Date of Publishing: May 23, 2025

Nestled in the heart of Cape Cod’s most sought-after locale, 15 Windy Hill Way presents an extraordinary opportunity in Chatham Real Estate. This exquisite residence offers a perfect blend of classic New England charm and modern luxury, all just steps away from Stage Harbor and the local Yacht Club. Designed with entertaining and relaxed coastal living in mind, this home is a rare gem on the market that promises a lifestyle of comfort, privacy, and elegance.

15 Windy Hill Way A Stunning Coastal Retreat in the Heart of Chatham Asking 6.75 Million 1

Spacious and Inviting Living Spaces

At over 5,600 square feet, 15 Windy Hill Way provides an expansive layout that perfectly balances openness with intimacy. The interiors boast soaring ceilings and rich hardwood floors that extend throughout the main living areas, filling the home with natural light. Whether you’re hosting a lively gathering or enjoying a quiet evening, the family room’s fireplace sets a cozy tone while the living room offers a sophisticated space to unwind.

15 Windy Hill Way A Stunning Coastal Retreat in the Heart of Chatham Asking 6.75 Million 4

15 Windy Hill Way A Stunning Coastal Retreat in the Heart of Chatham Asking 6.75 Million 5

Timothy P. Bailey, the listing agent from John C Ricotta & Associates, notes, “This home’s design seamlessly integrates indoor and outdoor living, making it ideal for both entertaining and family life. Every detail has been thoughtfully curated to reflect the coastal lifestyle that Chatham is known for.”

15 Windy Hill Way A Stunning Coastal Retreat in the Heart of Chatham Asking 6.75 Million 6

15 Windy Hill Way A Stunning Coastal Retreat in the Heart of Chatham Asking 6.75 Million 7

SEE MORE: A Masterpiece of Modern Luxury and Timeless Elegance: Massachusetts Home Priced at $21 Million

Gourmet Kitchen and Elegant Dining

The heart of the home is undeniably the gourmet kitchen, outfitted with granite countertops, abundant cabinetry, and a spacious island that invites both culinary creativity and casual dining. A bright breakfast nook with a picture window provides scenic views while accommodating an eight-seat table, perfect for morning coffees or intimate meals. Adjacent to the kitchen, the formal dining room offers an elegant setting for more sophisticated occasions.

15 Windy Hill Way A Stunning Coastal Retreat in the Heart of Chatham Asking 6.75 Million 8

This residence also features a finished basement with a full bath, adding versatility and space for activities or guest accommodations. The careful attention to detail throughout the home ensures every area serves both function and style, meeting the needs of modern homeowners.

15 Windy Hill Way A Stunning Coastal Retreat in the Heart of Chatham Asking 6.75 Million 9

15 Windy Hill Way A Stunning Coastal Retreat in the Heart of Chatham Asking 6.75 Million 10

SEE MORE: Exquisite Shingle-Style Estate in Massachusetts Asks $9.5 Million for Timeless Elegance and Modern Comfort

Outdoor Living and Waterfront Access

Outdoor enthusiasts will be captivated by the sizable deck overlooking the private swimming pool and hot tub — perfect for summer gatherings or tranquil evenings under the stars. The rooftop deck, often referred to as a widow’s walk, offers breathtaking water views that capture the essence of coastal living. Additionally, the property boasts deeded access to a secluded stretch of Stage Harbor Beach, allowing residents to enjoy quiet moments by the water with ease.

15 Windy Hill Way A Stunning Coastal Retreat in the Heart of Chatham Asking 6.75 Million 3

“As a specialist in Chatham Real Estate, I can say properties like this seldom come on the market,” Timothy Bailey shares. “The combination of water access, luxurious amenities, and location near town makes this a truly exceptional offering.”

SEE MORE: A Coastal Masterpiece: Modern Island Living Awaits in Massachusetts for $10,995,000

A Prime Location in Cape Cod

Situated on nearly one acre, 15 Windy Hill Way benefits from a serene in-town location with convenient access to shopping, dining, recreational facilities, and major highways. The proximity to the Yacht Club enhances the appeal for boating enthusiasts, while the nearby walking loops invite exploration of Chatham’s natural beauty. The area’s excellent schools and community amenities also make this property a perfect choice for families seeking a refined coastal lifestyle.

15 Windy Hill Way A Stunning Coastal Retreat in the Heart of Chatham Asking 6.75 Million 11

This home was built in 2007 and thoughtfully remodeled in 2015, ensuring that it combines classic charm with contemporary updates and energy-efficient systems. Its architectural style with shingle siding and pitched wood roof blends seamlessly into the New England coastal environment, reflecting a timeless aesthetic.

Discover 15 Windy Hill Way Today

Whether you are searching for a seasonal retreat or a year-round residence, 15 Windy Hill Way stands out in the competitive Massachusetts Real Estate market as a property that delivers both elegance and practical living. With five bedrooms and six baths, ample parking, and top-tier amenities, this home offers a lifestyle of luxury and convenience that few can match.

15 Windy Hill Way A Stunning Coastal Retreat in the Heart of Chatham Asking 6.75 Million 12

Timothy P. Bailey concludes, “This estate offers an unmatched blend of privacy, location, and luxurious living spaces. It’s truly a unique opportunity for buyers looking to invest in Cape Cod’s premier coastal community.”

For those interested in exploring this exceptional property, further details and scheduling a private tour are available via the Zillow. Connect with Timothy P. Bailey and his team at John C Ricotta & Associates to discover all that this remarkable home has to offer.

* This property might not for sale at the moment you read this post; please check property status at the above Zillow or Agent website links*