53

Bondville, VT Homes for Sale with Acreage

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  • /38

    $495,000

    $20K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,115 Sq Ft

    367 Stratton Gate Rd, Jamaica, VT 05343

    Nestled on 2.4 private acres along desirable Stratton Gate Road, this well-maintained four-bedroom, three-bath home offers the perfect balance of comfort, space, and year-round recreation. Just minutes from Stratton Mountain, you’ll enjoy easy access to skiing, golf, hiking, mountain biking, and all that Southern Vermont has to offer.Designed for gathering and relaxing, the home features two

    Agent Photo

    Alison Cummings

    Cummings & Co

    367 Stratton Gate Rd, Jamaica, VT 05343
  • /60

    $1,650,000

    • 3 Beds
    • 4 Baths
    • 5,072 Sq Ft

    36 Beaver St, Bondville, VT 05340

    Your Ultimate Vermont Mountain Retreat Awaits! Luxury log home plus a 2,250 sqft guest house! Just 4 miles from Stratton & minutes to Bromley, this inviting log home is the perfect year-round escape - crafted for adventure, relaxation, and making lasting memories in every season. Whether you’re hitting the slopes in winter, hiking through summer trails, or soaking in the stunning fall foliage,

    MaryKate Grey Stratton Real Estate

    36 Beaver St, Bondville, VT 05340
  • /13

    $2,525,000

    New Construction $100K PRICE INCREASE
    • 4 Beds
    • 3.5 Baths
    • 4,536 Sq Ft

    6 Stone Lodge Rd, Winhall, VT 05340

    FULLY FINISHED-Premier New Construction, offering 4500+ SF of luxury living on three levels, perched on 2.5 acres to maximize panoramic mountain and Bromley views. Just minutes to the Stratton Resort Base Lodge, this exceptional 4 bedroom/3.5 bath floor plan combines contemporary design, craftsmanship of the highest caliber and energy efficiency. Thoughtfully designed for comfort and performance,

    Kim Morgan-Wohler Wohler Realty Group

    6 Stone Lodge Rd, Winhall, VT 05340
  • /16

    $875,000

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    447 Rock Bottom Ln, Peru, VT 05152

    Historic Jack's Hill House, masterfully designed by Vermont Vernacular Designs. Nestled on approximately 21 private acres along a winding country road and bordered by National Forest, Still Meadows Farm offers a rare blend of timeless New England character, modern comfort, and unparalleled access to Vermont's outdoor lifestyle. Outdoor enthusiasts will appreciate the property's proximity to the

    Andy Reed Four Seasons Sotheby's Int'l Realty

    447 Rock Bottom Ln, Peru, VT 05152
  • /55

    $2,850,000

    New Construction $100K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 3,762 Sq Ft

    59 Garden Loop Rd, Winhall, VT 05340

    JULY 23 - Significant new price change today! - Move into this brand new stunning custom contemporary set on over 3 acres in coveted Stratton ski country. This exceptional modern design offers elevated living with superior craftsmanship and sweeping endless views. Featuring four well appointed ensuites with polished baths boasting radiant heated floors, half bath, family room and dual laundry

    Terry Hill Berkshire Hathaway HomeServices Stratton Home

    59 Garden Loop Rd, Winhall, VT 05340
  • /40

    $1,100,000

    • 5 Beds
    • 4.5 Baths
    • 4,453 Sq Ft

    6 Old Ridge Rd, Winhall, VT 05340

    Tucked into Stratton Mountain Resort’s sought after High Meadow neighborhood, 6 Old Ridge Road offers the rare combination of substantial square footage, significant recent exterior improvements, and the opportunity to personalize the interior aesthetic to your own taste. Encompassing over 4,600 sq. ft. across three finished levels, this expansive mountain home is designed for gathering,

