About this home

Welcome to 2037 Main Road, an extraordinary waterfront home on historic Westport Point where American history, timeless New England architecture, and an exceptional coastal lifestyle come together. Originally built in 1776, this remarkable residence has been thoughtfully updated while preserving the character and craftsmanship that make historic homes so special.Perfectly sited to capture breathtaking sunsets, the property overlooks the harbor with panoramic water views and features a private dock, making it easy to enjoy boating, kayaking, fishing, or simply relaxing by the water. Inside, the home is rich with historic charm, featuring wide plank hardwood floors, exposed hand-hewn beams, original woodwork, fireplaces, and period architectural details that reflect nearly 250 years of history. A thoughtfully designed addition blends seamlessly with the original home while expanding the living space and taking full advantage of the stunning waterfront setting. Large windows frame spectacular harbor views from both the first and second floors, filling the home with natural light and creating an effortless connection between the indoors and outdoors.The renovated kitchen complements the home's historic character while offering the functionality and conveniences today's homeowners appreciate. Throughout the home, pride of ownership is evident, with numerous improvements including owned solar panels, Pella windows, a newer roof, updated heating system, generator, and newer septic system, allowing you to enjoy the beauty of a historic property with the peace of mind of modern updates.Adding to the property's appeal is a charming detached cottage filled with rustic character. Ideal for guests, a home office, artist's studio, or private retreat, it offers incredible flexibility while maintaining the authentic coastal feel of the property.The beautifully landscaped grounds feature mature gardens and inviting outdoor spaces, making the most of the manageable lot while creating a peaceful waterfront setting for entertaining or quiet relaxation.Located in the heart of desirable Westport Point, you'll enjoy one of New England's most picturesque waterfronts, just moments from beaches, marinas, conservation land, and local dining. Historic waterfront properties with a private dock, guest cottage, stunning sunsets, and thoughtfully integrated modern improvements rarely become available. This is a unique opportunity to own a true legacy property.

Facts and features

Schools

• Westport Junior/Senior High School

  elementary · 5-12 · 7.3 mi

  5

• St. Vincent's School

  middle · 6-12 · 3.9 mi

• Westport Elementary School

  elementary · 1-4 · 7.4 mi

  6

• Alice A Macomber School

  elementary · K · 9.3 mi

Price history

• Aug 4, 2026 · Price Changed$1,995,000
• Jun 29, 2026 · Listed$2,177,600
• Aug 4, 1988 · Sold$312,500

Tax history

• 2026$11,704 tax · $1,607,700 assessed
• 2024$10,013 tax · $1,295,300 assessed
• 2023$9,782 tax · $1,198,800 assessed
• 2022$8,794 tax · $1,037,000 assessed
• 2021$7,561 tax · $877,200 assessed
• 2020$7,155 tax · $848,700 assessed
• 2019$6,993 tax · $845,600 assessed
• 2018$7,663 tax · $937,900 assessed

Home value

$1,975,000

• Collateral Analytics$1,975,000
• Cotality$1,960,800

Where it is