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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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: 6.87% last updated on Feb 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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18 The Green Woodstock VT 05091

Woodstock, VT18 The Green

Price$3,995,000

Est. Mortgage: $/month

MLS Number 5008434

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

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

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.87% last updated on Feb 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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61 Academy Circle Woodstock VT 05071

Woodstock, VT61 Academy Circle

Price$3,500,000

Est. Mortgage: $/month

MLS Number 5002873

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

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

Listed by Carol Wood of Williamson Group Sothebys Intl. Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.87% last updated on Feb 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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4945 South Road Woodstock VT 05071

Woodstock, VT4945 South Road

Price$2,485,000

Est. Mortgage: $/month

MLS Number 5028924

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

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

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

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$
%
$/month over payments
Federal 30-year interest rate: 6.87% last updated on Feb 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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851 Riverside Park Road Woodstock VT 05091

Woodstock, VT851 Riverside Park Road

Price$2,450,000

Est. Mortgage: $/month

MLS Number 5025630

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

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

Listed by Richard Higgerson of Higgerson & Company

$
$
%
$/month over payments
Federal 30-year interest rate: 6.87% last updated on Feb 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2706 East Woodstock Road Woodstock VT 05073

MLS Number 5020107

  • Commercial
  • County Windsor
  • Square Feet 6,000
  • Acreage 0.56

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

Listed by John Bassette of Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.87% last updated on Feb 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2706 East Woodstock Road Woodstock VT 05091

Woodstock, VT2706 East Woodstock Road

Price$2,000,000

Est. Mortgage: $/month

MLS Number 5020106

  • Residential Single Family
  • 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 owner's unit- 3 bedroom, 2 bath), and plans/space for an additional studio unit. Perfect opportunity for an investor to offset living expenses with this multi-unit property, or just have a super fancy home office downstairs. Potential diversified income streams with hospitality, residential rental, and retail/ food service all in one property. Current owners have redesigned and graded the parking lot to include 27 parking spaces and EV Conduit for 2 charging stations that can accommodate 4 vehicles, ADA access to building, and ADA accessible restrooms. Property boasts gorgeous patio views of the Ottauquechee River and Taftsville Covered Bridge.

Listed by John Bassette of Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.87% last updated on Feb 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2709 W Woodstock Road Woodstock VT 05091

Woodstock, VT2709 W Woodstock Road

Price$1,875,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4982843

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

INVESTMENT, MULTI-GENERATIONAL, MULTI FAMILY AND COMMERCIAL OPPORTUNITY .. priced below appraised value on land and buildings providing instant equity. 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, dining rooms, a tavern and six ensuite guest rooms- perfect for short term rentals. The residence is perfect for a more intimate gathering or apartment conversion with an open concept main level kitchen/living/dining experience with 3 ensuite bedrooms upstairs plus a separate ground 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 Ottauquechee 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: 6.87% last updated on Feb 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2709 W Woodstock Road Woodstock VT 05091

Woodstock, VT2709 W Woodstock Road

Price$1,875,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4999581

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

INVESTMENT, MULTI-GENERATIONAL, MULTI FAMILY AND COMMERCIAL OPPORTUNITY .. priced below appraised value on land and buildings providing instant equity. 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, dining rooms, a tavern and six ensuite guest rooms- perfect for short term rentals. The residence is perfect for a more intimate gathering or apartment conversion with an open concept main level kitchen/living/dining experience with 3 ensuite bedrooms upstairs plus a separate ground 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 Ottauquechee 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: 6.87% last updated on Feb 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2090 Randall Road Woodstock VT 05091

Woodstock, VT2090 Randall Road

Price$1,800,000

Est. Mortgage: $/month

MLS Number 5025879

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

Constructed in 2007 with a nod to the Gothic Style Vermont Farmhouse vernacular, this beautifully composed country home creatively integrates curated period detail with modern conveniences and systems. Conveniently located at the end of a picturesque tree lined dirt road just minutes from the Villages of both Woodstock and South Woodstock offering privacy and tranquility. The interior spaces of the home are creative, and inspiring, connecting seamlessly with the outdoors through classic covered porches and a spacious screened room. Enjoy lovely valley views beyond established perennial beds and mature plantings, with ancient stone walls lacing through. The kitchen is anchored by a AGA propane stove with custom cabinetry and soapstone counters. The dining room has a wall of built-ins, and reclaimed wide plank flooring. The living room is centered with a beautiful wood burning fireplace, and steps out to a screened porch. Three bedrooms, two bathrooms, and an oversized landing/office space on the second level complete the home. Oversized two car garage/barn with huge loft space for expansion. The leased Tesla Powerwall for peace of mind in the event of a power interruption. Perfect as a primary or second home.

