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$819,500
3 Beds ⋅ 2 Baths ⋅ 621169 MLS
Welcome to 22968 Drake Lane -- a charming canal-front home located on the desirable Cudjoe Key, one of the Lower Keys' wonderful communities. Set on a generous 7,500 SF lot with direct canal access and a private boat lift, this property is a true dream for anglers, divers, and boaters looking to get out on the water in minutes. with quick access to the backcountry flats as well as the open water beyond. Inside, the approximately 1000SF living area feels bright and spacious thanks to high ceilings throughout the main living areas. The updated kitchen, featuring granite countertops and stainless steel appliances, perfect for entertaining or everyday island living. Glass sliders lead from the living area out to a large covered porch, where you'll enjoy a peek-a-boo open bay view -- an ideal spot for morning coffee, evening cocktails, or simply soaking in the classic Florida Keys lifestyle.Downstairs, an oversized garage which holds 2 cars and possibly more offers abundant space for vehicles, boats, kayaks, fishing gear, and all the toys that come with life on the water, plus additional storage to keep everything organized. Located on Cudjoe Key in the heart of the Lower Keys, this home offers a peaceful, laid-back setting while remaining just minutes from the vibrant restaurants, nightlife, and culture of Key West. Enjoy easy access to some of the best fishing, diving, and snorkeling grounds in the world, right from your own backyard.Whether you're searching for a full-time residence, a weekend retreat, or a smart investment in one of the most desirable stretches of the Florida Keys, this canal-front gem checks every box. Boat lift, water access, and some updated finishes at this price point are increasingly rare in the Lower Keys market -- schedule your private showing today before this one is gone! A Bonus, this one has the potential for a partial seller financing to the right Buyer and low insurances.

22968 Drake Ln, Cudjoe
$849,000
3 Beds ⋅ 3 Baths ⋅ 620998 MLS
CUDJOE KEY CANALFRONT SPECIAL - LOWEST PRICED HOME IN CUTTHROAT HARBOR ESTATES. ASSUMABLE MORTGAGE AT 2.75% MOTIVATED SELLERS SAY BRING ALL OFFERS!! Situated on over 6,000 Square Feet on a deep water canal - this recently updated property provides easy boating access to both the Gulf and the Atlantic, making it a perfect home base for world class fishing, diving, SANDBARS and enjoying the keys lifestyle. New Upgrades Include - Fully remodeled kitchen All impact doors and windows All new split AC Units New flooring New Tankless Water Heater Upstairs, you'll find the fully remodeled kitchen with island which is perfect for entertaining and walk out to a large deck space. 1 Large bedroom and recently remodeled bathroom. The lower level features two bedrooms with a living room and an office space!!! A simple door and kitchenette could provide an owners lockout dividing both floors. Ample size lot provides room for Boat/RV parking in addition to a lush tropical landscape that provides afternoon shade on the majority of the property. This deal will not last long so do not delay on owning your piece of paradise. CALL LISTING AGENT MIKE KANE DIRECTLY FOR YOUR PRIVATE SHOWING AND SAVE!!!!!

22832 John Silver Ln, Cudjoe
$2,195,000
5 Beds ⋅ 3 Baths ⋅ 620325 MLS
TRANSIENT LICENSE * NIGHTLY RENTALS* PROVEN RENTAL INCOME* IDEAL 1031 EXCHANGE OPPORTUNITY Casa De Las Palmas Rarely does a Florida Keys property combine proven income, privacy, and future potential like this. Situated on nearly two acres spanning four lots, this unique compound offers a coveted transient license allowing nightly rentals and a well-established vacation rental business with a strong history of performance. Historically generating over $200,000 annually, with recent projections ranging from $250,000 to $300,000, this is an outstanding opportunity for investors, vacation rental operators, or buyers seeking a premier 1031 Exchange replacement property. More than just a rental property, this is a proven income-producing asset with an established guest base, and delivering the authentic Florida Keys experience that visitors seek. Rather than starting from scratch, a new owner can step into a property with a successful operating history and demonstrated demand. The property features a 4-bedroom, 2-bath main residence, relaxing pool, expansive outdoor living areas, and a separate concrete guest structure complete with bedroom, bath, and kitchenette. Fully fenced with two private entrances, the grounds offer exceptional privacy, abundant tropical landscaping, fruit trees, palms, and ample space for RVs, boat trailers, and recreational equipment. Over 100 Palm trees Future upside may exist through additional development opportunities, expansion of the existing compound, or further enhancement of the guest experience, subject to buyer verification and applicable regulations. Properties offering a transient license, multiple lots, substantial acreage, proven income, and future potential are increasingly rare in today's Florida Keys market. Whether you're seeking a high-performing vacation rental, a strategic 1031 Exchange acquisition, or a private Florida Keys retreat, this property is positioned to deliver value and Solid ROI from day one.

