423

Windham County VT Homes for Sale

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  • /38

    $1,075,000

    • 5 Beds
    • 2.5 Baths
    • 2,338 Sq Ft

    3715 Route 11, Londonderry, VT 05148

    Beautifully expanded and fully renovated 18th-century farmhouse, thoughtfully reimagined by Gray Interiors of Darien, CT. This home blends timeless charm with an elegant yet relaxed New England feel. All systems and mechanicals have been completely updated and modernized. Stylish barnboard accents complement marble countertops, custom cabinetry, high-end finishes like the Shaws sink, and upscale

    Cheyanne Pugliese

    3715 Route 11, Londonderry, VT 05148
  • /3

    $275,000

    • 4 Beds
    • 2 Baths
    • 2,000 Sq Ft

    2173 Vermont 8a, Whitingham, VT 05361

    4 bedroom 2 bath home located on 4.7 acres. Has a ground level access. Level parking and garden spots. There are huge White Pine trees surrounding this home. Showings delayed until September 29, 2025 to allow for cleaning. License to Sell is needed and in progress, Expected in October.

    Mark Yule BHG Masiello Brattleboro

    2173 Vermont 8a, Whitingham, VT 05361
  • /40

    $425,000

    • 2 Beds
    • 2 Baths
    • 1,386 Sq Ft

    152 Our Rd, Putney, VT 05346

    Delayed Showings - OPEN HOUSE Sat 9/20 from 10am to noon. Log Home Retreat on 4.7 Acres in Westminster, VT. Tucked back on a quiet road, is this welcoming 2-bedroom, 2-bath log home set on 4.7 private acres. A circular driveway brings you to the home, where a broad front porch invites you to slow down and take in the surroundings.Inside, you’ll find new flooring throughout

    Morriah Adams BHG Masiello Brattleboro

    152 Our Rd, Putney, VT 05346
  • /35

    $34,900

    • 1 Bed
    • 2 Baths
    • 745 Sq Ft

    341/43 Qtr.4,89 Grand Summit Way, Dover, VT 05356

    Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? This sleep 6 unit consists of two adjoining units; Studio unit (341) Queen murphy bed, kitchenette, full bathroom . Hotel unit (343) Two king beds, full bathroom. Units are located on the third floor mountain side of the hotel. Lock out units have the benefit of using the unit as a whole or stay in one side and rent the other

    Kelly Agrillo Southern Vermont Realty Group

    341/43 Qtr.4,89 Grand Summit Way, Dover, VT 05356
  • /6

    $49,000

    • Land
    • 10.2 Acres
    • $4,804 per Acre

    0 Kurn Hattin Rd, Putney, VT 05346

    Discover the potential of this 10.2 acre lot nestled in the scenic hills of Westminster. With road frontage on a paved, town maintained road and easy access to I-91, this property offers both privacy and convenience. Located in an accessible area with a peaceful, wooded setting, it’s an ideal opportunity to own a piece of Vermont’s natural beauty.

    Rebecca Hiam Southern Vermont Realty Group

    0 Kurn Hattin Rd, Putney, VT 05346
  • /79

    $275,000

    • Land
    • 22.32 Acres
    • $12,321 per Acre

    81 Parish Hill Rd Unit 26, Newfane, VT 05345

    Tucked away in the quiet hills of South Newfane, Vermont, this property presents an excellent opportunity to own a secluded off-grid retreat with endless potential. Spanning 22.32 acres of mixed timberland, the land offers both natural beauty and outdoor recreation, while the cabin provides a comfortable base that is already well on its way to completion.The cabin itself measures 715 square feet

    Chad Bruyette Whitetail Properties Real Estate

    81 Parish Hill Rd Unit 26, Newfane, VT 05345
  • /42

    $1,150,000

    • 3 Beds
    • 3 Baths
    • 2,121 Sq Ft

    4 Hardwood Hill, Stratton, VT 05360

    Welcome to your mountain retreat in the exclusive TreeTop community at Stratton Resort. This upscale 3 level, 3 BR, 3 BA + bonus loft room townhome offers the perfect blend of alpine charm & modern comfort. Perched on the mountain with panoramic vistas, enjoy year-round views from your private stone patio & spacious deck. Step outside & take advantage of ski-back access right to your door, plus a

