Windham, VT Homes

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  /30

  $579,000

  • 4 Beds
  • 2 Baths
  • 2,656 Sq Ft

  204 Meeting House Ln, Brattleboro, VT 05301

  Your Dream Home Awaits on Meetinghouse Lane! Nestled in the desirable and quiet neighborhood of Meetinghouse Lane, this contemporary home offers both privacy & charm. Surrounded by mature trees, the property feels like a peaceful retreat, while still being conveniently located. A paved driveway leads to an oversized two-car garage, connected to the house by a convenient breezeway. The expansive

  Desiree Stango Berkley & Veller Greenwood Country

  204 Meeting House Ln, Brattleboro, VT 05301
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  /18

  $2,295 per month

  • 2 Beds
  • 1 Bath
  • 1,400 Sq Ft
  • Condo for Rent

  131 Frost St Unit 2, Brattleboro, VT 05301

  Applications must be received prior to showings- Rent includes Wifi, snow removal from driveway, water/sewer - Tenants pays electric and Oil (at owners rate)- Large, light filled 3 bedroom first floor apartment in a 2 unit building. - In unit W/D included - Large and quiet back yard- Garage included with dedicated driveway - Ample storage with back barn/workshop- Pets

  131 Frost St Unit 2, Brattleboro, VT 05301
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  /34

  $334,500 Sold Aug 01, 2025

  • 1,120 Sq Ft
  • $299/SF
  • 57 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1984

  49 Hampshire Cir, Brattleboro, VT 05301

  Cute home at the end of the cul-de-sac. Large front deck with a slider that leads into a newly refinished kitchen, dining area and living room. A half bath with laundry complete the first floor. Two bedrooms upstairs with a full bath. First floor has a door that leads out back to another large deck. The third bedroom and family room in the walkout basement. Open house Saturday 6/21/25 from

  Darlene Conca Keller Williams Realty Metro-Keene

  49 Hampshire Cir, Brattleboro, VT 05301
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  /26

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 962 Sq Ft

  1 Wildwood Dr, West Brattleboro, VT 05301

  1 Wildwood Dr, West Brattleboro, VT 05301
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  /40

  $795,000

  • 3 Beds
  • 5 Baths
  • 2,663 Sq Ft

  1194 Ames Hill Rd, Brattleboro, VT 05301

  Welcome to The Appleshed. Starting as a storage structure within an old apple orchard, to a gentleman's hunting/fishing camp, to the cherished family home it is today, this property has had many lives and grown into a beloved gathering place for generations. Now it’s ready for its next chapter. Set on 63.8 acres with a babbling brook and breathtaking views of Mount Monadnock, this is a true

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  1194 Ames Hill Rd, Brattleboro, VT 05301
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  /10

  $1,800 per month

  • 1 Bed
  • 1 Bath
  • 535 Sq Ft
  • Apartment for Rent

  215 Main St Unit 204, Brattleboro, VT 05301

  Recently renovated One bedroom apartment on the second floor. This one-bedroom apartment has bright sun lit rooms, with additional locking storage in the building, along with an elevator to get to the second floor for the onsite laundry facilities. This is intown living at its best. Photos are virtually staged

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  215 Main St Unit 204, Brattleboro, VT 05301
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  /9

  $175,000 Sold Jul 31, 2025

  • Land
  • 14 Acres
  • $12,700 per Acre

  • 7 Days On Market

  0 E Orchard St Unit 5046918, Brattleboro, VT 05301

  Here's an excellent opportunity to have a larger parcel of land, 13+ acres, in Brattleboro, not only in town but right across the street from the Brattleboro Country Club! This property has not been available for over 35 years and now it's ready for your building plans. This wooded lot features a mature mix of hard and softwoods including some true giants. There's a stream coursing through it

