Pine Island Homes with Waterfront

Pine Island Homes with Waterfront

Welcome to Pine Island, a hidden gem nestled in Lee County, Florida, where serene waterfront living meets the vibrant charm of island life. This enchanting subdivision offers an idyllic escape for those seeking a tranquil retreat, surrounded by nature's beauty and the soothing sounds of the water.

Pine Island is known for its stunning homes that boast breathtaking waterfront views, providing residents with a unique opportunity to embrace the Florida lifestyle to the fullest. Imagine waking up to the gentle lapping of waves and the soft glow of sunrise over the water, all from the comfort of your own home. Whether you’re an avid fisherman, a boating enthusiast, or simply someone who enjoys the peace of nature, Pine Island offers the perfect backdrop for your next chapter.

The community is rich with amenities and recreational opportunities, from kayaking and paddleboarding to exploring the lush mangroves and wildlife that thrive in the area. With close proximity to charming local shops, delightful restaurants, and vibrant community events, Pine Island ensures that residents enjoy both relaxation and a sense of community.

Each home in this subdivision is thoughtfully designed with modern features, spacious layouts, and direct access to the waterfront, making it an ideal choice for families, retirees, or anyone looking to escape the hustle and bustle of city life. Experience the magic of Pine Island, where every day feels like a vacation, and where your dream home awaits. Discover the perfect blend of comfort, community, and coastal living in this enchanting Florida paradise.

Newest Pine Island Homes with Waterfront

$1,425,000
5 Beds ⋅ 3 Baths ⋅ Pine Island SubDv.
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
$599,000
2 Beds ⋅ 2 Baths ⋅ Pine Island SubDv.
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
$195,000
Pine Island SubDv.
Waterfront Gulf Access Lot – St. James City, Pine Island Build your dream waterfront home on this exceptional gulf-access lot in St. James City with no HOA restrictions. This property features a newer 52-foot concrete seawall and cap built by Honc Marine Construction, ideal for larger vessels, sailboats, and serious boaters. Enjoy one-turn access to the Intracoastal Waterway and minutes by boat to Sanibel, Captiva, and Fort Myers Beach, offering some of the best boating, fishing, and island hopping in Southwest Florida. A brand-new thick reinforced concrete pad is already in place, ready for a stilt home or mobile/modular build. City water and sewer are available (no well or septic needed), saving thousands in construction costs. A modular home floor plan is included for buyers looking to fast-track their build. This lot was previously the site of a highly profitable Airbnb rental, demonstrating strong income potential for short-term rental investors. The parcel is on the larger side for this neighborhood, offering extra space for parking, storage, outdoor living, or future expansion. No HOA, no deed restrictions, and endless possibilities!

3814 Dewberry Lane, St James City
$1,000,000
Pine Island SubDv.
Situated on approximately 3.40 acres in the desirable Weeki Wachee waterfront corridor, this expensive property offers a rare opportunity to build a custom home tailored to your vision. This is a rare find in this neighborhood. With an estimated 500+ feet of canal frontage the lot provides exceptional space, privacy, and flexibility for new construction. This is ideal for boating, kayaking, and taking advantage of Florida's coastal lifestyle. Located near the Weeki Wachee River and Gulf access points, this property combines natural beauty with everyday convenience. Whether you're looking to build a primary residence, private retreat, or investment property, this is a unique chance to secure acreage and waterfront in one of Hernando County's most sought-after areas.

10501 Pine Island Drive, Spring Hl
$175,000
Pine Island SubDv.
Build your dream home on this Gulf access homesite in Bokeelia, offering direct boating access to the surrounding waterways and the Gulf of Mexico. This single-family residential lot is ideally situated in a quiet area of Pine Island, providing a peaceful setting with natural surroundings and tropical landscape. Enjoy the convenience of launching your boat right from your future backyard and spending your days fishing, kayaking, or exploring nearby islands and waterfront destinations. The property provides ample space to design and build a custom home with room for outdoor living, a pool, and boat dock. Located just minutes from local marinas, boat ramps, waterfront restaurants, and island amenities, this lot offers the perfect balance of privacy and accessibility. Whether you’re looking to build a seasonal retreat or a full-time residence, this Gulf access property in Bokeelia presents a great opportunity to enjoy Southwest Florida boating and island living.