    Kim Morgan-Wohler Wohler Realty Group

    4 Hardwood Hill, Stratton, VT 05360
  • /39

    $849,000 New Construction

    • 2 Beds
    • 2.5 Baths
    • 2,020 Sq Ft

    101 North Rd, Wilmington, VT 05363

    Stunning new construction in the Chimney Hill community just outside the village of Wilmington, and a short drive to both the Mount Snow ski resort, Hermitage Club, and Lake Whitingham. Located on an easily accessible corner lot in the desirable B section at the bottom of the hill with unique double lot size allowing for tremendous expansion potential . This home was built sparing no expense and

    Adam Palmiter Berkley & Veller Greenwood/Dover

    101 North Rd, Wilmington, VT 05363
  • /31

    $33,500

    • 1 Bed
    • 2 Baths
    • 709 Sq Ft

    145/47 Qtr.1,89 Grand Summit Way, Dover, VT 05356

    Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? This sleep 6 unit consists of two adjoining units; Studio unit (145) Queen murphy bed, kitchenette, full bathroom and a balcony. Hotel unit (147) Two queen beds, full bathroom and balcony. Units are located the mountain side of the hotel just down the hallway from the Spa, ski locker, health club and pool.. Lock out units

    Kelly Agrillo Southern Vermont Realty Group

    145/47 Qtr.1,89 Grand Summit Way, Dover, VT 05356
  • /43

    $445,000

    • 3 Beds
    • 2.5 Baths
    • 2,872 Sq Ft

    1587 Upper Holbrook Rd, Whitingham, VT 05361

    Set on 3 beautiful acres, this well-maintained 3-bedroom plus loft, 2 1/2 bath home is truly move-in ready. Enter through a spacious mudroom with a convenient back opening for bringing in firewood for the cozy wood stove in the living room. The open-concept kitchen and dining area provide plenty of room for entertaining, while a den/game room just off the living room with a bar area (4X8) offers

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    1587 Upper Holbrook Rd, Whitingham, VT 05361
  • /30

    $295,000

    • 3 Beds
    • 2 Baths
    • 1,328 Sq Ft

    876 Vermont Route 100, Wilmington, VT 05363

    Great location for full-time local residents or seasonal visitors. Easy access from Route 100. Nice yard and solid house. This is a comfortable 3-bedroom house with a living room, kitchen, and dining room! Centrally located and easily accessible. Please come see it!

    Tony Tribuno Skihome Realty

    876 Vermont Route 100, Wilmington, VT 05363
  • /32

    $560,000

    • 2 Beds
    • 2 Baths
    • 1,775 Sq Ft

    162 Buttonwood Dr, Brattleboro, VT 05301

    BLACK MOUNTAIN ESTATES - where your next chapter begins. Welcome to Brattleboro’s premier 55+ active lifestyle community, where nature, connection, & comfort converge. For the first time, a limited number of homes are available for purchase as we transition to a Planned Community. Surrounded by majestic pines, a private nature trail, & open green space, residents enjoy a serene setting just 1

    Dan Normandeau Berkley & Veller Greenwood Country

    162 Buttonwood Dr, Brattleboro, VT 05301
  • /34

    $585,000

    • 2 Beds
    • 2 Baths
    • 1,775 Sq Ft

    24 Dogwood Dr, Brattleboro, VT 05301

    BLACK MOUNTAIN ESTATES - where your next chapter begins. Welcome to Brattleboro’s premier 55+ active lifestyle community, where nature, connection, & comfort converge. For the first time, a limited number of homes are available for purchase as we transition to a Planned Community. Surrounded by majestic pines, a private nature trail, & open green space, residents enjoy a serene setting just 1

    Dan Normandeau Berkley & Veller Greenwood Country

    24 Dogwood Dr, Brattleboro, VT 05301
  • /32

    $675,000

    • 3 Beds
    • 3 Baths
    • 2,216 Sq Ft

    12 Three Streams Way, Wilmington, VT 05363

    Beautiful 2006 chalet in the Chimney Hill community just a short drive from the Mount Snow Ski Resort and village Wilmington. This meticulous turn key home has been completely renovated and upgraded, and sits on a on a private lot in the Chimney Hill community on a quiet side road with access to snowmobile trails and winter views. Inside is a gorgeous great room space with vaulted ceilings and

