Woodstock, VT Real Estate

249 Sawyer Road Woodstock VT 05091

Woodstock, VT249 Sawyer Road

Price$3,750,000

Est. Mortgage: $/month

MLS Number 5018393

  • Residential Single Family
  • Full Bath 1
  • Address 249 Sawyer Road
  • Construction Existing
  • Bedrooms 3

This extraordinary residence offers breathtaking views of Billings Farm Preserve and the Green Mountains from nearly every corner, with Vermont's only national park directly in sight. The charming town of Woodstock, known for its boutiques and dining, is just a short walk away. Nestled at the end of a quiet road, the property offers unobstructed west-facing views for spectacular sunsets, surrounded by acres of undeveloped land. Woodstock's restrictive covenants ensure these views remain undisturbed, creating a peaceful, private escape. The expansive deck around the stunning pool is controlled via smartphone, with an automatic cover to ease maintenance. The adjacent pool house features a custom kitchen, a luxurious bathroom, and a cozy living area framed by floor-to-ceiling glass, offering year-round comfort with air conditioning and heated floors. The inground, heated, 30,000 gallon pool, can reach over 102 year-round, a rare feature in Vermont. An NBA hoops basketball net is installed in the shallow end for many days of fun, or if the deep end is more your style this pool offers a 9 foot deep end. This unique property offers proximity to skiing, golf, hiking, and more. The view encompasses the only National Park in Vermont. Marsh-Billings-Rockefeller in Vermont is the only national park to focus on conservation history and the evolving nature of land stewardship in America located right here in beautiful Woodstock VT! Contact us today to arrange a private tour!

Listed by Elevations Team of Real Broker LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 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
  • Full Bath 2
  • Address 61 Academy Circle
  • Construction Existing
  • Bedrooms 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: 6.67% last updated on Mar 20, 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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4945 South Road Woodstock VT 05071

Woodstock, VT4945 South Road

Price$2,485,000

Est. Mortgage: $/month

MLS Number 5028924

  • Residential Single Family
  • Full Bath 3
  • Address 4945 South Road
  • Construction Existing
  • Bedrooms 5

The John Arnold Cottle House is a landmark residence in the heart of South Woodstock, a rare blend of village convenience and country living. Built in 1811 by one of the area's earliest settlers, this stately Federal-style brick home has been thoughtfully restored to honor its historic charm while integrating modern comforts. Set on 2.7 acres, the property features 450 ft of frontage on Kedron Brook, along with a firepit, a barn, and a river meadow. The barn-currently used for storage-could easily be converted to accommodate a couple of horses or sheep. The 3-bedroom main house has elegant 12-over-12 windows, high ceilings, and beautifully preserved period details, including a 2nd-floor ballroom with a coved ceiling and fiddler's stage-a nod to its past as a lively gathering space. The newer addition overlooking the brook has a magnificent great room with 17' cathedral ceilings and a gourmet kitchen and wood burning brick fireplace. The renovated Kingsley Barn guest house offers 2 bedrooms, a loft, and a deck overlooking the brook. Below there is a heated workshop, ideal for puttering and creating. A timber bridge spans the waterway, connecting the property's field, barn and trails. With direct access to the Upwey Trail system and equestrian paths leading to the Green Mountain Horse Association, this property is ideal for outdoor enthusiasts. Located along South Road in the South Woodstock Historic District.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 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
  • Full Bath 1
  • Construction Existing
  • 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: 6.67% last updated on Mar 20, 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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2706 East Woodstock Road Woodstock VT 05073

MLS Number 5020107

  • Commercial
  • Village Taftsville
  • Year Built 1850
  • Square Feet 6,000
  • Acreage 0.56

