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Woodstock VT Real Estate & Homes for Sale

27 Properties Found

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$485,000

85 Townhouse Way Unit 18 Woodstock, VT 05091

MLS: 5041627 Photos
Beds:
2
Baths:
3.00
Sq.Ft.:
2,091
Status:
NEW LISTING
MLS#:
5041627
Type:
Condo
Lot size:
15 Acres
Year built:
1978
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Williamson Group Sothebys Intl. Realty
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ADDITIONAL INFORMATION

Fully furnished and equipped condo nestled in a small quiet community just 5 minutes from historic Woodstock. This is an end unit in very good condition- first floor comprised of a den//bedroom with pocket doors for added privacy and an adjacent 3/4 bath. New windows throughout. Spacious living room anchored by a wood burning fireplace with hardwood floors. A couple of steps down takes you into a kitchen with small eating area overlooking the back deck with a stunning crab apple tree. Tall ceilings allow this space to feel spacious with an abundance of natural light. Second floor consisted of a very large primary bedroom with ample closets and sitting area. Second bedroom is spacious with lots of sunlight. Lower level has a walk out patio with new slider doors, large family room with lots of option for use. Pets are allowed! Come take a look as its turn key with furnishing included! Seller to create a list of exclusion upon contract.

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$8,000,000

115 Eastman Road Woodstock, VT 05071

MLS: 5039451 Photos
Beds:
3
Baths:
4.00
Sq.Ft.:
5,384
Status:
Active
MLS#:
5039451
Type:
Single Family
Lot size:
68.92 Acres
Year built:
2015
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Williamson Group Sothebys Intl. Realty
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ADDITIONAL INFORMATION

Sorgenfrei, or "Carefree," was built by Ennis Construction in 2015, and this extraordinary property truly embodies that sobriquet. A stunning and uncommon confluence of the finest materials and the most energy efficient techniques, this home was carefully constructed to maximize worry-free enjoyment. The most advanced systems and a focused commitment to the highest quality make this home a testament to elegant durability. From the mahogany exterior to the hand crafted front doors and custom-wrought hardware, this spacious and meticulously considered home celebrates the skill of Vermont's most talented craftspeople. The unparalleled 180 degree views over the Woodstock valley are spectacular in every season, offering year-round sunlight and ever-changing vistas. With a gourmet kitchen custom-built for entertaining, a 1,000 bottle wine cellar, and a double-sided great room fireplace, Sorgenfrei perfects conviviality. The measures taken to ensure the property's efficiency and durability are too numerous to name - among them, an 18kw solar array, Pella Architect-Series windows, and custom mortise and tenon fir construction. At home among Woodstock's most lauded residences, and gorgeously situated in one of the area's most prestigious neighborhoods, this home is a testament to uncompromising vision and a paean to unparalleled enjoyment of Vermont's Green Mountains.

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$750,000

144 Butternut Lane Woodstock, VT 05073

MLS: 5039332 Photos
Beds:
4
Baths:
3.00
Sq.Ft.:
2,557
Status:
Active
MLS#:
5039332
Type:
Single Family
Lot size:
0.75 Acres
Year built:
1846
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Williamson Group Sothebys Intl. Realty
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ADDITIONAL INFORMATION

The Harry Emmons House an antique brick cape located in the village of Taftsville sited on an open flat village lot. Through the classic covered farm porch enter a gathering room with a brick fireplace, light-filled high ceilings, exposed beams in comfortably sized rooms, a country kitchen, sunny dining room, and a first-floor bedroom with dressing area. Moving upstairs, the second floor has two attractive bedrooms with a separate storage space. First floor laundry, 2-car barn garage, and additional living space for rental or au-pair complete the home. Conveniently located near the Village of Woodstock and the Upper Valley.

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$495,000

85 Townhouse Way Unit 14 Woodstock, VT 05091

MLS: 5039259 Photos
Beds:
2
Baths:
3.00
Sq.Ft.:
2,091
Status:
Active
MLS#:
5039259
Type:
Condo
Lot size:
15 Acres
Year built:
1978
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Williamson Group Sothebys Intl. Realty
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ADDITIONAL INFORMATION

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 comprised of a den//bedroom with pocket doors for added privacy and an adjacent 3/4 bath. Spacious living room anchored by a newer propane fireplace to curl up with a book on a cold winter day. A couple of steps down takes you into a renovated kitchen with small eating area overlooking the back deck. Tall ceilings allow this space to feel spacious with an abundance of natural light. Second floor consisted of a very large primary bedroom with ample closets and sitting area. A full bathroom and the second bedroom is a perfect size for guests. Lower level has a walk out patio with new slider doors, large family room with a small kitchen and eat-in area, spacious laundry and 3/4 bathroom. Newer Buderus boiler. Pets are allowed- Offered furnished with all new custom curtains. Come take a look at this turn key property!

