13

Woodbury, CT Homes for Sale with Acreage

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  • /36

    $759,900

    • 3 Beds
    • 3 Baths
    • 2,420 Sq Ft

    220 Upper Grassy Hill Rd, Woodbury, CT 06798

    Recently renovated from the studs up, this single-family ranch on the Woodbury/Roxbury town line offers the rare chance to own a truly like-new home with immediate availability. This three-bedroom home features all-new electrical, HVAC, spray-foam insulation, trim, drywall, hardwood floors, a beautifully updated kitchen, and three brand-new bathrooms. The main level offers a spacious layout with

    Agent Photo

    Tim Drakeley

    Drakeley Real Estate, Inc.

    (203) 902-5178

    220 Upper Grassy Hill Rd, Woodbury, CT 06798
  • /26

    $999,900

    • 3 Beds
    • 2.5 Baths
    • 2,042 Sq Ft

    27 Middle Quarter Rd, Woodbury, CT 06798

    Discover the charm of this beautiful antique home in the heart of Woodbury! Nestled on the serene Middle Quarter Road, this vintage gem is being restored by the current owner and is just a 2-minute stroll from coffee shops, top-notch restaurants, and the historic Main Street. The home will be meticulously updated from the ground up, featuring wide board antique flooring, a stunning great room

    Agent Photo

    Tim Drakeley

    Drakeley Real Estate, Inc.

    (203) 457-8490

    27 Middle Quarter Rd, Woodbury, CT 06798
  • /39

    $1,100,000

    • 4 Beds
    • 2.5 Baths
    • 3,545 Sq Ft

    45 N Gate Rd, Woodbury, CT 06798

    Welcome to Woodbury, a quintessential New England town. This house is located in a very desirable neighborhood, just north of the town center. An inviting covered front porch will greet you. This leads to a 2 story foyer and an open floor plan opens up in front of you! To the left is a formal LR/Den. (cozy up with a good book) To the right is formal Dining Room with a trey ceiling, seats 8-10

    Jeff Colt Showcase Realty, Inc.

    45 N Gate Rd, Woodbury, CT 06798
  • /39

    $1,800,000

    • 2 Beds
    • 3 Baths
    • 2,072 Sq Ft

    76 Cowles Rd, Woodbury, CT 06798

    Rare opportunity to own a spectacular 40-acre equestrian estate designed for exceptional horse care, training, and country living. This property features a 150' x 80' indoor riding arena with excellent lighting and 3 overhead doors, an immaculate 9-stall barn with concrete floors, mats, stall windows, hay racks, hay chute, 3 cross-tie areas, and convenient hay storage with conveyor system.

    Andy Adames William Raveis Real Estate

    76 Cowles Rd, Woodbury, CT 06798
  • /40

    $895,000 Open Sun 12PM - 2PM

    • 4 Beds
    • 3.5 Baths
    • 3,784 Sq Ft

    557 Upper Grassy Hill Rd, Woodbury, CT 06798

    Welcome to Upper Grassy Hill Living!

    Susan Corleto William Pitt Sotheby's Int'l

    557 Upper Grassy Hill Rd, Woodbury, CT 06798
  • /15

    $499,999

    • 3 Beds
    • 2.5 Baths
    • 1,846 Sq Ft

    110 Brushy Hill Rd, Woodbury, CT 06798

    Experience the charm of this classic Cape Cod style property, featuring 3 bedrooms and 2 cozy fireplaces that invite warm gatherings on 1 acre of land perfect for outdoor enjoyment. This country eclectic home blends timeless architecture with modern comfort, offering a serene retreat that captures the essence of country living. Whether you're relaxing by the fire or exploring the great outdoors,

    Jacqueline Voegeli Manzi Real Estate

    110 Brushy Hill Rd, Woodbury, CT 06798
  • /40

    $2,195,000

    • 4 Beds
    • 3.5 Baths
    • 3,551 Sq Ft

    382 Weekeepeemee Rd, Woodbury, CT 06798

    The Jesse Peck Lambert Homestead, built in 1805 & thoughtfully restored, provides a seamless blend of historic charm & modern comfort. Set on 6.42 acres in Northern Woodbury on the Washington border just 2 hours from NYC, this 4-bedroom/3.5-bath home provides a serene escape with timeless appeal. The newly designed kitchen is a chef's dream, featuring custom rift-sawn white oak cabinets, oiled

