Woodstock, VT Homes for Sale

/54
$2,599,000
- 9 Beds
- 11 Baths
- 5,993 Sq Ft
41 Pleasant St, Woodstock, VT 05091

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

Jennifer Falvey

KW Vermont Woodstock

(802) 347-9544

41 Pleasant St, Woodstock, VT 05091
/41
$1,495,000
- 4 Beds
- 1.5 Baths
7 Slayton Terrace, Woodstock, VT 05091

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

Keri Cole Williamson Group Sotheby's International Realty

7 Slayton Terrace, Woodstock, VT 05091
/32
$1,195,000
- 3 Beds
- 3.5 Baths
- 2,592 Sq Ft
26 Mount Peg Rd Unit A, Woodstock, VT 05091

Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

Mary Mayhew Snyder Donegan Real Estate Group

26 Mount Peg Rd Unit A, Woodstock, VT 05091
/31
$995,000
- 3 Beds
- 3.5 Baths
- 2,584 Sq Ft
26 Mount Peg Rd Unit B, Woodstock, VT 05091

Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

Mary Mayhew Snyder Donegan Real Estate Group

26 Mount Peg Rd Unit B, Woodstock, VT 05091
/28
$995,000
- 3 Beds
- 3.5 Baths
- 2,584 Sq Ft
26 Mount Peg Rd Unit C, Woodstock, VT 05091

Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

Mary Mayhew Snyder Donegan Real Estate Group

26 Mount Peg Rd Unit C, Woodstock, VT 05091
/33
$1,895,000
- 2 Beds
- 2.5 Baths
- 2,944 Sq Ft
2394 Fletcher Hill Rd, Woodstock, VT 05091

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

John Snyder Snyder Donegan Real Estate Group

2394 Fletcher Hill Rd, Woodstock, VT 05091
/31
$1,195,000
- 3 Beds
- 3.5 Baths
- 2,385 Sq Ft
26 Mount Peg Rd Unit D, Woodstock, VT 05091

Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage

Mary Mayhew Snyder Donegan Real Estate Group

26 Mount Peg Rd Unit D, Woodstock, VT 05091
/40
$2,950,000
- 6 Beds
- 6 Baths
- 5,433 Sq Ft
61 Academy Cir, Woodstock, VT 05071

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

Carol Wood Williamson Group Sothebys Intl. Realty

61 Academy Cir, Woodstock, VT 05071
/28
$3,300,000
- 3 Beds
- 4.5 Baths
- 3,682 Sq Ft
249 Sawyer Rd, Woodstock, VT 05091

Located in Woodstock, Vermont just one mile from the village green, the Alta House offers a rich quality of life filled with poolside sunsets, mountain vistas, proximity to town, and access to endless outdoor recreation opportunities. Enjoy the convenience of living close to the shops, cafes, and restaurants of Woodstock, while being tucked away in your own world above. The 3-bedroom primary

Andrew Bustin LandVest, Inc/Woodstock

249 Sawyer Rd, Woodstock, VT 05091
/38
$895,000
- 4 Beds
- 1.5 Baths
- 1,580 Sq Ft
51 River St, Woodstock, VT 05091

Beautiful residence with newer renovations...located in the heart of historic Woodstock. Sunlit rooms, open floor concept with handsome refinished original pine floors. Stunning kitchen with stainless appliances, oversized island and soapstone counters accent the new cabinetry. Large dining room for entertaining with lovely screened in porch with double doors that lead out to a privately enclosed

Gretchjen Smith Williamson Group Sothebys Intl. Realty

51 River St, Woodstock, VT 05091
/11
$779,000
- Land
- 6.46 Acres
- $120,588 per Acre
0 Barnard Rd Unit 20.002, Woodstock, VT 05091

A truly unique 6 acre parcel of land conveniently located in the heart of Woodstock! Tremendous development potential! Zoning allows both COMMERCIAL and RESIDENTIAL use! The 6 acres visually divide into 2 components with 2 diverse personalities. The 1st component is an extraordinary private building lot in the heart of Woodstock! Access to this 4 acre component initially leads through a pleasant

