Cudjoe Key Homes with Updated/Remodeled Property Condition

Cudjoe Key Homes with Updated/Remodeled Property Condition

Welcome to Cudjoe Key, a hidden gem nestled in the heart of the Florida Keys, within Monroe County. This enchanting island, known for its serene beauty and vibrant marine life, offers an idyllic escape for those seeking a slice of paradise. Just a short drive from the bustling city of Key West, Cudjoe Key boasts a tranquil atmosphere, making it the perfect destination for relaxation and adventure alike.

The real estate landscape in Cudjoe Key is thriving, particularly with homes that have been beautifully updated and remodeled. Imagine stepping into a modern sanctuary that seamlessly blends style and comfort, where every detail has been thoughtfully curated. From open-concept living spaces bathed in natural light to gourmet kitchens equipped with the latest appliances, these homes reflect a perfect harmony of luxury and functionality.

Many properties in Cudjoe Key feature stunning outdoor spaces, where you can soak in the breathtaking views of the surrounding waters or host gatherings with friends and family. Whether it's a charming waterfront cottage or a spacious family home, the updated properties here offer a unique opportunity to experience the laid-back island lifestyle without compromising on modern conveniences.

With its stunning sunsets, abundant recreational activities, and a close-knit community, Cudjoe Key is more than just a place to live; it’s a lifestyle choice. Whether you’re looking for a vacation retreat or a permanent residence, the homes in this picturesque island community promise a life filled with beauty, adventure, and tranquility. Discover your dream home in Cudjoe Key today!

Newest Cudjoe Key Homes with Updated/Remodeled Property Condition

111 Doubloon Ln, Cudjoe
$850,000
2 Beds ⋅ 2 Baths ⋅ 621355 MLS
Welcome to island waterfront living on desirable Cudjoe Key! Situated on an amazing corner lot, this beautifully maintained 2-bedroom, 2-bath home offers the perfect combination of comfort, convenience, and easy access to both the Atlantic & Gulf. Inside, you'll find an updated kitchen featuring beautiful cabinetry, granite countertops, vaulted ceilings and plenty of space for entertaining. Impact-resistant windows and doors provide added protection and contribute to the home's low insurance costs. Gorgeous screened in porch and outdoor shower overlooking the canal. Generous storage throughout makes it easy to keep all your fishing, boating, and island-living essentials close at hand. Boaters will love the quick access to open water, making it easy to spend your days fishing, diving, or exploring everything the Florida Keys have to offer. The oversized corner setting provides additional space and privacy while capturing the relaxed tropical lifestyle Cudjoe Key is known for.

111 Doubloon Ln, Cudjoe
22968 Drake Ln, Cudjoe
$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
1106 Thatch Ln, Cudjoe
$2,099,000
4 Beds ⋅ 4 Baths ⋅ 621161 MLS
Set along a peaceful canal on Cudjoe Key, this 2016 residence pairs solid CBS construction with an unmistakably elevated sense of island living. This 4 bedroom, 3.5 bath home features impact windows and doors and a standing seam metal roof, speaking to a level of craftsmanship built to endure, while 2,548 square feet of living space and roughly 1,370 square feet of balconies invite the surrounding water views and tropical air into everyday life. The main level is designed for both privacy and gathering, offering 3 guest bedrooms, 2 full baths and a laundry room alongside a second living area that opens onto a spacious covered balcony. One bedroom enjoys its own ensuite, while the remaining two share a well-appointed Jack and Jill bath. Ascend to the main living level and the home opens into a bright and airy Great room where kitchen, dining and living areas unfold together. Anchored by a substantial island and dining bar, the kitchen is finished with Silestone countertops, a sea glass tile backsplash and abundant custom cabinetry. Beyond, another expansive balcony extends the living space into the open air, ideal for evening entertaining or a quiet morning coffee. The primary suite occupies its own private wing upstairs, offering generous closets and a spa inspired ensuite with a jetted tub and separate walk-in shower. Outside, a heated and chilled concrete pool sets the stage for effortless indoor-outdoor living, while a 30-foot concrete dock with lighting and bubblers provides canal access for boating, paddling or an evening line in the water, with the open water just minutes beyond. Located just minutes from local restaurants, shopping and coffee shops, this a rare balance of quality, privacy and island sophistication, backed by a proven rental history that makes it as compelling an investment as it is a home.

1106 Thatch Ln, Cudjoe
22832 John Silver 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
116 Spanish Main Dr, 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
22939 Gasparilla Ln, Cudjoe
$1,399,000
3 Beds ⋅ 2 Baths ⋅ 619835 MLS
Welcome to your ROOFTOP RETREAT - a beautifully remodeled waterfront home at 22939 Gasparilla Lane in Cudjoe Key, where panoramic ocean views and relaxed Keys elegance come together in perfect harmony. From the spectacular rooftop deck to the light-filled interior, shimmering turquoise water creates a breathtaking backdrop throughout the home. This thoughtfully updated 3-bedroom, 2-bath concrete block residence offers 1,434 square feet of refined coastal living, enhanced by rich wooden ceilings that add warmth, character, and timeless island charm. The open living spaces flow effortlessly to the screened porch overlooking the canal -- the ideal setting for morning coffee, sunset cocktails, or unwinding after a day on the water. Designed with both comfort and functionality in mind, the property features a new metal roof, covered parking, fenced grounds, and a spacious downstairs utility/workshop area perfect for boating gear, paddleboards, fishing equipment, or hobbies. Perfectly positioned on a canal in the Lower Keys with easy boating access, Rooftop Retreat captures the essence of waterfront living with unforgettable ocean vistas and an inviting coastal atmosphere. Whether you're searching for a private island getaway, a second home, or an exceptional investment opportunity, this property delivers the very best of the Keys lifestyle.

