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.

739 Westerdale Road Woodstock VT 05091

Price$995,000

Est. Mortgage: $/month

MLS Number 4753809

  • Residential Single Family
  • Construction Existing
  • Bathroom 6
  • Bedrooms 4
  • Square Feet 3,960

This custom-built residence is privately situated on 10+ acres with lovely mountain views, a stream, woods and pond. The residence - constructed in 2003 - has been beautifully maintained, and is move-in-ready. Designed for one-level living, the 3-car attached heated garage walks into the main level complete with beautiful, open floorplan, cherry floors, a large gourmet kitchen, lots of light and windows, a lovely sunroom, a unique circular room that leads into the large 1st level master bedroom suite with walk-in closets, large bath area and it's own private office and balcony. There are 3 additional bedrooms and 2 baths upstairs (with expansion framed & ready both above the garage and in the lower level). Extensive landscaping and stone walls. A lovely stream and pond on the property can be viewed and heard from the master bedroom balcony. Superb mechanicals with top-of-the-line Viesmann radiant heating system, whole-house automatic backup generator, security/fire system, central AC in the upstairs bedrooms. If you are seeking a beautifully built and maintained residence, privately situated in an area of substantial homes just minutes to the Village Green, this is a must see.

Listed by John Snyder, Snyder Donegan Real Estate Group

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$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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
  • Village Woodstock
  • Construction Existing
  • Bathroom 4
  • Bedrooms 5

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: 3.75% last updated on Jul 11, 2019
* 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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3057 Church Hill Road Woodstock VT 05091

Price$950,000

Est. Mortgage: $/month

MLS Number 4758738

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 3
  • Square Feet 1,920

Privately sited in Woodstock, Vermont with long range views of Killington Peak, is this custom built 3-bedroom 3-bathroom timber-frame home with detached garage. Inside the spaces are warm and inviting, perfectly designed for Vermont's 4-season lifestyle. A wood-burning fieldstone fireplace with raised hearth on one-side and a Scandinavian woodstove on the other, is a central feature. On the south side of the fireplace is the kitchen and dining area with French doors that lead to a stone patio with views of Killington. On the other side, is a great room with stair case to the second floor. On the east side of the first floor is the master bedroom suite with private bath, a mud room entry hall and powder room. Upstairs there are two bedrooms each with French doors that open to a private balcony, one on the east side overlooking landscaped flower gardens; the other looking west across cascading ridgelines to Killington. In between the bedrooms is a full bathroom. Below grade is an unfinished basement with high ceilings, interior stairwell and exterior bulkhead. Next to the house is the 2-car garage with utility room. Upstairs is 350 square feet of additional living space with electric heat and a ¾ bathroom. Outside, there are beautifully laid stone walls, steps and terraces interspersed with plantings, shrubs and perennials. Located 3 miles from the Woodstock village green and 1.5 miles from the South Woodstock Country Store, this is a special turn-key offering.

Listed by Christopher Lang, LandVest, Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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 Watkins Way Woodstock VT 05091

Price$939,000

Est. Mortgage: $/month

MLS Number 4761952

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 3,688

Watkins House was built in 1868 on a prominent knoll to overlook the Ottauquechee River Valley and Mt. Tom, this classic colonial enjoys a wonderful view over Woodstock Village. Spacious in size and room proportion this 3,688 square foot home was completely renovated in 2018 by award winning builder for easy comfort and function, and includes a porch addition to capture the view and hillside breezes, total renovation of attached working barn with converted second floor to a one bedroom quest suite with kitchen, state of the art kitchen in main house, hidden magnolia surround sound entertainment system in Living room, with the most spectacular 3rd floor Master Bedroom/Spa with best Village views. Situated on a surprisingly generous .66-acre village parcel with level areas for gardens, beautiful stone patio, within walking to the Village center with its abundant amenities. Quite close to Mt. Peg Park access for hiking trails, and only slightly further to the amazing trail system of Mt. Tom/Marsh Billings Rockefeller Historical Park, additional recreational opportunities abound with Woodstock Country Club for golf, mountain biking, cross country skiing; Woodstock Health and Fitness Center for swimming, exercise facilities, Killington, Okemo, and historical Suicide ski and Mountain bike park, are all within an easy drive away. Seller/Owner is a Licensed Sales Agent in VT.

