luxury house for sale Grassy Key, United States

Enter the bougainvillea-lined gates of Casa Feliz, a private oceanfront retreat on Grassy Key with expansive water views, white sand beach, and a true resort-style experience in the Florida Keys. An exceptional investment opportunity, Casa Feliz is a strong producing vacation rental with rental history and future bookings already in place. Set on over 24,000 square feet of lush grounds with mature landscaping, fruit trees, fresh herbs, and .29 acres of bay bottom, this exceptional estate is designed for both relaxation and entertaining. A 148-foot observation dock invites kayaking, paddleboarding, fishing, and endless enjoyment of marine life, while the unique orientation captures both breathtaking sunrise and sunset views over the water, a rare and coveted feature in the Keys. Outdoor living is elevated with a resort-style saltwater pool featuring cascading waterfalls, spillover spa, and fully equipped poolside cabana complete with wet bar, refrigerator, ice maker, and cooking area. A fire table and beachside fire pit create the ultimate setting for entertaining or unwinding beneath the stars. Completely renovated down to the studs in 2022, the three-story residence was thoughtfully redesigned to maximize sweeping ocean views from nearly every room. Offering four custom bedroom suites, each with private en-suite bath, the home comfortably accommodates guests in luxury. The top-floor penthouse suite features a private balcony, 180-degree ocean views, custom 96-inch circular bed, and kitchenette with coffee station. Expansive accordion impact glass doors seamlessly blend indoor and outdoor living throughout. The gourmet kitchen showcases Café appliances, induction cooktop, quartz countertops, mosaic tile backsplash, wine cooler, glass shelving, and multiple dining areas ideal for hosting. Additional highlights include a movie theater, library loft, Control4 smart technology, custom millwork, local artist mural, and more. Discover why Grassy Key is the place to be.

Positioned along one of the most secluded and protected stretches of the Gulf of America, this extraordinary waterfront estate represents a rare combination of modern coastal architecture, complete privacy, and unparalleled natural beauty.Set across more than three private acres, the property enjoys over 200 feet of direct Gulf frontage, surrounded by pristine shoreline, tidal lagoons, crystal-clear waters, and a thriving marine ecosystem, creating a level of exclusivity and tranquility rarely found in today’s luxury real estate market.Completed in 2025 by the renowned Alderuccio Corporation, the estate was envisioned as a fully private waterfront resort, designed to deliver exceptional comfort, structural resilience, and timeless architectural appeal.Constructed entirely of reinforced concrete and impact-resistant glass, the residence offers outstanding durability, security, and performance while maintaining a sophisticated contemporary aesthetic.Encompassing approximately 10,000 square feet of finished living space distributed across three distinct residential structures, the estate has been thoughtfully designed to accommodate family, guests, and staff while preserving privacy and seamless functionality.Expansive walls of glass frame breathtaking Gulf views and create an effortless indoor-outdoor lifestyle, allowing every living space to embrace the spectacular sunsets and coastal beauty that define the Florida Keys.Highlights include:Over 3 private acres of Gulf-front landMore than 200 feet of direct waterfrontThree fully finished residential structuresHurricane-resistant concrete and glass constructionContemporary coastal architectureExpansive indoor and outdoor entertaining spacesExtraordinary privacy and seclusionDirect access to world-class boating and water recreationUninterrupted panoramic Gulf viewsPrivate resort-style lifestyle experienceSurrounded by untouched natural beauty and some of Florida’s most remarkable coastal landscapes, this exceptional estate offers a rare opportunity to own a true waterfront legacy property in the Florida Keys.Combining architectural excellence, absolute privacy, and a spectacular Gulf-front setting, this is a trophy estate created for the most discerning luxury buyers.Contact us for confidential information or to arrange a private presentation of this extraordinary Gulf-front estate.

