304

Windsor County VT Homes for Sale with Acreage

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  • /17

    $325,000

    • Land
    • 51.59 Acres
    • $6,300 per Acre

    334 Log Cabin Dr, Pomfret, VT 05067

    334 Log Cabin Drive offers 51.59 acres of hardwood forest in South Pomfret, Vermont, with east and south-facing aspects through an open canopy. The stand lets light in all winter and turns into a cathedral in October. Mature birch, beech, and maple rise from a clean understory with good spacing, and scattered spruce and hemlock anchor the margins. Leaf-off views sweep across the ridgeline with no

    Richard Higgerson Higgerson & Company

    334 Log Cabin Dr, Pomfret, VT 05067
  • /17

    $485,000

    • Land
    • 26.99 Acres
    • $17,970 per Acre

    00 Valley View Dr, Andover, VT 05143

    A premier location abutting the Ludlow border, close to Okemo with total privacy, long range panoramic views of distant mountains and valleys at an elevation of about 2000 feet. Peace and beauty abound yet easy access to all area amenities including skiing, golf, biking, hiking and all that Southern Vermont has to offer. A State wastewater permit is in place for a 6 bedroom home and a 2 bedroom

    Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

    00 Valley View Dr, Andover, VT 05143
  • /9

    $169,000

    $6K PRICE DROP
    • Land
    • 5.01 Acres
    • $33,733 per Acre

    476 Missing Link Rd, Springfield, VT 05156

    5 acres of magical Ct River frontage. This site boasts 2 wide open fields. The septic design for a 5 bdrm septic is in the first field. The seller has obtained permission from the state for a driveway curb cut (Missing Link Rd, is State Rte 5) The land sits 80 ft above the river, so flooding is not an issue but you'll have the most peaceful, private views of the water. There are 2 steep walking

    Victoria Woods Brattleboro Area Realty

    476 Missing Link Rd, Springfield, VT 05156
  • /36

    $235,000

    $15K 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
  • /56

    $455,000

    • 5 Beds
    • 1.5 Baths
    • 2,205 Sq Ft

    191 Route 100 N, Ludlow, VT 05149

    Nestled between Okemo Mountain and the lakes region, this inviting 5-bedroom home sits on 2 peaceful acres framed by mature trees and an expansive open yard. Filled with warmth and character, the home is a charming reminder of simpler times, offering large sun-filled rooms and generous gathering spaces throughout. At the heart of the home is the open kitchen and family room, where a cozy wood

    Suzanne Garvey Mary W. Davis Realtor & Assoc., Inc.

    191 Route 100 N, Ludlow, VT 05149
  • /57

    $795,000

    $55K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 2,500 Sq Ft

    1312 MacIntosh Hill Rd, Randolph, VT 05060

    Now offered at $795,000 – A Vermont farmhouse with a historic orchard, mountain views, and income potential. Set amid rolling hills and breathtaking mountain vistas, this classic Vermont farmhouse sits on one of the first Macintosh apple orchards in the country. Rich with history and surrounded by natural beauty, the property offers a rare blend of character, comfort, and opportunity. A

    Jason Saphire www.HomeZu.com

    1312 MacIntosh Hill Rd, Randolph, VT 05060
  • /17

    $25,000

    $25K PRICE DROP
    • Land
    • 2.07 Acres
    • $12,077 per Acre

    0 E Ash Rd, Plymouth, VT 05056

    Welcome to Hawk East lot 2-20. This 2.07 acres lot is one of the closest lots to the Hawk Mountain Resort. There is a nice level area in the middle of the property that would make a nice building site. Easy access to Route 100 and only minutes to Okemo or Killington. There are 4 lakes all within a few minutes as well. Plenty of hiking, biking, boating, and fishing in the area. All plans and

    Kevin Barnes William Raveis Real Estate Vermont Properties

    0 E Ash Rd, Plymouth, VT 05056
  • /60

    $1,275,000

    $150K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 4,204 Sq Ft

    411 Wood Rd, Hartford, VT 05001

    Open House 10-2 Saturday 6/13 - Commanding a spectacular position atop 35 pristine acres, this extraordinary contemporary estate offers sweeping, long-range panoramas of the Quechee Valley, the Woodstock hills, and the Quechee Ski Hill. Designed as a true sanctuary, the home spans over 4,000 square feet of impeccably curated living space, where architectural elegance and natural beauty exist in

