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Islamorada, FL 2-Story Homes for Sale

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  • /67

    $2,399,000

    • 3 Beds
    • 3 Baths
    • 1,066 Sq Ft

    126 Columbus Dr, Islamorada, FL 33036

    Incoming producing property with future bookings already in place! 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

    Agent Photo

    Jessica Wolf

    Luxe Properties

    (844) 443-0253

    126 Columbus Dr, Islamorada, FL 33036
  • /49

    $2,389,000

    • 2 Beds
    • 3 Baths
    • 1,230 Sq Ft

    254 Navajo St, Tavernier, FL 33070

    This house has 2 bedrooms and 2 bathrooms upstairs and 1-bedroom and 1-bathroom downstairs.Owner is a licensed real estate agent.

    Agent Photo

    Judy Rossignol

    Realty One Group Engage the Keys

    (844) 435-8872

    254 Navajo St, Tavernier, FL 33070
  • /62

    $3,475,000

    • 4 Beds
    • 4.5 Baths
    • 3,330 Sq Ft

    118 Pelican Rd, Tavernier, FL 33070

    Modern Coastal Luxury in Islamorada! Built in 2019, this 4-bed, 5-bath home blends sleek design with island charm. Each bedroom has a private ensuite, plus a full guest bath for added comfort. The gourmet kitchen features high-end appliances, custom cabinetry, and open-concept flow—perfect for entertaining. The spacious primary suite includes a spa-like bath, walk-in closet, and private balcony

    Alejandro Perez AmeriFirst Realty

    118 Pelican Rd, Tavernier, FL 33070
  • /36

    $2,260,000

    • 2 Beds
    • 2 Baths
    • 1,071 Sq Ft

    125 Cortez Dr, Islamorada, FL 33036

    Welcome to your slice of paradise in the sought-after Matecumbe Ocean View neighborhood! This beautifully upgraded concrete home (including the roof) is built for durability, comfort, and style. Fully fenced and thoughtfully designed, the exterior grounds features sleek new concrete and turf along the sides of the house for a clean, modern look.The backyard is an entertainer's dream with a full

    Natalie Ardis Coldwell Banker Schmitt Real Estate Co.

    125 Cortez Dr, Islamorada, FL 33036
  • /50

    $2,700,000

    • 3 Beds
    • 2 Baths
    • 2,010 Sq Ft

    189 Gulfview Dr, Islamorada, FL 33036

    Welcome to Port Antigua! This beautiful Key West-style home in Port Antigua boasts an open floor plan with a spacious kitchen featuring a large center island. The main living area on the second floor includes three bedrooms and two bathrooms, while the first floor offers an entertainment room that could serve as a fourth bedroom. Two sets of sliding glass doors lead to a screened-in porch

    Raul Hernandez Phantom Real Estate

    189 Gulfview Dr, Islamorada, FL 33036
  • /88

    $1,750,000

    • 4 Beds
    • 2 Baths

    162 Azalea St, Tavernier, FL 33070

    Plantation Key Colony - Completely UPDATED-Like New - 2/1 up and 2/1 down, plus -1- more Extra Room- Great to Live in or Great for Renting out Half and using the other half or making it a Double rental income. Large Concrete Dock 75 Ft. w/ 20,000lb Boat Lift. This Big Lot is 125x75 with a Tiki Hut & Hot Tub. Quick Direct access to Bay & Ocean. Beautiful Homeowners Park on the Bay with a Beach &

    Tracey Petrusha Venture Realty Group

    162 Azalea St, Tavernier, FL 33070
  • /2

    $1,999,999

    • 2 Beds
    • 2.5 Baths
    • 1,674 Sq Ft

    144 Anglers Way, Islamorada, FL 33036

    ANGLERS REEF OCEANFRONT HOME WITH DEEDED DOCK in Islamorada.7 DAY RENTALS ALLOWED. Dock accommodates up to a 31' boat. A beautiful 2-bedroom, 2.5-bath, 2-story home with 2 porches & a balcony overlooking the Atlantic Ocean. Located in the gated community of Anglers Reef, half way between Miami & Key West. This property contains 2 large bedroom suites on the 2nd floor. Home looks out to the