Life on the water begins the moment you arrive at this beautifully positioned open water home on prestigious Harbour Drive in Duck Key. Surrounded by swaying palms and tropical landscaping, this classic 2 Bedroom 3 Bathroom Florida Keys coastal cottage sits on an oversized 11,250 sq. ft. lot highlighted by a bright open-concept layout with panoramic views of Toms Harbor. Built with CBS construction, impact windows, and a metal roof, the property provides both durability and low-maintenance island living. For boaters, the property features 75 feet of concrete seawall and a dock with quick access to both the Atlantic Ocean and Gulf for world-class fishing, diving, and boating. The tropical backyard is designed for true Keys living, featuring a waterside tiki hut, shaded seating areas, and plenty of room for a future pool with a permitted convenience bathroom downstairs. An outdoor elevator, garage, and beautifully landscaped yard add comfort and curb appeal. Residents of Duck Key enjoy optional membership at Club Duck Key with access to a heated and chilled pool, pickleball and tennis courts, bocce ball, basketball, and a vibrant social calendar. Located just minutes from Marathon Jet Center, marinas, restaurants, and shopping, this Duck Key home offers the perfect balance of privacy, boating convenience, and island lifestyle.

Duck Key Pool Home with Legal Downstairs Living & Exceptional Flexibility. Beautifully updated 4BR/3BA pool home on the desirable island of Duck Key, thoughtfully renovated with permits and designed for comfortable coastal living. A standout feature of this home is the legal, permitted downstairs living area (pre-1973), which offers a private space complete with a living room, bedroom, bath, and kitchenette. This flexible layout is ideal for extended family, long-term guests, or creating a separate retreat within the home--an increasingly rare advantage in the Florida Keys. Upstairs, the main living area features updated finishes and generous closet space throughout, providing both comfort and functionality. The home is offered fully furnished and move-in ready, allowing for immediate enjoyment. Step outside to your own private tropical setting, featuring: a sparkling pool and tiki hut for entertaining; lush landscaping with pineapple, fig, starfruit, and avocado trees; a private putting green; and partial Atlantic Ocean views. Additional highlights include two attached garage spaces and access to a voluntary homeowners clubhouse. Conveniently located near Duck Key Marina and Hawk's Cay Resort amenities, with optional memberships available. A rare opportunity to own a versatile, move-in-ready home in one of the Florida Keys' most sought-after communities. Check out the marina and the perks of being a homeowner on Duck Key. https://www.duckkeymarina.com/ for boat slips, https://hawks-cay-resort.playbypoint.com/f/hawks-cay-resort/memberships, https://www.hawkscay.com/, and http://www.clubduckkey.com/ for memberships! All in your backyard.

Hawks Cay Resort Villa - Luxury, Lifestyle & Investment Potential. NIGHTLY RENTALS ALLOWED. This beautiful 2-bedroom, 1.5-bathroom end-unit villa is your gateway to paradise in the highly desirable Hawks Cay Resort. Perfectly positioned for both personal enjoyment and income generation, this property offers the best of both worlds: a tropical retreat and a savvy investment. • Prime Location: End-unit villa in Hawks Cay Resort, one of the Florida Keys' most sought-after destinations. • Upgraded Features: Impact windows & doors, metal roof, tile throughout, stainless steel appliances, and granite countertops. • Turnkey Condition: ready for immediate income generation or personal enjoyment. • Proven Performance: Comes with an outstanding rental history, making it an ideal short-term rental investment. • Nightly Rentals Allowed: Flexibility to maximize occupancy and income potential. Tax Advantages: Owning a short-term rental property has never been more financially attractive. The recently passed legislation provides powerful tax incentives for STR owners: • 100% Bonus Depreciation Restored: Investors can immediately expense qualifying assets like appliances, furnishings, and renovations—accelerating deductions and reducing taxable income. • Permanent 20% Qualified Business Income (QBI) Deduction: Structured as an LLC or S-Corp, owners can deduct up to 20% of qualified rental income annually, boosting long-term profitability. • 1031 Exchanges Protected: Investors can continue deferring capital gains when swapping properties, preserving portfolio flexibility. • Enhanced SALT Cap: Raised from $10,000 to $40,000, making high-tax states more attractive for STR investment. These provisions mean better cash flow, faster growth, and stronger ROI for savvy investors who act now. Imagine waking up to the serene beauty of the Florida Keys, enjoying resort amenities, and knowing the villa is working for you even when you're away.

