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$1,175,000
2 Beds ⋅ 3 Baths ⋅ 620715 MLS
Exceptional investment opportunity in the exclusive Bonefish Yacht Club -- one of the few Florida Keys communities permitted for lucrative short-term 7-day vacation rentals, making this a standout income-producing residence with strong year-round rental demand. This unit will convey with a deeded boat slip in Bonefish Marina, a separate condo association, buyer approval is required. This slip offers direct access to world-class fishing, diving, and cruising grounds, a major draw for vacation renters and boating enthusiasts alike. Set among just 34 single-family attached residences across more than four acres of beautifully maintained tropical grounds, this 1,464 sq. ft. townhome offers light-filled, three-level living. The main level features an open-concept kitchen with brand-new stainless steel appliances, a dedicated dining area, and a living space that flows seamlessly to a waterside balcony overlooking the marina -- perfect for alfresco dining and entertaining. Upstairs, the spacious primary suite includes a private waterfront balcony, walk-in closet, and en-suite bath, while the guest suite enjoys its own balcony, full bath, and generous closet space. The ground level offers a private tiled garage and storage area, ideal for vehicles, fishing gear, and water toys. Residents and guests enjoy resort-style amenities including a heated and chilled pool with expansive sun deck, tiki lounge with wet bar, tennis and pickleball courts, and a private community beach. Combining luxury waterfront living, world-class boating access, and exceptional 7-day rental income potential, this residence is a rare opportunity in one of the Florida Keys' most sought-after rental-approved communities -- ideal as a full-time home, second residence, or high-performing investment property.

96 Ave C, Unit 3, Marathon
$699,000
3 Beds ⋅ 2 Baths ⋅ 620713 MLS
Welcome to 203 Peachtree Avenue, a well-maintained 3-bedroom, 2-bath stilt home in Grassy Key offering peaceful salt pond views and plenty of space to enjoy the Florida Keys lifestyle. Set on a rare, fully fenced double lot, this property offers an exceptional amount of outdoor space that is hard to find in the Keys. Whether you envision room for pets to roam, space to garden, additional parking for trailers and recreational vehicles, or simply enjoying the privacy of a larger homesite, this oversized property provides endless possibilities. Inside, the home features 1,456 square feet of bright, open living space with wood-look flooring, a spacious kitchen with ample cabinetry and counter space, and a convenient laundry room. Large windows and sliding glass doors fill the home with natural light while opening to the expansive wraparound porch, where you can relax and enjoy tranquil salt pond views. The elevated design offers abundant covered parking and storage below, with column height tall enough to accommodate a boat, RV, or multiple vehicles. A metal roof, concrete pilings, tropical landscaping, and a private hot tub add to the home's appeal. Located just moments from Sunset Bay Park in Grassy Key, you'll enjoy a peaceful island setting while remaining close to Marathon's restaurants, shopping, marinas, and everyday conveniences. Whether you're searching for a full-time residence, weekend getaway, or island retreat with room to spread out, this unique property combines privacy, versatility, and the laid-back Florida Keys lifestyle.

203 Peachtree Ave, Marathon
$850,000
3 Beds ⋅ 2 Baths ⋅ 620710 MLS
Welcome to your perfect island retreat! This stunning 3-bedroom, 2-bath modular home combines modern comfort with coastal charm. Featuring a spacious open floor plan, the home boasts beautiful quartz countertops that add a touch of elegance to the well-appointed kitchen. The master suite is a true sanctuary, complete with an en suite bathroom and a generous walk-in closet. Enjoy peekaboo views of the Gulf from the comfort of your living room or relax on the composite decking in your fully fenced, spacious yard. The property also includes off-street parking and a convenient laundry room. With hurricane impact windows and doors, you'll feel secure in any weather. Just minutes from the vibrant city of Key West, this home is also close to a public boat ramp for all your maritime adventures. Don't miss the chance to make this coastal gem your own!

441 Ave A, Big Coppitt
$12,450,000
22 Beds ⋅ 21 Baths ⋅ 620702 MLS
Located on approximately 2 acres of upland and nearly one acre of bay bottom, this 21-room boutique hotel offers direct access to Florida Bay and stunning waterfront living in South Key Largo. Stretching from the Overseas Highway to the pristine waters of Florida Bay, the property is a true hidden gem. Family-owned, well maintained, and one of the Upper Keys' rarest bay front hospitality investment opportunities. Enjoy protected dockage with direct bay access, a private sandy beach, a concrete boat ramp, a heated and chilled swimming pool, outdoor grilling areas, and multiple tiki huts. Guests also benefit from spectacular year-round sunset views, creating a memorable Keys experience. 10 guest rooms have been tastefully renovated with a modern coastal design, while the remaining rooms have been refreshed with new paint and updated furnishings, delivering immediate rental income with strong upside potential to further increase revenue and value. Ideally located near dining, shopping, and the area's most popular attractions, this exceptional property offers a variety of possibilities: continue operating as a cherished boutique hotel, reposition to enhance performance, or redevelop into an even more valuable waterfront destination. A truly rare, turnkey investment with tremendous upside in one of the Florida Keys' most desirable locations.

