Woodstock Homes for Sale

Woodstock Homes for Sale

Welcome to Woodstock, a charming city nestled in the heart of [Region]. Known for its picturesque landscapes, friendly community, and rich history, Woodstock is a place where small-town charm meets modern conveniences.

In Woodstock, you'll find a wide variety of homes for sale to suit every lifestyle and budget. Whether you're looking for a cozy bungalow, a spacious family home, or a trendy downtown loft, True Real Estate has you covered. Explore our listings to discover your dream home in Woodstock.

With top-rated schools, beautiful parks, and a thriving local economy, Woodstock offers the perfect balance of suburban tranquility and urban amenities. Enjoy shopping and dining in the vibrant downtown area, or take a leisurely stroll along the scenic trails that wind through the city.

If you're considering a move to Woodstock, now is the perfect time to make your dream a reality. Contact True Real Estate today to learn more about homes for sale in this desirable city and start your journey to finding the perfect home in Woodstock.

Newest Woodstock Homes for Sale

$2,485,000
4 Beds ⋅ 5 Baths ⋅ 5107880 MLS
Built in 1807 by Tille Parker, 26 The Green is one of Woodstock Village’s earliest and perhaps prettiest houses. The Federal style residence originally served as a tavern and lodging for members of Vermont’s early legislature, giving the property an uncommon connection to both the town’s and the state’s history. Over a century later, it became the Daughters of the American Revolution House Museum. Listed on the historic register, the home underwent a comprehensive restoration in 1995 by noted preservationist Doug Guest, along with a thoughtfully designed addition. Distinctive original details remain, including five teardrop ornaments above the first-floor windows and the beautiful Palladian window over the front entrance. Together with the patina of more than two centuries, they give the house an authenticity that has been carefully preserved while incorporating the comforts of contemporary living. Inside, wide-board floors, finely proportioned rooms, five working fireplaces, period millwork, and abundant natural light create a sense of warmth and character. The capacious renovated kitchen opens to a sun-filled dining area overlooking the rear stone terrace, while gracious gathering rooms retain the scale and character of the original house. All bedrooms are en suite, an unusual convenience in a home of this age. Set back from Main Street along a quieter parallel road, the property enjoys one of Woodstock Village’s most appealing locations, with dining, the theater, galleries, cultural events, and the trails of Mount Tom all within an easy walk. A detached two-bay garage and off-street parking add another uncommon convenience for a village property. Beautifully restored and turnkey, 26 The Green offers the opportunity to live in an important early Vermont home without sacrificing the ease of contemporary village life.

26 The Grn, Woodstock
$1,040,000
3 Beds ⋅ 2 Baths ⋅ 5105489 MLS
Woodstock Village Home~ A rare opportunity to enjoy the best of Woodstock Village living from this charming and beautifully updated 3-bedroom, 2-bath home, once the town's blacksmith shop. Just steps from the heart of the village, you can leave the car at home and walk to shops, restaurants, galleries, cafés, and everything that makes Woodstock one of Vermont's most beloved destinations. Inside, an open-concept floor plan, beautiful wood floors, and abundant natural light create a warm and inviting atmosphere. Recent improvements include a new heat pump providing efficient heating and air conditioning, electrical upgrades, interior painting, and extensive basement work, enhancing both comfort and functionality. Outside is where this village property becomes truly special. The spacious fenced yard borders the Kedron Brook, creating a surprisingly peaceful setting in the heart of town. Relax on the deck and listen to the water, enjoy the newly planted fruit trees, or step through the yard to the nearby village footbridge spanning the brook--a picturesque connection to the surrounding neighborhood. Historic character, thoughtful improvements, a wonderful yard, and an exceptional walkable location come together in a home that captures the charm and ease of life in Woodstock Village.

13 High St, Woodstock
$195,000
2 Beds ⋅ 2 Baths ⋅ 5104613 MLS
property being sold by trustee, seller has no knowledge of age, or systems within the home. There is no Zoning in the town Woodstock. This property will need work to make it livable.

