4,425

Woodstock, CT Homes

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  • 52 Crooked Trail, Woodstock, CT 06281

    $456,000 Sold Jul 24, 2025

    • 1,789 Sq Ft
    • $255/SF
    • 8 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1987

    52 Crooked Trail, Woodstock, CT 06281

    Contemporary Charm Across from Witches Woods Lake! Step into this inviting 3-bedroom, 2.5-bath contemporary home offering a bright open floor plan, soaring vaulted ceilings, and gleaming hardwood floors throughout. Fireplaced living room, applianced kitchen and breakfast bar area, first floor laundry and large deck. Very private lot across from the Witched Woods lake!!. Central air keeps the home

    Cary Marcoux RE/MAX Bell Park Realty

    52 Crooked Trail, Woodstock, CT 06281
  • 381 Bungay Hill Rd, Woodstock, CT 06281
    381 Bungay Hill Rd, Woodstock, CT 06281
    381 Bungay Hill Rd, Woodstock, CT 06281
    /31

    $448,500

    • 4 Beds
    • 1.5 Baths
    • 1,904 Sq Ft

    381 Bungay Hill Rd, Woodstock, CT 06281

    Situated in tranquil Woodstock, this spacious four bedroom Cape is the ultimate hidden treasure. It's calm, tree-lined 4.23 acres opens up to offer a large yard to allow space for all of your outdoor activities. Inside, you will be met with a smooth-flowing layout, 9ft ceilings, and plenty of natural lighting. The first level homes two sizeable bedrooms that transition into the main living space

    Anna Marsh BHHS Realty Professionals

    381 Bungay Hill Rd, Woodstock, CT 06281
  • 50 Perrin Rd, Woodstock, CT 06281

    $587,000 Sold Jul 21, 2025

    • 3,456 Sq Ft
    • $170/SF
    • 200 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 1740

    50 Perrin Rd, Woodstock, CT 06281

    Set on a beautiful and quiet New England roadway, this 1740 antique home is a game changer for those looking for a property that can accommodate small animals! Currently the home for incredibly happy alpacas, sheep, and chickens! The 9 acres are mostly open and include a back pasture and a fenced area, run in and hay barn. There is an inground pool and detached 2-car garage, plus a small building

    Stephanie Gosselin CR Premier Properties

    50 Perrin Rd, Woodstock, CT 06281
  • 6 Meadowside Rd, Woodstock, CT 06281
    6 Meadowside Rd, Woodstock, CT 06281
    6 Meadowside Rd, Woodstock, CT 06281
    /21

    $71,000

    • 2 Beds
    • 1 Bath
    • 775 Sq Ft

    6 Meadowside Rd, Woodstock, CT 06281

    Welcome to beautiful Meadowside of Woodstock, CT Campground, your home away from home! This is a rare opportunity to own your very own campsite along with this 1986 Regal Prowler 34 Model with a custom additional living room/bedroom space that has been added on. Enjoy peace and serenity with this spacious lot bordering the Thompson town line with a beautiful stone wall. Lots of work has been done

    Diane White CR Premier Properties

    6 Meadowside Rd, Woodstock, CT 06281
  • 28 Crooked Trail, Woodstock, CT 06281

    $420,000 Sold Jul 18, 2025

    • 1,612 Sq Ft
    • $261/SF
    • 80 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1984

    28 Crooked Trail, Woodstock, CT 06281

    Welcome to 28 Crooked Trail! Nestled in a tranquil setting near Witches Woods Lake, this beautifully updated contemporary cape is sure to check all your boxes. Step inside & admire a remodeled eat-in kitchen (2022) w/ subway tiles, butcher block countertops and ample cabinet space, opening into a bright and inviting living area perfect for entertaining or unwinding after a day on the water.

