It started with a visit—maybe a quick weekend trip to festive Fort Myers Beach. Or perhaps it was a weeklong honeymoon at a romantic resort on Sanibel’s shores or a raucous golf outing with the guys in Naples. Whatever first brought you to Southwest Florida has beckoned you back with its gentle winds, lazy nights and carefree, sunny spirit.  Now you’re ready to make your stay a bit more permanent with a home of your own in paradise, saving you from those cold, gray days of winter.
Just think—a new home 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 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.

Lee County was created in 1887, and like seven other counties across the country, it is named for Confederate Gen. Robert E. Lee. Unlike these other counties, including those in Alabama, Mississippi and North Carolina, our Lee County offers glorious weather year-round and miles of scenic beaches, islands and protected preserves. It wasn’t until the turn of the century, however, when Thomas Edison and Henry Ford were spending their winters here, that Lee County began to bloom.

Today’s Lee County has five official cities—Cape Coral, Bonita Springs, Fort Myers, Fort Myers Beach and Sanibel Island—and a full-time population of 544,400, more than half of them (292,400) living in the unincorporated areas. By comparison, the first county census in 1890 recorded a population of 1,414 residents just three years after it was formed from Monroe County.
Among the 100 fastest-growing counties in the country, Lee County attracts an average of 11,600 new workers each year, and 48 percent of its population is between 25 and 64 years old. Lee County’s character is a split personality of scenic barrier islands, a burgeoning cosmopolitan River District in downtown Fort Myers, operating citrus groves, sprawling resort-like gated communities and quaint river towns. Water is a major player in the county’s ongoing development. Bays, backwaters and manmade canals provide access to the Gulf and the county’s miles-long stretch of the Caloosahatchee River.
Beaches

Of Lee County’s nearly 600 miles of shoreline, 50 miles are beaches and 20 of them are named, stretching from border-straddling Gasparilla Island south to Bonita Beach. The majority of the county’s beaches are located on barrier islands, many of which are uninhabited and destined to stay that way. Others are accessible only by boat, creating a way-it-used-to-be kind of feeling. Each of Lee County’s beaches has a unique personality. Here, we present them from north to south.

Gasparilla Island

Home to Boca Grande and road-accessible only via Charlotte County, Gasparilla Island has evolved from its fishing and phosphate roots to a world-class destination for jet setters and residents. The venue of the World’s Richest Tarpon Tournament, the island is protected by the Gasparilla Act, which limits allowable density and building heights. The island’s size—seven miles long and only half a mile wide—puts the beach and the waters of the Gulf and Charlotte Harbor within walking distance of almost any home.   The 142-acre Gasparilla Island State Park offers five beach access points. The often-photographed Boca Grande Lighthouse is found in the appropriately named Lighthouse Beach Park.
Golf carts are the preferred mode of travel, especially in and around the quaint downtown area, where the former railroad depot has been restored and now contains shops, offices and restaurants. Art galleries and antique shops are also found here. The historic 1913 Gasparilla Inn, with its white-washed architecture, columns and porches, recalls another time. 
Homes and condos are sprinkled throughout downtown and along the water. Boca Grande Isles, a gated neighborhood of 123 waterfront properties, appeals to the avid boater with its deep water and to nature lovers who enjoy watching the unfolding natural scenery along Hole in the Wall Bay. Homes on Gasparilla Island range from the mid-$300,000s to $10 million. Coral Creek Club, located in nearby Placida, offers a scenic Tom Fazio-designed golf course (limited to 225 members), a clubhouse, limited airport memberships and Old Florida cottages.
Lacosta Island is as far removed from civilization as one can get while so close to it. A remote barrier island between Gasparilla and North Captiva islands, the upper northern portion is Cayo Costa State Park, offering nine miles of beaches and 2,506 acres of pine forests, oak-palm hammocks and mangrove swamps. Uninhabited except for overnight campers, the island is reachable only by boat.

