Divider
Content Divider
Total Listings 71
Order By:

$2,195,000
Cudjoe Key
Cutthroat Harbor Estates   - MM: 23.00
2 Bed, 2 Baths, 1,292 SqFt Days Listed: 41
-4.36% ($100,000) 1 Price Change : Last Change 5 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Other Dockage22ft.

Experience the epitome of Florida Keys living in this stunning luxury waterfront home on Cudjoe Key. The back of the home has a South West Exposure, for endless ocean views and spectacular nightly sunsets. Constructed with poured concrete for unmatched durability and featuring a poured concrete floor, this home is a sanctuary of modern design and functionality. The property boasts impact-rated windows and doors installed in 2016, including custom 5-panel EuroWall stacking doors that create a seamless indoor-outdoor flow. Modern elegance is evident throughout, with stainless cable railings and a zero-grout tiled walk-around porch. Offered furnished with Restoration Hardware and Room & Board pieces valued at approximately $45,000 (art excluded), also includes TVs.The outdoor spaces feature a heated pool featuring a Coralina stone deck sourced from the Dominican Republic, designed to stay cool underfoot. New pool equipment, including a heater and pump installed in 2018. Boating enthusiasts will appreciate the 21.5 wood dock with a Slide-Moor Dock system, complete with water access, as well as a floating dock system perfect for kayaking and paddleboarding. The propertys tropical landscaping, accented with solar yard lighting & cozy lounge areas create wonderful, private space to enjoy serenity or entertain guests.The gourmet kitchen, updated in 2022, features quartz countertops, modern blue cabinets, and Samsung Bespoke appliances. Dont miss your chance to own this luxury retreat in the heart of Cudjoe Key. Just 22 miles to Key West and 3 hours from Miami. Fantastic bar/ restaurant/ and coffee shop within walking distance!

$2,249,000
Cudjoe Key
Cutthroat Harbor Estates   - MM: 23.00
4 Bed, 4 Baths, 2,074 SqFt Days Listed: 96
-8.20% ($201,000) 2 Price Changes : Last Change 1 Day Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 32ft.

Welcome to paradise at 22562 Jolly Roger Dr in beautiful Cudjoe Key! This custom built, 4-bedroom, 2-bath home features open water views, a designer kitchen with high-end finishes and Viking appliances. In addition, on the first floor there are two guest bedrooms, an office and bathroom. The second floor is where you will find the third bedroom as well the primary bedroom complete with private balcony, ensuite bathroom and walk in closet. Outside the property boasts double decker porches, covered hot tub, full swim spa, and new dock. In addition to the garage there is ample room for vehicles, boats and extra storage. The property is equipped with RV electrical and sewer hookups for added convenience. The property features impact windows and doors and is a stones throw from American Shoal, Lighthouse, Looe Key Reef, and Square Grouper restaurant.

$2,300,000
Cudjoe Key
Sacarma Bay   - MM: 21.00
5 Bed, 5 Baths, 1,978 SqFt Days Listed: 81
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Slip20ft.

Rare Licensed Oceanfront Short-Term Vacation Rental in the Lower Florida Keys. 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 2025 and 9-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. And Seller Financing is possible! Owning a vacation rental property means youre not just paying for vacations--youre 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.

$2,300,000
Cudjoe Key
Cudjoe Gardens   - MM: 21.00
3 Bed, 3 Baths, 2,047 SqFt Days Listed: 272
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits,Boat Lift100f

Wonderful Cudjoe Gardens property! High quality concrete construction and custom metal roof. This 3 bed 2 bathroom home has large, open living and wonderful outdoor living space- complete with pool, tiki and firepit. Exceptional boating- the 100 concrete dock is set up for 2 boats- with a 20,000 lb lift and davits rated to 10,000 lbs. Enjoy easy boating access to world class fishing and diving hotpots nearby!!! Enjoy backcountry sand bars and even bar hopping from your private dock. Cudjoe Gardens community has an optional homeowner association, A full service marina, boat ramp, marina store and restaurant. Just 25 minutes to Key West.

