Once you’ve visited Southwest Florida, or even stayed here for an extended period of time, you may find that when you’re back in your northern abode, you can hear the gentle wind, lazy nights and carefree spirit calling you back to this sunny paradise. You may relish the turning of the leaves and cheer at the first pop of daffodil buds when your weather finally starts to mellow, but during those cold, gray days of winter, you just know there’s another place to go—where you can stroll along the beach rather than duck icicles and sport fashionable sandals instead of lacing up fleece-lined boots. Yes, Florida’s playground is always open, and before you know it, you’re shopping for your winter home here and repeating that famous mantra that countless others before you have declared: “Yeah, I could get used to this.”
Most of the real estate transactions in Southwest Florida occur during our “season,” October through April, when tourists and seasonal visitors decide it’s time to buy their own piece of paradise, a place to call home for a week, a month or year-round. And they’ll find those homes in neighborhoods and communities that exactly fit their lifestyle, whether it’s a yachting community in Naples or Fort Myers, an equestrian estate in Golden Gate Estates or an island cottage on Matlacha. And no matter where our newcomers decide to live, they’re never too far from the beach, the mall, award-winning restaurants or the solitude of the outlying counties. Discover the many neighborhoods of Southwest Florida in this in-depth guide.
Florida’s largest county, Collier, has shed its fishing-town persona for a more polished, sophisticated identity that mingles with celebrities and luminaries who shop, dine and carouse here. That’s not to say that you can’t still find a slower, Old Florida vibe in Collier County among the unspoiled mangroves and backwater bays along the Everglades and Ten Thousand Islands. While it still attracts its fair share of seasonal retired residents, Collier County is getting younger. In fact, those aged 25 to 49 are the fastest-growing population, and the county’s median age has dropped to 43 in recent years.
The Gordon River and Wiggins Pass immortalize Collier County’s first modern-day settlers—Roger Gordon and Joe Wiggins, who arrived in Naples in the late 1860s. When Louisville Courier-Journal owner Walter Haldeman arrived in 1887, he and fellow well-heeled Kentuckians helped turn Naples into a winter playground for the rich and famous. The Naples Hotel soon became the social center for visiting celebrities, among them Thomas Edison, Harvey Firestone, Greta Garbo and Gary Cooper.
In the 1920s, Barron Gift Collier bought more than a million acres of swampland, including most of Naples. He then pledged his own money to build the 275-mile Tamiami Trail, linking Tampa to Miami, which officially opened in April 1928. The completion of I-75 and the Southwest Florida International Airport some 60 years later put Collier County officially on the map. Today it’s a study in paradoxical worlds—stretches of beaches boasting multimillion-dollar mansions and luxury high-rises and quiet fishing communities that recall another place and time.
Collier County Beaches
Consistently ranked among the world’s best, Collier County’s 17 miles of Gulf beaches can be reached within a half-hour drive from most anywhere in the county. Forming a winding ribbon of shell-strewn white sand, the county’s coastline extends south from Barefoot Beach at the Lee County line to Marco Island, the largest of the area’s famed Ten Thousand Islands. The shore alternates between more than three miles of city and county beach parks, state preserves, neighborhoods of beachfront cottages, mansions and high-rises and the Gulf-front resorts in Naples. Travel south from Naples and beaches give way to a mangrove-tangled coastline that signifies the beginning of the Everglades. Most beachfront homes are found in named communities, gated and nongated. Those not directly on the Gulf are within an easy walk and boast something their beachfront siblings can’t—deep water for a prized boat-in-your-backyard lifestyle. Yet living on the beach comes with a cost: higher home prices and some lack of privacy (all beaches are public).
Barefoot Beach is flanked by a county beach park and the 324-acre Barefoot Beach Preserve state park where visitors are updated daily on wildlife sightings—everything from bottle-nose dolphins to sea turtles and gopher tortoises. The neighborhood is a short walk or bike ride away from several restaurants (seafood is the specialty) and retail stores along Bonita Beach Road. The adjoining Bonita Springs beach access offers picnic and restroom amenities and wide shell-crushed beaches. Some of the best hotdogs around can be found under the umbrella of a curbside vendor. Nearby Doc’s Beach House, a two-story landmark, serves up burgers, sandwiches, seafood, a fabulous grouper sandwich and pitchers of beer. Open until 11 p.m., it’s also one of the most popular sunset-viewing spots on Bonita Beach.
