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Woodstock VT Real Estate

Once named the “Prettiest Small Town in America” Woodstock is the shire town of Windsor County, Vermont. Its picturesque village has won awards for its beautiful scenery and streetscapes making it a year-round destination. The town of Woodstock hosts several annual events and festivals including December’s Wassail Weekend in which the town transforms into a winter wonderland with lights, decorations, and charm. Woodstock is home to a welcoming, tight-knit community that embraces the town’s unique character. 

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2034 Long Hill Road Woodstock VT 05071

Woodstock, VT2034 Long Hill Road

Price$9,250,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4943673

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

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

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

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

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.9% last updated on 2024-02-22

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

318 Ebbin Lockwood Way Woodstock VT 05071

Woodstock, VT318 Ebbin Lockwood Way

Price$2,995,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4966761

  • Residential Single Family
  • Square Feet 6,443
  • Bathroom 4
  • Bedrooms 3
  • Construction Existing

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

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

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Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.9% last updated on 2024-02-22

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

2709 W Woodstock Road Woodstock VT 05091

Woodstock, VT2709 W Woodstock Road

Price$2,750,000The price has recently decreased

MLS Number 4982842

  • Commercial
  • Square Feet 7,769
  • Acreage 5.5
  • PricePerSqFt 353.97

Discover the epitome of Vermont charm at this mixed-use property along the Ottaquechee River in Woodstock,VT and just a short drive to Killington Resort. Spanning 5.5 acres, the setting is nothing short of enchanting, providing a perfect blend of natural beauty and versatile accommodations. The main attraction is a delightful Bed and Breakfast, housed in a charming building that exudes warmth and hospitality boasting a commercial kitchen, dining rooms and a tavern. Guests are treated to a unique and cozy experience, capturing the essence of Vermont's welcoming spirit. Adjacent to the B&B, another building offers a combination of a residential space and rental units. This provides a haven for those seeking a permanent residence or a temporary creative retreat. The property includes a motorcoach that can be used to generate income. As a backdrop to this picturesque property, the historic Lincoln Covered Bridge graces the view, completing the postcard-perfect scene. Whether guests are enjoying the comfort of the B&B with a restaurant and tavern, the patio and pergola or the gazebo, each aspect of this property contributes to a memorable and diverse Vermont experience. A variety of events can be hosted on this beautiful property offering both mountain and water views. Ideally situated between Killington Resort and the Village of Woodstock. *Snowmobile right from the Inn property -see Remarks

Listed by Susan Bishop of Four Seasons Sotheby's Int'l Realty

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

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.9% last updated on 2024-02-22

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

2709 W Woodstock Road Woodstock VT 05091

Woodstock, VT2709 W Woodstock Road

Price$2,750,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4982843

  • Multifamily
  • Units 3
  • Bathroom 11
  • Acreage 5.5
  • Square Feet 7,769

Nestled along the scenic Ottaquechee River on 5.5 acres and located in Woodstock VT with its quaint Main St and just a short drive to the Killington Resort, this exceptional property offers a unique blend of natural beauty and year round recreational opportunities including Snowmobiling out your back door! Whether this is a family compound or a multi family investment opportunity the multiple living spaces provide privacy while fostering a sense of togetherness, making it an ideal setting for gatherings and celebrations. Currently operating as an Inn with a commercial kitchen, several dining rooms a tavern and six ensuite guest rooms. The residence is ideal for Innkeepers/Owners or for a more intimate gathering overlooking the lawn and river beyond. Without a doubt, this riverside retreat is an invitation to create lasting memories with loved ones. The property also includes a motorcoach that can be used to generate income.

Listed by Susan Bishop of Four Seasons Sotheby's Int'l Realty

{$office->Name}


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

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.9% last updated on 2024-02-22

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

10 College Hill Road Woodstock VT 05091

Woodstock, VT10 College Hill Road

Price$2,395,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4985985

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 4,214

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 property website for more.

Listed by John Snyder of Snyder Donegan Real Estate Group

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

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.9% last updated on 2024-02-22

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

5798 South Road Woodstock VT 05071

Woodstock, VT5798 South Road

Price$2,250,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4968227

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 6
  • Square Feet 4,510

For nearly two centuries the iconic Kedron Valley Farm has served as the gateway to the village of South Woodstock. Prominently sited on a knoll with lovely valley views in every direction, this warm and inviting post and beam home has been fully rejuvenated, honoring the classic period detail. The main house is ideal for entertaining with bright, generous rooms, and cozy spaces. The living room runs front to back, centered by a brick fireplace with pine surround and exposed beams. The kitchen is well suited with excellent quality Thermador appliances, quartz counters and custom mahogany cabinetry. The spacious private primary suite features exposed beams, cathedral ceiling, new tandem bathrooms connected by a walk thru shower, plenty of closet space, laundry and AC. There are four additional guest suites, a TV and reading room w fireplace and built-ins, and clever loft spaces with offices. The charming, separate three-bedroom carriage house is perfect for guests, family or as an income producing rental unit. The property is anchored by a spectacular 4-story bank barn with six horse stalls, fenced paddocks and a run-in shed complete with power and water. The grounds are stunning with a beautiful brick terrace, level verdant lawns, grand, 175 year old maple trees, established perennial beds, a private swimming pond, apple orchard, and a fenced har-tru surfaced tennis court sited discreetly at the rear of the property. Seven minutes to Woodstock Village Green. Broker interest.

Listed by Danny Kogut of Williamson Group Sothebys Intl. Realty

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

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.9% last updated on 2024-02-22

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

144 & 232 Town Farm Road Woodstock VT 05071

Woodstock, VT144 & 232 Town Farm Road

Price$1,995,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4937127

  • Residential Single Family
  • Construction Existing
  • Bedrooms 8
  • Bathroom 5
  • Square Feet 3,748

Sense of place - the Lewis Farm: The classic Vermont farmstead with an iconic big red barn above Green Mountain Horse Association, the Lewis Farm's 130 acres of hayfields and woodlands span the Kedron Valley hillside just outside the village of South Woodstock. The legacy of stewardship by the Lewis family started in 1940: tending the land, restoring the spectacular barn and converting its lower level to well-planned stabling, conserving the most visible 30 acres along the road, and epitomizing the sense of community and engagement that characterizes South Woodstock and GMHA. Along with the 3-bedroom brick farmhouse, riding ring, and hilltop cabin, a light-filled 2-bedroom contemporary takes in the views, and a south-facing studio is set into the hillside. The houses and studio invite renovation or new construction to meet the quality of the site: the woodlands, hayfields, and farm pond, threaded by trails and farm roads to high meadows with valley views. The beauty of the land, authenticity, and character distinguish this generational offering. EC Fiber available.

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

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

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.9% last updated on 2024-02-22

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

144 & 232 Town Farm Road Woodstock VT 05071

Woodstock, VT144 & 232 Town Farm Road

Price$1,995,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4969259

  • Land
  • Acreage 130.39
  • PricePerSqFt 15300.25
  • Zoning Residential

Sense of place - the Lewis Farm: The classic Vermont farmstead with an iconic big red barn above Green Mountain Horse Association, the Lewis Farm's 130 acres of hayfields and woodlands span the Kedron Valley hillside just outside the village of South Woodstock. The legacy of stewardship by the Lewis family started in 1940: tending the land, restoring the spectacular barn and converting its lower level to well-planned stabling, conserving the most visible 30 acres along the road, and epitomizing the sense of community and engagement that characterizes South Woodstock and GMHA. Along with the 3-bedroom brick farmhouse, riding ring, and hilltop cabin, a light-filled 2-bedroom contemporary takes in the views, and a south-facing studio is set into the hillside. The houses and studio invite renovation or new construction to meet the quality of the site: the woodlands, hayfields, and farm pond, threaded by trails and farm roads to high meadows with valley views. The beauty of the land, authenticity, and character distinguish this generational offering. EC Fiber available.

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

{$office->Name}


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

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.9% last updated on 2024-02-22

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

2018 Church Hill Road Woodstock VT 05091

Woodstock, VT2018 Church Hill Road

Price$1,900,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4969169

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 4,610

Ideally oriented south and westerly this light-filled contemporary home engages you in the outdoors through expansive windows, decks and screened porch overlooking the spring-fed swimming pond. Designed for gracious country living the eat-in kitchen and generous great room are accented by a fieldstone fireplace and vaulted ceilings. The primary bedroom suite and two guest bedrooms are located on the main living level with a walk-out level offering an additional bedroom with media and exercise areas. A 'bonus room' used as a studio is available for many alternative pursuits. Fifty acres of private woodland and open meadows is laced with trails enabling access to nature year round. A small stable is a resource to take advantage of South Woodstock's network of horse trials and miles of gravel roads. A private retreat within minutes of Woodstock's Village Green or the South Woodstock and the Green Mountain Horse Association. The best of all possible worlds.

