253

Windsor County VT Houses for Sale

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  • /32

    $400,000

    • 2 Beds
    • 1 Bath
    • 1,324 Sq Ft

    2556 Church Hill Rd, Wood Stock, VT 05091

    Once an old school house, this home features stone walls, beautiful gardens, and a nice level yard with a stone patio. The year-round brook cascades over rocks and winds along the back side of the property. A covered porch leads inside, where the main floor offers an eat-in kitchen, a large living room and a dining area with French doors to the outside. There are also two bedrooms, an office with

    Dan Noble Snyder Donegan Real Estate Group

    2556 Church Hill Rd, Wood Stock, VT 05091
  • /29

    $360,000

    New Construction $55K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,100 Sq Ft

    696 Vermont Route 100, Ludlow, VT 05149

    LUDLOW: Lake Pauline Waterfront with Existing Footprint and Permit in Place.Opportunity to own a unique lakefront property on Lake Pauline with approximately 600 feet of shoreline and over an acre of land just minutes from Okemo Mountain Resort.The existing home is positioned close to the water within an established footprint that could not be replicated under current regulations. This

    Melissa Loughan Westside Real Estate

    696 Vermont Route 100, Ludlow, VT 05149
  • /21

    $2,950,000

    $350K PRICE DROP
    • 3 Beds
    • 4.5 Baths
    • 3,682 Sq Ft

    249 Sawyer Rd, Woodstock, VT 05091

    Located in Woodstock, Vermont just one mile from the village green, the Alta House offers a rich quality of life filled with poolside sunsets, mountain vistas, proximity to town, and access to endless outdoor recreation opportunities. Enjoy the convenience of living close to the shops, cafes, and restaurants of Woodstock, while being tucked away in your own world above. The 3-bedroom primary

    Andrew Bustin LandVest, Inc/Woodstock

    249 Sawyer Rd, Woodstock, VT 05091
  • /60

    $4,450,000

    • 7 Beds
    • 6.5 Baths
    • 6,245 Sq Ft

    53 Moon Shadow Dr, Ludlow, VT 05149

    Perched in an unrivaled location on the Moonshadow Trail, this spectacular mountain residence has been thoughtfully and extensively renovated to offer the perfect blend of luxury, comfort, and year-round recreation. Featuring 7 bedrooms and 61⁄2 baths, this exceptional home is designed to accommodate large gatherings while maintaining an inviting atmosphere throughout. The heart of the home is

    Kevin Barnes William Raveis Real Estate Vermont Properties

    53 Moon Shadow Dr, Ludlow, VT 05149
  • /57

    $1,150,000

    • 4 Beds
    • 3.5 Baths
    • 4,266 Sq Ft

    476 Dix Hill, Plymouth, VT 05056

    This perfect country get-away offers privacy, views to the west of Okemo Mountain and easy access to skiing and the lakes region, all just a short drive away. With over 4,000 sq. ft. and generous size rooms throughout, the (3) floors of quality living space have been beautifully updated and maintained by the current owners. A few of the homes many notable features include a large air lock entry,

    Roger Danyew Diamond Realty

    476 Dix Hill, Plymouth, VT 05056
  • /14

    $1,560,000

    New Construction $65K PRICE INCREASE
    • 4 Beds
    • 4.5 Baths
    • 3,120 Sq Ft

    4070 Tichenor Rd, Hartford, VT 05059

    The Thistle at Mountain Stream — To be built by Mountain Stream at Quechee Lakes, the Thistle offers 3,120 square feet of contemporary living across two levels, paired with a single-bay tuck-under garage, separate heated storage with optional rec-room conversion, and a detached two-car garage. A long, low silhouette under a sweeping shed roof, vertical board-and-batten siding, and a dramatic

    Richard Higgerson Higgerson & Company

    4070 Tichenor Rd, Hartford, VT 05059
  • /43

    $309,000

    • 3 Beds
    • 2.5 Baths
    • 2,174 Sq Ft

    147 Park St, Springfield, VT 05156

    Welcome to 147 Park Street! Situated on a 0.31-acre lot with a fully fenced yard, perennial flower gardens, and attractive landscaping, this home offers plenty of space both inside and out.Full of character and style, this spacious home features a thoughtful floor plan designed for everyday living. The large kitchen includes updated appliances, a generous dining area, and plenty of room for

