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South Woodstock, VT Homes for Sale

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  • /46

    $1,749,000

    • 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 distinguished brick Federal with a softly weathered, rose-hued patina and elegant architectural details. Set on over an acre behind a classic white picket fence, this historic property—reimagined under the direction of Laurence Rockefeller—comprises three luxurious residences

    Zoe Hathorn Washburn Snyder Donegan Real Estate Group

    39 Elm St Unit B, Woodstock, VT 05091
  • /22

    $645,000

    • 3 Beds
    • 1.5 Baths
    • 1,468 Sq Ft

    187 Dana Rd, Woodstock, VT 05091

    This delightful gambrel cape offers a wonderful combination of thoughtful and charming updates, energy efficient upgrades, and a coveted and convenient location! An intelligent interior design offers an all-season functional flow for everyday living as well as entertaining. Step inside by way of a spacious entryway/mudroom that also has direct entry from the attached garage. One will find the

    Mary Mayhew Snyder Donegan Real Estate Group

    187 Dana Rd, Woodstock, VT 05091
  • /40

    $3,500,000

    • 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
  • /42

    $8,000,000

    • 3 Beds
    • 3.5 Baths
    • 6,096 Sq Ft

    115 Eastman Rd, South Woodstock, VT 05071

    Sorgenfrei, or "Carefree," was built by Ennis Construction in 2015, and this extraordinary property truly embodies that sobriquet. A stunning and uncommon confluence of the finest materials and the most energy efficient techniques, this home was carefully constructed to maximize worry-free enjoyment. The most advanced systems and a focused commitment to the highest quality make this home a

    Keri Cole

    115 Eastman Rd, South Woodstock, VT 05071
  • /35

    $1,350,000

    • 4 Beds
    • 2.5 Baths
    • 2,668 Sq Ft

    513 Deer Brook Way Unit Lot 16, Woodstock, VT 05091

    This traditional New England Colonial home was professionally designed and custom built by the renowned Vermont Vernacular Builders. The home is strategically sited to enjoy the long views of the distant hills and to benefit from its southern exposure. This 4 bedroom is a quintessential classic example of pure Vermont living apparent in this gracious sun-filled home. There are wide board floors

    Chris Crowe Quechee Lakes Real Estate Center

    513 Deer Brook Way Unit Lot 16, Woodstock, VT 05091
  • /34

    $2,199,000

    • 4 Beds
    • 3.5 Baths
    • 3,564 Sq Ft

    15 Hathorn Hill Street Extension, Woodstock, VT 05091

    An incredibly rare combination of in-Village and country living. 4+ acres and privacy with a pond and heated in-ground pool, yet walk-to-the Green. The residence, designed and built by the well-respected design-build firm Ambrose Construction, offers modern amenities, appliances and construction with a “Vermont Farmhouse” aesthetic. The vaulted ceiling timber frame great-gathering room has

    John Snyder Snyder Donegan Real Estate Group

    15 Hathorn Hill Street Extension, Woodstock, VT 05091
  • /59

    $1,850,000

    • 2 Beds
    • 3 Baths
    • 2,106 Sq Ft

    7 North St, Woodstock, VT 05091

    Stunning Renovated Antique Cape in the Heart of Woodstock Village!Tucked away on over an acre of beautifully landscaped land directly abutting the Marsh-Billings-Rockefeller National Park, this fully renovated antique Cape offers the rare combination of historic charm, modern efficiency, and unbeatable walkability. Located in the heart of Woodstock Village, you can stroll to the village

