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Windsor County Real Estate for Sale

Explore the latest real estate for sale in Windsor County, Vermont. If you have any questions or if you'd like to see any of these properties in person, call 802-793-2002 or contact us online.

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326 Goodrich Road Chester VT 05143

MLS Number 4963698

  • Commercial
  • County Windsor
  • Square Feet 1,760
  • Acreage 25.99

This is a first class stone quarry operation which pumps out a beautiful stream of high grade gneiss stone, so indispensable for the building trades in constructing patios, steps, walls, chimneys, and every place beautifully ad naturally colored building stones are needed. The next owner of this business will of course be buying a highly profitable and proven going concern. However, the next owner will have seen the monumental opportunity in the $168,000,000, in unmined, and yet very minable stone as attested to by the attached professionally prepared geological report. Complete with $1.5 M worth of meticulously maintained equipment and an immaculate stone cutting shop, this offering spells opportunity writ large. While the Owner believes the next owner will be someone already in the industry, and he may be correct, I also believe that it could be anyone who sees the brilliance of buying assets for pennies on the currently shrinking and inflated dollar along with a proven and successful method for extracting same. But what do I know? I'm just a Realtor. But an entrepreurial MBA Realtor nonetheless who will be happy to show you this opportunity in person.

Listed by Lawrence Zupan of EXP Realty

$
$
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$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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3800 Weston Andover Road Andover VT 05143

Andover, VT3800 Weston Andover Road

Price$8,300,000

Est. Mortgage: $/month

MLS Number 5015743

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 8
  • Bathroom 8

A magnificent 10,062 SF family compound. Custom built, it comes fully furnished and equipped for immediate occupancy, featuring 7BR, 8BA, a separate 1BR guesthouse and office, a furnished and heated writers cabin overlooking the Connecticut River Valley, and an equipment barn, all situated on 384 acres of pristine hardwood forest, accessed by an 1800' paved driveway. Anchored by miles of woodland trails and located in Andover, Vermont, the offering includes outdoor sculpture and artwork, historic rock walls, open fields and building ruins from early settlers, along with direct access to the VAST trail system for winter trail riding. The main house features a soaring 2-story fireplace, post and beam timber frame construction, and a chef's kitchen with double appliances, Viking 60” cooktop and wood-fired interior pizza oven, while a reading loft and library add a calming vibe to the outdoor view. The primary suite has a 2BR, 2BA configuration on the main floor with 5 additional bedrooms with en suite baths. There are 6 garage bays supplied with commercial sinks, a 21' x 35' open design gym and exercise suite, and a media room with custom pool table and walkout to the ground floor. Designed for 4-season recreation, privacy and small batch maple syrup production, the hardwood forest, mountain trails, open fields, and additional access from another town road offer unlimited possibilities for the discerning buyer looking for a lifestyle in Vermont's iconic Green Mountains.

Listed by Steve Stettler and Gary Coger of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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327 Fletcher Schoolhouse Road Woodstock VT 05071
Pending

MLS Number 4993127

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 4

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

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$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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249 Sawyer Road Woodstock VT 05091

Woodstock, VT249 Sawyer Road

Price$4,150,000

Est. Mortgage: $/month

MLS Number 5018393

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 5

Listed by Elevations Team of Real Broker LLC

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$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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4 Morning Star Drive Ludlow VT 05149

Ludlow, VT4 Morning Star Drive

Price$4,100,000

Est. Mortgage: $/month

MLS Number 5017498

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 5
  • Bathroom 7

One of the most coveted homes on Okemo is ready for its new owner. Welcome to a spectacular, Montana lodge-style retreat nestled in a prime slopeside location on Okemo Mountain, adjacent to Solitude Village Day Lodge. This breathtaking ski-in/ski-out home sits at the top of Daybreak Trail, offering unrivaled mountain views in every direction. Crafted from Montana lodge pole pine and Vermont stone, this five-bedroom estate blends rugged elegance with luxurious comfort. Step inside to a spacious haven, complete with two grand stone fireplaces and an open-concept design. The chef's kitchen, with high-end appliances and a commercial hood, has access to the stone fireplace featuring a pizza oven. The open concept allows a seamless flow into the living and dining areas, creating the ideal apres-ski gathering space. This home offers endless relaxation with its expansive decking, six-person salt water hot tub, Danish sauna, steam room, and an outdoor fireplace. Each bedroom is an oasis of privacy, and many have an en-suite bath. The primary bedroom has dual walk-in closets and views both up Okemo and to the valley below. With immediate access to the Solitude chairlift and steps from Solitude Village's amenities and seasonal restaurant, this one-of-a-kind home delivers the ultimate mountain lifestyle. Experience unparalleled luxury, convenience, and craftsmanship at this slopeside residence. Visit the Okemo real estate community today. Taxes are based on current town assessment.

