Whippoorwill Homes for Sale

Welcome to Whippoorwill, a hidden gem nestled in the picturesque town of Old Lyme, Connecticut. Known for its serene ambiance and natural beauty, Whippoorwill offers a unique blend of tranquility and community spirit, making it the perfect place to call home.

This charming neighborhood is characterized by its lush landscapes, winding roads, and a sense of privacy that many homeowners cherish. Whippoorwill is surrounded by beautiful parks and nature reserves, inviting residents to enjoy outdoor activities like hiking, birdwatching, and leisurely strolls. The area is also conveniently located near the stunning Connecticut River, providing opportunities for boating and fishing enthusiasts.

Whippoorwill boasts a friendly community atmosphere, where neighbors become friends and families thrive. The local schools are highly regarded, offering excellent educational opportunities for children. With a range of community events throughout the year, you’ll find plenty of chances to connect with fellow residents and create lasting memories.

If you’re considering making Whippoorwill your home, you’ll be pleased to discover a variety of homes for sale that cater to different tastes and budgets. From charming single-family houses with spacious yards to modern, updated homes featuring the latest amenities, there’s something for everyone. Many properties showcase stunning views of the surrounding nature, allowing you to enjoy the beauty of Connecticut right from your doorstep.

Discover the warmth and charm of Whippoorwill—where your dream home awaits in this idyllic neighborhood. Explore our listings today and take the first step towards a new beginning in Old Lyme!

Newest Whippoorwill Homes for Sale

$1,899,999

4 Beds ⋅ 4 Baths ⋅ 24203798 MLS

This single level modern farmhouse blends clean contemporary design with timeless New England warmth, set at the end of a private drive in serene Old Lyme, Connecticut. Thoughtfully crafted for easy, elegant living, the home features four spacious bedrooms, an airy open layout, and abundant natural light throughout. A sunroom anchors the living space with year round views of the surrounding landscape, while covered porches and a covered patio extend the living area outdoors, creating effortless flow for relaxing or entertaining. The property abuts protected open space, offering a sense of privacy, nature, and quiet that's increasingly rare. With its refined finishes, one floor convenience, and peaceful setting, this home delivers the best of modern comfort and classic farmhouse character in one of Old Lyme's most tranquil locations.

41-1 Whippoorwill Rd, Old Lyme

$575,000

3 Beds ⋅ 2 Baths ⋅ 24198874 MLS

Welcome home to 91 Whippoorwill Road, a darling 3 bed, 2 bath Cape located in the charming coastal town of Old Lyme, CT! Enjoy the best of small-town living with convenient access to both New York and Boston. This enchanting property features a picturesque stream and abuts more than 20 acres of open space dedicated to the Old Lyme Land Trust, creating a peaceful natural backdrop just minutes from town and schools. Inside, a newly renovated white kitchen with new dishwasher, microwave and stove opens to a beautiful dining room designed to enhance every dining experience, from intimate dinners to lively gatherings. The sun-soaked family room offers a warm and welcoming space with direct access to the back deck, perfect for relaxing or entertaining. A first-floor primary bedroom and full bath provide comfortable main-level living. Upstairs are two additional bedrooms, a second full bath, and a generously sized walk-in closet offering excellent additional storage. A spacious, dry basement provides plenty of room for laundry, storage, hobbies, or future possibilities. Come experience the beauty, comfort, and convenience of life in Old Lyme!

91 Whippoorwill Rd, Old Lyme

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