WANT A SPACIOUS ISLAND HOME W/ PRIVATE WATERFRONT POOL & LAGOON VIEWS & ROOM TO BREATHE? THIS IS IT! Experience PINE ISLAND LIVING in this impressive SINGLE-STORY 2,619 S...

Here is a direct access waterfront 2bed 2bath manufactured home. It's huge at 1376 sqft. built in 1979 comes turnkey furnished. Extra large master suite which encompasses...

Your boat out back. Matlacha’s shops and restaurants nearby. A historic fisherman’s cottage to call your own. Completely renovated and fully furnished, this waterfront re...

BRAND NEW! FULLY FURNISHED! LAKEFRONT LIVING! Why settle for an older home when you can have BRAND-NEW construction, beautiful furnishings, and the Florida waterfront lif...

DIRECT GULF ACCESS – NO BRIDGES – APPROXIMATELY 5 MINUTES TO OPEN WATER! Welcome to your own slice of island paradise in desirable St. James City! This beautifully renova...

A TRULY UNIQUE PRIVATE WATERFRONT ESTATE IN MATLACHA... EXTREMELY RARE FOR MATLACHA! DISCOVER AN EXTRAORDINARY WATERFRONT ESTATE ,OFFERING THE BEST OF ISLAND LIVING IN...

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 count...

Island Living with Views of Charlotte Harbor & Boca Grande Pass! Discover the laid-back Pine Island lifestyle at this rare coastal retreat on Ebbtide Way in Bokeelia! ...

Discover the opportunity to own a piece of beautiful Bokeelia on Pine Island! This vacant residential lot offers the perfect setting to explore building your future Flori...

This unique 2-story Matlacha home offers plenty of space and privacy for the whole family! Situated on 75 ft of direct, no bridge, deep water Gulf access, this home is su...

GULF ACCESS, DEEDED WATERFRONT LAND & EXTENSIVE UPDATES IN CHERRY ESTATES! Welcome to relaxed island living at 2900 Binnacle Lane in St. James City, where your own canal-...

One or more photo(s) has been virtually staged, AI generated or rendered. BACK ON THE MARKET, buyers financing fell through and this is your opportunity to grab tour mov...

Charming, Recently Updated 2-Bed, 1-Bath Home in Bokeelia, Pine Island Welcome to this recently updated 2-bedroom, 1-bathroom home in Bokeelia, ideally located close t...

**Escape to the peaceful charm of Old Florida!** Nestled on the desirable north end of Pine Island in Bokeelia, this **half-acre lot** offers the perfect opportunity to b...

Experience exceptional waterfront living in St. James City, where a prime tip-lot location w/ 183 feet of seawall, expansive intersecting canal views & outstanding boatin...

Experience the dream of living on a sub-tropical island teaming with wildlife and palm trees. This is a very nice property, only one back from the canal with a canal view...

WATERFRONT SINGLE FAMILY LOT ... North end of Pine Island.. Direct Saltwater access to Charlotte Harbor... Seawall and small Wood Dock... Lot is cleared and ready for you...

Gulf access, rental income, and the colorful charm of Matlacha—all in one property. This updated duplex features two 1-bedroom, 1-bath units just steps from the island’s ...

Direct Gulf access, peaceful preserve views, and sunset evenings by the water—welcome to island living in St. Jude Harbors on laid-back Pine Island. Situated near the end...

Morning coffee by the canal, afternoons on the water, and evenings relaxing on the porch—welcome to life at 4924 Flamingo Drive. This remodeled 2-bedroom, 1-bath manufact...

CHARLOTTE SHORES! Very nice and meticulously maintained 3 bedroom, 2 bath pool home in beautiful Bokeelia. Home has a new metal roof, new hurricane rated garage door, new...

This awsome 2/2 home is located in beautiful Pine Island Cove 55+ community. This home is one of the largest in the community with 1608 sq.ft. It is located in the highes...

Picture it…. waking up to another beautiful Southwest Florida morning. The sun is shining, the fish are biting, and the laid-back island lifestyle of St. James City is al...

This newly renovated 2/2 home is located in Pine Island Cove 55+ community where you own your land, and the HOA is only $160.00 per month. This home has new roof 2023, mi...

STUNNING, COMPLETELY REMODELED WATERFRONT HOME IN BOKEELIA — 4 BEDROOMS, 3 BATHROOMS, AND NO STAIRS! Experience the best of Southwest Florida waterfront living in this be...

Key West Style 3/2 house with Cement pilings, wrap around porch, Cement pool & Spa, Classic 2-Stall Horse barn, 2.8 Total Acres, approximately 100 LYCHEE TREES at the Nor...

Create your coastal retreat on this cleared lot with southern rear exposure in desirable St. Jude Harbors. Zoned TFC-2, the property offers a range of potential residenti...

Great Gulf access. Less than 5 minutes out to San Carlos Bay and then on to the fishing, beaches, and restaurants the area is famous for. This 2 bedroom 2 bath home has...

A little dirt road, extra space, and plenty of Pine Island charm! This 0.51-acre lot is zoned RS-1, located in flood zone X, and ready for YOUR vision to come to life! Y...

YOUR FLORIDA ISLAND ESCAPE AWAITS ! Imagine mornings on the water, afternoons exploring the Gulf, and evenings watching the most beautiful sunsets all from the balcony of...

Water views in front, boating adventures out back—and more than half an acre to make island living your own! Welcome to 5442 Martin Cove, a 3-bedroom, 2-bath waterfront r...

Stunning Open-Water Views & Direct Gulf Access in the Heart of Matlacha! This is the view you’ve been waiting for! Discover a rare opportunity to build your dream hom...

Great location. Only 5 lots in from Stringfellow and a half acre lot. The half acre lot next door is also available. Spacious lot for your island home,,

Great location. Only 4 lots in from Stringfellow and a half acre lot. The half acre lot next door is also available. Spacious lot for your island home,,

Welcome to Paradise, Where the Gulf Meets Your Backyard! Situated on the highly desirable south end of Pine Island, access to the Gulf of Mexico or the white sand beaches...

Welcome to your own charming piece of paradise in Bokeelia! This beautifully remodeled 2 bedroom, 2 bathroom, 1 car garage home sits on an impressive 0.46 acre lot. Not i...

Experience the Charm of Bokeelia in this Never Lived-In 2024 Manufactured Home and Live the Island Life in Affordable Style! This 2 Bed, 2 Bath Home is Ready for You to ...

Experience coastal living at its finest with this exceptional Pine Island residence, designed for those who relish both nautical adventure and quiet luxury. Situated on a...

A Rare Waterfront Opportunity on Bokeelia! Discover the possibilities with this exceptional .46-acre property overlooking the beautiful waters of Charlotte Harbor! Ideall...

Rare Double Lot Alert – .63 Acres! Cleared, surveyed, and ready to build, this rare .63-acre double lot in Eagle Lake Estates offers the perfect slice of Florida living. ...

Built in 2015, this waterfront pool home in St. James City offers the perfect combination of newer construction, thoughtful updates and the exceptional boating lifestyle ...

iMMACULATE 2/2 home in beautiful Pine Island Cove 55 + community. Pine Island Cove community has a heated salt water pool, spa, picnic area, boat & Rv storage, club house...

MOVE-IN READY & BUILT IN 2023! Welcome to this beautifully maintained 3-bedroom, 2-bath manufactured home in Pine Island Villas in Bokeelia, offering modern comfort with ...

GORGEOUS GATED COMMUNITY IN BEAUTIFUL BOKEELIA! Build your dream home on this rare lakefront homesite in Calusa Ridge, directly along the community lake, this vacant lot...

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 o...

Pine Island Medical & Professional Office Building | Three Separate Suites 13960 Stringfellow Road, Bokeelia, FL 33922 Own Your Office. Lease Additional Space. Or Inve...

BUILD ON PINE ISLAND WITHOUT STARTING FROM SQUARE ONE! This approximately .26-acre homesite on a quiet cul-de-sac in Pine Island Village comes with something most vacant ...

Stop Dreaming. Start Building. Island Life Begins Here. Tucked away on Pine Island, this rare .34-acre homesite is more than land — it’s the launchpad to a lifestyle most...

Beautifully maintained home in a 55+ community. Immaculately kept and many updates includes but not limited to new asphalt shingle roof, new AC/heat, water heater, washer...

Price just reduced, Priced to sell fast! Welcome to your new Island Home Paradise! This home shines with an oversized corner homesite, extra parking, gulf access canal w...

