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Windham County CT Homes for Sale

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  • /14

    $300,000

    Coming Soon
    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    41 Little River Ln, Canterbury, CT 06331

    Country Cape nestled back on 1.39 acre at the end of cul de sac for privacy. Granite counters, stainless appliances in eat in kitchen with slider leading to enormous deck to enjoy your Summer evenings. Remodeled bathroom on 1 st floor with primary bedroom and newer flooring another room could be an office. Living room has newer flooring. Spacious bedroom on upper level and a smaller one and a

    Christine Johnson RE/MAX One

    41 Little River Ln, Canterbury, CT 06331
  • /16

    $329,000

    • 3 Beds
    • 1 Bath
    • 1,484 Sq Ft

    47 River Ridge Rd, Danielson, CT 06239

    Welcome to 47 River Ridge Road, where you will find a perfect combination of nature's playground and a peaceful private sanctuary. The home features 3 bedrooms, 1 bathroom. The newly updated bathroom offers a new motorized skylight. Settled on a quiet Cul-De-Sac, this home offers river access to Quinebaug River, right from your own backyard. A new beautiful over-sized deck is the perfect

    Megan Broneill REMAX Revolution

    47 River Ridge Rd, Danielson, CT 06239
  • /33

    $305,000

    • 3 Beds
    • 1 Bath
    • 1,225 Sq Ft

    47 Broad St, Danielson, CT 06239

    Welcome home to this charming and well-maintained 3-bedroom Cape, ideally situated on a corner lot in a picturesque neighborhood of period homes. Relax with your morning coffee or unwind in the evening on the inviting front porch, the perfect place to enjoy the neighborhood's timeless charm. Inside, you'll find nicely maintained living spaces that reflect pride of ownership and make this home

    Vivian Kozey CR Premier Properties

    47 Broad St, Danielson, CT 06239
  • /38

    $489,000

    • 1 Bed
    • 2 Baths
    • 2,139 Sq Ft

    109 Munyan Rd, Putnam, CT 06260

    Set on 8.07 scenic acres abutting Munson Brook, this unique property offers space, privacy, and flexibility just minutes from downtown Putnam. While town records list the home as a one-bedroom, the current layout offers three rooms being used as bedrooms, providing a variety of living options to suit your needs. Inside, you'll find 2,139 square feet of inviting living space featuring an

    Scott Pempek Berkshire Hathaway NE Prop.

    109 Munyan Rd, Putnam, CT 06260
  • /40

    $449,900

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

    29 Bingham Rd, Canterbury, CT 06331

    Move-in ready and beautifully maintained, this charming home offers 3 spacious bedrooms and 2 full bathrooms. The open floor plan creates a bright, welcoming living space that's perfect for everyday living and entertaining. The finished basement is an entertainer's dream, featuring a wet bar and a pool table that's included with the home. With thoughtful updates and plenty of space to relax and

    Laurie Hayes-Hagstrom On The Move Realty, LLC

    29 Bingham Rd, Canterbury, CT 06331
  • /26

    $365,000

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    847 Sterling Rd, Sterling, CT 06377

    *Highest and best offers by Monday, July 13th at 12pm* Nestled on a peaceful lot, 847 Sterling Road offers the perfect blend of comfort, functionality, and country charm. This well-maintained home features spacious living areas filled with natural light, creating a warm and inviting atmosphere for everyday living and entertaining. Outside, you'll find a standout heated three-car garage, providing

    Paula Decubellis Brian Buonaiuto

    847 Sterling Rd, Sterling, CT 06377
  • /34

    $359,900

    • 3 Beds
    • 1 Bath
    • 1,544 Sq Ft

    19 Thompson Pike, Dayville, CT 06241

    Welcome home to Killingly! Come check out this very well-maintained Raised Ranch in the Dayville neighborhood. This property features 3 bedrooms, 1 full bathroom, Eat-in-kitchen with dining area that has sliders to the upper deck. A living room, a family room, laundry area and utility room. Full walk-out basement to the back yard and prick patio. Large shed located in the yard as well. Property

