Windsor County VT Homes for Sale

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  /21

  $99,000

  • Land
  • 1.52 Acres
  • $65,132 per Acre

  0 Gold Coast Rd Unit 5089928, Bridgewater, VT 05035

  For many years the owners have enjoyed the serenity of this beloved campsite, as their Vermont Summer retreat. Now the time has come to pass their property on, for new owners to establish vacation memories of their own. The 1.5 acre parcel is wonderfully diverse! Near the height of the land an open area could well be the site for constructing a cabin. When facing South from this area a pleasant

  John Wetmore Wetmore Real Estate

  0 Gold Coast Rd Unit 5089928, Bridgewater, VT 05035
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  /41

  $5,150,000

  • 8 Beds
  • 7.5 Baths
  • 10,062 Sq Ft

  3800 Weston-Andover Rd, Andover, VT 05143

  Escape to Moosewalk Lane. This ultimate family compound is a fully furnished and equipped rural retreat in Andover, Vermont. Set on 384 acres rising to 2,200 feet, the tract blends seclusion and timeless craftsmanship, with miles of private trails for winter sports, horseback riding and recreational vehicles, all threading through open meadows, historic stone walls, and woodlands, with direct

  Steve Stettler Four Seasons Sotheby's Int'l Realty

  3800 Weston-Andover Rd, Andover, VT 05143
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  /57

  $3,749,000

  • 5 Beds
  • 5.5 Baths
  • 8,122 Sq Ft

  5685 Vermont 12, Barnard, VT 05031

  “HIGHLAND GLEN” – Rarely does a property capture the essence of Vermont as beautifully as Highland Glen. Set on twelve picturesque acres in the charming town of Barnard, this extraordinary estate blends timeless New England character with exceptional comfort, privacy, and recreation.Arrive by the iconic red barn and discover stunning gardens, apple orchard, meandering stone walls, flowing

  John Snyder Snyder Donegan Real Estate Group

  5685 Vermont 12, Barnard, VT 05031
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  /58

  $749,000

  • 3 Beds
  • 3 Baths
  • 2,697 Sq Ft

  1641 W Hill Rd, Rochester, VT 05767

  Welcome to The Birches — a peaceful end-of-road retreat where serenity, privacy, and Vermont’s natural beauty come together. Surrounded by more than 7,000 acres of conserved national forest land, this exceptional property offers unmatched tranquility, abundant wildlife, and direct access to outdoor adventure in every season.Set in a quiet mountain setting, this thoughtfully designed

  Brandon Fowler RE/MAX North Professionals

  1641 W Hill Rd, Rochester, VT 05767
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  /19

  $250,000

  • 2 Beds
  • 1 Bath
  • 968 Sq Ft

  133 Colonial Dr Unit 403, White River Junction, VT 05001

  *OFFER DEADLINE - 5/26 AT 5PM* Welcome to Oak Knoll Condominiums in White River Junction, VT. This 2 bedroom, 1 bathroom condo has been well updated and is ready for its next owner. New flooring on both levels, new appliances, and a custom laundry closet. The furnace is under four years old and the hot water tank was replaced two years ago, so the big ticket items are already done. Come check out

  Devin Josler Black House Real Estate

  133 Colonial Dr Unit 403, White River Junction, VT 05001
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  /36

  $449,000

  $30K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,094 Sq Ft

  75 Naulahka Ln, Hartford, VT 05059

  This Quechee retreat feels like a tree house. Combining three lots provides a level of privacy that is becoming increasingly rare in the Upper Valley, and the vertical layout makes excellent use of that wooded backdrop.By placing the Great Room behind two large picture windows, the design creates a seamless visual transition between the interior and the forest canopy.With a bedroom and full bath

  Linda Hicks Quechee Lakes Real Estate Center

  75 Naulahka Ln, Hartford, VT 05059
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  /43

  $360,000

  • 4 Beds
  • 3 Baths
  • 2,180 Sq Ft

  879 E Ash Rd Unit 8, Plymouth, VT 05056

  Ledges 8 at Hawk Resort offers the ultimate Vermont mountain retreat, featuring sweeping westerly views and year-round recreation. This spacious 4-bedroom, 3-bath end-unit townhouse spans three levels and is filled with natural light throughout. After a day on the slopes or trails, relax by the striking stone fireplace or unwind on the deck while taking in the mountain scenery. Start and end each