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$1,390,000

11 College Hill Road Woodstock, VT 05091

MLS: 5038647 Photos
Beds:
5
Baths:
4.00
Sq.Ft.:
3,953
Status:
Active
MLS#:
5038647
Type:
Single Family
Lot size:
0.6 Acres
Year built:
1919
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Snyder Donegan Real Estate Group
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ADDITIONAL INFORMATION

Welcome to 11 College Hill Road - Situated in the heart of Woodstock Village, this classic 1919 Gambrel offers space, charm, and incredible views of both the Ottauquechee River and the town's beloved Mount Tom. This beautifully maintained home is perched perfectly above the river with over a half an acre of landscaped outdoor space, including 50 feet of river frontage, mature fruit trees, and stunning perennial gardens. Inside, youâ??ll find hardwood floors throughout, a wonderful cookâ??s kitchen, and sun-filled rooms with views from nearly every window. The flexible layout in the main house features 4 bedrooms and 2 baths, including a spacious primary en-suite, large media/office/recreation room, and two additional above-grade bonus rooms. A separate well-appointed accessory dwelling, built in 2007, offers ideal guest accommodations or income potential, and the soaring ceilings are perfect for a gym or studio. From both structures, enjoy direct access to outdoor living with a huge deck, screened-in porch, and peaceful sounds of the nearby river rapids. Additional features include a heated garage, whole-house generator, lightning-fast internet, and town water/sewer. Walk to restaurants, shops, schools, and hiking trails. Minutes to year-round recreation and a short drive to world-class skiing. This is a must-see property. Book your private tour starting Saturday May 3, 2025.

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$489,500

11A Prospect Street Woodstock, VT 05091

MLS: 5037971 Photos
Beds:
2
Baths:
2.00
Sq.Ft.:
930
Status:
Active
MLS#:
5037971
Type:
Condo
Lot size:
0.12 Acres
Year built:
1860
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Williamson Group Sothebys Intl. Realty
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ADDITIONAL INFORMATION

Walk to everything Woodstock village has to offer from this sunny condo! Within an easy stroll of the Woodstock Inn, downtown restaurants, farmer's markets, and the Marsh Billings Rockefeller National Park, 11A Prospect is ideal for enjoying the charms of village living. Elevated above the Route 4 on a bucolic neighborhood side street, this well-kept home offers historic details with modern amenities - including updated wiring, roofing, systems, and a modern poured foundation. The kitchen communicates comfortably with the bright dining and living rooms, and a private deck takes advantage of Vermont's extraordinary summers. Two airy bedrooms with a shared bath occupy the second floor, and a third-floor attic space presents expansion opportunities. With a full, walk-out basement for storage, this easy-keeping condo is ideal both as a pied-à-terre or as a full-time village home.

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$775,000

339 Gully Road Woodstock, VT 05091

MLS: 5037463 Photos
Beds:
4
Baths:
3.00
Sq.Ft.:
2,688
Status:
Active
MLS#:
5037463
Type:
Single Family
Lot size:
5.1 Acres
Year built:
1975
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Four Seasons Sotheby's Int'l Realty
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ADDITIONAL INFORMATION

Peaceful Gully Road Retreat. Just minutes from Woodstock Village. Set on 5.1 private acres along quiet and desirable Gully Road, this beautifully updated four-bedroom, two and one-half bath home offers the perfect blend of peaceful country living and convenient proximity to Woodstock shops, restaurants, and schools. The main level features a light-filled, open-concept layout with a dramatic vaulted foyer, spacious kitchen/living/dining area, a half bath, and a versatile den. Step out onto the expansive wraparound deck, perfect for outdoor dining, entertaining, or simply enjoying the surroundings. Upstairs, the primary suite includes a walk-in closet, private balcony access, and a newly renovated three-quarter bath. Three additional bedrooms, an updated full bath, and a large laundry area complete the second level. Additional features include: Attached garage with workshop/storage space on the lower level, high-efficiency propane furnace and numerous recent updates including kitchen, bathrooms, and flooring. Two outbuildings: a one-bay barn and a three-bay open garage/shed for ample storage. Outdoor highlights: treehouse; level lawn; two brooks; firepit area; and walking trails A rare opportunity to own a private, move-in-ready property in a sought-after location, just minutes from the heart of Woodstock Village.

