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

Active With Contract

MLS Number 4830925

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,075

Nothing says "Woodstock living" like owning a home that fronts both River Street and Mountain Avenue in the Village! This circa 1826 home is an early example of Woodstock's renowned 19th Century architecture. The classic cape has been lovingly updated while retaining many of its original features. Leave your vehicle near the garage at the Mountain Ave. entrance to the property, walk through the large lawn with raised garden beds, and cross the wide veranda into the kitchen, whose central focus is a brick wood-fired oven in the beehive style. Beautiful cabinetry surrounds the well-appointed space; the floor has radiant heat & the stone countertop is also heated if you wish! An adjoining comfortable den leads into the living room, with wood stove, built-in bookshelves and bay window. A formal dining room with fireplace and renovated first-floor powder room complete the ground floor. Upstairs there are four rooms plus a full bath with tiled shower and soaking tub. The current configuration is two bedrooms, an office, and a storage space that could be an upstairs laundry. Outside, enjoy the shade of the wide covered veranda, allowing for al fresco dining or relaxing on the sofa. This is a rare village property with over-sized lot, allowing for an expansive lawn, garden space and views to Faulkner Park and Mt. Tom. There is ample parking, a one-car garage/tool shed, and an outdoor sauna! Walk to all the Village amenities and enjoy "The Prettiest Small Town in America"!

Listed by Susan Hickey, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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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119 English Mills Way Woodstock VT 05091

Woodstock, VT119 English Mills Way

Price$949,000

Est. Mortgage: $/month

MLS Number 4829245

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

Exquisitely maintained 4-bedroom, 4.5 bath, 4,800 sqft contemporary Saltbox situated on 5.1 acres of lawn and woods just four minutes to Woodstock village. This includes a large and gracious lower level in-law suite/apartment that could double as a home office/business opportunity. There is a magnificent Great Room with floor to ceiling windows for plenty of light and a substantial center fireplace for easy evening conversation. The fabulous large modern kitchen has cherry cabinetry, lots of counter space, and a quaint kitchen office area while the Family/TV room has an attractive Woodstock soapstone stove that comfortably heats the house. Round out the first floor with a practical mudroom, a den, a formal dining room, and milled cherry flooring throughout. Privately located, the first-floor master bedroom en suite boasts a Jacuzzi tub, large walk-in closet, and high ceilings with lots of windows that make the room bright and cheery. The second floor offers a second master bedroom en suite, two additional bedrooms with a common bath, and access to a large storage attic. Outside is a large wrap around deck, a 2 car attached garage, sunny and lovely raised garden beds, perennial gardens framing the brick walkways and deck, and a home located adjacent to Mt Tom's hiking trails - close to Suicide Six ski area. It is just 3-4 minutes to town, and the spacious living area makes this property an ideal family home.

Listed by John Bassette, Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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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1210 Barnard Road Woodstock VT 05091

Woodstock, VT1210 Barnard Road

Price$949,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4825156

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,952

Custom designed and built in 2003, this 3 bedroom home (4 bed septic) on 14.5 acres wows you from the get go. As you wind your way up the driveway, you are greeted by stonework, gardens and a beautiful multi tiered Brazilian IPE Deck (675 sf) that looks out over the Green Mountains and Gilbert's Hill. The contemporary house welcomes you with Granite Masonry and Vermont Slate on the front as well as on the back porch. Inside, the house is bright with an open floor plan. Off the large foyer entry is a lovely den/office with builtin shelves that connects to the extensive master bedroom suite with huge walk-in closet. On the other side of the foyer is the kitchen dining area with Granite counters and a large island. The kitchen leads to a spectacular living room with Cathedral Pine ceilings, a Granite wood burning fireplace and more mountain views. The first floor also boasts a guest bedroom with 3/4 bath, a 1/2 bath, walk-in pantry and a laundry room. Upstairs is a two room loft which includes a great hangout space and a 3rd bedroom. The basement hosts a nice sized mudroom, heated 2 car garage, and ample storage space with "finishing" potential. Less than 2 miles from Woodstock Village and just minutes to skiing, hiking, and the National Park, this location is ideal as a primary or 2nd home getaway.