John Wetmore Wetmore Real Estate

0 Barnard Rd Unit 20.002, Woodstock, VT 05091
/43
$530,000
- 3 Beds
- 2 Baths
- 1,920 Sq Ft
1514 South Rd, Woodstock, VT 05091

This tidy, well maintained Mid-Century Ranch home is conveniently located just 1.5 miles from the Village Green. Perched on a sunny knoll with a southern valley view, this well maintained home features open concept kitchen/dining, a large, bright living room, three bedrooms all with oak floors, a walk out basement providing opportunity for guest accommodation, or a hobby/play room. The 2 car

Danny Kogut Williamson Group Sothebys Intl. Realty

1514 South Rd, Woodstock, VT 05091
/39
$749,000
- 3 Beds
- 4 Baths
- 1,660 Sq Ft
37 South St, Woodstock, VT 05091

Welcome to this beautifully renovated residence in the vibrant heart of Woodstock Village. Enjoy unparalleled convenience with a short stroll to the Elementary School, Woodstock Inn, the picturesque Green, and an array of charming shops, restaurants, and bakeries that define village living. Nestled directly across from Vail Field, this home offers easy access to playgrounds, ball fields, and

Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

37 South St, Woodstock, VT 05091
/24
$646,500
- Land
- 37.85 Acres
- $17,081 per Acre
0 South Rd, Woodstock, VT 05071

Country land at the south end of Woodstock reaching from RT 106 to the top of the ridge. Potential for views with clearing at several levels. Trails through the property with access to the GMHA network. Stonewalls and a stream.About two miles to GMHA and South Woodstock village, one mile to VAST trail.40 minutes to skiing at Killington, less to Okemos. Seven miles into Woodstock Village.

Matthew Spittle Vermont Horse Country Real Estate

0 South Rd, Woodstock, VT 05071
/45
$675,000
- 4 Beds
- 3 Baths
- 3,190 Sq Ft
598 E Woodstock Rd, Woodstock, VT 05091

Historic Woodstock, Vermont – Spacious Home on Nearly 3 Acres. Welcome to a rare opportunity in the heart of Woodstock, one of Vermont’s most picturesque and sought-after villages. This expansive home offers generous living space with many rooms, providing flexibility for a large household, home offices, guest quarters, or the potential to create multiple apartments (buyer to verify local

Erika Smith Coldwell Banker LIFESTYLES - Hanover

598 E Woodstock Rd, Woodstock, VT 05091
/48
$1,600,000
- 3 Beds
- 3.5 Baths
- 3,294 Sq Ft
39 Elm St Unit B, Woodstock, VT 05091

The Richmond House – Unit B | Woodstock Village. An enduring Woodstock landmark, the iconic Richmond House (c.1826) is a proud brick Federal distinguished by its softly weathered rose-hued patina and refined architectural detail. Set on more than an acre behind a classic white picket fence and thoughtfully reimagined under the direction of Laurence Rockefeller, the property comprises three

Derek Cosentino Four Seasons Sotheby's Int'l Realty

39 Elm St Unit B, Woodstock, VT 05091
/60
$549,000
- Land
- 20.2 Acres
- $27,178 per Acre
00 Long Hill Rd, Woodstock, VT 05071

Discover the perfect blend of privacy and convenience with this exceptional 20.2-acre parcel, combining two lots into one remarkable opportunity. Featuring a 50 foot right-of-way for access, this wooded retreat offers multiple prime building sites. With selective clearing, you can take in breathtaking views in your choice of direction; east, south, north, or west. Located just minutes from South

Eric Johnston Four Seasons Sotheby's Int'l Realty

00 Long Hill Rd, Woodstock, VT 05071
/32
$239,000
- 1 Bed
- 1 Bath
- 856 Sq Ft
42 Heritage Condo Way Unit 23 D, Woodstock, VT 05091

Amazing opportunity to own a property that is perfect as a full time home or a vacation get away, in the highly desired Heritage Condo community. The setting is serene in a low density area. This condo has had many updates and is ready for new owners to add their personal touch. The charming living room complete with wood floors , a stone accent wall and double glass doors leading to a private