Rare opportunity to secure a prime waterfront homesite on highly desirable Duck Key. This property is being offered for land value, presenting the perfect canvas to design and build a custom island retreat exactly to your vision. Even better, the property is ROGO exempt, meaning no waiting for a new building permit -- a verified build right is already in place (letter on file). Boaters will appreciate the 82 feet of dockage and exceptionally quick ocean access. Two davits that are 5,500 lbs each one and a turner on one of them. Center Island is a prime location for privacy on Duck Key. Navigate under the Seaview Bridge and head out through the Headpins for fast access to open water, or take the main channel route for larger sportfishing vessels. Enjoy all the lifestyle perks Duck Key is known for, including nearby dining at Hawks Cay Resort, a welcoming island community. that is golf cart friendly. Fly into Marathon airport with your own plane or Million Air and then drive 15 minutes to your island oasis. Whether you're planning a full-time residence or luxury vacation escape, this is your chance to build your dream home in one of the Florida Keys' most sought-after boating enclaves.

Experience Florida Keys waterfront living in this beautifully updated residence in Harbor Village on Duck Key. This desirable property includes a deeded dock slip located directly behind the home, offering convenient, immediate access for boating and water activities with quick ocean access. The home features a light-filled, coastal-inspired floor plan with inviting living spaces and water views that enhance the relaxed island lifestyle. Enjoy seamless indoor-outdoor living with a private outdoor area overlooking the canal, ideal for morning coffee, entertaining, or unwinding after a day on the water. Located within the sought-after Hawks Cay Resort community, owners enjoy a resort-style setting with access to nearby amenities including boating, dining, and recreational offerings. This property presents an excellent opportunity for a second home, vacation retreat, or income-producing investment in one of Duck Key's most desirable waterfront communities.

Island living at its finest! Welcome to 334 E Seaview Dr, Duck Key, FL 33050 '' a spectacular 3-bedroom, 3-bath canal-front home nestled on prestigious Yacht Club Island. This beautifully remodeled residence offers approximately 1,792 sq ft of thoughtfully designed living space, highlighted by soaring cathedral ceilings and abundant natural light. The main level features a spacious primary en suite, a guest bedroom and full bath, and an inviting open layout perfect for both relaxing and entertaining. Upstairs, the versatile loft doubles as a third en suite or cozy den. Step outside into your own private paradise. The backyard is truly a showstopper featuring a lush turf lawn, custom putting green, swaying palms, and vibrant tropical landscaping. Whether you're lounging in the tiki hut, enjoying a drink at the outdoor bar, or firing up the grill in the summer kitchen, this space was made for hosting. The heated and chilled concrete pool and ambient lighting create the ultimate Florida Keys resort vibe. For boating enthusiasts, the 75-foot concrete dock, boat lift, and clear flow-through canal with direct ocean access make every day a water day. The home also includes impact windows and doors and a whole-house Generac propane generator for year-round peace of mind. There is a ground-level bonus space that buyers must-see! This property offers a rare blend of comfort, style, and island charm in a sought-after location. Come experience the magic of Duck Key - schedule your private showing today!

Experience refined oceanfront living on sought-after Duck Key. This double lot estate offers 138 feet of protected deepwater dockage, complete with a solid concrete seawall designed to accommodate a sportfishing yacht, multiple center consoles, and all of your waterfront lifestyle needs. A true boater's paradise, this property offers both privacy and exceptional access to the Atlantic Ocean. The fully remodeled residence is constructed of concrete with a new roof. Inside, seven spacious bedrooms and six bathrooms provide ample accommodations for family and guests. Coastal-inspired interiors feature wood-look tile flooring throughout, woven statement light fixtures, and soaring ceilings with exposed beams and pecky cypress accents. Expansive impact windows and doors frame sweeping ocean views, bringing natural light into nearly every room. The gourmet kitchen anchors the main living space as the heart of the home, with a striking 12' island that creates the perfect setting for gatherings. Outfitted with top-of-the-line appliances, this space is equally suited for everyday living with family or hosting unforgettable evenings of entertaining. Spa-like marble bathrooms further elevate the home, blending comfort with luxury. Designed for both style and function, the property also offers a rare 4+ car garage and abundant storage. Outdoors, a sparkling pool invites afternoons in the sun, while the expansive double lot offers unmatched opportunities for expansion. Whether envisioning a private guest house, a tennis or pickleball court, or exploring the option to build and sell, this rare property provides endless possibilities for both personal enjoyment and investment potential—an uncommon luxury in the Florida Keys. Balancing modern sophistication with coastal simplicity, this sanctuary captures the essence of waterfront living from sunrise over the Atlantic to evenings by the water, in one of the most desirable neighborhoods in the Florida Keys.