$2,395,000
Cudjoe Key
Cutthroat Harbor Estates   - MM: 23.00
4 Bed, 4 Baths, 2,440 SqFt Days Listed: 98
-4.01% ($100,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

This Beautiful Oceanfront Home in Cudjoe Key has undergone a full renovation and awaits its new owner! All new impact doors and windows, new AC, new flooring throughout and a stunning custom kitchen with granite countertops and stainless steel appliances are a few of the many updates in this amazing renovation .Offering Four generous size bedrooms with Three full bathrooms, it can easily accommodate a large family.The open floor plan of the living and dining room with massive cathedral ceilings , showcase this homes coastal character. Three sliders face the unmatched ocean view , and open to let the ocean breeze flow through the house. Step out on the 500sf covered porch to enjoy the indoor outdoor living and entertaining with breathtaking panoramic Oceanfront views.This spacious Oceanfront four bedroom home is being sold with the adjacent parcel, for a total 13,979 sf lot.and with the Best views in Cudjoe Bay, and plenty of room to add a pool, pool house, and garage, the options are truly endless. Do not miss this great opportunity, this is a one of a kind home. Call now to schedule your private tour.

$2,999,000
Cudjoe Key
Cudjoe Gardens   - MM: 21.00
4 Bed, 4 Baths, 2,604 SqFt Days Listed: 19
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift255ft.Concr

Welcome to this stunning CBS (Concrete Block Stucco) Home located in the desirable Cudjoe Gardens neighborhood on Cudjoe Key. This charming 4-bedroom, 3-bathroom residence offers 255 feet of seawall, perfect for boating enthusiasts with ample dock space and 2 boat lifts.As you approach this meticulously landscaped property, on a lot & half, youll be greeted by the serene ambiance of the tropical surroundings. Step inside and enjoy the spacious open-concept living area, where the kitchen flows seamlessly into the large living room. Beautiful granite countertops add a touch of luxury, and the keystone fireplace creates a cozy atmosphere.The home features a heated pool with a great outdoor seating area, ideal for relaxing or entertaining guests year-round. Whether youre enjoying a swim or savoring the scenic canal views, its easy to see why this home is perfect for outdoor living in paradise.Additional highlights include a large two-car garage, accordion shutters for storm protection, and a recently replaced metal roof for added peace of mind.This property is a boaters dream with quick access to the waters of the Florida Keys, making it an ideal place for fishing, kayaking, or just cruising around the beautiful surrounding area. Dont miss out on this incredible opportunity to own a piece of paradise in the Florida Keys. Call today for more information or to schedule a showing! Comes Furnished and ready for a new owner....Bring your boat and enjoy the finest fishing and diving spots in the Lower Keys. Quick commute to Key West & fine dining, fun and International Airport.....

$3,720,000
Cudjoe Key
Cutthroat Harbor Estates   - MM: 23.00
4 Bed, 4 Baths, 3,000 SqFt Days Listed: 279
-0.13% ($5,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Dock Privileges,Othe

BOATERS PARADISE Room for up to 3 BOATS or up to 42ft! with unobstructed sunset views over OPEN water year round on oversized CORNER lot w/water on 2 sides at the very end of a private road offering picture perfect sunsets in a protected bay! Boasting 323 of water frontage, this property includes 175 of open water and 148 of canal frontage featuring a 90 concrete dock at mouth of channel and a private kayak launch. Main level of the home features a wrap-a-round deck, a spacious living area, including a large master bedrm and bathrm 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. 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 its own updated kitchen with brand new SS appliances overlooking the water! Smart home panels & security cameras thruout. Being sold fully furnished w/exception of a few personal items. 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 Jet Ski Dock that holds 2 Jet Skis! 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 & restaurants. Home was recently tented & has fresh paint, lighting, updated electrical. Home is entirely fenced & Gated w/privacy PVC fencing. The best of all is the wide open water & gorgeous sunset views! Being Sold Turn Key & Seller financing offered at 4% Rate! Owner/Agent

$3,995,000
Cudjoe Key
Cudjoe Gardens   - MM: 21.00
4 Bed, 4 Baths, 3,817 SqFt Days Listed: 87
-16.75% ($804,000) 2 Price Changes : Last Change 6 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift150ft.Concr

Exquisite LUXURY Waterfront Estate in the exclusive Cudjoe Gardens. A STUNNING TURNKEY PARADISE, PRICE INCLUDES, 2 NEW HOBIE CAT KAYAKS, HIGH END DESIGNER FURNISHINGS & DECOR FROM RESTORATION HARDWARE, POTTERY BARN, AND MORE. This Custom Built Home 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 260 ft of water frontage offering deep draft. This gorgeous property offers an unparalleled tropical lifestyle, perfect for those who demand the best in comfort and elegance.Property Highlights4 Bedrooms + Office/Studio: 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 chefs 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, and 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 Keys

