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View All Latest Woodstock 1500+ Sq. Ft. Properties for Sale

16 Church St, Woodstock image
16 Church St, Woodstock $1,375,000

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 image
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 image
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 image
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
121 Townhouse Way Unit 24, Woodstock image
121 Townhouse Way Unit 24, Woodstock $497,500

Live Work Play, Retire and Play, or Just Play on the Weekends and Holidays! This wonderful 3 BR, 3 Bath Townhome/Condo has it all. Nestled in a small quiet wooded comm...

  • 3 Beds
  • 3 Baths
  • 5098210 MLS
  • ACTIVE Status
5 Downing Dr, Woodstock image
5 Downing Dr, Woodstock $430,000

Welcome to 5 Downing Drive, where a peaceful setting and convenient location come together in the heart of the White Mountains. Expansive windows fill the home with abund...

  • 3 Beds
  • 2 Baths
  • 5098036 MLS
  • ACTIVE UNDER CONTRACT Status
81 Meadow Ln, Woodstock image
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
1326 Curtis Hollow Rd, Woodstock image
1326 Curtis Hollow Rd, Woodstock $799,000

If you've been dreaming of the quintessential Vermont lifestyle, this exceptional property delivers the perfect blend of privacy, charm, and convenience. Nestled on over ...

  • 3 Beds
  • 3 Baths
  • 5097258 MLS
  • ACTIVE Status
2706 E Woodstock Rd, Woodstock image
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 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
  • ACTIVE UNDER CONTRACT Status
121 Townhouse Way Unit 20, Woodstock image
121 Townhouse Way Unit 20, Woodstock $465,000

Spacious, immaculate, and beautifully maintained Federal-style brick townhouse located in the prestigious village of Woodstock, often recognized as one of America’s most ...

  • 3 Beds
  • 3 Baths
  • 5095918 MLS
  • ACTIVE Status
473 Kendall Rd, Woodstock image
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
11 Maple St, Woodstock image
11 Maple St, Woodstock $649,000 ▼

A rare Woodstock Village opportunity! A Victorian style home located in Woodstock's much desired Maple Street neighborhood! Popular Vail Field recreation area is convenie...

  • 5095205 MLS
  • ACTIVE 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
2 High St, Woodstock image
2 High St, Woodstock $1,199,000

Beautifully Restored all the way down to the studs, c. 1890 Village Home in the Heart of downtown Woodstock! Extensively renovated while preserving its historic charm, th...

  • 3 Beds
  • 3 Baths
  • 5094456 MLS
  • ACTIVE UNDER CONTRACT Status
358 Cowdrey Path, Woodstock image
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
1113 Daniel Webster Hwy, Woodstock image
1113 Daniel Webster Hwy, Woodstock $589,900

Charming New Englander with Income-Producing Apartment in a Prime Location Well-maintained 4-bedroom, 3-bathroom New Englander-style single-family home featuring an atta...

  • 4 Beds
  • 3 Baths
  • 5093238 MLS
  • ACTIVE UNDER CONTRACT Status
66 Hollow Farm Rd, Woodstock image
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
85 Town House Way Unit 18, Woodstock image
85 Town House Way Unit 18, Woodstock $510,000

Enjoy the ease of townhouse living in this beautiful fully furnished end unit filled with natural light throughout. The setting is surrounded by woodlands and lovely la...

  • 2 Beds
  • 3 Baths
  • 5090924 MLS
  • ACTIVE UNDER CONTRACT Status
47 Pleasant St, Woodstock image
47 Pleasant St, Woodstock $695,000 ▼

Excellent opportunity for residential or office/commercial space with easy access and high visibility on Rt 4 coming into town, Currently configured as office space down...

  • 3 Beds
  • 2 Baths
  • 5089949 MLS
  • ACTIVE Status
1522 Barnard Rd, Woodstock image
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 image
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 image
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 image
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
11 Maple St, Woodstock image
11 Maple St, Woodstock $649,000 ▼

A rare Woodstock Village opportunity! A Victorian style home located in Woodstock's much desired Maple Street neighborhood! Popular Vail Field recreation area is convenie...

  • 4 Beds
  • 2 Baths
  • 5088170 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
88 Happy Valley Rd, Woodstock image
88 Happy Valley Rd, Woodstock $502,000 ▼

Step into a rare offering where timeless New England charm meets contemporary comfort. Originally built in 1846 and thoughtfully reimagined, this exceptional Taftsville, ...

  • 4 Beds
  • 3 Baths
  • 5085202 MLS
  • ACTIVE UNDER CONTRACT Status
2394 Fletcher Hill Rd, Woodstock image
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
51 River St, Woodstock image
51 River St, Woodstock $870,000

Beautiful residence with newer renovations...located in the heart of historic Woodstock. Sunlit rooms, open floor concept with handsome refinished original pine floors. ...

  • 4 Beds
  • 2 Baths
  • 5084320 MLS
  • CLOSED Status
37 South St, Woodstock image
37 South St, Woodstock $718,500 ▼

Great new price! Nestled in the vibrant heart of Woodstock Village, this beautifully renovated residence offers the ultimate "walk-to-all" lifestyle. Stepping inside, ne...

