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Woodstock VT Real Estate & Homes for Sale

38 Properties Found

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$2,485,000

26 The Green Woodstock, VT 05091

MLS: 5107880 Photos
Beds:
4
Baths:
5.00
Sq.Ft.:
4,864
Status:
NEW LISTING
MLS#:
5107880
Type:
Single Family
Lot size:
0.21 Acres
Year built:
1807
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: LandVest, Inc/Woodstock
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ADDITIONAL INFORMATION

Built in 1807 by Tille Parker, 26 The Green is one of Woodstock Village's earliest and perhaps prettiest houses. The Federal style residence originally served as a tavern and lodging for members of Vermont's early legislature, giving the property an uncommon connection to both the town's and the state's history. Over a century later, it became the Daughters of the American Revolution House Museum. Listed on the historic register, the home underwent a comprehensive restoration in 1995 by noted preservationist Doug Guest, along with a thoughtfully designed addition. Distinctive original details remain, including five teardrop ornaments above the first-floor windows and the beautiful Palladian window over the front entrance. Together with the patina of more than two centuries, they give the house an authenticity that has been carefully preserved while incorporating the comforts of contemporary living. Inside, wide-board floors, finely proportioned rooms, five working fireplaces, period millwork, and abundant natural light create a sense of warmth and character. The capacious renovated kitchen opens to a sun-filled dining area overlooking the rear stone terrace, while gracious gathering rooms retain the scale and character of the original house. All bedrooms are en suite, an unusual convenience in a home of this age. Set back from Main Street along a quieter parallel road, the property enjoys one of Woodstock Village's most appealing locations, with dining, the theater, galleries, cultural events, and the trails of Mount Tom all within an easy walk. A detached two-bay garage and off-street parking add another uncommon convenience for a village property. Beautifully restored and turnkey, 26 The Green offers the opportunity to live in an important early Vermont home without sacrificing the ease of contemporary village life. Showings start September 10th.

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$1,040,000

13 High Street Street Woodstock, VT 05091

MLS: 5105489 Photos
Beds:
3
Baths:
2.00
Sq.Ft.:
1,782
Status:
Active
MLS#:
5105489
Type:
Single Family
Lot size:
0.31 Acres
Year built:
1890
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Four Seasons Sotheby's Int'l Realty
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ADDITIONAL INFORMATION

Woodstock Village Home~ A rare opportunity to enjoy the best of Woodstock Village living from this charming and beautifully updated 3-bedroom, 2-bath home, once the town's blacksmith shop. Just steps from the heart of the village, you can leave the car at home and walk to shops, restaurants, galleries, cafés, and everything that makes Woodstock one of Vermont's most beloved destinations. Inside, an open-concept floor plan, beautiful wood floors, and abundant natural light create a warm and inviting atmosphere. Recent improvements include a new heat pump providing efficient heating and air conditioning, electrical upgrades, interior painting, and extensive basement work, enhancing both comfort and functionality. Outside is where this village property becomes truly special. The spacious fenced yard borders the Kedron Brook, creating a surprisingly peaceful setting in the heart of town. Relax on the deck and listen to the water, enjoy the newly planted fruit trees, or step through the yard to the nearby village footbridge spanning the brook--a picturesque connection to the surrounding neighborhood. Historic character, thoughtful improvements, a wonderful yard, and an exceptional walkable location come together in a home that captures the charm and ease of life in Woodstock Village.

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$399,600

121 Townhouse Way Way Unit 20 Woodstock, VT 05091

Photos
Beds:
2
Baths:
3.00
Sq.Ft.:
2,268
Status:
Active
MLS#:
5105357
Type:
Condo
Lot size:
15 Acres
Year built:
1982
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Housing Solutions RE, LLC
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ADDITIONAL INFORMATION

QUINTESSENTIAL WOODSTOCK VILLAGE LIVING: Offered at $399,600, this beautiful townhouse presents a rare opportunity to own a home in the heart of Woodstock Village at an exceptional value. Enjoy the charm, convenience, and lifestyle of Village living, with easy access to Woodstock's shops, restaurants, recreation, and the greater Upper Valley. THE HOME: The largest layout in a peaceful 24-home community, this immaculate Federal-style brick townhouse offers 2,268 sq. ft. of living space across three fully finished levels. It functions seamlessly like a single-family home, with an open floor plan, abundant natural light, a wood-burning fireplace, and stunning hardwood floors. The flexible layout includes two spacious upstairs bedrooms and a highly versatile first-floor flex room with pocket doors, perfect as a third bedroom, home office, or guest suite. KEY HIGHLIGHTS: Baths on every level. Private, oversized outdoor deck surrounded by mature woods and perennial gardens. Walking distance to the Woodstock Farmers' Market and National Park trailheads. A UNIQUE OWNERSHIP OPPORTUNITY: This home is offered under a local deed program with specific buyer qualifications, allowing eligible buyers the opportunity to own a Woodstock Village home at an exceptional value. Wondering if you qualify? Contact broker for a simple explanation of the requirements and to find out whether this opportunity could be right for you.