Homes in Barefoot Beach, found in just a handful of neighborhoods, range from condominiums, villas, cottages and three- and four-story Mediterranean and Florida-style homes. Homes have become bigger and more expensive over the years.
Vanderbilt Beach, south of Barefoot Beach, offers a multitude of waterfront options: single-family homes along canals, bays and the beach, and Gulf-front high-rises with views of the Gulf and Sanibel Island. The neighborhood demonstrates Southwest Florida’s ease in the art of juxtaposition; it’s sandwiched between the natural beauty of Delnor-Wiggins Pass State Park on the north and the cosmopolitan resorts, boutiques and restaurants to the south at Gulfshore Drive and Vanderbilt Beach Road, home to the Ritz-Carlton Beach Resort and Vanderbilt Beach Park.
Delnor-Wiggins Pass is coveted for its amenities that give visitors the opportunity to enjoy nature’s bounty, from snorkeling, sun worshipping and swimming to fishing and kayaking along estuaries and scuba diving the hard-bottom reef of the Gulf. Gulfshore Drive ends at Vanderbilt Beach’s southern boundary and is lined by condos, resorts and the occasional single-family home. Vanderbilt Beach Park offers sugary beaches and newly added parking, thanks to a new parking garage.
The 2,100-acre Pelican Bay community occupies the sprawling span of land between Vanderbilt Beach Road and Seagate Drive. Only a handful of luxury high-rises and The Strand, an exclusive triple-gated neighborhood of just a dozen multistory Mediterranean homes, enjoy an on-the-beach venue. Developer WCI Communities, however, brings the beach to Pelican Bay residents, who can opt for membership privileges in a private beach club. Prime shopping is close by at the tony Waterside Shops, where a recent renovation yielded a more contemporary look and exclusive boutiques from Gucci, Burberry, Hermès, Tiffany & Co. and other high-end designers and retailers. Other symbols of Naples’ growing cultural cachet are the newly renamed Naples Grande Resort and entertainment options at the nearby Naples Philharmonic Center for the Arts and Naples Museum of Art.
Neighboring clam pass Beach Park marks the northern point of Naples proper and its 10 miles of beaches that earned kudos in 2005 from the Travel Channel as America’s Best All-Around Beach. Beaches stretch along Gulf Shore boulevards north and south from Seagate Drive to Gordon Pass, the southernmost point of the famous Port Royal neighborhood. The coastal boulevard passes elegant high-rises, high-end resorts and restaurants, and offers glimpses of the Gulf between the homes, an eclectic mix of new estates and older cottages, some dating back to the late 1880s. Clam Pass’ three-quarter-mile boardwalk winds through scenic mangrove forests and over coastal dunes en route to the 35-acre county park, where amenities include picnic areas, rentals and a canoe launch. Naples Cay and Park Shore, just south of Naples Grande, are mainly high-rise condo communities, offering a mix of old and new buildings. Naples Cay is set on 33 acres of preserve and the white-sand beach of Clam Bay. Park Shore incorporates single-family homes and towers along Gulf Shore Boulevard North and the picturesque and oft-photographed Village on Venetian Bay, an upscale collection of restaurants, boutiques and galleries.
The northern sweep of Gulf Shore Boulevard takes in two of Naples’ oldest communities, The Moorings and Coquina Sands. Both feature mostly single-family homes (with some mid-rise condos) on larger landscaped lots (some waterfront) and homeowner associations with beach access. The Moorings, Naples’ largest subdivision with more than 4,000 residents, 1,300 acres and 1,938 homes and apartments, offers many waterfront homes, including some with mile-long views to the Village on Venetian Bay, and frontage along Moorings Bay, which provides access to the Gulf at Doctors Pass. Homes in Coquina Sands are nestled along winding streets lined with ficus, banyan and palm trees and sidewalks for jogging, biking and walking. Close to the Fifth Avenue shopping district, the neighborhood is within walking distance of the resorts along Gulf Shore Boulevard.
