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

57 River Street Woodstock VT 05091

Woodstock, VT57 River Street

Price$995,000

Est. Mortgage: $/month

MLS Number 4791575

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 2,075

Get away from the crowds. A beautiful home in a very prestigious town. Known as "The Prettiest Small Town in America" a Rockefeller town, renowned for it's rich history. This house has been renovated from top to bottom; filled with light, creating a happy and peaceful atmosphere. Steam shower. Move in ready. This house is also available with designated furnishings.Theater and Health Club, including a Rockefeller golf course are located in town. 20 minutes to Killington, Okemo, Dartmouth College and Hospital. A fabulous sauna in separate out building.

Listed by Dorothea Mongulla, High End Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 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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2525 Barnard Road Woodstock VT 05091

Woodstock, VT2525 Barnard Road

Price$850,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4807367

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 3,552

Classic Civil War era farmhouse thoughtfully and comprehensively renovated with modern mechanical systems, including installation of radiant heat in the main living level. The home enjoys wonderful natural light in all seasons. A flexible use floor plan consists of an eat-in Country Kitchen. spacious family room with field-stone fireplace, a study that is used periodically as a bedroom and a double living room with pellet stove. A winding stairway ascends to the second with 3 bedrooms sharing an enormous bathroom with laundry. The third floor attic has been repurposed as a master bedroom sanctuary. On summer nights the northerly windows can open to allow the sounds of water cascading in the boundary brook and lull you to sleep. Located north of Woodstock Village, the property is within walking distance of the Marsh-Billings-Rockefeller National Park, VAST corridor and a network of trails at the end of Grassy Lane that wander through hundreds of acres of unspoiled rural land. Horse barn, pond and two active brooks. Paddocks and open pasture invite agricultural activities. Barn mounted solar array is net metered to reduce or eliminate electrical expenses.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 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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509 Darling Road Woodstock VT 05071

Woodstock, VT509 Darling Road

Price$795,000

Est. Mortgage: $/month

Pending

MLS Number 4811921

  • Residential Single Family
  • Construction Existing
  • Bathroom 1
  • Bedrooms 3
  • Square Feet 1,008

A very rare opportunity to own 60 acres of land with total privacy and majestic long range views that include Mt. Ascutney all the way to Mt. Sunapee. The land is bordered by protected land so there will be no development that will be seen from the house sites . 40 Acres are in the Current Use Program with a 2 acre house site exemption. There is a large spring fed pond accessed by a path through the woods. Darling Road is a dead end road so one is assured of a very quiet , peaceful setting . The cabin is very cozy with a large screened porch and deck. Access to Woodstock and South Woodstock are less than 15 minutes away and Skiing at Okemo and Killington are 40 minutes away. All types of sports for every season are readily available . This is truly a SPECIAL property !

Listed by Carol Wood, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 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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492 Westerdale Road Woodstock VT 05091

Woodstock, VT492 Westerdale Road

Price$775,000

Est. Mortgage: $/month

MLS Number 4810501

  • 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: 2.88% last updated on Aug 6, 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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5070 South Road Woodstock VT 05071

Woodstock, VT5070 South Road

Price$700,000

Est. Mortgage: $/month

MLS Number 4771226

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 3
  • Square Feet 2,800

Completely renovated antique cape located in the historic village of South Woodstock . This classic cape dating to 1850 is being totally renovated with state of the art new kitchen, downstairs master bedroom with new bathroom. Upstairs two bedrooms with new shared bathroom. Open floor plan living room/dining room with french doors leading out to a very private well landscaped back garden/lawn. A special opportunity to own an antique home with all new systems .

Listed by Carol Wood, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 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
Active With Contract

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 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 4812129

  • 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: 2.88% last updated on Aug 6, 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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12 Cross Street Woodstock VT 05091

Woodstock, VT12 Cross Street

Price$675,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4816619

  • Residential Single Family
  • Village Woodstock
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4

12 Cross Street is a beautifully maintained and recently renovated historic residence located in the heart of Woodstock village, with much of the original woodwork, floors and doors and slate roof - as they were in 1905. Yet the residence has recently been thoroughly renovated to today's standards for insulation, heating, windows, kitchen and bathrooms. The first floor boasts a newer kitchen, breakfast area and walk-in pantry, mud room entry, formal dining room, living room, den, and first floor bedroom with half-bath. Upstairs are three bedrooms including a generously-sized master, with two newly-renovated full baths complete with radiant heat. Each upstairs bedroom has its own newer heat pump for heating and air conditioning. The current owners had an energy audit conducted and insulated all exterior walls and attic, and replaced windows and furnace - so the house is now “Energy Star” certified. Beautifully landscaped with a mix of gardens, lawn, a traditional covered porch, and a gorgeous stone patio to enjoy the sights and sounds of village life and entertain friends and family. A detached two-car garage/barn provides parking and ample room for storage, plus the driveway has room for 2-4 more cars, a bonus in the village! 12 Cross Street is sited along the lovely flowing Kedron Brook. The property is within walking distance of the Woodstock Inn & Resort, Woodstock Elementary School, and all the shops, restaurants, and amenities the Village has to offer.

