9 Under-The-Radar Retirement Towns In New York
New York, a northeastern state in the US, is known worldwide as an incredibly diverse state, regarded as a melting pot, with people, food, and influence from thousands of other countries. While its cost of living is known to be higher in general than the national average, particularly in and around New York City, there are some towns that fly under the radar, which are less expensive than most for retirees to comfortably spend their later years. Or, if you have the means to do so, you can splurge a little on housing and retire in a lakefront or canalside community that offers all of the lifestyle amenities that you have spent your entire life working to now enjoy.
Olean
Along the long Allegheny River, in western New York, is the town of Olean, home to just under 14,000 residents. It has a quiet, small-town feeling for those who want to escape the hustle of big cities. A great retirement alternative for those seeking affordability, Olean is surprisingly accessible to those with tighter budgets. It has notably reasonable housing prices, significantly cheaper than the New York average (around $484,000 as a state median home sale price, according to Zillow). The median sale price in Olean, as of October 2025, was only $178,000.
Olean is known for being a gateway town to the stretch of Allegheny Mountains known as the "Enchanted Mountains," so the town has absolutely beautiful surroundings. Neighboring Allegany State Park is great for hiking and camping for retirees who want to stay active. Allegany is actually the largest state park in New York, spanning 65,000 acres. Rock City Park, another perfect place to get outside, has marked trails that follow multiple unique rock formations, and since this park is a bit of a tourist attraction, it even has a gift shop. For more shopping, visit Christie's Boutique, which offers a little bit of everything, from clothing to paintings and pottery, all locally made.
Massena
On the St. Lawrence River, in far north New York, right on the border of Canada is the town of Massena. It is part of the Thousand Islands region, which is an archipelago of around 1,800 islands, and near the Adirondack Mountains, both of which bring plenty of tourists to the area. Despite these major attractions, Massena is quiet, relaxing, and suburban, with a tight-knit community of about 10,000 permanent residents. The town actually has very high rates of homeownership, meaning it generally has less listings than bigger cities, but there were still 77 listings last year, according to Zillow. Plus, with the median listing price being only $144,000 as of November 2025, if you are looking to retire into this area, and you snatch up your ideal property when it is available, it is very likely to be quite affordable.
Massena is a great place to enjoy your free time, whether you are just visiting or decide to stay for good. There is plenty to do that can occupy your time, including spending time watching ships and enjoying the views of the river at the Eisenhower Lock, one of seven locks along the seaway, which has a huge observation deck and multi-level views. Another good place to enjoy water views is the Massena Town Beach, a sandy beach on the river ideal for swimming, fishing, walking and playing sports. If your family is in town, going to Timequest Mini Golf is sure to be a fun time, even having a petting zoo on the grounds for the grandkids.
Dunkirk
In western New York, bordering Lake Erie, is the city of Dunkirk. It is a historic port town with a slow-paced, small-town feeling, complete with lakeside charm. You would not imagine this, with it being in New York and right on one of the Great Lakes, but Dunkirk has super affordable housing, with Zillow recording the town's median list price for 2025 at only $138,000. You would be hard-pressed to find lakeside living at prices any lower than that. Plus, Dunkirk is attractive to retirees who prioritize safety, with less crime than most cities in New York. For 2024, NeighborhoodScout lists Dunkirk as having lower than the national rates in every single violent crime category.
Dunkirk is a fun place to spend your time in general, with the Dunkirk City Pier offering opportunities for strolling along the waterfront, renting a boat to go fishing out on the water, or enjoying some dining and shopping. Two popular lakefront restaurants are 64 On The Pier and Off the Hook, both of which serve fresh-caught seafood among other dishes. Or, if you are looking to drink your calories, Steelbound Dunkirk is a local brewery, also lakeside, that is sure to satisfy.
Stony Point
Technically part of the New York City metropolitan area, but with a population of only 14,000, is the village of Stony Point, just north of the massive city. Right on the iconic New York staple, the Hudson River, this town is home to the oldest lighthouse on the Hudson, the aptly named Stony Point Lighthouse. It is a historic town in general, also the location of the Stony Point Battlefield State Historic Site, which was a crucial Revolutionary War battle site in the 1770's. Despite its long background and obvious tourist appeal, Stony Point is low-key and very peaceful, rich with Hudson Valley charm. Bear Mountain State Park, which has access to the Appalachian Trail, is nearby, too, so you will have plenty of places around town to explore and relax.
Despite being so near to the Big Apple, the village has a low crime rate, with NeighborhoodScout declaring it safer than 70% of US cities, and only having 3 violent crimes reported in 2024. Understandably, there are not a lot of homes listed for sale in Stony Point, and the median list price is quite high, nearing $900,000. However, some might look at that and recognize that if they can afford these rates, the luxury of living in the Hudson Valley is well worth it, especially being so close to the city, but in a quieter and safer area. Plus, according to RentHop, the average rent for a 3-bedroom in Stony Point is over under $3,000, compared to NYC's $6,500 for the same size home, so if you decide to go with a rental, you will save a lot of money.