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$595,000

20 Gully Road Woodstock, VT 05091

MLS: 5035826 Photos
Beds:
4
Baths:
3.00
Sq.Ft.:
2,678
Status:
Active
MLS#:
5035826
Type:
Single Family
Lot size:
2.6 Acres
Year built:
1903
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Bassette Real Estate Group
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ADDITIONAL INFORMATION

EXCEPTIONAL OPPORTUNITY IN WOODSTOCK, VT! - Classic Historic Vermont Farmhouse just outside of Woodstock Village! c.1903 Dormered Cape set on approx. 2.6 acres of level, open land bordered by a tranquil brook. The property offers a picturesque setting with extensive perennial gardens, a patio by the stream, firepits, covered front porch, rear porch, and deckâ??perfect for relaxing or entertaining. Inside, the home exudes warmth and comfort, featuring 2,600+ sqft, four bedrooms & three bathrooms. The inviting family room boasts a wood-burning fireplace, while the cozy living room is enhanced by a gas fireplace. The kitchen, with its soapstone Hearthstone brand woodstove and charming breakfast nook, is a delightful gathering space. Updates include newer windows, septic, appliances, and mechanicals, ensuring modern efficiency while maintaining the homeâ??s classic appeal. An oversized one-car garage provides ample storage and parking. There is additional storage above the garage with room for potential expansion into an office, game room or studio apartment. This classic Vermont farmhouse offers the perfect balance of historic charm and modern convenience, just 4 minutes from Woodstockâ??s vibrant village center. The Woodstock Green is only a 5 minute drive, as is skiing at Saskadena Six. Close to everything the Upper Valley has to offer while offering a peaceful retreat. A rare opportunity to own a piece of Vermontâ??s pastoral beauty!

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$226,000

67-1 Safford Commons Way Unit 1 Woodstock, VT 05091

MLS: 5035785 Photos
Beds:
2
Baths:
1.00
Sq.Ft.:
1,025
Status:
Active
MLS#:
5035785
Type:
Condo
Year built:
2022
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Martha E. Diebold/Hanover
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ADDITIONAL INFORMATION

This affordable 1,025 square foot condominium was built in 2022 and is conveniently located near amenities, shopping, and schools. 2 bedrooms, 2 baths. This unit is part of the Twin Pines Housing Trust's affordable housing program. Full price is $360,000. Twin Pines will pay the downpayment, so price to buyer is $226,000. An application to Twin Pines Housing Trust Homeownership program is required to purchase this condo. Household income limits are based on 120% AMI for Vermont Nonmetro.

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$239,000

442 E Woodstock Road Unit 4A Woodstock, VT 05091

MLS: 5035698 Photos
Beds:
2
Baths:
1.00
Sq.Ft.:
1,190
Status:
Active
MLS#:
5035698
Type:
Condo
Year built:
1980
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Martha E. Diebold/Hanover
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ADDITIONAL INFORMATION

Airy, tranquil and quiet, this former yoga studio space has been converted into a two bedroom condo. Sweeping views through the Palladian window, large living area with soaring vaulted ceiling, newer kitchen with granite counters and newer bath with walk in shower. Spacious entry can accommodate bikes, skis and more. Walking distance to shops, restaurants, entertainment and recreation in the beautiful historic village of Woodstock. This unit is part of Twin Pines Housing Trust's affordable housing program. Full price is $399,000. Twin Pines will pay the downpayment, so price to buyer is $239,000. An application to Twin Pines Housing Trust Homeownership Program is required to purchase this condo. Household income limits are based on 120% AMI for Vermont Nonmetro.

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$657,500

187 Dana Road Woodstock, VT 05091

MLS: 5033694 Photos

Open House:

Saturday, 5/17 1:00-3:00PM

More Open House Info >

Beds:
3
Baths:
2.00
Sq.Ft.:
1,468
Status:
Active
MLS#:
5033694
Type:
Single Family
Lot size:
1.71 Acres
Year built:
1955
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Snyder Donegan Real Estate Group
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ADDITIONAL INFORMATION