    Mary Paino Coldwell Banker LIFESTYLES - Quechee

    147 Park St, Springfield, VT 05156
  • /58

    $1,395,000

    • 3 Beds
    • 2.5 Baths
    • 2,112 Sq Ft

    683 Reservoir Rd, White River Junction, VT 05001

    Welcome to Trail’s End - an oasis of peace and tranquility suffused with the restorative power of nature. Set amidst lush gardens and rolling lawns, this gorgeous timber frame house blends traditional looks with modern sensibilities and amenities, offering comfortable, light-filled, and highly functional spaces throughout. The beautifully appointed main floor primary bedroom features a spacious

    Zoe Hathorn Washburn Snyder Donegan Real Estate Group

    683 Reservoir Rd, White River Junction, VT 05001
  • /58

    $675,000

    $74K PRICE DROP
    • 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 3-bedroom,

    Brandon Fowler RE/MAX North Professionals

    1641 W Hill Rd, Rochester, VT 05767
  • /32

    $2,300,000

    • 4 Beds
    • 4.5 Baths
    • 3,524 Sq Ft

    134 Chester Arthur Rd, Hartford, VT 05047

    A quality residence with 4.69 landscaped acres beautifully complimenting the estate! Entering into the grounds a graceful drive meanders through landscaped lawns to arrive at a stone patio and an appealing New England style residence. Conveniently, there is option to enter an attached garage with direct entrance to the residence. After crossing the stone patio, passing through the front door

    John Wetmore Wetmore Real Estate

    134 Chester Arthur Rd, Hartford, VT 05047
  • /34

    $489,000

    • 3 Beds
    • 2 Baths
    • 1,626 Sq Ft

    3208 Green Mountain Turnpike, Chester, VT 05143

    Located in the Historic Stone Village of Chester, this thoughtfully renovated and reimagined circa 1880 home combines modern minimalist style with artisan craftsmanship. Set on .33± acres, this light-filled property features wide-pine floors, exposed beams, and a Vermont Castings woodstove anchoring an inviting open-concept living space. The kitchen/dining area showcases country cabinets with

    Geralyn Donohue Four Seasons Sotheby's Int'l Realty

    3208 Green Mountain Turnpike, Chester, VT 05143
  • /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
  • /58

    $695,000

    $200K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 4,144 Sq Ft

    1607 Massey Rd, Springfield, VT 05156

    MOTIVATED SELLER!!! Nestled in the rolling countryside of Springfield, this 1810 Federal-style brick farmhouse stands proudly on 44 breathtaking acres—an offering rich in history, character, and Vermont lifestyle.Open fields stretch out from the home, ideal for gardens, small-scale farming, or simply soaking in the pastoral beauty. Wooded acreage invites exploration, wildlife watching, and

    Jessica Citera Cummings & Co

    1607 Massey Rd, Springfield, VT 05156
  • /26

    $110,000

    $9K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 240 Sq Ft

    505 Back Mountain Rd Unit 14, Windsor, VT 05089

    This beautifully crafted 2024 "Incredible Tiny Home" built by Amish Artisans, is ready for its next owner. Thoughtfully designed for efficiency and comfort, the home features a convenient kitchen, a spacious bathroom, and a loft sleeping area with stairs for easy access. A mini-split system provides both heating and cooling, ensuring year-round comfort. Step outside to enjoy the well-built

    Jenna Luce RE/MAX Upper Valley

    505 Back Mountain Rd Unit 14, Windsor, VT 05089
  • /60

    $1,395,000

    • 4 Beds
    • 3.5 Baths
    • 4,111 Sq Ft

    39 Wallis View Ln, Ludlow, VT 05149

    Set in the highly desirable South Hill Estates, this exceptional property pairs privacy with an unbeatable location just minutes from Okemo Mountain. Surrounded by nearly five acres, the home enjoys sweeping mountain views and a beautifully open landscape that invites year-round enjoyment. The yard is a true highlight—offering plenty of space to relax, entertain, and play. A picturesque pond

    Debra Staniscia Four Seasons Sotheby's Int'l Realty

    39 Wallis View Ln, Ludlow, VT 05149
  • /37

    $795,000

    • 3 Beds
    • 2.5 Baths
    • 2,066 Sq Ft

    62 Pullman Ln, Hartford, VT 05001

    A great opportunity to own a nearly brand new, (2020), Net Zero "Green" home in a lovely area of Wilder, VT. The hard working solar panels on the roof provide all the power needed to run this home, and then some. With a lovely open floor plan on the first floor, including a great kitchen living room/dining room, a bedroom and bath, and 2 bedrooms and a bath plus a huge office upstairs, there's a

