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$11,000,000
4 Beds ⋅ 4 Baths ⋅ 616886 MLS
Commanding 170 feet of private Florida Bay frontage, and situated on over and acre of precious Islamorada land, Eagle Point is a contemporary coastal estate that captures the essence of refined waterfront living. Designed for both serenity and sophistication, the residence blends clean architectural lines with the natural beauty of its tropical surroundings. Gated and beautifully landscaped, the property opens to sweeping open-water vistas framed by swaying palms and fruit trees orchard upon your entrance. Expansive glass walls flood the interiors with natural light, connecting elegant living and dining spaces to the outdoors providing vast screened porched both upstairs and down. The kitchen anchors the home with gorgeous views and function ideal for entertaining or quiet evenings at home. A downstairs flex room and private gym add versatility and wellness to daily life, while multiple rooftop terraces invite sunset gatherings and panoramic bay views. Outside, the resort-inspired amenities continue with a lagoon-style pool, putting green, and ample deepwater dockage with boat lift with Bay to Ocean access in minutes via Channels 2 or 5, offering effortless access to world-class boating and fishing. Just off the edge of the channel lies a rare bayside reef teeming with life and providing snorkeling right off your own dock. Located on the Lower Matecumbe island of Islamorada, Eagle Point balances modern coastal luxury with timeless island tranquility—an estate designed for those who seek both beauty and belonging by the water.

75280 Overseas Hwy, Islamorada
$3,300,000
3 Beds ⋅ 3 Baths ⋅ 618699 MLS
74560 Overseas Highway is a dynamic waterfront commercial asset with multiple revenue paths and significant redevelopment potential. Situated on a 15,000 SF parcel with generous on-site parking and 100 feet of seawall capable of accommodating up to 8 slips, the property delivers premier highway exposure and immediate Florida Bay and Atlantic Ocean access. Zoning supports four affordable housing units, one market-rate residence, and 5,640 SF of commercial space, creating a layered income strategy that blends residential density with marine-oriented business activity. The existing structure features expansive wraparound windows framing sweeping Atlantic views, plus a top-floor penthouse suite suited for owner occupancy, executive housing, or premium rental use (subject to approvals). The building configuration can also accommodate a rooftop helipad. Commercial Fishing zoning allows for uses such as a destination restaurant, seafood market, marine outfitter, charter or backcountry fishing headquarters, marina-support retail, or other enterprises aligned with the working waterfront. This is a high-visibility, commercial platform where housing, marine access, and US-1 frontage intersect to create compelling long-term value.

74560 Overseas Hwy, Islamorada
$6,700,000
4 Beds ⋅ 5 Baths ⋅ 616619 MLS
Iconic Islamorada Oceanfront Retreat. Welcome to The Last Resort, a one-of-a-kind oceanfront estate offering rare privacy and breathtaking natural beauty in the heart of Islamorada. Set on over an acre of lush tropical land, this coastal retreat boasts 165 feet of private sandy Atlantic beach, where you can launch a kayak or paddleboard right from your backyard and soak in endless turquoise views. Expansive covered verandahs, a 15' x 30' heated seaside pool, and beachside hammocks invite slow, sun-filled days and relaxed gatherings. Across the street, a separate canalfront parcel with a 37.5' concrete dock provides protected deep-water dockage and space for boats, trailers, and water toys — an extraordinary pairing of true beachfront living and convenient boating access. Inside, the home's 3,860 square feet is designed for easy Keys living with generous main-level living areas and bedrooms, plus a spacious upstairs suite with private bath and roof-top deck capturing panoramic ocean vistas. Four bedrooms and five baths accommodate family and guests comfortably, while breezy porches and open gathering spaces make entertaining effortless. Highlights you'll love: 165' of private sandy Atlantic beach with direct ocean entry, 37.5' private concrete dock on canalfront lot for boating convenience, 15' x 30' heated seaside swimming pool with expansive sun decks, over one acre of tropical privacy and mature landscaping, 4 bedrooms | 5 baths | 3,860 sq. ft. with thoughtful single-level layout plus upstairs suite and roof deck. A true Keys treasure, The Last Resort delivers a rare mix of sandy beach, deep-water dockage, and timeless coastal charm. Ann exceptional opportunity to create your own island legacy!