    Rich Jenkins Real Broker CT, LLC

    28 Crooked Trail, Woodstock, CT 06281
  • 328 County Rd, Woodstock, CT 06281
    328 County Rd, Woodstock, CT 06281
    328 County Rd, Woodstock, CT 06281
    /35

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,536 Sq Ft

    328 County Rd, Woodstock, CT 06281

    Charming Farmhouse located on a picturesque 1.2 acre corner lot in Woodstock CT! This 3 bedroom, 2 bath home blends historic charm with modern comfort. Featuring hardwood floors throughout, a spacious living room with cozy fireplace, and a large dining room perfect for gatherings. The cozy kitchen opens to a low-maintenance Trex deck, which is ideal for relaxing or entertaining while enjoying

    Shiloh Therrien The Neighborhood Realty Group

    328 County Rd, Woodstock, CT 06281
  • 222 Route 197, Woodstock, CT 06281

    $565,000 Sold Jul 18, 2025

    • 1,952 Sq Ft
    • $289/SF
    • 8 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1991

    222 Route 197, Woodstock, CT 06281

    Tucked away on nearly five acres of natural beauty, this Cape Cod charmer invites you to slow down, breathe deeply, and savor the life you've dreamed about. With 3 bedrooms, 2 full baths, and over 1,950 square feet that live far larger, this home offers the perfect blend of comfort and space to stretch out-both inside and out. Wake up with coffee on the oversized deck as morning light filters

    Brooke Gelhaus Compass Connecticut, LLC

    222 Route 197, Woodstock, CT 06281
  • 285 E Quasset Rd, Woodstock, CT 06281
    285 E Quasset Rd, Woodstock, CT 06281
    285 E Quasset Rd, Woodstock, CT 06281
    /18

    $450,000

    • 4 Beds
    • 1 Bath
    • 1,144 Sq Ft

    285 E Quasset Rd, Woodstock, CT 06281

    Discover the charm of lakeside living on peaceful Quasset Lake in Woodstock, CT. This cozy 4-bedroom, 1-bathroom cottage offers the perfect blend of comfort and country serenity. Set on a 0.84-acre lot with apx. 150 feet of private shoreline, it's an ideal retreat for boating, fishing, or simply enjoying peaceful waterfront views. The finished walk-out lower level extends the living space, making

    Jason Saphire www.HomeZu.com

    285 E Quasset Rd, Woodstock, CT 06281
  • 1340B Connecticut 169, Woodstock, CT 06281
    1340B Connecticut 169, Woodstock, CT 06281
    1340B Connecticut 169, Woodstock, CT 06281
    /24

    $49,900 Sold Jul 13, 2025

    • Land
    • 3.6 Acres
    • $13,861 per Acre
    • 58 Days On Market

    1340B Connecticut 169, Woodstock, CT 06281

    Approved oversized 3.6 acre subdivision lot features privacy & room to roam! For space & protection, this land boasts 396' of road frontage (36' longer than the length of a football field including both end zones)! Horses & ATVs OK. Road frontage boundaries are flagged with ribbons, bordering homes 1310 RT 169, the neighbor to the south, at the corner of stonewall, which further runs west as this

    Dennis Duga Dr. LAND

    1340B Connecticut 169, Woodstock, CT 06281
  • 0 Aplin Hill Ln, Woodstock, CT 06282
    0 Aplin Hill Ln, Woodstock, CT 06282
    0 Aplin Hill Ln, Woodstock, CT 06282
    /7

    $85,000

    • Land
    • 0.88 Acre
    • $96,591 per Acre

    0 Aplin Hill Ln, Woodstock, CT 06282

    The perfect blend of privacy and community. Lot 4 is the only rear lot in this quiet Woodstock Valley cul-de-sac, a rare chance to build in a growing neighborhood while enjoying the privacy of a wooded .88-acre setting. Conservation land borders the northern and eastern edges, creating a natural buffer that sets this lot apart from the rest. With construction now underway on neighboring Lots 3, 5

    Kristen Kaskela Berkshire Hathaway NE Prop.