Carol Wood Williamson Group Sothebys Intl. Realty

42 Heritage Condo Way Unit 23 D, Woodstock, VT 05091
/60
$950,000
- 3 Beds
- 2.5 Baths
- 2,794 Sq Ft
34 Midsomer Meadows Ln, Woodstock, VT 05091

Welcome to Starry Hill, a fully furnished, handcrafted, solid-timber Colonial privately nestled on 18.9 tranquil acres just 5 miles North of Woodstock. This 3-bedroom, 2.5 bath home was built over 4 years by a family of loggers and master craftsmen. Used recently as an AirBnB rental and ready for occupancy. This exceptional home features Eastern white pine walls, hemlock structural beams, and

John Bassette Bassette Real Estate Group

34 Midsomer Meadows Ln, Woodstock, VT 05091
/59
$14,900,000
- 7 Beds
- 10 Baths
- 12,520 Sq Ft
355 Greene Rd, Woodstock, VT 05071

Star Hill Farm is completely private, hidden on a hillside with pastoral and mountain views in the heart of South Woodstock. From the valley floor to the top of Meetinghouse Hill, you will be inspired by its beauty, a mesmerizing 183.7+/- acre oasis over gorgeous terrain with fields, woodlands, trails, and stone walls. The historic 2-bedroom guest house and party barn are fully restored, and

Chris Lang

355 Greene Rd, Woodstock, VT 05071
/7
$325,000
- Land
- 8 Acres
- $40,625 per Acre
1 Carlton Hill Rd, Woodstock, VT 05091

Sweet Spot - 8 acre building lot located within minutes of the Woodstock Village Green! Driveway is in place and a lovely building site has been cleared and power is at site. Wonderful opportunity to build your Vermont getaway or primary residence. Enjoy access to four season recreation, Marsh-Billings-Rockefeller National Park, theatre, arts, dining, shopping and a short commute to all

Mary Mayhew Snyder Donegan Real Estate Group

1 Carlton Hill Rd, Woodstock, VT 05091
/48
$6,750,000 New Construction
- 4 Beds
- 4.5 Baths
- 5,087 Sq Ft
412 Skyland Ln, Woodstock, VT 05091

Once the site of an 1850s homestead and now reimagined for 21st-century living, Skyland Farm is a private retreat on 63 acres. Mineral springs, glass architecture, and extraordinary views define this rare legacy property, just minutes from the village of Woodstock and with direct access to the trails of Mount Peg. Found at the end of a quiet lane, sweeping vistas of the Green Mountains and

Story Jenks LandVest, Inc/Woodstock

412 Skyland Ln, Woodstock, VT 05091
/37
$985,000
- 4 Beds
- 3 Baths
- 2,785 Sq Ft
1782 Randall Rd, Woodstock, VT 05091

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

Wade Treadway Wade I Treadway Real Estate

1782 Randall Rd, Woodstock, VT 05091
/47
$395,000
- 4 Beds
- 2 Baths
- 1,617 Sq Ft
5798 W Woodstock Rd, Woodstock, VT 05091

Classic Vermont farmhouse just minutes from the heart of Woodstock. This charming 4 bedroom , 2 bath home offers the character of a traditional New England property with comfortable , move in ready living spaces. The home features a bright eat-in kitchen, spacious dining room, and a welcoming living room with a wood-burning fireplace--perfect for cozy Vermont evenings. Freshly painted interiors

Carol Wood Williamson Group Sothebys Intl. Realty

5798 W Woodstock Rd, Woodstock, VT 05091
/8
$275,000
- Land
- 1.95 Acres
- $141,026 per Acre
3186 South Rd, Woodstock, VT 05091

1.95 Acre lot minutes from Woodstock Village, South Woodstock, and Green Mountain Horse Association. Kidder Brook runs along the North property boundary, and a sunny lawn area has multiple small gardens. There is a large clearing, and a well-cared for 1973 mobile home on a concrete slab on the property. This lot has tremendous potential in a fantastic location. House is being sold As-is.

