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Plantation Key, FL Homes for Sale with Pool

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  • /100

    $29,500,000

    • 6 Beds
    • 6 Baths
    • 3,104 Sq Ft

    79775 Overseas Hwy, Islamorada, FL 33036

    A once-in-a-lifetime opportunity to own one of South Florida's most iconic properties.Welcome to Tea Table Key, a breathtaking 15-acre private island estate, accessible by car or by boat, located just minutes from downtown Islamorada and directly across from the famous Alligator Reef Lighthouse.Surrounded by vivid turquoise waters, this extraordinary sanctuary offers complete privacy and a

    Agent Photo

    Pierre Bellion

    Ocean Sotheby's International Realty

    (855) 951-5685

    79775 Overseas Hwy, Islamorada, FL 33036
  • /55

    $2,495,000

    New Construction
    • 3 Beds
    • 3.5 Baths
    • 1,829 Sq Ft

    81906 Overseas Hwy Unit 2, Islamorada, FL 33036

    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

    Agent Photo

    Pierre Bellion

    Ocean Sotheby's International Realty

    (786) 917-2660

    81906 Overseas Hwy Unit 2, Islamorada, FL 33036
  • /73

    $4,650,000

    • 6 Beds
    • 5 Baths
    • 4,964 Sq Ft

    153 Stromboli Dr, Islamorada, FL 33036

    Exquisite Tri-Level Waterfront Estate in Islamorada! Step into luxury with this remarkable home in the prestigious Venetian Shores, designed for the most discerning buyer. Offering six bedrooms, five bathrooms, and a spacious 5000sqft of magnificently designed living space, this residence offers an open-concept floor plan with soaring ceilings, a fireplace and a grand living area. Enjoy seamless

    Lisa Frins Langley Knight Gardner Islamorada

    153 Stromboli Dr, Islamorada, FL 33036
  • /82

    $3,800,000

    New Construction
    • 4 Beds
    • 4.5 Baths
    • 2,574 Sq Ft

    82779 Old Hwy Unit 8, Islamorada, FL 33036

    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,

    The Florida Keys Sold Sisters Ocean Sotheby's International Realty

    82779 Old Hwy Unit 8, Islamorada, FL 33036
  • /79

    $3,800,000

    New Construction
    • 4 Beds
    • 4.5 Baths
    • 2,574 Sq Ft

    82779 Old Hwy Unit 14, Islamorada, FL 33036

    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,

    The Florida Keys Sold Sisters Ocean Sotheby's International Realty

    82779 Old Hwy Unit 14, Islamorada, FL 33036
  • /84

    $3,800,000

    New Construction
    • 4 Beds
    • 4.5 Baths
    • 2,574 Sq Ft

    82779 Old Hwy Unit 7, Islamorada, FL 33036

    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,

    The Florida Keys Sold Sisters Ocean Sotheby's International Realty

    82779 Old Hwy Unit 7, Islamorada, FL 33036
  • /100

    $8,490,000

    • 8 Beds
    • 6 Baths

    1101 Mastic St Unit 1, Islamorada, FL 33036

    Spectacular Bayfront Estate with Guesthouse in the Heart of Islamorada Experience luxury coastal living at its finest in this exceptional Gated bayfront estate, ideally situated in the heart of Islamorada. Set on a rare peninsula with over 225 feet of prime waterfront, this property offers unmatched privacy, panoramic views, and direct access to both the Florida Bay and Atlantic Ocean. The main

    Tracey Petrusha LoKation

    1101 Mastic St Unit 1, Islamorada, FL 33036
  • /64

    $6,750,000

    • 6 Beds
    • 5 Baths
    • 4,566 Sq Ft

    83407 Old Hwy, Islamorada, FL 33036

    This breathtaking three-story beachfront estate offers the ultimate blend of resort-style living and refined comfort. Featuring six spacious bedrooms and five luxurious bathrooms, and three inviting living rooms, home is designed to accommodate both relaxation and entertainment with ease. Set in a serene cove with a pristine natural beach, the home showcases floor-to-ceiling windows that frame

