• Sellers
  • Buyers
  • Client Testimonials
  • Join Us At Real
  • Register
  • Sign In
Filters Reset
Save Search (2)
Save your search to get Alerts
44 Properties

44 Properties Available In Woodstock

  • Default
  • Price-High To Low
  • Price-Low To High
  • Newest Listings
  • Beds (Most)
  • Baths (Most)
  • Year Built (Newest)
  • Square Feet (Biggest)
VT >Woodstock >
Market Insights
1326 Curtis Hollow RD, Woodstock, VT 05091
3D

$774,000

Price Dropped by $25K

Single Family Home

3 Beds 3 Baths 2,004 SqFt

1326 Curtis Hollow RD, Woodstock, VT 05091

If you've been dreaming of the quintessential Vermont lifestyle, this exceptional property delivers the perfect blend of...

Listed by Mandolyn McIntyre Crow of Real Broker LLC

PrimeMLS
36 Happy Valley RD, Woodstock, VT 05073
1/18 18

$1,695

New

Condo

1 Bed 2 Baths 9,400 SqFt

36 Happy Valley RD, Woodstock, VT 05073

Available November 1st for a 1 year lease or rent it furnished for the winter for the winter $2395. All utilities and i...

Listed by Gail Childs of Covered Bridge RE

PrimeMLS
26 The Green, Woodstock, VT 05091
1/28 28

$2,485,000

New

Single Family Home

4 Beds 5 Baths 4,864 SqFt

26 The Green, Woodstock, VT 05091

Built in 1807 by Tille Parker, 26 The Green is one of Woodstock Village's earliest and perhaps prettiest houses. The Fed...

Listed by Dia Jenks of LandVest, Inc/Woodstock

PrimeMLS
2 Townhouse WAY, Woodstock, VT 05091
1/15 15

$2,595

Active

Condo

3 Beds 3 Baths 1,800 SqFt

2 Townhouse WAY, Woodstock, VT 05091

Available December 1st 2026 through April 30th 2027 Fully Furnished. All utilities plus internet included - you write o...

Listed by Matt DePrizio of Covered Bridge RE

PrimeMLS
121 Townhouse WAY #20, Woodstock, VT 05091
1/28 28

$399,600

Price Dropped by $15K

Condo

2 Beds 3 Baths 2,268 SqFt

121 Townhouse WAY #20, Woodstock, VT 05091

QUINTESSENTIAL WOODSTOCK VILLAGE LIVING: Offered at $399,600, this beautiful townhouse presents a rare opportunity to ow...

Listed by Carol Robert of Housing Solutions RE, LLC

PrimeMLS
16 Church ST, Woodstock, VT 05091
1/60 60

$1,195,000

Price Dropped by $180K

Single Family Home

4 Beds 3 Baths 3,979 SqFt

16 Church ST, Woodstock, VT 05091

This wonderful Vermont Cape-style home is a peaceful hideaway with amazing views upriver towards Killington is within wa...

Listed by Laird Bradley of Williamson Group Sothebys Intl. Realty Phone: 802-457-2000

PrimeMLS
115 Eastman RD, Woodstock, VT 05071
1/29 29

$5,875,000

Active

Single Family Home

3 Beds 4 Baths 5,384 SqFt

115 Eastman RD, Woodstock, VT 05071

Sorgenfrei, German for "carefree" captures the spirit of this remarkable 68 acre property in one of South Woodstock's mo...

Listed by T Story Jenks of LandVest, Inc/Woodstock

PrimeMLS
2556 Church Hill RD, Woodstock, VT 05091
1/32 32

$400,000

Active

Single Family Home

2 Beds 1 Bath 1,324 SqFt

2556 Church Hill RD, Woodstock, VT 05091

Once an old school house, this home features stone walls, beautiful gardens, and a nice level yard with a stone patio. T...

