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Homes for Sale in 05143

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  • /2

    $90,000

    • Land
    • 4.05 Acres
    • $22,222 per Acre

    00 Hillcrest Rd, Andover, VT 05143

    Build your dream home or secluded retreat on this 4.05 acre wooded parcel on a quiet country lane close to shopping, skiing, snowmobiling, lakes and more. A wastewater permit is in place for a 5 bedroom home, and electricity is right at the street. It's less than 30 minutes to Magic Mountain or Bromley, or 35 to Stratton or Okemo. Charming Chester is 15 minutes away, and shopping in Londonderry

    Deborah Hanst

    00 Hillcrest Rd, Andover, VT 05143
  • /50

    $1,300,000

    • 3 Beds
    • 3 Baths
    • 4,714 Sq Ft

    1337 Andover Ridge Rd, Andover, VT 05143

    Vermont Mountain Retreat where adventure meets the view.At the top of the mountain, where the air feels a little crisper and the pace of life slows down, this distinctive Vermont log home offers a setting that makes every season feel special. Expansive mountain views stretch beyond the trees and can be enjoyed from the large decks, lawn and nearly every gathering space.The architecture is

    Lee Brown Four Seasons Sotheby's Int'l Realty

    1337 Andover Ridge Rd, Andover, VT 05143
  • /33

    $695,000

    • 3 Beds
    • 2.5 Baths
    • 2,232 Sq Ft

    717 Horsenail Hill Rd, Windham, VT 05359

    Brand-new construction in beautiful Windham, Vermont! This thoughtfully designed three-bedroom home with an additional bonus room offers the comfort, efficiency, and ease of new construction paired with a peaceful Vermont setting. Filled with natural light, the home features bright, welcoming living spaces and a versatile floor plan designed for both everyday living and weekend escapes. The bonus

    Carrie Mathews Winhall Real Estate

    717 Horsenail Hill Rd, Windham, VT 05359
  • /10

    $340,000

    • 3,608 Sq Ft

    145 S Main St, Chester, VT 05143

    Exceptional mixed-use opportunity with strong visibility on South Main Street in downtown Chester. This versatile property features two residentialapartments—a 2-bedroom, 1-bath unit and a 1-bedroom, 1-bath unit—alongside two commercial spaces, creating a diverse and stable income stream. A large barn addstremendous upside with the potential for additional units or expanded uses, subject to local

    The Nancy Jenkins Team Nancy Jenkins Real Estate

    145 S Main St, Chester, VT 05143
  • /48

    $700,000

    • 2 Beds
    • 3 Baths
    • 1,556 Sq Ft

    1260 Grafton St, Chester, VT 05143

    A wonderful retreat on 35+/- acres in Chester is ready for new owners to enjoy. The gated, serpentine driveway threads its way through the woods and by the large pond, taking in the lovely, open meadow with stone works and gardens leading to the classic custom 2+ bedroom, 3 bath chalet in an absolutely charming setting. As if transported from the Alps, the architectural features, such as handsome

    Geralyn Donohue Four Seasons Sotheby's Int'l Realty

    1260 Grafton St, Chester, VT 05143
  • /40

    $695,000

    • 4 Beds
    • 3.5 Baths
    • 2,585 Sq Ft

    294 Dale Rd, Weston, VT 05161

    Perched above Weston's coveted Dale Road in a private woodland setting, this handsome expanded cape was designed by Raymond Austin, architect of the famed Weston Playhouse. The home exudes graciousness and attention to detail in a living space that offers both cozy warmth and a light and open feeling. Surrounded by country gardens and with a south facing deck and mountain views, the property is a

    Steve Stettler Four Seasons Sotheby's Int'l Realty

    294 Dale Rd, Weston, VT 05161
  • /4

    $120,000

    • Land
    • 5.17 Acres
    • $23,211 per Acre

    0 Anderson Rd Unit 5106592, Grafton, VT 05154

    This 5.17-acre wooded parcel in Grafton offers a great opportunity for your future Vermont home, with potential mountain views through selective clearing. The property has been surveyed, and the subdivision has received Town of Grafton approval.Engineering plans for a proposed well and wastewater system have been completed and filed with the State of Vermont. The state wastewater permit is