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$1,075,000

648 Church Hill Road Road Woodstock, VT 05091

MLS: 5103213 Photos
Beds:
3
Baths:
3.00
Sq.Ft.:
3,030
Status:
Active
MLS#:
5103213
Type:
Single Family
Lot size:
5.1 Acres
Year built:
1947
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Williamson Group Sothebys Intl. Realty
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ADDITIONAL INFORMATION

This superbly cared-for cape-style home has been thoughtfully and comprehensively updated, with all bathrooms tastefully renovated with quality fixtures and finishes. The home features a creative, livable floor plan with a mix of open gathering rooms and comfortable private spaces, accented with crown molding and 8 1/2-foot ceilings on the main level. The main level has two entries, with additional direct access from the spacious 2-car garage. A mudroom connects the front and garage entries, and the back entry near the garden barn is close to the kitchen. The generous living room centers on a wood-burning fireplace with floor-to-ceiling windows spanning the width of the room. A gracious dining room adjoins the living room, den/bedroom, kitchen, and private stairway to the primary bedroom suite. The second level includes the primary bedroom with study/dressing room, walk-in closet, private balcony, and en suite bath with Italian marble vanity, tile, and surfaces. The second bedroom is illuminated by natural light and well-appointed en suite bathroom. A second-floor family/media room is separate from the sleeping areas. The property is within easy walking distance to the Village Green, shopping, entertainment, elementary school, and all resort amenities. A gem waiting to be discovered.

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$1,695,000

353 Cabot Road Road Woodstock, VT 05091

MLS: 5102668 Photos
Beds:
4
Baths:
3.00
Sq.Ft.:
3,542
Status:
Active
MLS#:
5102668
Type:
Single Family
Lot size:
18.4 Acres
Year built:
1972
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Snyder Donegan Real Estate Group
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ADDITIONAL INFORMATION

"BLISS HOUSE" Privately nestled on a picturesque hillside just minutes from the Woodstock Village Green, this beautifully renovated residence offers exceptional privacy, sweeping long-range mountain views, open meadows, mature gardens, a swimming pool, hot tub, and the perfect blend of Vermont charm and modern comfort. A thoughtful renovation transformed the kitchen and dining areas into a bright, open gathering space where spectacular mountain views are always on display. The newer gourmet kitchen features a large center island, Thermador appliances, quartz countertops, and abundant custom cabinetry. The spacious living room is centered around a handsome stone fireplace and offers multiple seating areas. French doors open to a newer southwest-facing deck with a large hot tub, creating the perfect setting to enjoy sunsets and panoramic views throughout the year. The main level also includes a generous primary suite with a walk-in closet and an ensuite bath featuring a soaking tub with mountain views and a separate shower. A mudroom with laundry connects directly to the oversized attached two-car garage. A circular staircase leads from the kitchen to a charming renovated tavern and wine room with French doors opening to a private brick patio, ideal for entertaining. Upstairs are a comfortable office, study, or media room, three additional bedrooms (two with long-range views), an updated full bath, and a separate half bath. The full concrete basement provides abundant storage and houses the mechanical systems. Additional amenities include a full-house automatic generator, ample parking for four or more vehicles in addition to the attached garage, and well-maintained grounds. BLISS HOUSE combines privacy, stunning views, quality renovations, and an exceptional location just minutes from Woodstock Village. Walk-through tour, video, drone aerials, and floor plans available online.

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$244,000

42-18 Heritage Condo Way Way Unit Unit 18D Woodstock, VT 05091

MLS: 5101220 Photos
Beds:
1
Baths:
1.00
Sq.Ft.:
856
Status:
Active
MLS#:
5101220
Type:
Condo
Lot size:
7 Acres
Year built:
1987
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Williamson Group Sothebys Intl. Realty
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ADDITIONAL INFORMATION

Easy living in this updated condo that is perfect for a primary or secondary residence. Located in a small condo community that is mostly owner occupied the setting offers a private living space. The deck looks out to well maintained grounds and woodlands. The updated kitchen and bathroom are well appointed. The main level has an open floor plan that includes the kitchen, dining area and living room . Upstairs , in addition to the bedroom, bath and laundry there is a wonderful bonus area that can be used in multiple ways and the sliding barn door provides privacy to the area. Located across from Woodstock Middle and Senior High School as well as the Woodstock Senior Center and just minutes from the center of the historic town of Woodstock voted one of the prettiest small towns in America ! Close to skiing at Killington and Woodstock's own Saskadena Six there is access to sports and activities for every season. Call for a private viewing .

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$1,195,000

16 Church Street Street Woodstock, VT 05091

MLS: 5100512 Photos
Beds:
4
Baths:
3.00
Sq.Ft.:
3,979
Status:
Active
MLS#:
5100512
Type:
Single Family
Lot size:
0.52 Acres
Year built:
1890
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Williamson Group Sothebys Intl. Realty
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ADDITIONAL INFORMATION