Listed by Danny Kogut of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.87% last updated on Feb 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1522 Barnard Road Woodstock VT 05091

Woodstock, VT1522 Barnard Road

Price$1,650,000

Est. Mortgage: $/month

MLS Number 5027640

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

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

Listed by Keri Cole of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.87% last updated on Feb 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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27 Slayton Woodstock VT 05091

Woodstock, VT27 Slayton, Unit 3

Price$1,585,000

Est. Mortgage: $/month

Pending

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: 6.87% last updated on Feb 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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458 Woodstock Road Woodstock VT 05091

Woodstock, VT458 Woodstock Road

Price$1,499,000

Est. Mortgage: $/month

MLS Number 4945772

  • Land
  • County Windsor
  • Square Feet 199,069
  • Acreage 4.57

Listed by John Wetmore of Wetmore Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.87% last updated on Feb 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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458 Woodstock Road Woodstock VT 05091

MLS Number 4945749

  • Commercial
  • County Windsor
  • Acreage 4.57

Listed by John Wetmore of Wetmore Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.87% last updated on Feb 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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608 Fletcher Hill Road Woodstock VT 05091

Woodstock, VT608 Fletcher Hill Road

Price$1,495,000

Est. Mortgage: $/month

MLS Number 5028430

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

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: 6.87% last updated on Feb 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1075 Westerdale Road Woodstock VT 05091

Woodstock, VT1075 Westerdale Road

Price$1,395,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5022674

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

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

Listed by Keri Cole of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.87% last updated on Feb 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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72 French's Road Woodstock VT 05091

Woodstock, VT72 French's Road

Price$1,390,000

Est. Mortgage: $/month

Active With Contract

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: 6.87% last updated on Feb 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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119 English Mills Way Woodstock VT 05091

Woodstock, VT119 English Mills Way

Price$1,150,000

Est. Mortgage: $/month

MLS Number 4991097

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

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

Listed by John Wetmore of Wetmore Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.87% last updated on Feb 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1548 Peterkin Hill Road Woodstock VT 05091

Woodstock, VT1548 Peterkin Hill Road

Price$1,125,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5023612

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

A classic, beautifully maintained residence in an exceptional location in South Woodstock, 8 minutes to the Village Green, in an area of substantial homes and estates, sited on 6 landscaped acres with mowed lawns, raised beds, stone patios and a charming red barn - suitable as a workshop, artist studio, storage for gear and motorized toys or for goats and chickens! The main residence features an open floorplan with modern kitchen, family room and sunny eat-in breakfast area all enjoying one of the homes 3 woodburning fireplaces. Also on the 1st floor is a larger formal dining room open to a living room with fireplace. The charming mud-entry area with slate floor has a private powder bath. Up the main front stairway is the privately situated primary bedroom suite with the 3rd fireplace, a walk-in closet and updated, lovely bathroom with glass/stone shower and separate free-standing tub. 2 other upstairs bedrooms (plus a smaller room with overflow bunk beds) share an updated hall bath that also has full-size laundry. The lower level has a fully finished workout/rec room. Above the attached/heated 2-car garage is a large private guest suite with vaulted ceilings, sitting/office area, kitchenette and an ensuite full bath. Off the kitchen is the outdoor and south-facing stone patio with lovely perennial gardens and stonewall for entertaining/ cookouts. This is a move-in-ready home, in an exceptional area! SEE FULL PROPERTY WEBSITE FOR FULL DETAILS!

