Upper Captiva Homes with Non-Gated Community Type

Upper Captiva Homes with Non-Gated Community Type

Welcome to Upper Captiva, a hidden gem nestled in the heart of Lee County, Florida. This enchanting island community boasts pristine beaches, stunning sunsets, and a laid-back atmosphere that invites you to unwind and embrace the beauty of coastal living. With no gated communities, Upper Captiva offers a unique sense of openness and accessibility, allowing residents and visitors alike to fully immerse themselves in the natural splendor of the area.

As you stroll along the sandy shores, you’ll be captivated by the tranquil ambiance and the sound of gentle waves lapping against the shore. Upper Captiva is renowned for its breathtaking views and unspoiled landscapes, making it a perfect escape for nature lovers and outdoor enthusiasts. Here, you can enjoy activities such as kayaking, fishing, and shelling, or simply relax on the beach with a good book.

The homes in Upper Captiva reflect the island's charm, featuring a range of architectural styles that blend seamlessly with the environment. From cozy beach cottages to modern coastal retreats, each property offers a unique opportunity to experience island living at its finest. With no gated restrictions, you’ll find a welcoming community where neighbors become friends, and the spirit of camaraderie thrives.

Upper Captiva is more than just a place to live; it’s a lifestyle. Discover the magic of island life in this serene enclave, where every day feels like a vacation. Whether you’re seeking a permanent residence or a seasonal getaway, Upper Captiva is ready to welcome you home. Come and experience the allure of this remarkable island paradise!

Newest Upper Captiva Homes with Non-Gated Community Type

$589,900
3 Beds ⋅ 2 Baths ⋅ 2026040242 MLS
Welcome to Sandy Toes Villa, where owning a piece of Southwest Florida paradise means trading traffic and busy streets for sandy paths, golf-cart rides, pristine beaches and true island living. Located on the exclusive, boat-access-only North Captiva Island, this beautifully updated 3-bedroom, 2-bath townhome offers the perfect combination of island getaway and proven vacation rental investment. Offered fully furnished and turnkey, Sandy Toes features impact windows and doors, tile flooring throughout, granite countertops, stainless steel appliances and tasteful updates throughout. Enjoy beautiful water views from the private lanai and easy access to the island’s beaches, with a golf cart available for purchase separately. Owners and guests enjoy access to the Safety Harbor Club and Island Club, with pools, tennis, pickleball, private beach access, kayaks, paddleboards, bikes and marina access. North Captiva also offers its own laid-back dining scene, including Mango’s Bar & Grill, Over the Waterfront and Mainstay/Barnacles, along with a private landing strip serving small aircraft—adding to the island’s truly unique accessibility and charm. Already established in a successful vacation rental program with $60,000+ in annual rental income, Sandy Toes offers the opportunity to own a piece of North Captiva while generating income when you're away. Barefoot beach days, boating, fishing, golf-cart adventures, waterfront dining and spectacular sunsets—this is Southwest Florida island living at its best!

370 Townhouse Lane Unit 65, Upper Captiva
$624,900
2 Beds ⋅ 2 Baths ⋅ 2026039278 MLS
Adorable island cottage on beautiful North Captiva Island with classic beach style. This bungalow offers three sleeping rooms, making great use of the space. The living room and kitchen area are full of charm with tongue-and-groove wood walls, an authentic coastal retreat style. The two levels of decking are great for watching sunsets and gathering with the family. The home is located on a valuable oversized lot, just a short stroll or golf cart ride to the nearest beach access. Plenty of room to add on or install a large pool and outdoor entertainment area. Impact windows and sliders throughout, plus new hardie-board siding. Don't miss out on the chance to affordably obtain your beach house dream goal on this one-of-a-kind island!

4561 Smugglers Drive, Upper Captiva
$89,000
2026036139 MLS
Turn your dream of owning a piece of a tropical paradise into a reality with this North Captiva Island building lot! Perched on the picturesque north end of the island, this property is just a short walk from the bay and white-sand Gulf beaches. You'll have endless opportunities for fishing, dolphin watching, eagle spotting, shelling, and enjoying the island's amazing sunsets. If you are a pilot, this lot is also close to the Salty Approach Airstrip. North Captiva Island is exclusively accessed by boat or private plane, making it a fun and unique place to live or vacation. While you really won't ever want to leave, two regular ferries are running throughout the day that can conveniently take you and your guests to and from your tropical escape. As a bonus, this property already has a well (which could potentially save you over 20k)... one less thing to worry about when you build your new vacation or retirement home!

