36,490

Windsor County, VT Homes

Section Image
  • 81 Main St, Chester, VT 05143
    81 Main St, Chester, VT 05143
    81 Main St, Chester, VT 05143
    /58

    $475,000

    • 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
  • 51-53 Pleasant St Unit 53B, Springfield, VT 05156
    51-53 Pleasant St Unit 53B, Springfield, VT 05156
    51-53 Pleasant St Unit 53B, Springfield, VT 05156
    /15

    $1,675 Per Month

    • 2 Beds
    • 1 Bath
    • 51-53 Pleasant St

    51-53 Pleasant St Unit 53B, Springfield, VT 05156

    51-53 Pleasant St Unit 53B, Springfield, VT 05156
  • 388 Alden Partridge Rd Unit 6E, Hartford, VT 05001
    388 Alden Partridge Rd Unit 6E, Hartford, VT 05001
    388 Alden Partridge Rd Unit 6E, Hartford, VT 05001
    /34

    $570,000

    Sold Jan 09, 2026

    388 Alden Partridge Rd Unit 6E, Hartford, VT 05001

    • 3 Beds
    • 3.5 Baths
    • 2,080 Sq Ft
    • Built 1983

    Last Sold Summary

    • 2% Below List Price
    • $274/SF
    • 5 Days On Market

    Last Listing Agent Linda Hicks Quechee Lakes Real Estate Center

    388 Alden Partridge Rd Unit 6E, Hartford, VT 05001
    • 5 Mountain Ave Unit 4, Woodstock, VT 05091
      5 Mountain Ave Unit 4, Woodstock, VT 05091
      5 Mountain Ave Unit 4, Woodstock, VT 05091
      /34

      Not Listed For Sale

      5 Mountain Ave Unit 4, Woodstock, VT 05091

      • 2 Beds
      • 2.5 Baths
      • 1,590 Sq Ft
      • Built 1880
      5 Mountain Ave Unit 4, Woodstock, VT 05091

      Last Sold Summary

      • 12 Days On Market

  • 1522 Barnard Rd, Woodstock, VT 05091
    1522 Barnard Rd, Woodstock, VT 05091
    1522 Barnard Rd, Woodstock, VT 05091
    /52

    $1,395,000

    $100K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 3,648 Sq Ft

    1522 Barnard Rd, Woodstock, VT 05091

    Just 2 miles from Woodstock Village, this gracious brick Cape on 6 open acres offers the perfect blend of privacy, comfort, and classic Vermont charm. Thoughtfully expanded and beautifully maintained, the home features a chef’s kitchen that opens seamlessly to a spacious gathering room designed for entertaining and everyday living. Multiple fireplaces—including a wood-burning and gas-ready—add

    Keri Cole Williamson Group Sothebys Intl. Realty

    1522 Barnard Rd, Woodstock, VT 05091
  • 398 Valley View Rd, White River Junction, VT 05001
    398 Valley View Rd, White River Junction, VT 05001
    398 Valley View Rd, White River Junction, VT 05001
    /13

    $115,000

    Sold Jun 24, 2026

    398 Valley View Rd, White River Junction, VT 05001

    • Land
    • 4.1 Acres
    • $28,049 per Acre

    Last Sold Summary

    • 50% Below List Price
    • 49 Days On Market

    Current Estimated Value $355,333

    Last Listing Agent Grayson VanHendrick Flex Realty

    398 Valley View Rd, White River Junction, VT 05001
    • 1650 Quimby Mountain Rd, Sharon, VT 05065
      1650 Quimby Mountain Rd, Sharon, VT 05065
      1650 Quimby Mountain Rd, Sharon, VT 05065
      /39

      Est $701,242

      Not Listed For Sale

      1650 Quimby Mountain Rd, Sharon, VT 05065

      • 4 Beds
      • 4 Baths
      • 2,289 Sq Ft
      • Built 1964
      1650 Quimby Mountain Rd, Sharon, VT 05065

      Last Sold Summary

      • 6 Days On Market

  • 55 Cherry Hill, Springfield, VT 05156
    55 Cherry Hill, Springfield, VT 05156
    55 Cherry Hill, Springfield, VT 05156
    /60