This stunning oceanfront end-unit townhome in the exclusive Bonefish Yacht Club offers the perfect blend of luxury living and resort-style amenities in the heart of the Florida Keys. Nestled within a private 34-residence community set across more than four acres of beautifully maintained tropical grounds, the property captures the feel of a secluded oceanside retreat. This residence conveys with a 40' legal liveaboard boat slip, providing deep-water dockage and immediate ocean access--an exceptional feature for serious boaters. Inside, the home offers 1,751 sq. ft. of light-filled living space featuring a gourmet chef's kitchen with stainless steel appliances, a dedicated dining area, and an open-concept living room that flows seamlessly to a waterside balcony overlooking the marina--perfect for alfresco dining and entertaining. The spacious primary suite features a private waterfront balcony, walk-in closet, and a beautifully appointed ensuite bath. The guest suite also enjoys its own balcony, a full bath, and generous closet space. The ground level includes a private garage and storage area, ideal for a vehicle, fishing equipment, and water toys--perfect for the avid angler. Bonefish Yacht Club residents enjoy exceptional amenities including a heated and chilled waterfront pool with expansive sun deck, a tiki lounge gathering area with wet bar and seating, tennis/pickleball courts, and a private community beach. Offering breathtaking water views, deep-water dockage, and beautifully maintained resort amenities, this residence delivers a rare opportunity to enjoy luxury waterfront living with effortless access to world-class boating, fishing, and the best of the Florida Keys lifestyle.

Welcome to your dream escape in the Florida Keys--this beautifully updated 3-bedroom, 3-bath oceanfront end-unit townhome in the highly sought-after Bonefish Yacht Club delivers the ultimate blend of coastal elegance and laid-back island living. Tucked inside an intimate marina community of just 34 residences spread across lush tropical grounds, this property offers both privacy and a true resort-style feel. Step inside to 1,945 sq. ft. of bright, open living space designed for comfort and entertaining. The modern chef's kitchen features stainless steel appliances, sleek finishes, and ample space for gathering, flowing effortlessly into the dining and living areas. Sliding doors open to a spacious waterfront balcony overlooking the marina--perfect for morning coffee, sunset cocktails, or entertaining with ocean breezes. The primary suite is a serene retreat, complete with its own private balcony, a walk-in closet, and a fully updated ensuite bath. Two additional bedrooms offer flexibility for guests, family, or a home office, each paired with well-appointed bathrooms for comfort and privacy. On the ground level, enjoy the convenience of a private garage and generous storage space--ideal for keeping your fishing gear, paddleboards, and all your Keys lifestyle essentials ready to go. Residents of Bonefish Yacht Club enjoy an array of premium amenities, including a temperature-controlled pool, expansive sun deck, tiki lounge with wet bar, tennis and pickleball courts, and a private sandy beach. Whether you're boating, fishing, or simply soaking in the views, this is island living at its finest. This is a rare opportunity to own a turnkey, oceanfront home in one of the Keys' most desirable communities--where every day feels like a vacation. This unit is a fully licensed 7-day rental.