    Cheri Tindall American Caribbean Real Estate, Christie's International Real Estate

    83407 Old Hwy, Islamorada, FL 33036
  • /33

    $3,995,000

    $500K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 4,014 Sq Ft

    87445 Old Hwy, Islamorada, FL 33036

    This stunning property spans 1.82 acres and is ideally located on the ocean in the heart of Islamorada, Florida Keys. A gated entry welcomes you leading to a Royal Palm-lined circular driveway up to a portico providing a grand entrance. Upon entering the foyer, the wrought iron staircase sets the stage for the impressive interior.With five spacious bedrooms and four well-appointed bathrooms, this

    Cheri Tindall American Caribbean Real Estate, Christie's International Real Estate

    87445 Old Hwy, Islamorada, FL 33036
  • /82

    $3,800,000

    New Construction
    • 4 Beds
    • 4.5 Baths
    • 2,574 Sq Ft

    82779 Old Hwy Unit 15, Islamorada, FL 33036

    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,

    The Florida Keys Sold Sisters Ocean Sotheby's International Realty

    82779 Old Hwy Unit 15, Islamorada, FL 33036
  • /29

    $4,799,000

    • 5 Beds
    • 4.5 Baths
    • 3,556 Sq Ft

    128 Leoni Dr, Islamorada, FL 33036

    SPECTACULAR HOME IN VENETIAN SHORES! 70' concrete dock on deep water canal which opens directly to Snake Creek for easy and quick access to bay or ocean; 5 bedrooms/4.5 baths; private master retreat with gorgeous bath on third level; marble floors throughout; elevator; FABULOUS chef's kitchen with Wolf gas range and huge island; large terraces and fantastic entertaining spaces; sound system

    Emily Romberg Real Estate Sales Force - Coral Gables

    128 Leoni Dr, Islamorada, FL 33036
  • /109

    $19,500,000

    New Construction $5K PRICE INCREASE
    • 6 Beds
    • 8 Baths
    • 6,692 Sq Ft

    87429 Old Hwy, Islamorada, FL 33036

    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-cochere entry sets the tone, leading to a single-level

    TEAM Walters Gloria, Rachel and Michae Ocean Sotheby's International Realty

    87429 Old Hwy, Islamorada, FL 33036
  • /87

    $24,995,000

    New Construction
    • 5 Beds
    • 8 Baths
    • 9,011 Sq Ft

    87895 Old Hwy, Islamorada, FL 33036

    Introducing a newly completed architectural masterpiece overlooking the turquoise waters of the Atlantic Ocean in the prestigious enclave of Plantation Key. Set on over two private acres, this extraordinary estate embodies the pinnacle of coastal elegance, modern luxury, and serene island living.Spanning more than 9,000 sq. ft. of interior living space (15,000+ sq. ft. under roof), this expansive

    Sam Williams Coldwell Banker Schmitt Real Estate Co.

    87895 Old Hwy, Islamorada, FL 33036
  • /66

    $630,000

    • 2 Beds
    • 1.5 Baths
    • 1,365 Sq Ft

    87200 Overseas Hwy Unit N2, Islamorada, FL 33036

    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

    Barbara Eads Barbara Eads Realty

    87200 Overseas Hwy Unit N2, Islamorada, FL 33036
  • /43

    $15,950,000

    • 6 Beds
    • 7 Baths
    • 6,680 Sq Ft

    20 Avacado St, Islamorada, FL 33036

    BAYSIDE, DEEP WATER, BREATHTAKING GULF VIEWSWelcome to one of Islamorada's premier rare bayside estate properties - a remarkable parcel that stretches from Overseas Highway all the way to the Bay. The home bestows privacy, unobstructed Gulf Views, and a deep-water basin for calm dockage cable of accommodating substantial vessels with immediate access to world class sportfishing waters. The

