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$399,000
2 Beds ⋅ 1 Baths ⋅ 618336 MLS
This two bedroom, one bathroom home within the Village of Islamorada is perfectly situated with close proximity to the Florida Bay and breathtaking bay and sunset views! Property is on a 3,600 SF parcel. A large screened porch is attached for lovely outdoor living. Separate laundry facility and storage building on site. Also included is a Keys style concrete guest cottage behind the home. This property has an immediate building right should you choose to demo and rebuild. A quote is available to demo and re-build a 1,169 SF, three bedroom, three bathroom new modular residence. The home is conveniently located near Founders Park, restaurants, schools and shopping. This is a fantastic opportunity to find your place in the Florida Keys!

135 Airstream Ln, Tavernier
$4,799,000
3 Beds ⋅ 3 Baths ⋅ 618338 MLS
An exceptional and increasingly rare opportunity to own a coveted stretch of waterfront on Tavernier Creek, one of the Florida Keys' most treasured waterways. Set along protected open water in the heart of Plantation Key, this refined residence offers immediate access to both the Atlantic Ocean and Florida Bay, a privilege few properties can claim in the Upper Keys. Thoughtfully reimagined with interiors designed by a notable Ocean Reef Club designer, the home blends classic island architecture with sophisticated modern coastal updates. Solid concrete construction, a new roof and multiple new air-conditioning systems within the last five years, and a full mosquito control system provide comfort and peace of mind. The three-bedroom, three-bath interior is filled with natural light, featuring floor-to-ceiling windows and French doors that frame creek views. The gourmet kitchen features a six-burner gas range, premium stainless steel appliances, and seamless flow into the living and dining areas, ideal for entertaining and everyday living. Hardwired electric shutters provide storm readiness without compromising design. Ample room for thoughtful expansion provides the opportunity to further customize. Outdoors, the property unfolds as a private resort-style retreat with a custom inground pool and tanning ledge, summer kitchen with wet bar, beverage refrigerator and ice maker, gas fire pit, and a covered rooftop terrace offering elevated sunset views over the water. For boating enthusiasts, the T-dock with boat lift offers protected deepwater dockage. A Chicago brick driveway, professional landscaping, and a rare enclosed garage enhance curb appeal and functionality. Centrally located between Tavernier and Islamorada and offered as one of the lowest price-per-square-foot opportunities on the creek, this exceptional residence presents a premier opportunity to own a designer-finished waterfront home with outstanding boating, privacy, and long-term investment potential.

171 Kahiki Dr, Tavernier
$500,000
1 Beds ⋅ 1 Baths ⋅ 617483 MLS
Premier 1 bedroom unit a stunning open water and pool view off your private balcony. Fully updated with the open concept kitchen open to the dining and living room. Stunning white cabinets and modern bathroom, Tile floors and granite countertops throughout the apartment. Comfortable queen size bed with a pull-out couch in the living room. The perfect place to lounge and enjoy your days! The condominium is right on the bay with two pools (one heated), a beautiful beach area, Marina with a new composite Dock, Fish cleaning stations, Tiki huts with BBQ grills and picnic tables, Remodeled workout room and game room, community room, fabulous sunsets and friendly residential atmosphere. Safe and secure gated community with 2 brand new elevator. Summer Sea is a multi-story residential waterfront condominium with a friendly atmosphere with on-site management. The community has successfully completed its milestone inspection and continues to show pride of ownership with numerous recent improvements, including two new elevators, a new composite dock, newly remodeled poolside bathrooms, and storm rated windows -- all completed with no special assessments. This condominium is on Plantation Key, Tavernier at MM88.5, just north of the famous Marker 88 Restaurant, a 5-star gourmet restaurant with outside bar. Four restaurants within walking distance. Marina is first come, first serve, other restrictions apply. One pet per apartment with no size restriction. NOTE: The apartment is rented January, February and March 2027 so rental income is already in place!

88500 Overseas Highway Unit 320, Tavernier
$175,000
616592 MLS
1 dry lot ''Transferable Development Right (TDR)'' for the Village of Islamorada. Receiver site must be scarified. No real property being exchanged.

1 Tdr, Not Provided
$999,999
2 Baths ⋅ 616512 MLS
Looking to purchase your own office space while also generating rental income? This property delivers both. Located in Islamorada, this two-story Key West/Conch-inspired building is zoned for mixed-use highway commercial. 50 feet of frontage along the Overseas Highway, providing strong visibility and signage potential. The exterior is accented by mature landscaping, with parking that includes four spaces in front of the building (per survey, now landscaped) and nine more spaces in the rear with direct access from Old Highway. Inside, the building offers a bright reception area and functional layout. The second floor features 5 one-room offices with a shared kitchenette and half bath, providing the potential of consistent income from annual or month to month tenants. On the ground level, the owner's suite includes a private office, a small meeting room, and a larger executive-style conference room, along with its own kitchenette and half bath. There is one additional office and locked storage room down another set of stairs bringing the total to 7 private offices and two conference rooms. Positioned in a central Upper Keys location, the property is just minutes from local courthouse, downtown Islamorada and Tavernier, with convenient access to local restaurants, shopping, and Founder's Park. With the space for an owner's own office and conference room this property presents an excellent investment in one of the most desirable areas of the Florida Keys.

