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Woodbury, CT Homes for Sale

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  • /40

    $899,900

    • 4 Beds
    • 2.5 Baths
    • 3,700 Sq Ft

    337 Main St S, Woodbury, CT 06798

    A Real Classic! Beautifully renovated with many original features. Located in the Historic District in the heart of Woodbury. Stroll along Main Street to parks, excellent restaurants, house of worship, conveniences and antique shops. Home is just lovely with exposed beams, wide board hardwood floors, 4 fireplaces, outside on the patio, primary bedroom, dining room and living room. One fireplace

    Agent Photo

    Marian Van Egas

    Berkshire Hathaway NE Prop.

    (475) 255-3184

    337 Main St S, 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
  • /40

    $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
  • /16

    $849,000

    • 3 Beds
    • 4 Baths
    • 3,082 Sq Ft

    148 Flanders Rd, Woodbury, CT 06798

    Country Living Abounds with this unique custom built one of a kind Cape nestled on 5 secluded acres. This home features an open floor plan with post and beam construction, beamed ceilings, oak floors, Plaster Walls, fully applianced Kitchen with breakfast bar, a spacious Family Room with brick fireplace, built-ins, & slider leading to back deck. The Living Room with fireplace is adjacent to a

    Ron Nettleton William Raveis Real Estate

    148 Flanders 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
  • /36

    $850,000

    • 5 Beds
    • 3.5 Baths
    • 3,033 Sq Ft

    20 Cowles Rd, Bethlehem, CT 06751

    This beautiful meticulous cape built in 2001 looks brand new with 5 bedrooms-the master is on the first floor with master bath-and 4 bedrooms on the second floor. All the rooms have hardwood floors and the large eat-in kitchen was just remodeled. Enjoy the oversized front porch securely hidden from the road as well as the back deck overlooking the large, level grounds with plenty of privacy. This

    Joyce Drakeley Drakeley Real Estate, Inc.

    20 Cowles Rd, Bethlehem, CT 06751
  • /36

    $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
  • /38

    $259,900 Coming Soon

    • 2 Beds
    • 2 Baths
    • 1,182 Sq Ft

    1 Upper Commons Unit 1, Woodbury, CT 06798

    Welcome to 1 Upper Commons, Woodbury - a beautifully sized 2-bedroom, 2-bath townhome offering approximately 1,182 square feet of comfortable, low-maintenance living in one of Litchfield County's charming communities. An elegant townhome offering comfort, flexibility, and exceptional value in a sought-after, beautiful community, with a woodsy, welcoming country setting and Pond access for this

    Odaine Jones GLR ESTATES LLC

    1 Upper Commons Unit 1, 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
  • /40

    $499,000

    • 3 Beds
    • 1.5 Baths
    • 2,102 Sq Ft

    14 Meadow Crest Dr, Woodbury, CT 06798

    Opportunity knocks! Your chance to reside in an exclusive cul-de-sac area of north Woodbury! Homes on this street rarely come on the market. Situated on almost 4.5 acres and within a short drive of Woodbury and Watertown centers, including prestigious, private Taft School, this three bedroom, 1.5 bath colonial awaits its new owners! Exterior features include a chicken coop, above ground pool,

    Katherine Parlato Drakeley Real Estate, Inc.

    14 Meadow Crest Dr, Woodbury, CT 06798
  • /21

    $355,000

    • 2 Beds
    • 2 Baths
    • 2,118 Sq Ft

    8 Tamarack Ln Unit 8, Woodbury, CT 06798

    3 bedrooms on 2 levels in this spacious end-unit condo offering 2118 ft of comfort, style, and a peaceful setting. Although listed as a 2-bedroom, the expansive heated and cooled lower level features additional rooms, one currently used as a bedroom with a closet, a large family room, plus a storage room, and a laundry room! Many options for a home office or gym. On the main level, the updated

    Jennifer Mayo William Raveis Real Estate

    8 Tamarack Ln Unit 8, Woodbury, CT 06798
  • /20

    $245,000

    • 2 Beds
    • 2.5 Baths
    • 1,983 Sq Ft

    14 Tamarack Ln, Woodbury, CT 06798

    Opportunity awaits in this end unit tucked away in the Woodlake Complex. While in need of some work & new paint colors, there are some nice improvements already in place such as newer windows, wood & tile flooring, & kitchen cabinets. This unit has both a deck & patio overlooking the treed rear yard. Both are accessible from rear sliders. The lower level is finished & has a half bath within the

    Gina Jacobs Gina Jacobs Real Estate

    14 Tamarack Ln, Woodbury, CT 06798
  • /38

    $275,000

    • 2 Beds
    • 2 Baths
    • 1,182 Sq Ft

    9 Highpoint Ct Unit 116E, Woodbury, CT 06798

    Owner occupied and thoughtfully maintained since August of 2000. A perfect 1st or 2nd. home. Included: one car garage, plus one assigned parking space, a deck and patio for grilling. Notice the wooded privacy in the back. Inside a convenient kitchen, a breakfast nook (Or computer area etc.) There is a large living/dining room combo. The Fireplace is sealed shut for safety. However, w/permits, you

    Terry Lee Adams Adams & Adams Real Estate

    9 Highpoint Ct Unit 116E, 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
  • /17

    $499,000

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

    34 Transylvania Rd, Woodbury, CT 06798

    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 kitchen/dining/livingroom. The lower

    Betsy Rosa Berkshire Hathaway NE Prop.

    34 Transylvania Rd, Woodbury, CT 06798
  • /38

    $450,000

    • 3 Beds
    • 2 Baths
    • 1,620 Sq Ft

    133 White Deer Rocks Rd, Woodbury, CT 06798

    Price adjusted to accommodate cosmetic updates. Newer Beckett boiler, C/A, oil tank, and roof is approx. 9-10 years old! This unique, 1997 ranch-style home is set beautifully on nearly 2 acres of mostly level, private land with small pond in Historic Woodbury! The open floor plan of this home offers abundant natural light with a spacious eat-in kitchen, granite countertops, ample cabinetry,

    Michelle Pavia William Raveis Real Estate

    133 White Deer Rocks 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
  • /22

    $249,000

    • 2 Beds
    • 2 Baths
    • 1,182 Sq Ft

    47 Woods Way Unit 47, Woodbury, CT 06798

    This Country House model, end unit in Woodbury's Woodlake community offers two spacious bedrooms, with their own full baths, a detached one car garage and open floor plan on the main level. The Woodlake community provides non-motorized boating on the lake, hiking trails, basketball, tennis courts, and a playground area to name a few. The full unfinished basement offers more storage space. New

    Katherine Parlato Drakeley Real Estate, Inc.

    47 Woods Way Unit 47, Woodbury, CT 06798
  • /27

    $200,000

    • 2 Beds
    • 1 Bath
    • 1,150 Sq Ft

    126 Sherman Hill Rd Unit B12, Woodbury, CT 06798

    This second level unit offers a living and dining combo, kitchen, two bedrooms and one full bath. Upstairs units have vaulted ceilings & additional windows that allow for even more daylight and sense of space. A floor to ceiling brick fireplace will draw you in the winter and a modern curved wall, as you enter the door, adds so much character. The complex offers an in-ground pool. HOA Includes

    Tiffany Clark RE/MAX Right Choice

    126 Sherman Hill Rd Unit B12, 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
  • /38

    $289,900

    • 2 Beds
    • 2 Baths
    • 1,457 Sq Ft

    9 Upper Commons Unit 9, Woodbury, CT 06798

    Welcome to 9 Upper Commons, Woodbury - Tucked away in a quiet, well-maintained community surrounded by mature trees and walking trails, this inviting 2-bedroom townhouse offers three levels for a comfortable, functional lifestyle. The main level features a spacious open-concept floor plan, ideal for everyday living or entertaining. Sliding doors off the dining area leads to your private