    Steven Koleno Beycome of Florida LLC

    20 Avacado St, Islamorada, FL 33036
  • /92

    $3,495,000

    • 4 Beds
    • 4.5 Baths
    • 2,539 Sq Ft

    80639 Old Hwy Unit 201, Islamorada, FL 33036

    Welcome to Your Florida Keys retreat or income-producing rental, with 7-day rentals approved! Maison Residences presents its final developer unit, #201, offering 4 bedrooms, 4.5 bathrooms and a spacious open layout designed for true oceanside living. Step off your private elevator into a grand room with soaring 10-foot ceilings and 9-foot stacked sliders that frame endless Ocean views. The open

    Jennifer Gomez LPT Realty, LLC

    80639 Old Hwy Unit 201, Islamorada, FL 33036
  • /40

    $1,600,000

    New Construction $99K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,277 Sq Ft

    36 Park Rd, Upper Matecumbe Key Islamorada, FL 33036

    Stunning new custom pool home in the heart of Islamorada. This exceptional, brand-new ground-level home was thoughtfully designed and expertly crafted with meticulous attention to detail. A professional interior designer curated high-end fixtures and elegant finishes throughout, creating a polished and inviting living space.Offering a rare 4-bedroom, 3-bathroom split floorplan, the home features

    AJ Vetter Palm House Real Estate

    36 Park Rd, Upper Matecumbe Key Islamorada, FL 33036
  • /48

    $1,300,000

    • 3 Beds
    • 2 Baths
    • 1,224 Sq Ft

    32 Park Rd, Islamorada, FL 33036

    Ideally located in the heart of Islamorada, this charming home is perfectly updated with a harmonious blend of old and new Keys characteristics and a light and airy layout and enclosed sun room that brings the lovely landscaping inside! A serene pool and oversized backyard with plenty of privacy provide book ends to lovely days of beat the heat splashes during the day and evenings of peace and

    The Florida Keys Sold Sisters Ocean Sotheby's International Realty

    32 Park Rd, Islamorada, FL 33036
  • /39

    $629,000

    • 2 Beds
    • 2 Baths
    • 1,337 Sq Ft

    87200 Overseas Hwy Unit A7, Islamorada, FL 33036

    Experience the ultimate Florida Keys lifestyle in this bright and spacious townhouse-style condo located in sought-after Executive Bay Club in Islamorada. Ideally situated next to Founders Park, this gated bayfront community offers an unbeatable combination of location, lifestyle, and investment potential. One of the standout features of this residence is the rare open kitchen layout, creating a

    Christian Hoheb Compass Florida, LLC

    87200 Overseas Hwy Unit A7, Islamorada, FL 33036
  • /36

    $1,150,000

    • 2 Beds
    • 2.5 Baths
    • 1,376 Sq Ft

    102 Anglers Way, Islamorada, FL 33036

    ANGLERS REEF HOME THAT PAYS FOR ITSELF! Islamorada's Upscale Oceanfront Gated Community that allows Vacation Rentals, This home features 2 bedrooms, 2.5 bathrooms with carport & 4 porches. Upgrades include Brazilian Cherry hardwood floors, kitchen with granite countertops and SS appliances with 2 breakfast bars & tons of cabinet space. The home also has a composite decking, metal roof & impact

    Scott Ofstein Berkshire Hathaway HomeServices Florida Realty - Coral Springs

    102 Anglers Way, Islamorada, FL 33036
  • /93

    $2,995,000

    New Construction
    • 4 Beds
    • 5 Baths
    • 3,467 Sq Ft

    114 Royal Ln, Islamorada, FL 33036

    Pickle Ball Estate is a stunning new luxury retreat in the heart of Islamorada, masterfully crafted by 4 Keys Construction. This brand-new four-bedroom, five-bathroom residence is a true standout, blending refined coastal design with resort-style living.Designed for both relaxation and entertainment, the home features a private pickleball court, making it a rare and exciting find in the Florida

    Alexander Pinero Pine River Realty, LLC

    114 Royal Ln, Islamorada, FL 33036
  • /59

    $1,300,000

    • 2 Beds
    • 2 Baths
    • 1,732 Sq Ft

    87851 Old Hwy Unit M5, Islamorada, FL 33036

    A New Standard of Paradise - Live with views of the Atlantic Ocean everyday. This home has been updated and beautified from top to bottom. Marble flooring throughout living areas. Eat in kitchen offers large island, snack counter and full size wine cooler. Dishwasher installed 12/25. There is also a hot water dispenser. Dining area and living area open to enclosed patio with private spiral