    Adam Palmiter Berkley & Veller Greenwood/Dover

    12 Three Streams Way, Wilmington, VT 05363
  • /28

    $449,000

    • 3 Beds
    • 2 Baths
    • 1,510 Sq Ft

    49 West Rd, Wilmington, VT 05363

    Lovely renovated chalet at the bottom of the Chimney Hill community with easy access to trails, hiking, lakes, and nearby Mount Snow. This lovely private parcel sits in the easily accessible lower section with nice seclusion and views out the rear, affording nice privacy yet with all the conveniences of community living. The interior boasts an open concept living space with natural light and

    Adam Palmiter Berkley & Veller Greenwood/Dover

    49 West Rd, Wilmington, VT 05363
  • /36

    $549,000

    • 3 Beds
    • 2.5 Baths
    • 2,044 Sq Ft

    11 Dutchman Ln Unit 4A, Wilmington, VT 05363

    This 3-bedroom plus loft, 2.5-bath end unit townhouse is in Powderhorn Village. The entrance boasts a mudroom, leading to a dining area adjacent to a fully equipped kitchen, complemented by a convenient powder room and living space with a wood-burning fieldstone fireplace. Access to an oversized deck and a bonus room with a hot tub and a private shower. Ascend to the second floor to find the

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    11 Dutchman Ln Unit 4A, Wilmington, VT 05363
  • /32

    $585,000

    • 2 Beds
    • 2 Baths
    • 1,775 Sq Ft

    161 Buttonwood Dr, Brattleboro, VT 05301

    BLACK MOUNTAIN ESTATES - where your next chapter begins. Welcome to Brattleboro’s premier 55+ active lifestyle community, where nature, connection, & comfort converge. For the first time, a limited number of homes are available for purchase as we transition to a Planned Community. Surrounded by majestic pines, a private nature trail, & open green space, residents enjoy a serene setting just 1

    Dan Normandeau Berkley & Veller Greenwood Country

    161 Buttonwood Dr, Brattleboro, VT 05301
  • /11

    $795,000

    • 4 Beds
    • 3 Baths
    • 3,409 Sq Ft

    633-635 Vermont Route 100, Stratton, VT 05360

    Great family compound or use one and rent the other. There are 2 homes on this property with direct access to VAST and the National Forest and `1.6 miles to the North entrance of Mt. Snow. Great opportunity with an excellent rental history. Both houses have full walk-out daylight lower levels, 2 decks and a hot tub at each home. Both homes were remodeled in 2014 including new roofs, windows and

    Ginny Read Read Realty LTD

    633-635 Vermont Route 100, Stratton, VT 05360
  • /59

    $275,000

    • 2 Beds
    • 1 Bath
    • 715 Sq Ft

    81 Parish Hill Rd, Newfane, VT 05345

    Nestled in the hills of South Newfane, Vermont, this off-grid property offers the perfect balance of seclusion, recreation, and comfort. Set on 22.32± acres of mixed timberland, the land features a meandering creek, wildlife habitat, and excellent hunting opportunities for deer and turkey. A 715 sq. ft. cabin, approximately 80% complete, serves as the centerpiece of the property. Built with a

    Chad Bruyette Whitetail Properties Real Estate, LLC

    81 Parish Hill Rd, Newfane, VT 05345
  • /30

    $369,000

    • 3 Beds
    • 2 Baths
    • 1,703 Sq Ft

    1089 Marlboro Rd, Brattleboro, VT 05301

    The one you have been waiting for! This traditional New England cape with a twist checks all the boxes! Remodeled in the 90's, it has a cook's delight for a kitchen with tons of cabinets and lots of countertops for baking prep...cookies and breads are a must!. The first floor was expanded to almost double the size of the living room, adding a fireplace and a main bedroom. Aging in place is easy

