Zip codes 33042 listings for sale

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$21,900,000 - Summerland Key, FL
0 Howell Key Summerland Key, FL - Welcome to Howell Key! This unique island oasis, purchased in 2010, was developed as an off-grid, private family retreat for a multi-generational remote getaway. Now, this breathtaking 9.69-acre turnkey opportunity is on the market, inviting you to live your offshore island dream or invest in a one-of-a-kind vacation rental experience. Situated off mile marker 25 in Summerland Key, Florida Keys, Howell Key is just a 5-minute boat ride from your private masterpiece. With direct access to both the Atlantic Ocean and the Gulf of Mexico, your watersport dreams can come true daily. Proximity by boat is close to Looe Key National Marine Sanctuary, many sand bars, and the famous 5-star Little Palm Island Resort and Spa. This inviting island sanctuary features dockage accommodating vessels up to 50 feet and an electric gate leading to the marina lagoon. The energy-efficient, immaculate five-bedroom, four-bath home boasts a saltwater pool, exposed beam ceilings, travertine tile throughout, and SIPS panel technology construction. Additional structures on Howell Key include a guest house, garage, animal pens, pickleball court, tiki hut with beach, helipad, and finger dock with a covered sitting area. Plus, a second ROGO-exempt permit allows for constructing another dream home. This is a completely turnkey, fully furnished property that provides a peaceful, tropical escape from the ordinary. This purchase includes a Shore Station Lot completely fenced in to leave vehicles and has a 58' seawall to accommodate your personal ferry. Full list of amenities included in the documents tab.
2012 | 5 | 4 | 3,392 sqft.
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$8,455,000 - Summerland Key, FL
1151 Ocean Drive Summerland Key, FL - TROPHY OCEANFRONT ESTATE! This one-of-a-kind luxury estate offers an unparalleled coastal lifestyle on 120 feet of prime oceanfront. Designed for the discerning buyer, this breathtaking property combines elegance with the ultimate boating experience.The centerpiece of this estate is the 120,000 lb boat lift, capable of accommodating a 70 ft yacht--a rare find in the Keys. The property also features a private mooring buoy, 2 additional boat lifts, and a private boat basin equipped with a compressor-operated bubbler system to keep seaweed at bay. With exclusive bay bottom rights, it's a true boater's paradise, offering the perfect space to keep your vessels safe. Inside, the estate is a showcase of luxury. It features 5 spacious bedrooms, an exercise room, 4 full baths, and 2 half baths, all thoughtfully designed for comfort and style. The main living area boasts vaulted ceilings and opens onto a massive tiled patio surrounding a raised pool and spa. This elevated design allows for a seamless flow between indoor and outdoor living, complete with a covered bar area for entertaining and breathtaking panoramic views of the Atlantic Ocean and Little Palm Island.The chef's kitchen is equipped with high-end appliances and an open layout, perfect for grand gatherings. A separate dining area is adjacent to the kitchen and living area. There is a laundry room and the 5th bedroom is currently set up as an office for added flexibility. The single-car garage provides peace of mind for your vehicle, large storage area under the house.Set on an expansive 37,400 sq. ft. lot, this estate is beautifully landscaped, resembling a resort with lush tropical gardens. A desalination plant and backup generator ensure complete self-sufficiency, while the private beach offers your own slice of paradise. This is a trophy property with unmatched boating capabilities and luxurious living. Don't miss your chance! Schedule your private tour today! Video tour https://tinyurl.com/1151Ocean
2007 | 5 | 5 | 3,952 sqft.