Listed by Laird Bradley of Williamson Group Sothebys Intl. Realty

{$office->Name}


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

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.9% last updated on 2024-02-22

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

72 Frenchs Road Woodstock VT 05091

Woodstock, VT72 Frenchs Road

Price$1,895,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4968402

  • Residential Single Family
  • Village Woodstock
  • Construction Existing
  • Bedrooms 6
  • Bathroom 4

Amazing opportunity to own a very special property on the market for the first time in over 50 years. Built in 1880, "Rose Hill" was one of the premier homes in the Woodstock Village area. The 6 bedroom 4 bath house sits on just under 4 private acres and is conveniently located less than a mile from the Village Green and the Woodstock Inn and only 1/4 of a mile from the Rec Center. Stone walkways, mature trees and old gardens dot the landscape. The over sized covered brick porch is waiting to reclaim the lovely views to the South. Inside, you are greeted by a large foyer that leads to the stately living room with a magnificent fireplace centering the room. To the left is the dining room which leads to the kitchen, and a window filled den is off to the right. There is a dutch door out to the porch and an eye catching staircase with a wood banister and ornate spindles that takes you upstairs. The 2nd floor is home to 6 bedrooms including a large center room with an elegant fireplace. In addition to the main house, there is a detached garage with a 2 bedroom apartment and a 2 bedroom cottage which includes a living room with fireplace, dining room, kitchen and bath. In need of updates and some renovations, this property is looking for the next steward to return the house to its former glory. Ideal as a primary residence, 2nd home getaway, or redevelopment investment. Short drive to the Woodstock CC and Saskadena 6, while Killington and Dartmouth are less than 30 minutes away.

Listed by Dan Noble of Snyder Donegan Real Estate Group

{$office->Name}


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

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.9% last updated on 2024-02-22

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

39 Elm Street Woodstock VT 05091

Woodstock, VT39 Elm Street, Unit Unit B

Price$1,585,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4982328

  • Condo
  • Square Feet 3,023
  • Bedrooms 3
  • New Contruction Existing
  • Village Woodstock

For good reason, the Richmond House is one of Woodstock's most photographed homes. This stately 1826 brick Federal with all the architectural trimmings and distinctly weathered rose-hued patina is a Woodstock Village landmark and is today, thanks to the previous direction of Laurence Rockefeller, divided into three luxurious condominiums. Sited behind a white picket fence on over an acre of land on Elm Street, the property is minute's walking distance of everything Woodstock Village has to offer. Accessed through a gracious front door and foyer, Unit B is one of the finest townhomes in the Village and occupies the top two floor of the building and just over 3000 square feet of finished space, providing the feeling of living in a single family home. Upon entry, the main floor consists of a combined living and dining room with a wood-burning fireplace, a spacious family room an en-suite study/bedroom also with a wood-burning fireplace. The kitchen opens onto the family room and this side of the building is illuminated by southern exposure. The hallway passage to the dining area ascends a few steps to a built-in bar that in turn opens onto a small balcony that overlooks the Village and the landscaped grounds. The second floor opens to a landing with built-in bookcases, a primary bedroom suite, and an en-suite guest room. An exceedingly rare opportunity to own a magical part of history in the heart of Woodstock Village.

Listed by Richard Higgerson of Higgerson Team Real Estate

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

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.9% last updated on 2024-02-22

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

458 Woodstock Road Woodstock VT 05091

Woodstock, VT458 Woodstock Road

Price$1,499,000The price has recently decreased

MLS Number 4945749

  • Commercial
  • Village Woodstock
  • Acreage 4.57

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 Commissioner of the 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 William Raveis Woodstock

{$office->Name}


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

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.9% last updated on 2024-02-22

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

Broker Reciprocity 

Copyright 2024 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated February 27, 2024 8:38 PM EST

 

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