Woodstock

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

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2034 Long Hill Road Woodstock VT 05071

Woodstock, VT2034 Long Hill Road

Price$8,950,000

Est. Mortgage: $/month

MLS Number 4943673

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 7

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Nov 7, 2024
* 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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115 Eastman Road Woodstock VT 05071

Woodstock, VT115 Eastman Road

Price$8,000,000

Est. Mortgage: $/month

MLS Number 5018286

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

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Nov 7, 2024
* 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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2358 Long Hill Road Woodstock VT 05091

Woodstock, VT2358 Long Hill Road

Price$6,750,000

Est. Mortgage: $/month

MLS Number 5011268

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

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Nov 7, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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327 Fletcher Schoolhouse Road Woodstock VT 05071
Pending

MLS Number 4993127

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

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

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Nov 7, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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249 Sawyer Road Woodstock VT 05091

Woodstock, VT249 Sawyer Road

Price$4,150,000

Est. Mortgage: $/month

MLS Number 5018393

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

Listed by Elevations Team of Real Broker LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Nov 7, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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18 The Green Woodstock VT 05091

Woodstock, VT18 The Green

Price$3,995,000

Est. Mortgage: $/month

MLS Number 5008434

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

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

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Nov 7, 2024
* 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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486 Benedict Road Woodstock VT 05071

Woodstock, VT486 Benedict Road

Price$3,500,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4986511

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 6
  • Bathroom 7

"BENEDICT HILL" - sited on 38 acres on a quiet gravel road in a premier location in South Woodstock is this truly classic Vermont estate property. Excellent equestrian / horse potential with historic 5-stall barn and fencing for pastures/paddocks already in place. The land component is comprised of split-rail fence lined pastures, meadows, woodlands, giant maple trees, ancient stone walls and gardens. The main “Stone House” c. 1820 - with period details and 10' ceilings has 4 bedrooms, 3 full and 2 half-baths, gourmet kitchen, a library-den, a wonderful living room and 3 fireplaces on the main level. A stone patio/covered porch spans the rear of the house, and a 2-car attached garage. The original barn was renovated into a fully finished barn/guest house comprised of a fabulous great room with 30-foot ceilings and stone fireplace, kitchen and dining areas. Open stairs lead up to a loft primary-bedroom and bath. Downstairs is a rec/family room, 2 bedrooms and full bath. The present owners have just completed many renovations. This is a rare opportunity to acquire one of the most special, pastoral Vermont properties to come on the market in years - yet is just 5 mins to the hamlet of South Woodstock, 12 mins to the Woodstock village green, and 20-30 mins to I-89, Hanover/Dartmouth and points beyond. SEE FULL PROPERTY WEBSITE.

Listed by John Snyder of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Nov 7, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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61 Academy Circle Woodstock VT 05071

Woodstock, VT61 Academy Circle

Price$3,500,000

Est. Mortgage: $/month

MLS Number 5002873

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

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

Listed by Carol Wood of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Nov 7, 2024
* 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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2055 Church Hill Road Woodstock VT 05091

Woodstock, VT2055 Church Hill Road

Price$2,950,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4997626

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • 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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Nov 7, 2024
* 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 05091

Woodstock, VT4945 South Road

Price$2,865,000

Est. Mortgage: $/month

MLS Number 5013744

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

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Nov 7, 2024
* 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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2394 Fletcher Hill Road Woodstock VT 05091

Woodstock, VT2394 Fletcher Hill Road

Price$2,800,000

Est. Mortgage: $/month

MLS Number 5012999

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 2
  • Bathroom 3

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Nov 7, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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318 Ebbin Lockwood Way Woodstock VT 05071

Woodstock, VT318 Ebbin Lockwood Way

Price$2,750,000

Est. Mortgage: $/month

MLS Number 4966761

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

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

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Nov 7, 2024
* 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
  • County Windsor
  • 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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Nov 7, 2024
* 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
  • County Windsor
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Nov 7, 2024
* 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 4985985

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 5
  • Bathroom 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: 6.79% last updated on Nov 7, 2024
* 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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2709 W Woodstock Road Woodstock VT 05091

Woodstock, VT2709 W Woodstock Road

Price$1,999,000

Est. Mortgage: $/month

MLS Number 4982843

  • Multifamily
  • County Windsor
  • Bathroom 11
  • Square Feet 7,769
  • Acreage 5.5

