Colonial Homes for Sale in Windsor County VT

Experience the Vermont lifestyle in this beautifully renovated 1864 Brick Federal style farmhouse set on 7.8 private acres just minutes from town. Rich in historic character and thoughtfully updated for modern living, this exceptional property offers the perfect blend of comfort, charm, and year-round recreation.Inside, you’ll find four spacious bedrooms, wide plank wood floors, and inviting

Gary Coger Four Seasons Sotheby's Int'l Realty

This gracious 1796 Brick Federal homestead was transformed into a popular gathering spot more than 60 years ago. The Barnard Inn has long been considered among the finest dining and hospitality venues in Vermont. It is currently operated as an event destination by the chef-owner and his family.Now, with children grown and off on their own paths, it is time to pass stewardship of the historic

Laird Bradley Williamson Group Sothebys Intl. Realty

Welcome to this versatile and well maintained mixed-use property offering three-unit potential in an excellent in town location, just minutes from the mountain. The property currently features two beautifully updated residential apartments plus a commercial office space, with the potential to convert the commercial space to a third residential unit, offering even greater income

Gary Coger Four Seasons Sotheby's Int'l Realty

If you're looking for the ultime village ski house look no more! This four bedroom three and a half bath TURN KEY home is nestled in the village of Proctorsville. Home to Singletons Store, Outer Limits Brewery, Murdoch's On The Green and much more walking distance away. Step into this lovely well appointed home and you'll feel right at home. The kitchen boasts granite counters with a large

Frank Provance Diamond Realty

Welcome to a truly special Vermont property where craftsmanship, comfort, and the beauty of the outdoors come together. Offering over 3,000 square feet of beautifully renovated living space, this distinctive home is filled with custom features and exceptional woodworking throughout.The heart of the home is the custom kitchen, featuring rich cherry cabinetry and timeless soapstone

Gary Coger Four Seasons Sotheby's Int'l Realty

Hart’s Crossing is a home and a haven featuring a custom 21st-century residence and a comprehensively restored Civil War-era guest house, set on 418 acres of private land. The property provides a refuge in nature, with a kingdom-sized backyard to explore and adventures that change with the seasons. Located at the end of a town-maintained road, the property is a 10-minute drive from either

Laird Bradley Williamson Group Sothebys Intl. Realty

QUINTESSENTIAL WOODSTOCK VILLAGE LIVING: Offered at $399,600, this beautiful townhouse presents a rare opportunity to own a home in the heart of Woodstock Village at an exceptional value. Enjoy the charm, convenience, and lifestyle of Village living, with easy access to Woodstock’s shops, restaurants, recreation, and the greater Upper Valley.THE HOME: The largest layout in a peaceful

Carol Robert Housing Solutions Real Estate LLC

This meticulous & well cared for home welcomes your family and friends with its stately front porch designed by Anne Wilson. The main level is a terrific place for entertaining with large open rooms, 9’ ceilings, radiant heat, crown moldings, an abundance of windows and natural light, handsome fireplace, and lovely oak flooring throughout. Open the french doors to a comfortable private deck

Gretchjen Smith Williamson Group Sothebys Intl. Realty

Built in 1807 by Tille Parker, 26 The Green is one of Woodstock Village’s earliest and perhaps prettiest houses. The Federal style residence originally served as a tavern and lodging for members of Vermont’s early legislature, giving the property an uncommon connection to both the town’s and the state’s history. Over a century later, it became the Daughters of the American Revolution House

Dia Jenks LandVest, Inc/Woodstock

Steeped in history and timeless elegance, this extraordinary circa-1860 Georgian Colonial estate offers over 8,000 square feet of refined living space where classic architecture meets remarkable craftsmanship. From the moment you enter, you are greeted by stunning period details including exquisite crown moldings, grand proportions, soaring ceilings, and beautifully preserved finishes that

Joe Castaluccio Winhall Real Estate

A rare opportunity to own approximately 39 acres and a genuine piece of Vermont history in the historic hamlet of Weathersfield Bow. Known historically as the former Danforth Inn, this circa-1780 property is far more than an old house, it is a remarkable collection of land, barns, history, and possibilities.The 39.11-acre parcel begins along U.S. Route 5 and extends deep into the

Elizabeth Story KW Vermont-Stowe

Imagine living in an 1806 home on a Vermont green. Located in the heart of the Green Mountains in the quaint town of Rochester, along the scenic Route 100 corridor. The property is currently a classic Vermont Inn with a chef-owned restaurant and tavern with lovely accommodations. Easily refurnished for private use. The home sits atop the Rochester Green. The village features galleries, shops, and

Kate Cassidy Four Seasons Sotheby's Int'l Realty

The Richmond House Unit B | Woodstock Village. An enduring Woodstock landmark, the iconic Richmond House (c.1826) is a proud brick Federal distinguished by its softly weathered rose-hued patina and refined architectural detail. Set on more than an acre behind a classic white picket fence and thoughtfully reimagined under the direction of Laurence Rockefeller, the property comprises three

Derek Cosentino Four Seasons Sotheby's Int'l Realty

Under $700K in Quechee Lakes! Beautifully updated, meticulously maintained, and truly turnkey, this spacious fourbedroom, 3 and a half-bath home combines timeless comfort with modern efficiency in one of Vermont's most sought-after four-season communities. Designed for both everyday living and effortless entertaining, the sun-filled main level features a spacious eat-in kitchen that flows