    Jessica Hunt Barrett & Valley Assoc. Inc

    0 Anderson Rd Unit 5106592, Grafton, VT 05154
  • /47

    $599,000

    $11K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,908 Sq Ft

    548 Crow Hill Rd, Chester, VT 05143

    Tucked away on a quiet country road, this well-maintained 4-bedroom Cape home offers the peaceful Vermont setting so many buyers are searching for.Set on 12.86 acres, the property has been a place where generations have gathered, and now it's ready for its next chapter. Thoughtfully updated and meticulously cared for, the home features a new roof along with numerous improvements that provide

    Jay Farrar Four Seasons Sotheby's Int'l Realty

    548 Crow Hill Rd, Chester, VT 05143
  • /60

    $995,000

    • 3 Beds
    • 3 Baths
    • 2,167 Sq Ft

    979 Andover Ridge Rd, Chester, VT 05143

    Up a serene mountain road above the clouds in the quiet town of Andover, you’ll discover a special mountain property. This home has been distinctively renovated for carefree enjoyment. This retreat is surrounded by natural beauty with unprecedented long-range views to the west of the Green Mountain ridgeline. This highly efficient, low-maintenance home has wonderful natural light with views from

    Joseph Karl William Raveis Real Estate Vermont Properties

    979 Andover Ridge Rd, Chester, VT 05143
  • /43

    $360,000

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,312 Sq Ft

    96 Lower Bartonsville Rd, Chester, VT 05143

    This tastefully updated ranch-style home is set on a unique one-acre parcel with a convenient location to the Williams River. Three bedrooms and two baths, thoughtfully updated interior with inviting living spaces and the convenience of one level living. A full basement provides valuable additional space and could be finished to create a family room, home office, recreation area, or even a gym.

    Agent Photo

    Jessica Citera

    Cummings & Co

    96 Lower Bartonsville Rd, Chester, VT 05143
  • /60

    $995,000

    • 3 Beds
    • 3 Baths
    • 2,821 Sq Ft

    179 Reed Rd, Athens, VT 05143

    Custom Swedish Cope Log Home on 14 plus acres in Southern Vermont.Hidden among the hills, this custom log home combines rugged craftsmanship with warm, open living spaces. Oversized timbers transported from Idaho were assembled in the Swedish Cope style, featuring traditional saddle notched logs that give the home its distinctive character.A cathedral style entry leads into a dramatic

    Julie Lowe Lowe's Real Estate, LLC

    179 Reed Rd, Athens, VT 05143
  • /12

    $149,000

    • Land
    • 17.7 Acres
    • $8,418 per Acre

    0 Trebo Rd, Chester, VT 05143

    Discover the perfect setting for your Vermont dream home or future development on this picturesque rural parcel. Set along scenic Trebo Road, a quiet country road lined with historic homes, open fields, and mature woodlands, this nearly 18-acre property offers exceptional potential. Highlights include approximately 1,500 feet of road frontage, a charming pond, beautiful stone walls, and a Vermont

    Agent Photo

    Gail Beardmore

    Engel & Völkers Okemo

    0 Trebo Rd, Chester, VT 05143
  • /40

    $354,000

    $5K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 900 Sq Ft

    302 Davidson Hill Rd, Chester, VT 05143

    If you're looking for your forever home or the perfect mountain getaway, take a peek at this locally built Green Mountain Log Home. Davidson Hill Road is home to many craftsman quality homes perched above Chester, overlooking Mt. Ascutney. The open concept first floor spills out onto the generous front deck, essentially doubling the first floor area to roam. Two nearly identical wooden clad