    Jane Darrach Martha E. Diebold/Hanover

    62 Pullman Ln, Hartford, VT 05001
  • /60

    $625,000

    $25K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 4,482 Sq Ft

    33 Acorn St, White River Junction, VT 05001

    Set in a peaceful neighborhood with scenic views and large backyard, this expansive home offers the perfect balance of space, comfort, and flexibility. With 5 bedrooms and several bonus living areas throughout, there is plenty of room to fit a variety of lifestyles and needs. Inside, you’ll find spacious living areas filled with natural light, along with a finished basement that adds even more

    The Malley Group KW Vermont

    33 Acorn St, White River Junction, VT 05001
  • /60

    $3,250,000

    $100K PRICE DROP
    • 5 Beds
    • 5 Baths
    • 3,212 Sq Ft

    166 Jewett Rd, Brownsville, VT 05037

    Stately hilltop home built by Silas Banister c.1800, recently undergone a complete restoration. Quality materials & craftsmanship throughout. It has gorgeous views of nearby Ascutney Mountain & long-range views of NH. The property consists of 98 acres made up of fields, hard & softwoods, trails, a large sugarbush (potential for a future boiling operation). Conserved by Upper Valley Land Trust,

    Dana Waters Dark Horse Realty

    166 Jewett Rd, Brownsville, VT 05037
  • /14

    $845,000

    • 2 Beds
    • 1 Bath
    • 600 Sq Ft

    234 Randall Rd, Wood Stock, VT 05091

    Randall Road Farm represents a rare opportunity to purchase a multigenerational family farmstead in an exceptionally desirable location. Long recognized as a well established farm raising Charolais beef cattle, poultry and hay. The owner has been the farmer/steward of many of the areas farms in the Woodstock and South Woodstock. The property has a single family dwelling, shop building with farm

    Wade Treadway Wade I Treadway Real Estate

    234 Randall Rd, Wood Stock, VT 05091
  • /40

    $699,000

    $50K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,423 Sq Ft

    441 Rhoades Hill Rd, Bethel, VT 05032

    Set within the scenic landscape of Barnard, this beautifully updated 3-bedroom, 3-bath home offers the perfect blend of Vermont charm and modern comfort. Surrounded by peaceful countryside and sweeping views, the property invites you to slow down and enjoy every season. Inside, the home is filled with warmth and character, featuring hardwood floors, natural woodwork, exposed beams, and an

    Daniel Preston KW Vermont Woodstock

    441 Rhoades Hill Rd, Bethel, VT 05032
  • /48

    $319,000

    • 4 Beds
    • 3 Baths
    • 3,548 Sq Ft

    16 Furnace St, Springfield, VT 05156

    Wonderfully renovated home with incredible income potential! This property features a fully updated, separate entrance 1-bedroom, 1-bathroom unit with its own electrical meter (shared baseboard heat between both sides). Market data suggests similar units in the area can command around $750/month in rent. For an owner-occupant, leveraging this 1-bed unit could significantly lower your net monthly

    Franchesca Collins Hall Collins Real Estate Group

    16 Furnace St, Springfield, VT 05156
  • /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
  • /38

    $413,900

    $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,888 Sq Ft

    273 Route 5 N, Windsor, VT 05089

    Motivated Seller - Price Improved!Own a remarkable piece of Vermont history in the heart of Windsor. Built circa 1790, this beautifully preserved brick-and-frame Colonial blends timeless New England character with the modern updates today's buyers appreciate. Rich in craftsmanship and architectural detail, this one-of-a-kind home offers the perfect balance of historic charm, everyday comfort,

    Allison Griep BHHS Verani Upper Valley

    273 Route 5 N, Windsor, VT 05089
  • /38

    $249,500

    • 4 Beds
    • 2.5 Baths
    • 1,922 Sq Ft

    3668 Vt Route 103 N, Chester, VT 05143

    Entrepreneurs and investors take note! This commercially zoned property offers exceptional potential for a home-based business, investment opportunity, or live/work lifestyle. The property features an oversized barn, multiple outbuildings, and ample space to support a wide variety of business ventures, workshops, storage, or hobby pursuits.The home is currently configured as two charming

    Daniel Vigeant Mary W. Davis Realtor & Assoc., Inc.

