Application Information: Rapid Approval

Association Fee Includes: Common Areas

Fireplace Features: Electric

Flooring: Other

Leasing Permitted Details: Okay To Lease; Short Term Rentals Allowed

Parking Features: Driveway; On Street

Property Condition: Resale

Special Listing Conditions: Auction

Appliances: Dishwasher; Disposal; Dryer; Microwave; Refrigerator; Water Heater; Range

Water Heater Details: Tankless Water Heater

Architectural Style: Key West; Traditional

Boat and Dock Features: Electric Available; Lift; Overnight

Construction Materials: Other

Cooling: Central Air; Electric

Association Type: Homeowner Association

Heating: Central; Electric

Interior Features: Other

Levels: Two

Listing Terms: Cash; Conventional; Lease Purchase; Owner May Carry; Private Financing Available; Trust Deed

Main Living Area: Entry Level

Membership: No Membership Available

Other Equipment: Generator

Pets Allowed YN: Yes

Pets Allowed: No Restrictions; Pet Restrictions Possible

Possession: Before Closing; Negotiable

Restrictions: No Restrictions

Roof: Metal

Sewer: Septic Tank

Storm Protection Details: Curr Owner Wind Mitig Cert Avail

Structure Type: House

Tax Information: City/County

Utilities: Cable Connected; Electricity Connected; Phone Connected; Water Connected; Propane

View: Water

Water Access: No Fixed Bridge; Other

Water Source: Public

Water View: Bay

Waterfront Features: Bayfront

Outdoor Living Spaces: Balcony; Patio

Balcony Details: Balcony - Covered

Patio Details: Patio - Covered

Room Types: Bedroom 2; Bedroom 3; Bedroom 4; Dining Room; Kitchen; Laundry; Living Room; Master Bedroom; Utility Room

