Previous Previous ImageNext Next Image
Slideshow Divider

Our mobile site is optimized for smaller screens.

TRY IT NO THANKS

and narrow your search. If you have fewer than 200 results, you can save your search.

Windsor County VT Real Estate

Find the latest real estate listings for sale in Windsor County, VT. Save your favorites to your account and get email notifications when similar properties hit the market. For more information, any questions you make have & to schedule a show, please feel free to contact us.

Search Windsor County listings by town:

Andover | Baltimore | Barnard | Bethel | Bridgewater | Cavendish | Chester | Hartford | Hartland | Ludlow | Norwich | Plymouth | Pomfret | Reading | Rochester | Royalton | Sharon | Springfield | Stockbridge | Weathersfield | West Windsor | Weston | Windsor | Woodstock

2034 Long Hill Road Woodstock VT 05071

Woodstock, VT2034 Long Hill Road

Price$8,950,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4943673

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 7
  • Square Feet 8,921

High up in the hills above South Woodstock, Little Baldy Hill Farm is set among rolling meadows with sweeping views of the Green and White Mountains. The 295 acre property offers complete privacy, miles of trails through spectacular classic Vermont landscapes, and a compound with every amenity carefully considered. Inspired by travels through Europe, the house was designed with a romantic, and very comfortable, take on country living. Arched windows and hallways, vaulted ceilings, a rounded tower and a great hall with a massive stone fireplace give context to spaces for gathering with friends and family and cozy nooks for reading. The property embraces its setting: taking in the views and light, with French doors inviting a walk in the courtyard gardens and the stone terrace, a splash in the pool, and quiet puttering in the greenhouse. The main house has four bedrooms en suite with a first floor primary and guest suite. The three-level carriage barn has a one bedroom guest apartment on the top floor. A ramp to the second floor allows for the storage of cars and carriages or makes for a great party barn or studio. Also on this level is a 5 stall stable with wash stall. The lower level houses a heated workshop and plenty of room for toys. The grounds include a tennis court, barn and pond and miles to explore. High speed internet. Surrounded by large landowners and yet close to GMHA and the South Woodstock Country Store. 2.5 hours to Boston. Delayed showings until 2.28.23

Listed by T Story Jenks and Dia Jenks of LandVest,Inc/Woodstock

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.94% last updated on 2024-05-23

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

322 Weed Road Hartland VT 05048

Hartland, VT322 Weed Road

Price$4,995,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4985551

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 6
  • Square Feet 4,286

Ferguson Farm is a restored, classic brick Federal home dating back to 1784, embraced by sugar maples and stone walls. Located just outside the village of Woodstock on a quiet gravel road, the property also features a four-level Shaker barn and offers views across 83 acres of undulating fields, woodlands, and a 4 acre swimming pond. What sets this place apart are those intangible qualities: a deep sense of belonging, classic beauty, and a relaxed, easygoing vibe. Thank years of good stewardship and thoughtful renovation for that. The main house, with four bedrooms and six baths, features a spacious farmhouse kitchen with an inviting sitting area by the fire. For the end of the day, take supper on the porch and soak in the views of the sun setting over the pond. The gardens yield a bountiful harvest of apples and flowers. The barn serves as a home for chickens and livestock, offering ample turnout space as well as a fantastic venue for gatherings, a guest bedroom, office accommodations, and bathroom as well as space for yoga or a gym. Plus, there's a workshop in the shed for when you want to tinker or be creative. An extensive network of well-maintained trails for riding, skiing or walking wind by the beaver pond, swimming pond and through the woods. In an area of large land holdings, just 10 minutes to Woodstock and easily accessed from Interstates 89 and 93 and the Lebanon Airport near Hanover.

Listed by T Story Jenks and Dia Jenks of LandVest,Inc/Woodstock

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.94% last updated on 2024-05-23

