Homes for Sale near Woodstock Union Middle School

/49
$1,595,000
- 5 Beds
- 3.5 Baths
- 3,648 Sq Ft
1522 Barnard Rd, Woodstock, VT 05091

Just 2 miles from Woodstock Village, this gracious brick cape on 6 open acres offers space, comfort, and classic Vermont charm. The expanded chef’s kitchen opens to a gracious gathering room ideal for entertaining, while 3 fireplaces—wood-burning, brick, and gas-ready—provide cozy warmth throughout. Upstairs, find 3–4 bedrooms including one with its own fireplace, plus a private guest room or

Keri Cole Williamson Group Sothebys Intl. Realty

1522 Barnard Rd, Woodstock, VT 05091
/48
$1,749,000
- 3 Beds
- 3.5 Baths
- 3,294 Sq Ft
39 Elm St Unit B, Woodstock, VT 05091

The Richmond House – Unit B | Woodstock Village. An enduring Woodstock landmark, the iconic Richmond House (c.1826) is a distinguished brick Federal with a softly weathered, rose-hued patina and elegant architectural details. Set on over an acre behind a classic white picket fence, this historic property—reimagined under the direction of Laurence Rockefeller—comprises three luxurious residences

Zoe Hathorn Washburn Snyder Donegan Real Estate Group

39 Elm St Unit B, Woodstock, VT 05091
/40
$3,500,000
- 6 Beds
- 6 Baths
- 5,433 Sq Ft
61 Academy Cir, Woodstock, VT 05071

Hyacinth House has been a landmark property in the historic village of South Woodstock from its early settlement in the 1800's. Sited on a knoll overlooking the Kedron Brook this grand residence has been carefully restored by talented craftsmen. Taking care to keep the beautiful original details the owners have brought the systems into the 21st century with the highest quality of materials. The

Carol Wood Williamson Group Sothebys Intl. Realty

61 Academy Cir, Woodstock, VT 05071
/42
$8,000,000
- 3 Beds
- 3.5 Baths
- 6,096 Sq Ft
115 Eastman Rd, South Woodstock, VT 05071

Sorgenfrei, or "Carefree," was built by Ennis Construction in 2015, and this extraordinary property truly embodies that sobriquet. A stunning and uncommon confluence of the finest materials and the most energy efficient techniques, this home was carefully constructed to maximize worry-free enjoyment. The most advanced systems and a focused commitment to the highest quality make this home a

Keri Cole

115 Eastman Rd, South Woodstock, VT 05071
/37
$1,185,000
- 4 Beds
- 3 Baths
- 2,785 Sq Ft
1782 Randall Rd, Woodstock, VT 05091

This early Woodstock residence was built in 1792 by Joseph Wood on a parcel of land he purchased in 1786 from Ebenezer Kingsley, one of Woodstock early settlers. A classic New England Cape of the period with the notable features of a central chimney with multiple fireplaces and a second story overhang on the gables. The house retains a great deal of original features and fabric including wide

Wade Treadway Wade I Treadway Real Estate

1782 Randall Rd, Woodstock, VT 05091
/41
$1,495,000
- 4 Beds
- 2.5 Baths
- 2,532 Sq Ft
7 Slayton Terrace, Woodstock, VT 05091

A rare in-village offering, 7 Slayton Terrace combines walkability, views, and beautifully renovated interiors—just steps from the heart of Woodstock. Sited on an oversized .79-acre lot overlooking Billings Farm, this 4-bedroom home offers the space and flexibility rarely found so close to the village center. The main house features a stunning new kitchen with high-end finishes and beautifully

Keri Cole Williamson Group Sothebys Intl. Realty

7 Slayton Terrace, Woodstock, VT 05091
/35
$1,350,000
- 4 Beds
- 2.5 Baths
- 2,668 Sq Ft
513 Deer Brook Way Unit Lot 16, Woodstock, VT 05091