  Bill Hickok Berkley & Veller Greenwood Country

  0 E Orchard St Unit 5046918, Brattleboro, VT 05301
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  /32

  Est $561,880 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,770 Sq Ft

  133 Briggs Rd, Brattleboro, VT 05301

  133 Briggs Rd, Brattleboro, VT 05301
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  /60

  $899,000

  • 4 Beds
  • 3.5 Baths
  • 3,685 Sq Ft

  155 Hillwinds N, Brattleboro, VT 05301

  Situated in Brattleboro’s premier, rural neighborhood, this much-loved home is a masterclass in thoughtful design, meticulous construction, & refined living. A grand dbl-door foyer welcomes you into a soaring entry hall that flows seamlessly into a sunken, dbl-height ceiling LR - complete w/ granite-surround FP, custom blt-ins, & crowned by a dramatic balcony overlook. Light pours in from every

  Dan Normandeau Berkley & Veller Greenwood Country

  155 Hillwinds N, Brattleboro, VT 05301
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  /12

  $1,180 per month

  • 1 Bed
  • 1 Bath
  • 500 Sq Ft
  • Townhouse for Rent

  995 Western Ave Unit 300, Brattleboro, VT 05301

  Kitchen/living room plus one bedroom on 3rd Floor.Walk to farmer’s market. Laundromat just across the street.Apartment is one of four units in quiet building, each with separate entrance.Lawn care and snow plowing provided.Balcony.Shower in bathroom (no bathtub). Large backyard with room to garden.One parking place only.No smoking.Pets

  995 Western Ave Unit 300, Brattleboro, VT 05301
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  /60

  $570,000 Sold Jul 31, 2025

  • 2,093 Sq Ft
  • $272/SF
  • 79 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1991

  290 Roel Rd, Brattleboro, VT 05301

  Welcome to your dream Vermont retreat. Tucked away on 15.6 private acres at the end of a quiet country road, this 2-bedroom, 2.5-bathroom home offers an inspiring blend of rustic elegance and modern comfort. Surrounded by mature oaks and sweeping views of Mount Monadnock, Black Mountain, and the rolling green hills. This home features classic post & beam construction, soaring cathedral ceilings,

  Flex Realty Group Flex Realty

  290 Roel Rd, Brattleboro, VT 05301
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  /14

  Est $280,412 Not Listed For Sale

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

  23 Robin Way, Brattleboro, VT 05301

  23 Robin Way, Brattleboro, VT 05301
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  /60

  $695,000

  • 3 Beds
  • 2.5 Baths
  • 2,315 Sq Ft

  23 Meeting House Ln, Brattleboro, VT 05301

  First Time on the Market – Premier Brattleboro Location!Nestled on one of the most desirable lots in one of Brattleboro’s finest neighborhoods, this well-maintained home is being offered for sale for the very first time! Custom-built by the current owner in 1970 with attention to detail, this spacious ranch offers comfort, functionality, and an impressive list of amenities.Perfect for

  Bert Inman RE/MAX Town & Country

  23 Meeting House Ln, Brattleboro, VT 05301
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  /12

  $2,200 per month

  • 1 Bed
  • 1 Bath
  • 790 Sq Ft
  • Apartment for Rent

  4 Elliot St Unit 6, Brattleboro, VT 05301

  The National, featuring this 2 Bedroom apartment with bright sunlit rooms, amazing hardwood floors and views of downtown and the mountain. Coin operated Laundry is on site and off street parking is available in the parking garage. The building is pet friendly

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  4 Elliot St Unit 6, Brattleboro, VT 05301
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  /18

  $335,000 Sold Jul 30, 2025

  • 1,174 Sq Ft
  • $285/SF
  • 36 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1956

  138 Cedar St, Brattleboro, VT 05301

  Welcome to this adorable 3-bedroom, 1-bath ranch-style home nestled in one of Brattleboro's most sought-after neighborhoods! Built in 1956, this lovingly cared for gem perfectly blends classic character with modern comfort. Many recent upgrades including CertainTeed Monogram vinyl siding and trim, freshly painted interior walls and so much more. The kitchen features a sleek Whirlpool glass top

