Woodstock Homes Between $500K and $1 Million

Woodstock, Vermont offers buyers myriad choices of beautiful and unique properties. A historic home in quaint Woodstock Village within walking distance to all the amenities you need, a secluded home with lots of land and views of the Green Mountains, a vacation home, or an investment property.

It’s also what Woodstock offers beyond beautiful homes that makes it special. For lovers of outdoors, there are miles of trails for hiking, biking, and horseback riding, and snowmobiling. Rivers in and around Woodstock offer fishing and kayaking.

For art lovers, there are galleries and theaters in town. For foodies, there are topnotch restaurants, many featuring farm-to-table cuisines.  Woodstock, Vermont is one of the loveliest towns in the Upper Valley. The area offers even more of the great amenities and attractions you'll find in Woodstock.

Woodstock, VT could be the perfect place for a family home, a vacation retreat, rental or investment property. Explore the homes below, then give Bassette Real Estate Group a call at 802-457-2244. Our agents and buyer brokers would love to help you find your perfect new home in Woodstock.

25 The Lane, Woodstock, VT 05091

Price$999,999

Est. Mortgage: $/month

MLS Number 4663484

  • Residential Single Family
  • Listing Agent Name Keri Cole
  • Construction Existing
  • Bathroom 6
  • Bedrooms 4

EXCEPTIONAL 14 ACRE PROPERTY, MINUTES FROM WOODSTOCK VILLAGE. Beautifully constructed with custom details like gorgeous millwork, Brazilian cherry floors, high ceilings, gracious family rooms, and a massive granite fireplace, this spacious home is perfectly equipped to accommodate your family and friends in comfort and luxury. Two ponds, a contemporary barn, an antique barn on a fieldstone foundation, an open-air cottage, an automatic generator, an oversized two-car garage, and a finished lower-level family room make this home the perfectly equipped Vermont retreat. A screened breakfast room opens off the gourmet kitchen, and a generously proportioned mahogany-floored porch runs the length of the house - the ideal spot for breezy summer days spent admiring the views to Killington. The first-floor master suite offers his and hers walk-in closets, a steam shower, and a claw-foot tub, and each of the three ample guest bedrooms enjoys an en suite bath. This home checks all the boxes!

Listed by Keri Cole, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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20 RIVER STREET, Woodstock, VT 05091

Price$995,000

Est. Mortgage: $/month

MLS Number 4707913

  • Residential Single Family
  • Listing Agent Name Laird Bradley
  • Village Woodstock
  • Construction Existing
  • Bathroom 4

A superbly renovated FEDERAL-STYLE FARMHOUSE sited overlooking a sloping lawn fronting on a tranquil stretch of the Ottauquechee River. Viewed from River Street, the front porch retains the appearance of the long time configueration as a 'twin home', before the two sides were graciously reconnected in a return to the original design and layout. The floor plan features spacious main level rooms with Master Suite, Eat-in-Country kitchen, living-dining room a secluded study and wonderful 'river room'. The second floor offers 4 bedrooms and two mirrored bathrooms. Privately situated and tastefully landscaped with native plants and shrubs. A classic Village home within walking distance of all popular amenities and activities.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2 Carlton Hill Road, Woodstock, VT 05091

Price$995,000

Est. Mortgage: $/month

MLS Number 4717944

  • Residential Single Family
  • Listing Agent Name John Bassette
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3

