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

$985,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24199485 MLS

Stately colonial with wonderful curb appeal. Thoughtfully designed and custom built with high-quality materials and timeless architectural details. Warm and inviting, this move-in-ready home on nearly two acres offers an exceptional blend of privacy, tranquility and convenience - tucked away on a quiet, desirable cul-de-sac surrounded by nature, yet just two miles to Old Lyme Village. Living area of 3,226 square feet plus an unfinished basement, walk-up attic and two-car garage. Open floor plan, high ceilings, large windows and drenched with light. A dramatic two-story foyer is flanked by a dining room and an office - both with French doors. The living room flows seamlessly into the eat-in kitchen featuring an expansive center island - perfect for entertaining. Large primary bedroom with a walk-in closet and en-suite bathroom. The enormous bonus room is versatile as a gym, playroom and TV room. Spacious living areas, walk-in closets, mudroom and abundant storage offer comfort and functionality. Dine alfresco, relax on the back deck and enjoy the peaceful surroundings. Professionally landscaped with perennial flowers that burst into color each spring. The fenced yard provides privacy in this friendly neighborhood ideal for walking, jogging and biking. Trails, beaches, golf, tennis, pickleball, shopping and restaurants are all nearby. Only two hours from New York and Boston with easy access via I-95, Route 9 and the train. Always dreamed of living on the shoreline...carpe diem!

6 Whippletree Ln, Old Lyme

$1,899,999

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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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