506

Windham County VT Homes for Sale

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  • /24

    $140,000

    • Land
    • 1.4 Acres
    • $100,000 per Acre

    0 Scattered Timber Rd Unit 5094122, Wilmington, VT 05363

    Build your dream mountain retreat on this exceptional 1.4-acre double lot (Lots 494 & 495) in the highly desirable Chimney Hill community. Gently sloping and situated at approximately 2,400 feet in elevation, this unique parcel offers outstanding privacy with seasonal winter valley views while directly abutting Green Mountain National Forest and HOA common land, helping preserve the peaceful

    Grayson VanHendrick Flex Realty

    0 Scattered Timber Rd Unit 5094122, Wilmington, VT 05363
  • /25

    $375,000

    • 4 Beds
    • 2.5 Baths
    • 2,066 Sq Ft

    313 Dover Rd, Newfane, VT 05362

    Step back in time while enjoying the comforts of today in this classic 1800s post-and-beam Cape set on 2 peaceful acres in the Vermont countryside. Rich in character and timeless charm, this 4-bedroom, 3-bath home showcases the warmth and craftsmanship of a bygone era with exposed beams, inviting living spaces, and room for family and guests. Outside, you’ll find established perennial gardens,

    Claire Renaud Berkley & Veller Greenwood Country

    313 Dover Rd, Newfane, VT 05362
  • /59

    $1,100,000

    $100K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 4,193 Sq Ft

    70 Hunter Ln, Jamaica, VT 05343

    Discover a truly unique four season home. In the summer, kayak and swim on a private pond. In the fall, hike the many trails that are available and enjoy the foliage. When the Winter comes, it's a ten minute trip to Stratton Mountain and afterwards, ice skate on your own back yard pond. In the spring, step outside to a private hot tub inviting you to to soak while overlooking the sprawling

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    70 Hunter Ln, Jamaica, VT 05343
  • /36

    $375,000

    $14K PRICE DROP
    • 3,460 Sq Ft

    733 Vermont 121, Westminster, VT 05101

    This 5-unit multi-family property presents a strong investment opportunity with steady, long-term tenants and consistent on-time rental history. Meticulously cared for over the years, the property features updated systems, public water, a double lot, and ample parking for tenants and guests alike.Current rents are below today’s market rates, offering clear opportunity for future income

    Morriah Adams BHG Masiello Brattleboro

    733 Vermont 121, Westminster, VT 05101
  • /29

    $599,000

    • 5 Beds
    • 2 Baths
    • 2,350 Sq Ft

    9282 Vt Route 100, Whitingham, VT 05361

    This Vermont Country Farmhouse has been recently completed renovated and is ready for turn key enjoyment. The property consists of 41+ acres with tremendous exposure and easy main road access, extensive pasture which could easily be used for farming, a 42x48 post and beam barn, multiple out buildings ideal for workshops and storage, and a location with easy access to Harriman Reservoir and not

    Adam Palmiter Berkley & Veller Greenwood/Dover

    9282 Vt Route 100, Whitingham, VT 05361
  • /26

    $499,000

    $20K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,537 Sq Ft

    4B Newfane Cir, Dover, VT 05356

    Welcome to effortless mountain living in the sought-after Greenspring community of West Dover, where comfort, convenience, and four-season recreation come together just minutes from Mount Snow.This beautifully updated 2-bedroom, 2.5-bath townhome is designed for both relaxing getaways and easy everyday living. Each spacious bedroom features its own private ensuite bath, offering comfort

    Mike Masters Four Seasons Sotheby's Int'l Realty

    4B Newfane Cir, Dover, VT 05356
  • /23

    $470,000

    • 4 Beds
    • 2 Baths
    • 2,016 Sq Ft

    6D White Oaks Loop Unit 7, Dover, VT 05356

    Welcome to this spacious end unit Timber Creek condominium, ideally located directly across from Mount Snow. This highly desirable community offers the perfect blend of mountain convenience and resort-style amenities, making it an exceptional year-round getaway. The main level features a welcoming mudroom entry with built-in bench and cubbies, opening into the dining area that flows seamlessly

