The 15 Coolest Houses in Connecticut!

When you think of Connecticut’s architecture, you may think of historical homes built in the Colonial times, symmetrical Georgian homes, and corniced Greek Revival homes. What you might not think of are Connecticut’s unusual homes including those built in a windmill, a former schoolhouse, or a castle. Continue reading to find 15 cool, unique, and downright strange homes located across Connecticut.

1. Windmill House, Essex, CT

As the name implies, this tiny home (considered any home under 1,000 square-feet) is built inside of a refurbished windmill. At only 840 square-feet, this home has three bedrooms located on multiple levels and one full bathroom. Located on the waterfront in Foxboro Point (11 Foxboro Rd.), this property is highly unique.

2. Tugboat Lighthouse Home, West Haven, CT

Located on 313 Benham Hill Road, this unusual home is modeled from a lighthouse and a former tugboat. A deck connects the house and tugboat, and the living space is 3,184 square-feet. This large home has four bedrooms and three bathrooms spread across the house. In the lighthouse portion of the home, there is an elevator that allows access to higher floors. Even more unusually, this house is not located on the water.

3. Oldest Home, Guilford, CT

Built in the 17th century in the post-medieval style, the oldest home in Connecticut is called the Old Stone House (or Henry Whitfield State Museum) and is currently a museum. For a taste of history, put yourself into the original owner’s, Reverend Henry Whitfield’s, shoes and tour the home to get a feel for what it must have been like to live in the 1600s.

4. Blue Winged House, Hamden, CT

This unusual private home might be the most fun of the bunch and certainly is the most colorful. The exterior of cool home is decorated with beautiful colors, unique shapes, and unusual add-ons. Unsurprisingly, the interior is just as creative, but at the same time seems to be a functional living space.

5. Geodesic dome, Bethlehem, CT

Another tiny home on the list—only 165 square feet—is this geodesic dome in the woods of Bethlehem. This tiny home is perhaps as eco-conscious as it gets without living in a tent. This dome was even built from wood sourced on the property, but appears to only consist of a bedroom.

6. Tiny Cedar Home, Branford, CT

Getting even tinier now, this 144-square-foot home is built entirely from cedar on a five-ton trailer. Tiny but functional, it consists of a full bathroom, custom kitchen, refrigerator and freezer, and space for a bed. 

7. 200-year-old mill, Newtown, CT

The owners of a 200-year old mill in Newtown are now allowing guests booked via Airbnb to rent a two-room suite with a private entrance and full bath. This historical property has beautiful gardens, a pool, and patio. The large windows that let in rays of sunlight encourage lazy mornings during your stay.

8. Connecticut Round House, Wilton, CT

If you drove by this home unexpectedly, you might think that you have seen a UFO! The Connecticut Round House is a private home that resembles a spaceship hovering over a small hill next to a pond. Designed by Richard T. Foster, it sits 12 feet off the ground on a base that can slowly rotate 360 degrees to allow for comprehensive views of the scenery through all glass walls. This home is 2,997 square-feet and consists of three bedrooms and two bathrooms. It is located on 112 Olmstead Hill Rd in Wilton.

9. Glass House, New Canaan, CT

The glass house is a historic home that was built in 1949 and is made entirely made from glass. It is currently an art museum that is open seasonally and holds visiting collections. Though lacking privacy, the glass construction allows for unobstructed views of Connecticut’s rolling hills and treed valleys.

10. Copper Beech Farm, Greenwich, CT

The most expensive home in Connecticut was recently sold for millions of dollars ($120 million) on 499 Indian Field Rd in one of Connecticut’s most exclusive towns. This 50-acre property is only 45 minutes away from New York City, making the location highly desirable. At a massive 13,519 square-feet, the main house has 12 bedrooms, seven full baths, and two half baths. It also features a library, solarium, and wine cellar.

11. Chrismark Castle, Woodstock, CT

This shockingly large, this 22,377 square-foot home looks like it is more suited for a Game of Thrones episode than a Connecticut home. With its moat and gates guarded by stately lion statues, I half expect to see dragons soaring over its turrets. This home has eight bedrooms and 8.5 bathrooms and ceilings are adorned with painted clouds. This castle is located on 450 Brickyard Road in Woodstock.

12. The Octagon House, Danbury, CT

Who needs a four-sided house when you can have eight sides? Try on an octagon house for size. Listed on the National Register of Historic Places, this is a unique house that is currently being restored by the town. Built in 1852, it followed designs outlined in Orson Squire Fowler’s 1848 book that led to an architectural fad in the U.S. in the 19th century. Few of these octagonal houses remain, and this one can be see on 21 Spring Street. 

13. Schoolhouse Turned Home, Haddam, CT

Located on 28 Old Turnpike Road in Haddam, this former 1800s schoolhouse was renovated into a stunning home in 2001. Though it is only 690 square-feet, it has an ample living space with one bedroom and one full bath. It has a gorgeous interior with all hardwood floors and a spacious kitchen with a full-sized refrigerator. 

14. Gillette’s Castle, East Haddam, CT

Built from 1914 to 1919 by actor William Gillette, this castle is truly a site to see. The knobby stone castle looks like something out of a fairytale and when you step indoors for a tour, you might be surprised by the built-in couches, tables on tracks, and distinct doors. Gillette’s Castle is open seasonally to tour and the grounds are open year-round.

15. Gaylordsville Spite House, New Milford, CT

Also known as the Cake House, this house has a sordid past and is called a spite house because the original owner modified it out of spite for the state. Though the story varies on the source you read, the former owner, Jan Pol, created the cake-like structure when the state took away an abandoned girl that he and his wife were caring for. This home is composed of five floors, each getting smaller as they go up—like a wedding cake. 

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