$4,295,000
Cudjoe Key
Cutthroat Harbor Estates   - MM: 23.00
3 Bed, 3 Baths, 2,295 SqFt Days Listed: 283
-27.82% ($1,655,000) 17 Price Changes : Last Change 5 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits,Davit Pads25f

Perched on the oceanfront, this extraordinary Cudjoe Key estate boasts breathtaking views from every vantage point, including the rooftop deck. The solid concrete construction, complete with impact-resistant doors and windows, concrete dock, and poolside cabana featuring a bar, sink, and ice machine, ensures a luxurious haven. Lush landscaping, meticulously maintained on a weekly basis, adds to the propertys allure. Upon entering the coded-entry home, a stunning living, dining, and kitchen area unfolds, complete with quartz countertops, stainless steel appliances, and a convenient laundry room. The kitchens center island is spacious and includes refrigerator and freezer drawers, a cooktop and barstools, making it a great entertaining area. The main levels ensuite bedroom, featuring double beds and a jack-and-jill bathroom, offers direct access to the oceanfront patio and a spiral staircase leading down to the pool. Ascend to the master suite, where a lavish bathroom awaits, complete with a jetted tub, double sinks, programmable commode, and walk-in shower, all set against the backdrop of dazzling ocean views. A third ensuite bedroom, features a walk-in shower, single sink, and expansive mirror, with the king-size bed positioned to maximize the stunning vistas. The private outdoor area, complete with a mermaid-adorned pool, large BBQ area, and cabana room, is perfect for outdoor entertaining. World-class fishing and diving opportunities are minutes away, with the Gulf and Atlantic within easy reach. This idyllic location also offers a front-row seat to the marine life of Cudjoe Bay, including porpoise, ospreys, sharks, stingrays, and manatees. Situated in a highly sought-after area of Cudjoe Key, this estate is surrounded by excellent restaurants and boasts wonderful views of the American Shoals Lighthouse.

$12,900,000
Cudjoe Key
Cudjoe Gardens   - MM: 21.00
7 Bed, 7 Baths, 4,888 SqFt Days Listed: 22
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits,Boat LiftCut/

Welcome to Cypress Point, an exceptional and highly private, 7-Bed, 6-Bath, 4,888 Sq Ft oceanfront estate spanning almost a full acre on Cudjoe Key, where luxury and coastal beauty uniquely blend. This custom DAsign Source built home is privately nestled behind an electric gate and boasts the finest finishes and amenities which include an oceanfront pool, outdoor theater, 6-hole golf green, bocci ball and 7-car garage. The grand entry greets you with rough-cut coral flooring, 8-foot doors and an expansive Great Room, offering sweeping ocean views. The gourmet Kitchen is ideal for entertaining and features a Viking stove and microwave, refrigerator, two farm sinks, quartz countertops, ice maker, wine cooler, wet bar and beverage cooler. The adjacent Butlers Pantry is equipped with a SubZero refrigerator/freezer for your added convenience. A pop-up television allows viewing from both the Kitchen and Living Room. The dining area is further enhanced by the vast water views and Summer Kitchen ideal for table side grilling. The main level also features 2 Guest Suites with ensuites and a third 2-Bedroom Family Suite with a private veranda overlooking the Atlantic Ocean. The third floor showcases the luxurious Primary Suite, complete with endless ocean views, private balcony, drop-down screen projector, morning kitchen, walk-in closet and a spa-like ensuite which includes a massive shower, linen closet and drop-down mirror with a television. The fifth Guest Suite with its private balcony completes the third-floor layout. Boating and water enthusiasts will enjoy the deep draft dockage with both 40K and 17K boat lifts, two davits and 6K swim platform. Further enhancing this coastal estate is impact doors and windows throughout, electric blinds, whole-house generator, two 1,000-gallon propane tanks and laundry chutes for your added convenience. The breathtaking open-water views from every room showcase the illuminating sunrises and sunsets in this picturesque estate.

$13,995,000
Cudjoe Key
Sacarma   - MM: 21.00
31 Bed, 31 Baths, SqFt Days Listed: 259
-3.45% ($500,000) 1 Price Change : Last Change 82 Days Ago
Multi-Units - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Ramp,Basin

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. Shared coin laundry, 2 swimming pools, 3 private driveways. 2 parcels on US 1 are zoned Sub Urban Commercial, excellent rental history. Property spans from US 1 to the Atlantic Ocean. Owner is licensed Realtor. Please do not walk on the property without an appointment

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 03-04-2025.
Back To TopMore Info
Terms / Privacy / Accessibility ADA