Islamorada FL Real Estate & Homes for Sale

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Beds:
7
Baths:
10.00
Sq.Ft.:
8,288
Status:
NEW LISTING
MLS#:
A12022973
Type:
Single Family
Subdivision:
Islamorada
Year built:
2017
Courtesy: Ocean Sothebys Intl Realty Gonzalo Del Negro 305-842-0559
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ADDITIONAL INFORMATION

Welcome to Serenity Cay, an exquisite Balinese-inspired estate where tranquility and luxury meet the endless beauty on the Florida Bay. A true masterpiece of engineering and design, this sprawling waterfront residence on nearly four acres offers an unparalleled blend of tropical elegance, sophisticated craftsmanship, and modern luxury. An expansive infinity-edge pool blends seamlessly into the sparkling waters of the bay while lush gardens create a serene oasis. The home's architecture showcases graceful, custom finishes and rich hardwoods, all hallmarks designs that evoke the spirit of the Islands. The interior is a seamless fusion of open-concept living spaces and private retreats. Soaring vaulted ceilings and vast windows invite abundant natural light and spectacular views of the bay, creating an indoor-outdoor flow. The primary suite serves as your personal sanctuary, complete with private terrace, spa-inspired bathroom, and walk-in closets fit for a connoisseur of fine living. Each guest has direct access to outdoor spaces and views. A versatile bunk room/media center sits just off the west wing of the home. The charming guest house is the perfect complement to the main home, nestled in its own secluded on site location this delightful addition exudes a warm, welcoming ambiance ideal for hosting guests, or as a private office or creative studio.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,152
Status:
NEW LISTING
MLS#:
619965
Type:
Multi-Family
Subdivision:
Port Of Call (88.5)
Lot size:
2,052 Acres
Year built:
1991
Courtesy: Ocean Sotheby's International Realty 305-712-8888
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ADDITIONAL INFORMATION

Welcome to Port of Call--an intimate oceanfront enclave on Plantation Key where refined coastal living meets the effortless rhythm of the Florida Keys. Tucked within this exclusive 10-residence boutique community, 136 Aregood Lane offers a rare blend of luxury, privacy, and true serenity. This beautifully appointed 2-bedroom, 2.5-bath townhome is designed for both relaxation and adventure, featuring weekly rental eligibility, assigned dockage, a community pool, and a private rooftop deck with sweeping ocean views. Flooded with natural light, the main living level flows seamlessly to a private balcony where gentle breezes and glimpses of turquoise water set the tone for quiet island living. The thoughtful floor plan provides generous space for entertaining, while the additional half bath on this level ensures comfort for guests. Upstairs, two spacious en-suite bedrooms--each with its own balcony--offer peaceful retreats after a day on the water. With all impact windows and doors, the home delivers both beauty and peace of mind, allowing you to enjoy the Keys lifestyle with ease. For boating enthusiasts, the assigned boat slip with direct ocean access opens the door to world-class fishing, diving, and cruising. Spend your days exploring the Atlantic, then return to unwind by the community pool or stroll the private beach area as the sun dips below the horizon. Perfectly positioned in the heart of Islamorada, you're just minutes from Islamorada's renowned dining, shopping, and cultural experiences--yet worlds away from the everyday. Whether you envision a full-time residence, a weekend escape, or a high-demand investment property, this exceptional townhome delivers unmatched flexibility with its weekly rental capability and coveted oceanfront amenities. Port of Call is a place where luxury feels effortless, the ocean is your backyard, and every day begins with possibility.

Beds:
4
Baths:
5.00
Sq.Ft.:
4,048
Status:
NEW LISTING
MLS#:
619928
Type:
Single Family
Subdivision:
Lower Mat Bch (74.0)
Lot size:
0.59 Acres
Year built:
1989
Courtesy: Palm House Real Estate 305-304-8841
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ADDITIONAL INFORMATION