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$5,999,000 - Big Torch Key, FL
4500 Filer Cove Road Big Torch Key, FL - Picture perfect Sunset Views over the open water at this 12-Acre waterfront compound located on Big Torch Key, a coastal community of large private estates located just 30 minutes outside of Key West. Driving down the gated 300' scenic driveway balmy breezes and tropical landscape lead you to the 4,315 sq. ft. open water residence. Once here you will enjoy world-class fishing and diving just minutes to the Ocean and Gulf from the protected canal front dockage complete with concrete dock, davits and boat house for gear storage. With over 2,000' of waterfront there is a massive amount of room for all of your toys. After a day out on the water you will want to play in your brand new infinity pool overlooking Keys famous sunsets over the open water and accessed directly from the Great Room. In the evening friends and family can gather on the pool side Porch or in the colossal Great Room featuring soaring ceilings and stunning views of the water while you cook up your catch in the Chef's Kitchen offering abundant cabinetry, breakfast bar, large pantry and premium appliances. At the end of the day Guests will retire in the main house Guest Suite or for more privacy in the separate 1,052 sq. ft. 2 Bedroom Guest Cottage while you retire in the 1,333 sq. ft. 2nd Story Master Suite, accessed by a grand cherry wood staircase or elevator, with private veranda overlooking the water. 2 roof top decks, one for garden and the other to view 360 degree panoramic views. The 12-acre property is completely private and has lots of amenities including paddle board and kayak access, nature trails, and waterfront Tiki to take in those wonderful sunsets.
1994 | 4 | 4 | 4,315 sqft.
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$5,992,000 - Summerland Key, FL
220 E Caribbean Drive Summerland Key, FL - Experience unparalleled luxury in this Brand New 2025 Custom Built Smart Home. 6,128 SQ FT concrete-constructed oceanfront home, situated in prestigious Summerland Key. With 90 feet of ocean frontage and breathtaking southwest views of the Atlantic Ocean, this home is the ultimate retreat for those seeking elegance, comfort, and adventure.The third floor is the heart of this home, featuring an infinity-edge pool and spa that frame magnificent sunsets and ocean vistas. Seamlessly blending indoor and outdoor living, the expansive entertainment areas promise unforgettable gatherings. This magnificent custom home offers five spacious bedrooms with ensuite bathrooms, including a dual primary suite that can serve as a 6th bedroom or an office. Additional features include: A state-of-the-art sound proof home theater room with Marantz 11.2 surround sound, 16' screen, and 8K JVC projector.Custom Canadian birch cabinetry and Thermador WiFi-enabled appliances throughout. A boater's Paradise
 designed for water enthusiasts, the property features: Two boat lifts (25,000 LB and 10,000 LB), A 6' x 90' concrete dock with two tiers for jet skis and kayaks. Deepwater access with a 90' wide, 28' deep channel leading directly to the Atlantic and Gulf.Proximity to world-class snorkeling and diving at Looe Key Coral Reef.Unmatched durability and sustanibility, built to exceed 180 MPH wind loads, solid concrete floors, walls & roof.This home includes: All high-impact Marvin & Euro-Wall windows and doors.70 solar panels (34.5 KW of power) and 4 Tesla Power Walls 57.6KW powers home.Three on-demand hot water systems and a 10,000-gallon rainwater cistern.Exceptional features include; Private elevator servicing all three levels. RV/Boat garage (15' W x 50' D x 14' H) with 50 AMP/220V service. Tesla charging station. WiFi-enabled smart home systems, including AC, pool pumps, and appliances. See Documents Tab / Possible Seller Financing.
2025 | 5 | 6 | 4,981 sqft.
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$5,500,000 - Summerland Key, FL
481 E Shore Drive Summerland 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 views, and access to a private airport for island residents less than two blocks from the property.Don't miss this unparalleled investment opportunity!Please note that I have a personal interest in this property.
1992 | 3 | 3 | 2,088 sqft.