    Jeff Phillips William Pitt Sotheby's Int'l

    382 Weekeepeemee Rd, Woodbury, CT 06798
  • /34

    $1,925,000

    • 3 Beds
    • 3 Baths
    • 2,992 Sq Ft

    819 Main St N, Woodbury, CT 06798

    Open Meadow Farm, a beautifully maintained property offering a blend of rural charm and modern conveniences. Set on 9.88 picturesque acres, this property features three fenced fields, ideal for horses or other livestock and a two-story barn equipped with four stalls, a tack room, gravel storage area and a gleaming concrete main floor. Recent updates include a paved driveway with turnaround, back

    Sindy Butkus Klemm Real Estate Inc

    819 Main St N, Woodbury, CT 06798
  • /40

    $1,995,000

    • 4 Beds
    • 4.5 Baths
    • 3,324 Sq Ft

    55 Good Hill Rd, Woodbury, CT 06798

    Step into History with Modern Comfort Experience the undeniable charm of this circa 1685 residence-one of the oldest continuously inhabited homes in the county. Thoughtfully restored and beautifully updated, this remarkable property blends centuries of character with today's modern conveniences. Inside, the open floor plan creates a warm and inviting flow, with three cozy sitting rooms

    Stacey Matthews W. Raveis Lifestyles Realty

    55 Good Hill Rd, Woodbury, CT 06798
  • /17

    $479,900

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

    34 Transylvania Rd, Woodbury, CT 06798

    Price Improvement for this Charming Country Retreat- A perfect alternative to Condo Living! Nestled on a serene 3 acre lot with picturesque stream, this property offers the tranquility of country living while maintaining easy access to nearby amenities. One level living- enjoy the convenience of the primary bedroom with spacious walk-in closet on the same level as the open floor plan

    Betsy Rosa Berkshire Hathaway NE Prop.

    34 Transylvania Rd, Woodbury, CT 06798
  • /32

    $314,900

    • 2 Beds
    • 1.5 Baths
    • 1,920 Sq Ft

    439 Washington Rd, Woodbury, CT 06798

    Investors and Contractors take notice! This versatile office space located on close to 10 acres of rural Woodbury land is ripe with opportunity. The 1,920 sqft office can potentially be converted into a single family residential ranch overlooking the babbling Sprain Brook below. Across the brook, with road frontage and access off of Hoop Pole Hill Rd, lies the majority of the acreage with a dry,

    Matthew Amatruda Drakeley Real Estate, Inc.

    439 Washington Rd, Woodbury, CT 06798
  • /19

    $449,000

    • 3 Beds
    • 1 Bath
    • 1,296 Sq Ft

    360 Old Sherman Hill Rd, Woodbury, CT 06798

    Come view this charming 3 bedroom, 2 full bath, single family home in beautiful Woodbury! Enjoy an above ground pool with a deck wrapped around it-perfect for relaxing year round while taking in the sweeping natural views out back. A spacious 2 car detached garage sits in the middle of a large private semi-circular driveway, offering plenty of parking and storage. Upon entering the front of the

    Levi Judqin Brass Moon Realty

    360 Old Sherman Hill Rd, Woodbury, CT 06798
  • /3

    $699,000 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 2,573 Sq Ft

    54 Bear Run, Woodbury, CT 06798

    Fantastic opportunity to own this beautifully maintained 4-bedroom, 2.5-bath Colonial on lovely cul-de-sac neighborhood, privately set back on a wooded lot which backs up to Land Trust in sought-after Bear Run Estates. Proudly offered by its original owners, this home features numerous updates including a high-efficiency propane furnace (2023), central A/C (2024), and whole-house Generac

    Becky Hood William Pitt Sotheby's Int'l

    54 Bear Run, Woodbury, CT 06798

Home Trends in Woodbury, CT

Housing Trends

Median Sale Price
$500,000
Median Single Family Sale Price
$634,500
Median Townhouse Sale Price
$325,000
Median 2 Bedroom Sale Price
$175,000
Median 1 Bedroom Sale Price
$124,250
Average Price Per Sq Ft
$285
Number of Homes for Sale
28
Last 12 months Home Sales
123
Months of Supply
2.70
Median List Price
$499,450
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
9%
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