Coquina Sands and Moorings residents are also close to Coastland Center shopping mall, Naples Zoo at Caribbean Gardens, Fleishmann Park, Naples Community Hospital and perhaps one of Naples’ best-kept secrets—the 9.5-acre Naples Preserve, a scrub oak community nestled into the southeast corner of U.S. 41 and Fleischmann Boulevard, just across from the mall. Although the unique glass and angular architecture of the preserve’s eco-center should tip off the unsuspecting, visitors delight in the .4-mile boardwalk and the feeling of traveling back in time and viewing Florida 10,000 years ago.
Beach outposts in Naples include Lowdermilk Beach Park, offering shade trees, picnic tables, concessions and sand volleyball; public access points at the eastern boundaries of Naples’ east-west avenues; and the picturesque Naples Pier, which extends 1,000 feet into the Gulf and is found at the west end of 12th Avenue South. The pier is especially popular with anglers; a bulk fishing license allows all to enjoy without an individual license. The facility also offers a concession stand, bait shop and volleyball nets. It’s another favorite spot to catch a sunset.
Gulf Shore Boulevard North assumes its southern coordinate at Central Avenue, and rambles south passing old cottages and multimillion-dollar beachfront estates, hidden behind thick landscaping. One of Naples’ most historic homes, the 1895 Palm Cottage, is found along the boulevard close to the beach. It was the home of Louisville Courier-Journal owner Walter Haldeman, who helped put Naples on the map. Gulf Shore Boulevard South eventually becomes Gordon Drive, the western boundary of Port Royal and the Port Royal Club, one of the world’s most exclusive members-only clubs.
Residents love Everglades City for what it doesn’t have—a shopping mall, a traffic light, high-rise condos, golf courses or any of the amenities of its more suburban Collier County siblings. The original county seat and the staging area for Barron Collier’s ambitious road-building undertaking (the Tamiami Trail), Everglades City is rich in history and prized for its natural setting, brushing up to the Everglades and Big Cypress National Preserve and set along the banks of Lake Placid and Chokoloskee Bay.
Yet with all this water, E.C. has no beaches. Inevitably residents are lured by the rural, small-town Americana delivered by E.C., all two miles by four blocks of it, and its ample opportunity for outdoor recreation—fishing, boating or kayaking around the Ten Thousand Islands or hiking and nature photography for landlubbers.
Everglades City becomes the center of the seafood universe each February with the annual Everglades Seafood Festival, featuring live music, rides, attractions and, you guessed it, seafood. Other nearby attractions include the Gulf Coast welcome center to Everglades National Park, the 11-mile Jane’s Memorial Scenic Drive in the Fakahatchee Strand State Preserve (home of the elusive ghost orchid) and Ochopee, where Everglades photographer Clyde Butcher hangs his shingle and displays his famous black-and-whites.
Everglades City and its surrounding environs—Pleasure Island, Plantation Island, Copeland and Chokoloskee Island (a pioneer trading post and home to the historic Ted Smallwood’s store) feature a variety of residential offerings—sportsmen’s cabins and condos right on the water, million-dollar estates, Barron Collier-era cottages, mobile homes and vacant lots.
Golden Gate City
Swing sets in the back yard, basketball hoops in the driveway and public facilities that offer an auditorium, gymnasium, aquatics center and fitness center are testament to this unofficial city’s appeal to families. Homes, even those on one of the area’s many canals, are still considered affordable here. As a result, Golden Gate City is becoming a great melting pot, attracting newcomers from Miami and other Southeast Florida venues, as well as first-time Collier County residents.
The conveniences of a full-fledged city are also offered here—mom-and-pop businesses, national chain supermarkets and restaurants, a public library and the tax collector. The Golden Gate Community Center has an auditorium, game and meeting rooms, a woodshop, kitchen and gymnasium. The county-run Golden Gate Community Park hosts children’s sports teams and pick-up games and offers several lighted softball, baseball and Little League fields, a lighted soccer/football field and lighted tennis and racquetball courts.
Golden Gate Estates
A rambling address of roughly 43,000 acres, Golden Gate Estates is Collier County’s largest neighborhood, sweeping south from Immokalee Road to Alligator Alley and east-to-west from DeSoto Boulevard to I-75. Its largeness makes owning a large tract of land possible, which appeals to former suburbanites and young families looking for room to spread out.