    0 Aplin Hill Ln, Woodstock, CT 06282
  • 18 Perrin Rd, Woodstock, CT 06281

    $476,500 Sold Jul 11, 2025

    • 2,125 Sq Ft
    • $224/SF
    • 3 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1832

    18 Perrin Rd, Woodstock, CT 06281

    OPEN HOUSE CHANGED TO SUNDAY JUNE 1 11-1 Charming Antique Home on 2.7 manicured acres in Woodstock. Step into timeless elegance with this beautifully maintained home. Bursting with character and modern comforts, this 3 bedroom, 2 full bath residence offers an inviting blend of old world charm and thoughtful updates. Inside, you'll find a graceful flow of living spaces, including a formal living

    Amy Archambault CR Premier Properties

    18 Perrin Rd, Woodstock, CT 06281
  • 76 Mill Brook Ln, Woodstock, CT 06281
    76 Mill Brook Ln, Woodstock, CT 06281
    76 Mill Brook Ln, Woodstock, CT 06281
    /40

    $1,100,000

    • 5 Beds
    • 4 Baths
    • 5,079 Sq Ft

    76 Mill Brook Ln, Woodstock, CT 06281

    Tucked away on 6.5 private acres in the prestigious MillBrook Estates, this 5,000+ sq ft custom home offers an exceptional blend of elegance, functionality, and luxury. A long paved drive leads to this stately residence, featuring 5 bedrooms, multiple living areas, and rich architectural details throughout. The grand foyer with a hydraulic chandelier sets the tone for the craftsmanship found

    Katie Totten William Raveis Real Estate

    76 Mill Brook Ln, Woodstock, CT 06281
  • 519 Route 169, Woodstock, CT 06281

    $500,000 Sold Jul 07, 2025

    • 2,266 Sq Ft
    • $221/SF
    • 92 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1850

    519 Route 169, Woodstock, CT 06281

    Prominently located on prestigious Woodstock Hill, this 1850 Greek Revival Farmhouse sits on the easterly side of the road, enjoying morning sun rises from its two porches! A short walk to The Woodstock Academy, the Woodstock Hill Congregational Church, and The Inn at Woodstock Hill, and just 45 minutes to Harford, 30 minutes to Worcester and 1.15 to Boston you simply cannot ask for a better

    Stephanie Gosselin CR Premier Properties

    519 Route 169, Woodstock, CT 06281
  • 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
  • 133 Calkins Rd, Woodstock, CT 06281

    $670,000 Sold Jun 30, 2025

    • 2,722 Sq Ft
    • $246/SF
    • 7 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 2003

    133 Calkins Rd, Woodstock, CT 06281

    133 Calkins Road, Woodstock, offers a unique blend of classic charm and modern updates. This 3-bedroom, 2.5-bathroom home sits on a picturesque 2.14-acre lot, providing ample space for outdoor enjoyment. The exterior presents a traditional colonial style, while the interior reveals a custom design that sets it apart from typical homes in the area. The property's meticulous landscaping is

    Jennifer Jackson Berkshire Hathaway NE Prop.

    133 Calkins Rd, Woodstock, CT 06281
  • 70 Laurel Hill Dr, Woodstock Valley, CT 06282
    70 Laurel Hill Dr, Woodstock Valley, CT 06282
    70 Laurel Hill Dr, Woodstock Valley, CT 06282
    /29

    $449,900

    • 3 Beds
    • 2.5 Baths
    • 1,682 Sq Ft

    70 Laurel Hill Dr, Woodstock Valley, CT 06282

    Get ready to fall in love with this fully renovated colonial, just one minute from the beach and offering stunning water views! What was once a charming 1,200 sq ft Cape has been recently completely reimagined into a spacious 1,600 sq ft Colonial. This like-new home now boasts 3 bedrooms, 2.5 bathrooms, and a fresh, modern layout perfect for everyday living and entertaining. The heart of the home

    Katelyn Battista Real Broker CT, LLC

    70 Laurel Hill Dr, Woodstock Valley, CT 06282
  • 55 Indian Spring Rd, Woodstock, CT 06281

    $500,000 Sold Jun 27, 2025

    • 1,697 Sq Ft
    • $295/SF
    • 35 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1977

