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Windsor County VT Homes for Sale

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  • /8

    $275,000

    $124K PRICE DROP
    • Land
    • 12 Acres
    • $22,917 per Acre

    1985 Gee Hill Rd, Royalton, VT 05068

    This breathtaking parcel is ready for you to hit the ground running literally. The driveway is in, the house site is cleared, and the sweeping mountain views are already on full display from ground level. Designed with a walk-out basement in mind, the layout is perfect for maximizing both light and landscape. Fully permitted for a 5-bedroom septic system, this property offers space, flexibility,

    Holly Hall Hall Collins Real Estate Group

    1985 Gee Hill Rd, Royalton, VT 05068
  • /33

    $695,000

    $55K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 2,285 Sq Ft

    47 Pleasant St, Woodstock, VT 05091

    Excellent opportunity for residential or office/commercial space with easy access and high visibility on Rt 4 coming into town, Currently configured as office space downstairs (which previously has been living space), combined with a separate two-bedroom apartment (with its own access) upstairs. The 1,335 sf lower level (Unit C) is currently a chiropractor's office space and was previously used

    John Snyder Snyder Donegan Real Estate Group

    47 Pleasant St, Woodstock, VT 05091
  • /41

    $5,150,000

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

    3800 Weston-Andover Rd, Andover, VT 05143

    Bringing generations together in a place that inspires connection, adventure, celebration, work and stewardship, Moosewalk Lane is a purpose built multigenerational family compound. Created over two decades and set on 384 private acres in Vermont's Green Mountains, Moosewalk Lane is offered fully furnished and equipped. Anchored by a 10,062 square foot timber frame home, guest house, writer's

    Steve Stettler Four Seasons Sotheby's Int'l Realty

    3800 Weston-Andover Rd, Andover, VT 05143
  • /58

    $640,000

    $109K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,697 Sq Ft

    1641 W Hill Rd, Rochester, VT 05767

    This exceptional off-grid property offers the perfect blend of self-sufficiency, comfort, and Vermont adventure. With a reliable solar system, automatic backup generator, and fiber internet, “The Birches” is well suited for either a full-time residence or a peaceful second home.Outdoor enthusiasts will love the location, with more than 7,000 acres of National Forest surrounding the property

    Brandon Fowler RE/MAX North Professionals

    1641 W Hill Rd, Rochester, VT 05767
  • /36

    $399,000

    $80K 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
  • /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
  • /12

    $225,000

    $25K PRICE DROP
    • Land
    • 16 Acres
    • $14,062 per Acre

    2840 Vt Route 14, Royalton, VT 05068

    Long White River frontage, high and dry house site offering pleasant view over Vermont Law School and level hay field. House site has utilities available and existing frontage on Route 14.

    Dean Goulet Dunrovin Real Estate

    2840 Vt Route 14, Royalton, VT 05068
  • /58

    $1,395,000

    $100K PRICE DROP
    • 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
  • /23

    $279,000

    $6K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,063 Sq Ft

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

    This completely furnished and cozy 2 bedroom Mill Run condominium is ready to be moved into as is! Set up to sleep 5, it is a is perfect vacation spot or a rental investment property or a full time home. As a member of Quechee Lakes Resort, owners and guests have access to all resort ammenities including golf, tennis, skiing, pools, Pickle Ball, dining, excercise club and locker rooms with saunas

    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

    $500,000

    $35K PRICE DROP
    • 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
  • /37

    $450,000

    $25K PRICE DROP
    • 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
  • /38

    $350,000

    $25K PRICE DROP
    • 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

    $143,000

    $15K PRICE DROP
    • Land
    • 17,424 Sq Ft
    • $357,500 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
  • /23

    $225,000

    $26K PRICE INCREASE
    • 1 Bed
    • 1 Bath
    • 992 Sq Ft

    389 Dothan Rd, White River Junction, VT 05001

    Adorable Adirondack-style one bedroom, one bath home nestled into a pine-covered hillside with a babbling brook right out the back door. Privately situated with a shed, deck, and balcony overlooking local wildlife and the surrounding natural beauty. The open concept living and dining area flows into the kitchen with pantry, creating a warm and inviting atmosphere. Unique open-air design makes

    Richard Ballou RE/MAX Upper Valley

    389 Dothan Rd, White River Junction, VT 05001
  • /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
  • /59

    $2,195,000

    $200K PRICE DROP
    • 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 has five rooms with beds (easily sleeps

    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
  • /17

    $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
  • /19

    $529,000

    $50K PRICE DROP
    • Land
    • 60.57 Acres
    • $8,734 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
  • /44

    $595,000

    $100K PRICE DROP
    • 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
  • /53

