Most Expensive vs. Cheapest Homes in Connecticut – You Won’t Believe #3

Most Expensive Homes in Connecticut

• Copper Beech Farm holds the record as the most expensive residential property ever sold in Connecticut, fetching an astonishing $138 million. This estate spans over 50 acres along the coast and is considered a rare opportunity for a high-caliber residence1.

• Other ultra-luxury homes in Connecticut, especially in Greenwich, range from around $10 million to over $44 million. For example:

  • 545 Indian Field Rd, Greenwich, listed at $44.6 million with 12,492 sqft.

  • 579 Indian Field Rd, Greenwich, at $43 million, 11,500 sqft.

  • 157 Long Neck Point Rd, Darien, at $35 million, 8,684 sqft.
    These homes typically feature 6 to 12 bedrooms, multiple bathrooms, and extensive amenities such as pools, tennis courts, and waterfront access23.

• A notable historic luxury estate is the former "Haroldyn House" at 21 Vista Dr., Greenwich, sold for $31.5 million in 2024. This Georgian colonial-style mansion dates back to 1939 and was once owned by Donald Trump and Ivana Trump. It boasts 11 bedrooms, 18 bathrooms, multiple pools, a tennis court, and over 750 feet of shoreline on six acres5.

Cheapest Homes in Connecticut

• While detailed listings of the absolute cheapest homes are less highlighted in luxury-focused sources, the Connecticut housing market has a very limited inventory overall, with some homes in less affluent areas like Waterbury available at significantly lower prices.

• The median home price in Hartford, Connecticut’s capital, is about $214,546, which is below the national median of $281,900, indicating more affordable options exist in urban centers compared to wealthy suburbs8.

• However, the state’s housing market is tight, with very low inventory and high demand driving prices up even in more modest neighborhoods. Many buyers are competing fiercely, often paying over asking prices, making affordable homeownership challenging6.

You Won’t Believe #3

• The third most expensive home sale or listing in Connecticut might surprise you because it is not just about size or luxury but also about historical significance and celebrity ownership. The "Haroldyn House" (21 Vista Dr., Greenwich) stands out as a fascinating blend of history, luxury, and celebrity, selling for $31.5 million after 15 years on and off the market. Its connection to a former president-elect and extensive renovations by Ivana Trump add a unique story behind its price tag5.

Summary

Connecticut’s housing market is characterized by extreme contrasts-from multimillion-dollar estates with celebrity ties to more affordable urban homes, though even these face stiff competition and rising costs. The third most expensive home’s blend of history and luxury is a surprising highlight in this spectrum12568.