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Windham County VT Homes for Sale

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  • /32

    $469,000

    $30K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,550 Sq Ft

    77 Buttonwood Dr, Brattleboro, VT 05301

    BLACK MOUNTAIN ESTATES - where your next chapter begins! Welcome to Brattleboro’s premier 55+ active lifestyle community, where nature, connection, & comfort converge. For the first time, a limited number of homes are available for purchase as we transition to a Planned Community. Surrounded by majestic pines, a private nature trail, & open green space, residents enjoy a serene setting just 1

    Dan Normandeau Berkley & Veller Greenwood Country

    77 Buttonwood Dr, Brattleboro, VT 05301
  • /2

    $90,000

    • 3 Beds
    • 1 Bath
    • 1,030 Sq Ft

    93 Clark St, Brattleboro, VT 05301

    An affordable opportunity for a new beginning, for both you and the home! Located in an evolving neighborhood where a new generation is investing, walk to downtown. This corner lot has off street parking, a bit of yard for some planting or sunning, and what the current owner has used as a workshop. This one will take cash or a rehab loan, but is being occupied so systems are working. Please, only

    Christine Lewis Brattleboro Area Realty

    93 Clark St, Brattleboro, VT 05301
  • /33

    $1,650,000

    • 5 Beds
    • 2.5 Baths
    • 4,443 Sq Ft

    874 Middletown Rd, Grafton, VT 05146

    Set along picturesque Middletown Road, just beyond the historic village of Grafton, this elegant five-bedroom residence enjoys a setting that feels both timeless and deeply peaceful. Perhaps it is the pleasing symmetry and classic proportions of the c.1815 brick Federal home with its Georgian floor plan. Perhaps it is the views of rolling meadows and rounded hills that unfold in both directions.

    Story Jenks LandVest, Inc/Woodstock

    874 Middletown Rd, Grafton, VT 05146
  • /48

    $629,000

    $15K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,329 Sq Ft

    774 Stratton Arlington Rd, Stratton, VT 05360

    Charming Log Cabin Compound Near Stratton and Mount SnowEscape to this quintessential Vermont retreat nestled on 1.2 private acres just minutes from Grout Pond, the Green Mountain National Forest, and a short drive to both Stratton and Mount Snow Resorts.The main log home offers three bedrooms and two baths with a warm, inviting open-concept living space. A stone fireplace anchors the

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    774 Stratton Arlington Rd, Stratton, VT 05360
  • /2

    $50,000

    • Land
    • 28 Acres
    • $1,786 per Acre

    non Pikes Falls Rd, Jamaica, VT 05343

    This is a land locked parcel. There is no right of way or easement to access it. This is a town sale property. There is a 30 day waiting period after a fully executed contract. The 30 days is a window for public feedback. Under the statute, if Town residence object to the sale, they have 30 days from the date of the notice to submit a petition to the Town. If a petition is signed by at least 5%

    Carrie Mathews Winhall Real Estate

    non Pikes Falls Rd, Jamaica, VT 05343
  • /6

    $475,000

    • Land
    • 188.9 Acres
    • $2,515 per Acre

    1301 Brockway Mills Rd, Bellows Falls, VT 05101

    Prime forested investment opportunity encompasses 190 acres, situated in the Northeast corner of Windham County. The property offers significant timber value and solar potential, making it attractive for both resource management and sustainable energy endeavors. The land borders Springfield and is conveniently located within easy reach of I-91, exit 6. It is also close to the villages of Chester

    Heidi Bernier Berkley & Veller Greenwood Country

    1301 Brockway Mills Rd, Bellows Falls, VT 05101
  • /23

    $260,000

    • 2 Beds
    • 1 Bath
    • 1,010 Sq Ft

    429 Vt Route 30, Newfane, VT 05345

    Discover the perfect blend of charm and tranquility in this delightful 2-bedroom bungalow nestled in the heart of Newfane Village. Fresh paint throughout, this home is move-in ready and awaiting its next owner. You can sit on the side deck and enjoy a spacious, yard ideal for gardening, entertaining, or simply soaking in the sounds of nature with direct access to a picturesque stream. You can

