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You are viewing Chester VT Homes between $1000000 and $99999999 dollars. You can change listings price from to do not use $ or , in amounts Switch to Land in Chester VT Condos in Chester VT Multi Family in Chester VT Commercial Listigs in Chester VT
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CHESTER VT Home for sale $$1,200,000 | $363 per sq.ft.

$1,200,000 | $363 per sq.ft. CHESTER VT HOME FOR SALE New Listing!

76 Goldthwaite Road 4 Beds | 3 Baths | Total Sq. Ft. 3308 | Acres: 7.8

Experience the Vermont lifestyle in this beautifully renovated 1864 Brick Federal-style farmhouse set on 7.8 private acres just minutes from town. Rich in historic character and thoughtfully updated for modern living, this exceptional property offers the perfect blend of comfort, charm, and year-round recreation. Inside, you'll find four spacious bedrooms, wide plank wood floors, and inviting gathering spaces designed for relaxed country living. The heart of the home is the warm and welcoming country kitchen featuring soapstone counters, a center island, and ample room for entertaining. A large living room with a pellet stove creates a cozy retreat after a day on the slopes or trails, while the den offers an ideal space for a home office or quiet study. The screened front porch captures the essence of Vermont living -- perfect for morning coffee, evening conversations, and taking in the peaceful surroundings. Outdoors, enjoy evenings around the firepit beneath star-filled skies, surrounded by the natural beauty and privacy of the property. A standout feature is the remarkable multi-level 55' x 40' barn, full of rustic character and endless potential. Having hosted countless gatherings and celebrations, it offers incredible space for entertaining, hobbies, storage, or future creative use. Tucked away just two miles from town, this serene retreat offers both privacy and convenience, with easy access to skiing, snowmobiling, hiking, and all the outdoor adventure and small-town charm that make Vermont so special. See MLS Property & Listing Details & 39 images. Includes a Virtual Tour

CHESTER VT Home for sale $$1,690,000 | $313 per sq.ft.

$1,690,000 | $313 per sq.ft. CHESTER VT HOME FOR SALE

1302 Popple Dungeon Road 5 Beds | 5 Baths | Total Sq. Ft. 5400 | Acres: 18

Set on 18 private acres, Popple Dungeon is a distinctive Vermont property offering the feel of a true country retreat. Owned by one family and designed and built by its owner, the Williamsburg-style reproduction Saltbox reflects a deep appreciation for traditional craftsmanship and enduring design. Inside, the home is defined by warm, handcrafted details--wide-plank wood floors, paneled walls, layered moldings, and reclaimed beams create a sense of comfort and authenticity throughout. The scale and layout offer a balance of inviting gathering spaces and quieter rooms, well-suited for both everyday living and hosting. Originally operated as a bed-and-breakfast, the home was thoughtfully designed to welcome guests while maintaining a natural flow and sense of privacy. The surrounding land provides a peaceful and private setting, with stone walls, established gardens, wildflowers, fruit trees, and a blueberry patch woven into the natural landscape. Open areas and wooded sections create a property that feels both curated and comfortably natural, offering space to explore, relax, and enjoy Vermont's changing seasons. A guest house and dedicated woodworking barn add to the property's appeal, offering flexibility for hosting, hobbies, or creative pursuits. Ideally located near the charming village of Chester, the property offers convenient access to year-round outdoor recreation, including skiing, hiking, biking, fishing, and scenic trails. Throughout the home, the builder's attention to detail is unmistakable, with thoughtfully crafted custom woodwork and timeless finishes that reflect a genuine commitment to quality and design. Quiet, private, and rooted in tradition, this is a property well suited for those seeking a classic Vermont retreat and lifestyle. See MLS Property & Listing Details & 53 images. Includes a Virtual Tour

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Town & Country Realty Claremont 26 Tremont Street Claremont, NH 03743 Telephone (603) 542-5188 (800) 542-5188 Fax (603) 542-6873 info@townandcountryrealty.com	Check out Town & Country Realty Assoc on Yelp	Town & Country Realty Ascutney PO Box 280 Rte 5 Ascutney, VT 05030 Telephone (802) 674-6311 (800) 542-5188 Fax (603) 674-6120 vtinfo@townandcountryrealty.com
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Chester Vermont MLS Listings Homes For Sale

You are viewing Chester VT Homes between $1000000 and $99999999 dollars.

$1,200,000 | $363 per sq.ft. CHESTER VT HOME FOR SALE New Listing!

$1,690,000 | $313 per sq.ft. CHESTER VT HOME FOR SALE