    Christine Lewis Brattleboro Area Realty

    1089 Marlboro Rd, Brattleboro, VT 05301
  • /39

    $625,000

    • 5 Beds
    • 4 Baths
    • 3,748 Sq Ft

    58 Oak St, Brattleboro, VT 05301

    Come experience the elegance and charm of this stunning in-town retreat! Close to the town common and vibrant downtown Brattleboro—home to fine dining, galleries, quaint shops, and live music venues. Step inside the main house and be welcomed by a country kitchen featuring a large island, ideal for gatherings. The home exudes Victorian character with soaring ceilings, hardwood floors, and

    Rebecca Seymour Brattleboro Area Realty

    58 Oak St, Brattleboro, VT 05301
  • /60

    $579,000

    • 2 Beds
    • 2 Baths
    • 850 Sq Ft

    794 White Rd, Windham, VT 05359

    Enjoy the best of Vermont living in this thoughtfully renovated home on a paved country road in Windham. Renovated down to the studs, this property offers upgrades inside and out—new standing seam roof, new siding, new windows, full-house generator, new central air and heating systems, plus new electrical and plumbing systems upgraded to 200 amps. The home is insulated with rockwool and foam

    Erica Reynolds Southern Vermont Realty Group

    794 White Rd, Windham, VT 05359
  • /43

    $599,000

    • 3 Beds
    • 2.5 Baths
    • 2,720 Sq Ft

    58 Buckboard Dr, Dover, VT 05356

    58 Buckboard | Dover, VermontSet on 1.46 private acres with sweeping mountain views, this beautifully updated 3 bedroom, 3 bath home offers a perfect blend of modern style and Vermont warmth.Inside, the heart of the home is the newly renovated kitchen, featuring a center island with quartz countertops, stainless steel appliances, and open shelving. The kitchen flows seamlessly into the

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    58 Buckboard Dr, Dover, VT 05356
  • /44

    $1,200,000

    • 4 Beds
    • 3 Baths
    • 4,193 Sq Ft

    70 Hunter Ln, Jamaica, VT 05343

    Discover a truly special Vermont retreat at 70 Hunter Lane, nestled in the private Cole Pond community of Jamaica. This exceptional residence offers over 4,200 square feet of living space, thoughtfully designed to blend comfort, luxury, and the natural beauty of its surroundings. Newer Stainless Steel appliances in kitchen!Featuring four spacious bedrooms, this home provides plenty of

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    70 Hunter Ln, Jamaica, VT 05343
  • /45

    $449,000

    • 3 Beds
    • 3 Baths
    • 1,768 Sq Ft

    52A Suntec Loop, Dover, VT 05356

    Brand NEW building exterior, windows, doors! Introducing the new and improved Suntec units! Welcome to this beautifully maintained, bright & spacious three bedroom, three bath townhome, offering the perfect blend of space, comfort, and convenience just minutes from Mount Snow’s main base lodge, Carinthia Lodge, and the Hermitage Club. This home features three large bedrooms with high ceilings, a

    Prema Fitzpatrick Skihome Realty

    52A Suntec Loop, Dover, VT 05356
  • /26

    $649,000

    • 3 Beds
    • 3 Baths
    • 2,170 Sq Ft

    14 Johnson Hill Rd, Dover, VT 05356

    Unique contemporary chalet just a short drive from the Mount Snow Ski Resort and village Wilmington, and with direct snowmobile trail access. This very cool open concept home has been completely renovated and upgraded, and sits on a on a private lot in the Dover Hills with beautiful lawn space and cul de sac driveway. Walk in through the spacious mudroom with plenty of room for gear, and head up

    Adam Palmiter Berkley & Veller Greenwood/Dover

    14 Johnson Hill Rd, Dover, VT 05356
  • /56

    $475,000

    • 6 Beds
    • 3 Baths
    • 3,954 Sq Ft

    430 Huckle Hill Rd, Vernon, VT 05354

    NEW PRICE!! LOTS OF OPTIONS!! This quality built home can be enjoyed as spacious one floor living. Inside, the main level features gleaming hardwood floors with radiant floor heat and an open-concept layout with vaulted ceilings. The bright kitchen offers granite countertops, stainless steel appliances, a breakfast bar, and space for a kitchen table. The adjoining dining area easily accommodates

