2026026549 MLS

A rare opportunity to secure one of the most visible and strategically positioned commercial assemblages on Sanibel Island's iconic Periwinkle Way corridor. Offering approximately 150 feet of prime frontage along the island's primary commercial artery, 1444 and 1446 Periwinkle Way present a unique chance to shape the future of one of Sanibel's most recognizable locations. The combined offering includes three existing structures spread across two commercial parcels, creating exceptional flexibility for investors, owner-users, developers, retailers, restaurants, garden concepts, professional offices, wellness destinations, galleries, showrooms, mixed-use redevelopment, and countless other possibilities. Imagine revitalizing the existing buildings into a collection of charming Old Florida commercial spaces, creating an inviting courtyard-style destination, or starting fresh with a completely new vision designed to maximize visibility, parking, and customer experience along one of the island's highest traffic corridors. Opportunities of this scale, frontage, and flexibility rarely become available on Sanibel, where commercial land has historically remained tightly held for decades. There has never been a more exciting time to invest in Sanibel's future. The island is experiencing a remarkable rebirth as businesses rebuild, reinvent, and reimagine what comes next. New concepts, new architecture, and new energy are returning to the Sanctuary Island, creating an environment unlike any other point in recent history. As long-established properties transition to new ownership and new ideas, buyers have a rare opportunity to become part of the next chapter of Sanibel's commercial evolution. Adjacent to the Bailey Homestead Preserve and Garden Center and neighboring the lands of SCCF, this highly visible location combines natural beauty with exceptional exposure and accessibility. Whether your vision is restoration, redevelopment, investment, or creating an entirely new island destination, 1444 and 1446 Periwinkle Way offer the location, flexibility, and visibility to bring that vision to life. Prime commercial frontage. Exceptional visibility. Endless possibilities. The future of Sanibel is being written now and this is your opportunity to help shape it.

1446 Periwinkle Way, Sanibel

Listing Courtesy of Pfeifer Realty Group LLC

$2,989,000

2026018701 MLS

Exceptional mixed-use investment opportunity in the heart of Sanibel Island’s Town Center Commercial District.Situated on highly traveled Palm Ridge Road, this unique property offers outstanding visibility, a consistent incomehistory, and the rare combination of commercial frontage with scenic lake views and tropical wildlife surroundings.The property consists of three buildings featuring seven remodeled residential apartments and six establishedcommercial units, along with two separate garage/storage rentals providing additional income. Several residentialunits enjoy peaceful lake views, enhancing tenant appeal. The residential component includes seven bedrooms andseven bathrooms, while the 6 commercial spaces are equipped with eight half-bathrooms, allowing for flexibleconfigurations suited to professional, retail, service, or live-work uses. This asset has a proven track record as anincome-producing property and has previously been utilized by the City of Sanibel, underscoring its versatility andlong-term value within the community. Ideally positioned with convenient access to Captiva and all areas of Sanibel,the property is located within one of the island’s most established and desirable commercial corridors. Occupancyhas remained consistently strong, with all commercial units currently leased and all but one residential unit occupied.Detailed rent rolls and financials are available to qualified buyers. For investors seeking to be part of the early stagesof Sanibel and Captiva’s resurgence, this property offers a rare opportunity to acquire a stabilized, income-producingasset while positioning for the next chapter of growth, revitalization, and long-term appreciation in one of SouthwestFlorida’s most iconic island markets.

2430 Palm Ridge Road Unit 2426, Sanibel

Listing Courtesy of Royal Shell Real Estate, Inc.