Sanibel Island

The scenic Sanibel Causeway, a series of islands and bridges (a new span is under construction), begins at the end of McGregor Boulevard in Punta Rassa on the mainland. Decades of careful preservation have helped to retain much of the naturalistic appeal of Sanibel. A majority of the island is under the management of the federal government at the 6,400-acre J.N. “Ding” Darling National Wildlife Refuge.  Visitors and residents prefer biking to driving, especially during high season when a left-hand turn is next to impossible in this town without a stoplight. Periwinkle Way, the island’s main drag, offers quaint shopping centers and boutiques, restaurants, art galleries and even live theater. Building laws limit condos and homes to just three stories, says Jane Reader Weaver, a realtor who’s specialized in Sanibel and Captiva property for 20 years. Multimillion-dollar estates, cottages and condos share the shoreline with several beaches—Lighthouse Beach Park, featuring the island’s 1884 landmark lighthouse; Gulfside City Park; and the most popular, Bowman’s Beach. Mid-island Tarpon Bay Beach is a good spot for swimming and windsurfing. Blind Pass Beach, the official midway point between the two islands, is considered one of the best shelling spots in the world.

Captiva Island

Captiva is separated from Sanibel by a thin swipe of water at Blind Pass. Sanibel-Captiva Road becomes Captiva Drive, along which most of the island’s multimillion-dollar homes are found. Homes are hidden behind thick foliage, but passersby get an occasional glimpse of winding, crushed-shell driveways leading to simple cottages, Spanish-Mediterranean mansions and contemporary South Beach-style getaways. Most homes have names and offer either the Gulf or Pine Island Sound in their back yards. “Captiva is all waterfront,” says Weaver. “It’s a narrow slice of heaven.”
Venture farther north and you’ll eventually arrive at Captiva’s village, a quaint collection of pastel-hued, beachy shops, galleries and boutiques as well as steps-from-the-water homes located along sandy lanes. Restaurants like the Bubble Room, decorated in 1950s movie and TV memorabilia, and the Mucky Duck are within walking distance; golf carts and electric cars are preferred by residents who live farther away. Captiva Beach, ranked among the most romantic in the nation, is never more than two blocks away, and some say it’s the perfect spot to catch the mystical green flash at sunset. The gated South Seas Resort occupies the northern two miles of Captiva.

Fort Myers Beach

If you’re looking for a lively party, check out Fort Myers Beach, especially in March and April. Southwest Florida’s slightly tamer version of spring break hotspots Fort Lauderdale and Daytona, Fort Myers Beach has one of the hippest vibes of the region. Restaurants and bars offer toes-in-the-sand dining, dancing and drinking and an eccentric energy that keeps traffic—automobile and pedestrian—flowing 24/7 around Times Square and Estero Boulevard. Gulf-front homes, older and newer, and more than two dozen beach accesses are sprinkled among the many rental cottages and condos. Side streets offer water in the back yards—canals opening to Matanzas Pass and Estero Bay farther south—and the beach within a block’s walk. Most of the island’s commerce—seafood restaurants, bars, boutiques, beach shops and tattoo parlors—is located on Estero Boulevard, and many places, like the Lani Kai, offer on-the-beach musical entertainment and rooftop terraces. Walk the beach or the sidewalk on your pub crawl, or rent a bike or a scooter to get around.
The beach is the star attraction along Estero Island, and never more than a couple of blocks away.  The 17.5-acre Bowditch Point Regional Park, located on the island’s northern tip, serves as a drop-in point along the newly opened Great Calusa Blueway, a 100-mile canoe/kayak trail meandering through Estero Bay and the scenic bays around Sanibel, Captiva and Pine islands.
Estero Island eventually ends around Lovers Key State Park, Florida’s most visited state park. The park spans four islands and is nestled between Fort Myers Beach and Bonita Beach, offering sand paths that wind through mangrove forests and around tidal lagoons to one of two remote beach access points. Canoeing and bicycling are popular here. Dog Beach Park is located along Estero Boulevard and is the only off-leash beach park for dogs in Southwest Florida.

Bonita Beach

Estero Boulevard becomes Hickory Boulevard as it traverses the Broadway Channel. Intermittent beach access provided by the county appears between condos, homes and restaurants as the boulevard travels south six miles to Bonita Beach Road and the Collier County border. Most homes here back up to water, either the Gulf on the west or the back waters of Estero Bay. Three-story Mediterranean architecture is popular; however, you will find Old Florida stilt homes, rentals and original cottages. Prices vary from the low $200,000s to several million dollars.
The two-and-a-half-acre Bonita Beach Park is found at the point where Hickory Boulevard curves into Bonita Beach Road.  The county-run park has beach volleyball, a gazebo, restrooms with showers and picnic shelters.

