256

Bennington County VT Homes for Sale

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  • /43

    $1,795,000

    $100K PRICE DROP
    • 6 Beds
    • 5.5 Baths
    • 5,178 Sq Ft

    144 Taconic Rd, Manchester, VT 05255

    “The Colonial” – Queen of Taconic Avenue One of the original summer “cottages” gracing historic Taconic Avenue, The Colonial is a crown jewel of Manchester Village. Painstakingly renovated, this stately home perfectly balances old-world charm with modern sophistication. The heart of the home is a stunning new chef’s kitchen, seamlessly blending timeless design with today’s comforts. All-new

    Sara Buckley Josiah Allen Real Estate, Inc.

    144 Taconic Rd, Manchester, VT 05255
  • /27

    $1,200,000

    • 2 Beds
    • 1 Bath
    • 1,056 Sq Ft

    233 Squires Rd, Manchester Center, VT 05255

    Tucked into the picturesque countryside of Manchester, this nearly 19-acre Vermont property offers a rare blend of privacy, income potential, and endless opportunity. Just minutes from downtown Manchester, the location provides easy access to the Orvis Fly Fishing School, Equinox Mountain, the Batten Kill River, and year-round recreation at Bromley Mountain Ski Resort. Surrounded by natural

    Mark Triller Real Broker LLC

    233 Squires Rd, Manchester Center, VT 05255
  • /6

    $56,900

    $18K PRICE DROP
    • Land
    • 4.2 Acres
    • $13,548 per Acre

    00 Heartwellville View Rd, Readsboro, VT 05350

    Nestled in the desirable Heartwelleview Road section of Alpenwald, this beautiful 4-acre lot offers the perfect blend of privacy and convenience. The property is partially cleared, making it easy to envision your dream home while still enjoying the natural beauty and tranquility of the surrounding forest. With power already available at the road and septic plans in place, much of the groundwork

    Colt Hazell Flex Realty

    00 Heartwellville View Rd, Readsboro, VT 05350
  • /51

    $1,795,000

    • 3 Beds
    • 3 Baths
    • 5,228 Sq Ft

    2167 Myers Rd, Shaftsbury, VT 05262

    Welcome to Hidden Ponds Farm - a breathtaking retreat set on 40 sprawling acres where history and refined country living meet in perfect harmony. This extraordinary early 1800s post-and-beam converted barn has been thoughtfully reimagined, preserving its authentic character while seamlessly integrating modern comforts. A magnificent 1,000-foot hand-placed stone wall winds gracefully across the

    Kelley Mccarthy Mahar McCarthy Real Estate

    2167 Myers Rd, Shaftsbury, VT 05262
  • /60

    $4,995,000

    $255K PRICE DROP
    • 9 Beds
    • 10 Baths
    • 7,900 Sq Ft

    1184 E Manchester Rd, Manchester, VT 05255

    Peacock Hollow, a c.1790 completely private estate, is gracefully sited on 29.9 acres surrounded by sweeping mountain views, a running stream, and bordered by the forest. This rare offering combines historic character with refined updates, creating a legacy property designed for both intimate living and grand entertaining. The 5,500 square foot main residence offers five beautifully appointed

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    1184 E Manchester Rd, Manchester, VT 05255
  • /26

    $850,000

    • 3 Beds
    • 3 Baths
    • 2,598 Sq Ft

    46 Ridge Rd Unit C-4, Winhall, VT 05340

    Experience four-season Vermont living in this beautifully appointed end-unit townhome in the highly sought-after Highgate neighborhood at Piper Ridge, one of Stratton Mountain's premier resort communities. Ideally located in Winhall, Vermont, just minutes from Stratton Mountain Resort, this spacious 3-bedroom, 3-bath residence offers exceptional privacy, abundant natural light, The thoughtfully

    Timothy Apps Four Seasons Sotheby's Int'l Realty

    46 Ridge Rd Unit C-4, Winhall, VT 05340
  • /47

    $1,500,000

    • Land
    • 38.57 Acres
    • $38,890 per Acre

    500 Nims Rd, Dorset, VT 05251

    This Majestic and Private 38 + acre parcel located nearby the Dorset Village, is tucked away on an elevated and prepped site which just happens to be one of the most dreamy and picturesque estate quality lands offered in all of Dorset. Just a mile from the Dorset Green and perched up on a knoll with nothing less than amazing mountain views to the south, east and the north. Absolutely stunning

    Laura Beckwith Josiah Allen Real Estate, Inc.

