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$639,900
2 Beds ⋅ 1 Baths ⋅ 617416 MLS
Introducing this charming and newly upgraded Keys Conch Cottage tucked away in the desirable Tropicana subdivision in the heart of Marathon. Set on an impressive 8,000+ sq ft lot, this property offers the rare benefit of flexible mixed-use zoning, allowing for short-term vacation rentals, home-based businesses, and even the potential to divide the side portion of the lot for an on-property business space, an exceptional opportunity for versatility and income potential. It is currently an active, licensed vacation rental with repeat guests already in place. Inside, you'll find a cozy 2-bedroom, 1-bath layout complemented by a large, oversized workshop ideal for storage. The home has been thoughtfully updated with 3 brand-new mini-split air conditioning systems, providing excellent cooling and energy efficiency. All appliances have been upgraded within the last year to matching white KitchenAid, giving the kitchen a clean, cohesive, modern look. Additionally, both the exterior and the entire interior of the home were freshly painted within the past year, offering a crisp, move-in-ready feel throughout. Brand-new impact windows and doors add further value with improved energy efficiency, security, and storm protection, while mature tropical landscaping enhances the authentic Old Florida Keys charm. Step into your private backyard retreat, where lush greenery creates a serene, secluded atmosphere. Enjoy a relaxing soak in the hot tub under the stars, entertain friends, or simply unwind in your own island oasis. The expansive lot provides ample parking for multiple vehicles, trailers, and boats—perfect for an active Keys lifestyle. With three public boat ramps just minutes away and close proximity to the world-famous Sombrero Beach, enjoying days on the water or in the sand is effortless. Whether you're seeking a personal island getaway, a strong income-producing investment, or a unique property with zoning flexibility this is the place for you!

543 74th St, Marathon
$1,425,000
3 Beds ⋅ 2 Baths ⋅ 618248 MLS
Discover the rare opportunity to own a premier developer's unit in one of Key West's most desirable waterfront communities. Perfectly positioned just across the street from world-famous Smathers Beach, this spacious 3-bedroom, 2-bath condo blends coastal luxury with unbeatable island convenience. Inside, expansive living spaces open to large windows and glass doors showcasing ocean views and endless natural light. The open-concept kitchen flows seamlessly into the dining and living areas—ideal for entertaining or relaxing after a day on the sand. Retreat to the ocean-view primary suite, complete with generous closet space and private bath. Two additional bedrooms offer the flexibility for guests, family, a home office, or rental income. Step outside and enjoy resort-style amenities—lush tropical grounds, shoreline paths, sparkling pool, and easy access to water sports, biking, and Key West's sunset scene. Whether you're seeking a primary residence, island getaway, or investment opportunity, this condo delivers everything that makes Key West living unforgettable. Highlights: *Rare developer's unit with expanded layout/premium features *Just steps to Smathers Beach, bike paths & sunrise walks *3 Bedrooms / 2 Bathrooms *Assigned covered parking bay and storage unit *Resort amenities & gated community *Minutes to Old Town, dining, airport & nightlife Your Key West waterfront life starts here—schedule your private showing today!

