Islamorada Luxury Real Estate, Luxury Homes For Sale

Oceanfront Compound includes 6 houses, 17 bedrooms, 14 baths. 3 Main Oceanfront homes each with its own guest house. Your own private, gated compound for corporate/family retreats. Spectacular CBS homes…

PEARL CITY - Home where well-known author, HERBERT ZIM, did all of his writing. 7.94 acre oceanfront estate is sited on desired Millionaire's Row. Five homes (7 lots) on 6.78 acres upland plus 1.16 acres…

HUGE OCEANFRONT PARCEL IN ISLAMORADA offering a deep water basin...rare for oceanfront! 200' on the ocean! You will enjoy this gated compound with a remodeled ground level home with many extras including…

This bayfront home has it ALL including a SUBSTANTIAL TAX DEDUCTION! Spacious home for a large family has elevator and 3rd floor master suite. Room for all your boats and water toys. 5.05 acres plus .52…

The Conch, Lobster, Pelican & Egret at Alligator Reef. Your own private, gated compound for corporate or family retreats. These new CBS homes consist of two 3/2 homes and a 2/2 accessory house behind…

JUST REDUCED TO MOTIVATE BUYERS!!! Prime property with over 4 acres on the Atlantic Ocean with 350' of sandy beach. Private channel cut all they way to the dock!Permitted Vacation Rental in the Village.…

Oceanfront acreage with rare deep water boat basin for large boats. Concrete seawall and boat ramp. Concrete house with 2/2 up and 1/1 apt down. Huge chickee hut bar, large detached garage. More than…

Oceanfront estate on desired Old Highway. Home has deep-water boat basin, great ocean views, and gracious, island-style home with beautiful swimming pool and spacious outdoor entertaining area. Privacy…

EXQUISITE OCEANFRONT ESTATE! Ocean views galore! Pool & spa, beach, dockage with lifts. 5 bd/5.5 bth, spacious master suite, huge workshop/tackle room, game room with guest quarters, elevator, rooftop…

ABOVE AND BEYOND contemporary ''work of art'' home in Plantation Key!! When only the best will do, look no further! Smart home technology offered in this 3bd/3.5ba pool home with outstanding bayviews,…

Spectacular gated oceanfront estate at a coveted Old Highway address in Islamorada. Ultimate privacy complemented by stunning landscaping, tennis court, swimming pool & spa, outdoor kitchen, fishing pier…

Extraordinary location! One of 12 direct oceanfront homes on 3.3 acres on Lower Matecumbe. Spacious home with unparalleled views offering exceptional quality throughout. Tarpon Point features the most…

Extraordinary location! One of 12 direct oceanfront homes on 3.3 acres on Lower Matecumbe. Spacious home with unparalleled views offering exceptional quality throughout. Tarpon Point features the most…

Extraordinary location! One of 12 direct oceanfront homes on 3.3 acres on Lower Matecumbe. Spacious home with unparalleled views offering exceptional quality throughout. Tarpon Point features the most…

BAYFRONT ESTATE ON 6 ACRES. Nearly 1/4 mile off US 1 you'll find this spacious, serene property with 245 ft. on the bay. Two CBS cottages each with private pier are a perfect Keys' getaway. Property is…

BAYFRONT ESTATE ON 6 ACRES-Nearly 1/4 mile off US 1 you’ll find this spacious, serene property with 245 ft. on the bay. Two 1/1 cottages, each with private pier, are a perfect Keys’ getaway, or build…

Bay front compound offers 7 residences comprised of 2 duplexes and 3 homes on over 1.5acres of prime Islamorada real estate. Immediate back country & offshore access. Dockage for multiple vessels from…

Extraordinary location! One of 12 direct oceanfront homes on 3.3 acres on Lower Matecumbe. Spacious home with unparalleled views offering exceptional quality throughout. Tarpon Point features the most…

Extraordinary location! One of 12 direct oceanfront homes on 3.3 acres on Lower Matecumbe. Spacious home with unparalleled views offering exceptional quality throughout. Tarpon Point features the most…

Extraordinary location! One of 12 direct oceanfront homes on 3.3 acres on Lower Matecumbe. Spacious home with unparalleled views offering exceptional quality throughout. Tarpon Point features the most…

This stunning, contemporary home is one of the most spectacular properties on the market at this time. Enter through the heavy, ornamental double iron & glass doors into the foyer flooded with natural…

Extraordinary location! One of 12 direct oceanfront homes on 3.3 acres on Lower Matecumbe. Spacious home with unparalleled views offering exceptional quality throughout. Tarpon Point features the most…

JUST REDUCED! La Playa Estate - Main Residence - offers 4BR/ 4.5BA and 200 ft. of ocean front - includes 150 ft. dock w/channel for great boating access for boats up to 3 ft. draft.Spacious rooms with…

Exquisite, Serene, Compelling...Prominently positioned on Upper Matecumbe Key, this magnificent oceanfront estate features panoramic views,soaring ceilings,custom gourmet kitchen,guest house,lush gardens,…

Privacy abounds at this resort like residence. Water frontage on 2 sides offers seclusion that is hard to find. Totally updated home provides 2 master suites in nearly 3000 sq. ft. Gourmet kitchen with…

