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$149,000
2 Beds ⋅ 2 Baths ⋅ 2026028789 MLS
Great location at Pine Island Center... Cute 2-bedrooms 2-baths, Vaulted ceilings, Nice Kitchen/Dining area Wood cabinets for plenty of space, Living area, Tile floors, Master bath is beautiful with Tiled walls in bathroom Shower & Bath tub, Wood cabinets .. Yard is 43x 80, raised Septic area, palm trees... very easy maintenance . Location is at the center of the Island, Library-school- pickleball & tennis, museum and little league field, also a 20 acre walkaround park... Great location- Check this property today !!

10419 Trotwood Avenue, St James City
$168,000
2 Beds ⋅ 2 Baths ⋅ 2026026516 MLS
Welcome to a great waterfront opportunity in St James city, you can own a new home with new A/C and brand new septic field in a community that offers quick access to the open water, community pool and club house, this property also offers a nice deck out back to relax on and enjoy the mornings and evenings.

4976 Curlew Drive, St James City
$345,000
3 Beds ⋅ 3 Baths ⋅ 226019909 MLS
Island Retreat with Income Potential on a Full Acre! Tucked away on a private 1-acre agricultural lot in Saint James City, this two-story home offers a great mix of peaceful country living and proven rental flexibility. The upstairs features an open living layout with lots of natural light, white kitchen cabinets, butcher-block countertops, and a full bathroom with a soaking tub. Outside, the property features a durable metal roof and a huge yard with no HOA restrictions, giving you plenty of room to build a pool, put up a pole barn, or park your boats, trailers, and RVs. What really makes this property stand out is the enclosed downstairs space, which has a successful history as an Airbnb rental. This self-contained studio is completely separate and comes ready to go with its own kitchen setup, navy cabinets, and a custom bathroom with a glass walk-in shower. Outdoors, there is a large wooden deck and a fire pit area that's perfect for entertaining. Whether you want to live upstairs and let the downstairs pay your mortgage, use it for family, or add it to your rental portfolio, this Pine Island property offers a ton of options.

4549 Courtney Road, St James City
$129,900
2 Beds ⋅ 1 Baths ⋅ 2026019104 MLS
Welcome to 4811 Flamingo Drive in the heart of St. James City—an authentic island escape where the water is your backyard and the lifestyle is all about simplicity, sunshine, and great fishing. This waterfront-access property has been enjoyed by a true fishing enthusiast, making it the perfect setup for anyone who lives for early mornings on the water and stories that get better with every cast. With direct access to open waters, you can be out to some of the area’s best fishing spots in minutes. The home itself offers a classic “fishing shack” feel and is ready for its next chapter. It does need updating, but that’s where the opportunity lies. Whether you choose to refresh it, renovate it, or keep it as a laid-back retreat, this property is all about location and lifestyle. Outside, there’s plenty of potential to create your ideal waterfront setup. The location currently comes with an older boat house but add a dock, boat lift, and make it your personal basecamp for island adventures. The large lot size adds value and ample room for trailers and fishing toys. Located in the relaxed, golf cart-friendly community of St. James City on Pine Island, this is the kind of place where neighbors wave, sunsets steal the show, and life revolves around the tides. There is a voluntary HOA that allows access to the community boat ramp and heated pool. The clubhouse is a great community location with bingo, dances, and games. If you’ve been searching for a true Florida fishing getaway with room to make it your own, this is it. Bring your vision, your boat, and your love for the water—4811 Flamingo Drive is ready to become your ultimate fishing retreat.

4811 Flamingo Drive, St James City
$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
$109,900
2 Beds ⋅ 2 Baths ⋅ 2026014415 MLS
HUGE PRICE REDUCTION-MOTIVATED SELLER-BRING OFFERS-BUY NOW OR LOSE! AWESOME remodeled 2BR/2BA home in 55+ Community on Pine Island!! Home features new flooring, kitchen cabinets, *(Granite Counters, New A/C, New Stainless Steel appliances to be installed with contract)* and large workshop/storage area. Community has amenities galore including Boat Ramp, Swimming Pool and Boat/R/V storage area.