  Debra Staniscia Four Seasons Sotheby's Int'l Realty

  879 E Ash Rd Unit 8, Plymouth, VT 05056
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  /46

  $589,000

  • 3 Beds
  • 2 Baths
  • 1,708 Sq Ft

  1099 Lilliesville Brook Rd, Bethel, VT 05032

  Open House from 10 AM - 1 PM on Saturday May 23. Lovely - this is the only way to describe this property. Just lovely. This home was built with the utmost care in 2016. There is an attached heated garage that enters into the mudroom that doubles as the laundry room and opens directly into your kitchen. The kitchen sink has a bay window overlooking the oversize screened in porch. There are

  Holly Hall Hall Collins Real Estate Group

  1099 Lilliesville Brook Rd, Bethel, VT 05032
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  /45

  $599,999

  • 6 Beds
  • 5 Baths
  • 4,184 Sq Ft

  49 Pleasant St, Ludlow, VT 05149

  If you are a skier, this is your hop-on-the shuttle to Okemo location. If you want to park your car and walk to restaurants and shops, this is a great home base to scoot out from. If you want to generate rental income, this is a property that can allow you to have your cake and eat it too. An easy keeper, without a lot of landscape to take care of, this large residence has hardwood floors and

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  49 Pleasant St, Ludlow, VT 05149
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  /43

  $525,000

  • 3 Beds
  • 2 Baths
  • 1,856 Sq Ft

  208 Great Hawk Rd, Rochester, VT 05767

  Tucked into the woods of Rochester’s sought-after Great Hawk community, this beautifully updated contemporary chalet embodies the timeless Robert Carl Williams design aesthetic, blending warmth, character, and thoughtful modern improvements. Signature architectural details include soaring vaulted ceilings, wide pine floors, and a dramatic fieldstone fireplace that anchors the open-concept living

  Kyle Kershner Killington Pico Realty

  208 Great Hawk Rd, Rochester, VT 05767
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  /6

  $250,000

  • Land
  • 16 Acres
  • $15,625 per Acre

  13 Happy Hollow Rd, South Royalton, VT 05068

  White River frontage, high and dry house site offering pleasant view over Vermont Law School and level hay field.

  Dean Goulet Dunrovin Real Estate

  13 Happy Hollow Rd, South Royalton, VT 05068
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  /52

  $1,495,000

  • 5 Beds
  • 3.5 Baths
  • 3,648 Sq Ft

  1522 Barnard Rd, Woodstock, VT 05091

  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

  Keri Cole Williamson Group Sothebys Intl. Realty

  1522 Barnard Rd, Woodstock, VT 05091
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  /52

  $1,495,000

  • 3 Beds
  • 3 Baths
  • 2,650 Sq Ft

  3090 South Rd, Woodstock, VT 05091

  Known affectionately as “Green Gable Farm,” this beautifully renovated 1884 Vermont farmhouse sits on 5 picturesque acres in Woodstock, complete with a year-round babbling brook, just minutes from South Woodstock, the Woodstock Inn Fitness Center, golf course, cross-country ski trails, mountain biking, and the Woodstock Village Green. The current owners undertook a comprehensive renovation,

  John Snyder Snyder Donegan Real Estate Group

  3090 South Rd, Woodstock, VT 05091
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  /49

  $149,900

  • 6 Beds
  • 2 Baths
  • 2,361 Sq Ft

  110 Valley St, Springfield, VT 05156

  2 unit investment property features a 4 bedroom and a 2 bedroom unit. Both units are up down configurations. The first unit features decent kitchen with washer and dryer, living room, 3/4 bath, 2 first floor bedrooms and 2 upstairs bedrooms with a covered porch in the rear. The second unit has a living room, large kitchen with washer/dryer hookups, large 3/4 bath, deck, bedroom down, and a

  Steve Schoppmeyer BHG Masiello Brattleboro

  110 Valley St, Springfield, VT 05156
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  /27

  $285,000

  • 2 Beds
  • 1.5 Baths
  • 1,063 Sq Ft

  253 Old Quechee Rd Unit 5C, Hartford, VT 05001

  This classy and cozy two bedroom Mill Run condominium is beautifully decorated and has been well maintained by the owners since 2004. Sit by the woodstove and relax. Have cocktails on the deck and enjoy the outdoors. Tiled bathrooms, updated kitchen, washer/dryer and more have been added and improved to create a cozy well-equipped vacation spot.The second bedroom has been re-designed to have four

  Jackie Jameson Jameson Real Estate

  253 Old Quechee Rd Unit 5C, Hartford, VT 05001
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  /12

  $389,000

  • Land
  • 4.73 Acres
  • $82,241 per Acre

  5209 Willard Rd, Hartford, VT 05059

  A thoughtfully assembled 4.73-acre homesite in Quechee Lakes’ Upper Willard Road neighborhood. Created from two combined lots, this property offers uncommon scale, privacy, and flexibility in one of the area’s more established settings. The land has been carefully curated by the current owner to take advantage of the natural Vermont landscape, with a mix of wooded surroundings and potential