    Keri Cole Williamson Group Sothebys Intl. Realty

    7 North St, Woodstock, VT 05091
  • /60

    $2,200,000

    • 3 Beds
    • 2.5 Baths
    • 5,422 Sq Ft

    2334 South Rd, Woodstock, VT 05091

    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

    Danny Kogut Williamson Group Sothebys Intl. Realty

    2334 South Rd, Woodstock, VT 05091
  • /60

    $1,399,000

    • 4 Beds
    • 4 Baths
    • 3,669 Sq Ft

    484 Route 12, Hartland, VT 05048

    South facing end of the road retreat, with long views! Equally appealing are expansive western views, for dynamic sunsets! Equestrian amenities of small horse barn, fenced paddocks and direct access to trails! This welcoming residence is certainly unique! A cape style home, with contemporary open floor plan, dramatic windows and a wide deck is seamlessly married to a rustic log cabin, with true

    John Wetmore Wetmore Real Estate

    484 Route 12, Hartland, VT 05048
  • /57

    $1,995,000

    • 3 Beds
    • 2.5 Baths
    • 2,688 Sq Ft

    20 The Green, Woodstock, VT 05091

    Stunning antique cape! Located in the 'heart' of Woodstock. Originally located on Central Street- this home was moved in the 1960's to this location and had an extensive renovation in 2011. The antique brick section was built in 1826- it boasts a spacious living room anchored with a large wood burning fireplace, original wide pine floors and lots of space for entertaining. Adjacent find a

    Gretchjen Smith Williamson Group Sothebys Intl. Realty

    20 The Green, Woodstock, VT 05091
  • /35

    $1,895,000

    • 5 Beds
    • 4.5 Baths
    • 4,214 Sq Ft

    10 College Hill Rd, Woodstock, VT 05091

    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

    John Snyder Snyder Donegan Real Estate Group

    10 College Hill Rd, Woodstock, VT 05091
  • /55

    $1,095,000

    • 4 Beds
    • 3.5 Baths
    • 2,710 Sq Ft

    2 Maple St, Woodstock, VT 05091

    Located in the Heart of Woodstock Village- fantastic location at the foot of the Mtn Peg trail system with easy access to Vail field and all of towns amenities. This beautifully renovated home is completely new. Handsome farmhouse vernacular style home with traditional slate floors, sliding barn doors and wood floors throughout first floor with an open concept for entertaining and all new

    Gretchjen Smith Williamson Group Sothebys Intl. Realty

    2 Maple St, Woodstock, VT 05091
  • /43

    $545,000

    • 3 Beds
    • 2 Baths
    • 2,616 Sq Ft

    371 Vermont 12, Hartland, VT 05048

    - Gingerbread Cottage on 12 Acres Near Woodstock & Quechee - Lovingly maintained by its current owner, this 3 bedroom, 2 bath home sits on 12 private acres of open land, woods, and trails. With over 2,500 sq. ft., the home blends character and comfort—featuring wide pine floors, vintage custom cabinetry, and a living room with exposed beams and a stone fireplace with a Vermont Castings

    Keri Cole Williamson Group Sothebys Intl. Realty

    371 Vermont 12, Hartland, VT 05048
  • /36

    $465,000

    • 3 Beds
    • 3 Baths
    • 1,600 Sq Ft

    2 High St, Woodstock, VT 05091

    FLASH OPPORTUNITY AWAITS – Historic c. 1890 1,600 sq/ft. unfinished home in the center of downtown Woodstock. In the heart of everything! LOOKING FOR A FAST SALE - AND A CASH BUYER. The home has been stripped back to framing and is ready for a builder or future investment. It is not currently habitable and will not be able to be sold or shown to someone looking for financing or construction loan

    John Bassette Bassette Real Estate Group

    2 High St, Woodstock, VT 05091
  • /37

    $845,000

    • 2 Beds
    • 1.5 Baths
    • 1,714 Sq Ft

    403 Horse Shoe Way, Woodstock, VT 05071

    Totally secluded on a rolling hillside, just 10 minutes from the Woodstock Village Green, this storybook Post and Beam cottage awaits your vision. From the reclaimed centuries old barn frame to the massive fieldstone fireplace, every detail is well thought, and impeccably executed honoring the Vermont tradition of reclaiming and utilizing locally sourced materials.The home was carefully, and