    Jackie Ellis KW Innovations

    87851 Old Hwy Unit M5, Islamorada, FL 33036
  • /93

    $524,999

    $65K PRICE DROP
    • 2 Beds
    • 2 Baths

    79901 Overseas Hwy Unit 204, Islamorada, FL 33036

    Spectacular Direct Ocean Views! Islamorada's Best-Kept Secret! This beautifully appointed 2-bedroom, 2-bath residence offers breathtaking, unobstructed ocean views from your private waterfront balcony. Step outside and enjoy a refreshing swim in the oceanfront pool or take a dip directly in the crystal-clear Atlantic. Perfectly situated near Bud & Mary's Marina and just minutes from Islamorada's

    Tracey Petrusha LoKation

    79901 Overseas Hwy Unit 204, Islamorada, FL 33036
  • /16

    $549,000

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,016 Sq Ft

    87455 Old Hwy 229 Hwy Unit 229, Plantation Key, FL 33036

    Beautifully maintained 2-bedroom, 2 bath townhouse condo located oceanside in the heart of Islamorada. This turn-key residence offers effortless island living with no updates needed—simply move in and enjoy. The home features a new A/C system installed in 2022, new appliances added in 2024, and fully replaced air ducts completed in 2024 for improved comfort and efficiency. Impact windows

    Jose Medina Main Assets Corp

    87455 Old Hwy 229 Hwy Unit 229, Plantation Key, FL 33036
  • /47

    $1,599,000

    New Construction
    • 4 Beds
    • 3 Baths
    • 2,048 Sq Ft

    124 Venetian Way, Islamorada, FL 33036

    Island Living in Prestigious Venetian Shores!Welcome to this newly custom-built four bedroom, three bathroom residence ideally positioned on a tranquil plugged canal in one of the most sought-after neighborhoods in the Florida Keys. Upstairs, enjoy a spacious open porch, ideal for outdoor dining that flows seamlessly into a light-filled open concept floor plan. The designer kitchen features solid

    Lisa Frins Century 21 Prestige Realty Grp, Tavernier

    124 Venetian Way, Islamorada, FL 33036
  • /68

    $24,995,000

    • 7 Beds
    • 10.5 Baths
    • 10,182 Sq Ft

    82719 Old Hwy, Islamorada, FL 33036

    Experience unparalleled oceanfront living at Chateau On The Ocean, a turnkey private estate set within an exclusive enclave in Islamorada. Here elevated coastal living reflects the sophistication of what has been referred to as the Hamptons of Miami. From the moment you arrive, a striking sense of privacy, scale, and intention is evident, with architecture and surroundings that feel truly

    Pamela DiMartino Coldwell Banker Realty

    82719 Old Hwy, Islamorada, FL 33036
  • /35

    $585,000

    • 2 Beds
    • 2.5 Baths
    • 1,303 Sq Ft

    80450 Overseas Hwy Unit 106, Islamorada, FL 33036

    Set in the very center of Islamorada's vibrant island community, this 2BD/2.5BA townhouse style condo in Sand Pebbles offers privacy, comfort, and convenience. The ground level features two spacious en-suite bedrooms, each with its own private porch. Upstairs, enjoy a bright open-concept living, dining, and kitchen area plus a convenient half bath. With 1,303 sq ft and multiple outdoor living

    The Jude Lindback Te Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

    80450 Overseas Hwy Unit 106, Islamorada, FL 33036
  • /34

    $645,000

    $35K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,354 Sq Ft

    87200 Overseas Hwy Unit 2, Islamorada, FL 33036

    ANCHOR IN PARADISE- 4 BEDROOM, 2 BATH IN ISLAMORADA- EXECUTIVE BAY CLUB, THIS IMMACULATE CONDO WILL CONVEY FULLY FURNISHED ALL COMPLETELY RENOVATED & UPDATED W/HURRICANE IMPACT WINDOWS, SLIDING GLASS DOORS, WASHER/DRYER DOWNSTAIRS. PERFECT RETREAT W/SANDY BEACH, POOL, TENNIS COURTS, CLUBHOUSE FOR GATHERINGS, DOCKAGE AVAILABLE, BRAND NEW ONSITE MARINA, WALKING DISTANCE TO 'FOUNDER'S PARK' & FINE

    Lidia Yoham Anchor Realty of FL, LLC.