Listed by John Snyder of Snyder Donegan Real Estate Group

$
$
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$/month over payments
Federal 30-year interest rate: 6.87% last updated on Feb 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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598 East Woodstock Road Woodstock VT 05091

MLS Number 5017395

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

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

Listed by Geoff Eckler of Real Broker LLC

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$
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$/month over payments
Federal 30-year interest rate: 6.87% last updated on Feb 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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234 Randall Road Woodstock VT 05091

Woodstock, VT234 Randall Road

Price$845,000

Est. Mortgage: $/month

MLS Number 4913852

  • Residential Single Family
  • County Windsor
  • Property Type Single Family
  • Bedrooms 2
  • Bathroom 1

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

Listed by Wade Treadway of Wade I Treadway Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.87% last updated on Feb 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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25 Linden Hill Street Woodstock VT 05091

Woodstock, VT25 Linden Hill Street

Price$795,000

Est. Mortgage: $/month

MLS Number 5028831

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

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

Listed by Laird Bradley of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.87% last updated on Feb 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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5851 South Road Woodstock VT 05071

Woodstock, VT5851 South Road

Price$699,000

Est. Mortgage: $/month

MLS Number 5014012

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

This charming home is an amazing opportunity to own a piece of history in the lovely village of South Woodstock , Vermont. Starting its life as the garage and home of Clyde Wood it has evolved over time with the present owners into a beautiful , meticulous residence. Much attention to detail can be found in every room from wide pine flooring to cathedral ceiling in the great room. The home is light filled with a large deck looking out to the Kedron Brook and the Green Mountain Horse Association fields . The Honey Shop is where the Wood family sold honey from the large Bass trees on the property. It is now a lovely room for entertaining or enjoying a quiet spot to take a nap or read a favorite book. The barn could easily convert to garage space with plenty of room for storage . The very back of the barn is the only part of the buildings that is in the Flood zone. The grounds are beautifully landscaped . Cross over the brook on the little bridge to miles and miles of trails. Country living at its best but only 6 miles from Woodstock Village and short distances to skiing , golf, biking, all season sports and of course fly fishing on the Kedron Brook out your back door !. Call today for an appointment .

Listed by Carol Wood of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.87% last updated on Feb 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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3914 South Road Woodstock VT 05071

Woodstock, VT3914 South Road

Price$695,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5024226

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

This South Woodstock contemporary residence was designed by the original architect-owner to showcase Vermont's changing seasons and capture views of the Kedron Brook as it wanders through the property past small meadows tucked in along the banks. The home can be accessed privately at grade level through the heated garage and mudroom, while guests enter via a covered entry to the upper level. The lower walk-out level of the home has two bedrooms, a shared bath, laundry and workshop. The elevated second floor is dedicated to gathering spaces including a great room with cathedral ceilings, eat in kitchen and family room that opens out on to a broad deck with overlooking the brook as it flows to the nearby Woodstock golf course and Athletic Club. The spacious primary bedroom offers an ensuite bathroom and abundant closet space. The main floor guest bedroom with loft is served by an adjacent bathroom. The two-stall multi-purpose barn opens to a small pasture and a fence yard for pets. A home for all seasons and reasons.

Listed by Laird Bradley of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.87% last updated on Feb 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1 Border Lane Woodstock VT 05091

Woodstock, VT1 Border Lane

Price$625,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5006149

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

Location, location location! Situated on a very desirable road within Woodstock Village, this 3 bedroom Ranch sits on just over 1 acre of open lawn surrounded by mature trees. The yard is tastefully landscaped and there is a beautiful patio out back, ideal for a morning cup of coffee, grilling dinner, or a nice glass of wine. As you enter through the front door, the bedrooms and a bath are off to the right. To the left, the long eat-in kitchen flows into to the dining area which connects to the living room. There is patio access, a large bow window and a gas fireplace to keep warm in the wintertime. At the end of the living room is a lovely sunroom that could also be a great office. Rounding out the first floor is a half bath, and access to the attached garage and full basement. Local shops and restaurants are within walking distance and you are just minutes from the Woodstock Country Club and Saskadena 6.

Listed by Dan Noble of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.87% last updated on Feb 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Copyright 2025 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated February 17, 2025 8:22 AM EST