Listed by Joseph Karl of William Raveis Vermont Properties

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$
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$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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18 The Green Woodstock VT 05091

Woodstock, VT18 The Green

Price$3,995,000

Est. Mortgage: $/month

MLS Number 5008434

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 6
  • Bathroom 8

Conveniently located on the southwest side of the picturesque Woodstock Village Green, this classic c1840 Greek Revival farmhouse is one of the town's finest residences. Lovingly stewarded and thoughtfully restored to the highest standard preserving the historic integrity and honoring the period detail, all while achieving the perfect unification of sophistication, functionality, modern comfort and convenience. The first level of the original home features generous spaces for entertaining and cozy, intimate rooms for quiet reflection. Original wide pine plank floors, oversized 6/6 windows, formal parlor and library each with a working fireplace. There is potential for a first-floor primary suite. The main house is further completed by 3 ensuite bedrooms and laundry on the second level, and two guest rooms with a shared bathroom on the third. The magnificent, attached c1750 oak gunstock post and beam barn frame was disassembled, imported from Hampshire, England and added to the home in the 1980's, providing a Great Room beyond compare. Anchored by a massive stone fireplace, Palladian windows and a well-appointed chef's kitchen, all located on the main level. There is a guest suite, three car garage, and courtyard entrance on the walk out lower level stepping out to lovely, landscaped grounds and gardens.

Listed by Danny Kogut and Carol Wood of Williamson Group Sothebys Intl. Realty

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$
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$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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322 Weed Road Hartland VT 05048

Hartland, VT322 Weed Road

Price$3,985,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4985551

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 6

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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501 Galaxy Hill Road Pomfret VT 05067

Pomfret, VT501 Galaxy Hill Road

Price$3,850,000

Est. Mortgage: $/month

MLS Number 5010256

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 6
  • Bathroom 5

MAPLE LANE FARM - With a sweeping, maple-lined drive, this property holds court in one of Pomfret's most beautiful neighborhoods. Seven perennial gardens offer beauty in every season - from the "Secret Shade Garden" (created during Covid spring) to the two 100' perennial borders to the "Dwarf Conifer Garden" (how they GREW!) - and nothing is more peaceful than a walk through the Paper Birch Grove. The 1850's main house was built to respect the land, making this home poised for entertaining both indoors and out. The kitchen communicates with a comfortable fire-lit living space and the formal dining room beyond. The family room is ideal for watching movies, assembling Liberty puzzles, or drawing the gardens. With a large first-floor bedroom suite and 2-3 upstairs bedrooms with a full bath, the period main home is as comfortable as it is charming; comprehensively updated systems (including a new cedar roof, fresh paint, and central air) make it effortless. The “Five-Star” guest cottage (with a large fire-lit bedroom, kitchen, and bath) sparkles beside a 50x25 heated swimming pool. A three-bed dormitory with an en suite bath provides delightful additional lodging. With ample storage, multiple garage bays, a fully equipped propane-fired sugar house, and a small red barn, this property is the perfect place to entertain and be entertained. Finished with an expert eye to design and detail, Maple Lane Farm is an uncommon opportunity to embrace an elevated Vermont experience.

Listed by Keri Cole of Williamson Group Sothebys Intl. Realty

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$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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207 Willey Hill Road Norwich VT 05055