97850 Overseas Hwy, Key Largo
$899,000
3 Beds ⋅ 4 Baths ⋅ 620709 MLS
Like-new Key Largo home offering the perfect combination of modern construction, low-maintenance living, and outstanding value! Built in 2022, this beautifully designed concrete residence spans nearly 2,000 square feet on a professionally landscaped, fully fenced corner lot. Enjoy all the benefits of newer construction, including lower insurance premiums, reduced maintenance costs, and the peace of mind that comes with a metal roof, impact windows and doors, and current building standards. A gated paver driveway welcomes you to a charming wraparound porch, ideal for relaxing and enjoying the tropical breeze. Inside, an open-concept floor plan is filled with natural light from expansive impact glass. The gourmet kitchen is designed for entertaining with quartz countertops, a tiled backsplash, stainless steel appliances, and a large center island overlooking the spacious living and dining areas. The first floor features a guest suite with a private bath, powder room, and generous pantry/storage closet. Upstairs, the primary suite offers a walk-in closet, luxurious ensuite bath, and a private screened balcony--the perfect place to start your day. An additional oversized bedroom with dual closets and ensuite bath, along with a convenient laundry room and linen storage, complete the second level. Outside, the private corner lot is a thoughtfully landscaped oasis with low-maintenance artificial turf, leaving more time to enjoy the Keys lifestyle. There's also room to add a pool if desired. Ideally located for an easy commute to the mainland, Ocean Reef Club, and the College of the Florida Keys' new Upper Keys campus, this home is also just minutes from the area's renowned marinas, waterfront dining, shopping, and world-class fishing and diving. If you've been searching for a newer, move-in ready home that offers lower ownership costs and exceptional value in today's market, this is it!

13 Coral Way, Key Largo
$6,000,000
4 Beds ⋅ 6 Baths ⋅ 620708 MLS
Coastal Luxury. Endless Lifestyle. A rare opportunity to own an extraordinary Plantation Key waterfront estate where captivating ocean views, 140 feet of protected dockage, direct Atlantic access, and exceptional craftsmanship come together in perfect harmony. Privately tucked away on a quiet cul-de-sac, this stunning coastal residence was thoughtfully designed for those who appreciate effortless luxury both on and off the water. Filled with natural light, the open-concept floor plan showcases soaring ceilings, walls of glass, and seamless indoor-outdoor living that frames beautiful water views throughout the home. At the heart of the residence, the gourmet chef's kitchen is beautifully appointed with premium appliances, including dual ovens, two dishwashers, generous preparation space, and an oversized island that effortlessly connects the living and dining areas, creating the perfect setting for entertaining family and friends. Step outside to an expansive covered terrace complete with a built-in barbecue, outdoor refrigerator, and multiple gathering spaces overlooking the resort-style saltwater pool and spa, lush tropical landscaping, and tranquil waterfront. Whether hosting sunset cocktails or enjoying a quiet morning coffee, every space has been designed to embrace the relaxed elegance of the Florida Keys. The thoughtfully designed floor plan offers four spacious bedrooms, four full baths, two half baths, a private elevator, and a luxurious primary suite featuring separate his-and-her walk-in closets. A spacious secondary living area, currently enjoyed as a waterfront fitness studio, offers endless possibilities as a media room, family room, home office, or guest retreat. For boating enthusiasts, this property is truly exceptional. Boasting 140 feet of protected dockage, a boat lift, five garages with direct canal-side access, and quick, easy access to the Atlantic Ocean, it is perfectly suited for everything from offshore fishing adventures to leisurely days on the water. Surrounded by beautifully established tropical gardens with irrigation and meticulously maintained grounds, this remarkable waterfront estate offers the perfect balance of privacy, sophistication, and relaxed coastal living

