Whippoorwill Homes for Sale

Welcome to Whippoorwill, a hidden gem nestled in the picturesque town of Old Lyme, Connecticut. This charming neighborhood is a serene retreat that offers an idyllic blend of natural beauty and community spirit. Known for its lush landscapes and tranquil surroundings, Whippoorwill is perfect for those seeking a peaceful lifestyle while still being close to the vibrant culture of the Connecticut shoreline.

As you stroll through the tree-lined streets, you'll discover a variety of beautifully maintained homes that reflect the area's rich architectural heritage. From quaint cottages to spacious family residences, there's something for everyone in Whippoorwill. Each property is thoughtfully designed to harmonize with the stunning natural environment, providing residents with both comfort and style.

Whippoorwill is not just about beautiful homes; it’s also about community. Neighbors often come together for seasonal events and gatherings, fostering a warm and welcoming atmosphere. Families will appreciate the nearby parks and recreational areas, which offer ample opportunities for outdoor activities, from hiking and biking to picnicking and birdwatching.

For those who enjoy coastal living, Whippoorwill is just a short drive away from the beautiful beaches of Old Lyme, where you can unwind by the shore or explore the charming local shops and restaurants.

Currently, there are several homes for sale in this enchanting neighborhood, making it an opportune time to invest in a piece of Whippoorwill. Whether you’re looking for a forever home or a weekend getaway, Whippoorwill offers an unparalleled lifestyle that combines the best of nature and community. Come and discover the charm of Whippoorwill—your dream home awaits!

Newest Whippoorwill Homes for Sale

$2,299,000

5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24183457 MLS

Set on more than 12 private acres in one of Old Lyme's most desirable locations, this exceptional new construction residence offers a rare combination of luxury, flexibility, and space to grow. Thoughtfully designed for today's lifestyle, the home features four bedrooms, including a spacious primary suite on the main level, and a beautifully appointed guest suite ideal for extended family, visiting guests, or a private home office. Inside, vaulted ceilings, custom millwork, rich hardwood floors, and a striking fireplace create an atmosphere of timeless elegance and warmth. The open concept design seamlessly blends sophisticated living with everyday comfort, while expansive windows invite natural light and frame picturesque views of the surrounding landscape. The property's expansive grounds are enhanced by stunning natural rock formations and thoughtfully designed outdoor living spaces, including a welcoming front paver patio and a large rear paver patio ideal for entertaining, dining al fresco, or simply enjoying the peaceful setting. With ample room for a pool, pool house, gardens, or additional recreational amenities, the possibilities are endless. Surrounded by natural beauty yet just minutes from the historic village of Old Lyme, beaches, marinas, and major commuting routes, this is a rare opportunity to enjoy the privacy of a country estate with the convenience of shoreline living. A truly exceptional property where luxury, craftsmanship, and nature come together.

41-B Whippoorwill Rd, Old Lyme

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