This delightful gambrel cape offers a wonderful combination of thoughtful and charming updates, energy efficient upgrades, and a coveted and convenient location! An intelligent interior design offers an all-season functional flow for everyday living as well as entertaining. Step inside by way of a spacious entryway/mudroom that also has direct entry from the attached garage. One will find the main level design to be a seamless flow from the lovely sunlit living room detailed with handsome woodwork framing a gas fireplace to the cozy kitchen/dining area that opens to an inviting three-season porch. A newly added half bath and a bonus room â?? perfect for an office/study/media room complete the main level. The upper-level offers three bedrooms â?? all with lovely views - and a full bath. Recent improvements include blown-in cellulose insulation and 2â? exterior insulation, new windows throughout, and a whole-house generator. The exterior landscape consists of 1.71 acres of plentiful open and level lawn area detailed with your quintessential stone wall. Private but convenient makes this location the perfect fit for a primary or vacation home. Enjoy easy access to a multitude of multi seasonal recreating including Killington, Saskadena 6, Marsh Billings Rockefeller National Park, and a terrific neighborhood trail system for hiking and mountain biking. Fabulous dining/shopping/ and the arts are just minutes away in the vibrant village of Woodstock. Schedule your private tour today!

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$1,995,000

20 The Green Woodstock, VT 05091

MLS: 5033342 Photos
Beds:
3
Baths:
3.00
Sq.Ft.:
2,688
Status:
Active
MLS#:
5033342
Type:
Single Family
Lot size:
0.33 Acres
Year built:
1826
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Williamson Group Sothebys Intl. Realty
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ADDITIONAL INFORMATION

Stunning antique cape! Located in the 'heart' of Woodstock. Originally located on Central Street- this home was moved in the 1960's to this location and had an extensive renovation in 2011. The antique brick section was built in 1826- it boasts a spacious living room anchored with a large wood burning fireplace, original wide pine floors and lots of space for entertaining. Adjacent find a quaint library with fireplace to curl up with a book on a cold winter day. Off the library is a bathroom and den/bedroom/office. Upstairs includes two more guest bedrooms and bathroom. The new back ell has beautiful architectural lines and features a large kitchen open into an informal and formal dining room anchored by an Austrian- Biofire wood stove. Handsome woodwork, immense amount of sunlight overlooking the perennial gardens. The back of the house has a gracious primary suite with an abundance of space including a reading nook, large en suite bathroom, generous walk in-closet and laundry. New foundation with poured concrete floors, ample storage space as well as an oversized 2 bay detached garage- with generator. Walk to all of towns amenities, restaurants and theatre. Easy stroll to Mtn Peg and Mtn Tom for those hiking enthusiasts. Championship golf, skiing and fly-fishing near by. This is truly an idyllic village home in historic Woodstock that is considered one of the 'prettiest towns in America".

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$755,000

13 Slayton Terrace Woodstock, VT 05091

MLS: 5033279 Photos
Beds:
3
Baths:
3.00
Sq.Ft.:
1,550
Status:
Active
MLS#:
5033279
Type:
Single Family
Lot size:
0.16 Acres
Year built:
1920
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Williamson Group Sothebys Intl. Realty
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ADDITIONAL INFORMATION

Charming cottage located in the heart of historic Woodstock Village with walking distance to all the shops, restaurants and town theatre. Mtn Peg walking trails just a 2 minute walk from front door for those hiking enthusiasts. This home is filled with an abundance of natural sunlight and features all hardwood floors throughout. New kitchen with butcher block counters, stainless appliances, maple flooring and lighting that opens into the dining room accented with a lovely bay window for additional lighting. High ceilings with moldings throughout. Living room features lots of windows and propane stove for those looking to curl up with a book on a cold winter day. Ample room for entertaining. New front door opens to a renovated wrap around covered porch for afternoon tea. Upstairs has 3 bedrooms, renovated bath, shiplapped walls along with all the charm that comes with a 1920's home. New windows, lovely perennial gardens accented with stunning apple tree in front yard when it bloom...as well as a privacy fence. Come take a look... charming cottage in one of America's prettiest towns.........Seller is a licensed real estate agent in the State of VT

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$1,800,000

484 Carlton Hill Road Woodstock, VT 05091

MLS: 5032740 Photos
Beds:
4
Baths:
5.00
Sq.Ft.:
4,100
Status:
Active
MLS#:
5032740
Type:
Single Family
Lot size:
7.66 Acres
Year built:
2008
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: KW Vermont Woodstock
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ADDITIONAL INFORMATION

Make this unique Adirondack-style home, with its rich stone and timber frame, and perfect location along the banks of the Ottauquechee River, your new Vermont retreat. Every window offers a stunning view of Mt. Tom, and the rushing river, making it a nature lover's paradise. The fieldstone fireplace soars two stories high in the great room, which is flooded with natural light through expansive thermal glass windows. This generous gathering space hosts a dining area and breakfast bar adjacent to an outstanding chef's kitchen. Crafted with meticulous attention to detail, this remarkable residence features four bedrooms and five bathrooms. The first-floor primary suite is a private sanctuary, boasting custom built-in 'his & hers' closets, a spacious spa-like bathroom, and a secluded sundeck. The tavern room, with its vaulted ceiling, stone fireplace and cherry wood bar makes this the go-to house for friends gathering at any time, but especially on Fourth of July. On the second floor, you'll find a luxurious Primary Bedroom with an en suite bath, an office/study with an adjacent ¾ bath, and a whimsical Children's Suite complete with cozy sleeping alcoves, and charming nooks.Conveniently located within walking distance to Woodstock High and Middle Schools, the Union Ice Arena, and the ever-popular Woodstock Farmer's Market grocery store, this splendid home offers the perfect balance of privacy without isolation.

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$1,895,000

10 College Hill Road Woodstock, VT 05091

MLS: 5031704 Photos
Beds:
5
Baths:
5.00
Sq.Ft.:
4,214
Status:
Active
MLS#:
5031704
Type:
Single Family
Lot size:
1.07 Acres
Year built:
1916
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Snyder Donegan Real Estate Group
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ADDITIONAL INFORMATION

10 College Hill is the perfect in-village residence, off the main road yet walk-to-everything. The original, historic residence was designed in 1916 by renowned architect John Russell Pope whose accomplishments include the Jefferson Memorial, and master plans for Dartmouth and Yale. It also enjoys modern additions and updates including a stunning first-level primary bedroom suite designed in 2012 by the respected local architect David Bielman. The front door welcomes guests with a pair of dutch-doors in a center entrance foyer, flanked by a classic dining room and elegant living room (both with fireplaces). The classic butlers pantry leads to the gourmet kitchen and a wonderful, sunny eat-in breakfast area. There are 4 additional BRs upstairs, 2 have ensuite baths plus a 3rd hall bath. There are also powder baths on the first floor and in the lower (basement) area. All BRs have central air. Mechanicals have been updated and well-maintained. 2 other offices on 1st and 2nd floor, and the basement has living space, a workout room, safe room, and ample storage. Beyond the kitchen is a mud-laundry room that leads to the covered (heated) brick walkway from the garage. The 1.05 acre parcel has professionally designed and executed gardens, patios and stone walls including new stone steps that lead up to a second new stone patio that enjoys sweeping vistas across to Mt Tom and the Marsh-Billings-Rockefeller National park. SEE FULL PROPERTY WEBSITE.

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$1,550,000

15 Central Street Woodstock, VT 05091

MLS: 5031244 Photos
Beds:
4
Baths:
3.00
Sq.Ft.:
6,014
Status:
Active
MLS#:
5031244
Type:
Single Family
Lot size:
0.05 Acres
Year built:
1840
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Williamson Group Sothebys Intl. Realty
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ADDITIONAL INFORMATION

15 Central Street is one of the finest commercial locations in Woodstock with two of the most creative and successful businesses as the anchor tenants. The property has adapted to changes of the course of its long history of uses including residential shop owner, a barber shop, a dance & pool hall, law office, architectural services and a variety of mercantile endeavors. Notably, the building was the headquarters of Lt Colonel Peter T. Washburn, who led the 1st Vermont Regiment troops in their crucial role at Gettysburg. He returned to become Adjutant and Inspector General to organize and direct Vermontâ??s military efforts through the rest of the Civil War from his offices at 15 Central Street. The current owner, recognizing it was time to adapt the building to the 21st Century, developed plans to upgrade and modernize the second and third floors for mixed use including an incredible residential unit with exposed brick walls and timber framing. The story high historic windows have been restored, and the second level has been reframed with new sheetrock for office or residential use. The third level partition walls have been removed to create a dramatic open area with views over the village to the north and south leaving the finishes and uses of the two levels up to your imagination. This is a once-in-a-lifetime opportunity to acquire a property with a remarkable history and become part of creating Woodstockâ??s future.

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$99,999

132 Riverbend Way Woodstock, VT 05091

MLS: 5029799 Photos
Beds:
3
Baths:
2.00
Sq.Ft.:
1,120
Status:
Active
MLS#:
5029799
Type:
Mobile Home
Year built:
2011
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: RE/MAX Upper Valley
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ADDITIONAL INFORMATION

Wonderful Woodstock location!!! 3 bedroom single wide mobile home ready for the new owner! Open concept kitchen and living room with plenty of closet space. Outside there is a large storage shed, a front porch and a deck under the tree. This home sits on a large corner lot! Only 13 miles to I-89!!

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$2,250,000

4945 South Road Woodstock, VT 05071

MLS: 5028924 Photos
Beds:
5
Baths:
4.00
Sq.Ft.:
3,502
Status:
Active
MLS#:
5028924
Type:
Single Family
Lot size:
2.57 Acres
Year built:
1811
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: LandVest, Inc/Woodstock
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ADDITIONAL INFORMATION

The John Arnold Cottle House is a landmark residence in the heart of South Woodstock, a rare blend of village convenience and country living. Built in 1811 by one of the area's earliest settlers, this stately Federal-style brick home has been thoughtfully restored to honor its historic charm while integrating modern comforts. Set on 2.7 acres, the property features 450 ft of frontage on Kedron Brook, along with a firepit, a barn, and a river meadow. The barnâ??currently used for storageâ??could easily be converted to accommodate a couple of horses or sheep. The 3-bedroom main house has elegant 12-over-12 windows, high ceilings, and beautifully preserved period details, including a 2nd-floor ballroom with a coved ceiling and fiddlerâ??s stageâ??a nod to its past as a lively gathering space. The newer addition overlooking the brook has a magnificent great room with 17' cathedral ceilings and a gourmet kitchen and wood burning brick fireplace. The renovated Kingsley Barn guest house offers 2 bedrooms, a loft, and a deck overlooking the brook. Below there is a heated workshop, ideal for puttering and creating. A timber bridge spans the waterway, connecting the propertyâ??s field, barn and trails. With direct access to the Upwey Trail system and equestrian paths leading to the Green Mountain Horse Association, this property is ideal for outdoor enthusiasts. Located along South Road in the South Woodstock Historic District.

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$795,000

25 Linden Hill Street Woodstock, VT 05091

MLS: 5028831 Photos
Beds:
3
Baths:
2.00
Sq.Ft.:
1,694
Status:
Active
MLS#:
5028831
Type:
Single Family
Lot size:
0.42 Acres
Year built:
1910
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Williamson Group Sothebys Intl. Realty
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ADDITIONAL INFORMATION

This classic early 20th Century farmhouse with 3 sunny bedrooms and two baths is sited on a quiet Village Street uphill above the Woodstock Elementary School and across from the public playground at Vail Field and the Woodstock Country Club golf course. The home has benefitted from the thoughtful additions of an eat-in kitchen and a front porch where you can enjoy long summer evenings. A comprehensive renovation several years ago opened the main level floorplan to eliminate partitions adapting the house to modern lifestyles. The backyard rises in tiers from the lower level with picnic table and grilling area to an elevated plateau used for expansive vegetable and flowers gardens. Truly a joyful place to call home in the heart of Woodstock's historic community.

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$2,450,000

851 Riverside Park Road Woodstock, VT 05091

MLS: 5025630 Photos
Beds:
4
Baths:
4.00
Sq.Ft.:
5,573
Status:
Active
MLS#:
5025630
Type:
Single Family
Lot size:
40 Acres
Year built:
1986
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Higgerson & Company
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ADDITIONAL INFORMATION

"All Seasons" is the ultimate Vermont retreat, designed for gatherings and getaways while seamlessly blending rustic charm with modern luxury. This 5,900-sq-ft barn-style home, just over five minutes from Woodstock Village via Route 4 and the Lincoln Covered Bridge, sits high on a knoll above the Ottauquechee River with views to Killington. A veritable mini-resort, the property offers unparalleled access to recreational pursuits. Its 40-acre grounds feature single-track biking, hiking, and snowshoeing trails, a firepit, patio, grills, and owned riverfront access. A 32-foot indoor pool, and hot tub under the stars make this a year-round haven. The acreage also includes a potential building lot with mountain views and an existing roadway, adding versatility. Nearby, enjoy world-class skiing, golf, and other outdoor activities, with Woodstock Village offering charming shops and restaurants. Inside, the chefâ??s kitchen boasts Viking appliances, granite counters, dual refrigerators, a pantry, and a custom island. Two expansive great rooms provide gathering spaces with large-screen TVs and plush seating, including a wet bar in the second-floor game room. Accommodations include four bedrooms, three full baths, and space for up to 12 guests. A highly successful Airbnb rental, â??All Sessonsâ?? is an extraordinary opportunity to own a Vermont escape combining privacy, beauty, and income potential in one of the regionâ??s most picturesque towns.