    Monique White Deerfield Valley Real Estate

    6D White Oaks Loop Unit 7, Dover, VT 05356
  • /37

    $900,000

    $50K PRICE DROP
    • Land
    • 20.7 Acres
    • $43,478 per Acre

    0 Crotty Dr, Town of Rockingham, VT 05101

    Investors, developers and builders take notice! This large, gently sloped parcel is one the last & largest undeveloped lots of land that fall within the Bellows Falls Village District. Just minutes from downtown and abutting Minard's Pond nature area, this property sits high on the hill with spectacular views available. With dozens of potential building locations and access to town water and

    Courtney Doubleday EXP Realty

    0 Crotty Dr, Town of Rockingham, VT 05101
  • /10

    $215,000

    • Land
    • 8.6 Acres
    • $25,000 per Acre

    00 Priest Dr, Putney, VT 05346

    Discover this 8.6-acre, mostly wooded parcel located on Priest Drive in Putney. Set along a paved, town-maintained dead-end road with limited through traffic, the property offers the opportunity to create a private getaway or future homesite set back among the trees. Located near River Road South and just minutes from Landmark College, the parcel is also convenient to Putney Village, Interstate

    Ayden Hardy BHG Masiello Keene

    00 Priest Dr, Putney, VT 05346
  • /50

    $389,000

    $46K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,344 Sq Ft

    27 Country Ct, Wilmington, VT 05363

    Amazingly private cul-de-sac, the nicest location in Chimney Hill! 4 Bedroom 2 Baths, Livingroom with wood stove and a wall of windows to let the outdoors in! Hot Tub on multi-tiered deck. Beautiful wooded lot to explore, garden shed and garage.Live the Resort lifestyle on Chimney Hill's 1,200-Acre Resort Campus, with 550-Acres owned in common by the Homeowners Association. Numerous multi-use

    Janet Boyd Boyd Real Estate

    27 Country Ct, Wilmington, VT 05363
  • /14

    $54,000

    $1K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 924 Sq Ft

    78 Shady Pines Park, Westminster, VT 05158

    Looking for an affordable home you can truly call your own? This could be the one! This 1989 mobile home is nestled on a large rented lot in the highly convenient Shady Pines Park in Westminster, VT. Just minutes from I-91, it offers easy access to Bellows Falls, Saxtons River, Walpole, and surrounding communities. The home features a spacious eat-in kitchen, three bedrooms, one and a half

    Derek Winchester ACORN REAL ESTATE GROUP LLC

    78 Shady Pines Park, Westminster, VT 05158
  • /44

    $18,000

    • 1 Bed
    • 2 Baths
    • 840 Sq Ft

    236, Qtr 2 89 Grand Summit Way, Dover, VT 05356

    Trailside! Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? Own this deeded quartershare property at Mount Snow Resort for 1 week every 28 days, on a rotating basis. This 1-of-a-kind, valley-view 1-bedroom, 2 full-bath unit has sleeping space for 4, an Open-Concept kitchen/dining room, and a living room with a queen sleeper sofa. There is a king-sized bed and a deck in the

    Donna Brown Skihome Realty

    236, Qtr 2 89 Grand Summit Way, Dover, VT 05356
  • /44

    $450,000

    $75K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,943 Sq Ft

    24 Antler Loop, West Dover, VT 05356

    This charming 3-bedroom, 2-bath dutch colonial home sits atop a knoll, overlooking a picturesque half-acre pond in the front yard. Nestled on 2.06 acres in a tranquil neighborhood, the property offers an excellent floor plan for family living. The home features spacious bedrooms, a cozy brick fireplace in the living room with a cathedral ceiling, and a dining area with pine floors and pond views.