    Carol Slocum Keller Williams Realty Metro-Keene

    430 Huckle Hill Rd, Vernon, VT 05354
  • /29

    $465,000

    • 3 Beds
    • 2 Baths
    • 1,814 Sq Ft

    132 Pratt Bridge Rd, Jamaica, VT 05343

    Welcome to this charming Vermont getaway, custom - built and lovingly maintained by the original owners. Ideally located just minutes from Stratton Mountain and within easy reach of Bromley and Magic for a full season of winter adventure. In the warmer months, enjoy nearby lakes perfect for swimming, paddling, or simply relaxing by the water.Inside, the home offers 3 bedrooms and 2 full

    Lisa Sullivan Four Seasons Sotheby's Int'l Realty

    132 Pratt Bridge Rd, Jamaica, VT 05343
  • /49

    $695,000

    • 4 Beds
    • 2.5 Baths
    • 3,104 Sq Ft

    153 Westminster Rd, Putney, VT 05346

    Combining the charm of an 1820's fully restored historic home, with a 1,600 sq. ft. addition (built in 2016), this fabulous property, close to the Putney Village, offers the best of both worlds. Wide pine flooring and exposed beams in the restored front half blend beautifully with the newly built addition, featuring 9’ ceilings, hardwood floors and a handsome stone fireplace. The expansive

    Heidi Bernier Berkley & Veller Greenwood Country

    153 Westminster Rd, Putney, VT 05346
  • /18

    $220,000

    • 3 Beds
    • 1 Bath
    • 1,050 Sq Ft

    5362 Us Route 5, Westminster, VT 05158

    Welcome to this move-in ready home, ideally situated in the heart of picturesque Westminster. This 3-bedroom, 1-bath home offers the perfect blend of charm, comfort and convenience. Step inside from the sunny, porch into a bright and functional kitchen featuring new countertops and easy access to the first-floor laundry area and recently renovated full bath. The layout flows seamlessly into the

    Karen Hoppe Berkley & Veller Greenwood Country

    5362 Us Route 5, Westminster, VT 05158
  • /59

    $599,000

    • 3 Beds
    • 2.5 Baths
    • 2,782 Sq Ft

    628 Townshend Rd, Grafton, VT 05146

    One of only two stone houses in the charming town of Grafton, this stately home is a truly special opportunity. Perched on a hill across from the renowned Grafton Cheese Company, the property offers easy access to village amenities and year-round recreation at Grafton Ponds Outdoor Center. Inside, you'll find a spacious and inviting layout: Large front living room with exposed beams, a beautiful

    Jessica Landers Barrett and Valley Associates Inc.

    628 Townshend Rd, Grafton, VT 05146
  • /20

    $469,000

    • 4 Beds
    • 2 Baths
    • 2,219 Sq Ft

    45 Dover Hill Rd, East Dover, VT 05341

    Recently renovated 1900s Colonial just outside the town of Dover, near the Mount Snow ski resort and village of Wilmington, and near Lake Whitingham, with easy access off a paved town road. This cozy Vermont retreat sits on 3+ acres with established trails, a gurgling brook wrapping around the home, bridge to access the rear upper meadow, perennial landscaping, and more. The home is being offered

    Adam Palmiter Berkley & Veller Greenwood/Dover

    45 Dover Hill Rd, East Dover, VT 05341
  • /30

    $1,040,000

    • 5 Beds
    • 4.5 Baths
    • 3,363 Sq Ft

    1189 Cole Pond Rd, Jamaica, VT 05343

    Discover a rare opportunity at this five-bedroom, 5-bath waterfront home in the Cole Pond community. Situated just minutes from skiing and steps from the water, this property is a year-round paradise for outdoor enthusiasts.The main home features a spacious four-bedroom, 3.5-bath layout. Its open-concept living and dining area is bathed in natural light from large windows, creating a

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    1189 Cole Pond Rd, Jamaica, VT 05343
  • /17

    $2,495,000

    • Land
    • 2.36 Acres
    • $1,057,203 per Acre

    4 Gold Medal Cir, Stratton, VT 05343

    This lot is only one mile from the Stratton Mountain Resort's Sun Bowl base area. The lot has views of Stratton's ski trails. The Powers Subdivision has 11 lots in total and 2.71 acres of common land. Additionally, there is 69 acres of conservation land making this community very private. Build your 4-bedroom dream home right here in one of the best planned communities in southern Vermont.