160 Mourning Dove Drive, Upper Captiva
$170,000
2026035553 MLS
Build Your Island Dream Home at 4471 Cutlass Dr on North Captiva Island, FL! Discover this opportunity to build your custom retreat on one of North Captiva's desirable streets. This high and dry lot offers the perfect canvas for your island vision, with a private well worth 25k-40k already in place to give you a head start on construction. The higher elevation offers a safe foundation for creating the home you've always imagined. Just a quick golf cart ride away are multiple beach access points, putting you within moments of the Gulf's sugar-sands or the preserve's hidden beaches and trails. Whether you're into shelling, hiking, kayaking, or simply soaking in the sunsets, you'll be surrounded by untouched natural beauty every day. The location also places you close to the resort area, with pools, tennis, shops, dining, and the ferry landing. That makes it ideal not only for an ultimate vacation retreat, but also for potential future rental income. With its beautiful location, existing well, and proximity to both the nature preserve and resort-style amenities, this lot is more than just a plot of land - it's your chance to design the island lifestyle most people only dream of.

4471 Cutlass Drive, Upper Captiva
$156,000
2026034990 MLS
Build your North Captiva dream home on this oversized 100' x 120' homesite located in a desirable higher-elevation area just five rows back from the Gulf! With approximately 0.28 acres of land, this generous parcel provides all the extra space needed to create your ideal custom vacation retreat, pool, outdoor entertaining areas, and lush landscaping. The property is close enough to the Gulf to enjoy the sounds of the surf, with convenient beach access leading to miles of beautiful sandy shoreline just a short golf cart ride away. A properly designed island home may offer the opportunity to capture Gulf and Bay views from upper living levels or a lookout deck, adding another dimension to this already appealing location. Spend your days walking the beach, shelling, swimming, exploring nearby preserve lands, or simply enjoying the slower pace of North Captiva. Island dining, shopping, ferry service, and resort amenities are all easily reached by golf cart. North Captiva is a private, boat-access-only barrier island known for its uncrowded beaches, abundant wildlife, protected natural areas, and distinctive golf-cart lifestyle. If you are looking for a high-elevation, oversized property with a view, don't miss this lot!

4531 Conch Shell Drive, Upper Captiva
$779,000
2 Beds ⋅ 1 Baths ⋅ 2026033883 MLS
Almost Beachfront!  Don't miss this cute beach cottage just steps to the beach with incredible views from the front porch.  Sit back, relax, and enjoy the Gulf  & Sunset, surrounded by the sounds of the surf, with the expansive grass airfield as a wonderful buffer from other homes. A perfect spot for your dream retreat this close to the beach. Start your mornings with a walk along the shoreline, spend the afternoon swimming and shelling, and return home to enjoy it all from the shady front porch. Upstairs features panoramic Gulf & Airstrip Views, plus two bedrooms & one bath, with a cozy living space. On the ground level, another bonus sleeping room and bath are great for extra guests. For aviation enthusiasts, the setting is especially unique: the property directly borders North Captiva's private grass airstrip, creating the possibility of turning the journey to your island home into part of the adventure. North Captiva is a boat-access-only barrier island known for miles of beautiful beaches, protected preserve lands, abundant wildlife, and its relaxed golf-cart lifestyle. Whether you're looking for a personal beach escape, vacation property, or a special North Captiva home with an aviation connection, this property offers a combination of beach proximity, Gulf views, privacy, and location that's difficult to duplicate at this price point.

210 Nighthawk Drive, Upper Captiva
$705,000
2 Beds ⋅ 2 Baths ⋅ 2026034184 MLS
Authentic Old Florida Island Charm and timeless appeal combine in this beautiful 2-bedroom cottage, offering classic character with thoughtful updates, including a new metal roof installed in 2023. Inside, soaring cathedral tongue-and-groove ceilings, oak floors, and rich pecky cypress walls create a warm and inviting atmosphere. The open-concept layout was ahead of its time, featuring a spacious kitchen with a wraparound dining bar that flows into the living and dining areas. All living spaces open to an oversized covered front porch, perfect for relaxed outdoor living. The primary suite features glowing wood finishes and an en-suite bathroom with a tub/shower combination. The second bedroom offers dual closets and a cozy nook for more storage or decor, making it ideal for accommodating guests with comfort and style. Below the house, a shady wood deck offers a great space for grilling and entertaining. An adjacent enclosed room houses a full laundry area and extra storage. The landscaped front yard features native plantings and a curving paver driveway. This home enjoys a prime location close to the ferry landing, just a short golf cart ride to both the Gulf's sandy shoreline and the bayside beaches along Pine Island Sound. Boating, fishing, shelling, and island exploration are all easily accessible from this quiet, scenic spot. This charming cottage offers the best of island living—historic style, modern comforts, and one of the best floor plans of a house this size on the island... all in a setting that captures the magic of North Captiva. Whether you're seeking a peaceful getaway, a year-round retreat, or a vacation rental to offset costs while you enjoy the island lifestyle, this is a rare opportunity to own a genuine piece of North Captiva's heritage.

