
Most expensive homes for sale in Connecticut
Buying a home is an investment—and an increasingly expensive one. The median value of a home in the United States reached $295,300 in June 2020, according to the National Association of REALTORS.
To learn more about home values in Connecticut, Stacker analyzed data from realtor.com to compile a list of the most expensive homes for sale in the state.
Home buyers have a lot to consider when house-hunting or looking to invest in rental properties, from the state of the housing market itself to taxes and potential resale value. The housing market grew robust and pricey in the last decade following the 2008 recession, but the market could be slowed by rising interest rates. Such a downturn can be good news for potential home-buyers, as you're more likely to be able to wager a deal on an otherwise overpriced house. Then there is the house itself to consider, including what kind of upkeep it requires (and those associated costs). Depreciation affects all homes at an average rate of 3.636% each year, which can be a help come tax season if you use your home for business or rentals—but may cost you later in capital gains taxes when you when you sell. Meanwhile, land value tends to increase over time depending on several factors including where the house is located and what amenities and homes are nearby. More desirable neighborhoods allow sellers to charge more; the mantra "location, location, location" has never been more relevant.
Keep reading to find out the most expensive homes for sale in Connecticut.

#50. 857 Lake Ave, Greenwich

#49. 425 N Maple Ave, Greenwich

#48. 61 Byram Shore Rd, Greenwich

#47. 550 Round Hill Rd, Greenwich

#46. 6 Bluewater Ln, Westport

#45. 10 Gray Ln, Westport

#44. 5 Stony Point Rd, Westport

#43. 25 Cowdray Park Dr, Greenwich

#42. 264 Hillspoint Rd, Westport

#41. 44 Mooreland Rd, Greenwich

#40. 27 Macedonia Brook Rd, Kent

#39. 564 Under Mountain Rd, Salisbury

#38. 21 Clapboard Ridge Rd, Greenwich

#37. 425 Round Hill Rd, Greenwich

#36. 2 Broad Rd, Greenwich

#35. 46C Senff Rd, Washington

#34. 62 Bermuda Rd, Westport

#33. 1099 Pequot Ave, Fairfield

#32. 82 Brookwood Ln, New Canaan

#31. 5 Hedley Farms Rd, Westport

#30. 25 Edgewood Dr, Greenwich

#29. 1093 Pequot Ave, Fairfield

#28. 25 Upper Cross Rd, Greenwich

#27. 205 Round Hill Rd, Greenwich

#26. 30 Round Hill Club Rd, Greenwich

#25. 36 Walsh Ln, Greenwich

#24. 32 Grahampton Ln, Greenwich

#23. Wallacks Pt, Stamford

#22. 429 Taconic Rd, Greenwich

#21. 3 Hekma Rd, Greenwich

#20. 160 John St, Greenwich

#19. 266 Michigan Rd, New Canaan

#18. 31 Vista Dr, Greenwich

#17. 6 Windrose Way, Greenwich

#16. 78 Mayo Ave, Greenwich

#15. 187 Umpawaug Rd, Redding

#14. 400 5 1/2 Mile Rd, Cornwall

#13. 543 Stanwich Rd, Greenwich

#12. 57 MT Tom Rd, Salisbury

#11. 640 Sasco Hill Rd, Fairfield

#10. 136 Field Point Cir, Greenwich

#9. 435 Round Hill Rd, Greenwich

#8. 471 Lake Ave, Greenwich

#7. 435 and 429 Round Hill Rd, Greenwich

#6. 14 Cowdray Park Dr, Greenwich

#5. 30 Field Point Dr, Greenwich

#4. 16 Hurlingham Dr, Greenwich

#3. 100 Sterling Rd, Greenwich

#2. 591 Riversville Rd, Greenwich