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$695,000

3914 South Road Woodstock, VT 05091

MLS: 5024226 Photos
Beds:
4
Baths:
3.00
Sq.Ft.:
3,584
Status:
Active
MLS#:
5024226
Type:
Single Family
Lot size:
5.1 Acres
Year built:
1984
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Williamson Group Sothebys Intl. Realty
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ADDITIONAL INFORMATION

This South Woodstock contemporary residence was designed by the original architect-owner to showcase Vermontâ??s changing seasons and capture views of the Kedron Brook as it wanders through the property past small meadows tucked in along the banks. The home can be accessed privately at grade level through the heated garage and mudroom, while guests enter via a covered entry to the upper level. The lower walk-out level of the home has two bedrooms, a shared bath, laundry and workshop. The elevated second floor is dedicated to gathering spaces including a great room with cathedral ceilings, eat in kitchen and family room that opens out on to a broad deck with overlooking the brook as it flows to the nearby Woodstock golf course and Athletic Club. The spacious primary bedroom offers an ensuite bathroom and abundant closet space. The main floor guest bedroom with loft is served by an adjacent bathroom. The two-stall multi-purpose barn opens to a small pasture and a fence yard for pets. A home for all seasons and reasons.

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$549,999

1613 West Woodstock Road Woodstock, VT 05091

MLS: 5022904 Photos

Open House:

Saturday, 5/24 10:00-2:00PM

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Beds:
3
Baths:
2.00
Sq.Ft.:
1,344
Status:
Active
MLS#:
5022904
Type:
Single Family
Lot size:
0.78 Acres
Year built:
1944
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: KW Vermont-Killington
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ADDITIONAL INFORMATION

WOODSTOCK-TURNKEY AND CONVENIENT! This totally renovated, move-in ready home located a few minutes to Woodstock Village, 20 minutes to Killington, 30 minutes to DHMC. Enjoy loads of recreational trails of all kinds, just minutes away.  Excellent spot with walking distance to the abutting Woodstock Union Middle School/High School. Newly Renovated inside and out. Spacious open concept living on main floor. The large, finished basement has a TV recreation area, workout space and pool table area. Custom built in cabinetry in the upstairs bedrooms. Private and wooded back yard with a covered porch, perennials, berries and gardens.  Huge potential to add-on, start a home business, create a rental unit or leave quaint and cozy as it is.  This property would be ideal for a primary residence or short-term rental investment property. Schedule your tour today of this sweet Woodstock GEM! PUBLIC OPEN HOUSE MAY 24, 2025, FROM 10AM TO 2PM. COME STOP BY TO SEE THIS TURNKEY HOME!

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$2,000,000

2706 East Woodstock Road Woodstock, VT 05091

MLS: 5020106 Photos
Beds:
4
Baths:
4.00
Sq.Ft.:
5,000
Status:
Active
MLS#:
5020106
Type:
Single Family
Lot size:
0.56 Acres
Year built:
1850
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Bassette Real Estate Group
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ADDITIONAL INFORMATION

INVESTMENT & RESIDENTIAL OPPORTUNITY - Rare historic building (The Taftsville Country Store - Woodstock VT) available for owner occupancy with multiple additional income units in the village of Taftsville. Just five minutes to the quintessential downtown New England Village of Woodstock! Property includes storefront space (approved for restaurant, café, or retail store), Post Office (with current lease), smaller Apartment 1 (with excellent AIRBNB rental history), larger Apartment 2 (The ownerâ??s unit- 3 bedroom, 2 bath), and plans/space for an additional studio unit. Perfect opportunity for an investor to offset living expenses with this multi-unit property, or just have a super fancy home office downstairs. Potential diversified income streams with hospitality, residential rental, and retail/ food service all in one property. 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.

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$3,750,000

249 Sawyer Road Woodstock, VT 05091

MLS: 5018393 Photos
Beds:
3
Baths:
5.00
Sq.Ft.:
3,865
Status:
Active
MLS#:
5018393
Type:
Single Family
Lot size:
2.37 Acres
Year built:
2009
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Real Broker LLC
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ADDITIONAL INFORMATION

