Browse All Woodstock VT Single Family Properties for Sale

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 $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 $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 $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 $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

5 Downing Dr, Woodstock $430,000

Welcome to 5 Downing Drive, where a peaceful setting and convenient location come together in the heart of the White Mountains. Expansive windows fill the home with abund...

3 Beds
2 Baths
5098036 MLS
ACTIVE UNDER CONTRACT Status

20 Potato Hill Rd, Woodstock $399,000

Experience tranquility in this charming 2+ bedroom ranch, perfectly situated on a private 1.22 acre lot. Enjoy the peaceful surroundings while being just a short drive fr...

2 Beds
1 Baths
5097869 MLS
ACTIVE UNDER CONTRACT Status

81 Meadow Ln, Woodstock $1,050,000

OPEN HOUSE - Sunday July 12th - 10:00am to 2:00pm. Perched high above the valley on 5 private acres, 81 Meadow Lane offers one of the most spectacular panoramic mountain ...

5 Beds
4 Baths
5097556 MLS
ACTIVE Status

19 Hamlet Dr, Woodstock $299,900

Nestled in a peaceful, natural setting overlooking scenic Mirror Lake, this small and charming cabin offers a true retreat for those seeking simplicity and a connection t...

3 Beds
2 Baths
5097289 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

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

18 The Grn, Woodstock $2,999,000

Centrally located on the southwest side of the historic Woodstock Village Green, this classic c1840 Greek Revival farmhouse is one of the town’s finest residences. Loving...

6 Beds
8 Baths
5096089 MLS
ACTIVE UNDER CONTRACT Status

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

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

2 High St, Woodstock $1,080,000

Beautifully Restored all the way down to the studs, c. 1890 Village Home in the Heart of downtown Woodstock! Extensively renovated while preserving its historic charm, th...

3 Beds
3 Baths
5094456 MLS
CLOSED Status

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

1294 Daniel Webster Hwy, Woodstock image

1294 Daniel Webster Hwy, Woodstock $519,000

Believed to be the oldest home in town, this remarkable c.1790 property offers a rare opportunity to own a piece of local heritage. Located in the town of Woodstock, and ...

5 Beds
3 Baths
5093544 MLS
ACTIVE Status

1113 Daniel Webster Hwy, Woodstock image

1113 Daniel Webster Hwy, Woodstock $589,900

Charming New Englander with Income-Producing Apartment in a Prime Location Well-maintained 4-bedroom, 3-bathroom New Englander-style single-family home featuring an atta...

4 Beds
3 Baths
5093238 MLS
ACTIVE UNDER CONTRACT Status

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

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

25 Sargent St, Woodstock $449,900

Well-maintained ranch-style home in the heart of North Woodstock offering easy one-level living with 3 bedrooms, 2 baths, and first-floor laundry. The level yard provides...

3 Beds
2 Baths
5089555 MLS
CLOSED 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

2605 Cox District Rd, Woodstock $785,000 ▼

This lovely four-bedroom, 2.5-bath cape features a two-car attached garage and a separate 700+/- sq. ft. one-bedroom apartment. The property also includes a separate outb...

5 Beds
4 Baths
5088406 MLS
ACTIVE UNDER CONTRACT Status

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 $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

88 Happy Valley Rd, Woodstock $502,000 ▼

Step into a rare offering where timeless New England charm meets contemporary comfort. Originally built in 1846 and thoughtfully reimagined, this exceptional Taftsville, ...

4 Beds
3 Baths
5085202 MLS
ACTIVE UNDER CONTRACT 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

51 River St, Woodstock $870,000

Beautiful residence with newer renovations...located in the heart of historic Woodstock. Sunlit rooms, open floor concept with handsome refinished original pine floors. ...

4 Beds
2 Baths
5084320 MLS
CLOSED Status

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

19 Davry Way, Woodstock $630,000

You know that feeling when you walk through a door and you can already see future memories being made? That's what you feel as you turn every corner of this gem. This tho...

3 Beds
2 Baths
5080038 MLS
CLOSED Status

23 Courtney Rd, Woodstock $400,000

This three-bedroom, one-bathroom home on an 0.22-acre lot in North Woodstock, New Hampshire offers prime access to the White Mountains. What sets this location apart is i...

3 Beds
1 Baths
5078682 MLS
CLOSED Status

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

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

22 Sharon Hill Dr, Woodstock $300,000

Perched atop Sharon Hill in the heart of North Woodstock, this unique 2-bedroom, 2-bath home offers charm, flexibility, and sweeping mountain views in one of the White Mo...

2 Beds
2 Baths
5076623 MLS
CLOSED Status

958 E Woodstock Rd, Woodstock $977,500

Set along East Woodstock Road with sweeping views across the Woodstock Valley, this thoughtfully renovated farmhouse pairs timeless Vermont character with a refined moder...

4 Beds
3 Baths
5075123 MLS
CLOSED Status

137 Laughlin Rd, Woodstock $712,000

Charming property located just minutes from historic Woodstock Green. The main house first floor features 3 bedrooms/ 1bath with formal dining room, living room and kitc...

5 Beds
3 Baths
5074725 MLS
CLOSED Status

69 Grandview Dr, Woodstock $560,000

Price Improvement to $599,900 — Don’t Miss This Opportunity in North Woodstock! Welcome to 69 Grandview — a beautifully renovated mountain retreat set on 1.2 acres in one...

4 Beds
2 Baths
5074112 MLS
CLOSED Status

819 Eastside Rd, Woodstock $499,900 ▼

This property enjoys all four seasons in the White Mountains.Snowmobile to corridor 11 just outside the door , Loon and Cannon , Waterville Valley just a short ride . Su...

3 Beds
2 Baths
5073667 MLS
ACTIVE Status

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

256 Barnard Rd, Woodstock $800,000

Discover the charm of historic Woodstock in this beautifully maintained late-1800s residence, set on just over an acre of flat, open lawn and ideally located within walki...

4 Beds
4 Baths
5069833 MLS
CLOSED Status

125 Shurtleff Ln, Woodstock $1,175,000

Beautifully sited just a short walk from Woodstock Village, this 2015 custom-built home blends modern comfort with timeless Vermont charm. Thoughtfully designed for every...

4 Beds
5 Baths
5069230 MLS
CLOSED Status

75 Pleasant St, Woodstock $525,000

Situated on a lovely .4 acre parcel in the heart of Woodstock Village, this newer construction open-concept home offers modern conveniences combined with superb access to...

3 Beds
1 Baths
5068156 MLS
CLOSED Status

33 Mountain Ave, Woodstock $1,150,000

Welcome to 33 Mountain Avenue – a mid-century modern gem poised perfectly on the edge of Faulkner Park and at the foot of Mt. Tom and once part of the Marianne Faulkner E...

2 Beds
4 Baths
5067740 MLS
CLOSED Status

3914 South Rd, Woodstock $660,000

This South Woodstock contemporary residence was designed by the original architect-owner to showcase Vermont’s changing seasons and capture views of the Kedron Brook as i...

4 Beds
3 Baths
5067285 MLS
CLOSED Status

23 Oakes St, Woodstock $460,000

More Space, More Privacy, Less Hassle - All for Less than a Condo! Well-maintained and full of charm, this Oakes Road home sits on a spacious lot in a peaceful neighborho...

2 Beds
1 Baths
5066982 MLS
CLOSED 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

4 Stanton St, Woodstock $655,000

Step back in time with this classic 1901 Gambrel-style residence, brimming with character and ready for your renovations and personal touch. Featuring 4 bedrooms and 3 ba...

4 Beds
3 Baths
5065029 MLS
CLOSED Status

1079 Fletcher Hill Rd, Woodstock $400,000

This charming 2-bedroom ranch house offers a nice layout for main floor living. Features include a sunroom entrance, two bedrooms, a full bath, laundry room, and a main l...

2 Beds
2 Baths
5064428 MLS
CLOSED Status

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Woodstock Single Family Real Estate

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