Discover the potential of this spacious parcel in the peaceful Bokeelia area of Pine Island. For buyers looking for acreage in Southwest Florida with a relaxed, natural s...

Build your dream home on beautiful Pine Island. This lot on a paved road offers the option to also purchase the adjacent lot for additional privacy. This lovely lot is cl...

Partially cleared lot on paved road close to restaurants, boat ramps and nature preserves. Adjacent lot is also available for purchase offering the option for additional ...

ST JUDE HARBORS!! Completely cleared lot on a paved road next to a preserve. The lot boasts being on a fresh water canal for great wildlife viewing and added privacy when...

Welcome to your private island retreat in the heart of St. James City, where your backyard opens to a true protected preserve alive with Southwest Florida wildlife. Watch...

Key West–style waterfront home with direct Gulf access and no HOA. This move in ready property features a 2 bedroom plus den, 2 bath main living level and a separate 1 be...

This is a 7,360+/- sf concrete multi-tenant warehouse zoned Industrial (IG), sits on 1.23 acres of land and located in Saint James City Industrial Park on Pine Island. As...

Peaceful Island Living in Pineland 7443 Pomegranate Drive • Bokeelia, Florida Looking for that Peaceful Easy Island Living? This is it! Tucked away in the charming Pin...

Island life, income potential, and a location that puts Bokeelia right outside your door. Check out this great opportunity to own a duplex on Pine Island! Tucked into t...

Discover an excellent opportunity to build in beautiful Bokeelia on Pine Island! This parcel offers the potential to build duplex homes, making it an attractive option fo...

BOATER’S PARADISE! Welcome to this beautifully renovated waterfront home featuring approximately 50 feet of seawall on a wide, deep canal with NO fixed bridges, offering ...

RARE DOUBLE-LOT OPPORTUNITY IN BOKEELIA! Built for durability, designed for island living, and offering exceptional space for your boats, RVs, and recreational toys! This...

Matlacha on Shoreview is a rare turnkey waterfront hospitality and short-term rental investment in the heart of Matlacha, Florida. Offering 12 furnished guest accommodati...

Tucked on Meadowlark Lane in Bokeelia, Pine Island, Florida, this +/-0.19 acre property offers an accessible entry point into one of Southwest Florida's more laid-back co...

**WATERFRONT GULF-ACCESS LOT WITH BRAND-NEW RIP-RAP SEAWALL!** Discover the opportunity to build your dream coastal retreat on this cleared, ready-to-build waterfront lot...

**WATERFRONT GULF-ACCESS LOT WITH BRAND-NEW RIP-RAP SEAWALL!** Discover the opportunity to build your dream coastal retreat on this cleared, ready-to-build waterfront lot...

**WATERFRONT GULF-ACCESS LOT WITH BRAND-NEW RIP-RAP SEAWALL!** Discover the opportunity to build your dream coastal retreat on this cleared, ready-to-build waterfront lot...

Welcome to easy island living in St. James Isles, formerly known as Cherry Estates, one of St. James City’s established waterfront communities. Built in 2024, this furnis...

Rare opportunity of its kind: This 1.1 acre freshwater corner lot, with over 500+ ft of waterfront and 350+ ft of road frontage is situated at the entrance to St. Jude Ha...

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...

Direct Gulf-access lot in the St. Jude Harbors subdivision of Pine Island (part of, and just north of St. James City), property wraps around the end of the canal and has ...

Rare triple waterfront property at the southern end of Pine Island on Emerald Ave! Situated on an oversized triple 180' x 110' lot with direct access to San Carlos Bay a...

Rare St. James City opportunity! WATERFRONT OFFICE/SHOP AND 2-BEDROOM APARTMENT ...C-1 zoned 100' x 130' waterfront lot in the heart of the business district, offering a ...

0.31 acres for sale in St. James City which offers a great opportunity to own a piece of beautiful Pine Island and enjoy the relaxed island lifestyle of Southwest Florida...

Welcome to your own private tropical oasis in beautiful Bokeelia! Set on 1.5 acres, this unique estate home offers the space, privacy, and laid-back island lifestyle ...

Welcome to island living in St. James City on Pine Island, Florida! This remodeled 3-bedroom, 2-bath Pine Island home sits on an oversized lot with plenty of room for you...