    Scott Ofstein Berkshire Hathaway Florida Realty

    144 Anglers Way, Islamorada, FL 33036
  • /30

    $1,950,000

    • 3 Beds
    • 2 Baths
    • 2,364 Sq Ft

    141 Ocean Dr, Tavernier, FL 33070

    Fisherman's Delights! This concrete fortress is nestled in a lush tropical setting, located on the Oceanside on a deep, clean, wide canal. 70' concrete dock accommodates larger boats. Solidly build CBS construction with reinforced concrete roof. Spacious rooms and living areas throughout. The first floor features a guest quarter with separate entrances, seller has set up as two apartments. Take

    Susan Holler LoKation

    141 Ocean Dr, Tavernier, FL 33070
  • /50

    $1,859,000

    • 3 Beds
    • 3 Baths
    • 1,804 Sq Ft

    178 Gulfview Dr, Islamorada, FL 33036

    Welcome to White Marlin – a true fisherman’s paradise! Step into this stunning 3-bedroom, 3-bathroom oasis complete with a private pool, boat ramp, and a 60-foot concrete dock. Inside, you’ll find an inviting open-concept design with a spacious kitchen featuring beautiful tile countertops, ideal for entertaining and family gatherings. Relax on the screened-in balcony or unwind on your private

    Raul Hernandez Phantom Real Estate

    178 Gulfview Dr, Islamorada, FL 33036
  • /51

    $1,795,000

    • 4 Beds
    • 3 Baths
    • 1,629 Sq Ft

    190 Gulfview Dr, Islamorada, FL 33036

    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

    Dominic Rivera Pine River Realty, LLC.

    190 Gulfview Dr, Islamorada, FL 33036
  • /18

    $1,650,000

    • 3 Beds
    • 2 Baths
    • 1,278 Sq Ft

    121 Venetian Dr, Islamorada, FL 33036

    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

    Robert Santana TruRes Real Estate Inc.

    121 Venetian Dr, Islamorada, FL 33036
  • /76

    $2,049,000

    • 3 Beds
    • 3 Baths
    • 1,295 Sq Ft

    155 Plantation Ave, Tavernier, FL 33070

    **Waterfront Paradise: Solid Concrete Home on Deep Water Canal**Nestled along a serene deep water canal, this exquisite solid concrete home awaits its new owner. Embark on a brick paver driveway that leads to a turn-key residence designed to impress.As a boater's paradise, this property boasts a private boat lift, davit, clean out station, and outdoor shower. Access to the community's boat ramp

    Mary Pecorino Coast to Coast RE Group

    155 Plantation Ave, Tavernier, FL 33070
  • /2

    $2,200,000

    • 4 Beds
    • 3 Baths
    • 1,708 Sq Ft

    120 Captains Ct, Tavernier, FL 33070

    Now Available! One-of-a-kind Opportunity in the desirable Kahiki Harbor neighborhood. 165' waterfront Corner Lot. Vintage 4 bedroom/3 bath Custom built Keys home. 2/2 upstairs and a Great Room with all doors opening to the walk-around porch Downstairs has 700' of additional enclosed storage, laundry, bathroom and two bedrooms. In the peaceful Kahiki Harbor neighborhood, deep water dockage all the

    Lisa Lapradd Beacon Property Services, Inc.

    120 Captains Ct, Tavernier, FL 33070
  • /63

    $599,900

    • 2 Beds
    • 3 Baths
    • 1,355 Sq Ft

    87200 Overseas Hwy Unit 5, Islamorada, FL 33036

    Discover the best of FL Keys living in this updated 2BR/3BA villa in Islamorada's Executive Bay Club! Features include wood-look tile thru-out, granite counters, SS appliances, tankless WH, new A/C & loft space for added flex. Spacious primary suite w/ built-in closets. Just steps to pool, beach, tennis, pickleball, bball & more. Enjoy pet-friendly living w/ first-come, first-serve boat dock

    Christian Hoheb Compass Florida, LLC.

    87200 Overseas Hwy Unit 5, Islamorada, FL 33036
  • /34

    $1,175,000

    • 2 Beds
    • 2 Baths
    • 3,186 Sq Ft

    269 Burgundy Dr, Tavernier, FL 33070

    Breathtaking Ocean Views and Breezes from this prime waterfront location with excellent boating access. Get your Island vibes in this cute, clean and ready to enjoy island home ~ Casa Cayo! In the heart of Tavernier! This delightful 2-bedroom, 2-bathroom manufactured home on stilts boasts breathtaking sunrise views from your private balcony and soothing ocean breezes all day long. With an

