9 Most Expensive Houses Currently on the Market in Connecticut

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The median home price in Connecticut is $317,500, which is about $60,000 less than the national average. Despite this, the most expensive homes in the state can give the priciest modern palaces a run for their literal money.

Continue reading to learn about the 9 most expensive houses in Connecticut, including the features and designs that have driven their price so far above the average for the state.

9. 7-11 Old Stagecoach Rd

Price: $28,000,000
City: Ridgefield
Size: 12,259 sqft
Rooms: 5 bed/9 bath
7-11 Old Stagecoach Rd
photo source: Zillow

The huge property at 7-11 Old Stagecoach Rd gets its value from the expansive 87 natural acres it encompasses. The house itself is a 5-bed, 9-bath estate totaling over 12,000 sqft of livable room. But the real draw of the place, known as the “Double H Farm,” is the land.

This property has stalls for 40 horses, a lounge for your racing trophies, huge barns, paddocks and sheds as far as the eye can see, and more for the skilled racing enthusiast. The Double H Farm could be yours for $28,000,000.

Did you know?

This property thrives on outdoor amenities. Included on-site are both outdoor and indoor riding rings, a jumping derby field, pool, tennis court, hot walkers, and more.

8. 30 Field Point Dr

Price: $30,000,000
City: Greenwich
Size: 18,068 sqft
Rooms: 11 bed/11 bath
30 Field Point Dr
photo source: Zillow

The house at 30 Field Point Dr is one of the oldest in the luxury housing markets in Connecticut, being built back in 1900. It’s a huge house, with 11 bedrooms and 11 bathrooms encompassing 18,068 sqft. The house is on a 6.38-acre property, done in the classic Georgian Colonial architectural style.

The house’s inner courtyard is done in classic brick, leading to the home’s grand center hall with a palatial fireplace and wood paneling everywhere you look. The home nearly doubled in size in a major renovation in 1991. Marble and wood accents abound in this $30,000,000 home.

Did you know?

The crown jewel of the house’s many rooms is a gorgeous library. It features a doorway taken directly from the Grosvenor House in London.

7. 15 Dairy Rd

Price: $34,990,000
City: Greenwich
Size: 16,359 sqft
Rooms: 7 bed/13 bath
15 Dairy Rd
photo source: Zillow

The house at 15 Dairy Rd in lush Greenwich, Connecticut is on a handsome 5.31-acre plot. The house is 16,359 sqft in size, encompassing 7 bedrooms and 13 bathrooms.

The mid-country main home is on a gated estate boasting immensely luxurious materials and classic workmanship, from the tree-lined gravel drive up to the vine-covered façade and grand entry hall.

The house features a wildflower garden and lawn created by the designer Reed Hilderbrand. The home’s features in addition to its numerous bedrooms include a billiard room, an indoor gym, theater room, and pool house connected to the main rooms by an underground tunnel. The house is connected by a sound system, fireplace, and formal tennis court.

The house is on the market for a price of $34,990,000.

Did you know?

Reed Hilderbrand is an exterior design firm known for many luxury properties, including the American Museum of Natural History Gilder Center, the Arnold Arboretum Leventritt Garden, the Chazen Museum of Art, Crystal Bridges, and Duke University Abele Quad.

6. 45 Binney Ln

Price: $35,000,000
City: Old Greenwich
Size: 13,428 sqft
Rooms: 8 bed/12 bath
45 Binney Ln
photo source: Zillow

The house at 45 Binney Ln is pretty new, built-in 2020 on a small 1.07-acre plot. However, the draw of this house, which is currently listed for $35 million, is the amount of waterfront property it sports on that one glorious acre. With over 200 feet of waterfront access, a boathouse, spa, terraces, gardens, and a private pier, the house is sure to give any outdoor enthusiast the time of their life.

The house has 8 bedrooms, 12 bathrooms, and 13,428 sqft of total living space. It has many indoor and outdoor entertainment spaces. In fact, one of the draws of this property is how it combines them. This includes an open floorplan interior that opens down into the wine room and scullery and out into the porch patios with their breathtaking waterfront views, which stretch to Long Island.

Did you know?

This house won the HOBI award in 2021, which stands for the Home Builders Association of Connecticut, Inc. It’s the most coveted homebuilding award in the state.

