Browse All Properties for Sale with Barn

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

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

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

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

2358 Long Hill Rd, Woodstock $6,673,000

Framed by groves of mature birch trees, a winding drive descends into a private valley surrounded by pastures, apple orchards, a spring-fed pond, and sweeping mountain vi...

5 Beds
4 Baths
5089158 MLS
PENDING Status

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

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

513 Deer Brook Way, Woodstock $1,100,000

Set on a sun-bathed hillside between Woodstock Village and the renowned slopes of Killington and Pico, this custom-built Colonial captures what buyers seek most in Vermon...

4 Beds
3 Baths
5077012 MLS
CLOSED Status

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

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

1362 Barnard Rd, Woodstock $2,097,500

Gilbert’s Hill, the very best of Vermont living - Iconic, 112-acre estate with a storybook history as the first “modern” ski run in the US. Located two miles from the v...

6 Beds
5 Baths
5066205 MLS
CLOSED Status

608 Fletcher Hill Rd, Woodstock $1,300,000

Open House Sunday, April 13, 12:00 to 2:00 - Tucked away in the serene forests of Woodstock, Vermont, this beautifully remodeled 11-room home offers 4 bedrooms, 4 bathroo...

4 Beds
4 Baths
5028430 MLS
CLOSED Status

1075 Westerdale Rd, Woodstock $1,275,000

This lovingly maintained property with mountain views has been enjoyed by a single family since its construction in 1985. The open-concept layout is anchored by a stone R...

3 Beds
4 Baths
5022674 MLS
CLOSED Status

13 Golf Ave, Woodstock $700,000

Charming circa 1880 cape in Woodstock Village! Located on a quiet dead-end street across from Mt Peg trail head... Walk to all of towns amenities, shops, restaurants an...

2 Beds
2 Baths
5043874 MLS
CLOSED Status

1548 Peterkin Hill Rd, Woodstock $1,100,000

A classic, beautifully maintained residence in an exceptional location in South Woodstock, 8 minutes to the Village Green, in an area of substantial homes and estates, si...

4 Beds
4 Baths
5023612 MLS
CLOSED Status

5851 South Rd, Woodstock $613,000

This charming home is an amazing opportunity to own a piece of history in the lovely village of South Woodstock , Vermont. Starting its life as the garage and home of Cly...

3 Beds
3 Baths
5014012 MLS
CLOSED Status

76 Grove Hill Rd, Woodstock $1,380,000

Great location, views and updated 3 BR / 2.5 BA contemporary cape, with a detached 3 car garage and a fully insulated/heated "geobarn" workshop with finished TV/Rec room ...

3 Beds
3 Baths
4997315 MLS
CLOSED Status

5250 W Woodstock Rd, Woodstock $1,700,000

The iconic Farmhouse Inn overlooking the Ottauquechee River is located west of Woodstock Village within 15- and 30-minutes’ drive of the Killington and Okemo ski resorts,...

9 Beds
9 Baths
4918791 MLS
CLOSED Status

587 Old River Rd, Woodstock $7,775,000

Old Fitch Farm is one of New England’s most extraordinary estates. This remarkable residence is sited graciously on a plateau with 1200' of frontage on the Ottauquechee R...

5 Beds
6 Baths
4923048 MLS
CLOSED Status

5798 South Rd, Woodstock $2,000,000

For nearly two centuries the iconic Kedron Valley Farm has served as the gateway to the village of South Woodstock. Prominently sited on a knoll with lovely valley views ...

5 Beds
6 Baths
4968227 MLS
CLOSED Status

113 Prosper Rd, Woodstock $1,500,000

A rare opportunity to advance a premier Woodstock estate to its finest possibilities. This circa 1840 four-bedroom antique Farmhouse is sited on 18+ acres of idyllic roll...

4 Beds
1 Baths
4959862 MLS
CLOSED Status

486 Benedict Rd, Woodstock $3,350,000

"BENEDICT HILL" - sited on 38 acres on a quiet gravel road in a premier location in South Woodstock is this truly classic Vermont estate property. Excellent equestrian /...

6 Beds
7 Baths
4986511 MLS
CLOSED Status

3090 South Rd, Woodstock $742,162

Exposed beams and wide board wood floors accentuate the classic interior of this 5 bedroom Woodstock home! Pastoral views, large terraced lawns and massive stonewalls def...

5 Beds
5 Baths
4935033 MLS
CLOSED Status

327 Fletcher Schoolhouse Rd, Woodstock image

327 Fletcher Schoolhouse Rd, Woodstock $4,205,000

ByBrook Farm: Reimagined, turnkey 1790s farmhouse set in one of Vermont's most loved valleys, perennial gardens, stone walls, a spring fed pond, a brook, and rolling mead...

4 Beds
4 Baths
4993127 MLS
CLOSED Status

3752 Densmore Hill Rd, Woodstock $573,000

Escape to the green mountains of Vermont! This 23.46 acres is ideally located just 2 miles south of Woodstock VT in the very desirable area of South Woodstock. As the say...

3 Beds
2 Baths
4976148 MLS
CLOSED Status

68 Russell Farm Rd, Woodstock $422,000

Here is the location you have been waiting for, 2 quiet, private acres only 3 miles to downtown Woodstock. When you walk into this 2017 double wide manufactured home you...

3 Beds
2 Baths
4975766 MLS
CLOSED Status

587 College Hill Rd, Woodstock $2,300,000

Absolutely incredible location on 5+ acres with fabulous long range views yet only a short 10 min walk to the Woodstock village green. This newer and beautifully maintai...

4 Beds
3 Baths
4966586 MLS
CLOSED Status

4662 W Woodstock Rd, Woodstock $462,500

Sited 4 miles west of Woodstock Village this split-level ranch enjoys a sunny southerly orientation providing light, warmth and energy from the roof-mounted solar array. ...

5 Beds
3 Baths
4979214 MLS
CLOSED Status

433 Cowdrey Path, Woodstock $975,000

Splendid contemporary cape and separate barn guest apartment idyllically nestled on an open and sunny hillside in the heart of South Woodstock horse country. The light an...

4 Beds
4 Baths
4932619 MLS
CLOSED Status

513 Deerbrook Way, Woodstock $1,200,000

This classic New England Colonial home is perched on a hillside to take advantage of the pleasant views of the distant hills and to benefit from its southern exposure. Th...

4 Beds
3 Baths
4972415 MLS
CLOSED Status

33 River St, Woodstock $1,580,000

BEAUTIFULLY renovated rare antique residence in the heart of historic Woodstock! Located in a premiere neighborhood within walking distance to all of towns amenities, hi...

4 Beds
4 Baths
5009557 MLS
CLOSED Status

4945 South Rd, Woodstock $1,850,000

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 ...

5 Beds
4 Baths
5028924 MLS
CLOSED Status

100 Pomfret Rd, Woodstock $875,000

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, ...

4 Beds
3 Baths
5044013 MLS
CLOSED Status

917 Carlton Hill Rd, Woodstock $875,000

Gorgeous contemporary, minutes from Woodstock! Spacious, light-filled, and thoroughly charming, this home feels like an escape - a mere 2.5 miles from the heart of Woods...

3 Beds
3 Baths
4997696 MLS
CLOSED Status

39 Elm St Unit Unit B, Woodstock $1,600,000

For good reason, the Richmond House is one of Woodstock's most photographed homes. This stately 1826 brick Federal with all the architectural trimmings and distinctly wea...

3 Beds
4 Baths
4982328 MLS
CLOSED Status

1059 Carlton Hill Rd, Woodstock $2,220,000

Set on over two picturesque acres along one of the most beautiful country roads in the area, this spacious and impeccably renovated contemporary farmhouse offers the perf...

5 Beds
5 Baths
5059827 MLS
CLOSED Status

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

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

61 Academy Cir, Woodstock $2,500,000 ▼

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 ...

6 Beds
6 Baths
5002873 MLS
ACTIVE UNDER CONTRACT Status

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