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Woodstock, CT Homes for Sale with Acreage

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  • /40

    $649,900

    • 4 Beds
    • 2.5 Baths
    • 2,682 Sq Ft

    37 Pulpit Rock Rd, Woodstock, CT 06281

    Location, location, location! Tucked away on a quiet scenic road just steps from historic Woodstock Hill and Woodstock Academy, this classic Colonial offers 2,682 sq. ft. of timeless charm on 1.6 acres-one of the most desirable and private settings in Woodstock. Inside, wide-plank oak floors, exposed beams, and two fireplaces create a warm and inviting atmosphere. The open kitchen and dining

    Agent Photo

    Carol Ryniewicz

    CR Premier Properties

    (860) 854-3110

    37 Pulpit Rock Rd, Woodstock, CT 06281
  • /12

    $235,000

    • Land
    • 5 Acres
    • $45,988 per Acre

    00 Joy Rd, Woodstock, CT 06281

    "Life is a Joy on Joy Road" Nestled in the heart of Woodstock, CT, this stunning 5.11-acre building lot offers the perfect balance of peaceful seclusion and easy access to modern conveniences. Surrounded by lush woodlands and gently rolling terrain, this property provides an idyllic setting for your dream home, offering privacy, natural beauty, and a connection to nature. Despite its serene

    Agent Photo

    Elizabeth Scranton

    Kazantzis Real Estate, LLC

    (860) 846-4563

    00 Joy Rd, Woodstock, CT 06281
  • /11

    $925,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 3,500 Sq Ft

    0 Joy Rd, Woodstock, CT 06281

    Luxury Ranch-Style Home To Be Built by DHS Copeland Builders - Woodstock, Ct Offered on a Private 5-Acre Parcel - Bring Your Plans or Use Ours! Discover the perfect blend of elegance and tranquility with this to-be-built luxury ranch-style home by the renowned DHS Copeland Builders. Centrally located in the heart of Woodstock, CT, this rare 5-acre parcel offers the ideal canvas for your dream

    Agent Photo

    Elizabeth Scranton

    Kazantzis Real Estate, LLC

    (860) 813-2921

    0 Joy Rd, Woodstock, CT 06281
  • /16

    $895,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 3,356 Sq Ft

    36 Olde Meadow Rd, Woodstock, CT 06281

    Welcome to Eastwood Estates - Luxury Living in the Heart of Woodstock! Discover the elegance and tranquility of Eastwood Estates, a prestigious enclave of just eight finer homes nestled in one of Woodstock's most desirable settings. This 3,356 sq ft Colonial TO BE BUILT is thoughtfully designed for those seeking timeless sophistication, quality craftsmanship, and a connection to nature. With 18

    Agent Photo

    Tina Lajoie

    William Raveis Real Estate

    (860) 374-2832

    36 Olde Meadow Rd, Woodstock, CT 06281
  • /40

    $715,000 Open Sat 12PM - 2PM

    • 4 Beds
    • 3.5 Baths
    • 4,536 Sq Ft

    101 Center Rd, Woodstock, CT 06281

    This beautiful sprawling custom colonial is set on 9 acres of land at the end of a winding long driveway and surrounded by open area. Grand living spaces with cathedral ceilings and a floor to ceiling fireplace, tons of natural light, 4 bedrooms & 3.5 bathrooms, a 1500 sqft in-law suite with additional bedroom, new appliances, spacious 2 car garage, and an out building with electricity and

    Jeff Valentine William Pitt Sotheby's Int'l

    101 Center Rd, 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
  • /34

    $550,000

    • 3 Beds
    • 2.5 Baths
    • 2,362 Sq Ft

    359 Barlow Cemetery Rd, Woodstock, CT 06281

    Welcome to 359 Barlow Cemetery Rd - a truly one-of-a-kind property set on 3.2 scenic acres that lead to the peaceful waters of Bungee Brook. This spacious home offers a versatile layout, featuring a large primary bedroom suite, two additional bedrooms, and a generous supplemental room on the upper level-perfect for a home office, gym, or guest space. The fully finished basement is an

