Refine Search
Map
Sort by
$725,000
A11703219 MLS
Florida Keys treasure ripe for rejuvenation! Located in the desirable Indian Harbor Community of Tavernier in Islamorada, this inviting 2-bedroom, 2-bath CBS home is a standout value in the Upper Keys. Featuring a durable metal roof, large downstairs storage, and a huge, screened patio that's perfect for entertaining. Upstairs, you'll find a massive veranda, the perfect spot for your morning coffee or an afternoon tropical cocktail. Exceptional HOA Park with a boat ramp, giving you easy access to fantastic backwater and ocean fishing, diving, sandbar adventures, and restaurant hopping. Whether you're seeking a full-time or seasonal residence, or a weekend getaway for nearby Tri-County residents, this home offers the ideal Florida Keys experience and opportunity you've been dreaming of!

155 Sioux St, Islamorada
$1,895,000
A11689021 MLS
Welcome to White Marlin — a true fisherman’s paradise! Step into this beautiful 3-bedroom, 3-bathroom coastal retreat, featuring an open-concept design perfect for relaxing or entertaining. The expansive kitchen with tile countertops offers ample space, and the screened-in balcony lets you enjoy serene views without interruptions. Outside, you’ll find a 60-foot concrete dock and boat ramp, ideal for fishing enthusiasts, and a refreshing pool to cool off after a day on the water. With a propane backup generator for peace of mind, you’re ready for any occasion. Unwind on your private beach and savor breathtaking sunsets over turquoise waters — a slice of paradise awaits you here!

178 Gulfview Dr, Islamorada
$1,500,000
A11688486 MLS
Islamorada Exclusive Anglers Reef Resort! An oceanfront gated community with resort -style amenities, marina, & 2 sandy beaches; this fully furnished, two-story single-family home, w/ 2 Bedrooms, 2.5 Baths, is a treasure for ocean lovers & investors alike. Premium features include impact windows & doors, stainless steel appliances, wood cabinetry, & granite countertops. A Boater’s Paradise with direct oceanfront access & proximity to the famous Islamorada sandbar, & a deeded boat slip is also available for sale, accommodating a boat up to 31 feet. Proven Rental Success, in a well-established program, this home has a 7-Day rental license, with over 175 five-star reviews, making it an ideal investment opportunity or personal retreat. Pet friendly community.

120 Anglers Way, Islamorada
$1,049,000
A11688370 MLS
ALL CONCRETE BUNKER in an X Zone, beautifully updated! With 2,200sqft under air, this 3/3 pool home has it all! Located in Islamorada's Plantation Key Colony, on a fully fenced & gated lot & a half in an X zone. The main living area offers vaulted & insulated ceilings & a true chef's kitchen, w/ a full suite of GE Cafe series stainless appliances. Back steps lead to the new heated & chilled in ground pool w/ jets & water fall, surrounded by travertine pavers & a new tiki with electric. Upgrades incl impact windows, new electrical throughout incl. underground service; new plumbing, LED lighting, all new HVAC & more! Join Plantation Key Colony's voluntary HOA (just $250 per year) to access private bayfront homeowner's park, beach, truck & trailer parking & boat ramp is just down the street.

220 Jasmine St, Islamorada
$1,950,000
A11685784 MLS
Discover unparalleled Keys living at 190 Gulfview Dr in Islamorada’s exclusive White Marlin Beach. This exquisite 4-bedroom, 3-bath home boasts 70 feet of private dockage with seamless access to both ocean and bay waters. Enjoy exceptional living areas, a sparkling pool with covered entertainment space, an expansive upstairs balcony, and abundant storage for your gear. The additional downstairs living area offers extra flexibility, perfect for guests. With private access to White Marlin Beach, you’ll be steps from pristine sands and breathtaking sunsets. This property offers exceptional rental history with repeat guests and strong cash flow which make this an outstanding investment. Embrace luxury island living at its finest!