Listed by John King, eXp Realty LLC

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$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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$899,000

Est. Mortgage: $/month

MLS Number 4698660

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,909

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

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$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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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1034 Dunham Hill Road Woodstock VT 05091

Price$899,000

Est. Mortgage: $/month

MLS Number 4757632

  • Residential Single Family
  • Village Woodstock
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4

Breathtaking views of mountains near and far greet you from every room in this sun-soaked, master builder's home. Located 2 minutes from the heart of Woodstock, this wooded property offers peace and privacy. The chef's kitchen boasts top-of-the-line stainless steel appliances. The open floor plan creates the perfect setting for large parties or you can settle down for some quiet time in front of the stunning fieldstone fireplace. The generously-sized deck and rolling lawns offer the perfect venues for outdoor entertaining. The first floor master bedroom suite has a luxurious bathroom and deck. The nearly-finished basement is a great space for an exercise room and a bonus room for the rowdy crowd. This home is a one-of-a-kind, must-see.

Listed by Jennifer Falvey, Snyder Donegan Real Estate Group

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$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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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6 Mountain Avenue Woodstock VT 05091

Price$749,500

Est. Mortgage: $/month

Pending

MLS Number 4754581

  • Residential Single Family
  • Village Woodstock
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3

This is a one-of-a-kind, in-town, immaculate, turn-key, charmer on a corner lot within view of Woodstock's historical covered bridge, in the highly desirable Mountain Avenue neighborhood.. The interior of this elegant home has been renovated with impeccable taste. The property has been designed and maintained by an award-winning, master gardener. This sun-filled home is a delightful marriage of antique charm and contemporary convenience. The wrap around porch and lovely gardens offer opportunities for outdoor entertaining. The open-kitchen and roomy dining area offer the perfect venue for indoor entertainment. The original barn has been converted into a two car garage with storage above. This home is a stone's throw from the Woodstock Green in one direction and Billing's National Park in the other. Hike up Mount Tom during the day and stroll to dinner in the evening.

Listed by Jennifer Falvey, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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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661 Deer Brook Way Woodstock VT 05091

Price$730,000

Est. Mortgage: $/month

MLS Number 4764089

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3,912

The whole package - private, extremely well-maintained and thoughtfully designed house, mountain view, and an incredible swimming pond - with convenient access to the village of Woodstock and Killington Mountain Resort. The multiple spring-fed swimming pond is truly exceptional with several docks for lounging, a diving board, and a screened-in cabana for dinner parties as well as a small room for changing into swim attire. The remaining ~13-acre land component is nicely landscaped with open space for recreation and a walking trail that leads to a brook. Entering the house, a spacious and bright mudroom connects the 2-car attached garage to the main living space. The chef's kitchen with walk-in pantry is well oriented to take in the view and connects seamlessly to the adjacent living space - with a sliding glass door that opens to an expansive deck. A formal entry, dining room, living room and half bath complete the first level. The master bedroom with bathroom is very private and features ample closet space, its own deck overlooking the pond and view, and a skylight that is positioned to gaze up at the stars at night. Three other bedrooms are also located on the second level. The finished walkout basement receives plenty of light and is currently setup as a den/bar and game room, with a ¾ bathroom, workshop, and hot tub room. Solid mechanicals include central AC, a separate air conditioning wall unit in the master bedroom, and a generator hook up.

