Woodstock Vermont MLS Listings Homes For Sale

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Under Contract WOODSTOCK VT Home for sale $$449,000 | $427 per sq.ft.

$449,000 | $427 per sq.ft. WOODSTOCK VT HOME FOR SALE

6 Highland Avenue 1 Beds | 1 Baths |   Total Sq. Ft. 1052  |  Acres: 0.5

A rare opportunity for Woodstock! An affordable Woodstock Village cottage! The advantage of contemporary solar powered energy efficiency, with connection to an energy storing Tesla battery! The property further benefits from valuable infrastructure components of the municipal sewer system and the Woodstock Aqueduct Water Company! An attractive interior features wood flooring throughout! A large enclosed porch serves the dual function of both a practical mud room entrance, in the winter, and a beautiful sitting area in warmer weather. When entering from this porch into the kitchen the warm feeling emanating from the cottage's wood paneled interior is immediately apparent. A butcher block counter top and contemporary kitchen cabinets and appliances accentuate the kitchen. Adjacent is a living/dining room, with multiple well placed windows. The generously sized bedroom with wood burning stove, vaulted ceiling and a comfortable sitting area is far more substantial than would be expected in a small home! A full bath with laundry area completes the cozy interior. This appealing cottage could become your affordable primary home or your fun Woodstock vacation retreat. A manageable size! This location is equally wonderful for the proximity to all the numerous amenities of village life, or for enjoying the peaceful solitude of the nearby trails that meander through the Mount Peg town forest! An appealing cottage on a well located village parcel! Obvious upside potential is very clear! See MLS Property & Listing Details & 39 images.


Under Contract WOODSTOCK VT Home for sale $$499,999 | $351 per sq.ft.

$499,999 | $351 per sq.ft. WOODSTOCK VT HOME FOR SALE
Price Change! reduced by $25,001 down 5% on October 23rd 2024

378 Fletcher Hill Road 4 Beds | 1 Baths |   Total Sq. Ft. 1424  |  Acres: 5

Privately located, in desirable South Woodstock! A comfortable home with the benefit of great outside spaces providing the opportunity for recreation, gardening or entertaining! South Woodstock is well known for the potential of having wonderful access to miles of trails enjoyed by equestrians, hikers and snowmobilers. The numerous amenities of historic Woodstock Village are just minutes away! The entrance to the property is via a level tree sided private driveway. By walking up a few steps from the driveway you enter the home into a bright kitchen. Adjacent to the kitchen is a Living room/dining room that features access to a balcony with views of distant hills. Well located within this space is a hearth with a wood pellet stove. At a further end of the main floor is an attractive room equally well suited to be a family room or a first floor bedroom. Completing the main floor is a full bath with both a shower and a tub. Accessed up stairs from the living room are two second floor bedrooms. One of these bedrooms features a private balcony, with hillside views. The full basement is entered either via an interior stairway or through a ground level door off the driveway. Within the basement is a laundry area, space used as a workshop and storage area. Mechanical systems are contemporary, with a newer furnace and hot water heater. Separated off the basement is a 15'x11' heated room currently used as living space. A comfortable home, in a great location within desirable Woodstock! See MLS Property & Listing Details & 35 images.


WOODSTOCK VT Home for sale $$545,000 | $182 per sq.ft.

$545,000 | $182 per sq.ft. WOODSTOCK VT HOME FOR SALE
Price Change! reduced by $105,000 down 19% on November 4th 2024

24 High Street 5 Beds | 2 Baths |   Total Sq. Ft. 2996  |  Acres: 0.2

Constructed in 1840, this post & beam home is situated in the heart of Woodstock Village. A short stroll across the Kedron Brook footbridge to shopping and restaurants, the property is just steps away from all of the amenities this renowned Vermont town has to offer. Woodstock Elementary School, Vail Field and the Woodstock Inn are also just around the corner. Historic High Street, once home to blacksmiths, farriers, and livery stables is a vibrant and connected neighborhood today. The front of the house is anchored by an award-winning ninety-foot mature perennial flower garden and antique stone wall. The private backyard includes raised vegetable beds, fieldstone walls, and terraced garden beds built into the hillside. The property abuts Mt. Peg and all it has to offer, including beautiful walks in the woods, birding, hiking, mountain biking, snowshoeing trails, and XC skiing. Once a two-family dwelling, this spacious single-family home offers a flexible floor plan with room for expansion. The second-floor family room includes a woodstove and opens to an end porch entrance and the backyard. The large second-floor front balcony offers plenty of room for outdoor dining and a birds' eye view of Woodstock Village, High Street and Mt. Tom. See MLS Property & Listing Details & 36 images.


VILLAGE OF TAFTSVILLE IN TOWN OF WOODSTOCK VT Home for sale $$595,000 | $350 per sq.ft.