    Terry Canto American Caribbean Real Estate

    269 Burgundy Dr, Tavernier, FL 33070
  • /38

    $1,175,000

    • 3 Beds
    • 3 Baths
    • 2,808 Sq Ft

    82260 Overseas Hwy, Islamorada, FL 33036

    Paradise Found: Renovated Jungle Treehouse! Welcome to your dream retreat in the heart of the Florida Keys. Nestled in the highly sought-after village of Islamorada, this exquisitely remodeled 3-bedroom, 3-bath estate redefines luxury living. Perfectly situated on a sprawling 15k+ square-foot lot, this property offers an unparalleled combination of elegance, privacy, and tropical charm. NEW 2024

    Andre Huyghues Despointes Sutter & Nugent LLC

    82260 Overseas Hwy, Islamorada, FL 33036
  • /2

    $1,199,999

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

    102 Anglers Way, Islamorada, FL 33036

    ANGLERS REEF HOMEf, Islamorada's Upscale Oceanfront Gated Community, 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 doors & windows. The community features 2 sandy

    Scott Ofstein Berkshire Hathaway Florida Realty

    102 Anglers Way, Islamorada, FL 33036
  • /79

    $5,299,000

    • 6 Beds
    • 5 Baths

    153 Stromboli Dr, Islamorada, FL 33036

    Exquisite Tri-Level Waterfront Estate in Venetian Shores! This luxury home features six bedrooms, five bathrooms, and 5000 sqft of living space. With an open-concept floor plan, soaring ceilings, and a grand living area, it offers seamless indoor-outdoor living with a wraparound veranda and stunning water views. The 10,000 sqft lot provides privacy, and the swimming pool is perfect for

    Will Langley Langley Knight Gardner Islamorada

    153 Stromboli Dr, Islamorada, FL 33036
  • /50

    $3,800,000

    • 4 Beds
    • 3.5 Baths

    145 Venetian Dr, Islamorada, FL 33036

    LUXURY CANAL FRONT HOME IN ISLAMORADA! Brand new offering of the most exquisite coastal designed home offering spacious floor plans, entertaining spaces, and oversized rooms. This meticulously maintained home offers a split floorplan with a living room, wet bar, sizeable bedroom and full bathroom on the ground floor overlooking the outdoor kitchen and in ground pool. The second level boosts 3

    Will Langley Langley Knight Gardner Islamorada

    145 Venetian Dr, Islamorada, FL 33036
  • /27

    $325,000

    • 1 Bed
    • 1 Bath
    • 598 Sq Ft

    92550 Overseas Hwy Unit 108, Tavernier, FL 33070

    Anchor condominium is a hidden gem in Tavernier on the Bay. This is a spacious one bedroom, one bath ground floor condo with a view of the bay from the bedroom. 15 days minimum rental period. There are boat slips (with a wait list) Sunset viewing deck, beach area, kayak storage and launch pad. This is the affordable get away place (Or home) you have been waiting for. Immediate bay and ocean

    Wiebke Westedt Lokation

    92550 Overseas Hwy Unit 108, Tavernier, FL 33070
  • /40

    $615,000

    • 2 Beds
    • 2.5 Baths
    • 1,350 Sq Ft

    87200 Overseas Hwy Unit F4, Islamorada, FL 33036

    This is the best buy in Executive Bay in a prime location, close to the bay and pool. 2 full baths upstairs and a half downstairs. This unit is one of very few that has an open kitchen without the divider wall. Light, bright and spacious describes it best. Located in Islamorada next to Founders Park, EBC offers first come dockage with additional slips just added in the redone marina, a beach area

    Wiebke Westedt Lokation

    87200 Overseas Hwy Unit F4, Islamorada, FL 33036
  • /63

    $1,350,000

    • 5 Beds
    • 4 Baths
    • 2,492 Sq Ft

    155 Fontaine Dr, Tavernier, FL 33070

    Live the dream in this elevated Plantation Key home designed for island living. The main house features 3 beds, 2 baths, with a freshly painted interior, new LED lighting, and ceiling fans. The upgraded kitchen includes stainless steel appliances, a gas cooktop, and a wine cooler. The lower level offers a finished storage area with bath facilities. Outdoors, enjoy a screened-in pool surrounded by

    Will Langley Langley Knight Gardner Islamorada

    155 Fontaine Dr, Tavernier, FL 33070
  • /19

    $625,000

    • 2 Beds
    • 2 Baths
    • 1,269 Sq Ft

    178 Arbor Ln, Tavernier, FL 33070

    Perfectly situated in Tavernier, this 2-bedroom, 2-bathroom modular home, built in 2020, blends modern comfort with coastal charm. With 1,269 sq. ft., the elevated home features impact-resistant windows and doors, filling the bright, open layout with natural light.The kitchen offers stainless steel appliances, white cabinetry, and a breakfast bar—ideal for casual meals. Coastal hues and

    Taylor Engel Coldwell Banker Schmitt R.E.

