45,944

Windham County, CT Homes

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  • 10 Laurel Hill Dr, Woodstock Valley, CT 06282
    10 Laurel Hill Dr, Woodstock Valley, CT 06282
    10 Laurel Hill Dr, Woodstock Valley, CT 06282
    /5

    $290,000

    • 2 Beds
    • 1.5 Baths
    • 1,196 Sq Ft

    10 Laurel Hill Dr, Woodstock Valley, CT 06282

    LOCATION, LOCATION, LOCATION!!!! This cozy 2-3 bedroom ranch is nestled on .40 of an acre lot with views of Lake Bunggee. Lake Bunggee is a private lake association for residents only. Access to the beach and boat launch is across the street. The roof is only 10 years old, electrical was updated and new wood decks on each side of the home. One floor living including a woodburning fireplace for

    Simonne Corriveau KW Legacy Partners

    10 Laurel Hill Dr, Woodstock Valley, CT 06282
  • 44 Red Bridge Rd, North Grosvenordale, CT 06255

    $230,000 Sold Aug 08, 2025

    • 1,266 Sq Ft
    • $182/SF
    • 9 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1949

    44 Red Bridge Rd, North Grosvenordale, CT 06255

    A single family home home close to town with spacious bedrooms and living space. Plenty of storage and parking. Close to all forms of transportation, schools and shopping. Come check it out today!!. Note: The property will be clean and clear at closing.

    Thomas Mele Dorrance Realty

    44 Red Bridge Rd, North Grosvenordale, CT 06255
  • 393 N Canterbury Rd, Canterbury, CT 06331
    393 N Canterbury Rd, Canterbury, CT 06331
    393 N Canterbury Rd, Canterbury, CT 06331
    /40

    $715,000

    • 5 Beds
    • 2 Baths
    • 2,443 Sq Ft

    393 N Canterbury Rd, Canterbury, CT 06331

    Price Drop and brush cleared right up to the pond! Built in 1750 and celebrating its 275th anniversary, this distinguished antique Colonial farmhouse remains a pristine exemplar of early New England architecture. Set on 8.5 acres and nestled on scenic route 169, the estate features a secluded pond, a gently winding brook, and two traditional barns-all original to its historic rural setting. This

    Adam Gumula Kazantzis Real Estate, LLC

    393 N Canterbury Rd, Canterbury, CT 06331
  • 123 Laurel Hill Dr, Woodstock Valley, CT 06282

    $680,000 Sold Aug 08, 2025

    • 1,944 Sq Ft
    • $350/SF
    • 30 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1958

    123 Laurel Hill Dr, Woodstock Valley, CT 06282

    Welcome to this one-of-a-kind lakefront retreat on beautiful Lake Bungee! Set on a double lot, this 3,372 sq ft home offers a rare combination of space, charm, and breathtaking views. With 3 bedrooms, 2 full bathrooms, and a layout designed for both relaxation and flexibility, this property is perfect as a year-round residence or a luxurious getaway. The original portion of the home features 2

    Chris Farrell Carbutti & Co., Realtors

    123 Laurel Hill Dr, Woodstock Valley, CT 06282
  • 271 Snake Meadow Hill Rd, Sterling, CT 06377
    271 Snake Meadow Hill Rd, Sterling, CT 06377
    271 Snake Meadow Hill Rd, Sterling, CT 06377
    /40

    $525,000

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

    271 Snake Meadow Hill Rd, Sterling, CT 06377

    Looking for a custom built home that's set on a peaceful setting? Welcome to this one owner owned home! Located JUST MINUTES OVER the RI line! This private country oasis awaits. This home has it all, including additional & separate living space above the attached 2 car garage. Step food inside this gorgeous home entering through the large mudroom right off the garage which is perfect for New

    Skyla Gagnon RE/MAX Bell Park Realty

    271 Snake Meadow Hill Rd, Sterling, CT 06377
  • 173 Kinne Rd, Canterbury, CT 06331

    $602,000 Sold Aug 08, 2025

    • 6,916 Sq Ft
    • $87/SF
    • 29 Days On Market
    • 6 Beds
    • 3.5 Baths
    • Built 1945

