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$3,995,000
5 Beds ⋅ 4 Baths ⋅ 620430 MLS
Discover a rare opportunity to own an exceptional oceanfront estate in the heart of Islamorada that seamlessly combines luxury living with an established, successful vacation rental history. Situated on 1.82 private acres with approximately 225 feet of ocean frontage, this Residential Estate-zoned property is currently licensed for legal 7-day vacation rentals, making it one of the limited number of properties within the Village of Islamorada offering this highly sought-after privilege. With a documented history as a successful income-producing vacation rental, this property offers the opportunity to enjoy an extraordinary Florida Keys lifestyle while rental income may help offset the costs of ownership. A gated entrance welcomes you through a majestic Royal Palm-lined circular driveway to an impressive, covered portico. Inside, a dramatic foyer and elegant wrought-iron staircase set the tone for a home featuring five spacious bedrooms, four beautifully appointed bathrooms, and breathtaking ocean views throughout. Enjoy spectacular sunrises from the observation pier or relax year-round in the heated and chilled saltwater pool. The home is beautifully appointed with quartz countertops, premium appliances, impact-resistant windows, and exceptional craftsmanship throughout. Whether you're seeking a luxurious private residence or a proven income-producing property to help offset costs, this ideal combination of both is a remarkable Islamorada estate that offers an exceptional blend of privacy, oceanfront beauty, and one of the most desirable licensed weekly vacation rental opportunities in the Florida Keys.

87445 Old Hwy, Islamorada
$1,750,000
619538 MLS
This luxury commercial property in the heart of Islamorada offers prime US-1 highway frontage with high visibility, dual access to Old Highway, and a large, lit highway sign for maximum exposure. Built in 2015, this 3,000 SF mixed-use building features 1,500 SF of premium commercial space on the ground floor, including a grand reception area, two executive offices, a spacious conference room, a full kitchen, and an ADA-compliant bathroom, making it ideal for medical, legal, real estate, or executive office use. The 1,500 SF second-floor residential unit includes two bedrooms, two bathrooms, a modern kitchen, and a private balcony, offering luxury accommodations for an owner-user or an excellent rental income opportunity. Never permanently occupied, it remains in brand-new condition with no expenses spared. HC-Highway Commercial zoning allows for flexible use, making this a prime opportunity for a business owner, investor, or real estate professional. This turnkey property has never been leased and has been owner-occupied since completion.

87847 Overseas Hwy, Islamorada
$2,600,000
4 Beds ⋅ 5 Baths ⋅ 618956 MLS
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 Keys. Spacious interiors, high-end finishes, and thoughtful craftsmanship throughout reflect 4 Keys Construction's latest masterpiece, including a gourmet kitchen equipped with premium Miele appliances. Ideally located, Pickle Ball Estate offers access to a community boat ramp, perfect for days on the water, and is just minutes from Founders Park, where you can enjoy beaches, events, sports facilities, and family-friendly amenities. Whether you are seeking a primary residence, a vacation home, or an investment property, Pickle Ball Estate delivers the ultimate Islamorada lifestyle with luxury, recreation, and island living at its finest.

114 Royal Ln, Islamorada
$3,800,000
5 Beds ⋅ 3 Baths ⋅ 618165 MLS
Tired of waiting on Uber or Freebee? Why not make this stunning bayfront estate your own private slice of paradise, right in the heart of Islamorada? Just a flip-flop stroll away from local favorites like MEAT Eatery, Shima, Marker 88, and City Hall Café, this property places you at the vibrant core of island living. Behind its private, fully fenced grounds, you'll discover sweeping bay views and a rare tiki hut at the end of the dock—your new go-to spot for toasting unforgettable sunsets. Upstairs, the open-concept living area spills out through sliding glass doors onto a spacious, screened-in terrace, perfect for laid-back evenings or lively gatherings. This level also features three bedrooms and two baths, providing plenty of space for guests or family. Step down from the terrace to your own tropical oasis, complete with a pool, backyard, beach, and dock. The ground floor adds even more flexibility with two additional bedrooms, a bath, and a relaxed living area—ideal for guests or extended family. Whether you're looking for your forever getaway in the Keys or a smart investment when you're not soaking it all in yourself, this property is a rare find. Come see why life really is better by the bay.