88101 Old Hwy, Islamorada
$399,000
607906 MLS
Seller is willing to consider all offers!! This ideally located property has an immediate building right should you choose to rebuild. Seller is in receipt of a quote for the demolition of the existing structure and the construction of a beautiful new three bedroom, three bathroom 1,169 SF modular residence. Upon completion of the home, you will have spectacular unobstructed views of the Florida Bay with gorgeous sunsets! The property is conveniently located near Founders Park, restaurants, schools and shopping. This is a fantastic opportunity to find your place on Plantation Key, (Islamorada) in the Florida Keys!

135 Airstream Ln, Tavernier
$630,000
2 Beds ⋅ 2 Baths ⋅ 617971 MLS
Private location for your pleasure at this roomy townhouse offering an abundance of space to enjoy. Spiral stairs leading to the primary suites with an additional loft for your quests. Soft carpet on the living area floors with tile in the remodeled kitchen and beautiful bathrooms. Two pets allowed, with first come first serve the waterfront area. Pool and club house for your recreation along with a nice, landscaped community for your pleasure. 28-day rentals permitted. Garden setting from you extended living room to enjoy the outdoors at your back yard.

87200 N Overseas Hwy Unit N2, 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
$6,500,000
4 Beds ⋅ 5 Baths ⋅ 618703 MLS
Very few things in life live up to the hype--but living on ''The Creek'' exceeds it. The location is world-class, the people-watching and boating scene never gets old, and the level of construction top-notch. What makes this property even more extraordinary is that the home itself now matches the setting. Following a meticulous two-year, top-to-bottom renovation, this residence was completely reimagined--from structural improvements to the finest design details--resulting in a flawless, move-in-ready showpiece. The main living level commands attention the moment you walk in, with dramatic vaulted ceilings, exposed wood beams, and an open-concept living and kitchen area designed for unforgettable entertaining. Two bedrooms and 1.5 bathrooms complete this floor with style and comfort. The entire third level is dedicated to a private primary suite that feels like a retreat in the sky. Wake up to elevated views over the Creek from your own private porch, admire the craftsmanship of the tongue-and-groove ceilings, and enjoy a stunning spa-style bathroom featuring a soaking tub within the shower and--finally--a large walk-in closet rarely found in Keys homes. The ground level offers a fully independent guest quarters with its own bedroom, bathroom, and full kitchen. Two functional garages with durable coated floors and bright LED lighting, plus a cabana bath accessible from both inside and outside for pool days. And then there's the backyard--where this home shifts from impressive to unforgettable. A full outdoor kitchen, heated pool, and hot tub set the stage, but the dock steals the show: deep-water dockage with two boat lifts (22,000 lb and 18,000 lb) and plenty of space for visiting boats, because friends will come. Tropical landscaping, an exterior elevator, and thoughtful details throughout complete a property that simply refuses to compromise. If you're looking for ordinary, keep scrolling. If you want a home you'll never get tired of walking into, this is it.

228 Tide Ave, Tavernier
$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
$18,999,000
6 Beds ⋅ 8 Baths ⋅ 615643 MLS
The Oasis Islamorada is a waterfront estate of exceptional scale, conceived as a private Florida Keys compound where architecture, land and water come together spanning nearly 3 meticulously landscaped acres. More than 400' of shoreline, sweeping ocean views and a protected deepwater basin create a marine setting rarely available within a single residential offering. Beyond the grand porte-cochère, the single-level main residence unfolds with soaring ceilings, white oak floors and 12-foot retractable glass walls that dissolve the boundary between interior and oceanfront living. At its center, a chef's kitchen pairs a cascading Calacatta marble island with Thermador appliances and a walk-in pantry, opening seamlessly to expansive living and dining spaces. The main residence includes four bedrooms and six full baths, with an impressive primary suite featuring a fireplace, dual walk-in closets, safe room and spa bath with steam shower. Additional suites offer en suite baths, private balconies and ocean views. A detached two-bedroom, two-bath guest residence brings the estate to six bedrooms while preserving privacy between owners and guests, with substantial grounds offering extraordinary flexibility for the future. Outside, the property assumes the scale of a private resort. Two resort-style pools with spas and sun decks are joined by a summer kitchen, alfresco dining and multiple waterfront terraces. A fitness center with sauna, soundproof theater and golf simulator complete the lifestyle offering. For the yachtsman, the protected deepwater basin accommodates substantial vessels with convenient direct Atlantic access. Built with an uncompromising focus on quality, security and enduring construction, The Oasis is more than an oceanfront residence. It is a legacy-scale Florida Keys estate offering the increasingly rare combination of acreage, significant shoreline, protected deepwater dockage, multiple residences and complete privacy within one extraordinary property