Andrew Hubbell Vermont Real Estate Company

3186 South Rd, Woodstock, VT 05091
/26
$479,000
- 2 Beds
- 3 Baths
- 2,091 Sq Ft
85 Townhouse Way Unit 14, Woodstock, VT 05091

Fully furnished condo nestled in a small quiet community just 5 minutes from "Historic Woodstock". Super location! This unit is in very good condition- first floor comprised of a den//bedroom with pocket doors for added privacy and an adjacent 3/4 bath. Spacious living room anchored by a newer propane fireplace to curl up with a book on a cold winter day. A couple of steps down takes you into a

Gretchjen Smith Williamson Group Sothebys Intl. Realty

85 Townhouse Way Unit 14, Woodstock, VT 05091

Vermont Windsor County Woodstock

Why Live in Woodstock

Woodstock, Vermont, is a picturesque small town known for its historic charm and scenic landscapes. The town features Federal-style and Colonial Revival homes from the 1800s and early 1900s, with brick exteriors or white siding, often complemented by white picket fences and well-maintained lawns. Downtown Woodstock is lined with brick storefronts housing local businesses, including home goods shops, a general store, and a variety of dining options. Notable spots include F.H. Gillingham & Sons, a historic general store, and The Prince and the Pauper, an upscale restaurant. Outdoor enthusiasts can enjoy year-round activities at Marsh-Billings-Rockefeller National Historical Park, which offers 20 miles of hiking trails, and the Woodstock Inn & Resort Nordic Center, which maintains 12 miles of cross-country skiing trails in winter. Mt. Peg provides a 2.5-mile hike to its summit, while Vail Field offers traditional park amenities. Woodstock also hosts several annual events, such as the Apple and Crafts Fair & Food Truck Festival and Wassail Weekend. The town's highly rated schools include Woodstock Elementary School, Prosper Valley School, and Woodstock Union High School and Middle School, which offers Advanced Placement courses and dual enrollment options. For practical needs, groceries are available at the Woodstock Village Market, with larger stores located 15 miles away in Lebanon, New Hampshire. Flood risk is present along the Ottauquechee River and Kedron Brook, with maps available from the Vermont Department of Environmental Conservation.

Learn more about living in Woodstock

Frequently Asked Questions

What is the average home price in Woodstock, VT?

Homes for sale in Woodstock, VT have an average home price of $1,458,533.

How many homes have sold over the last 12 months in Woodstock, VT?

70 homes have sold in Woodstock, VT over the last 12 months.

What are the most popular zip codes in Woodstock, Windsor County, VT?

The most popular zip codes in Woodstock, Windsor County, VT include 05091, 05149, 05001, 05071 and 05048.

How much do you need to make to afford a house in Woodstock?

The median home price in Woodstock is $910,000. If you put a 20% down payment of $182,000 and had a 30-year fixed mortgage with an interest rate of 6.3%, your estimated principal and interest payment would be $4,510 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $193K a year to afford the median home price in Woodstock. Learn how much home you can afford with our Home Affordability Calculator.

How are the schools in Woodstock, VT?

Woodstock, VT has highly rated public and private schools. Some of the best schools in Woodstock based on Niche Grades are Woodstock Senior Uhsd #4, Woodstock Elementary School and Woodstock Union High School. Browse all the schools in Woodstock, VT to learn more.

Home Trends in Woodstock, VT

On average, homes in Woodstock, VT sell after 86 days on the market compared to the national average of 56 days. The median sale price for homes in Woodstock, VT over the last 12 months is $789,000, down 10% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$789,000

Median Single Family Sale Price

$922,500

Median Townhouse Sale Price

$489,000

Median 2 Bedroom Sale Price

$480,000

Median 1 Bedroom Sale Price

$230,000

Average Price Per Sq Ft

$474

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

3.40

Median List Price

$910,000

Median Change From 1st List Price

Median Home Sale Price YoY Change

-10%

How to Buy a Home How to Finance a Home How to Sell a Home

Woodstock Types of Homes for Sale

More About Living in Woodstock

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