506

Windham County VT Homes for Sale

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  • /60

    $650,000

    • 4 Beds
    • 4 Baths
    • 3,392 Sq Ft

    23 Brook Rd, Saxtons River, VT 05154

    Enjoy Vermont country living just outside the historic village of Saxtons River! Set on 6.8+/- acres of open fields and woodland, this distinctive 3,392 sq. ft. home sits atop a knoll on town-maintained Brook Road, surrounded by mature maples, professionally maintained gardens and lovely views of neighboring hills, fields and farms. Follow scenic Route 121 along the Saxtons River to this special

    Carol Slocum Keller Williams Realty Metro-Keene

    23 Brook Rd, Saxtons River, VT 05154
  • /26

    $290,000

    • 5 Beds
    • 1.5 Baths
    • 2,167 Sq Ft

    207 Elliot St, Brattleboro, VT 05301

    Offered to the public for the first time in nearly 60 years, this majestic Colonial-style home is located in one of Brattleboro’s oldest neighborhoods. The property showcases exquisite original details, including maple floors and fine hardwood trim throughout both levels. Many of the original plaster walls and ceilings have been professionally restored and await your personal color choices. The

    Bill Hickok Berkley & Veller Greenwood Country

    207 Elliot St, Brattleboro, VT 05301
  • /22

    $315,000

    • 3 Beds
    • 3.5 Baths
    • 1,550 Sq Ft

    10 Tenth Ln Unit 31, Wilmington, VT 05363

    Lovely 3 bedroom, 3.5 bath townhouse just off the Haystack Club Golf Course with easy access to trails, the village of Wilmington, lakes, and the nearby Hermitage Club and Mount Snow ski resorts. The deck overlooks the green mountains and is just off the 10th fairway. This unit features a vaulted open concept living room with stone hearth and efficient wood stove, spacious dining area leading out

    Adam Palmiter Berkley & Veller Greenwood/Dover

    10 Tenth Ln Unit 31, Wilmington, VT 05363
  • /31

    $649,000

    • 5 Beds
    • 3.5 Baths
    • 2,830 Sq Ft

    36 Bears Den Rd, West Dover, VT 05356

    Lovely ski home home in an ideal location, offering the privacy of a single-family residence with the convenience of a groomed ski-home trail and direct shuttle service just steps from your front door.Nestled on a well-positioned lot in the desirable Bears Crossing community, the home backs directly to the ski-home trail with a bridge to cross right to your deck on your way home and

    Adam Palmiter Berkley & Veller Greenwood/Dover

    36 Bears Den Rd, West Dover, VT 05356
  • /27

    $249,900

    • 2 Beds
    • 1.5 Baths
    • 2,184 Sq Ft

    6 Church St, Wilmington, VT 05363

    Located in the heart of Wilmington, this charming two bedroom, one and a half bath home offers an excellent opportunity to create something truly special. Just a short walk to shops, restaurants, and everything downtown has to offer, the location is hard to beat. The home features an attached garage with potential unfinished space above, offering endless possibilities for expansion, a home

    Julie Lowe Lowe's Real Estate, LLC

    6 Church St, Wilmington, VT 05363
  • /33

    $459,000

    • 1 Bed
    • 2.5 Baths
    • 2,076 Sq Ft

    33 W Main St, Wilmington, VT 05363

    Unique opportunity to own a commercial building in the heart of downtown Wilmington. This historic structure has been completely overhauled and meticulously maintained by the current owners, and was the location of a successful restaurant for many years, with an income producing apartment upstairs. It is now being offered to a buyer with vision who may be looking for prime retail, restaurant, or

    Adam Palmiter Berkley & Veller Greenwood/Dover

    33 W Main St, Wilmington, VT 05363
  • /46

    $165,000

    • 3 Beds
    • 2.5 Baths
    • 2,376 Sq Ft

    1107 Broad Brook Rd, Guilford, VT 05301

    An exceptionally rare and enchanting waterside setting along Broad Brook. Hugged by the gentle curve of the water with direct frontage and stream access, this property offers a front-row seat to cascading waterfalls and the soothing soundtrack of rushing rapids right outside your door. It is the kind of storybook Vermont setting that simply cannot be replicated.The existing multi-level residence