87950 Overseas Hwy, Islamorada
$1,400,000
3 Beds ⋅ 3 Baths ⋅ 615089 MLS
Nestled on a generous half-acre lot in one of Plantation Key's most sought-after neighborhoods, this stunning 3-bedroom, 2.5-bath home with a dedicated office offers the perfect blend of comfort, style, and island living. Boasting 2,117 sq ft of interior space, this property also includes a small guest quarters—ideal for extended family or visiting friends. Step inside to discover a bright, open-concept layout with tasteful finishes and an easy flow from the living room to the dining area and kitchen. The dedicated office provides the flexibility to work from home in peace, while the spacious primary suite offers a private sanctuary complete with an en-suite bath. Step outside and you'll find an entertainer's paradise. The heated swimming pool with a waterfall is perfect for year-round enjoyment, while the covered outdoor entertainment area and cozy fire pit create the ideal setting for gatherings under the stars. The oversized two-car garage offers ample room for vehicles, tools, and toys—plus extra space for your boating or fishing gear. Lush tropical landscaping surrounds the home, offering privacy and a true sense of tranquility just minutes from schools, marinas, restaurants, and all that the Florida Keys lifestyle has to offer. The community offers one of the most premier homeowner parks in the Upper Keys with an exceptional blend of amenities and natural beauty. Enjoy a private beach, boat ramp, and temporary dockage—perfect for boating enthusiasts. Soak in breathtaking sunsets over the water and take advantage of a tranquil setting that captures the best of Florida Keys living. Whether you're looking for a full-time residence, vacation home, or investment opportunity, this rare gem on Plantation Key has it all.

145 Plantation Blvd, Islamorada
$795,000
3 Beds ⋅ 2 Baths ⋅ 609784 MLS
Solid as a Rock! This CBS home with a concrete roof is located in one of the best neighborhoods in Islamorada! Situated on an oversized lot with lots of mature native trees, this spacious three bedroom, 2 bath home is ready and waiting for you to enjoy. The screened porch across the front is perfect for relaxing and bird watching. The back yard is fully fenced and there is a circular driveway in the front for ease of parking and access. There's a nice sized storage shed in the back yard which could be a workshop. Right down the street is one of the best homeowners' parks in the area. This private, gated park offers a bayfront beach with lounge chairs, a roped off swimming area, volleyball, picnic tables, kayak and paddleboard storage and boat ramp. Enjoy fabulous sunsets nightly from Sunset Point.

100 Orange Ln, Islamorada
$364,125
1 Beds ⋅ 1 Baths ⋅ 607890 MLS
Welcome to your Affordable Islamorada Bungalow. Built in 2018, this 1b/1b home with an additional loft space for versatile use accessible with an upgraded staircase features CBS construction, impact windows and doors and sleek metal roof. Inside, the kitchen showcases quartz countertops and stainless-steel appliances, providing a functional and aesthetically pleasing space. The interior features include tile floors, walk in shower, and a stackable washer/dryer setup, ensuring efficiency in daily living. An inviting connection to the outdoors is established through a sliding glass door in the primary leading to the backyard. Neighborhood access to HOA park with BEACH, BOAT RAMP and walking distance to Founders Park. Buyer must live & work in Monroe County and meet income standards to purchase home. See 2023 Affordable Housing Fact sheet in Documents tab.Yearly maximum income for 1 person is $106,400, and 2 person is $121,520.

97 Orange Ln Unit 4, Islamorada
$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
$1,050,000
4 Beds ⋅ 3 Baths ⋅ 605846 MLS
Custom built in 2015, this 2,546sf Islamorada home has 4 bedrooms and 3 bathrooms. Beyond the large entry foyer is the Great Room boasting 23' high ceilings with expansive floor to ceiling windows. This open concept is the perfect place for entertaining and family gatherings! The well appointed kitchen features Bosch induction and double wall ovens, 2 dishwashers plus a walk in pantry with coffee center. Dual 9' sliding glass doors open to the covered outdoor living space. The spacious Primary ensuite with a walk-in closet is ground floor as are 2 well appointed bedrooms, and a centralized laundry room. The second floor is home to an open loft sitting area leading to the generously sized fourth bedroom ensuite. Not included in home's square footage is bonus finished flex space that can be hideaway play area and/or storage The home is located on an oversized 11,400sf lot with mature native vegetation. Plenty of room on the side of the house for a boat, RV and more! This CBS home has all impact windows and doors, a metal roof and a large air conditioned storage room at the back of the house. The bay front Homeowner's Park right at the end of the street is one of the nicest in Islamorada offering a boat ramp, beach area and endless sunsets! This home is located on Plantation Key, just minutes from Plantation Key Elementary School, Coral Shores High School, Treasure Village Montessori and the fabulous Founder's Park.