INVESTMENT & RESIDENTIAL OPPORTUNITY - Rare historic building (The Taftsville Country Store) available for owner occupancy with multiple additional income units in the village of Taftsville. Just five minutes to the quintessential New England Village of Woodstock! Property includes store with bath (approved for restaurant, café, or retail store), Post Office (with current lease), Apartment 1 (with excellent AIRBNB rental history), Apartment 2 (The owner's unit- 3 bedroom, 2 bath), and plans/space for an additional studio unit. Perfect opportunity for an investor to offset living expenses with this multi-unit property, or just have a super fancy home office downstairs. Potential diversified income streams with hospitality, residential rental, and retail/ food service all in one property. Current owners have redesigned and graded the parking lot to include 27 parking spaces and EV Conduit for 2 charging stations that can accommodate 4 vehicles, ADA access to building, and ADA accessible restrooms. Property boasts gorgeous patio views of the Ottauquechee River and Taftsville Covered Bridge.

Listed by John Bassette of Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 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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2706 East Woodstock Road Woodstock VT 05091

Woodstock, VT2706 East Woodstock Road

Price$2,000,000

Est. Mortgage: $/month

MLS Number 5020106

  • Residential Single Family
  • Full Bath 2
  • Village Taftsville
  • Construction Existing
  • Bedrooms 4

INVESTMENT & RESIDENTIAL OPPORTUNITY - Rare historic building (The Taftsville Country Store) available for owner occupancy with multiple additional income units in the village of Taftsville. Just five minutes to the quintessential New England Village of Woodstock! Property includes store with bath (approved for restaurant, café, or retail store), Post Office (with current lease), Apartment 1 (with excellent AIRBNB rental history), Apartment 2 (The owner's unit- 3 bedroom, 2 bath), and plans/space for an additional studio unit. Perfect opportunity for an investor to offset living expenses with this multi-unit property, or just have a super fancy home office downstairs. Potential diversified income streams with hospitality, residential rental, and retail/ food service all in one property. Current owners have redesigned and graded the parking lot to include 27 parking spaces and EV Conduit for 2 charging stations that can accommodate 4 vehicles, ADA access to building, and ADA accessible restrooms. Property boasts gorgeous patio views of the Ottauquechee River and Taftsville Covered Bridge.

Listed by John Bassette of Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 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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10 College Hill Road Woodstock VT 05091

Woodstock, VT10 College Hill Road

Price$1,999,000

Est. Mortgage: $/month

MLS Number 5031704

  • Residential Single Family
  • Full Bath 3
  • Address 10 College Hill Road
  • Construction Existing
  • Bedrooms 5

10 College Hill is the perfect in-village residence, off the main road yet walk-to-everything. The original, historic residence was designed in 1916 by renowned architect John Russell Pope whose accomplishments include the Jefferson Memorial, and master plans for Dartmouth and Yale. It also enjoys modern additions and updates including a stunning first-level primary bedroom suite designed in 2012 by the respected local architect David Bielman. The front door welcomes guests with a pair of dutch-doors in a center entrance foyer, flanked by a classic dining room and elegant living room (both with fireplaces). The classic butlers pantry leads to the gourmet kitchen and a wonderful, sunny eat-in breakfast area. There are 4 additional BRs upstairs, 2 have ensuite baths plus a 3rd hall bath. There are also powder baths on the first floor and in the lower (basement) area. All BRs have central air. Mechanicals have been updated and well-maintained. 2 other offices on 1st and 2nd floor, and the basement has living space, a workout room, safe room, and ample storage. Beyond the kitchen is a mud-laundry room that leads to the covered (heated) brick walkway from the garage. The 1.05 acre parcel has professionally designed and executed gardens, patios and stone walls including new stone steps that lead up to a second new stone patio that enjoys sweeping vistas across to Mt Tom and the Marsh-Billings-Rockefeller National park. SEE FULL PROPERTY WEBSITE.