202 Plantation Shores Dr, Tavernier
$999,000
2 Beds ⋅ 3 Baths ⋅ 620707 MLS
Welcome to your own slice of paradise in the heart of Key Colony Beach! This well-maintained 2-bedroom, 3-bath half duplex offers the ideal blend of comfort, convenience, and the coveted Florida Keys boating lifestyle. The bright, open floor plan creates an inviting space for entertaining and everyday living, while the wraparound balcony provides the perfect place to enjoy the island breeze and relax outdoors. Boaters will appreciate 37.5 feet of dockage with quick access to both the Atlantic Ocean and the Gulf of America through nearby Vaca Cut, making it easy to enjoy world-class fishing, diving, and waterfront adventures. The attached garage provides ample space for parking, storage, and all of your fishing and boating gear. The backyard features desirable easterly exposure, allowing you to enjoy beautiful morning sun and cooler afternoons. Located in one of the Florida Keys' most sought-after waterfront communities, you'll be just moments from Key Colony Beach's exceptional amenities, including Sunset Park, the par-3 golf course, waterfront restaurants, scenic walking and biking paths, pickleball and tennis courts. Whether you're searching for a full-time residence, vacation retreat, or investment opportunity, this waterfront gem offers everything you need to experience the relaxed island lifestyle that makes Key Colony Beach so special.

350 11th St, Key Colony
$2,485,000
3 Beds ⋅ 3 Baths ⋅ 620704 MLS
Refined coastal living at Tarpon Flats, Islamorada's most exclusive bayfront enclave. This intimate, gated community consists of just 12 luxury residences spread across four beautifully landscaped acres. A stately paver driveway welcomes you to impeccably manicured grounds, where the charm of Old Florida meets the timeless elegance of Nantucket. This three-story home offers a thoughtful layout and spectacular bay views throughout. The ground floor features covered parking, a versatile multi-purpose room, and access through a gracious foyer entry. Upstairs, the main living level boasts an open-concept kitchen and dining area with panoramic bay vistas, two bedrooms, two bathrooms, and a tranquil porch ideal for enjoying sunset skies. The top floor is reserved for the expansive master suite, complete with a private balcony and sweeping waterfront views. Tarpon Flats offers an amenity-rich lifestyle tailored to the discerning buyer. Enjoy a waterfront pool and gazebo, private beachfront access, generous dockage for your skiff, a charming greenhouse, and a tennis court with shaded seating for guests. Adding to the ease of ownership, the community provides a full-time concierge service and an on-site handyman, ensuring both comfort and convenience year-round. Sophistication, privacy, and natural beauty converge in this exceptional Islamorada retreat--come discover what makes Tarpon Flats truly one of a kind.

81250 Overseas Highway Unit 2, Islamorada
$1,900,000
3 Beds ⋅ 3 Baths ⋅ 620705 MLS
Welcome to 870 Copa D Oro, an exceptional waterfront retreat in the highly sought-after Flamingo Island neighborhood. Offered for the first time in 22 years, this rare property boasts an impressive 190 feet of pristine waterfront on an oversized 12,600-square-foot lot, offering breathtaking water views and endless opportunities for the boating enthusiast. This well-maintained CBS home features 2 bedrooms on the main level with a third bedroom in the upstairs loft, offering 1,560 square feet of thoughtfully designed living space. Rich wood ceilings and an abundance of natural light create a warm, inviting atmosphere filled with timeless Florida Keys charm and character. At the heart of the home is an updated chef's kitchen, complete with a Wolf gas range, new refrigerator, wine cooler, and beautiful wood cabinetry with granite countertops--perfectly blending style and functionality for everyday living or entertaining. Impact-rated doors and windows, screened porches on both the upper and lower levels, and a spacious balcony provide the perfect spaces to relax and take in the stunning waterfront views. Designed for the ultimate Florida Keys lifestyle, the property includes a permitted enclosure beneath the home, covered parking, and exceptional dockage featuring a 40-foot dock plus an additional cut-in slip for a smaller vessel, providing room for multiple boats. Whether you're looking for a full-time residence, vacation getaway, or premier waterfront investment, 870 Copa D Oro offers an unmatched combination of location, spectacular views, exceptional boating access, and the distinctive charm that makes Florida Keys waterfront homes so special.

870 Copa D Oro, Marathon
$2,795,000
4 Beds ⋅ 4 Baths ⋅ 620703 MLS
Modern elegance defines this exceptional custom-built waterfront estate offering 4 bedrooms, 3 full baths, and 1 half bath, complete with every amenity for luxury coastal living. Designed for effortless entertaining, the open-concept floor plan showcases a stunning gourmet kitchen featuring premium stainless steel appliances, quartzite and marble countertops, designer lighting, a beverage cooler, ice maker, and an elevator for added convenience. Expansive floor-to-ceiling sliding glass doors flood the home with natural light while seamlessly blending indoor and outdoor living. The entire third floor is dedicated to a luxurious primary suite, featuring a spa-inspired bath, an oversized walk-in closet, and a private retreat designed for comfort and relaxation. Perfectly situated in one of Key Largo's premier boating locations, the property offers a deep-water dock and an 18,000-pound boat lift and two jet ski docks with quick access to Florida Bay and the Atlantic Ocean.

