Woodstock Vermont MLS Listings Homes For Sale

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Under Contract WOODSTOCK VT Home for sale $$925,000 | $321 per sq.ft.

$925,000 | $321 per sq.ft. WOODSTOCK VT HOME FOR SALE

348 Laughlin Road 4 Beds | 3 Baths |   Total Sq. Ft. 2882  |  Acres: 2.08

Stunning contemporary extensively renovated and idyllically situated on a westerly facing hillside overlooking the village of Woodstock offers a coveted Woodstock location for those wanting a peaceful Vermont countryside vibe to unwind but the vibrant Woodstock Village life at the foot of your hill! The interior design presents a more refined open concept design that offers both openness but a more defined layout for functional separation and intimacy. A captivating light filled living room that opens onto a mahogany deck is centered upon a handsome fireplaced wall that is open on both sides to allow flow into a lovely eat-in kitchen detailed with quartz counters. A primary ensuite bedroom, study/office, and full bath complete the main level. The lower level presents a second living room that opens onto a patio and centers upon a second fireplace. Three bedrooms and a terrific laundry room/mudroom complete the lower level. Enjoy relaxing, entertaining, and taking in the sunsets from the westerly facing patio and deck. Perfect as a primary or secondary home with all season recreation, theatre and the arts, dining, and shopping just minutes away and easy access to all the amenities and major employment the Upper Valley has to offer. Showings begin with Public Open House Saturday Oct 4 from 1-3pm. See MLS Property & Listing Details & 31 images. Includes a Virtual Tour


WOODSTOCK VT Home for sale $$944,999 | $440 per sq.ft.

$944,999 | $440 per sq.ft. WOODSTOCK VT HOME FOR SALE
Price Change! reduced by $155,001 down 16% on September 8th 2025

509 Church Hill 3 Beds | 3 Baths |   Total Sq. Ft. 2150  |  Acres: 1.49

Enjoy in-town ease of living combined with Vermont country charm. This well maintained , efficient home provides first floor living with an additional lower floor ensuite bedroom /sitting area with direct access to lovely grounds and gardens. The light filled home is in excellent condition and is surrounded by fabulous perennial gardens, mature maple trees, raspberry and blueberry bushes , stone patio and 2 decks offering plenty of spaces for outdoor living and entertaining. The open floor plan provides easy flow and the large windows and glass doors bring the out of doors in. A big bonus is central air conditioning ! The detached 2 car garage provides lots of storage and work space area . Enjoy the charm and various amenities of Woodstock Village that consistently is named one of the prettiest small towns in America . Easy access to sports for every season.. Twenty minutes to the Upper Valley , two and a half hours to Boston and 5 hours to NYC. Call today for an appointment . See MLS Property & Listing Details & 55 images.


WOODSTOCK VT Home for sale $$985,000 | $513 per sq.ft.

$985,000 | $513 per sq.ft. WOODSTOCK VT HOME FOR SALE

72 Oak Ridge Way 3 Beds | 3 Baths |   Total Sq. Ft. 1920  |  Acres: 6.02

PRIME LOCATION! Tucked away at the end of a peaceful dead-end road in the Westerdale neighborhood is this Vermont Cape Cod home offers the perfect blend of privacy and convenience on just over 6 acres. Surrounded by mature trees and set on a wooded lot overlooking a tranquil pond, you'll enjoy the calm of nature right outside your doorstep. The freshly installed deck provides a serene spot. Well-planned interior space, inside you will find a warm and inviting atmosphere, offering an eat-in kitchen enhanced by the heat from the wood stove or relax by the fireplace in the living room open to the dining room. The primary bedroom with a full bath featuring a jacuzzi tub, while the remaining rooms provide flexible options for guests. Recent updates like a new oil tank and a new water pressure tank ensure reliable modern living. Located just minutes from the heart of Woodstock, this home gives you easy access to local favorites like the Billings Farm and year-round fun at Okemo Mountain Resort. Whether you're into skiing, hiking, or something entirely more relaxed, there's something nearby for everyone. The neighborhood boasts a strong sense of an upscale community while maintaining a rural, secluded vibe. It's that rare find that feels remote but keeps you close to all the essentials. Ideal for year-round living or a seasonal getaway, this property invites you to experience the best of Vermont in a setting that's equal parts comfort and character. See MLS Property & Listing Details & 54 images.