    173 Kinne Rd, Canterbury, CT 06331

    Dream homes demand dream settings. Situated in historical Canterbury, CT, you will find this beautiful 3,458 square foot Dutch Colonial sitting on a secluded 5.04-acre parcel. This stunning home features 6-bedrooms and 3.5 bathrooms, along with an in-ground swimming pool. First floor main suite offers a handicap accessible bathroom setup with wide door openings with a cozy living room and family

    Michelle Richardson Kazantzis Real Estate, LLC

    173 Kinne Rd, Canterbury, CT 06331
  • 4 Perrin Rd, Woodstock, CT 06281
    4 Perrin Rd, Woodstock, CT 06281
    4 Perrin Rd, Woodstock, CT 06281
    /40

    $565,000 Open Sat 12PM - 2PM

    • 5 Beds
    • 3.5 Baths
    • 4,172 Sq Ft

    4 Perrin Rd, Woodstock, CT 06281

    Welcome to the exquisite Ebenezer Stoddard house built in 1800 once an inn for travelers on an early state route. This 4100 sq ft home is filled with character, history and updates for modern convenience, while saving the historic charm! The home resides on an 1.2 acre lot, mostly cleared with plenty of room for family gatherings of any size! Entering the home into an official mudroom - leave

    Kerri Mullen CR Premier Properties

    4 Perrin Rd, Woodstock, CT 06281
  • 46 Union Dr, Ashford, CT 06278

    $270,100 Sold Aug 07, 2025

    • 1,248 Sq Ft
    • $216/SF
    • 5 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1976

    46 Union Dr, Ashford, CT 06278

    New Listing - Lake Community Living! Welcome to this charming 3-bedroom ranch, nestled in a peaceful lake community! Lake Chaffee Improvement Association (LCIA) has an annual dues/special tax of $236 which covers maintenance of common areas, meeting house, beach areas, boat launch, snow plowing and road maintenance. Lake Chaffee privileges include, swimming, great bass fishing, canoeing and 2

    Kim Ricard Priority Real Estate Group,LLC

    46 Union Dr, Ashford, CT 06278
  • 19 Thompson Pike, Dayville, CT 06241
    19 Thompson Pike, Dayville, CT 06241
    19 Thompson Pike, Dayville, CT 06241
    /30

    $350,000

    • 3 Beds
    • 1 Bath
    • 1,320 Sq Ft

    19 Thompson Pike, Dayville, CT 06241

    Welcome to this sweet raised ranch offering an open and inviting layout, perfect for comfortable living and entertaining. The kitchen features newer appliances, granite countertops, stylish cabinetry and an abundance of natural light. Step outside the kitchen onto a lovely composite deck, ideal for outdoor dining or relaxing while overlooking your lovely backyard. This home offers 3 bedrooms, 1

    Amy Archambault CR Premier Properties

    19 Thompson Pike, Dayville, CT 06241
  • 853 Pole Bridge Rd, Woodstock, CT 06281

    $412,050 Sold Aug 07, 2025

    • 1,803 Sq Ft
    • $229/SF
    • 19 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1982

    853 Pole Bridge Rd, Woodstock, CT 06281

    Escape to your own private country retreat on 10 peaceful acres in Northern Woodstock. Tucked away on a quiet private road near the MA line with easy access to I-84 & I-90, this classic Saltbox-style home by early Woodstock Builders Assoc. blends charm with seclusion. Surrounded by mature woods, stone walls, and wildlife, enjoy year-round natural beauty-from spring blooms to fiery fall foliage.

    Mary Collins Berkshire Hathaway NE Prop.

    853 Pole Bridge Rd, Woodstock, CT 06281
  • 117 Woodside St, Putnam, CT 06260
    117 Woodside St, Putnam, CT 06260
    117 Woodside St, Putnam, CT 06260
    /36

    $399,000

    • 4 Beds
    • 2 Baths
    • 2,014 Sq Ft

    117 Woodside St, Putnam, CT 06260

    Beautiful 4-bedroom, 2-bath Colonial offering 2,270 square feet of comfortable living space. The open-concept main level features exposed beam ceilings and an updated kitchen with brand new granite countertops and a convenient breakfast bar. Both bathrooms have been tastefully updated, and the home includes newer windows throughout. Enjoy a large fenced-in backyard, perfect for relaxing or

