These Are the 25 Worst Towns in Connecticut for Retiree Homebuyers on a Budget

For retirees looking to stretch their fixed housing budget in Connecticut, these 25 towns represent the most expensive real estate markets in the state according to the Zillow Home Value Index data.

Darien tops the list with a median home value of $2.04 million in 2024, while even the “most affordable” town on the list, Newtown, requires over $613,000 to buy a typical home. These markets, dominated by affluent New York City suburbs in Fairfield County and scenic coastal enclaves, have seen substantial price appreciation that puts them out of reach for most retirees on fixed incomes.

Notable Observations:

Unlike Colorado’s resort-town dominance, Connecticut’s most expensive markets cluster in Fairfield County, where New York City proximity commands premium prices, with four towns (Darien, Greenwich, New Canaan, and Westport) all exceeding $1.7 million median values.

Rural and scenic towns showed surprising strength, with Sharon and Salisbury both seeing nearly 88% appreciation from 2014 to 2024, suggesting growing demand for countryside living within reach of metropolitan areas.

The COVID-19 period significantly impacted prices, with towns like Westport and Old Saybrook seeing over 70% appreciation just in the five years from 2019 to 2024, indicating a dramatic shift toward suburban and coastal living preferences.

Here’s the full list.

1. Newtown, Connecticut

At the entry point of our list, Newtown demonstrates the robust nature of Connecticut’s luxury market, with median values climbing from $359,974 in 2014 to $379,105 in 2019, before reaching $613,441 in 2024. This charming town has seen property values appreciate by 70.4% over the decade, while maintaining a strong 61.8% growth rate from 2019 to 2024.

2. Old Saybrook, Connecticut

This coastal gem has experienced remarkable growth in its real estate market, starting at $342,622 in 2014, rising to $362,697 in 2019, and achieving $618,763 in 2024. Old Saybrook’s property values have surged by 80.6% over ten years, while posting an impressive 70.6% gain in the last five years.

3. Woodbridge, Connecticut

The upscale suburb of Woodbridge showcases steady appreciation, with median values progressing from $373,873 in 2014 to $379,785 in 2019, before reaching $618,991 in 2024. This community has experienced a solid 65.6% increase over the decade, while maintaining a robust 63.0% growth from 2019 to 2024.

4. Norwalk, Connecticut

This vibrant coastal city has seen significant value increases, beginning at $379,190 in 2014, advancing to $421,805 in 2019, and reaching $619,420 in 2024. Norwalk’s property values have grown by 63.4% over the decade, while showing a more moderate 46.8% appreciation from 2019 to 2024.

5. New Preston, Connecticut

This picturesque village has demonstrated strong market performance, with values rising from $358,417 in 2014 to $398,777 in 2019, before climbing to $634,101 in 2024. The town has posted a significant 76.9% appreciation over ten years, while maintaining a solid 59.0% growth in the last five years.

6. Sharon, Connecticut

This rural haven has seen dramatic appreciation, with median values starting at $339,071 in 2014, increasing to $360,263 in 2019, and reaching $637,193 in 2024. Sharon has experienced one of the highest appreciation rates at 87.9% over the decade, while posting an impressive 76.9% gain from 2019 to 2024.

7. Madison, Connecticut

This coastal community has maintained strong growth, with values progressing from $396,886 in 2014 to $392,422 in 2019, before achieving $652,285 in 2024. Madison’s real estate market has appreciated 64.4% over ten years, while showing a robust 66.2% increase in the last five years.

8. Cornwall, Connecticut

The scenic town of Cornwall demonstrates steady appreciation, with median values rising from $387,621 in 2014 to $396,235 in 2019, before reaching $653,143 in 2024. Property values have increased by 68.5% over the decade, while maintaining a strong 64.8% growth from 2019 to 2024.

9. Stamford, Connecticut

This major business hub has seen consistent growth, with values climbing from $431,616 in 2014 to $455,099 in 2019, before reaching $662,260 in 2024. Stamford’s market has appreciated by 53.4% over ten years, while showing a more moderate 45.5% increase from 2019 to 2024.

10. Sherman, Connecticut

This charming small town has experienced substantial growth, with median values increasing from $394,795 in 2014 to $414,443 in 2019, before achieving $662,871 in 2024. Sherman’s property values have risen by 67.9% over the decade, while posting a solid 59.9% appreciation from 2019 to 2024.