Listed by John Snyder of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 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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20 The Green Woodstock VT 05091

Woodstock, VT20 The Green

Price$1,995,000

Est. Mortgage: $/month

MLS Number 5033342

  • Residential Single Family
  • Full Bath 1
  • Address 20 The Green
  • Construction Existing
  • Bedrooms 3

Stunning antique cape! Located in the 'heart' of Woodstock. Originally located on Central Street- this home was moved in the 1960's to this location and had a full renovation in 2011. The antique brick section was built in 1826- it boasts a spacious living room anchored with a large wood burning fireplace, original wide pine floors and lots of space for entertaining. Adjacent find a quaint library with fireplace to curl up with a book on a cold winter day. Off the library is a bathroom and den/bedroom/office. Upstairs includes two more guest bedrooms and bathroom. The new back ell has beautiful architectural lines and features a large kitchen open into an informal and formal dining room anchored by an Austrian- Biofire wood stove. Handsome woodwork, immense amount of sunlight overlooking the perennial gardens. The back of the house has a gracious primary suite with an abundance of space including a reading nook, large en suite bathroom, generous walk in-closet and laundry. New foundation with poured concrete floors, ample storage space as well as an oversized 2 bay detached garage- with generator. Walk to all of towns amenities, restaurants and theatre. Easy stroll to Mtn Peg and Mtn Tom for those hiking enthusiasts. Championship golf, skiing and fly-fishing near by. This is truly an idyllic village home in historic Woodstock that is considered one of the 'prettiest towns in America".

Listed by Gretchjen Smith of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 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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484 Carlton Hill Road Woodstock VT 05091

Woodstock, VT484 Carlton Hill Road

Price$1,800,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5032740

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 4
  • Bathroom 5

Make this unique Adirondack-style home, with its rich stone and timber frame, and perfect location along the banks of the Ottauquechee River, your new Vermont retreat. Every window offers a stunning view of Mt. Tom, and the rushing river, making it a nature lover's paradise. The fieldstone fireplace soars two stories high in the great room, which is flooded with natural light through expansive thermal glass windows. This generous gathering space hosts a dining area and breakfast bar adjacent to an outstanding chef's kitchen. Crafted with meticulous attention to detail, this remarkable residence features four bedrooms and five bathrooms. The first-floor primary suite is a private sanctuary, boasting custom built-in 'his & hers' closets, a spacious spa-like bathroom, and a secluded sundeck. The tavern room, with its vaulted ceiling, stone fireplace and cherry wood bar makes this the go-to house for friends gathering at any time, but especially on Fourth of July. On the second floor, you'll find a luxurious Primary Bedroom with an en suite bath, an office/study with an adjacent ¾ bath, and a whimsical Children's Suite complete with cozy sleeping alcoves, and charming nooks.Conveniently located within walking distance to Woodstock High and Middle Schools, the Union Ice Arena, and the ever-popular Woodstock Farmer's Market grocery store, this splendid home offers the perfect balance of privacy without isolation.

Listed by Jennifer Kirkman and Jennifer Falvey of KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 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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1522 Barnard Road Woodstock VT 05091

Woodstock, VT1522 Barnard Road

Price$1,650,000

Est. Mortgage: $/month

MLS Number 5027640

  • Residential Single Family
  • Full Bath 3
  • Address 1522 Barnard Road
  • Construction Existing
  • Bedrooms 5

Just over 2 miles from the heart of Woodstock village, this gracious brick cape sits on six open acres. Designed to accommodate a Vermont lifestyle, this home welcomes you, whatever the season. The chef's kitchen has been expanded with a spacious entertaining room, and the grand dining room is ideal for hosting. A wood-burning fireplace in the main living room, a brick fireplace in the family room, and a gas-ready fireplace in the den make this home cozy during Vermont's cooler seasons. With 3-4 bedrooms on the second floor (one with fireplace), and an additional bedroom/office above the garage, 1522 Barnard Road offers plenty to a growing family and is a perfect retreat for guests. The surrounding grounds present an uncommon opportunity to own usable acreage in quick proximity to Woodstock. A covered porch for grilling, an entertainment patio, an inground pool with heat hookup, a garden space, an apiary, and a fenced chicken coop make summers at this home idyllic. Dogs can run free with over 5 acres of invisible fencing. Adjacent to the site of the country's first ski tow, winter offers fantastic snowshoeing opportunities and easy access to Saskadena 6. With quick access to I-89 and the Upper Valley beyond, this Woodstock home lends itself to both primary and second-home ownership. An increasing rarity in our market, this home is uniquely positioned to enjoy elbowroom and a more rural landscape, all just minutes from New England's quintessential village.