    3668 Vt Route 103 N, Chester, VT 05143
  • /56

    $3,650,000

    • 5 Beds
    • 4 Baths
    • 5,181 Sq Ft

    348 Turtle Hill Rd, Ludlow, VT 05149

    Set high with vistas of southern Vermont's valleys and mountains, "The Barn" is a remarkable custom timber frame retreat where exceptional craftsmanship meets breathtaking natural beauty. Completed in 2023 after two years of thoughtful design and construction, this residence was created to be a place of gathering, connection, and lasting memories for generations to come.Privately situated on

    Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

    348 Turtle Hill Rd, Ludlow, VT 05149
  • /54

    $1,300,000

    • 5 Beds
    • 4 Baths
    • 2,893 Sq Ft

    2141 Twenty Mile Stream Rd, Proctorsville, VT 05153

    Exceptional Vermont Log Home on 23.13 Acres with Horse Property & Mountain Living Appeal.Meticulously maintained and beautifully landscaped, this stunning five-bedroom, four-bath log home offers the perfect blend of rustic charm, modern comfort, and exceptional amenities. Set on 23+ private acres, the property features covered porches, a relaxing hot tub deck, stone patio, and expansive

    McLaughlin Team Mary W. Davis Realtor & Assoc., Inc.

    2141 Twenty Mile Stream Rd, Proctorsville, VT 05153
  • /4

    $1,300,000

    • 3 Beds
    • 2 Baths
    • 2,334 Sq Ft

    72 Wood Rd, Hartford, VT 05001

    US Route 4 in Vermont - the east/west corridor from I-89 and the Killington Ski Area. Highway frontage between Quechee and Woodstock, VT. Minutes from Dartmouth College in Hanover, NH; near the intersection of I-89 and 91 at the Connecticut River; also close to Northern New England’s major DH Medical complex and Cancer Center in Lebanon, NH, as well as the VA Hospital in White River Junction. 1.5

    Terry Boone Bassette Real Estate Group

    72 Wood Rd, Hartford, VT 05001
  • /16

    $109,900

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,321 Sq Ft

    31 Amsden Hollow Rd, Perkinsville, VT 05151

    Older farmhouse looking for someone to bring it back to what it once was currently has 3-4 bedrooms, two baths, two kitchens, level lot, shed in the front yard area and a brook in the back yard area.

    April Shepard Twin State Realty LLC

    31 Amsden Hollow Rd, Perkinsville, VT 05151
  • /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
  • /60

    $1,400,000

    • 5 Beds
    • 4.5 Baths
    • 3,224 Sq Ft

    81 Town Farm Rd, Ludlow, VT 05149

    Experience the essence of Vermont mountain living in this exceptional five-bedroom, four-and-a-half-bath retreat, ideally located just minutes from Okemo Mountain Resort and offering partial winter views of the mountain. Nestled on approximately one acre and boasting over 3,300 square feet of beautifully finished living space, this inviting home combines timeless mountain character with the

    Matthew Bellantoni Mary W. Davis Realtor & Assoc., Inc.

    81 Town Farm Rd, Ludlow, VT 05149
  • /48

    $5,950,000

    New Construction $1M PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 5,087 Sq Ft

    412 Skyland Ln, Woodstock, VT 05091

    Once the site of an 1850s homestead and now reimagined for 21st-century living, Skyland Farm is a private retreat on 63 acres. Mineral springs, glass architecture, and extraordinary views define this rare legacy property, just minutes from the village of Woodstock and with direct access to the trails of Mount Peg. Found at the end of a quiet lane, sweeping vistas of the Green Mountains and

    Story Jenks LandVest, Inc/Woodstock

    412 Skyland Ln, Woodstock, VT 05091
  • /37

    $865,000

    $320K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,785 Sq Ft

    1782 Randall Rd, Woodstock, VT 05091

    This early Woodstock residence was built in 1792 by Joseph Wood on a parcel of land he purchased in 1786 from Ebenezer Kingsley, one of Woodstock early settlers. A classic New England Cape of the period with the notable features of a central chimney with multiple fireplaces and a second story overhang on the gables. The house retains a great deal of original features and fabric including wide