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    24 Antler Loop, West Dover, VT 05356
  • /4

    $182,000

    • 3 Beds
    • 1.5 Baths
    • 1,114 Sq Ft

    23 Williams St, Brattleboro, VT 05301

    Cute as a button! Everyone knows this home painted as pretty as a picture, on the corner lot at the foot of Union Hill. The owners over the years have landscaped and created a magical setting........walk to downtown, coop and the MOOVER! Previous owners did a amazing renovation after Irene. An intown, affordable, vintage home with lots of character. 48 hour notice please in respect of the

    Christine Lewis Brattleboro Area Realty

    23 Williams St, Brattleboro, VT 05301
  • /22

    $85,000

    $1K PRICE DROP
    • Land
    • 6.2 Acres
    • $13,710 per Acre

    1297 River Rd, Jamaica, VT 05343

    Unique! Do you love to camp? swim? fish?.....this may be it for you....Over2000 feet of West River frontage with electric on site and just offpavement and at the intersection of 2 major access road to skiing andrecreation! Much of the frontage is in flood plain and it is subject to flowage rights of the dam, but an amazing site! The current owner has had a Jamaica cottage for camping

    Christine Lewis Brattleboro Area Realty

    1297 River Rd, Jamaica, VT 05343
  • /3

    $515,000

    Coming Soon
    • 3 Beds
    • 2 Baths
    • 1,643 Sq Ft

    868 Magic Cir, Londonderry, VT 05148

    The original home of Magic Mountain's founder, Hans Thorner. Lot is sited beautifully for a stunning mountain view! Wonderful open spaces, light and bright to bring in nature's magnificent settings...Living room features a wood burning fireplace with woodstove insert, also designed with plenty of gathering spaces along with a stunning and eco-friendly bamboo floor. Three bedrooms, two baths,

    Donna Murray Varick Associates Ltd

    868 Magic Cir, Londonderry, VT 05148
  • /3

    $249,000

    $150K PRICE DROP
    • Land
    • 36,590 Sq Ft
    • $296,429 per Acre

    8B Freestyle Cir, Dover, VT 05356

    Ski in and out at Mount Snow from one of the last two buildable lots on the mountain. If you understand the convenience of slopeside living this could be the location for you to build your dream home. This building site is part of the TrailsEdge PUD, sharing in their utilities and ski access to/from Mount Snow through the Snowdance Village ski trails. Note that this is the larger of 2 lots

    John Redd Skihome Realty

    8B Freestyle Cir, Dover, VT 05356
  • /31

    $219,000

    $40K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,136 Sq Ft

    279 North St, East Dover, VT 05341

    Rustic Hunting Cabin on 1+/- Acres. Spring water supply and a holding tank for septic in place. Several sleeping areas including a loft. One full bathroom. Kitchen with stove, ,microwave, refrigerator, stove, pellet stove, wood stove, 2 mini splits, washer & dryer. Plan your weekend runaway now!

    Janet Boyd Boyd Real Estate

    279 North St, East Dover, VT 05341
  • /40

    $445,000

    $44K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,560 Sq Ft

    494 W River St, Londonderry, VT 05155

    Lucky for the next Buyer that this home is back on market because last buyer could not secure financing!This comfortable home is situated in a peaceful and open sunny meadow surrounded by mature trees and 10 acres of Vermont woods offering total privacy. A view of Magic Mountain is a bonus as is the close proximity to shopping and dining. An important feature of the home is the newly added

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    494 W River St, Londonderry, VT 05155
  • /57

    $335,000

    $45K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 2,336 Sq Ft

    1033 Burrington Hill Rd, Whitingham, VT 05361

    Charming and character-filled 1835 post-and-beam Craftsman. This inviting five-bedroom, two and-a-half-bath home blends antique appeal with cozy comfort. A covered porch offers the perfect place to enjoy summer breezes, the sound of rainstorms, and peaceful evenings, while the deck is ideal for gathering with friends and family. Inside, wood floors and exposed hand-hewn beams highlight the home's

    Monique White Deerfield Valley Real Estate

    1033 Burrington Hill Rd, Whitingham, VT 05361
  • /40

    $755,000

    $320K PRICE DROP
    • 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
  • /60

