Whippoorwill Real Estate

Welcome to Whippoorwill, a serene and picturesque neighborhood nestled in the charming town of Old Lyme, Connecticut. Known for its tranquil ambiance and natural beauty, Whippoorwill offers a unique blend of rural charm and modern convenience, making it an ideal place to call home.

Surrounded by lush greenery and stunning landscapes, residents of Whippoorwill enjoy easy access to the scenic Connecticut River and the breathtaking coastline of Long Island Sound. This area is perfect for nature enthusiasts, with ample opportunities for hiking, birdwatching, and enjoying leisurely strolls along picturesque trails. The nearby Old Lyme State Forest provides an expansive playground for outdoor activities, ensuring that adventure is always just around the corner.

Whippoorwill is also steeped in a rich artistic heritage, being part of the historic Lyme Art Colony, which has attracted artists and creatives for over a century. Local galleries, art studios, and cultural events foster a vibrant community spirit, making it easy for residents to connect and engage with their neighbors.

Families will appreciate the highly-rated schools in the area, which prioritize academic excellence and holistic development. The welcoming community atmosphere is perfect for raising children, with plenty of parks and recreational facilities to explore.

Conveniently located just a short drive from I-95, Whippoorwill offers easy access to nearby cities while maintaining its peaceful, suburban charm. With its beautiful homes, friendly neighbors, and a strong sense of community, Whippoorwill truly embodies the best of Connecticut living. Discover your dream home in this enchanting neighborhood today!

Newest Listings in Whippoorwill

$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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