Bonita Springs

Bonita Springs emerged slowly from its slumber as a sleepy fishing town in the late 1980s—a timetable many credit to the arrival of Bonita Bay, a 2,400-acre master-planned community. Now a bona fide city, its population increased 5.97 percent between July 2004 and July 2005. Bonita Springs has dozens of gated communities, upscale shopping centers, top-rated restaurants and a growing base of commercial activity. Neighborhoods have grown along the city’s main waterway, the Imperial River, and its major thoroughfares, the Tamiami Trail and Bonita Beach Road.
Bonita Springs clings to its past along Old 41 Road near the Imperial River, where moss-draped trees create a canopy above a city park, and older homes provide a glimpse back in time. The Everglades Wonder Gardens recalls the popular roadside attractions of the 1950s and gives visitors an up-close-and-personal look at ’gators and other indigenous Florida wildlife. The 1920s Shangri-La Springs Resort, where the hot springs reportedly attracted the likes of  Thomas Edison, Henry Ford and Franklin D. Roosevelt, is also found in this county-designated historic neighborhood. Many restaurants and stores serve the growing Hispanic population.
Recently listed home prices in Bonita Springs range from the $120,000s for a mobile home or single-bedroom condo to more than $4 million in the gated communities of Bonita Bay and Pelican Landing. The city’s growth is also reflected in its annually increasing taxable value, which climbed nearly 31 percent during the last year.
CAPE CORAL

Cape Coral is Southwest Florida’s second-largest city and the fifth fastest-growing metropolitan area in the country, and its once vacant lots are beginning to sprout homes in various stages of construction. The 115-square-mile city, created in the 1950s by brothers Jack and Leonard Rosen, who marketed the Cape as a winter retreat to Northerners, boasts 400 miles of canals, large freshwater lakes and frontage along the Caloosahatchee River. Until recently, it lacked the gated communities that defined other Southwest Florida real estate markets; much of the remaining undeveloped acreage was owned by a single company. Commercial development has been somewhat slow to follow.
Most of Cape Coral’s commercial and retail outlets are found along three main roadways—Del Prado Boulevard, Pine Island Road and Cape Coral Parkway, home to the city’s downtown, a blocks-long district of pastel-painted restaurants, boutiques and offices that hosts many of the city’s annual events such as block parties, arts shows and holiday parades. Dead-end side streets feature a number of smaller neighborhoods, often with still undeveloped lots and canal frontage, offering no-bridge or one-bridge access to the river and Gulf. An active city-run parks department oversees a number of regional and neighborhood parks, including Sun Splash Family Waterpark, the Four-Mile Cove Ecological Preserve and the Cape Coral Sports Complex.

Riverfront

Many of Cape Coral’s first homes were built in the 1950s and ’60s along the Caloosahatchee River near Redfish Point, home to the Cape Coral Yacht Club, which offers a boat ramp, a 634-foot riverfront beach, picnic shelters, barbecue grills, a fishing pier, public pool and tennis and racquetball courts. A handful of the original Rosen-built homes still stand on Flamingo Drive. New nearby gated communities—Tarpon Point Marina, built on the site of the Rosens’ Rose Garden, and the Marina at Cape Harbour—have introduced an upscale component to the Cape’s real estate market. Cape Harbour offers a public waterfront with a marina, shops and Rumrunners, an award-winning restaurant. Inland homes access the river via a thread of wide canals.
Older riverfront homes, built just
30 to 40 years ago, are being razed and replaced by larger million-dollar homes. The most expensive are found in
neighborhoods facing the Fort Myers shore a mile across the river, with views of its two bridges—the Midpoint Bridge and Cape Coral Bridge. Price tags of $3 million and $4 million are now commonplace for homes along
the Caloosahatchee.

