Top 10 Most Expensive Homes in Connecticut [Update 2024]


The state of Connecticut is one of the most well-known coastal states in the United States, and it features an attractive combination of urban and rural areas. There are obscenely opulent mansions and manors tucked away in many of the nation’s metropolitan centers and seaside communities.

These extremely pricey mansions are architectural masterpieces that, in most cases, offer residents a contemporary and peaceful atmosphere in which to live. In addition, some of the highest income in Connecticut are the proud owners of some of the most costly homes in the state.

Below is a list of the most expensive homes in Connecticut.

1. Great Is, Darien – $100 million

Great Is, Darien is one of the Most Expensive Homes in Connecticut

Located in Darien, Great Is, listed at a price of $100 million, encompasses an area of more than 60 acres. The main house has 10 bedrooms and 8 full bathrooms.

Moreover, the house is situated along a mile of shoreline, allowing residents to enjoy the amazing scenic views right from their house. Initially, this house was built in 1905, and has gone through many renovations over the last 100 years.

2. 450 Brickyard Rd – $60 million

450 Brickyard Rd

450 Brickyard Rd is a stunning house in Woodstock, Connecticut that looks like a castle. Built in 2010, this single family home is a masterpiece of brilliant craftsmanship and superior design.

Along with a total area of 18,777 square feet, the house has 9 bedrooms, 12 fireplaces and 7 full bathrooms. In addition, the house is built on a 400-acre lot, making it one of the largest private properties in the state.

3. 11 Island Ln – $41.5 million

Situated in Connecticut’s premier city, Greenwich, 11 Island Ln is a luxurious house that was bound to be super expensive due to its location. It is the perfect single family home for any of Connecticut’s billionaires, featuring awe-inspiring views of the ocean and the mountains.

The house consists of 6 bedrooms, 7 full bathrooms, a swimming pool, spa and much more. The house itself has a total area of 12,972 square feet and was built in 2012 on a 1.6 acre lot.

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4. 555 Lake Ave – $39 million

555 Lake Ave is a stunning 18,954-square-feet Georgian styled mansion that has 8-acres of beautiful gardens and exquisite architectural excellence. The house has 8 bedrooms as well as 8 fireplaces and an elevator.

Furthermore, it features a garage that has the capacity to park 5 cars. Being one of the most expensive homes in Connecticut, the house is designed for a luxurious life.

5. 15 Dairy Rd – $35 million

15 Dairy Rd

15 Dairy Rd is a beautiful 16,359-square-feet luxury house in Greenwich that really looks like a palace. Built in 2008, this house has a mid-country vibe that is attractive to many people.

The house itself encompasses a total area of more than 5 acres, and features amazing entertainment facilities. Moreover, it consists of 7 bedrooms, 9 full bathrooms and a 4-car garage, while offering stunning views.

6. 30 Field Point Dr – $30 million

30 Field Point Dr is a fabulous house built on more than 6 acres of pristine land in Greenwich. The 18,068-square-feet house is built in the Classic Georgian Colonial style, and has had only two owners since it was built in 1900.

Also, the house consists of 11 bedrooms, 9 full bathrooms and a 6-car garage. However, the highlight of this house has to be the grand center hall with a fireplace and wood paneling.

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7. 16 Hurlingham Dr – $28 million

The newest house on this list, the house was constructed last year in 2021. Priced at $28 million, the house is definitely worth the investment considering its facilities and geography. Located in Greenwich, this house is an absolute architectural masterpiece that is constructed on a massive 10-acre lot.

The house features 6 massive bedrooms and 7 full bathrooms. Additionally, there is also a lake around the property and the house itself is surrounded by large green trees.

8. 7-11 Old Stagecoach Rd – $28 million

7-11 Old Stagecoach Rd is built on a huge 87-acre property, and the house itself encompasses an area of more than 12,259-square-feet. It is a four-story house that provides breathtaking panoramic views that will soothe your mind.

Moreover, there are stunning bedrooms and 6 full bathrooms that come along with its garage, which has a capacity of parking 7 cars. There is also a tennis court, a tranquil park and many other indoor amenities.

9. 591 Riverside Rd – $27.5 million

A quintessential English country estate with awe-inspiring breathtaking views, 591 Riverside Rd is one of the best homes in Connecticut. Located in Greenwich, this is the oldest house on our list, as it was built in 1775.

This classic house has managed to retain its stunning vintage design despite going through countless renovations over the years. It has 7 bedrooms, 9 full bathrooms, a 6-car garage and is built on an 18-acre lot.

10. 88 Cedar Cliff Rd – $25.5 million

88 Cedar Cliff Rd is a beautiful French Normandy designed house located in Riverside, Connecticut. The house has a total area of 9,000 square feet, featuring 6 bedrooms and 8 full bathrooms.

Moreover, the 1.7 acres of lots on which it is built have beautiful gardens, lawns, trees, porches, a pool and a spa. Additionally, there is also a garage that has the capacity to park 4 cars.

The city of Greenwich is one of the best places to live in the United States, and it is not surprising at all to see that most of Connecticut’s most expensive houses are situated in this city. In fact, the state is home to super luxurious, elegant and massive homes, which are owned by Connecticut’s richest.

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