    Trent Stephens Wohler Realty Group

    6 Old Ridge Rd, Winhall, VT 05340
  • /12

    $178,000

    $7K PRICE DROP
    • Land
    • 8 Acres
    • $22,250 per Acre

    4441 Vermont 30, Jamaica, VT 05343

    Set amidst a peaceful woodland setting, this 8.0± acre parcel offers the perfect balance of seclusion and convenience—tucked away for privacy yet easily accessible year-round.. Currently being subdivided from a larger tract, this parcel presents a rare chance to shape your vision from the ground up.A five-bedroom Wastewater Permit has been approved, and a professional boundary survey is

    Helen Nault

    4441 Vermont 30, Jamaica, VT 05343
  • /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
  • /38

    $1,250,000

    • 4 Beds
    • 3 Baths
    • 2,022 Sq Ft

    564 Goodaleville Rd, Jamaica, VT 05343

    10 MINUTES TO STRATTON RESORT | 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 Stratton Mountain

    Cheyanne Pugliese

    564 Goodaleville Rd, Jamaica, VT 05343
  • /12

    $450,000

    • Land
    • 10.26 Acres
    • $43,860 per Acre

    4.1 Pearl Buck Dr, Winhall, VT 05340

    One of the last significant VIEW lots available on the mountain , with unrivaled 360 degree views, including dead on views of Stratton Mountain trails. The pinnacle of this 10.26 acre lot is deserving of an exceptionally designed and expansive home in this premium location with commanding views.Prime for a legacy property in a most desirable location, just 5 minutes to the Stratton Base Area,

    Kim Morgan-Wohler Wohler Realty Group

    4.1 Pearl Buck Dr, Winhall, VT 05340
  • /38

    $375,000

    • Land
    • 1.23 Acres
    • $304,878 per Acre

    0 Winhall Hollow Rd Unit 5073717, Bondville, VT 05340

    Exceptional offering. This premier parcel defines phase II of Ravenwood, an enclave of distinctive and premier mountain residences. This notable site offers extraordinary mountain views, direct access from Winhall Hollow Road and still enjoys all the benefits and amenities of The Ravenwood Neighborhood Association. Combining, privacy, natural beauty and convenience, this well-established

    Kim Morgan-Wohler Wohler Realty Group

    0 Winhall Hollow Rd Unit 5073717, Bondville, VT 05340
  • /57

    $850,000

    • 5 Beds
    • 4 Baths
    • 3,218 Sq Ft

    4880 Pikes Falls Rd, Jamaica, VT 05343

    Welcome to your perfect four-season retreat nestled just minutes from Stratton Mountain Ski Resort. This authentic 5-bedroom, 4-bathroom log cabin plenty of space throughout, with ample natural light and that signature Vermont charm and cozy ambiance. A large kitchen, combined with an open dining area and expansive wrap around deck, offer a multitude of opportunities for seasonal gatherings no

    Mike England Michael England Real Estate

    4880 Pikes Falls Rd, Jamaica, VT 05343
  • /33

    $1,399,999

    • 6 Beds
    • 4 Baths
    • 3,800 Sq Ft

    121 High Meadow Rd, Winhall, VT 05340

    Bring the whole household to this great place with lots of room for fun. A 6-bedroom, 4-bathroom Adirondack-style Ski Chalet located in a neighborhood just minutes from the Stratton Mountain Ski Resort, with free door-to-mountain shuttle service on select days. Amenities include four (4) fireplaces, best hot-tub on the market, an in home gym, electric sauna, pool table, SuperChexx Bubble Hockey

    Ralph Harvey Listwithfreedom.com

    121 High Meadow Rd, Winhall, VT 05340
  • /15

    $59,900

    $15K PRICE DROP
    • Land
    • 2 Acres
    • $29,950 per Acre

    585 Sawmill Rd, Stratton, VT 05360

    Ready to build your Vermont dream home! Perfectly positioned between Stratton Mountain and Mount Snow, this exceptional 2-acre property offers the ideal blend of privacy, recreation, and convenience in the highly desirable Snow Mountain Farms community.Set within a picturesque mountain setting, the property is already prepared for construction with a cleared building envelope, driveway,