Listed by Dan Noble of Snyder Donegan Real Estate Group Cell: 802-356-6044

PrimeMLS
915 Peterkin Hill RD, Woodstock, VT 05091
1/58 58

$2,300,000

Active

Single Family Home

5 Beds 6 Baths 3,489 SqFt

915 Peterkin Hill RD, Woodstock, VT 05091

Exceptional Views to Killington! Perched high on a private knoll and surrounded by open lush meadows and surrounded by ...

Listed by Gretchjen Smith of Williamson Group Sothebys Intl. Realty Cell: 802-356-1873

PrimeMLS
3036 West Woodstock RD, Woodstock, VT 05091
1/22 22

$799,999

Active

Single Family Home

3 Beds 3 Baths 2,600 SqFt

3036 West Woodstock RD, Woodstock, VT 05091

On a small hill, amongst trees and beautiful gardens, sits this beautifully maintained log cabin with sweeping views of ...

Listed by Jennifer Kirkman of KW Vermont Woodstock Phone: 802-356-3722

PrimeMLS
36 Happy Valley RD, Woodstock, VT 05073
1/13 13

$1,450

Active

Condo

1 Bed 1 Bath 1,400 SqFt

36 Happy Valley RD, Woodstock, VT 05073

Lovely studio efficiency kitchen area, located in a Historic Hamlet of Woodstock Vermont. 7 miles to I89 and the Upper ...

Listed by Gail Childs of Covered Bridge RE

PrimeMLS
2706 East Woodstock RD, Woodstock, VT 05091
1/60 60

$1,645,000

Price Dropped by $50K

Single Family Home

4 Beds 4 Baths 4,800 SqFt

2706 East Woodstock RD, Woodstock, VT 05091

Gracious Single Family home and Investment Opportunity - This 3 bedroom, 2 bath brick colonial is approx. 2,300+/- sq/ft...

Listed by John F Bassette of Bassette Real Estate Group

PrimeMLS
5798 South RD, Woodstock, VT 05071
1/58 58

$2,950,000

Active

Single Family Home

8 Beds 8 Baths 6,200 SqFt

5798 South RD, Woodstock, VT 05071

Kedron Valley Farm c1850: A classic beauty, perched on a knoll overlooking the idyllic hills and lush meadows of the va...

Listed by Gretchjen Smith of Williamson Group Sothebys Intl. Realty Cell: 802-356-1873

PrimeMLS
358 Cowdrey PATH, Woodstock, VT 05071
1/46 46

$895,000

Price Dropped by $70K

Single Family Home

3 Beds 3 Baths 2,638 SqFt

358 Cowdrey PATH, Woodstock, VT 05071

This beautifully renovated, truly move-in-ready home has been thoughtfully updated throughout including a brand-new kitc...

Listed by John Snyder of Snyder Donegan Real Estate Group Cell: 802-280-5406

PrimeMLS
66 Hollow Farm RD, Woodstock, VT 05091
3D

$2,650,000

Price Dropped by $250K

Single Family Home

5 Beds 4 Baths 4,843 SqFt

66 Hollow Farm RD, Woodstock, VT 05091

CURTIS HOLLOW FARM, Exceptional estate on the western edge of Woodstock offering 105 diverse acres bordering Calvin Cool...

Listed by David Donegan of Snyder Donegan Real Estate Group Cell: 603-443-0044

PrimeMLS
1522 Barnard RD, Woodstock, VT 05091
1/58 58

$1,395,000

Active

Single Family Home

5 Beds 4 Baths 3,648 SqFt

1522 Barnard RD, Woodstock, VT 05091

Just 2 miles from Woodstock Village, this gracious brick Cape on 6 open acres offers the perfect blend of privacy, comfo...

Listed by Keri Cole of Williamson Group Sothebys Intl. Realty Cell: 410-200-3536

PrimeMLS
11 Maple ST, Woodstock, VT 05091
1/44 44

$595,000

Price Dropped by $54K

Single Family Home

4 Beds 2 Baths 2,288 SqFt

11 Maple ST, Woodstock, VT 05091

A rare Woodstock Village opportunity! A Victorian style home located in Woodstock's much desired Maple Street neighborho...

Listed by John Wetmore of Wetmore Real Estate

PrimeMLS
114 Oak Ridge WAY, Woodstock, VT 05091
3D

$2,500,000

Active

Single Family Home

4 Beds 4 Baths 5,127 SqFt

114 Oak Ridge WAY, Woodstock, VT 05091

See the property specific website with video, 3-D tour and more. Set against the timeless beauty of Woodstock's rolling ...

Listed by Tami Sullivan of Snyder Donegan Real Estate Group Phone: 603-254-6570

PrimeMLS
2394 Fletcher Hill RD, Woodstock, VT 05091
3D

$1,895,000

Active

Single Family Home

2 Beds 3 Baths 2,944 SqFt

2394 Fletcher Hill RD, Woodstock, VT 05091

Newly constructed Modern Vermont Farmhouse residence on 14 acres with absolutely amazing river views, 13-foot ceilings, ...

Listed by John Snyder of Snyder Donegan Real Estate Group Cell: 802-280-5406

PrimeMLS
85 Townhouse WAY #14, Woodstock, VT 05091
1/26 26

$450,000

Price Dropped by $15K

Condo

2 Beds 3 Baths 2,091 SqFt

85 Townhouse WAY #14, Woodstock, VT 05091

Fully furnished condo nestled in a small quiet community just 5 minutes from "Historic Woodstock". Super location! Thi...

Listed by Gretchjen Smith of Williamson Group Sothebys Intl. Realty Cell: 802-356-1873

PrimeMLS
39 Elm ST #B, Woodstock, VT 05091
1/54 54

$1,600,000

Active

Condo

3 Beds 4 Baths 3,294 SqFt

39 Elm ST #B, Woodstock, VT 05091

The Richmond House Unit B | Woodstock Village. An enduring Woodstock landmark, the iconic Richmond House (c.1826) is a p...

Listed by Derek Cosentino of Four Seasons Sotheby's Int'l Realty

PrimeMLS
249 Sawyer RD, Woodstock, VT 05091
1/21 21

$2,950,000

Price Dropped by $350K

Single Family Home

3 Beds 5 Baths 3,682 SqFt

249 Sawyer RD, Woodstock, VT 05091

Located in Woodstock, Vermont just one mile from the village green, the Alta House offers a rich quality of life filled ...

Listed by Andrew D Bustin of LandVest, Inc/Woodstock

PrimeMLS
355 Greene RD, Woodstock, VT 05071
1/59 59

$14,900,000

Active

Single Family Home

7 Beds 10 Baths 12,520 SqFt

355 Greene RD, Woodstock, VT 05071

Star Hill Farm is completely private, hidden on a hillside with pastoral and mountain views in the heart of South Woodst...

Listed by Christopher W Lang of Bravynia

PrimeMLS
26 Mt Peg RD #A, Woodstock, VT 05091
3D

$975,000

Price Dropped by $220K

Condo

3 Beds 4 Baths 2,592 SqFt

26 Mt Peg RD #A, Woodstock, VT 05091

Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunit...

Listed by Mary G Mayhew of Snyder Donegan Real Estate Group Cell: 802-356-3776

PrimeMLS
  • 1
  • 2

explore listings in Woodstock

  • Open House
  • Price Reduced
  • Virtual Tour
  • 3D Tour
IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.

SITE MAP

      Sellers
      Buyers
      Client Testimonials
      Join Us At Real
defaultdefault

Mandolyn & Tyler Crow License ID: 082.0134671

+1(802) 683-1617 mandolynvt@gmail.com

39 Central St, Woodstock, VT 05091, USA

Get My App

Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.

SITE MAP

      Sellers
      Buyers
      Client Testimonials
      Join Us At Real
defaultdefault

Mandolyn & Tyler Crow License ID: 082.0134671

+1(802) 683-1617 mandolynvt@gmail.com

39 Central St, Woodstock, VT 05091, USA

Get My App

Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility