18

Woodbury, CT Homes for Sale with No HOA Fee

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  • /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
  • /38

    $475,000

    • 4 Beds
    • 1 Bath
    • 1,836 Sq Ft

    242 Bacon Pond Rd, Woodbury, CT 06798

    Charming antique home in the heart of Woodbury with a separate legal 700 sq. ft. apartment over the detached 2-car garage, offering excellent rental income potential. Full of vintage character, this special property features wide board antique flooring, original details, built-ins, and three fireplaces, including one in the cozy eat-in kitchen. Set on a gorgeous long, treed in-town lot, the

    Agent Photo

    Tim Drakeley

    Drakeley Real Estate, Inc.

    (475) 882-8908

    242 Bacon Pond 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

    An incredible and rare opportunity awaits on this stunning 40-acre estate. Are you looking for a property that offers exceptional horse care, professional-level training facilities for dressage, show jumping, and cross-country, all set in a private and serene setting? You've found the right place. This remarkable equestrian property is thoughtfully designed for both serious riders and horse

    Andy Adames William Raveis Real Estate

    76 Cowles Rd, Woodbury, CT 06798
  • /40

    $684,000 Open Sat 11AM - 1PM

    • 4 Beds
    • 2.5 Baths
    • 2,874 Sq Ft

    74 Middle Quarter Rd, Woodbury, CT 06798

    Welcome to 74 Middle Quarter Rd-minutes from downtown, a charming antique colonial home that has been truly loved and thoughtfully maintained, offering the perfect blend of character, space, and everyday comfort. From the moment you step inside, you'll feel the warmth of the main level, featuring a farmhouse-style kitchen with an eat-in area and a cozy wood-burning stove-the kind of space where

    Jennifer Kelley Compass Connecticut, LLC

    74 Middle Quarter Rd, Woodbury, CT 06798
  • /34

    $499,000

    • 3 Beds
    • 2 Baths
    • 1,548 Sq Ft

    6 Weekeepeemee Rd, Woodbury, CT 06798

    Step back in time as you enter this enchanting 1846 cottage, where history and modern comfort blend seamlessly. Wide-board wood floors and exposed hand-hewn beams welcome you the moment you arrive, guiding you through rooms filled with character and warmth. The open-concept kitchen features a stainless steel gas stove and dishwasher, charming display cabinets, a farmhouse sink, and a delightful

    Dawn Hough Coldwell Banker Realty

    6 Weekeepeemee Rd, Woodbury, CT 06798
  • /40

    $895,000 Open House 4/12

    • 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
  • /39

    $419,000

    • 3 Beds
    • 2 Baths
    • 1,716 Sq Ft

    40 Church St, Woodbury, CT 06798

    Beautiful 3-bedroom, 2-bath home located in the heart of Woodbury. Currently the only raised ranch on the market, this property offers a wonderful opportunity in a highly desirable area. The home features a level yard, perfect for outdoor enjoyment, along with a fully finished basement complete with a full bath-ideal for entertaining or providing comfortable space for guests. The main level

    Juliana Suzio RE/MAX RISE

    40 Church St, 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
  • /40

    $799,000

    • 3 Beds
    • 2 Baths
    • 2,448 Sq Ft

    92 Minortown Rd, Woodbury, CT 06798

    Charming Gentleman's Farm on 5.76 Acres. Welcome to this beautifully maintained gentleman's farm, perfectly set on 5.76 level acres of open pasture and riding space. Ideal for horse enthusiasts, the property features four barns with a total of 10 stalls, two wash stalls, and a 20x60 meter riding arena with quality stone dust and sand footing. The grounds offer a wonderful mix of functionality and

    Heather Crabtree RE/MAX RISE

    92 Minortown 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
  • /2

    $400,000

    • Land
    • 0.51 Acre
    • $784,314 per Acre

    1545 Main St N, Woodbury, CT 06798

    Rare Main Street commercial property available in Woodbury, CT. The land and the building upon it are being sold in "as is, where is" condition. Neither the probate court system, the attorney, or the broker have any knowledge as to any deficiencies on the property or if they even exist Located in the OS 60 zone, interested parties should consult with the planning and zoning to verify their

    Mario Longobucco Coldwell Banker Commercial NRT

    1545 Main St N, 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
$621,750
Median Townhouse Sale Price
$330,000
Median 2 Bedroom Sale Price
$175,000
Median 1 Bedroom Sale Price
$124,250
Average Price Per Sq Ft
$277
Number of Homes for Sale
26
Last 12 months Home Sales
123
Months of Supply
2.50
Median List Price
$497,000
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
8%
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