    Tyler Buswell Vermont Real Estate Company

    302 Davidson Hill Rd, Chester, VT 05143
  • /60

    $225,000

    $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft

    3781 Flamstead Rd, Chester, VT 05143

    Nestled on 10 private acres between the towns of Chester and Springfield Vermont, this property offers an exceptional opportunity to build your dream home in a peaceful country setting. A driveway has already been installed, providing easy access to the center of the property where several potential homesites offer the possibility of beautiful mountain and valley views with selective clearing. An

    Amy Hill EXP Realty

    3781 Flamstead Rd, Chester, VT 05143
  • /60

    $1,600,000

    • 5 Beds
    • 5 Baths
    • 6,118 Sq Ft

    3 Eldredge Rd, Chester, VT 05143

    A rare opportunity to own a remarkable piece of Vermont and literary history. Lovingly designed and restored by the creators of the beloved Llama Llama children's book series and the accompanying Netflix animated series, this extraordinary mini-estate is offered for the first time by the family.The meticulously restored and maintained five-bedroom, five-bath, 6,100+ square foot post-and-beam

    Debra Staniscia Four Seasons Sotheby's Int'l Realty

    3 Eldredge Rd, Chester, VT 05143
  • /29

    $875,000

    • Land
    • 67.4 Acres
    • $12,982 per Acre

    00 Markham Ln, Weston, VT 05161

    An exceptional Weston land parcel with panoramic views, this property has been family land for generations and is now being offered for sale. A long tree-lined private drive slopes through forest to a cleared, sunny 4-acre field prepared for a house site. The site's elevation at almost 1800 feet backs onto forest and reveals stunning four-season views of the Green Mountain range, rolling hills,

    Steve Stettler Four Seasons Sotheby's Int'l Realty

    00 Markham Ln, Weston, VT 05161
  • /22

    $100,000

    • Land
    • 23,958 Sq Ft
    • $181,818 per Acre

    427 Depot St, Chester, VT 05143

    Situated in the heart of Chester, Vermont, this 0.55-acre parcel offers approximately 254 feet of frontage on Depot Street and 254 feet of frontage on First Avenue - both public, paved roads with a sidewalk accessible on Depot Street. The land is open, landscaped, and dotted with apple trees, creating a welcoming setting for your future plans. Town water and town sewer are available at the

    Taylor Medeiros-Batey KW Coastal and Lakes & Mountains Realty/Hanover

    427 Depot St, Chester, VT 05143
  • /58

    $879,900

    $45K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 2,800 Sq Ft

    1470 Popple Dungeon Rd, Chester, VT 05143

    Escape to the charm of Vermont in this spacious 5-bedroom, 3-bath country home, perfectly set amidst open meadows with a picturesque swim pond and peaceful surroundings. Designed for both everyday living and entertaining, this inviting property offers the perfect balance of rustic character and modern comfort. Step inside through the practical mudroom, where you'll be welcomed by a dramatic

    Joseph Karl William Raveis Real Estate Vermont Properties

    1470 Popple Dungeon Rd, Chester, VT 05143
  • /50

    $699,000

    $10K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,576 Sq Ft

    3319 E Hill Rd, Andover, VT 05143

    Set on just over 10 picturesque acres, 3319 East Hill Road offers a rare blend of privacy, comfort, flexibility, and four season Vermont recreation. The three bedroom, three bathroom main residence is filled with natural light and features vaulted ceilings, oversized windows, warm hardwood flooring, and a open concept layout that creates an easy flow between the kitchen, dining, and living areas.

    Thaddeus Abare Barrett and Valley Associates Inc.

    3319 E Hill Rd, Andover, VT 05143
  • /32

    $589,000

    • 3 Beds
    • 2 Baths
    • 1,946 Sq Ft

    314 Dorman Rd, Andover, VT 05143

    Silence is the first thing you notice. Set on 10+/- peaceful acres in Andover, this comfortable and well-maintained three-bedroom, two-bath home offers the kind of Vermont setting that is getting harder to find. No traffic noise, no bustle, just woods, privacy and room to breathe. Inside, the home is warm and inviting, with an easy layout equally suited to full-time living or weekends in the

    Daire Gibney Barrett and Valley Associates Inc.

