View All Latest Woodstock 2500+ 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

3036 W Woodstock Rd, Woodstock $799,999 ▲

On a small hill, amongst trees and beautiful gardens, sits this beautifully maintained log cabin with sweeping views of the surrounding mountains and river valley. Just ...

3 Beds
3 Baths
5098474 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

358 Cowdrey Path, Woodstock $965,000

This beautifully renovated, truly move-in-ready home has been thoughtfully updated throughout — including a brand-new kitchen, refreshed flooring, modernized bathrooms, f...

3 Beds
3 Baths
5094379 MLS
ACTIVE Status

1294 Daniel Webster Hwy, Woodstock image

1294 Daniel Webster Hwy, Woodstock $519,000

Believed to be the oldest home in town, this remarkable c.1790 property offers a rare opportunity to own a piece of local heritage. Located in the town of Woodstock, and ...

5 Beds
3 Baths
5093544 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

252-254 Lost River Rd, Woodstock $530,000

Great investment opportunity in the beautiful White Mountains. This could be strictly rental property or it could be your 2 bedroom home with 2 apartments for rental inc...

5089528 MLS
ACTIVE UNDER CONTRACT 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

2394 Fletcher Hill Rd, Woodstock $1,895,000

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

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

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

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

26 Mt Peg Rd Unit B, Woodstock $995,000

Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a...

3 Beds
4 Baths
5065230 MLS
ACTIVE Status

26 Mt Peg Rd Unit C, Woodstock $995,000

Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a...

3 Beds
4 Baths
5065228 MLS
ACTIVE Status

26 Mt Peg Rd Unit A, Woodstock $1,195,000

Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a...

3 Beds
4 Baths
5065227 MLS
ACTIVE Status

348 Laughlin Rd, Woodstock $920,000

Stunning contemporary extensively renovated and idyllically situated on a westerly facing hillside overlooking the village of Woodstock offers a coveted Woodstock locatio...

4 Beds
3 Baths
5064076 MLS
CLOSED Status

8 Cascades Dr Unit #273, Woodstock image

8 Cascades Dr Unit #273, Woodstock $650,000

Invite them all !! This 4 bedroom 4 bath condo spreads you out over 3 floors and offers Direct access and Views of the West Branch of the Pemigewasset River. The Associat...

4 Beds
4 Baths
4972721 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

339 Gully Rd, Woodstock $740,000

Peaceful Gully Road Retreat. Just minutes from Woodstock Village. Set on 5.1 private acres along quiet and desirable Gully Road, this beautifully updated four-bedroom, tw...

4 Beds
3 Baths
5037463 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

24 High St, Woodstock $460,000

Constructed in 1840, this post & beam home is situated in the heart of Woodstock Village. A short stroll across the Kedron Brook footbridge to shopping and restaurants, t...

5 Beds
2 Baths
4997618 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

326 Hall Cir, Woodstock $1,175,000

This timber framed home is sited to take advantage of sweeping long range southerly views of hayfields and forest land protected by a development restriction as a gift by...

4 Beds
3 Baths
4962162 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

45 Profile Dr, Woodstock $919,900

Welcome to 45 Profile drive in North Woodstock. The perfect setting for your new home or perhaps your White Mountain getaway. This is the first time this custom built 4 ...

4 Beds
3 Baths
4972085 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

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

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2500+ Sq. Ft. Woodstock Real Estate

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