    Mike Pereira REMAX Revolution

    19 Thompson Pike, Dayville, CT 06241
  • /23

    $395,000

    Coming Soon
    • 3 Beds
    • 1 Bath
    • 1,196 Sq Ft

    27 Mountain Hill Rd, North Grosvenordale, CT 06255

    Welcome home to this beautifully maintained 3-bedroom, 1-bath ranch, nestled on 0.76 acres in North Grosvenordale, CT. Offering 1,196 square feet of comfortable living space, this home has been lovingly cared for and is truly move-in ready. Step inside to find beautiful stone fireplace and hardwood floors that flow throughout much of the home, creating a warm and inviting atmosphere. The

    Chelsea Greene CR Premier Properties

    27 Mountain Hill Rd, North Grosvenordale, CT 06255
  • /2

    $450,000

    Open House 7/24 Coming Soon
    • 4 Beds
    • 2 Baths
    • 1,690 Sq Ft

    8 Plainview Dr, Plainfield, CT 06374

    Welcome to 8 Plainview Drive, a beautifully updated 4-bedroom, 2-bath Cape located on a quiet cul-de-sac in Plainfield. Situated on 0.81 acres, this home offers plenty of space while still being close to everything you need. Over the last few years, the home has seen extensive updates, including a new roof, vinyl siding, repaved driveway, farmer's porch, and front bedroom dormers, all completed

    Kelsie Griffin Wolfburg Kazantzis Real Estate, LLC

    8 Plainview Dr, Plainfield, CT 06374
  • /33

    $465,000

    • 3 Beds
    • 2.5 Baths
    • 1,792 Sq Ft

    11 Munyan Rd, Putnam, CT 06260

    Highest & Best offers by noon 7/13/26 Don't let the age fool you-this beautifully renovated ranch has been transformed from top to bottom, inside and out! Set on 2.5 private acres, this 3-bedroom, 21/2-bath, 1 car garage combines charm with modern updates, offering truly move-in-ready living. The interior has been completely refreshed with outdated paneling removed and replaced by custom

    Donna Navarro Signature Properties of N.E.

    11 Munyan Rd, Putnam, CT 06260
  • /22

    $219,900

    • 2 Beds
    • 1.5 Baths
    • 1,160 Sq Ft

    71 Sachem Dr, Plainfield, CT 06374

    Welcome to this desirable single-floor end unit condo, ideally situated in a quiet, sidewalk lined, neighborhood. Set back from the road, park in your 2 designated parking spots right in front of the welcome landscaped entry. Enter into a bright spacious open concept living room, dining, and kitchen. Freshly painted vaulted ceilings give this unit an airy feel that lives larger than its

    Elizabeth Zimmer Berkshire Hathaway NE Prop.

    71 Sachem Dr, Plainfield, CT 06374
  • /39

    $349,900

    • 5 Beds
    • 2 Baths
    • 2,808 Sq Ft

    27 Railroad St, Putnam, CT 06260

    Investment opportunity!! This up and down duplex is in Downtown Putnam, a destination town, where so many eat, work, and play. The 2 units were renovated before these amazing tenants moved in. The walk up attic is just waiting to be finished off to unlock even more income potential. The sooner you buy this one the sooner you will will be building equity. Make sure you stop by this one ASAP. ALL

    Matthew Noren RE/MAX Bell Park Realty

    27 Railroad St, Putnam, CT 06260
  • /34

    $450,000

    Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 1,918 Sq Ft

    125 Canterbury Rd, Plainfield, CT 06374

    SPRAWLING 1918 sq ft COUNTRY RANCH sits back on 7.62 ACRES offering plenty of room to build, grow and explore and is perfect for a homestead, animals, 4 wheeling, dirtbikes etc. GLEAMING HARDWOOD floors throughout this open floor plan great for entertaining. HUGE living room w/ BRIGHT BAY window open to STAINLESS APPLIANCE kitchen w/ LARGE ISLAND (stools convey) and dining area with FRENCH DOORS

    Christine Johnson RE/MAX One

    125 Canterbury Rd, Plainfield, CT 06374
  • /8

    $300,000

    • Land
    • 22.2 Acres
    • $13,514 per Acre

    0 Route 197, Woodstock, CT 06281

    22.2-acre building lot offering endless possibilities in desirable Woodstock! Whether you're a builder, investor, or looking for the perfect location to build your forever home, this property is ready for your vision. Approximately 0.5 acres have already been cleared, and valuable due diligence has been completed, including a town-approved septic design, engineered site plan, and professionally