Live the Vermont Dream in Woodstock, VT! Experience the charm of Woodstock with its quaint Main Street and enjoy the proximity to Killington Resort, just a short drive away. This exceptional property offers a unique blend of natural beauty and year-round recreational opportunities, perfect for creating lasting memories. Whether you're looking for a family compound or a multi-family investment opportunity, this property offers versatility like no other providing privacy while fostering a sense of togetherness. An ideal setting for gatherings and celebrations of all sizes. The property includes a commercial kitchen, several dining rooms, a tavern, and six ensuite guest rooms. The residence is perfect for a more intimate gathering with an open concept main level and 3 ensuite bedrooms while the motorcoach can be used to generate income and offers a special glamping experience with stunning mountain and water views of its own.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Nov 7, 2024
* 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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2709 W Woodstock Road Woodstock VT 05091

Woodstock, VT2709 W Woodstock Road

Price$1,999,000

Est. Mortgage: $/month

MLS Number 4999581

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 10
  • Bathroom 12

Vermont is calling you! Experience the charm of Woodstock, VT with its quaint Main Street and enjoy the proximity to Killington Resort, just a short drive away. This exceptional property offers a unique blend of natural beauty and year-round recreational opportunities, perfect for creating lasting memories. Whether you're looking for a family compound or a multi-family investment opportunity, this property offers versatility like no other providing privacy while fostering a sense of togetherness. An ideal setting for gatherings and celebrations of all sizes. The Inn building includes a commercial kitchen, several dining rooms, a tavern,and six ensuite guest rooms. The residence is perfect for a more intimate gathering with an open concept main level kitchen/living/dining experience with 3 ensuite bedrooms upstairs plus a main level, king bed suite with kitchenette while the motorcoach can be used to generate income and/or offers a special glamping experience with stunning mountain and water views of its own. Snowmobile right from your backyard! All this along the Otterquechee River on 5.5 acres in Woodstock VT! Unbelievable opportunity and location

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Nov 7, 2024
* 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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33 River Street Woodstock VT 05091

Woodstock, VT33 River Street

Price$1,695,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5009557

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

BEAUTIFULLY renovated rare antique residence in the heart of historic Woodstock! Located in a premiere neighborhood within walking distance to all of towns amenities, hiking on Mtn Tom in your backyard. Situated on a very large lot featuring an in-ground pool accented with arbor and pool house. Lovely perennial gardens and large backyard for those seeking a vegetable garden or room for entertaining friends and family. This 4000+ sq. ft residence has generous room proportions, lots of natural sunlight and plenty of nooks for those seeking a quiet place to read a book. Handsome original wide pine floors throughout. This home was fully renovated with updated wiring, plumbing and insulation but still maintains the antique charm of a true Vt farmhouse. Original doors, 2 refurbished sunrooms, 2 covered porches overlooking the river, studio, family room and formal living room accented with a wood burning stove. Large kitchen with soapstone counters with Wolfe Gas range, ample room for cooking. Large dining area for entertaining and a first floor bedroom en suite. 2nd FL offers large primary bedroom suite with cozy sunroom overlooking the pool with views to Mtn Tom. Don't miss the 3rd floor with 2 small offices and lots of storage. The attached barn has capacity for lots of storage and options for multiple use. Walk over beautiful covered bridge to access restaurants, movie theatre and shops. Snow shoeing, championship golf, fly fishing and skiing all minutes away!

Listed by Gretchjen Smith of Williamson Group Sothebys Intl. Realty

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$/month over payments
Federal 30-year interest rate: 6.79% last updated on Nov 7, 2024
* 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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27 Slayton Woodstock VT 05091

Woodstock, VT27 Slayton, Unit 3

Price$1,585,000

Est. Mortgage: $/month

MLS Number 4986623

  • Condo
  • County Windsor
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,677

A chance awaits to acquire a brand-new, Vernacular Elevator Duplex Townhome with breathtaking views of Woodstock village rooftops and scenic Billings Museum Farm. This rare gem features a distinctive private rooftop deck, situated in a secluded neighborhood boasting a remarkable walkability score. Crafted by acclaimed builder and award-winning architect, this Elevator home sets a standard for sustainability, honoring the area's rich conservation history. Each unit, serviced by an elevator spanning four levels, offers a garage accommodating two cars. Main living area, boasts an expansive open space for dining and living, complemented by a built-in gas fireplace. Luxurious kitchen opens to a private stone patio with an additional fireplace, creating an inviting outdoor retreat. Second floor, features two generously sized bedrooms with a full bath. Third floor elevator-accessible, leads to the primary bedroom with French doors opening onto a private deck showcasing views of the village and Billings Farm. Primary bath is featuring a steam shower and standalone soaking tub. Primary deck lies access to private rooftop deck, offering unrivaled village views. Photos are similar model unit. Model Unit available for showing. Builder licensed Real Estate Professional. The sale of this property being listed is contingent upon the proposed Seller (or "Contract Owner") completing his/her/its purchase of this property. "Seller" currently has this property under contract for purchase.