This wonderful Vermont Cape-style home is a peaceful hideaway with amazing views upriver towards Killington is within walking distance of Village shops, restaurants, and resort amenities. The home has overlooked the Ottauquechee River and the former Woodstock woolen mill since 1890. The old mill has long since been repurposed as a children's daycare center surrounded by community pools, basketball courts, and the Town's recreation center. On long summer days, the joyful sounds of children enjoying the wide sand beach and swimming holes float up from the river below. Over the years, the floor plan has been adapted on all three levels to modern lifestyles. The main level, entered from the garden walkway or garage, connects to an open country kitchen via a mudroom, which flows into the dining area and living room, offering extraordinary upriver views west toward Killington. A spacious main-floor primary bedroom with an en suite bath opens to a riverside deck, and an expanse of lawn and gardens surrounds the residence. Upstairs are two large bedrooms with a shared bath and a reading loft overlooking the living room below. The walkout lower level includes another bedroom, a bath, a recreation room, and a laundry. The home, like many in Woodstock Village, was damaged in August 2011 by Hurricane Irene. The property is not in the designated 100-Year floodplain that requires insurance. Irene was a FEMA-designated 500-year flood event that affected the basement; afterward, the owners replaced the lower-level sheetrock and the heating boiler and restored the riverbank.

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$400,000

2556 Church Hill Road Road Woodstock, VT 05091

MLS: 5099229 Photos
Beds:
2
Baths:
1.00
Sq.Ft.:
1,324
Status:
Active
MLS#:
5099229
Type:
Single Family
Lot size:
0.51 Acres
Year built:
1860
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Snyder Donegan Real Estate Group
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ADDITIONAL INFORMATION

Once an old school house, this home features stone walls, beautiful gardens, and a nice level yard with a stone patio. The year-round brook cascades over rocks and winds along the back side of the property. A covered porch leads inside, where the main floor offers an eat-in kitchen, a large living room and a dining area with French doors to the outside. There are also two bedrooms, an office with stairs to the basement, a full bath with laundry, and a mudroom. The 2nd floor attic, with a large dormer, offers many possibilities for additional space but requires installing stairs and building out the open area. The basement houses utilities and allows for significant storage. The house needs a few updates but has lots of potential and is a wonderful investment opportunity or a great way to get into a starter home in the Woodstock area. It is conveniently located just minutes from Woodstock Village and only a few miles from the Kedron Valley Inn, the South Woodstock Store, and the Green Mountain Horse Association.

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$497,500

121 Townhouse Way Way Unit 24 Woodstock, VT 05091

MLS: 5098210 Photos
Beds:
3
Baths:
3.00
Sq.Ft.:
2,268
Status:
Active
MLS#:
5098210
Type:
Condo
Lot size:
15 Acres
Year built:
1979
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Williamson Group Sothebys Intl. Realty
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ADDITIONAL INFORMATION

Live Work Play, Retire and Play, or Just Play on the Weekends and Holidays! This wonderful 3 BR, 3 Bath Townhome/Condo has it all. Nestled in a small quiet wooded community less than 5 minutes from the Historic Woodstock Center and conveniently located within walking distance of Woodstock Union Middle & High School. It is also located only 30 minutes from Killington Ski Resort and Okemo Ski Resort and 10 minutes from Saskadena Six. The location and price make this home a truly unique buying opportunity for several types of owners. The very private 24 home community is comprised of retirees, working families, and second home owners who want to enjoy all Vermont has to offer. The neighbors are awesome! This home is the most private in the complex as it is the very end unit surrounded on 3 sides by woods and streams. The unit is in very good condition and move in ready. The first floor is comprised of a den/bedroom with pocket doors for added privacy and an adjacent 3/4 bath. Also on the first floor is a spacious living room anchored by a propane fireplace, nicely crafted mantle and hardwood floors. A couple of steps down takes you into a renovated kitchen with stainless appliances and gleaming soapstone counters. A small eating area is surrounded by windows overlooking the back deck facing east with beautiful woods on 2 sides. Wildlife abounds. Tall ceilings and an abundance of natural light make the kitchen area a favorite space. The second floor consists of a very large primary bedroom with a seating area and three closets for an abundance of storage. The second bedroom is spacious with lots of sunlight. A good size full bathroom with tiled floors completes the second level. The lower level is a large family room with a walk out to a lovely patio. This level also has its own 3/4 bathroom, laundry area and several storage closets. The lower level has lots of options for use given the design. Open House- Saturday July 18th from 11am-1pm

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$799,999

3036 West Woodstock Road Road Woodstock, VT 05091

MLS: 5098474 Photos
Beds:
3
Baths:
3.00
Sq.Ft.:
2,600
Status:
Active
MLS#:
5098474
Type:
Single Family
Lot size:
2.9 Acres
Year built:
1996
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: KW Vermont Woodstock
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ADDITIONAL INFORMATION

On a small hill, amongst trees and beautiful gardens, sits this beautifully maintained log cabin with sweeping views of the surrounding mountains and river valley. Just a short drive outside of Woodstock Village, this cabin offers the perfect blend of privacy and convenience. Built in 1996, this thoughtfully crafted home features approximately 2,600 square feet of living space on 2.9 acres. The home offers 3 bedrooms and 2.5 bathrooms, with warm and inviting open living spaces anchored by both a fireplace and a wood stove, perfect for cozy Vermont evenings. A spacious porch takes full advantage of the South Easterly views, providing an ideal spot to relax and take in the natural surroundings. A detached 2-car garage with an accessory dwelling unit studio above, complete with a 3/4 bath; ideal for guests, rental potential, or a private office/studio. A potting shed and a wood shed complete the outdoor spaces, offering ample storage and outdoo hobbies. With its combination of rustic charm, modern utility, and an central location, this property is a rare opportunity to enjoy mountain living without sacrificing accessibility to nearby amenities and recreation.

