Pine Island Real Estate | Pine Island Properties between $300,000 and $400,000 for Sale

4 Beds ⋅ 4 Baths ⋅ 2026032000 MLS

Rare Duplex Opportunity on Nearly Half an Acre in the Heart of Bokeelia! Whether you're looking for an investment property, multi-generational living, or the perfect opportunity to live in one unit while renting the other, this well-maintained duplex checks all the boxes. Situated on an oversized lot of nearly 0.5 acres, this concrete block duplex features two spacious units, each offering 1,101 square feet, 2 bedrooms, 1.5 bathrooms, soaring vaulted ceilings in the living room, and tile flooring throughout for easy maintenance. Each unit also includes its own private screened lanai, perfect for enjoying the Florida lifestyle, along with a dedicated exterior storage closet for added convenience. Major updates have already been completed with a new roof and gutters installed in 2023. Conveniently located just minutes from Publix, Pine Island Road, local restaurants, shopping, and everyday amenities, this property offers the perfect balance of privacy and accessibility. With solid bones and room for cosmetic updates, this duplex presents an excellent opportunity to add value while generating rental income or creating your ideal owner-occupied investment. Don't miss your chance to own this Pine Island property with endless potential!

5484/5486 Birdsong Lane, Bokeelia

$389,000

3 Beds ⋅ 2 Baths ⋅ 2026030410 MLS

Island Living at an Incredible Value! Don't miss this opportunity to own an 1802 sf under air/2275 sf total beautiful partially furnished 3-bedroom, 3-bath concrete block one-owner home with a dedicated office and a 2-car garage in the charming community of Pine Island Village in beautiful St. James City, Florida. Priced below market value at just $215.87/sf, this home offers exceptional features and unbeatable value. Best of all this home is NOT in a Flood Zone!! No Flood Insurance required. Designed with comfort and functionality in mind, the spacious split-bedroom floor plan provides for creative use of the open concept living area with cathedral ceilings, and privacy for family and guests. The master has an en-suite bath, walk-in closet, reach-in closet and slider access to the back lanai. The home features durable tile flooring throughout, with carpet in the bedrooms, a walk-in pantry, convenient washer and dryer hookups, and separate office, all with abundant natural light. Enjoy Florida's outdoor lifestyle year-round from the two large tiled front and rear screened patios—perfect for morning coffee or evening relaxation. Listen to the birds and watch the palm trees sway as you pass the hours away in your private retreat! Built for peace of mind, this concrete block home includes impact-resistant windows and doors, a metal roof, and a newly installed whole-house Generac generator, ensuring comfort and security during any season. Residents of Pine Island Village enjoy access to a refreshing community pool while embracing the laid-back island lifestyle, all just minutes from shopping, dining, and everyday conveniences. This is your chance to own a move-in-ready island retreat at an exceptional price! Schedule your private showing today and discover the relaxed beauty of island living!

4406 Lake Heather Circle, St James City

$325,198

2026031044 MLS

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 Drive, Other

$342,423

2026027336 MLS

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 Drive, St James City

$399,000

6 Beds ⋅ 4 Baths ⋅ 2026024876 MLS

Exceptional opportunity to own a turnkey, income-producing duplex in the heart of Bokeelia. Built in 2005 and featuring a new roof installed in 2023, this well-maintained property offers two spacious units, each with 3 bedrooms, 2 bathrooms, and 1,117 square feet of living space. Both units feature modern finishes, private rear decks, and separate backyard areas, providing tenants with the comfort and privacy of a single-family home. Long-term tenants are already in place, creating immediate and reliable cash flow for investors. Whether you're looking to expand your investment portfolio or take advantage of a house-hacking opportunity by living in one unit and renting the other to offset your housing expenses, this versatile property is ready to perform from day one. With stable income, recent capital improvements, and strong rental appeal, this duplex is a rare opportunity on beautiful Pine Island.

5527 Judith Road, Bokeelia

$388,000

3 Beds ⋅ 2 Baths ⋅ 2026018936 MLS

Charming Island Retreat in Pine Island Village with 1469 sq/ft with an additional Florida room adding up to 1640 sq/ft under air. This beautifully maintained 3-bedroom, 2-bath residence is offered fully furnished with the perfect blend of comfort and coastal charm. High and Dry. Positioned on one of the highest points of the island, this home has never flooded and is not in a flood zone, providing added peace of mind. The kitchen features stylish cabinetry highlighted by custom shiplap accent walls and opens to the main living space, which boasts laminate flooring throughout, vaulted ceilings, and beautiful built-in cabinetry that adds elegance and functionality to the main living area. The third bedroom is currently being used as an office and features built-in cabinetry, offering a versatile space perfect for remote work or hobbies. Each bedroom includes a walk-in closet, ensuring ample storage for every room. Both bathrooms have been remodeled with unique mirror accents, and the primary en-suite features a built-in ceiling heater for added comfort. Step into the sunroom, a true highlight of the home, featuring brick flooring, a bamboo ceiling, and tranquil views of Lake Heather. It's the perfect spot to unwind, enjoy your morning coffee, entertain guests, or simply take in the breathtaking sunsets over the lake. Additional features include a 4-year-old roof, built-in smoke detectors, solar panels for energy efficiency, brand new washer and dryer that stay with the home, and a whole-home Aquasana water purifier system. Residents of Pine Island Village enjoy access to a community pool, and the location is just minutes from local shopping, dining, and all the island conveniences. Don’t miss the opportunity to own a slice of paradise in this welcoming island community!

