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

$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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