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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$8,950,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4943673

  • Residential Single Family
  • Full Bath 4
  • Address 2034 Long Hill Road
  • Construction Existing
  • Bedrooms 4

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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Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.69% last updated on 2024-12-05

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

115 Eastman Road Woodstock VT 05071

Woodstock, VT115 Eastman Road

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

Est. Mortgage: $/month

MLS Number 5018286

  • Residential Single Family
  • Full Bath 3
  • Address 115 Eastman Road
  • Construction Existing
  • Bedrooms 3

Sorgenfrei, or "Carefree," was built by Ennis Construction in 2015, and this extraordinary property truly embodies that sobriquet. A stunning and uncommon confluence of the finest materials and the most energy efficient techniques, this home was carefully constructed to maximize worry-free enjoyment. The most advanced systems and a focused commitment to the highest quality make this home a testament to elegant durability. From the mahogany exterior to the handcrafted front doors and custom-wrought hardware, this spacious and meticulously considered home celebrates the skill of Vermont's most talented craftspeople. The unparalleled 180 degree views over the Woodstock valley are spectacular in every season, offering year-round sunlight and ever-changing vistas. With a gourmet kitchen custom-built for entertaining, a 1,000 bottle wine cellar, and a double-sided great room fireplace, Sorgenfrei perfects conviviality. The measures taken to ensure the property's efficiency and durability are too numerous to name - among them, an 18kw solar array, Pella Architect-Series windows, and custom mortise and tenon fir construction. At home among Woodstock's most lauded residences, and gorgeously situated in one of the area's most prestigious neighborhoods, this home is a testament to uncompromising vision and a paean to unparalleled enjoyment of Vermont's Green Mountains.

Listed by Keri Cole of Williamson Group Sothebys Intl. Realty

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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: 6.69% last updated on 2024-12-05

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

2358 Long Hill Road Woodstock VT 05091

Woodstock, VT2358 Long Hill Road

Price$6,750,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5011268

  • Residential Single Family
  • Full Bath 3
  • Address 2358 Long Hill Road
  • Construction Existing
  • Bedrooms 5

Sited on 465 +/- private acres in South Woodstock, Birch Tree Farm was created as a retreat to bring family and friends together and to enjoy the great outdoors. The farm offers a variety of experiences, including pressing apples for cider, collecting eggs for breakfast, hiking to the cabin with 360 degree views, fishing or skating on the pond, enjoying miles of trails for walking, riding, or snowshoeing, and tapping trees for maple syrup. The relaxed vibe of the Lodge-style home, made of wood and stone, evokes a sense of mountain living, with design elements like exposed beams, a cathedral ceiling in the great room, a large stone wood burning fireplace, and floor-to-ceiling windows that frame expansive views of the mountains and the Ottauquechee Valley. Step out onto the wrap-around deck to take in an infinity pool, hot tub, stocked pond, and apple orchard. Landscape design by Shep Butler includes 10' hydrangea bushes, perennials gardens, stone walls, wild lupine in the meadow and a walled vegetable garden. The three-level bank barn, designed by award winning Boston architect John MacDonald and built by Housewright Construction, offers one of the finest barns in area with seven stalls, an office/tack room, and a versatile upper level for entertaining & recreation, as well as accommodating an overflow of guests. Nine fenced pastures, two run-in sheds, a two-level storage barn, and a chicken coop enhance the farm with miles of trails connecting to GMHA. Showings begin 8-30-24

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: 6.69% last updated on 2024-12-05

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

249 Sawyer Road Woodstock VT 05091

Woodstock, VT249 Sawyer Road

Price$4,150,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5018393

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

Listed by Elevations Team of Real Broker LLC

{$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: 6.69% last updated on 2024-12-05

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

18 The Green Woodstock VT 05091

Woodstock, VT18 The Green

Price$3,995,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5008434

  • Residential Single Family
  • Full Bath 2
  • Address 18 The Green
  • Construction Existing
  • Bedrooms 6

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

{$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: 6.69% last updated on 2024-12-05

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

61 Academy Circle Woodstock VT 05071

Woodstock, VT61 Academy Circle

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

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

{$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: 6.69% last updated on 2024-12-05

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

2055 Church Hill Road Woodstock VT 05091

Woodstock, VT2055 Church Hill Road

Price$2,950,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4997626

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

Nestled among verdant rolling hills, High Birch is located in one of the area's most desirable regions at the midpoint between Woodstock and South Woodstock Villages. Designed in 1976 by prominent New York architect Lewis Davis, of Davis, Brody and Bond renowned for his modernist skyscrapers that impacted the skyline of New York City, the home contrasts sleek interior spaces to the surrounding natural landscape. Private and tranquil with pristine views in every direction through walls of tall windows and sweeping ceilings, the rooms are spacious, bright and inspiring- ideal for entertaining and daily living, and communicate directly with exterior spaces, terraces and decks. The kitchen and bathrooms have all been entirely renovated by Studio Nexus honoring and accentuating the original Davis design. The multi-level Great Room is anchored by a raised, polished gray marble fireplace. The Primary Suite is located on the 2nd level featuring a curved wall of windows offering a panoramic view of the neighboring valley farms, complete with a spectacular spa like wet-room, dressing room and laundry. The 2nd level is further completed by three additional bedrooms and 2 bathrooms. The lower level has direct access to the 2-car garage, an office, and spacious bunkroom. The surrounding terraces and grounds are lovely with established perennial beds. There is a swimming/skating pond and a barn for animals, storage, or to house your own sugaring operation. Offered fully furnished.

