Woodstock VT Real Estate & Homes for Sale

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Beds:
4
Baths:
2.00
Sq.Ft.:
2,168
Status:
NEW LISTING
MLS#:
5116985
Type:
Single Family
Lot size:
5.84 Acres
Year built:
1813
Courtesy: Snyder Donegan Real Estate Group
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ADDITIONAL INFORMATION

Exquisitely charming four-bedroom, two-bath Cape set on 5.84 picturesque acres in a coveted West Woodstock location. The thoughtfully landscaped grounds feature open and lush level tiers, a lovely Goshen stone patio framed by an attractive stone wall, a seasonal pond, and a welcoming covered side porch, creating an inviting outdoor setting for relaxing, entertaining, and enjoying the peaceful surroundings. The interior is equally captivating, showcasing original wide pine flooring and a wonderful blend of timeless character and modern comforts. The kitchen is beautifully appointed with high-end appliances including a Sub-Zero refrigerator, Wolf induction/electric range, and handsome soapstone counters. A Jotul woodstove adds warmth and ambiance to the kitchen and dining area, while the living room offers the inviting charm of a wood-burning fireplace. Radiant heated slate flooring in the mudroom and radiant heated tiled flooring in the main level bath provide additional everyday luxuries. In addition, a first-floor bedroom and lovely updated bath with tiled walk-in shower offer the flexibility for single level living. Three additional bedrooms and full bath complete the second level. Thoughtful energy efficiency features include mini splits for year-round heating and cooling, complimented by an impressive 17KW solar array and a Tesla Powerwall. An attached two car barn garage offers excellent functionality, along with an approximately 300 square foot heated and air-conditioned office, ideal for working remotely, creative pursuits, or a private studio. A truly special offering that combines classic New England charm, distinctive architectural details, modern amenities, and an exceptional setting in one of Woodstock's most desirable locations. Perfect as a primary or vacation property within 15 minutes to the Killington Gondola and minutes to downtown Woodstock. Public Open House Sunday Nov 8 from 11AM - 1PM

Beds:
n/a
Baths:
1.00
Sq.Ft.:
3,000
Status:
NEW LISTING
MLS#:
5116691
Type:
Condo
Year built:
1880
Courtesy: Williamson Group Sothebys Intl. Realty
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ADDITIONAL INFORMATION

5 Central Street sits at the heart of Woodstock Village at the historic crossroads of commerce and travel for over 200 years. The Jones Block is the second story of the 1880 brick building, converted into three condominiums, with retail businesses fronting the ground-floor sidewalk and offices on the upper levels. The approximately 3,000-square-foot second floor is currently divided into 11 offices accessed directly off the Central Street sidewalk. Rear access from the Village parking lots is via stairs leading to the back hallway through the former barn. In the past, many of the commercial buildings in Woodstock Village combined service and retail use on the ground floor with living spaces above. This traditional use pattern continues in many buildings today, and the Jones Block could be adapted to meet demand for rental apartments in the greater Woodstock area.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,153
Status:
Active
MLS#:
5116353
Type:
Single Family
Lot size:
4.6 Acres
Year built:
1988
Courtesy: Four Seasons Sotheby's Int'l Realty
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ADDITIONAL INFORMATION

Tucked into the hills of South Woodstock, this charming Cape-style home offers privacy, mountain views, and a wonderful setting on 4.6 acres of lawn and woodland. Built in 1988 and thoughtfully remodeled in 2014, the home combines classic Vermont character with inviting, updated living spaces across three levels. The heart of the house is an open kitchen, dining, and gathering area with wide-plank wood floors, exposed timber accents, natural wood cabinetry, granite countertops, a professional-style gas range, and a breakfast bar. A woodstove set against a striking stone surround adds warmth to the gathering room, while generous windows bring the outdoors in. A separate living room provides a comfortable place to unwind. Upstairs, two bedrooms feature charming rooflines and wood floors, while a beautifully appointed bath offers a clawfoot soaking tub, separate tiled shower, and beadboard detailing. The walkout lower level features a spacious third bedroom, a three-quarter bath, and attractive cork flooring, providing comfortable accommodations for guests and additional living flexibility. Outside, an expansive deck overlooks the lawn, woodland, and surrounding hills, ideal for relaxing or entertaining. A covered entry, standing-seam metal roof, and attached two-car garage add practical appeal. Conveniently located near South Woodstock, Woodstock Village, and Route 4 toward Killington, the property offers year-round access to skiing at Killington and Saskadena Six, hiking, recreation, restaurants, and shopping throughout the Ottauquechee Valley. An inviting primary residence or Vermont getaway.