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    429 Vt Route 30, Newfane, VT 05345
  • /21

    $450,000

    • 4 Beds
    • 3.5 Baths
    • 1,800 Sq Ft

    16 Tenth Unit 40, Wilmington, VT 05363

    Beautiful 4 bedroom, 3.5 bath townhouse just off the Hermitage Club Golf Course with easy access to trails, the village of Wilmington, lakes, and the nearby Hermitage Club Ski Area and Mount Snow. The deck overlooks the 10th green and is beyond typical driving distance, so you can enjoy the sun while watching play. This unit has been updated including new carpet, new high efficiency wood stove in

    Adam Palmiter Berkley & Veller Greenwood/Dover

    16 Tenth Unit 40, Wilmington, VT 05363
  • /40

    $419,000

    • 3 Beds
    • 1.5 Baths
    • 1,908 Sq Ft

    1408 Hatch School Rd, Brattleboro, VT 05301

    This lovely New England cape is situated on 11 acres, surrounded by beautiful, level land and abundant wildlife. A charming wildlife pond is tucked behind the home, accompanied by a clearing for breathtaking nature scenes. The home has been lovingly cared for by the same family since it was built. Boasting granite countertops and spacious cabinets, the kitchen is well equipped. Two eating areas

    Monica Sumner BHG Masiello Brattleboro

    1408 Hatch School Rd, Brattleboro, VT 05301
  • /5

    $499,900

    • Land
    • 8.3 Acres
    • $60,229 per Acre

    340 Tyanoga Lot X, Whitingham, VT 05361

    WATERFRONT! WATERFRONT! 756' OF WATERFRONT!!Not only will you enjoy stunning lakefront living- you'll own part of the lake itself with this exceptional 8.3-acre parcel on beautiful Lake Sadawga.Nestled at the end of a quiet cul-de-sac, this private property offers water views and the perfect setting to build your dream home, for full-time living or a second home for quiet enjoyment. Much

    Pauline Green

    340 Tyanoga Lot X, Whitingham, VT 05361
  • /41

    $399,000

    • 3 Beds
    • 2 Baths
    • 1,989 Sq Ft

    200 Riverdale Rd, Townshend, VT 05353

    This classic Federal-style brick home blends historic character with thoughtful modern updates, offering a lifestyle that feels both grounded and effortlessly comfortable. Set on a dead-end road, the property enjoys the rare balance of peaceful country living and everyday convenience, all within moments of the local store, hospital, pharmacy, bank, and neighboring homes. Inside, you will be

    Lee Brown Four Seasons Sotheby's Int'l Realty

    200 Riverdale Rd, Townshend, VT 05353
  • /12

    $269,000

    • 3 Beds
    • 1.5 Baths
    • 1,248 Sq Ft

    333 US Route 5, Westminster, VT 05158

    Nestled on approximately nine plus acres in Westminster, Vermont, this charming three-bedroom, two-bathroom ranch-style home offers the perfect blend of privacy, comfort, and country living. Set back from Route 5, the property provides a peaceful retreat while remaining conveniently accessible. The expansive grounds feature mature fruit trees, open space for recreation or gardening, and

    Kassie Rubico Berkley & Veller Greenwood Country

    333 US Route 5, Westminster, VT 05158
  • /3

    $500,000

    • Land
    • 5.05 Acres
    • $99,010 per Acre

    Lot 1 Mountain Ridge Estates, Wilmington, VT 05363

    Being offered for the first time, is this spectacular newly cleared home site with stunning views of the Haystack and Mount Snow ridgeline and sunsets beyond. Mountain Ridge Estates abuts the Haystack Golf Club and are exclusive home sites for the discerning buyer looking to create a special spot in Vermont. This particular lot is 5+ acres overlooking the 18th hole and mountains beyond for year