$325,000

2026026479 MLS

Position your business or investment in a professionally updated office condominium located in one of Sanibel's most active commercial districts. This corner office condominium is one of only two commercial units in the plaza offering the largest floor plan, with approximately 1,200 square feet of air-conditioned space within a five-unit, partially elevated building that has been recently renovated with a new shingle roof and firewalls between each office condominium. Located at the end of the plaza, the corner location provides additional privacy, abundant natural light through extra windows and convenient parking for customers and staff. The current layout includes a reception area, three private offices and a private half bath, offering flexibility for a variety of professional and service-oriented businesses. Just steps from Jerry's Foods, this highly visible mid-island location benefits from consistent local traffic and convenient accessibility for island residents and visitors. The plaza has historically accommodated a diverse mix of successful businesses, including accounting, chiropractic, veterinary, wellness, real estate and vacation rental operations. For investors, the current tenant is on a month-to-month lease and has expressed willingness to execute a lease renewal, creating a potential opportunity for immediate income. Monthly condominium fees of $750 include building insurance, water, sewer, trash service and pest control, helping simplify ownership and operating expenses. Whether seeking a space for your professional service or medical business, a satellite office or income-producing investment, this office condominium offers a flexible floor plan, established commercial presence and a central Sanibel location.

1640 Periwinkle Way Unit 5, Sanibel

Listing Courtesy of Premier Sotheby's Int'l Realty

$1,495,000

2026022434 MLS

Premier opportunity to acquire a highly visible commercial property in the heart of Sanibel Island’s Town Center corridor.Located at 2341 Palm Ridge Road near CVS and Sanibel City Center, this professionally configured commercial building consists of three separate folios/units currently operating as one combined space with a long-standing professional office occupant in place. The property offers approximately 2,827 square feet with excellent accessibility,strong visibility, and 22 on-site parking spaces. The existing layout includes multiple private offices, conference space, reception area, kitchenette, restrooms, and flexible work areas suitable for a variety of professional and commercial uses including legal, financial, consulting, design, real estate, wellness, and other service-oriented businesses.Current occupancy provides immediate income with future flexibility for an owner-user, investor, continued tenancy,or potential multi-suite configuration. Historical records and prior marketing reference Units A, B & C with separate folios and individual tax parcels. Positioned just off Periwinkle Way within one of Sanibel’s most established commercial corridors, this is a rare opportunity to secure a well-located island commercial asset with long-term value and flexibility.

2341 Palm Ridge Road Unit A, B, C, Sanibel

Listing Courtesy of Portside Property Group

$3,000,000

2026018790 MLS

Opportunities like this don’t come along often. Own a prime piece of Sanibel Island; or three! With rare nightly rental zoning, exceptional income potential, and redevelopment already positioned to move forward, the Tropical Winds portfolio represents one of the island’s most unique and valuable investment opportunities. With an architect, engineer, and contractor already assembled and ready to begin immediately, the Tropical Winds portfolio presents a rare opportunity to accelerate redevelopment with a projected opening for the 2027 season if acquired in June. Now cleared and ready for reconstruction, the Tropical Winds portfolio presents a rare opportunity to reimagine multiple income-producing parcels in one of Sanibel’s most exclusive and tightly regulated sectors: nightly rentals. In a market where most properties are limited to 30-day minimum rentals, this offering stands apart with zoning that allows short-term vacation rentals, creating exceptional revenue potential in a highly supply-constrained segment. The portfolio includes a six-unit Gulf-front hotel with direct beach access and sweeping northwestern views of the Gulf of Mexico, along with two duplex properties that also benefit from coveted nightly rental eligibility: 1344 & 1350 Jamaica Drive; Lots zoned for two duplex constructions. Impacted by Hurricane Ian and now cleared, the properties offer a blank canvas for new, elevated construction. Sanibel’s post-Ian Build-Back provisions allow redevelopment within the original building footprint and volume, while enabling modern improvements such as elevated structures, enhanced views, under-building parking, storage, and increased storm resilience. The west-facing hotel site borders protected land, ensuring long-term privacy and unobstructed sunset views; an increasingly rare coastal advantage. This is a unique chance to develop higher-end accommodations while retaining the valuable nightly rental zoning that makes this portfolio truly exceptional.

