Whippoorwill Homes for Sale

Welcome to Whippoorwill, a picturesque neighborhood nestled in the heart of Old Lyme, Connecticut, within the scenic New London County. This charming community is known for its serene atmosphere, lush landscapes, and a rich tapestry of history that makes it a perfect place to call home. Whippoorwill is characterized by its tree-lined streets, spacious lots, and beautifully designed homes that reflect a blend of classic New England architecture and modern comforts.

As you explore Whippoorwill, you’ll find a strong sense of community among its residents. The neighborhood offers an array of recreational activities, from hiking and biking along the nearby trails to enjoying leisurely afternoons at local parks. The proximity to the Connecticut River and Long Island Sound provides ample opportunities for water sports, fishing, and stunning sunsets that will take your breath away.

For those considering a move, Whippoorwill boasts a selection of homes for sale that cater to various lifestyles and preferences. Whether you’re seeking a cozy cottage, a sprawling family home, or a charming ranch-style property, the real estate options here are diverse and appealing. Many homes feature expansive yards, updated interiors, and easy access to local amenities, including shops, restaurants, and schools.

With its idyllic setting and welcoming atmosphere, Whippoorwill is not just a neighborhood; it’s a community where memories are made, and a lifestyle is embraced. Discover your dream home in Whippoorwill, where tranquility meets convenience, and every day feels like a retreat. Don’t miss your chance to be a part of this enchanting neighborhood!

Newest Whippoorwill Homes for Sale

$365,000

3 Beds ⋅ 2 Baths ⋅ 24191954 MLS

Best/final offers in by 7/28 @ 2:00 This charming 3-bedroom, 2-bath ranch is tucked away on a quiet dead-end road in desirable Old Lyme. Set on a level lot with a paved driveway & plenty of parking, this property features a detached two-car garage, offering ample space for vehicles, boats, or storage. Inside, you'll find beautiful hardwood floors, a kitchen full of character, and a comfortable floor plan designed for everyday living. The primary bedroom includes a private full bath, while two additional bedrooms and a second full bath provide flexibility for family, guests, or a home office. A newer roof, updated plumbing, & newer insulation in the attic adds peace of mind, while the location offers an exceptional coastal lifestyle. Enjoy access to White Sands Beach, Rogers Lake, and Soundview Beach, perfect for swimming, boating, fishing, or simply relaxing by the water. Commuters will appreciate convenient access to the nearby train station with service to New York City, making weekend getaways or daily travel a breeze. Whether you're looking for a year-round residence, a vacation retreat, or a home close to shoreline amenities, this Old Lyme ranch offers the perfect combination of comfort, convenience, and location.

5 Blackwell Rd, Old Lyme

$2,299,000

5 Beds ⋅ 5 Baths ⋅ 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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