    500 Nims Rd, Dorset, VT 05251
  • /27

    $189,000

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,485 Sq Ft

    432 South St Unit D2, Bennington, VT 05201

    Welcome to easy living at Nathaniel Court! This spacious and light-filled tri-level condo offers the perfect blend of comfort, flexibility, and convenience in the heart of Bennington. Privately situated in a standalone building at the edge of the development, this well-maintained 3BR, 3BA home features generous living spaces, abundant natural light, and dedicated parking. A rare opportunity to

    Abi Gregorio

    432 South St Unit D2, Bennington, VT 05201
  • /2

    $4,979,900

    • 33,801 Sq Ft

    1000 Investors Ln, Manchester, VT 05255

    Exceptional opportunity to acquire a well-established Vermont investment portfolio consisting of 10 properties inclusive of 35 residential units and 5 commercial units located across the desirable communities of Brattleboro, Ludlow, Manchester, Cavendish, Shaftsbury, Proctorsville, and Chester. This diverse portfolio has been thoughtfully maintained and professionally managed, with many long-term

    The Nancy Jenkins Team Nancy Jenkins Real Estate

    1000 Investors Ln, Manchester, VT 05255
  • /7

    $997,000

    • Land
    • 23,086 Sq Ft
    • $1,881,132 per Acre

    153 Northside Dr, Bennington, VT 05201

    Level, .53-acre lot situated in Bennington’s high-traffic Planned Commercial (PC) District. This site offers a rare opportunity to save significantly on demolition costs and move straight into the design and permitting phase for a new commercial project. This busy corridor lot is located entirely outside of the flood zone, providing a clean slate for development and a more streamlined path for

    Lori Hurley Four Corner Properties LLC

    153 Northside Dr, Bennington, VT 05201
  • /52

    $2,285,000

    • 5 Beds
    • 4.5 Baths
    • 4,647 Sq Ft

    543 Lower Hollow Rd, Dorset, VT 05251

    A Serene Dorset Hollow Retreat Along the Mettowee River Tucked into the storied Dorset Hollow, this 4.6-acre retreat enjoys 488 feet of Mettowee River frontage, offering a rare blend of tranquility, comfort, and timeless Vermont charm. Expansive mountain views and the soothing sounds of the river surround you—fall asleep each night to its calming presence. Multiple outdoor spaces include a

    Britt Wohler

    543 Lower Hollow Rd, Dorset, VT 05251
  • /25

    $620,000

    • 4 Beds
    • 3 Baths
    • 1,768 Sq Ft

    35 Valley Pass St, Manchester, VT 05255

    Move right into this turnkey Cape offering 4 bedrooms and 3 bathrooms with extensive recent updates throughout. Combining classic New England charm with modern conveniences, this thoughtfully renovated home is designed for comfortable everyday living and effortless entertaining. The main level features a bright, open concept floor plan centered around a beautifully updated kitchen with quartz

    Katherine Zilkha Four Seasons Sotheby's Int'l Realty

    35 Valley Pass St, Manchester, VT 05255
  • /9

    $279,000

    $16K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,206 Sq Ft

    116 S Branch St Unit 118, Bennington, VT 05201

    Well-maintained two-family home offering spacious units, each featuring 2 bedrooms, a cozy kitchen, dining room, living room, full bath, and convenient in-unit washer and dryer hookups. Enjoy relaxing on the inviting covered front porch or the private covered back decks for each unit. Situated on a level half-acre lot, this property also includes off-street parking with a driveway and a 2-car