WOODSTOCK VT Home for sale $$985,000 | $354 per sq.ft.

$985,000 | $354 per sq.ft. WOODSTOCK VT HOME FOR SALE
Price Change! reduced by $200,000 down 20% on October 21st 2025

1782 Randall Road 4 Beds | 3 Baths |   Total Sq. Ft. 2785  |  Acres: 5.01

This early Woodstock residence was built in 1792 by Joseph Wood on a parcel of land he purchased in 1786 from Ebenezer Kingsley, one of Woodstock early settlers. A classic New England Cape of the period with the notable features of a central chimney with multiple fireplaces and a second story overhang on the gables. The house retains a great deal of original features and fabric including wide board flooring, horizontal wainscotting, period doors and hardware and a keeping room fireplace. Massive exposed beams substantiate the date of construction. The four bedrooms and three baths include a first floor primary en suite bedroom. Spacious rooms with unusually high ceilings and multi pane windows create a comfortable living space. Beautifully sited and located on the exclusive Randall Road within a grove of ancient sugar maples. See MLS Property & Listing Details & 37 images.


WOODSTOCK VT Home for sale $$1,150,000 | $518 per sq.ft.

$1,150,000 | $518 per sq.ft. WOODSTOCK VT HOME FOR SALE
Price Change! reduced by $150,000 down 13% on October 30th 2025

958 East Woodstock Road 3 Beds | 3 Baths |   Total Sq. Ft. 2220  |  Acres: 1.53

Just minutes from the heart of Woodstock, this 3-bedroom, 3-bath home with a dedicated office/family room has been transformed from the ground up into a modern, energy-efficient retreat. Taken down to the studs, the renovation was comprehensive--every system replaced, with all new wiring, plumbing, insulation, and mechanicals, along with a new roof, Pella windows, central heating, and air conditioning. A brand-new two-car garage will be completed before closing, adding convenience and value. Inside, light-filled spaces showcase new, wide-plank white oak flooring, a beautifully designed kitchen, and spa-like bathrooms. The thoughtful floor plan includes a private office, perfect for working from home or creative pursuits. Outdoors, a covered porch with handsome stone entry steps frames gorgeous northerly views, and the roomy 1.53 acre lot provides plenty of room for gardening and outdoor activities. This turnkey home is a rare find: a character-filled property where every detail has been reimagined, offering modern comfort, low-maintenance peace of mind, and proximity to all that makes Woodstock one of New England's most desirable communities. See MLS Property & Listing Details & 57 images. Includes a Virtual Tour


WOODSTOCK VT Home for sale $$1,200,000 | $439 per sq.ft.

$1,200,000 | $439 per sq.ft. WOODSTOCK VT HOME FOR SALE
Price Change! reduced by $50,000 down 4% on October 14th 2025

17 Linden Hill 4 Beds | 3 Baths |   Total Sq. Ft. 2736  |  Acres: 0.86

Open House! Saturday Oct 18 from 10-12. Once known as the Sunshine Nursery School, this home's history expands back to ~1870 and now it stands as a spacious and beautifully updated residence with an expansive terraced yard (one of the largest near the village) and elegant interiors. High ceilings, high-quality wood floors, and sun-filled rooms define the main level, where a gracious primary ensuite with step-in shower, and a glass-lined sunroom create an effortless flow. Thoughtful conveniences include a mini-split for year-round comfort, laundry on the main level, and an eight-foot slider off the dining room that opens to a private deck overlooking the backyard. Upstairs, an apartment with private entrance extends the home's versatility with its own kitchen, living area, ¾ bath, and two bedrooms--perfect for guests, extended family, or private quarters. Outdoors, the property is framed by beautifully established perennial gardens and an expansive yard, offering rare in-village green space on +-.89 acres! A paved drive, two-car garage with overhead storage, standby whole-house generator, and public water and sewer add to the ease of ownership. The location is unmatched--just a street away from the elementary school, Vail Fields, the Village Green, and miles of walking trails. Schedule a private showing and see this grand home for yourself! See MLS Property & Listing Details & 35 images.


WOODSTOCK VT Lake House for sale $$1,295,000 | $419 per sq.ft.

