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$999,000
3 Beds ⋅ 2 Baths ⋅ 620987 MLS
Charming Historic Old Town Key West Home, Ready for Its Next Chapter! Here's an opportunity for the buyer who sees possibility where others see a project. This 3-bedroom, 1.5-bath historic Key West home is tucked into the heart of Old Town, just minutes from the Historic Seaport, downtown, restaurants, shopping, and everything that makes island living so special. With classic Key West architecture, a welcoming front porch, hardwood floors, vintage windows, and plenty of original character, the home offers a wonderful starting point for a thoughtful renovation. The interior has been freshly painted, but this is a property that will require renovation and is best suited for a buyer ready to take on a true restoration project. Currently tenant occupied, the property also offers the advantage of existing rental income while a new owner makes plans, lines up contractors, or prepares for a future renovation or move-in. The existing floor plan includes generous living space, three bedrooms, a full bath downstairs, a half bath upstairs, and a private backyard with the potential to become a lush tropical retreat. For the right buyer, the appeal is undeniable: an authentic Old Town home, a highly desirable location, existing income, and the opportunity to restore, reimagine, and create something truly special. Bring your contractor, your creativity, and your vision. This one isn't pretending to be turnkey, but it just might be worth the work. *some photos digitally enhanced only to remove personal belongings

506 Grinnell St, Key West
$6,195,000
4 Beds ⋅ 5 Baths ⋅ 620986 MLS
Experience the ultimate Islamorada waterfront lifestyle in an exceptional contemporary custom bayfront residence, designed by its current owners, with sophisticated architecture, exceptional construction, and premier boating amenities. Perfectly positioned on a cul-de-sac to capture spectacular year-round sunsets across Florida Bay, the tri-level residence offers approx. 3,200 Sqft of living space, an additional 800 Sqft of covered, tiled balconies, four bedrooms, each with an en suite bathroom, plus a convenient half bath. Natural stone flooring, custom cabinetry, quality finishes, and an elevator serving all interior living levels. Built for lasting durability, the home features reinforced concrete construction, galvanized reinforcing steel, a solid concrete roof, impact windows & doors plus automatic hurricane curtains protecting the main waterfront terrace. The spectacular 1,400 Sqft rooftop sun deck crowns the residence, showcasing panoramic views across Florida Bay, unforgettable year-round sunsets, & a fire pit for entertaining or relaxing under the stars. Designed for the boating enthusiast, the property offers immediate deep-water access, two boat lifts at +/- 25,000 and 12,000 pounds, and an enclosed tackle room/workshop for fishing gear and marine equipment. Low-maintenance grounds feature artificial turf, coral rock hardscaping, and irrigated tropical landscaping. The spacious backyard offers ample room for a future resort-style pool overlooking Florida Bay adjacent to the existing chickee hut. A spacious double covered carport with 9.5-foot ceilings provides generous parking for multiple vehicles, trailers, golf carts & recreational equipment. Combining contemporary custom design, exceptional concrete construction, expansive indoor/outdoor living, premier boating amenities, breathtaking sunset views, and endless opportunities for waterfront entertaining, the residence represents luxurious bayfront living at its finest in the Florida Keys.

144 N Rolling Hill Rd, Islamorada
$3,700,000
3 Beds ⋅ 4 Baths ⋅ 620985 MLS
Awarded the Florida Keys Preservation Star, this meticulously restored single-family home offers an enchanting blend of historic Key West charm, modern luxury, and high-yield investment potential. Holding a coveted TRANSIENT LICENSE allowing profitable nightly rentals, this turnkey Old Town sanctuary sits just a half-block from world-famous Duval Street while enjoying a prime position near boutique shops, fine dining, and the Southernmost Point. Step inside through iconic yellow doors into a bright, sunny retreat defined by historic Dade County pine walls, gingerbread balustrade details, high soaring ceilings, and rich natural light. The main level flows into an open-concept living area and a sleek white kitchen equipped with stainless steel appliances, ample prep space, and an oversized island with seating for six--perfect for gathering family and friends. Designed for indoor-outdoor living, double sliders spill out to a well-appointed, covered lanai featuring a large outdoor TV and a rare air-conditioned half bath. Beyond the lanai lies a private tropical oasis enveloped by lush palm trees and fencing. Take a refreshing dip in the 8' x 14' heated pool with its soothing water feature, lounge in the sunshine on the deck, or host alfresco dinners using the gas grill. The interior layout offers total comfort and privacy for guests. The main floor houses two king-bedroom suites complete with walk-in showers, including one with direct access to the poolside sanctuary. Tucked upstairs for added seclusion, the third ensuite bedroom features a queen bed, vaulted ceilings, and sunny exposure. Completely renovated with impact windows, and dedicated off-street parking, this property is designed for effortless ownership. Whether retained as a high-performing vacation rental with proven revenue projections or enjoyed as a private island getaway, this home offers a rare chance to own a piece of Key West paradise.