Discover paradise in Islamorada, with beautiful ocean views, protected canal dockage, and resort-style amenities that you'll never want to leave! Blending luxury living with the Florida Keys lifestyle, this home is designed with both entertaining and relaxation in mind. You'll find modern touches throughout this fully-furnished 4 bed, 5 bath home with an abundance of natural light enhancing it's coastal charm. The main level showcases ocean views from the large kitchen, living and dining areas, a French door sunroom and a massive elevated patio for seamless indoor/outdoor entertaining. Head downstairs and bring your resort experience to life. Relax under the poolside beach cabana, complete with an outdoor kitchen and furnished interior bonus room with a full bath connected by interior stairs or elevator. Sunbathe on your sandy beach complemented by a well-manicured backyard with privacy landscaping, mangroves, palm trees and a turf lawn. Take a dip in the resort-style pool/spa, play a little putt-putt golf, or use the access steps to the canal and explore the oceanside bonefish flat. Located in the heart of the sportfishing capital of the world, this home has the avid fishermen and watersport enthusiasts covered. With 200' of waterfrontage and 90' of dockage, safely secure your boats on the 40,000# or 15,000# lifts in the deep protected canal. Within minutes you could head offshore chasing big game fish or run bayside to fish the backcountry or explore the Everglades park. Just steps away from your dock is a dedicated tackle room complete with a chest freezer, commercial ice machine, rigging bench, rod racks and tool storage. Accompanied by an oversized 2 car garage, you'll have plenty of room to store all your toys and cars. Concrete construction, newer Interlock Aluminum Slate Roofing and equipped with impact windows & doors, this home was built to withstand anything. Start living your dream today in this true Florida Keys retreat on beautiful Lower Matecumbe.

Beds:
1
Baths:
1.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
A12017273
Type:
Mobile Home
Subdivision:
WINDLEY KEY MOBILE HOME P
Lot size:
0.02 Acres
Year built:
1980
Courtesy: KB Realty Stanley Samy 786-619-4747
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ADDITIONAL INFORMATION

Escape to your own slice of paradise with this cozy and beautifully kept 1-bedroom, 1-bath Jayco RV. Whether you’re looking for a peaceful weekend retreat, a seasonal getaway, or a spot with great rental potential, this charming hideaway has it all. Wake up to the soothing sounds of the Atlantic and enjoy unforgettable sunrises and sunsets right from the jetty. Nestled in a rare, intimate oceanfront community, you’ll love the relaxed lifestyle and low association fees. Spend your days soaking up the sun, launching your kayak or small boat, or taking advantage of the fish-cleaning station and marina. It’s the perfect chance to own a tranquil oceanfront retreat—simple, serene, and full of coastal charm.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,110
Status:
NEW LISTING
MLS#:
619931
Type:
Single Family
Subdivision:
Venetian Shores (86.0)
Lot size:
0.22 Acres
Year built:
1978
Courtesy: Coldwell Banker Schmitt Islamorada 305-664-4470
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ADDITIONAL INFORMATION

What does everyone want? The smallest house in a great neighborhood! THIS IS THE ONE! Tucked away in the sought-after Venetian Shores neighborhood of Islamorada, this solid CBS waterfront home is perfectly positioned for enjoying the effortless boating lifestyle the Keys are known for. With 100 feet of dockage, a 15,000 lb. boat lift, and a fish cleaning station, this home is just one lot from Snake Creek which offers immediate access to both the Atlantic Ocean and Florida Bay. Enjoy peaceful Snake Creek views and the constant reminder that the water is always just moments away. Upstairs, the open floor plan is designed to capture natural light and Snake Creek views, with vaulted ceilings creating an airy coastal feel throughout the living, dining, and kitchen areas that span the width of the home. Three sets of sliding glass doors invite the outdoors in, opening the space to breezes and waterfront scenery. Two bedrooms and one full bath complete the upper level, while downstairs offers valuable storage space, a permitted full bath, and covered carport parking. The cleared lot provides exceptional flexibility with ample room for boats on trailers, additional vehicles, or the opportunity to expand the existing home and create an even larger waterfront retreat. Don't miss out on this exceptional value!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,026
Status:
NEW LISTING
MLS#:
619919
Type:
Condo/Townhouse
Subdivision:
Bay Harbour (75.0)
Year built:
2003
Courtesy: Ocean Sotheby's International Realty 305-712-8888
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ADDITIONAL INFORMATION

Experience luxury island living in the heart of Islamorada at Bay Harbour, one of the Florida Keys' most desirable waterfront communities. Unit 204 offers breathtaking ocean and lagoon water views and an exceptional blend of elegance, comfort, and investment potential. This spacious 3-bedroom, 2.5-bath residence has been fully remodeled and impeccably maintained, featuring beautiful high-end finishes throughout and a stunning designer kitchen perfect for entertaining. The oversized primary suite offers a true retreat with a spacious bedroom and a beautifully appointed spa-inspired primary bathroom. Offered 100% turnkey, this residence is ready for immediate enjoyment or income production, with the flexibility of 7-day rentals and a strong established, impressive rental history. Boaters will appreciate the assigned boat slip and private 20,000-pound boat lift, providing easy access to some of the best fishing and boating in the Florida Keys. Bay Harbour is known for its upscale amenities, prime location, and relaxed coastal lifestyle, making this an exceptional opportunity for both personal enjoyment and investment.

