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10 Most Expensive Homes in Connecticut (With Pictures)

exterior of residential mansion with terrace

Connecticut is a great place to live. It’s the third smallest state by area and is the southernmost state in New England. It also has one of the highest per capita incomes in the country, leading many people to wonder how much the homes cost there. Keep reading as we list the sale prices of 10 of the most expensive homes in the Constitution State.

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The 10 Most Expensive Homes in Connecticut

1. 54 Byram Drive, Greenwich, Connecticut

Sale Price: $17.1 million
Acres: 3.9
Bedrooms: 9
Baths: 10

Greenwich is one of the more affluent areas of Connecticut, where you can expect to find the high-priced homes that many people dream about purchasing, and it’s also where you will find the highest-priced home on this list. The house at 54 Byram Drive has nine bedrooms and 10 baths on almost 4 acres and even includes a swimming pool, large flower garden, and a practice green to work on your golf game.

2. 112-116 Beachside Ave, Westport, Connecticut

Sale Price: $16.5 million
Acres: 7.7
Bedrooms: 7
Baths: 9

While the house at 112-116 Beachside Ave, Westport, is the second most expensive house in Connecticut, you might consider it a bargain because it comes with nearly 8 acres of land, while many of these other homes have far less. It also has seven bedrooms, nine baths, and four garages. It has an attractive herringbone brick floor and sits right on the waterfront.

3. 1125 Pequot Ave, Fairfield, Connecticut

Sale Price: $16.5 million
Acres: 3.4
Bedrooms: 7
Baths: 11

Fairfield is a well-to-do area of Connecticut where you are likely to find many attractive and expensive homes. The house at 1125 Pequot Ave recently sold for $16.5 million and is just one example. It has seven bedrooms and 11 baths, with four garages for your vehicles. There is an observation deck for watching sunsets over the water, and there is even an elevator to make it easier to visit the many floors.

4. 340 Willow St, Fairfield, Connecticut

Sale Price: $16.35 million
Acres: 5.6
Bedrooms: 6
Baths: 9

The house at 340 Willow St in Fairfield is an expensive property in this area that someone recently bought for over $16 million. This property is perfect for the automotive fan because it has six garages to keep your cars in. It also has plenty of space, with more than 5.5 acres to explore, along with six bedrooms and nine baths to enjoy. There is also a solarium, tennis court, wine cellar, and a renovated 1930s boathouse.

5. 19 Lower Cross Road, Greenwich, Connecticut

Sale Price: $13.8 million
Acres: 10
Bedrooms: 7
Baths: 12

The home at 19 Lower Cross Road in Greenwich was built in 1990 and completely renovated in 2011, so it’s fairly modern and shouldn’t require any work for a while. It has seven bedrooms, 12 baths, five garages, a climate-controlled pool, a full-size commercial gym (complete with a steam room), and a tennis court. The huge 10-acre lot is also a big draw for this property, as it’s the biggest on this list so far.

6. 66 Glenwood Drive, Greenwich, Connecticut

Sale Price: $12.5 million
Acres: 1.3
Bedrooms: 8
Baths: 9

The house at 66 Glenwood Drive is extremely attractive and compact, without much land to maintain. It has eight bedrooms and nine baths and provides access to an exclusive club that only neighborhood residents can visit. Another attraction of this property is a small four-bedroom cottage that provides plenty of room for guests to stay.

7. 25 Butlers Island Road, Darien, Connecticut

Sale Price: $10.5 million
Acres: 1.2
Bedrooms: 6
Baths: 8

The property at 25 Butlers Island Road in Darien is one of the few that isn’t in one of the more affluent areas, like Greenwich or Westport. It’s also a small home, with just 1.2 acres. However, the view is breathtaking, as it sits on a little peninsula that enables water to surround the house on three sides. Swimming in the heated pool provides a perspective that feels like you are looking over a cliff, and there is even a built-in spa with a waterfall to help you relax.

8. 36 Herrick Road, Sharon, Connecticut

Sale Price: $10.5 million
Acres: 51.3
Bedrooms: 11
Baths: 13

The home at 36 Herrick Road in Sharron, Connecticut, provides the buyer with plenty of value because it sits on a 51.3-acre lot. The property has seven buildings, including the main house, guest house, library, pool house, and even a log cabin. The main house is an older building that was recently renovated to keep it up to date.

9. 328 Calkinstown Road, Sharon, Connecticut

Sale Price: $10 million
Acres: 34.5
Bedrooms: 6
Baths: 9

328 Calkinstown Road is a property in Sharon, Connecticut, that provides the buyer with a large plot of land suitable for horseback riding or any other activity. It’s a Federal-style mansion, with six working fireplaces and a library with 300-year-old paneling to help you get a sense of history while reading. Expansion ideas include a pool or a tennis court.

10. 23 Raiders Lane, Darien, Connecticut

Sale Price: $9.5 million
Acres: 1.3
Bedrooms: 5
Baths: 8

23 Raiders Lane is the least expensive property on this list and the second one from the Darien area of Connecticut. It’s a modern property that overlooks a historic cove and includes an elevator, private dock, hot tub, outdoor patios, and a view of the water from every room in the house.

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What Are the Most Expensive Areas to Live in Connecticut?

Connecticut has several areas packed with expensive homes. Greenwich is one of the most popular, and Darien and Westport are also near the top. Other areas include Fairfield and most recently, Sharon, which has hosted a few big sales.

Why Are the Houses So Expensive in Connecticut?

Many of the houses on this list and others that you might see are large mansions built in the first half of the 1900s. Many people are willing to pay more for the historical value, and most of these homes have an amazing water view and even provide access to a private dock. The many rooms and amenities also help attract people with money and convince them to stay.

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Connecticut is a great place for the rich and famous to live peacefully outside the hustle and bustle of a big city. The large homes provide every amenity, and the view is often spectacular, whether it’s watching the waves as the sun rises or the stars at night. The most expensive house on this list sold for $17.1 million, and you can find it in Greenwich along with many other costly homes, but you can find fancy homes in other areas too, like Westport, Fairfield, and Sharon, with many fetching a sale price above $10 million.

Featured Image Credit: Max Vakhtbovych, Pexels

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