    Danny Kogut Williamson Group Sothebys Intl. Realty

    403 Horse Shoe Way, Woodstock, VT 05071
  • /27

    $1,200,000

    • 5 Beds
    • 4.5 Baths
    • 3,486 Sq Ft

    19 Church St Unit EX, Woodstock, VT 05091

    Bright and spacious five bedroom, five bath in-village residence with Ottauquechee River frontage and less than 1-minute walk to the Woodstock Green. 2-car attached garage enters into the kitchen via a mud-laundry room. Eat-in kitchen with stainless appliances, granite countertops and a large sunny bay window leads to the formal dining room, and also opens to the patio, perfect for entertaining

    John Snyder Snyder Donegan Real Estate Group

    19 Church St Unit EX, Woodstock, VT 05091
  • /55

    $1,100,000

    • 3 Beds
    • 3 Baths
    • 2,150 Sq Ft

    509 Church Hill Rd, Wood Stock, VT 05091

    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 ,

    Carol Wood Williamson Group Sothebys Intl. Realty

    509 Church Hill Rd, Wood Stock, VT 05091
  • /39

    $775,000

    • 3 Beds
    • 2.5 Baths
    • 1,850 Sq Ft

    17 Golf Pond, Woodstock, VT 05091

    Nestled in the heart of the picturesque Village of Woodstock, this beautiful 3-bedroom, 2.5-bath home offers a perfect blend of classic Vermont charm and modern comfort. Overlooking a serene pond, the home boasts an open floor plan on the main level..Step inside to find warm wood floors throughout, a welcoming fireplace that anchors the spacious living area, a thoughtfully laid out kitchen

    Kasia Butterfield Coldwell Banker LIFESTYLES - Quechee

    17 Golf Pond, Woodstock, VT 05091
  • /19

    $695,000

    • Land
    • 61 Acres
    • $11,474 per Acre

    0 Noah Wood Rd, Woodstock, VT 05071

    Incredible location! 60+ acres situated on the corner of South Rd. (106) and Noah Wood Rd. in beautiful South Woodstock. The land rises from the roads to the crest of the hilltop with amazing view potential looking to the Northeast. Multiple building sites can be found throughout the property which offers great recreational opportunities including direct access to the VAST trail on the lower

    Dan Noble Snyder Donegan Real Estate Group

    0 Noah Wood Rd, Woodstock, VT 05071
  • /47

    $8,000,000

    • 3 Beds
    • 3.5 Baths
    • 5,384 Sq Ft

    115 Eastman Rd, Woodstock, VT 05091

    Sorgenfrei, or "Carefree," was built by Ennis Construction in 2015, and this extraordinary property truly embodies that sobriquet. A stunning and uncommon confluence of the finest materials and the most energy efficient techniques, this home was carefully constructed to maximize worry-free enjoyment. The most advanced systems and a focused commitment to the highest quality make this home a

    Keri Cole Williamson Group Sothebys Intl. Realty

    115 Eastman Rd, Woodstock, VT 05091
  • /28

    $495,000

    • 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

    Gretchjen Smith Williamson Group Sothebys Intl. Realty

    85 Townhouse Way Unit 14, Woodstock, VT 05091
  • /26

    $489,500

    • 2 Beds
    • 1.5 Baths
    • 930 Sq Ft

    11A Prospect St, Woodstock, VT 05091

    Walk to everything Woodstock village has to offer from this sunny condo! Within an easy stroll of the Woodstock Inn, downtown restaurants, farmer's markets, and the Marsh Billings Rockefeller National Park, 11A Prospect is ideal for enjoying the charms of village living. Elevated above the Route 4 on a bucolic neighborhood side street, this well-kept home offers historic details with modern