    Carrie Mathews Winhall Real Estate

    585 Sawmill Rd, Stratton, VT 05360
  • /4

    $400,000

    • Land
    • 8.01 Acres
    • $49,938 per Acre

    248 French Hollow Rd, Winhall, VT 05340

    Legacy family property, held until now for its premier location and extraordinary views of Stratton Mountain. Acreage offers a building site that is privately situated off the road with a 4 bedroom state septic permit and ready for the mountain home you have been hoping to create! A beautiful parcel with level plateau for building and a moderate slope down to its lower boundary. Surrounded by a

    Kim Morgan-Wohler Wohler Realty Group

    248 French Hollow Rd, Winhall, VT 05340
  • /13

    $120,000

    • Land
    • 4.68 Acres
    • $25,641 per Acre

    8559 Vt Route 30, Jamaica, VT 05343

    Double the Lots, Half the Drama.Why buy one lot when you can have two for the price of... well, this one? Here are 4.68 acres of "ready-to-go" land. Permits are secured for a 3 bedroom house on each lot, and the septic is already there, so you don't have to spend your weekends at town hall meetings. Build on both, or build on one and sell the other to that friend who always "forgets" their

    TG Glazer Winhall Real Estate

    8559 Vt Route 30, Jamaica, VT 05343
  • /50

    $1,800,000

    • 4 Beds
    • 5 Baths
    • 4,853 Sq Ft

    95 Middletown Rd, South Londonderry, VT 05155

    One-of-a-Kind Vermont Lifestyle PropertyHome, Income & Creative Opportunity Welcome to an exceptional Southern Vermont offering that blends refined country living with rare income and lifestyle flexibility. Set on 2.4 picturesque acres in South Londonderry, this beautifully restored 1865 property is first and foremost a warm and inviting 4-bedroom home—rich in character, thoughtfully updated,

    Eric Nathan Nathan Auction & Real Estate Inc.

    95 Middletown Rd, South Londonderry, VT 05155
  • /40

    $1,699,000

    • 4 Beds
    • 4 Baths
    • 2,951 Sq Ft

    1949 South Rd, Peru, VT 05152

    Discover Berry Hill Farm, an exceptional Vermont estate where inspired design, extraordinary craftsmanship, and natural beauty come together in one remarkable setting. Offering privacy, versatility, and a deep connection to the landscape, this unique property encompasses 15.52 acres across two separately deeded parcels, creating a rare offering for a Southern Vermont retreat. The contemporary

    Helen Nault

    1949 South Rd, Peru, VT 05152
  • /36

    $1,295,000

    $20K PRICE INCREASE
    • 5 Beds
    • 3.5 Baths
    • 3,040 Sq Ft

    4427 W Hill Rd S, Jamaica, VT 05343

    One-of-a-kind luxury lodge offering the comfort and amenities of a five-star retreat with the warmth and charm of a Vermont mountain home. The house provides all the space your friends and family could want—an expansive open layout perfect for gatherings, along with plenty of cozy, private spots for quiet moments. Enjoy movie nights in the 11-foot home theater, or relax in front of one of two

    Carrie Mathews Winhall Real Estate

    4427 W Hill Rd S, Jamaica, VT 05343
  • /32

    $849,000

    • 4 Beds
    • 3.5 Baths
    • 2,878 Sq Ft

    32 Benson Fuller Dr, Bondville, VT 05340

    Embrace Vermont living with this fully furnished, 4-bedroom, 3.5-bath contemporary home located just minutes from Stratton Mountain Resort. Situated on a serene 1-acre lot along a quiet road, this move-in-ready sanctuary offers effortless mountain comfort, high-end entertaining space, and practical updates throughout. Quality architectural details welcome you into a bright main level boasting a

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    32 Benson Fuller Dr, Bondville, VT 05340
  • /60

    $8,200,000

    • 6 Beds
    • 10 Baths
    • 10,763 Sq Ft

    557 Trager Rd, Jamaica, VT 05343

    Premier 416 acre Vermont Mountain Sanctuary -Luxury Estate with sweeping mountain views-a rare expression of outdoor and mountain living where nature inspired artistry, master craftsmanship and the environment converge in quiet harmony.. Set within an expansive private landscape, the 10,000+SF residence unfolds as a sanctuary oasis designed to elevate everyday living, remaining deeply rooted in

