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42-18 Heritage Condo Way Unit Unit 18D, Woodstock image
42-18 Heritage Condo Way Unit Unit 18D, Woodstock $244,000

Easy living in this updated condo that is perfect for a primary or secondary residence. Located in a small condo community that is mostly owner occupied the setting offer...

  • 1 Beds
  • 1 Baths
  • 5101220 MLS
  • ACTIVE Status
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
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
20 Potato Hill Rd, Woodstock image
20 Potato Hill Rd, Woodstock $399,000

Experience tranquility in this charming 2+ bedroom ranch, perfectly situated on a private 1.22 acre lot. Enjoy the peaceful surroundings while being just a short drive fr...

  • 2 Beds
  • 1 Baths
  • 5097869 MLS
  • ACTIVE UNDER CONTRACT 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
65 Riverfront Dr Unit 216, Woodstock image
65 Riverfront Dr Unit 216, Woodstock $640,000

This fully renovated, Pemigewasset Riverfront top-floor end unit offers exceptional privacy, abundant natural light, and the soothing sounds of the river from every room....

  • 3 Beds
  • 2 Baths
  • 5095794 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
1190 Long Hill Rd, Woodstock image
1190 Long Hill Rd, Woodstock $350,000 ▼

Tucked away on 11.58 private acres in the heart of South Woodstock, this peaceful Vermont retreat offers simplicity, seclusion, and endless potential. Located along sceni...

  • 1 Beds
  • 1 Baths
  • 5093181 MLS
  • ACTIVE 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
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
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
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
42 Heritage Condo Way Unit 23 D, Woodstock image
42 Heritage Condo Way Unit 23 D, Woodstock $230,000

Amazing opportunity to own a property that is perfect as a full time home or a vacation get away, in the highly desired Heritage Condo community. The setting is serene in...

  • 1 Beds
  • 1 Baths
  • 5079996 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
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
41 Jack O Lantern Dr Unit 22, Woodstock image
41 Jack O Lantern Dr Unit 22, Woodstock $392,500

Attention all golfers! This townhome is located on The Jack Golf Course! You'll enjoy walking to the club house and to the nearby association amenities. The townhome feat...

  • 3 Beds
  • 3 Baths
  • 5075202 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
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
42 Heritage Condo Way Unit 14D, Woodstock image
42 Heritage Condo Way Unit 14D, Woodstock $220,000

Welcome to your Woodstock affordable retreat! This inviting, end-unit, two-level townhouse in the sought-after Heritage Condominium community is nestled on a dead-end roa...

  • 1 Beds
  • 1 Baths
  • 5068588 MLS
  • CLOSED Status
45 Riverfront Dr Unit 242, Woodstock image
45 Riverfront Dr Unit 242, Woodstock $495,000

Fantastic river view and tranquility is what you'll find at this 3-bedroom, 2 full bath, waterfront condo in Deer Park. Open concept floor plan with kitchen, dining and l...

  • 3 Beds
  • 2 Baths
  • 5068260 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
3914 South Rd, Woodstock image
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
23 Oakes St, Woodstock image
23 Oakes St, Woodstock $460,000

More Space, More Privacy, Less Hassle - All for Less than a Condo! Well-maintained and full of charm, this Oakes Road home sits on a spacious lot in a peaceful neighborho...

  • 2 Beds
  • 1 Baths
  • 5066982 MLS
  • CLOSED Status
20 Jack O Lantern Dr Unit 27, Woodstock image
20 Jack O Lantern Dr Unit 27, Woodstock $420,000

Tucked into one of the best spots at The Jack O’ Lantern, this 3-bedroom, 2.5-bath condo overlooks open green space and is just steps from the pool, brand-new playground,...

  • 3 Beds
  • 3 Baths
  • 5066684 MLS
  • CLOSED 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
1362 Barnard Rd, Woodstock image
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 C, Woodstock image
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 image
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
26 Mt Peg Roa Unit D, Woodstock image
26 Mt Peg Roa Unit D, 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
  • 5065225 MLS
  • ACTIVE Status
93 Blake Hill Rd Unit B, Woodstock image
93 Blake Hill Rd Unit B, Woodstock $587,715

Stunning Views overlooking beautiful pastoral meadows as you gaze to the Pomfret Hills. This handsome condo has been completely renovated with cathedral ceilings accente...

  • 3 Beds
  • 3 Baths
  • 5064977 MLS
  • CLOSED Status
1079 Fletcher Hill Rd, Woodstock image
1079 Fletcher Hill Rd, Woodstock $400,000

This charming 2-bedroom ranch house offers a nice layout for main floor living. Features include a sunroom entrance, two bedrooms, a full bath, laundry room, and a main l...

  • 2 Beds
  • 2 Baths
  • 5064428 MLS
  • CLOSED Status
348 Laughlin Rd, Woodstock image
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
182 Rose Hl, Woodstock image
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
11 Jack O Lantern Dr Unit 35, Woodstock image
11 Jack O Lantern Dr Unit 35, Woodstock $350,000

Drive off Exit 30, pull into the Jack O’Lantern, hang up your keys, and step into this kind of easy living. This 3-bedroom, 2-bathroom condo with a loft is all about comf...

  • 3 Beds
  • 2 Baths
  • 5041527 MLS
  • CLOSED Status
65 Riverfront Dr Unit 216, Woodstock image
65 Riverfront Dr Unit 216, Woodstock $650,000

OPEN HOUSE CANCELLED - UNDER AGREEMENT Welcome to this fully renovated, luxury Pemigewasset riverside unit at Deer Park in Woodstock, NH. No expense was spared in the re...

  • 3 Beds
  • 2 Baths
  • 5023164 MLS
  • CLOSED Status
608 Fletcher Hill Rd, Woodstock image
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

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 .

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eXp Realty
(603) 219-6773
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