    Keri Cole Williamson Group Sothebys Intl. Realty

    11A Prospect St, Woodstock, VT 05091
  • /27

    $650,000

    • Land
    • 78 Acres
    • $8,366 per Acre

    0 Mecawee Rd, Woodstock, VT 05091

    Spectacular 77+ acre parcel on sought after Mecawee Rd. with a perfect combination of level, sloping and hilly terrain. There are multiple building sites including a large cleared area set back off the road with a driveway in place and utilities (electric & fiber optic) at the street. This past Fall, the Sellers went to great lengths to clear the land all the way down to the road opening up

    Dan Noble Snyder Donegan Real Estate Group

    0 Mecawee Rd, Woodstock, VT 05091
  • /9

    $275,000

    • Land
    • 0.43 Acre
    • $639,535 per Acre

    1054 W Woodstock Rd, Woodstock, VT 05091

    Ideally located parcel across West Woodstock Road from the Woodstock Farmers Market and 500 yards from the entry to Woodstock Union Middle & High School. Public water and sewer available with access off Prosper Road near the junction of US Road Route 4/West Woodstock Road. Building plans available. Multi-unit housing development potential in zero vacancy environment.

    Laird Bradley Williamson Group Sothebys Intl. Realty

    1054 W Woodstock Rd, Woodstock, VT 05091
  • /33

    $755,000

    • 3 Beds
    • 3 Baths
    • 1,550 Sq Ft

    13 Slayton Terrace, Woodstock, VT 05091

    Charming cottage located in the heart of historic Woodstock Village with walking distance to all the shops, restaurants and town theatre. Mtn Peg walking trails just a 2 minute walk from front door for those hiking enthusiasts. This home is filled with an abundance of natural sunlight and features all hardwood floors throughout. New kitchen with butcher block counters, stainless appliances,

    Gretchjen Smith Williamson Group Sothebys Intl. Realty

    13 Slayton Terrace, Woodstock, VT 05091
  • /4

    $84,900

    • Land
    • 3.80 Acres
    • $22,342 per Acre

    14 Hartland Hill Rd, Hartland, VT 05048

    Owner Will Consider Financing – Ask for Details!3.8 Acres of Wooded Serenity in Hartland, VTDiscover the perfect balance of privacy and convenience with this beautiful 3.8-acre wooded parcel tucked away in the quiet countryside of Hartland, Vermont. Set off the beaten path, this peaceful retreat offers a sense of seclusion while being just minutes from the vibrant communities of

    Kris Pettee EXP Realty

    14 Hartland Hill Rd, Hartland, VT 05048
  • /58

    $549,000

    • Land
    • 20 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

    Eric Johnston Four Seasons Sotheby's Int'l Realty

    00 Long Hill Rd, Woodstock, VT 05071
  • /43

    $2,250,000

    • 5 Beds
    • 3.5 Baths
    • 3,502 Sq Ft

    4945 South Rd, Woodstock, VT 05071

    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

    Story Jenks LandVest, Inc/Woodstock

    4945 South Rd, Woodstock, VT 05071
  • /48

    $795,000

    • 3 Beds
    • 2 Baths
    • 1,694 Sq Ft

    25 Linden Hill St, Woodstock, VT 05091

    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

    Laird Bradley Williamson Group Sothebys Intl. Realty

    25 Linden Hill St, Woodstock, VT 05091
  • /60

    $2,450,000

    • 4 Beds
    • 3.5 Baths
    • 5,573 Sq Ft

    851 Riverside Park Rd, Woodstock, VT 05091

    "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

    Richard Higgerson Higgerson & Company

    851 Riverside Park Rd, Woodstock, VT 05091
  • /6

    $54,900

    • Land
    • 29 Acres
    • $1,893 per Acre

    0 Rt 7 (Db 94 Dp 399), Royalton, KY 41464

    These 29 acres, per PVA map, are located in southern Magoffin County in Royalton, Kentucky, with the acreage running along both sides of RT 7. The property is located in the Salt Lick area outside Royalton and includes property on both sides of Salt Lick Road as well. The property is undeveloped but electric and public water are available. For those with visions of homesteading, the Licking River

    Doug Wireman First Choice Realty & Assoc.