    Jaclyn Smith Coldwell Banker Realty

    117 Woodside St, Putnam, CT 06260
  • 1668 North Rd, Dayville, CT 06241

    $515,000 Sold Aug 07, 2025

    • 1,998 Sq Ft
    • $258/SF
    • 18 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1981

    1668 North Rd, Dayville, CT 06241

    Private Retreat on Sought-After North Road! Nestled on 6.38 acres and set back from the road for ultimate privacy, this unique property offers nearly 2,000 square feet of living space with charm and character throughout. Built in 1981, this 3-bedroom, 2-bath home welcomes you with a stunning great room featuring a floor-to-ceiling stone fireplace, original beams, and beautiful stained glass

    Scott Pempek Berkshire Hathaway NE Prop.

    1668 North Rd, Dayville, CT 06241
  • 97 Blossom Dr, Pomfret, CT 06259
    97 Blossom Dr, Pomfret, CT 06259
    97 Blossom Dr, Pomfret, CT 06259
    /8

    $125,000

    • Land
    • 1.7 Acres
    • $73,529 per Acre

    97 Blossom Dr, Pomfret, CT 06259

    Two adjacent lots [97 BLOSSOM DR - 1.7 acres + 77 BLOSSOM DR - 2.3 acres] with south-facing slopes and scenic rolling hill views are available in a 26-lot subdivision. Both lots can be bought separately or together and offer walkout basement potential. This listing is for 97 ONLY. Underground utilities [lots would have well + engineered septic systems]. This subdivision features homes valued

    Sanam Solati New England Prestige Realty

    97 Blossom Dr, Pomfret, CT 06259
  • 486 Ashford Center Rd, Ashford, CT 06278

    $595,000 Sold Aug 07, 2025

    • 2,508 Sq Ft
    • $237/SF
    • 13 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1991

    486 Ashford Center Rd, Ashford, CT 06278

    Welcome to this custom-built Ranch offering 2,508 sq ft of well-designed living space, thoughtfully crafted for comfort, efficiency, and versatility. Step inside to discover an open-concept kitchen and living room adorned with striking wood beams, and a cathedral ceiling, creating a warm, expansive gathering space. The kitchen features a large pantry and flows effortlessly into the living

    Tina Lajoie William Raveis Real Estate

    486 Ashford Center Rd, Ashford, CT 06278
  • 77 Blossom Dr, Pomfret, CT 06259
    77 Blossom Dr, Pomfret, CT 06259
    77 Blossom Dr, Pomfret, CT 06259
    /9

    $125,000

    • Land
    • 2.3 Acres
    • $54,348 per Acre

    77 Blossom Dr, Pomfret, CT 06259

    Two adjacent lots [97 BLOSSOM DR - 1.7 acres + 77 BLOSSOM DR - 2.3 acres] with south-facing slopes and scenic rolling hill views are available in a 26-lot subdivision. Both lots can be bought separately or together and offer walkout basement potential. This listing is for 77 ONLY. Underground utilities [lots would have well + engineered septic systems]. This subdivision features homes valued

    Sanam Solati New England Prestige Realty

    77 Blossom Dr, Pomfret, CT 06259
  • 199 Mechanic St, Danielson, CT 06239

    $326,500 Sold Aug 07, 2025

    • 1,726 Sq Ft
    • $189/SF
    • 2 Days On Market
    • 5 Beds
    • 2 Baths
    • Built 1900

    199 Mechanic St, Danielson, CT 06239

    **Well-Maintained Two-Family Home** This versatile and lovingly cared for 2-family home offers the perfect opportunity for owner-occupants or investors alike. The spacious first-floor unit features 3 bedrooms, a bright and inviting living room, and a generous eat-in kitchen-perfect for family gatherings. Upstairs, the second unit offers 2 bedrooms, a cozy living room, and its own eat-in kitchen,

    Heather Ash Spadola RE/MAX One

    199 Mechanic St, Danielson, CT 06239
  • 367 Pine Hill Rd, Sterling, CT 06377
    367 Pine Hill Rd, Sterling, CT 06377
    367 Pine Hill Rd, Sterling, CT 06377
    /36

    $419,900

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft

    367 Pine Hill Rd, Sterling, CT 06377

    Charming Ranch House in Tranquil Sterling, CT, welcome to your dream home in a small-town atmosphere! Nestled on a stunning 1.46-acre lot in the picturesque town of Sterling, Connecticut, this beautifully updated ranch house presents an exceptional blend of comfort and modern elegance. Two-bedroom, one-bathroom, updated flooring, newer appliances, perfectly designed for relaxation and nature