    178 Arbor Ln, Tavernier, FL 33070
  • /44

    $675,000

    • 3 Beds
    • 1 Bath
    • 1,312 Sq Ft

    130 Ocean View Dr, Tavernier, FL 33070

    Discover why Ocean View Drive is the street to live on! See the charm of the historic Old Tavernier district with this inviting 3-bedroom, 1-bathroom home with beautiful water views just down the road. Situated at mile marker 91.5 on the oceanside, this property offers 1,312 sq ft of thoughtfully designed living space. There is plenty of room to build a secondary bathroom and expand your

    Taylor Engel Coldwell Banker Schmitt R.E.

    130 Ocean View Dr, Tavernier, FL 33070
  • /35

    $448,900

    • 2 Beds
    • 2 Baths
    • 1,100 Sq Ft

    87465 Old Hwy Unit 102, Islamorada, FL 33036

    LIVE THE DREAM IN THIS OCEANFRONT BUILDING IN THE BEAUTIFUL FLORIDA KEYS! LARGER THAN OTHER UNITS UNDER AIR AT 1100 SQ FT. TURN KEY STUNNING AND REMODELED, FRESHLY PAINTED, FULLY FURNISHED ALL ON ONE LEVEL 2 BEDROOM 2 FULL BATH CONDO IS MOVE IN READY! OR START MAKING MONEY AS A VACATION RENTAL RIGHT AWAY! $10,000.00 WORTH OF VACATION RENTAL BOOKINGS AND CONSULTING ARE INCLUDED WITH THIS CONDO

    Nancy Garcia The Keyes Company

    87465 Old Hwy Unit 102, Islamorada, FL 33036
  • /13

    $925,000

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft

    177 Iroquois St, Tavernier, FL 33070

    Beautifully renovated 3-bedroom, 2-bathroom home in desirable IndianHarbor, this property has been completely updated with high-end finishes and thoughtful details throughout.Open-concept living area and kitchen, The house features new large impact windows and a layout that utilized all of the space. The kitchen features brand-new stainless-steel appliances, custom cabinetry, quartzite

    Steven Koleno BEYCOME OF FLORIDA LLC

    177 Iroquois St, Tavernier, FL 33070
  • /49

    $1,250,000

    • 2 Beds
    • 2 Baths
    • 1,232 Sq Ft

    144 Dove Ave, Tavernier, FL 33070

    Don't miss out on this east of US 1 canal front home with amazing views. Updated kitchen with quartz counters, Impact windows and doors throughout with shutters for extra protection. Tile floors, paver driveway, screened patio with no see-um screens, Fenced area of yard for pets, custom shades, upgraded appliances, the list is long and impressive. Don't forget the tiki with custom lighting and

    Ophelia Angelone Action Realty LLC

    144 Dove Ave, Tavernier, FL 33070
  • /36

    $1,500,000

    • 2 Beds
    • 2.5 Baths
    • 1,137 Sq Ft

    120 Anglers Way, Islamorada, FL 33036

    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

    Scot Drucker Compass Florida, LLC.

    120 Anglers Way, Islamorada, FL 33036
  • /80

    $10,900,000

    • 4 Beds
    • 4.5 Baths
    • 4,512 Sq Ft

    170 Sapodilla Dr, Islamorada, FL 33036

    Discover the unparalleled beauty and tranquility of this Bayfront Estate, nestled on the pristine shores of Lower Matecumbe in the Florida Keys. Surrounded by lush, meticulously landscaped grounds, this exceptional property offers direct waterfront on the crystal clear waters of the Gulf. Experience breathtaking sunsets over the horizon, world-class tarpon fishing just steps away, and private