  Richard Higgerson Higgerson & Company

  5209 Willard Rd, Hartford, VT 05059
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  /36

  $535,000

  • 6 Beds
  • 4 Baths
  • 4,933 Sq Ft

  2 Pine St, Windsor, VT 05089

  Come see and appreciate this recently rejuvenated and extraordinary home that includes 6 bedrooms and 4 bathrooms as well as a 2 car garage! Located just off the downtown village area, this unique property features historical charm and character with vintage woodwork, custom wood floors, high ceilings, spacious rooms and the nooks and crannies a classic home has to offer! Relax on the rear porch

  Susan Bellville Bellville Realty

  2 Pine St, Windsor, VT 05089
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  /20

  $475,000

  • 3 Beds
  • 2 Baths
  • 1,346 Sq Ft

  111 Lakeland Dr Unit D, Quechee, VT 05059

  Experience the ultimate four-season lifestyle in this desirable end-unit condo at Quechee Lakes. Perfectly situated for both relaxation and adventure, this home offers ultimate convenience with both the Highland Golf Course and Lakeland Golf Courses just steps from your door, and the best of the Quechee Club just a short stroll away. Enjoy the ease of a first-floor primary bedroom and an open,

  Kasia Butterfield Coldwell Banker LIFESTYLES - Quechee

  111 Lakeland Dr Unit D, Quechee, VT 05059
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  /37

  $475,000

  • 5 Beds
  • 3 Baths
  • 2,056 Sq Ft

  57 Pleasant St, Ludlow, VT 05149

  Located in the heart of the Village of Ludlow, this versatile multi-family property features three well-appointed apartments with excellent rental potential. The property includes a private one-bedroom unit tucked away at the rear of the home with an upper-level bedroom retreat, plus two spacious two-bedroom apartments offering comfortable living areas and functional layouts. Enjoy a prime

  Katherine Burns William Raveis Real Estate Vermont Properties

  57 Pleasant St, Ludlow, VT 05149
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  /51

  $6,673,000

  • 5 Beds
  • 3.5 Baths
  • 4,165 Sq Ft

  2358 Long Hill Rd, Woodstock, VT 05091

  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

  Story Jenks LandVest, Inc/Woodstock

  2358 Long Hill Rd, Woodstock, VT 05091
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  /55

  $425,000

  • 3 Beds
  • 3 Baths
  • 1,746 Sq Ft

  1899 Rousseau Rd, Bethel, VT 05032

  I would like to invite you to view a remarkable listing that offers a serene rural retreat. Situated on five private acres, this one-of-a-kind custom log home is surrounded by lush garden beds and beautiful forests, providing an exceptional connection to nature and local wildlife. Despite its peaceful, tucked-away location, the property is conveniently positioned just three miles from downtown

  Jonathan Falby Green Light Real Estate

  1899 Rousseau Rd, Bethel, VT 05032
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  /57

  $429,900

  • 3 Beds
  • 2 Baths
  • 2,178 Sq Ft

  38 Marshall Ave, White River Junction, VT 05001

  Classic contemporary ranch home with touches of sophistication located in beautiful White River Junction, VT. This 3 bedroom 2 bath home radiates warmth and hospitality and could be perfect for single level living. Enjoy a fabulous open kitchen / dining room concept featuring cathedral style ceilings, laminate wood floors for easy cleaning, a dual sided fireplace, built-in bookcase, a breakfast

  Alex DeFelice The Clerkin Agency, P.C.

  38 Marshall Ave, White River Junction, VT 05001
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  /38

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,352 Sq Ft

  847 Simonsville Rd, Andover, VT 05143

  Looking to find your own peaceful piece of the Vermont countryside? Look no further than this move in ready homestead on 51.2 rolling acres with twopaddocks already fenced and ready waiting for your animals. Also complete with two spacious sheds for animals or storage, and a chicken coop ready to house them. Established asparagus patch, garden plot,blueberry bushes, apple trees, and even

  Erin Kendall EXP Realty

  847 Simonsville Rd, Andover, VT 05143
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  /13

  $158,000

  • Land
  • 17,424 Sq Ft
  • $395,000 per Acre

  29 Mill St, Hartland, VT 05048

  Superb IN-town North Hartland building lot with charming VT. sugar house to use for storage or maple sugaring! Also enjoy Hartlands benefit of school choice for high school students! Don't miss this opportunity to build your new home in the 2026 building season. A very Nice .40+/- acre in town parcel situated just across from Currier recreation park in North Hartland, VT. This lot is mostly level

  Alex DeFelice The Clerkin Agency, P.C.