Listed by John Snyder, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 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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2 Swain Street Woodstock VT 05091

Woodstock, VT2 Swain Street

Price$675,000

Est. Mortgage: $/month

Pending

MLS Number 4814534

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 2,414

Turnkey treasure privately located on a dead-end street in the heart of Woodstock Village! This contemporary colonial offers the right blend of an open concept function and flow interior and exterior space. The main level design is a wonderful composition of lofted ceilings, exposed beams, and hardwood floors that detail the living/dining area and superbly renovated custom kitchen which all access the lovely landscaped stone patio and deck. A master bedroom suite and nifty loft space with en-suite bedroom finish off the intelligent main level design. The lower level with slate tiled entryway includes a third en-suite bedroom, family room/bedroom, and mudroom/laundry room with direct access from the attached garage. Back-up Kohler Generator for peace of mind. Unique and rare opportunity to enjoy both the amenities of the vibrant village life of Woodstock and the quiet and solitude of Vermont living!

Listed by Mary Mayhew, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 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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965 Deer Brook Way Woodstock VT 05091

Woodstock, VT965 Deer Brook Way

Price$665,000

Est. Mortgage: $/month

MLS Number 4807039

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,192

House in the Sun is a perfect gem sited beautifully on 11.5 acres with spectacular long range views, a pristine pond, and forest area with trails and a stream. The cape style house is a tasteful architectural blend of classic Vermont charm and contemporary design. The open concept kitchen/living/dining area that opens to a deck is warm and inviting for gathering and entertaining while taking in the panoramic view. The main level also offers an office/den as well as a bedroom with full bath. The master bedroom suite on the second level is detailed with vaulted ceilings, exposed beams and lovely large windows that capture that view! There are two additional bedrooms and bath on the second level for family and guests. Enjoy all the seasons in Vermont swimming in the pond, exploring the stream, and hiking/snowshoeing the open field and forest paths. Private but conveniently located within minutes to dining, theatre and shopping in Woodstock Village and 15 minutes to Killington Mountain Resort.

Listed by Mary Mayhew, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 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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20 Lincoln Street Woodstock VT 05091

Woodstock, VT20 Lincoln Street

Price$635,000

Est. Mortgage: $/month

MLS Number 4813051

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 2,784

This energy efficient Geo-Barn is within walking distance of Village amenities and sited on a level 'double' lot with views overlooking Mt. Tom and Billings Farm. The open 'post & beam floor plan provides spacious. light-filled gathering rooms on the main floor with two private decks, a separate bedroom and office enabling single level living. Two sunny bedrooms on the second floor and a 'guest space' on the walk-out lower level provide flexibility for larger or smaller space demands with a total finished area of about 2400 sq. ft. There is potential VRBO income from the 'lock-out' lower area. The 'double lot' has been surveyed for subdivision, if desired.

Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 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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84 Barberry Circle Woodstock VT 05091

Woodstock, VT84 Barberry Circle

Price$620,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4807562

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 4
  • Square Feet 1,980

If you are looking for move-in-ready simple modern Vermont farmhouse living in a great neighborhood on a quiet cul-de-sac, this is it. This simple, shaker style home speaks of the modern Vermont farmhouse with a mixture of wonderful interior spaces, lots of light, hardwood floors throughout, open floorplan with updated kitchen that opens to dining room. Kitchen has Bertazzoni range, Bosch dishwasher and Jenn-Air stainless referigerator. Woodstove, propane woodstove in the wonderful 20x24 living room, fireplace in the den/piano room to keep you toasty on snowy Vermont nights. Two beautifully updated baths and four sweet upstairs farmhouse bedrooms. Enjoy the Vermont outdoor lifestyle with a pleasant yard, mature maple trees, raised bed gardens, a garden shed, a fun in-ground swimming pool, an outdoor shower, and a two car attached garage. Plenty of storage in the basement and garden shed for bikes, snowshoes, skis and holiday decorations. This house offers carefree relaxed Vermont living with easy access to the Woodstock Farmers Market, Killington skiing and 4 mins to the Woodstock village green.

Listed by John Snyder, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Aug 6, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

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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 August 10, 2020.