Rare opportunity to own a legal duplex being sold as A Single Family Home in the heart of Key Colony Beach in the beautiful Florida Keys. Located just one street off the Atlantic Ocean, 340-350 E Ocean Drive offers exceptional space, boating access, and an amazing investment opportunity with flexibility at a competitive price designed to sell. With 5 bedrooms, 3 bathrooms, and over 2,900 sq ft of living space, this property provides the rare opportunity to own a large waterfront home while still benefiting from the layout of a legal duplex. Sold together as a single property, it offers incredible versatility for full-time living, vacation use, or income-producing investment. Boaters will appreciate 50 feet of dockage with dual docks, allowing space for multiple vessels. Buyer and buyers agent to verify all info

Welcome to your slice of paradise in the heart of the Florida Keys. This Conch-style home is tucked away on a wide, clear, deep-water canal just 5 minutes from the crystal blue Atlantic Ocean. Boaters and anglers alike, will love the 60 ft concrete dock with boat lift—ideal for easy ocean access and unforgettable adventures on the water. World-class fishing, diving, snorkeling, and marine wildlife encounters all begin at your dock. Entertain in island style on the decked pool area, huge tiki hut, and screened patio, perfect for relaxing or hosting. The interior boasts a huge, updated kitchen with tons of cabinetry, seamlessly flowing into an open living, dining, and kitchen area with views of the screened patio, Tiki Hut, and pool. Enjoy resort-like living on Key Colony Beach with access to incredible amenities: golf, marina, pickleball, tennis, horseshoes, bocce ball, basketball, playgrounds, and Sunset Oceanfront Park. Everything you need is within reach—restaurants, shopping, post office, police & building departments, and 15 streets to walk, jog or bike. No problem getting here, only 3 miles to Marathon's Airport, 53 miles to Key West International Airport, 108 miles to Miami International Airport, and 139 miles to Ft Lauderdale Airport. Whether you're seeking a full-time residence, vacation retreat, or investment property, this home captures the best of island living in one perfect package.

Welcome to your dream waterfront escape in the Florida Keys! This beautifully updated 3 bedroom, 2 bath home is nestled in an exclusive neighborhood and offers the perfect blend of luxury, comfort, and island charm. Boasting 142 feet of protected dockage on an open bay, it's a boater's paradise with direct access to world-class fishing and diving. Enjoy stunning sunrises from this east-facing property. Soaring vaulted ceilings add to the airy, open feel of the home, while the convenience of an elevator makes access effortless. Step outside to your private coastal oasis featuring a large pool and a spacious downstairs entertaining areaideal for gatherings, grilling, or relaxing after a day on the water. This is more than just a homeit's a true Florida Keys lifestyle!

This waterfront residence in Key Colony Beach offers the perfect blend of refined comfort, thoughtful design, and effortless island living. Lovingly owned, gently used, and never rented, the home reflects true pride of ownership throughout. An elevator, updated kitchen, and custom baths set the stage, while soaring wood ceilings and an open-concept kitchen, dining, and living area create a light-filled space that flows seamlessly through stackable sliders to a spacious screened porchâ€''ideal for entertaining or unwinding in the coastal breeze. The generous primary suite is a private retreat with porch access and a skylit spa-style bath featuring a jetted tub, walk-in tiled shower, and dual vanities. The lower level is designed for true indoor-outdoor living, featuring a custom, inground swimming pool surrounded by elegant marble decking, along with expansive covered and uncovered paved patios. Mature tropical landscaping enhances privacy, while ample covered and uncovered parking adds everyday convenience. Boaters will love the 37.5-foot dock with boat lift, located on a wide, deep canal with quick, easy access, just minutes to both the open ocean and the Gulf via Vaca Cut. A permitted third full bathroom on the lower level sits next to a large, air-conditioned storage area with sliders that open directly to the patio and dock, making it ideal as an angler's room for fishing gear and water toys. Key Colony Beach is one of the Florida Keys' most desirable island communities, known for its wide, walkable streets, city-maintained infrastructure, and relaxed coastal charm. Residents enjoy access to marinas, a nine-hole golf course, tennis and pickleball courts, playgrounds, dining, and waterfront sunset parksâ€''all just steps or a short bike ride away. Perfectly positioned in the Middle Keys, Key Colony Beach offers a rare combination of small-town island living, world-class boating, and easy access to Marathon's shopping, dining, and local airport.

