Luxury homes for sale & real estate in Windsor, VT

Luxury Home for sale in Windsor, VT:

2687 GARVIN HILL ROAD- Surrounded by the rolling hills and natural beauty of the Woodstock countryside, 2687 Garvin Hill Road offers a quintessential Vermont lifestyle on 18.16 acres, just minutes from the heart of Woodstock Village. Landscaped grounds, old stone walls, and expansive acreage create an inviting setting for gardening, outdoor gatherings, walking the property, or simply enjoying the changing seasons. The 5-bedroom historic residence blends original charm and character with sophisticated upgrades, creating warm, comfortable living spaces without compromising modern convenience. A bright, light-filled kitchen and dining area flows beautifully into a formal dining room and a dram

Luxury Home for sale in Windsor, VT:

Located in the heart of the charming hamlet of South Woodstock, the iconic John Arnold Cottle House is widely considered one of Woodstock's finest early residences. Built in 1811, and listed on the National Historic Register, this stately home has been thoughtfully restored, and lovingly stewarded over the years honoring the period detail while creating the perfect unification of antiquity and modern functionality. The bright, spacious rooms flow seamlessly for daily living or entertaining. The impressive Kitchen-Great Room is anchored by a generous brick fireplace, and sweeping 17’ cathedral ceiling, and steps out to a private deck overlooking the brook, fields and trail systems bey

Luxury Home for sale in Windsor, VT:

HILLSIDE FARM - SOUTH WOODSTOCK, VERMONT. Hillside Farm estate presents an exceptional opportunity to embrace the quintessential Vermont country lifestyle on 10.1 picturesque acres in prestigious South Woodstock. Offered TURNKEY and FULLY FURNISHED, the sale includes an extraordinary array of shop equipment, mechanical equipment and property-maintenance and recreational equipment. Built by a master craftsman and builder, the residence showcases handsome timber-frame construction, warm woodwork and enduring craftsmanship throughout. Rolling meadows and pastures, woodland, two streams and a scenic pond create an idyllic setting for equestrian, agricultural and recreational pursuits. At the he

Luxury Home for sale in Windsor, VT:

Historic character, beautifully reimagined for modern Vermont living. Minutes from Woodstock Village, this extensively renovated four-bedroom home pairs the warmth and authenticity of its 150-year-old wide-pine floors and exposed beams with a remarkable collection of recent improvements. At the heart of the home is a brand-new, high-end kitchen with Bosch appliances and newly installed natural bluestone radiant heat flooring, complemented by thoughtfully updated baths, including one with a beautifully executed marble walk-in shower. A dramatic new three-story addition, wrapped in oversized casement windows, introduces abundant natural light and generous new living space while creating a com

Luxury Home for sale in Windsor, VT:

The property is located on Town Farm Hill Rd, one of the most beautiful ridgeline Vermont roads with long range mountain views to the east and south. At certain times of the day the lighting brings out the true meaning of “purple mountain majesty”. Over the years the seller has acquired multiple parcels to create this beautiful sanctuary setting. The house is positioned to take in the mountain views, spring-fed swimming pond, meadows, and apple orchard. Beautiful rolling fields, stonewalls, acres of forest, and outbuildings are many features of the property. It is surrounded by horse, mountain biking, and hiking trails for recreation. This modest 3-bedroom, 2-bathroom, center ch

Luxury Home for sale in Windsor, VT:

Stunning Contemporary on 7.6 acres - Sunny, Bright, and beautifully designed, this gorgeous home showcases exceptional workmanship, thoughtful details, and a wonderful connection to the outdoors. A gracious entrance lined with pear and cherry trees on this paved circular driveway, with center planting beds with seasonal blooming plants (roses, hostas, lilies, sunflowers, hydrangeas) and beautiful stonework, creates an impressive first arrival. Inside the heart of the home is the spectacular kitchen, featuring custom cabinetry, granite countertops, a country sink, and a gorgeous Elmira retro stove. The kitchen flows seamlessly into the dining and living areas with Oak floors, soaring vaulted