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

476 Salt Ash Road Plymouth VT 05056

Plymouth, VT476 Salt Ash Road

Price$4,850,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4976477

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 6
  • Square Feet 9,153

Serena Lodge was inspired by the legendary William Rockefeller estate in the Adirondack Mountains, known as The Point, which the current owners so loved. The 9,000+ square foot home was thoughtfully designed to perfectly capture the inviting look and warm feel of the renowned five-star enclave. The long drive welcomes one to the residence, which rests atop a knoll by a crisp creek with small waterfalls that create constant water music. The Great Room, the heart and soul of the home, features a striking stone fireplace, floor to ceiling windows, two sitting areas, and an accessible kitchen framed by a thick granite counter. Outdoors, a barbecue terrace and stairs lead to the creek. In the east wing, the primary suite offers tranquil privacy with sitting area, fireplace, and balcony. The west wing has four more en-suite bedrooms and a designated family room. An open stairway leads to artist studio, office and sitting area in the loft. The 25 x 38 foot Adirondack Room in the lower level is for games and TV, with convertibles for extra sleeping. There is a bonus room with bath and a wood shop that doubles as a car park. The house is fully air-conditioned, has high speed internet and a generator. A short drive to both Okemo and Killington, the Hawk community is managed by Hawk Services providing all the services one could desire. Living at Serena Lodge can be quiet or social, as active or relaxed as you like. The possibilities are as broad and grand as the majestic home itself.

Listed by Debra Staniscia of Four Seasons Sotheby's Int'l Realty

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.94% last updated on 2024-05-23

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

327 Fletcher Schoolhouse Road Woodstock VT 05071

Woodstock, VT327 Fletcher Schoolhouse Road

Price$4,300,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4993127

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 5,939

ByBrook Farm: Reimagined, turnkey 1790s farmhouse set in one of Vermont's most loved valleys, perennial gardens, stone walls, a spring fed pond, a brook, and rolling meadows. Quiet luxury. Just outside the hamlet of South Woodstock on 25 acres, the 2-bedroom 4,667 sf farmhouse and the 2-bedroom 1,273 sf guest cottage are connected by a stone pathway through the gardens. In the recent renovations of the main house, an additional 825 feet were added on for the kitchen and an extension to the upstairs bedroom suite. Vernacular character: Hand-plastered walls reflect the Vermont light, hand-planed boards, hand-hewed beams and a dining room mural by the Hudson River painter, Kevin Paulsen. Comfortable living, beautifully done. Attached to the farmhouse are two parking bays and a bank barn. On the lower level of the post and beam barn is a large gym or studio space. A picnic area on the top of the knoll has views of the rounded hills and the Kedron Valley-- a landscape that has not changed much over the last 200 years. New geothermal system, solar array and a hook-up for an electric car. The main dwelling has whole house A/C. EC fiber high speed internet. 0.2 miles from Kedron Valley Inn/Ransom Tavern and South Woodstock Country Store and less than a mile from GMHA, the oldest horse club in the country. 26m from Killington and 40m from Okemo. 2h 19m from Boston. Showings begin May 10th.

Listed by T Story Jenks and Dia Jenks of LandVest,Inc/Woodstock

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.94% last updated on 2024-05-23

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

2051 Gold Coast Road Bridgewater VT 05091

Bridgewater, VT2051 Gold Coast Road

Price$3,500,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4957886

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,562

Peace. Tranquility. Big views. Located in the Chateauguay No Town Conservation Area near Woodstock, Wolfstar offers a haven with breathtaking views of the Green Mountains. Meticulously reenvisioned in 2008 by Vermont architect David Beilman, this 15-acre property, cherished as a second home for 35 years, provides complete privacy and understated luxury. The 3,562 sq ft shingle-style home includes a first-floor primary suite, three additional bedrooms, 3.5 baths, and a large attached two-car garage. In 2013 a fabulous studio was added - perfect for art, exercise, media, or office. High-speed internet (shortly VTel 10G+). Craftsmanship and thoughtful design create a practical and stylish home, inviting shared moments by fireplaces, on the screened porch, or in the mature gardens and apple orchard. Facing west, the house enjoys sunsets over the mountains. With protected, abutting acres conserved by Vermont Land Trust, Wolfstar encourages relaxation and country pursuits. Extensive stonework enhances the home, offering spaces for entertainment. Host a gathering on the terrace and lawn, creating enduring memories in this beautiful place. Later, enjoy dark-sky star gazing! Offered turnkey with quality furnishings, Wolfstar is 5 miles from the Woodstock Farmers' Market, 6 miles from Woodstock village, 10 miles from Killington, and 2.5 hours from Boston. This unique opportunity invites you to embrace a balanced lifestyle - refined country living with access to the best of Vermont.

Listed by T Story Jenks and Dia Jenks of LandVest,Inc/Woodstock

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.94% last updated on 2024-05-23

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Broker Reciprocity 

Copyright 2024 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated May 25, 2024 11:23 PM EDT

 

New School Reconstruction

6 BR on Shelburne Bay, $3,995,000 Details

Killington Ski In-Ski Out

7BR, Hot Springs Hot Tub, $4,490,000 Details

 

Iconic Burlington Estate

7BR, 17.6 +/- ac, $14,000,000 Details