    55 Indian Spring Rd, Woodstock, CT 06281

    Don't miss this opportunity to secure your own lake property for the summer of 2025! Long ago 3 lots were combined to create this oversized 0.90 acre property across from Witches Woods Lake located in Woodstock Valley of northeast CT. A spectacular property for someone looking to have both lake access and enough outdoor space for gardening, pets, entertaining & backyard games. The other unique

    Lindsey L. Niarhakos RE/MAX One

    55 Indian Spring Rd, Woodstock, CT 06281
  • 1669 Route 169, Woodstock, CT 06281
    1669 Route 169, Woodstock, CT 06281
    1669 Route 169, Woodstock, CT 06281
    /39

    $1,250,000

    • 2 Beds
    • 2 Baths
    • 2,340 Sq Ft

    1669 Route 169, Woodstock, CT 06281

    Welcome to Hilltop Meadows-a one-of-a-kind, 60-acre luxury hay farm nestled in Connecticut's scenic "Quiet Corner." Set high above Route 169 in North Woodstock, this breathtaking property offers rolling meadows, mature forests, and serene privacy just 60 miles from Boston and 150 from Manhattan. The heart of the property is a newly updated 2-bed, 2-bath, 2,340 sq ft farmhouse blending historic

    Ryan De Lello William Pitt Sotheby's Internatiomal Realty

    1669 Route 169, Woodstock, CT 06281
  • 53 Andrews Rd, Woodstock, CT 06281

    $400,000 Sold Jun 20, 2025

    • 1,452 Sq Ft
    • $275/SF
    • 2 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1981

    53 Andrews Rd, Woodstock, CT 06281

    Set on nearly 3 peaceful acres in Woodstock, this 4-bedroom Cape offers a flexible layout with three bedrooms on the main level, including the primary, plus a spacious loft-style 4th bedroom upstairs. The home features many recent updates: Pergo flooring in the kitchen and full bath (2022), new dishwasher (2025), water heater (2022), furnace (2019), and a repointed chimney (2021) with liner

    Kristen Kaskela Berkshire Hathaway NE Prop.

    53 Andrews Rd, Woodstock, CT 06281
  • 175 Pulpit Rock Rd, Woodstock, CT 06281
    175 Pulpit Rock Rd, Woodstock, CT 06281
    175 Pulpit Rock Rd, Woodstock, CT 06281
    /39

    $1,836,000

    • 4 Beds
    • 3.5 Baths
    • 5,104 Sq Ft

    175 Pulpit Rock Rd, Woodstock, CT 06281

    A once-in-a-generation opportunity. Please visit this stunning Georgian estate situated on 55 hilltop acres in desirable Woodstock, CT. Enjoy breathtaking long views all the way to Rhode Island! A few of the exceptional assets offered include an elegant in-law apartment, a large 6 stall horse barn with office, an inviting in-ground pool, and 25 acres of fenced open pasture. As you approach the

    John Downs Berkshire Hathaway NE Prop.

    175 Pulpit Rock Rd, Woodstock, CT 06281
  • 25 Connecticut 197, Woodstock, CT 06281

    $28,500 Sold Jun 17, 2025

    • 920 Sq Ft
    • $31/SF
    • 49 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1990

    25 Connecticut 197, Woodstock, CT 06281

    Located in the sought-after Meadowside community, this spacious lot offers the perfect seasonal escape. The property features a newer 12x27 loft-style structure with ample room to accommodate multiple beds, same sized spacious living room area, plus a covered 12x28 area ideal for relaxing or entertaining. Also included is a well-maintained 10x26 1981 camper offering a king-size sleeping area,

    Melanie Taylor Berkshire Hathaway NE Prop.