530 Catherine St, Key West
$1,399,000
2 Beds ⋅ 2 Baths ⋅ 620984 MLS
Direct oceanfront living takes center stage, with turquoise water views, tropical surroundings, and multiple outdoor spaces creating a true Florida Keys escape. Outdoor living and boating are at the heart of this property. A tiki-covered deck offers a shaded place to relax and entertain just steps from the water, while the lower-level outdoor area includes a private hot tub surrounded by tropical landscaping. From the tiki porch, just feet from the house, enjoy frequent visits from sea turtles, porpoises, manatees, and colorful rainbow parrotfish. For those who love life on the water, each resident has the right to keep a boat in the community common area and enjoy access to the private boat ramp located on the island. The new owner will receive a key to the ramp, making it easy to get out and enjoy the water. The island also features a snorkeling beach, creating even more ways to experience the natural beauty and marine life of the Keys. Inside, the updated two-story residence features a bright, open living and kitchen layout designed to keep the ocean view front and center. Large windows and glass doors fill the space with natural light and create an easy connection to the outdoors. The refreshed kitchen features white cabinetry, butcher-block countertops, stainless-steel appliances, a subway tile backsplash, and a generous peninsula with seating and additional storage. The adjoining living area opens directly to the oceanfront deck, making indoor-outdoor living effortless. Upstairs, the primary bedroom offers beautiful ocean views and direct access to a private waterfront balcony, an ideal spot for morning coffee, evening cocktails, or simply taking in the breeze. Elevated on concrete pilings and finished with a Hardie board exterior and metal roof, the home is well suited to its waterfront setting. Covered parking beneath the residence adds everyday convenience while complementing the relaxed island lifestyle.

62900 Overseas Highway Unit 29, Conch
$1,400,000
4 Beds ⋅ 3 Baths ⋅ 620983 MLS
Prime waterfront living on Sombrero Beach Road! This vibrant 4BD/3BA retreat (1,840 sq. ft.) delivers the total Florida Keys lifestyle. Walk to sandy Sombrero Beach, keep your boat at your private 30-ft dock with direct ocean access, and relax in your secluded tropical backyard with a private in-ground pool. An ideal personal getaway or income generator, boasting $45k+ rental income in 2025 and $60k+ in 2026. Beach, boat, pool, and proven performance--schedule your private tour today!

241 Sombrero Beach Rd Unit # 1, Marathon
$165,000
620982 MLS
Harbour Cay Club, Marina, a piece of Marathon history, consists of 24 liveaboard slips situated in a protected basin. Slip 18 can accommodate a 42' LOA x 16' boat. Has 30/50 amp power pedestal. It is a private marina organized as a not-for-profit Florida corporation composed of 24 owners who live aboard their boats. The corporation has 24 shares and members are equity owners entitled to all the amenities of this immaculately maintained marina. The property includes a clubhouse with kitchen,, a guest quarter that can sleep six, two community bathrooms with showers, a laundry room, and a well-appointed workshop. Set on nearly an acre and half - enjoy breathtaking sunset views from the spacious Tiki Hut and Lanai. Rentals not allowed... Taxes are split among 24 owners. The buyer and their boat must be approved by Harbour Cay Club Marina Board of Directors. Visit: https://harbourcayclub.mycommunitysite.co/

