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.

153 Ribbett Way, Woodstock, VT 05091

Price$695,000

Est. Mortgage: $/month

MLS Number 4719234

  • Residential Single Family
  • Listing Agent Name Keri Cole
  • Construction Existing
  • Bathroom 2
  • Bedrooms 4

Wonderful Private Retreat - Minutes from Woodstock Village! Sunny and magical, this Ken Mackenzie-designed four-bedroom home enjoys southerly views across open meadows, a spring-fed swimming pond, and year-round stream. Well situated on 16 acres, the three-level main house offers stunning custom-cut cherry floors, a marble and stainless kitchen with gourmet appliances, and gorgeously updated bathrooms - making this home a joy for living and entertaining. An expansive deck brings the outdoors in, and open-concept living spaces are made cozy with reclaimed architectural elements, a specially commissioned Barbara Kaufman ceramic hearth, and artisanal built-in cabinetry. Owned by the same family for 38 years, this Woodstock property will delight you with its tranquil end-of-road privacy and enchanting architecture.

Listed by Keri Cole, Williamson Group Sotheby's International Realty

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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

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$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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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4946 South Road, Woodstock, VT 05071

Price$649,000

Est. Mortgage: $/month

MLS Number 4716050

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

Enjoy the very best of Vermont Village life in this gracious, fully restored c1854 Greek Revival home in the lovely hamlet of South Woodstock. There are 4 bedrooms in the main house with a spectacular 1 bedroom attached in-law apt for overflow guests, or a great income source. The expansive, level lawn with mature landscaping is perfect for entertaining. There's a charming period barn and antique stone walls behind. Just a short stroll to the Kedron Valley Inn, South Woodstock General Store, Post Office. Cross the road to access the Kedron Brook and miles and miles of trails for hiking. Green Mountain Horse Association is a half mile away. Five miles to the Woodstock Village Green and all it's amenities. This is a perfect location to enjoy all that Vermont has to offer !

Listed by Carol Wood, Williamson Group Sotheby's International Realty

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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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34 Mountain Avenue, Woodstock, VT 05091

Price$535,000

Est. Mortgage: $/month

MLS Number 4715214

  • Residential Single Family
  • Listing Agent Name Tambrey Vutech
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4

This lovely village home is located on a spacious corner lot, just steps from Faulkner Park,at the foot of Mt. Tom, on beautiful Mountain Ave.Rooms are generously sized and updated while retaining all of the charm and features of this antique home.Gleaming hardwood floors,built-in china cupboard in DR,custom library shelving and cabinets in the den & ample storage on all floors.The eat-in kitchen is comfortable for sharing a meal and opens onto a sunny deck in back,or a perfect covered porch which faces the Ottauquechee River & the historic stone building known as The Little Theater.The Living Room has a large seating area in front of the wood-burning fireplace,perfect for warming up on a chilly evening.Master BR suite with dressing table and full bath and a 2nd BR and full bath complete the second floor.The sunny 3rd floor has 2 BR w/built-ins and a 1/2 bath.Many happy memories have been made here over the years,both as a primary & second home.In recent years,a fire alarm system has been installed to allow use as a short-term rental,and FHW heating upgraded to a Buderus system.An easy walk to the trail system into MBR National Park,Billings Farm,shopping,schools,recreation,arts and hiking available in Woodstock Village.Less than an hours drive from several major ski areas and 15 min. or less to Quechee,GMHA,ArtisTree; 30 min. to DHMC & Dartmouth College.A home that offers choice-live here full time or seasonally and rent when desired.A rare find for the price & location!

Listed by Tambrey Vutech, KW Vermont

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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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115 Holt Way, Woodstock, VT 05091

Price$699,999

Est. Mortgage: $/month

MLS Number 4708728

  • Residential Single Family
  • Listing Agent Name Gretchjen Smith
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4

Lovely home situated along a babbling brook with short range views to the West. This property is the last house on a private road and just 3 miles to Woodstock Green. Exceptionally maintained home featuring- open floor concept with generous room proportions, abundance of natural light, wood burning fireplace, handsome kitchen with granite counters. First floor finishes out with formal living room, dining and media area...The family room opens to a generous size deck with firepit adjacent to front yard. Second floor boasts four large bedrooms. The master suite is newly renovated with gas fireplace, beautiful spa-like bathroom and office. A large barn/guest house in unfinished but designed for two bedrooms and single car garage. The property is minutes from Woodstock Resort fitness center, championship golf, fishing, skiing and snowshoeing. Turn key- we invite you to preview this cozy property. Good rental history for buyers interested in an investment property.

