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Big Pine Key Waterfront Homes on the Bay / Gulf Side of the Island For Sale

Total Listings 51
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$1,750,000
Big Pine Key
Pine Channel Estates   - MM: 29.50
2 Bed, 2 Baths, 1,444 SqFt Days Listed: 26
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits125ft.Concrete

15,500 SQ. FT. DOUBLE LOT in desirable Pine Channel Estates - bordered by areca palms providing a bit of privacy, the corner property offers an impressive 125 ft. of concrete seawall with a step-down dock and davits, and 20 ft. of concrete seawall across the end of the canal. The CBS home sits approximately in the middle providing elbow room all around - theres plenty of space for adding a pool, parking an RV, boat trailer and more. A huge, screened porch across the back overlooks the canal; 16 ft. pocket sliders open from the great room to the porch for extended outdoor living. 1444 sq. ft. of living area, 2BD/2BA with the potential to add a 3rd bedroom. Additional features include a convenient walk-around porch, covered parking, attractive paver drive, storage enclosure, metal hip roof. Excellent boat access to the ocean or back country for fishing and diving, and its a short boat ride across Pine Channel to the dock at Kikis Sandbar & Grille for lunch or dinner and music. Gorgeous sunsets can be enjoyed nightly as one looks down the length of the clean, deep canal. Add your personal touch and updates to create your exceptional piece of Keys paradise! Just 30 miles to Key West.

$1,750,000
Big Pine Key
Tropical Bay   - MM: 30.50
3 Bed, 3 Baths, 1,902 SqFt Days Listed: 49
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Fixed Brid

Welcome to Your Dream Home!Step into this exquisite custom-built residence, crafted with precision and style. This CBS (Concrete Block Structure) home boasts a pristine design with:Three Spacious Bedrooms & 2.5 Luxurious Baths: Perfect for family living and hosting guests. Impressive 10-Foot High Ceilings: Create an open, airy atmosphere throughout. Custom LED Lighting: Elegantly illuminates the space and enhances the modern ambiance.Chefs Delight Kitchen: Features Blue Bahia Quartz/Granite countertops and matching window sills, offering both beauty and functionality.Impact Windows and Doors: Provide security and energy efficiency while maintaining the homes sleek look.Travertine Floors: Add a touch of sophistication and durability.Paver Driveway: Welcomes you to your home with style.40 x 10 ft Concrete Dock: Equipped with a 15,000 lb boat lift, perfect for boating enthusiasts. Tropical Landscaping: Creates a serene, private oasis for relaxation.Easy Access to Both Ocean and Gulf: Via the scenic Bogie Channel, ideal for waterfront living. Experience luxury, convenience, and unparalleled beauty in this extraordinary home. Its not just a house; its your new lifestyle.

$1,875,000
Big Pine Key
Tropical Bay   - MM: 30.50
2 Bed, 2 Baths, 1,980 SqFt Days Listed: 24
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat LiftConcrete

Waterfront Paradise in Tropical Bay EstatesExperience luxurious open-water living in this beautifully remodeled home overlooking the stunning Bogie Channel. Wake up to breathtaking sunrises, enjoy magical moonlit waters, and explore world-class fishing and lobstering right from your 75-foot seawall with an 8-foot-deep boat slip.This 2,000 sq. ft. open-concept home features water views from nearly every room, a serene primary suite with private sitting area, and a chefs kitchen with a 4x8 granite island. The Florida room offers panoramic vistas, while the lush backyard boasts a pool, grassy space, and visits from Key Deer.With impact windows, shutters, a new metal roof, and a 2019 remodel, this home is move-in ready and perfect as a family retreat or high-end rental. Call today for your private showing!

$2,200,000
Big Pine Key
Pine Channel Estates   - MM: 29.50
4 Bed, 4 Baths, 2,808 SqFt Days Listed: 310
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift75ft.Concre

Step into over 2800 sq ft of luxurious living space in this tropical oasis. Nestled close to the open waters, this home boasts 75 ft of dockage on a crystal-clear, deep canal.This turnkey home is a complete package, offering all furniture, artwork, kitchenware, bedding, and more. Enjoy leisure time in the large 2nd story bonus living area with a pool table and included televisions.For boating enthusiasts, theres a boat lift and jetski lift, as well as a concrete seawall for added convenience. With no neighbors on either side, privacy is paramount.The property features impact-resistant doors and windows, a metal roof, and assumable flood insurance, keeping insurance costs low. A brand new Generac 24KW Whole House Generator with 2 propane tanks ensures the home remains powered for up to 5 full days.Outdoor entertaining is a breeze with a Lynx Barbecue Grill and Traeger Smoker Pro Series, both brand new.This home is impeccably maintained and truly one-of-a-kind in the lower keys. Just bring your flip flops and bathing suit, and youre all set for the ultimate tropical lifestyle!