20 Center Ln, Key Largo
$3,675,000
2 Baths ⋅ 620701 MLS
Rare chance to own a piece of the most iconic street in the Florida Keys. This turn-key commercial building at 1215 Duval Street is offered at a 7.0% cap rate with a solid, established long-time successful restaurant as the tenant and a lease already in place. (Note: the business is not for sale; the real estate and the income-producing lease are.) Positioned in the heart of Old Town's high-traffic corridor, the property benefits from year-round foot traffic, world-famous Duval Street exposure, and the enduring demand that makes Key West commercial real estate so limited and so coveted. With a dependable tenant and stabilized income from day one, this is a true passive, hands-off investment in one of the strongest small-market commercial locations in the country. Opportunities to acquire well-located Duval Street commercial real estate with an in-place lease and a proven tenant are exceedingly rare. Whether you're a 1031 exchange buyer seeking reliable cash flow or an investor looking to plant roots in paradise, 1215 Duval Street delivers location, income, and long-term upside. Schedule your private showing today.

1215 Duval St, Key West
$995,000
3 Beds ⋅ 2 Baths ⋅ 620700 MLS
OWNER FINANCING. 27452 ANGUILA LANE RAMROD KEY FOR RENT. REPAINTED INSIDE AND OUT. ALL NEW FLOORING. 1400 SQFT 180 MPH RATED 3/2 HOME. 300SQFT ENCLOSURE FOR ALL YOUR FISHING NEEDS.40' DOCK ON AN OVERSIZED CORNER LOT WITH LOTS OF ROOM FOR RV AN BOAT PARKING. MINUTES FROM LOOE KEY REEF. 9' CEILINGS, CROWN MOLDING AND CENTRAL AC. FULLY PEA ROCKED YARD FOR LOW MAINTENANCE. NEW METAL ROOF, HURRICANE WINDOWS AND DOORS. GRANITE COUNTERS. RENT IS $4,750 PER MONTH. $4,000 SECURITY. $8,950 AND YOUR IN. CALL FOR PRIVATE SHOWING show contact info . AVAIL NOW. OWNER REALTOR. RIDE BY FIRST AND IF YOU LIKE IT, CALL ERICA. LONG TERM LEASE CONSIDERED.PURCHASE $1,199,000.00, $50,000 DOWN PMT. WILL FINANCE BALANCE FOR 5 YEARS AT 8% NO WIND NO FLOOD INSURANCE REQUIRED. HUGE SAVINGS. HUGE OPPORTUNITY. NEGOTIABLE. OWNER REALTOR. RIDE BY IF YOU LIKE IT CALL FOR SHOWING. APPROX. MONTHLY PMT. $8,800.00

27452 Anguila Ln, Ramrod
$975,000
2 Beds ⋅ 2 Baths ⋅ 620699 MLS
Great opportunity. The condo is divided in to separate units, each having one bedroom and a bath. The property includes a 25x70 live aboard commercial deep water slip. Minutes from Key West. The area provides many choices for dinning , shopping ,nightlife, golf, beaches and a short ride to the Key West airport.

6810 Front St Unit B-13S & SNL 18, Stock Island
$995,000
2 Beds ⋅ 2 Baths ⋅ 620697 MLS
Embrace the laid-back lifestyle of the Florida Keys in this waterfront two-bedroom, two-bathroom condominium with beautiful water views. Soaring vaulted wood-beamed ceilings, a skylight, and expansive sliding glass doors fill the home with natural light while showcasing the sparkling water beyond. The open-concept living and dining areas flow seamlessly to a spacious wraparound balcony, creating the perfect setting to enjoy your morning coffee, entertain guests, or unwind with the island breeze. The functional kitchen opens to the main living area, making entertaining effortless. Located in Bay Villas, a boutique waterfront community of just nine residences, residents enjoy beautifully maintained grounds, a community pool, and inviting waterfront gathering spaces. Whether you're looking for a full-time residence, a seasonal getaway, or an investment opportunity, this waterfront retreat offers the relaxed charm that makes the Florida Keys so special.