Early Estates residents tamed swampland into canal-front lots and carved out the Estates’ original five-acre wooded tracts, many of which have now been subdivided to 1.25-acre lots. Still, buyers find enough property to own horses and build sprawling homesteads. The absence of homeowner associations means no annual fees and no one dictating architectural requirements.
Census statistics cast a revealing picture of Immokalee, a rural farm town where the majority of residents are Hispanic, male and have a median age of 24.7 years. Settled in 1873 by hunters, trappers, traders and ranchers, Immokalee is the birthplace of Arizona Cardinals running back Edgerrin James. This unincorporated town is facing a renaissance, thanks to the arrival of a university and a new town 10 miles away, and growing attention to the plight and substandard housing faced by migrant field workers.
Much of Immokalee’s retail and commercial base, including restaurants serving authentic Mexican cuisine and groceries, caters to the needs of the migrant workers and local farmers, and is found along Main Street and its side streets. The Seminole Casino is located on First Street, and the 599-acre Immokalee Seminole Reservation, created in the 1980s, is located on the outskirts of town, as is Corkscrew Swamp Sanctuary.
Ave Maria University’s permanent campus and the town of Ave Maria, both the brainchild of Domino’s Pizza founder and former Detroit Tigers owner Thomas Monaghan, are built nearby the town. The 5,000-acre project marks the first new major Catholic university in the country in the past 40 years, and the town is the first-ever modern municipality developed in conjunction with a university. It offers 11,000 homes in a variety of styles (including designated affordable housing units), a European-inspired town center, La Piazza, schools, parks and public facilities.
Isles of Capri
This chain of islands becomes stone crab central from mid-October to mid-May, Florida’s season for the succulent crustacean. Many Naples area restaurants and crab connoisseurs buy the claws right off the boat at Capri Fisheries on Kon Tiki Drive. Located two miles north of Marco Island, Isles of Capri was developed by Tennessean Leland L. “Doc” Loach, whose vision of an island hideaway came true when he purchased the 600-acre mangrove islands in 1955. Loach dredged canals, built a water plant, linked each island with land bridges and carved commercial and residential properties into the wilderness. Civilization seems far-flung; other than the Marco skyline seen from the southernmost island, Isles of Capri is surrounded by undeveloped mangrove islands, part of the Ten Thousand Islands chain.
Island homes include new and older condos, Old Florida fishing cottages and newer mansions. Most homes sit on the water, either canals or fingers of Johnson and Tarpon bays and Big Marco Pass. Boating and fishing are popular pastimes, evident by four on-island marinas and several restaurants that offer docks and tiki huts. The island chain also has two convenience stores, a community center and a fully staffed fire and rescue department.
Top the Jolly Bridge linking Marco Island to the mainland, and you’re likely to marvel at this 14-plus-square-mile island. From this vantage point homes seem flush with the surrounding water and the view carries west for miles. At street level however, Marco welcomes with all of the tropical magic that attracted the first population explosion in the 1960s—well-manicured landscaping and tropical homes set against canals, the Gulf and the city’s various inland waterways. Water brought the first settlers to the largest of the Ten Thousand Islands in the 1870s and continues to attract today’s new residents—mainly part- and full-time buyers who want a boat in the back yard and a carefree island lifestyle without sacrificing convenience and amenities—top shopping, restaurants and on-island healthcare.
Marco Island’s earliest settlers were the Calusa Indians, whose hand-carved works, including the most famous—the six-inch wooden Key Marco Cat—have been uncovered during archeological digs. The presence of these primitive people is still felt in Marco’s Caxambas section at the south end of the island, where a 50-foot shell mound creates the county’s highest point above sea level. It’s now home to the Estates and Marco’s highest concentration of multimillion-dollar single-family homes. As recently as the late 1800s, Marco was merely a point on the map. The island wasn’t really inhabited until after the Civil War and the arrival in the 1870s of homesteader William Thomas Collier (no relation to county patriarch Barron Gift Collier). Collier is credited with founding Old Marco village, located at the north end. His sprawling home site operates today as the Olde Marco Inn, and several Collier-era structures still stand.
