8241 MAIN Street, Bokeelia, FL 33922
$1,875,000 · Active
- 4 beds
- 5 baths
- 3,200 sq ft
- Single Family Residence
- Built 1914
- HOA $200/mo
- Lot 13,939.2 sq ft
- MLS# B26063000
- Kreamers
About this home
PUBLIC PRICING AUCTION - BIDDING IS EXTENDED UNTIL OCTOBER 17, 2026. List price is the minimum qualified bid of $1,875,000, determined by the public. View the terms of this sale and the process before bidding. A rare asset with many possibilities - waterfront estate, retreat, investment, or short-term rental. This historic estate blends early-1900s character with over $1 MILLION in high-end upgrades, and qualifies for 100% bonus depreciation on FF&E values. Located on the northern tip of Pine Island, where the views simply do not get better. Water views from nearly every window, and the primary suite has panoramic views of Charlotte Harbor. With 2 BOAT SLIPS and lift access, entry into Charlotte Harbor and the Gulf is quick and easy. 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. HISTORY AND SETTING 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 RESIDENCE 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. SYSTEMS, STRUCTURE AND PROTECTION 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. RANGE OF POSSIBLE USES 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 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 suit an artist, writer or creative professional seeking privacy and inspiration. It may suit the serious fisherman or boater who understands what proximity to Charlotte Harbor, Boca Grande Pass and the surrounding islands means. It may suit 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 AND PINE ISLAND 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 SALE 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 property is offered through the Public Pricing process, a seller-and-buyer collaboration in which qualified bidders determine the price. Bidding has been extended until October 17, 2026, and the property will be sold on or before that date at 4:30 PM Eastern. The seller reserves the right to accept an offer and sell prior to the published deadline. List price is the minimum qualified bid of $1,875,000, determined by the public. View the terms of this sale and the process before bidding. 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. Qualifying FF&E may offer depreciation benefits; any potential tax treatment should be confirmed with the buyer's independent tax professional.
Video Tour
Features
- Other
- Balcony
- No Fixed Bridge
- Other
- Bayfront
Presented by
BreakThru Realty · (786) 914-1017
Courtesy of
920 Real Inc. · Listing agent: Fred DeFalco
Schedule a showing
Call or text BreakThru Realty at (786) 914-1017 or email sales@breakthrurealty.com to see 8241 MAIN Street.
Questions About 8241 MAIN Street
- How much is 8241 MAIN Street?
- 8241 MAIN Street is listed at $1,875,000, which is about $586 per square foot. The listing page shows comparable active listings and recent closed sales nearby so you can judge the asking price against what buyers have actually paid.
- What are the association fees at 8241 MAIN Street?
- The listing reports an association fee of $200 per month. Confirm what the fee covers, the reserve funding and any pending special assessments before you make an offer; for a condo, ask for the milestone inspection report as well.
- What are the property taxes on 8241 MAIN Street?
- The listing reports annual property taxes of $8,871 for 2025. Taxes are reassessed at the sale price after a purchase, so a new owner's bill can differ from the current owner's; use the mortgage calculator on this page for an estimate.
- When was 8241 MAIN Street built?
- 8241 MAIN Street was built in 1914 and the listing describes its condition as resale. Age matters for insurance and financing in Florida: ask about the roof, the electrical panel and, for a condo built before the current code, the building's structural reserve study.
- How long has 8241 MAIN Street been on the market?
- 8241 MAIN Street has been listed for 44 days. Days on market and price changes are the first signals of how much room there is to negotiate.
- Is 8241 MAIN Street waterfront?
- Yes. The listing describes the water as no fixed bridge other bayfront. For a home with dockage, confirm the water depth at low tide, the seawall condition and whether the route to the inlet passes under any fixed bridges before you offer.
- How do I see 8241 MAIN Street?
- Request a showing from this page or call BreakThru Realty and a licensed agent will arrange a private tour, in person or by video, and answer anything the listing leaves out.