Beds:
7
Baths:
7.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
A12017379
Type:
Single Family
Subdivision:
Mat Ocean Bay
Lot size:
2.08 Acres
Year built:
2025
Courtesy: Langley Knight Gardner Islamorada Lisa Frins 305-522-1479
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ADDITIONAL INFORMATION

LUXURY BEACHFRONT ESTATE HOME! Come embrace this brand-new magnificent property where you will encounter a relaxing ambiance gracefully set on over 2 private acres of pristine bayfront offering deep-water dockage with a 20,000 lb boat lift, a white sandy beach and stunning unobstructed panoramic views of the Florida Bay located in desirable Lower Matecumbe. Spanning nearly 6,000 square feet of extraordinary living space with 7 bedrooms and 7 bathrooms. Thoughtfully designed for ultimate comfort, this estate features two separate guest wings, each offering three private bedroom suites, ideal for family, guests or an unparalleled private retreat. The gourmet chef's kitchen, perfect for entertaining, leads to an expansive and inviting great room, elegant tray ceilings, designer finishes, and sophisticated architectural details throughout. A private elevator offers effortless access between levels. Step outside to your own tropical sanctuary, where a stunning pool deck overlooks the sparkling waters of Florida Bay. Lush tropical landscaping provides privacy, while spacious covered terraces provide the perfect backdrop for unforgettable sunsets and year-round outdoor living. With weekly rentals permitted and a valuable vacation rental license in place, this rare offering combines luxurious personal enjoyment with outstanding investment potential. Experience the Florida Keys lifestyle in one of Lower Matecumbe's most exclusive waterfront settings.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,260
Status:
Active
MLS#:
619869
Type:
Single Family
Subdivision:
Mat Ocean Beach (75.0)
Lot size:
0.35 Acres
Year built:
1988
Courtesy: Coastal Realty of the Florida Keys 305-664-0077
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ADDITIONAL INFORMATION

Beautifully renovated oceanfront home in Islamorada offering 100 feet of direct ocean frontage, a sandy beach, breathtaking open water views, and mature tropical landscaping. This exceptional concrete stilt home has undergone a spectacular extensive coastal renovation, blending modern luxury with the relaxed elegance of the Florida Keys lifestyle. The residence features 3 bedrooms and 3 bathrooms with a bright, open-concept floor plan designed to maximize natural light and panoramic ocean views. The upstairs living quarters include a stunning new chef's kitchen with custom cabinetry, premium countertops, and high-end appliances, along with beautifully renovated bathrooms and spacious living and dining areas that flow seamlessly onto the elevated oceanfront porch. Recent upgrades include a brand new roof, all new impact windows and doors, renovated bathrooms, a fully redesigned kitchen, updated finishes throughout, and extensive coastal improvements designed for both style and durability. The gated and fenced property also features a gorgeous oceanfront swimming pool with updated pool equipment, outdoor shower, covered parking for multiple vehicles and boats, and abundant storage space. Outdoor enthusiasts will appreciate the impressive 90-foot oceanfront fishing pier with concrete pilings and low-maintenance composite decking, creating the perfect setting to fish, relax, entertain, or take in the spectacular sunrise views over the Atlantic Ocean. This is a rare opportunity to own a fully renovated luxury oceanfront retreat in Islamorada, known as the ''Fishing Capital of the World.''

Beds:
4
Baths:
5.00
Sq.Ft.:
2,574
Status:
Active
MLS#:
619832
Type:
Single Family
Subdivision:
Russell Estates (83.2)
Lot size:
7.61 Acres
Year built:
2020
Courtesy: Ocean Sotheby's International Realty 305-712-8888
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ADDITIONAL INFORMATION

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 either full time residency or 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.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,022
Status:
Active
MLS#:
619848
Type:
Single Family
Subdivision:
Misc Upper Matacumbe (82.0)
Lot size:
0.27 Acres
Year built:
2020
Courtesy: Flat Fee MLS Realty 813-642-6030
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ADDITIONAL INFORMATION

Experience all that Islamorada has to offer from this stunning home that was constructed in 2020. This two-story residence offers 3 spacious bedrooms and 2 full bathrooms on the ground floor. The second floor has a large great room - ideal for a home office, second living room, playroom, or media space--adding extra versatility to the layout. Additionally, there is another full bathroom upstairs. Step into an open-concept main living area with numerous windows to let in the natural light. Easy to clean tile throughout. The heart of the home is a modern kitchen featuring a large island, custom cabinetry, and premium finishes--perfect for entertaining and everyday living. The spacious side and backyard provide ample space for trailers, boats, or a future pool, making it perfect for outdoor enthusiasts. Speaking of pool, there is a current, valid pool permit that has been issued for the property and can be transferred to the next owner. This home is located just minutes from the ocean, marinas, shopping, and dining. It is zoned for highly rated Coral Shores High School. This home offers the rare opportunity to own an almost new, move-in-ready property in the Upper Keys. Don't wait--schedule your private showing today and make this modern island retreat your forever home!