32 Hilton Haven Rd Unit APT 5, Key West
$777,000
2 Beds ⋅ 2 Baths ⋅ 620695 MLS
Desirable 2 bedroom, 2 bath on a Private Street with Waterfront Access! Welcome home to this well maintained concrete block home, ideally located on a quiet private residential street. Enjoy exclusive access to a community park and private boat ramp reserved for owners, making it perfect for boating and outdoor enthusiasts. The property features lush tropical landscaping with mature fruit trees, a beautiful rock garden, and plenty of out door space to relax and entertain. Inside, you'll find a comfortable layout with spacious living areas, while the oversized two car garage offers ample room for vehicles, storage or a workshop. Plus an extra storage, office or artisan space. Whether you're a first time home buyer, looking to down size, or searching for the perfect family home, this property offers comfort, privacy, and a desirable neighborhood in a peaceful setting. Don't miss this opportunity to own a slice of PARADISE!

91 Dorsett Dr, Marathon
$679,000
620693 MLS
An exceptional opportunity to acquire two (2) Waterfront Transferable Development Rights (TDRs akaTBRs) for use within the Village of Islamorada. Offered together for $679,000, this represents an outstanding value at approximately $339,500 per TDR--well below the cost of purchasing comparable rights individually. These development rights may be transferred to an eligible receiver property within the Village, providing a rare opportunity for builders, developers, and property owners to secure valuable development potential at a discounted price. Buyer shall pay all closing costs associated with the transaction, including the Village transfer fee. A recent, successful transfer provides buyers with confidence in a proven Village transfer process. This sale does not include any real property.

2x Waterfront Tdr For Sale, Not Provided
$539,000
1 Beds ⋅ 1 Baths ⋅ 620692 MLS
Great opportunity to own your own home or have an excellent source of rental income. Currently the least expensive detached residence in Key West. Freshly painted interior and new AC. This renovated one bedroom condo cottage overlooking the large communal pool is just one block to vibrant White St with its cafes and restaurants, gourmet food stores, galleries and yoga studios. A short walk or bike ride to the beaches and the heart of Old Town, the Historic Seaport and Duval Street.....The compound has a large pool shared with only 3 other condos. There are lovely landscaped communal areas with fruit trees, sun decks, lounge chairs and outdoor dining areas.....Recent improvements to the home include a new metal roof, impact windows plus additional storm shutters. The condo has one bedroom, a full bath with shower above, full kitchen and double doors leading to the pool and patio area.

1318 Duncan St Unit 3, Key West
$59,000
2 Beds ⋅ 2 Baths ⋅ 620691 MLS
Remodeled Countryside Home in Vero Beach - This updated 2-bedroom, 2-bath mobile home offers +/-1,480 sq. ft. of comfortable living with a bright kitchen, spacious bedrooms, roomy sunroom, storage or man-cave, and tasteful modern touches throughout-all set within the peaceful, gated community of Countryside at Vero Beach. Residents enjoy access to a beautiful clubhouse for social gatherings, a new, resort-style pool and hot tub, and recreational options including tennis, pickleball, shuffleboard, Billiards, and bocce ball. The community also features a stocked, fishing lake, convenient on-site management, RV storage, a dog park, and laundry facilities-capturing the perfect blend of comfort, activity, and relaxed Florida countryside living.

8775 20th St Unit LOT 249, Vero Beach, Other
$475,000
2 Beds ⋅ 2 Baths ⋅ 620690 MLS
NEW PRICE.....Welcome to this beautifully updated condo at 3930 S. Roosevelt Blvd. #N108, offering the perfect blend of comfort, convenience, and island living. Overlooking the sparkling community pool, this inviting residence features a tastefully remodeled kitchen with modern finishes, newer flooring throughout, and a bright, open living space designed for easy living and entertaining. Enjoy your morning coffee or evening cocktail with relaxing pool views, while the covered parking bay provides the added convenience and protection every Key West homeowner appreciates. Residents also enjoy outstanding community amenities, including a newly completed state-of-the-art fitness center, adding even more value to this desirable complex. Located just minutes from beaches, shopping, dining, and Old Town Key West, this move-in-ready condo is ideal as a full-time residence, vacation getaway, or investment property. Don't miss this opportunity to own a beautifully updated piece of paradise in one of Key West's most desirable locations. Call today to set up your showing.... Very easy to show

