View All Latest Woodstock 3000+ Sq. Ft. 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

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 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

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

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

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

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

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 $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

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

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

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

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

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

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

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

26 River St, Woodstock $1,100,000

One of Woodstock's most beautiful Greek Revival homes sited on a landscaped village lot that rolls gently down to the Ottauquechee River. The riverfront lawn is sheltere...

6 Beds
4 Baths
4954906 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

7 Golf Ave, Woodstock $550,000

Super location! Nestled in the historic village of Woodstock- Built in 1832- this 3500+ squ foot home boast tall ceilings with handsome hardwood floors, kitchen with a...

5 Beds
3 Baths
4966983 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

418 Fletcher Hill Rd, Woodstock $625,000

Located on a lovely country road in South Woodstock this very charming custom built log home enjoys long range mountain views. Enjoy entertaining on the wrap around porch...

3 Beds
3 Baths
4966735 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

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

484 Carlton Hill Rd, Woodstock $1,800,000

Make this unique Adirondack-style home, with its rich stone and timber frame, and perfect location along the banks of the Ottauquechee River, your new Vermont retreat. Ev...

4 Beds
5 Baths
5032740 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

185 Lost River Rd, Woodstock $460,000

With nearly 5000 square feet of space, this property offers a number of possibilities and is a great opportunity for the creative buyer - particularly given the lack of t...

2 Baths
4962497 MLS
CLOSED Status

72 Frenchs Rd, Woodstock $1,200,000

In 1880, this lovely hilltop Gambrel Colonial was designed by the prominent Manhattan Architectural Firm, McKim, Mead and White. “Rose Hill” was one of Woodstock’s most p...

6 Beds
4 Baths
5014859 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

35 Pleasant Heights Dr, Woodstock $1,296,000

This fabulous home has the best view we've ever seen here in the Loon Valley. You'll enjoy looking into Franconia Notch and west towards Kinsman Notch. The home features ...

3 Beds
3 Baths
5009898 MLS
CLOSED Status

2409 South Rd, Woodstock $1,125,000

This splendid 1920 Vermont Farmhouse with Post and Beam Great Room and detached barn with a 1-bedroom guest apartment is sited beautifully on 2.74 acres that are detailed...

4 Beds
3 Baths
4961738 MLS
CLOSED Status

612 Church Hill Rd, Woodstock $1,400,000

MODERN COMFORT IN WOODSTOCK - Enjoy summer sunsets from the deck of this gracious five-bedroom Woodstock home. Built in 2009 and subsequently finished to exacting standa...

5 Beds
4 Baths
4958860 MLS
CLOSED Status

51 Watkins Way Unit Unit 2, Woodstock image

51 Watkins Way Unit Unit 2, Woodstock $1,900,000

51 Watkins Way, Unit 2 – Woodstock Village, Vermont Experience modern comfort and timeless Vermont vernacular style in this 2021 constructed 2,280 sq. ft. Elevator Barn ...

3 Beds
3 Baths
5059959 MLS
CLOSED Status

1133 Atwood Ln, Woodstock $1,499,000

**Price Improvement**Beautiful country contemporary home offers the best of Vermont living.Private yet convenient,just 6 miles from Woodstock Village and within 30 min. d...

3 Beds
3 Baths
4998131 MLS
CLOSED Status

2876 Hartland Hill Rd, Woodstock $1,570,000

This property is the quintessential classic Vermont farmhouse featuring the "big house, little house, backhouse, barn" concept. Conveniently located only 1.4 miles from ...

4 Beds
4 Baths
4967464 MLS
CLOSED Status

144 Town Farm Rd, Woodstock $1,800,000

Sense of place - the Lewis Farm: The classic Vermont farmstead with an iconic big red barn above Green Mountain Horse Association, the Lewis Farm's 130 acres of hayfields...

8 Beds
5 Baths
4937127 MLS
CLOSED Status

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3000+ Sq. Ft. Woodstock Real Estate

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