The Finger Lakes' 9 Best Retirement Towns Ranked

What if retirement were one long vacation—where breakfast comes with a lake view and every walk leads to a waterfall, winery, or farmer’s market? Upstate New York’s Finger Lakes region stretches across eleven glacial lakes, bordered by gentle hills and small towns that feel like home from the moment you arrive. Rich in history, it was once the heart of the Iroquois Confederacy and the birthplace of the women’s rights movement. Today, the area is dotted with villages offering reasonable housing, quality care, and the kind of community that appeals to retirees. Whether you crave stillness or stimulation, nature or neighborliness—both are here. Unwind, explore, and choose the perfect town to begin your most rewarding chapter yet.

Canandaigua

Canandaigua is scenic, welcoming, and ready to make you feel at home. With a median rental cost of $1,535, far below the state average of $3,100, it offers affordable access to Finger Lakes living. Thompson Health provides full-service care, including outpatient and geriatric programs. Seniors can also find top-tier assisted and independent living at Ferris Hills at West Lake, just minutes from downtown.

Start your mornings with a walk at Kershaw Park, where paved lakeside paths and benches make it perfect for relaxed exercise. Catch a summer concert at the Constellation Brands-Marvin Sands Performing Arts Center, which features reserved seating and accessible restrooms. For peaceful afternoons, seniors can visit Sonnenberg Gardens, where historic glasshouses and shaded walkways make for ideal reflective strolls.

Skaneateles

Skaneateles blends small-town calm with upscale lake living. The median home price is $576,000, reflecting high demand and its prized lakefront setting. Though there’s no hospital within the village, Auburn Community Hospital is just 7.5 miles away, providing a full range of medical services. Seniors in need of daily support can turn to Peregrine Senior Living at The Athenaeum of Skaneateles, which offers assisted care and wellness-focused programming.

Begin the day with a stroll around Skaneateles Lake, where the public pier and gazebo invite quiet moments by the water. The Skaneateles Library hosts lectures and book clubs for older adults in an accessible setting. Every summer, the Skaneateles Festival fills local venues with classical music performances tailored to relaxed daytime crowds.

Seneca Falls

Surrounded by lakes and canals, this historic village—sometimes called the birthplace of women’s rights—offers retirees significant affordability. The median home price in Seneca Falls is $181,000 as of March 2025, a steal compared to the state average of $481,000. Thus, it is one of the Finger Lakes’ greatest bargains. Seniors have easy access to Geneva General Hospital, 20 minutes away, and assisted living facilities throughout the region. At the center of the community, the Seneca County Senior Center fills days with exercise classes, games, and seasonal meals.

A walk around Van Cleef Lake offers breezes and benches by the water. You’ll learn about the history of the 1848 convention at the Women’s Rights National Historical Park, and the It’s a Wonderful Life Museum brings Hollywood nostalgia to the town.

Watkins Glen

With waterfalls, lakefront property, and an easygoing pace, Watkins Glen is the serene spot for retirees who yearn for tranquility and scenery. The median home value is $211,000, and single-story or lakefront properties are abundant. Schuyler Hospital provides essential services just a few minutes from the village square, and assisted living centers are within reach in Montour Falls, just down the road.

Start the morning walking along Watkins Glen State Park’s gentle trails, stone steps, and shaded overlooks. Benches, breezes, and space to sit and watch the sailboats go by are found at the Seneca Lake Pier. Seated wine tastings along the Seneca Lake Wine Trail offer sociable afternoons, weekday peace, and postcard scenery from the comfort of a chair.

Trumansburg

Surrounded by wooded hills and peaceful farmland, Trumansburg offers retirees a gentle pace and a strong sense of community. Homes have a median cost of $303,000 (March 2025) and are modest, often within walking distance of both shops and nature. The village features the Trumansburg Family Health Center, and full medical services are just 10 miles south at Cayuga Medical Center, and assisted living facilities offer additional support.

Mornings at the Trumansburg Farmers’ Market feature fresh produce, crafts, and live music with a welcoming rhythm. The Ulysses Philomathic Library provides book clubs, tech support, and quiet spaces for reading and connection. Just outside of town, Taughannock Falls impresses with a 215-foot drop and flat walking trails—ideal for low-impact adventures with big views.

Geneva

This town offers lake views with a college-town feel, an appealing option for retirees who want both calm and activity. The median home value is $197,000—a great price for its Seneca Lake setting. Geneva General Hospital offers full-service care, and Seneca Lake Terrace provides assisted living and memory care just minutes away.

Start your day in Geneva at Billsboro Winery, where weekday tastings bring lake views and a relaxed atmosphere. Catch a matinée at The Smith Opera House, a historic venue with wheelchair-accessible seating and senior discounts. For outdoor recreation, Seneca Lake State Park offers paved trails, benches, and wide-open views.

Hammondsport

Surrounded by wooded hills on the south shore of Keuka Lake, Hammondsport appeals to retirees seeking tranquility, beauty, and connection. The median home price is $317,000, ranging from lakeside properties to modest cottages. Though the village lacks a hospital, full medical care is available at IRA Davenport Memorial Hospital in nearby Bath. It’s a relaxed place where neighbors know each other by name and daily errands are done on foot.

Stop by the Pleasant Valley Wine Company for seated tastings and a tour of the nation’s oldest bonded winery. Shaded benches along the lakefront and level paths at Depot Park invite slow afternoons. In September, the Wings & Wheels Festival brings vintage cars and aircraft to town in a laid-back, lakeside celebration.

Auburn

Known for historic landmarks and small-town accessibility, Auburn offers services without sacrificing charm. At a median home price of $196,000, it’s one of the most affordable communities in the Finger Lakes. Seniors have full medical care at Auburn Community Hospital, with multiple assisted living and long-term care options nearby.

Seniors can tour the Seward House Museum and then visit the Willard Memorial Chapel, a National Historic Landmark with original Tiffany glasswork. The Merry-Go-Round Playhouse offers matinees in an accessible lakeside venue. At Emerson Park, wide walking paths and cool lake breezes along Owasco Lake make for a relaxing finish to any day.

Penn Yan

Along the northern shore of Keuka Lake, Penn Yan attracts retirees with lake scenery, local charm, and walkable streets. The median home price is $295,000, with a mix of single-story homes, cottages, and lakefront properties. Soldiers & Sailors Memorial Hospital offers full-service care just blocks from the village center, with assisted living and long-term support available nearby.

Seniors enjoy the Keuka Outlet Trail, a flat, shaded path linking Keuka and Seneca Lakes. The Yates County History Center features curated exhibits inside restored historic buildings. Every June, the Penn Yan Fly-In Breakfast draws vintage aircraft and local crowds, while Birkett Mills and Route 54 Antiques add flavor and character to the downtown.

Where Will You Unpack for Good?

Retirement doesn’t have to mean slowing down—it can mean better views, better food, and better mornings. Across the Finger Lakes, charming towns like Canandaigua, Skaneateles, and Seneca Falls invite you to trade traffic for trails, stress for scenery, and routine for the community. Whether you’re sipping wine in Hammondsport, browsing antiques in Penn Yan, or listening to live music in Trumansburg, each town brings its own rhythm of ease and enjoyment. These nine villages offer affordability, access to quality care, and natural beauty—each with a welcome mat at the door. So where will you spend your best years? Choose your favorite, pack your bags, and make retirement feel like a reward—not a retreat.