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Historic Shadow Point

Historic Shadow Point Vacation Rental in Key Largo

History of the Estate

This unique property is an unforgettable slice of 1920s Key Largo. Because of its size and location, Historic Shadow Point is very popular for family gatherings and other special events. We have catered to guests from all over the world, and many come back year after year.

The vintage Cottages are situated on a secluded, shady peninsula surrounded by water on three sides, with clear views of mangrove islands and abundant wildlife. Built in the 1900s by a sailing ship's captain, each house represents early Keys architecture from the pioneering times of Florida.

History of Hurricanes

1919 – There was only one hurricane during the 1919 hurricane season and it struck Key West. Passing through the Florida Straits from the southeast, the September 9 and 10 Great Hurricanes did severe damage to buildings and railroad docks at Key West. The estimated damage was $2,000,000 and the highest winds were estimated at 110 mph. No deaths were reported on the island; however, the steamer Valbanera was found sunken between Key West and the Dry Tortugas with 488 aboard. All perished.

1926 – In 1926, the first Overseas Highway was under construction. In September, a Great Hurricane struck Miami killing 200 and severely damaging the roadway and bridges being built in the Upper Keys. On October 21, a second hurricane passed just east of the Upper Keys doing more damage to the highway in Islamorada and Key Largo areas.

1929 – On September 28, a Great Hurricane, of which there is little written, passed through the Upper Keys with estimated winds of 150 mph. Reportedly, storm surges were 6 to 9 feet at Garden Cove. Railroad service was out for a week. Sections of the highway were washed out as far as Big Pine Key. The Coast Guard had to provide mail service for Key West.

1935 – The Great Labor Day Hurricane had the lowest barometric pressure ever recorded over land in North America (26.35 inches of Hg or 892 Mb) – yet NOAA has it as a Great and not an Extreme storm. However, much less intense Hurricanes Carol and Edna in 1954 are listed as Extreme Hurricanes.
Winds were estimated to exceed 200 mph with storm surges up to 18 feet. More than 400 residents and World War One veterans building new highway bridges perished. Forty miles of the railroad bed was destroyed. Most structures from Long Key to Plantation Key simply disappeared. With the railroad destroyed, the Middle and Lower Keys were isolated except by sea and air. The surviving railroad’s concrete bridges were later widened for vehicles and a continuous two-lane highway was opened in 1938.

1945 – The September 15 Great Hurricane did severe damage to the Homestead-Miami area. Homestead reported gusts to 196 mph. Carysfort Lighthouse measured a 138 mph gust. The Richmond blimp base in south Dade lost 25 blimps. However, the Upper Keys reported minimal hurricane damage just as it did in Hurricane Andrew. Being on the left side of a hurricane was a definite advantage.

1947 – Only one of the two Florida hurricanes of 1947 struck the Keys and it was in the Dry Tortugas area on October 11. Unfortunately, the anemometer was not oiled properly and stopped at 80 mph. Observers estimated 150 mph winds. It came ashore on the mainland at Cape Sable and dropped a lot of rain. In these earlier hurricanes, the reporting of tornadoes appeared to be rare; however, two were confirmed in the Miami area.

1948 – Again, only two hurricanes made landfall on Florida soil and both made contact with the Keys. The first arrived at Key West on September 21 with winds recorded at 122 mph at Boca Chica airport. Gusts were said to have reached 160 mph with a tidal surge of six feet.

     Two weeks later on October 5, a second hurricane came ashore at Key West and followed the highway up the Keys. This hurricane was similar to Hurricane Floyd in 1987 which also was not very damaging. Winds were estimated at 100 mph but were measured at Miami at 90 mph. 

1950 – This year marked the official naming of hurricanes, but the Major, Great, and Extreme descriptions continued until the Saffir-Simpson scale was adopted. Hurricane King came onshore above Fort Lauderdale, so only the uppermost Upper Keys experienced severe winds with a moderate storm surge. Hurricane Easy passed just west of Dry Tortugas, but no significant damage was reported in the Keys.

