Charleston Real Estate

Welcome to Charleston, a picturesque town nestled in Orleans County, Vermont. Known for its small-town charm and stunning natural beauty, Charleston offers a peaceful and idyllic setting for those looking to escape the hustle and bustle of city life.

With its close-knit community and welcoming atmosphere, Charleston is the perfect place to call home. Residents here enjoy a slower pace of life, where neighbors know each other by name and a strong sense of community pride abounds.

Nature lovers will delight in the abundance of outdoor recreational opportunities that Charleston has to offer. From hiking and biking trails to fishing and boating on nearby lakes and rivers, there is no shortage of ways to enjoy the great outdoors in this scenic town.

Charleston is also rich in history, with historic buildings and landmarks waiting to be explored. Take a stroll through the charming downtown area, where you'll find quaint shops, cozy cafes, and friendly locals eager to share the town's stories.

Whether you're looking to settle down in a peaceful rural setting or simply seeking a weekend retreat, Charleston has something for everyone. Come and discover the beauty and charm of this hidden gem in Vermont's Orleans County.

Newest Listings in Charleston

$190,000

3 Beds ⋅ 1 Baths ⋅ 5100819 MLS

Welcome home to this charming 3-bedroom, 1-bath home nestled on a beautiful half-acre lot with frontage along the picturesque Clyde River. Whether you're looking for a peaceful place to call home or a cozy Vermont retreat, this property offers the perfect blend of comfort and convenience. Inside, you'll find an open concept family room that flows seamlessly into the dining and kitchen, ideal for gathering with family and friends! The full bathroom also includes a convenient laundry area on the first floor, making everyday living easy. The unfinished basement offers plenty of storage. With both interior and exterior access, it's as functional as it is versatile. Outside, enjoy the beauty of your riverside setting, complete with a large storage shed for all your tools, toys, and outdoor equipment. The generous yard provides plenty of room for gardening, entertaining, or simply relaxing while taking in the peaceful surroundings. Located in the small town of West Charleston, you're just minutes from I-91, shopping, dining, schools, and other everyday conveniences, while still enjoying the tranquility of country living. Don't miss your chance to own this delightful Vermont property with river frontage and room to make it your own!

969 Vt Route 105, Charleston

$72,500

5099477 MLS

Paradise Lane – The Name Says It All Welcome to your own piece of Vermont's Northeast Kingdom. This beautiful property on Paradise Lane in East Charleston offers the perfect setting for a cabin, vacation getaway, or year-round home surrounded by nature, privacy, and spectacular scenery. With abundant wildlife, peaceful forests, and easy access to the region's best outdoor recreation, you'll enjoy the best of Vermont living in every season. Nearby Attractions Lake Willoughby approximately 2 miles Echo Lake approximately 3 miles *Island Pond approximately 6 miles Kingdom Trails approximately 20 miles Northwoods Stewardship Center approximately 5 miles Canadian Border approximately 20 miles Watch for moose, deer, black bears, wild turkeys, eagles, and countless songbirds right from your property. Spend your days hiking, biking, fishing, kayaking, snowmobiling, skiing, or simply relaxing in one of Vermont's most scenic and unspoiled regions. Paradise Lane the name says it all If you've been searching for peace, privacy, and endless outdoor adventure, this is where your Vermont dream begins.

224 Paradise Ln, Charleston

$385,000

3 Beds ⋅ 2 Baths ⋅ 5094156 MLS

Nestled among rolling countryside and surrounded by open agricultural landscapes, this charming raised ranch offers 10 acres of Vermont serenity with exceptional privacy and unobstructed rural scenery. Located in Charleston, this property provides a rare opportunity to enjoy a peaceful and tranquil setting. A generous entryway creates a practical transition into the residence while offering convenient access to the lower level, attached two-vehicle garage, and main living quarters. Upstairs, the thoughtfully arranged floorplan features an inviting kitchen space combined with an adjoining eating area, perfect for gatherings or everyday routines. Expansive windows throughout the central family room allow sunlight to pour inside, creating a bright and welcoming atmosphere. The sleeping quarters include a comfortable primary bedroom along with two additional bedrooms creating accommodations suitable for visitors, hobbies, remote employment, or growing households. A full bath finishes the upper floor and includes washer and dryer connections for added convenience. Downstairs, a versatile unfinished area presents numerous possibilities. With separate exterior access, laundry hook-ups, and another full washroom, the space could support entrepreneurial ventures, extended household arrangements, recreation, creative pursuits, or future customization to suit evolving needs. Outside, the acreage offers room for gardening, outdoor activities, animals, equipment, or simply appreciating the surrounding beauty. Additional highlights include a storage outbuilding, 200-amp electrical service, drilled well, onsite wastewater system, paved parking area, front deck, plus direct VASA trail accessibility for outdoor enthusiasts. ** NEW ROOF **

504 Fontaine Rd, Charleston

$714,900

3 Beds ⋅ 3 Baths ⋅ 5092047 MLS

Set on 48 acres with a private pond and miles of trails, this Charleston property delivers the full Northeast Kingdom lifestyle. The 3 bedroom home has been meticulously cared for, with recent updates including new floors, new windows, kitchen improvements, and a newer furnace—giving buyers peace of mind and move in comfort. The open floor plan is ideal for gatherings, complemented by 3 bathrooms, a finished basement, and a partially finished studio apartment above the garage that’s perfect for guests, rental potential, or extra space to spread out. The land includes a greenhouse and a classic sugarshack, along with a friendly agreement that allows a local producer to tap the maple trees without adding work for the homeowner. Outdoor enthusiasts will appreciate direct access to the snowmobile trail system right from the property. Located just minutes from Lake Willoughby, a short drive to Newport’s shopping, dining, and Lake Memphremagog, and conveniently positioned between Jay Peak and Burke Mountain for world class skiing, this is a rare opportunity to own a versatile, four season retreat offering privacy, recreation, and true Vermont character.