    Brooks Reavill

    411 Wood Rd, Hartford, VT 05001
  • /8

    $399,000

    • Land
    • 22.1 Acres
    • $18,054 per Acre

    1985 Gee Hill Rd, Royalton, VT 05068

    This breathtaking parcel is ready for you to hit the ground running—literally. The driveway is in, the house site is cleared, and the sweeping mountain views are already on full display from ground level. Designed with a walk-out basement in mind, the layout is perfect for maximizing both light and landscape. Fully permitted for a 5-bedroom septic system, with a second 5-bedroom design underway

    Holly Hall Hall Collins Real Estate Group

    1985 Gee Hill Rd, Royalton, VT 05068
  • /11

    $39,999

    • Land
    • 1 Acre
    • $39,999 per Acre

    341 Seavers Brook Rd, Springfield, VT 05156

    Easy building lot in a nice neighborhood in Springfield. Near the road roughly half of the property is flat with some clearing. This was actually a former home site, however the building was lost in a fire. Beyond the flat area (about 90 feet in) the topography rises up steeply and it would be difficult to build beyond this point. There is an old septic system on the property however it would

    David White OwnerEntry.com

    341 Seavers Brook Rd, Springfield, VT 05156
  • /31

    $349,000

    $100K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,788 Sq Ft

    1397 Popple Dungeon Rd, Chester, VT 05143

    Set on 3.30 acres in the hills of Chester, Vermont, this 1900-built home delivers the kind of setting people move here for—flowing water, open land, quiet roads, and easy access to the mountains. The property overlooks a gently moving brook and includes ownership on both sides of the water, giving you your own private stretch of stream and a natural buffer of woods and open space. A quiet paved

    Daire Gibney Barrett and Valley Associates Inc.

    1397 Popple Dungeon Rd, Chester, VT 05143
  • /13

    $189,000

    • Land
    • 1.7 Acres
    • $111,176 per Acre

    0 Meadow Ln, Hartford, VT 05001

    This 1.7-acre parcel on Meadow Lane offers a great opportunity to build in a quiet Hartford setting while still being close to everything the Upper Valley has to offer. The lot is tucked away at the end of the road, providing a bit more privacy while still being just a short drive to shopping, dining, and everyday conveniences in White River Junction and the surrounding area. Whether you're

    Randy Snelling KW Coastal and Lakes & Mountains Realty/Hanover

    0 Meadow Ln, Hartford, VT 05001
  • /57

    $649,000

    $50K PRICE DROP
    • 2.5 Baths
    • 7,445 Sq Ft

    66 Duttonsville School Dr, Cavendish, VT 05142

    Where History Meets Possibility — An 1862 Schoolhouse Reimagined. Step back in time and into opportunity. Built in 1862, this remarkable historic schoolhouse has been lovingly preserved, its character and craftsmanship thoughtfully maintained while seamlessly supporting modern use.Since 1973, the building has served as the home of a thriving distribution business—proof of its adaptability,

    Gail Beardmore Engel & Völkers Okemo

    66 Duttonsville School Dr, Cavendish, VT 05142
  • /50

    $550,000

    • 2 Beds
    • 2 Baths
    • 1,740 Sq Ft

    1043 Town Farm Rd, Ludlow, VT 05149

    South Hill Charmer! This inviting 2+ bedroom, 2-bath home checks all the boxes for the perfect vacation retreat, rental investment, or a combination of both. Warm and welcoming throughout, the home features beautiful wood floors, a cozy wood-burning fireplace, two separate living areas, and a newly expanded deck complete with a 6-person hot tub. The lower level is ideal for entertaining or

    Kevin Barnes William Raveis Real Estate Vermont Properties

    1043 Town Farm Rd, Ludlow, VT 05149
  • /19

    $219,000

    $10K PRICE DROP
    • Land
    • 68.5 Acres
    • $3,197 per Acre

    0 Spencer Hollow Rd Unit 5048342, Springfield, VT 05156

    Behold this rare opportunity to own 68 acres of pristine Vermont land located on a quiet, town-maintained dirt road in the peaceful hills of Springfield. This expansive parcel is a dream for outdoor enthusiasts—offering direct access to nature with miles of established trails, a diverse and healthy forest, and abundant wildlife. Bordering the beloved Muckross State Park—over 200 acres of

    Daire Gibney Barrett and Valley Associates Inc.