1901 S Roosevelt Blvd Unit 401E, Key West
$18,999,000
6 Beds ⋅ 8 Baths ⋅ 615643 MLS
A private sanctuary of coastal sophistication, The Oasis offers two residences spanning 2.85 meticulously landscaped acres with over 400 feet of pristine waterfront and a protected deepwater basin. Designed for elevated living, The Oasis blends resort-style amenities with the privacy and scale of a true Florida Keys compound. The grand porte-cochère entry sets the tone, leading to a single-level main residence with soaring ceilings, white oak floors, and 12' retractable glass walls that frame sweeping ocean views. The chef's kitchen is anchored by a Calacatta marble island, Thermador appliances, and a walk-in pantry, opening to a spacious great room and dining area ideal for entertaining. The main home features four bedrooms, six full bathrooms, and a soundproof theater room. The primary suite is a private retreat with a fireplace, dual walk-in closets, a safe room, and a spa-inspired bath with a steam shower. Each additional bedroom includes an en suite bath, private balcony, and ocean views. A detached guest house offers two additional bedrooms and bathrooms, creating a total of six bedrooms across the estate with endless space for expansion. The summer kitchen, alfresco dining areas, and multiple lounging terraces offer seamless indoor-outdoor living. The deepwater basin accommodates larger vessels and provides quick access to the Atlantic and Bay. Amenities rival a private resort: soundproof theater, fitness center with sauna, golf simulator, and two resort-style pools—each with a spa, sun deck, and outdoor entertaining spaces. Discreetly luxurious and effortlessly livable, The Oasis redefines waterfront living in the Florida Keys. Designed for ultimate security and safety, this home was built to provide unmatched peace of mind. Every element was designed with meticulous attention to detail and an uncompromising commitment to quality. The Oasis is not just a residence—it is a lifestyle statement in one of the Florida Keys' most desirable locati

87429 Old Hwy, Islamorada
$3,500,000
1 Baths ⋅ 598957 MLS
Investment Opportunity - Self-storage facility with excellent exposure to passing traffic, located directly on US Highway 1 near Mile Marker 10, just outside the City of Key West. Built in 2020, the property features approximately 90 climate-controlled interior storage units of various sizes, including both lockers and traditional units with roll-up doors. The site is also approved for 11 external stackable containers or can be utilized as open parking for trailers, RVs, or additional storage. The elevated three-story building consists of approximately 6,912 SF and is constructed with a poured concrete foundation and concrete/steel frame, along with impact-resistant windows and doors. The property includes a fully gated lot of approximately 22,500 SF, as well as security systems, a fire sprinkler system, elevator lift, two staircases, office space, and a restroom. Ideal for both investors and owner-users, offering strong income potential with the ability to generate passive income from the upper levels, while utilizing the ground floor as a large office or operational space. The expansive lot provides ample room for additional storage, equipment, vehicles, or business use. Please do not disturb business.

323 Overseas Hwy, Big Coppitt
$2,300,000
3 Beds ⋅ 3 Baths ⋅ 611841 MLS
Make all of your Florida Keys fantasies come true at Fantasy Harbor! We're willing to bet you never even knew this gated community on Islamorada's Lower Matecumbe existed. This concrete harborfront home is being offered for the very first time. Upstairs 2 bedroom 2 bathrooms suites with open and spacious harborview living areas plus downstairs bedroom and bathroom with a bonus party hut reminiscent of relaxing Bahamian nights after a day on the water. Quiet & private living situated just off the Florida Bay in a protected harbor with 99' concrete seawall on cap rock plus boat lift. This one is a winner!

76412 Overseas Hwy, Islamorada
$675,000
3 Beds ⋅ 2 Baths ⋅ 611488 MLS
Spacious New contemporary home in the Largo Gardens subdivision. This fabulous new home features many higher end finishes like whole house wood plank style Porcelain floors throughout, Oversized kitchen cabinets with durable Quartz counter tops, upgraded fully tiled baths with designer plumbing fixtures, illuminated mirrors and much more. The home includes a tankless water heater and full-sized Washer/Dryer hook-ups in laundry room. Rest easy knowing that this home is built solid. Impact windows and Impact French doors, all concrete walls, and a durable metal roof are some of the design elements that meet or exceed the demanding wind resistance standards for new homes. No conservation deed restriction or requirements allows for the use of the entire property. There is plenty of room for a future pool or boat/RV storage. This home is conveniently located near restaurants, shopping, and only 45minutes from the mainland.

16 Tina Pl, Key Largo
$675,000
2 Beds ⋅ 2 Baths ⋅ 616069 MLS
LOWEST PRICED HOME IN THE VILLAGE OF ISLAMORADA! Charming Home in a desirable Plantation Key Subdivision! This well-maintained Sheffield Steel home offers excellent curb appeal with lush, tropical landscaping. Inside, enjoy an open-concept layout with two bedrooms and two bathrooms, highlighted by beautiful Dade County Pine ceilings and an abundance of natural lighting. Step out onto the open upstairs balcony—perfect for relaxing and soaking in the Florida Keys lifestyle. The spacious front yard provides ample parking, and the ground level features a large storage room. Whether you're looking for a full-time residence or a great investment opportunity, this property checks all the boxes. Conveniently located near top-rated schools, shopping, restaurants, and hospital.