88 Lost River Rd, Woodstock
$899,900
5 Beds ⋅ 4 Baths ⋅ 5104119 MLS
Mountainside Road really leans into the Mountain get-away theme of New Hampshire. This property is currently being used as an Air B & B, featuring a main house with 4 bedrooms that can be combined with or leased separately with a studio apartment that has its own kitchen, bath, porch and private entry. The home offers great White Mountain Views, is directly across the Street from Lost River (swimming and waterfalls) and providing easy access to all the Lincoln / Woodstock attractions and Loon Mountain skiing. This was a primary home for decades, and the apartment was added for a caretaker to live on site. It has been meticulously updated and maintained through the years and a whole house generator provided comfort on those harsh winter nights. The Cottage or shed structure offers a place for projects or additional storage.

5 & 7 Mountainside Rd, Woodstock
$1,075,000
3 Beds ⋅ 3 Baths ⋅ 5103213 MLS
This superbly cared-for cape-style home has been thoughtfully and comprehensively updated, with all bathrooms tastefully renovated with quality fixtures and finishes. The home features a creative, livable floor plan with a mix of open gathering rooms and comfortable private spaces, accented with crown molding and 8 1/2-foot ceilings on the main level. The main level has two entries, with additional direct access from the spacious 2-car garage. A mudroom connects the front and garage entries, and the back entry near the garden barn is close to the kitchen. The generous living room centers on a wood-burning fireplace with floor-to-ceiling windows spanning the width of the room. A gracious dining room adjoins the living room, den/bedroom, kitchen, and private stairway to the primary bedroom suite. The second level includes the primary bedroom with study/dressing room, walk-in closet, private balcony, and en suite bath with Italian marble vanity, tile, and surfaces. The second bedroom is illuminated by natural light and well-appointed en suite bathroom. A second-floor family/media room is separate from the sleeping areas. The property is within easy walking distance to the Village Green, shopping, entertainment, elementary school, and all resort amenities. A gem waiting to be discovered.

648 Church Hill Rd, Woodstock
$1,695,000
4 Beds ⋅ 3 Baths ⋅ 5102668 MLS
"BLISS HOUSE" Privately nestled on a picturesque hillside just minutes from the Woodstock Village Green, this beautifully renovated residence offers exceptional privacy, sweeping long-range mountain views, open meadows, mature gardens, a swimming pool, hot tub, and the perfect blend of Vermont charm and modern comfort. A thoughtful renovation transformed the kitchen and dining areas into a bright, open gathering space where spectacular mountain views are always on display. The newer gourmet kitchen features a large center island, Thermador appliances, quartz countertops, and abundant custom cabinetry. The spacious living room is centered around a handsome stone fireplace and offers multiple seating areas. French doors open to a newer southwest-facing deck with a large hot tub, creating the perfect setting to enjoy sunsets and panoramic views throughout the year. The main level also includes a generous primary suite with a walk-in closet and an ensuite bath featuring a soaking tub with mountain views and a separate shower. A mudroom with laundry connects directly to the oversized attached two-car garage. A circular staircase leads from the kitchen to a charming renovated tavern and wine room with French doors opening to a private brick patio, ideal for entertaining. Upstairs are a comfortable office, study, or media room, three additional bedrooms (two with long-range views), an updated full bath, and a separate half bath. The full concrete basement provides abundant storage and houses the mechanical systems. Additional amenities include a full-house automatic generator, ample parking for four or more vehicles in addition to the attached garage, and well-maintained grounds. BLISS HOUSE combines privacy, stunning views, quality renovations, and an exceptional location just minutes from Woodstock Village. Walk-through tour, video, drone aerials, and floor plans available online.