1466 Overseas Hwy Unit Slip 18, Marathon
$1,800,000
620981 MLS
Key Colony Beach is one of the Florida's Keys most desired cities and due to this, there are very few buildable waterfront lots remaining and as of right now there are only 3 available and the next lot is priced at $2,650,000 making this the LOWEST PRICED Waterfront lot in all of Key Colony. Unlike most other cities in the keys, all Key Colony Beach lots are buildable, and permits will be issued once final plans are approved; no need to purchase building rights or have to wait years for a building permit. Lot has a Brand New 90Ft Seawall with Concrete Cap. What is even more special about this lot is that not only was the canal recently dredged, making it approximately 5 feet deep at low tide and approximately 40 feet wide; it offers rare privacy as across the canal will never have any homes built, which is very uncommon for Key Colony Beach. The lot is just shy of 10k sqft at 9756 and offers direct access to open ocean and the Bay via Vaca Cut in just minutes. For the avid boaters, there are three marine fuel docks just a short 8 minute boat ride away and two of them have bait tackle shops onsite. Key Colony's Sunset Park Beach is just a short walk from this lot and offers some of the best sunsets in the Florida Keys and it is dog friendly. For the avid golfers, Key Colony Beach Golf course is just a 3 minutes away and open to the public. Key Colony is also known for its annual lighted Boat Parade, which is a resident favorite. Do not miss the opportunity to acquire one of the last buildable waterfront lots in Key Colony. 180 12Th St just sold for $2,125,000 and was 415 sqft smaller. Plans are available for a 5 Bed, 5 Bath, 3,467 sqft Pool Home with multiple rear balconies overlooking the water views and surrounding tropical setting. by the very well-respected local builders Design Center. We have lenders offering construction financing up to 75% loan to value to finance the lot and the construction of the home or 40% loan to value for just the lot.

200 15th Circle Ky, Key Colony
$220,000
2 Beds ⋅ 2 Baths ⋅ 620980 MLS
One Owner. One Vision. One Seriously Good Price. Since 1981, this Florida Keys condo has had exactly one owner -- and he took excellent care of it. What he didn't do is renovate it, which means you're not buying someone else's idea of renovated. You're buying a blank canvas with great bones, and the lowest price tag on any condo in the entire Florida Keys. Upstairs: two bedrooms and a full bath, tucked away from the action. Downstairs: a convenient half bath and open floor plan with balcony. The layout works. The bones are solid. The rest is up to you. Outside, fresh paint gives the building a tropical look and covered parking means your car won't be baking in the sun when you get in. The neighborhood is quiet -- genuinely quiet, not ''quiet'' realtor-speak. Is it original condition? Yes. Is that a nice way of saying it needs updating? Also yes. But here's the thing: everyone's welcome to make it their own, and at this price, in this location, you can renovate exactly the way you want instead of living with someone else's 2019 flip-job decisions. This is the rare Keys listing where ''priced to move'' actually means something. Original charm, honest bones, and an entry point to island living that doesn't require winning the lottery first. HOA includes wind and flood insurance. Bring your vision (and maybe a paint roller). This one won't stay the cheapest condo in the Keys for long.

109 Stirrup Key Woods Rd Unit 1A1, Marathon
$825,000
5 Beds ⋅ 6 Baths ⋅ 620978 MLS
Spectacular oceanfront custom home is located at the Ocean Blue guard gated community at the Piscina Natural in Rio San Juan, 20 minutes from Playa Dorada & Puerto Plata Airport in Dominican Republic. Located on the Northern Coast. Main home includes 5 bedrooms & 4.5 baths, guesthouse has 1 bedroom, 1 bath kitchen living room & bathroom. Move in ready & home is completed furnished. Automatic whole house generator. Has full house generator. This is the only ocean front home in the community. Home is also gated & is all cement including the roof. Terraces with lounge chairs, a hammock, and grill for BBQ. Rio San Juan has one of the most beautiful beaches on the Coast & destination to many tourist from all over the world. Located Near Playa Caleton & Playa Grande. Great Air B & B Investment. Live your dream, vacation or live in one of the worlds most popular destinations. Great Air Air B & B Investment, vacation home or your live there full time.

306 E Ocean Blue Ave Unit 5, Other
$355,500
620977 MLS
Start building immediately with this Waterfront Transferable Development Right (TDR) for use in the Village of Islamorada for a Single Family Residence on the water. Buyer has to verify with the Village if TDR is applicable to vacant lot. Buyer has to pay all closing costs associated with the transaction and the transfer fees to the Village. The Letter of Development Rights Determination from the Village is on file and can be provided upon request.

