454

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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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

    Agent Photo

    Lisa Kelley

    Cummings & Co

    (802) 392-0114

    397 River St, Chester, VT 05143

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