Cudjoe Key Real Estate

Cudjoe Key Real Estate

Welcome to Cudjoe Key, a hidden gem nestled in the heart of the Florida Keys! This enchanting island, located in Monroe County, is the perfect blend of tropical paradise and laid-back island lifestyle. With its stunning vistas, crystal-clear waters, and vibrant marine life, Cudjoe Key offers a unique opportunity for those seeking a tranquil escape or a new place to call home.

Cudjoe Key is known for its idyllic surroundings, featuring lush landscapes and breathtaking sunsets that paint the sky in hues of orange and pink. The island is a haven for outdoor enthusiasts, offering a plethora of activities such as fishing, kayaking, and snorkeling. The nearby waters are teeming with colorful coral reefs and diverse marine species, making it a popular destination for both novice and seasoned divers.

Life on Cudjoe Key is all about community and connection. The island boasts a friendly atmosphere, with local shops, restaurants, and recreational facilities that cater to residents and visitors alike. Whether you're enjoying a leisurely meal at a waterfront eatery or participating in one of the many community events, you'll quickly feel the warmth and charm that Cudjoe Key has to offer.

For those looking to invest in real estate, Cudjoe Key presents a variety of options, from charming waterfront homes to cozy cottages tucked away in serene settings. With its prime location and natural beauty, this island paradise is not just a place to live; it's a lifestyle. Discover the allure of Cudjoe Key and let it captivate your heart—your dream home awaits!

Newest Listings in Cudjoe Key

$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
$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
$1,799,000
3 Beds ⋅ 2 Baths ⋅ 621138 MLS
OPEN WATER VIEWS - BRAND NEW CUSTOM WATERFRONT HOME - DOUBLE LOT & MOVE IN READY. This ELEVATED 3 bedroom, 2 bathroom CBS home is a must see! Solid steel and concrete, standing seam white metal roof with impact windows and doors rated to 185 MPH. 2,050 total sq ft of living space includes a front porch, utility room on the lower level and a lanai off the back. A total of 1500 sq ft of living space under air with a spacious open floor plan. An aluminum powder coated spiral stair case will lead you to an UPPER DECK where you can capture views of the sunrise and sunset along with panoramic views of Cudjoe Bay, the Atlantic Ocean and surrounding Keys. The kitchen features an Island with quartz countertops and custom cabinetry. Black stainless steel appliances. Tray ceilings and special features set this home apart. The front entrance and rear exit entry feature a red mahogany stained cypress ceiling matched perfectly to blend with the brass door handles. No details are spared with the elegance of the home's interior finishes. Ceramic tile cut on the diagonal throughout the interior and exterior porch and lanai. This home is being sold turn key with brand new furnishings as seen in the listing photos. Excellent boating access to both Cudjoe Bay and the Atlantic Ocean with 130' of canal frontage. Take over active permit for a 10 x 30 ft dock with all fees including mitigation fees already paid in full. Plenty of room for an in-ground 12 x 30 ft pool. Also possible to build on the adjoining lot with ROGO approval. Very low insurances, less than $4000 per year for Homeowners/Wind. Schedule your private showing and discover coastal living at it's finest in the Florida Keys!

22970 Gasparilla Ln, Cudjoe
$982,600
2 Beds ⋅ 2 Baths ⋅ 621115 MLS
Welcome to Oceanview Serenity, an exceptional, open-water retreat located in the gated community of Venture Out at Cudjoe Key (Mile Marker 23). This completely renovated 2-bedroom, 2-bathroom mid-rise offers rare, unobstructed turquoise ocean views as if you are floating on the water. A true boater's paradise, the property boasts a massive concrete seawall with effortless deep-water access. Critical structural and exterior updates provide unmatched peace of mind and substantial insurance benefits, including a brand-new roof, newly installed heavy-duty tie-down straps, and freshly refurbished, protected under-house support beams. Go inside to a bright, turnkey coastal interior where every detail has been thoughtfully updated, complete with a smart Nest thermostat for effortless climate control and energy efficiency. The main living space is framed by expansive windows that showcase panoramic water views. The heart of the home is a fully upgraded kitchen outfitted w/new appliances, and an oversized central island featuring generous built-in storage and a breakfast bar. The spacious primary suite serves as a luxurious private haven, highlighted by an upgraded ensuite bathroom complete with a double vanity and abundant storage. Outside, the covered deck offers the ultimate vantage point to relax in the ocean breeze and take in breathtaking Florida Keys sunrises over the water. Offered fully furnished and tastefully appointed, this home is 100% move-in ready to enjoy as a primary residence, private tropical getaway, or income-producing investment as a nightly rental. Venture Out is one of the rare communities in the Lower Keys that permits lucrative nightly rentals. Enjoy an incredible lineup of resort-style amenities, featuring a massive oceanfront saltwater swimming pool, an on-site marina store with a fuel dock, boat ramps, lighted tennis and pickleball courts, basketball, bocce, a vibrant recreation hall, and 24/7 gated security.