    $2,300,000

    • 6 Beds
    • 4.5 Baths
    • 8,656 Sq Ft

    55 Cherry Hill, Springfield, VT 05156

    Steeped in history and timeless elegance, this extraordinary circa-1860 Georgian Colonial estate offers over 8,000 square feet of refined living space where classic architecture meets remarkable craftsmanship. From the moment you enter, you are greeted by stunning period details including exquisite crown moldings, grand proportions, soaring ceilings, and beautifully preserved finishes that

    Joe Castaluccio Winhall Real Estate

    55 Cherry Hill, Springfield, VT 05156
  • 138 Ascutney St, Windsor, VT 05089
    138 Ascutney St, Windsor, VT 05089
    138 Ascutney St, Windsor, VT 05089
    /17

    $40,000

    Sold Oct 06, 2025

    138 Ascutney St, Windsor, VT 05089

    • 2 Beds
    • 1 Bath
    • 434 Sq Ft
    • Built 1952

    Last Sold Summary

    • 4% Above List Price
    • $92/SF
    • 6 Days On Market

    Last Listing Agent DJ Chabot Town and Country Realty

    138 Ascutney St, Windsor, VT 05089
    • 714 Beaver Meadow Rd, Norwich, VT 05055
      714 Beaver Meadow Rd, Norwich, VT 05055
      714 Beaver Meadow Rd, Norwich, VT 05055
      /39

      Est $806,058

      Not Listed For Sale

      714 Beaver Meadow Rd, Norwich, VT 05055

      • 3 Beds
      • 2 Baths
      • 1,985 Sq Ft
      • Built 1903
      714 Beaver Meadow Rd, Norwich, VT 05055

      Last Sold Summary

      • 6 Days On Market

  • Markham Mountain, Andover, VT 05143
    Markham Mountain, Andover, VT 05143
    Markham Mountain, Andover, VT 05143
    /16

    $3,150,000

    • Land
    • 506 Acres
    • $6,225 per Acre

    Markham Mountain, Andover, VT 05143

    Red Top is a breathtaking 506 +/- acre parcel in the town of Andover and on the border of Weston. Here, the rugged grandeur of the Green Mountains unfolds, offering extraordinary views to the South, where the mountain silhouettes stretch across the skyline and the imposing profile of Glebe Mountain asserts its presence.This land's historical roots run deep, originally belonging to the Marsh

    Story Jenks LANDVEST

    Markham Mountain, Andover, VT 05143
  • 30 Meadow Dr, Springfield, VT 05156
    30 Meadow Dr, Springfield, VT 05156
    30 Meadow Dr, Springfield, VT 05156
    /30

    $325,000

    Sold May 20, 2026

    30 Meadow Dr, Springfield, VT 05156

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • Built 1968

    Last Sold Summary

    • 5% Above List Price
    • $203/SF
    • 7 Days On Market

    Current Estimated Value $315,309

    Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

    30 Meadow Dr, Springfield, VT 05156
    • 574 Willard Rd Unit 1A, Hartford, VT 05001
      574 Willard Rd Unit 1A, Hartford, VT 05001
      574 Willard Rd Unit 1A, Hartford, VT 05001
      /18

      Not Listed For Sale

      574 Willard Rd Unit 1A, Hartford, VT 05001

      • 1 Bed
      • 1 Bath
      • 880 Sq Ft
      • Built 1978
      574 Willard Rd Unit 1A, Hartford, VT 05001

      Last Sold Summary

      • 17 Days On Market

  • 0 New Boston Rd, Thetford, VT 05074
    0 New Boston Rd, Thetford, VT 05074
    0 New Boston Rd, Thetford, VT 05074
    /15

    $237,000

    • Land
    • 221 Acres
    • $1,072 per Acre

    0 New Boston Rd, Thetford, VT 05074

    IntroductionThe ownership is selling their property in two separate parcels, divided by the town line. The +/-60 acre Strafford parcel is well suited to future home development with paved town road frontage and roadside electric service. The +/-220 acre Thetford parcel is well suited to a camp or seasonal off-grid home development with beautiful local views.Both parcels have