    25 Connecticut 197, Woodstock, CT 06281
  • 56 Laurel Hill Dr, Woodstock Valley, CT 06282
    56 Laurel Hill Dr, Woodstock Valley, CT 06282
    56 Laurel Hill Dr, Woodstock Valley, CT 06282
    /32

    $475,000

    • 3 Beds
    • 1.5 Baths
    • 1,008 Sq Ft

    56 Laurel Hill Dr, Woodstock Valley, CT 06282

    Charming 3-Bedroom Home on Double Lot - Lake Bunggee Waterfront Access! Discover the potential of this charming 3-bedroom home nestled in the heart of Connecticut's Quiet Corner, just steps from beautiful Lake Bunggee. Set on a spacious double lot, this property is waiting for your personal touches-bring your tools and imagination to make it your own! Enjoy lake life year-round with a walk-out

    Vivian Kozey CR Premier Properties

    56 Laurel Hill Dr, Woodstock Valley, CT 06282
  • 577 Route 197, Woodstock, CT 06281

    $530,000 Sold Jun 13, 2025

    • 1,826 Sq Ft
    • $290/SF
    • 33 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1840

    577 Route 197, Woodstock, CT 06281

    Welcome to this lovingly maintained 1840s farmhouse. Enjoy the large living room with skylights and plenty of windows to bring in the natural light, as well as a wood burning stove to keep you cozy on cold winter nights. Master bedroom and large ensuite can be found on the first floor, along with a cozy bright kitchen, dining room and office/den. Make your way upstairs to an updated bathroom and

    Jacqueline Kapusta Navick Properties LLC

    577 Route 197, Woodstock, CT 06281
  • 00 Prospect St, Woodstock, CT 06281
    00 Prospect St, Woodstock, CT 06281
    /2

    $99,900

    • Land
    • 12 Acres
    • $8,325 per Acre

    00 Prospect St, Woodstock, CT 06281

    Discover the perfect canvas for your dream home or private retreat on this stunning 12-acre parcel located in scenic Woodstock, Connecticut. This unique piece of land offers a peaceful setting with a blend of rolling topography, mature trees, and a beautiful pond-ideal for nature lovers, homesteaders, or anyone seeking privacy and serenity. The land features varied elevations, providing

    Mateusz Chojnicki CR Premier Properties

    00 Prospect St, Woodstock, CT 06281
  • 27 Meehan Rd, Woodstock, CT 06281

    $330,000 Sold Jun 12, 2025

    • 1,300 Sq Ft
    • $254/SF
    • 39 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1960

    27 Meehan Rd, Woodstock, CT 06281

    Situated on 3 scenic acres, this classic ranch-style home offers timeless charm and abundant potential. Being sold as-is, this property presents an excellent opportunity for buyers looking to invest in a solid home with room for customization.The residence features original hardwood floors throughout, while a cozy fireplace creates a welcoming gathering space during cooler months. A spacious

    Jamie Meadows William Raveis Real Estate

    27 Meehan Rd, Woodstock, CT 06281
  • 130 Tripp Rd, Woodstock, CT 06281
    130 Tripp Rd, Woodstock, CT 06281
    130 Tripp Rd, Woodstock, CT 06281
    /21

    $338,000 Pending

    • 2 Beds
    • 1 Bath
    • 1,222 Sq Ft

    130 Tripp Rd, Woodstock, CT 06281

    Great location in South Woodstock, if being close to town is important. Live comfortably in this 2 bedroom, one bath ranch with the addition that adds a great room with access to the 2 car garage. The lower level has potential for another finished room. The windows and siding were replace about 15 years ago, and the roof is one year old. The rear deck is small, but private, and the yard is level.

    Lynn Converse RE/MAX Bell Park Realty

    130 Tripp Rd, Woodstock, CT 06281
  • XOXO Connecticut 169, Woodstock, CT 06281

    $49,900 Sold Jun 12, 2025

    • Land
    • 3.6 Acres
    • $13,861 per Acre
    • 305 Days On Market

    XOXO Connecticut 169, Woodstock, CT 06281

    Approved oversized 3.6 acre subdivision lot features privacy & room to roam! For space & protection, this land boasts 396' of road frontage (36' longer than the length of a football field including both end zones)! Horses & ATVs OK. Road frontage boundaries are flagged with ribbons, bordering homes 1310 RT 169, the neighbor to the south, at the corner of stonewall, which further runs west as this

    Dennis Duga Northeast Realty

    XOXO Connecticut 169, Woodstock, CT 06281

Showing Results 81 - 120, Page 3 of 18

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