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

Active With Contract

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: 3.56% last updated on Sep 12, 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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 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: 3.56% last updated on Sep 12, 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: 3.56% last updated on Sep 12, 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$899,000

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: 3.56% last updated on Sep 12, 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$800,000

Est. Mortgage: $/month

MLS Number 4758738

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

Rare is the opportunity to buy a custom-built home in pristine condition on 5.59+/- acres with total privacy and long-range views of Killington and Pico in a choice location only 3 miles from the village green and 1.5 miles to the South Woodstock Country Store. Introducing 3057 Church Hill Road: with 3 bedrooms and 3 bathrooms, a ground-floor master suite and a detached 2-car garage with upstairs loft and 3/4 bathroom, this property is not to be missed. Inside the spaces are comfortable and relaxed, perfectly suited for Vermont's 4-season lifestyle. Outside, surrounded by woodlands including a hilltop oasis, there are beautiful landscaped stone walls, steps and terraces softened by shrubs and flower beds, a small stone pool for aquatic plants and several fruit trees. Special features include a two-story fieldstone fireplace with raised hearth on one-side and a Scandinavian woodstove on the other; a mortise and tenon timber frame; a private exterior balcony off each of the 2 upstairs bedrooms; clay tile floors with radiant heat, and the use of French doors and casement windows throughout to take in the views and summer breeze. At just under 2,000 square feet with an additional 350 square feet above the garage, this right-sized home is efficient to heat and maintain while also offering room for expansion with a full unfinished basement, excess storage space upstairs as well as a utility room off the garage.

Listed by Christopher Lang, LandVest, Inc/Woodstock

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$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 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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457 Peterkin Hill Road Woodstock VT 05071

Price$785,000

Est. Mortgage: $/month

MLS Number 4774508

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 2,360

Stunning long range mountain views on nearly 40 acres of mostly open level field/pasture and woods with a stream on a very desirable road with substantial neighboring properties in Woodstock just 11 mins to the Woodstock Green. An authentic three bedroom log cabin with open kitchen-dining-living area and covered porch all look out at the really amazing long-range mountain view. A sun porch, three bedrooms and two baths with a full concrete basement complete the log cabin itself. Nearby is a post-and-beam barn-office space, insulated and heated with overhead door, plus a separate large garden shed for storage of all kinds of outdoor toys, equipment, gardening supplies. The mostly level / gently sloping fields create a big playground, an area for gardens or animals, and/or a second building site with easy access further back on the property, which would also share the stunning long-range mountain view. Very rare opportunity to buy this kind of land and view with a charming and very livable log cabin, with lots of potential for renovations or new construction in a great location in Woodstock at an attractive entry price point.

Listed by John Snyder, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 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 Linden Hill Woodstock VT 05091

Price$725,000

Est. Mortgage: $/month

MLS Number 4772701

  • Residential Single Family
  • Construction Existing
  • Bathroom 7
  • Bedrooms 9
  • Square Feet 4,250

An exceedingly rare opportunity for Woodstock Village: antique 1850's house converted to 4 units in early 1970s and then renovated to a fine functional and aesthetic condition in 2000 while still preserving its 4 unit status. The largest apartment (8 rooms, 4 BR, 3 1/2 BA) occupies three levels of the original house, and enjoys rooms of generous proportion, high level detailing and fixtures, and fine interior finishes. Apartments either side (one of 5 rooms, 2 BR, 1 BA; the other of 3 rooms, 1 BR, 1 BA) have interconnected passage with the main apartment to allow substantial quarters of three discrete spaces for family or friends, or the passages may be closed off for independent use. A 4th apartment (4 rooms, 2 BR, 1 BA) has separate entry off terraced private lawns in the rear. All apartments have private entries, complete kitchens, wood burning fireplaces, separate utility capability, and share use of a generous common parking area. Walk to Village Center and all its many amenities!

Listed by John Snyder, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 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: 3.56% last updated on Sep 12, 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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13 RIVER Street Woodstock VT 05091

Price$698,000

Est. Mortgage: $/month

MLS Number 4774015

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

This historic Woodstock Village home is a short stroll over the Elm Street Bridge from all amenities. The 1850 structure was conceived originally as a 'farm cottage'. The home was restored and re-imagined in a comprehensive renovation in the early 1980's with Arts & Crafts period design elements. Right-sized for today's small house movement the home is beautifully landscaped with a spacious yard providing ample room for outdoor entertaining and gardens. A detached antique barn offers potential for use as a studio or recreational activities. Rare opportunity to own a Village home offering modern systems with delightfully diverse spaces.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 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: 3.56% last updated on Sep 12, 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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273 Tilley Way Woodstock VT 05091

Price$689,000

Est. Mortgage: $/month

MLS Number 4773612

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 3,140

Simple, calm, ready to go in a great location in South Woodstock horse country. The white clapboard home on a quiet shared drive faces west looking over the Kedron Valley and mountains (awesome sunsets). Inside, there is a feeling of tranquility, influenced by the airiness of the rooms and the cohesive palette of neutral paint colors. The 3,140 square foot, c1985, four-bedroom house was renovated in 2018/2019 and is move-in ready. The spacious living room has windows on both ends, a fire place and French doors to the outdoors. Adding to the coziness of the home are fireplaces in the master bedroom and reading room and a fireplace with a woodstove in the breakfast room. The property is stamped with Vermont authenticity as the drive passes over a cattle grate, and through a farmyard and apple orchard before arriving on the hill. Dairy cows can be seen grazing in pastures adjacent to the property. Stone walls and mature trees flank the front of the house. The 10.1-acre property is made up of two 5 acre lots, each with its own well and connected to town sewer. Walking distance to the Upwey Trail system, South Woodstock Country Store and the Kedron Valley Inn. Ideally located as a potential equestrian property in the heart of Woodstock horse country, connecting to hundreds of miles of trails and quiet dirt roads.

Listed by T Story Jenks, LandVest, Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 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 September 18, 2019.