    $535,000

    $25K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,397 Sq Ft

    14 High Top Rd Unit B124, Wilmington, VT 05363

    Section B Cul de Sac. Fabulous large house on an oversized lot! First time on the market in 20 years! 3+ bedrooms, 3 bathrooms, gas fireplace, large deck, workshop space, large driveway with plenty of level parking. Mudroom entry, laundry room, open concept living, dining and kitchen. Newer appliances, second fridge, first floor bedroom and bathroom, plus a study and two glass rooms that are

    Sigrid Pickering Chimney Hill Realty

    14 High Top Rd Unit B124, Wilmington, VT 05363
  • /51

    $899,000

    • 4 Beds
    • 4.5 Baths
    • 3,100 Sq Ft

    33 Carinthia Dr, Dover, VT 05356

    LOCATION, LOCATION, LOCATION!! 3000+ Sq ft, 4 beds plus den, 4.5 baths, 3 fireplaces, and an attached garage all in the Carinthia base area of Mount Snow Ski Resort!! This 4-bedroom, 4.5-bath home offers a versatile layout with multiple en-suite bedrooms, 3 wood-burning fireplaces, and a sauna, just steps from the slopes. The main level showcases a spacious sunken living room with cathedral

    Jacki Murano Southern Vermont Realty Group

    33 Carinthia Dr, Dover, VT 05356
  • /31

    $15,900

    • 1 Bed
    • 1 Bath
    • 673 Sq Ft

    302 Qtr 2 Grand Summit Way, Dover, VT 05356

    Own where you play! This sun-filled, top-floor one-bedroom condo is located in a quieter area of the Grand Summit Resort Hotel, with a large window overlooking the Sundance ski trail. Just steps from the slopes, it offers convenient access to year-round resort amenities. A deeded quarter-share provides approximately 13 weeks of vacation ownership annually, with one week every 28 days on a

    Patricia Fitzpatrick Skihome Realty

    302 Qtr 2 Grand Summit Way, Dover, VT 05356
  • /60

    $1,160,000

    • 5 Beds
    • 4 Baths
    • 3,664 Sq Ft

    82 N Brookwood Rd, Stratton, VT 05360

    Location , Location , Location! Situated on North Brookwood just below the covered brige you'll enjoy easy access to the Wanderer ski trail as well as the resort shuttle that picks you up at your driveway! This iconic resort property features a great room with custom wood barrel cathedral ceilings, a wall of glass, wood burning fireplace and wrap around deck. Designed for the mountain enthusiast,

    Kim Morgan-Wohler Wohler Realty Group

    82 N Brookwood Rd, Stratton, VT 05360
  • /30

    $289,000

    • 2 Beds
    • 1 Bath
    • 696 Sq Ft

    398 Tallwood Cir, Londonderry, VT 05148

    Welcome to 398 Tallwood Circle, a cozy Vermont retreat tucked into a quiet country setting in Londonderry. Set on 1.5 acres with a wooded backdrop, this 2-bedroom, 1-bath home offers privacy, character, and an ideal base for enjoying Southern Vermont.Inside, an inviting open living area features a vaulted wood ceiling, abundant natural light, and a wood stove for warmth and classic

    Grayson VanHendrick Flex Realty

    398 Tallwood Cir, Londonderry, VT 05148
  • /53

    $1,315,000

    $135K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 2,974 Sq Ft

    494-498 Goodaleville Rd, Jamaica, VT 05343

    4BR MAIN HOUSE, 1BR BARN APARTMENT, AND SEPARATE RESTORED VINTAGE BARN | Tucked along a quiet back road with the gentle sounds of the flowing Winhall River, this beautifully restored Vermont farmhouse feels worlds away, yet is just 10 minutes from Stratton Mountain Resort. Blending authentic character, exceptional craftsmanship, and modern comfort, the property offers a rare sense of privacy and