701 Spanish Main Dr Unit 198, Cudjoe
$459,000
621103 MLS
Canal-front Paradise Awaits! Incredible view from your seawall! RV Lot 609 in Venture Out. Experience the epitome of waterfront Florida Keys living on this Canal Front RV Lot with 40' Seawall nestled within an exclusive gated community. This beautiful canal front property boasts: * Prime Canal front Location: Enjoy direct access to the water from your private 40 ft seawall. * Community Boat Ramp and boat washdown station. * Community Amenities: Indulge in a resort-style lifestyle with access to a huge heated pool, spa, clubhouse, pickleball courts, tennis courts, basketball courts, bocce courts, ocean swimming area and more! * Well-Maintained: This RV Lot has been very well cared for and maintained and is ready for you to bring in your RV and enjoy. * Gated Community: Cruise around the property in your golf cart to the community store or to join in on the numerous community activities. Live with peace of mind in a secure and exclusive gated community. Don't miss this rare opportunity to own a piece of paradise! * Exclusivity: The gated community adds a sense of security and prestige. * Nightly Rentals Allowed! * Excellent rental income potential!!

701 Spanish Main Dr Unit 609, Cudjoe
$1,250,000
1 Baths ⋅ 621081 MLS
Prime Lower Keys Commercial Real Estate for sale. Excellent visibility and easy access from Overseas Hwy. Corner location at MM 21 and Blimp Rd. Total of 3 Parcels of Land. With the Submerged Baybottom parcels total over 3 Acres with Approx. 37,748 sf. or .87 Acres of useable uplands. Uplands portion is approx. 200' of highway frontage by 190' deep. Waterfront property with limited shallow water access for kayak and canoes. Existing 1,250 sf. CBS building on site may be enlarged or demo and entirely redevelope. Property has favorable SC- Suburban Commercial Zoning with many Commercial uses allowed and possible. Great location for a local contractor, retail convenience store, or marine/boat/trailer/ RV and Auto storage.

21423 Overseas Hwy, 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
$1,349,000
3 Beds ⋅ 2 Baths ⋅ 620916 MLS
Look no further--this exceptional property truly has it all. This beautifully maintained CBS home boasts open-water views and is situated on an oversized lot on an extra-wide, deep canal, great for bigger boats, and just three houses in from the end. You'll be up on plane in seconds, with unparalleled boating access to both the Atlantic and Gulf. Ideally located closest to the premier backcountry of the Lower Florida Keys, this is the perfect property for the fishing and diving enthusiasts and still only 20 minutes to Key West. Built by Tom Ryan Construction, this solid CBS 3-bedroom 2-bath home is almost 1,300 square feet, and has a spacious, open feel, created by the thoughtful layout and vaulted ceilings in the main living area. The kitchen features granite countertops, a convenient breakfast bar, and a dedicated dining area, making it ideal for both everyday island living and entertaining. The primary suite has a walk in closet and french doors leading out to the porch, while the second bedroom has a pocket door creating another convenient ensuite for guests. Most days you'll enjoy outdoor dining or cocktails and the relaxed island life from the covered, screened porch overlooking the canal with open water views of Kemp Channel. The views continue into the primary suite and kitchen, offering a beautiful waterfront backdrop throughout the home. The lower enclosure provides plenty of space for a vehicle, workshop, and storage. Two 500-gallon cisterns provide ample water for maintaining the lush tropical landscaping. The solid concrete step down seawall features davits each with a 5,500 lift capacity. This property is the ideal location to be able to spend a stellar day on the water, then head to Key West to one of the many fabulous restaurants for dinner, and finish the evening listening to live music or take in a show at one of our unique boutique theaters. You can have it all.