190 Gulfview Dr, Islamorada
$410,000
A11685804 MLS
Welcome to this beautifully updated and move-in ready 1-bedroom, 1-bath retreat in one of the most affordable waterfront communities in Islamorada. This condo offers the perfect blend of relaxation and adventure, first come-first serve dock for a 25-foot boat, a convenient boat ramp, and on-site boat storage—ideal for water lovers and boaters alike. Step inside to find a meticulously updated interior featuring coastal-inspired finishes, an open floor plan, and abundant natural light. Features include central a/c, and garage/storage. The living space flows seamlessly to the private balcony, perfect for enjoying tropical ocean breezes. Amenities include a heated pool, tennis and pickleball courts, all just steps from your front door. Comes fully furnished and ready to go.

119 Cortez Drive Unit #3G, Islamorada
$1,100,000
A11684015 MLS
Peaceful Palms - is a newly-built luxury coastal development situated in the gated community of Islamorada, FL. This upscale property features 15 high-end townhomes, all boasting an oceanfront location, as well as oceanfront views. You can enjoy spectacular views of the acclaimed Sandbar and Alligator Reef Lighthouse, as well as breathtaking sunrises. For boating enthusiasts, there are oceanfront docking facilities available for rent. Additional amenities include an oceanfront pool, making it an ideal location for a Florida Keys getaway and investment property.

84745 Old Highway Unit #1, Islamorada
$1,900,000
A11684745 MLS
Peaceful Palms - is a newly-built luxury coastal development situated in the gated community of Islamorada, FL. This upscale property features 15 high-end townhomes, all boasting an oceanfront location, as well as oceanfront views. You can enjoy spectacular views of the acclaimed Sandbar and Alligator Reef Lighthouse, as well as breathtaking sunrises. For boating enthusiasts, there are oceanfront docking facilities available for rent. Additional amenities include an oceanfront pool, making it an ideal location for a Florida Keys getaway and investment property.

84745 Old Highway Unit #14, Islamorada
$649,900
A11683792 MLS
Discover the ultimate in Florida Keys living with this fully renovated 2-bed, 2-bath villa in Islamorada’s exclusive Executive Bay Club! This bright unit offers a versatile loft space, granite countertops, stainless steel appliances, and stylish zebra shades throughout. The spacious master suite includes built-in closets, while the villa’s unbeatable location is just steps from the pool, private beach, and community amenities like pickleball, tennis, and basketball courts. With access to a community marina and the vibrant events at nearby Founders Park, this pet-friendly home offers both tranquility and rental potential. Don’t miss your slice of paradise—schedule a tour today!

87200 Overseas Hwy Unit #P8, Islamorada
$2,995,000
A11681144 MLS
SELLER MOTIVATED! Turnkey Restaurant opportunity with prime US1 Frontage in heart of downtown Islamorada! Rare 160-seat restaurant on a highly visible corner lot w/ high visibility on US1, offering ample parking & incredible potential. Accessible from both US1, Blackwood Dr & Old Hwy, this property is ideally located within walking distance to world class high-end resorts, boutique shops, art galleries, & other popular Islamorada attractions. Sale includes valuable Real Estate comprised of the 4,942 sqft building on a 16,746 sqft 'X' flood zone lot; Village Center zoning allows for many uses. All furniture, fixtures & equipment, food truck, transferable liquor license conveys, longtime local staff in place. Continue the legacy or bring your vision to the highly desirable Islamorada market!

81901 Overseas Hwy, Islamorada
$999,998
A11679617 MLS
Islamorada condominium that allows for Weekly Rentals ! Florida Keys living with 2-bedroom, 2.5-bathrooms in the Bay Harbour complex. HOA $ = Bld Ins.

101 Gulfview Dr Unit #102, Islamorada
$899,000
A11676718 MLS
Island Life Awaits...Islamorada Getaway and great investment property allowing weekly rentals. Unique penthouse condo features a spacious private rooftop deck offering views of both the Ocean and the Gulf. Plus, you'll have your own deeded covered parking spot. Beautifully remodeled, 3/2 and beautifully furnished! Fantastic layout - 1567sq ft of living space all on one level. The Summer Sea is pet friendly and offers first-come dockage to 26' OA. Bayside pool, spa, sunset beach, party room, gym, billiard room, storage and so much more. Some ocean views from almost every room. Above the unit is a private rooftop lounge with covered wet bar perfect for entertaining or just chilling while you soak in the views. Ideal for sunrise and sunset lovers.

88500 Overseas Hwy Unit #502, Islamorada
$1,200,000
A11668713 MLS
Available for weekly rentals. Peaceful Palms - is a newly-built luxury coastal development situated in the gated community of Islamorada, FL. This upscale property features 15 high-end townhomes, all boasting an oceanfront location, as well as oceanfront views. You can enjoy spectacular views of the acclaimed Sandbar and Alligator Reef Lighthouse, as well as breathtaking sunrises. For boating enthusiasts, there are oceanfront docking facilities available for rent. Additional amenities include an oceanfront pool, making it an ideal location for a Florida Keys getaway and investment property.

84745 Old Hwy Unit #4, Islamorada
$1,700,000
A11674250 MLS
Discover the ultimate waterfront retreat in the heart of Islamorada, in the highly sought after neighborhood of White Marlin Beach. This captivating 3-bedroom, 2-bathroom gem is a dream come true. The interior features an open floor plan with 9-foot ceilings and ceramic tile. Embrace the coastal lifestyle with stunning water views right from your backyard and revel in the convenience of a private boat ramp and dock. Take a short trip just a couple blocks away to your private homeowner's park with sandy beach. Safety and security are paramount, thanks to the fully fenced yard with electric sliding gate and impact windows and doors. The one-car garage, carport and shop provide space for multiple vehicles and hobby projects.

121 Venetian Dr, Islamorada
$4,949,000
A11673748 MLS
This property features 3 acres of industrial upland, complemented by an additional 9 acres of bayfront land, which can be negotiated, including plans for a 100' dock and two 30k lb boat lifts. The property has 150 ft of US1 frontage and is conveniently located north of the weigh station. The Village of Islamorada officially recognizes 1,972 sq. ft. of non-residential floor area, one market-rate dwelling unit, and two affordable housing units. The current zoning code permits the construction of over 30,000 square feet, based on 3.12 acres or 10,000 sq. ft. per acre. Presently, there are four structures on the property. The seller is open to subdividing to meet the buyer's needs. This is one of the few properties in Monroe County with a wide range of potential uses, including residential.

86560 Overseas Hwy, Islamorada
$1,685,900
A11662123 MLS
Welcome to this two story-waterfront property in the Florida Keys within Lower Matecumbe Key (near mile marker 74) three bedrooms and 3 baths total (2 bed/1bath on the second floor, 1bed/1bath on first floor, and 1 full bath on exterior) on the on the ocean side with 1,920 sq ft of living space. This unique canal front property offers a 6,600 sq ft total lot size with access to the open ocean and bay within minutes. 60 FT concrete dock offers space for your boats, jets ski's and more. 2 boat lifts included in the purchase, one can hold up to 10,000 lbs and other 15,000 lbs. Plenty of parking for multiple cars within the actual property. Furniture can be included in the sale. Call us today for in-person/virtual showings.

158 Iroquois Dr, Islamorada
$4,949,000
A11659094 MLS
This property features 3 acres of industrial upland, complemented by an additional 9 acres of bayfront land, which can be negotiated, including plans for a 100' dock and two 30k lb boat lifts. The property has 150 ft of US1 frontage and is conveniently located north of the weigh station. The Village of Islamorada officially recognizes 1,972 sq. ft. of non-residential floor area, one market-rate dwelling unit, and two affordable housing units. The current zoning code permits the construction of over 30,000 square feet, based on 3.12 acres or 10,000 sq. ft. per acre. Presently, there are four structures on the property. The seller is open to subdividing to meet the buyer's needs. This is one of the few properties in Monroe County with a wide range of potential uses, including residential.

86560 Overseas Hwy, Islamorada
$629,000
A11650295 MLS
Experience the ultimate Florida Keys lifestyle in this stunning 2-bedroom condo. Nestled in a prime location, this beautifully designed unit features an open layout living area with tile floors throughout. The kitchen is fully equipped with stainless steel appliances, and the spacious bedrooms include walk-in closets. The master bedroom offers an open balcony, and the unit also includes impact doors and a patio.The community provides a variety of amenities, including a swimming pool, private beach, marina, and tennis courts, ensuring there's always something to enjoy. With on-site boat storage and easy access to world-class fishing and boating, this condo is a dream come true for water enthusiasts.