Marco Island has six miles of beaches, six city parks, designated biking trails, upscale shopping and dining at the waterfront Esplanade, and a number of well-regarded spas and restaurants in resorts dotting the Gulf of Mexico, including the four-diamond Marco Beach Ocean Resort.
Sixty percent of Marco Island’s homes are on the water—the Marco River, the Gulf, canals and surrounding bays and estuaries. Most are real estate is within walking or biking distance of Marco’s beaches. Tigertail Beach, on the island’s north end, offers five boardwalks, a bathhouse, concessions, beach rentals, volleyball and views of Sand Dollar Island, which has the largest concentration of shorebirds in South Florida. Resident’s Beach, at the intersection of Collier Boulevard and San Marco Road, has chickee-hut-shaded picnic tables, restrooms and a children’s play area, and South Marco Beach is found on Collier Boulevard. Other public facilities include the Collier County Racquet Center, Frank E. Mackle Jr. Community Park and Caxambas Park.
Travel east along San Marco Road and momentarily leave civilization behind. The road’s nothingness eventually arrives at this tiny fishing village, a handful of crisscrossing streets surrounded by Goodland and Gullivan bays and Coon Key Pass and home to just 200 residents. Isolated from the mainland until the completion of a swing bridge and San Marco Road, built using shells from nearby shell mounds in the late 1930s, Goodland’s potential for real estate has only recently been discovered.
Goodland’s population swells each Sunday afternoon when in-the-know visitors and residents flock to Stan’s Idle Hour Seafood Restaurant. Nearly 5,000 people converge on Goodland each January for Stan’s three-day Mullet Festival, celebrating the fish, not the 1980s hairstyle. Fried and smoked mullet are on the menu, and Stan’s crowns a Buzzard Lope Queen and Princess. (Owner Stan Gober wrote The Buzzard Lope Song).
Naples is known internationally as a favorite winter retreat for celebrities and others in the rich-and-famous set. With its world-famous beaches, cosmopolitan shopping and dining along Fifth Avenue South, Third Street South and the newly renovated, designer-studded Waterside Shops, gracious beachfront homes and venue for the country’s premier wine festival each January, Naples’ star is on the rise. National media coverage of ritzy real estate never fails to mention this city by the sea. Naples has some of the most enviable addresses in the country, and it’s no wonder that those who live on the outskirts (the official boundaries incorporate just 12 square miles) consider themselves Neapolitans. Its mix of neighborhoods and homes—from gated country club communities to beachfront mansions and historic beach cottages to luxury condo communities—add to its charm. So does its rating in 2005 as the No. 1 Small Art Town in America, a credit to Naples’ offering of galleries, arts fairs, art centers, theaters and the Philharmonic Center.
Most of Greater Naples’ gated communities have been developed along the area’s major roads—Immokalee Road, Airport-Pulling Road, Tamiami Trail, Goodlette-Frank Road and Livingston Road. Their arrival along less developed stretches of road often signal the next hot growth spot, with shopping centers, restaurants and office parks popping up soon after. The completion of the Livingston Road extension created a major north-south link between south Naples and Lee County, and now boasts the newly opened North Collier Regional Park, featuring a 6,000-square-foot RecPlex facility with state-of-the-art fitness center, walking trails, a boardwalk spanning a wetland preserve and the Sun-n-Fun Lagoon water park.
Areas of Livingston Road and Vanderbilt Beach Road near I-75 are home to several equestrian estates and riding schools. Five-acre tracts provide ample room for barns and riding arenas in Livingston Woods, offering just under 400 single-family lots, large enough for horses, homes and guest homes. The neighborhood features a nice mix of Old Florida-style homes with front porches and widow’s walks and Mediterranean estates on lots typically one to two acres. It’s also close to the Community School, Barron Collier High School, shops and restaurants. The northern sweep of Livingston includes several gated communities: Tuscany Reserve, Mediterra, Delasol and Milano.