115 Fontaine Dr, Tavernier
$639,000
2 Beds ⋅ 3 Baths ⋅ 618452 MLS
Recently updated throughout, featuring a completely renovated spa/jacuzzi installation, brand new tile flooring throughout the entire unit, and freshly painted interior and exterior walls. Plantation shutters enhance the interior, while updated interior doors and modern hardware add a refined touch. The open layout offers tile flooring on the main level and wood laminate upstairs. The spa pool has been refinished and retiled, complemented by elegant tile accents along the surrounding privacy wall. Enjoy the private patio with landscape lighting, outdoor shower, and roll-down/accordion shutters for added protection. The kitchen features white cabinetry, a stylish backsplash, stainless steel appliances, and granite countertops. A motorized shade with a remote control along the sliding doors provides privacy and shade. Conveniently located next to the Fishing and Walking Pier access. Offered fully furnished with a few exclusions. Owners may enjoy the amenities of Hawk's Cay Resort with participation in the resort management program.

7026 Harbor Village Dr, Duck
$685,000
3 Beds ⋅ 2 Baths ⋅ 617211 MLS
Well maintained stilt family home with three bedrooms on the same floor. Open kitchen with beautiful white marble counter tops and white cabinets for the chef. Vaulted ceilings with plenty of windows allowing the natural light inside. Tile floors throughout this well-kept home. Metal roof for your security and plenty of outdoor space to enjoy the privacy. Room for a pool also. Lots of parking at this great location. Microwave is a convection and air fryer, all stainless-steel kitchen appliances. Washer and dryer stackable included. Newer sliding glass shower enclosure in primary bathroom. Move in condition and immaculate interior. Extra yard for your parking and entertaining needs. Storage shed in the private carport for extra storage. Open front porch to enjoy your morning coffee and afternoon tea time.

150 Peace Ave, Tavernier
$419,000
2 Beds ⋅ 1 Baths ⋅ 616216 MLS
Rare DOUBLE SIZE LOT on OPEN WATER with BOATING ACCESS and ROGO EXEMPT LETTER IN HAND!! This lot offers magnificent sunset views over the open water and has plenty of room to add a dock for your boat. There is a canal cut around the perimeter of Saddlebunch Key giving the property shallow boating access to the Atlantic and Gulf. This subdivision has a nice park with tennis & pickleball courts, bocce, basketball, a fenced playground and large grassy area to enjoy. Baby's Coffee is a short walk from this property. Located just 10 minutes from Key West, where you will find superior dining and nightly entertainment, unique boutique shopping, plus major grocery chains, gyms, and most anything you could need. Build your dream home now, and enjoy beautiful open water sunset views forever. ROGO EXEMPT LETTER IN HAND means no waiting and hoping for a building right, this property comes with one!

6 Beach Dr, Saddle Bunch
$6,499,000
601994 MLS
A rare opportunity to own a private island with approx. 40 acres and only minutes from Key West. So many possibilities: Build your own Equestrian Estate on approx. 6 acres of upland, ''The Southernmost stables'' with up to 12 horses. This property would be an excellent place to host large events like concerts, weddings, farm to table / wine tastings, or possibly therapeutic programs or retreats on a beautiful beach area. Easy to get to, as the island has access to the mainland via a ½ mile land bridge. The property is also located next to one of the largest mega yacht marinas and close to two upscale hotels. The owners used to run a small farm, bee keeping, music events, and kids summer camps on the island. One of the few places with untouched nature left in the Florida Keys. There are hives and bee boxes throughout the island - bees producing delicious mangrove honey. The property has about 40 acres of mangrove forest, beach berms, hammocks, upland and trails, and waterfront. 'I think having land and not ruining it is the most beautiful art that anybody could ever want to own.' - Andy Warhol Buyer to verify all information and uses.