    John Latham Fountains Land

    0 New Boston Rd, Thetford, VT 05074
  • 0 French Meadow Rd, Springfield, VT 05156
    0 French Meadow Rd, Springfield, VT 05156
    0 French Meadow Rd, Springfield, VT 05156
    /13

    $215,000

    Sold Jun 30, 2026

    0 French Meadow Rd, Springfield, VT 05156

    • Land
    • 46.06 Acres
    • $4,668 per Acre

    Last Sold Summary

    • 6% Below List Price
    • 27 Days On Market

    Last Listing Agent Jessica Landers Barrett and Valley Associates Inc.

    0 French Meadow Rd, Springfield, VT 05156
    • 230 S Main St, Rochester, VT 05767
      230 S Main St, Rochester, VT 05767
      230 S Main St, Rochester, VT 05767
      /21

      Est $171,882

      Not Listed For Sale

      230 S Main St, Rochester, VT 05767

      • Studio
      • 1,500 Sq Ft
      • Built 1920
      230 S Main St, Rochester, VT 05767

      Last Sold Summary

      • 4 Days On Market

  • 891 Vermont Route 100, Weston, VT 05161
    891 Vermont Route 100, Weston, VT 05161
    891 Vermont Route 100, Weston, VT 05161
    /12

    $245,000

    Pending
    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    891 Vermont Route 100, Weston, VT 05161

    Charming and efficient, this 2-bedroom, 1-bath home offers a cozy retreat in the heart of Weston, Vermont. Designed for single-level living and low maintenance, the layout makes the most of its space. The main living area features an open flow between the living room and eat-in kitchen, leading to a deck that is perfect for morning coffee or outdoor grilling. Two bedrooms and a full bath complete

    Andie Fusco Four Seasons Sotheby's Int'l Realty

    891 Vermont Route 100, Weston, VT 05161
  • 483 South St, Springfield, VT 05156
    483 South St, Springfield, VT 05156
    483 South St, Springfield, VT 05156
    /19

    $280,900

    Sold Dec 15, 2025

    483 South St, Springfield, VT 05156

    • 3 Beds
    • 1 Bath
    • 1,716 Sq Ft
    • Built 1972

    Last Sold Summary

    • 6% Above List Price
    • $164/SF
    • 5 Days On Market

    Current Estimated Value $285,442

    Last Listing Agent Kirsten Dole Coldwell Banker LIFESTYLES - Hanover

    483 South St, Springfield, VT 05156
    • 35 Depot St, Chester, VT 05143
      35 Depot St, Chester, VT 05143
      35 Depot St, Chester, VT 05143
      /17

      Est $83,511

      Not Listed For Sale

      35 Depot St, Chester, VT 05143

      • 4 Beds
      • Built 1880
      35 Depot St, Chester, VT 05143

      Last Sold Summary

      • 68 Days On Market

  • 6416 Vermont 107, Stockbridge, VT 05772
    6416 Vermont 107, Stockbridge, VT 05772
    6416 Vermont 107, Stockbridge, VT 05772
    /24

    $217,500

    • Land
    • 94 Acres
    • $2,314 per Acre

    6416 Vermont 107, Stockbridge, VT 05772

    Nestled among natural streams in the rolling hills of Vermont’s Green Mountains, this remarkable 94-acre parcel offers sweeping views overlooking the White River. Rich with potential for residential use or future development, the property includes a private septic system and a drilled well already in place. With 670 feet of frontage along VT Route 107, the land provides convenient access while

    Kate Jarvis Williamson Group Sothebys Intl. Realty

    6416 Vermont 107, Stockbridge, VT 05772
  • 255 Robert Frost Ln, Hartford, VT 05001
    255 Robert Frost Ln, Hartford, VT 05001
    /2

