Woodstock NH Real Estate, Homes, Condos for Sale

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 offers a private living space. The deck looks out to well maintained grounds and woodlands. The updated kitchen and bathroom are well appointed. The main level has an open floor plan that includes the kitchen, dining area and living room . Upstairs , in addition to the bedroom, bath and laundry there is a wonderful bonus area that can be used in multiple ways and the sliding barn door provides privacy to the area. Located across from Woodstock Middle and Senior High School as well as the Woodstock Senior Center and just minutes from the center of the historic town of Woodstock voted one of the prettiest small towns in America ! Close to skiing at Killington and Woodstock's own Saskadena Six there is access to sports and activities for every season. Call for a private viewing .

42-18 Heritage Condo Way Unit Unit 18D, Woodstock

$1,375,000

4 Beds ⋅ 3 Baths ⋅ 5100512 MLS

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 center) since 1890. On long summer days, the sounds of children enjoying the swimming holes and tubing in the rapid runs below float up. The floor plan has been adapted to modern lifestyles across three levels. The main level, entered from the garden walkway or garage, connects to an open country kitchen via a mudroom, which flows into the dining area and living room, offering extraordinary upriver views west toward Killington. A spacious main-floor primary bedroom with an en suite bath opens to a riverside deck, and an expanse of lawn and gardens surrounds the residence. Upstairs are two large bedrooms with a shared bath and a reading loft overlooking the living room below. The walkout lower level includes another bedroom, a bath, a recreation room, and a laundry. The soothing music of the water rose to a crescendo in August 2011 as Hurricane Irene swept into Vermont as a tropical storm, resulting in a FEMA-designated 500-year flood event that inundated basements, as it did many homes in Woodstock and other river towns. Subsequently, the owners have replaced the lower-level sheetrock and boiler and have invested in an engineered barrier wall. The home is within walking distance of Village shops, restaurants, and resort amenities. A peaceful hideaway close to everything.

16 Church St, Woodstock

$5,875,000

3 Beds ⋅ 4 Baths ⋅ 5099532 MLS

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 beauty of the Vermont countryside takes center stage. Built by Ennis Construction in 2015 on 68 acres, the three-bedroom home embodies the enduring appeal of timber frame architecture with soaring spaces, exposed fir beams, and exceptional craftsmanship. Mahogany clapboard siding lends timeless character to the exterior. Inside, walls of glass frame sweeping mountain views, filling the home with natural light and creating a seamless connection to the landscape. Nearly every principal room is oriented toward the views to the East. The open floor plan flows from the gourmet kitchen to the dining area and dramatic great room, anchored by a floor-to-ceiling double-sided stone fireplace. A sitting room, screened porch, deck, and the primary suite complete the main level. Upstairs are a loft office, two en suite guest bedrooms, and a media room, while the walk-out lower level is dedicated to recreation and relaxation with a gym, infrared sauna, workshop, and a temperature-controlled wine room for approximately 1,000 bottles. A three-bay garage provides ample space for vehicles, and gear. Complete end-of-road privacy, panoramic views over the Woodstock Valley, perennial gardens, open pasture for a few horses or sheep, and an extensive trail network connecting directly to the GMHA trail system create a quintessential Vermont lifestyle. Thoughtfully designed for ease of ownership, the property is as practical as it is beautiful, with an 18.5 kW solar array supporting near net-zero living. Just minutes from Woodstock Village, 16 miles from Killington Resort, and 26 miles from Okemo Mountain Resort.

115 Eastman Rd, Woodstock

$400,000

2 Beds ⋅ 1 Baths ⋅ 5099229 MLS

Once an old school house, this home features stone walls, beautiful gardens, and a nice level yard with a stone patio. The year-round brook cascades over rocks and winds along the back side of the property. A covered porch leads inside, where the main floor offers an eat-in kitchen, a large living room and a dining area with French doors to the outside. There are also two bedrooms, an office with stairs to the basement, a full bath with laundry, and a mudroom. The 2nd floor attic, with a large dormer, offers many possibilities for additional space but requires installing stairs and building out the open area. The basement houses utilities and allows for significant storage. The house needs a few updates but has lots of potential and is a wonderful investment opportunity or a great way to get into a starter home in the Woodstock area. It is conveniently located just minutes from Woodstock Village and only a few miles from the Kedron Valley Inn, the South Woodstock Store, and the Green Mountain Horse Association.

2556 Church Hill Rd, Woodstock

$799,999

3 Beds ⋅ 3 Baths ⋅ 5098474 MLS

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 a short drive outside of Woodstock Village, this cabin offers the perfect blend of privacy and convenience. Built in 1996, this thoughtfully crafted home features approximately 2,600 square feet of living space on 2.9 acres. The home offers 3 bedrooms and 2.5 bathrooms, with warm and inviting open living spaces anchored by both a fireplace and a wood stove, perfect for cozy Vermont evenings. A spacious porch takes full advantage of the South Easterly views, providing an ideal spot to relax and take in the natural surroundings. A detached 2-car garage with an accessory dwelling unit studio above, complete with a 3/4 bath; ideal for guests, rental potential, or a private office/studio. A potting shed and a wood shed complete the outdoor spaces, offering ample storage and outdoo hobbies. With its combination of rustic charm, modern utility, and an central location, this property is a rare opportunity to enjoy mountain living without sacrificing accessibility to nearby amenities and recreation.

3036 W Woodstock Rd, Woodstock

$2,300,000

5 Beds ⋅ 6 Baths ⋅ 5098424 MLS

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 extended cape styled home was renovated approx 15 years ago with handsome hardwood floors throughout. Large kitchen with Calcutta Marble, Electrolux stainless appliances and ample storage that opens into the dining room- The formal living room also has expansive views beyond the french doors to a covered porch across the back of the house for entertaining family and friends. The living room is anchored by a traditional propane fireplace, custom book shelves, lovely pocket doors... it's easy to want to curl up with a good book in the wintertime. Generous primary suite with custom built-ins, walk in closet and expansive bathroom located on first floor. There is a second guest bedroom with full bath on the first floor as well as a cozy den surrounded by built-in bookcases. Second floor features 3 very large bedrooms and 2.5 bathrooms including a clawfoot tub. A walk out basement for easy access to store patio furniture. Ample storage or potential for a workshop. There is a generator on site, 2 bay attached garage and barn/stables down below the property. The majority of the property is open and mowed to perfection. This estate has been well maintained and in a superior location. Killington/Pico and Okemo a short distance. Easy access to historic Woodstock, championship golf, tennis, cross country skiing and shopping. Come take a look. Not many properties with this exceptional view!

