Properties Near 466 Wheeler Road Windham, VT

Located in the heart of downtown Jamaica, Vermont, this spacious and beautifully designed Colonial home offers the perfect blend of charm, comfort, and convenience. With 5 bedrooms and 5 bathrooms, there’s plenty of space for a large family or frequent guests. Just minutes from premier ski resorts—Stratton, Bromley, and Magic Mountain—this home is an ideal base for winter and summer adventures. Step into the welcoming new mudroom, complete with cubbies and large window with bucholic views, then gather around one of the home’s inviting gas fireplaces for après-ski dining or relaxing winter nights. In the summer, enjoy cool comfort with central air and stroll to the local market, library, or take a scenic walk to Jamaica State Park. The renovated kitchen, along with updated furnaces and hot water tanks (2021), offer modern ease in a classic setting. The versatile third floor includes a full bathroom and endless potential for work, storage or play. A small barn is ready for your imagination—studio, office, garage or recreation room—plus a handy storage shed and an EV charging station complete this must-see Vermont retreat! Come explore the best of Vermont living—come home to Jamaica! This property has its own septic tank with a shared leach field. Road frontage and acreage are estimated.

This lovely, updated 1790 Cape blends timeless New England charm with modern functionality and post-and-beam construction. Ideally located just outside the quaint village of Jamaica, the home offers easy access to four major ski resorts—Stratton, Bromley, Magic Mountain, and Mount Snow. Step into the welcoming kitchen, where a cozy fireplace creates a perfect winter haven. A soaring cathedral ceiling adds an airy feel, while the adjacent breakfast nook, framed by expansive backyard views, is ideal for year-round dining. The spacious living room is bathed in natural light and anchored by a working fireplace, offering a warm and inviting atmosphere. A convenient first-floor bedroom and nearby handicap-accessible bathroom make single-level living an option. At the same time, the laundry room at the end of the hall adds to the home's functionality. Upstairs, you'll find two additional bedrooms and a cozy office. A charming two-bedroom apartment with a soaring ceiling, wood stove, and skylights sits above the oversized garage, easily fitting three vehicles. Whether used as guest quarters, an in-law suite, or a rental unit, it offers exceptional flexibility and added value. The property includes two lots: the main house rests on nearly an acre, with an adjacent lot of almost the same size directly to the north. If looking for a full-time residence, a seasonal getaway, or a rental investment, this property delivers!

This 3-bedroom 2-bath Chalet is quietly nestled on 2.6 acres in the heart of Vermont’s ski country. The upper level has a wonderful, spacious kitchen, with an open floor plan combining the dining area and living room, with wood-burning fireplace, has access to the the wrap around deck. One bedroom with a walk-in closet is also on the upper level. The lower level boasts 2-bedrooms, a full bath, and a family room with another wood burning fireplace. This home has been well maintained and was recently renovated throughout. Schedule a showing today!

Charming and meticulously maintained, this classic Vermont A-frame with a tasteful addition offers the perfect blend of character and comfort. Nestled on just under 2 acres, the home features 3 cozy bedrooms, warm wood accents, and inviting living spaces filled with natural light. Whether you're enjoying a quiet morning on the deck or taking in the peaceful surroundings, this property is a true Vermont retreat. Located in Windham, a quaint village rich in history and natural beauty, you'll find yourself in the heart of Southern Vermont. Established in the 18th century, Windham is known for its rolling hills, outdoor recreation, and close-knit community. A rare gem in a timeless setting!