7200 5th St, Stock Island
$2,699,000
3 Beds ⋅ 3 Baths ⋅ 616434 MLS
Welcome to 3206 Riviera Drive, Key West - a stunning canal-front retreat designed for the ultimate Key West lifestyle. This fully gated residence offers 60 feet of waterfront with no neighbors across, creating unmatched privacy and serene water views. Inside, a bright open floor plan with a wall of glass impact sliders connects indoor living to the outdoors. The spacious kitchen features a large island, high-end cabinetry, and a waterfront dining area perfect for entertaining. With 3 large bedrooms—each with closets (2 en-suite)—and 3 full baths plus a laundry room, this home combines comfort with style. Premium finishes throughout include high-end tile, custom cabinetry, and a thoughtful layout enhanced by two-zone AC and a home generator. Step outside to your private oasis: a screened back patio, redone heated pool, outdoor kitchen, outdoor bathroom, and shell stone limestone walkways that wind through beautifully landscaped gardens. Covered parking, tropical landscaping, and full gating complete the package. This is Keys living at its finest—stylish, secure, and ready to enjoy. Seller financing possible!

3206 Riviera Dr, Key West
$1,175,000
2 Beds ⋅ 2 Baths ⋅ 618827 MLS
An UNBEATABLE LOCATION1 This light-filled, Old Town condo just one block to Duval Street! This home shines with 23 windows on two levels and relaxes with its easy, breezy, tropical vibe, landscaped grounds and pool. Turn-key, renovated and furnished, this condo resides in the historic Campbell Building on Fleming Street, one of Old Town's most coveted. Enjoy a gorgeous interior with pine floors throughout, new ac mini splits in every room, plentiful storage and a spacious, modern kitchen. The hefty project of converting all 23 windows to impact glass has been done for you, ensuring superior wind protection, an extremely quiet inside space and low energy costs. This unit exudes charm and easy living and feels like a true home all with immediate access to the best of Key West. In a moment you can be dining at your favorite restaurant, watching the sunset at Mallory, listening to live music or hitting Fausto's market for those last minute grocery items. And you will love the balcony where you can take in the hustle and bustle of passer-byers from above, laze away the morning while sipping on your Cuban Coffee, enjoy cocktails under the stars or watch the Fantasy Fest Local's Parade from the best seat in the house! Unit 4 has been fully renovated and needs nothing but you! A custom designed kitchen with ample storage, stainless steel appliances, quartz counters and a white Kohler, porcelain farmer's sink overlooking Fleming below make cooking and entertaining a breeze and a joy. Only 9 units reside in the Campbell Building, all nestled on a beautifully landscaped compound with a large pool. This is a great place to live and will also make for a lucrative vacation rental. Enjoy living on Millionaire's Row with access to all that makes Key West the best place to live the island lifestyle.

617 Fleming St Unit APT 4, Key West
$845,000
5 Beds ⋅ 3 Baths ⋅ 616956 MLS
Welcome to your Key Largo retreat! This spacious 5 bedroom, 3 bathroom home offers the perfect blend of comfort, quality, and privacy. Built in 2018, the home features solid concrete construction with impact windows and doors throughout, ensuring peace of mind and long-lasting durability. Upstairs, you'll find 3 bedrooms and 2 bathrooms, including a bright open living area and modern finishes. Downstairs offers two additional bedrooms and one bathroom, ideal for guests, family, or a private home office setup. The fully fenced yard is surrounded by a lush privacy hedge that has a complete irrigation system, creating your own private oasis. Additional features include a garage, extra storage area, and a whole-house generator, providing convenience and security year-round. Located in beautiful Key Largo, this home is close to world-class boating, fishing, dining, and diving — the best of the Florida Keys lifestyle.