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$3,795,000 - Sugarloaf Key, FL
16705 Tamarind Road Sugarloaf Key, FL - Exquisite Open Water Estate on Prestigious Southpoint, Sugarloaf Key! Experience unparalleled luxury at this stunning solid concrete open water property, located just 20 minutes from the magic of Key West and Key West Airport. Situated on prestigious Southpoint, Sugarloaf Key, this magnificent estate offers breathtaking open water views and a lifestyle of elegance and comfort.Spanning 3,086 square feet of refined living space, this home features 3 bedrooms, 2 bathrooms, plus a versatile office/den and a large laundry room. The expansive 19,300 square foot lot is a tropical paradise, beautifully landscaped with fruit trees, an orchid house, landscape lighting, and irrigation from cisterns.Step inside to discover poured concrete floors that exude modern sophistication. The chef's kitchen is a culinary dream, equipped with Miele appliances and a Sub-Zero refrigerator. Entertain with ease in the separate bar area and enormous living space. The property also boasts a ducted vacuum system and a commercial-grade metal roof for added convenience and durability. Outdoor living reaches new heights with a stunning new pool, featuring a long ledge perfect for relaxing with cocktails. The large tiki hut serves as an outdoor lounge, complimented by a separate bar area under the house adjacent to the pool. The dock and boat lift provide direct access to the open water, making this home a boater's dream. Enjoy the convenience of an elevator, granting access from the garage and ground level to all floors. The rooftop deck offers 360-degree views, including vistas of the open ocean, perfect for sunset soirees or stargazing nights. This estate is designed for the discerning luxury buyer, offering the perfect blend of sophistication, comfort, and tropical charm. Don't miss the opportunity to own a piece of paradise on Sugarloaf Key! Low Insurances. Call for your private showing today! Video tour https://tinyurl.com/16705Tam
2015 | 3 | 2 | 3,086 sqft.
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$3,599,000 - Cudjoe Key, FL
20816 W 4Th Avenue Cudjoe Key, FL - LUXURY COLLECTION WATERFRONT ESTATE in the prestigious Cudjoe Gardens. A STUNNING TURNKEY PARADISE, SOLD AS IS WITH HIGH END DESIGNER FURNISHINGS & DECOR FROM RESTORATION HARDWARE, POTTERY BARN, & SERENA AND LILY. ALSO 2 HOBIE CATS. This Custom Built Home with a total of 5,373sf under roof is a masterpiece blending luxurious design with the serene beauty of the Florida Keys. Built on a sprawling waterfront ELEVATED corner lot of 16,500sf with 260FT of water frontage and deep draft. This gorgeous property offers an unparalleled tropical lifestyle, perfect for those who demand the best in comfort and elegance.Property Highlights4 Bedrooms + 5th Bedroom/office, Spacious, sunlit rooms designed for relaxation and productivity, including a versatile office or creative studio space which could be a 5th Bedroom.4 Full Bathrooms: Impeccably designed with high-end fixtures and finishes.Gourmet Kitchen: A chef's dream, featuring state-of-the-art appliances, custom cabinetry, and expansive Quartz countertops ideal for entertaining.Imported Italian & Moroccan Flooring: Stunning, high-quality flooring that enhances the luxurious ambiance throughout.12-16 Ft Ceilings: Create an open, airy feel while showcasing architectural sophistication.Saltwater Pool: Dive into the generously sized, chilled & heated concrete pool with water feature, lights and lounging platformOutdoor Kitchen: Stainless Steel Appliances, Spacious layout, Perfect for entertaining.2 Boat Lifts, 20k and 10kAdditional Amenities3 A/C Units: Individually climate-controlled zones, including the 3-car garage for comfort and convenience.Full Property Generator, 1000 gallon Propane Tank, Full Security System, Phantom SunShades for Screened in PorchThis meticulously designed property combines sophisticated interiors with exceptional outdoor living spaces. Located in a prime area of Cudjoe Key, this home offers privacy, stunning water views, and direct access to the pristine waters of the Lower K
2021 | 5 | 4 | 3,817 sqft.