7151 Drum Drive, St James City
$449,000
3 Beds ⋅ 3 Baths ⋅ 2026014958 MLS
Private and peaceful 3 bed/3 bath two-story home on 1.37 acres in St. James City with a flexible in-law suite. The upper level offers 2 bedrooms, 2 baths, open living, formal dining, den/office, and interior laundry. Sliding glass doors open to a wraparound wood porch on three sides. The kitchen features ample cabinetry, generous counter space, and a breakfast bar. The primary suite includes a walk-in closet, tiled walk-in shower, and porch access. The massive 1,120 sq ft lower level has a separate entrance and includes a full kitchen, living and dining area with wood-burning fireplace, bedroom, bath, and a 10' x 13' storage room with built-ins. Two sets of sliding doors lead to an oversized concrete patio. Additional features include a large shed with drive-in access, updated electrical panel, city water and septic, and the home has never flooded. No HOA or deed restrictions—room for boats, RVs, and future outbuildings. Convenient location near Matlacha, fishing, boating, dining, and beaches.

8677 Whispering Pines Drive, St James City
$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
$299,900
3 Beds ⋅ 3 Baths ⋅ 2026009100 MLS
Welcome to your slice of island life in St. James City, perfectly tucked just off 4th Ave and within easy walking distance to local restaurants, waterfront bars, live music, and some of the best fishing spots in Southwest Florida. Leave the car parked — dinner, sunset cocktails, and casting a line are all just steps away. This elevated 3-bedroom, 2.5-bath home offers a traditional layout with a touch of quasi-Victorian charm, giving it character you simply don’t find in cookie-cutter homes. Think inviting curb appeal, classic lines, and just enough personality to spark compliments from guests. Inside, the first floor is designed for everyday living and entertaining, featuring a comfortable living room, dedicated dining area, kitchen, and convenient half bath. Upstairs, you’ll find all three bedrooms, including the private master suite, along with two full bathrooms — keeping the living space downstairs and the quiet retreat upstairs exactly where it belongs. Whether you're searching for a great starter family home, a low point-of-entry snowbird escape, or simply a place where weekends feel like a permanent vacation, this home checks the boxes. Elevated construction adds peace of mind, and the property is super low maintenance, giving you more time to enjoy boating, fishing, kayaking, and the laid-back island lifestyle. St. James City is known for its relaxed atmosphere, world-class fishing, easy access to Pine Island Sound and the Gulf, and locally loved spots like waterfront seafood restaurants and neighborhood gathering places. It’s the kind of community where golf carts are common, sunsets are routine, and neighbors still wave. If you’ve been waiting for an affordable way to get into island living — without sacrificing charm or location — this is it. Because life’s too short not to live within walking distance of fresh seafood and a good fishing story.

2420 Poinciana Avenue, St James City
$300,000
3 Beds ⋅ 2 Baths ⋅ 226006113 MLS
SHORT SALE. Located on a quiet street in the heart of Saint James City. Situated on Florida’s largest island—a true boater’s paradise—this home offers incredible peace of mind with a metal roof and a rare history of no flooding. The layout is unique and functional, featuring a private primary suite and a large living room on the first floor. Upstairs, the home opens up with a second family room, the kitchen, a dining area, and two guest bedrooms, all with natural light. With both interior and exterior stairs and a spacious side patio, this home is built for easy transitions and enjoying the coastal breeze. The outside of this property is just as impressive as the inside, featuring a massive yard with plenty of room to breathe. Whether you’ve been dreaming of building a pool, adding a large workshop, or just need a secure spot to park your boat and RV, this oversized lot can handle it all. It’s rare to find this much space on Pine Island with a home this large. If you are looking for a comfortable, worry-free home with room to grow and play, this is the one you’ve been waiting for.

8628 Yukon Court, St James City
$449,999
2 Beds ⋅ 2 Baths ⋅ 226000198 MLS
Pictures available upon request. Welcome to your very own slice of island paradise in the heart of St. James City, where laid-back living meets endless waterfront adventure. This 2-bedroom, 1.5-bath home is situated on a large pie-shaped lot at the end of a quiet cul-de-sac, offering a MASSIVE 158 feet of double seawall, a concrete boat dock, and direct access to the Gulf with no bridges—an ideal setup for boaters. The expansive lot provides ample room for a future pool, workshop, RV, boat, boat lift, or additional storage, giving you flexibility and space to make it your own. Inside, the home features an open kitchen and dining area that creates a bright and airy feel, a spacious sunroom perfect for relaxing or entertaining, and an impressive amount of storage throughout. Recent updates include upgraded plumbing and electrical, a rebuilt HVAC system, a new water heater, and a roof replaced in 2021. A flooring credit is being offered at closing, allowing you to add your personal touch. St. James City, located on the southern tip of Pine Island, is known for its world-class fishing, waterfront dining, eclectic art community, and easy boat access to nearby islands such as Sanibel, Captiva, and Cayo Costa. With no traffic lights and a relaxed atmosphere, it offers a true escape from the hustle and bustle. Experience the tropical lifestyle with room to grow, unwind, and enjoy everything Southwest Florida has to offer.

