Weston Vermont Real Estate

Showings Start Saturday. OPEN HOUSE SATURDAY October 31 from 1-3 PM. Adorable and perfectly sized for simple country living, this inviting retreat in desirable Weston Heights offers comfort, character, and a wonderful Vermont setting. Tucked back in the woods with open lawn areas for play, a large deck for outdoor enjoyment, and winter views, it is truly a haven in every season. The upper-level living space features a cathedral ceiling, abundant glass, and a corner fireplace anchoring the great room. An efficient galley kitchen opens to the dining and living area, creating an easy flow for everyday living and entertaining. Sleeping quarters are on the lower level, offering separation and privacy, while convenient rear storage adds practicality. Ideally located in Weston's hills, enjoy summer theater, Vermont Country Store, an upscale restaurant, and a local bakery. Skiing at Okemo, Magic, Bromley, and Stratton, along with Viking Nordic skiing and numerous hiking trails, make this a delightful vacation getaway or year-round country escape. An exceptional bonus is the separately deeded adjacent lot, offering options to explore future development, retain for added privacy and protection, or consider selling separately, subject to applicable approvals. A charming retreat with a special connection to the outdoors and all that makes Vermont living so appealing. Measurements approximated.

Find your new home in the heart of Weston, VT with this inviting and comfortable three-bedroom home with one-level living in one of southern Vermont's prettiest small villages. From your entrance into the house by way of the new mudroom and entry area, you’ll find a small but highly-functional layout with an eat-in kitchen offering tons of cabinets and storage, a spacious sun-filled living room, and the bedrooms and full bath off the rear hall. During the warmer months, the long, wide, covered side porch is the perfect place to unwind with your morning coffee, cocktails, summer dining, or relaxing with friends after a day well spent. A full, unfinished basement with laundry and mechanicals offers space for storage or could be finished for additional living space. Outside, enjoy the beautifully maintained grounds with stunning stonework including the large stone fire pit with stone benches and seating for outside gatherings. Located just a few hundred yards from the beautiful Weston Village Green, you'll enjoy easy access to the renowned Weston Theater Company, local shops, several great restaurants, and the newly rebuilt and expanded Wilder Memorial Library. Mere minutes away, the town of Londonderry offers a popular seasonal farmers market, grocery shopping, dining, and everyday conveniences and Ludlow, Chester and Manchester are 15-30 minutes’ drive. Spend winters skiing and riding at Magic Mountain, Bromley, Stratton, Okemo, or Viking Nordic Center – all approximately 20 to 30 minutes away – and summer months will bring endless opportunities for hiking, mountain biking, kayaking, fishing, golf, and more as you explore Weston and the Green Mountain State. Whether you're seeking a primary residence, a second home, or a four-season Vermont retreat, this well-maintained Weston property offers an exceptional combination of village convenience, comfortable one-level living, and easy access to everything that makes southern Vermont such a special place to call home.

Quintessential 1880s Vermont farmhouse in bucolic Weston. Nestled on 7 private acres, this 4 bedroom, 3 bath retreat offers authentic pine floors, historical charm throughout with a tranquil pond greeting you upon arrival. It is the perfect blend or timeless character and rural serenity. BRAND NEW DRILLED WELL & MOUND SEPTIC SYSTEM just installed in August 2026. Updated electric makes this house ready for the next steward. The kitchen is authentic and you may choose to update. Situated in the picturesque town of Weston, one of Southern Vermont's most coveted historic villages. The village is home to the iconic Vermont Country Store and the renowned Weston Theater Company. The large swimming pond is spring fed from the babbling brook that boarders the back of the property. A quick drive away find skiing at Okemo Mountain Resort, Bromley, Magic and Stratton, while Summer days can be spent swimming at Hapgood Pond or exploring the West River. Grades 9-12 Have School Choice including Burr and Burton Acadamy. Your piece of Vermont history starts here. Come see this charming Vermont home being sold furnished. Call today!

Discover classic Vermont living at 74 Moses Pond Road in Weston, set on 11.4 beautiful acres along a quintessential Vermont country road. This warm and inviting three-bedroom home offers a wonderful combination of privacy, character, and convenience in one of southern Vermont’s most desirable locations. The property features an oversized barn/garage, providing exceptional space for vehicles, recreational equipment, a workshop, studio, or additional storage. Surrounded by the natural beauty of the Vermont countryside, the setting offers plenty of room to enjoy the outdoors while remaining close to the cultural and recreational attractions that make Weston so special. Enjoy convenient access to the renowned Weston Theater and Kinhaven Music School, along with charming village amenities and year-round activities. Outdoor enthusiasts will appreciate being within easy reach of some of Vermont’s premier ski destinations, including Okemo, Killington, Stratton, Magic Mountain, and Bromley. Whether you are searching for a full-time Vermont residence, weekend getaway, or four-season retreat, 74 Moses Pond Road offers an exceptional opportunity to enjoy a peaceful country lifestyle with recreation, culture, and the best of southern Vermont close at hand. Also Vast Trails are nearby for your Snowmobiling adventures!

