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Senior Community Guide

Small Towns

Connecticut metro areas:
Redding, Easton, Prospect, Durham, Essex, Bethany, Sherman, Woodbridge, Old Lyme, Lebanon, Litchfield, Haddam, Woodbury, New Hartford, Harwinton CT
Bridgeport-Stamford-Norwalk, CT
Danbury, CT
Hartford-West Hartford-East Hartford, CT
New Haven, CT
Norwich-New London, CT-RI
Springfield, MA-CT (Metropolitan NECTA)
Waterbury, CT
Worcester, MA-CT

55 community guide

CT Retirement Property types include single family homes, houses, condos, villas, townhomes, cottage homes, golf villas, patio homes, ranch condos and modular, manufactured or mobile homes located in parks, subdivisions, villages, lake property, lifestyle community, waterfront, townships, small towns, and cities, both rural, exurban, exurbia, suburan and urban.

CT 55 Plus Communities and Homes in Connecticut's Small Towns

There are many small towns in Connecticut perfect for retirement living. Among the most highly rated are: Redding, Easton, Prospect, Durham, Essex, Bethany, Sherman, Woodbridge, Old Lyme, Lebanon, Litchfield, Haddam, Woodbury, New Hartford, Wolcott, Harwinton CT. Many of Connecticut's small towns are in the northeast and northwest parts of the state.

Best Small Towns in Connecticut For Retirement Living:

Connecticut is one of the most beautiful states in New England, if not the country. From the distinct four seasons to the recreational opportunities found in the state, Connecticut offers something that every family member can enjoy. Connecticut's largest city is Bridgeport and the Greater Hartford area is among its most metropolitan region. Among the large cities in the Constitution State, there are hundreds of small towns that offer beauty and culture. Among the top rated small towns in Connecticut are:


With a population of just under 30,000 residents, Cheshire is one of the most charming small towns in Connecticut. The community is conveniently located between Hartford and New Haven so that residents can enjoy living in Cheshire but commuting to work in the city. Top-rated schools, affordable condominiums and garden-filled charm can all be found in the small town of Cheshire.


The warm community of Essex offers opportunities for the entire family to enjoy. Choose from shopping in antique stores to boat excursions along the river. Essex is a prime location for dining out in some of Connecticut's most unique restaurants and cafes. Gourmet food and gift shops line the main shopping hub and the Town Hall offers unique picture taking experiences.


Settled in 1721, Litchfield looks like it belongs in a storybook about the Colonial period. The town showcases 18th century architecture and rolling hills of greenery. In the fall, the landscape is more beautiful in person than in the books themselves. Restaurants and historic homes line the walkways and streets of this charming Connecticut town.

Scenic photo of Connecticut Home and Lighthouse


The historic town of Simsbury was founded in 1670 and is rich in history, culture and the heritage of New England. A vibrant and fun downtown shopping district offers unique restaurants and cafes as well as antique stores and quaint boutiques. The town offers an annual music festival that features the Hartford Symphony and is home an International Skating Center where Olympians have trained. The town is a popular place to visit and take in the history that the state of Connecticut has to offer.

South Windsor

The town of South Windsor is found twenty minutes from the buzz of the city Hartford and is one of the top ranked towns to live in Connecticut. The quality of life in the community boasts top rated schools and districts, a low crime rate and a beautiful housing market. The Connecticut River flows along the town and brings bountiful recreational opportunities to area residents and tourists. Shopping along the Promenade full of flowers and diversity is something enjoyed by many who frequent the beautiful town of South Windsor.


Tolland is a small community with 15,000 residents and home to several tech companies. Surprisingly enough, the town has not lost its historic charm despite the businesses taking up residence here. While CNC Software may be housed in the community, two large parks and a well-preserved historic district are what draw people's attention to the town of Tolland. The University of Connecticut is just a ten minute drive away and Hartford can be found 22 miles from the town.

Easton, CT

Upscale and good economy. Some say the "Low Key" way of life can not be beat! Bethany Safe place to live with high quality of living.

New Hartford

Excellent education, good schools.

Beacon Falls

Great small town feeling


55 Plus Communities in CT

Park of Walcott CT active 55 plus communityPark of Wolcott - CT Park Avenue, Wolcott, CT 06716 The Park of Wolcott is the most affordable Active Adult housing development in the rural community of Wolcott, CT. This Beautiful residential community offered by Tim Bobroske Construction Services Honored as 2009 Builder of the year.




Sleepy Hollow Hills - Niantic CT Van Winkle Way, Niantic, CT 06357 Sleepy Hollow Hills is the premier 55+ active adult community located on the beautiful shore line of Southeastern CT. Just 32 luxury homes will be built in this community located in Niantic, ranked 75th best small town in America by Forbes Magazine.

Connecticut small towns include:

Ansonia, Aspetuck, Avon, Baltic, Beacon Falls, Berlin, Bethel, Bethlehem, Bolton, Bozrah, Branchville, Bridgeport, Bridgewater, Bristol, Britol, Broad Brook, Brookfield, Burlington, Canaan, Cannondale, Canton, Canton Center, Central Village, Chaplin, Chester, Clinton, Colchester, Colebrook, Collinsville, Cornwall Bridge, Cos Cob, Cromwell, Danbury, Danielson, Darien, Dayville, Deep River, Derby, Durham, East Canaan, East Granby, East Hampton, East Hartford, East Haven, East Lyme, Ct, Eastford, Easton, Enfield, Essex, Fairfield, Falls Village, Farmington, Gaylordsville, Georgetown, Glastonbury, Granby, Greenfield Hill, Greens Farms, Greenwich, Groton, Guilford, Haddam, Hamdem, Hamden, Hampton, Hartford, Hebron, Higganum, Jewett City, Kensington, Kent, Killingworth, Lakeside, Lakeville, Lebanon, Ledyard, Litchfield, Lyons Plain, Madison, Manchester, Mansfield Center, Meriden, Middlebury, Middletown, Milford, Montville, Moodus, Morris, Mystic, Naugatuck, New Britain, New Canaan, New Hartford, New Haven, New London, New Milford, Newington, Niantic, Noank, North Branford, North Canaan, North Franklin, Ct, North Granby, North Grosvenor Dale, North Grosvenordale, North Haven, North Windham, Northford, Norwalk, Norwich, Oakdale, Old Greenwich, Old Lyme, Old Saybrook, Oneco, Orange, Oxford, Pawcatuck, Plainfield, Plainville, Plantsville, Plymouth, Pomfret Center, Preston, Prospect, Putnam, Quaker Hill, Quinebaug, Redding, Redding Center, Ridgefield, Riverton, Rockfall, Rockville, Rocky Hill, Rogers, Roxbury, Conn. Salem, Sandy Hook, Scotland, Connecticut, Seymour, Sharon, Shelton, Simsbury, Somers, South Glastonbury, South Kent, South Windham, South Windsor, Southington, Southport, Stafford Spring, Stafford Springs, Staffordville, Stamford, Ct, Sterling, Stonington, Storrs, Storrs Mansfield, Stratford, Taftville, Talcottville, Terryville, Thomaston, Thompsonville, Titicus, Tolland, Topstone, Torrington, Trumbull, Uncasville, Union, Vernon, Vernon Rockville, Wallingford, Warren, Washington Depo, Waterbury, Watertown, Weatogue, West Granby, West Hartford, West Hartland, West Haven, West Redding, West Simsbury, West Willington, Westbrook, Weston, Westport, Wethersfield, Willimantic, Willington, Wilton, Windsor, Windsor Locks, Winsted, Wolcott, Woodbridge, Woodbury, Woodstock, Woodstock Valley CT.