    0 Spencer Hollow Rd Unit 5048342, Springfield, VT 05156
  • /60

    $499,000

    $51K PRICE DROP
    • 960 Sq Ft

    544 Vulture Mountain Rd, Stockbridge, VT 05772

    A One-of-a-Kind VT Mountain Retreat with Strong Rental Income! Discover a truly unique family compound perched atop a private mountain, offering breathtaking views of conserved wilderness, including majestic Killington Peak & the beautiful White River below. Set on 1.2 acres, this remarkable property seamlessly blends vintage character w/thoughtful modern updates, creating the perfect retreat for

    Marni Rieger KW Vermont-Killington

    544 Vulture Mountain Rd, Stockbridge, VT 05772
  • /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
  • /30

    $650,000

    • 4,324 Sq Ft

    3630 Vt Route 103 N, Chester, VT 05143

    Exceptional Investment Opportunity in Chester, VT Discover this stunning, completely renovated property that beautifully combines modern amenities with unique character. Featuring two residential units. This home showcases high-quality upgrades throughout. Enjoy peace of mind with new electrical, plumbing, insulation, and energy-efficient windows. The kitchens and bathrooms have been meticulously

    Gary Coger Four Seasons Sotheby's Int'l Realty

    3630 Vt Route 103 N, Chester, VT 05143
  • /13

    $172,900

    • 3 Beds
    • 2 Baths
    • 1,359 Sq Ft

    136 Store Hill Rd, Bethel, VT 05032

    Property being sold "AS IS".State septic permitting is in progress. Located in quaint E. Bethel Village, this 1825 farmhouse offers an opportunity to finish to your taste.

    Dean Goulet Dunrovin Real Estate

    136 Store Hill Rd, Bethel, VT 05032
  • /31

    $153,000

    • Land
    • 4.7 Acres
    • $32,553 per Acre

    250 Fenton Rd, Chester, VT 05143

    Welcome to a place where the sound of the river becomes part of your daily rhythm. This 4.7-acre parcel with an end-of-road location offers an extraordinary 1,400 feet of frontage on the Williams River, creating a private and tranquil retreat just five minutes from the quintessential Vermont charm of Chester Village. The land unfolds beautifully: wide, flat, sun-filled fields stretch toward the

    Rachel Febbie EXP Realty

    250 Fenton Rd, Chester, VT 05143
  • /57

    $775,000

    $124K PRICE DROP
    • 2 Beds
    • 3 Baths
    • 2,250 Sq Ft

    60 Spencer Hollow Rd, Springfield, VT 05156

    Experience timeless elegance and rural charm at this meticulously crafted country estate, featuring a historical reproduction Shaker-style home designed by renowned architect McKee Wing Roth and built in 1991. Set on 15 deeded acres of rolling pastures, this unique estate blends traditional design with modern sustainability. Conveniently located 6.5 miles from the renowned Crown Point Country

    Kristen Breeden Southern Vermont Realty Group

    60 Spencer Hollow Rd, Springfield, VT 05156
  • /60

    $2,750,000

    $649K PRICE DROP
    • 7 Beds
    • 10 Baths
    • 13,410 Sq Ft

    51 E Ash Rd, Plymouth, VT 05056

    Welcome to Eureka House. This 7 bedroom Robert Carl Williams designed home is the ultimate in Vermont luxury and privacy. Enjoy unparalleled amenities like a 14-seat theater with stage, drive-through portico entrance, 2 story living room with gallery, 2 laundries, bedrooms are all en suite, and a 2 1/2-story carriage house with 3-car garage as well as living space above. The property is framed

    Kevin Barnes William Raveis Real Estate Vermont Properties

    51 E Ash Rd, Plymouth, VT 05056
  • /25

    $315,000

    $24K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 2,640 Sq Ft

    177 Vermont 14, Sharon, VT 05065

    Nestled along scenic Route 14 in Sharon, VT, this ranch-style home is being offered for the very first time since it was built in 1964. This inviting two-bedroom home offers comfortable living with plenty of space to gather and entertain. The walkout basement features a spacious family room, convenient kitchenette, and dedicated office space, ideal for working from home, creative projects, or

    Hartley White & Co Coldwell Banker LIFESTYLES - Hanover

    177 Vermont 14, Sharon, VT 05065
  • /37

    $399,000

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,148 Sq Ft

    40 Fenton Rd, Chester, VT 05143

    This property is a handy man's dream for someone who has a vision of finishing a house and turning it into their own sanctuary. The bones of the house are in place, furnace and piping for heat are in, rough plumping and wiring are done, and most sheet rock is completed. Gas fireplace is mounted and vented to outside and kitchen cabinets are on site. It boasts a little over 2000 square feet of