$2,300,000
Big Pine Key
Doctors Arm   - MM: 30.50
4 Bed, 4 Baths, 2,400 SqFt Days Listed: 710
+15.00% ($300,000) 1 Price Change : Last Change 269 Days Ago
Under Constru - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Dock Privileges

UNDER CONSTRUCTION NOW! Luxury water view home with an in-ground pool on a 14,680 sq ft lot with boating access. Brand new single level elevated CBS home over parking. Impact windows and doors, metal roof, 10-foot interior ceilings,stainless appliances and much more. Construction is nearing completion; dont delay!Get it under contract soon and customize your finishes!

$2,395,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
3 Bed, 3 Baths, 2,295 SqFt Days Listed: 216
-2.60% ($64,000) 1 Price Change : Last Change 144 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Fixed Brid

Located on the West Side of the Island with excellent boating access this beautiful pool home is an entertainers dream place. Stunning Sunsets & Sparkling waters for swimming, snorkeling, paddleboarding .... Home features 3 bedroom suites with full baths plus a powder room too. Impact doors and windows, tile floors throughout, Viking appliances, chefs kitchen, wet bar, icemaker & additional drink fridges. Large Tiki Hut with fans, concrete heated pool and chiller too. Bring your big Boat and Smaller one too.....2 boat lifts (20K and 12K), boat house, outdoor shower, swat mosquito system, RV hookup, Terminix warranty, video surveillance, large storage shed, full home surge protection, ample storage inside and out. All tropically landscaped, paver driveways & yard fenced for your pets and privacy. Full concrete seawall & covered boat slip. Home is offered mostly furnished and outdoor furniture is included too. Location! Location! Location!

$2,500,000
Big Pine Key
Punta Brisa   - MM: 31.00
3 Bed, 3 Baths, 1,890 SqFt Days Listed: 170
-21.88% ($700,000) 4 Price Changes : Last Change 1 Day Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Ramp,Other Dock

MOTIVATED SELLERS all offers considered! Smugglers Cove is keys living at its finest, nestled in the mangroves exuding privacy. This unique gated custom-built waterfront property is located on Bogie Channel with easy access to the Gulf & Atlantic. Offering split level living with legal ground level accommodations featuring stainless steel appliances, induction stove, a hammered copper farmhouse style sink, and a distinct 16 concrete countertop, custom bath with washer and dryer. The second floor is the master suite; with its own petite kitchen area, living room, office, bonus room, and separate washer and dryer. This is a dream property for fishing & lobster enthusiasts or nature lovers, you are surrounded by a wildlife sanctuary! Moor your boat up to the jetdock with seagate or out of the water onto the custom jetdock with kayak launch in your private 20ft deep boat basin/lagoon brimming with sea life. The owner is including 2 kayaks & Penn fishing poles. This stunning property features 2 private beaches, a 60ft pool, and a hot tub island which is encompassed by bamboo to allow absolute privacy. You will enjoy lush mature landscaping with automated irrigation to make upkeep easy. This property is equipped with state of the art security system, fully customizable solar lighting, a 6 fence, circular drive offering ample off street parking to accommodates all of your guests and has plenty of space for a RV and all of your toys! Life Is Great Behind The Gate! Workshop, bar, banquet, bbq area and greenhouse. 10% allotment to add on is also available, buyer to verify.

$2,600,000
Big Pine Key
Eden Pines Colony   - MM: 29.00
5 Bed, 5 Baths, 2,447 SqFt Days Listed: 2
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat RampConcrete

Escape to paradise! 5BR/3.5BA gated home in the Keys. Bamboo floors, fresh paint, screen patio. Elegant accents. Lush landscaping, private pool, hot tub. 2 levels, full bar, gourmet kitchen, walk-out patio. Master w/ walk-in closet. Stargaze from wrap-around porch. Must see this private oasis!

$2,900,000
Big Pine Key
Palm Villa   - MM: 30.50
3 Bed, 3 Baths, 2,486 SqFt Days Listed: 19
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift460ft.