    $1,490,000

    $200K PRICE DROP
    • 5 Beds
    • 5 Baths
    • 5,400 Sq Ft

    1302 Popple Dungeon Rd, Chester, VT 05143

    Set on 18 private acres, Popple Dungeon is a distinctive Vermont property offering the feel of a true country retreat. Owned by one family and designed and built by its owner, the Williamsburg style reproduction Saltbox reflects a deep appreciation for traditional craftsmanship and enduring design.Inside, the home is defined by warm, handcrafted details wide plank wood floors, paneled walls,

    Gary Coger Four Seasons Sotheby's Int'l Realty

    1302 Popple Dungeon Rd, Chester, VT 05143
  • /20

    $150,000

    • Land
    • 18.78 Acres
    • $7,987 per Acre

    00 Boynton Rd, Londonderry, VT 05148

    Londonderry, Vermont, features a 19-acre building lot that comes with an approved 5-bedroom State Waste Water permit. This location is conveniently situated within 20 minutes of four ski resorts: Stratton, Bromley, Okemo, and the local favorite, MAGIC MOUNTAIN. Additionally, Manchester is just 20 minutes away for those interested in shopping. The area also offers a wide variety of dining options.

    Mike England Michael England Real Estate

    00 Boynton Rd, Londonderry, VT 05148
  • /35

    $69,900

    $2K PRICE DROP
    • 1 Bed
    • 2 Baths
    • 775 Sq Ft

    368/370 Qtr I V Jackson Gore Inn, Ludlow, VT 05149

    Desirable third-floor lockout unit in Jackson Gore, ideally positioned facing the valley with beautiful, expansive views. Located just steps from the Round House, this residence offers exceptional proximity to the lifts, pools, and dining, making it a perfect year-round getaway. Unit C features: A spacious one-bedroom layout with lockout capability, offering flexibility for personal use or rental

    Laurene Skinner Mary W. Davis Realtor & Assoc., Inc.

    368/370 Qtr I V Jackson Gore Inn, Ludlow, VT 05149
  • /60

    $2,500,000

    • 4 Beds
    • 3.5 Baths
    • 5,127 Sq Ft

    114 Oak Ridge Way, Woodstock, VT 05091

    See the property specific website with video, 3-D tour and more. Set against the timeless beauty of Woodstock’s rolling countryside, this exceptional estate offers a rare blend of refined luxury and pastoral charm. Thoughtfully designed for both elegant entertaining and everyday comfort, the four-bedroom, four-bath residence centers around a stunning gourmet kitchen—complete with a Sub-Zero

    Tami Sullivan Snyder Donegan Real Estate Group

    114 Oak Ridge Way, Woodstock, VT 05091
  • /27

    $600,000

    $50K PRICE DROP
    • 2,674 Sq Ft

    5863 Vermont 14, Royalton, VT 05068

    Overlooking the magnificent White River and Second Branch, this attractive older home has been a labor of love for the past 30 years. The long list of upgrades, additions, improvements, etc. speak for themselves. The spacious first floor has been used as home occupation featuring a 350 sq. ft. impressive office space. The apartments can be opened up to be single family or collect a projected net

    Dean Goulet Dunrovin Real Estate

    5863 Vermont 14, Royalton, VT 05068
  • /22

    $90,000

    • 0.5 Baths
    • 200 Sq Ft

    1093 Old Bow Rd, Springfield, VT 05156

    This welcoming 3-acre recreational getaway—with on-site power, a driveway entrance, and multiple sleeping quarters—offers the perfect retreat for anyone who loves hiking, biking, skiing, or simply relaxing in nature. Already set up for comfortable camping, the property includes a tiny house equipped with essential amenities and a trailer featuring its own private toilet room. Additional

    Christine Lavery North New England Real Estate Group

    1093 Old Bow Rd, Springfield, VT 05156
  • /12

    $125,000

    $10K PRICE DROP
    • Land
    • 16.9 Acres
    • $7,396 per Acre

    00 Day Rd, Sharon, VT 05065

    A wonderful opportunity to build in the quaint town of Sharon, VT. This unique acreage consists of a smaller open meadow that feeds into a picturesque and private roughed in logging road wrapping around a larger thinned out wooded area - offering a variety of potential locations to build your dream home. Potential for lovely views. The location is off a private dead-end road with I-89 only a few

    Bonnie Bergeron Snyder Donegan Real Estate Group

    00 Day Rd, Sharon, VT 05065
  • /58

    $574,900

    $24K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,200 Sq Ft

    84 Old Barn Ln, West Windsor, VT 05089

    This is one of those homes you simply have to experience in person. The views alone are worth the visit. Perched above the valley with commanding, panoramic views of Mount Ascutney, this exceptional custom-built home offers a front-row seat to some of Vermont's most breathtaking scenery. From sunrise over the mountains to spectacular evening sunsets, every window showcases a landscape that