915 Peterkin Hill Rd, Woodstock

$497,500

3 Beds ⋅ 3 Baths ⋅ 5098210 MLS

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 community less than 5 minutes from the Historic Woodstock Center and conveniently located within walking distance of Woodstock Union Middle & High School. It is also located only 30 minutes from Killington Ski Resort and Okemo Ski Resort and 10 minutes from Saskadena Six. The location and price make this home a truly unique buying opportunity for several types of owners. The very private 24 home community is comprised of retirees, working families, and second home owners who want to enjoy all Vermont has to offer. The neighbors are awesome! This home is the most private in the complex as it is the very end unit surrounded on 3 sides by woods and streams. The unit is in very good condition and move in ready. The first floor is comprised of a den/bedroom with pocket doors for added privacy and an adjacent 3/4 bath. Also on the first floor is a spacious living room anchored by a propane fireplace, nicely crafted mantle and hardwood floors. A couple of steps down takes you into a renovated kitchen with stainless appliances and gleaming soapstone counters. A small eating area is surrounded by windows overlooking the back deck facing east with beautiful woods on 2 sides. Wildlife abounds. Tall ceilings and an abundance of natural light make the kitchen area a favorite space. The second floor consists of a very large primary bedroom with a seating area and three closets for an abundance of storage. The second bedroom is spacious with lots of sunlight. A good size full bathroom with tiled floors completes the second level. The lower level is a large family room with a walk out to a lovely patio. This level also has its own 3/4 bathroom, laundry area and several storage closets. The lower level has lots of options for use given the design. Open House- Saturday July 18th from 11am-1pm

121 Townhouse Way Unit 24, Woodstock

$430,000

3 Beds ⋅ 2 Baths ⋅ 5098036 MLS

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 abundant natural light, creating warm, inviting living spaces that bring the outdoors in. Step outside onto the spacious new wraparound deck, the perfect place to enjoy your morning coffee, entertain family and friends, or simply unwind while taking in the tranquil surroundings. Just minutes from Interstate 93, this property offers exceptional access to year-round recreation and local amenities. Loon Mountain, Cannon Mountain, hiking and biking trails, golf courses, rivers, restaurants, shopping, and the attractions of Lincoln and North Woodstock are all nearby. Whether you're looking for a full-time residence, a weekend getaway, or an investment property, this home offers the ideal combination of comfort, privacy, and accessibility in one of New Hampshire's premier four-season destinations.

5 Downing Dr, Woodstock

$500,000

5098035 MLS

Rare opportunity to own a multi-acre lot within walking distance of downtown North Woodstock. Level parcel with road frontage on Lost River Road and also frontage on Gordon Pond Brook. This would be a perfect location for a home with lots of privacy and still be within walking distance of downtown restaurants, shops and natural attractions. Close to Loon and Cannon Mountains too!

Map 105 Lot 20 Map 105, Woodstock

$399,000

2 Beds ⋅ 1 Baths ⋅ 5097869 MLS

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 from the local golf course, Pemi River, and Loon Mountain. This inviting home features a fully equipped kitchen, and offers the convenience of easy one-level living. Abundant natural light fills the spacious living areas, creating a warm and welcoming ambiance. You'll find one updated bathroom, and a full basement, providing plenty of potential for expansion or additional storage. Step outside to discover a beautifully manicured lawn and large deck, ideal for entertaining or relaxing in the fresh air. The property includes a carport for added convenience and is located on a town-maintained dead end road, ensuring accessibility throughout the year. Showings will begin at the open house on 7/5 from 10AM - 12PM!

20 Potato Hill Rd, Woodstock

$1,050,000

5 Beds ⋅ 4 Baths ⋅ 5097556 MLS

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 view settings in the White Mountains. With over 90 degrees of unobstructed views stretching across Franconia Notch and the surrounding peaks, this extraordinary property combines exceptional privacy with easy access to Lincoln, Woodstock, Loon Mountain Resort, hiking, golf, and year-round recreation. Blending historic New England character with thoughtful modern updates, the home has been carefully maintained and improved while preserving its timeless appeal. Warm, inviting living spaces, handcrafted details, and expansive windows create the perfect backdrop for gathering with family and friends after a day spent exploring the mountains. A truly rare offering, the property is configured in a unique tri-plex-style layout connected by enclosed breezeways, providing outstanding flexibility for today's buyers. With three full kitchens and accommodations for 18+ guests, it's ideally suited as a luxury vacation home, multi-generational retreat, corporate getaway, or income-producing investment with outstanding short-term rental potential. The thoughtful design allows large groups to enjoy time together while still providing privacy and separate living spaces. Major updates include standing seam metal roofing, updated electrical, plumbing, and heating systems, along with the added security of a whole-home standby propane generator, providing comfort and peace of mind in every season. Whether you're searching for an unforgettable second home, a one-of-a-kind family compound, or a versatile investment property in one of New Hampshire's premier four-season destinations, 81 Meadow Lane is a rare opportunity to own an exceptional mountaintop retreat where breathtaking sunsets, unmatched privacy, and endless mountain adventures await.

81 Meadow Ln, Woodstock

$299,900

3 Beds ⋅ 2 Baths ⋅ 5097289 MLS

Nestled in a peaceful, natural setting overlooking scenic Mirror Lake, this small and charming cabin offers a true retreat for those seeking simplicity and a connection to nature. With its rustic appeal, the property could be a cozy year-round residence, vacation rental or getaway escape, with three private rooms as well as a shared kitchen and common space. Located on 2.30 conserved acres with its own driveway, adjacent to the Hubbard Brook Research Foundation's Likens Conservation Campus, the home offers tranquil lake views and the soothing sounds of bird song and breezes through the trees. The cozy interior provides a comfortable space to unwind, while the compact footprint ensures easy maintenance and a low-impact lifestyle. Please note: although there is a friendly relationship with the neighbors, there is no legal right to access the nearby lakeshore, and access is subject to revocable permission. This property is priced to reflect the need for a new septic system installation (a septic system has already been designed) which may limit some loan types. This unique offering is perfect for buyers who value privacy, conservation, and a quiet lakeside ambiance.

19 Hamlet Dr, Woodstock

$799,000

3 Beds ⋅ 3 Baths ⋅ 5097258 MLS

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 30 acres in Woodstock, this classic farmhouse is surrounded by beautiful open fields, mature trees, and peaceful natural beauty. Inside, you'll find a spacious eat-in kitchen that's perfect for gathering with family and friends, while the inviting living room features exposed beams and a cozy wood stove that adds warmth and character. The first floor also offers a primary bedroom with an ensuite bath and the convenience of first-floor laundry. Upstairs are two additional bedrooms, a bonus room, and a separate office or flex space ideal for working from home. Outside, relax on the covered front porch, unwind on the patio, or soak in the hot tub while taking in the scenic surroundings. The classic Vermont barn offers abundant storage, space for vehicles or equipment, and includes an attached chicken coop. The land is truly the highlight, with a picturesque pond, perennial gardens, open pasture, and a mix of wooded acreage offering endless opportunities for recreation, gardening, or simply enjoying the outdoors. All of this is just minutes from Woodstock Village, world-class skiing, shopping, dining, and everything this sought-after region has to offer.