Norwich, VT207 Willey Hill Road

Price$3,750,000

Est. Mortgage: $/month

MLS Number 5012289

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 6
  • Bathroom 9

THE POND AT WILLEY HILL- Sophisticated, triple mint, recently renovated estate minutes from Norwich set within a private 17+ acre oasis. This elegant home features relaxing views of the wildlife-laden large pond accompanied by landscaped grounds and seasonal long-range views. A pool, woodland trail and park-like fenced area complete this unique property. The home underwent an extensive renovation overseen by premier builders O'Hara & Gercke. The kitchen is sunny, comfortable, and designed for a gourmet cook; the dining room is positioned to take in the views of the pond and grounds. The living room is inviting in the cold months with its stone fireplace and offers a deck overlooking the land in the warmer months and stargazing year-round. The main floor also offers are a private library/bedroom and a well-appointed bedroom with views. On the second floor, the spa-like primary bedroom suite is integrated with nature - enjoy the sunrise over the pond from bed and the blue sky from the tub. A second ensuite bedroom is also on the second floor. The lower level offers a family room, which opens to a stone patio and the grounds beyond, as well as a large multi-purpose room (bedroom, office). The two-bedroom guest house is spacious and versatile and has a successful rental history. Both homes have whole-house generators, and there is a detached four-bay garage. Quick access to the Town of Hanover, Dartmouth College, and the best of the Upper Valley.

Listed by David Donegan of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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400 Ruusunen Road Springfield VT 05156

Springfield, VT400 Ruusunen Road

Price$3,650,000

Est. Mortgage: $/month

MLS Number 5009236

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 6
  • Bathroom 5

Wild Trails Farm offers unparalleled privacy, encompassing 436 acres of natural splendor. At the heart of this retreat is a 5,600+ sq ft lodge that is both luxurious and eco-friendly, powered by solar and geothermal. It features 6 spacious bedrooms, 4.5 bathrooms, a gourmet kitchen with dual dining areas, common rooms, and sauna. The 2-car garage is currently utilized as a yoga studio, but could be easily converted back. Whether you're relaxing on the stone patio with sweeping southern views or enjoying the cozy screened-in rear porch, you'll find the perfect spot to savor the tranquil surroundings. The magical grounds include manicured lawns, two ponds, colorful gardens, and seasonal fruit and berry patches. A 20+ km trail network winds through the property, perfect for hiking, biking, snowshoeing, and cross-country skiing. The land includes many natural and historic features, including inspiring, long-range vistas and also connects directly to numerous trails, backroads and features off site. The property comprises several additional structures: a restored circa 1800 barn with a 2-bedroom apartment and renovated farm manager's room with bath; the Cider House, a delightful 1-bedroom post and beam residence; post-and-beam stable; and equipment barn. Other features include a greenhouse, raised garden beds, pretty stone walls, a remote 2-bedroom off-grid cabin with septic and well, and a treehouse with wood stove and views. A rare opportunity to own a truly majestic property.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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348 Turtle Hill Road Ludlow VT 05149

Ludlow, VT348 Turtle Hill Road

Price$3,650,000

Est. Mortgage: $/month

MLS Number 5020831

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 5
  • Bathroom 4

This custom timber frame home, is a stunning embodiment of traditional barn-style construction that seamlessly blends modern comforts with rustic charm. The private 13.58 acres is perched at the end of a secluded road, offering breathtaking 180-degree mountain views over to Okemo. Visiting this property in person is the only way to appreciate its intricate construction and the magic of its view. Every hour is like having a birds eye view of mother nature at work. The beating heart of the home is a magnificent freestanding fieldstone fireplace, creating a warm cozy spot for gatherings after a day spent on the slopes. All chefs, young and old, will love the open exhibition style kitchen equipped with high-end appliances and the massive granite island perfect for everyone to gather around and pitch in. The open loft area provides a unique vantage point overlooking the expansive living space below, enhancing the home's airy feel. Discover the hidden gem of a cupola-reminiscent of a barn's hayloft-that serves as a serene getaway, ideal for yoga, meditation, or simply curling up with a good book. Complete with a three-car oversized garage, this remarkable property is an unparalleled escape that harmonizes luxury and tranquility. Enjoy ultimate comfort with the convenience of a whole-house generator and the peace of mind that comes with underground utilities. Consider this your invitation to experience this gorgeous home

Listed by Suzanne Garvey and Matthew Bellantoni of Mary W. Davis Realtor & Assoc.,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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37 Brothers Road Hartland VT 05048