4819 Tradewinds Drive, Sanibel

Listing Courtesy of Pfeifer Realty Group LLC

$5,300,000

2026014066 MLS

Once in a generation opportunity to own not one, but two, of the few remaining motel/hotel establishments on Sanibel Island! Legally permitted for nightly rentals and generating close to $1,000,000 in annual revenue, the Palmview and Sandpiper Inns are powerhouse performers with strong historical and future rental performance. Receiving a ground up renovation in 2024 with existing management in place (if the new owner so desires), both are well outfitted to offer their new owner a consistent, worry-free, income for years to come! Agent possesses interest in this property.

706 Donax Street, Sanibel

Listing Courtesy of Premier Sotheby's Int'l Realty

$2,700,000

2026002508 MLS ⋅ Pelican Place Shopping Center BLDG.

Income-producing two-story commercial building in the heart of Sanibel’s Central Business District, offering 175 feet of prime Palm Ridge Road frontage and outstanding visibility. Zoned Town Center Limited, the preferred location for retail and mixed-use opportunities, and is designated G (Altered Lands) under the City of Sanibel Comprehensive Land Use Plan. The fully leased first floor provides immediate, stable cash flow, while each level offers 4,066 square feet of space. Constructed with steel-reinforced concrete slab and concrete stem wall footings for long-term durability and low maintenance. The second floor presents future residential potential, with architectural plans already prepared and subject to City approval—creating meaningful value-add and additional income upside. A strategic opportunity to secure high-visibility Sanibel commercial real estate with both current performance and long-term growth potential. Building currently being repainted & doors replaced on second floor.

2440 Palm Ridge Road, Sanibel

Listing Courtesy of Pfeifer Realty Group LLC

$1,100,000

2025018917 MLS

Open for business and available for immediate occupancy! Welcome to 1149 Periwinkle Way, a distinctive and recently refreshed Olde Florida–style business campus that perfectly blends charm, character, and functionality. This one-of-a-kind property features three free-standing office buildings, all connected by a spacious elevated deck surrounded by lush tropical landscaping—creating a unique setting for inspired island business. Building #2 is an elevated two-story structure offering approximately 1,500± sq. ft. on the main level and another 1,500± sq. ft. on the upper floor, each with its own entrance, two full bathrooms, and the top floor suites also feature a full kitchen. Previously home to a respected real-estate brokerage, property-management firm, and a full service spa- these flexible spaces are ideal for a professional office, creative studio, island inspired retail, or boutique enterprise. The ground level provides over 1,500± sq. ft. of climate-controlled storage along with a private two-car garage—a rare convenience on the island. Recently remodeled and meticulously maintained, this inviting campus is among Sanibel’s most appealing business centers, offering maximum visibility along Periwinkle Way, the island’s main travel artery. With immediate access to the Causeway, the location ensures exceptional convenience for clients and employees alike. Now is the moment to elevate your business and invest in Sanibel’s revitalized future—1149 Periwinkle Way is ready to welcome your vision!

1149 Periwinkle Way Unit 2, Sanibel

Listing Courtesy of Michael Saunders & Company

$550,000

2025015749 MLS

Prime Commercial Opportunity on Periwinkle Way Don’t miss this exceptional opportunity to own a commercial building with outstanding visibility and frontage along Periwinkle Way—one of the most traveled corridors on the island. Ideally located near the causeway, this 1,780 square foot space offers convenient access on and off the island, making it a strategic location for both local and visiting clientele. Positioned within the well-established Priscilla Murphy Center, the property benefits from proximity to popular restaurants, boutique shops, and financial institutions, ensuring a steady flow of potential customers. The center is professionally maintained, featuring brand-new, lush tropical landscaping and a recently upgraded pavered parking lot that enhances curb appeal and customer convenience. Whether you're looking to establish a new business or expand an existing one, this space provides a rare blend of location, accessibility, and community synergy.

1025 Periwinkle Way, Sanibel

Listing Courtesy of John R. Wood Properties

Selling Office: .

