27

Woodbury, CT Homes for Sale

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  • /26

    $1,100,000

    • 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

    $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
  • /25

    $299,990

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

    4 Fox Run Unit 4, Woodbury, CT 06798

    Welcome to this beautifully refreshed townhome in the highly desirable Woodlake Condominium Complex in Woodbury. Freshly painted throughout and filled with natural light, the main level features hardwood floors, a spacious living and dining area with a cozy fireplace, and a sliding door that opens to a private deck overlooking peaceful wooded surroundings. The updated kitchen includes granite

    Henrik K Kjaer Keller Williams Realty

    4 Fox Run Unit 4, 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
  • /40

    $649,900 Open Sun 1PM - 3PM

    • 3 Beds
    • 2.5 Baths
    • 2,264 Sq Ft

    13 Park Ln, Woodbury, CT 06798

    Set on a picturesque lot with mature landscaping and gorgeous outdoor spaces, this beautifully maintained home offers a flexible layout designed for both entertaining and everyday living. The front entry opens to a bright and inviting living room with built-ins and gas fireplace. The kitchen blends style and function with granite countertops, stainless appliances, and a natural flow into the

    Michael Wright RE/MAX Right Choice

    13 Park Ln, Woodbury, CT 06798
  • /23

    $675,000

    • 3 Beds
    • 2.5 Baths
    • 2,835 Sq Ft

    38 Barnhill Rd, Woodbury, CT 06798

    If you are looking for peace and tranquility, you will find it here in this expansive cape. Located on a quiet country road, it provides the privacy and tranquility as well as great spaces for a variety of lifestyles. For preparing great meals, this oversized kitchen is just the place. Enjoy friends and family as you prepare & dine. Spill over into the 25' x 22' family room with custom

    Donna Bannon BHGRE Gaetano Marra Homes

    38 Barnhill 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
  • /32

    $574,900

    • 4 Beds
    • 2.5 Baths
    • 2,256 Sq Ft

    31 McVeigh Rd, Woodbury, CT 06798

    Welcome home to 31 McVeigh Rd! Privately set on 1.70 acres in the Quassapaug neighborhood, this home blends comfort, efficiency, and convenience. The living room offers a wood-burning fireplace, while a 2019 high-efficiency wood stove in the family room adds warmth and helps lower heating costs. The main level features connected yet distinct spaces-living room, family room, dining area, and a

    Jennifer Bundock Coldwell Banker Realty

    31 McVeigh Rd, Woodbury, CT 06798
  • /23

    $550,000

    • 4 Beds
    • 2 Baths
    • 1,987 Sq Ft

    667 Upper Grassy Hill Rd, Woodbury, CT 06798

    Discover this meticulously maintained Cape-style home set on 3.4 private acres in Woodbury. The property offers exceptional curb appeal, featuring a paved circular driveway and a classic stone wall that sets a welcoming tone. Inside, a beautiful slate tile foyer opens to hardwood floors and a comfortable, well-designed layout that creates an inviting atmosphere. The main level includes a

    Rhya Szymansky Drakeley Real Estate, Inc.

    667 Upper Grassy Hill Rd, Woodbury, CT 06798
  • /38

    $519,000

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

    9 Hill View Ln, Woodbury, CT 06798

    Charming Dutch Colonial located in the desirable South Brook community in Woodbury, walking distance from the bustling shops and restaurants. This home is part of a small enclave of 21 single, detached residences. Features include a new wood roof, hardwood floors throughout, and a private backyard with patio. The first floor offers a formal dining room, an eat-in kitchen with ample cabinet and

    Christina Zainc BHGRE Gaetano Marra Homes

    9 Hill View Ln, Woodbury, CT 06798
  • /27

    $265,000

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

    5 Upper Commons, Woodbury, CT 06798

    Welcome to 5 Upper Commons, a well-maintained 2-bedroom farmhouse-style townhouse set in a quiet, wooded community with walking trails. This home offers three finished levels and a comfortable, functional layout. The main level features an open living and dining area and a practical kitchen with good cabinet space. Central air provides year-round comfort. Upstairs, both bedrooms include walk-in