    87200 Overseas Hwy Unit 2, Islamorada, FL 33036
  • /29

    $429,000

    $71K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,000 Sq Ft

    87455 Old Hwy Unit 248, Islamorada, FL 33036

    THIS OCEAN FRONT BEAUTY IS. PRICED TO SELL! RARE 2 BEDROOM CONDO WITH OCEAN VIEWS FOR LESS THAN $430,000. THIS SPACIOUS CONDO OFFERS THE PERFECT BLEND OF COMFORT & CONVENIENCE. FEATURING AN OPEN CONCEPT LIVING AREA, A WELL-APPOINTED UPDATED OPEN CONCEPT KITCHEN WITH WOOD CABINETRY, RECESSED LIGHTING, AND AMPLE STORAGE. NEW HOT WATER HEATER, 1/2 BATH DOWNSTAIRS, SPLIT BEDROOM LAYOUT UPSTAIRS FOR

    Nancy Garcia The Keyes Company

    87455 Old Hwy Unit 248, Islamorada, FL 33036
  • /39

    $655,000

    • 3 Beds
    • 3 Baths
    • 1,346 Sq Ft

    87200 Overseas Hwy Unit S3, Islamorada, FL 33036

    Welcome to effortless coastal living in the desirable Executive Bay Club community--where comfort, style, and resort-style amenities come together in a relaxed Keys setting. This nicely updated 3-bedroom plus loft townhouse offers a spacious and versatile layout designed for easy everyday living and entertaining. Upstairs, you'll find three inviting bedrooms, two full baths, and a charming

    Alina Davis Coldwell Banker Schmitt Islamorada

    87200 Overseas Hwy Unit S3, Islamorada, FL 33036
  • /49

    $2,850,000

    • 3 Beds
    • 3 Baths
    • 2,072 Sq Ft

    81250 Overseas Hwy Unit 2, Islamorada, FL 33036

    Experience 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

    AJ Vetter Palm House Real Estate

    81250 Overseas Hwy Unit 2, Islamorada, FL 33036
  • /39

    $1,199,990

    • 2 Beds
    • 2.5 Baths
    • 1,376 Sq Ft

    111 Anglers Way, Islamorada, FL 33036

    Your dream getaway in the heart of the Florida Keys! This light-filled, spacious 2br/2bth home is located in the highly sought-after Angler's Reef community in Islamorada. Fully furnished, tastefully decorated and turnkey, this well-maintained property is perfect for ocean lovers or savvy investors alike.With over 12 years in a successful vacation rental program and an active vacation rental

    Rosana Velilla Serrano & Associates Real Estate, LLC

    111 Anglers Way, Islamorada, FL 33036
  • /18

    $1,300,000

    $50K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,376 Sq Ft

    104 Anglers Way, Islamorada, FL 33036

    Exclusive Anglers Reef Resort-style oceanfront home in Islamorada -- a rare coastal gem. Nestled inside a gated community with resort-caliber amenities, a private marina and two sandy beaches, this fully furnished two-story single-family retreat offers 2 bedrooms and 2.5 baths -- ideal for saltwater lovers or savvy investors.Thoughtfully upgraded with elegant, durable finishes: impact-rated

    Rayden Vega Casa Miami Real Estate

    104 Anglers Way, Islamorada, FL 33036
  • /50

    $457,000

    $3K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,100 Sq Ft

    87465 Old Hwy Unit 215, Islamorada, FL 33036

    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

    Anthony Garcia The Keyes Company

    87465 Old Hwy Unit 215, Islamorada, FL 33036
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