$225,000

2025012910 MLS

LOCATION, LOCATION, LOCATION - COMPLETELY RENOVATED OFFICE 2024 - SANIBEL ISLAND This 987 square feet of flexibleoffice condo space comes complete with luxury vinyl plank flooring, pristine white cabinetry, built-in workspaces, multiple offices, waitingroom area, separate receptionist and assistant space, restroom within unit, two sinks, washer, dryer, full sized refrigerator. Ideal for avariety of business ventures, ie. a medical practice, veterinary services, pet grooming, a modern office environment plus many moretypes of businesses. This superior build-out should meet your expectations. Situated on Periwinkle Way, this location is at the heart ofSanibel Island, just across from the Bank of the Islands and near Jerry's Grocery Store. With high visibility and easily accessible parking,you'll be perfectly positioned to attract both locals and tourists. The area is buzzing with activity, offering proximity to beaches, golfing,boating, and shopping. Interested in seeing it or need more information? Feel free to reach out directly. With a bustling location anddynamic potential, your business could thrive here.

1640 Periwinkle Way Unit 3, Sanibel

Listing Courtesy of McCallion and McCallion

$950,000

225012975 MLS

Own a Piece of Sanibel History in a PRIME Location! Welcome to a rare opportunity to own one of Sanibel Island’s most iconic buildings, beautifully reimagined for modern use while honoring its rich past. This freestanding historic gem, originally built in 1913 and steeped in local history, began life as a Baptist Church before becoming the Sanibel Colored School in 1927. After decades of transformation—from a cherished school to an art gallery, gift shop, and most recently, Lily & Co. Jewelry—this building stands ready for its next chapter. Perfectly positioned in a high-traffic, high-visibility location, this property sits directly across from the upcoming Bailey’s Shopping Plaza and adjacent to the popular Doc Ford’s Rum Bar & Grille—a hotspot for foot traffic, cyclists, and vehicles alike. Zoned Town Center General—the most flexible zoning available on Sanibel—this space invites a wide range of commercial or creative possibilities: boutique retail, gallery space, café, studio, office, or a unique mixed-use concept. The seller has worked in partnership with the City of Sanibel to fully remediate and modernize the structure while preserving its historical charm. Recent upgrades include: Complete interior demo and rebuild Crawl space filled and reinforced with concrete Brand-new 24-gauge standing seam metal roof Seamless gutters and marine-grade exterior light poles All new drywall, base, casing, and interior doors Cali Longboard vinyl plank flooring throughout Fully updated plumbing and electrical systems Brand-new HVAC and mini-split systems Fresh interior and exterior paint Windows and doors re-caulked and sealed Whether you’re an investor, entrepreneur, or visionary seeking a landmark location with story and soul, this one-of-a-kind property offers endless potential in the heart of Sanibel Island. Don’t miss your chance to create something truly special—schedule your private tour today.

520 Tarpon Bay Road, Sanibel

Listing Courtesy of John R. Wood Properties

Selling Office: .

$900,000

225051226 MLS

Opportunity knocks for this Sanibel Island commercial property with 180 feet of direct Periwinkle Way frontage. The building is 2,151 square feet and the land has 0,42 acres. Zoning is Town Center Limited. The primary eco zone appears to be G and partially d-2. This property and 905 Fitzhugh could be sold together, offered at $ 2.4 M. The possibilities are plentiful.

1544 Periwinkle Way, Sanibel

Listing Courtesy of Pfeifer Realty Group LLC

Selling Office: .