4539 Pine Village Court, St James City

$375,000

4 Beds ⋅ 2 Baths ⋅ 2026011205 MLS

Brand New Roof and newer Airconditioners! Income-producing from day one, this well-maintained Pine Island duplex offers immediate returns with both units currently rented at $1,750/month, generating $3,500 in monthly income ($42,000 annually). Whether you’re looking to expand your investment portfolio or live in one unit while offsetting your expenses, this property delivers flexibility and real value in today’s market. Based on current pricing, an estimated mortgage payment of around $2,400/month with 10% down (buyer to verify with lender) creates a rare opportunity where the numbers make sense. Each unit features 2 bedrooms, 1 bathroom, a comfortable living area, a kitchen with dining space, tile flooring throughout, impact windows, and in-residence laundry. The layout is ideal for long-term tenants, seasonal residents, or owner-occupants seeking additional income. Set in a convenient Pine Island location, the property is close to local shopping, restaurants, parks, and boat ramps, making it especially appealing to tenants who enjoy the laid-back island lifestyle. Known for its world-class fishing, kayaking, boating, and natural beauty, Pine Island continues to attract both year-round residents and seasonal visitors alike. Whether you’re looking for steady rental income, a smart investment, or a way to live the island lifestyle while generating revenue, this duplex offers a unique and compelling opportunity.

5613/5615 Birdsong Lane, Bokeelia

$375,000

4 Beds ⋅ 2 Baths ⋅ 2026011195 MLS

Income-producing from day one, this well-maintained Pine Island duplex offers immediate returns with both units currently rented at $1,750/month, generating $3,500 in monthly income ($42,600 annually). Whether you’re looking to expand your investment portfolio or live in one unit while offsetting your expenses, this property delivers flexibility and real value in today’s market. Based on current pricing, an estimated mortgage payment of around $2,400/month with 10% down (buyer to verify with lender) creates a rare opportunity where the numbers make sense. Each unit features 2 bedrooms, 1 bathroom, a comfortable living area, a kitchen with dining space, tile flooring throughout, impact windows, and in-residence laundry. The layout is ideal for long-term tenants, seasonal residents, or owner-occupants seeking additional income. Set in a convenient Pine Island location, the property is close to local shopping, restaurants, parks, and boat ramps, making it especially appealing to tenants who enjoy the laid-back island lifestyle. Known for its world-class fishing, kayaking, boating, and natural beauty, Pine Island continues to attract both year-round residents and seasonal visitors alike. Whether you’re looking for steady rental income, a smart investment, or a way to live the island lifestyle while generating revenue, this duplex offers a unique and compelling opportunity.

5548/5550 Birdsong Lane, Bokeelia

$345,000

2 Beds ⋅ 3 Baths ⋅ 2026010703 MLS

Stilt home on an oversized lot in Saint James City! Has a closed in garage and workshop downstairs with additional room for guests. This property offers a quiet island retreat with all the convenience for waterfront living. Boating enthusiasts will love this location in Tropical Point! The home is just a few minutes’ walking distance from Tropical Point Park water access, perfect for kayaking and boating, which also provides easy access to explore the surrounding islands, some of the best fishing just right down the road. The home features a NEW metal roof, and a recently updated (UP-2-CODE) Electrical panel, and is ready for you to make it your own!!

3660 Tropical Point Drive, St James City

$332,000

4 Beds ⋅ 2 Baths ⋅ 226007617 MLS

Here is your opportunity to acquire a cash-flowing income-producing duplex in beautiful Bokeelia, Florida. Perfect for investors looking for multi-unit rental property. Immediate stable rental income with upside. Well maintained with a large yard and spacious back lanai for both units. Located just minutes from fishing, boating, shopping, dining, and public transit. Both units are well maintained and have central a/c units. No flooding or wind damage from any storms! Tenants pay both water and electric. This property is ideal for investors seeking a low-maintenance asset in a high-demand rental area. Four Point Inspection and Wind Mit is available! SELLING LOCAL PORTFOLIO INDIVIDUALLY OR TOGETHER. SEE OUR OTHER INVESTMENT PROPERTIES FOR SALE: MLS#s: 226007610, 226007622

5476 / 5478 Avenue C, Bokeelia

$345,000

2025024386 MLS

Don’t miss this buildable residential lot in St. James, FL with direct Gulf access and a seawall already installed. The lot is cleared, level, and construction-ready, offering the perfect setting for your Florida island-style waterfront home.