    Adam Palmiter Berkley & Veller Greenwood/Dover

    Lot 1 Mountain Ridge Estates, Wilmington, VT 05363
  • /9

    $99,000

    $26K PRICE DROP
    • Land
    • 10.04 Acres
    • $9,861 per Acre

    Lot 2 North St, Dover, VT 05431

    Discover the perfect Vermont retreat on this 10.48 acre wooded parcel, ideally located in the heart of ski country. Tucked away in East Dover, this private lot offers a serene, natural setting just minutes from Mount Snow and The Hermitage Club. Towering hardwoods and softwoods provide a peaceful forest backdrop ideal for building your dream mountain home or cabin escape. Whether you envision a

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    Lot 2 North St, Dover, VT 05431
  • /21

    $160,000

    • Land
    • 11.08 Acres
    • $14,440 per Acre

    0 Rose Ln Unit 5097818, Londonderry, VT 05148

    This 11-acre parcel is situated near Cole Pond, only a few miles from the Stratton Mountain Access Road. The lot offers several potential building sites, including an elevated area that boasts stunning views, as well as a lower option. A driveway extends approximately halfway up the property, providing access to the upper site, which features a remarkable vista of Bromley Mountain. As one

    Mike England Michael England Real Estate

    0 Rose Ln Unit 5097818, Londonderry, VT 05148
  • /37

    $299,000

    • 3 Beds
    • 2.5 Baths
    • 1,872 Sq Ft

    412 Western Ave, Brattleboro, VT 05301

    Move-in ready and full of potential, this charming Brattleboro home is ready for its next chapter. The main level features a bright, open-concept layout with a spacious kitchen and comfortable living area, creating an ideal space for everyday living and entertaining. Filled with natural light, the living room opens directly onto a private rear deck overlooking a manageable backyard—perfect for

    Keith Nowak Four Seasons Sotheby's Int'l Realty

    412 Western Ave, Brattleboro, VT 05301
  • /19

    $469,000

    • 2 Beds
    • 2.5 Baths
    • 1,912 Sq Ft

    15 Haymaker Ln Unit 6D, Wilmington, VT 05363

    Beautiful condo on the side of Haystack mountain at the beautiful exclusive Hermitage Club Ski Resort. Enjoy sunrise views out your living room windows in this immaculate 2 bedroom, 2.5 bath unit. Walk in from the spacious mudroom entry to a living area with wood burning fireplace, deck overlooking the view, tremendous light and views, kitchen with breakfast bar, updated appliances, and gas

    Adam Palmiter Berkley & Veller Greenwood/Dover

    15 Haymaker Ln Unit 6D, Wilmington, VT 05363
  • /18

    $73,140

    • Land
    • 10,890 Sq Ft
    • $292,560 per Acre

    Lot 4 -156 High Peak Way, Wilmington, VT 05363

    Lot 4 in the High Peak Development, a .25-acre wooded parcel offering an ideal opportunity to create your own Vermont getaway. Perfectly situated just a short drive from Mount Snow, The Hermitage Club, and the recreational offerings of the Deerfield Valley, this lot provides the charm of a cabin in the woods setting with exceptional convenience.With public sewer and public water access,

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    Lot 4 -156 High Peak Way, Wilmington, VT 05363
  • /20

    $149,000

    • Land
    • 24 Acres
    • $6,208 per Acre

    381 Whitaker Farm Rd, Marlboro, VT 05344

    24 improved acres in the hills of Marlboro offering a combination of privacy, accessibility, residential, and recreational potential. Recent driveway improvements have created excellent access into the property, leading to a cleared landing and potential building site set back from the road. Existing recreational and old logging trails meander throughout the acreage and are well-suited for

    Jacki Murano Southern Vermont Realty Group

    381 Whitaker Farm Rd, Marlboro, VT 05344
  • /27

    $799,000

    • 5 Beds
    • 3 Baths
    • 3,306 Sq Ft

    32 Old Town Rd, Dover, VT 05356

    Lovely mountain and sunset views from this absolutely immaculate home just south of the Mount Snow ski resort. Enjoy total privacy yet easy access to skiing, direct access to snowmobile trails, and nearby access to the villages of Wilmington and Dover for shopping and dining. The property consists of a level 2 acres with swimming pond, lawn space for summer fun, stone patio, storage shed, and

    Adam Palmiter Berkley & Veller Greenwood/Dover

    32 Old Town Rd, Dover, VT 05356
  • /28

    $325,000

    $60K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,499 Sq Ft

    1644 Upper Dummerston Rd, Dummerston, VT 05301

    Found It! Live all on one level and tuck the guests in upstairs! The kitchen is modern with lots of counter top for the bakers and cookie makers, The laundry lives next to the kitchen and there is a second bath for visitors and guests. The sweet spot is the huge living room with a wood stove insert in the lovely fireplace. Mini-splits are already up and running for help with both heating and

    Christine Lewis Brattleboro Area Realty

    1644 Upper Dummerston Rd, Dummerston, VT 05301
  • /36

    $382,000

    • 6 Beds
    • 2.5 Baths
    • 3,590 Sq Ft

    88 Westminster St, Town of Rockingham, VT 05101

    Welcome to this stately New Englander located in the heart of Bellows Falls, offering the perfect blend of historic character and generous living space. With over 4,500 square feet, this grand home provides 15 rooms, 6 bedrooms and the potential for 4 bathrooms across multiple levels, giving plenty of room for family, guests, home office space, or multi-generational living. Beautiful period

    Jamie Watson BHG Masiello Keene

    88 Westminster St, Town of Rockingham, VT 05101
  • /29

    $349,000

    $31K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,750 Sq Ft

    34 Main St, Wardsboro, VT 05355

    Lovely late 1800s farmhouse conveniently located in the village of Wardsboro, Vermont, just a short drive to both Mount Snow and Stratton ski resorts. Meticulously maintained, the home sits on a well-positioned parcel with ample parking, private lawn space, and direct snowmobile trail access, plus easy walking access to the nearby convenience store for everyday necessities. Inside, the home

    Adam Palmiter Berkley & Veller Greenwood/Dover

    34 Main St, Wardsboro, VT 05355
  • /55

    $399,000

    $19K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,378 Sq Ft

    6 Outer Limits Ln, Wilmington, VT 05363

    Nestled in the coveted Chimney Hill Community, this charming 3-bedroom, 2-bathroom turn-key home is a delightful find. The main level features a convenient bedroom and full bath, along with a laundry area, a well-appointed kitchen, a dining room, and a cozy living room complete with a gas fireplace. Double sliding doors lead to a spacious deck, inviting an abundance of natural light. The home

    Donna Brown Skihome Realty

    6 Outer Limits Ln, Wilmington, VT 05363
  • /2

    $129,900

    • Land
    • 3 Acres
    • $43,300 per Acre

    57 Cheney Brook Loop, Dover, VT 05356

    Rare 3 acre south facing parcel in an area of fine homes, an incredibly short distance from West Dover center dining, shopping, and golf & skiing. Yet, it is just off the paved main artery that provides access to Dover Hills. Plenty of room to provide buffering, a truly unusual offering that shouldn't be missed if you're interested in constructing what you can't find in a limited inventory

    Michael Purcell Berkley & Veller Greenwood/Dover

    57 Cheney Brook Loop, Dover, VT 05356
  • /32

    $19,250

    $11K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 671 Sq Ft

    302 Qtr.1, 89 Grand Summit Way, Dover, VT 05356

    Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? Benefits of Grand Summit ownership include the best ski in/out mountain location available. Use of the Grand Summit amenities all year round including valet parking, owners private lounge, private owners library, full service spa with saunas hot tubs and outdoor heated pool, private owners only ski/golf locker rooms for year

    Kelly Agrillo Southern Vermont Realty Group

    302 Qtr.1, 89 Grand Summit Way, Dover, VT 05356
  • /42

    $959,900

    • 4 Beds
    • 2.5 Baths
    • 3,300 Sq Ft

    598 Hubbard Hill Rd, Halifax, VT 05342

    Set on 65± acres, this four-bedroom, three-bath home offers the privacy, views, and outdoor lifestyle that so many buyers seek in Southern Vermont. Perched to capture sweeping mountain views and spectacular sunsets, the home welcomes you with a covered front porch where you can relax and take in the ever-changing landscape.Inside, the spacious floor plan is designed for comfortable year-round