    Julie Glover Mahar McCarthy Real Estate

    116 S Branch St Unit 118, Bennington, VT 05201
  • /21

    $210,000

    • Land
    • 4.51 Acres
    • $46,563 per Acre

    2740 Sandgate Rd, Arlington, VT 05250

    Set on 4.51 picturesque acres with an impressive 932 feet of frontage along the coveted Green River, this exceptional property is truly a fisherman's dream and a nature lover's paradise. Open meadows, mature trees, and beautifully maintained grounds create a peaceful setting that showcases the best of Vermont's natural beauty. A winding wooded walking path invites you to explore the landscape

    Moira Spivey Four Seasons Sotheby's Int'l Realty

    2740 Sandgate Rd, Arlington, VT 05250
  • /8

    $250,000

    • 2 Beds
    • 1 Bath
    • 924 Sq Ft

    924 Vt Route 7a, Shaftsbury, VT 05262

    Full of character and opportunity, this charming 2-bedroom, 2-bath home in Shaftsbury offers an affordable entry into homeownership or a fantastic addition to an investment portfolio. Once serving as the local post office, the property has a unique history and a cozy footprint that makes it ideal as a starter home, downsizing option, or rental property. Recent improvements include a beautifully

    The Nancy Jenkins Team Nancy Jenkins Real Estate

    924 Vt Route 7a, Shaftsbury, VT 05262
  • /3

    $1,295,000

    • Land
    • 52.61 Acres
    • $24,615 per Acre

    00 Montgomery Rd, Pownal, VT 05261

    A rare opportunity to own one of the most extraordinary parcels in the region. High Meadows Farm encompasses sweeping open meadows, mature woodlands, and truly breathtaking 360-degree views stretching from Mount Greylock to the south, Mount Anthony to the north, the Taconic Ridge to the west, and Dome and Pine Cobble to the east. Wander a secluded birch-lined pathway, discover a magnificent

    Ann Greenwood Alton + Westall Real Estate Agency, LLC

    00 Montgomery Rd, Pownal, VT 05261
  • /42

    $180,000

    • 3 Beds
    • 2 Baths
    • 1,640 Sq Ft

    105 Hicks Ave, Bennington, VT 05201

    Opportunity awaits at this unique property with an exceptional setting along the Walloomsac River. A true Vermont farmhouse offering three bedrooms and two bathrooms, situated on a flat, park-like lot with mature landscaping, open green space, and beautiful river frontage. The serene setting creates a peaceful atmosphere rarely found in properties with such versatile potential. A large barn

    Angela Bevin Maple Leaf Real Estate

    105 Hicks Ave, Bennington, VT 05201
  • /60

    $625,000

    • 3 Beds
    • 2.5 Baths
    • 3,295 Sq Ft

    142 Schenkar Rd, Pownal, VT 05261

    Welcome to your own private oasis! Set on 30 private wooded acres, this well-maintained three-bedroom, 2.5-bath Colonial presents a rare opportunity to enjoy expansive acreage, exceptional mountain views (including the Bennington Battle Monument!), and peaceful surroundings in a highly versatile tri-state location near the Vermont, Massachusetts, and New York borders. The 2,083 square-foot home

    Erin McCormick KW Vermont

    142 Schenkar Rd, Pownal, VT 05261
  • /43

    $2,100,000

    • 4 Beds
    • 3 Baths
    • 3,780 Sq Ft

    1228 Skiparee Rd, Pownal, VT 05260

    Welcome to Amara Farm, an equestrian paradise in Southern Vermont. This meticulously planned property offers a 13-stall barn designed with every detail in mind, ensuring comfort and efficiency for both horse and rider. The state-of-the-art indoor arena features GGT footing and a full wall of window providing top-quality conditions for training and performance. Turnout paddocks and outdoor arena

    Christiane Carroccio TPW Real Estate

    1228 Skiparee Rd, Pownal, VT 05260
  • /60

    $574,900

    $5K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 2,529 Sq Ft

    126 Simeon Dean Rd, Shaftsbury, VT 05262

    Horse enthusiasts take notice! Barn Recently renovated w New Electric, 3@12x12 stalls, new Loft & Heated Tack Rm added, or use as desired, Hobby Shop, Antiques, Storage. Wonderful Newly Fenced Pasture & Paddocks & Fencing around house for children or pets. Charming audible Paran Creek from the porch w/nearby adjoining access to serene 6acre Spring Fed Pond. Total of 17.47 acres for your complete