1960 – The Keys had gone a decade with only one tropical storm (1952). Hurricane Donna made up for the lack of tropical activity. Part of a poem reads, 
     “Donna was a husky lass,
      A lusty dame was she,
      She kicked her heels and swirled her skirts,
     And shrieked in fiendish glee. . . .”

For certain, Donna was no lady as she wreaked havoc in the Middle and Upper Keys. She was already reported as a “Killer Hurricane” while passing northern Cuba. In the early morning hours of September 10, the Keys experienced the worst hurricane since 1935. Reliable sources reported sustained winds of 140 with gusts to 180 mph. Tavernier reported an anemometer “solid against the peg at 120 mph for 45 minutes.” Lignum Vitae Key (owned by Hugh Merritt Matheson) reported 155 mph and Sombrero Lighthouse 150 mph. Tidal surges were from 8 to 13.5 feet. The Tea Table Relief Channel highway bridge and waterline were destroyed, temporarily isolating the Keys farther to the south. Amazingly, only four lives were lost.

1964 – Hurricane Cleo barely missed the Keys passing to the east on August 26. The Weather Bureau for the first time used cloud images from a space satellite as a hurricane tracking aid. A southwest hurricane named Isabell struck the Dry Tortugas area to our west on October 14. Key West had wind gusts to 76 mph.

1965 – Like Donna, Betsy was no lady either. On September 4, she was well north and east of even the Upper Keys. This was just a tease, because on September 5, she “changed her mind” and headed south for the Bahamas where she again changed her mind – heading almost due west for the Keys. Betsy and the second hurricane of 1935 are the only two American hurricanes recorded making landfall from the northeast.
     On September 8, 1965, Tavernier claimed to have been in the hurricane’s eye from 4:30 to 7:10 A.M. Sustained winds were reported at 125 mph with gusts to 165 mph. The Middle and Lower Keys were also severely damaged by Betsy. Big Pine Key reported gusts as high as 160 mph. Two tornadoes were confirmed – one at Marathon and one at Big Pine Key.

     As a side note, Betsy was the hurricane that the government was accused of “seeding.” There was project “storm fury” that experimented with spreading silver iodine crystals into clouds; however, this was never proven to be the case with Betsy.

1966 – Again two hurricanes involved the Keys. First, it was Alma who skirted past the Dry Tortugas on June 8 just to its west, but still, winds of 125 mph were measured at the Dry Tortugas weather station. Key West had gusts to 70 mph. 

     Inez was another hurricane that appeared to be missing the Keys to the east, then on October 3, she reversed herself and came back. During the day of October 4, she traveled the Keys from east to west with minimal damage. Again, Big Pine Key reported wind gusts up to 150 mph. Winds were measured on Plantation Key at 98 mph; therefore, one might suspect that Big Pine Key experienced a tornado-like Key Largo did during tropical storm Mitch in 1998.

1972 – For the record, in June, Hurricane Agnes missed the Keys to the west by hundreds of miles. In spite of this, on June 18 at about 2 A.M. a tornado hit Big Coppitt Key causing $350,000 of damage and ruining some 80 mobile homes. 

1987 – After 21 years of no hurricanes, Floyd came up from western Cuba as a tropical storm, then intensified to a minimal category 1 hurricane as it approached the Marquesas. On October 12, it barely maintained hurricane force (74 mph or above) for 12 hours during which time it managed to follow highway US 1 up through the Keys. One tornado touched down in Key Largo doing considerable damage.

1992 – Damages attributed to Hurricane Andrew are staggering and elusive - some estimates reach $30 billion. The Ocean Reef Club and the Anglers Club on North Key Largo were the hardest hit in Monroe County. The power lines bringing power to the Keys were also destroyed, but potable water was maintained. 

     For the record, Andrew made landfall at 4:30 A.M. on August 24 at about Cutler Ridge. NOAA establishes sustained winds of 145 mph with gusts over 175 mph. Its forward speed was 18 mph.