Beds:
1
Baths:
1.00
Sq.Ft.:
550
Status:
Active
MLS#:
619786
Type:
Condo/Townhouse
Subdivision:
Strattons (82.5)
Year built:
1988
Courtesy: Ocean Sotheby's International Realty 305-712-8888
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ADDITIONAL INFORMATION

Welcome to your island King suite overlooking the beautiful lagoon at the historic Cheeca Lodge & Spa. Income producing property allowing 28 fabulous owner days! Cheeca handles all vacation rentals making your investment hassle free. The resort offers a spa, Camp Cheeca for the kids, beachfront pool, 9-hole par 3 golf course, lush gardens, bike path, tennis courts, fitness center, 5 star dining, tiki bar, beach, dock, water sports, and fishing. Sleeper sofa in living area for additional sleeping. Monthly condo insurance is $854 in addition to the monthly association fee.

Beds:
1
Baths:
2.00
Sq.Ft.:
827
Status:
Active
MLS#:
619718
Type:
Condo/Townhouse
Subdivision:
The Palms A Condominium (905.0)
Year built:
1976
Courtesy: Ocean Sotheby's International Realty 305-712-8888
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ADDITIONAL INFORMATION

The Palms of Islamorada is one of Islamorada's true sweet spots! Enjoy the oceanfront pool with nearby steps leading directly into the water where you can take a refreshing dip while soaking in panoramic open ocean views. This spacious one-bedroom residence features a large primary bedroom and bathroom with a dressing area, plus an additional half bath for guests. Recent updates include newer appliances, water heater, and A/C for added comfort and peace of mind. Fresh interior paint and motorized blinds throughout plus impact doors and windows as well. Ideally located near Bud N' Mary's Marina and some of Islamorada's most celebrated restaurants, this property offers the perfect blend of relaxation, convenience, and the Florida Keys lifestyle.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,261
Status:
Active
MLS#:
619711
Type:
Condo/Townhouse
Subdivision:
Sand Pebbles (80.5)
Year built:
1983
Courtesy: Ocean Sotheby's International Realty 305-712-8888
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ADDITIONAL INFORMATION

Welcome to Sand Pebbles -- Islamorada's Hidden Gem. Located in the heart of the Village of Islamorada, this spacious 2-bedroom, 2-bathroom condo at the boutique community of Sand Pebbles offers the quintessential Florida Keys lifestyle you've been dreaming of. With only 16 units, Sand Pebbles delivers an intimate, low-key atmosphere that larger communities simply can't match -- your own private slice of island paradise. Step inside and discover a bright, airy layout designed for both relaxed living and effortless entertaining. The open-concept floor plan flows naturally, with two generously sized bedrooms and two full baths offering the perfect retreat after a day on the water. Community amenities that elevate everyday life: heated resort-style pool, tiki hut, garden areas, a bayfront observation pier, and on-site trailer storage. Boaters will enjoy easy access to the nearby Safe Harbor Angler House Marina for all of their boating needs. Located just moments from world-class sportfishing, diving, dining, and the eclectic local shops that make Islamorada truly special, Sand Pebbles places you at the center of it all while maintaining the peaceful, uncrowded feel of a private retreat.

Beds:
4
Baths:
4.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
A12010138
Type:
Single Family
Subdivision:
Lower Matecumbe
Lot size:
0.48 Acres
Year built:
1970
Courtesy: Realty One Group Engage the Keys Judy Rossignol 305-393-0523
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ADDITIONAL INFORMATION

The gated entrance supplies a perfect level of privacy. The approach sets the tone for the entire experience: peaceful, secluded, and authentically 'Old Florida,' yet elevated with the sophistication expected in a luxury Keys residence. Whether used as a full-time home, a seasonal retreat, or a legacy property to be enjoyed for generations, Casa Matecumbe offers a rare combination of location, land, and lifestyle that is nearly impossible to replicate. The main residence is thoughtfully positioned to maximize panoramic ocean views from nearly every room. Expansive windows and glass doors frame the turquoise water, inviting natural light to fill the interior spaces throughout the day. Upstairs there are 3 bedrooms and 2 baths as well as a gorgeous kitchen an open concept with dining under air conditioning or al fresco, Downstairs includes a large en-suite bedroom with water views as well as an additional kitchen and dining living area. Both levels offer a breezy indoor-outdoor living--with modern comforts including updated finishes, impact windows, and spacious living areas. This 4-bedroom House is the perfect vacation home for larger families wishing to enjoy the pool, the beach and the ocean in a private setting.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,123
Status:
Active
MLS#:
619722
Type:
Single Family
Subdivision:
Mat Ocean View (76.5)
Lot size:
0.17 Acres
Year built:
1979
Courtesy: Ocean Sotheby's International Realty 305-712-8888
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ADDITIONAL INFORMATION