Listed by Dan Noble, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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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1880 Randall Road Woodstock VT 05091

Woodstock, VT1880 Randall Road

Price$885,000

Est. Mortgage: $/month

Pending

MLS Number 4825894

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,656

With New England ingenuity, this classic white farmhouse was picked up and moved to this lovely site at the end of a driveway off Randall Road and was totally renovated. Tucked on a hillside above a swimming pond that looks over the rolling hills of Woodstock, there is the potential to open the views up further. This four-bedroom, two bath farmhouse offers a comfortable place to stay, room for Zoom calls and close to the amenities of the village of Woodstock. The stone patio in back is great for summer gatherings, a two-bay detached garage has room for skis and gear and there is a tiny cabin down by the pond with a bunkbed.

Listed by T Story Jenks and Dia Jenks, LandVest, Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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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154 Liberty Farm Road Woodstock VT 05091

Woodstock, VT154 Liberty Farm Road

Price$849,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4830954

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,602

The Herdsman House is an updated 1813 New England farmhouse on 5.84 private acres in Woodstock, Vermont. The owners have thoroughly insulated the house and added a 17-kW ground mounted solar array. Power outages are a thing of the past thanks to a Tesla Powerwall. The home runs 100% on site-generated electricity - no utility or heating bills! From the new mudroom with heated Vermont slate floors and a salvaged hemlock bench, to the kitchen with new Sub Zero/Wolf appliances and soapstone counters, the house is warm and welcoming. A dining area and family room with woodstove adjoin the kitchen. A private guest bedroom, custom bathroom with heated floor and large tiled shower, and a living room with wood burning fireplace and built-in cabinetry round out the first floor. Upstairs is a full bath and three bedrooms with plentiful storage/closet space. Out the back door is a 400 square foot Goshen stone patio surrounded by a vintage stone wall, a deer-proof vegetable garden, fruit trees, many established perennial flowerbeds, a seasonal pond, and year-round brook. Above the attached two car garage is more storage space and a heated/air conditioned 300 square foot office. Great for working from home, even when children are remotely learning in the main house! Conveniently located 5 minutes from downtown Woodstock and 15 minutes from the Killington Skyeship Gondola, this is a prime opportunity for a year-round family home or second home getaway!

Listed by John Wetmore, William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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: 2.81% last updated on Oct 29, 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 High Street Woodstock VT 05091

Woodstock, VT12 High Street

Price$725,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4835346

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,423

EXCEPTIONAL VILLAGE PROPERTY! Wonderful opportunity to own a terrific turn-key home in the heart of Woodstock Village. This 3 bedroom home, each with ensuite baths, was designed to enjoy easy access to the vibrant village life of Woodstock with it's wonderful restaurants, shops, arts/theatre, and abundant recreational activities. The open concept main living area is beautifully accented with a gorgeous updated and newly applianced kitchen, hardwood cherry floors, cathedral ceiling, and a picturesque view of Mount Tom and village life! The two additional bedroom suites for family/guests are both ample and private. The backyard and deck are perfect for relaxing, entertaining, and space to garden or take in the village street scape from the front deck. Intelligently designed mechanical systems that include radiant heat, central air, and state of the art Tesla Battery System will keep you comfortable and will give you peace of mind throughout all the seasons. The added bonus of the attached and heated 2 car garage with 4 additional off street village parking spaces makes this truly a unique village property!

Listed by Mary Mayhew, Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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$695,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4771226

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 4
  • 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: 2.81% last updated on Oct 29, 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: 2.81% last updated on Oct 29, 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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16 Lincoln Street Woodstock VT 05091

Woodstock, VT16 Lincoln Street

Price$675,000

Est. Mortgage: $/month

MLS Number 4834696

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,000

Pristine, fully refinished Cape in a desirable location just a short walk to the lovely downtown area of Woodstock. Wood burning fireplace in the living room. all new appliances and granite in the well designed kitchen. 3 bedrooms plus lots of space in the nicely finished lower level. This is a great house. Come take a look.

Listed by Barbara West, Quechee Associates, Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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

Active With Contract

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: 2.81% last updated on Oct 29, 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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45 Pleasant Street Woodstock VT 05091

Woodstock, VT45 Pleasant Street

Price$599,000

Est. Mortgage: $/month

MLS Number 4798290

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,554

Excellent In-Village opportunity. Conveniently located in the East end of Woodstock Village, This well maintained c1900 colonial home, most recently utilized as a suite of law offices can easily be transformed back to a private residence, or a multi family with abiloity to accommodate a home business with excellent street presence, lovely wrap around porch and plenty of parking. Also available for long term commercial lease.

Listed by Danny Kogut and Carol Wood, Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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 October 31, 2020.