Summary
- Delray Beach: A coastal town with a vibrant downtown, attracting retirees and second-home buyers with its upscale amenities and prime location.
- Boca Raton: An affluent community known for its high-end shopping and dining, appealing to snowbirds and professionals seeking luxury and a thriving financial hub.
- Hollywood: A coastal city with miles of beaches, condos, and dining, drawing urban professionals with its vibrant arts district and affordable real estate compared to its neighbors.
Florida is known for its immaculate sunny beaches, theme parks, and retiree communities, but the state is also home to some of the American attractions like the Kennedy Space Center and SeaWorld Orlando. Driven by demand from wealthy snowbirds, second homeowners, and professionals relocating for Florida’s business-friendly tax policies, home prices in many cities now rival New York and California.
While all of Florida saw home values skyrocket over 17.27% in the past couple of years amid the pandemic real estate boom, some cities stood out for their ultra-high prices. From historic coastal enclaves to upscale planned communities, here are the most expensive cities in Florida today based on median home values.
10
Delray Beach: Upscale Coastal Town With Vibrant Downtown
An upscale coastal town with vibrant Atlantic Ave downtown, tennis clubs & parks drawing retirees & second-home buyers.
Beautiful Lake Ida, Delray Beach, Florida
With a median home price of $358,004, the coastal Palm Beach County city of Delray Beach ranks among the most expensive real estate markets in Florida. Delray Beach has long been a popular destination for Northeasterners seeking sun in the winter, thanks to the many things the city offers.
However, the city’s inventory of high-end new construction homes and prime location between Palm Beach and Ft. Lauderdale make it desirable year-round. The walkable downtown along Atlantic Avenue features boutique shops and dining in a lively historic district.
Luxury golf communities like Gulf Stream and Highland Beach are situated just north of Delray. Proximity to the ocean also comes with a price tag, especially for single-family homes.
9
Fort Myers: Southwest Florida City With Beaches, Arts And Culture
Southwest beach town with arts, culture & historic neighborhoods attracting second-home buyers & retirees.
A street in Fort Myers, Florida
With its warm winter climate and tropical landscape, Fort Myers attracts retirees and vacationers alike. It is one of the beautiful beachside towns to retire to in Florida. Real estate follows suit, with median home values currently around $373,990.
Waterfront homes can far exceed that, especially in desirable areas like McGregor and Sanibel Island, where million-dollar homes abound. While the Fort Myers market remains relatively affordable compared to South Florida, demand drives up values, especially from buyers priced out of Naples to the south.
Historic neighborhoods near downtown offer historic charm, while gated golf communities appeal to retirees. With inventory limited, Fort Myers remains one of the hottest real estate markets in the state.
8
Winter Park: Charming Orlando Suburb With Upscale Homes And Shops
Charming Orlando suburb with lakes, shops & Rollins College appealing to families & professionals seeking small-town charm.
View of Winter Park, one of the best downtowns in Florida
Immediately north of Orlando, Winter Park boasts a median home value of $447,590. As home to Rollins College, Winter Park exudes an academic charm while providing luxury residential opportunities.
The city’s reputation as an upscale Orlando suburb draws wealthy home buyers to its historic neighborhoods like Winter Park Country Club and Virginia Heights. Walkable Park Avenue and Hannibal Square districts have high-end boutiques and acclaimed restaurants.
New communities like Baldwin Park have also emerged as hotspots for real estate. While generally more affordable than in South Florida, prices in Winter Park reflect the immediate access to Orlando amenities.
7
Hollywood: A Coastal City Between Miami And Fort Lauderdale
Coastal city between Miami & Fort Lauderdale with miles of beaches, condos & dining drawing urban professionals.
View of Hollywood Beach in the daytime in Florida
The Fort Lauderdale suburb of Hollywood ranks fifth most expensive in Florida, with median home values currently around $449,104. Long known as a residential beach community, Hollywood has seen property values surge in recent years as developers build modern high-rise condos to meet demand from urban professionals.
The city’s miles of beaches, waterfront Broadwalk, and popular Diplomat Resort are drawn, as is the vibrant Young Circle arts district. Established neighborhoods adjacent to the Intracoastal, like Hillcrest and Royal Poinciana, tend to be pricier thanks to their bungalow homes and proximity to dining and nightlife.
Overall, Hollywood real estate costs less than its southern neighbors but retains great access to beaches
6
Sarasota: Artsy Gulf Coast City With Luxury Homes And Amenities
Artsy Gulf Coast city with performing venues, museums & upscale amenities attracting cultured residents & retirees.
