Greater Woodstock Area Homes Between $500K and $1 Million

The greater Woodstock, Vermont area (including the towns of Barnard, Bridgewater, Hartland, Pomfret, Reading, West Windsor, and Woodstock) offers diverse real estate opportunities. Whether you’re looking for a historic home, a home in town near shops and galleries and all the amenities you need, a family home, a secluded getaway with lots of land, a vacation home, or investment real estate, the greater Woodstock area has plenty of choices.

Apart from beautiful homes and real estate, the greater Woodstock area of Vermont hosts some great cultural institutions and events like the Hall Art Foundation in Reading, the Woodstock Film Series, and Taste of Woodstock. Summer and winter recreation opportunities abound at Suicide 6 ski area and Mount Ascutney. For horse lovers, the Green Mountain Horse Association (GMHA) in South Woodstock has activities and events all summer long.

Greater Woodstock VT Homes for Sale

The greater Woodstock VT area could be the perfect place for a family home, a vacation retreat, rental property or investment real estate. 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.

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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1606 BRIDGEWATER CENTER Road Bridgewater VT 05035

MLS Number 4766474

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 5
  • Square Feet 4,794

Maple Lane Farm is one of the areas earliest homesteads with land used as a cornfield by a local farmer fronting on the North Branch of the Ottauquechee River. The historic 1790 Cape farmhouse and approximately 130 acres is located across the road in a cluster of historic barns and stonewalled gardens. The property rises to the height of Southgate Mountain, where a rustic cabin was built as a private retreat with sweeping views over the valley south and westerly. The warm patina of time and character remains throughout the home, which has been updated with modern mechanical systems, wiring and plumbing. The town of Bridgewater is midway between Woodstock Village, Killington and Okemo Ski areas, offering a rural experience within close proximity to popular shopping and recreational amenities.

Listed by Laird Bradley, 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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9295 Pomfret Road Pomfret VT 05053

Pomfret, VT9295 Pomfret Road

Price$944,000

Est. Mortgage: $/month

MLS Number 4829953

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 4,584

Own a historic 1809 schoolhouse that has grown into a custom-designed country home. The living room is accented with new hickory floors, plenty of windows, and a brick fireplace with a woodstove. The spacious country kitchen features cathedral ceilings, antique beams, large windows, a grand center butcher block island, and wood cookstove. The ground floor ensuite bedroom boasts a bathroom with a large jetted tile tub, walk-in shower, sauna, and radiant heat. The cozy artistic dining room is wonderfully decored with a life-size chess board mural, and track lighting to set the mood. Relax in the family room with its fireplace, a great place to study, or retreat. The unique upper-level bedrooms are centered around a charming play space and Dutch doors to the individual bedrooms. This home's far side offers two more bedroom spaces and a screened porch to relax and view the heated pool, gardens, and barn. This pool is heated, the yard is fenced, and a barn with storage, room for animals, and an open second-floor recreation space ample for a studio, fitness center, or even indoor basketball. The extensive garden space has an active asparagus patch, raised beds, berry bushes, and plenty of tillable space to grow your choice vegetables. The District Six Schoolhouse is located conveniently within minutes of the Upper Valley and pleasantly accessible to Pomfret/Woodstock. You'll be pleasantly welcomed on your visit of this property and all it has to offer.

Listed by Eric Johnston, Four Seasons Sotheby's Int'l 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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67 Advent Hill Road Hartland VT 05048

Hartland, VT67 Advent Hill Road

Price$925,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4826946

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 4,737

Excellent craftsmanship through out this well maintained post & beam high-ceilinged over-sized cape with magnificent mountain views situated on 19.6 acres of woods and fields in rural Vermont. A quiet peaceful place to escape from the busyness of life with all the amenities of the 21st century. Fabulous modern kitchen with Custom made butternut cabinetry, double wall ovens, newer over-sized Sub-Zero refrigerator, 6 burner gas cook-top, & walk-in pantry to provides plenty of space to prepare gourmet meals. There are extensive hardwood floors & tile throughout the home. The dining space is perfect for intimate dinners or spread out onto the patio to host larger gatherings, taking in the breath-taking mountain views and the cutting garden. Large and spacious, the living room has numerous windows to let in bright natural light and also easy access to the patio through the french doors. The family room has a Vermont Castings woodstove to provide a cozy space to curl up with a good book. There is a Master en-suite downstairs a three more bedrooms upstairs. With two office/studies and hi-speed fiber optic VTel internet, this home lends itself well for a home office or remote learning space for kids. Develop a home theater or exercise room in the finished basement space which also has plenty of storage. More dry storage is available above the two car attached garage & let's not forget the new whole house propane generator. 15 minutes to Woodstock or Quechee. 25-30 minutes to DHMC.

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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27 Graves Road Pomfret VT 05053

Pomfret, VT27 Graves Road

Price$925,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4826146

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,964

Ideally situated on 11 level acres of open and wooded Vermont countryside, nestled against forever protected federal Appalachian Trail corridor land, this circa 1998 Federal Period reproduction home offers a meticulously well-crafted four-bedroom, three and a half-bath private residence in a location chosen by the owners for its proximity to everything the Upper Valley has to offer - from the nearby Quechee Club (12 minutes), Woodstock Village (20 minutes) or downtown Hanover, New Hampshire home to Ivy League Dartmouth College (20 minutes.) Built by master craftsman and reproduction housewright, Doug Gest, the interior of the home exhibits all of the hallmarks that his company is known for; reclaimed, wide pumpkin pine antique flooring, hand applied skim coat plaster walls, hand planed woodwork including the custom kitchen cabinets, copious built-ins and a high level of attention to detail where any woodworking skills were required. Inside, an open concept first floor offers a pleasing combination of both formal casual spaces, well configured for entertaining and larger gatherings. Upstairs, four bedrooms and two baths including a spacious second floor owner's suite offer plenty of space for guests or family. Outside the eleven acres presents a detached garage/barn, open lawns and perennial gardens and landscaping and a well sited tennis court (hard court with cushion).

Listed by Richard Higgerson, 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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3759 Royalton Turnpike Barnard VT 05031

Barnard, VT3759 Royalton Turnpike

Price$895,000

Est. Mortgage: $/month

MLS Number 4833387

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 2,350

Featured in Early American Life, an unbelievably beautiful modernized home and estate with extensive period details on 25.5 acres with magnificent mountain views. This circa 1815 Center Chimney Cape was moved from Nova Scotia with original flooring, wall paneling, and detailing - meticulously rebuilt in a quintessential Vermont setting with timber frame barns, rolling meadows, ponds, mountain views, & mature landscaping. The home is anchored by a classic center chimney with four working fireplaces and rare & stunning white washed wood ceilings. With extensive cabinetry, soapstone sinks, and granite counter-tops, the kitchen is gorgeous and boasts a La Cornue dual fuel range and french door refrigerator. The gourmet in you will appreciate the extensive walk-in butler's pantry with over-sized side by side refrigerator/freezer, prep sink, built-in dishwasher and plenty of cabinets for storage. An open floor-plan family/entertaining space allows you to show off your culinary talents to friends and family. The overall look and feel of this sunny home is just beautiful with all the modern up-to-date conveniences and radiant floor heat. Enjoy a leisurely lunch on the deck or stone patio taking in the gorgeous views and rolling meadow valleys. Sturdy rebuilt timber frame barns (one a circa 1790 English scribe rule hay barn) are available for animal use, farming, an artist studio, or just storage. Close to the Twin Farms Resort. Don't miss out on this fantastic opportunity.

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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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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2769 Cloudland Road Pomfret VT 05067

Pomfret, VT2769 Cloudland Road

Price$875,000

Est. Mortgage: $/month

Pending

MLS Number 4808114

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,308

“Ourmont” The Cloudland Cottage is a very private site high above the Cloudland Road. This is not the modest little camp style cottage one would expect at the highest point off Cloudland Road. The main part of the home is a chinked log structure with a towering fieldstone chimney/fireplace in the center. This was built in 1927. The current owners added and renovated over the years. There are 2 wings with 4 bedrooms, that have been freshly renovated and three baths. 90 .8 acres of woodlands, fields, seasonal brooks, a part of a wetland/beaver pond, a snow mobile trail, a once used guest house and a camp. Ourmont has been used by the owners as a seasonal summer house. There are perennial gardens, majestic maples, sparkling white birch, stonewalls and terraces. Like several of the original summer homes built in the late 1930's and 40's, there has always been a "cement pond" or swimming pool, built primarily for fire protection. This is a new saltwater pool. A secondary home site is available with the same dramatic view to the West, overlooking the top of Suicide Six , several valleys and ridges to the distant Killington Peak. AMAZING, SPECTACULAR, FABULOUS

Listed by Lynne Bertram, Lynne Bertram Real Estate

$
$
%
$/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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362 UPPER Road Bridgewater VT 05035

Bridgewater, VT362 UPPER Road

Price$835,000

Est. Mortgage: $/month

MLS Number 4741360

  • Residential Single Family
  • Construction Existing
  • Bathroom 11
  • Bedrooms 13
  • Square Feet 6,246

Perfectly suited for either residential or commercial use, this unique property is anchored around an antique cape farmhouse built when the township was founded. In an exceptional location, close to both the historic village of Woodstock and Killington Mountain Ski Resort, and within walking distance of the Long Trail Brewpub and the Bridgewater Corners Country Store; the beautifully landscaped four acre grounds feature an in-ground swimming pool with sheltered deck overlooking the Ottaquechee River Valley. The spacious, sunny, 6,200 square feet of living space is arranged into two sections connected by an enormous commercial grade kitchen. The larger section, continuously and profitably operated as October Country Inn since 1975, has 10 bedrooms, 11 baths, two large dining/meeting /game rooms, and a spacious living room. The other section, used as the innkeepers residence, has 3 bedrooms, 1 bath, office and private living area. A large semi-finished basement houses a commercial sized pantry, laundry area, large workshop and general storage. This property could easily be used as a private home for extended family, with room to grow into a special and affordable multi-generational family compound, or continued as a turn-key opportunity to step in and take over October Country Inn's long standing, excellent four decades long reputation for outstanding hospitality to the traveling public in the tradition of New England's country inns dating back over 200 years.

Listed by Laird Bradley, 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.