    John Napier TPW Real Estate

    40 Fenton Rd, Chester, 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
  • /16

    $135,000

    • Land
    • 1.19 Acres
    • $113,445 per Acre

    5417 Fletcher Ln, Hartford, VT 05059

    Located in the highly desirable Upper Willard Road neighborhood of Quechee Lakes, this 1.19-acre parcel offers an excellent opportunity to build your Vermont retreat in one of the region’s premier four-season communities. The gently sloping terrain provides flexibility for a homesite, either closer to Fletcher Lane or further back at a higher elevation toward the west end of the property. Recent

    Richard Higgerson Higgerson & Company

    5417 Fletcher Ln, Hartford, VT 05059
  • /20

    $369,000

    • 2 Beds
    • 1 Bath
    • 1,140 Sq Ft

    3578 Royalton Turnpike Rd, Barnard, VT 05031

    All the advantages of single level living! Privately located, in a rural area of desirable Barnard Vermont, is a home of a manageable size, with a comfortable interior floor plan. An appealing amenity is an attached oversize 2 car garage, with direct entry into the home. In Vermont winters the ability to exit and enter a home under cover from the weather is so practical. When entering the home

    John Wetmore Wetmore Real Estate

    3578 Royalton Turnpike Rd, Barnard, VT 05031
  • /47

    $650,000

    • 3 Beds
    • 3 Baths
    • 2,134 Sq Ft

    309 Kinney Farm Rd, Sharon, VT 05065

    Privacy with a mountain view, simply lovely. This spacious 4 bed 3 bath home offers an attached studio apartment/ADU above the garage complete with a kitchen and one of the bathrooms if you are looking for extra space! The two car garage is ultra deep offering room for a workshop. With a wall of windows for a view and a chimney hookup this garage space could easily be heated with the addition of

    Holly Hall Hall Collins Real Estate Group

    309 Kinney Farm Rd, Sharon, VT 05065
  • /53

    $675,000

    Open Sat 11AM - 1PM
    • 3 Beds
    • 2.5 Baths
    • 2,352 Sq Ft

    46 Davenport Ln, Hartford, VT 05047

    Welcome to this immaculate and lovingly maintained Quechee Lakes home, where comfort, privacy, and beautiful southern views come together in a truly special setting.Gorgeously landscaped with easy-care perennials, the outdoor spaces are designed to be enjoyed throughout the seasons. A generous stone patio and attractive stone wall provide the perfect backdrop for morning coffee, relaxing

    Mary Paino Coldwell Banker LIFESTYLES - Quechee

    46 Davenport Ln, Hartford, VT 05047
  • /46

    $589,000

    • 4 Beds
    • 2 Baths
    • 2,528 Sq Ft

    164 Pine View Ln, Cavendish, VT 05142

    This beautiful, spacious country home is just four miles from Okemo Mountain. Privately sited on more than an acre, it’s perfect for primary or vacation living. Sleeps 12+, close to town but a world away. The open meadow is a safe place for dogs and everyone to play. Enjoy the 8ft deep x 40ft farmers porch, deck, patio and fire ring. The private setting includes only two other homes and two other

    Jason Saphire www.HomeZu.com

    164 Pine View Ln, Cavendish, VT 05142
  • /16

    $299,000

    • Land
    • 4.3 Acres
    • $69,535 per Acre

    00 Chateauguay Rd, Barnard, VT 05031

    A rare and beautiful parcel of land that is cleared, level and ready to be built upon with over 1200 feet of frontage along the North Branch of Locust Creek.Locust Creek runs year round with water falls and deep pools, not only pleasant to look at, but fun to play in.Site prep costs for a parcel like this will be considerably lower than wooded lots that require clearing and excavation.

    Stan Butler Four Seasons Sotheby's Int'l Realty

    00 Chateauguay Rd, Barnard, VT 05031
  • /60

    $1,200,000

    • 4 Beds
    • 4.5 Baths
    • 4,352 Sq Ft

    884 Bridgewater Center Rd, Bridgewater Corners, VT 05035

    Tucked on 13.68 private acres near the north branch of the Ottauquechee River, this one-owner Bridgewater estate was built from the ground up with uncommon care — and it shows in every detail. With 4,300 square feet of living space (6,700 total), the home is heated by radiant flooring throughout and served by a new furnace/boiler, a private septic system, and a private well known for its

    Tucker Adirondack Lange Lange & Lange

    884 Bridgewater Center Rd, Bridgewater Corners, VT 05035
  • /59

    $14,900,000

    $3M PRICE DROP
    • 7 Beds
    • 10 Baths
    • 12,520 Sq Ft

    355 Greene Rd, Woodstock, VT 05071

    Star Hill Farm is completely private, hidden on a hillside with pastoral and mountain views in the heart of South Woodstock. From the valley floor to the top of Meetinghouse Hill, you will be inspired by its beauty, a mesmerizing 183.7+/- acre oasis over gorgeous terrain with fields, woodlands, trails, and stone walls. The historic 2-bedroom guest house and party barn are fully restored, and

