Refine Search
Map
Sort by
$850,000
4 Beds ⋅ 2 Baths ⋅ 620906 MLS
Welcome to this beautifully updated island retreat in the heart of Duck Key! This spacious 4-bedroom, 2-bath home sits on a desirable corner lot, offering extra privacy and great outdoor space. Built solid with CBS construction and recently upgraded with a new metal roof and new impact windows and doors, NEW AC, NEW WATER HEATER, this home is move-in ready and built to handle Keys living with ease. Inside, you'll find nearly 2,000 sq ft of living space with a bright, open feel. The main floor features an updated kitchen with newer appliances, modern cabinetry, and sleek countertops, perfect for cooking and entertaining. The split-bedroom layout provides a private primary suite, while the additional bedrooms offer plenty of space for family or guests. The upstairs living area feels like a cozy treehouse, with large windows bringing in natural light and views of the lush surroundings. Step out to the open balcony and enjoy your morning coffee or evening sunsets. Outside, there's plenty of room for parking a boat, trailer, or golf cart. The corner lot location means more yard space and extra breeze. Located in the sought-after Duck Key community, you're just minutes from world-class fishing, boating, and local restaurants. With no HOA fees and solid storm protection, this property is a perfect full-time residence, vacation home, or rental investment. Don't miss this chance to own a stylish, updated Keys home that's ready for you to enjoy right away.

210 Schooner Ln, Duck Key
$1,975,000
3 Beds ⋅ 2 Baths ⋅ 620892 MLS
Meticulously upgraded island retreat offering resort-style outdoor living on 3 lots spanning 22,500 sq ft, luxury finishes, and smart technology throughout. The backyard oasis features a resort-style pool with an integrated lap lane, custom-blend glass waterline tile, and premium glass bead aggregate finish. Enjoy the sun shelf, waterfall wall, four therapy jets, kept comfortable all year long by a heat pump with chiller. The 18x28 gazebo offers exposed beams, a T&G ceiling, matching metal roof, full summer kitchen, bar, dining/lounge area, and a wood-burning pizza oven. Nearly 6,000 sq ft of travertine pavers cover the driveway, pool deck, and patio, with matching new travertine stairs and over 4,000 sq ft of turf. The covered patio features a new screen enclosure, plus an 8x11 storage shed with matching metal roof. The fully fenced yard includes a walk gate and 10-ft double gate for boat storage. Over 1,500 sq ft of enclosed garage that can accommodate 6 cars and still room for storage and other toys. Inside and out, the home has just been freshly painted (including gutters and railings) with new porcelain wood-plank tile flowing throughout the interior, entry, and terrace. The updated pantry/laundry offers quartz counters and custom built-in shelving. The primary suite showcases a reclaimed wood feature wall, matching platform king bed frame, custom nightstands, and a spa bath with quartz counters and handcrafted glass tile mosaic. Custom walk-in closets serve the primary and guest suites; the third bedroom has a custom media/storage closet. Smart features include a 12-speaker Sonos Wi-Fi system, whole-home smart lighting/pool/climate control, Starlink Gen 4 with wired routers, Ring camera monitoring, automated landscape lighting, and new AC (2026). This is more than a home, it's a fully reimagined island lifestyle.

122 S Bahama Dr, Duck Key
$2,400,000
3 Beds ⋅ 2 Baths ⋅ 620645 MLS
Welcome to 273 W Seaview Dr, your sanctuary in the heart of tropical paradise! This concrete fortress, built to withstand hurricanes, ensures peace of mind in any weather. The 3/2 house, completed in 2020, boasts modern amenities and stylish finishes, offering both safety and spaciousness. This property is perfect for a vacation home, allowing you to relax and enjoy the vibrant surroundings of Duck Key. The owner just recently added a pool as well. The sale of the property also included the garage connected to the property. Experience Florida's many attractions: no state income tax, an average of 230 sunny days annually, and stunning beaches. Duck Key also offers excellent public, private, and charter schools, as well as a welcoming, close-knit community. Embrace the island lifestyle and live securely and luxuriously in paradise!