125 Colson Dr, Cudjoe
$5,995,000
13 Beds ⋅ 7 Baths ⋅ 620213 MLS
Rare income-producing open-water compound on Cudjoe Key featuring 5 cottages plus a spacious main house. This gated, turnkey waterfront property offers direct open-water views, private dockage with ample boat space, on-site boat ramp, swimming pool, and lush tropical landscaping. Ideal for vacation rental income, corporate retreat, or private family compound. Each unit is well-appointed for guest comfort and positioned to maximize privacy. Excellent boating access to world-class fishing and diving. Strong investment opportunity in the Lower Keys with established income potential. Zoned Sub Urban Residential with one Buildable Sub Urban Commercial Lot, verify with the County. Included Parcel#'s Sub Urban Residential 00174920-000200, 00174920-000300, 00174920-000400, 00174920-000000, 00174920-000100, 00174920-000500. Sub Urban Commercial 00174920-000600. Owner is licensed Realtor. 5 (2 bedroom one bath cottages) and one (3 bedroom 2 bath house), 6 water meters, 6 electric meters. Heated salt water pool. The property is also listed with 9 additional units MLS #612522.

21470 Overseas Hwy, Cudjoe
$799,000
2 Beds ⋅ 2 Baths ⋅ 620174 MLS
SELLER ACCEPTING BACK-UP OFFERS: Discover your perfect boater's retreat in beautiful Cudjoe Key! This stilted 2-bedroom, 2-bathroom home is situated on a deep-water canal. Access to both the Atlantic and Gulf is easy and achievable in minutes, making it an ideal base for fishing, boating, and enjoying the Keys lifestyle. One of the home's standout features is its exceptional privacy. With no neighbors across the canal and no neighbors on one side, you'll enjoy peaceful water views and a secluded atmosphere rarely found in canal-front properties. Outside, the property features a 10,000-pound boat lift and davits, providing ample accommodations for your vessels. Downstairs, you'll find enclosed storage for all your gear along with covered parking. Mature tropical landscaping surrounds the property, creating a lush island setting. An RV hookup adds even more flexibility for guests and additional recreational vehicles. Inside, the home offers a wonderful open-concept layout. The kitchen features an abundance of hardwood cabinetry and a center island, creating an inviting space for cooking and entertaining. Off the living room, a spacious screened in deck is accessed through a fully opening sliding glass door, seamlessly blending indoor and outdoor living. High ceilings and beautiful cypress pine accents throughout the home add warmth and character, perfectly complementing the relaxed coastal lifestyle. Whether you're searching for a full-time residence, seasonal getaway, or investment opportunity, this waterfront gem combines privacy, character, boating amenities, and the relaxed island lifestyle that makes Cudjoe Key so desirable.

22822 Buccaneer Ln, Cudjoe
$895,000
3 Beds ⋅ 2 Baths ⋅ 620163 MLS
If you've been looking for the home you can live in while adding your personal touches to, you have found it. With 60' of composite dock on a 40' wide canal in a 3' control depth neighborhood, you can keep your boat right at your back door. This well-maintained home is in excellent condition and has been lovingly cared for by the original owner. With its metal roof, 240 mph vinyl siding, and Bahama shutters, this home is virtually maintenance-free and hurricane-resistant. Clean, solid, and move-in-ready, the only thing it needs is a little cosmetic updating to reflect your personal style. Come see it today and imagine making it your own.

135 Tortuga Ln, Cudjoe
$1,269,000
2 Beds ⋅ 2 Baths ⋅ 619922 MLS
Discover your personal sanctuary in the heart of Cudjoe Key, where authentic Florida Keys charm meets modern coastal luxury. This stunning 2-bedroom, 2-bathroom home has been thoughtfully updated to offer the ultimate waterfront lifestyle, just 21 miles from Key West's world-class dining and entertainment. The interior glows with natural light, highlighted by impact-resistant windows and elegant French doors leading to an open canal front balcony. The floor plan is designed for effortless living, featuring a sleek kitchen with a central island, 2025 updated Oven, Dishwasher, & microwave, remodeled bathrooms, a versatile bonus room, and a separate dining area that provides a front-row seat to the tranquil canal. For added convenience, the spacious walk-in closet includes an integrated washer and dryer, while a temperature-controlled thermostat and security system ensure year-round peace of mind. Perfectly situated for the avid mariner, the exterior features a concrete dock and a 10,000lb elevator boat lift. The lift currently accommodates a 2024 Boston Whaler 250 Outrage with twin 200hp Mercury Verado engines (no trailer), which is available for separate purchase. Enjoy a short, scenic canal ride from your backyard directly to the open ocean. Step outside into a secluded tropical retreat. The exterior boasts brand-new Hardie Board siding and a privacy fence encompassing an inground concrete pool finished with an elegant travertine pool deck. Beneath the home, a shaded entertaining space provides the perfect spot for lounging, complete with an outdoor shower and ample storage for kayaks, grill and water toys. Complete with a dedicated garage and plenty of parking, this property is the perfect home for family enjoyment as a primary residence or a seasonal retreat. Whether you are looking to make wonderful lifelong memories or simply wish to offset ownership expenses with a winter rental, this Cudjoe Key gem captures that sought-after ''Keys feel'' in every