Floridian style bayfront beauty in lovely Lower Matecumbe zoned residential estate and offering 1.73 acres of privacy. Sandy beach, pool and fabulous dockage. 2005 home with all of the bells and whistles,…

Tranquil 2 +/- acre estate, featuring 2 homes. Main is a 3 bedroom 3 bath with attached garage and carport. 2nd home is a large 2 bedroom 1 bath located above a huge 2 car garage. Both homes are all concrete…

ATLANTIC SUNRISE ON PLANTATION KEY! Two acres oceanfront with 250 ft on the water. Letter from Village of Islamorada gives this parcel 4 legal single family dwelling units and 3,255 sq. ft. of commercial…

HUGE home in Venetian Shores with 170ft. of dockage!! Beautifully remodeled 5 bedroom 3 bath home is perfect for Keys style living and entertaining. An elevator gives this home easy access. Split bedroom…

Exquisite design and details throughout, this gorgeous waterfront home located in prestigious Venetian Shores, with plenty of room for your yacht! Very impressive must see home with views of snake creek!…

Contemporary home on 200' waterfront - deep water protected dockage - 2 boat lifts (24K & 12K) - a boater's dream. The house is also a dream. Great room with cork floors, wet bar, dining area, kitchen…

Extraordinary location! One of 12 direct oceanfront homes on 3.3 acres on Lower Matecumbe. Spacious home with unparalleled views offering exceptional quality throughout. Tarpon Point features the most…

JUST REDUCED! MAGNIFICENT OCEANFRONT 5BD/5BA CUSTOM BUILT BY OWNER ON MATECUMBE OCEAN BAY BEACH. SPACIOUS TRI-LEVEL FLOOR PLAN, GOURMET KITCHEN, COMPLETE W/ DOCK & SANDY BEACH, GATED FOR PRIVACY, EXPANSIVE…

Islamorada's private, secluded gated community on the Bay, with pool, and boat dockage for each homeowner. This beautiful ground level home was completely rebuilt from the ground up in 2006. Travertine…

Magnificent sunrises from this ocean front home. Over an acre of land with 100' on the Atlantic plus additional .31 acre of bay bottom. The irreplaceable boat basin offers protection and deep water for…

NEARLY 4 ACRES ON THE BAY with existing CBS cottage. Build your bayfront estate home here. Pier dock extends into the bay offering deep-water dockage for several vessels. Bayfront of 125 feet plus the…

Extraordinary location! One of 12 direct oceanfront homes on 3.3 acres on Lower Matecumbe. Spacious home with unparalleled views offering exceptional quality throughout. Tarpon Point features the most…

PRESTIGIOUS CUSTOM BUILT HOME: THREE STORY INCLUDING DOWNSTAIRS GUEST SUITE, INTERIOR STAIRCASE WITH ELEVATOR, LIVING AREA WITH EXTENDED ASHTRAY CEILINGS, GOURMET KITCHEN, OFFICE, PRIVATE MASTER SUITE,…

This property is a lot and a lot with a house! Drop dead gorgeous sunsets and bayviews! You need to see this as it is one of the best bay front properties on the market today!

Extraordinary location! One of 12 direct oceanfront homes on 3.3 acres on Lower Matecumbe. Spacious home with unparalleled views offering exceptional quality throughout. Tarpon Point features the most…

Extraordinary location! One of 12 direct oceanfront homes on 3.3 acres on Lower Matecumbe. Spacious home with unparalleled views offering exceptional quality throughout. Tarpon Point features the most…

Extraordinary location! One of 12 direct oceanfront homes on 3.3 acres on Lower Matecumbe. Spacious home with unparalleled views offering exceptional quality throughout. Tarpon Point features the most…

Massive Oceanfront with protected boat basin for 2 large boats and add'l concrete dock along canal side of property. The waterfront features a huge pool and 2 big chickees for easy breezy outdoor entertaining.…

MASSIVE OCEANFRONT WITH BOAT BASIN. This great Islamorada home is impressive with its tree-lined long driveway and unparalleled ocean views. Unique features include an elevator, fireplace, stone floors…

Exclusive private enclave of 12 Key-West Style Residences - each with their own distinct interior finishes. This home enjoys an open sunset view from the private pool, patio, porches...living room, dining,…

CLASSIC KEY WEST IN ISLAMORADA - Oceanfront with sandy beach. Main house has 3BR/3BA, plus third floor lofted study. Beachfront cabana house gives you an additional 1BR/1BA guest room. Lush landsscaping,…

Gorgeous Bay Front Property with 'cut in' boat basin! Free form pool with walk in entry and hot tub. 1 Bedroom 1 bath up and two seperate ''Guest'' bedrooms and baths down. Owner is a Real Estate Professional.…

Owner says sell!! Not a short sale!! Located in the heart of Upper Matecumbe lies a spectacular Bayfront Hideaway. Enjoy sunsets from the porch, the pool; dock up to a 36ft center console; Includes 3…

Incredible ocean front 3/3/1 custom built by owner on Matecumbe Ocean Bay Beach.Top floor boasts 2 bedrooms 2 full baths,office & media room opens to spectacular 3rd floor ocean front sundeck. Main level…

BAYFRONT IN ISLAMORADA with unstoppable sunset views! 3 Bedrooms each with it's own Bath and 1 half bath for guests. Amenities include: Custom Brazilian cabinets with stainless steel appliances, granite…