1326 Curtis Hollow Rd, Woodstock

$1,695,000

4 Beds ⋅ 4 Baths ⋅ 5096963 MLS

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, upgraded systems, and fully furnished. Also included, is an additional 2,500+/- sq/ft (total) of an AirBNB rental/In-Law apartment, along with an active US Postal Service rental space, and generous storefront space in the former Taftsville Country Store. Expand your living space and use the large, open storefront as a home office or as an entertaining TV /Theatre room (we will even throw in two rows of reclining Theater seats)! The current owners use the place as a second home getaway. The rental offsets would be the Post Office lease (can be cancelled if the space is needed for other ventures) and whatever you choose to do with the smaller Airbnb one bedroom rental. Perfect opportunity for a vacation getaway/combo investment to offset living expenses with this small scale multi-unit property. Just five minutes to the quintessential downtown Village of Woodstock! Property consists of a spacious 3Brm/2Bth two story Owners quarters, storefront space with bath (approved for restaurant, café, or retail store), Post Office (with current lease), smaller one bedroom Apartment/In-Law rental (former AIRBNB rental), and additional storage space for second home toys. Current owners have redesigned, paved, and expanded the parking lot to include 21 parking spaces to the south side with four (4) 19Kw Electric Vehicle Charging stations, ADA access to building, and ADA accessible restrooms. Property boasts pretty patio views of the Ottauquechee River and Taftsville Covered Bridge. The historic village of Taftsville is known to be a wonderful community and is a desirable location for home ownership. Must see to appreciate!

2706 E Woodstock Rd, Woodstock

$174,999

5096885 MLS

Opportunities like this don’t come along often! Nestled in one of Woodstock’s most sought-after neighborhoods, this beautiful south-facing lot is the last available parcel in the development and is ready for your vision. The lot has already been cleared, saving you time and expense, and public water, public sewer, and electric are available at the street. Whether you’re dreaming of a year-round residence or the perfect mountain getaway, this property offers an incredible setting with beautiful mountain views in both directions. Enjoy the convenience of being just a short walk to the river and only minutes from the shops, restaurants, and attractions of both downtown Woodstock and downtown Lincoln. Outdoor enthusiasts will love the location, with Loon Mountain just minutes away and Cannon Mountain nearby, providing year-round recreation including skiing, hiking, biking, and more. Spend your days exploring everything the White Mountains have to offer and then easily return home! With a prime location, stunning surroundings, and utilities readily available, this is a rare opportunity to build exactly what you’ve been looking for in the heart of the White Mountains. Don’t miss your chance to own the final lot in this desirable neighborhood and create the home you’ve always imagined.

3 Profile Dr, Woodstock

$2,999,000

6 Beds ⋅ 8 Baths ⋅ 5096089 MLS

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. Lovingly stewarded and thoughtfully restored to the highest standard preserving the historic integrity and honoring the period detail, all while achieving the perfect unification of sophistication and functionality. The first level of the original home features generous spaces for entertaining and cozy, intimate rooms for quiet reflection. Original wide pine plank floors, oversized 6/6 windows, formal parlor and library each with a working fireplace. There is potential for a first-floor primary suite. The main house is further completed by 3 ensuite bedrooms and laundry on the second level, and two guest rooms with a shared bathroom on the third. The magnificent, attached c1750 oak gunstock post and beam barn frame was disassembled, imported from Hampshire, England and added to the home in the 1980’s, providing a great room beyond compare. Anchored by a massive stone fireplace, Palladian windows and a well-appointed chef’s kitchen, all located on the main level. There is an au pair suite, three car garage, and courtyard entrance on the walk out lower level stepping out to lovely, landscaped grounds and award winning gardens.

18 The Grn, Woodstock

$465,000

3 Beds ⋅ 3 Baths ⋅ 5095918 MLS

Spacious, immaculate, and beautifully maintained Federal-style brick townhouse located in the prestigious village of Woodstock, often recognized as one of America’s most beautiful small towns. Three finished levels, the larger size residence of 24 homes. Surrounded by mature woods, perennial gardens, & maple trees. A peaceful setting just minutes from Woodstock Village. The Woodstock Farmers’ Market is located at the end of the street. Outdoor enthusiasts will appreciate being less than one mile from trailheads leading into Marsh-Billings-Rockefeller National Historical Park, as well as nearby aqueduct and cycling trails. Killington Resort is approximately 20 minutes away. Gorgeous hardwood floors. The first level features a flexible room with pocket doors that can be used as guest bedroom, home office, studio, den, providing exceptional versatility for today’s lifestyle. The spacious floor plan lives more like a single-family home, with generous room sizes, abundant natural light, and a deluxe wood-burning fireplace. Additional features include: Full bathroom on each level Oversized private deck Covered bridge in town Brand new dryer Updated electrical and plumbing 2019 furnace This Property is conveyed subject to the Woodstock Community Trust Local Deeds covenant, a copy of which is attached to this listing.

121 Townhouse Way Unit 20, Woodstock

$640,000

3 Beds ⋅ 2 Baths ⋅ 5095794 MLS

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. Whether you're searching for a a four-season vacation home here in the White Mountains, or a property with strong rental appeal, or both, this beautifully updated residence checks every box. Year-round comfort is easy and economical with three Mitsubishi mini-splits providing efficient heating and cooling. The open-concept living space has been thoughtfully redesigned with custom cabinetry, updated flooring, and high-end appliances. Both full bathrooms and all three bedrooms have been completely remodeled, and not a single square inch was overlooked during the renovation. Every detail has been carefully considered, it is also being sold furnished, creating a truly move-in-ready property. located in Deer Park, one of the White Mountains' premier resort communities. It is known for offering some of the finest amenities in the region, including a private lake with sandy beach, indoor pool, hot tub, fitness center, racquetball courts, tennis and pickleball courts, game room, and scenic walking trails. Located in the heart of North Woodstock, this peaceful setting feels tucked away while remaining just minutes from Loon Mountain and the area's most popular attractions. Deer Park's winter shuttle service provides convenient transportation directly to Loon, making ski weekends and holiday weeks easy for owners and guests alike. Whether you're looking for a private mountain getaway, a place to gather with family and friends, or a property that can help offset ownership costs through rental income, this extensively renovated riverfront unit offers an exceptional combination of location, amenities, comfort, and value in the heart of the White Mountains.

65 Riverfront Dr Unit 216, Woodstock

$169,000

5095630 MLS

Instant equity in Woodstock! Bring your vision to life on this exceptional parcel of raw land, nestled in one of Vermont’s most coveted and quintessential communities. Offered below its current town-assessed value and backed by a recent independent appraisal valuation, this property delivers significant instant equity from day one. Whether you envision a private, tucked-away country estate or a seasonal retreat surrounded by classic Vermont scenery, this blank canvas is entirely ready for whatever you wish. Enjoy total autonomy and peaceful seclusion, all while remaining just minutes from the historic charm of Woodstock Village, local dining, and premier outdoor recreation. A rare, high-value investment opportunity where financial strategy meets local beauty. Bring your architect, your builder, and your dreams!

Iver Johnson Way, Woodstock

$26,500

2 Beds ⋅ 2 Baths ⋅ 5095563 MLS

This Quarter Share ownership, two bedroom condo (you have use 1 week per month) is a nicely updated unit located in the Notchbrook building. Step out your door to The Pemi River and just a short stroll to the club house. Inside you'll find 2 bedrooms, 2 full baths plus a Jaccuzi tub. Also features a gas fireplace to warm you on cold winter evenings and a full-size kitchen to cook for the entire family. Owning a quarter share is an affordable alternative to whole ownership. This is NOT a time share, you own the actual real estate. Condo fees include all utilities, maintenance and full use of all facilities. Deer Park has a fantastic amenities package which includes a beautiful spring fed pond with beach for swimming, indoor pool, hot tub, racquetball, weight & cardio rooms, tennis courts, ice skating, shuttle bus to Loon Mountain during the ski season and more. There is also an on-site rental program with worldwide RCI Exchange. Sorry, no pets allowed in the quarter share buildings.