    Kim Morgan-Wohler Wohler Realty Group

    557 Trager Rd, Jamaica, VT 05343
  • /18

    $295,000

    • 4 Beds
    • 2 Baths
    • 1,024 Sq Ft

    3380 Under the Mountain Rd, Londonderry, VT 05155

    Amazing opportunity to own 60 acres on desirable Under The Mountain Road. This location is perfect for nature and adventure lovers alike, with several ski areas nearby. Ski at Bromley, Magic, Stratton, or take advantage of the many hiking and biking trails. There is a barn on the property with a residence on the second floor offering 4 bedrooms with 2 bathrooms. Options to live in the barn/house

    Rebecca Seymour Brattleboro Area Realty

    3380 Under the Mountain Rd, Londonderry, VT 05155
  • /15

    $475,000

    $55K PRICE DROP
    • Land
    • 30 Acres
    • $15,833 per Acre

    00 W Hill Rd S, Jamaica, VT 05343

    Discover 30+ acres of coveted Vermont land, offering breathtaking views, open fields, stonewalls, large pond & established driveway. This unique property features an expansive, man-made pond that’s clean, deep, and perfect for paddling, swimming, or even stocking with fish. Excellent southern exposure for solar energy possibilities ,power line access adjacent to the property, this land offers

    Jacki Murano Southern Vermont Realty Group

    00 W Hill Rd S, Jamaica, VT 05343
  • /47

    $1,140,000

    $60K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 4,193 Sq Ft

    70 Hunter Ln, Jamaica, VT 05343

    Discover a truly special Vermont hidden treasure at 70 Hunter Lane, set within the private Highland Forest community in the Cole Pond community . Just five minutes to Stratton Mountain Resort, this exceptional property offers the perfect balance of privacy, convenience, and year-round recreation. This 4,200 square foot home features four bedrooms and three Bathrooms. The generous living spaces

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    70 Hunter Ln, Jamaica, VT 05343
  • /40

    $445,000

    $44K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,560 Sq Ft

    494 W River St, Londonderry, VT 05155

    This comfortable home is situated in a peaceful and open sunny meadow surrounded by mature trees and 10 acres of Vermont woods offering total privacy. A view of Magic Mountain is a bonus as is the close proximity to shopping and dining. An important feature of the home is the newly added Lochinvar high efficiency propane boiler with on demand hot water installed in November of 2025. The 4

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    494 W River St, Londonderry, VT 05155
  • /60

    $1,160,000

    • 5 Beds
    • 4 Baths
    • 3,664 Sq Ft

    82 N Brookwood Rd, Stratton, VT 05360

    Location , Location , Location! Situated on North Brookwood just below the covered brige you'll enjoy easy access to the Wanderer ski trail as well as the resort shuttle that picks you up at your driveway! This iconic resort property features a great room with custom wood barrel cathedral ceilings, a wall of glass, wood burning fireplace and wrap around deck. Designed for the mountain enthusiast,

    Kim Morgan-Wohler Wohler Realty Group

    82 N Brookwood Rd, Stratton, VT 05360
  • /47

    $1,450,000

    • 5 Beds
    • 4 Baths
    • 2,974 Sq Ft

    494-498 Goodaleville Rd, Jamaica, VT 05343

    10 MINUTES TO STRATTON RESORT | 4BR main house, 1BR barn apartment, and separate restored vintage barn | Just minutes from Stratton Mountain Resort, this beautifully restored Vermont farmhouse blends authentic character, exceptional craftsmanship, and modern comfort. Once the summer residence of renowned art historian Meyer Schapiro, the property retains the riverside beauty and creative spirit

    Cheyanne Pugliese

    494-498 Goodaleville Rd, Jamaica, VT 05343
  • /9

    $374,900

    • Land
    • 2.31 Acres
    • $162,294 per Acre

    0 Wall St, Winhall, VT 05340

    Offered as a set, this property presents a rare opportunity to own two separately deeded parcels in a location that is only minutes from Stratton Mountain yet worlds away from the bustle of the resort. Totaling 2.31 acres, this land is situated high on River Road where neighboring homes enjoy spectacular views of Stratton. Conceptual rendering showing the potential view is based on the current

    Cheyanne Pugliese

    0 Wall St, Winhall, VT 05340
  • /38

    $795,000

    • 4 Beds
    • 3.5 Baths
    • 4,104 Sq Ft

    25 Benson Fuller Dr, Bondville, VT 05340

    Where Mountains Meet Modern Living: Perched just moments from the energy of Stratton Mountain Resort, this contemporary mountain home reimagines what a Vermont getaway feels like. From the moment you step inside, the design does exactly what a great contemporary home should: it steps back and lets nature take center stage. Massive, soaring windows act as living art pieces, framing sweeping,

    Robin Apps Four Seasons Sotheby's Int'l Realty

    25 Benson Fuller Dr, Bondville, VT 05340
  • /46

    $1,599,000

    • 6 Beds
    • 5.5 Baths
    • 5,568 Sq Ft

    144 High Meadow Rd, Winhall, VT 05340

    Expansive Stratton Mountain Resort Residence with exceptional floor plan and renovation! Featuring an upscale redesign of two top floor primary suite bathrooms, updated kitchen and expanded finished lower level, this home is ready for mountain living and endless entertaining! Designed with multiple gathering rooms and fireplaces, you'll enjoy apres ski with and an incredible open floor plan. Game

    Kim Morgan-Wohler Wohler Realty Group

    144 High Meadow Rd, Winhall, VT 05340
  • /40

    $1,500,000

    • 7 Beds
    • 7.5 Baths
    • 8,364 Sq Ft

    251 Pratt Bridge Rd, Jamaica, VT 05343

    Cold Moon Farm: Where Dreams Take Root! Ever imagine waking up to mountain vistas & the gentle sound of contented goats? This legendary Vermont property, makes that dream a reality. This once-in-a-lifetime offering is brimming with possibilities, whether you crave a sprawling family haven, a luxurious personal retreat, or a chance to revive the farm's celebrated B&B. Prepare to be Enchanted! An

    TG Glazer Winhall Real Estate

    251 Pratt Bridge Rd, Jamaica, VT 05343
  • /38

    $775,000

    • 4 Beds
    • 4 Baths
    • 3,520 Sq Ft

    12 Stratton Ridge Rd, Winhall, VT 05340

    First time on the market, this spacious mountain home has been lovingly maintained by one family since it was built in 1980. Tucked away on a generous double lot at the dead end of a private road, the setting offers privacy along with a true Vermont feel—quiet and peaceful.Inside, the home features a bright, open layout with abundant natural light and warm woodwork throughout, creating an

    Carrie Mathews Winhall Real Estate

    12 Stratton Ridge Rd, Winhall, VT 05340
  • /12

    $299,999

    • Land
    • 10.05 Acres
    • $29,851 per Acre

    00 Garden Loop Rd, Winhall, VT 05340

    The largest remaining vacant lot on the Stratton Mountain access road. Ten acres deeded for one magnificent home. The lot is wooded with some clearing on the east side. There's a roughed-in driveway here too, making it the best spot for construction. In the center of the property is a small pond--about a tenth of an acre--and west of that a scenic perennial creek winds its way downhill along the

    David White OwnerEntry.com

    00 Garden Loop Rd, Winhall, VT 05340
  • /31

    $1,200,000

    • 1 Bath
    • 950 Sq Ft

    109 Winhall Hollow Rd, Winhall, VT 05340

    Experience the pinnacle of Green Mountain living on this extraordinary 23.5-acre property. Perfectly positioned to capture a stunning, direct-line-of-sight view of Stratton Mountain, this property is more than just a home—it is a private outdoor sanctuary meticulously designed by The Wadsworth Company for the modern adventurer. The centerpiece of the property is a striking, contemporary dwelling

