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140 Pearl Street, Fort Myers Beach
$1,125,000
3 Beds ⋅ 2 Baths ⋅ Hills T.P. SubDv.
This fully furnished, turnkey stilt home offers exceptional flexibility as a full-time residence, vacation getaway, or lucrative income-producing investment. Located in the desirable weekly rental zone, it’s a short walk to the Beach, Diamondhead, Margaritaville, and Times Square. Inside, coastal décor complements cathedral ceilings, abundant recessed lighting, tile flooring throughout, and granite windowsills. The kitchen is thoughtfully designed with granite countertops, soft-close cabinets and drawers, a pantry, under-cabinet lighting, a mosaic glass backsplash, and newer stainless-steel Whirlpool appliances. Both bathrooms feature matching granite counters and soft-close cabinetry for a cohesive look. Your primary bedroom includes a large walk-in closet, while the primary bath offers dual sinks and a walk-in shower. Outdoor amenities include a heated pool with paver deck and privacy fencing, and a large covered area for entertaining. The front porch is enhanced with two roll-down screens mounted at the top, providing adjustable shade and added comfort. Additional exterior features include a paver driveway and low-maintenance zero-scape landscaping. Notable features include impact windows, along with a new metal roof, AC, and pool heater installed in 2023. A rare opportunity to own a move-in-ready island home with quick off-island access just three-quarters of a mile away, ready to enjoy immediately or capitalize on strong rental demand.

140 Pearl Street, Fort Myers Beach
210 Pearl Street, Fort Myers Beach
$1,075,000
3 Beds ⋅ 2 Baths ⋅ Hills T.P. SubDv.
This is the opportunity you've been waiting for! Own your piece of paradise on Fort Myers Beach. This newly constructed home comes Fully Furnished and Turnkey. No need to wait months or years to have your dream home built. This 3 bed 2 bath Florida style elevated home designed and built by Woodland Homes in the most desired location on the Island. Walk to the Beach, shopping, restaurants and Time Square. This weekly rental zone provides the income you need and makes your dream family vacations a reality. Create your lifelong memories in the location your family can own and cherish for generations. This home features the luxury design with modern style to allow you and your quests to enjoy paradise in stress free comfort. Zero scape landscaping provides low maintenance piece of mind for "Absentee Ownership Made Easy." Room For Pool.

210 Pearl Street, Fort Myers Beach
170 Pearl Street, Fort Myers Beach
$925,000
3 Beds ⋅ 3 Baths ⋅ Hills T.P. SubDv.
Welcome to this beautifully remodeled 3-bedroom, 3-bathroom pool home located in the highly sought-after weekly rental area of Fort Myers Beach—just steps from the sand and directly across the street from beach access. Perfectly positioned near Times Square and Margaritaville, this property offers the ideal blend of luxury, location, and income potential. This home maximizes flexibility for both personal use and short-term rental income. Each space has been thoughtfully updated with modern finishes and built for durability and peace of mind. The downstairs features 3’ Hardie board throughout along with waterproof hardboard insulation in the walls, while the entire property boasts waterproof flooring and upgraded electrical outlets. Enjoy resort-style outdoor living with a private pool and fully equipped lanai, enhanced by advanced automation features. Control key systems remotely, including the variable-speed pool pump, pool heater, upstairs A/C and heating, lanai shades, exterior door locks and codes, security cameras, alarm system, ceiling fans, and irrigation system. This turnkey property offers strong rental potential in one of Southwest Florida’s most desirable beachside locations. Whether you’re looking for a high-performing investment or a coastal retreat with income-producing capability, this property delivers. This has been in a weekly rental program for quite some time. Strong rental history with future bookings.