3435 Sea Holly Lane, St James City
$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
$399,950
2 Beds ⋅ 2 Baths ⋅ 2025016539 MLS
POSSIBLE SELLER FINANCING. BRING ALL OFFERS. MOTIVATED SELLER. SELLING DUE TO HEALTH REASONS. Welcome to your waterfront paradise at 2592 York Rd, St James City! Situated on the sought-after Monroe Canal, this charming home features 60' of waterfront with a convenient boat lift. Inside, discover a modern oasis with an updated kitchen featuring granite countertops and an inviting eat-in area. The home boasts two spacious bedrooms, two bathrooms, and a cozy family room. Outside, you'll find ample parking for guests, storage sheds, and endless opportunities for outdoor adventures. Perfectly positioned near top-notch restaurants, marinas, and boat ramps, this location offers fantastic golf cart and bike rides. Enjoy easy access to the Intracoastal Waterway, leading to stunning outer islands and pristine beaches. Don't miss this opportunity!

2592 York Road, St James City
$499,000
2 Beds ⋅ 3 Baths ⋅ 2025016327 MLS
Live the dream on a Southwest Florida island! Nestled on beautiful Pine Island—just 2 miles south of Pine Island Center off Stringfellow Road and a quick 10-minute drive to historic Matlacha—this property offers the perfect blend of peace, privacy, and island charm. Enjoy 1.24 acres of AG-zoned tropical paradise, where you’ll have the freedom to bring all your big toys—boats, trailers, car collections, work vehicles, or campers. You’ll be close to marinas and boat ramps, with easy access to pristine white-sand Gulf beaches and some of the best fishing grounds in Southwest Florida. The property is fully fenced with a wide swing gate and even welcomes horses and animals. This spacious 2-bedroom, 3-bath home, with bonus living spaces, has been recently refloored and updated with all-new exterior stucco and paint, giving it a fresh, modern look and feel. A huge detached garage out back includes a 10' door, water, and electric—ideal for storage, hobbies, or a workshop. The home also features a bonus area (approx. 568 sq. ft. A/C) with a private entrance and interior access—perfect for guests, a home office, or a studio setup. Inside, you’ll find a bright, modern kitchen with stainless steel appliances and a breakfast bar that opens to the living and dining areas. French doors lead out to a covered, screened-in porch, ideal for relaxing or entertaining.

8642 Whispering Pines Drive, St James City
$275,000
2 Beds ⋅ 1 Baths ⋅ 225047802 MLS
Waterfront opportunity in Flamingo Bay! This newly renovated 2-bedroom, 1-bath mobile home offers durability, thoughtful upgrades, and peace of mind. Built with a solid 3/4" plywood subfloor and plywood interior walls, the home is exceptionally well-constructed. Following prior hurricane flooding, the property has been fully remediated by the seller. Inside, you’ll find an upgraded kitchen featuring modern cabinetry and granite countertops. Comfort is ensured year-round with new mini-split A/C and heating units in every room, including the enclosed back porch, which boasts new tile flooring. The home has also been elevated 16 inches to help prevent future water intrusion. Exterior improvements include the replacement of original aluminum siding with plywood and Hardie plank siding for enhanced strength and longevity. The backyard has been refreshed with new sod and an irrigation system, creating a great space to relax or entertain. Boaters will appreciate the updated seawall and cap (2020) along with a brand-new dock (2026), offering easy waterfront access. Ideal as a weekend getaway, vacation rental, or full-time residence—this property combines coastal charm with practical upgrades. Voluntary HOA of $275 per person per year gives access to boat landing, clubhouse, new saltwater pool and amenities. Initial fee of $500 due upon joining HOA. Opportunity to purchase lot to the south for sale by separate seller would give buyer full lot from street to canal front.

5012 Sandpiper Drive, St James City