The Luxury Retreats: 10 Coastal and Mountain Resort Towns

Many retirees dream of spending their days in a vacation town. Unfortunately, resort communities suffer from restricted housing supplies and local economies geared toward wealthy tourists rather than permanent residents.

• Aspen, Colorado: A world-renowned ski destination, Aspen is built for luxury. Real estate prices are firmly in the multi-million-dollar range, and everyday necessities are trucked up the mountain at a significant premium.
• Santa Barbara, California: Often referred to as the American Riviera, Santa Barbara offers perfect weather and ocean views. The barrier to entry, however, is immense. Strict zoning laws limit new construction, keeping property prices artificially high.
• Naples, Florida: Located on the Gulf Coast, Naples is famous for its high concentration of wealth and golf courses. While it caters beautifully to seniors, the cost of waterfront real estate and private club memberships requires a highly affluent demographic.
• Newport, Rhode Island: Famous for its Gilded Age mansions and sailing culture, Newport operates on a high-cost coastal economy. High property taxes and an expensive winter heating season make it a tough choice for budget-conscious retirees.
• Martha’s Vineyard, Massachusetts: Island living in the Northeast comes with severe logistical costs. Ferries are required for many essential services, and the off-season economy can be surprisingly expensive to navigate.
• Key West, Florida: Space is the ultimate luxury on an island. Real estate in Key West is strictly limited, and importing goods down the Overseas Highway drives up the cost of food, fuel, and medical supplies.
• Laguna Beach, California: This artistic enclave in Orange County boasts stunning coves and high-end galleries. It also features some of the highest housing costs in Southern California, combined with a high risk of coastal erosion and related insurance hurdles.
• Maui, Hawaii: Similar to Honolulu but with a more intense focus on luxury tourism, Maui presents immense affordability challenges. Rebuilding efforts following recent historical wildfires have further strained local resources and driven up housing costs.
• Jackson, Wyoming: Wyoming offers excellent tax benefits for retirees, leading wealthy individuals to flock to Jackson Hole. The resulting wealth concentration has created an extreme affordability crisis, where modest single-family homes sell for luxury estate prices.
• Sedona, Arizona: Known for its breathtaking red rock formations, Sedona has transformed from a quiet arts community into an expensive tourist hub. The cost of housing has surged, and the relatively isolated location increases the cost of advanced healthcare access.