108 Orange Ln, Islamorada
$364,125
1 Beds ⋅ 1 Baths ⋅ 608160 MLS
Newly Built in 2018 this Quaint Home Offers all the Charm of Islamorada at an Affordable Price. This 1Bedroom/ 1Bath Home Features CBS Construction, Impact Windows and Doors, SS Appliances, Quartz Countertops, Porcelain Tile and, a Huge 2nd Floor Loft. Located in the Gorgeous Plantation Beach Subdivision w/ access to the neighborhood HOA Park. HOA Park includes Beach Volleyball, Bayfront Protected Swimming Area, Beach, Boat Ramp and More. This home is 1 of 6 units In the Orange Ln. Affordable Housing Deed Restricted Community. Unit 6 is the Rear Unit, furthest from the Highway and has a Fully Fenced Back Yard. Buyers Must Live and Work in Monroe County and meet Income Standards to Qualify for Home Purchase. The yearly Maximum income for 1 person is $106,400, and 2 person is $121,520. See full 2023 Affordable Housing Facts Sheet in documents tab.

97 Orange Ln Unit 6, 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
$542,000
606260 MLS
In the sought-after Plantation Beach neighborhood on Plantation Key, an exceptional 12,000 sq. ft. vacant lot awaits, complete with an ACTIVE PERMIT. This centrally situated, prime property boasts proximity to Founders Park, various dining establishments, schools, the hospital, and more. Renowned for its family-friendly environment, the Plantation Beach subdivision features an impressive bayfront homeowners park complemented by a convenient boat ramp. Enjoy direct bay access and seamless ocean access through Tavernier Creek or Snake Creek. The lot, already cleared, stands ready for a fresh residence. The approved plans encompass a three-bedroom, two-bathroom layout with an additional bonus room upstairs. Downstairs has a one-bedroom, one-bathroom configuration coupled with a large workshop area. (Buyer has the option to make revisions to the current plans or submit new plans.) With the permit secured and paid for, seize the perfect opportunity to construct your dream home in the captivating Florida Keys.

114 Royal Ln, Islamorada
$9,000,000
5 Beds ⋅ 6 Baths ⋅ 608065 MLS
Luxury Oceanfront Estate in Islamorada - Island Living at Its Finest! Welcome to your private paradise where luxury meets tranquility. This exquisite oceanfront estate is a true gem, offering unparalleled elegance, stunning Atlantic Ocean views and a harmonious blend of island living and modern luxury. Nestled on the Atlantic Ocean, this estate boasts a prime location with 450 feet of pristine beachfront accessible via a private, gated entrance and a long winding breathtaking road. Spanning almost 8 acres of upland and an additional 2 acres of bay bottom, this expansive property provides a rare and generous slice of paradise in the Florida Keys. Between the main house and the guest house lies a heated pool and hot tub with a Keystone deck, creating the perfect spot to bask in the island lifestyle while overlooking the Atlantic Ocean. Grand porches at the back of the home invite you to enjoy the refreshing ocean breeze.The main house, encompassing 6652 sqft of living space. The entrance features marble flooring with two elegant staircases, setting the tone for the opulence that awaits within. Floor-to-ceiling windows in the living area invite abundant natural light and offer uninterrupted views of the Atlantic Ocean.The gourmet kitchen is a culinary masterpiece, featuring artisan-style cabinetry, a gas Thermador stove with double ovens, an oversized pantry, and a Sub Zero refrigerator.The main floor includes a luxurious guest suite with a Jacuzzi tub and spa-like showers, while the third story is dedicated to two grand master suites, ensuring privacy and comfort. A separate guest house, comprising 1161sqft, offers two oversized bedrooms with ensuite bathrooms, living room with an abundance of natural light. Both the main house and the guest house feature Brazilian Mahogany throughout, adding an extra touch of sophistication to this already magnificent residence. This property is not a home; it's a lifestyle. DOCK PERMIT APPLIED FOR! WEEKLY RENTALS ALLOWED!