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$3,500,000 - Cudjoe Key, FL
22815 Port Royal Lane Cudjoe Key, FL - DIRECT OCEAN FRONT - BOATERS PARADISE FOUND with room for 3 Boats on unobstructed sunset view over open water - oversized corner lot with water on 2 sides at end of a private road offering picture perfect sunsets in a protected bay! Boasting 323' of water frontage, includes 175' of open water and 148' of canal frontage featuring a 90' concrete dock, and a private kayak launch. The main level of the home features a wrap-a-round deck, a spacious living area, including 2 owner retreats, bathroom with jacuzzi tub, separate shower & his & hers vanities, 2nd bedroom, half bathroom and a chefs kitchen with Sub Zero Fridge. The third level has a private bedroom, bathroom and balcony accessible by a spiral staircase with ocean views. On the opposite side of the home is a private mother-in-law/teen suite that could be separated and or rented separately with an open floor plan that includes a large living area, 2 Story tongue & groove West Indies Great room w/wet bar and it's own updated kitchen with brand new SS appliances overlooking the water! Smart home panels & security cameras thruout. Outdoor living including new Giant 16ft Swim Spa w/55 jets, blue tooth ss & fiber optic lights that fits 14 people, outdoor sun TV, pool table, lounge chairs, multiple hammocks & grill. Boat Dockage is super with room for up to 42 ft boat plus a floating 2 Jet Ski Dock! Plenty of parking underneath 12ft concrete pillars for all the guests w/an efficiency for storage as well! Easy access with channel directly in front of home, super fishing spots & reefs! 20 mins to Key West w/plenty of shopping, Nightlife and super restaurants. Home was recently tented, has fresh paint, lighting, updated electrical, plumbing, hot water heater, new HVAC's 2025. Home is entirely fenced & Gated w/privacy PVC fencing. The best of all is the wide open water & gorgeous sunset views! Income producing 5 Star Air Bnb Rating! Seller Financing Avail at 4% RATE - Owner / Agent
2013 | 4 | 4 | 3,228 sqft.
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$3,500,000 - Lower Keys, FL
815 E Shore Dr Lower Keys, FL - SELLER FINANCING AVAILABLE!!! Paradise awaits at this stunning 7-bed, 6-bath waterfront estate in Summerland Key! Designed for luxury, privacy & adventure, this resort-style retreat boasts breathtaking open-water views, a private boat basin, and high-end amenities—just moments from exclusive Little Palm Island. Spanning 4,531 sq ft, (Spanning 4,531 sq ft, (12,603 sq ft gross) the main house features soaring cedar ceilings, ocean views & seamless indoor-outdoor living. A private suite, two guest bedrooms, two cottages & a widow’s peak lounge offer space for all. Enjoy a 3-tier heated/cooled pool, boat lift, tiki hut, shuffleboard & more. Upgraded with impact windows & mini-splits, this is ultimate Keys living. Schedule your tour! Monthly rental—do not walk property. (See Supplement)
1961 | 7 | 5 | 4,531 sqft.
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$3,499,000 - Cudjoe Key, FL
653 Sawyer Drive Cudjoe Key, FL - Spectacular Oceanfront Retreat with canal front dockage! Experience the ultimate in Keys living at this beautifully renovated 3 bedroom, 2 bath oceanfront oasis with an additional canal-front lot featuring boat dockage just across the street. This smart, solar-powered home with 6 Tesla Powerwalls, 2 EV chargers, plus an annual check for excess energy production offers eco-conscious luxury with remarkably low electric bills. Enjoy breathtaking ocean views from your private pool and raised spa, entertain effortlessly in the multiple outdoor living spaces, launch kayaks and paddleboards from your own sandy beach, or relax in the tropical breeze surrounded by lush landscaping.Inside, no detail has been overlooked. The home boasts hurricane impact doors and windows, new plank floor, and a fully updated designer kitchen with center island and exquisite lighted quartzite countertops. Wake up to stunning ocean views from the Primary Suite complete with custom built-out walk-in closet and beautifully updated bath. Offered turn key, this smart home seamlessly blends modern convenience with coastal charm. Kayaks, Paddle Boards and 2 almost new (less than 10 hours) 2022 Sea Doo GTX 300 Jet Ski's are also included in the sale to make this a fantastic vacation rental from day 1! Don't miss this rare opportunity to own a move-in-ready oceanfront property with additional dockage and lot included plus lot of toys--a true Florida Keys gem!
1995 | 3 | 2 | 1,714 sqft.