Coincidences mean a lot to Realtor Jaime Caballero, owner of Key West Vacation Properties & Realty.
Jaime, a Key West native since her birth in 1967, realized this during the COVID pandemic in 2020.
“During COVID, my husband Arnold would ride me around town when we wanted to get out of the house. We were bored and were looking for a new office space,” she said of her high school sweetheart and husband of 38 years. “At the end of February 2021, we stumbled across 323 Fleming Street and I instantly fell in love with it and had a contract in my hand by the end of the day.”
Coincidence number one: The day they closed on the property was May 7, 2021. Jaime started her real estate company on May 7, 2009.
Coincidence number two is when Jaime discovered that she had worked with one the previous owners of the building, the Spottswood family, for 13 years and where she started her career in property management. Bill Spottswood’s wife owned an accounting firm called Moore & Spottswood, CPA and with her business partner purchased 317 Fleming Street. After researching the history of the building, Jaime discover that 317 Fleming’s address had been changed to 323 Fleming Street. Today it is the only remaining building from the original plat since in 1939 the U.S. Navy condemned residential properties in Square 39 and all were razed or moved, except for this property.
Coincidence number three occurred when Jaime discovered that when 323 Fleming was military navy housing for married couples it was called Quarter J. J = Jaime. There is a plaque explaining the history of Quarter J on the outside of the building. The base closed in 1974.
Coincidence number four was the most profound for her. When she had the hardwood floors sanded down to their original texture in the upstairs conference room, she had recently lost her brother Gary Manning. Jaime said he was obsessed with monkeys and called himself the mangrove monkey. Once sanded down, a distinct image of a monkey was present in the grain of the flooring.
“It was all these little coincidences that made me realize that this property was meant to be,” she said.
Jaime and Arnold, along with their Key West renovation team of Zolton Boros Classic Wood Floors, Michael Monsalvatge of Mike’s Painting, Kolhage’s Appliances and Electronics, Curry Refrigeration and Air Conditioning and more, recently completed the nearly 18-month refurbishment.
Historian Sharon Wells was instrumental in helping with researching the history of the building and Bob Cerkleski of Key West Sea Store Antiques sold Jaime a majority of the picture frames used throughout the office.
“I went through 30,000 light fixtures to pick the lights for the rooms and exterior and 2,000 antique hardware selections for hinges, knobs, outlet covers and light switches,” Jaime said, adding the furnishings were acquired through Arhaus of Naples, Fl. “Discovering Arhaus was a godsend. I became obsessed with their furniture and their design team sat with me for six hours and became the voice of reason when I was trying to fit six pieces of furniture in an office that would only hold three.”
The two story structure was built between 1909 and 1911 and encompasses approximately 2,200 square feet with six offices, two conference rooms, downstairs lobby, kitchen and two bathrooms.
“We were really pleased to use all local vendors for this project,” she said. “We were lucky to be Zolton Boros’ last client before he retired and moved out of town after over 20 years (coincidence number five) and Michael Monsalvatge’s family goes back to the 1900s in Key West. He painted the inside and the outside of the building.”
Kolhage’s Appliances replaced all the appliances and helped design the color of the counter tops and cabinets. Lucy LeCompte from Home Depot designed the kitchen cabinets. Patrick Curry replaced all of the AC ducts and the two AC units.
In early November, Jaime was notified by the Greater Key West Chamber of Commerce that 323 Fleming Street had been selected to receive an Historic Preservation Award for the extensive renovation at their December meeting. The property is listed on Truman Annex National Register District, 1982 and in the 1984 U. S. Naval Station (Key West) District on the National Register of Historic Places.
“The attention to detail, not only on the interior, but as well as the exterior of the building has caught the eye of many,” wrote Robert Goltz, executive vice president of the Chamber. “The addition to having each of the rooms in your office have a theme that represents part of Key West history was a brilliant idea.”
Jaime said she was intrigued by the history of the property and really felt a passion to preserve it to its glory and honor the building and the town’s history.
“My passion from my soul for this city that I was born and raised in took over. I didn't have a budget, I had a ‘want’ to make it a piece of history to cherish forever. And with my brother and parents passing away recently, it made me feel like it was meant to be with every turn.”
Jaime’s parent’s and older brothers were born in Massachusetts. Her dad was in the Navy (coincidence six that the building was navy housing) for a short period of time and visited Bermuda and fell in love with it. He said Key West was the closest thing he could find to Bermuda so in 1957 he moved his family to Key West and that’s where Jaime and her sister were born.
One of the upstairs offices has special meaning for Jaime’s remembrance of her father who just passed away in September of 2022.
The room is themed with memorabilia of all the noteworthy ships that are a part of Key West history including the Singleton shrimp fleet, the USS Governor Cobb, the USS Maine and President Truman’s yacht, the USS Williamsburg.
Also in this room is a photo of the motor vessel the Jaime Ann that Jaime and her mother and father would stay on overnight at Christmas Tree Island, a 22-acre island visible from Mallory Square and sister to Sunset Key. While her dad would make his coffee in the mornings, Jaime would drive the 32-foot Owens cabin cruiser under the Fleming Key Bridge to get to her fourth grade class by bicycle. When not in school, Jaime would cross the street to the charter boats and Captain Tommy Lones, who owned the Gulfstream at the time would pay her about five dollars to hose the boat down after they returned from a fishing charter.
“When I was cleaning out the storage closet upstairs, I found the logbook for the motor vessel the Jaime Ann and the log told the same story of our sleeping at Christmas tree island so I guess that’s coincidence number seven.”
Other themes for the rooms include paying tribute to the restaurants and bars of Key West past and present in their kitchen area. A photo of the Bull and Whistle bar is included there.
“When I was in the third grade, my mom sent me to school for picture day with a t-shirt from that bar and I got sent home because back then it was frowned upon for a child to wear anything with a bar on it,” she said.
Jaime’s office just off the lobby on the first floor includes photos of all the presidents that visited Key West. Her daughter, Alexandria’s office across the lobby from Jaime’s, also a Realtor with the company, honors the Southernmost House and Customs House.
Alexandria graduated high school in 2008 and began working for Jaime at the front desk at Sunrise Suites the year before she started KWVPR. Now in her 14th year with her mom, they have been a mother-daughter real estate team since 2011 when she became a Realtor. Alexandria recently passed her broker’s test in June and is awaiting sitting for her broker’s exam. Once she is a licensed broker, Jaime plans to make her partner.
The upstairs conference room honors the Flagler railroad and it includes a photo of Flagler’s first ride on the train into Key West. The people surrounding him in the photo include Key West resident Wesley Archer’s relatives that were there that day of January 22, 1912. Archer is Arnold’s best friend from high school who helped the couple on the refurbishment of the building.
Jaime said there is an 8’x8’ room under Alexandria’s office which was the old cistern.
“I really wanted to make it a bricked sitting room but I figured it wouldn’t be approved,” she said. “We found an old Pepsi bottle from the 1970s down there and an originally carved wood handle screwdriver which is displayed in the upstairs Ship room.”
The lobby includes photos of all the writers of Key West including Ernest Hemingway, Tennessee Williams and American poet Elizabeth Bishop.
“The meaning for me behind honoring Elizabeth Bishop is that I sold that house at 624 White Street in 2019 for the family that bought it from Bishop,” Jaime said. “Today it is home to the Key West Literary Seminar so yet another piece of Key West history is being preserved for generations to come.”
The downstairs conference room is a little bit of Spottswood history, the company where Jaime began her property management career. It includes a map where owners put a pin marker on where they live as a tribute to them. There are also pictures on the wall of St. Mary’s Star of the Sea Church which became a Basilica in 2012 and Convent of Mary Immaculate. The convent was one of the buildings destroyed following the destruction and demise of architectural gems in the mid 1950s. In 1963, the Florida legislature granted Key West the authority to create an architectural review board. By 1986 this board had evolved and was renamed the Historic Architecture Review Commission (HARC) for the purpose of preservation and conservation of the character of historic buildings.
In the hallway upstairs are photos of homes Jaime has managed or sold over the years and around the corner includes photos of all the lighthouses of the keys she has visited along with maps of their locations. There is an empty frame representing the lighthouses Jaime still has on her bucket list to visit and eventually will add those photos as well.
Another office upstairs honors the history of Key West’s local economy including turtling, sponging, and of course fishing. In this room there are three photos of charter boats from Garrison Bight Marina: the Can’t Miss, the Greyhound and the Gulfstream. They are right across from Pelican Landing, a condo building in Key West Jaime continues to manage.
A retired fire fighter, Arnold serves as project manager for the company and has his office upstairs designed with photos and memorabilia of Cuba, fire and police. Arnold was born in Regla in June 1965 and his family came to Key West the same year on the Freedom Flights (known in Spanish as Los vuelos de la libertad) that transported Cubans to Miami twice daily, five times per week from 1965 to 1973.
What they call the bonus office upstairs is currently being used for their daughter Jacqueline’s autistic grandson Dominic, age 9, as a classroom and is decorated with pictures and items from all the places the couple has visited in their life together.
“When I first started looking for office space it was always going to be a dual use building for my real estate company as well as an autism school for Dominic,” Jaime said. “We unfortunately don’t have the resources here in Key West for autistic students, so Jacqueline quit her job as a bookkeeper at Poinciana Elementary School in order to homeschool him due to his special needs.”
Jaime added the reason they call it the bonus office is because this is where the stairs used to come up into the upstairs but were removed by Moore and Spottswood, CPAs during their renovation when they owned it.
The downstairs bathroom has framed antique postcards grouped by government buildings, businesses, tourist attractions and hotels and the bathroom upstairs has historic newspapers and buildings.
The exterior porches are Montauk black slate tile with three different sitting areas for clients and guests to enjoy and all the exterior doors are black with decorative hinges and door handles with glass that match the landscape lighting and exterior lighting.
On the front porch is also a sign commemorating the 200th anniversary of Key West in 2022.
Extra touches Jaime added include books throughout the office including a book on the St. Mary’s Star of the Sea in the conference room along with a variety of Key West coffee table books and cookbooks. In the lobby there is one book of each of the writers displayed on the walls and in the Flagler Railroad room is a spike from the original railroad along with books and a model of Car 91. Car 91 was the car Flagler and his wife always rode in.
She said they also left all the palm trees that align the building, 13 in all. According to some, the number 13 can signify a renewed passion and motivation. It also symbolizes tradition, organization, judgment and hard work.
“They were in the pictures I found in the public library and Library of Congress while researching the property,” she said. “History is important. I’m proud to be a conch and I’m proud to be able to preserve this piece of history.”
Jaime met her husband Arnold her senior year of high school in 1985 and they were married in 1987. In 1996, Arnold became a fire fighter and in 2003 she earned her real estate license and became an agent.
In 2009, Jaime became a real estate broker and started her own company. Later that same year she opened Key West Housekeeping Services to better serve her clients. In 2012 she opened Key West Residential Property Management in order to expand her long term property rental pool.
She has over 30 years in the real estate industry and is active in the National Association of Realtors, Florida Realtors which she will serve in 2023 as District Vice President covering Miami and the Florida Keys. She is also a member of the Key West Association of Realtors and served as president in 2021 and has been active with the National Association of Residential Property Managers serving as Florida State President in 2017 helping promote best practices for property management.
Today, Jaime and Arnold have three daughters, three granddaughters and one grandson. Their third daughter, Elizabeth, just graduated from law school in Boston and they are hoping one day she’ll move it back to Key West and work with the company as well.
“It was always important to me to raise my kids in Key West. It’s a small town and in our community everyone watches out for everyone,” she said. “Key West is a four mile by two mile island and when I was growing up we had a joke that we never spent two Christmas holidays in the same house.”
Jaime’s favorite house was the last one she lived in before getting married at 1004 Eaton Street, less than a mile from her new office.
“That’s where my daughter Alexandria was born in 1989. It was my parent’s house before they moved out of town and we lived there for four years from 1985 to1989 which was actually a record for the Manning family.”
Jaime said growing up on a small island like Key West as a teenager was challenging because she said nobody knew her name they just knew who she belonged to so she couldn’t get away with anything.
“But fast forward 20 years later and it was the best thing that ever happened to me because then I knew when my kids did something wrong and the residents knew who they belonged to,” she laughs.
As for advice to anyone wanting to undertake a restoration project like the one they just completed at 323 Fleming Street she says: “I never got into business to buy a building. It all just fell into place so nicely and when you work hard and don’t expect anything and do it because you love it, good things come.”
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