273 W Seaview Dr, Duck Key
$1,875,000
4 Beds ⋅ 4 Baths ⋅ 620609 MLS
Rare canal-front duplex on Duck Key's prestigious Indies Canal with 70 feet of new composite dockage, sweeping canal views, and deep-water access to both the Gulf and Atlantic. New roof, new AC, and precast concrete construction throughout -- this is a solid, storm-ready build with significant insurance advantages over at-grade alternatives and no deferred maintenance surprises. Two self-contained side-by-side units, each 2BD/2BA with in-unit washer/dryer, private canal-view balcony, open floor plan, and under-house storage. Unit 1 is fully renovated -- granite counters, stainless appliances, new Kitchenaide soft close cabinetry, updated baths, tile floors throughout. Unit 2 features upgraded tile floors and a bright open canvas with kitchen and baths ready for your finish. The options here are unusually flexible: rent both units for strong 28-day vacation rental income, live in one and let the other pay your carry, or convert the entire structure to a single-family waterfront compound -- there's even room for a pool. That kind of optionality, in a precast concrete above-flood building with a new roof and new dock, simply does not exist elsewhere on Duck Key. Monroe County 28-day minimum rental applies. Sold as a complete duplex; cannot be split.

126 N Indies Dr, Duck Key
$349,000
620546 MLS
Build your Florida Keys dream home on this exceptional oversized 9,212-square-foot corner lot in the exclusive community of Duck Key. This cleared lot offers a rare opportunity to create your own vision with approved plans for a thoughtfully designed 3-bedroom, 3.5-bath coastal residence featuring an open-concept layout, spacious walk-in laundry room, generous storage, garage, covered terrace, and a large backyard designed for island living. This property sits at #31 on the BPAS list with 42 ROGO points OR transfer a building right and build today! Nestled within one of the Keys' most sought-after waterfront communities, residents enjoy access to Duck Key's luxury amenities, including a resort-style swimming pool, tennis and pickleball courts, beautifully maintained streets, and a relaxed island atmosphere. The property is also just moments from the Duck Key Marina, offering convenient boating access to both the Atlantic Ocean and Gulf waters. Within walking distance, enjoy all that Hawks Cay Resort has to offer, including waterfront dining, a full-service marina, watersports, beach access, spa services, and resort-style amenities. Whether you're building a primary residence, vacation retreat, or investment property, this is an outstanding opportunity to secure a premium homesite in one of the Florida Keys' most desirable destinations.

101 S Bahama Dr, Duck
$899,900
3 Beds ⋅ 2 Baths ⋅ 620528 MLS
Welcome to an elevated island retreat in the heart of Duck Key. This well maintained 3-bedroom, 2-bath home offers a functional blend of comfort and classic Keys charm in one of the Florida Keys' most sought-after communities--all for UNDER $1 million. Perched elevated for maximum views and protection, the home features a durable METAL ROOF, brand-new impact-rated windows and doors, and a brand-new air conditioner. These thoughtful upgrades deliver peace of mind, energy efficiency, and stunning natural light throughout. Beautiful ocean and island views greet you from nearly every window, creating a bright, breezy atmosphere that perfectly captures coastal living. Step outside to the expansive covered balcony and huge screened terrace--ideal for morning coffee with sunrise views or evening gatherings under the stars. The generous huge backyard provides ample space to create your private oasis, whether you envision a pool retreat, additional outdoor living areas, or simply room to relax and play. One bedroom even offers charming peek-a-boo ocean views. Inside, the open-concept design flows effortlessly, making it easy to entertain or unwind. The home is move-in ready while offering excellent potential to customize--there's even room to enclose part of the patio and add a bath to further increase its value and living space. Practical luxury continues with dual covered carports (easily accommodating two cars), plus abundant extra parking for golf carts, boats, and guests. The large CBS construction ensures durability in this coastal environment. Prime Duck Key location puts you moments from two marinas, a public boat ramp, watersports, and top dining. Residents can join Club Duck Key for resort-style amenities including a heated and chilled pool, pickleball courts, grilling pavilion, and the elegant Grand Lanai with full kitchen--perfect for hosting friends and family. Enjoy year-round community events. This home is a hidden gem!