Own the fabulous Carlton Reservoir as your own swimming, fishing, and boating pond. Fantastic location with additional building lot for boat house, guest house, artist studio, or caretakers house. Beautiful stone walls, flat level building lot, and awesome zipline on approximately 10 acres of land and pond. Just around the corner is the fully renovated 3 bedroom/2.5 bath 3,165 sq. ft. contemporary cape with an additional finished 864 sq. ft. private media room for "wide screen TV movie nights". The house sits on an additional 13.75 acres. There is over 4,800 sq. ft. of heated space for living and home projects! The house enjoys magnificent views of rolling meadows and the hills of Marsh Billings Rockefeller National Park. There is a newly built GeoBarn with a custom workshop and private media room with high end finishes in both flooring and extra touches. We even have a tree house for the "kid". There is a spacious three car garage close to the home & lovely landscaped grounds make this home a beautiful place to escape from the hustle and bustle of life. An excellent opportunity to develop a family compound, vacation retreat, or handsome estate. Own you own little corner of heaven! Four minutes to WUHS, seven to downtown Woodstock, and 20 minutes to Killington. An ideal location for family or a vacation retreat. For full details on the home or to purchase the home with a smaller piece of land (without the pond), see MLS #4717399 at 76 Grove Hill Road, Woodstock.

Listed by John Bassette, Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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739 Westerdale Road, Woodstock, VT 05091

Price$995,000

Est. Mortgage: $/month

MLS Number 4728514

  • Residential Single Family
  • Listing Agent Name Richard Higgerson
  • Construction Existing
  • Bathroom 5
  • Bedrooms 4

Constructed in 2003, this custom home on just under 11 acres of beautifully manicured land was designed with the vernacular architectural style of Vermont barns in mind and enjoys a location that is convenient to Woodstock Village and nearby Killington and Okemo ski resorts. The center of the open interior floor plan house is a magnificent Great Room with oversized windows, high ceilings, cherry floors and a granite hearth with gas stove. The Great Room opens onto a mahogany deck that overlooks established perennial gardens, stonewalls, a brook fed pond stocked with trout and mountain views to the south. A chef's kitchen with granite counters, cherry cabinetry, a generous center island work space and stainless appliances opens onto an inviting south facing sunroom with a vaulted ceiling and oversized windows. Three bedrooms and two baths on the second floor long with 1600 sqft of additional space ready for finish in the lower level & heated, attached, direct entry 3 car garage.

Listed by Richard Higgerson, Four Seasons Sotheby's Int'l Realty

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$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1040 Dunham Hill Road, Woodstock, VT 05091

Price$990,000

Est. Mortgage: $/month

MLS Number 4705269

  • Residential Single Family
  • Listing Agent Name John Bassette
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4

Incredible, breath-taking views of Killington and the Green Mountains from every room in this home. Every detail of this custom built Post and Beam masterpiece was carefully thought through by the owner/builder, a timber frame master craftsman. With an open floor plan, the main level of this magnificent home has a fabulous well equipped chef's kitchen with energy efficient appliances, plenty of cupboards for storage, a lovely dining space, and an expansive Great Room with field stone fireplace and soaring cathedral ceilings. The first floor master bedroom suite has spectacular views from its own private deck, cathedral ceilings, and master bath with walk-in shower, soaking tub, and double sinks. Two large second floor bedrooms provide plenty of space for a growing family, or hosting family and friends. The mostly finished basement is waiting for your finishing touches and pricing includes a generous allowance to wrap up the details and flooring choices. Top quality materials throughout this home with advanced systems and radiant heat. Separated from the main living spaces by a generous mudroom/laundry area, is a finished and over-sized 2 car garage to complete the package. A fantastic opportunity to enjoy the beautiful Vermont scenery only 2-3 minutes to the Fitness Center and 5 minutes to Woodstock Village. A great place to enjoy Vermont as a vacation retreat. Come see what this impressive home has to offer!

Listed by John Bassette, Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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5 Church Street, Woodstock, VT 05091

Price$945,000

Est. Mortgage: $/month

MLS Number 4698660

  • Residential Single Family
  • Listing Agent Name Keri Cole
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4

EXTRAORDINARY RIVERFRONT HOME IN WOODSTOCK VILLAGE! Incomparably situated on nearly an acre of gorgeous lawns with direct river access and views of Mt. Tom, this historic village home has been impeccably updated and maintained. An open and airy kitchen boasts a gorgeous La Cornue range and a new Sub-Zero refrigerator - ideal for entertaining. Central air conditioning, a generator, and a new standing-seam roof make the antique home comfortable in every season. Large upstairs room provides flexible space for guest accommodation, a home office, or a play room. Walk to everything in New England's most beautiful village from this matchless Woodstock home.