$1,295,000 | $419 per sq.ft. WOODSTOCK VT LAKE HOUSE FOR SALE

16 Church Street Waterfront Owned 4 Beds | 3 Baths |   Total Sq. Ft. 3089  |  Acres: 0.52

16 Church has the most stunning view of the river from any house in the village that we have seen, perched up above a series of river rapids so the sounds of the river during the day or in the evening are incredibly peaceful and relaxing. Plus, 16 Church is privately nestled in, like a secret hideaway, yet steps to the village green (and a level walk to/from). And more unusual for the village, it has a two-car garage with a covered walkway into the mudroom entryway (plus more outside parking). The spacious kitchen/dining area opens to the vaulted-ceiling living room, which has an INCREDIBLE view up-river. A side door leads to the side-deck that has the same view and sound of the river for outdoor dining above the river. There is a propane woodstove in the living room and woodstove in the kitchen/dining. A 1st floor bedroom has an ensuite bath and small stack washer-dryer. Upstairs is a large bedroom looking out through the great room to the river, a smaller bedroom, a bath and lovely loft area above the living room. Downstairs is a large den/rec/office, a bedroom, a bathroom, the main laundry room and mechanical room, all renovated 11 years, post the Irene storm, when the river waters came up into the lower level. There are beautiful gardens in the front and rear of the house. SEE PROPERTY WEBSITE FOR 16 CHURCH ST WOODSTOCK FOR MORE DETAILS, FLOORPLANS HI REZ PHOTOS AND MORE. See MLS Property & Listing Details & 40 images.


WOODSTOCK VT Home for sale $$1,295,000 | $568 per sq.ft.

$1,295,000 | $568 per sq.ft. WOODSTOCK VT HOME FOR SALE New Listing!

33 Mountain Avenue 2 Beds | 4 Baths |   Total Sq. Ft. 2280  |  Acres: 0.8

Welcome to 33 Mountain Avenue - a mid-century modern gem poised perfectly on the edge of Faulkner Park and at the foot of Mt. Tom and once part of the Marianne Faulkner Estate. The spacious one-level design provides a seamless connection between the indoor and outdoor living space which includes two ensuite bedrooms, living/dining room with fireplace, kitchen, family room, office and attached one car garage. An exquisite multi-terraced exterior landscape design is predominately and privately located at the back of the property. Plentiful space for gardening, a fire-pit, or even an in-ground pool - where once there was one!  Take in the trails of Mt.Tom and Marsh-Billings-Rockefeller National Park just outside your door. Enjoy a lovely stroll along Mountain Ave and thru the iconic Middle Covered Bridge to tap into a multitude of dining options, shopping, and performances at Pentangle Arts. A rare, unique, and coveted Woodstock Village location! See MLS Property & Listing Details & 32 images. Includes a Virtual Tour


WOODSTOCK VT Home for sale $$1,295,000 | $485 per sq.ft.

$1,295,000 | $485 per sq.ft. WOODSTOCK VT HOME FOR SALE

513 Deer Brook Way 4 Beds | 3 Baths |   Total Sq. Ft. 2668  |  Acres: 8.32

This traditional New England Colonial, designed and custom built by Vermont Vernacular Builders, is sited to capture idyllic all-around mountain views and southern light. The spacious four-bedroom home features wide board floors, exposed beams, and a sun-filled chef's kitchen and den. New Thor stainless steel 48" propane range installed October 2025. Privately set on over 8 acres, the property offers true seclusion with the convenience of being just minutes to Woodstock Village, close to Killington and Okemo skiing, and near local favorites including Ramunto's Pizza and nearby event venues. Amenities include a private in-ground pool with expansive mountain views, plus an oversized garage/barn with storage and space above for potential guest quarters. An ideal countryside retreat for year-round living or a second home escape. See MLS Property & Listing Details & 40 images.


WOODSTOCK VT Home for sale $$1,495,000 | $590 per sq.ft.