    Katie Ladue Gilbert BHHS Verani Upper Valley

    84 Old Barn Ln, West Windsor, VT 05089
  • /17

    $325,000

    • Land
    • 51.59 Acres
    • $6,300 per Acre

    334 Log Cabin Dr, Pomfret, VT 05067

    334 Log Cabin Drive offers 51.59 acres of hardwood forest in South Pomfret, Vermont, with east and south-facing aspects through an open canopy. The stand lets light in all winter and turns into a cathedral in October. Mature birch, beech, and maple rise from a clean understory with good spacing, and scattered spruce and hemlock anchor the margins. Leaf-off views sweep across the ridgeline with no

    Richard Higgerson Higgerson & Company

    334 Log Cabin Dr, Pomfret, VT 05067
  • /13

    $519,999

    • Land
    • 65.6 Acres
    • $7,927 per Acre

    12 Old Route 12, Barnard, VT 05032

    Large wooded parcel ascending two hillsides, with a creek-carved valley in the middle. The eastern side is easy to explore thanks to over 1,500 feet of dirt roads cut through the trees. The western side ascends to a summit with sparse tree cover and amazing scenic views. Beyond this the land continues up and over the ridge line then downhill once again to the Stockbridge town line.This

    David White OwnerEntry.com

    12 Old Route 12, Barnard, VT 05032
  • /51

    $720,000

    $15K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,282 Sq Ft

    3755 Quechee Main St Unit 10A, Quechee, VT 05059

    Very rare opportunity to buy a unit in the park-like setting of the coveted Coach Road condominium community. Coach Road Unit 10A offers one of the most desirable locations in Quechee, within walking, biking, or a very quick golf cart ride to the clubhouse and all the amenities QLLA has to offer. This desirable three-bedroom, four-bath Quechee Lakes location on Coach Road is a lovely place to

    Lyndsey Freeman Quechee Lakes Real Estate Center

    3755 Quechee Main St Unit 10A, Quechee, VT 05059
  • /49

    $2,195,000

    • 3 Beds
    • 3 Baths
    • 2,997 Sq Ft

    9671 Vt Route 12, Barnard, VT 05031

    SPRING HILL FARM– A Storied Vermont Estate with Timeless Appeal. Set amidst the rolling hills of Barnard, Vermont, Spring Hill Farm is a distinguished country estate where historic charm and thoughtful stewardship come together across 207 acres of beautifully maintained landscape. Anchoring the property is a stately brick residence dating to 1795, offering a refined sense of heritage and

    Agent Photo

    Susan Hickey

    Snyder Donegan Real Estate Group

    9671 Vt Route 12, Barnard, VT 05031
  • /60

    $1,200,000

    $100K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,908 Sq Ft

    366 Knapp Pond Rd, Cavendish, VT 05142

    Did I read that right? 172 acres?! Impeccably renovated farmhouse on +-172 acres - what more could you ask for? ~131 acres of this property are located in Cavendish while the other ~41 are in Reading. Enjoy apples straight from the backyard. Listen and watch the brook babble down by the road and enjoy the peace that comes from this lovely home. All new Marvin Elevate windows, all new appliances,

    Franchesca Collins Hall Collins Real Estate Group

    366 Knapp Pond Rd, Cavendish, VT 05142
  • /60

    $2,200,000

    $295K PRICE DROP
    • 5 Beds
    • 9 Baths
    • 7,322 Sq Ft

    1497 Bowman Rd, Barnard, VT 05068

    Circa 1799 Vermont cape, thoughtfully restored and expanded to over 7,300 finished square feet on 12.5 private acres, minutes to Silver Lake and Woodstock village. Five bedrooms, nine baths, and a layout that balances everyday living with the ability to host. Original materials carry throughout, including wide pine floors, skim-coat plaster walls, hand-carved paneling, and period hardware, giving

    Richard Higgerson Higgerson & Company

    1497 Bowman Rd, Barnard, VT 05068
  • /46

    $1,325,000

    • 4 Beds
    • 2 Baths
    • 2,554 Sq Ft

    325 Cemetery Rd, West Windsor, VT 05089

    Farm at Gaelic Crossing is an equestrian property set on 26.72± acres, has dramatic views of Mount Ascutney and, after summer showers, the frequent and magical appearance of rainbows—often even double rainbows—across the wide, open sky. This updated c.1842 New England Cape offers 2,554 square feet of finished living space, including four bedrooms—two conveniently located on the first floor. Wide

    Story Jenks LandVest, Inc/Woodstock

    325 Cemetery Rd, West Windsor, VT 05089
  • /41

    $465,000

    $85K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,939 Sq Ft

    105 Craigue Hill Rd, Springfield, VT 05156

    Motivated Seller has reduced the price dramatically, on this 17 acre, property with a pond and 2 houses, just waiting for you to put your special touches on it. the private setting offers plenty of room for trails, gardens and more. Close to schools, shopping, medical services and recreation, this property offers privacy, views and a pond. This property also enjoys a beautiful guest house for

    Carol Cole BHG Masiello Brattleboro

    105 Craigue Hill Rd, Springfield, VT 05156

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