Listed by Jason Saphire of www.HomeZu.com

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Nov 7, 2024
* 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$1,575,000

Est. Mortgage: $/month

MLS Number 5018305

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

Open House Sunday 11/3 1:30 to 3:00 - 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: 6.79% last updated on Nov 7, 2024
* 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
  • County Windsor
  • Square Feet 199,069
  • Acreage 4.57

Listed by John Wetmore of William Raveis Woodstock

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$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Nov 7, 2024
* 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
  • County Windsor
  • Acreage 4.57

Listed by John Wetmore of William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Nov 7, 2024
* 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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72 French's Road Woodstock VT 05091

Woodstock, VT72 French's Road

Price$1,499,000

Est. Mortgage: $/month

MLS Number 5014859

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

In 1880, this lovely hilltop Gambrel Colonial was designed by the prominent Manhattan Architectural Firm, McKim, Mead and White. “Rose Hill” was one of Woodstock's most prominent residences featuring the exquisite workmanship of the region's finest craftsmen. The grand scale and proportion of the rooms and the elegant period detail harken back to days of gracious gatherings with a formal DR complete with custom built-ins, a Library and a Stately Living Room anchored by a central fireplace, with direct access to a brick portico that runs the length of the home- ideal for summer entertaining. The kitchen has custom built-ins, plenty of counter space, a pantry entry, and a secondary staircase to access the second floor. A combination of indigenous hardwood floors run throughout the entire home. The sweeping formal staircase brings you to the second level with a spacious landing, and a wall of built-ins. There are a total of six bedrooms including a roomy primary bedroom with a fireplace, and three bathrooms. To the rear of the home you'll find a separate 2-car garage with a two bedroom rental unit above. Follow the footpath down to a secluded, very sweet two-bedroom guest cottage. All sited on 3.68 AC offering privacy, and plenty of space for gardening, entertaining and recreation. Just a short stroll to the Village Green and the National Park. This very special property awaits your vision to return it to its former splendor.

Listed by Danny Kogut of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Nov 7, 2024
* 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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6453 South Road Woodstock VT 05071

Woodstock, VT6453 South Road

Price$1,340,000

Est. Mortgage: $/month

MLS Number 5003482

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

Round Top Cottage is sited on a knoll just outside the village of South Woodstock on 20 acres, offering complete privacy and views of the rolling hills framing the Kedron Valley. This three-bedroom lodge, fully renovated in 2024, blends modern amenities with rustic elegance. The open floor plan features cathedral ceilings in the main living and dining area, creating an inviting space to gather (or enjoy quiet time). The first floor primary suite has lovely light and a generous soaking tub. The second floor includes a sitting area, two bedrooms, and an office. In the summer, enjoy outdoor living with a fire pit for evening gatherings under the stars. Direct access to trails for all season exploration. Equestrians will appreciate the potential to build a small barn with a paddock, and the short hack over to Green Mountain Horse Association (GMHA). Close to skiing: 23 miles from Killington, 22 miles from Okemo, and 10 miles from Saskadena Six.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Nov 7, 2024
* 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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403 Horseshoe Way Woodstock VT 05071

Woodstock, VT403 Horseshoe Way

Price$1,250,000

Est. Mortgage: $/month

MLS Number 5004878

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 2
  • Bathroom 2

Discover an unparalleled woodland retreat nestled on a picturesque hilltop in South Woodstock, Vermont. This extraordinary timber frame home, a masterpiece of craftsmanship, offers breathtaking views of the pristine Green Mountain Horses Association show arenas and cross-country course. Each stone, beam, and timber has been meticulously and artfully placed by the current owner, reflecting a labor of love and dedication. This unique property has been cherished by the same family since 1965, imbuing it with a rich history and a profound connection to the land. The 2-bedroom, open-concept hillside retreat is enveloped by a serene hardwood forest, accessed via a private driveway aptly named Horseshoe Way. This path honors the farrier who envisioned and created this sanctuary as a tribute to a family of farmers who devoted their lives to their community. The home itself is a testament to Vermont's heritage, constructed from materials carefully curated from some of the state's most iconic early barns and sawmills. Every element of this residence tells a story, blending the past's rustic charm with modern comforts. Whether you seek a peaceful haven or a base for outdoor adventures, this South Woodstock retreat offers a unique opportunity to embrace a lifestyle of tranquility and natural beauty. Don't miss your chance to live on a parcel steeped in Vermont's history and create your own cherished memories in this remarkable woodland sanctuary.

Listed by Sandy Reavill of Real Broker LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.79% last updated on Nov 7, 2024
* 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 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 November 8, 2024 3:27 PM EST