2359 Sycamore Street, Other

$359,000

2 Beds ⋅ 2 Baths ⋅ 2025022633 MLS

DIRECT GULF ACCESS! Dreaming of living on the water with direct access? Here is your chance. It's not perfect but is priced accordingly. has had some major renovations. Located on an oversized corner lot in desirable St. James City. This 2BR, 2BA Pine Island Shores home is move-in-ready and is a great deal at this price. Step inside to find new flooring throughout, a new kitchen featuring stylish cabinetry, fixtures, and appliances, and fully renovated bathrooms with new tubs, showers, cabinets, and fixtures. Enjoy additional upgrades including a newer metal roof, new AC, new septic tank, new tankless water heater, new washer and dryer, new garage door, and an updated laundry room. Relax in the bright Florida room overlooking the canal, or head outside where this property truly shines. Boaters will love the 10,000 lb boat lift, composite dock, and concrete patio area, complete with electric and water at the dock. From here, you’ll enjoy direct access to San Carlos Bay, Matlacha Pass, Pine Island Sound, and the Gulf of Mexico—ideal for world-class fishing, cruising, and exploring the islands. This affordable move-in-ready home would make the perfect fish camp or weekend get-a-way!! Schedule your showing today! Note: Some of the photos have been virtually staged.

2390 Oleander Street, St James City

$390,000

2025021955 MLS

Build your tropical island dream home on this cleared Gulf access canal. This property is located in a gated community. Home site is located at the southern tip of St. James City, on Pine Island. Minutes to Sanibel, Captiva, Cabbage Key, Ft. Myers Beach and more . You will be boating to some of the best fishing spots and beautiful Beaches.

2417 Macadamia Lane, St James City

$359,000

2025020588 MLS

Residential lot 19 acres, (10 acres and 9 Acres of mangrove) the property has city and well water, electric service, septic tank, and a abandoned house and the conditions are not know by seller. The buyer and buyer's agent have verify all information in the Lee County Office.

11080 Ardon Lakes Drive, Bokeelia

$340,000

2025006419 MLS

BUILD YOUR DREAM HOME IN A NO FLOOD ZONE. Located in Bokeelia on Pine Island Ridge. This fenced and gated property has a large structurally engineered pole barn with a 4" slab. Perfect for RV, Boat, farm equipment storage. A permitted electrical box is in place located near the outbuilding. There is a pond on the property. The unpaved roads are graded for easy access. A great location that has country living feel but is located close to all the amenities the island offers. Close to marinas out to Charlotte Harbor and the Gulf of Mexico for all water activities.

Island Ridge Road, Bokeelia

$349,500

225019707 MLS

A little over a quarter acre waterfront lot for sale in St. James City! Home was demolished after suffering hurricane damage which will save buyer on impact fees to build new. An elevated home will afford spectacular views of Matlacha Pass. Although the lot is not suited for a private dock, there is access to the water via the Lee County public park to the south of the lot where small vessels such as kayaks, paddleboards or skiffs can be launched. The county owns the waterfront strip, the water can be accessed through the mangroves. Bring your plans and build your dream home!

5966 Cove Street, St James City

$335,000

3 Beds ⋅ 3 Baths ⋅ 225014802 MLS

Charming Pine Island Stilt Home with Attached Apartment – Ideal for Bed & Breakfast or Airbnb Ventures! This distinctive Pine Island property – a rare find among stilt homes with a fully permitted lower level, adding valuable space and versatility. This beautifully remodeled home offers over 1,600 sq. ft. of modern living, with stylish updates throughout, making it perfect as an investment opportunity or a spacious family retreat. With new roof, New mini split AC, New tankless water heater, 2 New Kitchens and 3 New Bathrooms - This property is ready for you to move in and experience the best of Pine Island living. Don’t miss the chance to own a versatile, income-generating home in one of Florida’s most unique coastal communities. Seller is offering $5000 towards concessions.

10925 Russell Road, Bokeelia

$379,000

3 Beds ⋅ 2 Baths ⋅ 224097608 MLS

TROPICAL HOMESITES!! Don't miss out on this great buy of a 3 bedroom, 2 bath home that is partially furnished. Home has a 2 car garage, very large Florida room and a screen porch, all for wonderful entertaining or just enjoying the lovely Florida weather. There is a shed for additional storage and a completely fenced yard. See today, buy tomorrow and start living the life.

3790 Tangelo Drive, St James City

Pine Island Properties between $300,000 and $400,000 for Sale

Newest Pine Island Properties between $300,000 and $400,000 for Sale