Listed by Danny Kogut 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: 6.69% last updated on 2024-12-05

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

4945 South Road Woodstock VT 05091

Woodstock, VT4945 South Road

Price$2,865,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5013744

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

The melding of the convenience of a premiere Village residence with the privacy and peace of a country estate is a rare balance. The John Arnold Cottle House achieves just such a balance. The three bedroom two story brick Federal home, built in 1811, has a prominent position on the main street in South Woodstock hamlet. It's setting belies the unique qualities the 2.7 acres offers. A drive to the lower level two car garage separates the main house and the renovated Kingley Barn, a two bedroom with loft guest house with a deck overlooking the Kedron Brook. There is a timber bridge crossing the Kedron Brook which accesses the open field and meadow and the two bay barn. The 450 feet of frontage on the Kedron Brook is an ideal tranquil retreat to enjoy the water element, firepit and surrounding environment with complete privacy. The John Arnold Cottle House has been fully renovated/restored with all of the best systems and finishes. The newer addition on the rear of the house has a gourmet kitchen, large brick fireplace, and relaxed living space.

Listed by Wade Treadway of Wade I Treadway Real Estate

{$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: 6.69% last updated on 2024-12-05

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

2394 Fletcher Hill Road Woodstock VT 05091

Woodstock, VT2394 Fletcher Hill Road

Price$2,800,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5012999

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 2,944

Newly constructed Modern Vermont Farmhouse residence on 14 acres with absolutely amazing river views, 13-foot ceilings, gourmet kitchen, oversized french doors and windows throughout, radiant-heated concrete floors, first rate finishes, appliances and mechanicals located just 6 minutes to the Woodstock village green and 17 minutes to the Killington Skyeship base lodge. The first level is comprised of a large, open-format living space with gourmet kitchen, dining and living spaces, plus a first level bedroom with modern ensuite bath. Upstairs is another large open floor plan living space with a half-bath, and a full bedroom with ensuite bath. Each side of the upstairs living space has loft sleeping bunk-areas for kids (of all ages!). SEE DEDICATED PROPERTY WEBSITE FOR VIDEOS, VIRTUAL WALKTHROUGH, FLOORPLANS AND MORE.

Listed by John Snyder 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: 6.69% last updated on 2024-12-05

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$2,750,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4966761

  • Residential Single Family
  • Full Bath 3
  • Construction Existing
  • 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

{$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: 6.69% last updated on 2024-12-05

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

2706 East Woodstock Road Woodstock VT 05073

Woodstock, VT2706 East Woodstock Road

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

MLS Number 5020107

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

INVESTMENT OPPORTUNITY - Rare historic building (The Taftsville Country Store) that is an opportunity awaiting with multiple income streams in the village of Taftsville just 5 minutes to the quintessential New England town of Woodstock! The property has 4 (5 potential) units including a gracious store space with bathroom that is approved for use as a restaurant, café, or small retail store. The second unit is a Post Office with current lease for 3 more years. The third unit is a 1 bedroom, 1 bath apartment (designed and approved for 2 bedroom, 2 bath) with an excellent AIRBNB rental history. The fourth unit is a 3 bedroom, 2 bath apartment which could be rented long or short term or owner occupied to offset living expenses. There is space for a fifth unit which has been designed and planned as a studio apartment which would be suitable for short term/residential rental. Current owners have redesigned, expanded, and paved the parking lot to include 27 parking spaces and EV Conduit for 2 charging stations that can accommodate 4 vehicles (not installed), ADA access to building, and an ADA accessible restroom are designed (not built). Significant investment has occurred on infrastructure and heating plant and all approvals are in place for future remodeling/restoration. Historic Preservation tax credits available. Property boasts pleasant exterior patio views to the Ottauquechee River & Taftsville Covered Bridge. Come with a vision for the "store" and make an opportunity happen!

Listed by John Bassette of Bassette 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:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.69% last updated on 2024-12-05

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

2706 East Woodstock Road Woodstock VT 05091

Woodstock, VT2706 East Woodstock Road

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

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 owners 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

{$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:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.69% last updated on 2024-12-05

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 December 6, 2024 7:54 AM EST

 

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