Southwest Cape Coral

Realtors identify Cape Coral’s southwest quadrant as the new hot spot. A three-square-mile L-shaped neighborhood west of Chiquita Boulevard, the area offers existing homes, many built within the last 15 years, and vacant lots, some located on the South Spreader Waterway with Gulf access. “It’s one of Southwest Florida’s safest neighborhoods,” says Lenora Marshall, an agent with Century 21 Sunbelt. “There’s also a nice mix of families with children, young professionals, retirees and part-time residents,” adds her associate Teri Kibbe. Statistics show the average southwest Cape home costs $405,000 for an off-water location and $820,000 for a waterfront home.

North Cape Coral

The Pine Island Road corridor, which links the mainland to the barrier islands of Little Pine Island and Pine Island, has grown up in the past decade. Overgrown, vacant lots on weed-choked streets, paved and platted decades ago, are steadily disappearing, being replaced by modest homes. New retail has recently opened at Pine Island Road’s intersection with Skyline Boulevard, and other development is quickly following. Also helping the area’s rising status are plans to improve Burnt Store Road into Charlotte County.

ESTERO

New development continues to flourish along or near the Estero River—mainly new-home neighborhoods and commercial development. The scenic river leads eventually to Estero Bay and portions of it remain undisturbed, offering a glimpse back in time. Estero has several gated communities, a major outlet mall (Miromar Outlets), an ice-hockey/entertainment venue (Germain Arena), the new International Design Center, two top-flight hotels (Embassy Suites and the Hyatt Regency Coconut Point Resort & Spa) and Florida Gulf Coast University, the state’s newest college. New shopping centers border the town’s north and south boundaries—Gulf Coast Town Center at Alico and Ben Hill Griffin roads and Coconut Point at Coconut Road and U.S. 41.
Though Estero is still unincorporated, civic-minded and well-organized residents have created self-governed review boards that would make any full-fledged city envious. The boards set standards for Estero’s architectural appearance and its streetscape, among other things. They will help to guide the final design plans for the upcoming Estero on the River project, a mixed-use development that will include homes and the 500-seat, $20 million Gulfshore Playhouse Theater. Traces of Estero’s past are still visible along Sandy Lane and Broadway Avenue, where banyan trees create a canopy overhead, goats run in small fields next to older homes with screened front porches, and the sprawling champion Mysore fig tree stands sentry at the intersection of the two roads.

FORT MYERS
River District

Downtown Fort Myers, now officially known as the River District to reflect the 40-block area’s relationship to the Caloosahatchee River, continues its meteoric development. Two new high-rise condominiums are now open, and an ongoing flurry of activity will bring a total of 3,800 new homes in the next few years. The impetus for the development was an unused waterfront and a vision by master planner Andrés Duany, the father of new urbanism who’s credited with reviving Fifth Avenue South in Naples and South Beach in Miami. The design philosophy, says Don Paight, Fort Myers’ director of downtown redevelopment, “brings everything together. People can live, work, shop, play and do everything in one area. With rising gas prices it just makes sense to be able to walk to work or take a water taxi or shuttle. It makes for a better lifestyle. You don’t spend your life on the road driving.”
The city is in the process of a $50 million project that will relocate utilities underground, restore brick streets and reintroduce 1930s-era streetlights into the historic district, which stretches from Bay Street to Second Street and from Monroe to Lee streets. The growing district offers retail stores, restaurants and offices and some residences on second floors. Paight says the surrounding new-home developments, which range from 32-story towers to mixed-use developments and low-rises with resort-style amenities, appeal to the target demographic of urban dwellers. 
The River District’s nightlife comes alive on the weekends. Favorite haunts include the charming Brick Bar, which often features jazz and blues magicians, Fat Cat’s Drink Shack, the Cigar Bar and EnVie and Level nightclubs. Fine dining is available at Veranda, Harold’s on the Bay, The Morgan House and the new Patio 33. During the day, rub elbows with government employees and attorneys for lunch at Second Street Deli. To the east of the district is historic Dean Park, a neighborhood of 1920s Victorian and Colonial homes and Florida-cottage bungalows that have been lovingly restored by new owners. To the south are the Fort Myers Skatium and the City of Palms Park, the spring-training home of the 2004 Major League Baseball champion Boston Red Sox.

