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Woodbury Center, CT Homes for Sale with Acreage

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  • /21

    $600,000

    • 9 Beds
    • 8 Baths
    • 4,492 Sq Ft

    137 & 141 Main St S, Woodbury, CT 06798

    Rare mixed-use investment opportunity on over an acre along Woodbury's desirable Main Street South. This unique property features a seven-unit residential building, a detached garage with an additional apartment above, and a separate commercial building offering approximately 2,000 square feet with its own dedicated entrance and access. Three of the residential units are currently occupied, while

    Taylor O'Keefe Drakeley Real Estate, Inc.

    137 & 141 Main St S, Woodbury, CT 06798
  • /37

    $699,000

    • 4 Beds
    • 1.5 Baths
    • 1,872 Sq Ft

    126 Main St N, Woodbury, CT 06798

    Classic 1930s Colonial set along Main Street in Woodbury, offering the timeless character and craftsmanship of the era. Thoughtfully set back from the road on an expansive lawn, the home features hardwood floors throughout, high ceilings, detailed moldings, interior French doors, charming built-ins, a generous foyer, and a graceful central staircase. The front-to-back living room is anchored by a

    Tim Drakeley Drakeley Real Estate, Inc.

    126 Main St N, Woodbury, CT 06798
  • /2

    $1,395,000

    $100K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 4,884 Sq Ft

    30 Hollow Rd, Woodbury, CT 06798

    Step through the doors of history and into one of Connecticut's most treasured colonial residences. Built in 1760 and proudly listed on the National Register of Historic Places, the Jabez Bacon House is a rare masterpiece of 18th-century American architecture that has endured with remarkable grace for over 260 years. This distinguished home has also been recognized for its exceptional

    Lisa Titcomb William Pitt Sotheby's Int'l

    30 Hollow Rd, Woodbury, CT 06798
  • /20

    $749,900

    $25K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,708 Sq Ft

    28 School St, Woodbury, CT 06798

    The Orton-Martin Homestead. One of Woodbury's oldest homes has been updated for today's lifestyle. History surrounds you with wide board flooring, library built-ins, two fireplaces and 1850 barn. This four -bedroom home offers spacious rooms, three finished levels and hidden delights. Enjoy picnics under the mature trees on your own fenced-in level yard. Sidewalks take you everywhere on Main St

    Sindy Butkus Klemm Real Estate Inc

    28 School St, Woodbury, CT 06798
  • /35

    $895,000

    • 4 Beds
    • 2.5 Baths
    • 2,283 Sq Ft

    253 Bacon Pond Rd, Woodbury, CT 06798

    Welcome to Bacon Pond House. A seamless blend of 19th-century soul and 21st-century luxury. Situated on over 3 acres, this antique Colonial has been thoughtfully revived to honor its heritage while offering every modern convenience. The interior, lovingly brought back to life, features wide-plank flooring and exposed hand-hewn beams that anchor the home's historic character. The rooms are

    Christian Jensen William Pitt Sotheby's Int'l

    253 Bacon Pond Rd, Woodbury, CT 06798
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