    Kate Barry EXP Realty

    1107 Broad Brook Rd, Guilford, VT 05301
  • /56

    $624,900

    • 4 Beds
    • 2.5 Baths
    • 2,904 Sq Ft

    37 Stowe Hill Rd, Wilmington, VT 05363

    Welcome to Spruce Hill Farm, circa 1890, a beautifully restored farmhouse set on 47.7 picturesque acres just minutes from the charming village of Wilmington, Lake Raponda, Lake Whitingham, Mount Snow Ski Resort, and The Hermitage Club at Haystack. Lovingly renovated by its current owners since 1997, this exceptional property seamlessly blends modern amenities with timeless New England charm.

    Monique White Deerfield Valley Real Estate

    37 Stowe Hill Rd, Wilmington, VT 05363
  • /49

    $399,000

    • 3 Beds
    • 2.5 Baths
    • 2,108 Sq Ft

    135 Winter St, Dummerston, VT 05301

    Set on 2.01 private Dummerston acres, this home pairs open-concept living with big mountain views, clean solar power, and room to grow.The main floor centers around everyday ease. A bright kitchen, dining, and living room anchored by hardwood floors and exposed beams looks straight out toward the surrounding hills. Off the main area, the primary bedroom serves as a true first-floor

    Kate Barry EXP Realty

    135 Winter St, Dummerston, VT 05301
  • /59

    $309,000

    $66K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,840 Sq Ft

    1192 Chapel Hill Rd, Whitingham, VT 05361

    Discover the perfect Vermont four-season retreat in this architecturally unique round home, set on a picturesque 1-acre corner lot in Southern Vermont. Offered fully furnished and move-in ready, this 1,840-square-foot, 3-bedroom, 2-full-bath property is ideal as a year-round residence, vacation home, or turnkey getaway.The welcoming lower level features three comfortable bedrooms, a

    Cliff Leinonen Four Seasons Sotheby's Int'l Realty

    1192 Chapel Hill Rd, Whitingham, VT 05361
  • /47

    $269,000

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,960 Sq Ft

    5 Camelot Dr, Wilmington, VT 05363

    Enjoy the perfect blend of convenience, privacy, and value with this 3-bedroom, 2-bath manufactured home offering approximately 2,000 square feet of comfortable living space. Tucked away on a nicely landscaped 0.43-acre lot, this home is perched above town, offering a peaceful setting while keeping you within walking distance of restaurants, shopping, local events, and the Moover shuttle for easy

    Chad Lackey Deerfield Valley Real Estate

    5 Camelot Dr, Wilmington, VT 05363
  • /35

    $549,000

    • 4 Beds
    • 2.5 Baths
    • 2,359 Sq Ft

    116 Teacher Rd, Jamaica, VT 05343

    Set on 14.4 acres bordering the beautiful Green Mountain National Forest, this lovingly maintained 4-bedroom, 2.5-bath Vermont retreat offers the perfect combination of privacy, comfort, and year-round recreation. Currently operating as a successful Airbnb with repeat renters, the property is being offered fully equipped as a turn-key vacation rental opportunity or exceptional full-time

    Carrie Mathews Winhall Real Estate

    116 Teacher Rd, Jamaica, VT 05343
  • /26

    $1,350,000

    • 7,660 Sq Ft

    131,133,141 Green St, Brattleboro, VT 05301

    What an opportunity to own 11 units in 3 separate buildings with a fantastic rental history. Close to downtown, schools, shopping and bus routes. Very well maintained properties with 3 - two bedroom units and 8 one bedroom units. On site laundry for the convenience of tenants. Wonderful features including hardwood floors and large windows for exceptional natural light. Great porches and very