Listed by Gretchjen Smith, Williamson Group Sotheby's International Realty

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$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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

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$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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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433 Cowdrey Path Lane, Woodstock, VT 05091

Price$549,500

Est. Mortgage: $/month

Active With Contract

MLS Number 4706824

  • Residential Single Family
  • Listing Agent Name Mary Mayhew
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3

This delightful Cape is idyllically nestled on an open and sunny hillside at the end of a town road and the beginning of a GMHA horse trail and surrounded by conserved land just minutes from the charming village of South Woodstock! The light and airy interior boasts an open concept gourmet kitchen with dining/living area that opens to both a gorgeous screened porch and deck! In addition, there is a warm and spacious family room to gather for fun and games or a movie. The master bedroom ensuite has a stunning vaulted ceiling with exposed beams and a lovely balcony overlooking the backyard. The additional two bedrooms share a full bath. Separate open staircase access to the master bedroom as well as the other bedrooms affords the option for more privacy for overnight guests. An upstairs laundry room is an added convenience. As a bonus there is a splendid Barn-Bunkhouse! The lower level of the barn has parking for one car and an ample storage area for equipment which one could easily convert back to a horse stall. Enjoy the convenience of being just around the corner from South Woodstock General Store, the Kedron Valley Inn, the Green Mountain Horse Association and just a short ride to the village of Woodstock. A truly special and versatile property!

Listed by Mary Mayhew, Snyder Donegan Real Estate Group

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$
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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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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19 Church Street, Woodstock, VT 05091

Price$585,000

Est. Mortgage: $/month

MLS Number 4706460

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

Bright and spacious in-village residence with Ottauquechee River frontage and less than 1-minute walk to the Woodstock Green. Attached 2-car garage and mudroom - built in 2008 - open to the eat-in kitchen with large bay windows, formal dining room, and to the patio. Patio is perfect for entertaining and relaxing in the sun. Master bedroom on the second level is bright and spacious and features an ensuite bath. Two other bedrooms on the second level share a bathroom, and an additional two bedrooms on the third level also share a bathroom. The lower basement level features a finished studio that is bright and open on the walkout side and perfect as an in-law suite or a single/couple tenant. Mechanicals in great order with a new furnace and hot water heater in 2017. Two additional parking spots convey with the property.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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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229 Blankey Cottage Lane, Woodstock, VT 05091

MLS Number 4706007

  • Residential Single Family
  • Listing Agent Name Dan Noble
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3

Best of both worlds!! Located just 1 mile from Woodstock Village, yet on 3.38 private acres at the end of a town maintained road with spectacular views of Killington and Green Mtns. The first floor is handicap accessible and consists of an open kitchen with center island and an eat-in dining area, large living room with stone fire place, beautiful sun room with views and 3 bedrooms. The master suite, with 3/4 bath, has spacious walk-in closets and opens onto the lovely 48 foot deck running along the backside of the house. The two additional bedrooms share a full hallway bath and first floor laundry is close by. First floor also has a mudroom, 1/2 bath and opens into heated 2 car garage. There is a partially finished lower level basement that opens onto the backyard and has a plummed bathroom and extra storage room. Lastly, there is a detached garage/workshop with a second floor for storage or potential living space.

Listed by Dan Noble, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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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858 Cabot Road, Woodstock, VT 05091

Price$549,900

Est. Mortgage: $/month

MLS Number 4705329

  • Residential Single Family
  • Listing Agent Name Andrew Holson
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4

Just minutes from the Woodstock Green, yet privately tucked in the hills with a stunning long-range mountain view, is this handsome and well maintained traditional Center Hall New England Cape. Entire kitchen renovated in 2018. Large open living room with beautiful woodburning fireplace and built-ins opens to a pleasant deck to enjoy the wonderful views. First floor also features a formal dining room, eat-in kitchen, den, and mudroom with direct access to two car garage. Four bedrooms on the second floor, including the master bedroom with ensuite bath. Property features a lovely brook, gracious landscaping and abuts 174 conserved acres. Central Air throughout the house. Wonderful Woodstock location for a primary residence or multi-season vacation home!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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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