    0 Rt 7 (Db 94 Dp 399), Royalton, KY 41464
  • /39

    $659,000

    • 3 Beds
    • 2.5 Baths
    • 1,958 Sq Ft

    5851 South Rd, Woodstock, VT 05071

    This charming home is an amazing opportunity to own a piece of history in the lovely village of South Woodstock , Vermont. Starting its life as the garage and home of Clyde Wood it has evolved over time with the present owners into a beautiful , meticulous residence. Much attention to detail can be found in every room from wide pine flooring to cathedral ceiling in the great room. The home is

    Carol Wood Williamson Group Sothebys Intl. Realty

    5851 South Rd, Woodstock, VT 05071
  • /59

    $1,850,000

    • 4 Beds
    • 6 Baths
    • 4,764 Sq Ft

    77 Newton Rd, Reading, VT 05062

    Welcome to this private property on a quiet country road in desirable Reading, VT, just 4 miles from South Woodstock. Only 30 minutes to Okemo Mountain Resort and 35 minutes to Killington Ski Area! This spacious 4-bedroom, 6-bathroom home comfortably sleeps 12. This home was made for entertaining! The updated kitchen features high-end appliances, leading to a dining area. Off the kitchen, an

    Susan Hickey Snyder Donegan Real Estate Group

    77 Newton Rd, Reading, VT 05062
  • /19

    $275,000

    • Land
    • 5.00 Acres
    • $55,000 per Acre

    95 Jenne Rd, Hartland, VT 05048

    5 acres of peacefully quiet land that are situated in an area well known to the equestrian community! Both the surrounding neighbors, on this seldom traveled country road, and numerous other properties in this broad community present as substantial privately sited homes. As you meander up Jenne Road to reach the parcel the classic large maple trees that typify the borders of pastoral Vermont

    John Wetmore Wetmore Real Estate

    95 Jenne Rd, Hartland, VT 05048
  • /13

    $1,789,000

    • Land
    • 100 Acres
    • $17,890 per Acre

    5000 Vermont 106, Reading, VT 05062

    Beautiful building lot of approximately 100 acres just 5 mins to South Woodstock, and privately situated with a driveway entrance directly on VT 106 for easy access. The parcel includes woods roads and trails, ancient stone walls, brooks, ponds and some cleared areas as potential future building sites with lovely southern exposure and long-range views of distant hills. The property contains two

    John Snyder Snyder Donegan Real Estate Group

    5000 Vermont 106, Reading, VT 05062
  • /39

    $1,499,000

    • Land
    • 4.57 Acres
    • $328,009 per Acre

    458 Woodstock Rd, Wood Stock, VT 05091

    It has been said that the highest and best use of this landmark Woodstock property would be a combination of constructing multiple residential units, in the private rear acreage, and commercial development, of the highly visible Route 4 road frontage. There is no question of the unlimited potential! Highly visible! Well located, on the East End entrance route to Woodstock Village! This property

    John Wetmore Wetmore Real Estate

    458 Woodstock Rd, Wood Stock, VT 05091
  • /14

    $845,000

    • 2 Beds
    • 1 Bath
    • 600 Sq Ft

    234 Randall Rd, Wood Stock, VT 05091

    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

    Wade Treadway Wade I Treadway Real Estate

    234 Randall Rd, Wood Stock, VT 05091
  • /48

    $7,250,000 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 65 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

    Story Jenks LandVest, Inc/Woodstock

    412 Skyland Ln, Woodstock, VT 05091

Frequently Asked Questions

What are the most popular zip codes in South Woodstock, VT?
The most popular zip codes in South Woodstock, VT include 05149, 05001, 05751, 03743 and 03773.
What are the most popular neighborhoods near South Woodstock, VT?
The most popular neighborhoods near South Woodstock, VT are South Woodstock, Quechee Lakes and Hartford Village.
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