    Susan Bellville Bellville Realty

    131,133,141 Green St, Brattleboro, VT 05301
  • /29

    $469,000

    $46K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,016 Sq Ft

    33D White Oaks Loop Unit 38, Dover, VT 05356

    Owners will consider offers.Nicely updated and uniquely private Timber Creek end-unit townhome with easy access and winter ski trail views. Ideally located directly across from the upper entrance to Mount Snow, Timber Creek offers shuttle service from your front door to the base area, along with convenient on-site management, exterior maintenance, snow removal, landscaping, and

    Adam Palmiter Berkley & Veller Greenwood/Dover

    33D White Oaks Loop Unit 38, Dover, VT 05356
  • /35

    $497,500

    • 4 Beds
    • 3 Baths
    • 2,200 Sq Ft

    51A Suntec Loop, Dover, VT 05356

    Beautifully remodeled Suntec townhome just down from the base of the Mount Snow ski resort. This larger style spacious 4 bedroom townhome sits about a mile south of Mount Snow, with direct access to snowmobile trails, and easy access to the nearby village of Wilmington and lakes. The unit has been recently fully renovated inside and out for turn key enjoyment. Featuring a large open concept floor

    Adam Palmiter Berkley & Veller Greenwood/Dover

    51A Suntec Loop, Dover, VT 05356
  • /29

    $199,900

    $25K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,017 Sq Ft

    1892 US Rt 5, Dummerston, VT 05346

    Local history suggests this charming Dummerston bungalow may have begun its life as a one-room schoolhouse. Offering 1,017 square feet of living space, the home features two bedrooms, a full bath, a dedicated dining area, and a separate laundry room. Its warm wood details and practical single-level layout provide an inviting starting point for restoration and personalization.Outside, the

    Linda Benoit Highland Realty

    1892 US Rt 5, Dummerston, VT 05346
  • /31

    $225,000

    • 2 Beds
    • 1 Bath
    • 1,352 Sq Ft

    12 River Front Dr, Bellows Falls, VT 05101

    Enjoy breathtaking views of the Connecticut River and the New Hampshire mountain range from this well-maintained 2-bedroom, 1-bath home situated on a scenic 0.60-acre lot. Relax with your morning coffee on the front porch overlooking the river or unwind on the second porch while taking in the peaceful surroundings. Inside, you'll find a bright and inviting home featuring two energy-efficient

    Rob Weltz

    12 River Front Dr, Bellows Falls, VT 05101
  • /59

    $345,000

    $10K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,586 Sq Ft

    21 Big Bend Loop, Wilmington, VT 05363

    Welcome to 21 Big Bend Loop in Wilmington, VT, where mountain charm, year-round adventure, and peaceful surroundings come together. Tucked among the trees, this chalet-style home offers the perfect escape, whether you're looking for a full-time residence, a weekend getaway, or an investment property in one of Southern Vermont's most desirable recreation areas.Step inside through the

    Kelsey Malloy Keller Williams Realty Metro-Keene

    21 Big Bend Loop, Wilmington, VT 05363
  • /43

    $549,900

    $25K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,812 Sq Ft

    1 Bucket Ln, Dover, VT 05356

    NEW PRICE! Exceptional Value in Vermont’s Ski Country! This beautifully renovated classic chalet just became an even better opportunity! Offering the perfect blend of rustic Vermont charm and modern updates, this home features vaulted ceilings, exposed beams, a dramatic floor-to-ceiling brick fireplace, gorgeous remodeled kitchen with quartz countertops, and an expansive deck ideal for

    Linda Benoit Highland Realty

    1 Bucket Ln, Dover, VT 05356
  • /20

    $595,000

    • 3 Beds
    • 3 Baths
    • 2,401 Sq Ft

    783 Wilmington Cross Rd, Whitingham, VT 05361

    Private 72 acre playground with 3 bedrooms, 3 bath log cabin. Lots of room to play, including a VAST trail in the rear. A great covered porch makes for enjoying the privacy just out side to large kitchen/living/dining room, or downstairs outside the equally large family room. Plenty of room for guests and a large barn or outbuildings for all your Vt outdoor stuff. Lake Whitingham is minutes down