5350 Marina Drive, Bokeelia
$2,750,000
4 Beds ⋅ 4 Baths ⋅ Pine Island SubDv.
A peaceful, modern, and comfortable lifestyle that is an effortless extension of its natural surroundings. Tucked deep in the Florida pines and palmettos on 10 dry acres with no wetlands, backing up to a 567-acre protected preserve, this 7,500 SF Modern Farmhouse is one of the most architecturally striking and structurally sound homes for sale. Constructed with solid concrete on both floors, PGT hurricane windows and doors, and red iron structural steel. Years of design, engineering, and lifestyle come together. Custom iron front doors, redwood walls, a custom welded staircase, and an Edison bulb chandelier. Everything is intentional. A 4,000 SF 1st floor features the primary suite and bedrooms. A 3,500 SF 2nd floor living space with a flex room/studio offers an open concept w/ dedicated spaces for dining & entertaining. No other home offers this balance of togetherness and privacy. Dolby Atmos theater w/ a 126-inch digital 8K projection screen rivaling commercial theaters. Cambria Quartz counters, modern art, steel beams, and concrete meet mature trees, private walking paths, a 3/4-acre pond, and ATV trails. A dedicated wine room w/ wine racks & shelving for stouts. Restaurant-style full bar w/ Zephyr full-size appliances. A whole-home 10-zone independent audio AV system with JBL speakers & Crown amplifiers. Built for those who want to live, work, and play! Bunker-strength construction, tech room, dedicated Xfinity pedestal & LCEC transformer, and underground utilities. The property has a 9.9 ft elevation - NEVER flooded. The RV garage is 70x30, totaling 2,100 SF, with 28-ft ceilings and drive-through access for 60+-ft RVs. Ideal for car collecting and boat storage, with 3 12x14 ft custom roll-up overhead doors, front & rear concrete pads, prewired for a 20-amp exhaust system, speaker system, epoxy floor, high-bay lighting, 400-amp electrical service, and industrial fans. Private road. ATVs, golf carts, horses, and a shooting/firing range all ok. BOATERS: Marinas 5 min. away & marinas at both ends of the island, boat launches, and easy water access. Four Winds Marina provides ample dry storage options. From here Cayo Costa, Useppa Island, Boca Grande, world-class tarpon fishing, and pristine barrier island beaches. Island dining with local favorites including Blue Dog Bar & Grill, the Yucatan Waterfront Tiki Bar & Grill, and legendary Tarpon Lodge — a hidden waterfront gem offering fine dining. Just over the bridge: The Seven Islands Project includes a Marriott-branded hotel, restaurants, a tiki bar, marina & boat slips, and a lagoon resort beach. Plus an outdoor amphitheater, community center, splash pad, kayak launch, dog park, and a food truck park. Cape Coral Grove will deliver a national grocer, local and national dining, retail, a luxury hotel, premium apartments, 4 public parks, and farmers' markets.

4412 Pinetree Boulevard, St James City
$1,000,000
Pine Island SubDv.
38 acres Total.. 2 parcels, 1 acre lot on stringfellow, 37 acre lot with overgrown palm grove with weed and brush... Well & Well house. Approximately 13.8 acres are Mangrove wetland. Located on West side of Stringfellow from the Winn Dixie Shopping Center.

10011 Stringfellow Road, St James City
$263,000
Pine Island SubDv.
MOTIVATED SELLER PRICED TO SELL RARE GULF ACCESS MIXED USE WATERFRONT LOT NO BRIDGES Don’t miss this exceptional opportunity to own one of the most versatile waterfront parcels in the highly desirable south end of Pine Island. This rare, build-ready lot offers direct Gulf access with no bridges, making it a boater’s dream, perfect for fishing, yachting, or island hopping. Zoned for both residential and commercial use, this property is ideal for investors, builders, or end users looking to create a private waterfront home, boutique business, or a unique combination of both. The possibilities are endless. A brand new seawall has already been installed, saving time and offering immediate value for your future plans. Set in a quiet, charming coastal community known for its relaxed island lifestyle, natural beauty, and premier water access, this property offers incredible upside in a market with limited availability. Vacant waterfront land with this level of flexibility and access is hard to find, especially at this price. The seller is motivated and ready to make a deal. Now is the time to secure your piece of paradise before it’s gone.

2891 Oleander Street, St James City
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