875 La Paloma Rd, Key Largo
$3,799,000
5 Beds ⋅ 4 Baths ⋅ 610297 MLS
Enjoy this OPEN WATER luxury lifestyle in the coveted area of Buccaneer Point Estates in south Key Largo. Prepare to be captivated by this 5 bedroom, 4 bath extraordinary waterfront masterpiece that combines modern elegance and over 3,900 sq. ft of living space with a tropical paradise ambiance. Nestled on the shores of the bay, this custom-designed home has been thoughtfully crafted with discerning clients in mind. This rare offering promises a lifestyle beyond compare, where every moment is infused with the allure of the Florida Keys. As you step inside, ascend the interior stairs from the grand foyer to the main living level, where cathedral ceilings and an abundance of natural light create an inviting atmosphere. Revel in the breathtaking water views framed by expansive windows and doors, seamlessly blending the beauty of the outdoors with the comfort of your luxurious sanctuary. The heart of this residence lies within the great room, where a well-appointed double island creates the perfect setting for entertaining while the expansive porch areas beckon you to soak in the tranquil vistas. Designed to accommodate a large family or gathering of friends, this home boasts two master ensuites on each level, ensuring privacy and comfort for all. In addition, three guest bedrooms with adjoining bathrooms provide ample space for everyone to unwind and recharge. For water enthusiasts, this home is a dream come true with an inviting in-ground heated pool, surrounded by a custom paved deck area and lush privacy landscaping. The deep water pier dock features a boat lift and jet ski lift. The spacious four-car garage with dual doors, a second refrigerator, an ice maker, and the potential for a bar or summer kitchen makes it a versatile space for hosting unforgettable backyard gatherings.

21 Mutiny Pl, Key Largo
$2,795,000
4 Beds ⋅ 3 Baths ⋅ 618526 MLS
Florida Keys luxury island living at its finest. Welcome to your private slice of tropical island living in coveted Cudjoe Gardens—a true boater's dream set on an oversized double canal-front lot (approx. 15,200 sq. ft.) with an impressive close to 200 feet of concrete seawall. This beautifully designed CBS home offers 4 bedrooms, 3 baths, and nearly 3,000 sq. ft. of living space, thoughtfully arranged for relaxed living and effortless entertaining. Recent renovations elevate the home even further, with the kitchen and primary bath completely and tastefully reimagined by D'Asign Source. The stunning chef's kitchen now features Omega cabinetry, elegant quartzite stone surfaces, premium KitchenAid appliances, and a striking black walnut round dining table that anchors the space with warmth and natural beauty—perfect for gathering with family and friends. Pocket sliding doors open the living areas to a spacious screened Florida Room (approx. 494 sq. ft.), seamlessly blending indoor and outdoor living. Outside, enjoy mature tropical landscaping, extensive paved driveways and walkways, and resort-style spaces designed for relaxing and entertaining. For boating enthusiasts, this property truly shines: approx. 4' control depth, quick access to the reef and backcountry, protected canals, and proximity to a full-service marina. The seawall is fully equipped with a cut-in boat slip, 15,000 lb. boat lift, davits, swim ladder, and outdoor shower—everything you need for life on the water. Additional highlights include a barrel tile roof, an attached 2 car garage, a versatile 676 sq. ft. garage space ideal for storage, hobbies, or island toys. Whether you're hosting sunset gatherings by the pool, heading out for a day on the water, or simply unwinding in your own tropical retreat, this remarkable property offers the perfect blend of comfort, style, and true Florida Keys lifestyle. Come see this exceptional canal-front retreat, where every day feels like a getaway.

20920 5th Ave, Cudjoe
$3,799,000
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
$349,000
1 Baths ⋅ 599087 MLS
Office Condo for Sale, centrally located in New Town on the 3rd floor of the Kennedy Center. This Professional Building caters to a diversity of innovative businesses and entrepreneurs in a friendly business environment. Unit 307/305B is approximately 2058sq.ft. with 2 entrances, open floor plan with many workspace options, kitchenette, full bathroom, waiting area, private balcony. This building offers adequate off-street parking, elevators, and public restrooms on each floor. Included in the monthly Assoc Dues: water, electric, building maint, building insurance.