     By 8:00 A.M., Andrew had passed over Naples on Florida’s west coast. Barometers establish a pressure of 27.23 inches of mercury (922Mb) making Andrew the third most intense hurricane making landfall in the U.S. after Camille in 1969 and the Great Hurricane of 1935. The last figures had 38 confirmed dead.

1998 – If we look at the hemisphere, 1998 was disastrous. Thousands of people perished in Central America from Hurricane Mitch and 602 from Hurricane Georges. The estimated number of victims of Mitch was 9,086 as of the NOAA report dated January 28, 1999.

     Hurricane Georges (pronounced Zhorzh) was a classical Cape Verde tropical system. He traveled westerly from just off the west coast of Africa to strike the Keys; well almost, as NOAA says the eye’s center was 12 miles south of Key West. Landfall was mid-morning of September 25 with maximum winds of 104 mph. From NOAA, the maximum sustained 2-minute wind at Key West was 55.2 mph at 8:53 A.M. with a peak wind gust of 88 mph. The highest wind gust recorded in the Keys was 110 mph at Marathon. Sombrero Key reported a sustained wind of 94 mph with a gust of 106 mph. Storm surges were reported from 4 to 6 feet in the Lower and Middle Keys. Key West recorded 8.38 inches of rain.

     Hurricane Mitch also came off the West Coast of Africa leaving on October 8. After meandering through much of the northern hemisphere, he arrived 5 miles west of Naples at 6:00 A.M. on 5 November. His sustained winds of 63 mph classified him as a tropical storm at the Keys. The highest wind actually measured during his trip from Africa was 193 mph, the location was not disclosed.

     The Upper Keys had a number of tornadoes from Mitch and the NOAA report only states that 645 houses were damaged,( Shadow Points yard was destroyed, but the houses still stood) or destroyed in Florida. There were two deaths from a fishing boat capsizing in Monroe County.

1999 – The preliminary NOAA report for Hurricane Irene indicates she reached hurricane status crossing the Florida Straits. On October 15, her eye passed over Key West at 8:00 A.M. Irene made landfall again near Cape Sable later that day at 3:00 P.M. Most of her hurricane-force winds were confined to her east at the Lower and Middle Keys. There were eight indirect deaths related to Irene, all on the mainland. Florida’s damage is estimated near $600 million.

     We will close with our disclaimer used by the  Weather Bureau: “Hurricanes are sometimes unpredictable”.


in August of 2017, Irma hit the keys and we offer photos of the damage in the tab above under Recent photos - Irma's visit.

Despite going through numerous hurricanes the house is still standing which is a testament to the builder and designer of which we know little. This property was acquired in 1923 by the same family who still owns it to this day.  They have worked very hard over the generations to keep the houses as original as possible. The homes are decorated with pieces reflecting the years of being connected to the local waters. Their ancestor, Marvin D. Adams, is responsible for constructing the canal that bisects Key Largo. Known as The Cut to locals, The Marvin D. Adams Waterway allows boaters to travel conveniently from the Atlantic Ocean side to the Gulf of Mexico in minutes. The structures on the property are likely the oldest original residential homes still intact and in use on all of Key Largo. 

Orchids at Historic Shadow Point

Orchids abound in the Garden 

Rainbow at Historic Shadow Point

A century of Rainbows has brightened Historic Shadow Point. Vacation Rental on the Water in Key Largo - Perfect for Family Gatherings and Weddings.

Wedding Tree

This tree is called the wedding tree. It has been on the property for over 100 years and even though it is wind-blown and mangled it stands steadfast.

View of Garden and Water at Historic Shadow Point

View of Property and Surrounding Water

Period Antiques

Old Radio Telephone
old telephone
record player
old high chair

Baby's Highchair
and stroller - 1920s

1934 type writer
1936 Underwood Typewriter
old washing machine
Old washing machine, New cooler!
cast iron pans

Cast Iron items

Curio cabinet with side desk

Curio cabinet with side desk

bottles collected over the years
Rare bottles
1926 electric stove
Electric Stove - 1926
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