11. Bridgewater, Connecticut

This rural community showcases strong market performance, with values rising from $414,611 in 2014 to $423,142 in 2019, before reaching $702,151 in 2024. Bridgewater has experienced a 69.4% increase over ten years, while maintaining a robust 65.9% growth from 2019 to 2024.

12. Lyme, Connecticut

This historic river town has seen significant appreciation, with median values climbing from $434,926 in 2014 to $438,254 in 2019, before achieving $725,247 in 2024. Lyme’s property values have increased by 66.8% over the decade, while posting a strong 65.5% gain from 2019 to 2024.

13. Redding, Connecticut

The wooded enclave of Redding shows steady growth, with values progressing from $519,519 in 2014 to $492,197 in 2019, before reaching $811,231 in 2024. This sought-after community has experienced a 56.2% increase over ten years, while posting a robust 64.8% appreciation from 2019 to 2024.

14. Salisbury, Connecticut

This northwestern Connecticut town has seen remarkable appreciation, with median values rising from $439,324 in 2014 to $471,776 in 2019, before climbing to $824,505 in 2024. Salisbury has posted one of the highest decade-long appreciation rates at 87.7%, while maintaining a strong 74.8% growth from 2019 to 2024.

15. Fairfield, Connecticut

This sought-after coastal town demonstrates consistent growth, with values increasing from $544,070 in 2014 to $544,560 in 2019, before reaching $856,158 in 2024. Fairfield’s property values have appreciated by 57.4% over ten years, while showing a solid 57.2% gain from 2019 to 2024.

16. Easton, Connecticut

This upscale community has maintained strong market performance, with median values starting at $584,314 in 2014, adjusting to $548,332 in 2019, before achieving $880,805 in 2024. Easton has experienced a 50.7% increase over the decade, while posting a robust 60.6% growth from 2019 to 2024.

17. Roxbury, Connecticut

This picturesque town shows impressive appreciation, with values climbing from $532,927 in 2014 to $537,853 in 2019, before reaching $900,428 in 2024. Roxbury’s property values have increased by 69.0% over ten years, while maintaining a strong 67.4% growth from 2019 to 2024.

18. Ridgefield, Connecticut

This affluent community demonstrates steady growth, with median values rising from $571,615 in 2014 to $560,601 in 2019, before achieving $904,808 in 2024. Ridgefield has experienced a 58.3% increase over the decade, while posting a solid 61.4% appreciation from 2019 to 2024.

19. Washington, Connecticut

This historic town has seen substantial appreciation, with values progressing from $544,677 in 2014 to $558,757 in 2019, before reaching $942,087 in 2024. Washington’s property values have grown by 73.0% over ten years, while showing a robust 68.6% increase from 2019 to 2024.

20. Wilton, Connecticut

This upscale suburb maintains strong market performance, with median values starting at $773,426 in 2014, adjusting to $713,302 in 2019, before climbing to $1,132,485 in 2024. Wilton has experienced a 46.4% increase over the decade, while posting a significant 58.8% growth from 2019 to 2024.

21. Weston, Connecticut

This prestigious community shows consistent appreciation, with values rising from $830,898 in 2014 to $749,751 in 2019, before reaching $1,240,395 in 2024. Weston’s property values have increased by 49.3% over ten years, while maintaining a strong 65.4% growth from 2019 to 2024.

22. Westport, Connecticut

This premier coastal town demonstrates remarkable growth, with median values starting at $1,151,542 in 2014, adjusting to $999,337 in 2019, before achieving $1,704,116 in 2024. Westport has experienced a 48.0% increase over the decade, while posting an impressive 70.5% appreciation from 2019 to 2024.

23. New Canaan, Connecticut

This exclusive community maintains its position among Connecticut’s elite markets, with values progressing from $1,366,644 in 2014 to $1,174,417 in 2019, before reaching $1,907,561 in 2024. New Canaan has seen a 39.6% increase over ten years, while showing a robust 62.4% growth from 2019 to 2024.

24. Greenwich, Connecticut

This world-renowned town continues to command premium prices, with median values climbing from $1,366,795 in 2014 to $1,330,656 in 2019, before achieving $2,011,348 in 2024. Greenwich has experienced a 47.2% increase over the decade, while maintaining a strong 51.2% appreciation from 2019 to 2024.

25. Darien, Connecticut

The crown jewel of Connecticut’s luxury real estate market, Darien tops the list with median values starting at $1,394,309 in 2014, adjusting to $1,273,299 in 2019, before reaching an impressive $2,039,963 in 2024. This prestigious community has experienced a 46.3% increase over ten years, while posting a substantial 60.2% growth from 2019 to 2024.