$1,495,000 | $590 per sq.ft. WOODSTOCK VT HOME FOR SALE

7 Slayton Terrace 4 Beds | 3 Baths |   Total Sq. Ft. 2532  |  Acres: 0.79

A rare in-village offering, 7 Slayton Terrace combines walkability, views, and beautifully renovated interiors--just steps from the heart of Woodstock. Sited on an oversized .79-acre lot overlooking Billings Farm, this 4-bedroom home offers the space and flexibility rarely found so close to the village center. The main house features a stunning new kitchen with high-end finishes and beautifully updated bathrooms throughout. Natural light floods the living spaces, which flow easily for everyday living or entertaining. A large, unfinished studio apartment is ready for your design--perfect for an in-law suite, au pair quarters, or as a short- or long-term rental. Above the detached barn, a finished space provides a quiet work-from-home setup or creative studio. With close proximity to the Mt. Peg trail system, this location offers direct access to hiking, mountain biking, and nordic skiing, while the restaurants, shops, and cultural amenities of Woodstock Village are just a short stroll away. A rare opportunity for turn-key living in one of Vermont's most picturesque towns. Showings begin 7/5 with an open house from 10:30am - 12:30pm. See MLS Property & Listing Details & 41 images. Includes a Virtual Tour


WOODSTOCK VT Home for sale $$1,595,000 | $437 per sq.ft.

$1,595,000 | $437 per sq.ft. WOODSTOCK VT HOME FOR SALE
Price Change! reduced by $55,000 down 3% on July 5th 2025

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

Just 2 miles from Woodstock Village, this gracious brick cape on 6 open acres offers space, comfort, and classic Vermont charm. The expanded chef's kitchen opens to a gracious gathering room ideal for entertaining, while 3 fireplaces--wood-burning, brick, and gas-ready--provide cozy warmth throughout. Upstairs, find 3-4 bedrooms including one with its own fireplace, plus a private guest room or office above the garage. A covered porch, sunny patio, inground pool with heat hookup, apiary, and dedicated garden create an idyllic outdoor lifestyle. Over 5 acres of invisible fencing allow pets to roam freely. Adjacent to the site of the country's first ski tow, with easy access to Saskadena Six and fantastic winter recreation. Bonus: a heated, plumbed two-floor barn/workshop with its own car bay--ready to become a media/game room, studio, or guest space. Easy access to I-89 and the Upper Valley. A rare opportunity for acreage, privacy, and proximity to one of New England's most iconic villages. See MLS Property & Listing Details & 49 images. Includes a Virtual Tour


VILLAGE OF WOODSTOCK IN TOWN OF WOODSTOCK VT Home for sale $$1,600,000 | $266 per sq.ft.

$1,600,000 | $266 per sq.ft. VILLAGE OF WOODSTOCK IN TOWN OF WOODSTOCK VT HOME FOR SALE

15 Central Street 4 Beds | 3 Baths |   Total Sq. Ft. 6014  |  Acres: 0.05

15 Central Street is one of the finest commercial locations in Woodstock with two of the most creative and successful businesses as the anchor tenants. The property has adapted to changes of the course of its long history of uses including residential shop owner, a barber shop, a dance & pool hall, law office, architectural services and a variety of mercantile endeavors. Notably, the building was the headquarters of Lt Colonel Peter T. Washburn, who led the 1st Vermont Regiment troops in their crucial role at Gettysburg. He returned to become Adjutant and Inspector General to organize and direct Vermont's military efforts through the rest of the Civil War from his offices at 15 Central Street. The current owner, recognizing it was time to adapt the building to the 21st Century, developed plans to upgrade and modernize the second and third floors for mixed use including an incredible residential unit with exposed brick walls and timber framing. The story high historic windows have been restored, and the second level has been reframed with new sheetrock for office or residential use. The third level partition walls have been removed to create a dramatic open area with views over the village to the north and south leaving the finishes and uses of the two levels up to your imagination. This is a once-in-a-lifetime opportunity to acquire a property with a remarkable history and become part of creating Woodstock's future. See MLS Property & Listing Details & 43 images.


Under Contract WOODSTOCK VT Home for sale $$1,695,000 | $402 per sq.ft.

$1,695,000 | $402 per sq.ft. WOODSTOCK VT HOME FOR SALE
Price Change! reduced by $304,000 down 18% on October 3rd 2025