88011 Old Hwy, Islamorada
$1,150,000
607846 MLS
Introducing a RARE and exceptional opportunity in the heart of Islamorada, FL. This clean, vacant commercial property boasts an impressive 400 feet of frontage along both US1 and Old Highway, offering unparalleled visibility in a highly sought-after location. With a total of 33,904 square feet of vacant land, this property comprises four separate mixed-use parcels, as well as one parcel zoned for medium-density residential use according to the FLUM map. Buyer to verify development options. Situated in close proximity to a new major development, and less than 5 miles away from the renowned Founders Park, which offers a marina, boat ramp, and an array of recreational amenities, this property is ideally positioned for maximum exposure and accessibility. The entire property is fully fenced in, providing security and privacy, and is ready for development, offering a blank canvas for your commercial vision. The seller has already prepared plans for a commercial building with less than 1,000 square feet, providing a convenient starting point for potential buyers. Furthermore, a comprehensive survey and vegetation survey have been completed, ensuring a smooth and informed development process. All five parcels are included in the sale, presenting a unique and versatile investment opportunity in the coveted Florida Keys. Don't miss out on this chance to acquire prime commercial real estate in one of Islamorada's most desirable locations. Seize the opportunity to become a part of this thriving community and unlock the potential for a prosperous venture in this vibrant coastal paradise.

87462 Old Hwy, Islamorada
$835,000
2 Beds ⋅ 2 Baths ⋅ 605682 MLS
Privacy in Paradise! 2 Bed/2 Bath Home in Plantation Beach, Islamorada. This beautiful home is nestled in lush, tropical native landscape, situated on a large, oversized lot of 15,750 sq. ft. that is elevated well above flood. The huge backyard patio is perfect for entertaining guests or simply enjoying the outdoors. The kitchen is well appointed with plenty of cabinetry and the living room features a faux coral wall that adds a touch of luxury. The bedrooms are very comfortable and of good size, the primary bedroom boasts an updated bathroom. This home has been well-maintained by the current owners. You will love living in the quaint community of Plantation Beach! This quiet neighborhood offers one of the best Bayfront homeowners parks with a boat ramp and beach, launch your kayak, canoe or paddleboard and enjoy the sunsets. Located close to Founders Park, schools, restaurants, and shopping yet a world away. Come and enjoy all that Islamorada has to offer! Schedule a showing today to experience this amazing home for yourself!

116 Coconut Ln, Islamorada
$5,970,000
4 Beds ⋅ 3 Baths ⋅ 612474 MLS
An incomparable bayside Islamorada compound with an exempted deep-dredge boat basin, this enchanting property provides 100' of direct waterfront and .7 acres of professionally manicured mature grounds. Move-in ready 4-bedroom residence offered for only the second time in a generation also provides an opportunity to build a one-of-a-kind property in the coveted Plantation Beach estate area. Enter via a gated entrance with stately mature mahogany trees and towering palms to your own private retreat. The serene and private sanctuary includes a saltwater infinity pool, complete with a spa, heater, and chiller. With year-round direct sunset views, enjoy golden hour evenings lit with tiki torches and landscape lighting throughout. This two-story above-flood traditional keys home offers four bedrooms and three full baths, with an interior staircase that includes separate quarters and an extra kitchenette - an ideal layout for family living or hosting guests. Additional features include a whole house generator, a security system, a spacious garage, and dolphin swim-bys. The neighborhood offers a homeowner's park with a boat ramp, beach, and picnic area. It is on a quiet street amongst prestigious estates in a most desirable Plantation Key neighborhood.

178 Plantation Blvd, Islamorada
$965,000
3 Beds ⋅ 3 Baths ⋅ 615889 MLS
Attractive Islamorada Concrete Home with In-Law Quarters in Exceptional Subdivision! Welcome to this inviting three bedroom, three bathroom home with an open living area and welcoming kitchen. This spacious residence features a separate in-law quarters—perfect for guests or extended family. The professionally landscaped front yard and private courtyard create unbeatable curb appeal, with covered parking and additional expansive open parking. Enjoy access to one of Islamorada's premier homeowner's parks with a sandy beach, boat ramp, and awe-inspiring sunset views. Don't miss this rare opportunity to own your slice of paradise in the Florida Keys!

141 Plantation Blvd, Islamorada