    Andrew King Stratton Real Estate

    4 Gold Medal Cir, Stratton, VT 05343
  • /26

    $32,000

    • 1 Bed
    • 2 Baths
    • 791 Sq Ft

    249/251 Qtr 3 Grand Summit Way Unit 249/251 Qtr 3, Dover, VT 05356

    Trailside, best ski in/out mountain location. A really comfortable unit sleep 8. Unit 251 includes a kitchenette, comfortable living room setting, a sleep sofa a Murphy bed and full bath. Unit 249 boasts 2 queen size beds a full bathroom, and a deck with views of the mountain to enjoy skiers on the slope and fireworks. Just imagine entertaining family and friends! Benefits of ownership include

    Sheila Joyce-Albano Skihome Realty

    249/251 Qtr 3 Grand Summit Way Unit 249/251 Qtr 3, Dover, VT 05356
  • /48

    $32,000

    • 1 Bed
    • 2 Baths
    • 846 Sq Ft

    226/228, Qtr 2 Grand Summit Way Unit 226/228, Qtr 2, Dover, VT 05356

    Experience the ultimate in flexibility and mountain living with this deeded quartershare at the Grand Summit Hotel. Enjoy 13 weeks of vacation annually—one week every 28 days—on a rotating basis. Use it, rent it, or trade it for other destinations! This spacious valley-side lockout unit comfortably sleeps 8 and features 2 full baths, a kitchen/dining area, and stunning valley views. Unit 226 is a

    Donna Brown Skihome Realty

    226/228, Qtr 2 Grand Summit Way Unit 226/228, Qtr 2, Dover, VT 05356
  • /2

    $70,000

    • Land
    • 1.47 Acres
    • $47,619 per Acre

    0 Huckle Hill Rd Unit 5059719, Vernon, VT 05354

    Amazing Opportunity to Build Your Forever Home!This beautiful south-facing, open lot offers the perfect setting for your dream home, with convenient access to power right at the road. The back portion of the property is graced with mature trees, providing shade and a natural pathway to nearby VAST snowmobile and hiking trails.Enjoy the peace of a quiet country setting where you can

    Kerry Mulverhill

    0 Huckle Hill Rd Unit 5059719, Vernon, VT 05354
  • /54

    $335,000

    • 5 Beds
    • 2 Baths
    • 1,944 Sq Ft

    2015 Vermont 30, Townshend, VT 05353

    Perfectly situated on the scenic road to Stratton Mountain—just 25 minutes from the slopes—this charming turn-of-the-century mixed-use property offers endless potential. Step inside to discover original period woodwork, gleaming hardwood floors, and classic details that give this roomy home its timeless character.The property also boasts a large two-story post-and-beam barn, lovingly restored

    Craig Ruggless EXP Realty

    2015 Vermont 30, Townshend, VT 05353
  • /35

    $2,197,000

    • 5 Beds
    • 4.5 Baths
    • 5,110 Sq Ft

    14 Tarheel Trail, Wilmington, VT 05363

    This custom built 2018 log home, designed by RH Log Works and Hilderbrand Interiors, offers the ultimate in sophistication and luxury. Featured in Better Homes and Gardens, New England Home and Country Home magazines, this 5 bedroom, 4.5 bathroom sanctuary (plus extra bunk room) is nestled on 2.2 wooded acres with a river running alongside. Just 4 minutes from Hermitage Club and 10 minutes from

    Adam Palmiter Berkley & Veller Greenwood/Dover

    14 Tarheel Trail, Wilmington, VT 05363
  • /35

    $249,900

    • Land
    • 13 Acres
    • $19,223 per Acre

    2137 Brockway Mills Rd, Town of Rockingham, VT 05143

    What a great opportunity here for someone to start their own family farm! Consisting of two barns and 13 beautiful acres with a building site which overlooks the open land, the barns, and the mountain view beyond, including 1490 foot Mt Ephraim. Located just up the road from the Brockway Mills Gorge, a very scenic local landmark. The Williams River with swimming holes and even a space for

    Glenn Olney Barrett and Valley Associates Inc.

    2137 Brockway Mills Rd, Town of Rockingham, VT 05143

Showing Results 121 - 160, Page 4 of 11

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