Impeccably Designed Islamorada Waterfront Retreat! Welcome to your private island oasis! This stunning 3BR/3BA solid concrete waterfront home on Lower Matecumbe Key combines comfort and style with the ultimate Florida Keys lifestyle. Beautifully updated, this turnkey residence is move-in ready for immediate enjoyment. The inviting floor plan features a well-appointed kitchen with quartz countertops and stainless appliances with open living concept, a spacious primary en suite, and a versatile downstairs guest suite with bedroom and living area--perfect for hosting family and friends or creating your own private retreat. Situated on a canal with immediate ocean access, the property includes 75 feet of concrete dockage with boat lift for the boating enthusiast. The resort-style backyard is designed for endless entertaining with a heated pool, expansive sun deck, screened porch, and multiple indoor-outdoor living spaces--your personal vacation paradise. Located just minutes from Islamorada's acclaimed restaurants, local marinas, world-class fishing, and island attractions, this exceptional home offers the perfect balance of waterfront tranquility and vibrant Keys living. Whether you're lounging poolside, departing for a day on the water, or gathering with loved ones, every day feels like a getaway. Low Flood Insurance currently $2075 available to transfer.

Beds:
8
Baths:
6.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
A12009440
Type:
Single Family
Subdivision:
Strattons Subdivision Pb2-
Year built:
1984
Courtesy: LoKation Real Estate Tracey Petrusha 305-896-1080
View additional info

ADDITIONAL INFORMATION

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 residence features 7 spacious bedrooms and 5 beautifully appointed bathrooms designed with both elegance and comfort in mind--perfect for entertaining or hosting large gatherings. A dramatic third-floor Bird's Nest Sky Lounge features 360-degree glass walls and a walkout rooftop deck, capturing breathtaking vistas in every direction. Expansive living areas and thoughtfully designed spaces capture stunning water views from every angle. A private 1-bedroom, 1-bathroom guesthouse provides the ideal retreat for visitors, accommodating extended family, or potential rental income or creating a secluded retreat. For boating enthusiasts, the estate includes an impressive 85+ foot deep-water yacht slip and four boat lifts, offering seamless access to both the Bay and Ocean--an unparalleled fishing advantage in the Florida Keys.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,975
Status:
Active
MLS#:
619672
Type:
Single Family
Subdivision:
Plantation Lake Estates (87.0)
Lot size:
0.36 Acres
Year built:
2002
Courtesy: Berkshire Hathaway HomeServices Keys Real Estate - Islamorada 305-664-4444
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ADDITIONAL INFORMATION

Welcome to 310 North Drive, located in the gated community of Plantation Lake Estates. This solid concrete 4-bedroom, 2-bath home offers 1,975 sq ft of living space and sits on a rare 16,000 sq ft double lot with no neighbors on three sides, providing exceptional privacy. The home features recently renovated kitchen and bathrooms, a spacious wraparound porch, and an oversized 1,500+ sq ft garage/workshop. The seller is installing all impact windows and doors prior to closing, adding significant value and peace of mind. Enjoy access to the neighborhood's newly updated homeowners park, complete with a boat ramp and 72-hour dockage. Conveniently located directly across from Founders Park, offering beaches, a marina, pool, and pickleball courts. A rare opportunity combining concrete construction, privacy, boating access, and a prime location in one of Islamorada's most desirable gated communities.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,337
Status:
Active
MLS#:
A12006598
Type:
Condo
Subdivision:
EXECUTIVE BAY CLUB
Year built:
1980
Courtesy: Compass Florida, LLC. Christian Hoheb 954-540-8715
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ADDITIONAL INFORMATION

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 more spacious and inviting main living area ideal for everyday living or entertaining. EBC is highly desirable for boaters and investors alike, with first-come, first-served dockage available for boats, immediate bay access, and quick ocean access via Snake Creek and Tavernier Creek. Residents and guests enjoy a private sandy beach with beautiful sunset views, plus community amenities that include a renovated pool and clubhouse, tennis courts, pickleball courts, BBQ area, kayak launch, kayak storage, trailer parking, and secure gated entry. Short-term rentals are allowed with a 28-day minimum, making this an excellent opportunity for full-time living, a vacation getaway, or an income-producing property. Located in the heart of Islamorada and within walking distance to Founders Park events, recreation, and nearby dining, this property offers the ideal blend of waterfront enjoyment, boating convenience, and rental flexibility in one of the Florida Keys’ most desirable communities.