    Athan Zeno William Raveis Real Estate

    9 Upper Commons Unit 9, Woodbury, CT 06798
  • /24

    $315,000 Coming Soon

    • 2 Beds
    • 2 Baths
    • 1,542 Sq Ft

    24 Fox Run, Woodbury, CT 06798

    The works been done, now come and enjoy this recently renovated Country House model! Wood floors on the main level, Updated kitchen, Fireplace is decorative only. Spacious bedrooms, two full baths, deck and garage. For those who qualify there is an assumable 2.99% financing available. WOW Opportunity Knocks.

    Sindy Butkus Klemm Real Estate Inc

    24 Fox Run, 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
  • /27

    $304,900

    • 2 Beds
    • 3.5 Baths
    • 1,762 Sq Ft

    13 Clubhouse Dr Unit 13, Woodbury, CT 06798

    Welcome to this well-maintained 3-level condo in the desirable Woodlake community. This spacious unit offers 2 bedrooms, 3 full baths and 1 half bath, plenty of natural light, and a large private deck off the main living area. The kitchen features stainless steel appliances, with washer and dryer conveniently located on the upper level. A fully finished walkout lower level with a full bathroom

    Lance Camby Robert C White & Company LLC

    13 Clubhouse Dr Unit 13, Woodbury, CT 06798

Why Live in Woodbury

Woodbury, CT, established in 1673, is renowned as the "Antiques Capital of Connecticut," with over 50 antiques dealers offering a range of items from trinkets to 18th-century furniture. The town's historic charm is complemented by modern amenities, including a variety of dining options such as the 1754 House and Woodbury Brewing Co., which also serves as a nightlife hub with live music and events. Outdoor enthusiasts can explore Orenaug Park, featuring a fire tower with panoramic views of the Pomperaug River Valley, and Hollow Park, which hosts community events like the annual Fire Department Carnival. The Flanders Nature Center & Land Trust provides educational programs and extensive trails across 2,100 acres. Woodbury's residential areas showcase a mix of historic saltbox-style Colonials and Cape Cods alongside contemporary homes, often situated on multi-acre lots. The town is served by Regional School District 14, with schools earning solid ratings, and the highly-rated Kent School nearby. Community events are frequent, with holiday gatherings at Hollow Park and literary events at the Woodbury Library. The town's proximity to Route 6 ensures convenient commuting, while maintaining a somewhat rural atmosphere.

Frequently Asked Questions

What is the average home price in Woodbury, CT?
Homes for sale in Woodbury, CT have an average home price of $587,650.
How many homes have sold over the last 12 months in Woodbury, CT?
130 homes have sold in Woodbury, CT over the last 12 months.
What are the most popular zip codes in Woodbury, CT?
The most popular zip codes in Woodbury, CT include 06798, 06783, 06751, 06795 and 06762.
How much do you need to make to afford a house in Woodbury?
The median home price in Woodbury is $499,900. If you put a 20% down payment of $100,000 and had a 30-year fixed mortgage with an interest rate of 6.11%, your estimated principal and interest payment would be $2,430 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $104K a year to afford the median home price in Woodbury. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Woodbury, CT?
Woodbury, CT has highly rated public and private schools. Some of the best schools in Woodbury based on Niche Grades are The Taft School, Westover School and The Woodhall School. Browse all the schools in Woodbury, CT to learn more.

Home Trends in Woodbury, CT

Housing Trends

Median Sale Price
$507,500
Median Single Family Sale Price
$640,000
Median Townhouse Sale Price
$314,950
Median 2 Bedroom Sale Price
$183,250
Median 1 Bedroom Sale Price
$124,250
Average Price Per Sq Ft
$270
Number of Homes for Sale
22
Last 12 months Home Sales
130
Months of Supply
2.00
Median List Price
$499,900
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
9%
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