Acreage Description: 1/4 To Less Than 1/2 Acre Lot; Less Than 1 Acre Lot

Some properties are easy to describe by bedrooms, bathrooms, square footage and comparable sales. 8241 Main Street is not one of them. Formerly known as the historic Bokeelia Tarpon Inn, this 4-bedroom, 5-bath waterfront estate on the northern end of Pine Island combines more than a century of Old Florida history with more than $1 million in improvements, restoration, design and modernization by the current owners. It may also be purchased turn-key, creating an unusual opportunity for a buyer who wants to begin enjoying the property without first undertaking years of renovation and furnishing. What makes 8241 Main Street particularly difficult to duplicate is not any single feature. It is the combination of history, waterfront setting, artistic character, boating access, privacy, flexibility and location within one of Southwest Florida's most distinctive island environments. The home dates to 1914 and has evolved through generations of Pine Island history. Its identity has long been connected to Bokeelia's fishing heritage and the extraordinary waters surrounding the north end of the island. Today, the residence retains the character and proportions of an earlier Florida while incorporating extensive modern improvements designed for comfort, resiliency and everyday use. The setting is exceptional. From the northern end of Pine Island, the property enjoys expansive water views, including panoramic views toward Charlotte Harbor from the primary suite. Water can be seen from many areas of the residence, creating a constant visual relationship between the home and the surrounding coastal environment. For boaters and anglers, the location opens into an extraordinary Southwest Florida water system. The property includes two boat slips with lift access and provides boating connections into the Charlotte Harbor, Matlacha Pass and greater Pine Island Sound region, with access toward Boca Grande, Cayo Costa, North Captiva, Captiva and the Gulf. This is an area whose fishing history stretches back generations and remains internationally associated with tarpon and some of Florida's most celebrated inshore and coastal fishing. The experience begins before entering the home. The grand covered front area creates a natural place to sit, entertain, enjoy coastal breezes and take in the waterfront surroundings. Throughout the property, historic character has been preserved while new improvements have been incorporated with unusually thoughtful attention to materials and design. The gourmet kitchen is a centerpiece rather than simply a functional room. It features a Big Chill refrigerator and Big Chill Classic gas range, unlacquered brass hardware, a designer Zephyr ventilation hood with commercial-grade baffle system, brass pot filler, soapstone countertops and full-height soapstone backsplash, custom solid-wood cabinetry, glass-front upper cabinets, a custom integrated drainboard sink, restored antique pantry door, period-inspired leaded-glass transom and classic herringbone brick flooring. The principal living areas are bright, open and filled with natural light. Porcelain tile flooring and a Touchstone built-in electric fireplace complement the home's historic architecture without attempting to disguise its age or character. Upstairs, solid-wood floors and custom hardwood stair treads continue the traditional feel of the residence. The expansive primary suite includes vaulted tongue-and-groove ceilings, decorative beam detailing, panoramic water views and a built-in electric fireplace. The spa-inspired primary bathroom includes water jet-cut marble mosaic tile, a freestanding soaking tub, Kingston Brass floor-mounted tub filler with hand shower, custom solid-wood cabinetry and thoughtfully selected finishes intended to feel more like a private retreat than an ordinary residential bathroom. The improvements extend well beyond finishes and decoration. Major property features include: • Metal roof • Two A/C systems • Spray-foam insulation • Walkable attic with additional storage • Navien high-efficiency tankless water heater • Permanently installed Generac standby generator • HOOT aerobic wastewater treatment system • Impact-resistant windows • Electric hurricane protection throughout the home • Kevlar hurricane protection for the upstairs lanai • James Hardie shake siding • High-performance AZEK decking • New railings and stairs • Front deck supported by 24 new structural columns • Covered upstairs porch with tongue-and-groove pecky cypress ceiling • Custom-built pergola with electric • Two boat slips and boat-lift access The grounds are as individual as the residence. Mature landscaping includes fruit-bearing orange, lemon, lime, fig, blackberry and combination citrus trees, together with a substantial coral fountain, rose garden, landscape lighting and outdoor areas intended for relaxation and gathering. Yet the physical improvements tell only part of the story. The possibilities for this property are unusually broad. A future purchaser may see it first as a distinctive private waterfront residence. Another may envision a multi-generational family estate or legacy property. An entrepreneur may see a Florida base from which to live, work and entertain. A company or closely held business may see an executive residence or private corporate retreat. A hospitality-minded purchaser may see the property's historic identity and flexible configuration differently again. It may appeal to an artist, writer or creative professional seeking privacy and inspiration. It may appeal to the serious fisherman or boater who understands what proximity to Charlotte Harbor, Boca Grande Pass and the surrounding islands means. It may appeal to a naturalist, photographer or environmentally minded purchaser attracted to the mangroves, aquatic preserves, wildlife and comparatively undeveloped character of this part of Southwest Florida. And for someone relocating to Florida, the turn-key nature of the property presents another possibility: establish an immediate furnished waterfront residence while taking the time to determine what a permanent Florida lifestyle ultimately looks like. Bokeelia itself is part of the opportunity. Located at the northern end of Pine Island, Bokeelia remains dramatically different from much of highly developed coastal Florida. The island is surrounded by an extraordinary combination of estuarine waters, mangrove systems, fishing grounds, protected aquatic environments and barrier islands. Pine Island Sound lies to the west and Matlacha Pass to the east, with Charlotte Harbor immediately associated with the island's northern end. This is an area where boating, fishing and nature are not amenities added by a developer. They are part of the geography and culture. Pine Island's relationship with these waters reaches back thousands of years. The Calusa built an extraordinarily sophisticated fishing-based society throughout Southwest Florida's estuarine environment. Pine Island remains home to important archaeological and environmental research, while the surrounding Pine Island Sound and Matlacha Pass waters are protected Florida aquatic preserves. For the right purchaser, that distinction matters. 8241 Main Street is not simply another waterfront subdivision home that happens to have a dock. It occupies a place within a much larger story involving fishing, marine transportation, island settlement, conservation, wildlife and Old Florida. The current owners did not simply purchase the property. They invested more than $1 million in creating what exists today—preserving its individuality while making substantial improvements in design, finishes, systems, structure and protection. They have now relocated and are ready for the property to pass to its next owner. The opportunity is therefore not merely to purchase what exists on paper. It is to acquire a property whose history, location, waterfront character and range of future possibilities are exceedingly difficult to reproduce. For qualified buyers interested in understanding the property more deeply, additional due diligence is available through the property's private information portal, including extensive photography, property information, improvement details, available inspection materials and additional questions and answers. 8241 Main Street deserves to be evaluated in person, understood in context and considered for what it could become in the hands of its next owner. All property information is believed to be accurate but is not guaranteed. Buyers should independently verify square footage, dimensions, boating access and depths, zoning and permitted uses, association matters, improvements, tax treatment and any other information material to their intended ownership or use. Any potential tax benefits, including depreciation treatment of qualifying FF&E, should be reviewed with the buyer's independent tax professional. I especially like the structure because it starts with "this cannot be understood through ordinary comparable sales", moves into the experience and improvements, then opens the buyer's imagination to all the different uses, and finally explains why Bokeelia itself matters. I would not repeat the phrase "100% Bonus Depreciation" as an absolute MLS claim without the tax disclaimer. The original listing makes that statement, but the safer and more sophisticated approach is to say qualifying FF&E may offer depreciation benefits and should be confirmed with the purchaser's tax professional. PUBLIC PRICING AUCTION SEPT 12TH - BID NOW. Public Pricing LLC Auctions. List price is deposit amount due from highest bidder at contract. A Rare Asset - Many Possibilities Very Fun Tax Shelter Florida Waterfront Estate & Retreat... Lifestyle • Investment • Escape. Perfect Executive or Family Retreat and Rent Airbnb also. This historic estate blends early 1900s character with over $1 MILLION in high-end upgrades. PLUS.