Winhall Real Estate

06/01/2026

❄️ WINTER SEASONAL RENTAL AVAILABLE 2026/27 – $22,000 | Winhall, VT ❄️

Enjoy the ultimate Vermont ski season from this beautifully updated 3BR/2BA home on Glendon Hills Road. Conveniently located just 10 minutes to Stratton, 5 minutes to Bromley, and 10 minutes to Manchester's shops and restaurants.

Features include a stunning stone fireplace, reclaimed wood accents, updated kitchen and baths, full laundry room, dedicated bunk room, and a spacious deck with grill for après-ski gatherings.

Tucked away at the end of a quiet dead-end road and bordering National Forest, you'll have direct access to outdoor adventures including snowshoeing and the Catamount Trail.

📍 Winhall, Vermont
💲 $22,000 for the winter season
📞 Winhall Real Estate | 802-297-1550

06/01/2026

05/29/2026

🏡✨ Just Listed in Winhall, Vermont ✨🏡

Experience the perfect blend of historic Vermont charm and modern comfort in this beautifully updated New England farmhouse, just 1 mile from Stratton Mountain Access Road.

Featuring 4 bedrooms, 2 baths, exposed beams, hardwood floors, and a cozy cast iron wood stove, this special home offers warmth, character, and year-round adventure. Located just steps from the VAST snowmobile trail, you'll enjoy easy access to skiing, hiking, snowmobiling, and all that Southern Vermont has to offer.

Adding to its unique appeal, this home was once a gathering place for legendary folk singer Arlo Guthrie—a property rich in history, character, and soul.

Whether you're looking for a primary residence, weekend retreat, or investment opportunity, this farmhouse captures the very best of Vermont living.

📍 140 Route 30, Winhall, VT
💲495,000 | MLS #5091404

📞 Carrie Mathews | 802-236-8458

05/29/2026

OPEN HOUSE | Sunday, 5/31 | 11 A.M. – 2 P.M.
📍287 Powder Mill Road, Londonderry, VT
Available for $474,500

Nestled in the heart of Vermont’s scenic countryside, this beautifully maintained log cabin offers the perfect blend of rustic charm and cozy comfort. Surrounded by nature and timeless New England beauty, the home welcomes you with warm wood interiors, exposed beams, and an inviting atmosphere ideal for year-round living or the perfect weekend getaway.

Enjoy peaceful mornings on the porch, cozy evenings by the fire, and the tranquility only Vermont can offer. Conveniently located between Bromley, Magic, and Stratton Mountains, this charming retreat also sits just minutes from Manchester, VT and its popular shops and outlets.

Whether you’re searching for a ski home, a serene escape, or a full-time Vermont lifestyle, this enchanting property captures the essence of mountain living.

Hosted by Joe Castelluccio
📞 732-979-4750 for more information

05/29/2026

🏡 CLOSED | 1768 Barnumville Road, Manchester, Vermont 🏡

Some real estate stories are about much more than buying a home—they're about building a new life.

After visiting Vermont for a wedding, Joe Castelluccio's buyers fell in love with everything our beautiful state has to offer. The mountains, the communities, the lifestyle, and the unmistakable charm of Vermont inspired them to make a bold decision: leave California behind and make Vermont home.

Joe was honored to help them turn that dream into reality and guide them through their successful relocation journey.

Congratulations to our buyers and everyone involved in making this special closing happen! Wishing you many years of happiness and wonderful memories in your new Vermont home.

Thinking about making a move, buying your first home, or relocating to Vermont? Let Joe help make your real estate dreams come true.

📞 Joe Castelluccio | 732-979-4750

Winhall Real Estate — Opening Doors Since '74.

05/27/2026

🏡 OPEN HOUSE | Sunday, 5/31 | 11 A.M. – 2 P.M.
📍287 Powder Mill Road, Londonderry, VT
Available for $474,500

Nestled in the heart of Vermont’s scenic countryside, this beautifully maintained log cabin offers the perfect blend of rustic charm and cozy comfort. Surrounded by nature and timeless New England beauty, the home welcomes you with warm wood interiors, exposed beams, and an inviting atmosphere ideal for year-round living or the perfect weekend getaway.

Enjoy peaceful mornings on the porch, cozy evenings by the fire, and the tranquility only Vermont can offer. Conveniently located between Bromley, Magic, and Stratton Mountains, this charming retreat also sits just minutes from Manchester, VT and its popular shops and outlets.

Whether you’re searching for a ski home, a serene escape, or a full-time Vermont lifestyle, this enchanting property captures the essence of mountain living.

Hosted by Joe Castelluccio
📞 732-979-4750 for more information

05/26/2026

A uniquely designed home finds its next chapter 💙

264 French Hollow Road in Winhall, VT was more than just a home for Kristin Pirie and her husband, Iain — it was a beloved mountain retreat that was even featured in a recent issue of Stratton Magazine. After many wonderful years enjoying the Vermont lifestyle, a job relocation made it time for a new chapter.

Fortunately, the home found the perfect next owners: a young couple passionate about skiing and snowboarding who instantly fell in love with the property and its incredible setting. Planning to live there full time while working remotely, they are excited to embrace mountain living and create memories of their own for years to come.

Despite many moving parts along the way, the transaction came together beautifully, and it was a true pleasure working alongside the buyers and their agent to make it happen.

Congratulations to all involved in this special sale! ✨

If you’re considering your next move in Southern Vermont, please contact one of Kristin’s trusted colleagues at Winhall Real Estate.
📞 802-297-1550

05/26/2026

✨ Just Listed in Jamaica, Vermont ✨
4427 West Hill Road South | Offered at $1,295,000

Experience a one-of-a-kind luxury Vermont lodge blending five-star amenities with the warmth and charm of a mountain retreat. Set on 11.12 private acres, this stunning property was designed for unforgettable gatherings and peaceful escapes alike.

Enjoy expansive open living spaces, an 11-foot home theater, two fireplaces, a spectacular great room with a 90-inch TV, plus incredible outdoor amenities including a six-person hot tub, eight-person sauna, outdoor dining area, and fire pit surrounded by the beauty of Vermont’s forests.

Whether entertaining family and friends or enjoying a quiet mountain getaway, this extraordinary home offers the perfect balance of comfort, luxury, and connection.

📍 Jamaica, VT
🛏 5 Bedrooms
🛁 4 Bathrooms
🌲 11.12 Acres
MLS #5090616

Listed by Carrie Mathews
📞 802-236-8458

05/26/2026

Bittersweet closings are often the most meaningful 💛

After 22 wonderful years at 17 Roundtree Road in Winhall, VT, Sarah Nichols has officially closed the sale of the home where she created so many cherished memories raising her children. As both the homeowner and Listing Agent, this transaction was especially close to her heart.

While saying goodbye to a beloved family home is never easy, Sarah is excited for this next chapter — living closer to her grown children in Connecticut and looking forward to future grandchildren and new memories ahead.

Congratulations, Sarah, on this meaningful milestone and a successful closing!

Please call 802-297-1550 for help with your next real estate transaction from one of Sarah's trusted colleagues.