140 Mourning Dove Drive, Upper Captiva
$89,000
2026031238 MLS
Build your island dream home steps from the Gulf beaches on beautiful North Captiva Island! Located on a quiet circle in a higher elevation area, this desirable homesite offers an exceptional opportunity to enjoy coastal living in one of Florida's most peaceful barrier island communities. Just a short walk to beach access, you'll enjoy miles of white sand shoreline, world-class shelling, spectacular sunsets, and the relaxed island lifestyle North Captiva is known for. Resort amenities, shopping, dining, the ferry landing, and preserve trails are all just a short golf cart ride away. Imagine watching gulf views and great sunsets from your lookout, and maybe even some from your highest living floor. Whether you're planning a vacation retreat, an investment property, or your forever island home, this ideally located parcel, with potential views, provides the perfect setting to bring your vision to life.

552 Coral Circle, Upper Captiva
$389,000
2026025092 MLS
Incredible Views of the Gulf from this perfectly located lot just steps to the beach! 4601 Oro Pesos Ln offers an exceptional opportunity to build your custom island dream home. Imagine sitting in your living room, looking out at the Gulf and sunsets, then walking approx. 120 feet to the beach. This generously sized 100' x 105' parcel is partially cleared and ideally positioned only two parcels back from the beach. Enjoy convenient access to beaches, preserve trails, island amenities, and the peaceful lifestyle that makes the island one of Florida's hidden coastal treasures. Opportunities to build new with this combination of proximity to the beach and water views this good are becoming increasingly rare on North Captiva, particularly at this price point!

4601 Oro Pesos Lane, Upper Captiva
$595,000
2026023733 MLS
An incredibly rare opportunity on North Captiva Island! This collection of 4 adjacent lots spans a generous 1.13 acres, offering unmatched potential for a private estate with tropical gardens, a multigenerational retreat, or a 4-residence sanctuary. Enjoy exceptional privacy and the potential for sweeping bay and preserve views from upper levels over and around just 1 row of homes. Ideally located near island dockage, the ferry landing, and club amenities, this property combines seclusion with convenience. Lots may be purchased individually or as a tailored collection that fits your vision.

4430 Conch Shell Drive, Upper Captiva
$865,000
3 Beds ⋅ 2 Baths ⋅ 2026020831 MLS
Dock your boat and enjoy water views from an end-unit townhome, while you build your dream home on an incredible lot with direct views toward the beach and Gulf! Introducing a unique island ownership combination: Townhome #60 at 370 Townhouse Ln (Parcel ID: 05-45-21-03-00000.0600) in Safety Harbor Club, paired with a separate buildable homesite at 4580 Oyster Shell Dr, offered together as an exceptional package. The townhome offers immediate enjoyment with beautiful harbor views, shared community dockage steps away, and full access to all Safety Harbor Club amenities, including a heated pool, tennis courts, pickleball, clubhouse, dining, convenient ferry landing, and private Gulf beach access. Perfectly positioned within Safety Harbor Club, the townhome provides an ideal home base for boating, beach days, and island living, with rental or personal-use flexibility. Included in this package is 4580 Oyster Shell Dr, a valuable homesite with incredible views!  You will be stunned by the amazing view corridor looking down onto the sugar-sand beach and sparkling Gulf waters beyond.  Imagine watching the sun set every night right from your living room. This lot plus townhome combination is a must-see!

4580 OYSTER SHELL DR & 370 TOWNHOUSE Lane Unit 60, Upper Captiva
$148,000
2026020794 MLS
A rare opportunity to own an extraordinary piece of North Captiva Island’s untouched South End coastline. This oversized parcel stretches along the island’s serene mangrove shoreline on the bay, offering a setting defined by privacy, natural beauty, and peaceful seclusion...  with incredible views of a breathtaking beach in both directions. Nestled among some of the most pristine and preserved areas of North Captiva with good water depth for a dock, this property is just steps from one of the nicest beaches in all of SW Florida, where shelling, fishing, and breathtaking sunsets become part of everyday life. This is your chance to own a meaningful piece of one of Florida’s most unique barrier islands. A place to preserve, enjoy, and hold as part of your island legacy. Whether your vision is immediate or simply for the future, properties in this naturally protected and peaceful setting are becoming increasingly rare. North Captiva Island remains one of Florida’s hidden coastal treasures—boat-access only, surrounded by preserve lands, and defined by a slower pace where nature still leads the way. Secure your piece of paradise on the South End of North Captiva, where you will be able to park your boat on one side, and enjoy the beach and sunsets on the other!

11657 Redfish Shores Drive, Upper Captiva
Start Your Search