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    109 Winhall Hollow Rd, Winhall, VT 05340
  • /38

    $625,000

    • 3 Beds
    • 2 Baths
    • 2,288 Sq Ft

    1 Beaver St, Bondville, VT 05340

    Ideally located between Manchester and the mountains, this home offers the perfect blend of convenience, comfort, and Vermont charm. Just 10 minutes to Stratton, 5 minutes to Bromley, and 12 minutes to Manchester, you’ll enjoy easy access to skiing, dining, shopping, and year-round recreation.Inside, the home features a spacious living room filled with natural light, creating a warm and

    Carrie Mathews Winhall Real Estate

    1 Beaver St, Bondville, VT 05340
  • /22

    $430,000

    • 5 Beds
    • 2 Baths
    • 1,664 Sq Ft

    13 Golden Triangle Rd, Winhall, VT 05340

    The ideal opportunity in a prime location, minutes from Stratton Mountain, Bromley Mountain, and the charming town of Manchester, this 5-bedroom, 2-bathroom home has what you need for your primary Vermont residence or a quiet place to getaway. The spacious living room and dining area is complimented by a wrap around porch. This home is low maintenance and setup well for those who want a

    Mike England Michael England Real Estate

    13 Golden Triangle Rd, Winhall, VT 05340
  • /53

    $4,500,000

    • 5 Beds
    • 5.5 Baths
    • 5,700 Sq Ft

    24 Sawmill Rd, Stratton, VT 05360

    Experience the ultimate Stratton Mountain lifestyle from this exceptional ski home, perfectly positioned in one of the resort's most coveted locations. Offering the rare advantage of deeded access to Stratton's impeccably groomed ski trail, this extraordinary property places world-class skiing just steps from your front door—an amenity few homes can claim and even fewer can match.Designed for

    Carrie Mathews Winhall Real Estate

    24 Sawmill Rd, Stratton, VT 05360
  • /11

    $260,000

    • Land
    • 3.3 Acres
    • $78,788 per Acre

    0 Mountain Haunts Unit 5099438, Winhall, VT 05340

    The 3.3-acre parcel of land located on Mt Haunts Road in Winhall has received approval for the construction of a four-bedroom residence, presenting an outstanding opportunity for prospective homeowners. This exceptional site boasts views of Stratton Mountain Resort, allowing residents to monitor the mountain's snow conditions from the comfort of their own home each morning, as well as enjoy views

    Mike England Michael England Real Estate

    0 Mountain Haunts Unit 5099438, Winhall, VT 05340
  • /9

    $195,000

    • Land
    • 1.2 Acres
    • $162,500 per Acre

    4769 Pikes Falls Rd, Jamaica, VT 05143

    This 1.2-acre parcel offers what few properties in Southern Vermont can—a front-row seat to one of the region’s most breathtaking natural landscapes. Abutting the renowned Pikes Falls swimming hole and waterfall, this land enjoys immediate proximity to a setting protected by the Conservation Society of Southern Vermont. Glamping has become one of Vermont’s most sought-after experiences, and this

    Rachel Febbie EXP Realty

    4769 Pikes Falls Rd, Jamaica, VT 05143
  • /12

    $150,000

    $25K PRICE DROP
    • Land
    • 2.26 Acres
    • $66,372 per Acre

    0 Stratton Gardens Rd Unit 5072896, Winhall, VT 05340

    Welcome to the Stratton Gardens Community. Build your Vermont home on this 2+ acre parcel in Stratton Gardens. Ease of access right off the Stratton Mountain Access Road, and all the amenities of Stratton Gardens Association- highlights include-Private Shuttle Bus service to the Mountain, Road Maintenance, Plowing, Landscaping, and Trash removal.State Waste Water Permit in place for approved

    Tara van de Velde Four Seasons Sotheby's Int'l Realty

    0 Stratton Gardens Rd Unit 5072896, Winhall, VT 05340

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