  Claire Renaud Berkley & Veller Greenwood Country

  138 Cedar St, Brattleboro, VT 05301
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  /13

  Not Listed For Sale

  0 Middle Rd, Brattleboro, VT 05301

  0 Middle Rd, Brattleboro, VT 05301
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  /27

  $550,000

  • 3 Beds
  • 3 Baths
  • 3,148 Sq Ft

  672 E Orchard St, West Brattleboro, VT 05301

  You can't beat this location, overlooking the Brattleboro Country Club golf course. This home was built circa 1919, and has many cool vintage features such as retro curved metal kitchen cabinets and baths. Generous rooms include a large living room with two field-stone fireplaces, a spacious family room. This is a 3 bedroom house with 3 full bathrooms, but it's really about how you configure

  John Hatton Berkley & Veller Greenwood Country

  672 E Orchard St, West Brattleboro, VT 05301
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  /2

  $1,300 per month

  • 1 Bed
  • 1 Bath
  • Condo for Rent

  498 Marlboro Rd Unit N35, Brattleboro, VT 05301

  Property Id: 15107811 bed, 1 bath apartment in Brattleboro, VT! This unit features modern amenities like a microwave, oven, and refrigerator. Enjoy off-street parking, on-site laundry, and a beautiful lawn. Pets are welcome! Don't miss out on this gem for $1,300/month. Book your viewing today!

  498 Marlboro Rd Unit N35, Brattleboro, VT 05301
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  /44

  $405,000 Sold Jul 28, 2025

  • 1,066 Sq Ft
  • $380/SF
  • 33 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1998

  156 Sherwood Cir, Brattleboro, VT 05301

  YOU CAN GET THERE FROM HERE! NEW ENGLAND CHARM AND FLEXIBLE SPACES...YOUR LUSH RETREAT AWAITS! A short drive to the cultural and foodie hub of southeastern Vermont, this slice of heaven is where your dreams take root. Follow a scenic road to a vibrant green lot where a terraced rock wall dotted with ferns and hostas signals your arrival. A large covered porch invites you to pull up a chair,

  Fine Homes Group International Keller Williams Realty-Metropolitan

  156 Sherwood Cir, Brattleboro, VT 05301
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  /12

  Est $493,078 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 3,400 Sq Ft

  58 Oak St, Brattleboro, VT 05301

  58 Oak St, Brattleboro, VT 05301
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  /60

  $649,000

  • 3 Beds
  • 2 Baths
  • 2,731 Sq Ft

  49 Tyler St, Brattleboro, VT 05301

  Rare opportunity to own this iconic Queen-Anne Victorian in Brattleboro’s coveted Tyler Street neighborhood. A remarkable and extremely rare blend of country and in-town living. Extraordinary and stunning views of the Connecticut River & Mount Wantastiquet. Lovingly cared for by the same owner for the past 29 yrs. This home sits proudly on the expansive 0.85-acre corner lot, in the core of

  Dan Normandeau Berkley & Veller Greenwood Country

  49 Tyler St, Brattleboro, VT 05301
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  /12

  $2,000 per month

  • 1 Bed
  • 1 Bath
  • 535 Sq Ft
  • Apartment for Rent

  215 Main St Unit 203, Brattleboro, VT 05301

  This amazing apartment is available immediately. The view from the large windows in the kitchen and living room are of downtown Brattleboro. Recently renovated this space offers shared living room and kitchen with a large one bedroom apartment. The building has designated off street parking, and elevator in the building, along with laundry facilities and additional storage as well. Schedule

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  215 Main St Unit 203, Brattleboro, VT 05301
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  /23

  $356,000 Sold Jul 28, 2025

  • 1,550 Sq Ft
  • $230/SF
  • 38 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1929

  122 Marlboro Ave, Brattleboro, VT 05301

  122 Marlboro Avenue is in a highly sought out, in-town neighborhood known for its peace and quiet, friendly neighbors, and super-convenient location. This solid, 3-4 bedroom, 2 bath home sits attractively on a sunny and level lot and comes with an oversized garage and attached workshop (and potential to add additional living space). This home provides a completely renovated and modernized