    Allen Gammons BHHS Commonwealth/Robert Paul

    367 Pine Hill Rd, Sterling, CT 06377
  • 40 S Prospect St, Putnam, CT 06260

    $22,000 Sold Aug 07, 2025

    • Land
    • 1.05 Acres
    • $20,952 per Acre
    • 72 Days On Market

    40 S Prospect St, Putnam, CT 06260

    Buildable Lot! 1.05 Acres in Windham, CT - R-7 Zoning = Mobile, Modular, or Multi-Family Allowed - Power at Street - No HOA - Road Access! Located minutes from downtown Putnam and just under an hour to Hartford, Worcester, and Providence-offering rural charm with urban convenience. Daily essentials like schools, groceries, gas, restaurants, and healthcare are within 10 minutes. Gently sloped

    Derek Greene Derek Greene

    40 S Prospect St, Putnam, CT 06260
  • 66 Bebbington Rd, Ashford, CT 06278
    66 Bebbington Rd, Ashford, CT 06278
    66 Bebbington Rd, Ashford, CT 06278
    /39

    $2,995,000

    • 5 Beds
    • 4.5 Baths
    • 5,977 Sq Ft

    66 Bebbington Rd, Ashford, CT 06278

    PROMINENT 55-ACRE EQUESTRIAN FACILITY w/PRIMARY 6,000SF RESIDENCE w/2 APARTMENTS! Nestled amid a peaceful countryside, this exceptional horse property presents a rare opportunity to acquire a versatile estate that seamlessly combines elegant residential living w/impressive equestrian facilities. A turnkey sanctuary for those seeking solitude, sophistication, & functionality. A private gated entry

    Kiara Rusconi William Raveis Real Estate

    66 Bebbington Rd, Ashford, CT 06278
  • 34-38 Plainfield Rd, Plainfield, CT 06354

    $275,000 Sold Aug 07, 2025

    • 3,332 Sq Ft
    • $83/SF
    • 1 Day On Market
    • 7 Beds
    • 4 Baths
    • Built 1870

    34-38 Plainfield Rd, Plainfield, CT 06354

    Estate 3 family waterfront on MOOSUP RIVER handyman special! One unit will be available June 1st 3-4 bedrooms. Other 2 units have 2 bedrooms each and CITY WATER /SEWER on 3.2 ACRES w/ ENORMOUS 1368 sq ft BARN w/ basement. LARGE lot for parking. Farmers porch along the front and tenants are month to month, responsible for their own water, oil and electric! Updated boilers multi is in need of

    Christine Johnson RE/MAX One

    34-38 Plainfield Rd, Plainfield, CT 06354
  • 361 Westminster Rd, Canterbury, CT 06331
    361 Westminster Rd, Canterbury, CT 06331
    361 Westminster Rd, Canterbury, CT 06331
    /38

    $375,000

    • 2 Beds
    • 1.5 Baths
    • 1,048 Sq Ft

    361 Westminster Rd, Canterbury, CT 06331

    Step into history with modern comfort at 361 Westminster Road in Canterbury, CT. Originally built in 1800, this beautifully restored 2-bedroom, 1.5-bath home blends classic New England character with thoughtful updates throughout. Featuring brand-new flooring, fresh paint, a new roof, and ductless air conditioning units, this home is completely move-in ready. The updated kitchen showcases butcher

    Adam Gumula Kazantzis Real Estate, LLC

    361 Westminster Rd, Canterbury, CT 06331
  • 103 Reilly Rd, Hampton, CT 06247

    $450,000 Sold Aug 07, 2025

    • 1,800 Sq Ft
    • $250/SF
    • 1 Day On Market
    • 4 Beds
    • 3 Baths
    • Built 2025

    103 Reilly Rd, Hampton, CT 06247

    GORGEOUS 2025 Raised Ranch with OPEN FLOOR Plan has living/ dining area and STAINLESS APPLIANCES in Kitchen w/ white shaker cabinets, GRANITE counters and ISLAND. HARDWOOD throughout, carpet in bedrooms and lower level bedroom. CENTRAL Air/ forced hot air, one year warranty. 3 bedrooms on main level with 2 full bathrooms and lower level has a bedroom a family room, Laundry and a FULL bathroom