1 Waterfront, Not Provided
$740,000
3 Beds ⋅ 2 Baths ⋅ 620976 MLS
Welcome to your ultimate Florida Keys getaway! This beautifully refreshed Key Largo home shines with brand-new interior and exterior paint, plus a stylish new kitchen backsplash. Inside, soaring vaulted ceilings create a bright, airy coastal ambiance, complemented by a versatile bonus loft area that is perfect for a home office. Escape to the spacious master bedroom, complete with his-and-her closets, while the spa-like master bath offers a luxurious steam walk-in shower and a relaxing whirlpool tub. Step outside to your private oasis featuring a covered back patio perfect for entertaining, with plenty of remaining space to build your dream pool! Nestled in a highly desirable neighborhood, water enthusiasts will love the immediate ocean access via the community boat ramp just down the street. Enjoy the ultimate convenience of being minutes away from local waterfront restaurants, shopping, Publix, and a nearby state park. Move right in and start living the effortless Keys lifestyle you've been dreaming of!

118 First St, Key Largo
$2,150,000
4 Beds ⋅ 3 Baths ⋅ 620975 MLS
DIRECT OCEAN ACCESS IN PORT LARGO! Solid concrete 4-bedroom, 3-bath home featuring an open floor plan and 75 feet of dockage. Ideal for boating and fishing enthusiasts, with direct access to the Atlantic and easy access to offshore fishing, diving, snorkeling, sandbars, and cruising. Conveniently located in Key Largo near restaurants, marinas, dive shops, fishing charters, and waterfront attractions. Just minutes from Key Largo Community Park, one of the nicest recreational parks in the Upper Keys, offering tennis, recreation, green space, and the Jacobs Aquatic Center. Home also features a transfer switch at the electrical panel for generator operation. A great opportunity to enjoy the Florida Keys waterfront lifestyle with plenty of dockage and direct ocean access.

478 Bahia Ave, Key Largo
$250,000
620974 MLS
Discover a prime opportunity to build your Florida Keys dream home in Key Largo Ocean Resort, complete with marina, pool, clubhouse and tennis courts. This oceanside community is in a prime location in Key Largo and is ROGO-exempt, and comes available with HOA-approved plans.

94825 Overseas Hwy Unit UNIT 156, Key Largo
$95,000
620973 MLS
Live the Florida Keys lifestyle without the Florida Keys price tag at **Bonefish Marina on Coco Plum**. This 30' x 13' boat slip offers an easy, affordable way to call the Keys home—right on the water. Step aboard and head straight out to fishing grounds, sandbars, snorkeling spots, and dive sites, all just minutes away. The slip includes water, electric, and a dock box, making everyday living simple and comfortable. As a slip owner or lessee, you'll enjoy access to a laid-back marina community with a clubhouse, tiki bar, workshop, Wi-Fi, fish cleaning stations, kitchen, showers, bathrooms, and laundry facilities. Free parking and pump-outs add even more convenience—no extra hassle, no extra cost. When you're not on the water, take a short stroll to **Coco Plum Beach** or enjoy all that Marathon has to offer, from dining to shopping and island events. Best part? The boat is also for sale—meaning you could move in and start living the Keys dream right now. If you've been looking for a truly affordable way to live in the Florida Keys, this is it. Call today and make island living your everyday reality.

97 Oo Plum Dr Unit C, Marathon
$2,000,000
3 Beds ⋅ 3 Baths ⋅ 620970 MLS
Canal front living, right where you want it. Set along one of Islamorada's most popular canals, this turnkey 3-bedroom, 3-bath home offers a waterfront setup that makes living easy. With 50 feet of deepwater dockage, a 10,000-lb. boat lift, and direct access to the Florida Bay, this one is hard to beat. Inside, the main level is bright and open, with vaulted ceilings, 2 spacious bedrooms, 2 baths and a beautiful kitchen with top-of-the-line appliances. A large screened-in porch off the living room and primary suite extends the living space and takes full advantage of the canal views. The lower level offers a private 1-bedroom, 1-bath en-suite apartment, ideal for guests or family. Outside, the backyard blends tropical landscaping with a spacious pavered area, creating an easy-to-maintain and welcoming spot to relax. The double-sided garage provides flexible space for storage, parking or recreation. Open both garage doors to extend the backyard or easily bring fishing gear to and from the boat. The cargo lift, filet table, storage shed and generous parking make this home as practical as it is inviting. Add in solid construction with a concrete roof, a great Plantation Key location and easy access to everything you need (both on and off the water), and you've got a home built for enjoying everything the Keys are about.