Small neighborhoods and gated communities intermingle with some of the most exclusive private golf courses—the Royal Poinciana Club and the Hole in the Wall—along Goodlette-Frank Road, whose southern terminus boasts Bayfront, a vividly painted mixed-use development of high-end boutiques, restaurants, art galleries and four floors of luxury condos. Tin City, Old Naples and Fifth Avenue South are close by, and residential amenities include a heated pool, tennis courts, fitness center, on-site boat slips and a clubhouse.
This neighborhood of 350 estate-size homes is just north of Port Royal, placing it just blocks from the beach and the exclusive shops and restaurants of Fifth Avenue South and Third Street South. Developed by Forrest Walker & Sons in the late 1950s, all but 30 of Aqualane Shores’ home sites sit on water, either deep-water manmade canals or Naples Bay. Like its neighbor to the south, the 300-acre Aqualane Shores is prized for its mature, tropical landscaping and tree-shaded streets; however many of those early Walker & Sons homes (home sites originally cost just $2,500) are being torn down and replaced by mega homes.
This neighborhood, set under a canopy of towering trees with traffic-controlling roundabouts, is the more affordable sibling to neighboring Coquina Sands and The Moorings. Hidden behind office buildings fronting Tamiami Trail and a shaded promenade with benches along Goodlette-Frank Road, Lake Park is close to Coastland Center and Fleischmann Park, a mile from the beach and within walking distance of Lake Park Elementary. Many of its houses are originals from the 1950s—smallish two- or three-bedrooms that have been lovingly remodeled or updated.
A 22-by-four-block neighborhood of about 3,000 homes and 10,000 residents, Naples Park is a neighborly sort of place, an amalgamation of new families, retirees and newcomers. Its location to the west of Tamiami Trail places it close to shops, restaurants and Naples’ entertainment venues. Nearby amenities include beach accesses, a library and a public park with racquetball facilities, a jogging path and tennis. Boaters and nature lovers will love spending time at nearby Delnor-Wiggins Pass State Recreation Area. Buyers will find older homes that are typical of those built in the mid-1900s—two bedrooms, one bath and carports—and newer homes.
There’s a certain mystique associated with living in Naples’ original neighborhood. Old Naples packs savvy and sophistication into its two square miles, a sweep that includes new Gulf-front estates and historic cottages, private condominiums and boutique hotels along quiet streets radiating from its two main centers—Fifth Avenue South and Third Street South, offering world-famous shopping at upscale boutiques, galleries, cosmopolitan bars, theaters and parks. In Old Naples, the beach is at best a few steps away and at worst a short bike ride. Residents can opt out of cooking for the evening and walk to dinner or stock up at Tony’s off? Third, an upscale market that offers supplies and staples, wines and cheese, and gourmet dinners to go. Close to beach clubs and marinas, Old Naples gives even landlocked homeowners the chance to own a boat and offers tree-lined green space at Cambier and Rodgers parks. Old-growth trees create a canopy overhead, and blooms and gardens add punches of color to this anything-but-urban scene.
Sandwiched between some of Naples’ busiest roadways (Tamiami Trail and Goodlette-Frank Road), Pine Ridge’s neighborhood often surprises first-time visitors with the size and number of its homes, seven large lakes and the presence of horse stables and riding arenas. The neighborhood offers large private lots, often boasting tennis courts, miniature soccer fields, guesthouses and either brand-new or 1970s-era homes. Located on the east side of Tamiami Trail, just south of Pine Ridge ?Road, the sprawl of commercial development and shopping centers eventually gives way to gracious homes fronting Trail Boulevard.
Perhaps Naples’ most recognizable address, Port Royal was developed more than 50 years ago by John Glen Sample, who built his personal fortune as an advertising executive in Chicago. So smitten was Sample with Naples, he purchased the city’s southernmost two miles along the Gulf and began taming swamplands, hammocks and beachfront into roughly 560 mostly waterfront lots. His ambition was simple, he want to “make this the finest place to live in the United States.” Today Sample’s prophecy holds true. Large shade trees create a canopy above the neighborhood’s streets; manmade peninsulas, coves and bays bring water into most back yards; and manicured hedges and enviable landscaping provide privacy. Many beachfront property owners have added to their land holdings, acquiring bayfront real estate to dock a boat. Sprawling mansions five times the size of the original 2,000-square-foot homes have replaced those first homes, and property values reach beyond the million-dollar mark.