Beds:
1
Baths:
1.00
Sq.Ft.:
550
Status:
Active
MLS#:
619668
Type:
Condo/Townhouse
Subdivision:
Strattons (82.5)
Year built:
1988
Courtesy: Coldwell Banker Schmitt Key Largo 305-451-4422
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ADDITIONAL INFORMATION

Welcome to the iconic Cheeca Lodge & Spa Resort--a rare opportunity to own a premier, income-producing property in the heart of Islamorada. This beautifully appointed one king-bedded room with kitchen, private screened in balcony, with owners closet, offers the ideal blend of personal retreat and investment potential. Set within one of the Florida Keys' most celebrated resorts, owners and guests enjoy a true luxury experience, featuring exceptional dining, new ballroom, two tiki bars, a full-service spa, fitness center, and multiple resort-style pools, 9 hole, Par 3 golf course, The property boasts direct beach and dock access, along with lighted tennis courts, pickleball courts and a wide array of water sports, all surrounded by lush tropical landscaping. Nightly rentals are permitted, creating strong income potential, while professional onsite management provides seamless maintenance and guest services. Ideally located just moments from Islamorada's renowned restaurants, galleries, breweries, shopping, and vibrant art district, this is a unique chance to own within one of the Keys' most historic and sought-after destinations.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,124
Status:
Active
MLS#:
619594
Type:
Condo/Townhouse
Subdivision:
Las Maravillas (75.5)
Lot size:
0.02 Acres
Year built:
1988
Courtesy: Coastal Realty of the Florida Keys 305-664-0077
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ADDITIONAL INFORMATION

Fully furnished turn key townhome in Islamorada at Las Maravillas is available, one of only 10 private residences on the bayside on Lower Matecumbe in the Village. Dockage, covered parking, trailer storage, beautiful pool, gated and fenced grounds highway to bay right on Lower Matecumbe Bight. 2 bedrooms with Jack and Jill bathroom on the top floor could be converted to two bathrooms. Half bath, kitchen, dining and living area on main level. Storage room and drive thru parking underneath suitable for medium size boat on trailer or two cars. Tropical vegetation and fruit trees and nice landscaping. Kitchen and baths are modern. updated stainless appliances. Carpet and tile throughout. This is the opportunity to get into the keys at a modest price and enjoys the keys life. Owner occupied so notice is appreciated. Easy to show. Call ahead for appointment.

Beds:
3
Baths:
4.00
Sq.Ft.:
4,537
Status:
Active
MLS#:
619577
Type:
Single Family
Subdivision:
Penn Key Club (83.0)
Lot size:
0.3 Acres
Year built:
1987
Courtesy: Ocean Sotheby's International Realty 305-712-8888
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ADDITIONAL INFORMATION

Welcome to your legacy retreat in Islamorada's premier gated waterfront community. A rare blend of privacy, prestige, and resort‑style living awaits in this Key West-inspired residence, set within one of Islamorada's most exclusive gated bayfront communities. Surrounded by manicured tropical landscaping and timeless architectural charm, this home offers an elevated island lifestyle defined by serenity and sophistication. A palm‑lined entrance leads to a vibrant exterior with wraparound porches and sun‑filled interiors framed by lush garden views. The spacious three‑bedroom layout is designed for effortless indoor‑outdoor living, with multiple gathering spaces opening to expansive patios ideal for entertaining, unwinding, or savoring golden sunsets. Mature palms, bougainvillea, and the scent of salt air create a secluded sanctuary that feels worlds away. Residents enjoy exclusive access to a resort‑style pool, private beach, kayak launch, and a breathtaking sunset point reserved for owners. A protected marina provides direct access to world‑class sport fishing and boating, while full‑time on‑site property management ensures peace of mind whether you're home or away. Perfectly positioned in the heart of Islamorada, the home offers effortless proximity to fine dining, boutique shopping, and the legendary waters that define the sport fishing capital of the world. Whether you're seeking a seasonal escape or a long‑term legacy investment, this property delivers enduring value wrapped in unmatched natural beauty. Experience the rare combination of luxury, leisure, and privacy that makes the Legacy Retreat truly exceptional.