Listed by Andrew Holson, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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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28 The Green Street Woodstock VT 05091

Price$699,000

Est. Mortgage: $/month

MLS Number 4698305

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,037

An elegantly proportioned brick townhouse, of genteel style and character, situated on the picturesque Woodstock Village Green! A gracious 3 story interior, with attractive antique detailing, 9 foot high ceilings, exposed beams, wood floors and multiple fireplaces. On the ground floor is the kitchen, a dining room with fireplace, a living room with fireplace, a classic entry hall and a half bath. On the second floor is a great room with fireplace, 2 bedrooms and a full bath. On the third floor is the primary bedroom suite, with walk-in closet and full bath. The front exterior of the residence features a formal covered entry. The rear exterior of the residence features an elevated brick patio. An useful amenity is off street parking. There is additional parking and storage in a detached garage. An opportunity to acquire a charming village townhouse residence, ideally located on the Woodstock Village Green!

Listed by John Wetmore, William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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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492 Westerdale Road Woodstock VT 05091

Price$699,000

Est. Mortgage: $/month

MLS Number 4721629

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3,349

This exciting property offers 4 bedrooms, 3.5 baths, and is a scant 3 miles to Woodstock village and minutes to skiing. There is a two-stall horse barn with fenced pasture on this 5.2 acre level lot with power, water, and insulated tack room abutting riding/walking trails. This home features easy transitions between indoor and outdoor spaces and is perfect for entertaining: a screened lounge, country porch, patios and decks surround an in-ground pool. Professional landscaping has maintained the mature perennial beds. The spacious master bedroom takes full advantage of the beautiful pastoral view and has a Jacuzzi tub and walk-in closet. The generous, yet cozy, family room has a fireplace, pine floors and natural light from the many windows. The efficient kitchen has dual ovens & stone counter tops. Plenty of storage throughout, plus mudroom with laundry. Work from home? The detached two car garage has a heated office with separate entrance, plus a workshop. Built in 1981 with addition/renovations 1996. Broker owned.

Listed by Geoff Eckler, Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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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271 Gabert Road Woodstock VT 05091

Price$695,000

Est. Mortgage: $/month

MLS Number 4753233

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 3
  • Square Feet 4,480

Enjoy stunning views from this gracious, private country home. The open floor plan affords easy flow for entertaining. The large windows take in the distant views as well as the beautifully landscaped grounds, gardens and pond. The main level includes large living room with fireplace, dining room with balcony, gourmet kitchen with custom cherry cabinets , bedroom and bath large, laundry and 2 car attached garage. The master suite includes bedroom with balcony, private sitting room that could be used as a nursery, office, and spacious his and her master bath. Lower level has 30x15 family room with fireplace as well as bedroom with bath. There is a generator and for year round comfort, air conditioning. Large closets, lots of storage and generous proportioned rooms filled with lots of sunlight as the house is oriented to the South. The property has the possibility of another homesite. Minutes to historic Woodstock and all of its amenities . Close to Killington and world class skiing. This is truly a very special property !

Listed by Carol Wood and Gretchjen Smith, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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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353 Cabot Road Woodstock VT 05091

Price$695,000

Est. Mortgage: $/month

MLS Number 4737344

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 3,542

A very comfortable Woodstock home, beautifully sited, on 18 acres, to enjoy long views and substantial sun light! The practical floor plan features a primary bedroom suite, with ensuite bath and walk in closet, on the first floor. For convenience, in Winter weather, direct access from an oversize garage leads into a long mud room. The living room is designed for entertaining! This central gathering area is anchored on one end, by a dramatic stone fireplace, features wood beams overhead, and ever changing pastoral views over a large open field, toward distant hills. The first floor is completed with a view oriented dining room, a well designed kitchen and a formal entry foyer. On the second floor are 3 bedrooms, full bath and a den. A full basement provides multiple areas for workshop space and has a fully finished office space, with a private walk out entrance. An inground swimming pool provides Summer entertainment. The diverse land is comprised of both acres of open land and a sugarbush with a sugarhouse structure. A beloved family homestead that is waiting for its next generation of occupants.

Listed by John Wetmore, William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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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Copyright 2019 New England Real Estate Network, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this web site comes in part from the IDX Program of NEREN. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated July 17, 2019.