Madison : Connecticut


What It Is Like to Retire in Madison

Madison is a charming small town on Connecticut’s Long Island Sound. Its real estate values are the highest in Connecticut east (towards Boston) of New Haven, reflecting its desirability as a place to live.

As a retirement community there is much to find in this town of just under 19,000. It has a compact downtown with cute stores and the active, well-stocked E.C. Scranton Memorial Library. RJ Julia’s is one of the country’s top independent book stores, attracting best-selling authors on a regular basis. Located on a beautiful green is the First Congregational Church of Madison, a classic house of worship that dates to 1840. Graceful homes built by colonial sea captains flank both sides of the Boston Post Road (U.S. Route 1), reflecting the village’s heritage as a colonial ship-building center. The town features sandy beaches, private and public, that attract substantial numbers of “summer” residents.  Children and grandchildren love to visit this tourist destination, which is a plus. Transportation is good with a train station downtown that connects to Amtrak and (NY’s) Metro North in New Haven. The Madison Beach & Recreation Department has an extensive list of programs and activities to keep all ages busy and engaged.

For more information on taxes check out this  retirement guide for Connecticut.  You might also enjoy this Wall Street Journal article about Madison and nearby Guilford.


Where to Retire in Madison and Home Prices

This upscale community has many desirable neighborhoods for active adults, including numerous developments featuring condos, town houses and 55+ associations. Some of the condo associations include The Mews (in the heart of the downtown), Windemere, Oxford Fells, Kensington Acres, Strathmore Farms, and many more. Many new residents are retirees from Fairfield County and the New York suburbs.
Zillow reports the Medium Home Value was $536,816 in late 2021, up 24.5% .  Beachfront homes sell for millions and pay very high taxes. Condominiums can vary in price from the $200's to $1MM, depending on which development.


What Is Special about Madison

• Walkable, charming downtown • Accessible public beaches – the Surf Club, East Wharf, West Wharf, Hammonasset State Park • RJ Julia’s Bookstore • Deacon John Grave House – house dating back to the 1600’s and continuously occupied by one family • E.C. Scranton Memorial Library – architect Henry Bacon (who designed the Lincoln Memorial in Washington) •The Madison Beach Hotel has just been rebuilt and provides a nice place on the water for a drink, meal, or weekend stay • New downtown Senior Center has many programs and facilities

What Is Not Special about Madison

• Traffic in the summer • High property values make it expensive to move here  • Limited availability of restaurants in town and few restrooms in coffee houses • Big box shopping can be inconvenient distances • Police department has had numerous public scandals • Properties along the water have very high property taxes.

Who Will Like Retirement in Madison

Madison is a growing, vital community with all types and ages of people living there. Increasingly it is pre-dominated by families with young children (parents commute to New Haven, Hartford, or Fairfield County) and people over 60.


Local Economy Is Driven by

Education, banking and finance, medical, tourism, real estate, light manufacturing

Climate and Physical Environment

Madison is situated on the Long Island Sound midway between New Haven and Old Saybrook. Going away from the water the land encounters a series of hilly ridges. Its climate is milder in winter and summer than just a few miles inland, thanks to waters of Long Island Sound. The average July high is 84. The average January high is 36 and the low is 20. The wettest month is October (5").

Restaurants & Cultural Scene

The E.C. Scranton Memorial Library features many programs.  There are plans to expand the library with many new features with drive-up book-drop. Madison Arts Cinema features first run films. The Madison Sculpture Mile has placed dozens of significant sculptures downtown. Occasional concerts in the First Cong. Church & on the green, especially the 4th of July RJ Julia’s Bookstore has frequent book talks by big name authors. Many interesting art galleries worth a visit. Long Wharf Theatre and the Yale Rep provide first rate plays in New Haven. Shoreline Institute of Lifelong Learning


Crime in Madison is practically nonexistent - barely 20 percent of the national average.

Medical Facilities

 Yale New Haven Emergency Clinic (Guilford, 1 mile); Yale New Haven Hospital (New Haven, 15 miles); St. Raphael's Hospital (New Haven, 15 miles)



New Haven Airport (15 Miles); Providence Airport (Providence 70 Miles); Bradley Airport (Hartford, 70 miles)


Valuable Links

City of Madison

Madison on Wikipedia
Madison Chamber of Commerce


What people are saying about Madison

Madison, CT, update
I lived next door to Madison for 22 years. It\'s one of the most gorgeous and charming colonial towns anywhere. It also has roughly five miles of waterfront, part of it the huge Hammonasset State Park. This is a great town for walking, amazingly scenic bike-riding and beautiful residential architecture, both along the waterfront and inland. Some residents love the atmosphere so much that they even commute to New York City, which is a couple of hours away by train, at least. If you have the money and want the four seasons and appreciate colonial history, I can\'t think of a more stunning town.
Posted by elafreniere on November 25, 2020
Retiring in Madison
I received this question from a California visitor to Topretirements. My response follows: I explored Madison using Google Earth and found the area very interesting. It reminds me of places like Mamaroneck & Rye, N.Y. Also checked out the home prices there, and discovered that you can get something nice for about $300,000. Since you are a native there, do you have an opinion of this town as a retirement area. All we really want is convienient shopping ... etc... A close proximety to N.Y.C. is also desireable. Or perhaps you can suggest some other areas... Any suggestions would be welcomed. Response: Madison is a beautiful area. Great old charming town with a green and strong zoning. Many people are retiring here from different places, especially the New York suburbs. Traffic not so bad, more charming, slower pace, more for your money. That said, $300,000 gets you a starter home or a small condo. Some condos even much more than that. Shopping OK with some boutiques and one of the country's best independent bookstores (RJJulias). But outlet shopping in next towns, Clinton & Westbrook. You can take the train from Madison's new train station to New Haven - then step across the platform and be in NY's Grand Central in about an hour and a half. Guilford, Mystic, Old Lyme, Old Saybrook, Essex, Chester all beautiful towns too.
Posted by madman on July 12, 2010
retiring in madison
Heh, if you were thinking about retiring in Madison or Guilford, you might be interested in this article from the Wall Street Journal. Retirees like its location midway between NY and Boston, and how it is charming without the hassle of places closer to those cities.
Posted by madman on May 16, 2009

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