$2,999,000

225044961 MLS

This bank-owned property presents an iconic Sanibel development opportunity offering 200 feet of frontage on Periwinkle Way, 2.5-plus acres of land and waterfront features. Presenting a once-in-a-generation opportunity to acquire one of Sanibel Island’s most storied and strategically located commercial parcels. Formerly home to the iconic Jacaranda Restaurant and Bar, a beloved institution that served generations of islanders and visitors, and most recently the Tipsy Turtle, this legacy property is ready for its next chapter. Ideally along 200 feet of frontage on Periwinkle Way, Sanibel’s main thoroughfare and commercial spine, the property spans over 2.5 acres of developable land zoned General Commercial and D2 Upland Wetland. This premier site offers exceptional development flexibility, with initial assessments suggesting the potential to construct 8-9 residential units. Alternatively, zoning allows for a mixed-use development, combining residential living with a commercial component. The final residential count in this scenario would vary depending on footprint of the commercial structure, allowing for a custom-tailored approach to suit investor or developer goals. Adding to its appeal, the property features a scenic central lake and frontage along the tranquil Sanibel River at the rear—rare natural amenities that enhance its desirability for residential or hospitality development. Whether reimagined as an upscale enclave, a vibrant mixed-use destination or a new community hub, this property represents a unique and irreplaceable opportunity in the heart of Sanibel Island. Iconic history. Prime location. Boundless potential.

1223 Periwinkle Way, Sanibel

Listing Courtesy of Premier Sotheby's Int'l Realty

$1,095,000

225051228 MLS

This commercial building off Periwinkle Way offers 3,000 square feet and 100 feet of side street frontage with .027 acres. This building has 1,500 square feet on each level; the first floor is all open, and the upper floor currently has an apartment with 2 bedrooms/offices. Zoning is Town Center Limited. The primary eco zone appears to be G and partially d-2.

905 Fitzhugh Street, Sanibel

Listing Courtesy of Pfeifer Realty Group LLC

$225,000

225020845 MLS

Rare opportunity to own Periwinkle Way fronted commercial property for such a price. Located in The Town Center Commercial District, it is in the center of the action. Next door is a shopping/office/services center and across the street is the F.I.S.H. complex and the San Cap Bank. Its location on the bike path further enhances its visibility. Formerly home to several successful restaurants and the original Cheeburger Cheeburger. The Town Center General Commercial Districts allows myriad uses, including: retail, office, services, (take out) restaurant an more. Higher floor area ratios are also permitted. There are two structures, one frame and one CBC. Subject to build back (126-212). Some provisions have been extended and currently expire at the end of the year. May be able to rebuild on the same “footprint” even if it is relocated on the parcel (respecting setbacks, etc.). This could allow up to eight parking spaces. Property has deeded access to the lift station just East of the parcel.

2411 Periwinkle Way, Sanibel

Listing Courtesy of Kingfisher Real Estate, Inc.

Selling Office: .

$2,459,000

224021129 MLS

Welcome to the Driftwood Inn, a boutique gem located in Sanibel Island's Resort Housing district, offering nightly rentals. This is a rare opportunity to acquire one of a few properties with nightly rentals on Sanibel Island. This well-established property is in one of Florida's most coveted beach destinations. Featuring four charming two-bedroom / two-bathroom cottages with full kitchens and screened lanais just seven houses from the beach access. Meticulously maintained, efficiently managed, and conveniently located near restaurants and shops, the Inn provides a perfect balance of island tranquility and accessibility. The Driftwood’s Island charm, peaceful grounds, and ideal location make it a top choice for island vacationers. Recent renovations exceeding $600,000 make it a turnkey investment opportunity with reservations already secured. Projections for 2024 forecast a robust gross rental income of $315,000, supported by strong occupancy and loyal repeat guests. The Driftwood Inn offers the perfect combination of rental income and real estate value appreciation, making it a sound investment opportunity in the hospitality market.

711 Donax Street, Sanibel

Listing Courtesy of Pfeifer Realty Group LLC

Selling Office: .

$625,000

223080335 MLS

Great investment opportunity. Commercial office space located very close to the Sanibel Causeway. There are six separate office spaces including reception area and conference room. Property currently has a tenant with a three year lease.

1149 Periwinkle Way Unit 3, Sanibel

Listing Courtesy of VIP Realty Group,Inc

Selling Office: .

