Under 500k

MLS Number 5095551

• Residential Single Family
• Full Bath 2
• Address 81 Main Street
• Construction Existing
• Bedrooms 5

Step into a piece of Chester's history with this sprawling Folk Victorian offering over 3,800 square feet of living space, five bedrooms, and four bathrooms. Rich in character and architectural detail, this home offers the space and flexibility to accommodate a variety of lifestyles. Inside, you'll find generously sized rooms throughout, including a spacious living room anchored by a wood-burning fireplace and a large entertainment room complete with a wet bar, creating an ideal setting for gatherings, celebrations, or relaxing at home. The thoughtfully designed primary suite features a beautiful en-suite bathroom, while first-floor laundry adds everyday convenience. The flexible floor plan provides abundant space for family, guests, remote work, hobbies, or multi-generational living. Outside, a paved driveway leads to a detached one-car garage, and the level backyard offers plenty of room for recreation, gardening, pets, or outdoor entertaining. Mature trees and established landscaping create a natural buffer from the road, providing a sense of privacy while remaining just moments from Chester's village amenities, shops, restaurants, and community events. Combining historic character, generous living space, and a highly desirable location, this is a rare opportunity to own one of Chester's classic homes. Conveniently located just minutes from I-91 and within easy reach of Okemo Mountain Resort, Magic Mountain, Bromley Mountain, Stratton Mountain, and other Southern Vermont outdoor destinations, this property offers year-round access to skiing, hiking, recreation, and travel throughout the region.

Listed by Betsy Adamovich of Real Broker LLC

MLS Number 5101598

• Condo
• Square Feet 1,483
• Bedrooms 2
• New Contruction Existing
• Complex Meadow Mist

Step into ease and comfort at 13 Clover Lane, an end-unit townhome in Hinesburg’s Meadow Mist community. A zero-step entry welcomes you into the bright, open main living space, where natural light fills the living and dining areas. The kitchen features energy-efficient appliances and flows seamlessly for effortless everyday living. Just off the main hall is the primary bedroom and a full bathroom with a step-in shower designed for accessible, one-level living. Downstairs, a partially finished lower level offers flexible bonus space: a cozy family room with a Murphy bed, a second bedroom, another full bath with step-in shower, and a generous storage area. Outside protected wetlands provide a peaceful natural backdrop as well as sweeping mountain views. Sidewalks lead you directly to shops, restaurants, and village cafs. Additional highlights include a Lunos whole-house ventilation system, fire sprinklers, an attached garage, and 20 acres of shared common land with a gazebo and playground. Perfect for retirees or anyone seeking an accessible and low-maintenance lifestyle in a vibrant Vermont community. Now vacant and ready for immediate occupancy

Listed by Julie Danaher of Ridgeline Real Estate

MLS Number 5102524

• Residential Single Family
• Full Bath 1
• Address 90 Congress Street
• Construction Existing
• Bedrooms 4

Some homes simply feel like home the moment you step inside, and this is one of them. Spacious, warm, and filled with character, each room feels wonderfully grand while still offering an undeniable sense of comfort and belonging. The inviting front porch sets the tone, offering the perfect place for morning coffee, unhurried conversations, and front porch talks that linger into the evening. Inside, the front parlor welcomes you with a beautiful antique mantel, inviting you to imagine the generations who have entered through the front door. The more commonly used rear entrance opens into a charming room featuring hardwood floors, built-in bookshelves, and a cozy gas stove. Create a personal library, display treasured photographs, or simply enjoy this inviting space as part of your daily comings and goings. The kitchen offers an abundance of custom pantry storage along with peaceful views of the beautifully landscaped backyard. Outside, meandering pathways wind through thoughtfully established gardens, creating a private setting for meditative walks, quiet coffee sits, and moments spent appreciating the changing seasons. The home's generous rooms provide flexibility for gathering, relaxing, working, and creating, while a secret third-floor play space offers a magical place where imaginations can be set free. The basement includes a large workshop where much of the custom craftsmanship found throughout the home was lovingly created. Clearly cherished and carefully maintained, this is a true heartstrings home... cozy, character-filled, and awaiting its next owner to begin a new chapter of memory-making.

Listed by Leigh Horton of Your Journey Real Estate

MLS Number 5100623

• Residential Single Family
• Full Bath 1
• Address 430 Pleasant Heights
• Construction Existing
• Bedrooms 3

This spacious raised ranch, set on an oversized lot, offers privacy, sweeping mountain views, and ample space to spread out. The open kitchen features rich wood cabinetry, an island and a dining area. The kitchen/dining area flow seamlessly to a beautiful living room with windows framing the hillsides. There are Three bedrooms; one with convenient laundry hidden in it. The home features mini split heat pumps, ample closet spaces, and lots of natural light. The lower level is standout. Large, versatile family/game room with wood flooring, a TV mount, and space for a home office or gaming setup. This level offers excellent space for a home theater, gym, or with the right permitting, a guest suite. An oversized attached garage offers room for 3 vehicles, equipment or storage. A dream setup for outdoor enthusiast of all kinds. The level grassy yard features a long driveway leading up from the road, offering both a sense of privacy and a beautiful view. With easy access to Rutland & Killington, this property combines quiet country living, with everyday convenience. Snowmobile and ATV trails are just minutes away, take advantage of the area hunting, fishing, skiing, and hiking. The garage's extra depth makes it easy to store your toys, tools, or a workshop setup. Perfectly updated, whether you're upsizing everyday life or looking for a basecamp for your adventures. This home delivers space, private outdoor areas, and beautiful Vermont views.

Listed by Leo Pond of Four Seasons Sotheby's Int'l Realty

MLS Number 5089210

• Residential Single Family
• Full Bath 2
• Address 100 Derby Gore Road
• Construction Existing
• Bedrooms 3

Tucked well back from the road on 5 lovely acres, this well cared for original-owner log home offers the privacy and country setting buyers are searching for while still being just minutes from Derby's in-town conveniences. Built in 2002, the home enjoys lovely sunset views and a beautifully landscaped setting featuring stone walls, flower beds, patios, decks, apple trees, and a fenced raised-bed vegetable garden. Inside, the main level offers a warm and inviting layout with an open kitchen and dining area flowing into a gracious living room, along with a relaxing 3-season porch to enjoy the surrounding scenery. The main floor also includes a room currently used as an office that could serve as a bedroom, plus direct access to the attached sugar house where you can make your own maple syrup. A full bath and additional half bath complete the main level. Upstairs you'll find two bedrooms and a central bath, while the full unfinished basement provides excellent storage, workshop space, or future finishing potential. Gardeners and homesteaders will appreciate the greenhouse with prime southern exposure, allowing you to extend the growing season well beyond summer. Additional outbuildings include a substantial 5-bay garage/shed with four bays in front and one in the rear for equipment, vehicles, and toys, plus another detached shed ideal for workshop or garden storage space. The driveway is shared initially but becomes private as you approach the home. The neighboring motocross track also offers weekend racing events for those who enjoy motorsports or outdoor recreation. Enjoy the best of Vermont country living with nearby lakes, skiing, snowmobiling, ATVing, hiking, and everyday amenities all within easy reach.

Listed by Nicholas Maclure and Howard Birchard of Century 21 Farm & Forest