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    598 Hubbard Hill Rd, Halifax, VT 05342
  • /9

    $250,000

    • Land
    • 3.79 Acres
    • $65,963 per Acre

    000 Fort Dummer Heights, Brattleboro, VT 05301

    Easy to build!!! The land is open, so no fuss with a lot of prep. Beautiful high meadow, in a nice little neighborhood tucked up against the state park, what more could you want? This land has gone thru several transitions and plans for development by it's builder owner, but we now have the simplest! There are potentially a couple of options for hooking to town sewer with neighbor cooperation.

    Christine Lewis Brattleboro Area Realty

    000 Fort Dummer Heights, Brattleboro, VT 05301
  • /49

    $575,000

    • 4 Beds
    • 3.5 Baths
    • 2,964 Sq Ft

    8 Deer Run, Wilmington, VT 05363

    Located in the desirable Chimney Hill community, this beautifully maintained 4 bedroom, 4 bath home offers the perfect combination of comfort, convenience, and year-round recreation. Designed for gathering and relaxing, the open-concept floor plan features vaulted ceilings, abundant natural light, and seamless flow between the kitchen, dining, and living areas. A cozy gas fireplace creates a warm

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    8 Deer Run, Wilmington, VT 05363
  • /2

    $149,000

    • Land
    • 16.74 Acres
    • $8,901 per Acre

    9 Brown Rd, Wilmington, VT 05363

    Nice private almost 17 acre site with driveway, dug well, dug pond, sitework and ski area and Mountain views. Log cabin or post and beam home is a great fit. VAST snowmobile trail runs through the property. Beautiful bright and sunny exposure.

    Mark Yule BHG Masiello Brattleboro

    9 Brown Rd, Wilmington, VT 05363
  • /59

    $549,000

    $76K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,782 Sq Ft

    628 Townshend Rd, Grafton, VT 05146

    One of only two stone houses in the charming town of Grafton, this stately home is a truly special opportunity. Perched on a hill across from the renowned Grafton Cheese Company, the property offers easy access to village amenities and year-round recreation at Grafton Ponds Outdoor Center. Inside, you'll find a spacious and inviting layout: Large front living room with exposed beams, a beautiful

    Jessica Landers Barrett and Valley Associates Inc.

    628 Townshend Rd, Grafton, VT 05146
  • /17

    $329,000

    Open Sat 11AM - 1PM $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,280 Sq Ft

    550 S Main St, Brattleboro, VT 05301

    Lovely level lot, close to schools, hospital, shopping, State park and downtown. The best of everything, and BRAND NEW!!! Be the the envy of all your friends, with this wonderful, open concept, one level home. Primary bedroom on one end with an ensuite for privacy! New, shiny appliances, good sized island for cooking or hanging out and both a tub and a walk in shower. Special in so many ways,

    Christine Lewis Brattleboro Area Realty

    550 S Main St, Brattleboro, VT 05301
  • /35

    $2,399,000

    $100K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 3,569 Sq Ft

    662 Howe Farm Rd, Jamaica, VT 05343

    Discover this renovated timber frame home nestled on 366 acres of private land. Offering a seamless blend of historic character and modern comfort, this 4 bedroom plus office, 4 and a half bathroom home showcases attention to detail. The gourmet kitchen, inviting living spaces, bonus game room and home gym are complemented by a sunlit dining space with a greenhouse sunroom, adding a touch of

    Andie Fusco Four Seasons Sotheby's Int'l Realty

    662 Howe Farm Rd, Jamaica, VT 05343
  • /15

    $149,900

    $10K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 685 Sq Ft

    39 Brookside Dr Unit 7, Brattleboro, VT 05301

    Move right in! This condo has had some updates to include new scratch resistant vinyl plank flooring, new bathroom vanity, new kitchen range and freshly painted interior. Located in a prime location with quick, easy access to I91 and a stones throw to the Whetstone Brook, Farmers Market and Living Memorial Park. Shared basement with assigned storage space. Association fees include heat,