This extraordinary residence offers breathtaking views of Billings Farm Preserve and the Green Mountains from nearly every corner, with Vermont's only national park directly in sight. The charming town of Woodstock, known for its boutiques and dining, is just a short walk away. Nestled at the end of a quiet road, the property offers unobstructed west-facing views for spectacular sunsets, surrounded by acres of undeveloped land. Woodstockâ??s restrictive covenants ensure these views remain undisturbed, creating a peaceful, private escape. The expansive deck around the stunning pool is controlled via smartphone, with an automatic cover to ease maintenance. The adjacent pool house features a custom kitchen, a luxurious bathroom, and a cozy living area framed by floor-to-ceiling glass, offering year-round comfort with air conditioning and heated floors. The inground, heated, 30,000 gallon pool, can reach over 102° year-round, a rare feature in Vermont. An NBA hoops basketball net is installed in the shallow end for many days of fun, or if the deep end is more your style this pool offers a 9 foot deep end. This unique property offers proximity to skiing, golf, hiking, and more. The view encompasses the only National Park in Vermont. Marsh-Billings-Rockefeller in Vermont is the only national park to focus on conservation history and the evolving nature of land stewardship in America located right here in beautiful Woodstock VT! Contact us today to arrange a private tour!

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$659,000

5851 South Road Woodstock, VT 05071

MLS: 5014012 Photos
Beds:
3
Baths:
3.00
Sq.Ft.:
1,958
Status:
Active
MLS#:
5014012
Type:
Single Family
Lot size:
0.68 Acres
Year built:
1920
Contact:
Inquire About This Property, [email protected], 877-559-9633
Courtesy: Williamson Group Sothebys Intl. Realty
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ADDITIONAL INFORMATION

This charming home is an amazing opportunity to own a piece of history in the lovely village of South Woodstock , Vermont. Starting its life as the garage and home of Clyde Wood it has evolved over time with the present owners into a beautiful , meticulous residence. Much attention to detail can be found in every room from wide pine flooring to cathedral ceiling in the great room. The home is light filled with a large deck looking out to the Kedron Brook and the Green Mountain Horse Association fields . The Honey Shop is where the Wood family sold honey from the large Bass trees on the property. It is now a lovely room for entertaining or enjoying a quiet spot to take a nap or read a favorite book. The barn could easily convert to garage space with plenty of room for storage . The very back of the barn is the only part of the buildings that is in the Flood zone. The grounds are beautifully landscaped . Cross over the brook on the little bridge to miles and miles of trails. Country living at its best but only 6 miles from Woodstock Village and short distances to skiing , golf, biking, all season sports and of course fly fishing on the Kedron Brook out your back door !. Call today for an appointment .

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Andrea D. Conner, License 71221, Xome Inc., License 68390, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Ste 100, Lewisville, TX 75067


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Woodstock Real Estate

Woodstock is located in Vermont. Woodstock, Vermont has a population of 3,011. Woodstock is more family-centric than the surrounding county with 33.72% of the households containing married families with children. The county average for households married with children is 26.01%.

The median household income in Woodstock, Vermont is $104,716. The median household income for the surrounding county is $63,787 compared to the national median of $69,021. The median age of people living in Woodstock is 53.8 years.

Woodstock Weather

The average high temperature in July is 81.4 degrees, with an average low temperature in January of 6.3 degrees. The average rainfall is approximately 46.1 inches per year, with 82.3 inches of snow per year.

Woodstock Map

Woodstock Real Estate Market Conditions

  • Median sales price

    $575,000
    19.1%
    change since last quarter

  • # Active listings

    41
    30-day change

Woodstock Schools and Demographics

Education near Woodstock, VT

City County
High School Graduates 98.07 94.16
College Degree - 2 year 8.78 8.49
College Degree - 4 year 58.54 40.21
Graduate Degree 21.92 12.49
Expenditures per Student 26,463 26,463
Students per Teacher 12.3 12.3

Elementary Schools near Woodstock, VT

Grades Students P/T Ratio ZIP
Barnard Academy PK - 06 70 10.3 05031
Bridgewater Village School PK - 06 37 6.2 05034
Ottauquechee School PK - 05 244 12.1 05059
Pomfret School PK - 06 53 8.5 05067
Woodstock Elementary School PK - 06 176 9.5 05091

Middle Schools near Woodstock, VT

Grades Students P/T Ratio ZIP
Woodstock Union Middle School 07 - 08 145 10.1 05091

High Schools near Woodstock, VT

Grades Students P/T Ratio ZIP
Woodstock Senior UHSD #4 09 - 12 347 8.9 05091

Demographics near Woodstock, VT

City County
Neighborhood Type Small town
Population 3,011 57,593
Population Density 68 59
Median Age 53.8 47.8
People per Household 2.3 2.3
Median Household Income 104,716 63,787
Average Income per Capita 56,639 39,377

Real estate near Woodstock

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