10 College Hill Road 5 Beds | 5 Baths |   Total Sq. Ft. 4214  |  Acres: 1.07

10 College Hill is the perfect in-village residence, off the main road yet walk-to-everything. The original, historic residence was designed in 1916 by renowned architect John Russell Pope whose accomplishments include the Jefferson Memorial, and master plans for Dartmouth and Yale. It also enjoys modern additions and updates including a stunning first-level primary bedroom suite designed in 2012 by the respected local architect David Bielman. The front door welcomes guests with a pair of dutch-doors in a center entrance foyer, flanked by a classic dining room and elegant living room (both with fireplaces). The classic butlers pantry leads to the gourmet kitchen and a wonderful, sunny eat-in breakfast area. There are 4 additional BRs upstairs, 2 have ensuite baths plus a 3rd hall bath. There are also powder baths on the first floor and in the lower (basement) area. All BRs have central air. Mechanicals have been updated and well-maintained. 2 other offices on 1st and 2nd floor, and the basement has living space, a workout room, safe room, and ample storage. Beyond the kitchen is a mud-laundry room that leads to the covered (heated) brick walkway from the garage. The 1.05 acre parcel has professionally designed and executed gardens, patios and stone walls including new stone steps that lead up to a second new stone patio that enjoys sweeping vistas across to Mt Tom and the Marsh-Billings-Rockefeller National park. SEE FULL PROPERTY WEBSITE. See MLS Property & Listing Details & 35 images.


Under Contract WOODSTOCK VT Home for sale $$1,750,000 | $323 per sq.ft.

$1,750,000 | $323 per sq.ft. WOODSTOCK VT HOME FOR SALE
Price Change! reduced by $450,000 down 26% on August 23rd 2025

2334 South Road 3 Beds | 3 Baths |   Total Sq. Ft. 5422  |  Acres: 31.43

Offered for the first time, the exclusive private residence of one of Woodstock's most notable and prolific builders, Hank Savelberg. Located just five minutes from the Woodstock Village Green, this whimsical, private, contemporary hillside estate was lovingly constructed featuring well thought, connected open spaces with expansive glass walls and dramatic sweeping wooden ceilings. The entire home is a unique showplace of clever spaces, built-ins, with custom detail throughout; featuring mahogany, cherry, and locally sourced stone. The ten room- three bedroom, three bath main residence was carefully sited to optimize a stunning northeasterly view, and to communicate directly with exterior terraces, and established gardens overlooking a pond, rolling hills and fields. There is a detached one bedroom guest house (or caretaker's cottage), garage, horse barn, equipment shed and two garden sheds. Easy access to hiking trails. Three minutes to Fitness Ctr., 15 minutes to Saskadena Six skiing. 2.25 hours to Boston, 4.5 to NYC. Property enrolled in Current Use. See MLS Property & Listing Details & 60 images.


VILLAGE OF TAFTSVILLE IN TOWN OF WOODSTOCK VT Home for sale $$1,800,000 | $360 per sq.ft.

$1,800,000 | $360 per sq.ft. VILLAGE OF TAFTSVILLE IN TOWN OF WOODSTOCK VT HOME FOR SALE
Price Change! reduced by $200,000 down 11% on August 8th 2025

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 - Woodstock VT) available for owner occupancy with multiple additional income units in the village of Taftsville. Just five minutes to the quintessential downtown New England Village of Woodstock! Property includes storefront space (approved for restaurant, café, or retail store), Post Office (with current lease), smaller Apartment 1 (with excellent AIRBNB rental history), larger 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, 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. See MLS Property & Listing Details & 60 images.


WOODSTOCK VT Lake House for sale $$1,900,000 | $645 per sq.ft.

$1,900,000 | $645 per sq.ft. WOODSTOCK VT LAKE HOUSE FOR SALE ON RIVER OTTAUQUECHEE RIVER

2394 Fletcher Hill Road Waterfront Owned 1000 Ft. of shoreline | 2 Beds | 3 Baths |   Total Sq. Ft. 2944  |  Acres: 14.9

Newly constructed Modern Vermont Farmhouse residence on 14 acres with absolutely amazing river views, 13-foot ceilings, gourmet kitchen, oversized french doors and windows throughout, radiant-heated concrete floors, first rate finishes, appliances and mechanicals located just 6 minutes to the Woodstock village green and 17 minutes to the Killington Skyeship base lodge. The first level is comprised of a large, open-format living space with gourmet kitchen, dining and living spaces, plus a first level bedroom with modern ensuite bath. Upstairs is another large open floor plan living space with a half-bath, and a full bedroom with ensuite bath. Each side of the upstairs living space has loft sleeping bunk-areas for kids (of all ages!). SEE DEDICATED PROPERTY WEBSITE FOR VIDEOS, VIRTUAL WALKTHROUGH, FLOORPLANS AND MORE. See MLS Property & Listing Details & 33 images.