3930 S Roosevelt Blvd Unit N108, Key West
$499,000
2 Beds ⋅ 2 Baths ⋅ 620689 MLS
This bright, private 2BR/2BA corner unit sits at the end of the west wing, with an extra window that fills the space with light and only one shared wall for real quiet. This unit comes with covered parking. The kitchen is outfitted with stainless steel appliances, and a full-size washer and dryer means laundry day never means leaving home. A covered parking space (#122) comes with the sale. Las Salinas Condominiums is one of the best-kept communities in Key West, and it shows. The pool is sun-drenched and inviting, and the fitness center may be the best on the island, with private access to cardio and strength rooms that are always spotless and always stocked with quality equipment. Monthly fees of $535 cover building insurance, exterior maintenance, and full on-site management, so ownership here is refreshingly hands-off. Step outside and you're close to a grocery store, a day spa, and a bus stop for easy island transportation. Just past the entrance, the two-mile Smathers Beach promenade is calling, whether that's a sunrise walk, a bike ride, or a spot to watch the sky change color every evening. Add in open-lot parking for a second vehicle, plus storage and bicycle rooms, and this is a home built for the way you actually want to live in Key West. Call today to schedule a private showing.

3930 S Roosevelt Blvd Unit W314, Key West
$499,000
2 Beds ⋅ 2 Baths ⋅ 620688 MLS
Welcome to Casa Clara, one of Key Colony Beach's most sought-after oceanfront communities, where relaxed island living meets resort-style amenities. This inviting 2-bedroom, 2-bath condo offers an exceptional opportunity to enjoy the Florida Keys as a full-time residence, vacation getaway, or income-producing rental. Enjoy ocean views and refreshing sea breezes from both side patios, creating a seamless indoor-outdoor lifestyle. The condo is being sold furnished, including housewares, making it move-in or rental ready from day one. Casa Clara is a well-established oceanfront community of 83 residences that has been recently and completely renovated, offering over 500 feet of private white-sand beach that is cleaned daily. Resort-style amenities include an oceanfront swimming pool, tennis and pickleball courts, shuffleboard, a fishing pier with cleaning station, elevator access, on-site management, and beautifully landscaped courtyards, all overlooking the Caribbean-blue waters of the Atlantic. The walkable Key Colony Beach lifestyle is second to none--enjoy peaceful beach days, sunset strolls, and easy access to restaurants, shops, parks, marinas, charter boats, and a par-3 golf course. 14-day rentals are permitted, providing excellent flexibility and strong rental demand. The community also offers ample parking, nearby boat trailer storage, and allows one pet (per association policy)--a valuable feature in an oceanfront condo. Whether you're lounging by the pool, walking the beach at sunset, or welcoming guests seeking an authentic Florida Keys experience, this Casa Clara condo delivers comfort, lifestyle, and long-term value.

201 E Ocean Dr Unit 1-211, Key Colony
$2,060,000
5 Beds ⋅ 3 Baths ⋅ 620686 MLS
Rare Licensed Oceanfront Short-Term Vacation Rental in the Lower Florida Keys, with SELLER FINANCING OFFERED! Welcome to Fandango, a highly successful transient (daily-weekly) vacation rental home offering an exceptional investment opportunity and a personal retreat. This stunning 5-bedroom, 3-bathroom property, built in 2011 and expanded in 2018, was thoughtfully designed as the ultimate family vacation rental retreat. Featuring an adjacent oceanfront parcel with a private beach, kayaks, and a floating dock for fishing or docking boats up to 24 feet, this property provides everything needed for fun and relaxation. Outdoors, enjoy a sparkling swimming pool, soothing hot tub, tropical landscaping with coconut palms and banana trees, and a screened-in porch for al fresco dining. Inside, the open floor plan includes four king bedrooms and a fifth bedroom with a queen and single bed, smart TVs, and updated appliances. Centrally located at MM21.5, Fandango is just 20 minutes from Key West, 10 minutes from Big Pine Key, and 15 minutes from Bahia Honda State Park, with dining options nearby, including a 5-star restaurant within a mile. This property is offered fully furnished and equipped, including bookings into 2027 and 10-years' average income of $160+k. Professional property management is in place, ensuring both secure investment returns and worry-free family vacations. This low-maintenance, turn-key home offers the rare opportunity to own one of the few legally licensed short-term rentals in the Lower Keys. Owning a vacation rental property means you're not just paying for vacations--you're building equity and unlocking financial benefits, all while eliminating the scramble for accommodations every trip. Show up, relax, and let your investment work for you.