Riverfront

The Caloosahatchee River divides Fort Myers and Cape Coral, reaching a mile wide at its fullest. Some of the earliest development in Fort Myers took place along the river, mainly on the city’s famous royal-palm-lined McGregor Boulevard and its cul-de-sac side streets. The winter homes of Thomas Edison and Henry Ford are found west of downtown, encircled by white picket fences and botanical gardens. The homes and Edison’s laboratory are open to guests and host a number of special events, including a holiday house and activities associated with the Edison Festival of Light, a three-week celebration of the city’s most famous resident.
The neighborhood offers diverse architecture, from older two-story brick estates and mid-1950s ranch homes to Spanish-style haciendas and Mediterranean revival homes mixed with the occasional contemporary or Old Florida (some nearly a century old). Most homes are on large lots and hidden behind decades-old landscaping and tidy hedges, and some include a sweep of river in the back yard. The area is favored by families with children because of its neighborliness—families tend to know one another and children walk to school. Many homes have been occupied by the same owners since the 1970s or earlier, and some have a storied past—once home to the first bank president or the first funeral home director in the area. And now the next generation is returning; adults who grew up in Fort Myers want their kids to grow up in the same neighborhood they did. Recent sales have ranged from $155,000 for a small condo to more than $3.7 million for a 5,400-square-foot home on the Caloosahatchee River.
Newcomers like Charles and Kimberly Cook are captivated by the charm of the area’s older homes. The Cooks are renovating a 65-year-old home on Gasparilla Drive, just off McGregor Boulevard. “I had never been to Fort Myers before, and although I’m a fourth-generation Florida native, I’m not really into palm trees; I’m from the center of the state,” says Kimberly. “But when I drove down McGregor that first time and saw the big palms, then turned onto Gasparilla and saw the river at the end of the street, I thought, this is beautiful.”
Edison Park offers a similar way of life, but is not on the river. Found directly across from the Edison homestead, it was designed by the inventor’s good friend, the late Jim Newton, and offers 1970s-era homes priced in the high $200,000s, as well as a mix of newer and older residences priced to more than $1 million. The Fort Myers Country Club is within walking or biking distance of most homes.

South Fort Myers

Fort Myers’ jagged city boundaries continue south until about Colonial Boulevard. Anything south of the city limits is known as south Fort Myers, an unincorporated area of Lee County that was home to nearly 50,000 people in 2000. It’s a large swath of land between Lehigh Acres, San Carlos Park and the Caloosahatchee that incorporates several distinct neighborhoods, including Cypress Lake, Iona-McGregor, Punta Rassa, Whiskey Creek and The Villas. Proximity to the beaches, the HealthPark Medical Center and a county park attract many residents to the area.
Iona-McGregor follows McGregor Boulevard en route to Fort Myers Beach, and because of its proximity to water, offers some homes along canals leading to the Caloosahatchee River and overlooking Cape Coral on the river’s west bank. Located off McGregor are the sprawling Gulf Harbor Yacht & Country Club and the ungated Town and River Estates, offering older homes, some on canals. Commercial development includes restaurants, retail stores and the Tanger Outlet Center at the triangular intersection of McGregor and Summerlin. Punta Rassa is home to the Sanibel Harbour Resort & Spa and a number of condo buildings. Turn from Summerlin Road onto John Morris Road and you’ll eventually find Fort Myers’ only beach, the 731-acre Bunche Beach, where natural tidal wetlands offer a look at Florida’s more wild side.
Whiskey Creek, a 1,500-home subdivision dating from 1969, borders its namesake creek off McGregor Boulevard and is north of Iona-McGregor. Selling points include an executive golf course, a mix of condos, 55-and-older multifamily housing and single-family homes, and a great location—close to the Barbara B. Mann Performing Arts Hall, and a number of restaurants and shops.
The Villas, a 1,350-home neighborhood behind the upscale Bell Tower Shops, was platted in the 1950s and boasts mature landscaping, large lots and mostly older homes. The first planned residential neighborhood developed south of Fort Myers, The Villas has a community center, a two-and-a-half-acre park and a voluntary but active homeowners association.
A number of subdivisions and gated communities are found on each side of the Tamiami Trail as it heads south to San Carlos Park. Nearby Lakes Regional Park on Gladiolus Drive is a 279-acre oasis in the middle of all this development, with more than half the park dedicated to freshwater lakes for fishing, canoeing and swimming. Two of the area’s newest high-rises at Riva Del Lago offer resort-style amenities.
Destinations in the eastern portion of south Fort Myers include the Southwest Florida International Airport, the Six-Mile Cypress Slough Preserve and Hammond Stadium, the spring-training home of the Minnesota Twins.