    Ilya Whittemore Lamacchia Realty

    0 Route 197, Woodstock, CT 06281
  • /22

    $239,900

    • 1 Bed
    • 1 Bath
    • 961 Sq Ft

    31 Mason Rd, Brooklyn, CT 06234

    RESTORE THE HOME AND FALL IN LOVE WITH THE LAND! This unique property offers a setting that is increasingly difficult to find. The main homesite encompasses 1.1 acres with a waterfall view, while an additional 0.9-acre parcel across the road includes ownership along Blackwell Brook, peaceful water views, and your own private spot to fish. Whether you're enjoying your morning coffee while

    Agent Photo

    Tina Lajoie

    Signature Properties of N.E.

    31 Mason Rd, Brooklyn, CT 06234
  • /31

    $595,000

    • 3 Beds
    • 2.5 Baths
    • 1,464 Sq Ft

    107 N Society Rd, Canterbury, CT 06331

    Spacious 3-bedroom, 2.5-bath home situated on 16.4 picturesque acres on a quiet country road in Canterbury. This property offers a wonderful mix of open fields and wooded land, making it ideal for horses, hobby farming, recreation, or simply enjoying privacy. The home features a dedicated office, cedar closet, attached 2-car garage, and numerous updates including newer windows, siding, doors, and

    Kristen Tarryk Duprey Real Estate, LLC

    107 N Society Rd, Canterbury, CT 06331
  • /38

    $524,900

    • 3 Beds
    • 2 Baths
    • 1,380 Sq Ft

    321 Day St, Brooklyn, CT 06234

    Welcome to this beautiful 2019 Raised Ranch, offering the perfect blend of modern comfort and peaceful country living. This inviting home features 3 generously sized bedrooms, 2 full bathrooms, hardwood floors and central air. The heart of the home is the stunning kitchen, complete with granite countertops, a large center island, stainless steel appliances, and plenty of space for cooking,

    Agent Photo

    Christine Costa

    Kazantzis Real Estate, LLC

    321 Day St, Brooklyn, CT 06234
  • /9

    $45,000

    • 1 Bed
    • 1 Bath
    • 510 Sq Ft

    25 Route 197 Unit 29, Woodstock, CT 06281

    Welcome to Beautiful Meadowside of Woodstock Campground, a private, gated 100 site co-op campground in Connecticut's quiet Corner. Unit 29 features a 1998 Four Winds mobile home model 30fk and a 30 foot by 9.5 foot combination room added on to the front. The trailer has a kitchen, living room dining room combo with a pull out bed, full bath, and bed room. The addition had a bigger eating area and

    Margaret Young CR Premier Properties

    25 Route 197 Unit 29, Woodstock, CT 06281
  • /21

    $349,900

    • 3 Beds
    • 2 Baths
    • 2,062 Sq Ft

    277 Old Colony Rd, Eastford, CT 06242

    Brand new 2026 septic, roof, siding, windows, plumbing, electrical, sheetrock, insulation, lights, interior/exterior doors! Beautiful brand new applianced kitchen with granite counter and white shaker cabinets. All new flooring, carpet and refinished hardwoods. 2 brand new bathrooms with tiled showers, brand new toilets and vanities. All new baseboard and trim. TWO brand new paved driveways with

    Christine Johnson RE/MAX One

    277 Old Colony Rd, Eastford, CT 06242
  • /40

    $849,900

    • 3 Beds
    • 2 Baths
    • 1,696 Sq Ft

    84 Dark Lantern Hill Rd, Danielson, CT 06239

    Welcome to your own private country retreat! This exceptional log home offers the perfect blend of rustic charm and modern updates, nestled on a picturesque property designed for those seeking peace, privacy, and room to roam.The heart of the home is the brand-new great room addition, featuring soaring cathedral ceilings, abundant natural light, and direct access to a spacious deck overlooking

