5 Charming Small Towns Where America's Wealthy Retire

Dutch Colonial shingle style house in Vineyard Haven, Martha's Vineyard, Massachusetts. The home has a hydrangea bush and an ocean view.

(Image credit: Getty Images/David Sailors)

Money certainly can't buy good taste, but in these affluent small cities and towns, good architecture, lush gardens and natural beauty add up to true charm. Whether your net worth is a million or more, some communities really are worth the higher housing prices.

Here we highlight five wealthy small towns, along with their attributes, amenities, hospitals and access to major urban centers.

Retirees should conduct an honest self-evaluation of their physical strengths and limitations, as well as their tolerance for living in a relatively remote (as opposed to more accessible) corner of the country. Your neighbors may have private jets; you may not be as well-positioned.

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1. Martha's Vineyard, Massachusetts

Houses along North Water Street in Edgartown on Martha's Vineyard, Massachusetts, USA.

The vibe. This sprawling, scenic island located south of Cape Cod has long been a magnet for the Clintons and the Obamas, but it’s not just a seasonal retreat for boldfaced names. In little more than a decade since 2010, the year-round population has doubled to more than 20,000 — but the summer crowds swell that number by a multiple of 10.

The widest sandy strands of this triangular land mass are in the south, where people wave to strangers from their beach towels (the Vineyard is known for its friendliness). The epicenter of the island’s activity and charm is historic Edgartown.

The island has a good share of historic sights, art galleries, cute general stores, indie shops (including bookstores, boutiques and ice cream parlors) and stunning coastal bluffs. Artists, writers and musicians abound, and concerts at the historic Tabernacle may include local talent or national acts.

Each town has its own character, from the mansions of West Chop to the cottages near the Menemsha fishing village. The historic village of Oak Bluffs, with its charming gingerbread homes, has long been the summer destination of the Black elite.

There is a strong commitment to environmental conservation on the island, resulting in ample hiking and biking trails and coastal protection.

Some areas of Martha's Vineyard, like Edgartown and other low-lying coastal areas, face a "major" flood risk.

Healthcare. Martha’s Vineyard Hospital is located in Oak Bluffs in the north of the 96-square-mile island. A medivan transports seniors and patients with disabilities from the Vineyard to Boston hospitals once a week for $40. For emergencies that the hospital can't handle, patients may be airlifted to hospitals in Boston.

Median home sale price. $1.48 million in October 2025, according to Redfin.

Access. Martha’s Vineyard Airport is served by major airlines such as Delta, American and JetBlue. You can reach Boston by taking a ferry (which can transport your car) and then driving for two hours. A passenger ferry can get you from New York City to the Vineyard in about five hours during the high season.

2. Saratoga Springs, New York

Saratoga Springs is a city in Saratoga County, New York, United States. The name reflects the presence of mineral springs in the area, which has made Saratoga a popular resort destination.

The vibe. A longtime retreat from New York City, Saratoga Springs has a population of more than 28,000 people. It attracts an interesting and eclectic crowd: Some visit for the city’s namesake mineral springs, while thoroughbred horse racing enthusiasts are drawn to the Saratoga Race Course. For the literary-minded, the famed artists’ and writers’ retreat, Yaddo, is an ideal destination. The well-regarded Skidmore College lends the historic city a college-town atmosphere, while offering readings and musical and visual arts events open to the public.

Though Saratoga Springs' town motto is "Health, History and Horses," you could add "great food" to the slogan, despite the lack of alliteration. As part of the Hudson Valley, the town is near many farms and breweries. In addition, the area is ideal for hiking and boating, and is about one hour from the Hudson River.

Healthcare. Saratoga Hospital is affiliated with Albany Med Health System.

Median home sale price. $759,900 in October 2025, according to Redfin.

Access. By car, Saratoga Springs is a 45-minute drive from Albany and more than three hours from Manhattan. By express train, Saratoga Springs is about four hours from Moynihan Train Hall (adjacent to Penn Station), New York. It's also on Amtrak's Adirondack Line, known for being one of the most beautiful train routes for fall foliage.

3. Telluride, Colorado

View of snow-covered mountains from one of Telluride's main streets.

The vibe. Arguably the loveliest resort town in Colorado, Telluride is a haven for skiers and winter sports enthusiasts. Still, summers are popular, with rafting, swimming, tubing, mountain biking, fishing, and rock climbing available. Surrounded by mountains on all sides, the town features a historic center listed on the National Register of Historic Places.

If festivals are your thing, then Telluride could be a great fit. The annual Telluride Film Festival has been around for more than 50 years and has only grown in prestige. There are 14 festivals each year celebrating Bluegrass, Americana and Blues music, wine, yoga and more. The retiree-friendly town offers free bus and gondola services, reducing reliance on car travel.

The town has an extreme flood risk, so be sure to check risk maps before you purchase a property.

Healthcare. The nearly 50-year-old Telluride Medical Center offers 24-hour trauma and emergency services.

Median home sale price: $1.38 million in October 2025, according to Redfin.

Access. Telluride, with a population of around 2,500, is somewhat remote, though it contains a regional airport. Montrose Regional Airport (1.5 hours away) is the better, more equipped option in some cases. Denver is a six-hour drive away; even Albuquerque, New Mexico, is a bit closer. Retiring or relocating to Telluride is best for those who are fit and generally healthy. Very wealthy Telluride residents are opting for private planes.

4. Carmel-by-the-Sea, California

Aerial view of houses along Ribera beach during sunset at Carmel by the Sea.

The vibe. One of the most enchanting coastal spots on the Monterey Peninsula, the remote town of Carmel-by-the-Sea has a population of over 3,000. Human-scale Ocean Avenue counts as the main street, and it’s a beauty, dotted with alfresco restaurants and cottage hotels. Walking or driving along the roads that branch off from Ocean Avenue is a delight, with rises, falls and twists among the Spanish colonial and storybook homes.

At the end of Ocean, you’ll find stunning Carmel Sunset Beach, which is broad and gently sloping, a favorite for sunbathers, picnickers, and surfers. History and culture abound, and include the 18^th-century Carmel Mission Basilica, the Sunset Center for live entertainment, the Carl Cherry Center for the Arts, and the Carmel Heritage Society. Nearby 17-Mile Drive ranks as one of the finest coastal routes in the country and the exalted Pebble Beach golf courses and resorts are just minutes away. The serpentine Pacific Coast Highway, which leads south to Big Sur, is renowned for its beauty, but be sure to check for road closures. Note that Carmel-by-the-Sea's wildfire risk is considered "major."

Health care. Nearby hospitals in and around the Monterey Peninsula include the Community Hospital of the Monterey Peninsula and Pacific Grove Healthcare Center.

Median Home Sale Price. $2.481 million in October 2025, according to Redfin.

Access. Carmel is on the Central Coast of California, about 2.5 hours south of San Francisco and its international airport.

5. Palm Beach, Florida

Port of Palm Beach, Florida. It's a sunny day and the water is a bright blue.

The vibe. Palm Beach, positioned in the northern section of the tri-county region of Great Miami, is a tiny and very exclusive (9,000 year-round residents), beach community located on a sandy, pretty barrier island. Anchored by the legendarily ornate Breakers Palm Beach oceanfront resort, the town is rife with palatial homes and dozens of billionaires (and yes, Mar-a-Lago).

Local hotspots include bougainvillea-lined Worth Avenue, with its high-end boutiques (apparel and household goods), eateries, fountains and pedestrian vias. Swifty’s at the Colony Palm Beach hotel is one of the loveliest dining venues in town, but don’t miss Buccan, Bice, Renato’s and buzzy outposts of Manhattan favorites like Sant Ambroeus and La Goulue.

One major downside of Palm Beach is its climate risk. Over 90% of properties are at risk of flooding in the next 30 years, according to First Street.

Healthcare. Good Samaritan Medical Center and St. Mary’s Medical Center are across the bridge in the more bustling and commercial West Palm Beach.

Median home sale price. $5.5 million in October 2025, according to Redfin.

Access. In addition to the resources in West Palm, Palm Beach is a 2.5-hour drive to Miami, with Boca Raton and Fort Lauderdale along the route. West Palm Beach, Fort Lauderdale and Miami are home to major international and executive airports. The Tri-Rail Line connects West Palm Beach to local airports and nearby towns.

Drew Limsky joined Kiplinger Digital as a freelance retirement writer because he believes that every day offers opportunities to make better financial decisions, and that it’s never too late to learn how to enhance your financial position and lifestyle. Drew is the former editor of Lexus magazine, Cadillac magazine, South Florida Business & Wealth, Business Jet Traveler, Interiors South Florida, and Mariner (for Holland America). Drew’s writing credits include The Wall Street Journal, New York Times, LA Times, Washington Post, Boston Globe, Yahoo, Worth, AD, Robb Report, Metropolis, Men’s Journal, and Business Insider. An Emory grad, Drew earned his JD and PhD at NYU, and lives in Miami Beach, Brooklyn, and Cape Cod.

With contributions from