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New Listings in Woodstock

42-18 Heritage Condo Way Unit Unit 18D, Woodstock image
42-18 Heritage Condo Way Unit Unit 18D, Woodstock $244,000

Easy living in this updated condo that is perfect for a primary or secondary residence. Located in a small condo community that is mostly owner occupied the setting offer...

  • 1 Beds
  • 1 Baths
  • 5101220 MLS
  • ACTIVE Status
16 Church St, Woodstock image
16 Church St, Woodstock $1,375,000

This wonderful Vermont Cape-style home has overlooked the Ottauquechee River and the former Woodstock woolen mill (now the 'new' mill and community pools and recreation c...

  • 4 Beds
  • 3 Baths
  • 5100512 MLS
  • ACTIVE Status
115 Eastman Rd, Woodstock image
115 Eastman Rd, Woodstock $5,875,000

Sorgenfrei German for "carefree" captures the spirit of this remarkable property in one of South Woodstock's most desirable locations: a place where life slows and the be...

  • 3 Beds
  • 4 Baths
  • 5099532 MLS
  • ACTIVE Status
2556 Church Hill Rd, Woodstock image
2556 Church Hill Rd, Woodstock $400,000

Once an old school house, this home features stone walls, beautiful gardens, and a nice level yard with a stone patio. The year-round brook cascades over rocks and winds ...

  • 2 Beds
  • 1 Baths
  • 5099229 MLS
  • ACTIVE Status
3036 W Woodstock Rd, Woodstock image
3036 W Woodstock Rd, Woodstock $799,999 ▲

On a small hill, amongst trees and beautiful gardens, sits this beautifully maintained log cabin with sweeping views of the surrounding mountains and river valley. Just ...

  • 3 Beds
  • 3 Baths
  • 5098474 MLS
  • ACTIVE Status
915 Peterkin Hill Rd, Woodstock image
915 Peterkin Hill Rd, Woodstock $2,300,000

Exceptional Views to Killington! Perched high on a private knoll and surrounded by open lush meadows and surrounded by antique stonewalls. This 5 bedroom, 4 bathroom ex...

  • 5 Beds
  • 6 Baths
  • 5098424 MLS
  • ACTIVE Status
121 Townhouse Way Unit 24, Woodstock image
121 Townhouse Way Unit 24, Woodstock $497,500

Live Work Play, Retire and Play, or Just Play on the Weekends and Holidays! This wonderful 3 BR, 3 Bath Townhome/Condo has it all. Nestled in a small quiet wooded comm...

  • 3 Beds
  • 3 Baths
  • 5098210 MLS
  • ACTIVE Status
1326 Curtis Hollow Rd, Woodstock image
1326 Curtis Hollow Rd, Woodstock $799,000

If you've been dreaming of the quintessential Vermont lifestyle, this exceptional property delivers the perfect blend of privacy, charm, and convenience. Nestled on over ...

  • 3 Beds
  • 3 Baths
  • 5097258 MLS
  • ACTIVE Status
2706 E Woodstock Rd, Woodstock image
2706 E Woodstock Rd, Woodstock $1,695,000

Gracious Single Family home and Investment Opportunity - This 3 bedroom, 2 bath brick colonial is approx. 2,300+/- sq/ft with beautiful old wood flooring, newer kitchen, ...

  • 4 Beds
  • 4 Baths
  • 5096963 MLS
  • ACTIVE Status
121 Townhouse Way Unit 20, Woodstock image
121 Townhouse Way Unit 20, Woodstock $465,000

Spacious, immaculate, and beautifully maintained Federal-style brick townhouse located in the prestigious village of Woodstock, often recognized as one of America’s most ...

  • 3 Beds
  • 3 Baths
  • 5095918 MLS
  • ACTIVE Status
Iver Johnson Way, Woodstock image
Iver Johnson Way, Woodstock $169,000

Instant equity in Woodstock! Bring your vision to life on this exceptional parcel of raw land, nestled in one of Vermont’s most coveted and quintessential communities. Of...

  • 5095630 MLS
  • ACTIVE Status
473 Kendall Rd, Woodstock image
473 Kendall Rd, Woodstock $2,225,000

Nestled in amongst flowering lilacs, ancient apple trees, and terraced English perennial gardens, this lovingly restored classic antique stone cape has all the convenienc...

  • 4 Beds
  • 3 Baths
  • 5095556 MLS
  • ACTIVE Status
11 Maple St, Woodstock image
11 Maple St, Woodstock $649,000 ▼

A rare Woodstock Village opportunity! A Victorian style home located in Woodstock's much desired Maple Street neighborhood! Popular Vail Field recreation area is convenie...

  • 5095205 MLS
  • ACTIVE Status
5798 South Rd, Woodstock image
5798 South Rd, Woodstock $2,950,000

Kedron Valley Farm c1850: A classic beauty, perched on a knoll overlooking the idyllic hills and lush meadows of the valley with approx 32 acres. This stunning extended...

