Whippoorwill Real Estate

Welcome to Whippoorwill, a hidden gem nestled in the picturesque town of Old Lyme, Connecticut. This charming neighborhood is a serene retreat, perfect for those seeking a harmonious blend of natural beauty and community spirit. Whippoorwill offers a tranquil lifestyle, surrounded by lush greenery, rolling hills, and the soothing sounds of nature.

One of the standout features of Whippoorwill is its close-knit community. Residents here take pride in their neighborhood, fostering a warm and welcoming atmosphere. Whether you're enjoying a leisurely stroll along the tree-lined streets or participating in local events, you'll quickly feel at home among friendly neighbors who share a love for this idyllic setting.

Nature enthusiasts will appreciate the proximity to the stunning Connecticut River and the nearby Old Lyme Preserve, where scenic trails invite exploration and outdoor adventures. Spend weekends kayaking, hiking, or simply soaking in the breathtaking views that this area has to offer. The nearby beaches along the Long Island Sound provide a perfect escape for sunbathing, picnicking, and enjoying the coastal lifestyle.

Families will also find Whippoorwill an ideal place to settle down, with access to highly-rated schools and recreational facilities. The vibrant arts scene in Old Lyme, known for its historic art colony, offers cultural experiences that enrich the community.

With its blend of natural beauty, community warmth, and a wealth of recreational opportunities, Whippoorwill is more than just a neighborhood; it’s a place where memories are made and cherished for a lifetime. Come discover the charm of Whippoorwill and envision your future in this enchanting corner of Old Lyme!

Newest Listings in Whippoorwill

$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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