94 Sacarma Dr, Cudjoe
$449,999
1 Beds ⋅ 1 Baths ⋅ 620685 MLS
Ocean-View Waterfront Retreat in Gated Venture Out on Cudjoe Key. NIGHTLY RENTALS ALLOWED Enjoy the Florida Keys lifestyle in this well-maintained 1-bedroom, 1-bathroom waterfront home located in the highly desirable gated community of Venture Out. With ocean views, direct boating access, excellent amenities, and nightly rentals permitted, this property is ideal as a vacation home, income-producing investment, or full-time residence. The home features numerous updates, including a new roof in 2018, air-conditioning system in 2020, and hot water heater in 2025. Additional improvements include newer impact-resistant windows, Bahama shutters, powder-coated storm panels, and updated mobile home tie-downs for added peace of mind. Boaters will appreciate the 35-foot concrete seawall with dock whips and quick access to the backcountry, offshore waters, and Atlantic Ocean. A concrete slab beneath the home provides valuable storage for fishing gear, kayaks, bicycles, and other Keys essentials. Venture Out offers an impressive array of amenities, including a large oceanfront saltwater swimming pool, community marina with fuel station, boat ramp, and boat wash-down area. Residents and guests also enjoy lighted tennis and pickleball courts, basketball and bocce courts, a recreation hall, waterfront pavilion, and regular community activities. The golf-cart-friendly neighborhood makes it easy to enjoy everything the community has to offer. Whether you are searching for a relaxing island escape, strong rental opportunity, or waterfront home in the Lower Keys, this property delivers an exceptional combination of location, boating access, amenities, and investment potential. Schedule your private showing today and experience this special Cudjoe Key property for yourself.

701 Spanish Main Dr Unit 246, Cudjoe
$1,695,000
2 Beds ⋅ 2 Baths ⋅ 620684 MLS
Fully furnished, 2b/2b designer-complete home is close to the heart of Old Town Key West, yet far enough from the maddening crowd. Late-1800s Conch house with detached guest cottage were gutted, reconfigured and restored in 2021. New roof, infrastructure and new state-of-the-art chef's kitchen. Casement windows open to the back garden that has 8 varieties of bananas. And what a fine garden it is: Orchids & herbs & fruit, oh my. Salvaged Dade County pine walls light up with windows galore. A side yard connects the 1b/1b primary residence to the en-suite detached cottage. On-demand hot water heater. Outdoor shower. Hot tub. Off-street parking. Rear garden entrance to property from Havana Lane offers front and back access. Meticulous detail throughout makes this A MUST SEE. Low fee insurance costs available upon request.

907 Frances St, Key West
$2,989,000
4 Beds ⋅ 5 Baths ⋅ 620683 MLS
BRAND NEW CONSTRUCTION * LICENSED VACATION RENTAL WITH RENTALS IN PLACE FOR 2026 & 2027. Indulge in the art of refined coastal living in this brand new luxury waterfront residence, where timeless elegance meets modern design across four bedrooms and four and a half baths, thoughtfully crafted for both elevated comfort and effortless entertaining. Boasting an impressive 99 feet of composite dockage, this exceptional property invites carefree days on the water, while the resort-style outdoor setting captivates with a sparkling pool, a spa that transforms into a rejuvenating cold plunge, and a beautifully designed backyard finished with lush turf, elegant pavers, and full fencing for privacy. Inside, a spacious open concept living and dining area unfolds with impeccable attention to detail, highlighted by sophisticated champagne bronze finishes and stunning wood plank tile that flows throughout, creating a warm yet contemporary ambiance. A private elevator provides effortless access to every level, including the expansive 880 square foot enclosed lower level, designed as the ultimate entertainment retreat featuring a sleek wet bar and dual impact glass doors that open on demand to blend indoor and outdoor living in a truly dramatic fashion. Each bedroom serves as its own private sanctuary, complete with a luxurious ensuite bath, offering comfort, privacy, and a sense of exclusivity for both residents and guests alike. This is more than a home, it is a statement of lifestyle, where every detail has been curated to deliver the pinnacle of waterfront luxury living. Property is being sold turnkey and vacation rental ready.

300 N Anglers Dr, Marathon
$11,700,000
6 Beds ⋅ 8 Baths ⋅ 620680 MLS
Sunset Sanctuary. Natural beauty and captivating sunsets of the Florida Keys define this newly completed gated waterfront estate on Lower Matecumbe Key. Surrounded by a serene coastal landscape and native birdlife, the property offers boating access to both Florida Bay and the Atlantic Ocean. Completed in 2025, the three-level main residence features two primary suites, three guest bedroom suites, media room, an elevator, and a custom kitchen showcasing mahogany cabinetry and Thermador appliances. Expansive balconies extend the living spaces into the natural surroundings. The third-level Sunset Lounge elevates entertaining with a full bar, wine storage, generous seating, a mega-TV, and views toward Florida Bay. Outdoors, the property features a saltwater pool and spa, covered dining and entertaining areas, a private pickleball court, and a dock with boat lift. A detached guest house provides comfortable accommodations with added separation from the main residence. This distinctive Islamorada estate brings together natural beauty, recreation, boating access, and elevated island living.