    $895,000

    Sold Nov 25, 2025

    255 Robert Frost Ln, Hartford, VT 05001

    • 4 Beds
    • 5.5 Baths
    • 3,244 Sq Ft
    • Built 2000

    Last Sold Summary

    • $276/SF
    • 0 Days On Market

    Last Listing Agent Linda Hicks Quechee Lakes Real Estate Center

    255 Robert Frost Ln, Hartford, VT 05001
    • 600 Kendricks Corner Rd, Perkinsville, VT 05151
      600 Kendricks Corner Rd, Perkinsville, VT 05151
      600 Kendricks Corner Rd, Perkinsville, VT 05151
      /6

      Est $78,167

      Not Listed For Sale

      600 Kendricks Corner Rd, Perkinsville, VT 05151

      600 Kendricks Corner Rd, Perkinsville, VT 05151

      Last Sold Summary

      • 16 Days On Market

  • 115 Prior Rd, Cavendish, VT 05142
    115 Prior Rd, Cavendish, VT 05142
    115 Prior Rd, Cavendish, VT 05142
    /41

    $725,000

    $70K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,128 Sq Ft

    115 Prior Rd, Cavendish, VT 05142

    Living and working in the country with privacy, wildlife, snowmobiling from your front door, skiing at Okemo, and the overall beauty of Vermont would be a dream come true, right? Well, here's your opportunity with this pretty log home on 19 acres on a dead-end town-maintained road. Inside the house, you will love the open concept of the living room, and the kitchen and dining room with cathedral

    Glenn Olney Barrett and Valley Associates Inc.

    115 Prior Rd, Cavendish, VT 05142
  • 6196 Stage Rd, Woodstock, VT 05091
    6196 Stage Rd, Woodstock, VT 05091
    6196 Stage Rd, Woodstock, VT 05091
    /60

    $1,520,000

    Sold Sep 30, 2025

    6196 Stage Rd, Woodstock, VT 05091

    • 4 Beds
    • 4 Baths
    • 2,408 Sq Ft
    • Built 2015

    Last Sold Summary

    • 2% Above List Price
    • $631/SF
    • 4 Days On Market

    Last Listing Agent Eric Johnston Four Seasons Sotheby's Int'l Realty

    6196 Stage Rd, Woodstock, VT 05091
    • 00 Hemlock Hill Dr, Ludlow, VT 05149
      00 Hemlock Hill Dr, Ludlow, VT 05149
      00 Hemlock Hill Dr, Ludlow, VT 05149
      /17

      Not Listed For Sale

      00 Hemlock Hill Dr, Ludlow, VT 05149

      00 Hemlock Hill Dr, Ludlow, VT 05149

      Last Sold Summary

      • 1,056 Days On Market

  • 273 Birch Landing Rd Unit 23, Plymouth, VT 05056
    273 Birch Landing Rd Unit 23, Plymouth, VT 05056
    273 Birch Landing Rd Unit 23, Plymouth, VT 05056
    /60

    $549,000

    Under Contract
    • 3 Beds
    • 3 Baths
    • 1,990 Sq Ft

    273 Birch Landing Rd Unit 23, Plymouth, VT 05056

    Experience the ultimate Vermont lifestyle in this immaculate, two-level townhome located in the highly desirable Lakeside Birch Landing Community on Echo Lake. This sun-drenched property perfectly combines lakeside tranquility with convenient access to world-class skiing at nearby Okemo and Killington resorts.The main floor features a bright, open-concept layout designed for seamless

    Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

    273 Birch Landing Rd Unit 23, Plymouth, VT 05056
  • 109 Okemo Ridge Rd Unit C201, Ludlow, VT 05149
    109 Okemo Ridge Rd Unit C201, Ludlow, VT 05149
    109 Okemo Ridge Rd Unit C201, Ludlow, VT 05149
    /32

    $370,000

    Sold Dec 12, 2025

    109 Okemo Ridge Rd Unit C201, Ludlow, VT 05149

    • 1 Bed
    • 1 Bath
    • 640 Sq Ft
    • Built 1984

    Last Sold Summary

    • $578/SF
    • 32 Days On Market

    Current Estimated Value $372,867

    Last Listing Agent Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

    109 Okemo Ridge Rd Unit C201, Ludlow, VT 05149
    • 111 Lakeland Dr Unit B, Hartford, VT 05001
      111 Lakeland Dr Unit B, Hartford, VT 05001
      111 Lakeland Dr Unit B, Hartford, VT 05001
      /33