164 Deer Park Dr Unit 177D, Woodstock

$2,225,000

4 Beds ⋅ 3 Baths ⋅ 5095556 MLS

Nestled in amongst flowering lilacs, ancient apple trees, and terraced English perennial gardens, this lovingly restored classic antique stone cape has all the conveniences of modern living, while honoring and preserving the charming period detail. Built in 1860, the home is an impressive example of snecked ashlar stone construction, which was introduced to this region by Scottish immigrants in the early 1800’s. The rooms are spacious, bright and inviting with exposed hand- hewn beams and pine plank floors running throughout. The updated country kitchen with soapstone counters connects to a cozy reading room with bookshelves and woodstove, and a utility/mudroom with ¾ bath, and laundry. The formal dining room offers plenty of space for gatherings. The front to back Living Room is anchored by a woodburning fireplace, and steps out to a private sunroom, and a guest room/office. Moving upstairs, there are four bedrooms and a bathroom. The 18thcentury hip roofed, post and beam English bank barn has a huge, sweeping loft space ideal for parties and entertaining. The lower level can accommodate animals, hobbies or a home occupation. The barn is surrounded by lush green pastures, and rail fencing which lead you to a network of beautiful trails for hiking. A short stroll to The Kedron Valley Inn, KV Pond, The South Woodstock Store, and Green Mountain Horse Assn. A five-minute drive to the Woodstock Village Green. Easy access to Hanover, DHMC, skiing, golf, dining, shopping and recreation.

473 Kendall Rd, Woodstock

$649,000

5095205 MLS

A rare Woodstock Village opportunity! A Victorian style home located in Woodstock's much desired Maple Street neighborhood! Popular Vail Field recreation area is conveniently nearby! For children in Maple Street's Neighborhood, Woodstock Elementary School is just a short walk away. Currently the residence is configured as home to 2 generations of occupants. A ground floor apartment conveniently accessed from 3 sides of the home comfortably provides accommodation for practical single level living. The main entrance is through a spacious 12'x10' mudroom. A great attribute in Vermont winters! On 1 end of a well thought out floor plan is a generously sized bedroom with a nearby bathroom. Midway in the apartment is a nicely appointed kitchen that then leads to an appealing dining area. Through a door off the dining area several steps lead to a laundry room that conveniently has an exit leading out to the rear of the property. A living room off the dining area completes the attractive apartment. Well placed windows throughout this ground floor provide pleasant views and natural light. A spacious 2nd floor apartment, with 2 levels of living space, is accessed through a private doorway on the front exterior of the residence. A flight of stairs leads up to the primary apartment area consisting of a bedroom, a dining room, a living room, a kitchen and a bath. Off the kitchen is a partially finished laundry area and then stairs leading down to a ground level workshop. Above the primary apartment is a useful 2 room attic area and a potential bath. Although this 2nd floor apartment has been a full time residence, a new owner will certainly choose to renovate some components of the apartment. The landscaped lot has much appeal with space for gardens and for relaxing outside. Residents in this neighborhood can enjoy walking to village amenities of shopping, dining and cultural events. A Victorian style home full of enormous potential! Location, location!

11 Maple St, Woodstock

$2,950,000

8 Beds ⋅ 8 Baths ⋅ 5094600 MLS

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 antique post and beam cape is complete with a large traditional 4 story barn with 6 horse stables and equipment sheds offers everything one could wish for in a country property. The grounds include gracious old maples, beautiful perennial gardens, antique moss covered stonewalls, an apple orchard, large swimming pond and a privately sited tennis court. The Estate is meticulously cared for and combines antique craftsmanship with modern touches. The Main house consists of 5 bedrooms including a first floor primary suite with private bath, vaulted ceilings and new large walk in closet. Kitchen features thermador appliances and quartz counters anchored by a large dining room with stunning wood floors. An expansive cozy living room centered by a handsome brick fireplace to curl up with a book on a snowy day. The rooms are spacious and inviting with an abundance of light, exposed original hand-hewn beams and easy access for outdoor entertaining on the brick patio or the new east terrace. Enjoy a separate 3 bedroom Guest House for friends/family with good rental income history. New Tesla Tower for backup power. Located in the heart of horse country and the village of South Woodstock. Enjoy skiing, championship golf and fly fishing on the Black River. Easy access to shopping, restaurants and Upper Valley. Only 8 minutes to Woodstock, 2.5 hours to Boston and 5 hours to NYC. Kedron Valley Farm is a stunning, quintessential farm in the heart of GMHA.

5798 South Rd, Woodstock

$965,000

3 Beds ⋅ 3 Baths ⋅ 5094379 MLS

This beautifully renovated, truly move-in-ready home has been thoughtfully updated throughout — including a brand-new kitchen, refreshed flooring, modernized bathrooms, fresh interior paint, a new garage door, an automatic full-house generator, and more. The property is offered FULLY TURNKEY, with nearly all furniture and furnishings conveying with the sale (artwork excluded). Privately sited in desirable South Woodstock—just seven minutes to the Woodstock Green—this home blends comfort, style, and convenience. The open-concept main level brings together the kitchen, dining area, and living room, where a vaulted ceiling and sleek propane fireplace create a warm, contemporary feel. The dining area opens onto a spacious deck and a flat backyard abutting conserved land, offering peaceful views and serene outdoor relaxation. A updated 1st-floor den/office provides flexibility and could easily serve as a 4th bedroom. Upstairs, the primary bedroom features a walk-in closet and a newly updated ensuite bath with elegant glass-tile walls. Two additional bedrooms share a renovated hallway bath. The finished lower level includes a dedicated laundry room and two rooms perfect as game/rec/gym/play rooms or offices. The attached two-car garage leads into a practical mudroom with built-in benches, hooks, and cubbies—ideal for Vermont living. With excellent mechanical systems, a full-house automatic generator, and updates already completed, this home offers effortless ownership in a prime location. If you’re seeking a turnkey, stylishly updated home just minutes from town, this South Woodstock gem is the one!

358 Cowdrey Path, Woodstock

$519,000

5 Beds ⋅ 3 Baths ⋅ 5093544 MLS

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 just 5 minutes from the Jack O'Lantern Golf Course and 10 minutes from Loon Mountain Ski Resort, the location is ideal for those who appreciate the outdoors and the four-season lifestyle of the White Mountains. For more than 50 years, this home has been treasured by the same family as a second home, where generations of children, grandchildren, and cousins have gathered to enjoy hiking, skiing, snowmobiling, kayaking, golf, and all the recreational opportunities the region has to offer. The home features 10 rooms, including 5 bedrooms, 2 bathrooms, with 2,629 square feet of living space, providing plenty of room for family and friends to gather. A standout feature is the large barn, once home to the Woodstock Canoe Company, offering exceptional space for storage, hobbies, a workshop, or future possibilities. An added bonus is the studio loft apartment, providing a private retreat for guests or potential rental income opportunities. As part of the Pine Crest Homeowners Association, owners enjoy access to a swimming pool and tennis court, adding even more opportunities for recreation and relaxation. Combining history, location, and lifestyle, this is a unique opportunity to create your own lasting family memories in the heart of New Hampshire's White Mountains.