219 Schooner Ln, Duck Key
$1,649,000
3 Beds ⋅ 4 Baths ⋅ 620472 MLS
DUCK KEY Showpiece. 2023 CBS home with high-end finishes features 3 bedrooms, 4 baths, large pool overlooking tropical island foliage in a private setting. Open floor plan, gourmet kitchen equipped with quartz countertops, custom cabinetry, and a distinctive full-wall ceramic backsplash. An additional 750+/- sqft of lower-level living includes a full bath that is perfect for a 4th bedroom, guest suite or game room. Designer touches and premium builder finishes throughout. Fenced outdoor living space, balconies, dedicated BBQ w/outdoor kitchen area, shed, privacy & more. Built for peace of mind, the property features a metal roof, full impact windows & doors ensuring low insurance costs. The current $1,288.94+/- flood policy is fully assumable. Ample parking and extensive storage are available inside and out. Custom furnishings included with some exclusions. Experience the relaxed island lifestyle that Duck Key has to offer. Easy access to world-class amenities at the Hawk's Cay Resort, nearby boat ramps, dining options, and a variety of activities. Membership to the exclusive Club Duck Key is available to further enhancing the island experience. Don't miss your chance to own a piece of paradise--schedule your showing today! This home is a must see. B&BATVAI

239 W Seaview Dr, Duck Key
$1,398,000
3 Beds ⋅ 2 Baths ⋅ 620387 MLS
Extensively renovated CBS pool home in desirable Duck Key featuring luxury finishes, smart-home technology, and contemporary coastal design. This beautifully updated Florida Keys retreat offers an exceptional blend of modern style and island living, highlighted by a dramatic multi-story screened porch that captures natural light, tropical breezes, and seamless indoor-outdoor living. The designer kitchen serves as the heart of the home, showcasing an oversized quartz waterfall island, premium smart appliances, custom cabinetry, and a spacious walk-in pantry. Throughout the home you'll find soaring tongue-and-groove ceilings, oversized interior doors, designer lighting, and high-end finishes throughout. The luxurious bathrooms have been thoughtfully redesigned with custom tile work, floating vanities, LED mirrors, premium fixtures, and spa-inspired showers that create a true resort-style experience. Thoughtful upgrades and attention to detail are evident throughout every room. Outside, enjoy a beautiful new pool surrounded by an expansive paver deck, creating the perfect setting for entertaining or relaxing in the Florida Keys sunshine. The impressive screened outdoor living area offers a unique architectural feature, providing an inviting space to enjoy island breezes year-round. Elevated construction provides abundant enclosed storage, flexible bonus space, and room for hobbies, fitness equipment, or additional storage needs. Professionally prepared engineering plans for a future expansion are also available, offering additional flexibility and value for future owners. Located in the sought-after community of Duck Key, just minutes from world-class boating, fishing, waterfront dining, and resort amenities. A rare opportunity to own a fully renovated luxury home in one of the Florida Keys' most desirable island communities.

209 Corsair Rd, Duck Key
$1,195,000
3 Beds ⋅ 3 Baths ⋅ 620310 MLS
Welcome to your private island retreat on prestigious Plantation Island in Duck Key, where resort-inspired outdoor living and the relaxed elegance of the Florida Keys come together. Designed to embrace the island lifestyle, this exceptional residence is centered around a spectacular resort-style pool featuring a beach entry, cascading waterfalls, lush tropical landscaping, and inviting spaces to entertain, unwind, or simply enjoy the tropical surroundings in complete privacy. This extraordinary outdoor setting is truly the heart of the home. Inside, the thoughtfully designed layout offers three bedrooms and three bathrooms, with the third bedroom and full bath privately situated on the lower level. The split-level design provides added privacy and flexibility, making it ideal for overnight guests, extended family, a private home office, or multigenerational living. Perfectly positioned on a desirable corner lot just across from the ocean, you'll enjoy one of the Keys' most welcoming island communities. Explore Duck Key by golf cart, spend your days on the water from one of the nearby marinas, or enjoy waterfront dining and the spa at Hawks Cay Resort just moments away. Residents also have the opportunity to become part of the island's vibrant social community through optional memberships and organizations, including Club Duck Key, the Duck Key Fishing Club, and the Duck Key Property Owners Association. For those who travel frequently, the home is conveniently located near the Marathon Airport, offering convenient access for private aviation. The mainland and Key West are both within easy reach, making this an exceptional full-time residence, seasonal escape, or second home. Offering a rare combination of resort-style outdoor living, flexible accommodations, and an unmatched island lifestyle, this is more than a home--it's a place to slow down, reconnect, and experience the very best of Duck Key. B&BATVAI