    Lisa Harrison J. Christopher Real Estate Group

    84 Dark Lantern Hill Rd, Danielson, CT 06239
  • /39

    $630,000

    Open Wed 5PM - 7PM
    • 3 Beds
    • 3 Baths
    • 3,340 Sq Ft

    373 Chase Rd, Thompson, CT 06277

    Welcome to your private, beautifully landscaped retreat in Thompson. This meticulous colonial offers generous space inside and out, featuring a stunning granitetopped kitchen with undercabinet lighting, JennAir cooktop, cabinetpacked storage, and a slider leading to the Trex deck. The open layout flows into a bright living room with a large island, plus a charming dining room and a cozy family

    Michelle Fanion Century 21 North East

    373 Chase Rd, Thompson, CT 06277
  • /25

    $500,000

    • 3 Beds
    • 1.5 Baths
    • 2,014 Sq Ft

    21 Fairfield Dr, Woodstock, CT 06281

    Welcome home to this charming colonial tucked away on a peaceful cul-de-sac, offering privacy and picturesque views on a full acre of land. As you step in through the fresh new mudroom, you will find a spacious, bright living room, a separate dining room, and a beautiful kitchen with stainless steel appliances, a breakfast bar, abundant cabinet space, and access to a private back deck overlooking

    Patricia Scarpa Marino Realty LLC

    21 Fairfield Dr, Woodstock, CT 06281
  • /20

    $295,000

    • 2 Beds
    • 1.5 Baths
    • 1,218 Sq Ft

    257 Sabin St Unit 21, Putnam, CT 06260

    This townhouse offers both convenience and spaciousness. Located nicely to all shopping, parks, hospital and the highway. End unit with a one car garage. The fully applianced kitchen, and 1/2 bath. On the upper level are 2 large bedrooms and a full bath. Each bedroom has plenty of closet space. New gas/range/oven, microwave does not work AGENT RELATED TO SELLER

    Robin Smith RE/MAX Bell Park Realty

    257 Sabin St Unit 21, Putnam, CT 06260
  • /11

    $319,900

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

    54 Main St, North Grosvenordale, CT 06255

    Colonial style 1400 sq ft home featuring 3 bedrooms and 2 full bath. NEW ROOF from 2022. Boiler from 2015. New hot water baseboard installed throughout house in 2021. 1.40 acres total was 2 lots when purchased in 2022, may be additional value or potential build lot if town allowed you to revert back to 2 lots.

    Joseph Bonneau eXp Realty

    54 Main St, North Grosvenordale, CT 06255
  • /34

    $549,000

    • 3 Beds
    • 2 Baths
    • 1,977 Sq Ft

    182 Stawicki Rd, North Grosvenordale, CT 06255

    Escape to the peace and quiet of country living in this charming Cape Cod-style home offering 3 bedrooms and 2 full bathrooms. From the moment you arrive, you'll appreciate the picturesque setting and the inviting spaces both inside and out. The home features a practical mudroom, perfect for keeping everyday life organized, and a spacious two-car garage complete with a loft above-ideal for

    Courtney Ravenelle RE/MAX Bell Park Realty

    182 Stawicki Rd, North Grosvenordale, CT 06255
  • /40

    $620,000

    • 4 Beds
    • 3 Baths
    • 3,023 Sq Ft

    269 Black Hill Rd, Plainfield, CT 06374

    Experience the comfort of one-level living in this custom-built ranch-style home set on a spacious lot in Plainfield, offering the perfect blend of privacy, functionality, and everyday convenience. With approximately 3,000 square feet of living space, this thoughtfully designed home features 4 bedrooms, 3 full bathrooms, plus a dedicated office that can easily serve as a 5th bedroom. Step inside

    Darius Baturo Berkshire Hathaway NE Prop.