$595,000 | $350 per sq.ft. VILLAGE OF TAFTSVILLE IN TOWN OF WOODSTOCK VT HOME FOR SALE
Price Change! reduced by $100,000 down 17% on December 2nd 2024

105 Happy Valley Road 3 Beds | 1 Baths |   Total Sq. Ft. 1700  |  Acres: 0.44

PRICE REDUCTION!! A Quintessential Historic 3 Bedroom, 1,700 sq/ft. Home in Woodstock's coveted Taftsville Village. The "Levi D. Hall House" was built in 1848 by D. Taft & Sons and has been a loved and well-maintained home by the same family for nearly 70 years. Enter into beautiful natural light and a home in pristine condition throughout. The classic country kitchen has high ceilings with original exposed beams, a gas fireplace to add warmth to your colder Vermont days, and direct access to an oversized one car garage. In the Dining and Living Rooms you are greeted with more high ceilings and an abundance of natural light, and the first-floor bedroom/full bath suite has a private dressing area with large closet space. Moving upstairs, there are two attractive bedrooms with wide pine floors and an easy and logical dormer expansion option for larger bedrooms and a large common bath (future investment). There is a generous bonus room for a great home office just off the garage and the property boasts mature perennial beds. Expansive storage space exists above the barn/garage. Attractive covered porch, new furnace in 2023, and upgraded wiring throughout. Be sure to view the Unbranded Tour link. See MLS Property & Listing Details & 40 images. Includes a Virtual Tour


WOODSTOCK VT Home for sale $$599,000 | $446 per sq.ft.

$599,000 | $446 per sq.ft. WOODSTOCK VT HOME FOR SALE
Price Change! reduced by $50,900 down 8% on February 13th 2025

1613 West Woodstock Road 3 Beds | 2 Baths |   Total Sq. Ft. 1344  |  Acres: 0.78

WOODSTOCK-TURNKEY AND CONVENIENT! This totally renovated, move-in ready home located a few minutes to Woodstock Village, 20 minutes to Killington, 30 minutes to DHMC. Enjoy loads of recreational trails of all kinds, just minutes away.  Excellent spot with walking distance to the abutting Woodstock Union Middle School/High School. Newly Renovated inside and out. Spacious open concept living on main floor. The large, finished basement has a TV recreation area, workout space and pool table area. Custom built in cabinetry in the upstairs bedrooms. Private and wooded back yard with a covered porch, perennials, berries and gardens.  Huge potential to add-on, start a home business, create a rental unit or leave quaint and cozy as it is.  This property would be ideal for a primary residence or short-term rental investment property. Schedule your tour today of this sweet Woodstock GEM! See MLS Property & Listing Details & 46 images.


Under Contract VILLAGE OF WOODSTOCK IN TOWN OF WOODSTOCK VT Home for sale $$625,000 | $457 per sq.ft.

$625,000 | $457 per sq.ft. VILLAGE OF WOODSTOCK IN TOWN OF WOODSTOCK VT HOME FOR SALE
Price Change! reduced by $50,000 down 8% on December 10th 2024

1 Border Lane 3 Beds | 2 Baths |   Total Sq. Ft. 1368  |  Acres: 1.04

Location, location location! Situated on a very desirable road within Woodstock Village, this 3 bedroom Ranch sits on just over 1 acre of open lawn surrounded by mature trees. The yard is tastefully landscaped and there is a beautiful patio out back, ideal for a morning cup of coffee, grilling dinner, or a nice glass of wine. As you enter through the front door, the bedrooms and a bath are off to the right. To the left, the long eat-in kitchen flows into to the dining area which connects to the living room. There is patio access, a large bow window and a gas fireplace to keep warm in the wintertime. At the end of the living room is a lovely sunroom that could also be a great office. Rounding out the first floor is a half bath, and access to the attached garage and full basement. Local shops and restaurants are within walking distance and you are just minutes from the Woodstock Country Club and Saskadena 6. See MLS Property & Listing Details & 30 images.


WOODSTOCK VT Home for sale $$625,000 | $391 per sq.ft.

$625,000 | $391 per sq.ft. WOODSTOCK VT HOME FOR SALE
Price Change! reduced by $300,000 down 48% on February 4th 2025

2 High Street 3 Beds | 3 Baths |   Total Sq. Ft. 1600  |  Acres: 0.07

OPPORTUNITY AWAITS - Historic c. 1890 1,600 sq/ft. home in the center of downtown Woodstock. In the heart of everything! The majority of this 3 bedroom, 3 bathroom home is stripped down and ready for remodeling - and we have a contractor ready to go for a custom Winter project. Step in early to add your own personality and or discuss intended improvements. The home includes a lovely first floor sunlit living room walking out to a pleasing covered porch that overlooks the bustle of town. Existing home features unique stained glass windows and doors, gorgeous hardwood and pine floors, and a large unfinished 3rd floor for expansion capability. Current layout includes: first floor with an Open Floorplan kitchen to a gracious dining area, and a separate front living room with private study with adjoining 3/4 bath. Upstairs has 3 bedrooms, the layout for 2 baths, and a walk-up stairway to a large unfinished attic space which could be finished off. There is a paved driveway with basement level garage/storage and additional alternative design plans are included for a more expansive solution. See MLS Property & Listing Details & 36 images.


Under Contract WOODSTOCK VT Lake House for sale $$695,000 | $194 per sq.ft.

$695,000 | $194 per sq.ft. WOODSTOCK VT LAKE HOUSE FOR SALE

3914 South Road Waterfront Owned 4 Beds | 3 Baths |   Total Sq. Ft. 3584  |  Acres: 5.1

This South Woodstock contemporary residence was designed by the original architect-owner to showcase Vermont's changing seasons and capture views of the Kedron Brook as it wanders through the property past small meadows tucked in along the banks. The home can be accessed privately at grade level through the heated garage and mudroom, while guests enter via a covered entry to the upper level. The lower walk-out level of the home has two bedrooms, a shared bath, laundry and workshop. The elevated second floor is dedicated to gathering spaces including a great room with cathedral ceilings, eat in kitchen and family room that opens out on to a broad deck with overlooking the brook as it flows to the nearby Woodstock golf course and Athletic Club. The spacious primary bedroom offers an ensuite bathroom and abundant closet space. The main floor guest bedroom with loft is served by an adjacent bathroom. The two-stall multi-purpose barn opens to a small pasture and a fence yard for pets. A home for all seasons and reasons. See MLS Property & Listing Details & 40 images. Includes a Virtual Tour


VILLAGE OF WOODSTOCK IN TOWN OF WOODSTOCK VT Home for sale $$795,000 | $469 per sq.ft.

$795,000 | $469 per sq.ft. VILLAGE OF WOODSTOCK IN TOWN OF WOODSTOCK VT HOME FOR SALE

25 Linden Hill Street 3 Beds | 2 Baths |   Total Sq. Ft. 1694  |  Acres: 0.42

This classic early 20th Century farmhouse with 3 sunny bedrooms and two baths is sited on a quiet Village Street uphill above the Woodstock Elementary School and across from the public playground at Vail Field and the Woodstock Country Club golf course. The home has benefitted from the thoughtful additions of an eat-in kitchen and a front porch where you can enjoy long summer evenings. A comprehensive renovation several years ago opened the main level floorplan to eliminate partitions adapting the house to modern lifestyles. The backyard rises in tiers from the lower level with picnic table and grilling area to an elevated plateau used for expansive vegetable and flowers gardens. Truly a joyful place to call home in the heart of Woodstock's historic community. See MLS Property & Listing Details & 48 images. Includes a Virtual Tour


WOODSTOCK VT Home for sale $$845,000 | $1,408 per sq.ft.

$845,000 | $1,408 per sq.ft. WOODSTOCK VT HOME FOR SALE

234 Randall Road 2 Beds | 1 Baths |   Total Sq. Ft. 600  |  Acres: 6.07

Randall Road Farm represents a rare opportunity to purchase a multigenerational family farmstead in an exceptionally desirable location. Long recognized as a well established farm raising Charolais beef cattle, poultry and hay. The owner has been the farmer/steward of many of the areas farms in the Woodstock and South Woodstock. The property has a single family dwelling, shop building with farm office, hay and dairy barns, multiple storage and ancillary structures. Whether looking to engage in the localvore food movement or looking to build a residential home on arguably the most desirable land parcel a stones throw from Woodstock Village, this property has location, setting and features that would be hard to replicate. The upper pasture with easy access has great views, privacy and a commanding location. See MLS Property & Listing Details & 14 images.


WOODSTOCK VT Home for sale $$995,000 | $312 per sq.ft.

$995,000 | $312 per sq.ft. WOODSTOCK VT HOME FOR SALE

598 East Woodstock Road 4 Beds | 3 Baths |   Total Sq. Ft. 3190  |  Acres: 2.94

This stately, rambling gambrel home offers privacy, convenience, antique charm, and room for everyone. Walking distance to the east end of Woodstock village, on 2.9 lush acres including a fenced backyard, a fenced vegetable garden, and extensive perennial beds. The home is a stunning mixture of antique touches and modern functionality, with beautiful built-ins and closet spaces at every turn. The home has a suite of rooms on the first floor that are perfect for a home-based business or studio area (or 2 extra bedrooms plus bonus room), and a one-bedroom full bath (with office & kitchen) in-law suite upstairs with private ground-level access. The main part of the home includes three additional bedrooms, a library, a music room, living room, dining room, two full baths, dressing room, and three-season enclosed porch. The charming eat-in kitchen includes beautiful display cabinets, hand painted tiles, and built-in pantry and laundry. In the stunning custom cherry wood library with marble fireplace and private deck, bibliophiles will find more than enough shelf space for their entire book collection, and a quiet, peaceful setting in which to read. Two readers in the family? The upstairs music room is similarly equipped, also with stunning cherry wood built-ins and detailing. Two staircases provide ample access to the upstairs and contribute to the ambling nature of the home. Walk to restaurants and a river front park! See MLS Property & Listing Details & 32 images.


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