87200 Overseas Hwy Unit #A7, Islamorada
$2,695,900
A11648297 MLS
Welcome to this beautiful Florida Keys home, 1,827 SqFt living area (larger than tax roll) fully renovated 3 bedroom, 3 bath waterfront property situated in Lower Matecumbe Key with 7,500 SQ FT lot. New seawall was completed and elevated in 2021. Boaters paradise with 75FT of dockage, under 5 minute ride to open ocean + easy access to bay as well, plenty of space to install a boat lift. Canal depth is estimated to be 10-12 FT. This unique layout offers 2 bedrooms and 2 baths on the second floor with a full kitchen and spacious living room area, washer and dryer. First floor offers 1 bedroom and 1 bath, washer and dryer, full kitchen and its own washer and dryer for your convenience (separate living units). New roof/hurricane impact windows throughout. Easy storage space. Ample parking.

126 Columbus Dr, Islamorada
$646,000
A11645312 MLS
Beautiful move-in ready, meticulously just renovated 2bed/2bath townhome condo in the heart of the Florida Keys offers the perfect blend of luxury and convenience. This beauty just finished renovations and features a bonus low-ceiling third bedroom with windows connected to the master bedroom upstairs. Unassigned parking for 3 plus guest parking. Community pool, tennis courts, marina access, deeded sandy beach. New kitchen with granite counters and stainless appliances. Miele washer/dryer. Modern tile on the first floor, luxury vinyl planks on the second floor. Deeded backyard. Monthly rentals including Airbnb/VRBO allowed. Pet friendly. Easy to show.

87200 Overseas Hwy Unit #C3, Islamorada
$640,000
A11643860 MLS
Enjoy access to a community pool, Tennis Courts, sandy bayfront beach, lush landscaping services, a manned front gate, 31 Boat slips for boats up to 28 ft available on a first come, first serve basis, 6 mooring pilings, fishing areas, fish cleaning tables, kayak launch, and much more! This inviting 2-bedroom, 1.5-bath unit, boasts updated bathrooms and kitchen, ensuring a modern and comfortable living space.

87200 Overseas Hwy Unit #M4, Islamorada
$599,000
A11644286 MLS
Be ready to be captivated by this stunning townhome in the sought-after Executive Bay Club! The home features 2 bedrooms, 3 baths, a spacious kitchen, an open floor plan, outdoor living space, and an additional loft area. Entertain guests on the backyard patio while savoring delightful afternoons. The community offers numerous perks, including a gated entrance with 24-hour security, a pool, clubhouse, tennis courts, and an array of amenities. Located in the heart of Islamorada, you'll have convenient access to top-notch restaurants, shopping, and the renowned Founder's Park.

87200 Overseas Hwy Unit #C4, Islamorada
$7,650,000
A11633525 MLS
THE LAST RESORT offers breathtaking views of the Atlantic Ocean, complemented by expansive & covered verandahs, poolside Chaise lounge chairs and beachfront hammocks that invite you to soak in the beauty of the surroundings. This home is the Historic, 1922 residence of Roger and Sarah Albury. With 165' of private sandy beach at your disposal and a 15 x 30 heated swimming pool by the seaside, relaxation and enjoyment are easily obtained. All of this is set on over one acre of lush tropical land, providing a serene and private retreat. Additionally, the property features a 37.5' private concrete dock on the adjacent canal, offering convenient access to the water for boating enthusiasts. Located in the heart of the Florida Keys,