    269 Black Hill Rd, Plainfield, CT 06374
  • /2

    $400,000

    • 6 Beds
    • 2 Baths
    • 2,652 Sq Ft

    78 S Main St, Brooklyn, CT 06234

    Exceptional investment opportunity! This well-maintained two-family property is business zoned, offering endless possibilities for investors, business owners, or those seeking a live/work opportunity. Each spacious unit features approximately 1,500 square feet with 3 bedrooms, providing strong rental appeal and excellent income potential. Whether you're looking to continue its use as a

    Andrea Kazantzis, CCIM Kazantzis Real Estate, LLC

    78 S Main St, Brooklyn, CT 06234
  • /29

    $175,000

    • 2 Beds
    • 1 Bath
    • 848 Sq Ft

    96 Canterbury Rd Unit B, Plainfield, CT 06374

    FULLY FURNISHED! Move right in to this charming 2-bedroom, 1-bath townhouse-style condominium. This inviting home features a bright and spacious living area and an eat in fully applianced kitchen & brand new carpeting throughout. The second level houses the full bathroom and two bedrooms. Enjoy low-maintenance living with the condo fee covering grounds maintenance, snow removal, trash pickup &

    Lisa Gervais Team Bassett Realty LLC

    96 Canterbury Rd Unit B, Plainfield, CT 06374
  • /40

    $699,000

    • 4 Beds
    • 2.5 Baths
    • 2,634 Sq Ft

    272 Horse Hill Rd, Ashford, CT 06278

    Nestled at the end of a long, winding driveway, this exquisite Colonial home offers timeless New England elegance on over three private, picturesque acres. Surrounded by classic stone walls, sprawling lawns, mature gardens, and inviting outdoor dining spaces, this exceptional property is a secluded retreat rich in historic details and charm. Inside, you'll find four spacious bedrooms with one on

    Jay Kelly William Raveis Real Estate

    272 Horse Hill Rd, Ashford, CT 06278
  • /31

    $499,900

    • 4 Beds
    • 4.5 Baths
    • 2,818 Sq Ft

    113 Starkweather Rd, Plainfield, CT 06374

    Nestled on 11.6 acres of open and wooded land, this spacious farmhouse offers the perfect blend of comfort, privacy, and productive outdoor space. The four-bedroom, four-bath home features an open floor plan that creates a bright, welcoming atmosphere ideal for both everyday living and entertaining. The expansive yard provides ample room for gardening, small-scale farming, or simply enjoying the

    Daniel Deojay RE/MAX Bell Park Realty

    113 Starkweather Rd, Plainfield, CT 06374
  • /35

    $599,000

    Open Fri 3PM - 7PM
    • 5 Beds
    • 4 Baths
    • 2,760 Sq Ft

    21 Linkkila Ln, Chaplin, CT 06235

    Private Country Retreat with In-Law Suite on Nearly 4 Acres. Welcome to 21 Linkkila Lane in Chaplin, Windham County, Connecticut-a beautifully updated log home offering exceptional privacy, flexible living space, and modern upgrades on nearly four picturesque acres. The main residence features three spacious bedrooms and three full bathrooms, highlighted by an extensively renovated kitchen,

    Derek Greene Derek Greene

    21 Linkkila Ln, Chaplin, CT 06235
  • /40

    $1,995,000

    $505K PRICE DROP
    • Land
    • 153.1 Acres
    • $13,031 per Acre

    317 Bebbington Rd, Ashford, CT 06278

    CROOKES ORCHARD - A LEGACY FARM OF EXTRAORDINARY BEAUTY AND OPPORTUNITY! One of Northeast Connecticut's most beloved agricultural destinations, presents an exceptionally rare opportunity to acquire 153 contiguous acres of working orchard, farmland, & scenic countryside. The property encompasses approximately 32 acres of improved cropland w/sprawling hay fields, picturesque ponds, & Bebbington

    Kiara Rusconi William Raveis Real Estate

    317 Bebbington Rd, Ashford, CT 06278
  • /2

    $299,900

    • 6 Beds
    • 3 Baths
    • 2,700 Sq Ft

    14 Carey St, Willimantic, CT 06226

    Excellent opportunity to own a spacious 2-family home with great flexibility for investors or owner-occupants. The first unit offers 2 bedrooms and 1 full bath, while the second unit features a generous 4-bedroom, 2-bath layout, providing plenty of space for larger households or strong rental potential. A 2-car garage adds valuable parking and storage, making this property even more attractive.