155 Plantation Ave, Islamorada
$279,000
3 Beds ⋅ 3 Baths ⋅ 620968 MLS
Experience all the allure of Fishermans Cove fractional Ownership. where you can enjoy unparalleled views at a fraction of the price. This property cannot be rented out only the condo owners can Revel in the spaciousness of this expansive 3-bedroom, 3-bath condo, boasting direct bay access that sets the stage for breathtaking sunsets. Step into a haven of convenience, as this meticulously designed property anticipates your every need - simply pack your toothbrush and you're all set. Fishermans Cove does not permit rentals, ensuring that exclusive privileges are reserved solely for property owners. Enjoy unrestricted access to the expansive rooftop owners' deck, stay active in the fully equipped gym, and luxurious private cabanas designed just for you. Embark on your own expeditions with the distinct advantage of having two boats ready for your use: a 26' Sea Fox and a 24' Contender. As well as the convenience of access to both bayside and the ocean. On average Owners take advantage of spending an average of 5 to 7 weeks per year within these highly coveted residences, although the opportunity for enjoyment extends beyond this range with no limit, allowing you to truly embrace a life of lavishness and tranquility. Strategically situated above the renowned Big Chill, you'll have easy access to dining and entertainment experiences. The swift journey from Miami grants you a short trip, conveniently placing an array of experiences at your fingertips.

104000 Overseas Hwy Unit UNIT 6-6, Key Largo
$880,000
4 Beds ⋅ 2 Baths ⋅ 620967 MLS
Live in one unit and rent the other or enjoy the flexibility of this bright and versatile duplex . Featuring two separate 2-bedroom, 1-bath units, this elevated property offers a comfortable layout, abundant natural light, and a peaceful setting surrounded by nature. The property features a durable metal roof, has been recently painted, and offers ample covered parking with plenty of space for an RV and boats. The spacious outdoor area provides room to create your own private oasis and potentially add a pool. A wonderful opportunity to live, invest, or generate rental income in the Florida Keys!

187 & 189 Casa Court Dr, Tavernier
$525,000
2 Beds ⋅ 1 Baths ⋅ 620966 MLS
Discover the charm of this updated 2-bedroom, 1-bath home, ideally located in the heart of Marathon. Built in 1957, this classic Keys home offers character, comfort, and plenty of outdoor space. The open-concept living area creates an inviting flow for everyday living and entertaining, while the original terrazzo floors add timeless Florida charm. Situated on a large, beautifully shaded lot, the backyard possibilities are endless. There is plenty of space to create your own private outdoor oasis, including room for a pool, entertaining area, garden, or additional outdoor living space. A screened-in back porch provides the perfect spot to relax and enjoy the island breeze. The spacious storage shed offers abundant room for tools, bikes, fishing gear, or could easily become your own private man cave or hobby space. With its convenient location in the heart of Marathon, generous lot, mature shade trees, updated interior, and classic terrazzo flooring, this property offers a wonderful opportunity to enjoy the laid-back Florida Keys lifestyle with plenty of room to make it your own.

354 96th Street Ocean St, Marathon
$11,000,000
5 Beds ⋅ 5 Baths ⋅ 620965 MLS
Extraordinary opportunity to own one of the Florida Keys' most spectacular oceanfront residences. Set along a breathtaking stretch of pristine shoreline, this remarkable estate seamlessly blends exceptional architecture, sophisticated design and an unparalleled waterfront lifestyle. Set on nearly an acre with 100 feet of white-sand Atlantic Ocean frontage, this newly completed renovation by acclaimed D'Asign Source delivers exceptional design, craftsmanship and timeless elegance with breathtaking ocean views from virtually every room. This residence features 5 bedrooms, 4 full bathrooms and 1 half bath, a residential elevator, full-size tennis/pickleball court and spectacular infinity-edge pool with spa. The grand open-concept living space features custom shellstone flooring and seamless indoor-outdoor living. A stunning chef's kitchen is appointed with a complete suite of Miele appliances, including three ovens, two dishwashers, panel-ready refrigerator and freezer, built-in coffee maker and six-burner cooktop with integrated extractor. Additional highlights include a butler's pantry, dedicated laundry room and two expansive bonus rooms ideal for a gym or game room. The top floor offers a luxurious primary suite enhanced by cathedral ceilings, oceanfront terraces and spa-inspired bathroom along with two additional en suite guest rooms. Outdoor living is exceptional, with generous covered entertaining areas, a fully equipped summer kitchen and an infinity pool and spa that appear to merge with the endless turquoise waters of the Atlantic. The gated and fenced grounds provide privacy and include a two-car garage, car lift, whole-house generator and buried propane tank. With WEEKLY rentals permitted with a Vacation Rental license, this rare offering combines luxurious personal enjoyment with outstanding investment potential. This remarkable estate offers a combination of sophisticated luxury, resort-style amenities and unmatched beachfront living in Islamorada