22939 Gasparilla Ln, Cudjoe
22961 John Avery Ln, Cudjoe
$895,900
2 Beds ⋅ 2 Baths ⋅ 619710 MLS
Reduced over 100k for a quick sale! Boater's Paradise in Cudjoe Key under 1 million! Bring your boat, jet skis, and sense of adventure! This upgraded two-story coastal retreat is designed for water lovers, featuring over 60 feet of dock space complete with shore power, plumbing, and brand-new dual jet ski davits plus a boat lift -- perfect for launching into the Florida Keys lifestyle. The lower level offers a bonus unit, storage and covered porch. Upstairs, the main residence features a bright, open-concept living space with large impact-resistant windows and doors installed by the previous owners, offering both natural light and storm protection. The home is energy-efficient and move-in ready. Located in a quiet and highly desirable neighborhood in Cudjoe Key, this fully furnished gem is a rare opportunity to own a true Keys boater's dream home. Whether you're an avid fisherman or just looking for the ultimate waterfront lifestyle, this property is a must-see!

22961 John Avery Ln, Cudjoe
22953 John Silver Ln, 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
21640 Overseas Hwy, Cudjoe
$2,800,000
4 Beds ⋅ 3 Baths ⋅ 619615 MLS
SPECIAL DAILY TRANSIENT LICENSE!!! Experience one of the Lower Keys' rarest offerings at 21640 Overseas Highway,an extraordinary 1.2 acre open-water estate with panoramic ocean views, resort style amenities, and true investment upside. Opportunities like this almost never come to market from Key West to Summerland. With 3,286 sq ft per appraisal, this 4-bedroom waterfront residence delivers the scale, privacy, and setting luxury buyers search for but rarely find. From the moment you enter, the home is designed around the water. Expansive living areas, soaring ceilings, and oversized windows frame endless blue views while natural light fills the interior. The spacious layout offers multiple entertaining zones, generous bedroom suites, and the kind of footprint that allows a buyer to enjoy immediately or elevate into a signature Keys showplace. Outside is where this property separates itself from nearly everything else on the market. The massive parcel creates room to breathe, entertain, and enjoy waterfront living on a level almost impossible to replicate today. A private pool, sandy beach area, dockage, mature tropical grounds, and open-water backdrop combine to create a true resort atmosphere. Sunrise coffee, sunset cocktails, paddleboarding, boating, and stargazing all happen from your own backyard. Under the home, an immense garage / storage / workshop space offers rare functionality for collectors, boating gear, vehicles, trailers, hobbies, or business use. Very few waterfront homes in the Keys offer this level of usable enclosed space. For investors, this property's transient rental license potential is a major value driver. Large open-water estates with acreage and premium amenities command exceptional demand in the vacation market. With the right presentation and management plan, this is the type of asset that can serve as both a personal retreat and a high-performing income property. Lets take a look!!!

21640 Overseas Hwy, Cudjoe
22542 Jolly Roger Dr, 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
22978 Port Royal Ln, 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* Great Opportunity for affordable canal front home *

22978 Port Royal Ln, Cudjoe
20920 5th Ave, Cudjoe
$2,795,000
4 Beds ⋅ 3 Baths ⋅ 618526 MLS
Florida Keys luxury island living at its finest. Welcome to your private slice of tropical island living in coveted Cudjoe Gardens—a true boater's dream set on an oversized double canal-front lot (approx. 15,200 sq. ft.) with an impressive close to 200 feet of concrete seawall. This beautifully designed CBS home offers 4 bedrooms, 3 baths, and nearly 3,000 sq. ft. of living space, thoughtfully arranged for relaxed living and effortless entertaining. Recent renovations elevate the home even further, with the kitchen and primary bath completely and tastefully reimagined by D'Asign Source. The stunning chef's kitchen now features Omega cabinetry, elegant quartzite stone surfaces, premium KitchenAid appliances, and a striking black walnut round dining table that anchors the space with warmth and natural beauty—perfect for gathering with family and friends. Pocket sliding doors open the living areas to a spacious screened Florida Room (approx. 494 sq. ft.), seamlessly blending indoor and outdoor living. Outside, enjoy mature tropical landscaping, extensive paved driveways and walkways, and resort-style spaces designed for relaxing and entertaining. For boating enthusiasts, this property truly shines: approx. 4' control depth, quick access to the reef and backcountry, protected canals, and proximity to a full-service marina. The seawall is fully equipped with a cut-in boat slip, 15,000 lb. boat lift, davits, swim ladder, and outdoor shower—everything you need for life on the water. Additional highlights include a barrel tile roof, an attached 2 car garage, a versatile 676 sq. ft. garage space ideal for storage, hobbies, or island toys. Whether you're hosting sunset gatherings by the pool, heading out for a day on the water, or simply unwinding in your own tropical retreat, this remarkable property offers the perfect blend of comfort, style, and true Florida Keys lifestyle. Come see this exceptional canal-front retreat, where every day feels like a getaway.

20920 5th Ave, Cudjoe
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