    Agent Photo

    Amy Rio

    Better Homes and Gardens Real Estate Executive Real Estate

    14 Carey St, Willimantic, CT 06226
  • /28

    $359,000

    $10K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,918 Sq Ft

    705 Lainey Ln, Killingly, CT 06239

    Welcome to 705 Lainey Lane - a beautiful end-unit townhouse in Killingly, Connecticut! This move-in ready two bedroom home with a possible third bedroom features two full baths and a half bath, plus two driveway parking spaces, a one-car attached garage, and is just minutes from the Rhode Island border and easy access to 395 North and South. Enjoy peaceful views of the pond right on your

    Michelle Richardson Kazantzis Real Estate, LLC

    705 Lainey Ln, Killingly, CT 06239
  • /15

    $74,900

    • Land
    • 17,424 Sq Ft
    • $187,250 per Acre

    182 Baxter Rd, Woodstock, CT 06281

    Imagine waking each morning to shimmering lake views and the peaceful sounds of nature. Tucked away on a quiet dead-end road in Woodstock's coveted Quassett Lake community, this exceptional homesite offers the rare opportunity to create a custom retreat in one of northeastern Connecticut's most treasured settings. Perched above the road with a gentle rise in elevation, the property enjoys

    Jennie Kesselman Berkshire Hathaway NE Prop.

    182 Baxter Rd, Woodstock, CT 06281
  • /21

    $295,000

    • 3 Beds
    • 2 Baths
    • 1,467 Sq Ft

    602 N Main St, Danielson, CT 06239

    Full of character, this 3-bedroom, 2 full bath home offers a spacious and functional layout in a convenient, walkable location. The main level features a large living room, a spacious kitchen with plenty of room to cook and gather, a dedicated dining room, a versatile bonus room perfect for a home office or playroom, and the convenience of first-floor laundry. All three bedrooms are located

    Skyla Gagnon RE/MAX Bell Park Realty

    602 N Main St, Danielson, CT 06239
  • /40

    $600,000

    • 3 Beds
    • 2 Baths
    • 2,599 Sq Ft

    1638 North Rd, Dayville, CT 06241

    Welcome home to this stunning, thoughtfully renovated property where classic New England charm meets modern living. Expanded and beautifully updated. A truly unique home. Step inside to a cozy library-style living room featuring a propane fireplace, custom built-ins, coffered ceilings, and detailed trim work. French doors lead to the showstopping gourmet kitchen, completely redesigned with dual

    Skyla Gagnon RE/MAX Bell Park Realty

    1638 North Rd, Dayville, CT 06241
  • /20

    $264,900

    • 2 Beds
    • 1.5 Baths
    • 1,088 Sq Ft

    18 Ballou St Unit 10, Putnam, CT 06260

    Easy living in this Townhouse Condo! 2 spacious bedrooms, Large Living room, Kitchen with appliances and dining room with slider to a Private Deck. 1 Car Garage completes this unit for anyone looking for convenience! Minutes to 395 for commuters and only a mile from all the wonderful shops and eateries downtown Putnam has to offer. Come see for yourself!

    Rachael Zagurski RE/MAX One

    18 Ballou St Unit 10, Putnam, CT 06260
  • /2

    $125,000

    • Land
    • 1.06 Acres
    • $117,925 per Acre

    86 Ference Rd, Ashford, CT 06278

    Here is a rare opportunity to buy a FULLY Approved 1.06 Acre Building lot in the beautiful new Subdivision of Ashford Meadow Estates, Known as Lot #4 in Ashford's Newest 6 lot subdivision featuring picturesque land in Eastern CT's quiet corner. Build your own or have Titan Construction build a custom home for you. Custom homes currently offered include ranch and colonial farmhouse style and start

    Mark Massaro Coldwell Banker Realty

    86 Ference Rd, Ashford, CT 06278
  • /28

    $625,000

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

    350 Hartford Pike, Dayville, CT 06241

    Live in this lovely house. 4-5 bedrooms 2.5 bathrooms. Eat-in kitchen, formal living room and formal dining room, first floor office, family room and laundry room. Most rooms have tin ceilings. The second floor is 4 bedrooms and 2 full bathrooms. Have your business in the former church...3300 sq ft with a balcony and a half bathroom. Handicap accessible. You could have your business on the first

    Mark Benard Brunet and Company Real Estate

    350 Hartford Pike, Dayville, CT 06241

Showing Results 41 - 80, Page 2 of 8

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