Listed by Keri Cole of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 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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15 Central Street Woodstock VT 05091

Woodstock, VT15 Central Street

Price$1,550,000

Est. Mortgage: $/month

MLS Number 5031244

  • Residential Single Family
  • Village Woodstock
  • Address 15 Central Street
  • Construction Existing
  • Bedrooms 4

15 Central Street is one of the finest commercial locations in Woodstock with two of the most creative and successful businesses as the anchor tenants. The property has adapted to changes of the course of its long history of uses including residential shop owner, a barber shop, a dance & pool hall, law office, architectural services and a variety of mercantile endeavors. Notably, the building was the headquarters of Lt Colonel Peter T. Washburn, who led the 1st Vermont Regiment troops in their crucial role at Gettysburg. He returned to become Adjutant and Inspector General to organize and direct Vermont's military efforts through the rest of the Civil War from his offices at 15 Central Street. The current owner, recognizing it was time to adapt the building to the 21st Century, developed plans to upgrade and modernize the second and third floors for mixed use including an incredible residential unit with exposed brick walls and timber framing. The story high historic windows have been restored, and the second level has been reframed with new sheetrock for office or residential use. The third level partition walls have been removed to create a dramatic open area with views over the village to the north and south leaving the finishes and uses of the two levels up to your imagination. This is a once-in-a-lifetime opportunity to acquire a property with a remarkable history and become part of creating Woodstock's future.

Listed by Laird Bradley and Danny Kogut of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 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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15 Central Street Woodstock VT 05091

MLS Number 5031228

  • Commercial
  • Village Woodstock
  • Address 15 Central Street
  • Year Built 1840
  • Square Feet 6,612

15 Central Street is one of the finest commercial locations in Woodstock with two of the most creative and successful businesses as the anchor tenants. The historic building has adapted to changes over the course of its long history of uses including residential, barber shop, a dance & pool hall, law office, architectural services and a variety of mercantile endeavors. Notably, the building was the headquarters of Lt Colonel Peter T. Washburn, who led the 1st Vermont Regiment troops in their crucial role at Gettysburg. He returned to the roles of Adjutant and Inspector General to organize and direct Vermont's military efforts through the rest of the Civil War from his offices at 15 Central Street. The current owners, recognizing it was time to adapt the building to the 21st Century, developed plans to upgrade and modernize the second and third floors for mixed use including an incredible residential unit with exposed brick walls and timber framing. The story high historic windows have been restored, and the second level has been reframed with new sheetrock. The third level partition walls have been removed to create a dramatic open area with views over the village to the north and south leaving the finishes and uses of the two levels up to your imagination. This is a once-in-a-lifetime opportunity to acquire a property with a remarkable history and become part of creating Woodstock's future. Note: Gross income reduced in 2024 due to renovation

Listed by Laird Bradley and Danny Kogut of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 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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458 Woodstock Road Woodstock VT 05091

Woodstock, VT458 Woodstock Road

Price$1,499,000

Est. Mortgage: $/month

MLS Number 4945772

  • Land
  • Address 458 Woodstock Road
  • Acreage 4.57
  • Area VT-Windsor
  • Utilities Telephone Available

It has been said that the highest and best use of this landmark Woodstock property would be a combination of constructing multiple residential units, in the private rear acreage, and commercial development, of the highly visible Route 4 road frontage. There is no question of the unlimited potential! Highly visible! Well located, on the East End entrance route to Woodstock Village! This property owned by Gerrish Corporation, commonly known as “Woodstock East,” located at 458 Woodstock Road, Woodstock, Vermont, contains 4.5 acres, more or less. The property is located in the Commercial/Light Industrial Zone, allowing a multitude of commercial, industrial and residential uses of the property. The property was the site of a substantial gasoline spill in 1973. However, the property was enrolled in the Vermont Brownsfield Reuse Environmental Liability Limitation Act program (10 V.S.A. 6641-6656) in 1999 and was successfully remediated. On June 5, 2012 the Vermont Agency of NaturalResources signed a Certificate of Completion, thereby providing protection to third party purchasers of the property pursuant to 10 V.S.A 6653(a) from any liability arising from any contamination on the property which occurred prior to that date, making this one the safest properties in Vermont from a pollution liability perspective. Location, location, location!!

Listed by John Wetmore of Wetmore Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 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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458 Woodstock Road Woodstock VT 05091

MLS Number 4945749

  • Commercial
  • Village Woodstock
  • Address 458 Woodstock Road
  • Acreage 4.57
  • Area VT-Windsor

It has been said that the highest and best use of this landmark Woodstock property would be a combination of constructing multiple residential units, in the private rear acreage, and commercial development, of the highly visible Route 4 road frontage. There is no question of the unlimited potential! Highly visible! Well located, on the East End entrance route to Woodstock Village! This property owned by Gerrish Corporation, commonly known as “Woodstock East,” located at 458 Woodstock Road, Woodstock, Vermont, contains 4.5 acres, more or less. The property is located in the Commercial/Light Industrial Zone, allowing a multitude of commercial, industrial and residential uses of the property. The property was the site of a substantial gasoline spill in 1973. However, the property was enrolled in the Vermont Brownsfield Reuse Environmental Liability Limitation Act program (10 V.S.A. 6641-6656) in 1999 and was successfully remediated. On June 5, 2012 the Vermont Agency of NaturalResources signed a Certificate of Completion, thereby providing protection to third party purchasers of the property pursuant to 10 V.S.A 6653(a) from any liability arising from any contamination on the property which occurred prior to that date, making this one the safest properties in Vermont from a pollution liability perspective. Location, location, location!!

Listed by John Wetmore of Wetmore Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 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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608 Fletcher Hill Road Woodstock VT 05091

Woodstock, VT608 Fletcher Hill Road

Price$1,399,000

Est. Mortgage: $/month

MLS Number 5028430

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4

Open House Saturday, March 22, 12:00 to 2:00 - Tucked away in the serene forests of Woodstock, Vermont, this beautifully remodeled 11-room home offers 4 bedrooms, 4 bathrooms, and 4,225 sq. ft. of luxurious living space on 5.4 private acres. The open-concept design is flooded with natural light, featuring a stunning chef's kitchen with high-end stainless steel appliances, Vermont soapstone counters, custom cabinetry, and a spacious and sunny dining room. The cozy living room boasts one of two wood stoves, creating a warm and inviting space for relaxation. The massive family room is home to the second wood stove. There are two primary en-suites, each with a fireplace and spa-like bathroom, one in a private wing of the home, while the additional bedrooms and updated baths provide comfort and style. Outside, a large, partially screened-in deck and hot tub offer perfect spots to unwind and enjoy the tranquil surroundings-there is even a sauna off the rec room! Plenty of storage is available in the two-car garage or the two-stall barn. With solar panels, propane heating, two fireplaces, and two wood stoves, this home combines eco-friendly features with modern amenities. Its peaceful setting, just minutes from downtown Woodstock, is also close to the Green Mountain Horse Association, VAST snowmobile trails, Killington Mountain, Mount Tom, and the Saskadena Six Ski Area, making it a perfect full-time residence or seasonal escape. Enjoy Vermont living or work from home with EC Fiber!

Listed by Sandy Reavill of Real Broker LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 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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1075 Westerdale Road Woodstock VT 05091

Woodstock, VT1075 Westerdale Road

Price$1,395,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5022674

  • Residential Single Family
  • Full Bath 2
  • Address 1075 Westerdale Road
  • Construction Existing
  • Bedrooms 3

This lovingly maintained property with mountain views has been enjoyed by a single family since its construction in 1985. The open-concept layout is anchored by a stone Rumford fireplace, which along with the southern exposure warms the large easy-to-keep space. The first floor master boasts ample storage with a sliding door for quick access to the grounds. Across from the main house via a covered breezeway is a large 2 car garage, gorgeous horse barn with hay loft and a cozy studio apartment, making this the perfect spot for a variety of uses. Equally comfortable as a part-time or full-time home, this property is conveniently located on the western side of Woodstock, just twenty minutes from Killington's Skyeship gondola and ten minutes from downtown Woodstock. With over forty acres on prestigious Westerdale road, owners enjoy privacy and expansion potential. Offered for the first time since its inception, this property is an exceedingly rare opportunity for rolling acreage in a highly coveted location.

Listed by Keri Cole of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 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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119 English Mills Way Woodstock VT 05091

Woodstock, VT119 English Mills Way

Price$1,150,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4991097

  • Residential Single Family
  • Full Bath 3
  • Construction Existing
  • Bedrooms 5
  • Bathroom 5

An expansive 5 bedroom home, in a private location, conveniently just a few minutes drive from Woodstock Village! Among often sought amenities are a ground floor primary bedroom suite with private bath, a dramatic great room with cathedral ceiling and wood burning fireplace, a generously sized lower level in-law/guest suite with kitchen, dining, living room and bedroom with bath, 3 additional upper level bedrooms with 2 full baths, a family room with an attractive soap stone wood burning stove, a bright kitchen with cherry cabinets and an attached 2 car garage. The well conceived design presents the practical opportunity for single level living utilizing the gracious ground floor bedroom suite. Alternatively, the 5 bedrooms, on 3 levels, can satisfy a whole gang! The lower level private suite could present comfortable accommodations for an in-residence caregiver. Outside, a large wrap around deck transitions to pleasant sunny lawn areas with perennial gardens. Within walking distance are Mt. Tom's hiking trails! The property benefits from owner's who have taken pride in maintaining their beloved home! An attractive home that benefits from a thoughtful interior design! Equally suited for use as a well located year round residence or to be the vacation home that can accommodate friends and family alike! Skiing at Suicide Six as well as all the well known Woodstock Village amenities of shopping, dining and cultural events are just minutes away! Truly a great Woodstock property!

Listed by John Wetmore of Wetmore Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 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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598 East Woodstock Road Woodstock VT 05091

MLS Number 5017395

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3

This stately, rambling gambrel home offers privacy, convenience, antique charm, and room for everyone. Walking distance to the east end of Woodstock village, on 2.9 lush acres including a fenced backyard, a fenced vegetable garden, and extensive perennial beds. The home is a stunning mixture of antique touches and modern functionality, with beautiful built-ins and closet spaces at every turn. The home has a suite of rooms on the first floor that are perfect for a home-based business or studio area (or 2 extra bedrooms plus bonus room), and a one-bedroom full bath (with office & kitchen) in-law suite upstairs with private ground-level access. The main part of the home includes three additional bedrooms, a library, a music room, living room, dining room, two full baths, dressing room, and three-season enclosed porch. The charming eat-in kitchen includes beautiful display cabinets, hand painted tiles, and built-in pantry and laundry. In the stunning custom cherry wood library with marble fireplace and private deck, bibliophiles will find more than enough shelf space for their entire book collection, and a quiet, peaceful setting in which to read. Two readers in the family? The upstairs music room is similarly equipped, also with stunning cherry wood built-ins and detailing. Two staircases provide ample access to the upstairs and contribute to the ambling nature of the home. Walk to restaurants and a river front park!