    314 Dorman Rd, Andover, VT 05143
  • /25

    $229,000

    • Land
    • 27.8 Acres
    • $8,237 per Acre

    00 Quarry Rd, Chester, VT 05143

    27.8 +/- acre wooded parcel close to Chester Village with beautiful views. Driveway is roughed in and a clearing prepared at the entry to the land for a house site and a Vt state approved 4 bedroom wastewater Permit. Newly opened views from the plateau along the ridge accessed by an established logging road are a must see. Soil tests indicate a 3 bedroom home site is possible at the scenic

    Geralyn Donohue Four Seasons Sotheby's Int'l Realty

    00 Quarry Rd, Chester, VT 05143
  • /60

    $649,000

    • 3 Beds
    • 2 Baths
    • 2,204 Sq Ft

    168 Chandler Rd, Chester, VT 05143

    Welcome to your private gated mini-estate...an enchanting sanctuary where every detail delights the eye. Nestled adjacent to meticulously manicured woods, this one-of-a-kind residence blends storybook charm with thoughtful, high-end finishes. A sweeping entry leads past intimate outdoor living spaces centered around a dramatic floor-to-ceiling exterior fireplace, perfect for cool evenings and

    Diane Rousseau Four Seasons Sotheby's Int'l Realty

    168 Chandler Rd, Chester, VT 05143
  • /16

    $650,000

    • Land
    • 10.03 Acres
    • $64,806 per Acre

    00 Little Pond Rd, Andover, VT 05143

    Located in the town of Andover, VT, this 10.4 acre parcel, showcasing an amazing long range mountain view, awaits the home of your dreams. The approach to the property is gorgeous with dramatic views and large neighboring parcels. The house site is tucked in the forest, with a roughed-in driveway already in place. This property has been thoughtfully composed, setting the stage for your custom

    Geralyn Donohue Four Seasons Sotheby's Int'l Realty

    00 Little Pond Rd, Andover, VT 05143
  • /38

    $249,500

    • 1,922 Sq Ft

    3668 Vt Route 103 N, Chester, VT 05143

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

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

    3668 Vt Route 103 N, Chester, VT 05143
  • /60

    $525,000

    $100K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,656 Sq Ft

    758 Weston-Andover Rd, Chester, VT 05143

    A rare opportunity to own two well-maintained homes on one beautiful country property! The main residence offers 3 bedrooms and 3 baths with a warm, inviting interior featuring hardwood floors, abundant built-ins, and thoughtfully designed living spaces that blend character with everyday comfort. Step outside to the back deck overlooking beautifully landscaped gardens and a spacious lawn, an

    Kevin Barnes William Raveis Real Estate Vermont Properties

    758 Weston-Andover Rd, Chester, VT 05143
  • /58

    $445,000

    $30K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 3,865 Sq Ft

    81 Main St, Chester, VT 05143

    Step into a piece of Chester's history with this sprawling Folk Victorian offering over 3,800 square feet of living space, five bedrooms, and four bathrooms. Rich in character and architectural detail, this home offers the space and flexibility to accommodate a variety of lifestyles. Inside, you'll find generously sized rooms throughout, including a spacious living room anchored by a wood-burning

    Betsy Adamovich Real Broker LLC

    81 Main St, Chester, VT 05143
  • /33

    $449,000

    $40K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,626 Sq Ft

    3208 Green Mountain Turnpike, Chester, VT 05143

    Located on the edge of the Historic Stone Village of Chester, this thoughtfully renovated and reimagined circa 1880 home combines modern style with artisan craftsmanship. Set on .33± acres, this light-filled property features wide-pine floors, exposed beams, and a Vermont Castings woodstove enhancing an inviting open-concept living space. The kitchen/dining has butcher block counters, attractive

