Homes with Pools for Sale in Big Pine Key, FL

Home with a Pool for sale in Big Pine Key, FL:

Welcome to 27416 Tobago Lane, where waterfront living and the Florida Keys lifestyle come together. This home offers open-water views and an abundance of indoor and outdoor spaces designed to make the most of island living. Boaters will appreciate the 10,000-lb boat lift and Jet Ski davit, while the fenced yard, lush tropical landscaping and multiple outdoor areas create your own private retreat. One of the home's most memorable features is the 3rd-story observation and sun deck. Take in the open-water views and ocean breeze during the day, then enjoy unobstructed stargazing and meteor showers at night. Tucked into the tropical landscaping you'll also discover a private meditation garden, o

Home with a Pool for sale in Big Pine Key, FL:

Exceptional Investment Opportunity in the Lower Florida Keys! Owner and private financing are available. This is one of the very few vacation rental properties licensed for daily, weekly, or monthly rentals. Boasting an impressive occupancy rate and generating up to $400,000 annually, this property offers stress-free, passive income in Summerland Key, a premier location. Discover a rare gem in the heart of the Lower Keys! Recently remodeled to perfection, this luxurious three-bedroom beach house includes a sunroom with a palatial ocean view, currently used as a fourth bedroom. Just 20 miles from vibrant Key West, this coastal retreat features a private natural beach, breathtaking ocean view

Home with a Pool for sale in Big Pine Key, FL:

Spectacular sunset views from this custom-built, fully furnished 4-5 bedroom, 5½ bath oceanside home in beautiful Breeze Swept Beach Estates. Situated on an oversized 10,500 sq. ft. fenced lot, the property offers plenty of parking for boats, RV's, and jet skis. This custom home features 3,224 sq. ft. under air and an additional 1,276 sq. ft. of sunset and sunrise viewing decks, including a panoramic 360° view from the rooftop widow's walk. The expansive open-concept living, dining, and kitchen area features cathedral ceilings, creating a bright and inviting space. The updated kitchen boasts quartz countertops with a counter-to-ceiling quartz backsplash, stainless steel appliance

Home with a Pool for sale in Big Pine Key, FL:

There are very few places left in the Florida Keys where you can experience true waterfront privacy, EXPANSIVE acreage, protected dockage, open-water views, and direct boating access all from a single property. Blue Fish Point is one of those rare places. Set on an extraordinary 2.84-acre point lot on Big Torch Key, this represents a unique opportunity to own one of the Lower Keys' most remarkable private waterfront estates. Encompassing more than 1,000 feet of shoreline and surrounded by water on multiple sides, the property offers an unmatched combination of seclusion, natural beauty, boating convenience, and future potential. For serious boaters, anglers, and those seeking a private wate

Home with a Pool for sale in Big Pine Key, FL:

* Construction process underway. Expected completion November/December 2026 Embrace the ultimate Keys lifestyle in this spacious 1,500 sqft home, ideally situated along a boating canal in the Lower Florida Keys, and close to Key West! Tucked away in a quiet, peaceful neighborhood. Inside, the home features generous living space, providing ample room to stretch out and make it your own. Indoor-outdoor living is at its best here, with a private swimming pool just steps from the back door--perfect for unwinding after a day on the water or enjoying sunny Florida afternoons. For boaters, the canal location offers easy water access, along with the convenience of a 10,000-pound boat lift t

Home with a Pool for sale in Big Pine Key, FL:

Beach House Paradise in Summerland Key. Nestled in one of the Lower Keys' most desirable oceanside communities, this exceptional oceanfront retreat offers the perfect blend of luxury, privacy, and island living. A charming thatched-covered lanai and custom bamboo-etched glass doors welcome you into an open-concept floor plan where floor to ceiling windows frame breathtaking Atlantic Ocean views. The spacious living area flows effortlessly to an expansive waterfront terrace overlooking the pool, creating the ultimate indoor-outdoor lifestyle. Designed for entertaining, the lower level features a custom tiki-style bar, outdoor cooking area, hot tub, and multiple gathering spaces. Relax by the