109 Columbus Dr, Islamorada
$2,495,000
3 Beds ⋅ 4 Baths ⋅ 617838 MLS
Perfectly positioned in the heart of Upper Matecumbe Key, this stunning residence places you in downtown Islamorada--just a short stroll to the area's most celebrated restaurants, art galleries, and island attractions. Privately gated and approached by a Chicago paver driveway, this absolutely turn-key 3-bedroom, 3.5-bath residence is part of an exclusive collection of just eight bayfront homes and was completed in 2020 with refined design, upscale finishes, all stainless-steel Bosch appliances, and exceptional craftsmanship throughout. Elegant interiors and thoughtful details create a sophisticated yet relaxed island lifestyle. The home features a private pool with a wood deck at the rear--ideal for entertaining or unwinding in complete privacy--while residents also enjoy access to a community bayfront pool overlooking breathtaking sunset views. An assigned boat slip on the bay provides effortless access to Florida Bay and the Atlantic beyond. Boat lift currently in place can hold boats up to 5,000Lbs. Adding to its appeal, 7-day rentals are permitted, making this property a rare and superior investment opportunity in one of Islamorada's most walkable and desirable locations. Ideal for a full-time residence, island getaway, or income-producing asset, this home offers an exceptional blend of luxury, lifestyle, and flexibility. Coral Cove is located in an X flood zone, providing additional peace of mind.

81906 Overseas Hwy Unit 2, Islamorada
$4,600,000
5 Beds ⋅ 6 Baths ⋅ 617341 MLS
Welcome to paradise at 117 Leoni Drive in the exclusive Venetian Shores neighborhood! This stunning 4,100 sq. ft., canal-front home offers bay and ocean access via snake creek, 70 feet of dockage, and luxurious living with 5 bedrooms and 6 bathrooms. Built with precision and modern style, this brand-new custom CBS residence boasts lush landscaping, a sparkling pool, and high-end finishes throughout. Step upstairs to find a tranquil master suite with an expansive walk-in closet, a beverage center, a large shower, and dual vanities. Three additional guest suites with private bathrooms, a spacious living area, a large laundry room, and a versatile bonus room complete the upper level, providing ample space for relaxation and recreation. On the main floor, the gourmet kitchen is a chef's dream, featuring top-of-the-line appliances, storage pantry, Taj Mahal quartzite countertops, a wine cooler, and custom cabinetry throughout. A private guest room with an ensuite bathroom is perfect for the friends and family to visit for a staycation. The open-concept main living area flows seamlessly into the outdoors where a full bath and outdoor kitchen await. Relax by the lounge pool, enjoy synthetic grass surroundings, and take advantage of the full dock. This canal-front oasis is a rare find in the coveted Upper Keys and offers the perfect blend of luxury, comfort, and convenience. Your slice of paradise awaits!

117 Leoni Dr, Islamorada
$1,075,000
617028 MLS
ACTIVE BUILDING AND DOCK PERMITS. START BUILDING TODAY! Your tropical dream awaits with the lowest-priced waterfront lot featuring an active building permit in Islamorada. Imagine waking up to sunlit mornings, salty breezes, and the soft embrace of warm sand beneath your feet. Welcome to White Marlin Beach, where your vision of paradise comes to life. Vacant lots with active building permits are a rare find, and this one is ready for you to create your dream retreat. Picture a three-bedroom, four-bathroom island escape blending coastal charm with modern luxury. Two spacious, sunlit stories are designed for relaxation, complete with an elevator to ensure comfort and convenience. Expansive porches invite you to unwind, sip your morning coffee with bay views, feel the ocean breeze in your hair, and enjoy evenings under a canopy of stars. New construction offers more than a fresh startâ€''it brings favorable insurance rates, a solid foundation, and the confidence of quality craftsmanship. This is your gateway to maritime bliss. The private homeowners' park features one of the few sandy beaches in the Keys, perfect for building sandcastles, watching sunsets, and creating cherished memories. This property offers convenient access to vibrant dining, boutique shopping, and an inspiring arts scene. It's more than just a property; it's an invitation to embrace the island lifestyle. Opportunities like this don't wait. Ready to turn your dream into reality? Dive into your future at White Marlin Beachâ€''your tropical oasis is calling!