Hartland, VT37 Brothers Road

Price$3,500,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4994787

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 3

Hartland Highlands is a singular Vermont agrarian paradise. The property's 277 pastoral acres, improved on over two decades of meticulous stewardship and management, feature rolling meadows, mixed northern hardwood forests, four ponds, three brooks, and miles of interior roads and trails. Conveniently located between Hanover, NH, and Woodstock, VT, this is one of the largest parcels of land currently available in the Upper Connecticut River Valley. The historic, expanded cape on the western side of Brothers Road is bounded by perennial gardens, antique stonewalls, heritage maples, and sweeping lawns. Built circa 1850, the house retains its original pine floors and exposed hand-hewn beams and enjoys an elevated, sunny position above the pastures. Views from the property extend to Smarts Mountain in the north and dramatic vistas of Mount Ascutney to the south. The heart of the home is an inviting, open eat-in kitchen that flows into the living and dining rooms. There is a spacious formal living room with a wood burning fireplace as well as a three-season glass and screened-in porch, and first-floor laundry and half-bathroom. Upstairs is a large primary suite with attached bath and two additional bedrooms served by a bath off the wide hallway and landing. Across Brothers Road to the east lies a significant barn complex offering a variety of purposes. This idyllic refuge offers a myriad of possibilities as the potential exists for the development of additional house sites.

Listed by Richard Higgerson of Higgerson & Company

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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61 Academy Circle Woodstock VT 05071

Woodstock, VT61 Academy Circle

Price$3,500,000

Est. Mortgage: $/month

MLS Number 5002873

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 6
  • Bathroom 6

Hyacinth House has been a landmark property in the historic village of South Woodstock from its early settlement in the 1800's. Sited on a knoll overlooking the Kedron Brook this grand residence has been carefully restored by talented craftsmen. Taking care to keep the beautiful original details the owners have brought the systems into the 21st century with the highest quality of materials. The back ell seamlessly ties into the original brick Federal and offers additional spaces for entertaining guests including the Pine Room with its' large fireplace for snowy winter nights. The brick Federal consists of formal living room, dining room, library and gourmet kitchen with walk in pantry. On the second floor there are 2 ensuite bedrooms,4 more bedrooms, 2 baths and large laundry room. The third floor offers the surprise of a family room that was originally a ballroom with curved ceiling. There is also a bright studio and half bath on that level. The new attached oversize 2 car garage is accessed from the Pine Room and the fully renovated basement. The 10 acres comprises of lovely landscaping around the home and plenty of land for gardens and animals. The 18th century barn and corn crib lend much charm to the setting. Walk to the charming village store and enjoy dinner on the porch of the Ransom Tavern. Only 5 miles to Woodstock and a short drive to multiple ski areas. South Woodstock is truly a bucolic place to call home! Call today for a private viewing.

Listed by Carol Wood of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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51 East Ash Road Plymouth VT 05056

Plymouth, VT51 East Ash Road

Price$3,399,000

Est. Mortgage: $/month

MLS Number 5025237

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 7
  • Bathroom 10

Welcome to Eureka House. This 7 bedroom Robert Carl Williams designed home is the ultimate in Vermont luxury and privacy. Enjoy unparalleled amenities like a 14-seat theater with stage, drive-through portico entrance, 2 story living room with gallery, 2 laundries, bedrooms are all en suite, and a 2 1/2-story carriage house with 3-car garage as well as living space above. The property is framed with beautiful stonework, patios, gardens, and a gently babbling stream. Exceptional craftsmanship coupled with the very finest materials makes this one of the nicest homes in the Hawk Resort community. Need to work remotely - the generous office suite provides what is needed to stay connected and affords some very nice views too. Game time is easy with a 2nd living room with billiards, an arcade game on the lower level, and a gaming/puzzle space on the top level. There's even a fun bunk room with a kid-sized bathroom. The carriage house is perfect for a private guest house or caretaker. The home has recently undergone system and mechanical upgrades to bring it up to date for easy living. Being sold fully finished makes it a true turn-key residence. Okemo Ski Resort is about 10 minutes away, Rutland Regional Airport is about 30 minutes away, and lots of hiking, biking, shopping, and fly fishing are close by. You must see it in person to appreciate this quality home in the Okemo Valley. Visit the Okemo real estate community today. Taxes are based on current town assessment.