This traditional New England Colonial home was professionally designed and custom built by the renowned Vermont Vernacular Builders. The home is strategically sited to enjoy the long views of the distant hills and to benefit from its southern exposure. This 4 bedroom is a quintessential classic example of pure Vermont living apparent in this gracious sun-filled home. There are wide board floors

Chris Crowe Quechee Lakes Real Estate Center

513 Deer Brook Way Unit Lot 16, Woodstock, VT 05091
/27
$1,200,000
- 5 Beds
- 4.5 Baths
- 3,486 Sq Ft
19 Church St Unit EX, Woodstock, VT 05091

Bright and spacious five bedroom, five bath in-village residence with Ottauquechee River frontage and less than 1-minute walk to the Woodstock Green. 2-car attached garage enters into the kitchen via a mud-laundry room. Eat-in kitchen with stainless appliances, granite countertops and a large sunny bay window leads to the formal dining room, and also opens to the patio, perfect for entertaining

John Snyder Snyder Donegan Real Estate Group

19 Church St Unit EX, Woodstock, VT 05091
/34
$2,199,000
- 4 Beds
- 3.5 Baths
- 3,564 Sq Ft
15 Hathorn Hill Street Extension, Woodstock, VT 05091

An incredibly rare combination of in-Village and country living. 4+ acres and privacy with a pond and heated in-ground pool, yet walk-to-the Green. The residence, designed and built by the well-respected design-build firm Ambrose Construction, offers modern amenities, appliances and construction with a “Vermont Farmhouse” aesthetic. The vaulted ceiling timber frame great-gathering room has

John Snyder Snyder Donegan Real Estate Group

15 Hathorn Hill Street Extension, Woodstock, VT 05091
/59
$1,745,000
- 2 Beds
- 3 Baths
- 2,106 Sq Ft
7 North St, Woodstock, VT 05091

Stunning Renovated Antique Cape in the Heart of Woodstock Village!Tucked away on over an acre of beautifully landscaped land directly abutting the Marsh-Billings-Rockefeller National Park, this fully renovated antique Cape offers the rare combination of historic charm, modern efficiency, and unbeatable walkability. Located in the heart of Woodstock Village, you can stroll to the village

Keri Cole Williamson Group Sothebys Intl. Realty

7 North St, Woodstock, VT 05091
/60
$1,995,000
- 3 Beds
- 2.5 Baths
- 5,422 Sq Ft
2334 South Rd, Woodstock, VT 05091

Offered for the first time, the exclusive private residence of one of Woodstock's most notable and prolific builders, Hank Savelberg. Located just five minutes from the Woodstock Village Green, this whimsical, private, contemporary hillside estate was lovingly constructed featuring well thought, connected open spaces with expansive glass walls and dramatic sweeping wooden ceilings. The entire

Danny Kogut Williamson Group Sothebys Intl. Realty

2334 South Rd, Woodstock, VT 05091
/43
$1,395,000
- 4 Beds
- 3 Baths
- 4,864 Sq Ft
15 Central St, Woodstock, VT 05091

15 Central Street is one of the finest commercial locations in Woodstock with two of the most creative and successful businesses as the anchor tenants. The property has adapted to changes of the course of its long history of uses including residential shop owner, a barber shop, a dance & pool hall, law office, architectural services and a variety of mercantile endeavors. Notably, the building

Laird Bradley Williamson Group Sothebys Intl. Realty

15 Central St, Woodstock, VT 05091
/34
$475,000
- 3 Beds
- 2 Baths
- 1,489 Sq Ft
6852 U S 4, Bridgewater, VT 05035

This 1885 antique story and a half cape has been comprehensively updated during the long ownership of the sellers who made the home more energy efficient with all new windows, recent heating system, modern kitchen and bathrooms. The home creatively blends an historic floor plan defined by a traditional living room and dining room with the more casual lifestyle of today. The open concept Vermont

Laird Bradley Williamson Group Sothebys Intl. Realty

6852 U S 4, Bridgewater, VT 05035
/18
$249,500
- 1 Bed
- 1 Bath
- 856 Sq Ft
56 Heritage Condo Way Unit 9, Woodstock, VT 05091

Lots of upgrades to this quiet, two level condo, with lovely views off back baloney. Bonus- new mini split heat pump providing both air conditioning and heat. Kitchen has some upgraded as well with a new dishwasher. This open floor concept condo provides lots of natural sunlight. Cozy up in the living room/dining room and read a book during the winter months overlooking the spacious

Gretchjen Smith Williamson Group Sothebys Intl. Realty

56 Heritage Condo Way Unit 9, Woodstock, VT 05091
/32
$80,000
- 3 Beds
- 2 Baths
- 1,008 Sq Ft
185 Riverbend Way, Woodstock, VT 05091

Start your Vermont dream with this affordable 3-bedroom, 2-bath mobile home just minutes from downtown Woodstock, VT. Located in a quiet, private community with stunning mountain views and direct river frontage on the Ottauquechee, this home is a rare opportunity to enjoy scenic living at a budget-friendly price. Perfect as a first home, vacation getaway, or investment, this property is also

Mendi Michael Engel & Völkers Okemo

185 Riverbend Way, Woodstock, VT 05091
/19
$480,000
- 2 Beds
- 1 Bath
- 768 Sq Ft
37 Atwood Ave, Woodstock, VT 05091

Charming, updated, and perfectly located—this turnkey gem is your ticket to easy living in one of the area’s most adorable neighborhoods! With all the major systems recently upgraded - including a new furnace, hot water heater, Tesla Powerwall, and water purification system - this efficient home is move-in ready.Inside, you’ll love the fresh renovations: a modern kitchen with

Keri Cole Williamson Group Sothebys Intl. Realty

37 Atwood Ave, Woodstock, VT 05091
/59
$279,500
- 2 Beds
- 1 Bath
- 1,076 Sq Ft
643 Vermont 12, Hartland, VT 05048

Charming and affordable home on a level 1-acre lot with open yard and serene wooded backdrop. This expanded ranch offers 2 bedrooms and 1 full bath, with a practical layout including first-floor laundry and a spacious second-floor bedroom addition. Originally built in 1940 with an upstairs expansion in the 1980s, the home features a drilled well, private septic, and several recent updates

John Bassette Bassette Real Estate Group

643 Vermont 12, Hartland, VT 05048
/57
$985,000
- 3 Beds
- 2 Baths
- 2,760 Sq Ft
616 Rose Hill Rd, Woodstock, VT 05091

This is a rare opportunity to own 10.1 acres of land in a coveted area of Woodstock that includes a 1988 Frizzell Builders house and a detached oversized garage with a second floor for storage . The property was part of the King Farm which is now in Vt. Land Trust as conserved land , until it was split off in the late 1980's when the Colby family came into ownership and built the existing house

Carol Wood Williamson Group Sothebys Intl. Realty

616 Rose Hill Rd, Woodstock, VT 05091
/53
$798,000
- 2 Beds
- 2 Baths
- 1,308 Sq Ft
392 Gully Rd, Woodstock, VT 05091

Built in 2019, this charming Cape-style home is nestled on five sunny, private acres just minutes from Woodstock Village. Thoughtfully designed and beautifully constructed, the home offers efficient, low-maintenance living in a coveted location. With excellent solar exposure, stunning sunset views, and lovely hillside scenery, it’s bright, warm, and welcoming year-round.The interior

Keri Cole Williamson Group Sothebys Intl. Realty

392 Gully Rd, Woodstock, VT 05091
/54
$985,000
- 3 Beds
- 3 Baths
- 1,920 Sq Ft
72 Oakridge Way, Woodstock, VT 05091

PRIME LOCATION! Tucked away at the end of a peaceful dead-end road in the Westerdale neighborhood is this Vermont Cape Cod home offers the perfect blend of privacy and convenience on just over 6 acres. Surrounded by mature trees and set on a wooded lot overlooking a tranquil pond, you’ll enjoy the calm of nature right outside your doorstep. The freshly installed deck provides a serene spot.