    Cheyanne Pugliese

    494-498 Goodaleville Rd, Jamaica, VT 05343
  • /47

    $895,000

    • 3 Beds
    • 4 Baths
    • 3,981 Sq Ft

    257 Dover Hill Rd, Dover, VT 05341

    Experience the best of Vermont living in this exceptional 3-bedroom, 4-bath Energy Star timber frame home set on 6.9 acres of beautiful land, with a mix of open lawn and mature forest. Designed to take full advantage of its stunning 50-mile long-range views, the home offers warmth, character, and plenty of space to gather. The inviting great room features a striking double-sided gas fireplace,

    Patrice Schneider Southern Vermont Realty Group

    257 Dover Hill Rd, Dover, VT 05341
  • /11

    $120,000

    • Land
    • 10.2 Acres
    • $11,765 per Acre

    0 S Hill Rd, Jamaica, VT 05343

    The South Jamaica Parcels consist of two contiguous lots situated along South Hill Road and Schoolhouse Road in South Jamaica, Vermont. Each parcel offers an excellent building opportunity, featuring level, buildable terrain and the convenience of power already available at the street making them ideal, low-hassle sites for a future home.Parcel I is a 10-acre building site located on

    Thom Milke Fountains Land Inc.

    0 S Hill Rd, Jamaica, VT 05343
  • /26

    $499,000

    • 3 Beds
    • 2.5 Baths
    • 1,912 Sq Ft

    11 Dutchman Ln Unit 4A, Wilmington, VT 05363

    Beautiful three story Powderhorn townhome on the slopes of Haystack Mountain at the exclusive Hermitage Club Ski Resort - a true four-season retreat with thoughtful upgrades that set it apart from anything else in the development. Wake up to sunrise winter views over the mountains through expansive windows thanks to the end unit location. Enjoy woodsy scenery over your private deck and great

    Adam Palmiter Berkley & Veller Greenwood/Dover

    11 Dutchman Ln Unit 4A, Wilmington, VT 05363
  • /60

    $750,000

    • 6 Beds
    • 4.5 Baths
    • 3,259 Sq Ft

    492 Dover Rd, Newfane, VT 05351

    Own a piece of Vermont history with this charming 1854 home, formerly known as The ThreePenny Lodge and now known as The Cardinal Lodge, nestled in the heart of desirable Newfane near skiing, trails and year-round recreation. Cross a picturesque, covered bridge on your way home and discover a property full of character, currently operating as a successful Airbnb with a live-in caretaker. Whether

    Kerry Mulverhill

    492 Dover Rd, Newfane, VT 05351
  • /35

    $315,000

    New Construction $35K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 640 Sq Ft

    203 Fairview St, Brattleboro, VT 05301

    PRICE IMPROVEMENT! MOTIVATED SELLER! Welcome to this brand NEW, beautiful home, professionally blower-door tested at an exceptional 1.7 providing outstanding airtightness, energy efficiency, & year-round comfort. Completed in July 2026 & designed for low-maintenance living, the home benefits from net-metered solar credits that have offset the owner’s electrical needs, including heating & cooling.

    Kristen Ziter Taylor Brattleboro Area Realty

    203 Fairview St, Brattleboro, VT 05301
  • /7

    $279,000

    • Land
    • 45 Acres
    • $6,200 per Acre

    Lot 0 Saddada Rd, Whitingham, VT 05361

    Lovely pastoral parcel of land in Whitingham Vermont with mountain views. This parcel sits conveniently on the MA border for easy access into the Deerfield Valley or Heath area. The 45 acre parcel is about half pasture and half mature woodlands, with easy access of the quiet country road, old stone walls, views of the mountains to the west, and a serene setting.