    Denise Byers Green Mountain Premiere Properties

    126 Simeon Dean Rd, Shaftsbury, VT 05262
  • /27

    $645,000

    $30K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,432 Sq Ft

    4928 Main St Unit 2, Manchester Center, VT 05255

    Fabulous two bedroom two bath condominium converted in 2017 in the heart of Manchester Center. Many fine features: Marvin windows, hardwood flooring, central air conditioning, forced hot air heat, private second floor sundeck, mountain views. This one level second floor unit is accessed by private elevator and offers pretty mountain views through the oversized 9 foot windows. The living room has

    David Halligan Four Seasons Sotheby's Int'l Realty

    4928 Main St Unit 2, Manchester Center, VT 05255
  • /15

    $389,000

    New Construction
    • 4 Beds
    • 2 Baths
    • 2,516 Sq Ft

    319 Chester Knoll Dr, Bennington, VT 05201

    Build Your Dream Home—Without Starting From Scratch Now is your chance to own a brand-new home and still make it your own.This beautifully designed new construction home is currently underway and offers buyers the exciting opportunity to select their own finishing touches and create a space that reflects their style and vision.Featuring 4 bedrooms and 2 full bathrooms, this thoughtfully

    Lilli West Maple Leaf Real Estate

    319 Chester Knoll Dr, Bennington, VT 05201
  • /60

    $695,000

    $55K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,000 Sq Ft

    57 Pearl Buck Dr, Bondville, VT 05340

    WAKE UP TO UNPRECEDENTED MOUNTAIN VIEWS once called Terra Bella with ownership over four decades and now this can be the Winhall/Stratton residence you have been searching for. From the moment you drive in you are captivated with incredible scenery off prestigious Pearl Buck Drive. Offered on 3.5 acres.The main level boasts newly refinished oak floors, two bedrooms, a den or living area with

    Terry Hill Berkshire Hathaway HomeServices Stratton Home

    57 Pearl Buck Dr, Bondville, VT 05340
  • /52

    $285,000

    $4K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,411 Sq Ft

    262 Union St, Bennington, VT 05201

    Just a short walk to downtown shopping and dining you can move right into this well-maintained and thoughtfully updated 3-bedroom, 2-bath home offering comfortable living spaces, modern conveniences, and plenty of room to spread out both inside and out.The heart of the home is the spacious, updated kitchen featuring a center island, abundant counter top space, and generous cabinetry, and even

    William Paquin Maple Leaf Real Estate

    262 Union St, Bennington, VT 05201
  • /12

    $399,500

    $11K PRICE DROP
    • Land
    • 2.7 Acres
    • $147,963 per Acre

    2937 Dorset Rd W, Dorset, VT 05251

    Prime Buildable Lot in Dorset! Embrace the Best of All Worlds! Discover a rare opportunity to own a ready-to-build lot in the heart of Dorset, perfectly positioned to offer unparalleled access to the town's finest attractions. Just moments from scenic hiking trails, the picturesque Dorset Green, and the esteemed Dorset Field Club, this property is your gateway to a lifestyle of outdoor adventure

    Andrea Kaplan Four Seasons Sotheby's Int'l Realty

    2937 Dorset Rd W, Dorset, VT 05251
  • /23

    $252,500

    $7K PRICE DROP
    • Land
    • 17.6 Acres
    • $14,347 per Acre

    88 Cedar Ln, Peru, VT 05152

    Tucked away in the heart of the Green Mountains, this stunning 17.60-acre parcel in picturesque Peru, Vermont, is a rare opportunity to create your dream retreat. The land is richly wooded, offering a serene natural setting filled with mature trees and gently rolling terrain that promises a spectacular display of fall foliage—an ever-changing canvas of vibrant reds, oranges, and golds each

    Joe Castaluccio Winhall Real Estate

    88 Cedar Ln, Peru, VT 05152
  • /48

    $230,000

    • 3 Beds
    • 1.5 Baths
    • 1,128 Sq Ft

    104 Short St, Bennington, VT 05201

    Blending vintage charm with modern updates, this beautifully refreshed 3-bedroom, 2-bath home offers comfortable in-town living close to local amenities. Recent improvements include a newer roof installed just three years ago and new flooring throughout, creating a fresh and inviting atmosphere. Other additions include new kitchen appliances, furnace, and heat pump hybrid water heater, making the