142 Gulfview Dr, Islamorada
$24,995,000
5 Beds ⋅ 8 Baths ⋅ 617705 MLS
Newly completed private oceanfront estate on 2+ acres in Plantation Key, offering an extraordinary combination of scale, privacy, dockage, and resort-style living in the heart of the Florida Keys. Designed for luxury coastal living, entertaining, and extended stays, this exceptional estate features over 9,000 sq. ft. of interior living space and more than 15,000 sq. ft. under roof. Set behind a gated entry, the residence offers 5 ensuite bedrooms, 5 full baths, 3 half baths, multiple flex spaces, an elevator, expansive covered porches, and seamless indoor-outdoor living. Additional luxury spaces include an in-home theater, private gym, and a massive office overlooking the ocean, all of which could easily serve as additional bedrooms, creating the potential for an 8-bedroom layout. The outdoor spaces are designed to showcase the Atlantic Ocean setting, with a resort-style pool, jacuzzi, generous lounging areas, and sweeping oceanfront views. Boaters will appreciate the 80-ft dock, 20,000 lb boat lift, and 160-ft jetty, creating outstanding access for enjoying the Keys lifestyle. With vacation rental zoning, the property also offers investment flexibility for those seeking personal use, income potential, or a legacy estate. Private oceanfront acreage of this scale is increasingly rare in the Upper Keys, making 87895 Old Hwy a standout opportunity for the buyer seeking a newly completed Florida Keys estate with privacy, presence, flexible living space, and exceptional waterfront amenities.

87895 Old Hwy, Islamorada
$750,000
3 Beds ⋅ 2 Baths ⋅ 613083 MLS
All NEW NEXT TO MARINA & POOL Stunning Islamorada 3 full bedrooms 2 brand new bathrooms plus oversized loft with additional queen and three twin beds. This Townhouse has ALL NEW kitchen, new bar, new built-ins, new custom fishing closet & storage, brand new 4 ton AC unit, 2 brand new Bathrooms with showers, new extended loft area, new full size Washer/Dryer, new BBQ area with new patio chicago brick pavers plus private patio shaded area with beautiful palms trees, serena & lily furniture inside, new electric panel, new electric water heater, new 80' smart OLED TV, new area just for refreshments, coffee and bar, new 4 ton AC unit, high end hurricane impact windows and doors that are reflective and cannot see inside. New Electric car charging electric panel exclusive to this unit. Best area in the community next to pool and marina with two pickleball courts and basketball court in the rear. Sleeps easily over 10 people. King bed in the master bedroom, 2 queen mattress in additional bedroom and loft along with 5 twin mattresses. Rented in winter for over $6,500 a month! Call today! This community features a new private beach, marina, dock and clubhouse. Being SOLD fully furnished and fully equipped with high end appliances (FRIGIDAIRE), high end furniture (SERENA & LILY) and furnishings. See 3 Videos: https://youtu.be/P8cOME8P_kY; https://youtu.be/b6RmPMU8pvk; https://youtube.com/shorts/BEo0F_YzVFE;

87200 Overseas Hwy Unit V9, Islamorada
$2,500,000
3 Beds ⋅ 3 Baths ⋅ 618461 MLS
Located in the highly desirable Venetian Shores neighborhood in Islamorada, this canal front home offers 70 feet of dockage with a brand new concrete dock and seawall, making it an excellent opportunity for boating enthusiasts. Enjoy quick and convenient access to both the Atlantic Ocean and Florida Bay through Snake Creek, one of the most sought-after boating access points in the Florida Keys. This prime location allows for easy navigation whether heading offshore or exploring the backcountry. Situated on a 7,000 square foot lot, the property features a two-bedroom, two-bathroom layout upstairs, along with a one-bedroom, one-bathroom downstairs, offering additional flexibility for guests, extended family, or bonus space. The home has been freshly painted and is ready for immediate enjoyment, while also presenting an opportunity to update, expand, or build new in a neighborhood known for redevelopment and custom homes. For boaters, this property is ready to go--complete with a new concrete dock and seawall, ideal for accommodating a large vessel. A boat lift permit has already been applied for and approved by the Village of Islamorada, providing added value and convenience for the next owner. Venetian Shores is known for its wide canals, excellent water access, and close proximity to dining, marinas, and local amenities. Whether you're looking for a primary residence, vacation home, or future investment, this property offers strong potential in one of Islamorada's most desirable waterfront communities.

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

87429 Old Hwy, Islamorada
$2,300,000
3 Beds ⋅ 3 Baths ⋅ 611841 MLS
Make all of your Florida Keys fantasies come true at Fantasy Harbor! We're willing to bet you never even knew this gated community on Islamorada's Lower Matecumbe existed. This concrete harborfront home is being offered for the very first time. Upstairs 2 bedroom 2 bathrooms suites with open and spacious harborview living areas plus downstairs bedroom and bathroom with a bonus party hut reminiscent of relaxing Bahamian nights after a day on the water. Quiet & private living situated just off the Florida Bay in a protected harbor with 99' concrete seawall on cap rock plus boat lift. This one is a winner!