The laid-back Lower Keys are calling you.... experience life at a slower pace on this .81 acre open water estate with a 2-bedroom, 2-bath main house as well as a 1-bedroom, 1-bath guest cottage overlooking Bogie Channel. Entertain in the large, poolside tiki or on the covered platform at the end of the 463 ft. pier where family and friends can relax as they watch the sunset after a fun day on the water. The platform is equipped with a boat lift, floating jet ski dock and outdoor kitchen. Completely renovated, the 2-story CBS primary home offers the potential of adding a 3rd bedroom in the 1,950 sq. ft. living area.* Expansive impact-resistant windows capture spectacular sunrises and moonrises over the sprawling grounds and open water. Also nestled on the property is the renovated 536 sq. ft.*, frame-stucco guest cottage where your visitors can have their own space. The 35,330 sq. ft. property is fenced and accented by well-planned lighting. Monroe Countys quiet Palm Villa Park borders the south property line; the county also owns the large parcel to the north across the street with the intention of leaving it undeveloped. Tastefully furnished and move-in ready, this peaceful piece of paradise is just minutes from local shopping and eateries, yet only 30 miles from the excitement of Key West. *Source: Property Record Card

$3,500,000
Big Pine Key
Dolphin Estates   - MM: 33.00
3 Bed, 3 Baths, 1,020 SqFt Days Listed: 244
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Other Dockage200ft.C

Rare Waterfront Property on No Name Key: Your Gateway to Natural Florida Keys Living. Are you seeking privacy, breathtaking open water views, and exclusive boat dockage? Look no further than this exceptional offering nestled in the heart of the Natural Florida Keys. Situated on the private and secluded No Name Key, just a stones throw away from Big Pine Key, this nearly 2-acre property presents a unique opportunity to own a slice of paradise.Key Features: 2 Acres of Open Water Bliss: Comprising four parcels of land, including two zoned for Commercial Fishing Special District , this property offers versatility and potential for various uses. Whether you envision it as a private retreat or a commercial venture, the possibilities are endless. Protected Deep Water Boat Basin: Boasting a secure deep-water boat basin with direct access to Bogie Channel, this property is a boaters dream. Enjoy seamless navigation to the backcountry, Gulf of Mexico, and Atlantic Ocean, with Bahia Honda and the iconic 7 Mile Bridge just a quick boat ride away. The basin can accommodate multiple vessels with 200 of dockage already, this boaters paradise comes equipped with a permit for an additional 330 feet of concrete seawall and four 3-foot by 25-foot finger piers.Spectacular Waterfront Views: Lot 4 features an existing 3 bedroom 1 bathroom house with nearly 270 degrees of unobstructed open water views. If you prefer to build your dream home, build it on lots 1&2 and keep 3&4 for commercial fishing. Wake up to mesmerizing sunrises and unwind with picturesque sunsets. Your Gateway to Endless Possibilities:Whether youre seeking a tranquil retreat, a commercial endeavor, or the ultimate waterfront sanctuary, this property offers unparalleled opportunities. With plans underway for a new home, you can customize your perfect haven amidst the serene beauty of the Florida Keys. Dont miss out on this rare chance to own a piece of paradise with the very few areas for commercial fishing.

$4,999,500
Big Pine Key
Pine Channel Estates   - MM: 29.50
4 Bed, 4 Baths, 2,812 SqFt Days Listed: 41
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift50ft.

LUXURY LIVING IN THE LOWER KEYS where the pace of life is a bit slower, and the fishing and diving are exceptional. The 16,875 sq. ft. property features 150 ft. of frontage along a 46 ft. wide canal, a 50 ft. concrete dock, and two boat lifts (the larger lift is 21,000 lbs.) Its a private, tropical setting where one can relax under the tiki or in the heated, salt system pool, enjoy down time in the hot tub, and entertain on the primary canal-side porch overlooking protected lands across the canal to the north. This impressive home offers 2812 sq. ft. of living area and an open floor plan with cathedral ceilings, wall-to-wall glass doors and windows in the great room, a formal dining area, a study that can easily be a fourth bedroom, and a master suite with water views. For guests theres a two-bedroom, one-bath wing boasting its own laundry room and canal-side porches. 3-zone central air and heat. Spacious two-car garage and ample ground level storage; plenty of space for guest parking and room to park your motor home and boat trailer. Fly privately into the Marathon International Airport or commercially into Key West International Airport.

The information being provided by the Florida Keys MLS is exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. Data last updated on 01-04-2025.
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