Listed by Geoff Eckler of Real Broker LLC

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$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 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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19 Linden Hill Street Woodstock VT 05091

Woodstock, VT19 Linden Hill Street

Price$875,000

Est. Mortgage: $/month

MLS Number 5031942

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • Bedrooms 3
  • Bathroom 4

Perched along scenic Linden Hill, this stunning village home offers exceptional privacy, comfort, and spacious interiors. A paved driveway leads to a one-car garage with a covered entrance, ensuring effortless access in all seasons. Inside, a generous mudroom provides a practical transition into the inviting living room, featuring a cozy propane fireplace, or the well-appointed kitchen with sleek stainless steel appliances. The sunlit dining room, complete with French doors, opens to a charming patio-perfect for outdoor relaxation. The main level also features a private primary suite with an attached bathroom and laundry, along with a conveniently located half-bath for guests. Upstairs, two additional bedrooms, a full bathroom, and a dedicated office space provide ample living accommodations. Equipped with four energy-efficient mini-split systems for year-round climate control, the home also features a forced hot air system for added warmth during colder months. The full basement, with its poured concrete foundation and impressive ceiling height, offers excellent storage or potential for further customization. Ideally situated less than half a mile from the Village Green and Woodstock Country Club, this central location is truly unbeatable. Don't miss the opportunity to experience this exceptional home-schedule your private showing today!

Listed by Holly Hall and Franchesca Collins of Hall Collins Real Estate Group

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$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 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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234 Randall Road Woodstock VT 05091

Woodstock, VT234 Randall Road

Price$845,000

Est. Mortgage: $/month

MLS Number 4913852

  • Residential Single Family
  • Full Bath 1
  • Address 234 Randall Road
  • Construction Existing
  • Bedrooms 2

Randall Road Farm represents a rare opportunity to purchase a multigenerational family farmstead in an exceptionally desirable location. Long recognized as a well established farm raising Charolais beef cattle, poultry and hay. The owner has been the farmer/steward of many of the areas farms in the Woodstock and South Woodstock. The property has a single family dwelling, shop building with farm office, hay and dairy barns, multiple storage and ancillary structures. Whether looking to engage in the localvore food movement or looking to build a residential home on arguably the most desirable land parcel a stones throw from Woodstock Village, this property has location, setting and features that would be hard to replicate. The upper pasture with easy access has great views, privacy and a commanding location.

Listed by Wade Treadway of Wade I Treadway Real Estate

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$
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$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 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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25 Linden Hill Street Woodstock VT 05091

Woodstock, VT25 Linden Hill Street

Price$795,000

Est. Mortgage: $/month

MLS Number 5028831

  • Residential Single Family
  • Full Bath 1
  • Village Woodstock
  • Construction Existing
  • Bedrooms 3

This classic early 20th Century farmhouse with 3 sunny bedrooms and two baths is sited on a quiet Village Street uphill above the Woodstock Elementary School and across from the public playground at Vail Field and the Woodstock Country Club golf course. The home has benefitted from the thoughtful additions of an eat-in kitchen and a front porch where you can enjoy long summer evenings. A comprehensive renovation several years ago opened the main level floorplan to eliminate partitions adapting the house to modern lifestyles. The backyard rises in tiers from the lower level with picnic table and grilling area to an elevated plateau used for expansive vegetable and flowers gardens. Truly a joyful place to call home in the heart of Woodstock's historic community.

Listed by Laird Bradley of Williamson Group Sothebys Intl. Realty

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$
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$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 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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6963 South Road Woodstock VT 05071

Woodstock, VT6963 South Road

Price$795,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5032545

  • Residential Single Family
  • Full Bath 1
  • Address 6963 South Road
  • Construction Existing
  • Bedrooms 2