    Lindsey Martin Maple Leaf Real Estate

    104 Short St, Bennington, VT 05201
  • /24

    $215,000

    $20K PRICE DROP
    • 1,300 Sq Ft

    340 Pleasant St, Bennington, VT 05201

    Downtown Bennington duplex offering an excellent opportunity for first-time homebuyers, owner-occupants, or investors. The first-floor unit has been completely renovated with a new kitchen, updated bathroom, and new flooring throughout. Recent improvements include a repointed foundation, fully completed siding, a new roof, and a gravel driveway. Live in one unit and help offset your mortgage with

    Melissa Nebelski Real Broker LLC

    340 Pleasant St, Bennington, VT 05201
  • /42

    $325,000

    $20K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,768 Sq Ft

    2154 U S 7, Pownal, VT 05261

    Charming antique Cape full of character and opportunity. This 3-bedroom, 1-bath home offers timeless New England charm with warm, inviting living spaces and a flexible layout ready for your personal touch. A first-floor bedroom and first-floor laundry provide the convenience of single-level living, while additional bedrooms upstairs offer flexibility for guests or office space. Original details

    Angela Bevin Maple Leaf Real Estate

    2154 U S 7, Pownal, VT 05261
  • /27

    $290,000

    $30K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,190 Sq Ft

    196 Granger Hollow Rd, North Bennington, VT 05257

    Currently being used as a primary home a vacant 2nd home, this property could be either a single family residence with/without an in-law house or as a 2 unit multifamily with 2 separate houses with your tenants paying all utilities responsible for their own plowing and yard upkeep. This quiet country location has 2 homes located on its 2 acres. The main home is a 3 bedroom ranch featuring a large

    Steve Schoppmeyer BHG Masiello Brattleboro

    196 Granger Hollow Rd, North Bennington, VT 05257
  • /14

    $2,395,000

    $105K PRICE DROP
    • Land
    • 227 Acres
    • $10,551 per Acre

    00 Vermont 11, Peru, VT 05152

    Bordering Green Mountain National Forest with sweeping views of Stratton, Bromley, and Magic Mountains, this 227 +/- acre offering in Peru, Vermont captures the scale, privacy, and natural beauty that define Southern Vermont mountain living.Spanning two distinct parcels, the offering includes 199 +/- acres bordering National Forest land and a separate 28 +/- acre parcel positioned to capture

    Kevin Moran Four Seasons Sotheby's Int'l Realty

    00 Vermont 11, Peru, VT 05152
  • /40

    $419,000

    $60K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,861 Sq Ft

    120 Village St, East Dorset, VT 05253

    Antique charmer in the village of East Dorset was originally built in the 1850s by famous lumberman, F.G. Harwood. An addition was added in 1900, followed by several improvements over time the colonial farmhouse boasts approximately 3,861 sq. ft. including an oversized two car garage all on 1.1 acres. With a sprawling footprint that features a primary bedroom suite with oversized closet, 4

    Dana Kingsley Josiah Allen Real Estate, Inc.

    120 Village St, East Dorset, VT 05253
  • /18

    $79,000

    $30K PRICE DROP
    • Land
    • 17 Acres
    • $4,647 per Acre

    00 Bill T Dr, Readsboro, VT 05350

    Significant price reduction! This gently sloping 17-acre parcel should not be overlooked. This property offers a dead-end location on a town-maintained road, providing you with privacy and convenience. Nestled in the charming town of Readsboro and surrounded by the beautiful Green Mountains, you will have easy access to VAST snowmobile trails and VASA ATV trails. Plus, you are just a stone's