170 Pearl Street, Fort Myers Beach
265 Tropical Shores Way, Fort Myers Beach
$800,000
Hills T.P. SubDv.
Discover an exceptional opportunity with this WEEKLY RENTAL GULF ACCESS oversize 74x109 homesite. With brand new HONC SEAWALL tucked away along one of the most desirable boating streets in Fort Myers Beach. Perfectly positioned just three homes away from open bay waters, this property delivers the ideal balance of privacy, views, and immediate access to Southwest Florida’s renowned boating lifestyle. Surrounded by protected mangroves and tranquil waterways, the lot enjoys peaceful natural scenery paired with bay vistas stretching toward Estero Bay, creating a serene backdrop for your future residence. Design and build an elevated dream home tailored to maximize sweeping sunset views from your upper-level living spaces or expansive outdoor deck — where golden skies fade into the horizon over the nearby Gulf of Mexico. Boaters will appreciate direct gulf access and the added value of a new Honc Marine seawall providing a strong foundation for your dock and lift. A meter and power are onsite to speed the progress of your build. Whether your vision includes a luxury waterfront residence, vacation escape, or income-producing investment, the location offers outstanding flexibility. Situated on a weekly rental-friendly street, future owners can capitalize on strong short-term rental demand while enjoying effortless access to beaches, dining, and island amenities. Rarely does a homesite combine protected mangrove views, bay scenery, premier boating access, and income potential in one offering — an exceptional canvas ready for your coastal vision.

265 Tropical Shores Way, Fort Myers Beach
225 Tropical Shore Way, Fort Myers Beach
$800,000
Hills T.P. SubDv.
Located at 225 Tropical Shores, Fort Myers Beach, this 71 ft x 108 ft waterfront lot offers canal frontage with quick, direct access to the Gulf of Mexico via the Back Bay. The property includes a covered boat dock with lift, providing immediate boating convenience in a well-established canal setting. Situated on a weekly rental street, the lot allows flexibility for future development, whether as a primary residence, secondary home, or income-producing property (subject to local regulations). Its size and configuration support a variety of building options for a custom home or investment project. The location provides proximity to area beaches, marinas, dining, and entertainment, including Times Square and Margaritaville, while maintaining a canal-front setting ideal for water access and coastal living.This property presents a rare opportunity to build in one of Fort Myers Beach’s desirable boating areas with existing dock infrastructure already in place. Buyer to verify all zoning, building, and rental requirements.

225 Tropical Shore Way, Fort Myers Beach
150 Pearl Street, Fort Myers Beach
$700,000
3 Beds ⋅ 3 Baths ⋅ Hills T.P. SubDv.
Just a short walk to the Gulf, Margaritaville, and Times Square, this charming elevated beach cottage is perfectly located in the sought-after weekly rental zone. Ideal as a full-time home, vacation getaway, or income-producing rental. Vaulted tongue-and-groove ceilings and abundant natural light highlight the open interior. The remodeled kitchen features Maple cabinetry, quartz countertops, subway tile backsplash, under-cabinet lighting, and new appliances. Additional updates include newer A/C units, new water heater, tile and plank flooring, solid-core pine doors, custom trim, Andersen impact windows, and a durable metal roof. The guest suite has its own bath, while the primary offers a spacious walk-in shower with tongue-and-groove detail. Downstairs, a bonus room with full bath and mini-split AC adds extra living space, ideal for a home office, studio, or rental option. Enjoy a fenced backyard, Island Bay Marina at the end of the street with rental slips, and off-island access just ¾ mile away.

150 Pearl Street, Fort Myers Beach
162 Tropical Shores Way, Fort Myers Beach
$625,000
4 Beds ⋅ 8 Baths ⋅ Hills T.P. SubDv.
Looking for a solid long-term investment? This triplex checks all the boxes. Located on one of the best streets in Fort Myers Beach, just two blocks — about a 5-minute walk — from the beach. The property sits on a deep water canal with direct access to the ocean and no neighbors behind. It’s in a great, family-friendly neighborhood — ideal for vacationers or anyone looking for a short- or long-term rental. The layout includes one 2-bedroom, 2-bath unit and two 1-bedroom, 1-bath units, giving you plenty of options for rental income. Fort Myers is making a strong comeback, and this is a smart time to buy in. Photos are virtually staged to spark your imagination. Call us today to schedule your private tour.