    Adam Gumula Kazantzis Real Estate, LLC

    359 Barlow Cemetery Rd, Woodstock, CT 06281
  • /40

    $599,900

    • 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
  • /31

    $1,250,000

    • 3 Beds
    • 2.5 Baths
    • 3,983 Sq Ft

    584 Prospect St, Woodstock, CT 06281

    For those who belong to the land. Over 100 acres of private, usable terrain at the CT/MA line, Bear Hill Estate is a fully realized lifestyle retreat for the discerning equestrian or outdoor enthusiast, with effortless access to I-395, I-84, and the Mass Pike. At its heart sits a 3 bed, 2.5 bath custom log home-crafted from white pine logs hand-felled in Nova Scotia, where the bespoke cabinetry

    Jennie Kesselman Berkshire Hathaway NE Prop.

    584 Prospect St, Woodstock, CT 06281
  • /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
  • /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 Int'l

    1669 Route 169, Woodstock, CT 06281
  • /40

    $659,999

    • 3 Beds
    • 3.5 Baths
    • 3,078 Sq Ft

    39 Grey Fox Landing, Woodstock, CT 06281

    This meticulously cared-for Colonial is nestled in a desirable neighborhood and offers the perfect blend of comfort and versatility. The spacious room above the garage has been beautifully finished, making it ideal for an in-law suite, guest space, or bonus room. The kitchen features granite countertops, stainless steel appliances(all approximately 5 years old), and flows seamlessly into the main

    Andrea Kazantzis, CCIM Kazantzis Real Estate, LLC

    39 Grey Fox Landing, Woodstock, CT 06281
  • /27

    $325,000

    • 2 Beds
    • 1 Bath
    • 1,125 Sq Ft

    28 Oak Dr, Woodstock Valley, CT 06282

    LAKE LIFE IN WOODSTOCK. This charming year-round home in Woodstock, CT, offers a unique opportunity to embrace a peaceful lake lifestyle. Built in 1955, the residence sits on a generous 1.1-acre multi-tiered lot, providing ample privacy and seasonal lake views. KEY FEATURES: Deeded Beach Rights: Enjoy direct access to Bungee Lake with deeded beach rights, including access to association beaches

    Donna Copeland William Raveis Real Estate

    28 Oak Dr, Woodstock Valley, CT 06282
  • /36

    $575,000

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

    104 Pulpit Rock Rd, Woodstock, CT 06281

    This 4 Bedroom 2.5 bath meticulously maintained Colonial style home offers a seamless blend of classic charm and modern comfort creating an inviting and functional living environment. High ceilings and abundant natural light illuminate the rich engineered wood floors and detailed crown molding throughout. Enjoy this beautiful kitchen featuring custom Brunarhans cabinetry and granite countertops,

    Belinda Culp Berkshire Hathaway NE Prop.

    104 Pulpit Rock Rd, Woodstock, CT 06281
  • /39

    $1,986,000

    • 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
  • /40

    $679,000 Open Sun 1PM - 3PM

    • 3 Beds
    • 2 Baths
    • 2,669 Sq Ft

    402 Perrin Rd, Woodstock, CT 06281

    Welcome to this charming 2.7-acre property, where functionality meets potential. Perfectly suited for horse enthusiasts, this small yet mighty property provides endless possibilities-whether you're looking to house your own horses, run a boarding business, or provide training. The beautifully remodeled antique home exudes warmth and character, featuring a cozy living room with a wood stove, a

    Kelly Ryan William Raveis Real Estate

    402 Perrin Rd, 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
  • /2

    $99,000

    • Land
    • 10 Acres
    • $10,270 per Acre

    0 Rt 198, Woodstock, CT 06281

    This beautiful laurel-rich hard and soft wood land has wide frontage on CT 198 and on town road Pole Bridge Road, making this an easily accessible home sites. Property is sold AS-IS, contingent on clear title. There is a special permit for a commercial Building. Septic plan and building design are at the Town Hall. Please note: there is not yet driveway access to this property.

    Nicole Gleason CR Premier Properties

    0 Rt 198, Woodstock, CT 06281
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