1294 Daniel Webster Hwy, Woodstock

$589,900

4 Beds ⋅ 3 Baths ⋅ 5093238 MLS

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 attached apartment that offers excellent rental income potential or can serve as a comfortable in-law suite. This home has seen numerous updates, including a new roof with a transferable lifetime warranty, new windows, new siding, blown-in insulation, and a new propane-fueled wall furnace. All appliances are included, making this property truly move-in ready. A quality Reeds Ferry shed provides additional storage and functionality. Enjoy the convenience of being close to some of New Hampshire's most popular outdoor attractions, including golf courses, Loon Mountain Resort and Cannon Mountain Ski Area, snowmobile trails, grocery shopping, and a variety of restaurants. Experience the charm of small-town living while being just a couple of miles from the town center. Whether you're looking for a primary residence, a multi-generational living arrangement, or a property with supplemental income potential, this home offers exceptional versatility and value. Highlights: 4 bedrooms, 3 bathrooms Attached apartment/in-law suite New roof with transferable lifetime warranty New windows and siding New propane wall furnace Blown-in insulation All appliances included Reeds Ferry shed Close to skiing, golf, shopping, dining, and recreation Minutes from town center This property combines classic New England character with modern updates and outstanding income potential.

1113 Daniel Webster Hwy, Woodstock

$350,000

5093182 MLS

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 scenic Long Hill Road, surrounded by rolling countryside, woodland trails, and some of the area’s most distinguished estates. The property features a cozy 1-bedroom, 1-bath home with an open, efficient layout designed for quiet country living. Whether envisioned as a weekend escape, hunting camp, minimalist homestead, or future building site, the land is the true centerpiece. Mature woods, natural clearings, and serene surroundings create a setting that feels worlds away while remaining just minutes from the villages of South Woodstock and Woodstock. The area is known for its equestrian estates, scenic drives, hiking, and classic Vermont charm. The existing residence offers approximately 536 square feet of living space and sits privately on a gently sloping parcel with ample room to expand, garden, recreate, or build anew. A rare opportunity to own acreage in one of Vermont’s most sought-after rural settings. From 1985 to 2020, a three-bedroom house, occupied by a family of four, was on the property and utilized the current septic system without issues. The seller did have a soil evaluation done as well as a septic inspection. Both reports are attached in the documents.

1190 Long Hill Rd, Woodstock

$350,000

5093158 MLS

Secluded, peaceful and fully developed 1.5-acre lot awaits your new mountain dream home’s foundation. Ready to build! Perfectly located for your family’s year-round getaways just two miles to I-93 but seemingly a world away, this land is set just a mile from the quaint but bustling Main Street in North Woodstock, five miles to Loon Mountain and a short walk to the spectacular Ice Castles winter wonderland. Imagine driving up your new home site’s 260-foot private boulder-lined driveway to this quiet, wooded land with a 295-foot lot line on the White Mountain National Forest. Artistically designed boulder walls throughout the site create a beautiful and naturally aesthetic layout for a 50 x 32 foot home. Features an array of landscaping already planted and blooming. Developed over the last several years, the lot features include utility pole already placed with three Schedule 80 underground conduits (one 3”, two 2”), a 500-gallon buried propane tank hidden behind a big rock wall and laid out to provide adequate space from your home’s generator, water well recently drilled by Capital Well, and also an approved pipe and stone septic system design. Owner’s fully developed site plan and design architecture conveys to buyer. This lot is one of the most private, quiet home site in North Woodstock’s premier Lost Valley neighborhood, which offers the small number of Lot Owners a beautiful in-ground pool, tennis and basketball courts for a nominal annual Lot Owner’s fee. Please no drive-bys; lot is clearly posted No Trespassing and only accessible while in the presence of an agent by appointment only.

15 Otter Brook Rd, Woodstock

$11,900

1 Beds ⋅ 2 Baths ⋅ 5092964 MLS

This Quarter Share ownership, one bedroom condo (you have use 1 week per month) is a nicely updated unit located in the Notchbrook building. Step out your door to The Pemi River and just a short stroll to the club house. Inside you'll find 1 bedroom, 2 full baths plus a Jaccuzi tub. Also features a gas fireplace to warm you on cold winter evenings and a full-size kitchen to cook for the entire family. Owning a quarter share is an affordable alternative to whole ownership. This is NOT a time share, you own the actual real estate. Condo fees include all utilities, maintenance and full use of all facilities. Deer Park has a fantastic amenities package which includes a beautiful spring fed pond with beach for swimming, indoor pool, hot tub, racquetball, weight & cardio rooms, tennis courts, ice skating, shuttle bus to Loon Mountain during the ski season and more. There is also an on-site rental program with worldwide RCI Exchange. Sorry, no pets allowed in the quarter share buildings.

164 Deer Park Dr Unit 168D, Woodstock

$395,000

5092107 MLS

Rare opportunity to own 8 +/- acres of land in South Woodstock Village with easy access off of Rt. 106. This parcel is being divided off of a 10.87 acre lot. There is a wonderful , open site ideal for building your dream home offering privacy , trails and a short walk to the South Woodstock Country Store, Kedron Valley Inn , dining at the Ransom Tavern and a swim in the Kedron pond ! 5 miles into Woodstock Village , skiing available at multiple resorts including Okemo and Killington as well as local Saskadena Six. Green Mt. Horse Association is around the corner . The year round access to outdoor activities is endless. Call today for more information and a viewing . Subject to completion of the subdivision of the parcel.

Rte 106, Woodstock

$525,000

3 Beds ⋅ 2 Baths ⋅ 5092031 MLS

RIVER VIEW, 3RD FLOOR, END UNIT in The Glen at Deer Park! Furnished, well maintained condo in this beautiful park-like setting. 3rd floor unit offers vaulted ceiling and skylight to enhance the open floor plan. Great on-site amenities, including rec center and a lake with beaches. Only minutes to Loon Mountain for winter activities, and close to Franconia Notch State Park for summer fun. Cable and Internet included in the condo fee. Rental history available. Open House on Sunday July 5th from 9:00 to 11:00.