Listed by Keri Cole, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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4662 Cloudland Road, Woodstock, VT 05091

Price$945,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4709960

  • Residential Single Family
  • Listing Agent Name John Snyder
  • Construction Existing
  • Bathroom 5
  • Bedrooms 4

Premier location, location, location - on Cloudland Road just up from River Road and a pleasant walk to Billings Farm and downtown Woodstock for amazing bike riding, walking, and running right out the door. Privately situated in a well-landscaped setting is this immaculately maintained newer construction 3,154 sf 3 bedroom cape with vaulted ceiling mini-great room open to lovely gourmet kitchen with custom-made cherry cabinets. A charming dining area is next to kitchen. Half bath and mudroom at entrance. 1st level MBR with ensuite bath, two bedrooms a sitting room and full bath upstairs. Partially finished basement has a workout/TV area and office. Just across the driveway from the cape is a barn-garage with two bays of garage with overhead doors, a third covered bay for vehicles and equipment, and upstairs is a 1,298 sf fully finished in-law apartment with vaulted ceiling, kitchen, bath, dining, sitting area and bedroom with ensuite bath - all with its own entrance and two-level private deck area. Property has a brook flowing through it and is well landscaped with stonewalls, a charming patio, flower gardens and a garden shed with chicken coop. Excellent mechanicals in both buildings. Beautifully maintained, privately and peacefully sited on approximately 5 acres - exceptionally located less than three mins from the Village of Woodstock. This one is all about move-in-ready, and location location location.

Listed by John Snyder and Andrew Holson, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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18 Pleasant St, Woodstock, VT 05091

Price$895,000

Est. Mortgage: $/month

MLS Number 4700852

  • Residential Single Family
  • Listing Agent Name Danny Kogut
  • Construction Existing
  • Bathroom 3
  • Bedrooms 5

The Historic Eaton House is surrounded by a wealth of beautiful period homes in the heart of Woodstock's Historic District. This c1840 Greek Revival inspired home is on a .55 acre village parcel with a long, level manicured lawn fronting the Kedron Brook. The spacious bright rooms flow seamlessly for entertaining and daily living. The home has been thoughtfully stewarded over the years maintaining the period detail with quality updates and custom built-ins to accommodate modern living. Front and rear staircases access the five+ spacious bedrooms on the second level. The well proportioned living room features a wood burning fireplace. The formal dining room has lovely built- in china cabinets flanking french doors. The private outdoor deck is perfect for summer entertaining and relaxation. Attached 2 car garage. Top quality updated systems. Just a short stroll to the Outtauquechee River, and within blocks of shops, restaurants and all village amenities.

Listed by Danny Kogut, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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125 Hoadley Road, Woodstock, VT 05091

Price$885,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4631074

  • Residential Single Family
  • Listing Agent Name Carol Wood
  • Construction Existing
  • Bathroom 4
  • Bedrooms 3

A handsome timber frame house situated on 78 acres of open and wooded land protected by conservation easement., designed to take advantage of privacy,quiet, an overflowing spring-fed pond and year round brook. Splendid solar exposure for great natural light .Living Room/Dining Room and Kitchen all open to each other and provide wonderful access to 4 decks opening to the pond, brook, and lovely perennial gardens. Kitchen features high quality appliances , custom cherry cabinets, with island/bar to provide a great gathering space while cooking and entertaining. Main level bedroom with bath , spectacular 2nd level master suite with cathedral ceiling, sitting room, balcony, walk-in closets and luxurious bath. Lower level consists of bedroom suite with sitting room and kitchenette. Exceptional grounds include trails for hiking, horseback riding, 24x28 barn could easily accommodate horses for this property which is in the center of the spectacular Green Mt. Horse Assoc. trail system. Just a short stroll to the village of South Woodstock and a 5 minute drive to the Woodstock Green. Convenient to skiing, spa, fitness center and recreation.

