Investment, Property, Vacation homes & real estate

Off the beaten path...real estate in sleepier Florida


Not everyone who comes to Florida is here for the bright lights of Miami or the attractions of Orlando, some yearn for sleepy towns where time moves a bit slower and the rhythm keeps pace with nature. There are still many hidden spots through-out Florida and although their residents prefer to keep them this way, they are also very welcoming to new residents who often leave behind busy business lives and quickly fall into the local pace, whether it is for a winter escape or as a year round resident.

Remember that Florida is a peninsula and therefore surrounded by water on 3 sides. The west coast is on the Gulf of Mexico and boasts calm, brilliant blue waters and soft, sugary sand. There are no waves (except during big storms) on this coast and there are little beach towns dotted from the north by Pensacola all the way down past Alligator Alley to Naples and further south to the keys. Denise Assersohn, a Realtor originally from London lives in Hudson, Florida with her husband Bert and two dogs “the biggest decision we often make each day is whose boat to have sunset happy hour on” Denise has lived in Hudson for 7 years after living in Orlando for 35 years “We just love the feel of our little town, everyone is friendly and life is really enjoyable here and surprisingly affordable” According to Denise, it is still quite possible to find property on the canals minutes from the Gulf for less than $300,000 and direct gulf access beginning in the $600,000’s. “Hudson is incredible value for money unlike some other towns that have become popular in recent years like Sarasota and Naples but prices are definitely creeping up quite quickly now so it will not stay this way for long”.  Next door to Hudson is even sleepier Aripeka with vast amounts of sea marshes and the occasion houses dotted on stilts among the reeds. Aripeka is a quaint village from another time and nobody is in any rush to change that.

Siesta Key

Siesta Key is a popular key (island) in Sarasota County that is voted America’s top beach almost every year due to its sugary white sand and very rustic, natural feel. Siesta Key is not somewhere that you can find high rise condos and fancy restaurants, in fact many residents don’t bother with much more than shorts and flipflops and prefer it to stay this way. The natives are a friendly group, so much so that Andy and Jayne Appleyard picked up from Yorkshire, England and moved to a waterfront home on Siesta Key with their two sons who now go to the local high school and now live in their own laid back slice of heaven “…living on the water and by the beach out-ways the hassle of been on the road, it’s like being in paradise” says Jayne who now runs the Gallery Salon and Spa on the key. Small houses can be found on Siesta Key beginning in the $400,000’s and waterfront above $1,000,000.

The West Coast has many such cities, towns and beaches along the entire stretch of the state, each with its own personality and some more populated than others, some pricier than others but all exuding their own natural charm and beauty. One thing that they all share are the arguably the planet’s most beautiful sunrises and sunsets so it’s really hard to go wrong no matter where you end up and much like Denise, life moves a bit slower and sunset happy hour isn’t hard to find.

In the Center of Florida, while landlocked in between both coasts, most cities and towns will be about an hour or so away from either coast and as is normal through-out the state, there are lakes dotted everywhere so waterfront might simply be “freshwater” in these towns.

Winter Park

Winter Park is a quaint neighbor of Orlando known for oak canopied, brick streets. The main promenade, Park Avenue is home to historic Rollins College and many café trottoirs and boutique shops. The Winter Park chain of lakes is home to beautiful mansions and although Winter Park is pricier than its Orlando neighbor, those who live there don’t tend to leave. Prices for non-waterfront begin in the $400,000 range and go up into the millions for lakefront on a waterski lake.

Crystal River

Located two hours from Tampa Bay, the town of Crystal River is part of Florida’s Nature Coast incorporating one of Florida’s purest spring fed water systems. Crystal River and neighboring Homosassa River are home to one of the largest populations of the state’s endangered manatees who love the consistent water temperatures. The homes on these rivers are still quite affordable beginning in the high $200K range. Kayaking, paddleboarding, and snorkeling the springs of Florida are something not to be missed and if you find yourself lost in such a place, it’s questionable whether you might really want to be found.


Just south of Gainesville, Micanopy is a slice of yesteryear as though untouched by time. A glass of lemonade on the front porch after a morning out horse riding is just the ride speed for this sleepy town originally founded as a frontier trading post in 1821. Now on the historic registry, Micanopy has a thriving antique district and plenty of available land for horse lovers. Property ranges from raw land at less than $100,000 to equestrian ranches into the millions.

Heading to the east coast of Florida puts you right on the Atlantic Ocean and home to world famous Miami Beach and year round surfing. Again, the coastline is vast and the drive along A1A will take you winding along tourist corridors like Daytona Beach and into some smaller towns that like to hide and remain off the map.

St. Augustine, Ponte Vedra

Anyone seeking the fountain of youth need go no further than St. Augustine on the northeast coast. Founded in 1565 by Spanish explorers, it is the oldest continuously inhabited European-established city within the borders of the continental US. Home to Castillo de San Marcos, a 17th-century Spanish stone fortress with views of the St. Augustine Inlet, the legendary Fountain of Youth, Flagler College, Spanish colonial architecture, and gorgeous beaches, there is always much to do and see in St. Augustine. Property begins in the mid $300,000’s and goes into the millions for beachfront.

Fernandina Beach

Fernandina Beach is located on Amelia Island  and boasts pristine beaches and a historic architectural grace that makes it popular for walking tours and carriage rides. It is home to Florida’s oldest continuously operated drinking establishment, The Palace Saloon and of course the beach and watersports lovers will never run out of things to do.   Non beach front homes can be found from about $300,000 and beachfront from the millions. 


A village comprised of 6 islands, if you close your eyes and envision yourself lying on a beach hammock on a deserted island paradise, you might be in Islamorada. While it isn’t deserted and still as connected with modern life as necessary, it has charm that is timeless. This is the ultimate of sleepy beach towns although many before have had the same idea and prices are up there with condos beginning at about $300,000 and beachfront into the millions. Nothing fancy mind you, it’s a flipflop and fishing kind of life!




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