45 Riverfront Dr Unit 243, Woodstock

$2,900,000

5 Beds ⋅ 4 Baths ⋅ 5091062 MLS

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 bedrooms and 4 baths, filled with abundant natural light and thoughtfully designed for both large gatherings and quiet retreat spaces. The open-concept main level includes a spacious living room with picture windows overlooking the landscaped grounds, a recently updated chef’s kitchen with a stunning Mercury/Aga range, and generous dining space nearby. On the east side of this level, the original historic homestead—with its native timbers and stone fireplace—creates a warm and intimate dining experience. A wraparound deck provides additional space for outdoor dining and entertaining, while bedroom with its own bath completes this floor. Upstairs are 4 additional bedrooms, several featuring charming portal windows with views over the surrounding fields & hills. The primary suite is spacious and inviting, highlighted by exposed historic timbers, a sitting area, direct access to an upper deck, and a spa-inspired bath. On the uppermost level, the cupola offers the perfect yoga studio or quiet reading nook, complete with its own private deck. The grounds are truly magical, with an extensive trail network throughout the property and direct access to a magnificent waterfall and swimming hole just beyond the lot line within the State Forest. Large level lawns, mature landscaping, and a brook flowing along the southern side of the property add to its private tranquility. Nestled beside the brook is the guest house, known as the Brook House—a well-maintained 3-bedroom, 2-bath home privately sited away from the main residence, with its own lawn and deck overlooking the water below. With a convenient location offering easy access to Woodstock and Bridgewater Villages and a short drive to Killington Mountain Resort, this stunning estate is the consummate blend of privacy, charm, and modern convenience.

66 Hollow Farm Rd, Woodstock

$850,000

5091005 MLS

The justifiably proud owner of this property points out these features: Potential "Barnominium." Conveniently located just 1/4 mile from Woodstock Village town line and just 40 minutes from Killington Ski area. Built for an auto collection. Full bathroom, blown in insulation in ceiling, foam spray insulation in walls (with bug mesh in walls.) 3/4" sheet rock! All electrical is done in 3/4' conduit with many 4 plug in outlets. No electrical behind sheetrock. Extra LED lighting in ceiling. Office area in entrance. All inside doors are pocket doors. Epoxy colored floors. 2 ceiling Modine brand 100K heaters. 200 AMP electrical service with outlet for welder or power washer. The building has town sewer AND has sewer outlet port for RV septic dump. There is a high producing artesian well with a 3 phase VFD well pump for constant high pressure! There are 3 12' overhead doors and high ceilings! This well designed building is on 1.47 acres. There is also the potential for building a residence on the property. This high quality building is in a small quiet development in Woodstock!

97 Valley View Rd, Woodstock

$510,000

2 Beds ⋅ 3 Baths ⋅ 5090924 MLS

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 landscaped grounds . The bright living room complete with wood burning fireplace steps down to a lovely kitchen with dining area .Walk out through double sliding doors onto a private deck for one of two outdoor living spaces. There is an office/den as well as a powder room on the first floor . Upstairs there are two generous sized bedrooms and a full bath. The lower room is finished into a very large family room with a woodstove, bathroom and laundry. Open the sliding doors to a patio for the second outdoor space perfect for entertaining friends or a quiet space to relax. The location is only a few minutes to the center of Woodstock and a short drive to Killington. Call for a private viewing.

85 Town House Way Unit 18, Woodstock

$695,000

3 Beds ⋅ 2 Baths ⋅ 5089949 MLS

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 downstairs (which previously has been living spacce), combined with a separate two-bedroom apartment (with its own access) upstairs. The 1,335 sf lower level (Unit C) is currently a chiropractor's office space and was previously used as natural food store and barber shop. The 950 sf upstairs two-bedroom apartment (Unit D) has been leased out by the month for approx $2,000 per month, and has two separate bedrooms, a kitchen, sitting area, balcony and full bath. Or you could re-combine the two units into a larger 2,285 sf in-town residence or office space. There are 4 dedicated parking spaces for the two units, plus other parking in the rear that is shared with the other two units (A & B) of this commercial condo complex. This is a great opporunity to own a highly visible, move-in-ready building right on Route 4.

47 Pleasant St, Woodstock

$1,395,000

5 Beds ⋅ 4 Baths ⋅ 5089552 MLS

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 expanded and beautifully maintained, the home features a chef’s kitchen that opens seamlessly to a spacious gathering room designed for entertaining and everyday living. Multiple fireplaces—including a wood-burning and gas-ready—add warmth and character throughout the home. The flexible floor plan includes 3–4 bedrooms, highlighted by an upstairs bedroom with its own fireplace, plus a private guest suite or office above the garage—ideal for visitors, remote work, or creative space. Outdoor living is equally exceptional. Enjoy a covered porch, sunny patio, dedicated garden space, apiary, and an in-ground pool with heat hookup for extended seasonal enjoyment. More than 5 acres of invisible fencing allow pets to roam freely across the open landscape. Perfectly positioned for year-round recreation, the property sits adjacent to the site of America’s first ski tow and offers easy access to Saskadena Six, Killington, and outstanding winter activities throughout the region. A standout feature is the heated and plumbed two-story barn/workshop with its own vehicle bay—offering endless possibilities as a media or game room, studio, workshop, fitness space, or future guest quarters. With easy access to I-89 and the Upper Valley, this rare offering combines acreage, versatility, and close proximity to one of New England’s most iconic villages.

1522 Barnard Rd, Woodstock

$530,000

5089528 MLS

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 income. The 2 apartments have been recently renovated. This property is close to downtown North Woodstock and Lincoln. Near Loon, Waterville Valley, and Cannon Mountain all of the area's outdoor attractions!

252-254 Lost River Rd, Woodstock

$235,000

1 Beds ⋅ 1 Baths ⋅ 5089181 MLS

This beautifully updated 1-bed, 1-bath condo offers the perfect combination of modern comfort and an unbeatable mountain-town location. Outdoor enthusiasts will appreciate the prime location between Loon & Cannon Mountains, with hiking, skiing, and recreational trails accessible right from your doorstep. Summertime activities include mountain biking cycling, camping, and opportunities to explore local swimming holes along the Pemigewassett River and beyond!. Ideally situated on Main Street in downtown North Woodstock, you’ll enjoy being just steps from local restaurants, breweries, coffee shops, & charming boutiques, while also being minutes from amenities in vibrant downtown Lincoln. Fully renovated at the end of 2024, this unit showcases an open concept layout with lots of natural light, brand-new flooring, a completely redesigned kitchen & full bathroom, updated plumbing, a newly installed water heater, and is being offered almost fully furnished—delivering a truly turnkey, move-in-ready experience. The bedroom is spacious and large enough for a king-sized bed and dressers, and has a walk-in closet. As a desirable 1st-floor unit, the condo features dual entry points for added convenience and easy accessibility. Additional highlights include low HOA fees, a private porch with outdoor storage closet, and convenient on-site laundry within the building. There is also a separate closet in the building for bike storage if desired. The association is pet friendly & allows rentals with a 30-day minimum, offering excellent flexibility for extended stays or investment potential while maintaining a welcoming residential atmosphere. Whether you’re searching for a full-time residence, weekend retreat, or investment opportunity in one of New Hampshire’s most sought-after destinations, this turnkey condo offers the very best of mountain living with downtown convenience.