87429 Old Hwy, Islamorada
$439,000
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
$1,390,000
2 Beds ⋅ 2 Baths ⋅ 616971 MLS
Located on a tranquil canal-front setting in the desirable Plantation Key Colony, this impeccably updated, turnkey ground-level residence offers two bedrooms, two baths, 50 ft of coveted dockage, and boat slip with immediate bay access. Meticulously maintained and ready for carefree island living. The home's concrete, ground-level construction enhances both durability and ease of maintenance, while a fresh, clean aesthetic unfolds inside and out. Recent upgrades and improvements include brand new metal roof, impact windows and doors, new interior and exterior paint, new interior doors, energy efficient appliances, new sewer line, and re-thatched tiki hut. Updates to the attached pull through garage includes new door rollers, lock hardware, and upgraded flooring and wall finishes, all designed to keep the property in turnkey condition. This home is for those who embrace water-based recreation with easy bay and ocean access via Tavernier Creek, a boat slip with ramp through the garage, and new fish cleaning station with electric and water hookup. The voluntary homeowners association offers a bayfront HOA park with a new boat ramp, beach, and picnic area. With its ideal location and exceptional features, this canal home presents a unique opportunity to embrace the vibrant lifestyle of the Upper Keys.

251 Azalea St, Tavernier
$6,500,000
4 Beds ⋅ 3 Baths ⋅ 610778 MLS
Open Oceanfront Estate with Deep Water Dockage on 1.5 Acres on Millionaires' Row... Islamorada's premier address. New dock with two boat lifts (16,000 lb. and 10,000 lb.) to enjoy one of the best boating locations in the Keys, plus a 4,103 s.f. home with 4 bedrooms, 3 full baths, a large heated pool, winding private driveway, and a soaring central atrium surrounded by walls of windows to frame the ocean view. Open ocean views from the living room, Florida room, porches, master bedroom and upstairs loft. Living room with wet bar and pass-through window to the gourmet kitchen and separate dining room, all with Saturnia stone floors. Direct boating access to the best offshore fishing and diving, plus quick Florida Bay access. RE Zoning allows weekly rentals for great income potential. The sandy backyard is shaded by palms and the large pool is fenced for privacy. The winding drive from the gate to the home is dotted with seating spots for enjoying the wildlife and tropical foliage. There is also a separate storage room and workshop downstairs, a gardening shed and landscape lighting along the driveway. Call today!

88547 Old Hwy, Tavernier
$2,200,000
3 Beds ⋅ 2 Baths ⋅ 618660 MLS
First time on the market, this beautiful oceanside Key West/Bahama style home features 3 bedrooms/2 bathrooms, split floorplan for privacy, open living & entertaining area highlighted by soaring vaulted ceilings and abundant natural light. Spacious living area flows effortlessly onto an expansive lanai creating the perfect setting for outdoor dining, relaxing evenings, and enjoying the waterfront surroundings. The ground level features an impressive 2,376 square foot garage space (rarely found in the Keys) ideal for vehicles, boats, storage & workshop. Coveted corner lot with 215 feet of concrete dockage with davits. The canal provides direct ocean access to Tavernier Creek offering convenient & efficient passage to both the ocean and the bay, making this location especially desirable for anglers and cruisers alike. This is an opportunity to own a special waterfront home with exceptional dockage, oversized 10,000 square foot lot, tropical landscaping, and a paver driveway. This home is located near schools, shopping, restaurants, marinas (to fuel your boat). movie theater, and hospital.

216 Sonny Rd, Tavernier
$1,849,000
4 Beds ⋅ 2 Baths ⋅ 617994 MLS
Beautiful Double Waterfront Lot in Prestigious Plantation Key Colony. This stunning 4-bedroom, 2-bath waterfront home sits on a Rare Double Lot with a Private Boat Ramp & Boat lift, . Step outside to your Private Oasis complete with a Private Tiki hut - Gorgeous secluded in-ground Pool and Cabana Hut Bungalow - The open-concept kitchen features Granite countertops and stainless steel appliances, ideal for effortless entertaining--Perfect for Boaters and outdoor enthusiasts. Tucked away in a quiet neighborhood, yet just minutes from restaurants, shopping, and top-rated schools, this home truly offers the best of island living. Seller will consider all reasonable offers.

150 Azalea St, Tavernier
$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
$429,000
2 Beds ⋅ 2 Baths ⋅ 618010 MLS
This is a modern, fully updated beautiful 2 bedroom, 1.5 bath condominium at Summer Sea must be seen to be appreciated. Check out the photos, video and floorplan.

88500 Overseas Highway Unit 429, Tavernier