76412 Overseas Hwy, Islamorada
$2,650,000
616329 MLS
100 x 717 ft lot approximately 1.66 acres ocean front with real sand on the beach on Lower Matecumbe in Islamorada MM76.2. Remains of prior Utility building on property. incredible location for an ocean front beach front micro-estate in the Village of Islamorada.

76291 Overseas Hwy, Islamorada
$443,000
2 Beds ⋅ 2 Baths ⋅ 617381 MLS
WELCOME TO PARADISE BY THE SEA! THIS SPACIOUS CONDO LOCATED IN HIGHLY DESIRED PLANTATION KEY/SLAMORADA ON MILLIONAIRE'S ROW. THIS OCEANFRONT BUILDING OFFERS THE PERFECT BLEND OF COMFORT & CONVENIENCE, THIS BEAUTY FEATURES AN OPEN CONCEPT LIVING AREA THAT LIGHT AND BRIGHT! WELL APPOINTED KITCHEN WITH WOOD CABINETS, & FIRST FLOOR HALF BATHROOM. WALK UPSTAIRS TO A COZY SPLIT BEDROOM FLOOR PLAN FOR PRIVACY. PRIMARY SUITE INCLUDES A WALK-IN CLOSET. OUTSIDE OFFERS COVERED PARKING, PLENTY OF GUEST PARKING, STORAGE UNIT, NEW ROOFS ON BOTH BUILDINGS, LOW MONTHLY MAINTENANCE FEE INCLUDES WATER, HEATED POOL, COMMUNITY ROOM WITH KITCHEN, DOCK/FISHING PIER, , GYM, & SAUNA. WHETHER YOU'RE LOOKING FOR YOUR NEW HOME, A WEEKEND VACATION GETAWAY, OR INVESTMENT PROPERTY, THIS CONDO IS MOVE-IN READY & PERFECTLY LOCATED WITHIN WALKING DISTANCE TO RESTAURANTS AND SHOPPING! EASY ACCESS FROM OLD HIGHWAY OR US 1, THIS DEVELOPMENT HAS IT ALL! NEW ROOFS ON ENTIRE COMPLEX! Driving Directions:

87465 Old Hwy Unit 215, Islamorada
$6,150,000
5 Beds ⋅ 6 Baths ⋅ 618481 MLS
Big, beautiful, and exceptionally solid, this waterfront Islamorada residence is perfectly situated on Sandy Cove Basin with protected deep-water dockage for multiple boats and direct bay access. A gated, pavered double driveway leads to an inviting foyer where marble floors and a private elevator welcome you. The elevated living level features a spacious great room with fireplace and coral accents, ideal for entertaining, along with a chef's kitchen offering custom teak cabinetry, granite countertops, island cooktop, and premium Sub-Zero and Bosch appliances. Wide screened porches extend the living space and capture open waterfront views. The home offers 5 bedrooms and 5.5 baths, a resort-style pool, and excellent updates including a new dock, new boat lift, and new A/C systems. A privacy wall enhances the secluded feel of this quiet, one-street neighborhood known for its consistently lovely homes. An exceptional opportunity for refined island living with outstanding boating access.

137 Sapodilla Dr, Islamorada
$1,075,000
3 Beds ⋅ 4 Baths ⋅ 617029 MLS
ACTIVE BUILDING AND DOCK PERMITS. BUILD RIGHT AWAY. Your tropical dream awaits with the lowest-priced waterfront lot featuring an active building permit in Islamorada. Imagine waking up to sunlit mornings, salty breezes, and the soft embrace of warm sand beneath your feet. Welcome to White Marlin Beach, where your vision of paradise comes to life. Vacant lots with active building permits are a rare find, and this one is ready for you to create your dream retreat. Picture a three-bedroom, four-bathroom island escape blending coastal charm with modern luxury. Two spacious, sunlit stories are designed for relaxation, complete with an elevator to ensure comfort and convenience. Expansive porches invite you to unwind, sip your morning coffee with bay views, feel the ocean breeze in your hair, and enjoy evenings under a canopy of stars. New construction offers more than a fresh start—it brings favorable insurance rates, a solid foundation, and the confidence of quality craftsmanship. This is your gateway to maritime bliss. The private homeowners' park features one of the few sandy beaches in the Keys, perfect for building sandcastles, watching sunsets, and creating cherished memories. This property offers convenient access to vibrant dining, boutique shopping, and an inspiring arts scene. It's more than just a property; it's an invitation to embrace the island lifestyle. Opportunities like this don't wait. Ready to turn your dream into reality? Dive into your future at White Marlin Beach—your tropical oasis is calling!