The Ringling Museum, Sarasota, Florida
Sarasota offers world-class arts and culture, especially in Ringling Museum, on Florida’s cultured Gulf Coast, along with real estate prices to match its refined amenities. The median home value in Sarasota is currently $462,710.
Demand stems from the city’s reputation as a thriving retirement destination, historic downtown, starchitect-designed condos, and wealthy enclaves like Longboat Key. The overall housing inventory may be more reasonably priced than South Florida, but make no mistake — Sarasota has its share of exclusive multi-million dollar homes, especially along the bayfront of Lido Key.
Between the acclaimed Sarasota Orchestra and Ringling Museum of Art, real estate is a premium in Florida’s cultural capital.
Lighthouse at Boca Raton, Florida
Affluent Boca Raton has emerged as a major financial hub and boasts a median home value of $569,966. As one of South Florida’s most expensive residential areas, Boca Raton has long attracted wealthy retirees, families, and snowbirds.
Gated country club communities and sparkling new developments cater to the luxury market. Top-rated schools, high-end shopping at Mizner Park, the half-billion-dollar One City Center complex under construction, and the presence of companies like Office Depot and Bluegreen Vacations all help make Boca Raton one of Florida’s most desirable places to live.
Home prices are at a premium, especially along the Intracoastal Waterway.
4
Winter Garden: A Fast-Growing Orlando Suburb With New Developments
Fast-growing Orlando suburb with a quaint downtown, trails & new resort communities drawing luxury buyers.
Located 14 miles west of Orlando, the small city of Winter Garden packs plenty of charming appeal with a median home price of $572,225. Known for its historic downtown filled with cafes and independent shops, Winter Garden exudes small-town vibes with big city amenities nearby.
The popular Farmers Market draws crowds weekly, while the West Orange Trail threads through town. Expensive homes can be found along the chain of lakes that distinguishes Winter Garden’s landscape or within the upscale Keene’s Pointe resort community.
With its access to Orlando’s attractions and quaint atmosphere, demand for real estate remains high in Winter Garden. New housing developments continue to extend residential options.
3
Naples: Wealthy Beach Town With High-End Resorts and Golf
An exclusive beach paradise with world-class golf, shopping & dining enticing wealthy snowbirds & second homeowners.
A beautiful house surrounded by palm trees in Naples, Florida
As southwest Florida’s premier luxury destination with plenty of things to do, Naples claims mature palm trees, world-class resorts, mega-yachts, and a median home price of $594,106.
Long a favorite winter escape for Midwest CEOs and retirees, the Naples housing market boasts some of the state’s most expensive properties. Prominent golf communities such as Tiburon, Treviso Bay, and The Quarry offer multi-million dollar homes in perfectly manicured settings.
The walkable historic district along 5th Avenue South and the famed Naples Pier fuels demand for condos and apartments downtown. Developments like Naples Reserve and Fiddler’s Creek cater to the affluent buyer, helping solidify Naples as Florida’s exclusive paradise tucked along the Gulf Coast.
2
Key West: A Tropical Island City With Historic Charm
Key West is one of the most expensive cities with a current median home value of $1,073,367.
Southernmost Beach Resort in Key West, Florida, USA
The island city of Key West boasts the highest home prices in Florida, with a current median value of $1,073,367. Located at the southernmost point of the continental United States, Key West is known for its pastel-hued Caribbean architecture, literary heritage as the home of Ernest Hemingway, thriving arts scene, and laid-back “Margaritaville” vibe.
Demand from wealthy second-home buyers and vacation rental investors has made the island a luxury real estate hotspot. Homes in walkable Old Town command the highest prices, while judicial limits on density help keep inventory restricted. However, this shouldn’t scare budget-conscious travelers, as there are many cheap places to stay on the beach.
1
Coral Gables: Historic Miami Suburb With Mediterranean Architecture
Historic Miami suburb with Mediterranean revival architecture, boutiques & gardens enticing urban elite.
The entrance of Coral Gables Museum, Florida
This ritzy Miami suburb draws the wealthy with its reputation as an enclave of wealth and luxury. Coral Gables has a median home price of $1,345,718. The “City Beautiful” shines with its historical Mediterranean revival architecture, lush tree-lined streets, boutique hotels, and destination dining.
The Venetian Pool is a must-visit Mediterranean Paradise. Coral Gables home values rose over 15.4% in the past year amid high demand from buyers competing for limited inventory. The prestigious Village of Merrick Park and the University of Miami campus attract affluent residents.
For home buyers seeking luxury, Coral Gables offers stately estates, waterfront property, and private golf communities tucked among the city’s iconic mansions. Proximity to downtown Miami, beaches, and airports also add to the high cost of living.
While not everyone will want to live in the most expensive cities in Florida, they may be worth a visit while traveling in the state.
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