    Chris Lang

    355 Greene Rd, Woodstock, VT 05071
  • /53

    $1,490,000

    $200K PRICE DROP
    • 5 Beds
    • 5 Baths
    • 5,400 Sq Ft

    1302 Popple Dungeon Rd, Chester, VT 05143

    Set on 18 private acres, Popple Dungeon is a distinctive Vermont property offering the feel of a true country retreat. Owned by one family and designed and built by its owner, the Williamsburg-style reproduction Saltbox reflects a deep appreciation for traditional craftsmanship and enduring design.Inside, the home is defined by warm, handcrafted details—wide-plank wood floors, paneled walls,

    Gary Coger Four Seasons Sotheby's Int'l Realty

    1302 Popple Dungeon Rd, Chester, VT 05143
  • /46

    $850,000

    $75K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,970 Sq Ft

    1877 Willard Rd, Hartford, VT 05047

    Stunning Deck House perfectly designed for light, views, and easy Vermont living. Soaring floor-to-ceiling glass in the entryway and stairwell connects all levels and creates a warm, treehouse-like feel, drenched in natural light. Honey-colored hardwood floors warm the main level, while wall-to-wall carpet and tile finish the rest of the spaces. The main level also features a striking stone

    Derek Cosentino Four Seasons Sotheby's Int'l Realty

    1877 Willard Rd, Hartford, VT 05047
  • /51

    $495,000

    Open House 6/27 Coming Soon
    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft

    3078 Vt Route 10, Chester, VT 05143

    This well-maintained property in Chester is in close proximity to many of Vermont's best ski mountains. It is not likely that you would drive by this property without it catching your eye. From the meticulous grounds with beautiful trees to the Vermont native stone wall lining the road, to the established perennial beds to the paved driveway leading back to this pleasing home with an attached

    Tyleen Murray Kelley Real Estate, Inc.

    3078 Vt Route 10, Chester, VT 05143
  • /44

    $675,000

    • 4 Beds
    • 2.5 Baths
    • 2,600 Sq Ft

    518 Baltimore Rd, Chester, VT 05143

    Nestled on 10 picturesque rolling acres, just minutes from Chester Village Green and Okemo Mountain Resort, this beautiful country home offers the perfect blend of charm, comfort, and convenience. The property features established gardens, apple trees, blueberry bushes, and a stone patio—ideal for relaxing or entertaining.Inside, you’ll find two levels of well-designed living space. The

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

    518 Baltimore Rd, Chester, VT 05143
  • /29

    $360,000

    New Construction $55K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,100 Sq Ft

    696 Vermont Route 100, Ludlow, VT 05149

    LUDLOW: Lake Pauline Waterfront with Existing Footprint and Permit in Place.Opportunity to own a unique lakefront property on Lake Pauline with approximately 600 feet of shoreline and over an acre of land just minutes from Okemo Mountain Resort.The existing home is positioned close to the water within an established footprint that could not be replicated under current regulations. This

    Melissa Loughan Westside Real Estate

    696 Vermont Route 100, Ludlow, VT 05149
  • /14

    $215,000

    • Land
    • 22.29 Acres
    • $9,646 per Acre

    0 Jericho St Unit 5062382, Hartford, VT 05001

    Discover 22.29+/- acres on Jericho Street in Hartford, VT. This wooded parcel offers a peaceful mix of mature trees and natural beauty—perfect for building your dream home, creating your own private trail system, or simply enjoying the quiet serenity of the outdoors. Includes a recent topographic and boundary survey, providing valuable insight and a strong starting point for your future plans.

    Heather Ashline BHHS Verani Upper Valley

    0 Jericho St Unit 5062382, Hartford, VT 05001
  • /40

    $1,400,000

    • Land
    • 250.7 Acres
    • $5,584 per Acre

    00 Route 100n, Plymouth, VT 05056

    Imagine owning 250 acres of unspoiled land in Vermont's coveted Lake Region, featuring five separate access points to the crystal-clear waters of Echo Lake. Whether you're envisioning a private family retreat, a recreational paradise, a conservation property, or a future development opportunity, this remarkable offering offers endless possibilities. Miles of established trails wind through the

    Kevin Barnes William Raveis Real Estate Vermont Properties

    00 Route 100n, Plymouth, VT 05056

Showing Results 201 - 240, Page 6 of 8

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