Beds:
5
Baths:
6.00
Sq.Ft.:
5,456
Status:
Active
MLS#:
A12000712
Type:
Single Family
Subdivision:
MATECUMBE SANDY BEACH
Lot size:
0.41 Acres
Year built:
2000
Courtesy: Ocean Sothebys Intl Realty Annie Hagen 305-304-1762
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ADDITIONAL INFORMATION

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.

Beds:
5
Baths:
6.00
Sq.Ft.:
4,770
Status:
Active
MLS#:
A12000654
Type:
Single Family
Subdivision:
MATE OCEAN BAY SUBD SEC 1
Lot size:
0.88 Acres
Year built:
2012
Courtesy: Ocean Sothebys Intl Realty Annie Hagen 305-304-1762
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ADDITIONAL INFORMATION

Set on 1.38 acres of pristine oceanfront in the Florida Keys, this private estate offers the perfect blend of luxury, serenity, and tropical beauty. With an enormous 150-foot private beach, this stunning 4,770-square-foot residence presents an unparalleled opportunity to experience the magic of oceanfront living.The home features five bedrooms and five and a half baths, including separate guest quarters for added privacy. Towering 30-foot ceilings create a grand, open atmosphere, while expansive windows frame breathtaking views of the Atlantic Ocean. Offered turnkey, this estate is move-in ready, with exquisite furnishings that complement its elegant design.Step outside to a resort-style infinity-edge pool with spa. A spacious two-car garage provides convenience, while the estate's zoning allows for weekly rentals, making it a remarkable investment opportunity.This property is more than just a home--it's a tropical oasis where you can kayak, fish, or build sandcastles right from your backyard. Whether you seek a family getaway or a primary residence, this estate offers the best of both worlds: a tranquil retreat surrounded by nature yet still within the comforts of the United States.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,224
Status:
Active
MLS#:
619533
Type:
Condo/Townhouse
Subdivision:
Coral Harbour (88.0)
Lot size:
14 Acres
Year built:
1979
Courtesy: Coldwell Banker Schmitt Islamorada 305-664-4470
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ADDITIONAL INFORMATION

Islamorada luxury condo and boat slip for boats to 44' - the perfect combination for serious boaters! Located within a 14-acre, resort-style ocean front community of just eight buildings, this home sits in a peaceful low-rise building with only three units. As an end unit with no one above or below, it feels very much like a single-family home. Windows on three sides bring in natural light and a comfortable, airy feel throughout. The kitchen and baths are up-to-date and beautiful. The layout includes 2 bedrooms and 2 baths, plus a screened porch and an expansive 650+/- sq ft open patio overlooking a peaceful swimming lagoon, surrounded by mature trees. You'll want to dine outdoors every night! It's a quiet, private setting that still keeps you close to everything. Impact windows and doors throughout - and - electric roll down shutters for the screen porch. For boaters, the marina is a standout. There's a ramp, shore power, ice, and a private fuel dock exclusively for owners which is an uncommon and valuable feature. It's not just more convenient to gas up at home... it's less expensive than local marinas too! This unit comes with a slip that can accommodate up to a 44' boat and is in a prime location, close to shore and just a short distance from the unit. It's also near a popular gathering spot where owners tend to unwind and connect at the end of the day. Community amenities include an oceanfront pool, clubhouse, a lighted tennis court, and an additional court for tennis or pickleball. The grounds are lush, green, well-kept and spread out, giving the entire property a relaxed, uncrowded feel. Pet-friendly with no size restrictions. If you're looking for a low-maintenance Keys home with excellent dockage and a true Keys boating lifestyle, this one checks the boxes. Offered beautifully furnished. An absolute must-see! Using exterior measurements, total footprint is 2,650 sf +/-.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,358
Status:
Active
MLS#:
619524
Type:
Condo/Townhouse
Subdivision:
Executive Bay (87.0)
Year built:
1980
Courtesy: Coldwell Banker Schmitt Islamorada 305-664-4470
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ADDITIONAL INFORMATION

Welcome to Executive Bay Club in beautiful Islamorada, Florida Keys! Located at Mile Marker 87 bayside, just north of Founders Park, this highly sought-after, pet-friendly waterfront community offers the perfect blend of convenience and Florida Keys living. This completely remodeled 2-bedroom, 2-bath condo is move-in ready and thoughtfully upgraded throughout. Unlike many units, this property features two full bathrooms (one upstairs and one downstairs) and no spiral staircase, offering improved functionality and ease of living. The interior boasts a brand-new kitchen with new appliances, new cabinetry, updated flooring, and fresh paint throughout, creating a clean, modern coastal feel. An indoor laundry room with stackable washer and dryer adds everyday convenience. The bright, open floor plan flows seamlessly to a private patio through sliding glass doors, providing a shaded outdoor space with added privacy--perfect for relaxing after a day on the water. Executive Bay Club is a gated, amenity-rich community featuring a pool, tennis courts, sandy bayfront beach, lush tropical landscaping, and a manned entrance. Boating enthusiasts will appreciate 31 boat slips for vessels up to 28 feet (first come, first serve), 6 mooring pilings, fishing areas, fish cleaning stations, and a kayak launch. Ideally located within the community, this unit is just steps from the pool, tennis courts, and community center. If you're searching for a waterfront condo in Islamorada or a Florida Keys retreat, this property offers an exceptional opportunity to enjoy island living at its best.

