9 Best Connecticut Towns For Retirees

Connecticut is unrivaled for quality of life, healthcare access, neighborhood safety, education, and its population of retirees. It is home to several highly regarded hospitals, many nationally recognized for excellence in several specialties, including cancer treatment, orthopedics, and heart care. We have not even touched on its short but stunning coastline or small, charming towns, many of which provide relaxation and adventure in equal doses. Discover below the nine best small towns to retire in Connecticut.

Putnam

Putnam is a small town with a lively downtown area, cute little shops that are almost always open, and a quaint little venue to see a play called The Bradley Playhouse. The theatre is on Front Street and has a history that dates back to 1901. You will also find several fantastic restaurants for a slow-paced brunch, including The Stomping Ground, which is loved for its laid-back vibe and live music shows. A retiree can keep fit at places like the River Mills Heritage Trail, float down the Quinebaug River, or get snug with a classic at the Putnam Public Library. The best part is that Putnam is incredibly budget-friendly, boasting a June 2025 median listing price of just $369,500. Westview Health Care Center is a short drive away in nearby Dayville.

Torrington

If you want to retire in Connecticut but pay the price points of Kansas or Indiana, Torrington is among the best options to work with. In June 2025, Torrington's median listing home price was just $285,000. Sue Grossman Still River Greenway is a cool place to enjoy a flat, smooth ride through scenic wetlands alongside the Still River, while the beautiful Stillwater Pond State Park is a fun place to fish, swim, or hang out with a close friend. Other fun outdoor venues include the Naugatuck River, which flows through the town, and Coe Memorial Park, which has colorful flowers and plants. Meanwhile, Charlotte Hungerford Hospital is a 109-bed, general acute care hospital serving patients since 1916.

Glastonbury

Located in an area known for fresh fruits and apple orchards, Glastonbury is a clean, calm town conveniently situated within arm's reach of downtown Hartford, the state's capital and one of Connecticut's largest cities. Consequently, retirees here enjoy immediate access to top-notch amenities and cultural attractions, including excellent schools, Hartford Hospital, and assisted-living facilities like The Residence at Glastonbury. Outdoor attractions include the river-fronting Gay City State Park, a 1,570-acre space offering hiking, biking, and swimming opportunities, the easily accessible J.B. Williams Park, as well as the Salmon River State Forest, which has lots of nice rocky spots next to the river for relaxing and hearing the sound of moving water. In June 2025, the median listing home price in Glastonbury was $595,000, which is a reasonable bargain, especially considering that according to data from realtor.com, the statewide median for the same period $561,725.

Cheshire

In June 2025, the median listing home price in Cheshire was $567,000, which almost mirrors the statewide median of $561,725. A retiree here will enjoy a section of the phenomenal Farmington Canal Heritage Trail, a paved, well-maintained trail that meanders next to or near the Farmington River. The town's future could not be brighter with a place like the Ball & Socket Arts, which is transforming an abandoned industrial campus into an innovative and dynamic arts destination. Meanwhile, Cheshire Park is small but has plenty of trails to discover, while Broad Brook Reservoir boasts a tranquil environment where you can take in peaceful water views. To cap it off, the highly rated Hospital of Central Connecticut Emergency Room - Bradley Memorial Campus is a heartbeat away in Southington, so no need to worry about healthcare access.

Windsor Locks

With Hartford just 14 miles south and a median listing price that almost looks too good to be true, Windsor Locks is a location every retiree will want to pay attention to. The median listing home price in Windsor Locks was $299,900 in June 2025, nearly half the statewide median. Windsor Locks is a small town with a fantastic community and several great places to hang out. Outdoor pleasure points include the Connecticut River, which flows through the town’s eastern rim, the Farmington River, which boasts several recreational opportunities, and the well-maintained Spring Park, where you can sit and hear the birds sing. Some well-regarded healthcare options include Hartford Hospital and the Hospital of Central Connecticut (HOCC), which boasts one of the region's most advanced, patient-centered cancer programs.

Groton

If you have ever dreamt of retiring on the water without paying a fortune, Groton is among your best options in Connecticut. In June 2025, Groton's median listing home price was $450,000. The town is known as the Submarine Capital of the World and hosts the Naval Submarine Base New London, meaning the environment is relatively safe and peaceful. You can paddle the Thames River, enjoy an afternoon round of golf at the well-maintained Shennecossett Golf Course, or wait for a magical sunset at Eastern Point Beach, a clean, peaceful place with spectacular views on almost every side. The best part is that you are at the doorstep of Lawrence & Memorial Hospital, a 2023 recipient of the Joint Replacement Excellence Award.

New Milford

New Milford is another decently priced retirement community in Connecticut, with attractions and amenities that further improve its appeal. In June 2025, the median listing home price in New Milford was $569,000, just slightly above the statewide median. If you prioritize safe and peaceful spaces, you will be happy to note that Safewise ranked New Milford the 6th-safest town in Connecticut for 2025. New Milford is incredibly family-friendly and boasts a walkable, tree-lined downtown with beautiful buildings and small shops. Elephant's Trunk Flea Market is among the best in the state, while New Milford Hospital, right at your doorstep, is among America’s 100 Best Hospitals for Cardiac Care. You can have evening walks over the bridge at the Lovers Leap State Park, float down the Housatonic River, or enjoy hours of palpable calm and quiet at the Lynn Deming Park, a tucked-away slice of paradise with a small, sandy beach.

Coventry

If you fancy retiring a 25-minute drive from downtown Hartford in an unbelievably peaceful and rustic location, Coventry should be on your radar. Woods, trails, gardens, and several outdoor venues will surround you. Moreover, you will enjoy town events and festivals where you run into everyone you know or have met before. Retirees have several recreational opportunities, especially at Wangumbaug Lake, Eagleville Pond, and Bolton Notch State Park, a cool, dog-friendly walking, hiking, and biking area. According to data from Realtor.com, in June 2025, the median listing home price in Coventry was $405,000, which is way below the statewide median. Windham Hospital in neighboring Willimantic has received several awards and recognitions for healthcare access, including patient safety and heart attack response.

West Simsbury

The median listing home price in West Simsbury was $519,500 in June 2025. Home to just under 3,000 residents, West Simsbury offers the advantages of small-town living, including the opportunity to establish genuine and authentic relationships. For big-city amenities, Hartford is just about 25 minutes down the road. The best thing is that outdoor lovers have the privilege of living close to the trail-laden Stratton Brook State Park, a beautifully maintained outdoor oasis surrounded by nature and quiet solitude. Meanwhile, Simsbury Farms Recreation features a well-maintained golf course on a rolling terrain, while the funnily named Onion Mountain Park has trails that provide a solid workout. For any medical emergency, the UConn John Dempsey Hospital in Farmington is a three-time, back-to-back Outstanding Patient Experience Award winner.

With its close ties to New York City, the Cultural Capital of the World, an empty nester in Connecticut is always conveniently within a whisper of top-level cultural attractions and amenities. Plus, there is a chance you will be close to Yale, one of the most prestigious universities in the world. Suppose you want to mingle with intelligent and interesting folks, access some of the best hospitals in New England, or enjoy epic outdoor adventure opportunities. In that case, it is hard to argue with Connecticut. From affluent locations with classic neighborhoods to fun, laid-back spots such as West Simsbury, you won't miss finding a retirement place with your name on it.