Listed by Kevin Barnes of William Raveis Vermont Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2051 Gold Coast Road Bridgewater VT 05034

Bridgewater, VT2051 Gold Coast Road

Price$2,995,000

Est. Mortgage: $/month

MLS Number 4957886

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 4

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! Located 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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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210 Bear Hill Road Plymouth VT 05056

Plymouth, VT210 Bear Hill Road

Price$2,950,000

Est. Mortgage: $/month

MLS Number 5023210

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 6
  • Bathroom 8

Luxury properties of this caliber don't come on the market often, so if you are seeking the ultimate getaway retreat, you need to experience this one for yourself. Designed by famed Vermont Architect Robert Carl Williams and exquisitely crafted by Moore Construction, this Vermont Masterpiece features the finest finishes and most thoughtful details at every turn. Floor to vaulted-ceiling windows offer incredible mountain views. And with custom stonework surrounding three separate fireplaces on the main floor, and radiant floor heat throughout, you won't find a cozier place to relax and recharge. The open concept main floor combines kitchen, dining and living areas - perfect for entertaining - and the professional kitchen is certainly up to the task. Six en-suite bedrooms can sleep up to 22 comfortably. Other amenities include a pro-level fitness room, sauna, steam room, game room and a massive custom built stone hot tub outside that can seat 10+. Central AC keeps things comfortable all year round, and a Kohler whole house generator helps to keep the party going no matter the weather. Although it's located just minutes from both Okemo and Killington resorts, as well as world class hiking, biking and paddling, this beautiful post and beam residence is incredibly private, making this, perhaps, the perfect Green Mountain getaway property. This property is being sold professionally furnished & equipped and is turnkey, call for a private showing.

Listed by Bret Williamson of Killington Valley Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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340 North Hartland Road Hartford VT 05001

MLS Number 5026321

  • Commercial
  • County Windsor
  • Square Feet 13,144
  • Acreage 1.4

LOCATION, LOCATION, LOCATION!! PRIME in town Building and Land at the crossroads of I 89 and I 91 featuring a 12,000 +/- Square Foot Building on 1.40 +/- Acres. Build your business a new location along this high traffic main corridor. This Superb site is next door to Dunkin Donuts in White River Junction and would possibly be a great location for a car dealership, grocery store, restaurant or hotel. Become business neighbors with the V.A. Hospital, many prominent national hotel chains, Dunkin Donuts, McDonalds and several national automobile franchisees. Located just off I 89 & I91 in beautiful White River Jct., VT. this is a ONE OF A KIND LOCATION WITH HIGH VISIBILTY and HIGH TRAFFIC COUNT!! Seller is also willing to offer the property for $2,200,000. with less land and parking to be negotiated for the amount of land / parking area needed for each Buyers particular project.

Listed by Alex DeFelice of The Clerkin Agency,P.C.

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$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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318 Ebbin Lockwood Way Woodstock VT 05071

Woodstock, VT318 Ebbin Lockwood Way

Price$2,750,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4966761

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 4

Serene, private, contemporary: Sited on a ridge above South Woodstock village, the 54 acre property offers complete seclusion in an elegant setting with an extensive network of trails. The three bedroom main dwelling is sleek and elegant, with an open floor plan crafted to take in the beauty of the site with abundant use of organic material designed to integrate the design with the surrounding Vermont countryside. The two bedroom guest cottage has its own garage and entrance off of Ebbin Lockwood Way. The 6,048 s/f main house and 1,584 s/f guest cottage were designed by architect, Michael Weinberger. The property was recently renovated: main house was upgraded and many new system improvements. From the stone terrace, there are views of a cascading waterfall flowing into a small Koi pond and perennial gardens. On the Northeast side, an outside sitting area takes in views of a long, rolling meadow with a pond and a glimpse of the local hills. The main house includes a detached garage with additional storage space. Less than 1/2 mile from South Woodstock Country Store and Kedron Valley Inn/Ransom Tavern and one mile from Green Mountain Horse Association. 25 min. from Mt. Ascutney mountain biking trails, 38 min. from Killington and 2:23 hrs. from Boston.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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5518 Vt Route 12 Barnard VT 05031

