41-B Whippoorwill Road, Old Lyme (Whippoorwill), CT, 06371 | $2,299,000

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 and Rhode Island coastlines 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

  • Town: Old Lyme
  • Rooms: 10
  • Bedrooms: 5
  • Baths: 4 full / 1 half
  • Laundry: Main Level
  • Style: Ranch,Farm House
  • Year Built: 2026
  • Garage: 3-car Attached Garage,Driveway
  • Heating: Hydro Air,Zoned
  • Cooling: Central Air
  • Basement: Full,Unfinished,Concrete Floor
  • Above Grade Approx. Sq. Feet: 4,694
  • Acreage: 12.78
  • Est. Taxes: $2,391
  • HOA Fee: $100 Monthly
  • Lot Desc: In Subdivision,Lightly Wooded,Borders Open Space
  • Elem. School: Per Board of Ed
  • Middle School: Lyme-Old Lyme
  • High School: Lyme-Old Lyme
  • Appliances: Allowance
  • MLS#: 24183457
  • Website: https://www.raveis.com
    /eprop/24183457/41bwhippoorwillroad_oldlyme_ct?source=qrflyer
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Listing courtesy of William Pitt Sotheby's Int'l   Phone: (860) 434-2400

Room Information

Type DescriptionDimensionsLevel
Bedroom 1 9 ft+ Ceilings,Jack & Jill Bath,Walk-In Closet,Hardwood Floor15.0 x 13.1Main
Bedroom 2 9 ft+ Ceilings,Jack & Jill Bath,Walk-In Closet,Hardwood Floor15.8 x 13.7Main
Bedroom 3 Hardwood Floor23.0 x 12.0Upper
Den Gas Log Fireplace,Hardwood Floor22.5 x 17.9Main
Dining Room 9 ft+ Ceilings,French Doors,Hardwood Floor15.1 x 12.1Main
Eat-In Kitchen 9 ft+ Ceilings,Breakfast Bar,Island,Pantry,Hardwood Floor13.2 x 19.5Main
Living Room Cathedral Ceiling,Fireplace,Hardwood Floor24.0 x 21.0Main
Office Hardwood Floor10.5 x 10.2Upper
Primary BR Suite 9 ft+ Ceilings,French Doors,Walk-In Closet,Hardwood Floor20.1 x 17.2Main
Primary BR Suite Bedroom Suite,Walk-In Closet,Hardwood Floor16.0 x 16.6Upper

William Raveis Family of Services

Our family of companies partner in delivering quality services in a one-stop-shopping environment. Together, we integrate the most comprehensive real estate, mortgage and insurance services available to fulfill your specific real estate needs.

Customer Service

888.699.8876

Contact@raveis.com

Our family of companies offer our clients a new level of full-service real estate. We shall:

  • Market your home to realize a quick sale at the best possible price
  • Place up to 20+ photos of your home on our website, raveis.com
  • Provide frequent communication and tracking reports showing the Internet views your home received on raveis.com
  • Showcase your home on raveis.com with a larger and more prominent format
  • Give you the full resources and strength of William Raveis Real Estate, Mortgage & Insurance and our cutting-edge technology

To learn more about our credentials, visit raveis.com today.

Frank KolbSenior Vice President - Coaching & Strategic, William Raveis Mortgage, LLC

NMLS Mortgage Loan Originator ID 81725

203.980.8025

Frank.Kolb@raveis.com

Our Executive Mortgage Banker:

  • Is available to meet with you in our office, your home or office, evenings or weekends
  • Offers you pre-approval in minutes!
  • Provides a guaranteed closing date that meets your needs
  • Has access to hundreds of loan programs, all at competitive rates
  • Is in constant contact with a full processing, underwriting, and closing staff to ensure an efficient transaction

Robert ReadeInsurance Sales Director, William Raveis Insurance

860.690.5052

Robert.Reade@raveis.com

Our Insurance Division:

  • Will Provide a home insurance quote within 24 hours
  • Offers full-service coverage such as Homeowner's, Auto, Life, Renter's, Flood and Valuable Items
  • Partners with major insurance companies including Chubb, Kemper Unitrin, The Hartford, Progressive,
    Encompass, Travelers, Fireman's Fund, Middleoak Mutual, One Beacon and American Reliable

Ray CashenPresident, William Raveis Attorney Network

203.925.4590

For homebuyers and sellers, our Attorney Network:

  • Consult on purchase/sale and financing issues, reviews and prepares the sale agreement, fulfills lender
    requirements, sets up escrows and title insurance, coordinates closing documents
  • Offers one-stop shopping; to satisfy closing, title, and insurance needs in a single consolidated experience
  • Offers access to experienced closing attorneys at competitive rates
  • Streamlines the process as a direct result of the established synergies among the William Raveis Family of Companies

41-B Whippoorwill Road, Old Lyme (Whippoorwill), CT, 06371

$2,299,000

Customer Service

William Raveis Real Estate

Phone: 888.699.8876

Contact@raveis.com

Frank Kolb

Senior Vice President - Coaching & Strategic

William Raveis Mortgage, LLC

Phone: 203.980.8025

Frank.Kolb@raveis.com

NMLS Mortgage Loan Originator ID 81725

5/6 (30 Yr)
Adjustable Rate Jumbo*
30 Year
Fixed-Rate Jumbo
15 Year
Fixed-Rate Jumbo
Loan Amount $1,839,200 $1,839,200 $1,839,200
Term 360 months 360 months 180 months
Initial Interest Rate** 5.500% 6.000% 6.000%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.165% 6.086% 6.183%
Monthly Tax Payment $199 $199 $199
H/O Insurance Payment $125 $125 $125
Initial Principal & Interest Pmt $10,443 $11,027 $15,520
Total Monthly Payment $10,767 $11,351 $15,844

* The Initial Interest Rate and Initial Principal & Interest Payment are fixed for the first and adjust every six months thereafter for the remainder of the loan term. The Interest Rate and annual percentage rate may increase after consummation. The Index for this product is the SOFR. The margin for this adjustable rate mortgage may vary with your unique credit history, and terms of your loan.

** Mortgage Rates are subject to change, loan amount and product restrictions and may not be available for your specific transaction at commitment or closing. Rates, and the margin for adjustable rate mortgages [if applicable], are subject to change without prior notice.

The rates and Annual Percentage Rate (APR) cited above may be only samples for the purpose of calculating payments and are based upon the following assumptions: minimum credit score of 740, 20% down payment (e.g. $20,000 down on a $100,000 purchase price), $1,950 in finance charges, and 30 days prepaid interest, 1 point, 30 day rate lock. The rates and APR will vary depending upon your unique credit history and the terms of your loan, e.g. the actual down payment percentages, points and fees for your transaction. Property taxes and homeowner's insurance are estimates and subject to change.  The Total Monthly Payment does not include the estimated HOA/Common Charge payment.