23057 Bluegill Ln, Cudjoe
$514,900
620843 MLS
Premier Waterfront RV Lot in Venture Out | 35' Seawall, Ocean Views & Proven Rental Income! Whether you are looking for your own personal Florida Keys getaway or a high-performing investment property, this lot offers the perfect blend of luxury, location, and lucrative returns. Boasting a consistent rental history, this turn-key property is a proven income producer with established guest demand. • Prime Waterfront & Ocean Views: Enjoy breezes and water views right from your patio. • 35-Foot Concrete Seawall: Perfect for boaters and anglers! Equipped with dock posts, cleats, swim ladder and quick, direct access to both the Atlantic Ocean (for offshore fishing/diving) and the Gulf backcountry (for calm-water cruising). • Spacious Pad & Full Hookups: Accommodates large RVs with plenty of room for outdoor lounging and dining. Equipped with 30/50 amp electric, water, and sewer connections. • Proven Cash-Flow Investment: Strong year-round and seasonal rental track record with repeat visitors. Located at Mile Marker 23, Venture Out is one of the Lower Keys' premier resort communities. Ownership includes full access to a wealth of luxury resort features: • 🏊 Heated Saltwater Swimming Pool & Hot Tub • 🚤 Private Marina, On-Site Fuel Station, Boat Ramp & Wash Station • 🎾 Tennis, Pickleball, Bocce Ball, and Basketball Courts • 🛒 On-Site Convenience Store, Fish Cleaning Stations, & Bathhouses • 🔒 24/7 Gated Security Patrol for complete peace of mind

701 Spanish Main Dr Unit LOT 266, Cudjoe
$350,000
620822 MLS
Prime Cudjoe Key Commercial Opportunity! Cleared Suburban Commercial parcel offering outstanding highway frontage and excellent visibility on the Overseas Highway. Zoning SC allows for a variety of uses flood zone AE 9 tier 3 lot. For investment or owner-use. Owner financing may be available to qualified buyers. Bring your vision and capitalize on one of the Lower Keys' high-exposure commercial locations. Buyer to verify all info. No trespassing . Cameras on site.

22776 Overseas, Cudjoe
$249,000
1 Beds ⋅ 1 Baths ⋅ 620746 MLS
Welcome to Unit 533 in the gated waterfront community of Venture Out on Cudjoe Key! This well-maintained home features a spacious addition that provides extra living space and versatility. The addition includes a comfortable living area and a flex room currently used as additional sleeping space--ideal for guests, a home office, or hobby room. The property is currently occupied by a long-term tenant, offering an opportunity for a buyer seeking immediate rental income. The home offers a functional layout suitable for full-time living, seasonal enjoyment, or future investment use. Venture Out permits transient rentals with no minimum-night requirement, giving owners flexibility in how they choose to use the property. Community amenities include a large heated and chilled saltwater pool, hot tub, swimming lagoon, full-service marina with boat ramp and fuel dock, and convenient boating access to both the Gulf of Mexico and the Atlantic Ocean. Residents and guests also enjoy pickleball, tennis, bocce ball and basketball courts, a playground, two community centers, organized activities, and on-site church services. Looking for a fresh start? The property may also offer the potential to be converted into an RV lot or rebuilt to suit your vision, subject to current building regulations and community requirements. Schedule your private showing and explore the possibilities at Unit 533!

701 Spanish Main Dr Unit 533, Cudjoe
$2,060,000
5 Beds ⋅ 3 Baths ⋅ 620686 MLS
Rare Licensed Oceanfront Short-Term Vacation Rental in the Lower Florida Keys, with SELLER FINANCING OFFERED! Welcome to Fandango, a highly successful transient (daily-weekly) vacation rental home offering an exceptional investment opportunity and a personal retreat. This stunning 5-bedroom, 3-bathroom property, built in 2011 and expanded in 2018, was thoughtfully designed as the ultimate family vacation rental retreat. Featuring an adjacent oceanfront parcel with a private beach, kayaks, and a floating dock for fishing or docking boats up to 24 feet, this property provides everything needed for fun and relaxation. Outdoors, enjoy a sparkling swimming pool, soothing hot tub, tropical landscaping with coconut palms and banana trees, and a screened-in porch for al fresco dining. Inside, the open floor plan includes four king bedrooms and a fifth bedroom with a queen and single bed, smart TVs, and updated appliances. Centrally located at MM21.5, Fandango is just 20 minutes from Key West, 10 minutes from Big Pine Key, and 15 minutes from Bahia Honda State Park, with dining options nearby, including a 5-star restaurant within a mile. This property is offered fully furnished and equipped, including bookings into 2027 and 10-years' average income of $160+k. Professional property management is in place, ensuring both secure investment returns and worry-free family vacations. This low-maintenance, turn-key home offers the rare opportunity to own one of the few legally licensed short-term rentals in the Lower Keys. Owning a vacation rental property means you're not just paying for vacations--you're building equity and unlocking financial benefits, all while eliminating the scramble for accommodations every trip. Show up, relax, and let your investment work for you.

94 Sacarma Dr, Cudjoe
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