$2,300,000

223071401 MLS

Prime Location and Rare Opportunity! Well-established Gas and Service Station situated in one of the most coveted spots on Sanibel Island. Positioned conveniently on Periwinkle Way, just west of the four-way intersection, this station stands as one of only two automotive gas stations available on both Sanibel and Captiva Islands. Its exceptional visibility makes it a promising investment opportunity. The property features two gas pumps, totaling five nozzles, ensuring efficient service. Additionally, there are two indoor and two outdoor service bays that could potentially be transformed into retail convenience spaces. For ample storage needs, there is a spacious yard at the rear of the property, and a detached one-bedroom cottage is also included. This property was damaged due to Hurricane Ian and needs work to bring it back to its former glory. Sold As-Is. Don't miss out on this rare chance to own a service station in such a prime location!

1067 Bailey Road, Sanibel

Listing Courtesy of Pfeifer Realty Group LLC

Selling Office: .

$3,200,000

223071391 MLS

OVERVIEW: Rare investment opportunity to own a hotel with nightly rentals on Sanibel Island. Perfectly positioned investment location along the islands bike path and walking distance to beaches, shopping, dining establishments FEATURES: 12 nightly units and 1 managers cottage or possible monthly rental, each with private bathroom and kitchen. Efficiencies, studios, and three spacious A-frame cottages. 2.44-acres boasts spacious grounds, including a large pool, picnic areas, bike storage, ample parking, tranquil pond, office area, laundry facility and storage. VERSATILITY: Whether you envision a boutique hotel recreated within the existing footprint or redesigning for residential development, it offers the flexibility to explore both options. SANIBEL RARITY One of the few properties on Sanibel Island permitted for nightly rentals. VISIBILTY: located along the island's main road while benefiting from its set-back position, allows amble privacy. HIGHLIGHTS: Ideal visibility and located just under a mile from the beautiful white sandy beaches, this is an exceptional opportunity to create a unique hospitality experience. Don’t miss this chance to own a piece of Sanibel and transform this iconic 1959 motel into a sought-after boutique hotel.

1245 Periwinkle Way, Sanibel

Listing Courtesy of Pfeifer Realty Group LLC

Selling Office: .

$600,000

223039078 MLS

One of Sanibel Island's Iconic Cottages located on Periwinkle Way, "downtown Sanibel." This cottage has graced Periwinkle Way for over 50 years and weathered storms like a champ. This commercial property is situated on a conforming lot and boasts Olde Florida Style with a cozy front porch, soaring ceilings with cross beams, cupula, back deck and metal roof. Sellers have obtained an estimate to elevate the structure using a unified hydraulic jacking system. Property offers five private offices, reception area and storage. This parcel has been occupied by real estate companies for the last 53 years and could be an excellent retail store. Don't miss this one! COTTAGE CAN BE REBUILT ON THE PROPERTY, CONTACT YOUR AGENT FOR DETAILS.

2000 Periwinkle Way, Sanibel

Listing Courtesy of VIP Realty Group,Inc

Selling Office: .

$1,650,000

223037280 MLS

This is a truly once in a generation opportunity to own Sanibel's iconic Dairy Queen and two surrounding properties. Located near the four-way-stop in a sought-after location with high visibility and great traffic count, this combined offering features three parcels totaling approximately one acre of land and boasting approximately 200 feet of highly desirable Periwinkle frontage. This property features the Dairy Queen restaurant and land including the grandfathered franchise agreement at a very desirable split, a duplex and land behind the restaurant, and a third vacant piece of land adjacent to the west. This popular eatery has been visited by generations of islanders and vacationers alike. Everyone recognizes the Sanibel Dairy Queen, and this reputation is waiting for a new owner and operator. The buildings sustained hurricane damage. This is your opportunity to rebuild a once thriving and iconic island business.

1046/1048/1090 Periwinkle Way, Sanibel

Listing Courtesy of Premier Sotheby's Int'l Realty

Selling Office: .

Sanibel Florida Commercial Properties for Sale

Sanibel Florida Commercial Properties