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Andrea D. Conner, License # BK3437731, Xome Inc., License CQ1043756, [email protected], 844-400-XOME, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Use of search facilities of data on the site, other than a consumer looking to purchase real estate, is prohibited. © 2026 MIAMI Association of REALTORS®, all rights reserved.


Andrea D. Conner, License # BK3437731, Xome Inc., License CQ1043756, [email protected], 844-400-XOME, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

The data relating to the real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Florida Keys Board of Realtors® Florida Keys MLS, Inc. Real Estate listings held by brokerage firms other than the owner of this site are marked with the MLS logo and detailed information about them includes the name of the listing broker's office. Information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that data is deemed reliable but is not guaranteed accurate.




Islamorada 33036 Real Estate

Islamorada is located in Florida. Islamorada, Florida 33036has a population of 7,051. Islamorada 33036 is less family-centric than the surrounding county with 16.45% of the households containing married families with children. The county average for households married with children is 20.65%.

The median household income in Islamorada, Florida 33036 is $77,423. The median household income for the surrounding county is $73,153 compared to the national median of $69,021. The median age of people living in Islamorada 33036 is 55.3 years.

Islamorada Weather

The average high temperature in July is 89.3 degrees, with an average low temperature in January of 62 degrees. The average rainfall is approximately 47.7 inches per year, with 0 inches of snow per year.

Islamorada Map

Islamorada Real Estate Market Conditions

  • Median sales price

    $1,150,000
    26.6%
    change since last quarter
  • # Active listings

    207
    30-day change

Islamorada Schools and Demographics

Education near Islamorada, FL

City County
High School Graduates 96.13 92.07
College Degree - 2 year 10.44 7.93
College Degree - 4 year 39.54 35.69
Graduate Degree 11.76 9.88
Expenditures per Student 20,907 20,907
Students per Teacher 14.7 14.7

Elementary Schools near Islamorada, FL

Grades Students P/T Ratio ZIP
Big Pine Academy PK - 08 177 12.6 33043
Gerald Adams Elementary School PK - 05 544 13.3 33040
Horace O'Bryant School PK - 08 1,059 14.3 33040
Key Largo School PK - 08 847 14.1 33037
Key West Montessori Charter School KG - 08 149 16.6 33040
Monroe Virtual Instruction Program (District Provided) KG - 05 6 33040
Ocean Studies Charter KG - 05 104 11.2 33070
Plantation Key School PK - 08 435 12.8 33070
Poinciana Elementary School PK - 05 663 15.1 33040
Sigsbee Charter School KG - 08 478 17.1 33040
Stanley Switlik Elementary School PK - 05 566 14.2 33050
Sugarloaf School PK - 08 526 15 33042
Treasure Village Montessori Charter School PK - 08 213 14.2 33036

Middle Schools near Islamorada, FL

Grades Students P/T Ratio ZIP
Glynn Archer Elementary School PK - 05 394 15.8 33040

High Schools near Islamorada, FL

Grades Students P/T Ratio ZIP
Coral Shores High School 09 - 12 733 17.4 33070
Key West Collegiate School 09 - 12 78 15.3 33040
Key West High School 09 - 12 1,193 16.8 33040

Ungraded Schools near Islamorada, FL

Grades Students P/T Ratio ZIP
* Keys Center 08 - 12 11 11 33040
Academic Connections for Excellence 06 - 12 11 33040
Adult/Vocational/Community Education AE - AE 0 33040
Hurricane Island Outward Bound 06 - 12 12 33037
Marathon School 06 - 12 667 18.5 33050
Monroe Virtual Academy (Course Offerings) 06 - 12 0 33040
Monroe Virtual Franchise 06 - 12 4 33040
Monroe Virtual Instruction Program KG - 12 0 33040

Demographics near Islamorada, FL 33036

Zip Code City
Neighborhood Type Small town
Population 7,051 82,244
Population Density 1,094 84
Median Age 55.3 48
People per Household 2.2 2.4
Median Household Income 77,423 73,153
Average Income per Capita 60,315 50,050

Real estate near Islamorada