162 Tropical Shores Way, Fort Myers Beach
137 Pearl Street, Fort Myers Beach
$600,000
Hills T.P. SubDv.
Build your elevated coastal retreat with room for a pool in the ultimate island location! This vacant lot offers a rare chance to design and build your dream single-family beach cottage on one of Estero Island’s most beloved streets. Just steps from the sugar-white sands of the Gulf, you’ll enjoy easy strolls to Margaritaville, a dozen restaurants, beach bars, shops, and lively island attractions—all right at your doorstep. BUILDER INTRODUCTIONS ARE AVAILABLE. Set in a high-performance location surrounded by charming cottages and coastal homes, this property combines the best of island living with incredible convenience. Imagine building an elevated coastal retreat complete with breezy porches, sun decks, and a sparkling pool—perfect for entertaining or relaxing after a day at the beach. With short-term rental potential, this lot is not only an opportunity to create your own private getaway but also a smart investment in one of Southwest Florida’s most desirable destinations. Whether you’re dreaming of a full-time residence, a seasonal escape, or an income-producing property, this site delivers unmatched flexibility. Estero Island is known for its walkable charm, friendly community, and endless outdoor activities, from boating and paddleboarding to breathtaking sunsets. Owning on one of the island’s most adorable and desirable streets ensures you’ll always be part of the quintessential beach lifestyle. Don’t miss your chance to secure this prime coastal lot and bring your vision of paradise to life!

137 Pearl Street, Fort Myers Beach
159 Pearl Street, Fort Myers Beach
$580,000
2 Beds ⋅ 2 Baths ⋅ Hills T.P. SubDv.
Charming tropical beach cottage that is raised off the ground! Home had NO water with Hurricane Helene or Hurricane Milton! Of course everyone got water with IAN. No structural damage at all! Contractor replaced roof and electrical throughout in 2022. This house has loads of fun outdoor space! The front has a tropical feel with palm trees and a paver deck, and the back has privacy fence and a huge paver deck for entertaining and relaxing. There is room for a pool. Lot is basically Maintenance free so if you only come for 6 months, you just relax and enjoy! This home is located in the weekly rental zone on the Island, so 7-day rentals are available! This would be a fantastic beach rental! The Florida style furnishing make you feel like you are on vacation and it's ready to move in now! BOATERS: There is a marina at the end of Pearl St. It is under repair from Ian but should open in the near future. Also if your boat is on a trailer there is a boat ramp one block away from the house. RV’ers: If you want to put your RV in the driveway for extra space there is a 30 AMP plug as well as Sewer Hookup!

159 Pearl Street, Fort Myers Beach
2101 Estero Boulevard, Fort Myers Beach
$550,000
Hills T.P. SubDv.
Step into a rare chance to own one of Fort Myers Beach’s most coveted commercial addresses. Positioned on the prominent corner of Estero Boulevard and Pearl Street, this storied location—once home to the iconic Armondo’s Spa—offers a commanding presence in the heart of the island. Zoned Commercial Boulevard, it delivers the freedom and flexibility to create almost any high-profile commercial venture imaginable. Just 150 feet from the Gulf of America, with direct beach access on Pearl, this parcel offers sweeping Gulf views and constant foot traffic from one of the busiest stretches of Estero. The redevelopment wave sweeping the island is opening doors for bold, visionary projects—whether it’s a boutique hotel, luxury retail showcase, or a signature dining destination. Add to that its prime location near the newly opened Margaritaville Resort, the Pier, Times Square, and a growing collection of restaurants and shops transforming Fort Myers Beach, and the potential here is nothing short of extraordinary. Opportunities like this are almost never available to the market. 2101 Estero Boulevard is ready for its next chapter—will you be the one to write it?

2101 Estero Boulevard, Fort Myers Beach
243 Pearl Street, Fort Myers Beach
$520,000
2 Beds ⋅ 2 Baths ⋅ Hills T.P. SubDv.
Old Florida 1950s elevated bungalow w/ attached inlaw flat and a separate workshop located in a WEEKLY RENTAL zone with a small marina and park at the end of the street! New Metal Roof 2019, HVAC new 2022, New Electric Panel 2022, Interior remodel 2023 including all new appliances and washer/dryer. Close to all the action yet not too close! Would make a great getaway or income producing rental or start fresh and build new in a prime location to maximize your return on your investment! Just 125 yards to the bay front park and Island Bay marina which offers 24 slips for rent (no commercial and limits on live aboards) or just .2 miles to the beach/trolley stop .7 miles to Margaritaville & 1.2 miles to Times Sq/Restaurants and more!

243 Pearl Street, Fort Myers Beach