Experience ultimate waterfront luxury living with this stunning 5-bedroom, 3-bath residence (versatile bonus den can be used as 5th bedroom), perfectly positioned on a tranquil, sheltered waterway in a tucked away neighborhood. Thoughtfully designed and impeccably furnished, this home showcases high-end finishes and designer dcor throughout, creating a sophisticated yet comfortable coastal retreat. A rare highlight of this property is the indoor swimming pool, allowing for year-round enjoyment in complete comfort and privacy. Outside, you'll find a tropical oasis backyard for relaxing or entertaining. Feel free to cast a fishing line off your private dockage with 30 ft of waterfront. With direct access to the Atlantic Ocean or Gulf of Mexico, this is a dream for boating and fishing enthusiasts. Enjoy paddle boards or kayaks in your own private lagoon. The spacious open concept living areas are ideal for entertaining. Each bedroom opens up to the indoor pool providing a relaxing sanctuary for family and guests alike. Whether you're seeking a full-time residence or a luxury vacation escape, this exceptional waterfront home combines resort-style amenities, impeccable design, and an unbeatable location for the perfect Keys lifestyle.

Fantastic 6 Bedroom, 4 Bath 3,248 sq. ft. waterfront pool home in Key Colony Beach, an upscale coastal community of waterfront homes that allows weekly rentals and offers a plethora of amenities including gorgeous beaches, a beach club, golf, tennis, pickleball, restaurants, parks, shopping and more! World-class fishing and diving are just minutes from your 75' concrete dock on a 100' wide crystal clear canal offering quick ocean access. After a day on the water relax by your waterfront pool or take a bike ride to one of the great restaurants the island has to offer. The 2-story home is perfect for large families and guests with living areas on both floors and 2 Primary Suites. The home has been beautifully updated including new impact doors and windows and metal roof installed in 2023. The tropically landscaped yard offers lots of curb appeal and privacy. This home is zoned for duplex and with a few modifications can be turned into one. Please ask your agent for more details. Can be sold Turn Key!

Discover exceptional waterfront living in the heart of Key Colony Beach. This concrete constructed half duplex offers over 2,100 square feet with three bedrooms, three bathrooms inside and 37.5 feet of dockage. A highly desirable interior staircase welcomes you from the above flood first floor, seamlessly connecting both levels of the home. Downstairs is completely built above flood and features a one-bedroom, one-bathroom suite with an additional living area, ideal for guests or extended family. Step through sliding glass doors to a spacious wood deck and 37.5 feet of dockage. Enjoy the ocean breeze and shade under the lush buttonwood tree. Upstairs, enjoy open-concept living with a bright, airy kitchen, dining, and living area designed for effortless entertaining. The primary suite boasts a recently renovated bathroom with step-in tiled shower, quartz topped double vanity and tiled flooring. Nearby, a second guest bedroom offers its own ensuite for added comfort and privacy. Recent updates include a newer AC, a 2018 standing seam metal roof, and termite tenting with a transferable warranty, providing peace of mind for years to come. With its downstairs living, expansive square footage, and thoughtfully designed layout, this property presents a unique opportunity to own a well-cared-for waterfront residence in one of the most desirable areas of the Florida Keys. Key Colony Beach welcomes primary and seasonal guests with the 9-hole par 3 golf course, tennis and pickle ball courts, Sunset Park, City Hall, police department, multiple restaurants, boat ramp and marina. Enjoy the island lifestyle with amenities galore!