    Christine Johnson RE/MAX One

    103 Reilly Rd, Hampton, CT 06247
  • 30 Tyrone Rd, Pomfret Center, CT 06259
    30 Tyrone Rd, Pomfret Center, CT 06259
    30 Tyrone Rd, Pomfret Center, CT 06259
    /40

    $1,375,000

    • 4 Beds
    • 6 Baths
    • 4,907 Sq Ft

    30 Tyrone Rd, Pomfret Center, CT 06259

    Welcome to 30 Tyrone Road, Pomfret Center, CT. 4 Beds | 4 Full Baths | 2 Half Baths | Nearly 5,000 Sq Ft | 3.13 Acres- Set on over 3 acres in the heart of Pomfret Center, this newly built custom home offers nearly 5000 square feet of thoughtfully designed living space with panoramic scenic views and exceptional craftsmanship throughout. This property is the perfect balance of luxury,

    Jennifer Mahr RE/MAX Bell Park Realty

    30 Tyrone Rd, Pomfret Center, CT 06259
  • 64 Spaulding Rd, Plainfield, CT 06374

    $510,000 Sold Aug 06, 2025

    • 1,200 Sq Ft
    • $425/SF
    • 7 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1984

    64 Spaulding Rd, Plainfield, CT 06374

    Welcome to this beautifully maintained one level ranch sitting on a serene 22.54 acres of land! This beautiful property abuts the 25 acre state forest! This property is 2 separate lots, the back lot has 40ft right away and has already been perked. Front lot (that the home sits on) also has site perked are well for a future addition. Both lots are 11.27 each. This home features 3 beds & 1 bath.

    Skyla Gagnon RE/MAX Bell Park Realty

    64 Spaulding Rd, Plainfield, CT 06374
  • 23 Little Bungee Hill Rd, Woodstock Valley, CT 06282
    23 Little Bungee Hill Rd, Woodstock Valley, CT 06282
    23 Little Bungee Hill Rd, Woodstock Valley, CT 06282
    /40

    $595,000

    • 4 Beds
    • 2 Baths
    • 2,160 Sq Ft

    23 Little Bungee Hill Rd, Woodstock Valley, CT 06282

    The pictures really tell the story with this one. Down a quiet road on a 1.22 acre lot within sight of Lake Bunggee, this 2160 sq ft, 4 Br, 2 Ba home has been rebuilt from the floor joists up. Rich with custom touches and all new electrical, plumbing, insulation, roofing, etc. Pull up the double wide driveway (paved in 2023) to a two car garage (575 sq ft, plus loft), where you'll never get

    Alan Berman Signature Properties of NewEng

    23 Little Bungee Hill Rd, Woodstock Valley, CT 06282
  • 126 Labby Rd, North Grosvenordale, CT 06255

    $380,000 Sold Aug 06, 2025

    • 1,152 Sq Ft
    • $330/SF
    • 7 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1988

    126 Labby Rd, North Grosvenordale, CT 06255

    Welcome to Labby Road in beautiful Thompson, Connecticut! This raised ranch offers three bedrooms and one and a half bathrooms, along with plenty of additional storage space to meet your needs. As you step through the front door, you'll be greeted by a spacious living room that flows seamlessly into the dining area-perfect for entertaining or everyday living. The kitchen is just off the dining

    Linda Desaulniers The Neighborhood Realty Group

    126 Labby Rd, North Grosvenordale, CT 06255
  • 842 Hartford Pike, Dayville, CT 06241
    842 Hartford Pike, Dayville, CT 06241
    /2

    $2,816,000

    • Land
    • 11 Acres
    • $256,000 per Acre

    842 Hartford Pike, Dayville, CT 06241

    Property is basically level and gently sloping, Ideal site for development of Professional or Medical offices, Dental, Clinics, Retail outlets, Restaurants, Multi-Family units, Also by "Special Permit" Banks, Hotels & Motels, Self service storage facilities, distribution centers etc. See Sections 430 & 420.1 of the Killingly Zoning Regulations for a more comprehensive lists of permitted uses

    Derek Greene Derek Greene

    842 Hartford Pike, Dayville, CT 06241

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