142 Gulfview Dr, Islamorada
$2,400,000
3 Beds ⋅ 4 Baths ⋅ 616205 MLS
Simply the best location, exclusive & extremely private. This is a rare find and a single-family home that's rarely available. It's tucked away in the prestigious ''Plantation Lake Estates,'' a highly sought-after gated community with an on-site boat ramp and park. This Coastal-Styled Beach Home is in a prime location at Mile Marker 87, across the street from Founders Park, which has a beach, tennis courts, a full-service marina, a dog park, sports fields, and Olympic-size lap pools. This home boasts a stunning great room with a gorgeous coral fireplace and soaring wood beam ceilings. They all overlook the glistening Atlantic Ocean, providing priceless views and sunrises. The home has a metal roof, a modern kitchen, updated baths, and impact windows and doors. The exterior has been reinforced with rebar and stucco. There are three inviting bedrooms, including a third-floor master en-suite with a private porch. A large ''rec room'' with a cabana kitchen is perfect for indoor-outdoor entertaining. You'll have world-class fishing and diving right in your own backyard.

316 North Dr, Islamorada
$6,500,000
611386 MLS
Once in a lifetime investment in the heart of Islamorada. This exceptional property offers a wide range of potential uses as it includes two Village Center parcels stretching from Highway to Bay, currently featuring a spacious 3,995 sqft restaurant and bar with a coveted 5COP liquor license - no food quota. Village Center zoning allows for multiple use opportunities including, but not limited to, single family estate, multi family compound, luxury townhomes, vacation rentals, restaurants, marinas, general store with package sales, and much more. The property spans 30,415 sqft. Includes a Bayfront boat basin, and plans for an additional 100' dock to be constructed. The Village of Islamorada officially recognizes three waterfront market-rate dwelling units . The three waterfront Transferable Development Rights (TDRs) can be utilized onsite, transferred to another location, or sold to a receiver site. The Village Center Zoning would allow up to 8 market-rate dwelling units to be developed on site for a new luxury townhome community, with the transfer in of additional TDRs. Whether you're looking to rehab a local iconic business, start a new business, redevelop the entire site, or create a spectacular residential estate, this unicorn property is perfectly located. ***Buyer to verify ALL information.***

81910 & 81908 Overseas Hwy, Islamorada
$7,400,000
5 Beds ⋅ 6 Baths ⋅ 616417 MLS
Experience Islamorada living at its absolute finest with this remodeled oceanfront estate. Situated on 200 feet of sandy waterfront with unobstructed views of the Atlantic Ocean and Alligator Reef Lighthouse, this ground-level residence is designed for resort-style living. Inside, the home features 5 spacious ensuite bedrooms and 5.5 baths, highlighted by a luxurious primary suite with a coffee bar, spa-like bathroom, and walk in closet. The spacious kitchen with double islands opens seamlessly to the main living and dining area, where the panoramic ocean views create the ultimate backdrop. An entertainment room with a wet bar, game tables, and lounge seating is perfect for hosting, while the expansive Florida room—complete with its own AC and walls of windows—brings the outdoors in. The outdoor amenities are nothing short of spectacular - including a new concrete pool (2023) with a spacious paver deck, sandy beach, tropical landscaping, and a private pier with dockage. The detached three-bay garage offers abundant storage, including one 40' bay - perfect for the boat or RV. Zoned for weekly vacation rentals, this rare property offers the opportunity for short-term rental income in a highly desirable Islamorada location. This is the one you've been waiting for - paradise found.

80201 Overseas Hwy, Islamorada
$5,999,999
5 Beds ⋅ 6 Baths ⋅ 618158 MLS
Brand new 2026 coastal luxury in Islamorada's White Marlin Beach. 181 Nautilus Dr offers the ultimate Keys lifestyle with 5 bedrooms, 5.5 baths, and 5,320 SF of living area across three levels. Served by a private elevator that opens on all floors. Designed for indoor/outdoor living, enjoy a resort-style pool and a modern outdoor setting ideal for entertaining. Built for peace of mind with impact glass doors and windows and a concrete flat roof, the home features a state-of-the-art chef's kitchen and elevated finishes throughout. Boaters will love approximately 70' of concrete dockage on a straight seawall plus a 15,000-lb boat lift (remote-controlled). Enjoy quick bay access and ocean access via the Channel 5 Bridge, known for its high-clearance fixed span (approx. 65' vertical clearance) (buyer to verify vessel requirements and navigation). The White Marlin Beach community is also known for a gated private sandy neighborhood beach with amenities, an exceptional Islamorada bonus.