5. 555 Lake Ave

Price: $39,000,000
City: Greenwich
Size: 18,954 sqft
Rooms: 8 bed/13 bath
555 Lake Ave
photo source: Zillow

The huge house has a presidential, palatial façade with 18,954 sqft of space. This is split up between 8 bedrooms and 13 bathrooms, in addition to numerous indoor amenities. The house was built in 2001 on an 8.23-acre plot landscaped as pristinely as a public park.

The house was designed in the Georgian brick mansion style that opens on an old-style reception hall with a three-story crystal chandelier, covered in Wenge walnut floors. It leads into the formal dining room and huge fireplace, surrounded by a custom bar. The main suite of the house has a balcony overlooking the stone terrace and pool house.

Did you know?

The house features many other luxury amenities, including an outdoor kitchen and pizza oven, rotisserie grill, mosaic pool, home theater, gym and yoga room, wine cellar, and two butler’s pantries. But the masterpiece of the property has to be the two-story library made from English mahogany, complete with a brass upper gallery.

4. 7 John St

Price: $39,500,000
City: Greenwich
Size: Undisclosed
Rooms: 10 bed/16 bath
7 John St
photo source: Zillow

7 John Street is a house in the luxury housing community of Greenwich, Connecticut, which like many houses on this list is valued in proportion not only to its amenities but its extensive estate. In this case, the natural land surrounding this mansion encompasses 22 acres of woodland landscape. This is also among the oldest houses in this area, designed in 1937.

The property is known as the Robin Hill Farm and has not been available for purchase for over a generation of owners. The house has recently been restored with new additions on the property, originally designed by the landscape architect Jacqueline Osty. The landscape includes stables, paddocks, two cottages, a riding ring, and a grazing field, all for the avid horse enthusiast.

The property is listed for $39.5 million.

Did you know?

The house was originally designed by Augusta L. Noel, the interior designer who also created the prestigious Whitney Museum.

3. Undisclosed Address

Price: $40,000,000
City: Greenwich
Size: 14,887 sqft
Rooms: 6 bed/10 bath
Undisclosed Address
photo source: Zillow

The house at this undisclosed address in Greenwich, Connecticut is one of the most recently built properties on this list, completed in 2020. The estate has 14,887 sqft of living space, with 6 beds and 10 baths, on a property of 27 acres of gorgeous natural landscape.

The house was built in the French Norman style, which gives it a limestone and steel façade that combines classic design with modern functionality. The whole house features bronze highlights and includes interior amenities such as an inside pool and a full-length skylight.

The house is currently on the market for an even $40 million.

Did you know?

The house’s extensively landscaped exterior also features many luxury amenities, including a Har-Tru tennis court, pavilion, slate boat house, private dock, gazebo, and on-site walking paths that lead right to the Greenwich horseback trails.

2. 11 Island Ln

Price: $41,500,000
City: Greenwich
Size: 12,972 sqft
Rooms: 6 bed/9 bath
11 Island Ln
photo source: Zillow

The house at 11 Island Ln in Greenwich, Connecticut was built in 2012 on a small, 1.6-acre plot that makes up for its size by being on a private peninsula with panoramic views of the water on 280 degrees of the property. This amounts to over 732 feet of direct shoreline.

The home is 12,972-sqft of living space with 6 bedrooms and 9 bathrooms, including a large oval pool, sauna, built-in pizza oven, spa, private pier, boathouse, and private beaches for fishing and kayaking.

The house is on the market for $41.5 million.

Did you know?

Greenwich, Connecticut is well-known as one of the most luxurious and exclusive property areas in the state. Within that already exclusive city is the 24-hour guarded luxury community of Belle Haven, where this property is located.

1. 450 Brickyard Rd

Price: $60,000,000
City: Woodstock
Size: 18,777 sqft
Rooms: 9 bed/10 bath
450 Brickyard Rd
photo source: Zillow

The most expensive house in Connecticut is 450 Brickyard Rd. This absolute palace was built in 2010 and encompasses 18,777 sqft of living space broken between 9 bedrooms, 10 bathrooms, and a ton of amenities.

The inside of the house has a stunning entry hall fit for royalty, 12 full fireplaces, a huge bespoke kitchen, and more.

The outside of the castle glitters with 126-foot-tall towers while the inside features that rustic charm with hardwood floors made from over 25 species of wood. The home features a raised stage with an auditorium for film and theater lovers, a pool and dock, and a full circular bar.

This palatial property is on the market for a cool $60 million.

Did you know?

The home is on 400 acres of beautiful nature, including not only the Woodstock Castle but a 30-acre pond.


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