    Michael Purcell Berkley & Veller Greenwood/Dover

    783 Wilmington Cross Rd, Whitingham, VT 05361
  • /57

    $489,000

    • 4 Beds
    • 2.5 Baths
    • 2,108 Sq Ft

    207 S Pine Banks Rd, Putney, VT 05346

    Set back from a scenic country road just minutes from the heart of Putney, this south-facing, 1,536-square-foot contemporary home offers an idyllic Vermont setting across 11.10 private, level acres. The primary residence features a functional, light-filled layout with 3 bedrooms, 1.5 baths, an eat-in kitchen with pine cabinetry, and spacious living and dining areas complemented by a cozy wood

    Kate Barry EXP Realty

    207 S Pine Banks Rd, Putney, VT 05346
  • /19

    $379,000

    • 1 Bed
    • 1 Bath
    • 680 Sq Ft

    2M Carinthia Rd, Dover, VT 05356

    One of a kind opportunity to be trailside at Mount Snow in a truly turn key completely updated unit. A rare chance to own a unit at Glen Run, at the base of Carinthia, with easy access to the earliest and latest trails open via the magic carpet, as well as to the newly built base lodge. This convenient one bedroom unit is on the ground floor affording easy access in and out via the rear slider,

    Adam Palmiter Berkley & Veller Greenwood/Dover

    2M Carinthia Rd, Dover, VT 05356
  • /52

    $1,997,000

    • 4 Beds
    • 4.5 Baths
    • 3,631 Sq Ft

    14 Talon Dr, Stratton, VT 05360

    Perfectly positioned between Stratton Mountain and Mount Snow, this exceptional custom timber frame home by Wadsworth Design Build offers the best of Southern Vermont living. Tucked within a private neighborhood and backing directly to the Green Mountain National Forest, the property provides a peaceful setting with immediate access to hiking, snowshoeing, and year-round outdoor recreation right

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    14 Talon Dr, Stratton, VT 05360
  • /22

    $399,000

    • 3,286 Sq Ft

    19 Canal St, Brattleboro, VT 05301

    Located in the heart of Brattleboro, this fully occupied and consistently high-performing investment property offers an outstanding opportunity for investors seeking strong cash flow and steady rental demand. Currently configured with 9 individual rentable rooms, the property has been successfully exclusively rented to The New England Center for Circus Arts students for years and maintains an

    Karen Hoppe Berkley & Veller Greenwood Country

    19 Canal St, Brattleboro, VT 05301
  • /8

    $250,000

    $230K PRICE DROP
    • Land
    • 5.08 Acres
    • $49,213 per Acre

    10 Overlook Dr, Dover, VT 05356

    A rare opportunity to own one of the last remaining lots in the prestigious Peaks/Greenspring community! This home development site offers 5.08 acres of land and features full panoramic mountain and woodland views to the south, including mountain views to undeveloped national forest land. This property is one of the most private lots in The Peaks community, providing a full immersion in the woods

    Patricia Fitzpatrick Skihome Realty

    10 Overlook Dr, Dover, VT 05356
  • /31

    $425,000

    • 2 Beds
    • 2 Baths
    • 1,110 Sq Ft

    65 E Birch Rd Unit 43, Stratton, VT 05155

    Welcome to Your Stratton Mountain GetawayDiscover the ultimate in mountain convenience with this turnkey, ground level condo in the highly sought after Vantage Point community. Featuring a spacious 2 bedroom, 2 bathroom layout, this home boasts a bright, open concept living, dining, and kitchen area designed for effortless entertaining and relaxation. Positioned in an unbeatable location,

    Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

    65 E Birch Rd Unit 43, Stratton, VT 05155
  • /46

    $734,000

    • 3 Beds
    • 5 Baths
    • 4,285 Sq Ft

    258 Chester Rd, Grafton, VT 05146

    Set on a beautifully landscaped parcel just minutes from the heart of historic Grafton, this meticulously maintained residence offers timeless New England charm, exceptional craftsmanship, and inviting spaces. Surrounded by mature trees, perennial gardens, and lush lawns, the property provides a peaceful setting with the perfect balance of privacy and convenience.Inside, warm hardwood floors,

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    258 Chester Rd, Grafton, VT 05146
  • /2