      Not Listed For Sale

      111 Lakeland Dr Unit B, Hartford, VT 05001

      • 3 Beds
      • 2 Baths
      • 1,346 Sq Ft
      • Built 1982
      111 Lakeland Dr Unit B, Hartford, VT 05001

      Last Sold Summary

      • 2 Days On Market

  • 2-66 Goshawk Dr, Plymouth, VT 05056
    2-66 Goshawk Dr, Plymouth, VT 05056
    2-66 Goshawk Dr, Plymouth, VT 05056
    /17

    $53,000

    • Land
    • 1.5 Acres
    • $35,333 per Acre

    2-66 Goshawk Dr, Plymouth, VT 05056

    Dreaming of building your own Vermont-style home but hoping to find an affordable parcel? This lot at Hawk Resort is the perfect opportunity. With power and other utilities already on site and the ability to connect to the community septic system, you’ll be well on your way to breaking ground on your dream home. Tucked among the trees in a peaceful natural setting, this property offers privacy

    Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

    2-66 Goshawk Dr, Plymouth, VT 05056
  • 93 Litchfield St, Springfield, VT 05156
    93 Litchfield St, Springfield, VT 05156
    93 Litchfield St, Springfield, VT 05156
    /28

    $197,700

    Sold Jul 07, 2025

    93 Litchfield St, Springfield, VT 05156

    • 2 Beds
    • 1 Bath
    • 640 Sq Ft
    • Built 1941

    Last Sold Summary

    • 1% Below List Price
    • $309/SF
    • 47 Days On Market

    Current Estimated Value $198,194

    Last Listing Agent Debra Staniscia Four Seasons Sotheby's Int'l Realty

    93 Litchfield St, Springfield, VT 05156
    • 122 Parrish View Rd, West Windsor, VT 05037
      122 Parrish View Rd, West Windsor, VT 05037
      122 Parrish View Rd, West Windsor, VT 05037
      /39

      Not Listed For Sale

      122 Parrish View Rd, West Windsor, VT 05037

      • 2 Beds
      • 2.5 Baths
      • 1,400 Sq Ft
      • Built 2007
      122 Parrish View Rd, West Windsor, VT 05037

      Last Sold Summary

      • 47 Days On Market

  • 58 Lakeshore Dr, Ludlow, VT 05149
    58 Lakeshore Dr, Ludlow, VT 05149
    58 Lakeshore Dr, Ludlow, VT 05149
    /30

    $3,500,000

    • 4 Beds
    • 3 Baths
    • 2,571 Sq Ft

    58 Lakeshore Dr, Ludlow, VT 05149

    One-of-a-kind Lake Rescue sanctuary with 179 feet of shoreline, stone walls, perennial gardens, apple trees, and a sprawling flat lawn perfect for games and gatherings. Offering exceptional flexibility, this special setting on 4.35 acres has the potential to become a family compound, multi-generational retreat, or income-producing investment. A 3-bedroom septic permit is already in place,

    Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

    58 Lakeshore Dr, Ludlow, VT 05149
  • 00 Carlton Hill Rd, Woodstock, VT 05091
    00 Carlton Hill Rd, Woodstock, VT 05091
    00 Carlton Hill Rd, Woodstock, VT 05091
    /15

    $120,000

    Sold Apr 17, 2026

    00 Carlton Hill Rd, Woodstock, VT 05091

    • Land
    • 3.54 Acres
    • $33,898 per Acre

    Last Sold Summary

    • 19% Below List Price
    • 0 Days On Market

    Last Listing Agent Sandy Reavill

    00 Carlton Hill Rd, Woodstock, VT 05091
    • 238 South St, Hartford, VT 05088
      238 South St, Hartford, VT 05088
      238 South St, Hartford, VT 05088
      /28

      Not Listed For Sale

      238 South St, Hartford, VT 05088

      • 3 Beds
      • 1.5 Baths
      • 1,170 Sq Ft
      • Built 1883
      238 South St, Hartford, VT 05088