1010 Kennedy Dr Unit 307, Key West
$2,220,000
5 Beds ⋅ 3 Baths ⋅ 617279 MLS
New construction waterfront home featuring 5 bedrooms and 3 bathrooms with a flexible split-level layout ideal for guests or extended family. The property offers a private pool, outdoor kitchen and grill area, and spacious outdoor entertaining space. Boaters will appreciate the 40-foot private dock with easy access to the open water. Additional features include a garage and ample storage. A great opportunity for waterfront living in Tavernier.

115 Azalea St, Tavernier
$2,650,000
616329 MLS
100 x 717 ft lot approximately 1.66 acres ocean front with real sand on the beach on Lower Matecumbe in Islamorada MM76.2. Remains of prior Utility building on property. incredible location for an ocean front beach front micro-estate in the Village of Islamorada.

76291 Overseas Hwy, Islamorada
$649,000
2 Beds ⋅ 2 Baths ⋅ 618622 MLS
Welcome to your piece of paradise in the exclusive gated community of Venture Out on Cudjoe Key. This stunning high-rise, built in 2024, embodies the perfect blend of modern luxury and island life. As you step inside, you are greeted by an inviting atmosphere that captures the essence of coastal living. The master bedroom boasts an en suite bathroom, offering a serene retreat at the end of the day. This high-rise is more than just a home, it's a lifestyle waiting for you to embrace. 9' Tall ceilings with sturdy construction boasting 2x6 walls adds to the luxury feel of this recently built property. Impact rated windows and doors for added protection from the elements to keep you and your family safe. Venture Out is a vibrant community that embraces the spirit of island living, offering many amenities designed to cater to both owners and guests. Spend your afternoons soaking in the warmth of the heated pool. The marina invites boating enthusiasts to indulge their passions, while the boat ramp provides seamless access to adventure on the waters. For those seeking a little friendly competition, the courts for tennis, bocce ball, basketball, and pickleball create an atmosphere of active recreation. At the recreation hall, residents gather for activities and social events, creating a strong sense of community.

701 Spanish Main Dr Unit 29, Cudjoe
$12,450,000
5 Beds ⋅ 7 Baths ⋅ 618181 MLS
Welcome to Villa Splendida in exclusive Duck Key, Florida. This custom built estate has been curated from the gated entrances to the 180' of protected ocean front dockage. Featuring a classic Mediterranean styling the spacious grounds host a variety of mature tropical plantings, fruit trees, and ease of maintenance turf throughout. The home itself is spacious and comfortable allowing elegant flow throughout the property. Enter to soaring 2-story grand room with open floor plan into the dining and chefs kitchen with walk-in pantry, Wolf and Subzero appliances, a first level guest suite, undersea themed theater room, laundry, powder room and open water views and poolside access from all rooms. The second level hosts two guest suites, a mezzanine with sweeping views of the lower level and open ocean, and a sumptuous primary suite with expanded ensuite, walk-in closet and private oceanfront balcony. There is also a separate attached guest cottage complete with laundry. The elevated patio incorporates a custom beach entry pool with infinity edge waterfall, spa, outdoor kitchen and space perfect for entertaining or just lounging at your own private oceanfront resort. Just steps from the pool is 180' of protected dockage complete with a 57k lb boat lift and jet ski lift platform that will hold up to 6 jet skis. Additional amenities include: a custom sound system throughout the entire property inside and out, large capacity ice machine, 4+ car garages, fully fenced and gated for privacy, mature landscaping and lighting, multiple laundry facilities, and full under house access and storage. Call today for more information and to schedule a private tour of this one-of-a-kind Duck Key estate.

