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View All Latest Woodstock 5000+ Sq. Ft. Properties for Sale

115 Eastman Rd, Woodstock image
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
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
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
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
355 Greene Rd, Woodstock image
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 image
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
587 Old River Rd, Woodstock image
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
318 Ebbin Lockwood Way, Woodstock image
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
486 Benedict Rd, Woodstock image
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
268 Willow Brook Rd, Woodstock image
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 image
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 image
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
11 Well Rd, Woodstock image
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
851 Riverside Park Rd, Woodstock image
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 image
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
412 Skyland Ln, Woodstock image
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 image
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
61 Academy Cir, Woodstock image
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

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 .

5000+ Sq. Ft. Woodstock Real Estate

Our website features the best real estate search for 5000+ sq. ft. properties available in Woodstock and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!

Address Search

Karolina Burtt - Realtor
eXp Realty
(603) 219-6773
Contact Me

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603-219-6773

eXp Realty
6 Loudon Rd. Suite 504
Concord, NH 03301
Office: 888.398.7062 x165

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