stainless steel appliances, and a convenient center island. The home is also move-in ready with important updates like a newer roof and a brand new tankless hot water heater. The outside of the property is just as inviting, sitting on a large, fenced-in lot that is perfect for enjoying the Florida sun. If you have a boat or an RV, there is plenty of extra parking space available on the property. Best of all, you are only steps away from the community boat ramp, giving you instant access to the incredible fishing and boating waters of Charlotte Harbor. Whether you are looking for a full-time residence or a peaceful vacation spot, this home is a beautiful find in a great location.

15869 Missouri St, Bokeelia

5841 Sabal Ave, St. James City
$299,000
2 Beds ⋅ 2 Baths ⋅ 2026016776 MLS ⋅ Pine Island BLDG.
Welcome to your perfect slice of island living! This beautifully updated 2-bedroom, 2-bath cottage on Pine Island offers everything you need, whether you’re searching for a relaxing getaway or your forever home. This home has been completely renovated with hurricane hardening in mind, featuring a durable metal roof and a strong track record through recent storms with minimal impact. Step inside and enjoy a comfortable, move-in-ready space designed for easy coastal living. Relax and unwind on the large screened porch, perfect for enjoying those island breezes, or take advantage of the oversized storage area and bonus room, ideal for a workshop, hobby space, or easily converted into additional living space. What truly sets this property apart? Opportunity. The sale includes the adjacent 75x150 parcel, giving you room to expand, build a second home, store your boat and toys, or even run a small business. The possibilities here are endless. And for the boating lifestyle? It doesn’t get easier than this is a community boat ramp sits directly across the street, offering quick and convenient access to the water with no fees. All of this is tucked away in the laid-back charm of Pine Island, yet just 30 minutes to Cape Coral and Fort Myers, giving you the perfect balance of island tranquility and city convenience. If you’ve been dreaming of space, flexibility, and true Southwest Florida living....this is it

5841 Sabal Ave, St. James City

13300 Morningstar Ln, Bokeelia
$280,000
2026037142 MLS ⋅ Pine Island BLDG.
This horseperson's dream property is a perfect getaway in paradise on Pine Island, close to fishing, boat ramps, and restaurants and bars. 2.56+ or - acres with stellar improvements. Property has well water, city water, and electric. There is a large gravel pad for RV's with hook ups, two shipping containers, (45 ft and 20 ft) with electric and lights for feed, hay, tack, and equipment storage. Two pole barns, one with two 10 x 10 stalls and one with two 12 x 12 stalls and custom swing gates. Both pole barns are elevated and matted. Property is fenced with no climb and electro braid top line to keep critters out and horses in. 16 ft entry gates, newer well pump, and the east fence line was replaced in 2025. Quiet and peaceful on a dead end road, safe and functional. Very well maintained. This property is located on the highest elevation on the island and did not flood during the past 3 storms. Zoning is AG-2 and a single family residence is allowed.

13300 Morningstar Ln, Bokeelia

11851 Stringfellow Rd, Bokeelia
$175,000
2026020112 MLS ⋅ Pine Island BLDG.
OFFERING SELLER FINANCING!!! A RARE TURNKEY OPPORTUNITY! Positioned in the heart of Pine Island, this beautifully maintained 0.72-acre property is the perfect blend of investment potential and island lifestyle. This unique parcel comes loaded with value, featuring over 450 Christmas palm trees included in the sale making it ideal for a nursery operation, landscaping business, or simply creating your own tropical oasis. The layout is clean, organized, and ready for immediate use. Infrastructure is already in place with electric on site and a well fed irrigation system that services the entire property, saving you significant time and upfront costs. Whether you’re looking to expand an agricultural venture or build something new, the groundwork is already done. The property offers excellent accessibility and visibility, while still maintaining the peaceful, laid-back charm that Pine Island is known for. Surrounded by natural beauty and just minutes from fishing, boating, and local favorites, this location delivers both convenience and lifestyle. Whether you're an investor, entrepreneur, or someone dreaming of owning a piece of island land with income potential, this property checks all the boxes. Ready. Equipped. Profitable Potential. Opportunities like this don’t come around often.

11851 Stringfellow Rd, Bokeelia

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