Beds:
5
Baths:
6.00
Sq.Ft.:
3,154
Status:
Active
MLS#:
5115063
Type:
Single Family
Lot size:
0.31 Acres
Year built:
1900
Courtesy: Covered Bridge RE
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ADDITIONAL INFORMATION

Currently operating as an award winning B&B, this thoughtfully designed, flexibly configured income property is also ideal as a primary residence. Situated at 45 Pleasant Street, just a short stroll from the shops, restaurants and galleries of Woodstock Village, the property overlooks East End Park and the Ottauquechee River Trail, offering an exceptional blend of village convenience as well as natural beauty and outdoor recreation. Inside, historic Vermont charm meets sophisticated contemporary design, with rich finishes, warm hardwood floors, dramatic tilework, custom built-ins and thoughtfully designed lighting throughout. Beautifully appointed baths feature contemporary tile, glass-enclosed showers and upscale finishes reminiscent of a luxury boutique hotel. Guest accommodations offer comfort and privacy, with each principal guest room featuring a king bed, private bath and wet bar equipped with refrigerator, microwave and coffee maker. The expansive 420-square-foot suite includes a separate living room and spa-inspired bath with double vanity, heated floors, heated towel rack and jetted tub. Inviting common areas, a guest lounge, wraparound porch, decks, gardens and fire-pit areas create wonderful spaces for entertaining or relaxation. A dedicated yoga/Pilates studio offers additional flexibility for wellness activities or personal enjoyment. The private upper-level owner's quarters feature two bedrooms, two beautifully appointed baths, a full eat-in kitchen and finished attic space, providing exceptional flexibility for an owner/operator, extended family or full-time residence. Enjoy Woodstock's four-season lifestyle, from skiing and snowshoeing to hiking, golf, cycling and exploring Vermont's scenic countryside. Whether envisioned as a private residence, hospitality venture or investment property, this distinctive offering combines an established rental platform, exceptional location and versatile living spaces. A rare opportunity to make it your own!

Beds:
5
Baths:
3.00
Sq.Ft.:
3,294
Status:
Active
MLS#:
5113873
Type:
Single Family
Lot size:
0.55 Acres
Year built:
1856
Courtesy: Snyder Donegan Real Estate Group
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ADDITIONAL INFORMATION

EATON HOUSE- Steeped in history and ideally situated in Woodstock's Historic District, the Eaton House is a handsome Greek Revival-inspired residence built in 1856. Set on a beautifully landscaped .55-acre lot bordering the lovely Kedron Brook, the property offers a rare combination of historic character, modern comfort, and effortless Village living. The interiors are bright and charming, seamlessly blending architectural details with thoughtful updates. The main level is designed for both everyday living and entertaining, with a well-appointed kitchen and dining area complemented by a gracious formal dining room featuring built-in china cabinets and French doors. Adjacent the dining room at the front of the house is a formal sitting room, while across the foyer, a spacious living room with built-in bookshelves centers around a cozy fireplace. Upstairs, five bedrooms and two baths provide generous accommodations for family and friends. Outside, a private deck off the kitchen offers a peaceful setting for outdoor dining and hosting social gatherings. An attached two-car garage and upgraded mechanical systems, including mini-splits for heating and cooling, add modern convenience. Just a short stroll from Woodstock Village's acclaimed shops, restaurants, galleries, cultural, and recreational offerings, this exceptional property captures the timeless appeal of Village living while offering the comfort and functionality of today. Enjoy the annual Wassail Parade from your own front porch, and view of the Mount Tom Star from the ell of the house. Note: some photos virtually adjusted.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,562
Status:
Active
MLS#:
5113057
Type:
Condo
Year built:
1985
Courtesy: Snyder Donegan Real Estate Group
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ADDITIONAL INFORMATION

Enjoy expansive views from every level of this beautifully updated, 3-bedroom, 3-full-bath Blake Hill condominium. As a highly desirable end unit, this property welcomes you with a classic bluestone entryway and a large wrap-around porch perfect for outdoor relaxing. Inside, the multi-level floor plan offers exceptional privacy, with an open-concept main level showcasing soaring vaulted ceilings, a dining area, and a living room centered around a cozy wood-burning fireplace with custom built-ins. The large chef's kitchen features stylish appointments, upscale appliances, and a premium Sub-Zero refrigerator. Adjacent the kitchen is a large bedroom with an attached bath, perfect accommodations for friends or family, while a functional mudroom rounds out the main floor. An en suite primary bedroom and sitting area/office serves as a secluded retreat on the entire second level. The fully finished ground level adds significant living space with a sizable third bedroom, full bath, secondary family room with its own fireplace, and massive extra bonus room with dedicated storage. Residents also enjoy access to the community swimming pool, which was completely updated in the summer of 2026. With its proximity to Woodstock Village and the Upper Valley's many cultural and recreational offerings, this turnkey property is a must-see. Note: Some photos are virtually staged. Public Open House: Sunday, October 11 from 11am-1pm.

Beds:
2
Baths:
3.00
Sq.Ft.:
2,268
Status:
Active
MLS#:
5113819
Type:
Condo
Year built:
1982
Courtesy: Williamson Group Sothebys Intl. Realty
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ADDITIONAL INFORMATION

**Classic Woodstock character, generous living spaces, and the ease of low-maintenance living.** Just minutes from Woodstock Village, this beautifully maintained Federal-style brick townhouse offers privacy, comfort, and convenience in an established residential community. With approximately 2,268 square feet of finished living space across three levels, the home offers the comfort and flexibility of a single-family residence without the demands of extensive property maintenance. Freshly painted and updated with new hardwood floors, the inviting interior features a fireplace, comfortable gathering spaces, and a versatile first-floor bonus room with pocket doors, ideal for an office, den, or studio. The eat-in kitchen opens to an oversized deck overlooking lawns, perennial gardens, mature trees, and surrounding woodland. A finished walkout lower level adds valuable living space, with natural light, a full bathroom, laundry, and direct backyard access. Association services include lawn care, snow removal, trash collection, and common grounds maintenance, leaving more time to enjoy Woodstock. The location is exceptional. Woodstock Farmers' Market is just down the street, while nearby trailheads connect to Marsh-Billings-Rockefeller National Historical Park. Woodstock Village, the Woodstock Inn & Resort, Billings Farm & Museum, and outstanding dining and shopping are minutes away.

Beds:
1
Baths:
1.00
Sq.Ft.:
536
Status:
Active
MLS#:
5113625
Type:
Mobile Home
Lot size:
11.58 Acres
Year built:
2021
Courtesy: Vermont Real Estate Company
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ADDITIONAL INFORMATION

A rare opportunity to own 11.58 private acres in S. Woodstock, ideally situated in one of Vermont's most sought-after rural settings. With an existing driveway, well, electric service, septic system, and a modest mobile home already in place, this property offers the infrastructure and flexibility to enjoy the land now while considering its future potential. The land is the true centerpiece. Wooded acreage, natural clearings, gentle slopes, and a peaceful country setting create an ideal backdrop for a Vermont getaway, recreational property, hunting retreat, equestrian use, or future building site. The existing 536-square-foot, 1-bed, 1-bath mobile home provides a simple place to stay while enjoying everything the property and surrounding area have to offer. For equestrian enthusiasts, the location is especially compelling. The property is within approximately two miles of the Green Mountain Horse Association (GMHA) and sits directly along the GMHA Paul Kendall Trail, providing an exceptional connection to one of Vermont's premier equestrian communities and trail networks. The surrounding area is renowned for its horse farms, riding trails, open countryside, and beautiful back roads. The property is also well positioned for the quintessential Vermont second-home lifestyle, with Killington Resort, Saskadena Six, Billings Farm & Museum, Woodstock, and South Woodstock all within easy reach. Enjoy skiing, hiking, horseback riding, cycling, farm visits, fine dining, and the timeless character of the Woodstock area, then return to your own private acreage. From 1985 through 2020, a family of four occupied a three-bedroom home and used the existing septic system without reported issues. The seller has also completed a soil evaluation and septic inspection, with both reports available in the attached documents. Lastly, the seller would be willing to discuss removal of the mobile home if it is not needed by the new buyer. Schedule a private tour today!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,520
Status:
Active
MLS#:
5113572
Type:
Single Family
Lot size:
5.1 Acres
Year built:
1979
Courtesy: Hall Collins Real Estate Group
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ADDITIONAL INFORMATION

Welcome to this newly updated sun-filled craftsman home, ideally located just 4 miles from the heart of Woodstock Village and 11 miles from Killington Ski Resort. Set on 5 acres with a lovely pond, this property offers the perfect blend of privacy, convenience, and Vermont charm. The home features a bright and inviting interior with one bedroom on the main level and two additional bedrooms and a full bath on the lower level. A spacious wraparound porch extends the living space outdoors, providing the perfect spot to relax, entertain, and enjoy the peaceful surroundings. Whether you're looking for a primary residence, Vermont getaway, or a home base for year-round recreation, this beautifully updated chalet offers easy access to skiing, dining, shopping, hiking, and everything the Woodstock and Killington areas have to offer.

Beds:
5
Baths:
5.00
Sq.Ft.:
4,328
Status:
Active
MLS#:
5112419
Type:
Single Family
Lot size:
18.16 Acres
Year built:
1966
Courtesy: Snyder Donegan Real Estate Group
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ADDITIONAL INFORMATION

2687 GARVIN HILL ROAD- Surrounded by the rolling hills and natural beauty of the Woodstock countryside, 2687 Garvin Hill Road offers a quintessential Vermont lifestyle on 18.16 acres, just minutes from the heart of Woodstock Village. Landscaped grounds, old stone walls, and expansive acreage create an inviting setting for gardening, outdoor gatherings, walking the property, or simply enjoying the changing seasons. The 5-bedroom historic residence blends original charm and character with sophisticated upgrades, creating warm, comfortable living spaces without compromising modern convenience. A bright, light-filled kitchen and dining area flows beautifully into a formal dining room and a dramatic vaulted great room–showcasing exposed hand-hewn beams and a wood-burning fireplace–as well as a sizable screened porch overlooking the grounds, all of which provide an ideal setting for entertaining family and friends. Adjacent to the kitchen on the other side of the house is a more intimate living room with a second fireplace, an office, and a bedroom with full bath, offering the possibility of one-level living. Upstairs, there is an en suite bedroom and two additional bedrooms that share a full bath. The lower level adds versatile finished space with a 5th bedroom guest suite with recreation space. An attached three-bay garage and barn provide ample room for vehicles, outdoor equipment, and all the gear that comes with four-season Vermont living. The attached barn has two horse stalls. There are two beautiful ponds on the property, the larger is well positioned in the backyard towards the view. Beyond the property, Woodstock's extensive network of hiking and biking trails, nearby rivers, golf, skiing, and other year-round recreation along with shops, restaurants, and galleries are all within easy reach. Some photos are digitally enhanced.

Beds:
5
Baths:
4.00
Sq.Ft.:
3,502
Status:
Active
MLS#:
5111700
Type:
Single Family
Lot size:
2.57 Acres
Year built:
1811
Courtesy: Williamson Group Sothebys Intl. Realty
View additional info

ADDITIONAL INFORMATION

Located in the heart of the charming hamlet of South Woodstock, the iconic John Arnold Cottle House is widely considered one of Woodstock's finest early residences. Built in 1811, and listed on the National Historic Register, this stately home has been thoughtfully restored, and lovingly stewarded over the years honoring the period detail while creating the perfect unification of antiquity and modern functionality. The bright, spacious rooms flow seamlessly for daily living or entertaining. The impressive Kitchen-Great Room is anchored by a generous brick fireplace, and sweeping 17' cathedral ceiling, and steps out to a private deck overlooking the brook, fields and trail systems beyond. There is a lovely Primary ensuite bedroom, two additional guest rooms and a cozy loft space on the second level. The Kingsley Barn has been transformed into an impeccably appointed two-bedroom lofted guest house with a heated studio space below, and a strong rental history. Cross the brook to the fields and find another barn for storage or animals. Direct access to the GMHA and VAST trail systems for riding, hiking, cross country skiing, and recreation. A short stroll to South Woodstock Store, Kedron Valley Inn and Ransom Tavern. 5 minutes drive to Woodstock Village Green. Furnishings available.

Beds:
3
Baths:
4.00
Sq.Ft.:
2,975
Status:
Active
MLS#:
5111623
Type:
Single Family
Lot size:
10.1 Acres
Year built:
1977
Courtesy: Bassette Real Estate Group
View additional info

ADDITIONAL INFORMATION

SIGNIFICANT PRICE REDUCTION - SOUTH WOODSTOCK - HILLSIDE FARM estate presents an exceptional opportunity to embrace the quintessential Vermont country lifestyle on 10.1 picturesque acres in prestigious South Woodstock. Offered TURNKEY and FULLY FURNISHED, the sale includes an extraordinary array of shop equipment, mechanical equipment and property-maintenance and recreational equipment. Built by a local master craftsman and builder, the residence showcases handsome timber-frame construction, warm woodwork and enduring craftsmanship throughout. Rolling meadows and pastures, woodland, two streams and a scenic pond create an idyllic setting for equestrian, agricultural and recreational pursuits. At the heart of the home, the spacious country kitchen features cherry cabinetry, gas cooktop, and an antique Stewart woodstove. The 20' x 18' great room offers wide pine floors, exposed framing and a soaring cathedral ceiling, overlooking a lovely 14 foot deep pond and scenic vista. The primary suite includes double closets and an ensuite bath with radiant heat, Jacuzzi tub and shower. Additional bedrooms, dining room, and a home office provide flexible living space. The lower level offers a game room with woodstove and pool table, a small kitchenette, and 3/4 bath. The property is remarkably well equipped with a greenhouse, two-stall horse stable, multiple barns and outbuildings, garage workshop, mechanic's shop, and a substantial 23' x 35' woodworking shop. Tucked into the woods is a delightful rustic cabin complete with kitchenette, woodstove, porch and nearby outhouse; an inviting retreat surrounded by nature and set just above one of two babbling brooks. Located in the heart of South Woodstock's celebrated horse country, Hillside Farm enjoys proximity to the renowned GMHA and the area's extensive network of scenic riding trails. This is a rare opportunity to own a gentleman's farm that is move-in ready for a VT homestead or second home. Photos electronically decluttered.

Beds:
4
Baths:
5.00
Sq.Ft.:
3,774
Status:
Active
MLS#:
5111035
Type:
Single Family
Lot size:
6.7 Acres
Year built:
2012
Courtesy: Snyder Donegan Real Estate Group
View additional info

ADDITIONAL INFORMATION

Privately set on 6.7 acres just three minutes from the Woodstock Village Green, this Greek Revival-inspired farmhouse offers views of Mount Tom and the Pomfret Hills. Built by noted local designer and builder Chris Ambrose, it combines the character of the 115-year-old farmhouse that once stood here with energy-efficient modern living. Salvaged floors, beams, doors and hardware bring history to light-filled rooms with oversized Andersen windows and French doors. Custom cabinetry, honed granite and quartz countertops, and carefully chosen fixtures complement the reclaimed details. The kitchen features a five-burner range, pot filler, farmhouse sink, beverage center and generous pantry. The vaulted primary suite offers reclaimed beams, mountain views, a walk-in closet and a bath with a cast-iron clawfoot tub. A second spacious suite has built-ins and a marble bath. Gather by the fireplace, currently fitted with a gas insert, relax on the screened porch, or entertain on the 18-by-32-foot terrace overlooking the hills. A finished lower level with a family room, bunkroom and full bath helps the home sleep up to 13. Radiant heat, mini-split heating and cooling, a Viessmann tankless water heater, whole-house water filtration and high-speed internet support year-round comfort. A standing-seam metal roof, copper details, stone walls, birch trees and an outdoor shower complete this distinctive Woodstock retreat. SEE 306MEOKIWAY PROPERTY WEBSITE FOR VIDEO, VIRTUAL WALK-THROUGH, FLOORPLANS AND MORE.

Beds:
4
Baths:
3.00
Sq.Ft.:
3,306
Status:
Active
MLS#:
5110412
Type:
Single Family
Lot size:
3.34 Acres
Year built:
1850
Courtesy: Williamson Group Sothebys Intl. Realty
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ADDITIONAL INFORMATION

Historic character, beautifully reimagined for modern Vermont living. Minutes from Woodstock Village, this extensively renovated four-bedroom home pairs the warmth and authenticity of its 150-year-old wide-pine floors and exposed beams with a remarkable collection of recent improvements. At the heart of the home is a brand-new, high-end kitchen with Bosch appliances and newly installed natural bluestone radiant heat flooring, complemented by thoughtfully updated baths, including one with a beautifully executed marble walk-in shower. A dramatic new three-story addition, wrapped in oversized casement windows, introduces abundant natural light and generous new living space while creating a compelling architectural counterpoint to the original home. Nearly every major element has been addressed: new ultra-durable Everlast Advanced Composite siding, interior paint, new roof, all new windows, heat and AC pumps throughout, and a whole-house generator provide the comfort, efficiency, and peace of mind of a thoroughly updated property. Outside, the setting is quintessential Vermont. A new natural bluestone patio and walkway open to an expansive, level lawn bordered by the Kedron Valley Brook, where natural swimming holes invite summer afternoons by the water. Established landscaping, a pond, firepit, and the sound of the brook create an unexpectedly private retreat remarkably close to town. The property also features a historic 2,100-square-foot classic red barn with approved septic plans, offering incredible potential for unique expansion. Just minutes from Woodstock Village, with excellent proximity to the Mt. Peg trail system, Woodstock Inn & Resort amenities, and GMHA, this is a rare opportunity to enjoy the soul and craftsmanship of an historic Vermont home with the ease, light, and livability of a comprehensive modern renovation. Old Vermont soul. Entirely new chapter. Showings begin Saturday, 9/19/2026, with an open house from 1-3:30.

Beds:
4
Baths:
3.00
Sq.Ft.:
3,542
Status:
Active
MLS#:
5102668
Type:
Single Family
Lot size:
18.4 Acres
Year built:
1972
Courtesy: Snyder Donegan Real Estate Group
View additional info

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.

Beds:
1
Baths:
1.00
Sq.Ft.:
856
Status:
Active
MLS#:
5101220
Type:
Condo
Lot size:
7 Acres
Year built:
1987
Courtesy: Williamson Group Sothebys Intl. Realty
View additional info

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 .

Beds:
4
Baths:
3.00
Sq.Ft.:
3,979
Status:
Active
MLS#:
5100512
Type:
Single Family
Lot size:
0.52 Acres
Year built:
1890
Courtesy: Williamson Group Sothebys Intl. Realty
View additional info

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.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,004
Status:
Active
MLS#:
5097258
Type:
Single Family
Lot size:
30.18 Acres
Year built:
1850
Courtesy: Real Broker LLC
View additional info

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.

Beds:
3
Baths:
4.00
Sq.Ft.:
5,384
Status:
Active
MLS#:
5099532
Type:
Single Family
Lot size:
68.92 Acres
Year built:
2015
Courtesy: LandVest, Inc/Woodstock
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ADDITIONAL INFORMATION

Sorgenfrei, German for "carefree" captures the spirit of this remarkable 68 acre property in one of South Woodstock's most desirable locations: a place where life slows and the beauty of the Vermont countryside takes center stage. At the end of a quiet road, the property combines sweeping mountain views, and exceptional privacy with a thoughtfully designed hand-crafted, timber frame home. Outside, perennial gardens give way to open pasture suitable for a few horses or sheep, woodland trails for riding, hiking, cross-country skiing, and snowshoeing and direct access to the GMHA trail system. Built in 2015, the three-bedroom residence is defined by soaring spaces, exposed fir beams, walls of glass, and craftsmanship that feels substantial without being formal. Nearly every principal room is oriented toward the eastern views, bringing the surrounding mountains and changing Vermont landscape into daily life. The main level is equally comfortable for quiet everyday living or a houseful of guests, with an open kitchen, dining area, and dramatic great room centered around a floor-to-ceiling double-sided stone fireplace. A more intimate sitting room, screened porch, expansive deck, and primary suite are also located on this floor. Upstairs are a loft office, two en suite guest bedrooms, and a media room. The walk-out lower level adds a gym, infrared sauna, workshop, and temperature-controlled wine room with capacity for approximately 1,000 bottles. An 18.5 kW solar array supports near net-zero living, while a three-bay garage accommodates vehicles, sporting equipment, and the gear that comes with an active Vermont life. Just minutes from Woodstock Village, 16 miles from Killington Resort, and 26 miles from Okemo Mountain Resort.

Beds:
2
Baths:
1.00
Sq.Ft.:
1,324
Status:
Active
MLS#:
5099229
Type:
Single Family
Lot size:
0.51 Acres
Year built:
1860
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.

Beds:
4
Baths:
4.00
Sq.Ft.:
4,800
Status:
Active
MLS#:
5096963
Type:
Single Family
Lot size:
0.56 Acres
Year built:
1850
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*

Beds:
8
Baths:
8.00
Sq.Ft.:
6,200
Status:
Active
MLS#:
5094600
Type:
Single Family
Lot size:
32 Acres
Year built:
1850
Courtesy: Williamson Group Sothebys Intl. Realty
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ADDITIONAL INFORMATION

Kedron Valley Farm c1850: A classic beauty, perched on a knoll overlooking the idyllic hills and lush meadows of the valley with approx 32 acres. This stunning extended antique post and beam cape is complete with a large traditional 4 story barn with 6 horse stables and equipment sheds offers everything one could wish for in a country property. The grounds include gracious old maples, beautiful perennial gardens, antique moss covered stonewalls, an apple orchard, large swimming pond and a privately sited tennis court. The Estate is meticulously cared for and combines antique craftsmanship with modern touches. The Main house consists of 5 bedrooms including a first floor primary suite with private bath, vaulted ceilings and new large walk in closet. Kitchen features thermador appliances and quartz counters anchored by a large dining room with stunning wood floors. An expansive cozy living room centered by a handsome brick fireplace to curl up with a book on a snowy day. The rooms are spacious and inviting with an abundance of light, exposed original hand-hewn beams and easy access for outdoor entertaining on the brick patio or the new east terrace. Enjoy a separate 3 bedroom Guest House for friends/family with good rental income history. New Tesla Tower for backup power. Located in the heart of horse country and the village of South Woodstock. Enjoy skiing, championship golf and fly fishing on the Black River. Easy access to shopping, restaurants and Upper Valley. Only 8 minutes to Woodstock, 2.5 hours to Boston and 5 hours to NYC. Kedron Valley Farm is a stunning, quintessential farm in the heart of GMHA.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,638
Status:
Active
MLS#:
5094379
Type:
Single Family
Lot size:
2 Acres
Year built:
2004
Courtesy: Snyder Donegan Real Estate Group
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ADDITIONAL INFORMATION

This beautifully renovated, truly move-in-ready home has been thoughtfully updated throughout including a brand-new kitchen, refreshed flooring, modernized bathrooms, fresh interior paint, a new garage door, an automatic full-house generator, and more. The property is offered FULLY TURNKEY, with nearly all furniture and furnishings conveying with the sale (artwork excluded). Privately sited in desirable South Woodstock just seven minutes to the Woodstock Green, this home blends comfort, style, and convenience. The open-concept main level brings together the kitchen, dining area, and living room, where a vaulted ceiling and sleek propane fireplace create a warm, contemporary feel. The dining area opens onto a spacious deck and a flat backyard abutting conserved land, offering peaceful views and serene outdoor relaxation. A updated 1st-floor den/office provides flexibility and could easily serve as a 4th bedroom. Upstairs, the primary bedroom features a walk-in closet and a newly updated ensuite bath with elegant glass-tile walls. Two additional bedrooms share a renovated hallway bath. The finished lower level includes a dedicated laundry room and two rooms perfect as game/rec/gym/play rooms or offices. The attached two-car garage leads into a practical mudroom with built-in benches, hooks, and cubbies, ideal for Vermont living. With excellent mechanical systems, a full-house automatic generator, and updates already completed, this home offers effortless ownership in a prime location. If you're seeking a turnkey, stylishly updated home just minutes from town, this South Woodstock gem is the one!

Beds:
3
Baths:
3.00
Sq.Ft.:
1,950
Status:
Active
MLS#:
5094456
Type:
Single Family
Lot size:
0.07 Acres
Year built:
1890
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.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,285
Status:
Active
MLS#:
5089949
Type:
Single Family
Year built:
1920
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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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 Real Estate

Woodstock is located in Vermont. Woodstock, Vermont has a population of 3,011. Woodstock is more family-centric than the surrounding county with 33.72% 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 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 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

    $990,000
    19.1%
    change since last quarter
  • # Active listings

    59
    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

City County
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