WESTON-EASTON-REDDING, CT — A sprawling three-home compound in Redding, a modernist architectural showpiece in Weston and a private lake estate in Easton are among the most expensive properties for sale across the three towns.
The 10 priciest residential listings identified on Zillow as of Oct. 26 range from $1,575,000 to $7,725,000, featuring everything from waterfalls and tennis courts to heated swimming pools, private lakes and homes designed for entertaining.
Here's a look at the 10 most expensive homes across Weston, Easton and Redding.
No. 1: 206 Umpawaug Road, Redding — $7,725,000
The most expensive property on the list is a seven-acre Nantucket-style compound in Redding's Umpawaug neighborhood.
Built in 2008, the estate includes a main residence, carriage house with an in-law suite and an award-winning pool house. Zillow lists 13,094 square feet, seven bedrooms, eight full bathrooms and five half bathrooms.
Inside are a primary suite with a fireplace and steam shower, an elevator, wine cellar, home theater and billiards room. Outside are a heated gunite pool and spa.
No. 2: 10 Dragonwood Lane, Weston — $6,500,000
Known as the Origami House, this modernist estate was designed by Manhattan-based Leroy Street Studio and built in 2013.
The 8,586-square-foot home sits on 15.57 acres spanning four separately deeded parcels. Its cube-like design draws inspiration from folded geometry, while a glass-enclosed great room was inspired by the Louvre Pyramid in Paris.
The property also features a koi sanctuary with two waterfalls, a gated driveway and a lighted tennis court.
No. 3: 294 Maple Road, Easton — $4,999,000
A private lake is among the highlights of this 15.43-acre shingle-style estate.
Built in 2013, the 7,070-square-foot home has five bedrooms, five full bathrooms and four half bathrooms. Features include geothermal heating and cooling, an elevator, four fireplaces and a kitchen with Sub-Zero and Wolf appliances.
Outside are a saltwater gunite pool, pool house, outdoor kitchen and fire pit. The property also includes a separate building lot.
No. 4: 8 Norfield Woods Road, Weston — $3,895,000
This planned luxury home by Tomas Brothers Builders sits on 2.35 acres along a cul-de-sac in Lower Weston.
The proposed 6,000-square-foot residence features six bedrooms, five full bathrooms and one half bathroom. The listing says construction is expected to be completed in less than a year.
No. 5: 76 Lords Highway, Weston — $3,450,000
Built in 2001, this 9,974-square-foot estate sits on 2.51 acres near Weston's school campus.
The six-bedroom home has seven full bathrooms and four half bathrooms, with a floating staircase, walnut floors and a banquet-sized dining room featuring a curved wall of windows.
Other highlights include a living room with a coffered ceiling and an octagonal office.
No. 6: 32 Bernhard Drive, Weston — $2,999,000
Tucked at the end of a long driveway on a cul-de-sac, this 1997 home offers 6,198 square feet on just over 2 acres.
The four-bedroom property includes four full bathrooms and two half bathrooms.
Outside are a heated gunite swimming pool, hot tub, stone patio and outdoor shower. The asking price was reduced by $201,000 on Oct. 19.
No. 7: 16 Katydid Lane, Weston — $2,895,000
This newly constructed home by Thomas Sturges Construction sits on 2.25 acres along a private lane.
The 5,000-square-foot property features five bedrooms, five full bathrooms and one half bathroom.
The asking price was reduced by $180,000 on Oct. 21.
No. 8: 115 Limekiln Road, Redding — $2,495,000
This gated estate sits on 9.54 acres and was designed with architectural inspiration from H.H. Richardson, according to the listing.
Built in 1989, the 7,328-square-foot home has four bedrooms, five full bathrooms and two half bathrooms.
A former owner who was a classical pianist reportedly hosted concerts in the home's living and dining rooms, which offer enough space for a concert grand piano.
No. 9: 15 Adirondack Trail, Easton — $2,275,000
This custom-built home sits on 3 level acres and was constructed in 1997.
The 7,575-square-foot residence has five bedrooms, four full bathrooms and one half bathroom.
Features include a two-story foyer, music room and Palladian windows.
No. 10: 23 Norton Road, Easton — $1,575,000
Rounding out the list is a renovated home in Lower Easton with seasonal reservoir views.
Built in 1961, the 5,079-square-foot home sits on 3.03 acres and features five bedrooms, three full bathrooms and one half bathroom, with room for a potential sixth bedroom, according to the listing.
Outdoor features include a covered porch and large deck.
Prices and listing details are based on Zillow listings reviewed Oct. 26, 2026, and may change. Only properties listed for sale or offered as new construction were considered. Pending listings, vacant land and multifamily properties were excluded.
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