235 W Seaview Cir, Duck Key
$2,697,500
4 Beds ⋅ 4 Baths ⋅ 620247 MLS
Most sell due to medical expenses! Discover the pinnacle of island luxury in this stunning canal-front estate located in prestigious Duck Key. Completely transformed by a 2022 remodel, this 4-bedroom, 4-bathroom residence offers an effortless blend of modern sophistication and relaxed Keys living. Set on a generous 12,500-square-foot lot, the resort-style outdoor space features a custom tiki hut with an outdoor kitchen, a sparkling saltwater pool, and a 100-foot concrete seawall. Serious boaters will love the brand-new 20,000-pound lift with 50-amp service and a custom storage shed. The interior features over 3,400 square feet of beautifully finished space, including a gourmet kitchen featuring premium appliances, a bright Florida room, and expansive living areas. The thoughtful layout provides two bedrooms on the main level and two additional bedrooms upstairs, each with a private ensuite bath. The upper level also features a large balcony that captures sweeping views of the crystal-clear canal. Built with solid CBS construction, impact windows and doors, and a metal roof, this home combines refined design with peace of mind. Truly an exceptional value, this Duck Key masterpiece is ready for its new owner. Schedule your private showing today to experience the elegance and serenity of this remarkable home.

1100 S Indies Dr, Duck Key
$2,595,000
3 Beds ⋅ 3 Baths ⋅ 620076 MLS
Some homes simply arrive finished -- and this Duck Key showstopper is one of them. Dressed in modern coastal farmhouse finishes and positioned along a serene canal, it delivers the rare combination most buyers spend years searching for: a seamlessly curated interior, serious boating infrastructure, and not a single update needed. The palette flows effortlessly throughout -- soft whites, warm creams, and sun-bleached sand tones that feel both elevated and livable. The main living area commands attention with soaring vaulted ceilings, anchored by a sweeping wall of windows that frames the canal like a living painting. Step through to the expansive screened patio and the boundary between indoors and out dissolves entirely. The kitchen centers around a substantial quartz island, flanked by custom oversized cabinetry and stainless appliances. Screened enclosures at both the front and rear include dedicated storage for fishing tackle and marine gear -- because the lifestyle here demands it. And then there is the dock. At a rare ninety-three feet in length with an exceptional beam width, fully equipped with water, electric, and a 24,000-pound boat lift, this is not a recreational amenity -- it is a destination. Few properties in the Keys offer this combination of length, width, and capacity. Architectural details speak to the quality throughout: a crisp standing-seam metal roof, impact-resistant windows and doors, an oversized motor court, and intentionally low-maintenance grounds. Inside, porcelain tile floors, LED-lit vanity mirrors, a double vanity in the primary suite, oversized closets, and new plumbing and light fixtures complete a home finished with genuine care. The existing patio deck can be converted back into a future swimming pool. This is Duck Key living at its finest. Schedule your private showing today.

248 W Seaview Dr, Duck Key
$844,000
2 Beds ⋅ 2 Baths ⋅ 619521 MLS
Discover one of the best values in Duck Key -- a spotlessly maintained, move-in-ready two bedroom two bath home on Plantation Island that checks every box for the savvy first-time Keys buyer or the discerning second-home seeker looking for low-maintenance island living at one of the best neighborhoods in the Middle Keys. This spacious, elevated residence welcomes you with an open, airy floor plan that feels expansive from the moment you walk in. Natural light pours through generous living spaces designed for easy entertaining and effortless everyday comfort. Step out onto the screened balcony and let the warm Keys breeze remind you exactly why you fell in love with this place. What truly sets this home apart is the jaw-dropping four-car garage -- an extraordinary luxury in the Keys that gives you all the room you need for vehicles, golf carts, water toys, and gear, with plenty left over. No more hunting for storage. No more compromises. Whether you're searching for your first foothold in paradise or a beautifully turnkey retreat that practically takes care of itself, this Duck Key gem delivers the lifestyle without the hassle. Priced to make your Keys dream a reality today. Exceptional value. Unbeatable location. This is the one!

