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

$100,000

3 Beds ⋅ 4 Baths ⋅ 5114458 MLS

Opportunity knocks! This West Charleston fixer upper is priced to reflect its condition and represents a genuine chance to build equity in one of Vermont’s most scenic lake communities, just a quarter mile from fishing and water access on beautiful Echo Lake. The setting alone is worth the drive. Lake, mountain, and countryside views surround the property, delivering the kind of Vermont backdrop that buyers pay a premium for when it comes turnkey. Here, you get the views and the value with the upside of your own sweat equity. Whether you’re a contractor, an investor, or a handy buyer ready to roll up your sleeves, this property offers a rare entry point into a desirable Northeast Kingdom lakeside neighborhood. Echo Lake is a gem, clean, quiet, and beloved by anglers and outdoor enthusiasts. Properties this close to water access at this price point don’t stay available for long. Bring your vision and your tool belt. The hard part is finding the opportunity and this is it. HUD foreclosure, Buyer to verify all information. Pre 1978, possible LBP. Prop avail to Owner Occupants for the first 15 days. HUD Foreclosure, sold as is (UI) Needs to be purchased with a rehab/construction loan or cash. Buyer to verify all data, property sold as is.

91 W Echo Lake Rd, Charleston

$215,000

3 Beds ⋅ 1 Baths ⋅ 5114281 MLS

This charming 3-bedroom Cape offers 1,584 square feet of thoughtfully updated living space, combining modern comforts with warm, rustic character. Recently remodeled throughout, this inviting home features a beautifully renovated kitchen with stainless steel appliances, an updated full bath, new flooring, warm pine walls and ceilings, stylish barn-style doors, and new windows and exterior doors. Enjoy the peace of mind that comes with low-maintenance vinyl siding, a durable metal roof, and full weatherization for efficient heating and year-round comfort. Additional highlights include a dedicated laundry room, attached two-car garage with new doors, a shed and a walk-out lower level. Step outside onto the spacious back deck and take in the peaceful surroundings sitting high above overlooking the picturesque Clyde River. The level backyard offers plenty of room for outdoor enjoyment, gardening, or simply relaxing and taking in the views. Complete with a drilled well, conventional on-site septic system, and access to high-speed Xfinity internet and cable, this property offers a wonderful blend of comfort, convenience, and natural beauty. An exceptional value with so many updates already completed; don't miss your opportunity to make this move-in-ready home your own! Schedule your showing today!

1333 Vermont Route 105, Charleston

$299,000

4 Beds ⋅ 2 Baths ⋅ 5111850 MLS

Country home located on 45 acres in both Derby and Charleston. House is in Charleston. Survey to be completed in October. Tenants to be gone on 12/1/26. Acreage, road frontage and taxes can vary depending on final survey. Classic floor plan with an archway between the kitchen and dining room. 1st floor bedroom and bath. 3 bedrooms and bath on 2nd floor. Full walkout daylight basement under the house and garage. Class 3 road ends at this farm. Rented to 4 single guys currently. Only 2 owners since it was built in 1965. Large glass-enclosed porch across the whole side of the house.

77 Wheeler Rd, Charleston

$500,000

2 Beds ⋅ 2 Baths ⋅ 5111421 MLS

Wow!!! Winterized home directly on a sandy level beach on Echo Lake. Road frontage is estimated. A rare opportunity to become a homeowner on one of the most pristine lakes. About 530 acres and over a mile long. This charming home has had only 2 owners. The first was for over 50 years. This home started as an A Frame and then a large addition added to its living space. 1st floor has a large living room with brick fireplace and open to the kitchen. Large entry and a sun room of sorts that is being used as a bedroom. 3/4 bath here too. 2nd floor has a large office currently used as an office/ bunk room, 2 bedrooms and a 1/2 bath. And, EVERY room except 1 bedroom faces the lake. Both upstairs bedrooms have private balconies. The town says this is a 2 bedroom house. I count 3 to 4.

994 W Echo Lake Rd, Charleston

$197,000

5111012 MLS

Waterfront development opportunity!! Discover the possibilities with this exceptional 1.59-acre parcel offering approximately 390 feet of owned shoreline on beautiful Pensioner Pond in Charleston, Vermont. Whether you're looking for an investment opportunity, future income-producing property, or a special waterfront retreat in Vermont’s Northeast Kingdom, this property offers a unique head start with significant planning already completed. The property is approved for a 4-unit multifamily dwelling, consisting of two 2-bedroom units and two 1-bedroom units. The project has not yet been constructed, allowing the new owner the opportunity to bring the approved plans to life. State-approved plans are already in place for a subsurface leach field and drilled well, taking important steps out of the development process. Adding to the property's potential, the Town of Charleston has no municipal zoning and does not issue town zoning permits, although all applicable Vermont state regulations and permitting requirements still apply. The setting is what truly makes this property stand apart. Pensioner Pond encompasses approximately 170 acres and reaches a maximum depth of 39 feet. Vermont Fish & Wildlife maintains a public fishing access on the pond, and its waters support brook trout, bullhead, chain pickerel, smallmouth bass, and yellow perch. With opportunities for fishing, paddling, boating, wildlife watching, and simply enjoying life along the water, Pensioner Pond provides the classic Northeast Kingdom recreational experience.

2970 Vt Route 105, 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

$674,900

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

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Charleston Real Estate

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