109 Columbus Dr, Islamorada
$5,500,000
A11626493 MLS
LOCATION, LOCATION, LOCATION!!! PRIME LOCATION! RARE OCEANFRONT PROPERTY IN ISLAMORADA WITH GORGEOUS OPEN WATER VIEWS AND BEATIFUL WHITE SANDY BEACH. THIS GATED PARADISE WITH CONCRETE BLOCK CONSTRUCTION FEATURES AN AMAZING OPEN LAYOUT WITH ASTONISHING BREAKFAST NOOK, DINING ROOM, LIVING ROOM AND GREAT CHEF KITCHEN PERFECT FOR ENTERTAINING. THIS BREATHTAKING HOME IS READY FOR YOU TO TAKE ADVANTAGE OF THIS EXCLUSIVE AND PRESTIGIOUS COMMUNITY. AFTER A DAY OUT FISHING OR BOATING, COME HOME AND WATCH THE OCEAN VIEWS FROM YOUR OWN PRIVATE POOL AND BACK YARD OR ENJOY FINE DINING JUST MINUTES AWAY! A TRULY ONE-OF-A-KIND PROPERTY!!! WEEKLY RENTAL ALLOWED!!! APPOINTMENT ONLY!!!

75761 Overseas Hwy, Islamorada
$750,000
A11615067 MLS
Stunning Islamorada 3/2 plus loft fully furnished & equipped with new kitchen, bar, built-ins fishing+storage, 2 brand new Bathrooms, new extended loft area, new high end appliances, new full size Washer/Dryer, new BBQ area new patio pavers, private palms trees, Serena & Lily furnish, new electric, new electric water heater, new car charging, new 80" smart OLED TV, new bar, coffee and bar, new 4 ton AC unit, high end hurricane impact windows and doors that are reflective and cannot see inside. Best area next to pool & marina. Sleeps over 10 people. King in master, 2 queen mattress in additional bedroom and loft along with 5 twin mattresses. Rented in winter for $6k a month! See 3 videos: https://youtu.be/P8cOME8P_kY; https://youtu.be/b6RmPMU8pvk; https://youtube.com/shorts/BEo0F_YzVFE;

87200 Overseas Hwy, Islamorada
$14,000
A11611110 MLS
***INDUSTRIAL PROPERTY FOR LEASE *** 3 buildings on site *** Service Bays *** Storage *** Office *** 1 Acre Plus. This is set up for a maintenance location for large trucks and equipement. With INDUSTRIAL ZONING you have endless options. Located just North of the Weigh station before the Snake bridge in Islamorada.

86490 Overseas Hwy, Islamorada
$3,450,000
A11605185 MLS
Modern Meets Coastal! Welcome to this Masterpiece in Port Antigua! Step inside to luxury, in this 2019 build, 4 bedrooms and 4 bathrooms, with a primary suite on each level, it boasts a modern coastal design and your very own private beach in the neighborhood. 56' of deepwater dockage on an extra-wide 90' canal, with an additional 45' of waterfrontage with the possibility of expansion to add more dockage. Room for a pool! Private beach and boat and amazing sunsets at your fingertips! Call for appointment.

96 W Plaza Del Sol, Islamorada
$394,500
A11591147 MLS
Dry Cleaner business FOR SALE! Turn Key operation. One of the only Dry Cleaners where all of your Dry Cleaning needs are done on site, in the Florida Keys. Family owned and operated, serving satisfied customers for the past 32 years. This is an Exceptional business opportunity! **Seller may consider some financing** Call for more details.

89015 Overseas Hwy, Islamorada
$5,495,000
A11577221 MLS
Nestled at the secluded end of a private road in Islamorada's premier boating neighborhood, is a remarkable property with breathtaking bay vistas and unmatched seclusion. Completely rare 200 feet along Florida Bay on 3/4 of a lush green acre! Floating dock for flats boat is right behind the house and two slips in the private marina just 800 feet away, each accommodating boats up to 40’ LOA. The sprawling one-level home features cathedral ceilings, oversized windows framing panoramic bay views. A screened porch offers a serene bay-facing retreat, while the primary suite and a separate wing with office and guest quarters ensure ample space for relaxation and hosting. 3,000SF+/- under AC and abundant outdoor living spaces, PLUS 1500sf garage and 560sf workout room. Metal roof, mostly impact.

140 Gulfside Dr, Islamorada
$720,000
A11553370 MLS
**Nightly Rental Condotel at Historic Cheeca Lodge Resort and Spa. King bed, living room, kitchen, porch.**

81801 Overseas Hwy Unit #709, Islamorada