    $350,000

    $30K PRICE DROP
    • 3,312 Sq Ft

    573 S Main St, Brattleboro, VT 05301

    Just around the corner! From the middle and high school, Oak groveelementary! Pop around the corner for all the high school games,exercise at the track. Interstate is minutes away for easy access towork or play! One apartment is over 1,000 square feet so tons of roomfor owner occupancy! 2 nice front porches. Worth looking at for eitheryour own home or as an investment. Masks

    Christine Lewis Brattleboro Area Realty

    573 S Main St, Brattleboro, VT 05301
  • /60

    $3,995,000

    • 4 Beds
    • 5.5 Baths
    • 5,500 Sq Ft

    816 Black Bear Rd, Jamaica, VT 05343

    Set atop the Vermont hillside with stunning views, offering 4 bedrooms with additional sleeping rooms accommodating up to 16 family and friends. A custom-built home by The Wadsworth Design Build/Vermont Barns is an example of craftsmanship blended with modern luxury. Timber-framed architecture, this four-bedroom, six-bath estate offers a warm, rustic elegance that embraces its natural

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    816 Black Bear Rd, Jamaica, VT 05343
  • /41

    $2,699,000

    $2M PRICE DROP
    • 6 Beds
    • 3 Baths
    • 3,309 Sq Ft

    36 Woffenden Rd, Wilmington, VT 05363

    Discover the quintessential Vermont lifestyle at historic Wheeler Farm! Nestled amid its own 260+/- acres of scenic beauty, this 6-bedroom farmhouse embodies rural farmhouse charm. Open meadows, green hay fields and the sugarhouse's steam on spring days barely begin to tell the story of all this special property holds.Boasting a coveted southeast exposure, the home and land are cheerful

    Melissa Ellis Southern Vermont Realty Group

    36 Woffenden Rd, Wilmington, VT 05363
  • /45

    $1,165,000

    • 4 Beds
    • 2.5 Baths
    • 3,338 Sq Ft

    1472 Carpenter Hill Rd, Guilford, VT 05301

    The Governor Carpenter Homestead, a pivotal piece of American history in Guilford, VT, is now accepting applications for its next Steward. This remarkable property was constructed in 1772 by Benjamin Carpenter, Vermont's first Lieutenant Governor. Lovingly maintained for decades, the residence combines historic integrity with modern functionality. Key features include: Architectural Significance:

    Thomas Dahlin Berkley & Veller Greenwood Country

    1472 Carpenter Hill Rd, Guilford, VT 05301
  • /44

    $350,000

    $75K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft

    25 Upper Handle Rd Unit A, Dover, VT 05356

    Welcome to this inviting 3-bedroom plus loft, 2-bath Apple Hill condominium is perfectly located just minutes from Mount Snow. This spacious and well-maintained home offers a comfortable layout for a relaxing Vermont getaway. The updated kitchen and dining area feature a charming window seat, while the open-concept living room boasts another cozy window seat and a wood-burning fireplace for those

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    25 Upper Handle Rd Unit A, Dover, VT 05356
  • /33

    $339,000

    • 3 Beds
    • 2 Baths
    • 1,160 Sq Ft

    57 Timber Ln, Wardsboro, VT 05360

    OPEN HOUSE - Sunday, Sept 6, 10:00 am - 12:00 pm - Conveniently located between Mount Snow and Stratton Resort you'll find this three-bedroom, two-bathroom home surrounded by lush perennial gardens that thrive in the sun of the one-acre lot's southern exposure within the desirable Snow Mountain Farms community of Wardsboro, Vermont.The main level features an inviting open-concept layout that

    Kim Meeker Southern Vermont Realty Group

    57 Timber Ln, Wardsboro, VT 05360
  • /2

    $25,000

    • Land
    • 26,136 Sq Ft
    • $41,667 per Acre

    28 Upper Howes Way, Wilmington, VT 05363

    Sweet Spot tucked away in a quiet corner of the Hill, ready for you to build your vacation getaway. Recent soil tests are favorable for a 3-bedroom house. Enjoy all the amenities Chimney Hill offers on its 1,200 Acre Resort Campus, including year-round swimming, seasonal tennis and pickleball, ice skating with a warming hut full of skates to use, hiking, biking, snowmobiling right from your house

    Sigrid Pickering Chimney Hill Realty

    28 Upper Howes Way, Wilmington, VT 05363
  • /42

    $439,000

    $86K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,508 Sq Ft

    147 Gilbert Rd, Guilford, VT 05301

    This sweet home is nestled in the serene, and quiet location of Gilbert Rd, a dead end, located on the edge of Newfane but in the quaint town of Marlboro, VT. It has been completely renovated within the past few years by a local high-end builder with an eye for energy efficiency. His workmanship is evident in the renovation. The result: this pristine home gleams with its fresh and inviting

    Monica Sumner BHG Masiello Brattleboro

    147 Gilbert Rd, Guilford, VT 05301
  • /39

    $55,000

    • Land
    • 21,780 Sq Ft
    • $110,000 per Acre

    404 Fox Mountain Rd, Wilmington, VT 05363

    Top of the Hill. Build your dream home! One of 2 remaining lots on the new Fox Mt. Cul de Sac, and the only single lot. These have had recent soil tests showing the lot is suitable for a 3-bedroom home. The Lot is oriented to the Southwest, towards Bennington. Plus, enjoy all the amenities Chimney Hill, the Deerfield Valley and Southern Vermont offer including world class skiing and shredding,

    Sigrid Pickering Chimney Hill Realty

    404 Fox Mountain Rd, Wilmington, VT 05363
  • /42

    $1,115,000

    $135K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,022 Sq Ft

    564 Goodaleville Rd, Jamaica, VT 05343

    Set along a quiet back road on the Winhall River, this beautifully reimagined former schoolhouse blends timeless Vermont character with thoughtful modern updates. Built around the historic Goodaleville Road schoolhouse with a timber-frame addition and renovated by Vermont Country Builders, the home reflects exceptional craftsmanship, energy efficiency, and enduring design. Just 10 minutes from

    Cheyanne Pugliese

    564 Goodaleville Rd, Jamaica, VT 05343
  • /41

    $289,000

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    8E Dover Green Loop Unit 8E Dover Green Loop, Dover, VT 05356

    Adjusted to $289,000 making this the best value in Dover Green. Enjoy the best of Southern Vermont from this beautiful townhome in the sought-after Dover Green community, located just minutes south of Mount Snow. Whether you're looking for a year-round residence, a low-maintenance second home, or the perfect Vermont getaway, this spacious three bedroom, 2 two bath home offers comfort,

    Donald Koelsch Deerfield Valley Real Estate

    8E Dover Green Loop Unit 8E Dover Green Loop, Dover, VT 05356
  • /39

    $475,000

    $44K PRICE DROP
    • Land
    • 80.11 Acres
    • $5,929 per Acre

    47 Whites Hill Rd, Dover, VT 05341

    Escape to Your Private 80-Acre Paradise – Nature, Adventure, and Opportunity Await!Discover the perfect blend of natural beauty and endless outdoor adventure on this breathtaking 80-acre property, nestled in a peaceful and pristine setting. With towering maple trees ready for harvesting or simply to enjoy for their beauty and shade, this land offers both recreational enjoyment and income

    Joe Castaluccio Winhall Real Estate

    47 Whites Hill Rd, Dover, VT 05341
  • /21

    $19,000

    $5K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 673 Sq Ft

    222 Q1, 89 Grand Summit Way, Dover, VT 05356

    An opportunity to own at the beautiful and conveniently located trailside, Grand Summit Hotel. Enjoy the ski-on, ski-off lifestyle, while also experiencing the luxuries of hotel amenities, directly at the base of Mount Snow! This valley facing, sleep 6 unit is perfect for family, guests or great rental options. The unit features a fully-equipped kitchen, dining area and living room with a queen

    Prema Fitzpatrick Real Broker LLC

    222 Q1, 89 Grand Summit Way, Dover, VT 05356

Showing Results 41 - 80, Page 2 of 13

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