353 Cabot Rd, Woodstock
$450,000
3 Beds ⋅ 2 Baths ⋅ 5102664 MLS
Enjoy peace, privacy, and endless possibilities on 2 quiet acres, just 3 miles from downtown Woodstock! This adorable ranch-style double-wide offers a bright, open-concept kitchen, dining, and living area perfect for entertaining or relaxing by the wood-burning fireplace. Vaulted ceilings and abundant natural light enhance the spacious feel. The impressive kitchen features solid hickory cabinetry, stainless steel appliances, a tile backsplash, pot filler, apron-front sink, oversized island with extensive storage, and a charming window seat with additional storage. The primary suite includes a spacious bathroom with double sinks, a stand-up shower, soaking tub, and direct access from both the bedroom and bathroom to a large walk-in closet. The property’s standout feature is the nearly new, never-used, three-story barn measuring approximately 40' x 28'. With 14-foot ceilings and 13-foot entry doors, it is ideal for RV storage, classic cars, animals, a workshop, or other recreational uses. Above the barn is an additional 20' x 40' open space, accessed by interior stairs, offering approximately 800 square feet of storage or potential finished space. The barn may also offer future residential conversion possibilities, subject to all required permits and approvals. Additional features include a 30-amp electrical hookup in the driveway for an RV or hot tub, a lovely brook that feeds a private pond, and a peaceful mountain setting. Perfect for year-round living, a second-home getaway, or a potential Airbnb opportunity!

68 Russell Farm Rd, Woodstock
$1,195,000
4 Beds ⋅ 3 Baths ⋅ 5100512 MLS
This wonderful Vermont Cape-style home is a peaceful hideaway with amazing views upriver towards Killington is within walking distance of Village shops, restaurants, and resort amenities. The home has overlooked the Ottauquechee River and the former Woodstock woolen mill since 1890. The old mill has long since been repurposed as a children’s daycare center surrounded by community pools, basketball courts, and the Town’s recreation center. On long summer days, the joyful sounds of children enjoying the wide sand beach and swimming holes float up from the river below. Over the years, the floor plan has been adapted on all three levels to modern lifestyles. 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 home, like many in Woodstock Village, was damaged in August 2011 by Hurricane Irene. The property is not in the designated 100-Year floodplain that requires insurance. Irene was a FEMA-designated 500-year flood event that affected the basement; afterward, the owners replaced the lower-level sheetrock and the heating boiler and restored the riverbank.

16 Church St, Woodstock
$5,875,000
3 Beds ⋅ 4 Baths ⋅ 5099532 MLS
Sorgenfrei, German for "carefree" captures the spirit of this remarkable 68 acre property in one of South Woodstock's most desirable locations: a place where life slows and the beauty of the Vermont countryside takes center stage. At the end of a quiet road, the property combines sweeping mountain views, and exceptional privacy with a thoughtfully designed hand-crafted, timber frame home. Outside, perennial gardens give way to open pasture suitable for a few horses or sheep, woodland trails for riding, hiking, cross-country skiing, and snowshoeing and direct access to the GMHA trail system. Built in 2015, the three-bedroom residence is defined by soaring spaces, exposed fir beams, walls of glass, and craftsmanship that feels substantial without being formal. Nearly every principal room is oriented toward the eastern views, bringing the surrounding mountains and changing Vermont landscape into daily life. The main level is equally comfortable for quiet everyday living or a houseful of guests, with an open kitchen, dining area, and dramatic great room centered around a floor-to-ceiling double-sided stone fireplace. A more intimate sitting room, screened porch, expansive deck, and primary suite are also located on this floor. Upstairs are a loft office, two en suite guest bedrooms, and a media room. The walk-out lower level adds a gym, infrared sauna, workshop, and temperature-controlled wine room with capacity for approximately 1,000 bottles. An 18.5 kW solar array supports near net-zero living, while a three-bay garage accommodates vehicles, sporting equipment, and the gear that comes with an active Vermont life. 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
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