Cold Spring
North of Stony Point and about an hour's drive from New York City is the tiny village of Cold Spring. It is also in the Hudson Valley and on the river, in a prime location. It is very small, with fewer than 2,000 residents, and is highly appealing due to its charming Main Street. Lined with cafes, like Cold Spring Coffeehouse, and antique stores, like Cold Spring Antique Center, Main Street is filled with historic architecture, which creates a truly picturesque Hudson River village. Needless to say, there is a ton of outdoor recreation close by as well, such as Hudson Highlands State Park, great for hiking and camping, or Foundry Dock Park, a riverfront square with waterfront paths and benches.
Cold Spring not only feels safe, it statistically is safer than nearby New York City. NeighborhoodScout ranks it as 76% safer than other US cities, and the violent crime rate is actually listed at 0%. Like Stony Point, it is harder to claim a place to live in Cold Spring, as there are fewer for-sale listings than in some other towns in New York. Compared to the big cities, though, this village has much cheaper rent, with a listing available on RentHop at $2,500 for a 2-bedroom, versus NYC's $5,500 for the same amount of space.
Fairport
The village of Fairport, home to only 5,500 people, is only 10 miles east of the upstate city of Rochester. Fairport is a perfect alternative to fast-paced city living while still being near plenty of amenities, often called the "Crown Jewel of the Erie Canal" because of its quaint canalside charm. Full of historic lift bridges, gorgeous waterfront parks, shops and cafes lining the walkable streets, it is known to be a friendly little village with low crime rates, specifically listed at 0.19 per 1,000 residents for violent crime, and 6.16 per 1,000 residents for property crime. Compared to New York state overall, in which you have a 1 in 257 chance of being a victim of a crime, you only have a 1 in 5,353 chance in Fairport.
This is also a pretty affordable town for New York standards, with a median list price of $332,000 according to Zillow, and there are 50 listings currently for sale, despite it being a very small town. There is a lot to do as well, including buying some local produce or floral arrangements at the seasonal outdoor Fairport Farmers Market, grabbing dinner and a drink with friends at Tin Cup Social, an upscale sports bar, or catching a local live music show at B-Side.
Penn Yan
Penn Yan, a village in the Finger Lakes region, lies at the northern tip of Keuka Lake. The town is entrenched in natural beauty, home to amazing outdoor attractions like the Keuka Lake Outlet Trail, a gorgeous paved walking and biking trail which travels along the lake, past waterfalls, and even some old ruins. Steeped in lakeside charm, Penn Yan is also unique for having a large Mennonite community, so you will see plenty of typical Amish businesses, like bakeries such as Oak Hill Bulk Foods, and see horses and buggies rolling down the streets. Also in town is Windmill Farm & Craft Market, selling a wide array of handmade Amish-style goods.
Penn Yan also offers a lower than average cost of living, so even tho the median listing price is recorded by Zillow at about $511,000, and rentals are rare, when they are available, prices for rentals are historically extremely low. Also, what you spend on a mortgage or rental, you will save on the cost of living, with BestPlaces listing the cost of living in Penn Yan as 13% below the US average, and a whopping 27% lower than New York's overall. Besides, the lakefront living is well worth the price.
Lockport
At 20,000 residents, the city of Lockport is not a small town in terms of population, but it has a very quiet, community-oriented, family-friendly feeling about it. Located on the Erie Canal in Niagara County, close to the famous Niagara Falls, Lockport is named after the "Flight of Five," its locks and dam system, which has been noted as a historically innovative model for controlling water levels. You can see these locks up close and personal on an Erie Canal Cruise.
This city has various other attractions too, such as the Erie Canal Discovery Center, a museum with art, exhibits, and gifts themed after the canal, the historic Palace Theatre, which shows both films and stage productions, and pottery classes at Imagine That. Another benefit of retiring in Lockport is that it is known to have a lower cost of living than both the national average, where it is 13% lower, and the New York state average, where it is 28.4% lower. Housing is generally quite cheap, too, with a median sale price on Zillow listed at only $242,000.
Cooperstown
Cooperstown, decidedly a small town with a population of less than 2,000, is a thoroughly charming town in the foothills of the Catskill Mountains on Otsego Lake, an ancient glacial lake. Clearly, Cooperstown is in a prime location near extremely diverse landscapes, so residents can do pretty much anything they could ever want to do. Hiking on the mountains and boating on the lake are at the top of the list for many, but Cooperstown also has a lovely, walkable downtown strip with unique shops and diners, like local staple Doubleday Cafe. Other popular draws include the National Baseball Hall of Fame and the Fenimore Art Museum, which is inside a stunning Georgian museum once owned by the famous American novelist, James Fenimore Cooper.
As far as housing goes, retirees looking to buy in the Cooperstown area may notice that there are not too many housing listings, currently only 30 on Zillow, in fact, and the mildly high-priced (for New York) median list price of $572,000. Luckily, there are rentals available, and many of them have incredibly affordable rent, with a 4-bedroom home currently listed at only $2,500 on RentHop. Cooperstown has low crime rates as well, safer than 50% of other US cities according to NeighborhoodScout, with a violent crime rate of only 1.09 per 1,000 residents.
For retirees checking out New York...
You should get everything you desire in the place where you will spend the golden years of your life. That might be an affordable city like Massena or Dunkirk, so you have more money to spend with your family, doing things like taking your grandchildren to Massena Town Beach or spending time relaxing with friends at Lake Erie. Or, you may be more interested in a posh lifestyle, in places like Cold Spring or Cooperstown, where anything you wish to spend time doing is right outside your front door. No matter what your retirement goals are, New York can meet them!
