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$2,100,000
3 Beds ⋅ 3 Baths ⋅ 621070 MLS
Experience the best of Duck Key waterfront living with deep-water boating access, ocean views, and spectacular sunsets--all from this ideally located home on desirable Yacht Club Island. The main living level features 2 bedrooms and 2 baths with a bright, open floor plan and an updated kitchen designed for easy Keys living and entertaining. A spacious screened porch and multiple open decks extend the living space outdoors, capturing refreshing ocean breezes and beautiful water views. The elevated lower level offers a legal third bedroom and bath, along with a separate living area, open porch, and deck--ideal for guests, extended family, or a private mother-in-law suite. Boaters will appreciate approximately 75 feet of dockage, deep-water access, and a quick ride to the open Atlantic. After a day on the water, relax beneath the tiki hut overlooking the west-facing canal and enjoy colorful Florida Keys sunsets and tropical breezes. Located in one of Duck Key's most enjoyable walking and biking communities, this property combines boating, outdoor living, and island convenience in one exceptional package. Currently the lowest-priced waterfront home on Duck Key, this is an outstanding opportunity to own your piece of paradise in the Florida Keys.

364 E Seaview Dr, Duck Key
$824,000
3 Beds ⋅ 2 Baths ⋅ 620660 MLS
Seller has this property listed with VRBO. Rental income for 2025 was over $100,000 for the year. Wide water views from this beautiful renovated furnished condo boasting a fantastic floor plan compared to other condos, is attractively decorated with an updated and modern coastal look. Many windows for natural light and a huge L-shaped balcony boasting pocket sliding doors for indoor/outdoor living space. Kitchen has white countertops, newer SS appliances, and a terrific bar/butler's pantry w/ wine refrigerator. Main bedroom opens to the balcony, has large step-in shower and dual sinks. Other features include impact glass windows & doors, natural stone floors, plantation shutters, a barn door, extra storage and covered parking (trucks & pets OK). Full-time residents can homestead this property and receive mail or use as a vacation home with the option to rent through on-site Hawks Cay or personally through rental outlet of your choice (Airbnb, VRBO, VACASA, etc.). Optional membership to resort fitness center, tennis, kids and adult activities. Seller will respond to all offers.

8302 Marina Villas Dr Unit 8302, Duck Key
$2,200,000
3 Beds ⋅ 2 Baths ⋅ 620645 MLS
Welcome to 273 W Seaview Dr, a private retreat in the heart of Duck Key, home to Hawks Cay Resort and some of the best boating and fishing waters in the Florida Keys. Built in 2020 on a 15,247 SF lot, this concrete home is elevated on concrete pilings and engineered to withstand hurricane force winds, with impact windows and doors throughout for lasting peace of mind and favorable insurance considerations. The main living level is reached by two separate entries, a front stairway and a rear balcony, and offers 3 bedrooms, 2 full bathrooms, and an in unit washer and dryer across a bright, thoughtfully finished floor plan with custom exterior finishes, drywall interiors, a flat clay tile roof, and forced air cooling. Below, the ground level provides extensive covered parking and storage space, along with a shaded open porch, ideal for boat gear or beach equipment. Outdoors, the property has been extensively upgraded. The owner just completed a brand new 288 SF pool with a paver deck, and recently added a paver brick driveway and multiple brick and tile patio areas for entertaining. The yard is enclosed with wrought iron fencing and gates for added privacy. A standout feature is the detached 2,046 SF garage on the south side of the property, built in 2023 with room for up to nine vehicles, a rare find for boat owners, car collectors, or anyone in need of serious storage space in the Keys. This property suits a vacation home or full time residence equally well. Duck Key offers a welcoming, close knit island community along with excellent public, private, and charter schools nearby. Enjoy the Florida Keys lifestyle: no state income tax, roughly 230 sunny days a year, and some of the most stunning beaches, fishing, and boating waters in the country. Live securely, comfortably, and luxuriously in paradise, and schedule your private showing today.

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
$679,000
2 Beds ⋅ 2 Baths ⋅ 620133 MLS
PRIVACY GALORE! For buyers who crave true seclusion and one level living, this rare gem delivers unmatched privacy with absolutely no stairs to climb. Soaring tall ceilings and dramatic walls of glass in the living room and kitchen frame a lush, private sanctuary of tropical foliage and towering trees -- nature's own privacy screen. Step onto the wrap-around screened balcony and let yourself be swept away by the symphony of birdsong surrounding you on all sides. This spacious two-bedroom, two-bath condo offers incredible flexibility, with the dining room easily convertible into a third bedroom -- giving you room to grow without ever sacrificing your privacy. Both bathrooms have been beautifully and thoughtfully updated. The kitchen shines with granite countertops and stainless steel appliances, all bathed in natural light from your very own private tropical backdrop. Your privacy extends beyond the unit itself -- a large, secured outdoor storage area on the first floor keeps your kayaks, bikes, and personal belongings safe and out of sight. And when you're ready to venture out, you're just a short walk from several restaurants and the world-famous Hawks Cay Resort Marina, where adventure awaits -- right before you retreat back to your own private paradise.

8301 Marina Villas 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
$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 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
$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
$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
$7,199,000
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
$3,695,000
4 Beds ⋅ 4 Baths ⋅ 618166 MLS
If you're searching for the look, feel, and scent of brand-new construction—complete with soaring vaulted ceilings—on exclusive Duck Key, this is the one. This solid concrete waterfront home has been completely reimagined from top to bottom by the current owner, with no expense spared and uncompromising attention to detail throughout. Every major system and finish is brand new, including impact-rated windows and doors, plumbing, electrical, air conditioning systems, flooring, interior doors, trim, bathrooms, and kitchens. The home is outfitted with top-of-the-line stainless VIKING appliances, underscoring the quality and craftsmanship found at every turn. Enjoy spectacular wide canal views and a layout designed for both comfort and entertaining. The lower level offers a versatile bedroom/office with a full bath, along with a second bedroom overlooking the pool and canal. A brand-new wet bar and entertaining area complete the space, making it ideal for hosting family and friends. Both garages are air-conditioned and equipped with separate built-in dehumidifiers. The outdoor living area is just as impressive. The pool has been fully refinished with glass mosaic tile, including stunning mosaic accent walls, and the surrounding space has been thoughtfully upgraded. A covered porch features an ice maker and refrigeration—perfect for relaxed Keys-style entertaining. Boaters will appreciate the upgraded boat lift and quick access to open water. Spend your days enjoying crystal-clear water, refreshing Atlantic Ocean breezes, and being just minutes from world-class fishing and diving—the Florida Keys at its finest. This home was remodeled as the owner's forever home, and it shows in every detail. The level of care and precision is exceptional. There are simply too many upgrades to list—this is a home you must experience in person to fully appreciate the fit, finish, and quality. And yes, you're just a short golf cart ride from the world-famous Hawks Cay Resor

362 E Seaview Dr, Duck Key