Listed by Carol Wood, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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694 CHURCH HILL ROAD, Woodstock, VT 05091

Price$865,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4725559

  • Residential Single Family
  • Listing Agent Name Laird Bradley
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4

This Mid-20th Century Contemporary residence with an attached Guest Cottage is refined, sophisticated and filled with light having been renovated to a high standard of fit & finish. The kitchen is a true cook's environment with thoughtful attention to every detail. The space elegantly blends form and function yielding a work of art. Inspired minimalist landscaping surrounds a wide deck accented with built-in seating and a field stone fire-pit. The covered outdoor's kitchen invites entertaining in all seasons. The gracious home is sited on nearly 10 acres of private land with a woodland pond. The rural setting is located less than a mile from Woodstock Village and all resort amenities offering seclusion without isolation.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2876 Hartland Hill Road, Woodstock, VT 05091

MLS Number 4721296

  • Residential Single Family
  • Listing Agent Name Christopher Lang
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4

Classic Vermont farmstead featuring "big house-little house-back house-barn" architecture located on Hartland Hill 1.4 miles from the Village of Woodstock. Ideally suited for equestrian purposes or other types of farm animals. The house, built in 1807 using hand-hewn timber frames, has four bedrooms, three bathrooms, a living room, family room, dining room & kitchen. Features include exposed beams, original wide-pine floors and a field-stone fireplace. The attached 47' x 48' post & beam barn, one of the nicest in Woodstock, includes a half-court basketball court, large hayloft, central parking bay, grain room, two stock yards, five box stalls and exterior paddock. Four-bedroom mound septic system installed Nov, 2009. Multiple upgrades to house in the past 5 years including new windows, new standing seam roof, rebuilt chimneys, new oil tanks, new exterior deck, fencing and new barn lighting. Conveniently located on the east side of Woodstock with quick access via Happy Valley Road to points east including Dartmouth College and Hanover, NH. The current owner is the sister of the listing broker.

Listed by Christopher Lang, LandVest, Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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76 Grove Hill Road, Woodstock, VT 05091

Price$755,000

Est. Mortgage: $/month

MLS Number 4717399

  • Residential Single Family
  • Listing Agent Name John Bassette
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3

DESIRABLE NEIGHBORHOOD! Fully renovated 3 bedroom/2.5 bath 3,165 sq ft contemporary cape with an additional finished 864 sq ft private media room for "wide screen TV movie nights". There is over 4,800 sqft of heated space for living and home projects! The house enjoys magnificent views of rolling meadows and the hills of Marsh Billings Rockefeller National Park. There is a newly built GeoBarn with a custom workshop and private media room with high end finishes in both flooring and extra touches. There are numerous home living spaces (Craft Room, (2) Family Rooms, Living Room, Media Room, Office, & Dining Room). The modern 2004 kitchen renovation has plenty of cupboards for storage and there are newer 2013 Kitchen Aid appliances. There is a private master bedroom suite with built-in double closets, air conditioning, and a newly redone tiled master bath. Two additional bedrooms with hardwood floors share a common bath. The large family room has a gracious fireplace (and woodstove) to stay warm and cozy during those cold winter months. Lovely private porch and patio can accommodate large gatherings to enjoy the views as you eat a relaxing meal. We even have a tree house for the "kid". There is a spacious three car garage close to the home & lovely landscaped grounds make this home a beautiful place to retreat from the hustle and bustle of life. Four minutes to WUHS, seven to downtown Woodstock, and 20 minutes to Killington. An ideal location for family or a vacation retreat.

Listed by John Bassette, Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 4.63% last updated on Dec 13, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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