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 make 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 Homes for Sale

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: 3.65% last updated on Jan 16, 2020
* 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: 3.65% last updated on Jan 16, 2020
* 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: 3.65% last updated on Jan 16, 2020
* 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

Active With Contract

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: 3.65% last updated on Jan 16, 2020
* 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: 3.65% last updated on Jan 16, 2020
* 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 4786056

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 4,084

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

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$
%
$/month over payments
Federal 30-year interest rate: 3.65% last updated on Jan 16, 2020
* 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$695,000

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: 3.65% last updated on Jan 16, 2020
* 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 immaculate 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: 3.65% last updated on Jan 16, 2020
* 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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6656 South Road Woodstock VT 05071

Woodstock, VT6656 South Road

Price$650,000

Est. Mortgage: $/month

MLS Number 4756440

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 3,031

This classic Antique Cape style Farmhouse is located on the southerly side of South Woodstock across from the Green Mt. Horse Association, with direct access to miles of horse riding trails. The period detail is intact and a handsome timber frame is revealed with 9' ceilings above the spacious living-dining room. The bright, spacious country kitchen is an ideal place for friends and family to gather and enjoy a morning meal. The combination family room and library opens onto a broad patio, lovely gardens and playground.The homestead includes a guest apartment periodically rented, and additional potential for economic or home business use in a separate Vermont-style building with heat, electrical service and 1/2 bath. The historic horse barn with paddocks is 'right sized' for recreational horse activity. Verdant, level fields ideal for pasturing. Perfect opportunity for a "Bed and Board" facility! 6 minutes to the Woodstock Village Green. Close proximity to skiing, hiking, biking and VAST trail system.

Listed by Danny Kogut, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.65% last updated on Jan 16, 2020
* 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

Woodstock, VT28 The Green Street

Price$599,000

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: 3.65% last updated on Jan 16, 2020
* 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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32 The Green Woodstock VT 05091

Woodstock, VT32 The Green

Price$599,000

Est. Mortgage: $/month

MLS Number 4766737

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

Prominently situated, at #32 the Woodstock Village Green, is a circa 1803 traditional style home, with a tastefully renovated contemporary interior! From the covered front porch a resident can enjoy the relaxing pleasure of viewing the beautiful brick Woodstock Town Hall, the impressive neighboring stone church, or the passing activity of village life. From this central location the residents conveniently walk to the numerous Woodstock amenities of shopping, dining and cultural events. The stylish interior living space encompasses 3 levels! The ground floor is entered from either the front porch or through a rear entrance, with a foyer. A more open floor plan features a bright kitchen with adjacent dining area, a comfortable living room, a den, the entry foyer and a 3/4 bath. On the upper floor is the primary bedroom, with en suite full bath, 2 additional bedrooms and a 3/4 bath. The lower level is dedicated to fun! The lower level family room and bar area are either accessed from an interior stairway or through an exterior door that opens to a below street level courtyard. The owners have achieved an impressive history of rental income, with this desirable property!

Listed by John Wetmore, William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.65% last updated on Jan 16, 2020
* 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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4548 West Woodstock Road Woodstock VT 05091
Active With Contract

MLS Number 4767264

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 4,677

"Deer Brook Farm" - Minutes from Woodstock Village and fifteen miles from Killington, this fully restored five-bedroom Colonial Farmhouse with attached two-bedroom apartment sits on nearly five acres, comprising established perennial beds, mature fruit trees, open meadow, and wooded hillside. Steeped in local history, the property was originally known as the Kole Family Farm. The entire home has been expertly restored under the guidance of the current owners, who imbued the period details with a comfortable elegance. The sunny and graciously proportioned rooms are ideal for hosting friends and family with ease, and state of the art systems - including a Buderus boiler and fiber-optic internet - ensure every comfort. The spacious dining room opens onto a private terrace; double French doors lead to a grand living room, complete with a handsome wood-burning fireplace. Each of the five bedrooms boasts an en suite bath and new Mitsubishi heat pumps. The attached two-bedroom, two-bath apartment with private deck is ideal as a long- or short-term rental unit, private guest accommodations, or as an in-law apartment. The post and beam barn can be adapted to support a gentleman's farm, a more formal garage, or a vaulted studio/workshop space. Currently operated as a multi-award-winning hospitality property, Deer Brook Farm offers the uncommon advantages of a traditionally licensed B&B with the additional value of AirBnB-style bookings. Also available fully furnished!

Listed by Danny Kogut and Keri Cole, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.65% last updated on Jan 16, 2020
* 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 2020 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 January 22, 2020.