    Angela Sherman Brattleboro Area Realty

    39 Brookside Dr Unit 7, Brattleboro, VT 05301
  • /9

    $165,000

    • Land
    • 1.9 Acres
    • $86,842 per Acre

    Lot A Sweet Pond Rd, Guilford, VT 05301

    Beautiful open 1.9-acre parcel on scenic Sweet Pond Road in Guilford, VT. Featuring open pastureland, generally level terrain, and excellent southern exposure, this property offers a wonderful opportunity for a primary residence, homestead, recreation property, or investment. A classic stone wall borders the western edge, adding timeless Vermont character. Buyers to verify utility availability

    Erica Reynolds Southern Vermont Realty Group

    Lot A Sweet Pond Rd, Guilford, VT 05301
  • /49

    $799,000

    $51K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,600 Sq Ft

    1 Lower Highlands Rd, West Dover, VT 05356

    Custom-built 4-bedroom, 2.5-bath home ideally located less than a mile from Mount Snow. The main level welcomes you with an inviting foyer off the covered front porch and offers a well-designed layout featuring a spacious living room, formal dining room, comfortable family room, versatile den, and a well-appointed kitchen. Additional conveniences include a half bath, dedicated laundry area, and a

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    1 Lower Highlands Rd, West Dover, VT 05356
  • /20

    $195,000

    • Land
    • 4.86 Acres
    • $40,123 per Acre

    0 Stoney Brook Rd, Londonderry, VT 05148

    Long-range views of Stratton and Bromley define this 4.86 +/- acre offering in Londonderry, where elevation, privacy, and natural beauty come together in a compelling Southern Vermont setting. The access road and future building site are already roughed in, creating a strong foundation for a thoughtfully designed Vermont retreat.Supported by a State of Vermont wastewater permit for a

    Kevin Moran Four Seasons Sotheby's Int'l Realty

    0 Stoney Brook Rd, Londonderry, VT 05148
  • /16

    $275,000

    • 2 Beds
    • 2 Baths
    • 1,440 Sq Ft

    10 Riverfront Dr, Bellows Falls, VT 05101

    This recently renovated home is located on and with gorgeous views of the Connecticut River, frontage suitable for a wharf. Two bedrooms, two full baths and a beautifully crafted stone and brick fireplace. A large, private backyard, inviting family gatherings, just minutes to I91 and Okemo Mountain. Motivated Seller

    Robert Alger Alger Real Estate Agency

    10 Riverfront Dr, Bellows Falls, VT 05101
  • /47

    $545,000

    • 2 Beds
    • 1 Bath
    • 1,576 Sq Ft

    211 Pleasant Valley Rd, Brattleboro, VT 05301

    Perched atop this scenic hillside on 6 acres, this distinctive contemporary home and classic gambrel two-story barn once enjoyed sweeping easterly views to Mount Wantastiquet and distant Mount Monadnock. Glimpses of the long-range views exist but will need to be reclaimed. Located on highly desirable Pleasant Valley Road in West Brattleboro, the property offers an exceptional combination of rural

    Chris Long BHG Masiello Brattleboro

    211 Pleasant Valley Rd, Brattleboro, VT 05301
  • /23

    $525,000

    • 3 Beds
    • 2.5 Baths
    • 3,268 Sq Ft

    7 Mill Rd, West Dover, VT 05356

    When you picture a rustic and woodsy Vermont retreat, but with modern comforts, this is that home. Spacious chalet style home located conveniently on the MOOver shuttle route 3 miles from the Mount Snow Ski Resort. This 3 bedroom, 2.5 bath home has exposed natural woodwork throughout, a great open concept floor plan with large vaulted living room and wood burning fireplace on brick hearth,

    Adam Palmiter Berkley & Veller Greenwood/Dover

    7 Mill Rd, West Dover, VT 05356

Showing Results 361 - 400, Page 10 of 12

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