Join us for Brokers Open House today 4-6 pm! This stunning, fully renovated waterfront home in Key Colony Beach offers the ultimate Florida Keys lifestyle, combining high-end finishes with practical, top-tier enhancements for durability and comfort. Step into a bright, open-flow sanctuary anchored by wood-look tile flooring and crisp custom shiplap walls. The heart of the home is a culinary showpiece, featuring an expanded island with hand-selected quartzite countertops, a farmhouse sink, and an instant hot water system. The sunroom offers an elevated retreat with its tongue-and-groove ceiling, while the bathrooms have been transformed with sleek barn-door glass showers and designer finishes. Designed for the elite boater, the outdoor oasis features a 15,000 lb boat lift and a newly replaced dock (2026). The backyard is a private tropical resort, finished with limestone pavers, a composite raised deck, and a brand-new tiki hut. For the dedicated angler, the garage is thoughtfully equipped with a commercial-grade ice maker and a dedicated bait freezer, ensuring you are always ready for a day on the reef. Every inch of the property has been modernized, from the hurricane impact glass that frames every view to the all-new PVC sewer infrastructure installed in 2023. The saltwater pool is optimized for year-round perfection with a dedicated heater and chiller, while new landscaping and privacy palms create a secluded sanctuary. A circular paver driveway and an expanded outdoor storage closet provide the final touches of convenience to this masterpiece. Call today for your private tour! No sign on the property.

Experience sweeping ocean views and breathtaking sunsets, from both floors of living in this beautifully updated oceanfront residence in Key Colony Beach—the gem of the Florida Keys. The spacious primary suite features an extended living area on the enclosed balcony with amazing blue water & sunset views, a custom bath, and a generous walk-in closet. Two large guest bedrooms offer comfort and privacy for family or visitors. The gourmet kitchen boasts abundant cabinetry, stunning granite countertops, and opens to a light-filled living and dining area complete with a wet bar and panoramic ocean vistas—perfect for entertaining. This home suits any lifestyle: a high-performing vacation rental, a seasonal retreat for snowbirds, or a full-time residence in a meticulously maintained community of just 31 condos and townhomes. Enjoy resort-style amenities including a large oceanfront pool surrounded by expansive sun decks, a fishing pier with breathtaking sunset views, grilling and private lounging areas, covered parking garage, bike and kayak storage, plus guest parking, shuffleboard, and tennis/pickleball courts. Ideally located near marinas, restaurants, shopping, and local attractions, your island dream awaits in paradise.

Experience Key Colony Point with sweeping ocean views and unforgettable sunsets from both levels of this beautifully updated end-unit oceanfront residence in Key Colony Beach— a true gem of the Florida Keys. With a coveted corner location, this residence is wrapped in extra windows and natural light, creating a bright, airy coastal atmosphere you'll feel the moment you walk in. The spacious primary suite is a private retreat, featuring an extended sitting area on the enclosed balcony with mesmerizing blue-water and sunset views, a custom-designed bath, and a generous walk-in closet. Two large guest bedrooms provide comfort and privacy for family and friends, making hosting effortless. At the heart of the home, the gourmet kitchen offers abundant cabinetry and stunning granite countertops, flowing seamlessly into the sun-filled living and dining areas. A wet bar and panoramic ocean backdrop set the stage for easy entertaining, sunset cocktails, or quiet mornings with the sound of the waves. Whether you're seeking a full-time island residence, a seasonal escape, or a strong vacation rental investment, this delivers. The impeccably maintained community of just 31 condos and townhomes offers resort-style amenities, including a large oceanfront pool with expansive sun decks, a fishing pier with postcard-worthy sunsets, grilling and private lounging areas, covered garage parking, bike and kayak storage, guest parking, shuffleboard, and tennis/pickleball courts. Perfectly located near marinas, dining, shopping, and local attractions, this light-filled end unit offers the best of oceanfront living—privacy, views, and the effortless Florida Keys lifestyle you've been waiting for. It is a licensed 7-day rental with rental history.

