Wayside Inn Historic District Homes for Sale

Welcome to the enchanting Wayside Inn Historic District, a gem nestled in the heart of Sudbury, Massachusetts. Rich in history and charm, this unique subdivision offers a delightful blend of old-world elegance and modern convenience. The Wayside Inn, established in 1716, is not just a landmark; it’s a testament to the area’s storied past and vibrant community spirit. As you stroll through the picturesque streets, you’ll be captivated by the stunning architecture, lush landscapes, and the sense of tranquility that permeates this historic enclave.

The Wayside Inn Historic District is more than just a beautiful setting; it’s a community where neighbors become friends and history comes alive. With its proximity to the Sudbury River and numerous parks, residents enjoy a plethora of outdoor activities, from scenic walks to leisurely picnics. The local schools are highly regarded, making this area an ideal choice for families looking to settle in a nurturing environment.

Currently, there are charming homes for sale in this coveted district, each offering a unique character and a slice of history. From beautifully restored colonial homes to modern residences that respect the area’s heritage, there’s something for everyone. Imagine living in a place where every corner tells a story and each day unfolds with the promise of new adventures.

If you’re seeking a home that combines historical charm with contemporary comforts, the Wayside Inn Historic District in Sudbury is the perfect destination. Explore the available properties today and become part of this extraordinary community!

Newest Wayside Inn Historic District Homes for Sale

$2,495,000

4 Beds ⋅ 4 Baths ⋅ 73571809 MLS

Once in a blue moon, an estate comes to market that is truly unlike anything else. Custom built and set amid magnificent gardens inspired by the landscapes of Europe, Japan, and Morocco, 82 Old Garrison Road in Sudbury is a remarkable expression of architecture, artistry, and nature. Reimagined and reconstructed in 2004, this architecturally distinctive contemporary estate offers four bedrooms, four baths, and more than 4,500 square feet of living space, privately set on approximately five beautifully cultivated acres. Designed to create a seamless connection between indoors and out, the home unfolds through light-filled living spaces, walls of glass, and unexpected architectural moments, each framing a different view of the surrounding landscape. At the heart of the property are gardens cultivated over many years as a true labor of love. Meandering paths lead through an ever-changing landscape of specimen plantings, perennial gardens, tranquil water features, intimate gathering spaces, a small orchard, and a greenhouse. Around each turn is something new to discover, creating an experience that feels worlds away while remaining in the heart of Sudbury. The grounds are equally suited to relaxation and entertaining, with an in-ground pool surrounded by lush plantings and multiple outdoor spaces that invite long afternoons, quiet mornings, and memorable gatherings beneath the open sky. Inside, the home is warm, sophisticated, and wonderfully individual. Expansive windows bring the gardens into nearly every room, while thoughtfully designed living and entertaining spaces reflect the same creativity found throughout the grounds. The flexible layout provides versatile accommodations for residents and guests, complemented by distinctive spaces for dining, gathering, working, and retreat. A three-car garage, whole-house generator, metal roof, warm cedar-shingle exterior, and expansive ipe decking add substance and practicality. Set within Sudbury’s storied Wayside Inn Historic District, the property feels remarkably removed while remaining connected to the heart of town. More than a home, 82 Old Garrison Road is a private world unto itself, shaped by imagination and an extraordinary appreciation for beauty. For the discerning buyer seeking privacy, originality, and a property that simply cannot be replicated, this is a rare opportunity to become the next steward of one of Sudbury’s most distinctive estates.

82 Old Garrison Rd, Sudbury

Listing courtesy of Listing Agent: Peace Nguyen from Listing Office: Engel & Volkers Wellesley.

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