  Stephanie Peduzzi-Baker Brattleboro Area Realty

  122 Marlboro Ave, Brattleboro, VT 05301
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  /3

  Est $406,254 Not Listed For Sale

  • Studio
  • 2 Baths
  • 2,863 Sq Ft

  394 Canal St, Brattleboro, VT 05301

  394 Canal St, Brattleboro, VT 05301
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  /18

  $425,000

  • 3 Beds
  • 2 Baths
  • 2,074 Sq Ft

  36 Spruce St, Brattleboro, VT 05301

  New Price! $25,000.00 price drop and a revised offering... If you saw this home before you want to take a second look! The 2nd floor is now vacant! ..and ready for owner occupancy. The basement, barn and lower building are empty and ready for all YOUR stuff. Plenty of undercover storage for boats, special vehicles or lots of other toys. A workshop? Home is just right for 2 family use or

  Christine Lewis Brattleboro Area Realty

  36 Spruce St, Brattleboro, VT 05301
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  /13

  $1,500 per month

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft
  • Condo for Rent

  98 High St Unit 3, Brattleboro, VT 05301

  Property Id: 120577Charming, light, 1bedroom apartment is just a three-minute walk from downtown Brattleboro. The 3rd floor apartment is located in a grand Victorian house that includes a turret, front porch, and two third-floor outside decks. There is also a fenced-in patio with garden space in the back.The apartment has 4 rooms with a spacious central hallway and is suitable

  98 High St Unit 3, Brattleboro, VT 05301
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  /26

  $347,000 Sold Jul 25, 2025

  • 1,435 Sq Ft
  • $242/SF
  • 22 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1890

  157 Pine St, Brattleboro, VT 05301

  Be impressed by this stately in-town Victorian home with an airy and open-concept feel, handsome historical features, and many thoughtful and attractive upgrades. Enter this lovely home loaded with charm and character and be prepared to be wowed with high ceilings and the gorgeous hardwood floors! A highlight of the house is an attractive kitchen with appealing custom cabinetry, granite and

  Stephanie Peduzzi-Baker Brattleboro Area Realty

  157 Pine St, Brattleboro, VT 05301
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  /26

  Est $241,377 Not Listed For Sale

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

  17 Evergreen Ln, Brattleboro, VT 05301

  17 Evergreen Ln, Brattleboro, VT 05301
• 

  

  /59

  $547,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 5,850 Sq Ft

  628 S Main St, Brattleboro, VT 05301

  Absolutely Gorgeous In-Town Home with Exceptional Attention to Detail.This stunning residence offers over 5,000 square feet of meticulously designed living space in the main house, plus a fully separate accessory dwelling with two independent living areas—ideal for extended family, guests, or producing income. Additionally there is a two-car garage with an integrated service pit for

  Kerry Mulverhill Brattleboro Area Realty

  628 S Main St, Brattleboro, VT 05301
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  /29

  $365,000 Sold Jul 25, 2025

  • 1,620 Sq Ft
  • $225/SF
  • 10 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 2006

  28 Greenleaf St, Brattleboro, VT 05301

  West Brattleboro contemporary cape situated on a large private partially fenced lot with fruit trees, raised bed gardens and plenty of outdoor recreational space. This sturdy, well-built house offers low maintenance and quality finishes like the standing seam metal roof and cement siding. Ample large windows bring the outside IN and provide lots of natural light. Interior features include: a

  Chris Long BHG Masiello Brattleboro

  28 Greenleaf St, Brattleboro, VT 05301
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  /37

  Est $430,399 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,594 Sq Ft

  94 Brets Rd, Brattleboro, VT 05301

  94 Brets Rd, Brattleboro, VT 05301
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  /35

  $525,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 2,456 Sq Ft

  1073 Upper Dummerston Rd, Brattleboro, VT 05301

  This very Vermont country home is nestled on a peaceful, beautifully landscaped 1.5 acre lot along Upper Dummerston Road. Built with unparalleled craftsmanship by some of the region’s finest artisans, the home exudes exceptional quality throughout. At the heart of the residence is a large chef's kitchen, complete with a gas fireplace, granite countertops, solid maple cabinetry, and premium Wolf

  Thomas Dahlin Berkley & Veller Greenwood Country

  1073 Upper Dummerston Rd, Brattleboro, VT 05301
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  /27

  $487,500 Sold Jul 25, 2025

  • 1,618 Sq Ft
  • $301/SF
  • 12 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1985

  32 Christie Ln, Brattleboro, VT 05301

  This will be your favorite new listing. Tucked on a pocket of land, just beyond Memorial Park, you're in a neighborhood but it feels private, you see trees out every window. Custom-built home, 3 bedrooms, 2 1/2 updated baths, built in 1985. Incredibly warm and comfy. Cathedral ceiling with a wall of windows. Great kitchen for cooking, plenty of room for multiple chefs. Cozy nook for a small

  John Hatton Berkley & Veller Greenwood Country

  32 Christie Ln, Brattleboro, VT 05301
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  /20

  Est $253,663 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,100 Sq Ft

  149 Canal St, Brattleboro, VT 05301

  149 Canal St, Brattleboro, VT 05301
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  /20

  $495,000 Under Contract

  • 3 Beds
  • 3 Baths
  • 2,400 Sq Ft

  21 Howard St, Brattleboro, VT 05301

  This beautiful Victorian home is just a short stroll from vibrant Brattleboro and has access to a huge town trail network. Nicely landscaped and has a partially fenced yard for pets or children. The house has lovely Victorian detailing and includes 3 covered porches. The formal entry has hardwood flooring, period staircase, stained glass window and a 3/4 bath. The adjacent front parlor includes

  Robert Doyle Berkley & Veller Greenwood Country

  21 Howard St, Brattleboro, VT 05301
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  /29

  $330,000 Sold Jul 25, 2025

  • 1,352 Sq Ft
  • $244/SF
  • 16 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1890

  64 Meadowbrook Rd, Brattleboro, VT 05301

  SWEET! Sitting on 3/4 of an acre of lovely level land, a corner lot and lots of room for gardening and play! There is a 2 car garage (owner is putting on new doors ) that has been a workshop with insulation, electric and was heated....This gentle one way street encourages sitting on the traditional front porch with a good book, or close your eyes, and nap a bit. The sunny side also has a

  Christine Lewis Brattleboro Area Realty

  64 Meadowbrook Rd, Brattleboro, VT 05301
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  /30

  Not Listed For Sale

  • 8 Beds
  • 4 Baths
  • 3,854 Sq Ft

  100 Frost St, Brattleboro, VT 05301

  100 Frost St, Brattleboro, VT 05301
• 

  

  /20

  $299,000

  • 3 Beds
  • 1 Bath
  • 1,178 Sq Ft

  17 Winter Ct, Brattleboro, VT 05301

  Classic Ranch Style Home! Just starting out or thinking of downsizing? This could be the one! Nestled in a sweet neighborhood, this charming ranch offers easy one-level living just minutes from downtown shopping, schools, and recreation. Set on a manageable 0.2 acre lot, this home features a bright enclosed porch/bonus room perfect for morning coffee, reading, or relaxing year-round. Continuing

  Liz LaVorgna Berkley & Veller Greenwood Country

  17 Winter Ct, Brattleboro, VT 05301
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  /2

  $185,000 Sold Jul 18, 2025

  • 2,562 Sq Ft
  • $72/SF
  • 6 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1870

  17 Thomas St, Brattleboro, VT 05301

  Large 2 unit apartment building on a quiet one way street and is an easy stroll to downtown Brattleboro. There is a partially fenced yard, off street parking, 2 covered porches and shed off the rear of this home. Each spacious unit provides 2 bedrooms, bath, living room and kitchen (the lower unit also has a dining room). Full basement with newer boilers and tenants pay for heat, electric and

  Robert Doyle Berkley & Veller Greenwood Country

  17 Thomas St, Brattleboro, VT 05301
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  /31

  Est $339,534 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  47 Sherwood Cir, Brattleboro, VT 05301

  47 Sherwood Cir, Brattleboro, VT 05301

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