    Michael Purcell Berkley & Veller Greenwood/Dover

    Lot 0 Saddada Rd, Whitingham, VT 05361
  • /59

    $412,250

    $13K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,345 Sq Ft

    52 Ruth Way, Wilmington, VT 05363

    Welcome to this inviting 4-bedroom, 3-bathroom home nestled on a tranquil street, cherished by one family for nearly two decades. This residence exudes warmth and comfort, offering the perfect blend of functionality and charm. As you step through the covered front door, a cozy mudroom/entry area sets the tone for the welcoming atmosphere throughout the home. The spacious living room is ideal for

    Donna Brown Skihome Realty

    52 Ruth Way, Wilmington, VT 05363
  • /53

    $400,000

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft

    256 Trail Rd, Putney, VT 05346

    Welcome to your private Vermont retreat! Nestled on 2.5 pristine acres, this unique home perfectly blends quiet country living with exceptional functional versatility.As you pull up the scenic drive, you will immediately notice the beautiful, established orchard featuring multiple fruiting apple, pear, and peach trees dotting the expansive lawn. The main residence welcomes you with a classic

    Logan Nicoll KW Vermont

    256 Trail Rd, Putney, VT 05346
  • /17

    $729,000

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft

    778 Stratton Mountain Access Rd Unit 2103, Stratton, VT 05155

    Ski-In/Ski-Out Perfection: Your Premier Stratton Mountain Retreat! Experience the ultimate Vermont lifestyle in this rare 2-bedroom, 2-bathroom condo, perfectly positioned for true ski-in/ski-out convenience. Located just steps from the Villager Chairlift and the bustling heart of Stratton Village, this residence offers a seamless transition from the slopes to your front door.Designed with

    Robin Apps Four Seasons Sotheby's Int'l Realty

    778 Stratton Mountain Access Rd Unit 2103, Stratton, VT 05155
  • /33

    $495,000

    • 4 Beds
    • 2.5 Baths
    • 2,550 Sq Ft

    172 Franklin Rd, Vernon, VT 05354

    Almost new! This amazing transformation has brought this 80's home to a new and exciting level! This home is a traditional tri-level with an open concept kitchen and dining room with room enough for a cozy sitting area or a huge center island, The 28x30 foot living room is just steps away, anchored by a wood stove, sporting a sweet 1/2 bath and access to the new back deck. One bedroom and bath

    Christine Lewis Brattleboro Area Realty

    172 Franklin Rd, Vernon, VT 05354
  • /15

    $119,000

    • Land
    • 10.9 Acres
    • $10,917 per Acre

    0 Under the Mountain Rd, South Londonderry, VT 05155

    10+ acres on beautiful Under the Mountain Road, home to horse farms, stone walls, and pure country charm! This property offers a blank slate to bring your vision to life; whether you are looking to build a small efficient home, a large country estate, or a self-sufficient homestead. There is a small rustic camp already on the property, and a small wetland area towards the back. Bordered by

    Rebecca Seymour Brattleboro Area Realty

    0 Under the Mountain Rd, South Londonderry, VT 05155
  • /38

    $645,000

    • 4 Beds
    • 3 Baths
    • 2,740 Sq Ft

    1161 Little Pond Rd, Londonderry, VT 05148

    Beautifully renovated 4-bedroom home with a stylish 2-bedroom accessory dwelling, offering the perfect blend of modern comfort, flexibility, and Vermont charm. Whether you're looking for space for extended family, guests, or the potential for rental income, this thoughtfully designed property offers endless possibilities.Step inside to discover contemporary upgrades throughout, where every

    Carrie Mathews Winhall Real Estate

    1161 Little Pond Rd, Londonderry, VT 05148
  • /48

    $450,000

    • 5 Beds
    • 1.5 Baths
    • 2,218 Sq Ft

    1877 Fort Bridgman Rd, Vernon, VT 05354

    Neat as pin, inside, outside, upside down...rarely will you find a homeas meticulous as this including basement, grounds and garages. Sunriseto sunset, watch the drama unfold as the skies turn to gold and velvetand you catch the summer breeze on the decks or listen to the rain asyou cozy in on the covered farmer's porch. One level living at it'sbest with a first floor bedroom

    Christine Lewis Brattleboro Area Realty

    1877 Fort Bridgman Rd, Vernon, VT 05354

Showing Results 241 - 280, Page 7 of 13

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