181 Nautilus Dr, Islamorada
$3,524,000
7 Beds ⋅ 4 Baths ⋅ 618670 MLS
A Keys compound built to enjoy now-grow into the future, or internally convert to a 3,524 sq ft primary home without structural changes, while retaining a Waterfront Transferable Development Right (TDR/TBR) in Islamorada (approx. $650K value). Exceptional opportunity in the coveted White Marlin Beach community at MM74, this canal-front luxury family compound offers rare multi-family autonomy, strong income performance, & resort-style amenities; ideal for an owner-user, investor, or legacy Keys retreat. With two autonomous 2BR/1BA residences upstairs & a separate 3BR/2BA finished, a/c area downstairs, providing privacy, flexibility, & seamless multi-generational or guest use. In total, the compound offers 7 bedrooms & 4 bathrooms, comfortably accommodating up to 24 guests. Designed for both lifestyle & performance, when fully rented, can generate $16,000+ per month in rental income. Zoning & multiple building rights support future expansion or redevelopment. Outdoors, enjoy a resort-style waterfront setting with a private pool, expansive concrete sun deck, outdoor shower, & 70-foot concrete dock with fish-cleaning station, all situated on a 6' control-depth canal with easy access to both bay & ocean waters; ideal for boating, fishing, diving, and paddle sports. Interior finishes reflect modern coastal luxury, including updated kitchens with quartz countertops & stainless appliances, spa-inspired baths with glass-enclosed showers, large-format tile flooring, recessed lighting, & turnkey furnishings. Multiple balconies & patios capture steady breezes & tranquil water views, with manatees frequently passing by. Enjoy private gated access to White Marlin Beach, just a short walk away, offering bay-side sunset views, with the Atlantic Ocean beach also nearby. Grocery stores, marinas, restaurants & bike paths are all within minutes. Rarely does a property offering this level of unity with autonomy, along with amenities, income potential in Islamorada

110 Gulfview Dr, Islamorada
$2,750,000
3 Beds ⋅ 3 Baths ⋅ 616500 MLS
'Turnkey Deepwater Boater's Retreat with Private Beach Access in the Heart of Islamorada' Tucked away on a quiet cul-de-sac in one of the most desirable enclaves in Islamorada, this fully renovated 3-bedroom, 3.5-bath concrete residence delivers the ultimate Florida Keys lifestyle--where luxury, durability, and world-class boating converge. Built for peace of mind and longevity, the home features solid concrete construction and a concrete roof, offering superior storm resilience and insurance advantages rarely found in the Keys. Designed for serious boaters, the property boasts 90 feet of deepwater dockage with immediate access to both the bay and the Atlantic Ocean--no bridges, no delays, just open water within minutes. Inside, the home is completely turnkey, with updated finishes and a seamless indoor-outdoor flow ideal for entertaining or extended stays. Expansive balconies and a large outdoor patio overlook the wide canal, creating a private waterfront setting perfect for sunset dining or relaxing after a day on the water. The oversized paved driveway provides ample parking for guests, trailers, or multiple vehicles -- an uncommon convenience in this area. What truly sets this property apart is access to a rare, highly coveted private beach area, widely regarded by locals as one of the finest in the Florida Keys, offering a unique blend of boating and beach lifestyle that is seldom available in a single property. Whether you're seeking a primary residence, a luxury second home, or an income-producing waterfront asset, this property delivers unmatched versatility and strong potential for high-end monthly rentals.

