View All Latest Woodstock 3500+ 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

5 & 7 Mountainside Rd, Woodstock $899,900 ▼

Mountainside Road really leans into the Mountain get-away theme of New Hampshire. This property is currently being used as an Air B & B, featuring a main house with 4 bed...

5 Beds
4 Baths
5104119 MLS
ACTIVE 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 $5,875,000

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

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
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

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

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

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

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

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

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

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

15 Hathorn Hill Ext, Woodstock $2,210,000

An incredibly rare combination of in-Village and country living. 4+ acres and privacy with a pond and heated in-ground pool, yet walk-to-the Green. The residence, designe...

4 Beds
4 Baths
5043750 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

3086 South Rd, Woodstock $2,900,000

Beautifully and extensively renovated residence, newer construction barn-garage with five overhead doors and an attached one-bedroom apartment (ADU). The land component ...

4 Beds
5 Baths
5039367 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

11 College Hill Rd, Woodstock $1,320,000

Welcome to 11 College Hill Road - Situated in the heart of Woodstock Village, this classic 1919 Gambrel offers space, charm, and incredible views of both the Ottauquechee...

5 Beds
4 Baths
5038647 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

4945 South Rd, Woodstock $1,850,000

The John Arnold Cottle House is a landmark residence in the heart of South Woodstock, a rare blend of village convenience and country living. Built in 1811 by one of the ...

5 Beds
4 Baths
5028924 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

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3500+ Sq. Ft. Woodstock Real Estate

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