    Monique White Deerfield Valley Real Estate

    00 Bill T Dr, Readsboro, VT 05350
  • /12

    $1,295,000

    • Land
    • 52 Acres
    • $24,904 per Acre

    0 Montgomery Rd, Pownal, VT 05261

    A rare opportunity to own one of the most extraordinary parcels in the region. High Meadows Farm encompasses sweeping open meadows, mature woodlands, and truly breathtaking 360-degree views stretching from Mount Greylock to the south, Mount Anthony to the north, the Taconic Ridge to the west, and Dome and Pine Cobble to the east. Wander a secluded birch-lined pathway, discover a magnificent

    Ann Greenwood ALTON & WESTALL REAL ESTATE AGENCY, LLC

    0 Montgomery Rd, Pownal, VT 05261
  • /10

    $125,000

    • Land
    • 5.77 Acres
    • $21,664 per Acre

    0 East Rd, Shaftsbury, VT 05262

    Set along scenic East Road in Shaftsbury, this 5.77-acre wooded parcel offers a beautiful opportunity to create a private Vermont homesite in one of the area’s most appealing rural settings. The land is currently wooded, allowing the next owner to decide how much to clear for a driveway, yard, gardens, or building site, with potential for a mountain view to the north with selective clearing.

    Jenifer Prouty Hoffman Hoffman Real Estate

    0 East Rd, Shaftsbury, VT 05262
  • /49

    $650,000

    • 5 Beds
    • 3 Baths
    • 5,524 Sq Ft

    81 Honeysuckle Ln, North Bennington, VT 05257

    Nestled on 9.89 secluded acres in North Bennington, this exceptional 4-bedroom, 3-bath home offers the perfect blend of character, comfort, and versatility. The sprawling residence features a beautiful interior highlighted by stunning post-and-beam cathedral ceilings and inviting living spaces designed for both everyday living and entertaining. The heart of the home is the large open space

    Kelley Mccarthy Mahar McCarthy Real Estate

    81 Honeysuckle Ln, North Bennington, VT 05257
  • /42

    $3,900,000

    • 5 Beds
    • 7 Baths
    • 11,736 Sq Ft

    2236 River Rd, Manchester, VT 05254

    Set on more than 18 picturesque acres along desirable River Road in Manchester Village, this extraordinary, converted farm offers a rare blend of historic character, modern comfort, & endless possibilities. Thoughtfully transformed into a multi-use residential compound, the property features four distinct living, working, & entertaining spaces, each with its own personality and purpose.

    Carol O`Connor Four Seasons Sotheby's Int'l Realty

    2236 River Rd, Manchester, VT 05254
  • /52

    $850,000

    $120K PRICE DROP
    • 6 Beds
    • 8 Baths
    • 5,764 Sq Ft

    24 Vt Route 11, Londonderry, VT 05148

    Some properties simply hold stories within their walls. Formerly the beloved Nordic Inn, this iconic Landgrove property has been thoughtfully reimagined into a gathering place designed for modern Vermont living while honoring its rich history of hospitality, adventure, and connection. Inside, six ensuite bedrooms, spa-inspired baths, multiple fireplaces, a chef’s kitchen, sun-filled all-season

    Nancy Jensen Four Seasons Sotheby's Int'l Realty

    24 Vt Route 11, Londonderry, VT 05148
  • /37

    $575,000

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,786 Sq Ft

    14 Marisa Ln, Dorset, VT 05251

    Welcome to your next chapter in the charming heart of Vermont, where easy living meets thoughtful design in this beautifully crafted one-level duplex townhouse. If you've been dreaming of a home that eliminates stairs from your daily routine while still delivering style and substance, your search ends here. Step inside and discover an open floor plan that feels both spacious and inviting across

    Julie Citron RE/MAX Four Seasons

    14 Marisa Ln, Dorset, VT 05251
  • /19

    $182,000

    $13K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,590 Sq Ft

    176 Glen Ave, Readsboro, VT 05350

    Charming and spacious 3-bedroom, 1-bath home situated on approximately 1.90 acres, offering warm character and generous living space. Beautiful wood floors flow throughout the home, complemented by fresh paint, making this property truly move-in ready.The expansive wrap-around porch is a standout feature, perfect for enjoying quiet mornings, relaxing afternoons, or entertaining family and

    Cassandra Ehrlich BHG Masiello Brattleboro

    176 Glen Ave, Readsboro, VT 05350

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