122 Court Contessa, Islamorada
$475,000
2 Beds ⋅ 2 Baths ⋅ 616492 MLS
Condo for Sale - Islamorada, Plantation by The Sea 2 Bedrooms | 1.5 Bathrooms | Furnished | Two-Story Townhouse Style Experience the unique lifestyle of the Florida Keys in this spectacular furnished condo at Plantation by The Sea! Located in prestigious and convenient Islamorada, this exclusive two-story townhouse-style condo is the perfect retreat for those seeking comfort and authentic coastal living. Fully furnished and equipped - just bring your suitcase and get ready to enjoy! Key Features: 2 spacious bedrooms 1.5 bathrooms Kitchen with modern appliances and functional cabinetry Community Amenities: Heated ocean-view pool Fitness center with modern equipment and sauna Community room with billiards, ping-pong, and board games Extra-long fishing pier Community BBQ area (Boats and jet skis are not permitted) Asking Price: $475,000 Rental Option: $2,700 per month Showings: By appointment only - No sign on property. Call now to schedule your private showing!

87465 Old Hwy Unit 218, Islamorada
$2,250,000
618778 MLS
BPAS AWARD LETTER IN HAND. PERMIT READY FOR PICK UP! BUILD RIGHT AWAY. 150 FT CONCRETE DOCK AND SEAWALL. Welcome to Port Antigua, this highly coveted neighborhood is know for its beautiful sandy beach, wide crystal-clear canals, and deep-water dockage.129 Porto Vista Ct is located on a quiet cul-de-sac. This oversized 8,436 sq ft lot provides space, privacy, and exceptional dockage! Quick Ocean access via channel 5 bridge. This is truly a boater's dream, with direct access to world-class fishing and diving right from your backyard. Don't miss this opportunity to own a slice of paradise. BUILDING PERMIT APPLICATION # PRSFC2O2OO1254 BPAS AWARD LETTER IN HAND. Do not walk property without agent.

129 Porto Vista Ct, Islamorada
$3,950,000
4 Beds ⋅ 5 Baths ⋅ 618400 MLS
The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort considered and exuding coastal living with stunning ocean views. Four bedrooms, four and one-half bathrooms three-floor villa offers 2,574 sq ft of interior plus 1,169 sq ft patios. Contemporary island architecture with an open, airy, and light-filled design. Residences are being offered fully furnished and amenities include open-concept kitchen, dining, and living spaces, powder room, ample closets, two oceanfront balconies, laundry room, 8 ft interior doors, and a 2-car garage with electric charging and added storage. The Beach Club delivers a luxurious experience with its pristine 600ft beach, private boat basin with ample dockage, two oceanfront pools, an oceanfront bar, fitness center, playgrounds for the kids, pickleball courts, unique driving range that extends into the ocean, plus a plethora of water activities allowing guests to fully immerse themselves in the Keys lifestyle. The privacy and exclusivity of this community set itself apart as a gated secluded beach destination environment surrounded by lush, mature landscaping that allows for effortless multigenerational vacations complete with and attentive staff. Open model unit available to show anytime. Some interior photos are from comparable villas within the property and not exact villa listed.

82779 Old Hwy Unit 14, Islamorada
$2,730,000
3 Beds ⋅ 3 Baths ⋅ 618876 MLS
Set within a private gated enclave, this top-floor, corner unit captures the essence of Islamorada living. Quietly elevated, effortlessly refined, and deeply connected to the surrounding seascape. Positioned to embrace sweeping Atlantic Ocean views and the iconic Alligator Reef Lighthouse, expansive walls of glass invite natural light and open water vistas into nearly every space, including each bedroom and even the baths. Thoughtfully updated with a clean, modern aesthetic, the residence balances comfort with simplicity. A minimalist kitchen appointed with Bosch appliances flows into open living spaces designed for relaxation, complemented by floating bathroom vanities, recessed lighting, blackout blinds, owner and storage closets, and carefully considered modern finishes. One of the few properties in Islamorada permitting extremely rare weekly rentals, this offering provides uncommon flexibility for both personal use and investment ownership. Beyond the residence, the community unfolds as a peaceful coastal retreat featuring a white sandy beach, resort-style pool, bocce courts, swimming pier, kayak and paddleboard launch, and a cocktail dock where the rhythm of island living naturally unfolds. The covered oceanfront balcony captures steady year-round breezes and uninterrupted views across the Atlantic. Several nearby full-service marinas provide convenient access for effortless boating throughout the Keys. Just down the Old Road, Gibb Reese Park offers open green space, shaded playgrounds, pickleball courts, gathering areas, and community amenities that enhance everyday living. Located minutes from renowned Islamorada dining, boutique shopping, and the Morada Way Arts District, Maison provides seamless access to the destination's most sought-after experiences while maintaining privacy within a boutique waterfront setting. A residence defined not by excess, but by serenity, exclusivity, and connection to one of the Florida Keys' most iconic landscapes.