116 Spanish Main Dr, Cudjoe
$949,000
3 Beds ⋅ 2 Baths ⋅ 619680 MLS
Where boating lifestyle and modern coastal design align, this fully renovated 3-bedroom, 2-bathroom home in Cudjoe Key delivers exceptional waterfront living. This completely reimagined residence is ideally positioned on a premier corner canal lot, offering approximately 190 feet of concrete seawall and dockage along two waterways, an exceptional setting for boating and waterfront enjoyment. Thoughtfully renovated throughout, the home showcases a clean coastal-modern design with new impact windows and doors, an elevated interior finish, and a beautifully updated kitchen featuring sleek cabinetry, premium surfaces, and an open layout ideal for entertaining. Light-filled living spaces flow seamlessly onto the newly replaced covered rear porch, where tranquil canal views create the perfect backdrop for relaxed indoor/outdoor living. The exterior stairs have also been recently replaced, complementing the home's refreshed and well-maintained feel. Boating enthusiasts will appreciate the 10,000 lb boat lift, expansive seawall/dockage, and quick access to open water via Cudjoe Bay. Downstairs, a large enclosure provides abundant storage space for tools, fishing gear, and boating equipment, an invaluable feature for Keys living. Located on a quiet street in an established neighborhood, this property offers a rare combination of modern updates and generous waterfront in the Lower Florida Keys.

22953 John Silver Ln, Cudjoe
$1,725,000
4 Beds ⋅ 3 Baths ⋅ 619558 MLS
Oceanfront living on Cudjoe Key, where broad covered balconies, generous outdoor space, and a private boat launch put Keys waterfront life within reach. This four-bedroom, three-bath home is a study in coastal architecture -- large impact glass doors and windows frame open water views and pull natural light into every room. Soaring 26' ceilings and rich wood beams anchor the open-concept main level, which includes a renovated kitchen, dining space, living room, laundry, and two bedrooms with two full baths. Upstairs, a third bedroom sits at the top of the stairs, and a catwalk leads to the fourth bedroom with ensuite bath and a walkout deck framing panoramic open water views. The home has been restored to its former glory with modern updates layered in -- rustic accents meet open, light-filled spaces that let the oceanfront setting do the talking. Adjacent lot also available for even more ocean enjoyment. Seller financing available: 50% down, 6% for 15 years, no flood or wind insurance required. This home needs to be seen to be fully appreciated. Schedule your showing today.

22542 Jolly Roger Dr, Cudjoe
$875,000
2 Beds ⋅ 1 Baths ⋅ 619325 MLS
Ocean side location enjoy diving , fishing, dining from your boat come home to relax on your deck watching the sunset. Open floor plan new upgrades throughout.Several pictures added with staged furnishing for you to see what rooms could look like.Extra large property with plenty of room for your R/V, boats. Your own boat launch with plenty of dockage on your concrete seawall. Beautifully landscaped. Two large storage sheds with additional interior storage underneath the home. Here is a piece of paradise to grab and hang onto too. Only 20 minutes to Key West. Seller motivated Seller is motivated to sell this one of a kind location with private boat ramp with 90 feet of concrete seawall. Very large property* Plenty of room for all your requirements can keep R/V , boat trailer, extra vehicle and more* OCEAN SIDE* Some of the best boating opportunities in the Florida Keys* New Price to sell ASAP

22978 Port Royal Ln, Cudjoe
$5,995,000
13 Beds ⋅ 7 Baths ⋅ 618705 MLS
Rare income-producing open-water compound on Cudjoe Key featuring 5 cottages plus a spacious main house. This gated, turnkey waterfront property offers direct open-water views, private dockage with ample boat space, on-site boat ramp, swimming pool, and lush tropical landscaping. Ideal for vacation rental income, corporate retreat, or private family compound. Each unit is well-appointed for guest comfort and positioned to maximize privacy. Excellent boating access to world-class fishing and diving. Strong investment opportunity in the Lower Keys with established income potential. Zoned Sub Urban Residential with one Buildable Sub Urban Commercial Lot, verify with the County. Included Parcel#'s Sub Urban Residential 00174920-000200, 00174920-000300, 00174920-000400, 00174920-000000, 00174920-000100, 00174920-000500. Sub Urban Commercial 00174920-000600. Owner is licensed Realtor The property is also listed with 9 additional units MLS #612522.

21470 Overseas Hwy, Cudjoe
$12,999,999
31 Beds ⋅ 19 Baths ⋅ 612522 MLS
Located on Cudjoe Key, only 20 miles from Key West. Transient use property, over 3.5 acres, 15 units (15 ROGO exemptions) over 300 feet of water frontage, boat basin, 3 concrete docks, one wooden dock, boat ramp. Excellent rental history, shared coin laundry, 2 swimming pools. 2 parcels on US 1 are zoned Sub Urban Commercial, 3 private driveways. Property spans from US 1 to the Atlantic Ocean. Owner is licensed Realtor. Please do not walk on the property without an appointment. Seller is licensed Realtor

21540 21470 Overseas Hwy, Cudjoe