75751 Overseas Hwy, Islamorada
$3,999,999
5 Beds ⋅ 4 Baths ⋅ 620964 MLS
Spectacular luxury modern home built in 2020, located on a corner lot with over 200 feet of waterfront. This home has four stories, featuring elegant finishes and a gourmet chef's kitchen with a quartz waterfall island. Enjoy the rooftop with new turf and spiral staircase to infinite bay views. The expansive outdoors includes a full kitchen, 80' of composite dock with an additional 125' of seawall on main canal. with a 20k LB Neptune boat lift. Approved pool plans are available. This boater's paradise provides direct bay and ocean access via Jewfish Creek or Adams Cut. Additional features include a mosquito misting system and elevator. Available fully furnished and move in ready. Live the dream.

475 Bahia Honda Rd, Key Largo
$1,375,000
4 Beds ⋅ 3 Baths ⋅ 620962 MLS
All this home needs is YOU! Located just one block in from the bay in Key Largo's popular Sexton Cove, this 2014 build offers 4 bedrooms, including an office/den/4th bedroom, 2.5 baths along with a laundry room and workshop! The spacious floorplan offers a nice sized living area with a proper dining space, and open kitchen with granite tops, wood cabinets and island for entertaining. The generous primary suite includes ample closet space & large en suite bath with shower, tub, dual sinks & water closet. With coveted Southeast exposure, the double decker covered porches overlook your 62ft concrete dock with davits and the 80ft wide canal - perfect for taking in the morning sunrise and afternoon cocktails! This solidly built home has been fortified with impact windows & doors, a metal roof and a new ac installed in 2026. Fully furnished down to the dishes along with a fully stocked workshop with a work bench, ice machine and more. Covered parking for 3 cars and tons of open space for your RV, boat trailer and even room for a pool! Sexton Cove offers a private boat ramp just down the street, membership is optional at just $150 per year. The 80ft wide, yet short canal offers direct access to the Florida Bay and the ocean beyond for excellent proximity to the world class fishing, boating and diving Key Largo is known for. Numerous bars & restaurants nearby that can be reached by car, foot or boat! Close enough to the mainland yet a world away.... call today and enjoy the beauty of Keys living!

3 Snipe Rd, Key Largo
$1,439,000
4 Beds ⋅ 3 Baths ⋅ 620960 MLS
Welcome to 219-2 Sombrero Beach Road, a 4-bedroom, 3-bath waterfront retreat where mornings can begin with a walk to Sombrero Beach, afternoons can be spent on the boat, and evenings end around your private pool beneath the palms. The location is the difference. From here, one of Marathon's most loved beaches is just moments away, while 31 feet of private dockage puts the ocean within easy reach. Whether the day calls for fishing offshore, snorkeling, a sandbar run, or simply staying home by the pool, this property makes it remarkably easy to enjoy the reasons people come to the Florida Keys in the first place. Inside, 1,840 square feet offers four spacious bedrooms, three baths, an open living area, abundant natural light, and a relaxed coastal atmosphere designed for gathering. Outside, tropical landscaping surrounds a private pool and cabana-style entertaining area, creating a secluded space for long afternoons, dinners outside, and time with family and friends. And for buyers looking beyond the lifestyle, the numbers deserve attention. The property generated $115,000 in rental income in 2025, offering an established income history in one of Marathon's most recognizable vacation destinations. Current annual insurance costs are also notably attractive for a waterfront property, with approximately $4,262 for wind and $1,520 for flood insurance. That combination is difficult to replicate: Sombrero Beach within walking distance, your boat at the dock, a private pool in the backyard, four bedrooms for family and guests, and the ability to generate meaningful vacation-rental income when you're away. This isn't simply a place to own in the Florida Keys. It's a property designed to let you actually use them. Beach. Boat. Pool. Income. It's all here.

219 Sombrero Beach Rd Unit # 2, Marathon
$299,000
620958 MLS
2,244 square foot commercial zoned lot would be ideal for one or more food vendor trucks, with excellent visibility and heavy traffic. Make an offer today!