    Wade Treadway Wade I Treadway Real Estate

    1782 Randall Rd, Woodstock, VT 05091
  • /22

    $199,000

    • 1 Bed
    • 448 Sq Ft

    1440 Stevens Rd, Bridgewater, VT 05034

    Serenity and nature await you on 2 beautiful acres and a well loved seasonal one bedroom camp with propane vented wall heater and gas cookstove. Located almost at the end of the Bridgewater town maintained road. Beyond the town maintained road is Killington and at that portion of the road it is not maintained by the municipality. Enjoy access to VAST and VASA trails. Awesome mountain biking,

    Marni Rieger KW Vermont-Killington

    1440 Stevens Rd, Bridgewater, VT 05034
  • /47

    $395,000

    $44K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,617 Sq Ft

    5798 W Woodstock Rd, Woodstock, VT 05091

    Classic Vermont farmhouse just minutes from the heart of Woodstock. This charming 4 bedroom , 2 bath home offers the character of a traditional New England property with comfortable , move in ready living spaces. The home features a bright eat-in kitchen, spacious dining room, and a welcoming living room with a wood-burning fireplace--perfect for cozy Vermont evenings. Freshly painted interiors

    Carol Wood Williamson Group Sothebys Intl. Realty

    5798 W Woodstock Rd, Woodstock, VT 05091
  • /52

    $12,950,000

    • 5 Beds
    • 10 Baths
    • 8,827 Sq Ft

    3147 Mount Hunger Rd, Barnard, VT 05031

    Offered as a fully curated legacy estate, Honey Hill Farm encompasses 264.4 extraordinary acres of pastoral beauty, panoramic mountain views, and an unrivaled network of private trails, with an additional contiguous 42.6-acre parcel available for purchase. More than a luxury property, Honey Hill offers the experience of a private park, with nearly 10 miles of trails winding through forests, open

    Keri Cole Williamson Group Sothebys Intl. Realty

    3147 Mount Hunger Rd, Barnard, VT 05031
  • /50

    $1,600,000

    • 4 Beds
    • 4.5 Baths
    • 4,636 Sq Ft

    328 Gravelin Rd, Perkinsville, VT 05151

    High Shelter Farm offers the ultimate Vermont lifestyle on 271 extraordinary acres of fields, forests, and breathtaking views. Once a working farm, this remarkable property features over six miles of professionally designed trails by John Morton of Morton Trails, providing year-round recreation for cross-country skiing, snowmobiling, ATV adventures, hiking, and exploration. Direct access to

    Gary Coger Four Seasons Sotheby's Int'l Realty

    328 Gravelin Rd, Perkinsville, VT 05151
  • /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
  • /27

    $525,000

    $14K PRICE DROP
    • 6 Beds
    • 2 Baths
    • 2,304 Sq Ft

    81 High St, Cavendish, VT 05142

    This 1850s renovated property located right in the heart of the village adapts perfectly to your lifestyle or investment goals. This home functions seamlessly as a spacious 5-bedroom, 2-bathroom home or is ready to operate as two separate income-generating rental units. The unfinished third floor can easily be converted into additional living space, a master suite, or a bonus room. The spacious

    Tyleen Murray Kelley Real Estate, Inc.

    81 High St, Cavendish, VT 05142
  • /60

    $3,250,000

    • 5 Beds
    • 6.5 Baths
    • 5,728 Sq Ft

    191 Moon Shadow Dr Unit M19, Ludlow, VT 05149

    Solitude home at the top of the hill awaits! Solitude on Okemo Mountain, where this exceptional five-bedroom home captures the ultimate ski location, breathtaking long-range views, and unparalleled privacy. Perfectly positioned to embrace the beauty of the surrounding mountains, this residence offers a rare opportunity to enjoy true slope-side living in one of Vermont’s most sought-after resort

    Katherine Burns William Raveis Real Estate Vermont Properties

    191 Moon Shadow Dr Unit M19, Ludlow, VT 05149
  • /14

    $299,900

    • 5 Beds
    • 2 Baths
    • 1,772 Sq Ft

    3 Lark Ln, Springfield, VT 05156

    Welcome to 3 Lark Lane in Springfield, VT! This expanded 5-bedroom home offers flexible living space and many updates throughout. A spacious addition created a large bonus room along with an expansive kitchen and dining area perfect for everyday living and entertaining. The updated kitchen with granite countertops offers plenty of cabinet and counter space with an open flow into the dining area.

    Bobbie Lynn Thomas The Thomas Group of Northern New England, LLC

    3 Lark Ln, Springfield, VT 05156

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