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Browse All Woodstock VT Single Family Properties for Sale

39 Snow King Rd, Woodstock image
39 Snow King Rd, Woodstock $699,000

Welcome to Lost Valley! Tucked into a quiet North Woodstock neighborhood, 39 Snow King Road offers a welcoming White Mountains getaway with 3 bedrooms, 2 baths, and thoug...

  • 3 Beds
  • 2 Baths
  • 5115650 MLS
  • ACTIVE Status
18 Pleasant St, Woodstock image
18 Pleasant St, Woodstock $1,750,000

EATON HOUSE- Steeped in history and ideally situated in Woodstock’s Historic District, the Eaton House is a handsome Greek Revival-inspired residence built in 1856. Set o...

  • 5 Beds
  • 3 Baths
  • 5113873 MLS
  • ACTIVE Status
139 Doe Hill Way, Woodstock image
139 Doe Hill Way, Woodstock $549,000

Welcome to this newly updated sun-filled craftsman home, ideally located just 4 miles from the heart of Woodstock Village and 11 miles from Killington Ski Resort. Set on ...

  • 3 Beds
  • 2 Baths
  • 5113572 MLS
  • ACTIVE Status
8 Golf Ave, Woodstock image
8 Golf Ave, Woodstock $549,000

Nestled in the heart of historic Woodstock. This 1875 colonial abuts Mt. Peg with direct access to the trail system. A large shed in the backyard could be used as a wor...

  • 3 Beds
  • 2 Baths
  • 5113119 MLS
  • PENDING Status
2687 Garvin Hill Rd, Woodstock image
2687 Garvin Hill Rd, Woodstock $2,600,000

2687 GARVIN HILL ROAD- Surrounded by the rolling hills and natural beauty of the Woodstock countryside, 2687 Garvin Hill Road offers a quintessential Vermont lifestyle on...

  • 5 Beds
  • 5 Baths
  • 5112419 MLS
  • ACTIVE Status
4945 South Rd, Woodstock image
4945 South Rd, Woodstock $2,175,000

Located in the heart of the charming hamlet of South Woodstock, the iconic John Arnold Cottle House is widely considered one of Woodstock's finest early residences. Built...

  • 5 Beds
  • 4 Baths
  • 5111700 MLS
  • ACTIVE UNDER CONTRACT Status
6405 Folding Hills Rd, Woodstock image
6405 Folding Hills Rd, Woodstock $1,500,000 ▼

SIGNIFICANT PRICE REDUCTION - SOUTH WOODSTOCK - HILLSIDE FARM estate presents an exceptional opportunity to embrace the quintessential Vermont country lifestyle on 10.1 p...

  • 3 Beds
  • 4 Baths
  • 5111623 MLS
  • ACTIVE Status
811 Eastside Rd, Woodstock image
811 Eastside Rd, Woodstock $359,900

Welcome to this beautifully maintained 4-bedroom, 2-bath home offering over 2,000 square feet of comfortable living space in a prime location. Ideally situated just minut...

  • 4 Beds
  • 2 Baths
  • 5111583 MLS
  • ACTIVE UNDER CONTRACT Status
306 Meoki Way, Woodstock image
306 Meoki Way, Woodstock $2,095,000

Privately set on 6.7 acres just three minutes from the Woodstock Village Green, this Greek Revival-inspired farmhouse offers views of Mount Tom and the Pomfret Hills. Bui...

  • 4 Beds
  • 5 Baths
  • 5111035 MLS
  • ACTIVE UNDER CONTRACT Status
23 Biscuit Hollow Rd, Woodstock image
23 Biscuit Hollow Rd, Woodstock $449,000

This nicely updated ranch on a country acre is a rare opportunity to live in Woodstock without breaking the bank. Perfect for downsizing, one-level living, starting out, ...

  • 3 Beds
  • 1 Baths
  • 5110580 MLS
  • ACTIVE UNDER CONTRACT Status
2033 South Rd, Woodstock image
2033 South Rd, Woodstock $1,395,000

Historic character, beautifully reimagined for modern Vermont living. Minutes from Woodstock Village, this extensively renovated four-bedroom home pairs the warmth and ...

  • 4 Beds
  • 3 Baths
  • 5110412 MLS
  • ACTIVE Status
26 The Grn, Woodstock image
26 The Grn, Woodstock $2,485,000

Built in 1807 by Tille Parker, 26 The Green is one of Woodstock Village’s earliest and perhaps prettiest houses. The Federal style residence originally served as a tavern...

  • 4 Beds
  • 5 Baths
  • 5107880 MLS
  • PENDING Status
2 River St, Woodstock image
2 River St, Woodstock $1,100,000

Lovely cottage nestled on the Ottauquechee River in the heart of historic Woodstock. Incredible river frontage with sprawling lawn for entertaining or just sitting enjoy...

  • 4 Beds
  • 3 Baths
  • 5106838 MLS
  • PENDING Status
13 High St, Woodstock image
13 High St, Woodstock $990,000

Woodstock Village Home~ A rare opportunity to enjoy the best of Woodstock Village living from this charming and beautifully updated 3-bedroom, 2-bath home, once the town...

  • 3 Beds
  • 2 Baths
  • 5105489 MLS
  • CLOSED Status
88 Lost River Rd, Woodstock image
88 Lost River Rd, Woodstock $195,000 ▼

property being sold by trustee, seller has no knowledge of age, or systems within the home. There is no Zoning in the town Woodstock. This property will need work to make...

  • 2 Beds
  • 2 Baths
  • 5104613 MLS
  • ACTIVE Status
5 & 7 Mountainside Rd, Woodstock image
5 & 7 Mountainside Rd, Woodstock $899,900 ▼

Seller is Offering a $10,000 Credit at closing to buy down the interest rate or apply towards closing costs. Mountainside Road really leans into the Mountain get-away the...

  • 5 Beds
  • 4 Baths
  • 5104119 MLS
  • ACTIVE Status
648 Church Hill Rd, Woodstock image
648 Church Hill Rd, Woodstock $1,225,000

This superbly cared-for cape-style home has been thoughtfully and comprehensively updated, with all bathrooms tastefully renovated with quality fixtures and finishes. The...

  • 3 Beds
  • 3 Baths
  • 5103213 MLS
  • CLOSED Status
353 Cabot Rd, Woodstock image
353 Cabot Rd, Woodstock $1,695,000

"BLISS HOUSE" Privately nestled on a picturesque hillside just minutes from the Woodstock Village Green, this beautifully renovated residence offers exceptional privacy, ...

  • 4 Beds
  • 3 Baths
  • 5102668 MLS
  • ACTIVE UNDER CONTRACT Status
68 Russell Farm Rd, Woodstock image
68 Russell Farm Rd, Woodstock $450,000

Enjoy peace, privacy, and endless possibilities on 2 quiet acres, just 3 miles from downtown Woodstock! This adorable ranch-style double-wide offers a bright, open-concep...

  • 3 Beds
  • 2 Baths
  • 5102664 MLS
  • CLOSED Status
16 Church St, Woodstock image
16 Church St, Woodstock $1,195,000 ▼

This wonderful Vermont Cape-style home is a peaceful hideaway with amazing views upriver towards Killington is within walking distance of Village shops, restaurants, and ...

  • 4 Beds
  • 3 Baths
  • 5100512 MLS
  • ACTIVE Status
115 Eastman Rd, Woodstock image
115 Eastman Rd, Woodstock $5,350,000 ▼

Sorgenfrei, German for "carefree" captures the spirit of this remarkable 68 acre property in one of South Woodstock's most desirable locations: a place where life slows a...

  • 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
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
5 Downing Dr, Woodstock image
5 Downing Dr, Woodstock $399,000 ▼

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 image
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
  • CLOSED Status
81 Meadow Ln, Woodstock image
81 Meadow Ln, Woodstock $1,050,000

OPEN HOUSE - SUNDAY 10/11 - 10:00AM TO 12:00PM. Perched high above the valley on 5 private acres, 81 Meadow Lane offers one of the most spectacular panoramic mountain vie...

  • 5 Beds
  • 4 Baths
  • 5097556 MLS
  • ACTIVE Status
19 Hamlet Dr, Woodstock image
19 Hamlet Dr, Woodstock $245,000

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
  • CLOSED Status
1326 Curtis Hollow Rd, Woodstock image
1326 Curtis Hollow Rd, Woodstock $750,000 ▼

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 $1,645,000 ▼

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 image
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
  • PENDING Status
473 Kendall Rd, Woodstock image
473 Kendall Rd, Woodstock $1,995,000

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
  • CLOSED 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
2 High St, Woodstock image
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 image
358 Cowdrey Path, Woodstock $849,000 ▼

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

  • 3 Beds
  • 3 Baths
  • 5094379 MLS
  • ACTIVE Status
1294 Daniel Webster Hwy, Woodstock image
1294 Daniel Webster Hwy, Woodstock $459,000

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
  • CLOSED Status
1113 Daniel Webster Hwy, Woodstock image
1113 Daniel Webster Hwy, Woodstock $560,000

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
  • CLOSED Status
66 Hollow Farm Rd, Woodstock image
66 Hollow Farm Rd, Woodstock $2,650,000 ▼

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 UNDER CONTRACT 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
25 Sargent St, Woodstock image
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 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
2358 Long Hill Rd, Woodstock image
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 image
2605 Cox District Rd, Woodstock $737,500

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
  • CLOSED Status
11 Maple St, Woodstock image
11 Maple St, Woodstock $595,000 ▼

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
88 Happy Valley Rd, Woodstock image
88 Happy Valley Rd, Woodstock $515,000

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
  • CLOSED Status
2394 Fletcher Hill Rd, Woodstock image
2394 Fletcher Hill Rd, Woodstock $1,695,000 ▼

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 image
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 image
37 South St, Woodstock $680,000

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

  • 3 Beds
  • 2 Baths
  • 5081166 MLS
  • CLOSED Status
19 Davry Way, Woodstock image
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 image
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

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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eXp Realty
(603) 219-6773
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