193 Main St Unit 115, Woodstock

$6,673,000

5 Beds ⋅ 4 Baths ⋅ 5089158 MLS

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 views, arriving at Birch Tree Farm. Spanning more than 465 acres, this extraordinary Vermont retreat offers an immersive four-season lifestyle -- from pressing fresh cider from the orchard and tapping maple trees for syrup to harvesting honey and gathering fresh eggs for breakfast. Miles of trails traverse varied terrain, including the summit of Old Baldy Mountain (2,409 feet). The retreat includes a lodge-style residence, a modern barn, and several ancillary farm buildings. The wood and stone lodge-style home carries a relaxed mountain vibe. Thoughtfully renovated in 2026, the interiors balance scale and warmth: exposed beams, a cathedral ceiling in the great room, and a substantial wood-burning stone fireplace anchor the space, while floor-to-ceiling windows draw in sweeping views of the mountains. The wrap-around deck takes in an infinity pool, hot tub, and stocked pond. In spring, wild lupine carpet the meadow; in autumn, the apple orchard comes into its own. Landscape design by Shep Butler includes 10’ hydrangea bushes, perennials gardens, stone walls and a walled vegetable garden. The three-level bank barn, designed by award winning Boston architect John MacDonald and built by Housewright Construction, offers one of the finest barns in area with 7 box stalls, a farm manager’s office/tack room, and a versatile upper level for entertaining, recreation, and movie night as well as accommodating an overflow of guests. Nine fenced pastures, run-in sheds, chicken coop, apiary, and direct access to GMHA’s trail network support an exceptional equestrian and recreational lifestyle. 157 acres conserved by VLT. 3.1 miles from GMHA, 3.8 miles from South Woodstock Country Store and Post Office, Less than a half hour from Killington, 2.5 hours from Boston.

2358 Long Hill Rd, Woodstock

$785,000

5 Beds ⋅ 4 Baths ⋅ 5088406 MLS

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 outbuilding ideal for a workshop or additional storage. The primary living space boasts a modern kitchen with updated cabinetry, granite countertops, and cherry floors. The open-concept family and dining rooms flow into a bright living room equipped with a Woodstock soapstone woodstove, brick hearth, and built-in bookshelves. A three-season porch offers additional space for entertaining. Showings to start May 18, 2026. Open House on May 23, 2026 from 11am to 1pm. The first-floor master suite includes a private full bathroom, two large closets, and a deck. Upstairs, you will find three additional bedrooms, an office/study, and a full bathroom. The separate one-bedroom apartment provides an excellent opportunity for rental income or private guest accommodations. Additional features include a two-car garage and a dog fence/kennel. Located near Mount Tom trails, the home is just five minutes from Woodstock, two minutes from the high school, and twenty minutes from Killington, making it a perfect primary residence or vacation getaway.

2605 Cox District Rd, Woodstock

$529,000

5088279 MLS

Incredible location! 60+ acres situated on the corner of South Rd. (106) and Noah Wood Rd. in beautiful South Woodstock. The land rises from the roads to the crest of the hilltop with amazing view potential looking to the Northeast. Multiple building sites can be found throughout the property which offers great recreational opportunities including direct access to the VAST trail on the lower corner. Parcel is mostly wooded with a large Maple Grove currently tapped by a local syrup producer. Green Mountain Horse Assoc. is just around the bend and the South Woodstock Country Store and Kedron Valley Inn are just a few minutes away. Woodstock Village is 6 miles down the road. Amazing spot to build your primary residence or second home getaway.

Noah Wood Road, Woodstock

$649,000

4 Beds ⋅ 2 Baths ⋅ 5088170 MLS

A rare Woodstock Village opportunity! A Victorian style home located in Woodstock's much desired Maple Street neighborhood! Popular Vail Field recreation area is conveniently nearby! For children in Maple Street's Neighborhood, Woodstock Elementary School is just a short walk away. Currently the residence is configured as home to 2 generations of occupants. A ground floor apartment conveniently accessed from 3 sides of the home comfortably provides accommodation for practical single level living. The main entrance is through a spacious 12'x10' mudroom. A great attribute in Vermont winters! On 1 end of a well thought out floor plan is a generously sized bedroom with a nearby bathroom. Midway in the apartment is a nicely appointed kitchen that then leads to an appealing dining area. Through a door off the dining area several steps lead to a laundry room that conveniently has an exit leading out to the rear of the property. A living room off the dining area completes the attractive apartment. Well placed windows throughout this ground floor provide pleasant views and natural light. A spacious 2nd floor apartment, with 2 levels of living space, is accessed through a private doorway on the front exterior of the residence. A flight of stairs leads up to the primary apartment area consisting of a bedroom, a dining room, a living room, a kitchen and a bath. Off the kitchen is a partially finished laundry area and then stairs leading down to a ground level workshop. Above the primary apartment is a useful 2 room attic area and a potential bath. Although this 2nd floor apartment has been a full time residence, a new owner will certainly choose to renovate some components of the apartment. The landscaped lot has much appeal with space for gardens and for relaxing outside. Residents in this neighborhood can enjoy walking to village amenities of shopping, dining and cultural events. A Victorian style home full of enormous potential! Location, location!

11 Maple St, Woodstock

$2,500,000

4 Beds ⋅ 4 Baths ⋅ 5087228 MLS

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 blend of refined luxury and pastoral charm. Thoughtfully designed for both elegant entertaining and everyday comfort, the four-bedroom, four-bath residence centers around a stunning gourmet kitchen—complete with a Sub-Zero refrigerator, Wolf range, dual dishwashers, prep sink, and a generous granite island perfect for gathering. Beyond the kitchen, a gracious butler’s pantry, inviting den, game room, and large living room create a home that is as functional as it is inviting. Expansive windows frame unobstructed views, bringing the surrounding landscape into every room, while modern efficiencies—including a whole-house generator and rooftop solar—offer peace of mind and sustainability. Equestrians and hobby enthusiasts alike will appreciate the impeccably maintained grounds: a four-stall barn with heated tack room, double run-in shed within the six-acre pasture, a greenhouse, and an additional five-bay garage/shop provide endless flexibility for pursuits and storage. The primary three-car garage ensures convenience close to home. With two wells servicing the property and an included separate, buildable lot with a four-bedroom septic design, the estate presents a unique opportunity for expansion or multigenerational living. All of this, just seven minutes from the charm of Woodstock Village and under twenty minutes to world-class skiing, creates a lifestyle defined by privacy, beauty, and effortless access to Vermont’s finest amenities.

114 Oak Ridge Way, Woodstock

$345,000

5085318 MLS

Your dream home starts right here — with a blank canvas in one of Vermont's most coveted communities. This exceptional buildable lot on Oak Ridge Way presents a rare opportunity to design and construct your ideal residence on a quiet side road in Woodstock. Nestled within a highly sought-after neighborhood, surrounded by million dollar homes, this property offers the kind of setting that inspires architects and homeowners alike. Picture your morning coffee on a wraparound porch, overlooking the existing neighboring pond and seasonal splendor that make this corner of New England absolutely legendary. The generous lot size provides ample outdoor space for landscaping, gardens, recreational areas, or whatever your imagination conjures. A septic permit is already in place and a house site has been cleared removing two of the biggest hurdles in the building process and letting you move forward with confidence and momentum. The surrounding community adds tremendous value to daily life here. Outdoor enthusiasts will appreciate nearby Aqueduct Trails for recreation and exploration, while the breathtaking Quechee Gorge is just a short drive away. The beloved Woodstock Farmers'Market keeps your kitchen stocked with fresh, local goodness all season long or spend the day downtown shopping in the unique shops and restaurants plus it's just a short drive to I89. Opportunities like this in Woodstock don't sit around waiting. Contact us today to learn more about this remarkable lot and start turning your vision into reality.

