41 Whippoorwill Rd

New London County CT 06371

4694 sq. ft.

12.78 ac.

Single-Family

Last sold for $2,100,000

Tammy Tinnerello, last sold this property on 15 October 2026 after 565 days on market.

Overview

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. Beyond the property itself, 41-2 Whippoorwill Road offers the opportunity to experience the unparalleled lifestyle that has made Old Lyme one of Connecticut's most cherished shoreline communities. Rich in history, culture, and natural beauty, Old Lyme is known for its picturesque village center, renowned art heritage, preserved open spaces, beautiful beaches, marinas, and miles of scenic trails. Residents enjoy a relaxed coastal lifestyle with convenient access to everyday amenities while remaining connected to major metropolitan areas. Positioned between New York City and Boston, Old Lyme offers easy access via Interstate 95 and Amtrak rail service, making weekend escapes and business travel remarkably convenient. Boston is approximately two hours away, while New York City can be reached in just over two hours. The property's location also places you within easy reach of some of New England's most desirable destinations. Explore the vibrant waterfront, boutique shopping, acclaimed restaurants, and maritime charm of downtown Mystic. Spend afternoons enjoying the beautiful beaches, boutiques, and renowned dining scene of Westerly and Watch Hill, Rhode Island, home to some of the region's most spectacular coastal vistas. Whether boating on Long Island Sound, enjoying a sunset dinner overlooking the water, or strolling through charming seaside villages, the best of the Connecticut coastline is at your doorstep. Offering exceptional privacy without sacrificing convenience, 41-2 Whippoorwill Road represents a rare opportunity to embrace the quintessential New England coastal lifestyle in one of the shoreline's most sought after communities.

Features

5 bedrooms

5 bathrooms

6 carspaces

3 garage spaces

4694 sq. ft. floor area

12.78 ac. lot size

Single-Family

Estimated Value

Based on this property and similar 5 bedroom single-family properties sold in New London County over the last 12 months, the estimated median property value of 41 Whippoorwill Rd is $1.19m.

Median value

$1.19m

Estimated value range

$600k - $3.25m

Median days on market

Estimated value trend

32%

increase over the last 12 months

Average days on market is based on recent, comparable sales in New London County. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 41 Whippoorwill Rd

2026

Sold

$2,100,000

15 Oct 2026 by Tammy Tinnerello, of William Pitt Sotheby's Int'l

2025

Sold

$251,000

18 Feb 2025 by Allyson Cotton, of William Pitt Sotheby's Int'l

2021

Sold

$165,000

26 Apr 2021 by Nancy Johnson, of William Pitt Sotheby's Int'l

Happy sellers in New London County

We have insufficient information to provide an overview of customer satisfaction for New London County. Viewing the agent profiles, reviews and sales for New London County can provide insights for this location.