LEHIGH ACRES

Once a 20,000-acre tax shelter for a Chicago businessman-cum-Florida rancher, today’s Lehigh Acres is experiencing sizzling construction activity, with 600 new-home construction permits issued monthly, taxable property values that increased 88 percent during the last year and a population of 42,400. Lee Ratner saw Lehigh’s potential in 1954 when he subdivided his Lucky Lee Ranch, making the east Lee County community the first post-World War II retirement community in Florida. Today the 95-square-mile Lehigh has 152,000 lots (some on lakes and canals), a mix of new and old homes and is one of the more affordable real estate markets in Southwest Florida, sought out by young families and first-time homebuyers. The median age has dropped from 38 in 2000 to 36.5.
Proving Lehigh’s affordability: Condos are priced under and around $100,000 and homes start around $200,000. Some newer, larger homes are approaching the $1 million mark.

NORTH FORT MYERS

Development has slowly pushed its way out of downtown Fort Myers and into North Fort Myers, where new gated communities mingle with mini farms. Waterfront (canals, lakes and the Caloosahatchee River) is often found in the mix, where $1 million homes offer deep-water sailboat access. The area has a solid commercial base and a major tourist attraction—the Shell Factory and Nature Park with its Waltzing Waters. The river, Cape Coral and Charlotte County define the area’s 70 square miles.

PINE ISLAND

An island just 17 miles long by two to four miles wide, Pine Island offers several distinct personalities—from the arts and fishing town of Matlacha on Little Pine Island to the peace and quiet of Bokeelia on its northern tip and the more populated St. James City at its southern point. One thing you won’t find on Pine Island: beaches. There aren’t any, and residents are content for it to stay that way.

Matlacha

Home of the “fishingest bridge in the world,” Matlacha was originally inhabited by squatters, who built fishing camps along Pine Island Road. Today these small cottages are considered historic gems, and some are now used as art galleries and shops. Side streets display Matlacha’s fishing and shrimp fleet and a combination of older and newer homes, most on the canals that reach into Matlacha Pass. Residents like the area’s laid-back ambiance and its walk-to-anywhere location. There’s even a park, bait and tackle shops, a few restaurants and a bar. Pastel buildings and painted light poles reflect Matlacha’s artistic side.

Pineland/Bokeelia

Tiny Pineland, found at the three-point convergence of Pine Island and Stringfellow roads, has amenities reserved for much larger places. There’s a post office (albeit one of the country’s smallest), a marina, a bible college, a marine research institute, an Indian archaeological site and even a golf course. Pineland also boasts a working novelist—Randy Wayne White. There’s a restaurant and hotel—the 1926 Tarpon Lodge and Restaurant, overlooking Pine Island Sound. Charters to the surrounding islands—Sanibel, Captiva, Useppa and Cabbage Key (a restaurant there is rumored to be Jimmy Buffet’s inspiration for Cheeseburger in Paradise)—are available at nearby Pineland Marina.
Bokeelia seems virtually undiscovered despite its port, restaurants (the Lazy Flamingo and Captain Cons, which serves fabulous grouper) and art galleries. Homes here embody Florida’s past—some have white picket fences, tin roofs, widow walks and wraparound porches for watching the sun set over Black Bay and Charlotte Harbor. Anglers say Bokeelia’s shallow waters are ideal for snook, trout and grouper.

St. James City

About two-thirds of Pine Island’s residents live in St. James City, accessed eight and a half miles due-south on Stringfellow and past Elks, Moose and fisherman’s clubs and co-ops. St. James City has a thriving commercial base with businesses that take advantage of its ties to the sea. There are several marinas and fishing charters and establishments like the Waterfront Restaurant and Marina, said to attract diners from 50 miles away with its burgers and grouper sandwiches, and the Double Nichol Pub, a tavern and sandwich shop, where the specialty is “the Father,” a toasted sandwich with bologna, pepperoni, salami, cappicola, provolone, jalapeños, oil, lettuce, tomato and onion.