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$2,300,000

915 Peterkin Hill Road Road Woodstock, VT 05091

MLS: 5098424 Photos
Beds:
5
Baths:
6.00
Sq.Ft.:
3,489
Status:
Active
MLS#:
5098424
Type:
Single Family
Lot size:
9 Acres
Year built:
2003
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Williamson Group Sothebys Intl. Realty
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ADDITIONAL INFORMATION

Exceptional Views to Killington! Perched high on a private knoll and surrounded by open lush meadows and surrounded by antique stonewalls. This 5 bedroom, 4 bathroom extended cape styled home was renovated approx 15 years ago with handsome hardwood floors throughout. Large kitchen with Calcutta Marble, Electrolux stainless appliances and ample storage that opens into the dining room- The formal living room also has expansive views beyond the french doors to a covered porch across the back of the house for entertaining family and friends. The living room is anchored by a traditional propane fireplace, custom book shelves, lovely pocket doors... it's easy to want to curl up with a good book in the wintertime. Generous primary suite with custom built-ins, walk in closet and expansive bathroom located on first floor. There is a second guest bedroom with full bath on the first floor as well as a cozy den surrounded by built-in bookcases. Second floor features 3 very large bedrooms and 2.5 bathrooms including a clawfoot tub. A walk out basement for easy access to store patio furniture. Ample storage or potential for a workshop. There is a generator on site, 2 bay attached garage and barn/stables down below the property. The majority of the property is open and mowed to perfection. This estate has been well maintained and in a superior location. Killington/Pico and Okemo a short distance. Easy access to historic Woodstock, championship golf, tennis, cross country skiing and shopping. Come take a look. Not many properties with this exceptional view!

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$12,950,000

3147 Mount Hunger Road Road Barnard, VT 05091

MLS: 5097482 Photos
Beds:
5
Baths:
10.00
Sq.Ft.:
8,827
Status:
Active
MLS#:
5097482
Type:
Single Family
Lot size:
264.4 Acres
Year built:
1852
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Williamson Group Sothebys Intl. Realty
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ADDITIONAL INFORMATION

Offered as a fully curated legacy estate, Honey Hill Farm encompasses 264.4 extraordinary acres of pastoral beauty, panoramic mountain views, and an unrivaled network of private trails, with an additional contiguous 42.6-acre parcel available for purchase. More than a luxury property, Honey Hill offers the experience of a private park, with nearly 10 miles of trails winding through forests, open meadows, cascading brooks, waterfalls, and around a spring-fed pond. Whether for hiking, cross-country skiing, horseback riding, mountain biking, or quiet exploration, the land offers a seldom-found level of privacy and recreation. The main residence has been masterfully reimagined through a full-scale renovation, blending timeless craftsmanship with modern luxury. At its heart lies an expansive gourmet kitchen with custom marble finishes and bespoke detailing. A four-season room with floor-to-ceiling glass doors dissolves the boundary between indoors and the breathtaking landscape beyond. Formal living spaces flow seamlessly into a richly appointed bar and billiards room and onward to a spectacular library, where exquisite millwork and tailored lighting create an atmosphere of quiet grandeur. Each bedroom suite is generously scaled and paired with indulgent ensuite baths. An extraordinary spa offers infrared and salt therapies and opens directly to a heated pool surrounded by nature. Modern systems ensure comfort and security, including radiant heat, central air, water purification, and a whole-house generator. The iconic red barn has been fully restored, with upper-level entertaining and fitness space and a beautifully appointed guest apartment below. Offered as a fully curated turnkey estate, Honey Hill includes exquisite custom furnishings thoughtfully selected to complement the home and setting, allowing for immediate enjoyment. Privately sited behind gates and shown by appointment only, Honey Hill Farm is a world unto itself and legacy in the making.

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$774,000

1326 Curtis Hollow Road Road Woodstock, VT 05091

MLS: 5097258 Photos
Beds:
3
Baths:
3.00
Sq.Ft.:
2,004
Status:
Active
MLS#:
5097258
Type:
Single Family
Lot size:
30.18 Acres
Year built:
1850
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Real Broker LLC
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ADDITIONAL INFORMATION

If you've been dreaming of the quintessential Vermont lifestyle, this exceptional property delivers the perfect blend of privacy, charm, and convenience. Nestled on over 30 acres in Woodstock, this classic farmhouse is surrounded by beautiful open fields, mature trees, and peaceful natural beauty. Inside, you'll find a spacious eat-in kitchen that's perfect for gathering with family and friends, while the inviting living room features exposed beams and a cozy wood stove that adds warmth and character. The first floor also offers a primary bedroom with an ensuite bath and the convenience of first-floor laundry. Upstairs are two additional bedrooms, a bonus room, and a separate office or flex space ideal for working from home. Outside, relax on the covered front porch, unwind on the patio, or soak in the hot tub while taking in the scenic surroundings. The classic Vermont barn offers abundant storage, space for vehicles or equipment, and includes an attached chicken coop. The land is truly the highlight, with a picturesque pond, perennial gardens, open pasture, and a mix of wooded acreage offering endless opportunities for recreation, gardening, or simply enjoying the outdoors. All of this is just minutes from Woodstock Village, world-class skiing, shopping, dining, and everything this sought-after region has to offer.

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$1,645,000

2706 East Woodstock Road Road Woodstock, VT 05091

MLS: 5096963 Photos
Beds:
4
Baths:
4.00
Sq.Ft.:
4,800
Status:
Active
MLS#:
5096963
Type:
Single Family
Lot size:
0.56 Acres
Year built:
1850
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Bassette Real Estate Group
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ADDITIONAL INFORMATION

Gracious Single Family home and Investment Opportunity - This 3 bedroom, 2 bath brick colonial is approx. 2,300+/- sq/ft with beautiful old wood flooring, newer kitchen, upgraded systems, and fully furnished. Also included, is an additional 2,500+/- sq/ft (total) of an AirBNB rental/In-Law apartment, along with an active US Postal Service rental space, and generous storefront space in the former Taftsville Country Store. Expand your living space and use the large, open storefront as a home office or as an entertaining TV /Theatre room (we will even throw in two rows of reclining Theater seats)! The current owners use the place as a second home getaway. The rental offsets would be the Post Office lease (can be cancelled if the space is needed for other ventures) and whatever you choose to do with the smaller Airbnb one bedroom rental. Perfect opportunity for a vacation getaway/combo investment to offset living expenses with this small scale multi-unit property. Just five minutes to the quintessential downtown Village of Woodstock! Property consists of a spacious 3Brm/2Bth two story Owners quarters, storefront space with bath (approved for restaurant, café, or retail store), Post Office (with current lease), smaller one bedroom Apartment/In-Law rental (former AIRBNB rental), and additional storage space for second home toys. Current owners have redesigned, paved, and expanded the parking lot to include 21 parking spaces to the south side with four (4) 19Kw Electric Vehicle Charging stations, ADA access to building, and ADA accessible restrooms. Property boasts pretty patio views of the Ottauquechee River and Taftsville Covered Bridge. The historic village of Taftsville is known to be a wonderful community and is a desirable location for home ownership. Must see to appreciate! *Main Level Photos Have Been Electronically Decluttered*

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$839,500

217 South Perry Road Road Barnard, VT 05091

MLS: 5097016 Photos
Beds:
3
Baths:
3.00
Sq.Ft.:
2,667
Status:
Active
MLS#:
5097016
Type:
Single Family
Lot size:
2.7 Acres
Year built:
1978
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Williamson Group Sothebys Intl. Realty
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ADDITIONAL INFORMATION

This spacious, well-maintained Gambrel-style home is designed for gracious country living, with a post-and-beam frame that creates large gathering spaces accented by two fireplaces, thoughtful features, and abundant natural light. The private parcel, landscaped with perennials and flowering shrubs, is positioned on a rise overlooking the Barnard Valley towards Woodstock, a few miles south. The location offers a highly desirable balance of privacy and proximity to all resort amenities, shopping, schools, and services, all within a few minutes' drive. A versatile floor plan can be configured with 3 or 4 bedrooms, each capturing views of the surrounding countryside. The superb eat-in kitchen with a breakfast bar is central to the home, surrounded by a dining area and a family room with a well-equipped entertainment center. A separate living room connects to places for celebrating the seasons: a bluestone-paved patio in summer and a greenhouse addition with ideal solar exposure, providing a welcome source of warmth and light in winter. Highlights include updates focused on energy efficiency and modern living, such as high-speed fiber-optic service, an airtight wood stove, a gas fireplace, a heat pump water system, and Tesla batteries, which add resilience. Close to miles of trails, skiing, golf, fishing, and all of Vermont's outdoor attractions.

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$2,999,000

18 The Green Woodstock, VT 05091

MLS: 5096089 Photos
Beds:
6
Baths:
8.00
Sq.Ft.:
5,142
Status:
Active
MLS#:
5096089
Type:
Single Family
Lot size:
0.36 Acres
Year built:
1840
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Williamson Group Sothebys Intl. Realty
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ADDITIONAL INFORMATION

Centrally located on the southwest side of the historic 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 and functionality. 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 an au pair suite, three car garage, and courtyard entrance on the walk out lower level stepping out to lovely, landscaped grounds and award winning gardens.

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$1,199,000

2 High Street Woodstock, VT 05091

MLS: 5094456 Photos
Beds:
3
Baths:
3.00
Sq.Ft.:
1,950
Status:
Active
MLS#:
5094456
Type:
Single Family
Lot size:
0.07 Acres
Year built:
1890
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Bassette Real Estate Group
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ADDITIONAL INFORMATION

Beautifully Restored all the way down to the studs, c. 1890 Village Home in the Heart of downtown Woodstock! Extensively renovated while preserving its historic charm, this 3-bedroom, 3-bathroom residence offers the perfect blend of character and modern convenience right in the center of EVERYTHING. Major renovations and improvements include updated spray foam insulation, walls, windows, wiring, flooring, appliances, even structural supports, and dual new heating systems with Central AC. Abundant natural light highlight the homeâ??s timeless appeal and the new deck over the garage insures you won't miss any of the action in town. The main level features a sun-filled living room with fireplace, private study with adjoining 3/4 bath, and an open-concept kitchen and dining area with quartz countertops, stainless appliances, and direct access to a welcoming covered porch overlooking the quaint New England charm of downtown Woodstock. Upstairs are three bedrooms, including a spacious primary suite with private bath and double closets. A second full bath features a tiled shower, soaking tub, and new Washer & Dryer. The finished third floor provides an exceptional bonus space ideal for a family room, office, studio, playroom, or guest accommodations, along with a separate storage room. Additional amenities include a paved driveway, lower-level garage/storage area, town water and sewer, dual Bosch propane boilers, propane 75G hot water, central air conditioning, and low-maintenance village living. Enjoy being just steps from Woodstockâ??s renowned restaurants, shops, galleries, recreation, and community events. A rare opportunity to own a move-in-ready historic home in one of Vermontâ??s most desirable village locations.

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$2,650,000

66 Hollow Farm Road Road Woodstock, VT 05091

MLS: 5091062 Photos
Beds:
5
Baths:
4.00
Sq.Ft.:
4,843
Status:
Active
MLS#:
5091062
Type:
Single Family
Lot size:
105.1 Acres
Year built:
1988
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Snyder Donegan Real Estate Group
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ADDITIONAL INFORMATION

CURTIS HOLLOW FARM, Exceptional estate on the western edge of Woodstock offering 105 diverse acres bordering Calvin Coolidge State Forest. The updated main house features 5 bedrooms and 4 baths, filled with abundant natural light and thoughtfully designed for both large gatherings and quiet retreat spaces. The open-concept main level includes a spacious living room with picture windows overlooking the landscaped grounds, a recently updated chef's kitchen with a stunning Mercury/Aga range, and generous dining space nearby. On the east side of this level, the original historic homestead—with its native timbers and stone fireplace—creates a warm and intimate dining experience. A wraparound deck provides additional space for outdoor dining and entertaining, while bedroom with its own bath completes this floor. Upstairs are 4 additional bedrooms, several featuring charming portal windows with views over the surrounding fields & hills. The primary suite is spacious and inviting, highlighted by exposed historic timbers, a sitting area, direct access to an upper deck, and a spa-inspired bath. On the uppermost level, the cupola offers the perfect yoga studio or quiet reading nook, complete with its own private deck. The grounds are truly magical, with an extensive trail network throughout the property and direct access to a magnificent waterfall and swimming hole just beyond the lot line within the State Forest. Large level lawns, mature landscaping, and a brook flowing along the southern side of the property add to its private tranquility. Nestled beside the brook is the guest house, known as the Brook House—a well-maintained 3-bedroom, 2-bath home privately sited away from the main residence, with its own lawn and deck overlooking the water below. With a convenient location offering easy access to Woodstock and Bridgewater Villages and a short drive to Killington Mountain Resort, this stunning estate is the consummate blend of privacy, charm, and modern convenience.

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$695,000

47 Pleasant Street Street Woodstock, VT 05091

MLS: 5089949 Photos
Beds:
3
Baths:
2.00
Sq.Ft.:
2,285
Status:
Active
MLS#:
5089949
Type:
Single Family
Year built:
1920
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Snyder Donegan Real Estate Group
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ADDITIONAL INFORMATION

Excellent opportunity for residential or office/commercial space with easy access and high visibility on Rt 4 coming into town, Currently configured as office space downstairs (which previously has been living space), combined with a separate two-bedroom apartment (with its own access) upstairs. The 1,335 sf lower level (Unit C) is currently a chiropractor's office space and was previously used as natural food store and barber shop. The 950 sf upstairs two-bedroom apartment (Unit D) has been leased out by the month for approx $2,000 per month, and has two separate bedrooms, a kitchen, sitting area, balcony and full bath. Or you could re-combine the two units into a larger 2,285 sf in-town residence or office space. There are 4 dedicated parking spaces for the two units, plus other parking in the rear that is shared with the other two units (A & B) of this commercial condo complex. This is a great opporunity to own a highly visible, move-in-ready building right on Route 4.

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$1,395,000

1522 Barnard Road Road Woodstock, VT 05091

MLS: 5089552 Photos
Beds:
5
Baths:
4.00
Sq.Ft.:
3,648
Status:
Active
MLS#:
5089552
Type:
Single Family
Lot size:
6.2 Acres
Year built:
1850
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Williamson Group Sothebys Intl. Realty
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ADDITIONAL INFORMATION

Just 2 miles from Woodstock Village, this gracious brick Cape on 6 open acres offers the perfect blend of privacy, comfort, and classic Vermont charm. Thoughtfully expanded and beautifully maintained, the home features a chef's kitchen that opens seamlessly to a spacious gathering room designed for entertaining and everyday living. Multiple fireplaces—including a wood-burning and gas-ready—add warmth and character throughout the home. The flexible floor plan includes 3–4 bedrooms, highlighted by an upstairs bedroom with its own fireplace, plus a private guest suite or office above the garage—ideal for visitors, remote work, or creative space. Outdoor living is equally exceptional. Enjoy a covered porch, sunny patio, dedicated garden space, apiary, and an in-ground pool with heat hookup for extended seasonal enjoyment. More than 5 acres of invisible fencing allow pets to roam freely across the open landscape. Perfectly positioned for year-round recreation, the property sits adjacent to the site of America's first ski tow and offers easy access to Saskadena Six, Killington, and outstanding winter activities throughout the region. A standout feature is the heated and plumbed two-story barn/workshop with its own vehicle bay—offering endless possibilities as a media or game room, studio, workshop, fitness space, or future guest quarters. With easy access to I-89 and the Upper Valley, this rare offering combines acreage, versatility, and close proximity to one of New England's most iconic villages.

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$595,000

11 Maple Street Street Woodstock, VT 05091

MLS: 5088170 Photos
Beds:
4
Baths:
2.00
Sq.Ft.:
2,288
Status:
Active
MLS#:
5088170
Type:
Single Family
Lot size:
0.15 Acres
Year built:
1900
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Wetmore Real Estate
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ADDITIONAL INFORMATION

A rare Woodstock Village opportunity! A Victorian style home located in Woodstock's much desired Maple Street neighborhood! Popular Vail Field recreation area is conveniently nearby! For children in Maple Street's Neighborhood, Woodstock Elementary School is just a short walk away. Currently the residence is configured as home to 2 generations of occupants. A ground floor apartment conveniently accessed from 3 sides of the home comfortably provides accommodation for practical single level living. The main entrance is through a spacious 12'x10' mudroom. A great attribute in Vermont winters! On 1 end of a well thought out floor plan is a generously sized bedroom with a nearby bathroom. Midway in the apartment is a nicely appointed kitchen that then leads to an appealing dining area. Through a door off the dining area several steps lead to a laundry room that conveniently has an exit leading out to the rear of the property. A living room off the dining area completes the attractive apartment. Well placed windows throughout this ground floor provide pleasant views and natural light. A spacious 2nd floor apartment, with 2 levels of living space, is accessed through a private doorway on the front exterior of the residence. A flight of stairs leads up to the primary apartment area consisting of a bedroom, a dining room, a living room, a kitchen and a bath. Off the kitchen is a partially finished laundry area and then stairs leading down to a ground level workshop. Above the primary apartment is a useful 2 room attic area and a potential bath. Although this 2nd floor apartment has been a full time residence, a new owner will certainly choose to renovate some components of the apartment. The landscaped lot has much appeal with space for gardens and for relaxing outside. Residents in this neighborhood can enjoy walking to village amenities of shopping, dining and cultural events. A Victorian style home full of enormous potential! Location, location!

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$2,500,000

114 Oak Ridge Way Woodstock, VT 05091

MLS: 5087228 Photos
Beds:
4
Baths:
4.00
Sq.Ft.:
5,127
Status:
Active
MLS#:
5087228
Type:
Single Family
Lot size:
17.65 Acres
Year built:
1993
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Snyder Donegan Real Estate Group
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ADDITIONAL INFORMATION

See the property specific website with video, 3-D tour and more. Set against the timeless beauty of Woodstockâ??s rolling countryside, this exceptional estate offers a rare blend of refined luxury and pastoral charm. Thoughtfully designed for both elegant entertaining and everyday comfort, the four-bedroom, four-bath residence centers around a stunning gourmet kitchenâ??complete with a Sub-Zero refrigerator, Wolf range, dual dishwashers, prep sink, and a generous granite island perfect for gathering. Beyond the kitchen, a gracious butlerâ??s pantry, inviting den, game room, and large living room create a home that is as functional as it is inviting. Expansive windows frame unobstructed views, bringing the surrounding landscape into every room, while modern efficienciesâ??including a whole-house generator and rooftop solarâ??offer peace of mind and sustainability. Equestrians and hobby enthusiasts alike will appreciate the impeccably maintained grounds: a four-stall barn with heated tack room, double run-in shed within the six-acre pasture, a greenhouse, and an additional five-bay garage/shop provide endless flexibility for pursuits and storage. The primary three-car garage ensures convenience close to home. With two wells servicing the property and an included separate, buildable lot with a four-bedroom septic design, the estate presents a unique opportunity for expansion or multigenerational living. All of this, just seven minutes from the charm of Woodstock Village and under twenty minutes to world-class skiing, creates a lifestyle defined by privacy, beauty, and effortless access to Vermontâ??s finest amenities.

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$1,895,000

2394 Fletcher Hill Road Woodstock, VT 05091

MLS: 5084536 Photos
Beds:
2
Baths:
3.00
Sq.Ft.:
2,944
Status:
Active
MLS#:
5084536
Type:
Single Family
Lot size:
14.9 Acres
Year built:
2021
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Snyder Donegan Real Estate Group
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ADDITIONAL INFORMATION

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.

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$718,500

37 South Street Street Woodstock, VT 05091

MLS: 5081166 Photos
Beds:
3
Baths:
2.00
Sq.Ft.:
1,660
Status:
Active
MLS#:
5081166
Type:
Single Family
Lot size:
0.19 Acres
Year built:
1900
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: KW Coastal and Lakes & Mountains Realty/Hanover
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ADDITIONAL INFORMATION

Great new price! Nestled in the vibrant heart of Woodstock Village, this beautifully renovated residence offers the ultimate "walk to all" lifestyle. Stepping inside, newly installed pine flooring guides you through an inviting main level designed for both daily living and effortless entertaining. The cozy living room anchors the home with its warm gas fireplace, while the spacious dining area flows seamlessly into a stunning, expanded kitchen equipped with sleek quartz countertops, and elegant cabinetry. Upstairs, three comfortable bedrooms provide peaceful retreats, highlighted by a versatile sitting room off the primary bedroom that easily transforms into a private study or playroom. Modern peace of mind is built right in, thanks to a new second floor bath, new energy efficient propane furnace, upgraded 200 AMP electrical wiring, and many more upgrades. Outside, the classic covered porch serves as your front-row seat to the serene village surroundings. Directly across the street, the open green spaces of Vail Field invite you to enjoy playgrounds, ball fields, pickleball/tennis courts or simply walk the dog. Just a short, picturesque stroll away, the very best of Woodstock awaits...from the historic Woodstock Inn and the iconic Village Green to the local elementary school and an array of charming artisan shops, bakeries, and restaurants. For the athlete, this home puts you in the heart of the premier Vermont cycling communities and world class skiing. Complete with a two-car garage with plenty of room to store your outdoor gear, featuring a customizable, partially finished space above, this move in ready gem perfectly blends timeless New England charm with modern sophistication. IMPORTANT NOTE: this home is verified as NOT being in a flood zone! Flood insurance is NOT needed. Come and see this charming updated home in the beautiful village of Woodstock!

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$450,000

85 Townhouse Way Way Unit 14 Woodstock, VT 05091

MLS: 5077683 Photos
Beds:
2
Baths:
3.00
Sq.Ft.:
2,091
Status:
Active
MLS#:
5077683
Type:
Condo
Lot size:
15 Acres
Year built:
1978
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Williamson Group Sothebys Intl. Realty
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ADDITIONAL INFORMATION

Fully furnished condo nestled in a small quiet community just 5 minutes from "Historic Woodstock". Super location! This unit is in very good condition- first floor comprised of a den//bedroom with pocket doors for added privacy and an adjacent 3/4 bath. Spacious living room anchored by a newer propane fireplace to curl up with a book on a cold winter day. A couple of steps down takes you into a renovated kitchen with small eating area overlooking the back deck. Tall ceilings allow this space to feel spacious with an abundance of natural light. Second floor consisted of a very large primary bedroom with ample closets and sitting area. A full bathroom and the second bedroom is a perfect size for guests. Lower level has a walk out patio with new slider doors, large family room with a small kitchen and eat-in area, spacious laundry and 3/4 bathroom. Newer Buderus boiler. Pets are allowed- Offered furnished with all new custom curtains. Come take a look at this turn key property!

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Andrea D. Conner, License 71221, Xome Inc., License 68390, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Ste 100, Lewisville, TX 75067


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Woodstock 05091 Real Estate

Woodstock is located in Vermont. Woodstock, Vermont 05091has a population of 3,011. Woodstock 05091 is more family-centric than the surrounding county with 37.05% of the households containing married families with children. The county average for households married with children is 26.01%.

The median household income in Woodstock, Vermont 05091 is $104,716. The median household income for the surrounding county is $63,787 compared to the national median of $69,021. The median age of people living in Woodstock 05091 is 53.8 years.

Woodstock Weather

The average high temperature in July is 81.4 degrees, with an average low temperature in January of 6.3 degrees. The average rainfall is approximately 46.1 inches per year, with 82.3 inches of snow per year.

Woodstock Map

Woodstock Real Estate Market Conditions

  • Median sales price

    $430,000
    19.1%
    change since last quarter

  • # Active listings

    51
    30-day change

Woodstock Schools and Demographics

Education near Woodstock, VT

City County
High School Graduates 98.07 94.16
College Degree - 2 year 8.78 8.49
College Degree - 4 year 58.54 40.21
Graduate Degree 21.92 12.49
Expenditures per Student 26,463 26,463
Students per Teacher 12.3 12.3

Elementary Schools near Woodstock, VT

Grades Students P/T Ratio ZIP
Barnard Academy PK - 06 70 10.3 05031
Bridgewater Village School PK - 06 37 6.2 05034
Ottauquechee School PK - 05 244 12.1 05059
Pomfret School PK - 06 53 8.5 05067
Woodstock Elementary School PK - 06 176 9.5 05091

Middle Schools near Woodstock, VT

Grades Students P/T Ratio ZIP
Woodstock Union Middle School 07 - 08 145 10.1 05091

High Schools near Woodstock, VT

Grades Students P/T Ratio ZIP
Woodstock Senior UHSD #4 09 - 12 347 8.9 05091

Demographics near Woodstock, VT 05091

Zip Code City
Neighborhood Type Small town
Population 3,011 57,593
Population Density 68 59
Median Age 53.8 47.8
People per Household 2.3 2.3
Median Household Income 104,716 63,787
Average Income per Capita 56,639 39,377

Real estate near Woodstock

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