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 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.

View all Homes for Sale in Woodstock

20 RIVER Street Woodstock VT 05091

Woodstock, VT20 RIVER Street

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: 3.69% last updated on Nov 7, 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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4662 Cloudland Road Woodstock VT 05091

Woodstock, VT4662 Cloudland Road

Price$985,000

Est. Mortgage: $/month

MLS Number 4781136

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 4,452

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, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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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119 English Mills Way Woodstock VT 05091

Woodstock, VT119 English Mills Way

Price$925,000

Est. Mortgage: $/month

MLS Number 4781034

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 4,488

119 English Mills Way is a property you will love to call home. Privately situated on 5.1 acres yet only a short drive to the Village of Woodstock. Well maintained 4 bedroom home with guest or in-law suite in the full walk-out basement. Enjoy the bright and sunny great room with cathedral ceilings, magnificent fireplace and loads of windows. A first floor master suite with Jacuzzi tub is privately located away from the other bedrooms. There are plenty of spaces for all your family gatherings, a lovely kitchen with cherry cabinets opens to a cozy dinning area. The 2nd. floor boast another master bedroom/bath and two additional bedrooms. The exterior is loaded with perennial gardens, walkways and a large wrap around deck. The In-law suite has a full kitchen, 3/4 bath, bedroom, dining room and large walk-out family room along with plenty of storage and much more.

Listed by Gerry Stark and Richard Atherley, RE/MAX Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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

Woodstock, VT1034 Dunham Hill Road

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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

Woodstock, VT5 Church Street

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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

Woodstock, VT3057 Church Hill Road

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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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1782 Barnard Road Woodstock VT 05091

Woodstock, VT1782 Barnard Road

Price$799,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4782792

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 3
  • Square Feet 3,004

EXCEPTIONAL CUSTOM HOME - MINUTES FROM WOODSTOCK! Built in 2015 and expanded in 2017 by Ambrose Custom Builders, this fine family home is ideal for full-time residents or as an easy-keeping vacation property. Perched atop a scenic hillside, the bucolic location belies its easy proximity to Woodstock (1.5 miles), Killington (16 miles), Hanover (20 miles), and the Upper Valley beyond. Gorgeous fits and finishes, an open floor plan, a bunk room, a spacious screened porch, and a media & games room make this home perfect for accommodating and entertaining friends and family with ease. Unique in a marketplace of antique houses, this is a rare opportunity to to purchase a ready-made custom home constructed by one of the area's most reputable and in-demand builders.

Listed by Keri Cole, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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

Woodstock, VT457 Peterkin Hill Road

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: 3.69% last updated on Nov 7, 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

Woodstock, VT5 Linden Hill

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: 3.69% last updated on Nov 7, 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

Woodstock, VT13 RIVER Street

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: 3.69% last updated on Nov 7, 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

Woodstock, VT273 Tilley Way

Price$689,000

Est. Mortgage: $/month

Active With Contract

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: 3.69% last updated on Nov 7, 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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614 Deer Brook Way Woodstock VT 05091

Woodstock, VT614 Deer Brook Way

Price$675,000

Est. Mortgage: $/month

MLS Number 4765815

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 3,368

First time to the Market! Exceptionally maintained contemporary home with an abundance of natural light and views to the south. Nestled in an open field off a private, quiet road. Lovely perennials gardens accented with large stone steps to lower level. This emaculate home has an open floor plan with handsome kitchen with high-end appliances, granite counters and island with second sink, it is adjacent to the dining room with entry to living room with large picture windows and accented with stone faced wood burning fireplace. First floor also contains an year-round sunroom with vaulted ceilings and lots of windows - The entire home feels like nature is at your step with beautiful large windows amplifying nature outdoors. Second floor consists of a large master bedroom suite, generous walk-in closet, vast bathroom with soaking tub for relaxation. The second room to be used as an office or tv room. Lower level was created with privacy in mind- 2 bedrooms with full bathroom, laundry and storage. Both rooms have large windows to take in the wonderful views of open meadow. This property has a 3 story elevator for easy access to entire house, security system and 2 storage closets on exterior. Super location for those looking for skiing at Okemo, Killington/Pico and Suicide Six Ski areas, championship golf, fly-fishing on the Black River, shopping and restaurants 10 minutes away in the heart of historic Woodstock. Turn-key...come take a look!

Listed by Gretchjen Smith, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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 November 12, 2019.