  • 8 Beds
  • 8 Baths
  • 5094600 MLS
  • ACTIVE Status
358 Cowdrey Path, Woodstock image
358 Cowdrey Path, Woodstock $965,000

This beautifully renovated, truly move-in-ready home has been thoughtfully updated throughout — including a brand-new kitchen, refreshed flooring, modernized bathrooms, f...

  • 3 Beds
  • 3 Baths
  • 5094379 MLS
  • ACTIVE Status
1190 Long Hill Rd, Woodstock image
1190 Long Hill Rd, Woodstock $350,000 ▼

Tucked away on 11.58 private acres in the heart of South Woodstock, this peaceful Vermont retreat offers simplicity, seclusion, and endless potential. Located along sceni...

  • 5093182 MLS
  • ACTIVE Status
1190 Long Hill Rd, Woodstock image
1190 Long Hill Rd, Woodstock $350,000 ▼

Tucked away on 11.58 private acres in the heart of South Woodstock, this peaceful Vermont retreat offers simplicity, seclusion, and endless potential. Located along sceni...

  • 1 Beds
  • 1 Baths
  • 5093181 MLS
  • ACTIVE Status
Rte 106, Woodstock image
Rte 106, Woodstock $395,000

Rare opportunity to own 8 +/- acres of land in South Woodstock Village with easy access off of Rt. 106. This parcel is being divided off of a 10.87 acre lot. There is a ...

  • 5092107 MLS
  • ACTIVE Status
66 Hollow Farm Rd, Woodstock image
66 Hollow Farm Rd, Woodstock $2,900,000 ▼

CURTIS HOLLOW FARM, Exceptional estate on the western edge of Woodstock offering 105 diverse acres bordering Calvin Coolidge State Forest. The updated main house features...

  • 5 Beds
  • 4 Baths
  • 5091062 MLS
  • ACTIVE Status
97 Valley View Rd, Woodstock image
97 Valley View Rd, Woodstock $850,000

The justifiably proud owner of this property points out these features: Potential "Barnominium." Conveniently located just 1/4 mile from Woodstock Village town line and j...

  • 5091005 MLS
  • ACTIVE Status
47 Pleasant St, Woodstock image
47 Pleasant St, Woodstock $695,000 ▼

Excellent opportunity for residential or office/commercial space with easy access and high visibility on Rt 4 coming into town, Currently configured as office space down...

  • 3 Beds
  • 2 Baths
  • 5089949 MLS
  • ACTIVE Status
1522 Barnard Rd, Woodstock image
1522 Barnard Rd, Woodstock $1,395,000 ▼

Just 2 miles from Woodstock Village, this gracious brick Cape on 6 open acres offers the perfect blend of privacy, comfort, and classic Vermont charm. Thoughtfully expand...

  • 5 Beds
  • 4 Baths
  • 5089552 MLS
  • ACTIVE Status
Noah Wood Road, Woodstock image
Noah Wood Road, Woodstock $529,000 ▼

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 th...

  • 5088279 MLS
  • ACTIVE Status
11 Maple St, Woodstock image
11 Maple St, Woodstock $649,000 ▼

A rare Woodstock Village opportunity! A Victorian style home located in Woodstock's much desired Maple Street neighborhood! Popular Vail Field recreation area is convenie...

  • 4 Beds
  • 2 Baths
  • 5088170 MLS
  • ACTIVE Status
114 Oak Ridge Way, Woodstock image
114 Oak Ridge Way, Woodstock $2,500,000

See the property specific website with video, 3-D tour and more. Set against the timeless beauty of Woodstock’s rolling countryside, this exceptional estate offers a rare...

  • 4 Beds
  • 4 Baths
  • 5087228 MLS
  • ACTIVE Status
Oak Ridge Way, Woodstock image
Oak Ridge Way, Woodstock $345,000

Your dream home starts right here — with a blank canvas in one of Vermont's most coveted communities. This exceptional buildable lot on Oak Ridge Way presents a rare opp...

  • 5085318 MLS
  • ACTIVE Status
2394 Fletcher Hill Rd, Woodstock image
2394 Fletcher Hill Rd, Woodstock $1,895,000

Newly constructed Modern Vermont Farmhouse residence on 14 acres with absolutely amazing river views, 13-foot ceilings, gourmet kitchen, oversized french doors and window...

  • 2 Beds
  • 3 Baths
  • 5084536 MLS
  • ACTIVE Status
37 South St, Woodstock image
37 South St, Woodstock $718,500 ▼

Great new price! Nestled in the vibrant heart of Woodstock Village, this beautifully renovated residence offers the ultimate "walk-to-all" lifestyle. Stepping inside, ne...

  • 3 Beds
  • 2 Baths
  • 5081166 MLS
  • ACTIVE Status
85 Townhouse Way Unit 14, Woodstock image
85 Townhouse Way Unit 14, Woodstock $465,000 ▼

Fully furnished condo nestled in a small quiet community just 5 minutes from "Historic Woodstock". Super location! This unit is in very good condition- first floor com...

  • 2 Beds
  • 3 Baths
  • 5077683 MLS
  • ACTIVE Status
598 E Woodstock Rd, Woodstock image
598 E Woodstock Rd, Woodstock $659,000 ▼

Historic Woodstock, Vermont – Spacious Home on Nearly 3 Acres. Welcome to a rare opportunity in the heart of Woodstock, one of Vermont’s most picturesque and sought-after...

  • 4 Beds
  • 3 Baths
  • 5077210 MLS
  • ACTIVE Status
39 Elm St Unit B, Woodstock image
39 Elm St Unit B, Woodstock $1,600,000

The Richmond House Unit B | Woodstock Village. An enduring Woodstock landmark, the iconic Richmond House (c.1826) is a proud brick Federal distinguished by its softly wea...

  • 3 Beds
  • 4 Baths
  • 5076786 MLS
  • ACTIVE Status
249 Sawyer Rd, Woodstock image
249 Sawyer Rd, Woodstock $2,950,000 ▼

Located in Woodstock, Vermont just one mile from the village green, the Alta House offers a rich quality of life filled with poolside sunsets, mountain vistas, proximity ...

  • 3 Beds
  • 5 Baths
  • 5072035 MLS
  • ACTIVE Status
South Rd, Woodstock image
South Rd, Woodstock $646,500

Country land at the south end of Woodstock reaching from RT 106 to the top of the ridge. Potential for views with clearing at several levels. Trails through the property ...

  • 5070692 MLS
  • ACTIVE Status
355 Greene Rd, Woodstock image
355 Greene Rd, Woodstock $14,900,000 ▼

Star Hill Farm is completely private, hidden on a hillside with pastoral and mountain views in the heart of South Woodstock. From the valley floor to the top of Meetingho...

  • 7 Beds
  • 10 Baths
  • 5066210 MLS
  • ACTIVE Status
26 Mt Peg Rd Unit B, Woodstock image
26 Mt Peg Rd Unit B, Woodstock $995,000

Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a...

  • 3 Beds
  • 4 Baths
  • 5065230 MLS
  • ACTIVE Status
26 Mt Peg Rd Unit C, Woodstock image
26 Mt Peg Rd Unit C, Woodstock $995,000

Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a...

  • 3 Beds
  • 4 Baths
  • 5065228 MLS
  • ACTIVE Status
26 Mt Peg Rd Unit A, Woodstock image
26 Mt Peg Rd Unit A, Woodstock $1,195,000

Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a...

  • 3 Beds
  • 4 Baths
  • 5065227 MLS
  • ACTIVE Status
26 Mt Peg Roa Unit D, Woodstock image
26 Mt Peg Roa Unit D, Woodstock $1,195,000

Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a...

  • 3 Beds
  • 4 Baths
  • 5065225 MLS
  • ACTIVE Status
5798 W Woodstock Rd, Woodstock image
5798 W Woodstock Rd, Woodstock $395,000 ▼

Classic Vermont farmhouse just minutes from the heart of Woodstock. This charming 4 bedroom , 2 bath home offers the character of a traditional New England property with ...

  • 4 Beds
  • 2 Baths
  • 5063810 MLS
  • ACTIVE Status
1 Carlton Hill Rd, Woodstock image
1 Carlton Hill Rd, Woodstock $325,000

Sweet Spot - 8 acre building lot located within minutes of the Woodstock Village Green! Driveway is in place and a lovely building site has been cleared and power is at ...

  • 5063317 MLS
  • ACTIVE Status
41 Pleasant St, Woodstock image
41 Pleasant St, Woodstock $2,599,000

This exquisite Victorian invites you to embracequintessential New England living in a charming downtown setting. This property in Woodstock, VT offers a rare blend of his...

  • 9 Beds
  • 11 Baths
  • 5062350 MLS
  • ACTIVE Status
412 Skyland Ln, Woodstock image
412 Skyland Ln, Woodstock $5,950,000 ▼

Once the site of an 1850s homestead and now reimagined for 21st-century living, Skyland Farm is a private retreat on 63 acres. Mineral springs, glass architecture, and ex...

  • 4 Beds
  • 5 Baths
  • 5044620 MLS
  • ACTIVE Status
00 Long Hill Rd, Woodstock image
00 Long Hill Rd, Woodstock $525,000 ▼

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 righ...

  • 5031426 MLS
  • ACTIVE Status
1782 Randall Rd, Woodstock image
1782 Randall Rd, Woodstock $865,000 ▼

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 classi...

  • 4 Beds
  • 3 Baths
  • 5052613 MLS
  • ACTIVE Status
234 Randall Rd, Woodstock image
234 Randall Rd, Woodstock $845,000

Randall Road Farm represents a rare opportunity to purchase a multigenerational family farmstead in an exceptionally desirable location. Long recognized as a well establi...

  • 2 Beds
  • 1 Baths
  • 4913852 MLS
  • ACTIVE Status

board logoCopyright 2026 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, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated .

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