      Last Sold Summary

      • 5 Days On Market

  • S-1C Great Roaring Brook Rd, Plymouth, VT 05056
    S-1C Great Roaring Brook Rd, Plymouth, VT 05056
    S-1C Great Roaring Brook Rd, Plymouth, VT 05056
    /25

    $115,000

    • Land
    • 10 Acres
    • $11,500 per Acre

    S-1C Great Roaring Brook Rd, Plymouth, VT 05056

    Ten-acre wooded parcel with potential views located near the top of Great Roaring Brook Rd. The topography is rolling too steep with multiple buildings sites, rock crop outs, and streams throughout. A wonderful opportunity to design and build your Vermont dream home. Located between Ludlow and Woodstock with equal distance to Killington and Okemo Ski areas. Close to Lake Rescue and Echo Lake for

    Terry Davis Williamson Group Sothebys Intl. Realty

    S-1C Great Roaring Brook Rd, Plymouth, VT 05056
  • 38 Cardinal Dr, Hartford, VT 05001
    38 Cardinal Dr, Hartford, VT 05001
    38 Cardinal Dr, Hartford, VT 05001
    /26

    $325,000

    Sold Aug 15, 2025

    38 Cardinal Dr, Hartford, VT 05001

    • 4 Beds
    • 2 Baths
    • 1,340 Sq Ft
    • Built 1930

    Last Sold Summary

    • 11% Below List Price
    • $243/SF
    • 6 Days On Market

    Last Listing Agent Josh Hunt Snyder Donegan Real Estate Group

    38 Cardinal Dr, Hartford, VT 05001
    • 976 Hard Rd Unit 2, Hartford, VT 05001
      976 Hard Rd Unit 2, Hartford, VT 05001
      976 Hard Rd Unit 2, Hartford, VT 05001
      /19

      Not Listed For Sale

      976 Hard Rd Unit 2, Hartford, VT 05001

      • 2 Beds
      • 3.5 Baths
      • 1,426 Sq Ft
      • Built 1972
      976 Hard Rd Unit 2, Hartford, VT 05001

      Last Sold Summary

      • 11 Days On Market

  • 37 Robinson Ave, Rochester, VT 05767
    37 Robinson Ave, Rochester, VT 05767
    37 Robinson Ave, Rochester, VT 05767
    /56

    $519,000

    $30K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,704 Sq Ft

    37 Robinson Ave, Rochester, VT 05767

    This beautifully updated property in charming Rochester, VT offers exceptional flexibility for investors or owner-occupants. Five bedrooms in total this home has space for everyone. All units have been nicely updated throughout and are well-suited for short or long-term rental, with a strong STR income history already in place. Major system upgrades include a new standing seam roof, new furnace,

    Nathan Mastroeni

    37 Robinson Ave, Rochester, VT 05767
  • 51 River St, Woodstock, VT 05091
    51 River St, Woodstock, VT 05091
    51 River St, Woodstock, VT 05091
    /38

    $870,000

    Sold Jun 25, 2026

    51 River St, Woodstock, VT 05091

    • 4 Beds
    • 1.5 Baths
    • 1,580 Sq Ft
    • Built 1853

    Last Sold Summary

    • 3% Below List Price
    • $551/SF
    • 10 Days On Market

    Current Estimated Value $820,207

    Last Listing Agent Gretchjen Smith Williamson Group Sothebys Intl. Realty

    51 River St, Woodstock, VT 05091
    • 32 Route 103 S Unit F3, Ludlow, VT 05149
      32 Route 103 S Unit F3, Ludlow, VT 05149
      32 Route 103 S Unit F3, Ludlow, VT 05149
      /48

      Est $385,109

      Not Listed For Sale

      32 Route 103 S Unit F3, Ludlow, VT 05149

      • 3 Beds
      • 2 Baths
      • 1,125 Sq Ft
      • Built 1984
      32 Route 103 S Unit F3, Ludlow, VT 05149

      Last Sold Summary

      • 14 Days On Market

Showing Results 241 - 280, Page 7 of 18

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