Manchester Homes with Guest Quarters Exterior Features

Welcome to Manchester, Vermont, a picturesque town nestled in the heart of Bennington County, where the charm of New England meets the beauty of the Green Mountains. Renowned for its stunning landscapes, vibrant arts scene, and rich history, Manchester is the perfect place to call home. With its quaint downtown filled with unique boutiques, artisanal eateries, and cultural attractions, residents enjoy a lifestyle that blends small-town warmth with modern conveniences.

One of the standout features of homes in Manchester is the availability of properties with guest quarters. These homes are designed to accommodate friends and family, providing a welcoming space for visitors while ensuring privacy and comfort. Imagine hosting gatherings in your spacious backyard, complete with a lovely patio, while your guests enjoy their own cozy retreat just steps away.

The exterior of these homes often showcases classic Vermont architecture, with charming details such as clapboard siding, covered porches, and beautiful landscaping that enhances the natural beauty of the surroundings. Many properties are set against a backdrop of lush greenery, offering breathtaking views of the mountains and easy access to outdoor activities like hiking, skiing, and fishing.

Living in Manchester means embracing a vibrant community spirit, with local events, farmers' markets, and seasonal festivities that bring neighbors together. Whether you're seeking a year-round residence or a seasonal getaway, Manchester's homes with guest quarters offer the perfect blend of comfort, style, and functionality in a truly enchanting setting. Come experience the magic of Manchester, where every day feels like a retreat!

Newest Manchester Homes with Guest Quarters Exterior Features

$3,900,000

5 Beds ⋅ 7 Baths ⋅ 5096230 MLS

Set on more than 18 picturesque acres along desirable River Road in Manchester Village, this extraordinary, converted farm offers a rare blend of historic character, modern comfort, & endless possibilities. Thoughtfully transformed into a multi-use residential compound, the property features four distinct living, working, & entertaining spaces, each with its own personality and purpose. Throughout the property, authentic antique details have been carefully preserved & integrated into the design. Original barn doors, handcrafted woodwork, exposed beams, & custom trim accents create a warm & inviting atmosphere while seamlessly blending with modern updates & amenities. The former horse barn stalls have been creatively reimagined into a charming office, library, & 3/4 bath, providing an inspiring space for work, study, or quiet retreat. A covered walkway leads to an impressive barn, ideal for large gatherings, celebrations, creative pursuits, or even a prized car collection.. A third living area serves as an exceptional landing place for family, guests, or multigenerational living. Barn-inspired architectural elements continue throughout, complemented by multiple bedrooms, and bathrooms, Completing the compound is a separate one-bedroom cottage, offering privacy & flexibility for guests, caretakers, or your personal slice of serenity. Outside, the grounds are equally captivating. Mature plantings & meticulously maintained landscaping showcase several perennial gardens that bloom throughout the seasons. A heated in-ground pool provides the perfect place to relax. Across the street, additional acreage framed by classic Vermont stone walls and a large stream-fed pond adds another dimension to the estate, with space for future residences, guest accommodations, or a private family compound. A truly exceptional offering in the heart of Historic Manchester Village.

2236 River Rd, Manchester

$1,795,000

6 Beds ⋅ 6 Baths ⋅ 5086670 MLS

“The Colonial” – Queen of Taconic Avenue One of the original summer “cottages” gracing historic Taconic Avenue, The Colonial is a crown jewel of Manchester Village. Painstakingly renovated, this stately home perfectly balances old-world charm with modern sophistication. The heart of the home is a stunning new chef’s kitchen, seamlessly blending timeless design with today’s comforts. All-new windows, updated electrical and plumbing, and thoughtful improvements throughout breathe new life into this historic residence while preserving its character and grace. The first floor offers multiple inviting sitting areas, a formal dining room ideal for gatherings, and elegant spaces for entertaining. Upstairs, the second floor features four beautifully appointed bedrooms and three fully renovated bathrooms, including twin en-suites. The master suite is highlighted by a spa-inspired bath, complete with a soaking tub overlooking the majestic slopes of Mount Equinox. A versatile third floor offers additional guest rooms or flexible living space. Outdoors, the wraparound porch—often called the finest sitting porch in Manchester Village—sets the stage for warm summer evenings, conversation, and al fresco dining. A detached carriage house provides further opportunity as a private in-law apartment or a spacious work-from-home retreat. Steeped in history yet fully renewed for modern living, The Colonial is a true gem in the heart of Manchester Village. Homes of this caliber rarely come to

144 Taconic Rd, Manchester

$4,995,000

9 Beds ⋅ 10 Baths ⋅ 5063499 MLS

Peacock Hollow, a c.1790 completely private estate, is gracefully sited on 29.9 acres surrounded by sweeping mountain views, a running stream, and bordered by the forest. This rare offering combines historic character with refined updates, creating a legacy property designed for both intimate living and grand entertaining. The 5,500 square foot main residence offers five beautifully appointed bedrooms, five fireplaces, original wood and marble floors, and handsome moldings throughout. The home has been thoughtfully expanded to include a sun-filled country kitchen with custom cabinetry, formal and informal dining rooms, a library, family room, and multiple living spaces that open to marble terraces and gardens. Enhancing the estate are extraordinary amenities, including a marble in-ground swimming pool with stone terrace, a tennis court, and a one-bedroom caretaker’s cottage with attached garage for on-site management or guest overflow. A 2,400 square foot three-bedroom guest house, created from the original c.1796 post-and-beam barn, blends historic charm with modern comfort. A goat and chicken barn, equipment barn, and a separate 30’ x 60’ seven-bay toy and car barn provide abundant storage and the opportunity for a true Vermont farmstead lifestyle or a spectacular car collection. The grounds are equally captivating, featuring mature landscaping, open meadows, orchards, perennial gardens, and stone walls. Pergolas, walkways, and extensive marble terraces.

1182 1184 East Manchester Rd, Manchester

Start Your Search

board logo Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated .