View All Latest Woodstock 4000+ Sq. Ft. Properties for Sale

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
ACTIVE Status

115 Eastman Rd, Woodstock $5,875,000

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

81 Meadow Ln, Woodstock $1,050,000

Perched high above the valley on 5 private acres, 81 Meadow Lane offers one of the most spectacular panoramic mountain view settings in the White Mountains. With over 90 ...

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

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 $2,650,000 ▼

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 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

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

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

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

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

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

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

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

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

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

268 Willow Brook Rd, Woodstock $1,215,000

This elegant residence is an Award Winning Lindal Cedar Home. Private sited on the edge of Woodstock Village it is within walking distance of the nearby King Farm and the...

4 Beds
5 Baths
4968234 MLS
CLOSED Status

43 Main St, Woodstock $1,050,000

A rare waterfront multifamily gem just minutes from Loon Mountain and a short stroll to the charming downtown North Woodstock. With nearly 200 feet of frontage on the sce...

5045376 MLS
CLOSED Status

2055 Church Hill Rd, Woodstock $2,850,000

Nestled among verdant rolling hills, High Birch is located in one of the area’s most desirable regions at the midpoint between Woodstock and South Woodstock Villages. Des...

5 Beds
5 Baths
4997626 MLS
CLOSED Status

119 English Mills Way, Woodstock $1,075,000

An expansive 5 bedroom home, in a private location, conveniently just a few minutes drive from Woodstock Village! Among often sought amenities are a ground floor primary ...

5 Beds
5 Baths
4991097 MLS
CLOSED Status

11 Well Rd, Woodstock $1,049,077

A once in a lifetime property awaits a lucky new owner! Built to host family and friends, this custom home is like no other, built for comfort, entertainment and relaxati...

6 Beds
6 Baths
4951209 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

851 Riverside Park Rd, Woodstock $1,800,000

"All Seasons" is the ultimate Vermont retreat, designed for gatherings and getaways while seamlessly blending rustic charm with modern luxury. This 5,900-sq-ft barn-style...

4 Beds
4 Baths
5025630 MLS
CLOSED Status

41 Pleasant St, Woodstock $2,599,000

This exquisite Victorian invites you to embracequintessential New England living in a charming downtown setting. This property in Woodstock, VT offers a rare blend of his...

9 Beds
11 Baths
5062350 MLS
ACTIVE 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

2334 South Rd, Woodstock $1,650,000

Offered for the first time, the exclusive private residence of one of Woodstock's most notable and prolific builders, Hank Savelberg. Located just five minutes from the W...

3 Beds
3 Baths
5043416 MLS
CLOSED Status

10 College Hill Rd, Woodstock $1,650,000

10 College Hill is the perfect in-village residence, off the main road yet walk-to-everything. The original, historic residence was designed in 1916 by renowned architec...

5 Beds
5 Baths
5031704 MLS
CLOSED 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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4000+ Sq. Ft. Woodstock Real Estate

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