Barnard, VT5518 Vt Route 12

Price$2,675,000

Est. Mortgage: $/month

MLS Number 4882340

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 6
  • Bathroom 6

An historic brick residence prominently located in an affluent and growing community! Conveniently situated within walking distance to the Elementary School, to year round recreation on beloved Silver Lake and to the classic Barnard General Store. All the amenities of Woodstock Village are just minutes away! World class medical care at Dartmouth Hitchcock Hospital and year round cultural events at Dartmouth College are well under an hour away! The spacious 1st floor consists of a state-of-the-art commercial kitchen, to please any gourmet chef, elegant formal dining rooms and for casual entertaining a tavern complete with bar. Upstairs you'll find a designer kitchen with ample cooking, eating & lounging spaces, 5 bedrooms & cozy reading nooks. A beautifully framed detached barn presents, on a lower level, a newly renovated yoga studio and guest suite with radiant floor heat! A large great room is above, for entertaining or studio space. These compelling structures are nestled on a well maintained 10 acres which include expansive lawns, gardens, and lush meadow paths leading to a secluded pond with a gazebo. Nearby the pond additional property value is provided by existence of a site for an additional 2 bedroom residence, with certified septic. A significant residence complimented by an extraordinary detached auxiliary building, with well conceived grounds! An opportunity to create a home base that could be long enjoyed by every generation of the family! Genuine Vermont appeal!

Listed by John Wetmore of Wetmore Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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5518 Vt Route 12 Barnard VT 05031

MLS Number 4882232

  • Commercial
  • County Windsor
  • Square Feet 8,363
  • Acreage 10

Established commercial property, minutes from Woodstock & Dartmouth. The historic brick building contains residential-commercial opportunities & the famous Barnard Inn restaurant, chef-owned 48 years. A stately residence for a family who wants to reside in an affluent growing community walking distance to school, Silver Lake and general store. Additionally, a site for weddings, retreats, renowned dining (newly renovated kitchen), hot yoga studio & boutique inn onsite. A welcome transition, after raising a family in the residence, the chef is excited for next stages of life. Nestled on 10 acres with gardens & meadow paths to a secluded pond with gazebo, the perfect wedding location. A 2-bedroom house site with certified septic for expansion ready at the pond. The main buildings first floor consists of a state-of-the-art commercial kitchen, elegant dining rooms & tavern. Upstairs you'll find a designer kitchen with ample cooking, eating & lounging spaces, 5 bedrooms & cozy reading nooks for your private residence and/or Inn. Unique to the region, Barnard's late noise curfew & ample parking make this an ideal versatile location for events in either the detached reception barn or under custom tents on the dedicated upper lawn designed for this use. The barn also has newly renovated yoga studio & guest suite with radiant floor heat. Bright summer gardens, gorgeous autumn foliage, adjacent VAST trails & ski mountains, a nature paradise, you'll fall in love with this property

Listed by John Wetmore of Wetmore Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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113 North Village Road Ludlow VT 05149

MLS Number 5012032

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 5
  • Bathroom 6

This beautiful and very spacious newly constructed home, with energy efficient upgrades, has over 6,000 square feet of living space on three levels. Within walking distance to the slopes, located close to the Base Lodge area, this home has everything a ski home needs. Enter through the carefully crafted front door into one of the two mudrooms, or through the two car garage or by the side mudroom and you will see walls of three-pane glass picture windows (for insulation and acoustics) looking at your mountain range view. An open floorplan with vaulted ceilings, large chef's kitchen with an island, hickory flooring, dining and living room with a fireplace that has a metal insert with internal blowing. There are 5 and a half bathrooms, plenty of spacious bedrooms, and a beautiful media/recreation room with a wall of windows, vaulted ceiling and view, which will be a fun space for entertaining guests! A hot tub, and covered porch/deck add to the exterior ambiance. Radiant heat on the ground floor, air recuperation system, 2x8 walls, foam insulation in walls and roof and more!

Listed by Elissa Scully of Mary W. Davis Realtor & Assoc.,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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851 Riverside Park Road Woodstock VT 05091

Woodstock, VT851 Riverside Park Road

Price$2,450,000

Est. Mortgage: $/month

MLS Number 5025630

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 4

"All Seasons" is the ultimate Vermont retreat, designed for gatherings and getaways while seamlessly blending rustic charm with modern luxury. This 5,900-sq-ft barn-style home, just over five minutes from Woodstock Village via Route 4 and the Lincoln Covered Bridge, sits high on a knoll above the Ottauquechee River with views to Killington. A veritable mini-resort, the property offers unparalleled access to recreational pursuits. Its 40-acre grounds feature single-track biking, hiking, and snowshoeing trails, a firepit, patio, grills, and owned riverfront access. A 32-foot indoor pool, and hot tub under the stars make this a year-round haven. The acreage also includes a potential building lot with mountain views and an existing roadway, adding versatility. Nearby, enjoy world-class skiing, golf, and other outdoor activities, with Woodstock Village offering charming shops and restaurants. Inside, the chef's kitchen boasts Viking appliances, granite counters, dual refrigerators, a pantry, and a custom island. Two expansive great rooms provide gathering spaces with large-screen TVs and plush seating, including a wet bar in the second-floor game room. Accommodations include four bedrooms, three full baths, and space for up to 12 guests. A highly successful Airbnb rental, “All Sessons” is an extraordinary opportunity to own a Vermont escape combining privacy, beauty, and income potential in one of the region's most picturesque towns.

Listed by Richard Higgerson of Higgerson & Company

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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18 Timber Creek Road Ludlow VT 05149

Ludlow, VT18 Timber Creek Road

Price$2,300,000

Est. Mortgage: $/month

MLS Number 5026376

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 5

Timber Creek on Okemo - A Mountain Retreat Like No Other. Discover the perfect blend of privacy and convenience with this stunning Timber Creek home, nestled on 3.31 serene acres at SouthFace Village on Okemo Mountain. Just steps from the Sunshine Quad, you'll enjoy unparalleled mountain access alongside exclusive amenities. This 4-bedroom, 5-bathroom, 3-level timber frame home offers an inviting open floor plan, ideal for hosting family and friends. Soaring cathedral ceilings showcase the craftsmanship of the timber frame design, while the crackling wood-burning fireplace serves as the centerpiece of the cozy living area making this the perfect mountain retreat. The chef's kitchen, featuring a large island, encourages lively gatherings, conveniently open to the dining room perfect for shared meals and many memories. The main level boasts an en suite bedroom, while upstairs you'll find three additional bedrooms, two with private baths making for great guest quarters. The lower level is designed for fun, with a spacious family room perfect for movie or game nights. With a two-car garage, mudroom for all your gear, and access to SouthFace Village amenities-including easy access to the Sunshine Quad located within Southface Village offering you great mountain access, a recently constructed clubhouse, heated outdoor pool and spa, fitness center, locker, and private parking-you'll have everything you need for a luxurious mountain lifestyle!

Listed by Katherine Burns of William Raveis Vermont Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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63 Main Street Ludlow VT 05149

MLS Number 4942384

  • Commercial
  • County Windsor
  • Square Feet 17,016
  • Acreage 1

THE KEY IS ALREADY TURNED! Of course the term turnkey is meant to imply that you need only unlock the door to take over your new business. Sports Odyssey redefines the term because even the aspects of these two sterling business locations in Ludlow and Dover which a new owner might not know to ask for, have already been built in to these successful, yet poised-for-growth enterprises. Ski rentals across the child-adult spectrum? Of course! Cutting edge ski equipment sales of the best brands? You bet! Onsite equipment for ski and snowboard maintenance? State of the art! Inviting displays, sitting areas and fitting rooms? Thought of that! Massive storage and inventory capacity? Beautifully maintained and inviting facilities which bring the consumer joy? Abundant parking? Great proximity to the slopes? Yes, we have it all. These already successful going concerns are poised for even more growth based on the expanding ski market and the strong and continuing influx of new sports vacation traffic in Vermont. Successfully built and managed by a highly professional two-brother team who will be happy to help you with a successful transition period, and share their years of successful experience in building your new business. Call today for a tour. These properties are as good as it gets! See MLS# 4942451 for Dover.

Listed by Zachary Zupan and Lawrence Zupan of EXP Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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121 Snowbridge Road Ludlow VT 05149

Ludlow, VT121 Snowbridge Road, Unit S5

Price$2,250,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4967802

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 5

Located directly on the Sachem Trail, this wonderful slopeside home in the Snowbridge community is on the market for the first time by its original owners. Open main level plan includes a well designed kitchen with breakfast bar leading to a separate dining area with windows overlooking the trail. The expansive living room is majestically centered by a woodburning fireplace and accesses a wrap around deck with direct slope views. The owners' suite is privately tucked away and features a gas fireplace, whirlpool tub, walk in closet, and privacy balcony. A large loft area occupies the upper floor and overlooks the main level fireplace facade. The lower level offers two additional bedrooms, one ensuite, a family room with gas fireplace and wet bar, a bonus room, and a media room with theatre seating and screening. A well positioned mud room completes this impressive floor plan and puts you a few quick steps to the slopes. Recent exterior renovations completed in Spring 2024.

Listed by Andre Menard of Mary W. Davis Realtor & Assoc.,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Copyright 2025 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 January 21, 2025 7:22 AM EST