SAN CARLOS PARK, THREE OAKS

Escalating home prices, proximity to the international airport and university, and a new shopping center (the mega Gulf Coast Town Center) have placed this south Lee County community on an upward spiral. Close to the major amenities of its larger neighbors—Fort Myers to the north and Bonita Springs to the south—San Carlos Park and Three Oaks are the ideal midpoint for folks who work in Naples and Fort Myers. Many residents moved into San Carlos more than five years ago, when homes sold in the low $100,000s and attracted young families and first-time buyers. Two recreational facilities—the 36-acre Three Oaks Park and the Karl Drews Community Center—offer programs for children and adults, youth sports and playgrounds. Baseball and soccer fields at Three Oaks Park stay busy most weekday and weekend nights. Many of the vacant lots from a few years ago now have homes. Lots in San Carlos tend to lack deed restrictions and city water and sewer service (a majority of homes use wells and septic tanks). Newer areas, like neighboring Three Oaks, have central water and sewer services and deed restrictions. 

RURAL LEE COUNTY

Even Lee County’s rural edge is changing. Gated communities along Palm Beach Boulevard/S.R. 80, once considered too far removed from the amenities of Fort Myers, are proliferating. Verandah, located along the Orange River, and River Hall, a 2,000-acre community by new-to-Southwest-Florida developer LandMar Group, take advantage of the slower way of life this area affords. Far-off towns like Alva and Buckingham have also kindled interest from buyers who want a more rural lifestyle and larger lots that can accommodate mini-ranches and horses.
Many of the homes in Fort Myers Shores, found along the south bank of the Caloosahatchee River east of S.R. 31, back into canals leading to the river. Travel farther east along S.R. 80 and signs of civilization and development relax. Land restrictions have kept vacant property in Buckingham, the site of a World War II Army training camp for airplane gunners, fairly large in size. Neighboring Olga is located on the Caloosahatchee. Development has followed with a new Publix-anchored shopping center at routes 80 and 31. Recreational outlets are just miles apart—a marina at Sweetwater Landing, Hickey Creek Mitigation Park, Franklin Lock Recreational Area and the Caloosahatchee Regional Park, a 768-acre facility on the north shore with two walking trails, mountain bike and equestrian trails, primitive campsites and breathtaking views of the namesake river.
Just east of the park is Alva (Latin for white), named by Danish sea captain and botanist Peter Nelson for the white flowers growing along the riverbank. As one of Lee County’s first county commissioners, Nelson platted out the village of modern-day Alva, laying out a network of streets and setting aside property for schools, parks, churches and the first library in South Florida. Today Alva’s surrounding citrus groves and pastures are being transformed into gated communities, five- to 10-acre residential tracts and grand riverfront homes surrounded by moss-draped live oaks. Alva’s quaint century-old United Methodist Church is the oldest church in continuous use in Southwest Florida.

COLLIER

Florida’s largest county, Collier, has shed its fishing-town persona for a more polished, sophisticated identity that often attracts celebrities and luminaries who shop, dine and vacation 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 group, 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 time and place. Home prices in some areas now command more than $20 million—well above the $125 of a turn-of-last-century beachfront lot.

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 almost 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 non-gated. 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,” says Barefoot Beach Realty’s Nick Fontana, who’s been selling Barefoot Beach property for nearly 20 years and has seen most of the neighborhood’s original beach cottages razed and replaced.
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. Residents and beach visitors soon discover the area’s close-to-everything amenities, including top-star dining at Baleen in LaPlaya Beach & Golf Resort; Da Ru Ma, a Japanese steak house; or the Turtle Club, part of the quaint Vanderbilt Beach Resort.
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 such as Gucci, Burberry, Hermès, Tiffany & Co. and other high-end designers and retailers. Other symbols of Naples’ growing cultural cachet are the newly renovated 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 one-quarter-mile boardwalk and the feeling of traveling back in time and viewing what Florida looked like some 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.

Everglades city

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 opportunities for outdoor recreation—fishing, boating or kayaking around the Ten Thousand Islands or hiking and nature photography for landlubbers. In fact, Jan Brock, the sole real estate agent in Everglades City until a recent land rush a few years ago, sees a residency pattern. Southeast Floridians, she says, will buy a weekend escape, gradually lengthening their visits until it’s finally time to make the move permanent. “Everglades City is laid back. You know you can’t be at the mall in five minutes, and you really don’t care,” she says.
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. Prices range from nearly $200,000 to more than $1 million.