2001 Flagler Ave, Key West
$575,000
2 Beds ⋅ 1 Baths ⋅ 620957 MLS
Charming Key West living in a fantastic central location! This inviting end-unit condo offers an easy, low-maintenance opportunity to own a piece of the island, whether you're looking for a full-time residence, Key West getaway, or investment property. The bright interior features tile floors, granite countertops, central A/C and a functional kitchen, while the fenced outdoor space adds a rare touch of private outdoor living. Surrounded by tropical landscaping and just a short bike ride from Old Town, beaches, restaurants, shopping and everything Key West has to offer. A great opportunity to enjoy the Key West lifestyle or add an island property to your investment portfolio.

1332 Seminary St Unit 103, Key West
$549,000
2 Beds ⋅ 2 Baths ⋅ 620955 MLS
NEW LISTING!!! This Key West estate townhome is ready for you to move in! This well-maintained, owner-occupied home is bright and features two bedrooms, centrally located in town. The updated kitchen boasts granite countertops, a tile backsplash, ample cabinet space, a breakfast bar, and a dining area. A convenient half bath is located on the main level, along with full-size laundry. The spacious second floor includes two large bedrooms with generous closets, bamboo flooring, and balcony access. There is a modern full bath on the second floor and a linen closet in the hallway. Additional features include impact-rated doors and windows, ductless AC units on the bedroom level, a storage shed, and more. Enjoy a large fenced yard perfect for entertaining and pets with room for gardens. Best of all, there are no HOA fees!

3207 Eagle Ave, Key West
$1,469,000
3 Beds ⋅ 3 Baths ⋅ 620954 MLS
*Construction process underway. Expected completion November/December 2026 Embrace the ultimate Keys lifestyle in this spacious 1,500 sqft home, ideally situated along a boating canal in the Lower Florida Keys, and close to Key West! Tucked away in a quiet, peaceful neighborhood. Inside, the home features generous living space, providing ample room to stretch out and make it your own. Indoor-outdoor living is at its best here, with a private swimming pool just steps from the back door--perfect for unwinding after a day on the water or enjoying sunny Florida afternoons. For boaters, the canal location offers easy water access, along with the convenience of a 10,000-pound boat lift to safely store your boat out of the water. After a day of fishing, cruising, or exploring, dock your vessel with ease and relax as you take in the beautiful waterfront views. Or stay on the screened in covered porch and enjoy the Keys breeze! The roughly 1100 sqft garage/lower enclosure offers abundant storage space for all your tools, pool toys, and outdoor gear, keeping everything organized and clutter-free. Plus, with a newly built home designed to the latest building codes, you'll benefit from low insurance rates, ensuring peace of mind and minimized risk from tropical weather. This home offers the ideal combination of comfort, convenience, and the laid-back Florida Keys lifestyle. Don't miss the opportunity to make it yours--schedule your private showing today at the model home. Photos are of model home and may not fully depict to be built home. Seller is licensed FL real estate agent.

27374 Guadaloupe Ln, Ramrod
$3,795,000
5 Beds ⋅ 4 Baths ⋅ 620953 MLS
NEW CONSTRUCTION | FULLY FURNISHED | 45' BOAT SLIP | OPEN GULF VIEWS Experience elevated Florida Keys living in this newly constructed, fully furnished 5-bedroom, 4-bath waterfront residence in the exclusive gated community of Emerald Flats. Perfectly positioned with unobstructed open Gulf views and no rear neighbors, this exceptional home combines privacy, luxury, and outstanding boating access. Designed to maximize its spectacular waterfront setting, the home features two primary suites, each opening to a full-length deck with breathtaking sunrise and open-water views. Enjoy seamless indoor-outdoor living with a private pool, sandy beach area, and deeded 45' boat slip offering protected deep-water dockage just steps from your door. Home is prepped with an elevator shaft which currenly offers locking owners/ additional storage. Beautifully appointed and offered completely turnkey, the residence is currently operating as a successful vacation rental with an established rental history, providing the opportunity for immediate income while still serving as an exceptional personal retreat. Ideally located in the heart of Marathon, just minutes from world-class fishing, seconds from 7 mile bridge, boating, waterfront dining, beaches, and everything the Florida Keys lifestyle has to offer. A rare opportunity to own a new-construction, turnkey Gulf-front home with spectacular open-water views, dual primary suites, exceptional boating access, and income potential.