77350 Overseas Hwy, Islamorada
$995,000
3 Beds ⋅ 3 Baths ⋅ 620681 MLS
Experience the best of the Florida Keys in this beautifully appointed 3-bedroom, 2.5-bath waterfront townhome in the desirable Bonefish Townhomes community. Offering panoramic Atlantic Ocean and canal views, this property is designed for those who love life on the water. A 62-foot deeded boat slip with a lift is located just outside your back door, making it effortless to head offshore or enjoy quick access to both the Atlantic Ocean and the Gulf through nearby Vaca Cut. Four private balconies provide multiple spaces to relax, with two overlooking the open water and two offering views of the marina. The lower balcony features a spiral staircase leading directly to your dock for ultimate convenience. Inside, the split-bedroom floor plan offers comfort and privacy, while the open living spaces are filled with natural light and designed to maximize the surrounding water views. Covered parking, generous storage, and room for all your boating and fishing gear complete the package. Residents of Bonefish Townhomes enjoy resort-style amenities, including a heated and chilled pool, tennis and pickleball courts, a spacious tiki gathering area, and a scenic walking and biking path throughout Coco Plum. Coco Plum Beach is also just a short stroll away. Whether you're searching for a primary residence, vacation getaway, or investment opportunity, this property checks every box. Weekly rentals are permitted with a 7-day minimum, making it an excellent option for those looking to generate rental income while enjoying the Florida Keys lifestyle. Schedule your private showing today and discover why Bonefish Townhomes remains one of Marathon's most sought-after waterfront communities.

95 Coco Plum Dr Unit 2D, Marathon
$75,000
620678 MLS
Vacant lot in the Key By the Sea community offering an ideal private storage opportunity, especially for a neighboring property owner seeking additional space for trailers, vehicles, or boats on a trailer. Living in an RV on this parcel is not permitted. Lot 8E measures approximately 31 feet in depth by 30.5 feet in width and is currently undeveloped with no structure in place. A Buyer may pursue a building right through the City of Marathon or acquire one privately in order to construct or place a code compliant structure in accordance with local regulations. Utilities including city sewer, water, and electric service are available within the community, and there are no impact fees related to prior utility installation. Key By the Sea offers convenient amenities including a boat ramp with direct Atlantic Ocean access, laundry facilities, a clubhouse, and pet friendly policies. Each parcel is individually owned with its own real estate number, and the monthly association fee is approximately $191. A rare and affordable opportunity to secure flexible use property in the Florida Keys, whether for private storage today or future building potential.

6099 Overseas Hwy Unit LOT 8E, Marathon
$649,000
1 Beds ⋅ 1 Baths ⋅ 620677 MLS
Crystal-clear turquoise waters, swaying palms, and gentle ocean breezes create the perfect Florida Keys escape. The historic Cheeca Lodge is located in the heart of Islamorada, which is recognized as ''The Sport Fishing Capital of the World''. Islamorada is renowned for fine dining, water sports, The Art District, galleries, shopping and breweries. The resort encompasses 27 acres with 1,200' of beach frontage and a 525' fishing pier. This beautiful one-bedroom King suite, with additional sleeper sofa in the living room and private screened balcony, overlooks the garden and waterfall. This is a luxury, income-producing property. Nightly rentals are allowed, with onsite management, an owner's closet, and owner's use of up to 28 days. The resort offers a 24-hour shuttle, valet parking, concierge service, 5-star fine dining, ballroom, conference room, a spa, fitness center, beach, pools, dock, tiki bars, 9-hole par 3 golf course, Pickle Ball courts, lighted tennis courts, lush gardens, bike path, fishing, diving, snorkeling, water sports and Camp Cheeca for children.

81801 Old Hwy Unit 754, Islamorada
$1,200,000
1 Baths ⋅ 620675 MLS
Exeptional opportunity at your fingertips. Oversized parcel located on the corner of US 1 and N Marlin Ave in Key Largo. Three highway lots providing 125 ft of direct US 1 frontage plus alleyway behind property. This corner location allows for easy access onto the property both on US 1 and on the north side of the property. This is a large open space for many opportunities. Ground level concrete building, open and ready for a clean slate, includes large open space, high ceilings, central AC, half bath, and access from both front and back of the building. To complete this package, this property is located in an''X'' flood zone, is completely fenced around entire property, and is zoned mixed use for many possiblities. Contact Listing Agent for additional information

104980 Overseas Hwy, Key Largo