80639 Old Hwy Unit 309, Islamorada
$3,250,000
4 Beds ⋅ 3 Baths ⋅ 616450 MLS
Venetian Shores Has It All! Welcome to your slice of paradise in the heart of Islamorada's most sought-after boating community. This beautiful 4 bedroom, 3 bath coastal retreat is designed for both relaxation and entertainment, featuring 70 feet of deep-water dockage along a 100-foot wide canal - just seconds from open water via Snake Creek. Step inside the front door to access the elevator and interior stairs. Upstairs, the main living area offers 2 bedrooms and 2 baths, a wide open floor plan, and a gourmet kitchen with a large center island, granite countertops, stainless steel appliances, and a dedicated workstation. Enjoy sunset cocktails from the screened canal-side terrace, accessed via impact-rated sliding glass doors. Downstairs, the ground level is a haven for guests and fun - featuring a pool table, a comfortable tv area, 2 more bedrooms and a full bath, laundry room, and garage for all your gear. The backyard is pure Keys magic - complete with a heated pool, tiki hut, hot tub and an expansive deck for sunbathing or relaxing in the shade. Boaters will love the 70 ft concrete dock with a 15,000 lb boat lift, 50 amp shore power and fish cleaning station. This home checks every box for the ultimate island lifestyle - whether you're heading east to the Atlantic or west to Florida Bay's backcountry to enjoy fishing and breathtaking sunsets. Live the dream in Venetian Shores - where the boating is easy and the living is even better.

136 Giardino Dr, Islamorada
$6,495,000
608979 MLS
Beautiful 200' of oceanfront property on Lower Matecumbe Key. This offering consists of one 100' lot, vacant with TDR & contiguously, a 100' lot with a triplex apartment building (3 TDRs),.This gives you endless possibilities for redevelopment of the property. The vacant lot has an additional 200' of bay bottom. Fantastic 180° ocean views make for gorgeous sunrises on the naturally sandy beaches. View Alligator Lighthouse, watch dolphins, manatees, and birds feeding on fish right in front of you. At night, beautiful full moon risings, cruise ships with their lights passing, and plenty of stars. Launch kayaks from the beach to do a little tarpon fishing and bonefish are making a comeback so you can wade with your fly rod for a thrill. Also snorkel for lobster in season in all the little crevices and holes off shore of the property. Recap: 200' of oceanfront made up of 1 vacant lot with TDR, 1 lot with 3 apartments, bay bottom on the vacant lot, for a total of 4 TDRs on the property Note: One of the owners is a State of Florida Real Estate Licensee

75131 Overseas Hwy, Islamorada
$427,000
2 Beds ⋅ 2 Baths ⋅ 616280 MLS
BEAUTIFUL CONDO WITH OCEAN VIEWS FOR LESS THAN $430,000! LIVE THE DREAM IN THIS OCEANFRONT RESORT STYLE PROPERTY IN THE HIGHLY DESIRABLE PLANTATION BY THE SEA ON THE OCEAN IN THE BEAUTIFUL FLORIDA KEYS! LOCATED ON HIGHLY SOUGHT AFTER MILLIONAIRES ROW! UPON ENTERING THIS GATED COMMUNITY, THE OCEAN GREETS YOU AS YOU PARK IN YOUR DESIGNATED COVERED PARKING SPACE. UPON ENTERING YOUR CONDO, THIS PARTIALLY UPDATED CONDO WITH OPEN CONCEPT KITCHEN, WELCOMES YOUR HOME TO A CHEF'S DREAM KITCHEN WITH PLENTY OF CABINET SPACE. NEW WATER HEATER, SCREENED IN PATIO ON THE FIRST FLOOR AND GORGEOUS OCEAN VIEWS FROM THE SECOND FLOOR. CLUBHOUSE/COMMUNITY ROOM, FITNESS ROOM, SAUNA, KAYAK STORAGE, LONG AND WIDE FISHING PIER/DOCK ALLOWS YOU TO TIE UP YOUR BOAT FOR LOADING AND UNLOADING WALK TO WORLD CLASS RESTAURANTS, SHOPPING, AND FOUNDER'S PARK. ALL ARE CLOSE! TAKE ADVANTAGE OF THIS AMAZING OPPORTUNITY TO LIVE FULL TIME WHERE OTHERS VACATION, OR START A VACATION RENTAL BUSINESS HERE IN THE BEAUTIFUL FLORIDA KEYS!

87455 Old Hwy Unit 248, Islamorada