Devil's Den Real Estate

Welcome to Devil's Den, an enchanting neighborhood nestled in the heart of Weston, Connecticut. Renowned for its natural beauty and serene ambiance, Devil's Den offers a perfect blend of suburban charm and outdoor adventure. This picturesque area is characterized by its lush landscapes, rolling hills, and an abundance of recreational opportunities, making it an ideal place for families, nature lovers, and anyone seeking a tranquil lifestyle.

One of the neighborhood's crowning jewels is the Devil's Den Preserve, a sprawling 1,700-acre nature sanctuary managed by the Connecticut Audubon Society. Here, residents can explore miles of well-maintained hiking trails, observe diverse wildlife, and enjoy breathtaking views of the surrounding woodlands. The preserve is a haven for outdoor enthusiasts, offering year-round activities such as hiking, birdwatching, and even cross-country skiing in winter.

Devil's Den is not just about nature; it also boasts a close-knit community atmosphere. The neighborhood is known for its excellent schools, making it a prime choice for families. Weston High School consistently ranks among the top in the state, ensuring that children receive a quality education in a supportive environment.

Local amenities include charming boutiques, cozy cafes, and farmer’s markets, all contributing to the vibrant community spirit. The town’s commitment to preserving its natural resources and fostering a strong sense of community makes Devil's Den a truly special place to call home.

Whether you’re looking for a peaceful retreat or an active lifestyle, Devil's Den in Weston, CT, offers the perfect backdrop for your next chapter. Come discover the charm and beauty of this remarkable neighborhood!

Newest Listings in Devil's Den

$2,250,000

4 Beds ⋅ 6 Baths ⋅ 24201533 MLS

Nestled on over 3 breathtaking acres with over 500 feet of frontage on the west branch of the Saugatuck River, this exceptional property offers the perfect blend of privacy, outdoor living and natural beauty. Surrounded by mature trees and lush lawns, the setting is nothing short of spectacular--truly one of the most beautiful in Weston. The spacious home is thoughtfully designed with an open floorplan that seamlessly connects the main living areas, making it ideal for entertaining. It features four generously sized bedrooms, each with its own private bathroom. The main level includes a large living room and a den each with a fireplace and river views, an elegant dining room, and a family room off the expansive kitchen--all flowing effortlessly from one to the next. There is a second story great room with oversized windows and beautiful views. This bright and airy room with cathedral ceilings and a full bathroom can easily be converted into a fifth bedroom. Just outside, your own private oasis awaits--an expansive deck overlooking the river, scenic landscaping, and a stone patio with gunite pool--perfect for summer relaxation or entertaining under the stars. In addition to the numerous recent improvements to the key systems of the home, the driveway has been redone and the house has been painted on the interior and exterior. Whether you're looking for a peaceful retreat or a forever home, this extraordinary property offers an unparalleled lifestyle in an idyllic setting.

6 Old Orchard Dr, Weston

$6,500,000

4 Beds ⋅ 5 Baths ⋅ 24196609 MLS

Welcome to 10 Dragonwood Lane - The Iconic Origami House Set on an extraordinary 15.57-acre estate spanning four separately deeded parcels, 10 Dragonwood Lane is a one-of-a-kind architectural masterpiece that seamlessly blends modern design, luxury, and nature. Known as the Origami House, this remarkable residence offers unparalleled privacy, tranquility, and future development potential while bordering a serene nature preserve. A winding, tree-lined driveway leads past flowering cherry trees, a private electronic gate, and a lighted tennis court before unveiling the home's breathtaking contemporary design. Conceived by the renowned Leroy Street Studio of Manhattan, the approximately 8,500-square-foot residence draws inspiration from the art of folded geometry. Sculptural cube-like forms create dramatic ceiling heights, expansive walls of glass, and light-filled interiors that effortlessly blur the distinction between indoor and outdoor living. At the heart of the home is the spectacular Glass Great Room, inspired by I.M. Pei's iconic Louvre Pyramid. Enclosed by glass on three sides, this extraordinary space opens onto an expansive terrace overlooking one of two cascading waterfalls within the estate's nationally recognized koi sanctuary. Designed for both sophisticated everyday living and grand-scale entertaining, the residence offers:

10 Dragonwood Ln, Weston

$2,995,000

4 Beds ⋅ 6 Baths ⋅ 24176936 MLS

Extraordinary riverfront modern retreat set against a breathtaking backdrop of waterfall, woodland, and sweeping water views in one of Weston's most remarkable settings. Surrounded by preserved land and trails of Devil's Den Preserve, this extensively renovated residence offers a rare connection to nature paired with sophisticated design and luxury amenities. Walls of glass, soaring ceilings, and thoughtfully reimagined interiors create a seamless relationship between indoors and out. The stunning chef's kitchen was completely redesigned. A dramatic four-season sunroom with floor-to-ceiling window systems opens at the touch of a button to create an unparalleled indoor-outdoor living experience. The primary suite is a serene riverfront retreat featuring expansive views and a spa-inspired bath with heated floors, steam shower, soaking tub, glass-front sauna overlooking the water, and custom closets. Three additional ensuite bedrooms are on the second level. Additional highlights include a spectacular media room, billiard room, office/gym space, stone terraces, and a beautifully positioned pool overlooking the river. An exceptional offering combining architectural sophistication and an immersive, private natural setting.

22 Pent Rd, Weston

Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.