Oak Ridge Way, Woodstock

$502,000

4 Beds ⋅ 3 Baths ⋅ 5085202 MLS

Step into a rare offering where timeless New England charm meets contemporary comfort. Originally built in 1846 and thoughtfully reimagined, this exceptional Taftsville, Vermont residence is set along Happy Valley Brook, creating a private sanctuary defined by peace, beauty, and understated elegance. Historic character is beautifully complemented by carefully curated upgrades, including energy-efficient heat pumps, enhanced electrical systems, basement insulation, and newer windows—ensuring comfort and efficiency in every season. Recent capital improvements, such as updated siding, a newer drilled well, and new oil and propane tanks, underscore the home’s turnkey reliability, while generator-ready capability provides an added layer of confidence. Enjoy a kitchen built for making memories anchored by a newly installed and sleek granite island perfect for connection and celebration. Outdoors, the revitalized grounds invite both quiet relaxation and effortless entertaining, all framed by the natural splendor of this picturesque village setting. Positioned on coveted Happy Valley Road, the property offers a lifestyle as desirable as the home itself—where morning strolls and evening bike rides become part of your daily rhythm. Just minutes from the boutiques, dining, and charm of Woodstock, as well as convenient access to Interstate 89, this location perfectly balances a charming, village-like setting with accessibility. Imagine summer evenings spent beside the gently flowing stream, gathered around a glowing fire under the stars—an experience that captures the very essence of elevated Vermont living.

88 Happy Valley Rd, Woodstock

$1,895,000

2 Beds ⋅ 3 Baths ⋅ 5084536 MLS

Newly constructed Modern Vermont Farmhouse residence on 14 acres with absolutely amazing river views, 13-foot ceilings, gourmet kitchen, oversized french doors and windows throughout, radiant-heated concrete floors, first rate finishes, appliances and mechanicals located just 6 minutes to the Woodstock village green and 17 minutes to the Killington Skyeship base lodge. The first level is comprised of a large, open-format living space with gourmet kitchen, dining and living spaces, plus a first level bedroom with modern ensuite bath. Upstairs is another large open floor plan living space with a half-bath, and a full bedroom with ensuite bath. Each side of the upstairs living space has loft sleeping bunk-areas for kids (of all ages!). SEE DEDICATED PROPERTY WEBSITE FOR VIDEOS, VIRTUAL WALKTHROUGH, FLOORPLANS AND MORE.

2394 Fletcher Hill Rd, Woodstock

$11,250

1 Beds ⋅ 2 Baths ⋅ 5083900 MLS

One bedroom, 2 bathroom, gas fireplace, fully furnished and ready to be enjoyed! Gas fireplace for ambience and A/C. Located on the lower level. Enjoy 13 weeks of ownership on a rotating basis at the highly sought-after Deer Park resort with all the amenities you could ever need. 5 acre spring fed swimming pond with beach, multi-million dollar clubhouse with indoor pool, racquetball courts, tennis, fitness room, etc. Enjoy the skating rink by the club house. Use this quarter share one week of every month, or exchange for a different location for a small fee through RCI or Intervale International. Showings from 11-1 on Fridays only.

164 Deer Park Dr Unit 161D, Woodstock

$718,500

3 Beds ⋅ 2 Baths ⋅ 5081166 MLS

Great new price! Nestled in the vibrant heart of Woodstock Village, this beautifully renovated residence offers the ultimate "walk-to-all" lifestyle. Stepping inside, newly installed pine flooring guides you through an inviting main level designed for both daily living and effortless entertaining. The cozy living room anchors the home with its warm gas fireplace, while the spacious dining area flows seamlessly into a stunning, expanded kitchen equipped with sleek quartz countertops, and elegant cabinetry. Upstairs, three comfortable bedrooms provide peaceful retreats, highlighted by a versatile sitting room off the primary bedroom that easily transforms into a private study or playroom. Modern peace of mind is built right in, thanks to a new second-floor bath, new energy efficient propane furnace, upgraded 200 AMP electrical wiring, and many more upgrades. Outside, the classic covered porch serves as your front-row seat to the serene village surroundings. Directly across the street, the open green spaces of Vail Field invite you to enjoy playgrounds, ball fields, pickleball/tennis courts or simply walk the dog. Just a short, picturesque stroll away, the very best of Woodstock awaits—from the historic Woodstock Inn and the iconic Village Green to the local elementary school and an array of charming artisan shops, bakeries, and restaurants. For the athlete, this home puts you in the heart of the premier Vermont cycling communities and world class skiing. Complete with a two-car garage with plenty of room to store your outdoor gear, featuring a customizable, partially finished space above, this move-in-ready gem perfectly blends timeless New England charm with modern sophistication.

37 South St, Woodstock

$215,000

1 Beds ⋅ 2 Baths ⋅ 5081100 MLS

Waterfront condo with beautiful views of the Pemigewasset River in desirable Deer Park Resort. This well-maintained first-floor, handicap-accessible 1-bedroom unit features an open-concept layout, renovated kitchen, and recently updated heating and cooling system. The spacious primary bedroom offers a private full bath, with a second full bathroom for guests. Open Concept kitchen with maple cabinetry and quartz counter tops. Enjoy a private balcony overlooking the serene mountain river. High energy efficiency AC installed in 2024. A private locker for skies and gear, and washer/drier area in the basement. Direct access to the pond and the beach. Parking right next to the building. Conveniently located near the clubhouse with access to premium amenities including an indoor pool, hot tub, fitness center, game room, racquetball/pickleball courts, and a 5-acre spring-fed pond with sandy beach. Just minutes to Loon Mountain and close to Cannon Mountain, Lost River Gorge, Clark’s Trading Post, Whale’s Tale Water Park, and Flume Gorge, as well as downtown Lincoln and Woodstock. Short-term rentals allowed; unit has rental history. Offered fully furnished and equipped, ideal for personal use or investment.

10 Lakeside W Dr Unit 53, Woodstock

$499,500

2 Beds ⋅ 3 Baths ⋅ 5080430 MLS

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 the most sought-after communities in the Loon Mountain area. Recent updates include fresh interior paint, new carpeting throughout, new kitchen supplies, and a refurbished firebox in the cozy wood-burning fireplace. Each of the two upstairs bedrooms serves as a private master suite, complete with its own attached bath—offering comfort and convenience for residents and guests alike. Deer Park is known for its exceptional amenities, including an indoor pool, hot tub, racquetball court, fitness rooms, game room, basketball and tennis courts, and a beautiful 5-acre spring-fed pond with a sandy beach—perfect for summer relaxation. During ski season, enjoy the added convenience of a shuttle service to Loon Mountain. This property is being offered fully furnished, making it truly move-in ready.

11 Cascade Dr Unit 288, Woodstock

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