249 W Seaview Dr, Duck Key
$1,100,000
3 Beds ⋅ 2 Baths ⋅ 619487 MLS
Experience island living on Yacht Club Island in Duck Key, an exclusive oceanfront community known for privacy and a relaxed coastal setting. This 3-bedroom, 2-bath residence features a modern, updated interior in the heart of the Florida Keys. Bright, open living areas offer neutral finishes, tile flooring throughout, and the screened in porch and expansive windows frame Atlantic Ocean views. The kitchen is appointed with quartz waterfall countertops, stainless steel appliances, and abundant cabinetry. The 3 bedrooms are split across two levels, providing added privacy. Bathrooms include glass-enclosed showers and updated contemporary finishes. Positioned on a corner lot, the property provides space for outdoor enhancements, with potential for a pool or tiki hut. Optional separate membership in the exclusive Club Duck Key is available, offering pickleball, tennis, a pool, clubhouse, and variety of community activities. Nearby, the full-service Duck Key Marina provides wet and dry slips for boating enthusiasts. This beautiful, walkable oceanfront island community offers unlimited possibilities as your next primary residence, second home, or investment opportunity.

309 Jasmine St, Duck Key
$3,000,000
2 Beds ⋅ 2 Baths ⋅ 619370 MLS
This 2 bed 2 bath home on the second floor. Recently gone through major renovations from top to bottom- inside out. Open concept with brazilian wood floor, fully furnished, chefs kitchen with top of the line wolf appliances. A warp around balcony to enjoy the water and spectacular sunset views. On the lower level you have a one car garage used as storage a separate laundry room, cabana bath and a room. New pool with jacuzzi, hot tub and a tiki hut with a TV. A 75ft dock

232 W Seaview Dr, Duck
$5,895,000
6 Beds ⋅ 6 Baths ⋅ 619297 MLS
This magnificent, exclusive estate on Duck Key offers a rare opportunity to own one of the most impressive waterfront properties in the Middle Keys. Set on a large, elevated, fully fenced and gated lot, the home boasts over 123 feet of protected deep-water dockage with approximately a 10-foot draft--ideal for serious boaters--along with sweeping, unobstructed views of Lake Lucille. Designed for both relaxation and entertaining, the outdoor space is truly resort-style. Enjoy a beautifully updated pool and spa, enhanced by new water features and a state-of-the-art outdoor sound system. The poolside cabana bar, complete with grill and a full-bath, creates the perfect setting for hosting guests in a private tropical oasis. Inside, the home is filled with natural light and elevated by soaring ceilings and elegant travertine marble floors. The spacious chef's kitchen is thoughtfully designed with seamless access to outdoor living areas, making indoor-outdoor entertaining effortless. The primary suite is conveniently located on the main level, while all guest bedrooms and bathrooms have been tastefully updated. Additional highlights include a rare wraparound balcony, a patio overlooking the pool and lake, a two-car garage, and an expansive basement offering exceptional storage. Boating enthusiasts will appreciate the multiple boat and jet ski lifts, as well as a floating dock. This is waterfront living at its finest--combining luxury, privacy, and unparalleled access to the open water.

152 N Indies Dr, Duck Key
$399,000
619149 MLS
Build your dream in the Florida Keys on this cleared corner lot in sought-after Duck Key. Much of the groundwork has already been complete allowing you to focus on designing your ideal island retreat. Next quarter the property will be at 42 points, after that next step to 44 points = permit. After 42 points which should be obtained in May, 2026, another 2 points can be gained by filing already updated house plans to make it more possible to obtain permit in 2026. Nestled in a peaceful and desirable community, Duck Key offers a tranquil lifestyle surrounded by natural beauty, making it perfect for full-time living, a vacation home, or an investment opportunity. Whether you're an individual buyer or a developer, this property presents exceptional potential in a desirable Keys location. Ownership also offers the opportunity to join the Duck Key Club, where you can enjoy resort-style amenities including a clubhouse, swimming pool, jacuzzi, tennis, and pickleball, perfect for embracing the Florida Keys lifestyle.

223 Schooner Ln, Duck
$3,550,000
3 Beds ⋅ 3 Baths ⋅ 619042 MLS
Motivated Seller...Welcome to your dream coastal retreat on Duck Key, where BREATHTAKING COASTLINE VIEWS and refined island living exist in perfect harmony. This beautifully curated DESIGNER RESIDENCE is a three-bedroom, three-bath oceanfront concrete home by D'Asign Source, blending timeless elegance with modern comfort through soft earth tones, quality finishes, and sweeping panoramic views of the turquoise waters beyond. Inside, a spacious chef's kitchen anchors the home--ideal for entertaining--while a thoughtfully designed split floor plan offers privacy and flow. Two guest bedrooms enjoy direct ocean views, and the expansive primary suite is a serene sanctuary featuring a luxurious en-suite bath with designer tile, dual vanities, custom cabinetry, and a built-in makeup station. Step outside into your private waterfront oasis. A custom oceanfront pool deck and generous covered patio create the perfect setting for relaxation after a day on the water. A 25,000 POUND BOAT LIFT and seawall provide effortless access to the open ocean with no fixed bridges, making this an exceptional location for boating, paddleboarding, and kayaking directly from your dock. Additional features include a screened-in balcony with electric shutters, two large storage rooms, an L-shaped two-car garage, ample outdoor parking, and a wide driveway. Located on a golf cart-friendly island, Duck Key offers convenient access to restaurants, bars, shops, and social clubs. Whether you enjoy fishing, boating, or simply soaking in spectacular sunsets, Duck Key delivers an unparalleled waterfront lifestyle. Surrounded by crystal-clear waters and shallow sandbars teeming with marine life, this home is not just a residence--it's a destination. Schedule your private showing today and experience the very best of Duck Key living.

250 W Seaview Cir, Duck Key
$2,899,000
2 Beds ⋅ 3 Baths ⋅ 619033 MLS
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.

425 Harbour Dr, Duck Key
$4,400,000
618564 MLS
8,190 SF vacant lot on Duck Key Island along a deep water canal with open water views. Located next to Hawks Cay Resort, which offers dolphin swims, dining by a Michelin-rated chef, and a marina. Duck Key is centrally positioned near luxury restaurants in the Keys, Grassy Key sandbar, deep drops for offshore fishing, clear Bahamian waters, nearby reefs for lobstering and reef fishing, and the Islamorada Humps for tuna. Weekly rentals are not allowed on the island, creating a residential feel with more locals than tourists. The property includes a barrier in front for storm protection and is ROGO-exempt due to a previous home on the site. Ready to build your dream home. Schedule a viewing today.

318 E Seaview Cir, Duck
$4,250,000
4 Beds ⋅ 4 Baths ⋅ 617294 MLS
An Oceanfront Masterpiece with Infinite Horizons Commanding a premier position above the crystal-clear waters of the Atlantic, this exceptional open-water estate represents the pinnacle of refined island living. With its highly sought-after southern exposure, 258 W Seaview Circle is immersed in golden sunlight throughout the day, offering uninterrupted panoramic ocean views and the gentle cadence of waves just steps from the residence. Beyond the protective breakwater, a pristine sandy shoreline and natural sandbar unfold—an idyllic extension of your private coastal sanctuary. Designed to seamlessly balance sophisticated entertaining with effortless relaxation, the estate features an impressive 112-foot bi-level dock and seawall, perfectly suited for the discerning boating enthusiast. The oceanfront terrace is anchored by a striking 50-foot lap pool, elevated eight feet above sea level to maximize views and serenity. Framed by a charming Tiki hut, lush tropical landscaping, and curated ambient lighting, the outdoor living spaces transform into an enchanting seaside retreat as evening falls. Inside, classic craftsmanship is paired with modern elegance. This four-bedroom, three-and-a-half-bath residence offers a coral rock fireplace, private elevator, and a generously proportioned gourmet chef's kitchen designed for both everyday indulgence and elevated culinary experiences. Every detail—from the architectural finishes to the meticulously maintained grounds—reflects exceptional care, quality, and pride of ownership. Whether hosting intimate gatherings beneath the stars, savoring tranquil mornings overlooking endless blue horizons, or setting out for a day on the water, 258 W Seaview Circle delivers an unrivaled lifestyle in Duck Key, widely regarded as the Middle Keys' most prestigious enclave. Residents enjoy access to two marinas, watersports, and local dining within this charming, golf cart-friendly island community.

258 W Seaview Cir, Duck Key
$1,399,000
3 Beds ⋅ 3 Baths ⋅ 616464 MLS
Discover a rare opportunity in the heart of Duck Key at 1 Trinidad Street. This exceptional compound spans over an acre of land, offering remarkable potential for redevelopment, expansion, or as a long-term investment. Whether you choose to renovate the existing home, design your dream estate, or hold as a strategic asset, the scale and privacy this property provides are unmatched in the area. The existing structure is a solid, concrete-built three-story home featuring 3 bedrooms, 2.5 bathrooms, porcelain flooring, and impact windows—a durable foundation to enjoy now or reimagine entirely to suit your vision. Prime Location: Ideally situated directly across from the Duck Key Clubhouse, just steps from the pool, tennis courts, and social amenities, this property blends lifestyle appeal with investment value—offering one of the most sought-after settings in the Florida Keys.

1 Trinidad St, Duck Key
$2,350,000
3 Beds ⋅ 3 Baths ⋅ 618104 MLS
Welcome to your private island retreat in the heart of Duck Key. Perfectly positioned just a few homes from the Seaview Channel, this exceptional waterfront residence offers instant access to both the Atlantic Ocean and the Gulf of Mexico—an ideal setting for boaters, entertainers, and families alike. This beautifully maintained home features three bedrooms and three baths, including downstairs living space, providing flexible options for guests, extended family, or a private suite. The remodeled kitchen and bathrooms showcase a European design, with wood cabinetry, granite countertops, and refined finishes throughout. Indoor-outdoor living is at the heart of this property. Step outside to a gorgeous pool and Jacuzzi, surrounded by a spacious pool deck with a built-in bar area, perfect for entertaining under the Florida sun. A large screened-in balcony captures beautiful water views in every direction, offering a serene space to relax and unwind. This space could easily be enclosed to add more living space. Additional highlights include a one-car garage, 75 feet of concrete dockage, and a fabulous canal setting just moments from open water. Easy to show and ready to enjoy, this Duck Key home delivers the very best of Keys living—luxury, lifestyle, and location.

272 W Seaview Dr, Duck Key
$614,000
2 Beds ⋅ 2 Baths ⋅ 618430 MLS
Hawks Cay Harbor Village Villas offer a luxurious and tranquil retreat in the stunning Florida Keys. Nestled within the renowned Hawks Cay Resort on Duck Key, these waterfront villas boast breathtaking views of the sparkling waters of the Gulf of Mexico and the resort's private marina. This property has a beautiful patio and spa dipping pool overlooking the canal. With their spacious floor plans, these villas feature contemporary coastal designs, providing guests with a real Keys experience. This particular villa is priced at a competitive price to sell quickly. You can enjoy this as your own private get a way to the Keys for your family vacation as well as these owners have rented it out and received a nice ROI. Walk to the restaurant, the spa, tennis courts, large family pool, etc.

7028 Harbor Village Dr, Duck Key
$1,374,499
4 Beds ⋅ 3 Baths ⋅ 618156 MLS
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.

247 W Seaview Cir, Duck Key
$2,950,000
617185 MLS
An exquisite opportunity awaits the discerning visionary: a rare, expansive oceanfront lot gracing the serene shores of Duck Key, one of the Florida Keys' most exclusive and coveted enclaves. This prestigious parcel, nestled on the tranquil, sought-after side of West Seaview Drive, offers unparalleled south exposure--delivering golden morning light, refreshing ocean breezes, and mesmerizing sunsets over the turquoise Atlantic. Already enhanced with premium infrastructure, including a concrete seawall for enduring protection, a private dock, and a dedicated boat lift, the lot is meticulously prepared for immediate realization of your bespoke waterfront estate. In this gated island sanctuary renowned for its refined luxury, deep-water access, and intimate community elegance, envision crafting a timeless masterpiece: your personal oceanfront legacy, where every detail reflects sophistication and the sea becomes an extension of your living space. ROGO approval is required to proceed with construction, underscoring the exclusivity and measured prestige of this once-in-a-generation opportunity. Secure this irreplaceable canvas and elevate your life to extraordinary heights in paradise.

