Whippoorwill Real Estate

Welcome to Whippoorwill, a charming neighborhood nestled in the heart of Old Lyme, Connecticut. Located in New London County, Whippoorwill offers residents a peaceful and idyllic setting to call home.

One of the highlights of living in Whippoorwill is its close-knit community feel. Neighbors often gather for social events and get-togethers, creating a friendly and welcoming atmosphere. The neighborhood is known for its well-maintained properties, manicured lawns, and tree-lined streets, giving it a picturesque and serene ambiance.

Whippoorwill boasts a prime location that provides easy access to a variety of amenities. Within a short distance, residents can find a range of shopping options, including boutiques, grocery stores, and specialty shops. There are also several dining establishments offering a diverse culinary experience.

Nature enthusiasts will appreciate the abundance of outdoor recreational opportunities in the area. Whippoorwill is surrounded by beautiful parks, hiking trails, and nature reserves, providing ample opportunities for walking, jogging, and exploring the scenic surroundings. The nearby Connecticut River and Long Island Sound offer opportunities for boating, fishing, and other water activities.

Families with children will find excellent educational options in the highly regarded schools of Old Lyme. The neighborhood is also home to various community centers, sports clubs, and recreational facilities, ensuring there is always something for everyone to enjoy.

With its peaceful atmosphere, friendly community, and convenient location, Whippoorwill is an ideal place to call home. Whether you're looking for a close-knit community or access to outdoor activities, this neighborhood has it all. Come and discover the charm and beauty of Whippoorwill in Old Lyme, Connecticut.

Newest Listings in Whippoorwill

$985,000

3 Beds ⋅ 3 Baths ⋅ 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 ⋅ 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

$949,000

4 Beds ⋅ 3 Baths ⋅ 24194469 MLS

Beautifully maintained Colonial set on a quiet, picturesque lot offering the perfect blend of comfort, flexibility, and resort style outdoor living. The spacious kitchen is the heart of the home, featuring abundant workspace, multiple dining areas, and seamless access to a sun filled four season room overlooking the private backyard. A flexible main level room offers the option of a bedroom, home office, or den. Upstairs you'll find four generously sized bedrooms, including one currently used as a home office, providing versatility for today's lifestyle. The finished lower level offers additional living space ideal for a home gym, recreation room, media room, or playroom. Step outside to your own private retreat featuring a pickleball court, above ground lap pool with integrated spa, putting green, expansive lawn, and spectacular sunset views that create the perfect setting for entertaining or relaxing. Surrounded by mature landscaping and peaceful views, the property offers exceptional privacy while remaining just minutes from Old Lyme Village, beaches, marinas, golf, shopping, and restaurants. Offering flexible living spaces, an incredible backyard designed for recreation, and a sought after location, this exceptional home is ready to be enjoyed in every season.

6 Jericho Dr, 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

Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.