WOODSTOCK VT Lake House for sale $$1,995,000 | $358 per sq.ft.

$1,995,000 | $358 per sq.ft. WOODSTOCK VT LAKE HOUSE FOR SALE ON RIVER OTTAUQUECHEE RIVER
Price Change! reduced by $455,000 down 23% on September 25th 2025

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


Under Contract WOODSTOCK VT Home for sale $$2,400,000 | $497 per sq.ft.

$2,400,000 | $497 per sq.ft. WOODSTOCK VT HOME FOR SALE

1059 Carlton Hill Road 5 Beds | 5 Baths |   Total Sq. Ft. 4832  |  Acres: 2.64

Set on over two picturesque acres along one of the most beautiful country roads in the area, this spacious and impeccably renovated contemporary farmhouse offers the perfect balance of charm and modern comfort. Just minutes from Woodstock and South Woodstock, the property enjoys both convenience and a peaceful setting. The home features generous living and entertaining spaces (remodeled in 2016 by Sargent Design Company), multiple porches, and seamless indoor-outdoor flow. The main residence offers 5 bedrooms, including a large primary suite, while the converted barn includes a private guest apartment, ideal for hosting company. Highlights include a hot tub, indoor and outdoor fireplaces, and thoughtful updates throughout that make the home as efficient and easy to maintain as it is elegant. With open spaces designed for gatherings and cozy corners for retreat, this home is equally suited for year-round living or a Vermont getaway. Outdoor enthusiasts will appreciate the home's proximity to skiing at Killington and Saskadena Six, as well as easy access to hiking, biking, and countless four-season activities. A truly exceptional property blending timeless farmhouse character with today's modern luxuries. See MLS Property & Listing Details & 50 images. Includes a Virtual Tour


Under Contract WOODSTOCK VT Home for sale $$2,599,000 | $434 per sq.ft.

$2,599,000 | $434 per sq.ft. WOODSTOCK VT HOME FOR SALE

41 Pleasant Street 9 Beds | 11 Baths |   Total Sq. Ft. 5993  |  Acres: 0.46

This exquisite Victorian invites you to embracequintessential New England living in a charming downtown setting. This property in Woodstock, VT offers a rare blend of historic charm and modern convenience, all within one of Vermont's most beloved communities. Woodstock is often hailed as "the prettiest small town in America," and for good reason. The village is a vibrant resort town with maple-lined streets, stately homes, artisanal boutiques, and a warm and welcoming spirit. The town and assorted local organizations offer cultural and family fun activities offered throughout the year. Currently being used as a 7-room Inn boasting an additional 2-bedroom owner's quarters, this property could be returned to operating as a private residential property with zoning permit. Please contact for more information on making this beautiful place your dream home! See MLS Property & Listing Details & 54 images.


Under Contract VILLAGE OF WOODSTOCK IN TOWN OF WOODSTOCK VT Home for sale $$2,600,000 | $650 per sq.ft.

$2,600,000 | $650 per sq.ft. VILLAGE OF WOODSTOCK IN TOWN OF WOODSTOCK VT HOME FOR SALE

2 Pleasant Street 4 Beds | 4 Baths |   Total Sq. Ft. 3998  |  Acres: 0.37

2 PLEASANT STREET- This stately brick Federal is a historic landmark property in the heart of Woodstock Village, home to many storied families in the town and state's history, notably Julius Converse, Governor of Vermont in 1872, and Laurance Rockefeller. Though it has been well-renovated and maintained over the years, it retains many of its historic features to beautifully blend modern convenience with original charm. The first floor features oversized, recently updated windows and several spacious high ceiling gathering rooms including a formal living room, dining room, library, and central family room. A cozy eat-in kitchen with fireplace on the north side of the house opens to a lovely landscaped yard shaded by mature maple trees. The second floor, also punctuated by high ceilings and windows to give it a bright and spacious feel, features a primary bedroom on the front side of the house with an adjoining dressing area, walk in closets, and full bath. Adjacent the primary is another sizable bedroom with its own bath, while two additional bedrooms with shared bath round out the level. The detached barn garage has space for one car and plenty of additional storage. Idyllically sited and within walking distance of local shopping, dining, schools, hiking trails, and Marsh-Billings-Rockefeller National Historic Park, this iconic Woodstock home is a rare gem. See MLS Property & Listing Details & 43 images. Includes a Virtual Tour