219 W Seaview Dr, Duck
$4,385,000
3 Beds ⋅ 3 Baths ⋅ 618298 MLS
First time ever offered, this extraordinary open-water estate commands a premier position on Duck Key overlooking the crystal-clear waters of Tom's Harbor and iconic bridge. Spanning two expansive lots with an impressive 152 feet of water frontage, this iconic residence—designed by renowned architect Dale Baldwin—delivers rare scale, privacy, and timeless Florida Keys elegance. A dramatic double-door entrance opens to a light-filled open floor plan defined by white-washed vaulted and tray ceilings, walls of windows, and sweeping harbor views. The chef's kitchen features black granite countertops, a statement island, butler's pantry, and premium appliances including Thermador double ovens, Jenn-Air cooktop with grill, Whirlpool French-door refrigerator, and GE trash compactor. A formal dining space for twelve, pass-through bar and billiards area, and spacious living zones create an exceptional environment for elevated entertaining overlooking the water. The oversized primary suite offers a private waterfront retreat with spa-inspired bath, expansive walk-in closet, and balcony overlooking open water. All bedrooms enjoy private balconies. Additional highlights include abundant storage, interior stairways, laundry room, white ceramic tile floors, and plush carpeted bedrooms. Outdoors, a screened balcony, resort-style pool with paver deck, and mature tropical landscaping frame the ultimate island lifestyle. The expansive T-dock provides outstanding versatility for a boat lift, jet ski lift, and kayak launch. Built with solid concrete construction, standing-seam metal roof, accordion shutters, subfloor access, two-car garage, and a grand half-circular driveway. A landmark offering where architectural distinction meets open-water serenity on prestigious Duck Key.

112 Bimini Dr, Duck Key
$1,099,000
3 Beds ⋅ 2 Baths ⋅ 618642 MLS
SELLER FINANCING OFFERED! Welcome to this BRAND NEW spacious corner lot in the heart of Duck Key. Elevated for added peace of mind, this 3-bedroom, 2-bath stilt home features soft coastal tones, sleek tile flooring throughout, window treatments and impact-resistant windows/doors for storm protection and energy efficiency. Duck Key is a charming, golf cart-friendly island known for its laid-back lifestyle and sense of community. Optional membership to the nearby social club offers access to top-tier amenities including a resort-style pool, tennis and pickleball courts, a full kitchen, and a beautiful Grand Lanai - perfect for gatherings and entertaining. Boaters will love the convenience of Duck Key Marina, offering both indoor and outdoor storage, fuel, and boat rentals - all just minutes from your doorstep. Don't miss your chance to live in one of the Keys' most desirable neighborhoods in the Florida Keys!

224 W Seaview Dr, Duck Key
$1,170,000
3 Beds ⋅ 2 Baths ⋅ 618139 MLS
Perfectly positioned on a coveted CORNER LOT just steps from Club Duck Key, this 2021-built residence embodies refined coastal living with the strength and security of elevated rigid CBS construction. Designed for effortless ownership, the NEWER HOME features solid concrete construction, a metal roof, and full impact windows and doors—delivering exceptional durability, energy efficiency, and low-maintenance peace of mind. Nearly 1,500 square feet of thoughtfully designed interiors showcase SOARING 9 FOOT CEILINGS with cove detailing, recessed lighting, engineered laminate flooring, and plantation shutters. The OPEN CONCEPT layout flows seamlessly into a designer kitchen appointed with quartz countertops, a statement island, white soft-close cabinetry, glass tile backsplash, and stainless appliances—perfect for both sophisticated entertaining and relaxed island living. The primary suite offers a serene retreat with a SPA-INSPIRED BATHROOM, soaking tub, dual vanities, and a walk-in closet. Two additional guest bedrooms and a beautifully finished bath provide comfort and versatility. A dedicated laundry room with utility sink, cabinetry, beverage refrigerator, and instant hot water enhances everyday convenience. Outdoor spaces are equally impressive, featuring an expansive covered carport, elegant brick pavers, a large enclosed storage room, and a tiled covered balcony ideal for morning coffee or sunset gatherings. With immediate access to resort-style amenities including a heated and chilled pool, hot tub, tennis, pickleball, marinas, and dining, this exceptional property offers the ultimate blend of quality construction, lock-and-leave ease, and premier proximity in the heart of Duck Key.

101 San Juan St, Duck Key
$7,499,000
7 Beds ⋅ 6 Baths ⋅ 616613 MLS
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.

308 Sabal St, Duck Key
$2,444,000
2 Beds ⋅ 2 Baths ⋅ 618772 MLS
Rare opportunity to secure a prime waterfront homesite on highly desirable Duck Key. This is 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, deep water 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.

154 S Indies Dr, Duck Key