  29 Mill St, Hartland, VT 05048
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  /48

  $395,000

  • 2 Beds
  • 1 Bath
  • 680 Sq Ft

  38 Northshore Dr, Ludlow, VT 05149

  Lake Rescue Retreat.Embrace the lakeside lifestyle in this quintessential Vermont cottage on Lake Rescue. Nestled on a spacious lot, this property perfectly blends historic character with future opportunity. You can choose to use the existing structure as your ultimate summer escape, remodel it to your exact taste, or build your brand-new dream lakeside home from the ground up.A fully

  Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

  38 Northshore Dr, Ludlow, VT 05149
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  /39

  $255,000

  • 1 Bed
  • 1 Bath
  • 1,664 Sq Ft

  1417 Dublin Rd, Plymouth, VT 05056

  Tucked away on a beautifully secluded lot, this charming home offers the perfect blend of privacy and comfort. The heart of the house features an open-concept kitchen, living, and dining area—ideal for easy entertaining or quiet evenings in.The layout includes a cozy primary bedroom plus a versatile bonus room, perfect for a home office or guest space. Convenience is key with a dedicated

  Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

  1417 Dublin Rd, Plymouth, VT 05056
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  /57

  $299,900

  • 3 Beds
  • 1.5 Baths
  • 956 Sq Ft

  427 Maple St, White River Junction, VT 05001

  Bring your vision to this charming 3-bedroom Cape in the heart of White River Junction, featuring period details and a cozy fireplace. This "diamond in the rough" offers 1.5 baths, a two-car garage, and a walk-to-town location, needing only cosmetic updates to shine. A rare opportunity for character and convenience!

  Dorothy Griswold The Clerkin Agency, P.C.

  427 Maple St, White River Junction, VT 05001
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  /59

  $2,395,000

  • 3 Beds
  • 5 Baths
  • 4,329 Sq Ft

  719 Walker Hill Rd, Barnard, VT 05068

  An exquisite, private retreat for artists, writers, nature-lovers, composers or simply as a quiet, serene getaway gathering house on 66 stunningly beautiful acres with stone walls, gardens, patios, open lawns, a beautiful swimming pond, in-ground heated saltwater pool with stone patio, and a breathtakingly beautiful outdoor screened pergola. The residence was constructed using reclaimed frames

  John Snyder Snyder Donegan Real Estate Group

  719 Walker Hill Rd, Barnard, VT 05068
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  /28

  $219,000

  • 1 Bed
  • 1 Bath
  • 744 Sq Ft

  16 Hemlock Ridge Dr Unit 101, White River Junction, VT 05001

  Charming 1-Bedroom Condo conveniently located just 3 miles to Dartmouth College and surrounding area with easy interstate access as well. This inviting one bedroom condo at the Barn at Hemlock Ridge offers the perfect blend of comfort and utility. The layout features an additional versatile room ideal for a dedicated home office or study space. Association dues cover both heat and hot water.

  Dorothy Griswold The Clerkin Agency, P.C.

  16 Hemlock Ridge Dr Unit 101, White River Junction, VT 05001
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  /60

  $549,900

  • 1 Bed
  • 1 Bath
  • 960 Sq Ft

  544 Vulture Mountain Rd, Stockbridge, VT 05772

  A One-of-a-Kind VT Mountain Retreat with Strong Rental Income! Discover a truly unique family compound perched atop a private mountain, offering breathtaking views of conserved wilderness, including majestic Killington Peak & the beautiful White River below. Set on 1.2 acres, this remarkable property seamlessly blends vintage character w/thoughtful modern updates, creating the perfect retreat for

  Marni Rieger KW Vermont-Killington

  544 Vulture Mountain Rd, Stockbridge, VT 05772
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  /11

  $225,000

  • Land
  • 27.2 Acres
  • $8,272 per Acre

  0 E Hill Rd, Andover, VT 05143

  Nestled in the heart of Vermont’s scenic countryside, this beautiful 27.2-acre parcel offers the perfect setting to build your dream home or mountain retreat. Mostly wooded with over 800 feet of road frontage, the property combines privacy, natural beauty, and easy access to some of Southern Vermont’s most desirable destinations.Enjoy mountain and scenic views that provide ideal building

  Gary Coger Four Seasons Sotheby's Int'l Realty

  0 E Hill Rd, Andover, VT 05143
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  /41

  $815,000

  • 5 Beds
  • 3.5 Baths
  • 3,284 Sq Ft

  2605 Cox District Rd, Woodstock, VT 05091

  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

  Bonnie Bergeron Snyder Donegan Real Estate Group

  2605 Cox District Rd, Woodstock, VT 05091
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  /32

  $264,900

  • 3 Beds
  • 1 Bath
  • 1,050 Sq Ft

  13 Brierbrook Ln, Springfield, VT 05156

  Check out this sweet ranch home in a desirable cul-de-sac, but a short distance to schools, the shopping plaza, hospital, as well as downtown amenities. The roomy eat-in kitchen has plenty of cabinet space and a small bay window overlooking the yards. The living room is delightful with a large picture window and a cozy nook for, whatever, TV, bookcase, your desire! Three bedrooms and a full

  Carol Cole BHG Masiello Brattleboro

  13 Brierbrook Ln, Springfield, VT 05156
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  /19

  $579,000

  • Land
  • 60.57 Acres
  • $9,559 per Acre

  0 Noah Wood Rd, Woodstock, VT 05071

  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

  Dan Noble Snyder Donegan Real Estate Group

  0 Noah Wood Rd, Woodstock, VT 05071
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  /39

  $1,200,000

  • 4 Beds
  • 3 Baths
  • 3,308 Sq Ft

  76 Goldthwaite Rd, Chester, VT 05143

  Experience the Vermont lifestyle in this beautifully renovated 1864 Brick Federal-style farmhouse set on 7.8 private acres just minutes from town. Rich in historic character and thoughtfully updated for modern living, this exceptional property offers the perfect blend of comfort, charm, and year-round recreation.Inside, you’ll find four spacious bedrooms, wide plank wood floors, and inviting

  Gary Coger Four Seasons Sotheby's Int'l Realty

  76 Goldthwaite Rd, Chester, VT 05143
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  /11

  $695,000

  • 4 Beds
  • 2 Baths
  • 2,288 Sq Ft

  11 Maple St, Woodstock, VT 05091

  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

  John Wetmore Wetmore Real Estate

  11 Maple St, Woodstock, VT 05091
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  /9

  $300,000

  • Land
  • 9.8 Acres
  • $30,612 per Acre

  00 Stagecoach Rd, Norwich, VT 05055

  Discover peace and privacy on this 9-acre wooded lot situated near the end of a quiet private road. This natural haven offers excellent seclusion while remaining just 10 minutes from town amenities. With a mix of hardwood and softwood, the property features a significant stand of hemlock and oak —potentially providing enough timber to build your own custom timber-frame home right from the

  Linda White EXP Realty

  00 Stagecoach Rd, Norwich, VT 05055
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  /43

  $1,299,000

  • 4 Beds
  • 3 Baths
  • 4,372 Sq Ft

  278 Lawrence Hill Rd, Weston, VT 05161

  Set in the heart of Vermont’s four season playground, this impeccably maintained 4 bedroom, 3 bath home with a private swimming pond offers the perfect balance of comfort, space and outdoor living. Thoughtfully built by the previous owners and meticulously maintained by the current owners, the property reflects care, pride, and attention to detail, with many thoughtful upgrades and improvements

  Lisa Sullivan Four Seasons Sotheby's Int'l Realty

  278 Lawrence Hill Rd, Weston, VT 05161
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  /40

  $500,000

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft

  7429 US Route 4, Bridgewater, VT 05034

  THE SUGAR HOUSE — Beautifully renovated in 2007, this light-filled Vermont home is ideally located in the heart of historic Bridgewater, just 10 minutes from the charm, dining, and culture of the village of Woodstock. Offering the perfect balance of four-season recreation and classic New England character, the property is equally suited as a primary residence, weekend retreat, or investment

  Keri Cole Williamson Group Sothebys Intl. Realty

  7429 US Route 4, Bridgewater, VT 05034
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  /39

  $349,000

  • 4 Beds
  • 3 Baths
  • 3,332 Sq Ft

  397 River St, Chester, VT 05143

  Some properties just radiate a certain warmth, charm and magic and this home is definitely one of them. Imagine sitting on the front porch and listening the soft rustle of the willow tree leaves and the babbling brook trickling by, then you step inside and feel that you have walked into a home that was truly loved. The large kitchen offers nice upgrades including tile floor, granite countertops

  

  Lisa Kelley

  Cummings & Co

  (802) 392-0114

  397 River St, Chester, VT 05143

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