Pine Island Homes under $500,000

Pine Island Homes under $500,000

Welcome to Pine Island, a hidden gem nestled in the picturesque Bokeelia, Florida. This enchanting island, located in Lee County, is renowned for its stunning natural beauty, charming communities, and laid-back lifestyle. With its lush landscapes, serene waterways, and rich wildlife, Pine Island offers a unique blend of tranquility and adventure, making it the perfect place to call home.

One of the most appealing aspects of Pine Island is the variety of homes available, particularly for those looking for options under $500,000. Whether you’re a first-time homebuyer, a retiree seeking a peaceful retreat, or a family looking for a welcoming community, Pine Island has something for everyone. You can find charming single-family homes, cozy cottages, and even waterfront properties that provide breathtaking views and easy access to the island’s abundant recreational activities.

Imagine waking up to the sound of gentle waves and the scent of salt air, with the beautiful Gulf of Mexico just a stone’s throw away. Residents of Pine Island enjoy a plethora of outdoor activities, including fishing, kayaking, and biking along scenic trails. The island also boasts a vibrant local culture, with delightful restaurants, art galleries, and farmers' markets that celebrate the region's rich heritage.

With its affordable housing options and idyllic surroundings, Pine Island is not just a place to live; it’s a lifestyle. Discover the charm of this unique island community and find your dream home today. Embrace the tranquility and adventure that await you in beautiful Bokeelia!

Newest Pine Island Homes under $500,000

5938 Sailfish Road, Bokeelia
$399,000
4 Beds ⋅ 2 Baths ⋅ 2026045476 MLS
Sailfish Inn Duplex - 4/2 duplex in the Heart of Pine Island. Fully renovated - Metal roof, all new appliances including washers and dryers on each side. Granite counter tops and new cabinets. Full laundry room. Property comes fully furnished. Use for yourself, annual rentals or short term rental, all viable options. One side is leased on an annual lease. Beautiful new Zoysia and new sprinkler system in 2025. Backyard has a privacy fence and fire pits on each side for cozy warm nights by the fire. Insulated storage building is perfect for beach bikes and any other storage. The owner is no longer able to travel to Florida for the winter and is motivated to pass it along to someone new. Very few multi family available on the Island. Perfect time to find your spot in Paradise.

5938 Sailfish Road, Bokeelia
5476 Avenue D, Bokeelia
$219,000
3 Beds ⋅ 2 Baths ⋅ 226035741 MLS
Handyman special! 3 bedroom and 2 bath POOL HOME! Newer roof already installed. Pavers in the outdoor pool area and fenced yard. 1 car garage. Located next 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! 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 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
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
15925 Quail Trail, Bokeelia
$270,000
2 Beds ⋅ 1 Baths ⋅ 224077294 MLS
Welcome to your own piece of paradise in Bokeelia, Florida! This charming single family home boasts 2 bedrooms, 1 bathroom, and a prime location near the Gulf of Mexico. Imagine waking up each morning and taking a short stroll to the nearby fishing pier to catch your dinner or enjoying a delicious meal at one of the local restaurants. The landscaped yard with a beautiful mango tree adds to the Florida feel of this quaint home, creating a serene and tropical oasis. With extra outbuildings and a covered parking area connected to a workshop, there is plenty of space for all of your hobbies and projects. The wooded area next to the property provides added privacy, making this home the perfect retreat from the hustle and bustle of everyday life. Whether you are looking for a peaceful getaway or a permanent residence, this home offers the best of both worlds. Don't miss out on the opportunity to own a piece of paradise in Bokeelia - schedule a showing today and make this dream home yours! This house and surrounding area has never flooded!

15925 Quail Trail, Bokeelia
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