Escape to paradise and build your dream estate on this rare, oversized waterfront lot in Bokeelia’s highly sought-after Serenity Cove community. Offering direct Gulf acce...

Welcome to laid-back island living in Matlacha Isles, a quaint boating community with no city restrictions. This Gulf Access, Pool home features 60 feet of seawall and a ...

Discover the peace, privacy, and natural beauty of Pine Island with this spacious 1-acre homesite at 14999 Martinique Way in Bokeelia. This property offers plenty of room...

This 55+ Pine Island 2010 home offers a great room, open-concept kitchen floor plan with 2 bedrooms, one with a private entrance out to the canal. The floors are all new...

Tucked away in the private waterfront community of Buttonwood Key, this custom-built 2024 home combines privacy, thoughtful design and the ultimate Pine Island boating li...

HARBORFRONT OPPORTUNITY! The Beachhouse Lodge is a unique waterfront property featuring five units, including a third-floor penthouse formerly occupied by the owner, thre...

Welcome to paradise at 3064 Sloop Road, a true boater’s dream tucked away in the serene island community of Saint James City, FL. This spectacular property offers the ult...

BUILD YOUR ISLAND DREAM in beautiful Saint James City! This oversized approximately 0.275-acre residential lot offers an exciting opportunity to create your own slice of ...

Prime commercial opportunity in the heart of Pine Island Center! This 3.87-acre, mostly cleared parcel is zoned Commercial (CC) and offers exceptional visibility and acce...

Build your island home on this CLEARED ½-acre lot in desirable St. James City on Pine Island! This homesite is ready for your plans, with water already brought to the pro...

Experience owning a slice of paradise in this fully and tastefully remodeled home. Each room has been extensively updated to enjoy comfortable island living within its ...

0.2569 ACRE CLEARED RS1 LOT ON POMEGRANATE DR (ENTERANCE RD TO GOLF COURSE) WALKING DISTANCE TO TARPON LODGE HOTEL AND RESTURANT, PINELAND MARINA AND GATOR IN THE ROUGH ...

Seller is offering $15,000 in seller concessions. Set on a quiet private road in Bokeelia's Serenity Cove, this two-story waterfront pool home offers direct Gulf access w...

Welcome to Pine Island! Bring your boat, trailer, camper, and a toothbrush! Enjoy a relaxed lifestyle in the heart of beautiful St. James City! This TURNKEY furnished ele...

A BOATER'S DREAM WITH DEEP-WATER SAILBOAT ACCESS, A 30K-POUND LIFT, AND BIG-WATER VIEWS! Completed in 2026 - With views of intersecting canals, Jug Creek, and a deep-wate...

Paradise awaits in this spacious, beautifully maintained pool home nestled on a private .344-acre lot in desirable Alden Pines, Bokeelia. Built in 1999 with concrete stuc...

This 3-bedroom, 2-bath mobile home is a wonderful opportunity for a small family, retired couple, or anyone looking to enjoy the relaxed Pine Island lifestyle while ownin...

Welcome to 5711 Linden Lane, a spacious and beautifully upgraded Pine Island home offering the perfect blend of comfort, convenience, and island lifestyle. Ideally locate...

1.8 miles north of Pine Island Rd, across from 40+ acre Diocese of Venice church and just north of Pelletier Rickert Physical Therapy. Assemblage of ten 25'X155' lots, cr...

Highest Point on the Island, NO flooding, NO hurricane Damage and newer metal roof! A rare opportunity to own a completely renovated private estate nestled on nearly five...

Welcome to this incredibly charming turn key furnished waterfront cottage paradise! Tucked beneath sprawling oaks, mature mahoganies and swaying palms, this secluded St. ...

BRING THE BOAT, TRAILER, KAYAKS & ALL THE TOYS! Welcome to 3680 Mango Street in St. James City, where laid-back island living meets flexibility and opportunity. With no H...

RARE INDUSTRIAL LOT OPPORTUNITY ON PINE ISLAND! This is your chance to own the ONLY currently available lot in Pine Island Industrial Park—and one of the few industria...

WIDE LAKE VIEWS, A BRAND NEW 2026 KITCHEN AND PEACEFUL PINE ISLAND LIVING! Welcome to Pine Island Village in Saint James City, where tranquil water views, an open layout ...