301 Ixora St, Duck
$2,845,000
7 Beds ⋅ 7 Baths ⋅ 617788 MLS
Exceptional canal-front opportunity with proven income potential. This expansive 7-bedroom, 7-bath residence offers outstanding flexibility as a legal duplex with an interior lockout, allowing it to function seamlessly as a large single-family home or as two separate living spaces. The configuration includes a generous 5BR/4BA main residence paired with a private 2BR/2BA guest wing, topped off by a convenient pool bath located in the game room, making it ideal for multigenerational living, guests, or vacation rental use. The main living space welcomes you with a dramatic two-story entry, an open-concept great room, multiple dining areas, wet bar, and a well-appointed kitchen that flows to a waterside balcony. The lower-level unit features its own open living and kitchen area, providing privacy and versatility. Four bedrooms are ensuite, complemented by 2 primary suites overlooking the water. Recent upgrades include complete concrete spalling repairs and a fresh exterior repaint, adding peace of mind and refreshed curb appeal. Mediterranean-inspired design elements are carried throughout, along with impact windows and doors, multiple balconies, and inviting indoor-outdoor living spaces. Outside, enjoy a heated pool, spa, covered poolside lanai, and 75 feet of concrete dockage with quick boating access to both the Atlantic Ocean and the Gulf of America. Additional features include a two-car garage and ample off-street parking. This property has a strong, established vacation rental history and is currently an active rental.

580 & 590 10th St, Key Colony
$945,000
2 Beds ⋅ 2 Baths ⋅ 618566 MLS
Located near a canal 'T', this oceanside property offers easy docking for larger boats and sailboats in the 50 ft. wide, flow-through canal, putting the Atlantic and back-country within easy reach. The rooftop deck is a wonderful vantage point for panoramic neighborhood and water views. Nestled in mature vegetation, the one-owner, custom-built, board and batten cedar home has been well-maintained and is ready for the next owner to personalize. Step inside the wood privacy fence to discover the mahogany, buttonwood, Hong Kong Orchid trees and more that provide cooling shade on the 6100 sq. ft. property. The wood walkway and 10 ft. wide dock area were custom-designed, and the canal-side tiki provides a touch more shade. Additional features of this 2-bedroom, 2-bath home are the east facing porch that captures sunrises, moonrises and breezes; central air; impact-resistant sliding glass doors on the main level; great storage and covered parking on the ground level. Welcome to Jolly Roger Estates!

683 Blackbeard Rd, Little Torch
$680,000
2 Beds ⋅ 2 Baths ⋅ 617778 MLS
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 villa is working for you even when you're away.

5110 Sunset Village Dr, Duck Key
$325,000
2 Beds ⋅ 2 Baths ⋅ 616731 MLS
Discover one of the best-priced properties in the Florida Keys! A beautifully updated 2-bedroom, 2-bathroom top-floor condo on sought-after Duck Key. Offering a flexible layout, tasteful upgrades, and a brand-new air-conditioning system, this home delivers comfort and value in equal measure. The main living area features a renovated kitchen with quartz countertops, stainless steel appliances, and modern finishes throughout. The primary suite is inviting and private, while the second bedroom offers exceptional versatility with its own entrance, wet bar, and kitchenette, perfect for hosting guests, creating a separate living space, or utilizing additional privacy. Set within a pet-friendly(with some restrictions) 12-unit building with a new roof (2018) and a peaceful atmosphere, residents enjoy a sense of privacy that's hard to find. Just minutes away, Duck Key Marina offers boat launch and storage options with no bridges to open water, giving direct access to world-class fishing and diving. Whether you're looking for a full-time residence, weekend retreat, or investment property, this condo represents one of the best values in the Keys, a move-in-ready opportunity to own your slice of island life.

1129 Pebble Beach Lane, Unit 11, Duck Key
$774,500
2 Beds ⋅ 2 Baths ⋅ 616611 MLS
REDUCED !!!!! GREAT DEAL!!! Welcome to Unit H5 at Kawama Yacht Club -- a beautifully updated 2-story, 2 bed / 2 bath townhouse offering 918 sq ft of turnkey living space. Adjacent to the pool area with serene lagoon views, this fully furnished unit is vacation rental-friendly with proven income history. Located in a gated oceanfront community with premium amenities including: 2 Swimming pools Private saltwater lagoon for kayaking, swimming & beach relaxation Large tiki hut for events & gatherings Tenis/ Pickle Courts Private marina with deeded slips Oceanfront grills & firepits HOA covers exterior maintenance, insurance, pest control & more. Weekly rentals allowed. Minutes from top fishing, diving, and dining spots -- live the Key Largo lifestyle or invest in paradise! Text Listing agent for showings

