10 Fabulously Expensive Homes in Connecticut!

With its beautiful shoreline and convenience to New York City, Connecticut has long been the favored state for luxury homes owned by the rich and famous. This has remained true over time, as one of the most expensive residential properties ever sold in the United States went for $120 million in Greenwich. You can find some truly immaculate real estate here. Here are some of the most magnificent estates in Connecticut!  

1. Katharine Hepburn’s Home, Old Saybrook, CT

On and off the market for several years, Katherine Hepburn’s family home was recently purchased for $11 million. This beautiful home is located directly on the water. Beautiful rooms are spread throughout its three floors, and large picture windows let in ample sunlight. Each of its six bedrooms have their own bathrooms, and most rooms have a fireplace. It also has a private beach, a tennis court, and a dock. 

View Property Details

2. Cobb Island Drive, Greenwich, CT

Situated on the serene Cos Cob Harbor, 7 Cobb Island Drive recently sold for just over $15 million. This luxury home is located on 10 acres of waterfront property and has five bedrooms. It has a beautiful outdoor pool and spa, tennis court, and barn perfect for parties.

View Property Details

3. Donald Trump’s Former Estate, Greenwich, CT

Located on a six-acre peninsula, this three-story home was once owned by Trump. Sold for $54 million, this mansion boasts eight bedrooms, 10 full bathrooms, staff apartments, and a guest house. The grounds are exquisitely manicured and there is of course, a pool.

View Property Details

4. Copper Beech Farm, Greenwich, CT

Sold in 2014 for $120 million, Copper Beech Farm made the record as the most expensive home sold at the time. This property has 50 acres along the waterfront and is conveniently located just 45 minutes away from New York City. This extensive home was built in 1896 and features a main home that has 12 bedrooms, nine bathrooms, and a library within its 13,500 square-feet. Other perks of the home include a wine cellar and a solarium.

View Property Details

5. Thimble Islands Portfolio Home, Branford, CT

Purchase a house and get an island with it by buying the deed to this expensive home on one of the Thimble Islands. Located off the cost of Branford, this home has 14 bedrooms and 8.5 bathrooms located throughout its 13,100 square feet. If that isn’t enough, you get an entire private island that is landscaped with trees, rock gardens, a swimming pool, gazebo, and more. All this is currently for sale for $50 million.

View Property Details

6. Belle Haven Home, Greenwich, CT

Located on Glenwood Drive, this custom shingle-style home provides views of Long Island. Sold for $15 million, this home features five bedrooms, hardwood cherry floors, and a guest suite. The grounds have a pool, gardens, pool house, and detached garage.

View Property Details

7. Conyers Farm Home, Greenwich, CT

The largest home in Greenwich, and in the exclusive Conyers Farm gated community, was purchased for $45 million in 2004. This luxury, 80-acre estate features an 8,000-square foot home, three guest cottages, and a horse stable large enough for 22 horses. This mansion was recently listed in 2015 for $65 million.

View Property Details

8. Round Hill Manor, Greenwich, CT

The most expensive Connecticut home currently brokered by Sotheby’s is Round Hill Manor, listed at nearly $40 million. This red brick estate has nine bedrooms, eight full bathrooms, and four half bathrooms. It features built-in bookshelves, an open kitchen with state-of-the-art appliances and fixtures, and luxury bathrooms with walk-in showers and large bathtubs. 

View Property Details

9. Great Island, Darien, CT

This location is simply mind-blowing. For an astronomical $175 million, this 63-acre island could be yours. About an hour outside of New York City, Great Island includes immaculate views of Long Island Sound, an equestrian facility with 20 stalls and interior ring, a jumping arena and polo field for horses, a caretaker’s home and greenhouse, several guest cottages, and an incredible amount of land. 

View Property Details

10. Clapboard Ridge Road, Greenwich, CT

Situated on 5.34 acres, this sprawling home is listed for about $20 million. Zillow currently has the location listed as “Off Market.” This six-bed, 9.5-bath home covers 16,863 square-feet. The stunning two story entry hall will make you feel like royalty and the antique bronze French doors are breathtaking. This home also features a paneled library with a fireplace, an office and covered porch, a formal dining room with a fireplace, billiards rooms, and more. 

View Property Details

Select a Connecticut town to find the Best Things-To-Do and Places To Go around you
Find Real Estate Agents and Realtors Near You
Enter City / State or Zip code below
Select your town to find the Best Things To Do and Places To Go around you: