Woodstock Vermont MLS Listings Homes For Sale

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WOODSTOCK VT Home for sale $$1,150,000 | $245 per sq.ft.

$1,150,000 | $245 per sq.ft. WOODSTOCK VT HOME FOR SALE
Price Change! reduced by $300,000 down 26% on February 15th 2025

119 English Mills Way 5 Beds | 5 Baths |   Total Sq. Ft. 4698  |  Acres: 5.1

An expansive 5 bedroom home, in a private location, conveniently just a few minutes drive from Woodstock Village! Among often sought amenities are a ground floor primary bedroom suite with private bath, a dramatic great room with cathedral ceiling and wood burning fireplace, a generously sized lower level in-law/guest suite with kitchen, dining, living room and bedroom with bath, 3 additional upper level bedrooms with 2 full baths, a family room with an attractive soap stone wood burning stove, a bright kitchen with cherry cabinets and an attached 2 car garage. The well conceived design presents the practical opportunity for single level living utilizing the gracious ground floor bedroom suite. Alternatively, the 5 bedrooms, on 3 levels, can satisfy a whole gang! The lower level private suite could present comfortable accommodations for an in-residence caregiver. Outside, a large wrap around deck transitions to pleasant sunny lawn areas with perennial gardens. Within walking distance are Mt. Tom's hiking trails! The property benefits from owner's who have taken pride in maintaining their beloved home! An attractive home that benefits from a thoughtful interior design! Equally suited for use as a well located year round residence or to be the vacation home that can accommodate friends and family alike! Skiing at Suicide Six as well as all the well known Woodstock Village amenities of shopping, dining and cultural events are just minutes away! Truly a great Woodstock property! See MLS Property & Listing Details & 41 images.


Under Contract WOODSTOCK VT Home for sale $$1,390,000 | $379 per sq.ft.

$1,390,000 | $379 per sq.ft. WOODSTOCK VT HOME FOR SALE
Price Change! reduced by $209,000 down 15% on January 22nd 2025

72 French's Road 6 Beds | 4 Baths |   Total Sq. Ft. 3668  |  Acres: 3.68

In 1880, this lovely hilltop Gambrel Colonial was designed by the prominent Manhattan Architectural Firm, McKim, Mead and White. "Rose Hill" was one of Woodstock's most prominent residences featuring the exquisite workmanship of the region's finest craftsmen. The grand scale and proportion of the rooms and the elegant period detail harken back to days of gracious gatherings with a formal DR complete with custom built-ins, a Library and a Stately Living Room anchored by a central fireplace, with direct access to a brick portico that runs the length of the home- ideal for summer entertaining. The kitchen has custom built-ins, plenty of counter space, a pantry entry, and a secondary staircase to access the second floor. A combination of indigenous hardwood floors run throughout the entire home. The sweeping formal staircase brings you to the second level with a spacious landing, and a wall of built-ins. There are a total of six bedrooms including a roomy primary bedroom with a fireplace, and three bathrooms. To the rear of the home you'll find a separate 2-car garage with a two bedroom rental unit above. Follow the footpath down to a secluded, very sweet two-bedroom guest cottage. All sited on 3.68 AC offering privacy, and plenty of space for gardening, entertaining and recreation. Just a short stroll to the Village Green and the National Park. This very special property awaits your vision to return it to its former splendor. See MLS Property & Listing Details & 45 images. Includes a Virtual Tour


Under Contract WOODSTOCK VT Home for sale $$1,395,000 | $540 per sq.ft.

$1,395,000 | $540 per sq.ft. WOODSTOCK VT HOME FOR SALE

1075 Westerdale Road 3 Beds | 4 Baths |   Total Sq. Ft. 2584  |  Acres: 41.45

This lovingly maintained property with mountain views has been enjoyed by a single family since its construction in 1985. The open-concept layout is anchored by a stone Rumford fireplace, which along with the southern exposure warms the large easy-to-keep space. The first floor master boasts ample storage with a sliding door for quick access to the grounds. Across from the main house via a covered breezeway is a large 2 car garage, gorgeous horse barn with hay loft and a cozy studio apartment, making this the perfect spot for a variety of uses. Equally comfortable as a part-time or full-time home, this property is conveniently located on the western side of Woodstock, just twenty minutes from Killington's Skyeship gondola and ten minutes from downtown Woodstock. With over forty acres on prestigious Westerdale road, owners enjoy privacy and expansion potential. Offered for the first time since its inception, this property is an exceedingly rare opportunity for rolling acreage in a highly coveted location. See MLS Property & Listing Details & 50 images.


WOODSTOCK VT Home for sale $$1,495,000 | $354 per sq.ft.

$1,495,000 | $354 per sq.ft. WOODSTOCK VT HOME FOR SALE

608 Fletcher Hill Road 4 Beds | 4 Baths |   Total Sq. Ft. 4228  |  Acres: 5.4

Open House Sunday, March 2, 12:00 to 2:30 - Tucked away in the serene forests of Woodstock, Vermont, this beautifully remodeled 11-room home offers 4 bedrooms, 4 bathrooms, and 4,225 sq. ft. of luxurious living space on 5.4 private acres. The open-concept design is flooded with natural light, featuring a stunning chef's kitchen with high-end stainless steel appliances, Vermont soapstone counters, custom cabinetry, and a spacious and sunny dining room. The cozy living room boasts one of two wood stoves, creating a warm and inviting space for relaxation. The massive family room is home to the second wood stove. There are two primary en-suites, each with a fireplace and spa-like bathroom, one in a private wing of the home, while the additional bedrooms and updated baths provide comfort and style. Outside, a large, partially screened-in deck and hot tub offer perfect spots to unwind and enjoy the tranquil surroundings--there is even a sauna off the rec room! Plenty of storage is available in the two-car garage or the two-stall barn. With solar panels, propane heating, two fireplaces, and two wood stoves, this home combines eco-friendly features with modern amenities. Its peaceful setting, just minutes from downtown Woodstock, is also close to the Green Mountain Horse Association, VAST snowmobile trails, Killington Mountain, Mount Tom, and the Saskadena Six Ski Area, making it a perfect full-time residence or seasonal escape. Enjoy Vermont living or work from home with EC Fiber! See MLS Property & Listing Details & 53 images. Includes a Virtual Tour


WOODSTOCK VT Home for sale $$1,650,000 | $452 per sq.ft.

$1,650,000 | $452 per sq.ft. WOODSTOCK VT HOME FOR SALE

1522 Barnard Road 5 Beds | 4 Baths |   Total Sq. Ft. 3648  |  Acres: 6.2

Just over 2 miles from the heart of Woodstock village, this gracious brick cape sits on six open acres. Designed to accommodate a Vermont lifestyle, this home welcomes you, whatever the season. The chef's kitchen has been expanded with a spacious entertaining room, and the grand dining room is ideal for hosting. A wood-burning fireplace in the main living room, a brick fireplace in the family room, and a gas-ready fireplace in the den make this home cozy during Vermont's cooler seasons. With 3-4 bedrooms on the second floor (one with fireplace), and an additional bedroom/office above the garage, 1522 Barnard Road offers plenty to a growing family and is a perfect retreat for guests. The surrounding grounds present an uncommon opportunity to own usable acreage in quick proximity to Woodstock. A covered porch for grilling, an entertainment patio, an inground pool with heat hookup, a garden space, an apiary, and a fenced chicken coop make summers at this home idyllic. Dogs can run free with over 5 acres of invisible fencing. Adjacent to the site of the country's first ski tow, winter offers fantastic snowshoeing opportunities and easy access to Saskadena 6. With quick access to I-89 and the Upper Valley beyond, this Woodstock home lends itself to both primary and second-home ownership. An increasing rarity in our market, this home is uniquely positioned to enjoy elbowroom and a more rural landscape, all just minutes from New England's quintessential village. See MLS Property & Listing Details & 60 images. Includes a Virtual Tour


WOODSTOCK VT Home for sale $$1,800,000 | $743 per sq.ft.

$1,800,000 | $743 per sq.ft. WOODSTOCK VT HOME FOR SALE

2090 Randall Road 3 Beds | 3 Baths |   Total Sq. Ft. 2423  |  Acres: 18.9

Constructed in 2007 with a nod to the Gothic Style Vermont Farmhouse vernacular, this beautifully composed country home creatively integrates curated period detail with modern conveniences and systems. Conveniently located at the end of a picturesque tree lined dirt road just minutes from the Villages of both Woodstock and South Woodstock offering privacy and tranquility. The interior spaces of the home are creative, and inspiring, connecting seamlessly with the outdoors through classic covered porches and a spacious screened room. Enjoy lovely valley views beyond established perennial beds and mature plantings, with ancient stone walls lacing through. The kitchen is anchored by a AGA propane stove with custom cabinetry and soapstone counters. The dining room has a wall of built-ins, and reclaimed wide plank flooring. The living room is centered with a beautiful wood burning fireplace, and steps out to a screened porch. Three bedrooms, two bathrooms, and an oversized landing/office space on the second level complete the home. Oversized two car garage/barn with huge loft space for expansion. The leased Tesla Powerwall for peace of mind in the event of a power interruption. Perfect as a primary or second home. See MLS Property & Listing Details & 44 images.


VILLAGE OF TAFTSVILLE IN TOWN OF WOODSTOCK VT Home for sale $$2,000,000 | $400 per sq.ft.

$2,000,000 | $400 per sq.ft. VILLAGE OF TAFTSVILLE IN TOWN OF WOODSTOCK VT HOME FOR SALE

2706 East Woodstock Road 4 Beds | 4 Baths |   Total Sq. Ft. 5000  |  Acres: 0.56

INVESTMENT & RESIDENTIAL OPPORTUNITY - Rare historic building (The Taftsville Country Store) available for owner occupancy with multiple additional income units in the village of Taftsville. Just five minutes to the quintessential New England Village of Woodstock! Property includes store with bath (approved for restaurant, café, or retail store), Post Office (with current lease), Apartment 1 (with excellent AIRBNB rental history), Apartment 2 (The owner's unit- 3 bedroom, 2 bath), and plans/space for an additional studio unit. Perfect opportunity for an investor to offset living expenses with this multi-unit property, or just have a super fancy home office downstairs. Potential diversified income streams with hospitality, residential rental, and retail/ food service all in one property. Current owners have redesigned and graded the parking lot to include 27 parking spaces and EV Conduit for 2 charging stations that can accommodate 4 vehicles, ADA access to building, and ADA accessible restrooms. Property boasts gorgeous patio views of the Ottauquechee River and Taftsville Covered Bridge. See MLS Property & Listing Details & 60 images.


WOODSTOCK VT Lake House for sale $$2,450,000 | $440 per sq.ft.

$2,450,000 | $440 per sq.ft. WOODSTOCK VT LAKE HOUSE FOR SALE ON RIVER OTTAUQUECHEE RIVER

851 Riverside Park Road Waterfront Owned 48 Ft. of shoreline | 4 Beds | 4 Baths |   Total Sq. Ft. 5573  |  Acres: 40

"All Seasons" is the ultimate Vermont retreat, designed for gatherings and getaways while seamlessly blending rustic charm with modern luxury. This 5,900-sq-ft barn-style home, just over five minutes from Woodstock Village via Route 4 and the Lincoln Covered Bridge, sits high on a knoll above the Ottauquechee River with views to Killington. A veritable mini-resort, the property offers unparalleled access to recreational pursuits. Its 40-acre grounds feature single-track biking, hiking, and snowshoeing trails, a firepit, patio, grills, and owned riverfront access. A 32-foot indoor pool, and hot tub under the stars make this a year-round haven. The acreage also includes a potential building lot with mountain views and an existing roadway, adding versatility. Nearby, enjoy world-class skiing, golf, and other outdoor activities, with Woodstock Village offering charming shops and restaurants. Inside, the chef's kitchen boasts Viking appliances, granite counters, dual refrigerators, a pantry, and a custom island. Two expansive great rooms provide gathering spaces with large-screen TVs and plush seating, including a wet bar in the second-floor game room. Accommodations include four bedrooms, three full baths, and space for up to 12 guests. A highly successful Airbnb rental, "All Sessons" is an extraordinary opportunity to own a Vermont escape combining privacy, beauty, and income potential in one of the region's most picturesque towns. See MLS Property & Listing Details & 60 images. Includes a Virtual Tour


WOODSTOCK VT Lake House for sale $$2,485,000 | $710 per sq.ft.

$2,485,000 | $710 per sq.ft. WOODSTOCK VT LAKE HOUSE FOR SALE ON BROOK/ KEDRON BROOK

4945 South Road Waterfront Owned 450 Ft. of shoreline | 5 Beds | 4 Baths |   Total Sq. Ft. 3502  |  Acres: 2.57

The John Arnold Cottle House is a landmark residence in the heart of South Woodstock, a rare blend of village convenience and country living. Built in 1811 by one of the area's earliest settlers, this stately Federal-style brick home has been thoughtfully restored to honor its historic charm while integrating modern comforts. Set on 2.7 acres, the property features 450 ft of frontage on Kedron Brook, along with a firepit, a barn, and a river meadow. The barn--currently used for storage--could easily be converted to accommodate a couple of horses or sheep. The 3-bedroom main house has elegant 12-over-12 windows, high ceilings, and beautifully preserved period details, including a 2nd-floor ballroom with a coved ceiling and fiddler's stage--a nod to its past as a lively gathering space. The newer addition overlooking the brook has a magnificent great room with 17' cathedral ceilings and a gourmet kitchen and wood burning brick fireplace. The renovated Kingsley Barn guest house offers 2 bedrooms, a loft, and a deck overlooking the brook. Below there is a heated workshop, ideal for puttering and creating. A timber bridge spans the waterway, connecting the property's field, barn and trails. With direct access to the Upwey Trail system and equestrian paths leading to the Green Mountain Horse Association, this property is ideal for outdoor enthusiasts. Located along South Road in the South Woodstock Historic District. See MLS Property & Listing Details & 40 images. Includes a Virtual Tour


WOODSTOCK VT Lake House for sale $$3,500,000 | $644 per sq.ft.

$3,500,000 | $644 per sq.ft. WOODSTOCK VT LAKE HOUSE FOR SALE

61 Academy Circle Waterfront Owned 6 Beds | 6 Baths |   Total Sq. Ft. 5433  |  Acres: 10

Hyacinth House has been a landmark property in the historic village of South Woodstock from its early settlement in the 1800's. Sited on a knoll overlooking the Kedron Brook this grand residence has been carefully restored by talented craftsmen. Taking care to keep the beautiful original details the owners have brought the systems into the 21st century with the highest quality of materials. The back ell seamlessly ties into the original brick Federal and offers additional spaces for entertaining guests including the Pine Room with its' large fireplace for snowy winter nights. The brick Federal consists of formal living room, dining room, library and gourmet kitchen with walk in pantry. On the second floor there are 2 ensuite bedrooms,4 more bedrooms, 2 baths and large laundry room. The third floor offers the surprise of a family room that was originally a ballroom with curved ceiling. There is also a bright studio and half bath on that level. The new attached oversize 2 car garage is accessed from the Pine Room and the fully renovated basement. The 10 acres comprises of lovely landscaping around the home and plenty of land for gardens and animals. The 18th century barn and corn crib lend much charm to the setting. Walk to the charming village store and enjoy dinner on the porch of the Ransom Tavern. Only 5 miles to Woodstock and a short drive to multiple ski areas. South Woodstock is truly a bucolic place to call home! Call today for a private viewing. See MLS Property & Listing Details & 40 images. Includes a Virtual Tour