Embrace the RARE opportunity to own 1.75 acres of open water paradise in the prestigious, gated community of Stirrup Key. Over 750' feet of direct, open Gulf frontage, you'll enjoy spectacular sunrises and sunsets from nearly every vantage point, including a charming sunset gazebo overlooking the iconic Seven Mile Bridge in the distance. The custom Mediterranean-style residence captures the essence of resort living with expansive pavered patios, sparkling elevated pool, and spacious lounging areas absolutely perfect for entertaining against a stunning Gulf backdrop. Five protected basin docks provide sheltered boating access in the marina, while terraced tropical gardens cascade toward the water, lined with mature palms and lush landscaping for a serene coastal ambiance. Inside, soaring cathedral ceilings, wood plantation shutters, and an airy great room with real coral fireplace showcase timeless Keys craftsmanship. The split-bedroom layout ensures privacy, with a luxurious master suite featuring dual closets and skylit bath, plus separate guest quarters. Additional highlights include an elevator, 12,000-gallon cistern, huge garage for cars and golf carts, and a large lower-level storage area with workbenches, pool table, and extra laundry facilities. This gated community, with unique architecture, fewer lots, limited rentals and higher quality restrictions help to sustain a premium and private feel. Only minutes from the Marathon Airport, this one-of-a-kind estate combines open-water grandeur with island tranquility, a true Florida Keys sanctuary.

Experience the charm and character of this Gulf-front Old Florida Keys fishing lodge located in Stirrup Key, one of Marathon's most exclusive gated communities. Known for its large estate lots, deep-water access, and serene open-Gulf vistas, Stirrup Key offers privacy, prestige, and a true island lifestyle, just minutes from the conveniences of Marathon. The property consists of two lots in total for a combined size of 39,500 sf. The home sits on one of the few deep-water sites in Stirrup Key with an upgraded 165-foot pier dock with 6 new pilings, where the water is so clear you can watch tarpon, angelfish, snapper, nurse sharks, lobsters, and rays gliding beneath the dock. Beautifully maintained and elevated above flood, the residence features 3 bedrooms, 3 baths, and a loft that can serve as a fourth bedroom or home office. A brand new roof and impact windows, and sliders were recently installed for peace of mind. The open-concept great room boasts massive ceilings and walls of windows showcasing 180-degree Gulf views. A spacious kitchen with a center island and new range, Gulf front bar, wide overhanging eaves, exposed wood beams, and natural stone accents showcase classic tropical lodge architecture, perfect for entertaining. The primary suite with a large ensuite bath provides comfort and style, while a screened porch opens to the heated pool, positioned behind lush landscaping for afternoon shade. Outdoors, you'll find a sandy beach area, irrigated native landscaping, and expansive decks perfect for sunset gatherings. Additional amenities include two garage bays, one carport bay, a workshop, a garden shed, and abundant storage. Stirrup Key residents enjoy the peace of a gated, low-density community with a 365-day rental minimum, ensuring tranquility and exclusivity year-round. With its unmatched combination of deep water, open-Gulf views, and spacious multi-lot layout, this property is a true rarity in the Florida Keys with potential for expansion.

INVESTORS will appreciate and experience waterfront living at its finest in this beautiful 2 story residence with a ground level elevated entry that has been renovated to achieve the perfect blend of coastal living with upscale entertaining in mind. Thoughtfully designed with an open and airy interior space, and grand entrance that flows effortlessly onto two outdoor balconies makes this residence perfect for entertaining or relaxing and enjoying the bay and sunset views. Features include a beautiful granite kitchen, custom and private bar area, open concept great room and neutral tiled flooring. The spacious chef's kitchen with granite counter tops and stainless steel appliances, a second level master suite with walk in closet, en suite bathroom with jetted tub and separate shower, three well appointed guest bedrooms, 3 bathrooms and office space off the main living area. Windowed porches allow for more living space outside of air-conditioned space as well as more entertaining room. Enjoy fishing off the dock or boating in and out of the area. The nearby community park boasts a small beach, and boat ramp which can be used to launch your boat. Restricted rentals makes this community even more desirable due to less vacation rentals and more serenity. This open water bay front home is located near Marathon Airport and the property can be purchased on one lot or can be combined with two parcels for potentially more living space, a cabana accessory structure, pool, putting green, or pickle ball court. West of Marathon Airport in a gated bay side community. Buy both for future potential living space or simply enjoy the green space overlooking the Florida Bay. Additional lot can be purchase separately and is contiguous to this home on 120 Pirates Cove Drive in exclusive and gated Stirrup Key.