1688 Vt Route 5a, Charleston

$498,800

6 Beds ⋅ 5 Baths ⋅ 5088299 MLS

One of the most spectacular properties in the Northeast Kingdom. Built by master carpenter Daniel Lamadeleine, the property features not just one but two beautiful homes on a gorgeous, level ten-acre wooded lot including a three-and-a-half-acre meadow, a beautiful stream and pond potential. 673 is a stunning structure, a modern 2BR+ twin lofts, handcrafted kitchen, dining area and a family room looking out over the meadow and an especially unusual Dr. Seussian leaning pine. Over the gorgeous chef's kitchen, check out the insanely hip winch-powered, open-frame elevator for access to the western loft. The ground floor includes a massive pine floor and pine wall L-shaped open studio, a floor-to-ceiling window potential office and a half bathroom. 675 is a traditional 4BR cape that has been used as a rental to significantly offset carrying costs and property taxes. A soaking tub and secret ground-floor bedroom closet appears to be just a bookcase. This rare mix of stunning homes and prime property with an occupancy-ready rental cottage offers utilitiy, style and investment appeal. Poised to launch the artist, craftsperson, micro-farmer or urbanite looking to get away from it all. Dazzle guests. Raise chickens, lambs, pigs or build an equestrian riding ring and farm barn. Ski Burke, Jay Peak and paddle the NEK ponds and lakes including nearby majestic Lake Willoughby. Paradise. The 2,964 square feet are for both homes finished square footage combined and the Barn house likely has considerably more finished square footage than is stated on the lister card.

675 Sanderson Hill Rd, Charleston

$434,000

3 Beds ⋅ 2 Baths ⋅ 5087854 MLS

Set on 10.10± acres, this inviting 3-bedroom, 2-bath home offers comfortable living along with an exciting opportunity for added value and future development. The home features a functional layout, spacious mudroom ideal for Vermont living, and an attached 2-car garage with additional storage above. A standout feature of the property is the potential for a separate 2± acre building lot, already equipped with its own septic system and electrical service. The lot could be ideal for building a new home, guest accommodations, an investment property, or future family use. The seller is offering the opportunity to purchase the building lot separately for $50,000, subject to subdivision approval. The lot shares the existing drilled well with the main residence. Prefer to keep the entire property? Purchase all 10.10± acres and enjoy the flexibility to develop the additional lot in the future or potentially generate rental income. Subdivision is required prior to a separate sale of the building lot. Whether you're looking for acreage, a comfortable Vermont home, an investment opportunity, or the flexibility to secure a future building site, this property offers possibilities rarely found at this price point.

93 Carpenter Blvd, Charleston

$69,000

5084113 MLS

10.1 acre rural parcel in West Charleston, VT with paved road frontage on Dane Hill Rd. Soil report is available and the property is suitable for a septic system. Electricity available at the street through Barton Electric. Needs well and septic. Low annual taxes of just $696. A clean, straightforward parcel in a quiet Vermont setting ideal for a primary residence, seasonal retreat, or investment.

2840 Dane Hill Rd, Charleston

$295,000

1 Beds ⋅ 1 Baths ⋅ 5059945 MLS

Motivated sellers invite you to bring your vision and complete this unique log cabin retreat on 10.1 private acres in Charleston, Vermont. Tucked away at the end of a secluded private drive, this property offers the peace, privacy, and North Country charm that are increasingly hard to find. The cabin is already well on its way to becoming the ultimate four-season getaway. A wraparound porch and private bedroom balcony overlook the surrounding woods, while the cathedral ceiling creates an inviting atmosphere for relaxing after a day outdoors. Fully off-grid with solar power, battery storage, and a propane generator, providing modern comforts in a truly secluded setting. Adventure begins right outside your door with direct access to VAST and VASA trails, making it easy to explore some of Vermont's premier snowmobile and ATV trail networks. A 2-car garage beneath the home and an oversized carport provide ample space for storing snowmobiles, ATVs, UTVs, and all your outdoor gear. A generous supply of building materials will convey with the sale, giving the next owner a valuable head start on bringing their plans to life. Just a short drive from Island Pond and local amenities, yet surrounded by nature, this property offers a rare opportunity to create a custom retreat tailored to your needs. Whether you're seeking a recreational basecamp, seasonal escape, or private off-grid haven, the groundwork is already in place. Sellers are motivated and ready to consider offers.

2569 10 Mile Square Rd, Charleston

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