Nancy Greenwood Watson Realty & Associates

72 Oakridge Way, Woodstock, VT 05091
/40
$465,000
- 3 Beds
- 3 Baths
- 1,600 Sq Ft
2 High St, Woodstock, VT 05091

FLASH OPPORTUNITY AWAITS – Historic c. 1890 1,600 sq/ft. unfinished home in the center of downtown Woodstock. In the heart of everything! LOOKING FOR A FAST SALE - AND A CASH BUYER. The home has been stripped back to framing and is ready for a builder or future investment. It is not currently habitable and will not be able to be sold or shown to someone looking for financing or construction loan

John Bassette Bassette Real Estate Group

2 High St, Woodstock, VT 05091
/32
$899,500
- 4 Beds
- 3 Baths
- 3,190 Sq Ft
598 E Woodstock Rd, Woodstock, VT 05091

This stately, rambling gambrel home offers privacy, convenience, antique charm, and room for everyone. Walking distance to the east end of Woodstock village, on 2.9 lush acres including a fenced backyard, a fenced vegetable garden, and extensive perennial beds. The home is a stunning mixture of antique touches and modern functionality, with beautiful built-ins and closet spaces at every turn. The

Geoff Eckler Real Broker LLC

598 E Woodstock Rd, Woodstock, VT 05091
/37
$845,000
- 2 Beds
- 1.5 Baths
- 1,714 Sq Ft
403 Horse Shoe Way, Woodstock, VT 05071

Totally secluded on a rolling hillside, just 10 minutes from the Woodstock Village Green, this storybook Post and Beam cottage awaits your vision. From the reclaimed centuries old barn frame to the massive fieldstone fireplace, every detail is well thought, and impeccably executed honoring the Vermont tradition of reclaiming and utilizing locally sourced materials.The home was carefully, and

Danny Kogut Williamson Group Sothebys Intl. Realty

403 Horse Shoe Way, Woodstock, VT 05071
/60
$859,000
- 7 Beds
- 7 Baths
- 4,581 Sq Ft
7137 Us Route 4, Bridgewater, VT 05034

The historic Bridgewater Inn consists of a 3-bedroom, 3-bath spacious home excellent for families or groups. The home has two covered porches, a large eat-in kitchen, living room with gas fireplace and two game rooms. The house has new furniture, paint and floors along with new flush mounted mini splits.Attached are 4 turnkey suites with entrances separate form the home. The property is

Laura Derderian Killington Valley Real Estate

7137 Us Route 4, Bridgewater, VT 05034
/55
$980,000
- 3 Beds
- 3 Baths
- 1,656 Sq Ft
509 Church Hill Rd, Wood Stock, VT 05091

Enjoy in-town ease of living combined with Vermont country charm. This well maintained , efficient home provides first floor living with an additional lower floor ensuite bedroom /sitting area with direct access to lovely grounds and gardens.The light filled home is in excellent condition and is surrounded by fabulous perennial gardens, mature maple trees, raspberry and blueberry bushes ,

Carol Wood Williamson Group Sothebys Intl. Realty

509 Church Hill Rd, Wood Stock, VT 05091
/32
$779,000
- 4 Beds
- 4 Baths
- 2,436 Sq Ft
168 Thorn Apple Ln, Hartford, VT 05047

Sweet 4 bedroom / 4 bath home nestled between Hillside and High Pastures Road. Accessed by a private road, you will find this property to be located in a great setting that’s quiet and has views of the Woodstock hillside. This home offers nice generous size rooms throughout and a wonderful floor plan. On the main floor, there is a nice size kitchen open to a large living room with a wood burning

Lisa Baldwin Coldwell Banker LIFESTYLES - Hanover

168 Thorn Apple Ln, Hartford, VT 05047
/50
$945,000
- 4 Beds
- 2.5 Baths
- 2,044 Sq Ft
100 Pomfret Rd, Woodstock, VT 05091

Charming, Unique, and Ideally Located! Welcome to 100 Pomfret Road—a beautifully updated farmhouse set on four level, picturesque acres just a short walk from Mt. Tom, Billings Farm, and the heart of downtown Woodstock. This rare find blends timeless character with everyday convenience in a peaceful, brookside setting.Inside, you’ll find a sun-drenched home featuring four

Keri Cole Williamson Group Sothebys Intl. Realty

100 Pomfret Rd, Woodstock, VT 05091
/19
$695,000
- Land
- 61 Acres
- $11,474 per Acre
0 Noah Wood Rd, Woodstock, VT 05071

Incredible location! 60+ acres situated on the corner of South Rd. (106) and Noah Wood Rd. in beautiful South Woodstock. The land rises from the roads to the crest of the hilltop with amazing view potential looking to the Northeast. Multiple building sites can be found throughout the property which offers great recreational opportunities including direct access to the VAST trail on the lower

Dan Noble Snyder Donegan Real Estate Group

0 Noah Wood Rd, Woodstock, VT 05071
/47
$8,000,000
- 3 Beds
- 3.5 Baths
- 5,384 Sq Ft
115 Eastman Rd, Woodstock, VT 05091

Sorgenfrei, or "Carefree," was built by Ennis Construction in 2015, and this extraordinary property truly embodies that sobriquet. A stunning and uncommon confluence of the finest materials and the most energy efficient techniques, this home was carefully constructed to maximize worry-free enjoyment. The most advanced systems and a focused commitment to the highest quality make this home a

Keri Cole Williamson Group Sothebys Intl. Realty

115 Eastman Rd, Woodstock, VT 05091
/38
$690,000
- 4 Beds
- 3 Baths
- 2,557 Sq Ft
144 Butternut Ln, Woodstock, VT 05091

The Harry Emmons House an antique brick cape located in the village of Taftsville sited on an open flat village lot. Through the classic covered farm porch enter a gathering room with a brick fireplace, light-filled high ceilings, exposed beams in comfortably sized rooms, a country kitchen, sunny dining room, and a first-floor bedroom with dressing area. Moving upstairs, the second floor has two

Scott Monahan Williamson Group Sothebys Intl. Realty

144 Butternut Ln, Woodstock, VT 05091
/9
$275,000
- Land
- 0.43 Acre
- $639,535 per Acre
1054 W Woodstock Rd, Woodstock, VT 05091

Ideally located parcel across West Woodstock Road from the Woodstock Farmers Market and 500 yards from the entry to Woodstock Union Middle & High School. Public water and sewer available with access off Prosper Road near the junction of US Road Route 4/West Woodstock Road. Building plans available. Multi-unit housing development potential in zero vacancy environment.

Laird Bradley Williamson Group Sothebys Intl. Realty

1054 W Woodstock Rd, Woodstock, VT 05091
/57
$1,895,000
- 3 Beds
- 2.5 Baths
- 2,688 Sq Ft
20 The Green, Woodstock, VT 05091

Stunning antique cape! Located in the 'heart' of Woodstock. Originally located on Central Street- this home was moved in the 1960's to this location and had an extensive renovation in 2011. The antique brick section was built in 1826- it boasts a spacious living room anchored with a large wood burning fireplace, original wide pine floors and lots of space for entertaining. Adjacent find a

Gretchjen Smith Williamson Group Sothebys Intl. Realty

20 The Green, Woodstock, VT 05091
/33
$729,000
- 3 Beds
- 3 Baths
- 1,550 Sq Ft
13 Slayton Terrace, Woodstock, VT 05091

Charming cottage located in the heart of historic Woodstock Village with walking distance to all the shops, restaurants and town theatre. Mtn Peg walking trails just a 2 minute walk from front door for those hiking enthusiasts. This home is filled with an abundance of natural sunlight and features all hardwood floors throughout. New kitchen with butcher block counters, stainless appliances,

Gretchjen Smith Williamson Group Sothebys Intl. Realty

13 Slayton Terrace, Woodstock, VT 05091
/35
$1,895,000
- 5 Beds
- 4.5 Baths
- 4,214 Sq Ft
10 College Hill Rd, Woodstock, VT 05091

10 College Hill is the perfect in-village residence, off the main road yet walk-to-everything. The original, historic residence was designed in 1916 by renowned architect John Russell Pope whose accomplishments include the Jefferson Memorial, and master plans for Dartmouth and Yale. It also enjoys modern additions and updates including a stunning first-level primary bedroom suite designed in

John Snyder Snyder Donegan Real Estate Group

10 College Hill Rd, Woodstock, VT 05091
/58
$549,000
- Land
- 20 Acres
- $27,178 per Acre
00 Long Hill Rd, Woodstock, VT 05071

Discover the perfect blend of privacy and convenience with this exceptional 20.2-acre parcel, combining two lots into one remarkable opportunity. Featuring a 50 foot right-of-way for access, this wooded retreat offers multiple prime building sites. With selective clearing, you can take in breathtaking views in your choice of direction; east, south, north, or west.Located just minutes from

Eric Johnston Four Seasons Sotheby's Int'l Realty

00 Long Hill Rd, Woodstock, VT 05071
/43
$2,250,000
- 5 Beds
- 3.5 Baths
- 3,502 Sq Ft
4945 South Rd, Woodstock, VT 05071

The John Arnold Cottle House is a landmark residence in the heart of South Woodstock, a rare blend of village convenience and country living. Built in 1811 by one of the area's earliest settlers, this stately Federal-style brick home has been thoughtfully restored to honor its historic charm while integrating modern comforts. Set on 2.7 acres, the property features 450 ft of frontage on Kedron

Story Jenks LandVest, Inc/Woodstock

4945 South Rd, Woodstock, VT 05071
/48
$795,000
- 3 Beds
- 2 Baths
- 1,694 Sq Ft
25 Linden Hill St, Woodstock, VT 05091

This classic early 20th Century farmhouse with 3 sunny bedrooms and two baths is sited on a quiet Village Street uphill above the Woodstock Elementary School and across from the public playground at Vail Field and the Woodstock Country Club golf course. The home has benefitted from the thoughtful additions of an eat-in kitchen and a front porch where you can enjoy long summer evenings. A

Laird Bradley Williamson Group Sothebys Intl. Realty

25 Linden Hill St, Woodstock, VT 05091
/60
$2,450,000
- 4 Beds
- 3.5 Baths
- 5,573 Sq Ft
851 Riverside Park Rd, Woodstock, VT 05091

"All Seasons" is the ultimate Vermont retreat, designed for gatherings and getaways while seamlessly blending rustic charm with modern luxury. This 5,900-sq-ft barn-style home, just over five minutes from Woodstock Village via Route 4 and the Lincoln Covered Bridge, sits high on a knoll above the Ottauquechee River with views to Killington. A veritable mini-resort, the property offers

Richard Higgerson Higgerson & Company

851 Riverside Park Rd, Woodstock, VT 05091
/6
$54,900
- Land
- 29 Acres
- $1,893 per Acre
0 Rt 7 (Db 94 Dp 399), Royalton, KY 41464

These 29 acres, per PVA map, are located in southern Magoffin County in Royalton, Kentucky, with the acreage running along both sides of RT 7. The property is located in the Salt Lick area outside Royalton and includes property on both sides of Salt Lick Road as well. The property is undeveloped but electric and public water are available. For those with visions of homesteading, the Licking River

Doug Wireman First Choice Realty & Assoc.

0 Rt 7 (Db 94 Dp 399), Royalton, KY 41464
/60
$1,850,000
- 4 Beds
- 3.5 Baths
- 5,000 Sq Ft
2706 E Woodstock Rd, Woodstock, VT 05091

INVESTMENT & RESIDENTIAL OPPORTUNITY - Rare historic building (The Taftsville Country Store - Woodstock VT) available for owner occupancy with multiple additional income units in the village of Taftsville. Just five minutes to the quintessential downtown New England Village of Woodstock! Property includes storefront space (approved for restaurant, cafe, or retail store), Post Office (with current

John Bassette Bassette Real Estate Group

2706 E Woodstock Rd, Woodstock, VT 05091

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Copyright 2025 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. 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.