813 39th St Gulf St, Marathon
$16,000,000
4 Beds ⋅ 3 Baths ⋅ 620952 MLS
Own an entire private island in the heart of the Florida Keys. Located just ¼ mile offshore from Marathon, East Sister Rock Island offers extraordinary privacy surrounded by turquoise waters, yet remains only minutes from the mainland. The property encompasses approximately 6.5 acres, including approximately 5.8 acres of surrounding seabed that create an exceptional marine setting for snorkeling, swimming, kayaking, paddle boarding, fishing and exploring the crystal-clear waters of the Keys. At the center of the island is a beautifully updated 3-bedroom, 2-bath main residence with a detached guest house, offering over 5,000 total SF of living and entertaining space. Recent interior renovations include a beautifully updated kitchen with gorgeous countertops and modern finishes. A 12-foot-wide wraparound veranda captures panoramic water views, Atlantic sunrises and spectacular Florida Keys sunsets. Designed for the ultimate island lifestyle, the property features a waterfront pool and spa, tropical landscaping, multiple outdoor lounging and dining areas, and a 100-foot deep-water dock with ample dockage. World-class fishing, diving, snorkeling, boating and water-sports begin just outside your door. East Sister Rock is equipped for self-sufficient island living with solar and wind power, battery storage, backup generator, desalination system and substantial freshwater cistern capacity. A private helipad provides an additional point of access. Few properties offer this combination of privacy, accessibility, marine surroundings and established island infrastructure. Seller is also open to exploring select Joint Venture opportunities. Note the sale includes 99 E Ocean Drive on the mainland which has a private dock space.

1 E Sister Rock Is, Marathon
$649,000
1 Beds ⋅ 1 Baths ⋅ 620950 MLS
Opportunity awaits on 82nd Street Ocean in Marathon! Located on the oceanside in the desirable Lida Subdivision, this canal front property offers an exciting opportunity to own a piece of the Florida Keys waterfront lifestyle. Featuring approximately 50 feet of concrete dockage with quick and convenient access to the Atlantic Ocean, this property is ideally positioned for boaters looking to spend more time on the water. Currently improved with a 1 bedroom, 1 bath manufactured home, the real opportunity lies in the waterfront setting and its future potential. Much of 82nd Street has transformed over the years with newer elevated single family homes, making this an attractive option for a buyer looking to enjoy the property today or explore the possibility of creating a custom waterfront residence in the future. With 50 feet of waterfront, existing concrete dockage, generous outdoor space, and close proximity to the open Atlantic, this property offers a combination that is increasingly difficult to replicate in the Florida Keys. Bring your vision and discover the possibilities at 647 82nd Street Ocean in Marathon.

647 82nd Street Ocean St, Marathon
$1,190,000
5 Beds ⋅ 3 Baths ⋅ 620951 MLS
A rare opportunity to own a never-before-offered, newly constructed residence in Key Largo's South Creek Village. Built by Construct All and meticulously maintained, the home reflects a thoughtful approach to modern Keys living, with solid CBS construction, a metal roof, impact-resistant windows and doors, and clean, coastal interiors that feel both considered and comfortable. Set on a corner lot, the five-bedroom, three-bath floor plan offers flexibility for family, visiting guests, or extended stays. Natural light carries through open living spaces and into a well-appointed kitchen with generous counterspace, custom cabinetry, and an easy connection to the main gathering areas. Beyond the interiors, the property offers something increasingly difficult to find in the Keys: room to make the grounds your own. There is ample space for a pool, along with accommodations for an RV, boats, trailers, and multiple vehicles. The 12'+ carport is equipped with electric hurricane screens, providing an added layer of storm protection. South Creek Village also offers a private, voluntary homeowners association with access to a waterfront park and boat ramp, as well as first-come dockage for up to 72 hours, an uncommon convenience for launching, loading, or keeping the boat nearby for a weekend on the water. From here, the best of Key Largo is close at hand, with marinas, waterfront dining, parks, John Pennekamp Coral Reef State Park in your backyard, and the surrounding waters offering endless opportunities for fishing, diving, snorkeling, and boating. Equally suited to year-round living or time spent away, this is a home defined not simply by its newer construction, but by the freedom it affords: space for family, space for the boat, and a natural connection to the water and lifestyle that make the Florida Keys unlike anywhere else. Just an hour from Miami and centrally positioned near the best dining and attractions Key Largo has to offer.

646 Cabrera St, Key Largo