    Geralyn Donohue Four Seasons Sotheby's Int'l Realty

    3208 Green Mountain Turnpike, Chester, VT 05143
  • /20

    $85,000

    • Land
    • 3.99 Acres
    • $21,303 per Acre

    00 Simonsville Rd, Andover, VT 05143

    ANDOVER 3.99 Acres on the Williams River that was once a part of the Historic Jaquith Homestead. Walk the old mowing road that winds through the property, leading to three meadow areas along the river. The central meadow has a designated home site for a 4 bedroom state approved septic. The owners have just had the house location resighted to make sure it is out of the flood zone. A great spot for

    Geralyn Donohue Four Seasons Sotheby's Int'l Realty

    00 Simonsville Rd, Andover, VT 05143
  • /14

    $87,500

    • Land
    • 10.4 Acres
    • $8,413 per Acre

    00 Snell Rd, Chester, VT 05143

    CHESTER 10.4+/- acre parcel of land offers offers 180 degree ridgeline views with clearing from an elevated plateau for either a house site or a camp site with a home closer to the town maintained road. A nice stream meanders through the property which is dotted with large rocks and stone walls. There is 245 ft. of frontage on Snell Road and utility pole at the road. Close to Okemo and Magic

    Geralyn Donohue Four Seasons Sotheby's Int'l Realty

    00 Snell Rd, Chester, VT 05143
  • /22

    $79,000

    $6K PRICE DROP
    • Land
    • 5 Acres
    • $15,800 per Acre

    0 Linden Way Unit 5093908, Chester, VT 05143

    Privacy doesn't have to mean isolation!!Wooded acreage, village convenience, and modern connectivity are rarely found in the same package. This newly approved 5 acre parcel in Chester, Vermont offers a private setting surrounded by mature forest while remaining just minutes from the historic village center. Accessed via a private right-of-way, the property provides a peaceful location for a

    Daire Gibney Barrett and Valley Associates Inc.

    0 Linden Way Unit 5093908, Chester, VT 05143
  • /35

    $372,500

    $8K PRICE DROP
    • Land
    • 24.5 Acres
    • $15,204 per Acre

    1992 Andover Ridge Rd, Andover, VT 05143

    Perched at the top of Andover Ridge Road, this exceptional Vermont building lot offers breathtaking 180-degree panoramic long-range views stretching across rolling mountain ranges and endless Green Mountain scenery. With a newly constructed driveway already in place and a state wastewater permit secured and the system installed, this property is well positioned for your future dream home or

    Claudia Harris Mary Mitchell Miller Real Estate

    1992 Andover Ridge Rd, Andover, VT 05143
  • /17

    $75,000

    • 2 Beds
    • 1 Bath
    • 620 Sq Ft

    1144 Potash Brook Rd, Chester, VT 05143

    Nice country spot with older mobile home on it. Property is located in a flood zone so if removed could not be replaced with a permanent structure. Power, septic and electric on sight along with a 1 car garage. Home could be repaired, would also make a great spot for a snowbird wanting a spot in Vermont or anyone looking to park an RV. Property is sold AS IS CASH ONLY

    Agent Photo

    Julie Buffum

    Buffum Realty

    1144 Potash Brook Rd, Chester, VT 05143
  • /41

    $5,150,000

    • 8 Beds
    • 7.5 Baths
    • 10,062 Sq Ft

    3800 Weston-Andover Rd, Andover, VT 05143

    Bringing generations together in a place that inspires connection, adventure, celebration, work and stewardship, Moosewalk Lane is a purpose built multigenerational family compound. Created over two decades and set on 384 private acres in Vermont's Green Mountains, Moosewalk Lane is offered fully furnished and equipped. Anchored by a 10,062 square foot timber frame home, guest house, writer's

    Steve Stettler Four Seasons Sotheby's Int'l Realty

    3800 Weston-Andover Rd, Andover, VT 05143
  • /39

    $1,200,000

    • 4 Beds
    • 3 Baths
    • 3,308 Sq Ft

    76 Goldthwaite Rd, Chester, VT 05143

    Experience the Vermont lifestyle in this beautifully renovated 1864 Brick Federal style farmhouse set on 7.8 private acres just minutes from town. Rich in historic character and thoughtfully updated for modern living, this exceptional property offers the perfect blend of comfort, charm, and year-round recreation.Inside, you’ll find four spacious bedrooms, wide plank wood floors, and inviting

    Gary Coger Four Seasons Sotheby's Int'l Realty

    76 Goldthwaite Rd, Chester, VT 05143
  • /47

    $549,000

    $20K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,464 Sq Ft

    3341 Trebo Rd, Chester, VT 05143

    Set along a quiet country road, this inviting 4-bedroom, 2.5-bath home offers the perfect blend of comfort, space, and Vermont charm. The open-concept layout features high ceilings and abundant natural light, creating a warm, airy feel throughout. A spacious primary suite includes a jetted tub and walk-in closet, providing a true retreat at day’s end.Step outside to a sunny, open lot with

    Daire Gibney Barrett and Valley Associates Inc.

    3341 Trebo Rd, Chester, VT 05143
  • /12

    $99,999

    $20K PRICE DROP
    • Land
    • 3.24 Acres
    • $30,864 per Acre

    508 Mattson Rd, Chester, VT 05143

    This property offers so many possibilities! Nestled on a quiet dirt road in scenic Chester just 10 mile from Okemo, this 3.24-acre parcel offers the perfect blend of open space and wooded privacy. The front of the lot features a sunny, open field with a pole barn, ideal for storage, hobbies, or future expansion. As you move toward the back of the property, the land gently slopes up to a wooded

    Agent Photo

    Jessica Citera

    Cummings & Co

    508 Mattson Rd, Chester, VT 05143
  • /9

    $119,000

    $10K PRICE DROP
    • Land
    • 7.95 Acres
    • $14,969 per Acre

    0 Green Mountain Turnpike Unit 5081034, Chester, VT 05143

    Nestled in the picturesque hills of Chester, this inviting 7.95+/- acre property offers the perfect blend of privacy, beauty, and potential. Wander through a peaceful forest where moss covered stones, classic Vermont stone walls, and soft woodland light create a truly serene setting. With some thoughtful clearing, this parcel could open up to stunning views overlooking the charming fields and

    Thaddeus Abare Barrett and Valley Associates Inc.

    0 Green Mountain Turnpike Unit 5081034, Chester, VT 05143
  • /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
  • /22

    $279,000

    • 5 Beds
    • 3 Baths
    • 1,812 Sq Ft

    2100 Baltimore Rd, Chester, VT 05143

    COUNTRY LIVING ON 4.97 ACRES, JUST 6 MILES TO SPRINGFIELD SHOPPING PLAZA. 9 ROOM HOME OFFERS GROUND FLOOR WITH APPLIANCED KITCHEN W/ DINING AREA, LIVING ROOM, SUNROOM, FULL BATH, FRONT BEDROOM, & ANOTHER BEDROOM W/ FULL BATH. THE SECOND FLOOR HAS 2 BEDROOMS PLUS ANOTHER BEDROOM W/ 3/4 BATH AND WALK-IN CLOSET. SEVCA RECENTLY INSULATED ENTIRE HOUSE AND ADDED A NEW FHA OIL FURNACE IN THE SUMMER OF

    Don Chabot Town and Country Realty

    2100 Baltimore Rd, Chester, VT 05143
  • /36

    $225,000

    $25K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 980 Sq Ft

    64 County Rd, North Springfield, VT 05150

    Enjoy the ease of single-level living in this 2008 single-wide home set on 2.5 peaceful Vermont acres. The open-concept kitchen and living area is filled with natural light, creating a warm and inviting atmosphere. Offering three bedrooms, one full bath, and a convenient laundry area. Recent improvements include new carpeting and fresh interior paint, making this home truly move-in ready. The

    Carol Slocum Keller Williams Realty Metro-Keene

    64 County Rd, North Springfield, VT 05150

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