Browse All Woodstock VT Above $1M Properties for Sale

A chance awaits to acquire a brand-new, Vernacular Elevator Duplex Townhome with breathtaking views of Woodstock village rooftops and scenic Billings Museum Farm. This ra...

3 Beds
3 Baths
4986623 MLS
CLOSED Status

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

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 $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 $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

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

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 $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 $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 $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

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 $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

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 $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

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

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

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 $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 $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 $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

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

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 $1,695,000 ▼

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

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

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

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

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

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

182 Rose Hl, Woodstock $2,350,000

This historic home was built in 1904 by John Cotton Dana for his family around 1904. The Danas were a prominent family in Woodstock . The Dana House , home of the Woodst...

5 Beds
5 Baths
5002465 MLS
CLOSED Status

739 Westerdale Rd, Woodstock $2,425,000

Absolutely stunning, newly renovated residence, privately situated towards the end of a quiet town road in Woodstock, in an area of other substantial homes. Lovely mount...

4 Beds
5 Baths
5056790 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

2090 Randall Rd, Woodstock $1,700,000

Constructed in 2007 with a nod to the Gothic Style Vermont Farmhouse vernacular, this beautifully composed country home creatively integrates curated period detail with ...

3 Beds
3 Baths
5025879 MLS
CLOSED Status

2 Maple St, Woodstock $1,145,000

Located in the Heart of Woodstock Village- fantastic location at the foot of the Mtn Peg trail system with easy access to Vail field and all of towns amenities. This be...

4 Beds
4 Baths
5049138 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

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

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

2018 Church Hill Rd, Woodstock $1,810,000

Ideally oriented south and westerly this light-filled contemporary home engages you in the outdoors through expansive windows, decks and screened porch overlooking the sp...

4 Beds
4 Baths
4969169 MLS
CLOSED Status

4411 Church Hill Rd, Woodstock $1,850,000

"The Schoolhouse," is a turn-key village home overflowing with charm and character. Sited on a hill overlooking the picturesque village of South Woodstock, this light-fil...

3 Beds
3 Baths
5001980 MLS
CLOSED Status

55 S Station Rd, Woodstock $1,225,000

Nestled in the White Mountains, this 6-bedroom colonial home sits on 11 private acres with over 1,000 feet of riverfront along the Pemi River, offering endless opportunit...

6 Beds
5 Baths
5035510 MLS
CLOSED Status

57 Main St, Woodstock $1,350,000

Investment opportunity in the heart of the White Mountains. The main Inn was built by Edwin Mattson, a local mill owner, in 1912. He designed it in the craftsman style an...

4991292 MLS
CLOSED Status

50 Upper Grandview, Woodstock $1,495,000

WELCOME TO THE WHITE MTNS – Beautiful and sustainable custom-built, single family home located in N. Woodstock with unobstructed views through Franconia Notch. Proximal t...

5 Beds
4 Baths
4967381 MLS
CLOSED Status

4980 South Rd, Woodstock $1,050,000

This stately home is one of the brick federals built in the early 1800's in the historic village of South Woodstock. Located in what is known as the "Valley of the Kedro...

3 Beds
3 Baths
4997220 MLS
CLOSED Status

16 Depot St, Woodstock $1,395,000

Embrace the epitome of luxury living with this exquisite five bedroom, three bath RIVERFRONT property. Nestled in the heart of the White Mountains, this home offers a uni...

5 Beds
3 Baths
4981043 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

318 Ebbin Lockwood Way, Woodstock $2,750,000

Serene, private, contemporary: Sited on a ridge above South Woodstock village, the 54 acre property offers complete seclusion in an elegant setting with an extensive netw...

3 Beds
4 Baths
4966761 MLS
CLOSED Status

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Above $1 Million Woodstock Real Estate

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