Perfectly situated in the heart of one of Southern Vermont's most picturesque villages. Just a short drive from Stratton Mountain, Okemo Mountain Resort, Bromley Mountain, and Magic Mountain, this beautifully preserved property offers the ideal combination of historic character and modern comfort. Thoughtfully maintained, the home showcases classic New England architecture with warm pine floors, reclaimed barn wood accents, and abundant natural light throughout. Spacious living and gathering areas make entertaining effortless, while intimate sitting spaces provide the perfect setting to relax after a day of skiing, hiking, or exploring Vermont's scenic countryside. The expansive primary suite is a private retreat featuring tranquil river views, a walk-in closet, dressing room, and a beautifully appointed en-suite bath. Each additional bedroom offers its own dedicated bathroom, creating comfort and privacy for family and guests alike. Outside, enjoy mornings on the front patio overlooking the sounds of the river or spend evenings around the backyard fire pit. Located just a short walk from the Village Green, charming shops, dining, and the acclaimed Weston Playhouse, you'll experience the best of village living while remaining close to Southern Vermont's premier ski resorts, golf courses, hiking trails, and outdoor recreation. This property is a timeless treasure, ready to be cherished by generations to come. See for yourself!

Set on 3.4 private acres, this 3-bedroom, 3-bathroom Lindal Cedar home offers the rare combination of quiet mountain views and a location just a short walk from the heart of Weston Village. Inside, the living room is anchored by a cathedral ceiling and large windows that overlook Andover Ridge, bringing in ample natural light. The layout also includes a partially finished walk-out lower level, providing extra living area that can easily be tailored into a game room, home office, or completed as a separate suite. Outside, you can take in the scenery from the expansive deck. Recent improvements include a brand-new roof and skylights. This property is rounded out by a classic post and beam barn, offering excellent space for a workshop or extra storage. A beautifully sited home that perfectly balances Vermont privacy with village convenience.

Perched above Weston's coveted Dale Road in a private woodland setting, this handsome expanded cape was designed by Raymond Austin, architect of the famed Weston Playhouse. The home exudes graciousness and attention to detail in a living space that offers both cozy warmth and a light and open feeling. Surrounded by country gardens and with a south facing deck and mountain views, the property is a slice of Vermont heaven both inside and out. The first floor has a welcoming mud room with laundry and powder room, a relaxed family room/kitchen with wood burning fireplace, walk-in pantry, and deck access, a formal dining room and spacious living room with gas fireplace, and a private bedroom with ensuite bath. The second floor includes 2 guest bedrooms, one currently used as a home office, sharing a full bath, plus a primary suite with a large bedroom, ensuite bath, and walk in closet. The full dry basement offers plenty of storage space, and the attached 2 car garage will be a special comfort in the winter months. Thanks to fiber optic internet and a standby generator, you'll be able to communicate and work from home while enjoying the peace and quiet of your own Green Mountain retreat. Weston is one of Vermont's most picturesque and vibrant villages, graced with the Weston Theater, The Vermont Country Store, dining at The Hub and The Left Bank, concerts at Kinhaven, and four seasons of outdoor recreation within a short drive to Stratton, Bromley, Magic, and Okemo Mountain resorts. Come see this special property for yourself, and you may well become its next lucky owners! Showings begin September 2.

Discover the possibilities of this spacious Weston retreat, offering over 5,400 square feet of finished living space and a remarkably flexible layout just 8 miles from Okemo Mountain Resort. Designed with two complete living levels, each featuring its own kitchen, primary ensuite, living and dining areas, laundry, screened porch and separate exterior entrances, the home offers exceptional versatility for extended stays, remote work, recreation and gatherings. The main level is highlighted by a dramatic great room with soaring ceilings, exposed timber trusses, warm wood floors and a loft overlooking the living space. The spacious kitchen features granite countertops, a center island, gas range and pantry. The walkout lower level offers its own complete living areas, additional flex rooms and radiant floor heat, providing comfortable, independent spaces within the home. An attached two-car garage includes workshop and storage areas, with finished bonus space above. Outside, enjoy landscaped grounds, stonework, a patio, expansive lawn, 1/2 basketball court and the West River along the property's southern boundary. A whole-house generator adds convenience and peace of mind. Minutes from Weston village, with its renowned theater, shops and restaurants, and within easy reach of Okemo, Bromley, Magic Mountain and Stratton, the location offers year-round access to Vermont's mountain lifestyle. A distinctive property offering the space, flexibility and comfort to enjoy Vermont on your own terms. Per FEMA mapping, the residence is in Zone X (0.2% annual-chance flood hazard), while portions of the land are in higher-risk areas. Improvements include the nearby state-replaced bridge and recent drainage work on the front of the property creating a swale, berm and raised driveway to help redirect runoff. Sellers do not carry flood insurance. Flood history, mitigation details and mapping are available in disclosures.

Renovated in 2024, this timber frame sits on 5.75 pastoral acres. This property offers sunrise views, beautiful sun all day and a peaceful setting with pond on a quiet country road. The house has 4 bedrooms, 3 full baths, and an office. Wide plank original pine floors, open timber frame concept and all new baths with heated floors. Custom white oak cabinets in the kitchen and baths, with professional stainless appliances with stone countertops. Primary bedroom with full bath, pine walls and beams offering a full bar with a drawer refrigerator with microwave. Views of the mountains and the pond from oversized windows. The screened in porch offers morning sun and a beautiful sunrise with direct connect bbq grill. The partially finished lower level offers a gym and storage space. The fresh water pond has a sandy beach. New septic system and whole house generator. The two car garage added in 2024 has radiant heat, corian finish floor , and a timber carport, along with a newly paved driveway. The sunny garden area has an outdoor shower and hot tub with cold plunge are on the granite patio. Come enjoy the pasture, fruit trees, blueberry bushes and 5 acres of fields perfect for animals and gardening. Entire property has electric fence for dog containment. House sits on the corner of Piper Hill rd and Old Tavern rd with stone walls lining both sides of property. Come see this beautiful setting and enjoy one level living at its best! Close to Okemo and Stratton and mins to the Weston village. Owner is a licensed real estate agent.

Classic Alpine Chalet with Guest House and Amenities. Embrace the Vermont mountain lifestyle in this four-season retreat, where classic 1970's alpine design meets the beauty of its natural surroundings. More than a private retreat, this property is a gateway to the many pleasures of Southern Vermont, from skiing and snowshoeing in winter to hiking, tennis, gardening, farmers markets, antiquing, galleries, Manchester shopping, the Weston Playhouse and Northshire Bookstore throughout the year. Set on a picturesque property with a private pond, tennis court and delightful gardens, the estate offers peace, privacy and plenty of opportunities to enjoy the outdoors. The main residence was designed to bring the outdoors in, with dramatic cathedral ceilings and expansive walls of glass that fill the rooms with light and frame views of the mountains, gardens and woods. A cozy den with brick fireplace is a comfortable spot to unwind, while a game room offers space for entertaining. There are three spacious bedrooms, including a private en-suite, along with two additional baths, one featuring a jetted tub and private sauna. A massive wraparound deck provides a wonderful place to take in the mountain setting. A split-rail fence creates a courtyard where you will find a curated flower garden, and the tennis court offers hours of play. The separate guest house provides complete privacy and includes a cathedral-ceilinged main room, bedroom and full bath, adding approximately 1,000 square feet of living space not included in the main house square footage or room count. A meandering path winds through the woods to a serene pond. Just 2 miles from Weston Village, 25 minutes to Manchester and within 30 minutes of four ski areas, this is a special Vermont retreat and a wonderful base for enjoying all that the area has to offer in every season.

Meticulously maintained and thoughtfully updated, this distinctive Post-and-Beam home is set on 2.23 beautifully landscaped acres, surrounded by the natural beauty of Southern Vermont. The soaring family room is filled with natural light and anchored by a dramatic floor-to-ceiling fireplace. The spacious dining area flows seamlessly into an extended bar and gourmet kitchen, with direct access to an expansive deck overlooking the wooded grounds. The home offers three bedrooms and 2.5 baths, including a first-floor primary suite. The expanded gourmet kitchen features state-of-the-art stainless steel appliances, induction range, granite countertops, extensive custom cabinetry, and a wet bar. First-floor laundry and a half bath add everyday convenience. Recent improvements include a new roof and exterior paint in 2026, along with fresh interior paint in 2025. The tastefully finished, walk-out lower level provides additional living and entertaining space, along with ample storage. Outdoors, the expansive deck invites relaxed dining and entertaining amid the beautifully landscaped grounds. Additional highlights include an oversized Car Barn with a heated workshop and abundant second-level storage, a tastefully designed storage shed that echoes the home’s architectural style, a whole-house generator, and owned solar. Ideally located just minutes from Weston Village, its restaurants and amenities, the renowned Weston Theatre, and the Vermont Country Store, the property is also within 30 minutes of Okemo, Magic, Stratton, and Bromley ski areas. Combining timeless Post-and-Beam character, modern updates, and a beautiful natural setting.