  • 3 Beds
  • 2 Baths
  • 5081166 MLS
  • ACTIVE Status
11 Cascade Dr Unit 288, Woodstock image
11 Cascade Dr Unit 288, Woodstock $499,500 ▼

Major Price Reduction of $35K!!! Welcome to the White Mountains of New Hampshire! This beautifully maintained 2-bedroom, 3-bath townhome is located in Deer Park, one of ...

  • 2 Beds
  • 3 Baths
  • 5080430 MLS
  • ACTIVE Status
57 Townhouse Way Unit 9, Woodstock image
57 Townhouse Way Unit 9, Woodstock $456,250

This beautiful Woodstock West Townhouse offers effortless, low-maintenance living in one of Vermont’s most charming four-season destinations. The main level welcomes you ...

  • 3 Beds
  • 3 Baths
  • 5080108 MLS
  • CLOSED Status
19 Davry Way, Woodstock image
19 Davry Way, Woodstock $630,000

You know that feeling when you walk through a door and you can already see future memories being made? That's what you feel as you turn every corner of this gem. This tho...

  • 3 Beds
  • 2 Baths
  • 5080038 MLS
  • CLOSED Status
1646 Daniel Webster Hwy Unit Unit 42, Woodstock image
1646 Daniel Webster Hwy Unit Unit 42, Woodstock $410,000

Here is an opportunity for you! Conveniently located off Exit 30 at the Jack O’Lantern Resort, this 3-bedroom, 3-bathroom condo—with a loft and lock-off suite option—offe...

  • 3 Beds
  • 3 Baths
  • 5078772 MLS
  • ACTIVE UNDER CONTRACT Status
85 Townhouse Way Unit 14, Woodstock image
85 Townhouse Way Unit 14, Woodstock $465,000 ▼

Fully furnished condo nestled in a small quiet community just 5 minutes from "Historic Woodstock". Super location! This unit is in very good condition- first floor com...

  • 2 Beds
  • 3 Baths
  • 5077683 MLS
  • ACTIVE Status
14 Ridge Dr Unit C-38, Woodstock image
14 Ridge Dr Unit C-38, Woodstock $649,000

Unit 38-14 Ridge Drive C — Where Mountain Living Meets Lakeside Charm! Welcome to your dream White Mountains retreat! This well maintained 3-bedroom, 3-bathroom townhome ...

  • 3 Beds
  • 3 Baths
  • 5077255 MLS
  • CLOSED Status
598 E Woodstock Rd, Woodstock image
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 image
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 image
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
7 Sundance Rd Unit 4, Woodstock image
7 Sundance Rd Unit 4, Woodstock $425,000

Welcome to your new home or home away from home located in beautiful Woodstock NH. This unique townhome offers a versatile floor plan that is warm and inviting. Cozy up b...

  • 2 Beds
  • 3 Baths
  • 5075449 MLS
  • ACTIVE Status
958 E Woodstock Rd, Woodstock image
958 E Woodstock Rd, Woodstock $977,500

Set along East Woodstock Road with sweeping views across the Woodstock Valley, this thoughtfully renovated farmhouse pairs timeless Vermont character with a refined moder...

  • 4 Beds
  • 3 Baths
  • 5075123 MLS
  • CLOSED Status
137 Laughlin Rd, Woodstock image
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
69 Grandview Dr, Woodstock image
69 Grandview Dr, Woodstock $560,000

Price Improvement to $599,900 — Don’t Miss This Opportunity in North Woodstock! Welcome to 69 Grandview — a beautifully renovated mountain retreat set on 1.2 acres in one...

  • 4 Beds
  • 2 Baths
  • 5074112 MLS
  • CLOSED Status
819 Eastside Rd, Woodstock image
819 Eastside Rd, Woodstock $499,900 ▼

This property enjoys all four seasons in the White Mountains.Snowmobile to corridor 11 just outside the door , Loon and Cannon , Waterville Valley just a short ride . Su...

  • 3 Beds
  • 2 Baths
  • 5073667 MLS
  • ACTIVE Status
4 Jack Olantern Dr Unit 31, Woodstock image
4 Jack Olantern Dr Unit 31, Woodstock $410,000 ▼

Welcome to your golf course retreat where comfort meets convenience in this thoughtfully designed, 3 bedrooms plus loft, 3 bath condo nestled in the heart of New Hampshir...

  • 3 Beds
  • 3 Baths
  • 5072362 MLS
  • ACTIVE Status
249 Sawyer Rd, Woodstock image
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 image
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 image
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
33 Mountain Ave, Woodstock image
33 Mountain Ave, Woodstock $1,150,000

Welcome to 33 Mountain Avenue – a mid-century modern gem poised perfectly on the edge of Faulkner Park and at the foot of Mt. Tom and once part of the Marianne Faulkner E...

  • 2 Beds
  • 4 Baths
  • 5067740 MLS
  • CLOSED 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 .

1500+ Sq. Ft. Woodstock Real Estate

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eXp Realty
(603) 219-6773
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603-219-6773

eXp Realty
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Concord, NH 03301
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