Katie Ladue Gilbert BHHS Verani Upper Valley

Stepping onto the grounds, it becomes immediately clear that they simply do not make homes like this anymore. This magnificent 1897 Victorian mansion, recently painted in a crisp white exterior, stands as a remarkable testament to an era of unmatched craftsmanship. Yet, for all its grand presence, it remains a well-kept secret. The entry is so subtle off the paved road that a passerby would never

Franchesca Collins Hall Collins Real Estate Group

This Beautiful Homestead Ready property features a lovely exposed post & beams, with flooring that is tile, pine in bedrooms and some reclaimed hard wood, and rough sawed wood ceilings, 3 bedroom 2 baths both with walk in showers, mudroom, large living room with welcome area near the front door, excelently designed kitchen with a large center island open to the dining room which has sliders to a

Mary Chamberlin Dave Walthour Real Estate

Between Woodstock and Killington, on 13.68 private acres near the north branch of the Ottauquechee River, this one-owner estate was built from the ground up with uncommon care. Offered at $1,150,000, below its April 2026 appraisal. Four bedrooms, five baths and 4,352 finished square feet, with radiant floor heat throughout, a new furnace and boiler, a standing seam metal roof, a private well

Tucker Adirondack Lange Lange & Lange

Price improvement plus a new septic leach field! What a sweet historic home just waiting for the right person to give it some TLC to bring it back to its beautiful original state! The house is very straight and solid, so that anyone can easily live in it as they do the cosmetics to their personal taste. Attached to the main body of the house is a very nicely done and spacious in-law apartment

Glenn Olney Barrett and Valley Associates Inc.

Turnkey and meticulously maintained, this 4-unit multifamily property offers strong cash flow and peace of mind for its next owner. The property features three 2-bedroom, 1-bath units and one spacious 4-bedroom, 2-bath unit, offering an attractive mix for a variety of tenants. Investors can add a stable, well-cared-for asset to their portfolio, while owner-occupants could live in one unit and use

The Nancy Jenkins Team Nancy Jenkins Real Estate

Set in the highly desirable South Hill Estates, this exceptional property pairs privacy with an unbeatable location just minutes from Okemo Mountain. Surrounded by nearly five acres, the home enjoys sweeping mountain views and a beautifully open landscape that invites year-round enjoyment. The yard is a true highlight-offering plenty of space to relax, entertain, and play. A picturesque pond

Debra Staniscia Four Seasons Sotheby's Int'l Realty

Set in a peaceful neighborhood with scenic views and large backyard, this expansive home offers the perfect balance of space, comfort, and flexibility. With 5 bedrooms and several bonus living areas throughout, there is plenty of room to fit a variety of lifestyles and needs. Inside, you’ll find spacious living areas filled with natural light, along with a finished basement that adds even more

The Malley Group KW Vermont

Stately hilltop home built by Silas Banister c.1800, recently undergone a complete restoration. Quality materials & craftsmanship throughout. It has gorgeous views of nearby Ascutney Mountain & long-range views of NH. The property consists of 98 acres made up of fields, hard & softwoods, trails, a large sugarbush (potential for a future boiling operation). Conserved by Upper Valley Land Trust,

Dana Waters Dark Horse Realty

Historic Rowen Farm offers a rare blend of authentic Vermont character, privacy and turnkey ease. Set on 77+ acres of meadow and woodland, the circa-1812 Federal farmhouse has been extensively restored while preserving its soul: original wide-plank floors and exposed beams, original doors and period details, and four wood-burning fireplaces.Inside, approx 3,860 square feet of light-filled

Kim Prins Four Seasons Sotheby's Int'l Realty

This 1850s renovated property located right in the heart of the village adapts perfectly to your lifestyle or investment goals. This home functions seamlessly as a spacious 5-bedroom, 2-bathroom home or is ready to operate as two separate income-generating rental units. The unfinished third floor can easily be converted into additional living space, a master suite, or a bonus room. The spacious

Tyleen Murray Kelley Real Estate, Inc.

Fully furnished condo nestled in a small quiet community just 5 minutes from "Historic Woodstock". Super location! This unit is in very good condition- first floor comprised of a den//bedroom with pocket doors for added privacy and an adjacent 3/4 bath. Spacious living room anchored by a newer propane fireplace to curl up with a book on a cold winter day. A couple of steps down takes you into a

Gretchjen Smith Williamson Group Sothebys Intl. Realty

An exceptional opportunity to acquire two well-maintained multifamily properties offered together as an 11-unit investment package near Okemo Mountain Resort. The portfolio features seven 2-bedroom, 1-bath apartments, two 1-bedroom, 1-bath apartments, and two spacious 4-bedroom, 2-bath units, providing a versatile mix designed to appeal to a broad tenant base. Significant improvements include two

The Nancy Jenkins Team Nancy Jenkins Real Estate

This beautifully renovated, truly move-in-ready home has been thoughtfully updated throughout including a brand-new kitchen, refreshed flooring, modernized bathrooms, fresh interior paint, a new garage door, an automatic full-house generator, and more. The property is offered FULLY TURNKEY, with nearly all furniture and furnishings conveying with the sale (artwork excluded). Privately sited in

John Snyder Snyder Donegan Real Estate Group