Enchanting cottage perched on a private knoll with short range views. This property consist of 33 acres with a mixture of open meadow and woods for those looking for an afternoon of walking or snowshoeing. It is currently enrolled in the Current Use Forestry program. Stunning perennial gardens enhance the handsome stone walls and stone walk way to the residence. It's a Garden enthusiasts haven with different variety of ferns. This cozy cottage boast 2 bedrooms, 1.5 baths with 2 loft spaces. It's a perfect open floor plan for entertaining with wide pine floors, exposed beams and anchored by a pellet stove in the living room to cozy up with a book on a winter afternoon. This residence has the advantage of being on one level. Large mudroom leads out to a wonderful covered porch or sunbath on the south-facing back deck in the afternoons. There is a large detached 2 bay garage and generator hook up. Just minutes to GMHA and the Kedron Valley Inn. Championship golf, skiing and fly-fishing on the Black River near by. Woodstock Green is approx 6 miles for access to all the stores, restaurants and amenities. It's a lovely cottage being sold by the original owners- come take a look!

Listed by Gretchjen Smith and Carol Wood of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 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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71 Central Street Woodstock VT 05091

MLS Number 5030980

  • Commercial
  • Village Woodstock
  • Address 71 Central Street
  • Year Built 1990
  • Square Feet 3,678

A highly visible commercial building located in Historic Woodstock Village! Architecturally designed to afford multi-use potential! 3 distinct interior spaces can function and flow together as components of a single commercial enterprise or these spaces can stand apart, as 3 separate units. Unit A comprises 1,435 square feet and is located on the east side of the lower and upper levels of the brick portion of the building. Unit B comprises 712 square feet and is located on the west side of the lower level in the wooden frame portion of the building. Unit C comprises 1,531 square feet and is located on the west side of the upper level of the wooden frame portion of the building. A prime site for a retail store, a restaurant with the added benefit of outside seating options, an office space conveniently within walking distance of all the amenities of Woodstock Village, or a combination of several of these different commercial options. This attractive brick building benefits from street level access directly on the village sidewalk as well as separate second floor access. Currently, an active restaurant is a tenant.

Listed by John Wetmore of Wetmore Real Estate

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$
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$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 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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13 Slayton Terrace Woodstock VT 05091

Woodstock, VT13 Slayton Terrace

Price$785,000

Est. Mortgage: $/month

MLS Number 5033279

  • Residential Single Family
  • Address 13 Slayton Terrace
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3

Charming cottage located in the heart of historic Woodstock Village with walking distance to all the shops, restaurants and town theatre. Mtn Peg walking trails just a 2 minute walk from front door for those hiking enthusiasts. This home is filled with an abundance of natural sunlight and features all hardwood floors throughout. New kitchen with butcher block counters, stainless appliances, maple flooring and lighting that opens into the dining room accented with a lovely bay window for additional lighting. High ceilings with moldings throughout. Living room features lots of windows and propane stove for those looking to curl up with a book on a cold winter day. Ample room for entertaining. New front door opens to a renovated wrap around covered porch for afternoon tea. Upstairs has 3 bedrooms, renovated bath, shiplapped walls along with all the charm that comes with a 1920's home. New windows, lovely perennial gardens accented with stunning apple tree in front yard when it bloom...as well as a privacy fence. Come take a look... charming cottage in one of America's prettiest towns.

Listed by Gretchjen Smith of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 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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548 West Woodstock Road Woodstock VT 05091

MLS Number 5032952

  • Commercial
  • Square Feet 8,450
  • Acreage 0.2
  • Area VT-Windsor
  • PricePerSqFt 82.84

Over 8,000 square feet of versatile space now available for sale or lease at the historic Mill Mall in Woodstock, Vermont! This expansive commercial condo Unit A-1B offers endless possibilities and is located in a prime, high-traffic area on Route 4, perfectly positioned between Killington and downtown Woodstock. With its large footprint, the space can easily accommodate multiple tenants or one larger business looking for ample room to grow. Whether you're seeking a location for a brewery, restaurant, retail store, or warehouse/storage, this property offers the flexibility and visibility needed to succeed. Come be part of the ongoing revitalization of this iconic property!

Listed by Andy Paluch of Longview Commercial Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.67% last updated on Mar 20, 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 March 26, 2025 10:12 AM EDT