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. It is home to the Golden Gate Aquatic Complex, featuring several heated pools, a 110-foot water slide and a fully equipped fitness center. Small condos, nestled along the fairways of the public golf course, start in the mid-$100,000s; single-family homes range from around $200,000 to about $500,000.

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 immense size 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, says Bruce Farrell, a real estate agent with Century 21 and the self-proclaimed Estates King. “People who move to the Estates want to get away from having a neighbor right in their back yard,” he says. The price spread of homes here is across the board—anywhere from $300,000 for older homes with a more eastern address to more than $2 million.

IMMOKALEE

Census statistics cast a revealing picture of Immokalee, a rural farm town where the majority of residents are Hispanic (71 percent), male (56.4 percent) and are of 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 set to debut this year. 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 will offer 11,000 homes in a variety of styles (including designated affordable-housing units), a European-inspired town center, La Piazza; schools; parks; and other public facilities. The 100-foot tall Oratory will serve as the visual heart of the university, and given Florida’s flat landscape, will likely be seen from miles away.

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.

MARCO ISLAND

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. Marco is a city, voter-approved in August 1997, and by best guesses is expected to reach build-out around 2010. About 300 new homes are built each year.
Sixty percent of Marco Island’s homes are on the water—the Marco River, the Gulf, canals and surrounding bays and estuaries. Offerings include multimillion-dollar estate homes, efficiency condos starting in the mid- to high-$100,000s, time-shares and decent single-family homes, priced, on average, at about $600,000. Most are 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.

Goodland

Travel east along San Marco Road and you’ll 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 only recently attracted interest in its real estate. Condos are now part of  the existing housing mix, mostly Old Florida homes that sell from the high $300,000s to more than $1 million—a contrast to the town’s 1949 inhabitation by squatters, whom developers relocated from Marco’s Caxambas neighborhood.
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

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 seldom 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—adds 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’ three-dozen or so 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 new 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 of 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.
Hot right now is Collier Boulevard, where new gated communities join un-gated 1960s and 1970s neighborhoods along many of the boulevard’s radiating roadways. The link to Marco Island, Collier Boulevard, gets increasingly upscale as it heads west, passing the 3,000-acre Lely Resort, Treviso Bay brushing against the 25,000-acre Rookery Bay National Estuarine Research Reserve, and the 4,000-acre Fiddler’s Creek.

Aqualane Shores

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. Homes, both old and new, are priced from about $1.5 million.

Lake Park

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. Large lots with pools, mature landscaping and fruit trees are also a big attraction, and prices (primarily in the mid-$400,000s to $700,000s) are what Moorings and Coquina Sands were five years ago.

Naples Park

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, and prices from the $300,000s to more than $1 million.

Old Naples

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.

Pine Ridge

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. It’s on the east side of Tamiami Trail, just south of Pine Ridge  Road, and the sprawl of commercial development and shopping centers eventually gives way to gracious homes fronting Trail Boulevard. Condos, found in Emerald Woods to the north of the neighborhood boundaries, start in the high $200,000s. Single-family homes, even those sold “as is,” start just below $1 million and top out around $4.5 million.

Port Royal

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. It’s a secluded neighborhood whose fate was determined by the arrival of the Ritz-Carlton, says long-time Naples builder Gary Carlson. “The Ritz brought in a whole new clientele to Naples,” he says. Today prices fluctuate from $2.25 million for a nonwaterfront likely teardown to nearly $25 million.

Royal Harbor, Oyster Bay,
Golden Shores

Royal Harbor is Naples’ only 100 percent waterfront community. All of the 419 single-family homes in this triangle of a neighborhood sit on Naples Bay or a series of deep-water canals that lead to the Gulf. Though located on the east side of the bay, Royal Harbor is close to Tin City, Bayfront, Fifth Avenue South and the beaches. Homes vary from new to 1960s originals; most have pools and docks in the back yard, and cost from about $1 million to $6.5 million. Adjoining Oyster Bay and Golden Shores also offer waterfront homes plus some condos and villas, priced from about $300,000 to $2.1 million.