1500 Ocean Bay Dr Unit H5, Key Largo
$1,100,000
1 Beds ⋅ 2 Baths ⋅ 617909 MLS
Charming Old Town Retreat in X Flood Zone! Step into island living with this beautifully renovated 1-bedroom, 1.5-bath home, plus sleeping loft and cabana, in the heart of Old Town Key West. Thoughtfully updated with quartz countertops, custom wood cabinetry, and top-of-the-line stainless steel appliances, this home seamlessly blends modern comfort with historic charm. A cozy sleeping loft offers extra space for guests or lounging, while a separate structure on the property can serve as a studio, guest room, or private cabana. Nestled on a generously sized lot in the desirable X flood zone, this home also conveys with a 1/10 interest in a private parking lot behind the residence—a rare Key West perk! Don't miss your chance to own a versatile and stylish island escape in one of Key West's most sought-after neighborhoods.

738 Olivia St, Key West
$940,000
4 Beds ⋅ 4 Baths ⋅ 616376 MLS
BUYERS — A Rare Opportunity Awaits! If traditional bank financing isn't an option but you do have the means to purchase, this is your moment. With 30% down and verifiable income to support monthly payments, you can secure a beautiful home in one of the most desirable communities in the Florida Keys. Owner Financing Available. Welcome to Key Largo Ocean Resort (KLOR)—a vibrant, gated oceanfront community that has evolved from a modest trailer park co‑op into a premier enclave of modern luxury homes. Perfectly situated in the heart of the Florida Keys, KLOR blends relaxed island living with upscale amenities, creating an unmatched lifestyle experience. This spacious 4-bedroom, 3.5-bathroom residence is truly one of a kind. Designed with comfort, functionality, and family living in mind, it offers: • A generous open layout • A dedicated laundry room • A charming peek‑a‑boo ocean view • Ample covered space downstairs for your boat, golf cart, and outdoor gear Whether you're seeking a turnkey vacation rental, a fully furnished primary home, or a second home getaway, this property is ready to welcome you. Enjoy effortless short‑term rental setup or settle into year‑round island serenity. KLOR offers an impressive array of amenities, including: 🛥️ Full‑service marina (all slips currently occupied; waiting list available) 🚤 Private concrete boat ramp with direct ocean access 🏊‍♂️ Resort‑style swimming pool 🏋️‍♀️ Modern fitness center 🎾 Tennis and basketball courts 🏠 Clubhouse and more.

94825 Overseas Highway Unit 281, Key Largo
$398,000
618535 MLS
This property includes a transferable development right (TBR) that is already secured to the lot, making it ROGO-exempt and ready to build today. Even better, the TBR does not expire, giving you the flexibility to build now or hold the property and build later with no time pressure. Situated on a spacious corner lot on a desirable street, the property is located just one block from Club Duck Key, where members enjoy resort-style amenities including a swimming pool, jacuzzi, tennis and pickleball courts, and a clubhouse — all enhancing the relaxed island lifestyle Duck Key is known for. For boaters, the location is equally appealing. Store your boat at Duck Key Marina and enjoy convenient, seamless access to the open water, world-class fishing, and endless days on the bay or ocean. Just minutes away, the renowned Hawks Cay Resort offers additional dining, marina services, watersports, and spa amenities, giving owners the option to enjoy a full resort experience close to home. Duck Key is widely regarded as one of the most desirable communities in the Middle Keys, prized for its peaceful atmosphere, well-maintained homes, boating lifestyle, and easy access to both Marathon and Islamorada. With no ROGO wait, no uncertainty, and a build-ready path forward, this is a rare chance to design and build your dream home in paradise — on the only ROGO-exempt lot currently available on Duck Key.

143 S Indies Dr, Duck