    Patti Lindback Langley Knight Gardner Islamor

    170 Sapodilla Dr, Islamorada, FL 33036
  • /29

    $799,000

    • 2 Beds
    • 2 Baths
    • 1,120 Sq Ft

    125 S Rolling Hill Rd, Tavernier, FL 33070

    Charming and Tranquil Home in the Heart of Islamorada. Experience serene living in this delightful 2-bedroom, 2-bathroom retreat on Plantation Key. Perfectly situated, this home offers convenient access to top schools, fantastic dining options, the beautiful Founders Park and Beach, and other neighborhood amenities. The property boasts a spacious, fenced corner lot with ample RV and boat parking,

    Shelby Morris American Caribbean Real Estate

    125 S Rolling Hill Rd, Tavernier, FL 33070
  • /28

    $589,000

    • 2 Beds
    • 1.5 Baths
    • 1,358 Sq Ft

    87200 Overseas Hwy Unit 4, Islamorada, FL 33036

    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

    Taylor Engel Coldwell Banker Schmitt R.E.

    87200 Overseas Hwy Unit 4, Islamorada, FL 33036
  • /62

    $750,000

    • 3 Beds
    • 2 Baths
    • 1,355 Sq Ft

    87200 Overseas Hwy, Islamorada, FL 33036

    All NEW 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

    Ivette Agusti Premier Properties

    87200 Overseas Hwy, Islamorada, FL 33036
  • /47

    $3,875,000

    • 4 Beds
    • 4 Baths
    • 3,004 Sq Ft

    96 W Plaza Del Sol, Islamorada, FL 33036

    Modern Meets Coastal! Welcome to this Masterpiece in Port Antigua! Assumable 2.8% interest rate! This won't last. 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

    Shelby Morris American Caribbean Real Estate

    96 W Plaza Del Sol, Islamorada, FL 33036
  • /60

    $22,500,000

    • 8 Beds
    • 14 Baths
    • 8,949 Sq Ft

    94100 Overseas Hwy, Tavernier, FL 33070

    Experience Absolute Paradise! A Legacy Florida Keys Estate offering ultimate privacy & tranquility. The Orchid Cove Estate spans 14.5 Acres offering 1,000 ft. of waterfront & Private Beaches accessed through a grand entrance surrounded by a breathtaking canopy of exotic trees. Award winning Botanical gardens surround the property featuring impeccably curated nature trails leading to the main

    Esther Percal BHHS EWM Realty

    94100 Overseas Hwy, Tavernier, FL 33070
  • /35

    $757,000

    • 3 Beds
    • 3 Baths
    • 1,764 Sq Ft

    100 Iroquois Dr Unit 8, Islamorada, FL 33036

    Welcome to your own paradise in Islamorada, Florida! This stunning retreat offers the perfect blend of modern luxury and serene island living. Step inside this meticulously remodeled 3-bedroom, 3-full bathroom home and be amazed by the expert craftsmanship and attention to detail. The contemporary design fits seamlessly with the tropical surroundings while providing an elegant and comfortable

    April Nixon RE/MAX Trend

    100 Iroquois Dr Unit 8, Islamorada, FL 33036
  • /52

    $2,295,000 New Construction

    • 5 Beds
    • 3 Baths

    115 Azalea St, Tavernier, FL 33070

    This stunning property offers the perfect blend of resort-style living and waterfront luxury, with a spacious 65-foot dock for your boat, and direct bay access. it's a paradise for those who love the water. Enjoy activities like fishing, swimming in the private pool with a jacuzzi overlooking the serene sea, or grilling in the outdoor built-in barbeque area. The house also has high-impact windows

    Merlin Perez Golden International Realty Corp

    115 Azalea St, Tavernier, FL 33070
  • /38

    $590,000 Pre-Foreclosure

    • 2 Beds
    • 2 Baths
    • 1,352 Sq Ft

    87200 Overseas Hwy Unit C3, Islamorada, FL 33036

    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,

    Maria Pilar Revoredo One Sotheby's International Re

    87200 Overseas Hwy Unit C3, Islamorada, FL 33036
  • /50

    $850,000

    • 3 Beds
    • 3 Baths

    313 Bayview Ave, Key Largo, FL 33037

    Stunning 3 Bedroom, 3 Bath Keys Retreat with Rooftop Deck, In-Law Quarters & Water Views!Welcome to your dream home in the heart of the Florida Keys! This beautifully crafted 3-bedroom, 3-bath home is built entirely of CBS construction with a solid concrete roof, offering peace of mind in paradise. Enjoy breathtaking bay views from the expansive rooftop deck—perfect for sunsets, entertaining,

    Rodolfo Sardina Seaside Realty LLC

    313 Bayview Ave, Key Largo, FL 33037
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