    Rafael Monegro Coldwell Banker Realty

    5 Upper Commons, 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
  • /9

    $335,000

    • 3 Beds
    • 1 Bath
    • 1,089 Sq Ft

    54 Mountain Rd, Woodbury, CT 06798

    Welcome to the Historic town of Woodbury! Don't miss the opportunity to own this beautiful and well maintained home which offers a functional layout and abundant natural light. Features include spacious living areas, a well-appointed kitchen, comfortable bedrooms and a private outdoor space ideal for relaxing or entertaining. Conveniently located near schools, shopping, and major routes. A

    Genesis Hernandez BHGRE Shore & Country

    54 Mountain Rd, Woodbury, CT 06798
  • /21

    $355,000

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

    8 Tamarack Ln Unit 8, Woodbury, CT 06798

    Unique opportunity! This spacious end-unit condo offers 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 kitchen

    Jennifer Mayo William Raveis Real Estate

    8 Tamarack Ln Unit 8, Woodbury, CT 06798
  • /40

    $1,275,000

    • 3 Beds
    • 5 Baths
    • 4,059 Sq Ft

    373 Transylvania Rd, Woodbury, CT 06798

    This unique allergy free home is made for entertaining. 4000 ft. home with 3 bedroom suites each containing its own full bath. Total of 5 Bathrooms. 3 Fireplaces. Chef's kitchen with granite counters, double ovens, center island, bow window w/bench seat & walk out to solid mahogany wood deck. Formal dining room has tray ceiling. Living room with fireplace and full bar. Bright piano

    Beatriz Conroy William Raveis Real Estate

    373 Transylvania 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
  • /21

    $749,900

    • 4 Beds
    • 4 Baths
    • 2,980 Sq Ft

    432 Quassapaug Rd, Woodbury, CT 06798

    Welcome to Eastfield Farms Etates. This Colonial features an open floor plan for comfortable everyday living an entertaining alike. The large foyer flows to both the formal living room with french doors and formal dining room. Both with crown molding and accent lighting. Just down the hall step into the spacious kitchen with center island, granite counter tops stainless appliances. The dining

    Ray Manzi Manzi Real Estate

    432 Quassapaug Rd, Woodbury, CT 06798
  • /40

    $377,750

    • 3 Beds
    • 2.5 Baths
    • 2,069 Sq Ft

    2 South Meadows Unit 107B, Woodbury, CT 06798

    Welcome Home to your new 2026 dream home! This beautiful, peaceful, calm upscale residence, offers 3 Levels of quiet elegance. Move in & enjoy the vacation at home..."Woodlake Life Style". Each room is thoughtfully purposed and decorated with a classy style. The kitchen spacious "open" concept, with Corian countertops. Cherry toned flooring adds a warm welcome to the first floor, as does the

    Terry Lee Adams Adams & Adams Real Estate

    2 South Meadows Unit 107B, Woodbury, CT 06798
  • /27

    $215,000

    • 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
  • /39

    $710,000 Open Sat 11AM - 1PM

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

    74 Middle Quarter Rd, Woodbury, CT 06798

    Welcome to a piece of New England history-an 1835 Farmhouse lovingly updated for today's living while preserving all its timeless charm. Set on 4.7 acres with a sun-kissed field framed by quiet woodlands, this property offers the perfect balance of country serenity and in-town convenience. From here, you can stroll into the heart of Woodbury, known for its storybook charm, delightful restaurants,

    Heather Crabtree RE/MAX RISE

    74 Middle Quarter 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
  • /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
  • /35

    $599,000

    • 3 Beds
    • 3 Baths
    • 2,227 Sq Ft

    105 Minortown Rd, Woodbury, CT 06798

    NEW PRICE! Don't wait! This ranch-style home might be the perfect fit! Just minutes from town, the property offers a variety of opportunities. The main level features three bedrooms, two bathrooms, a living room with a gas log fireplace, a formal dining room, and a spacious eat-in kitchen. The partially finished lower level includes a family room, office space, and a full bath. Built in 2008, the

    Sindy Butkus Klemm Real Estate Inc

    105 Minortown Rd, Woodbury, CT 06798
  • /38

    $350,000

    • 2 Beds
    • 2 Baths
    • 1,267 Sq Ft

    10 Hazel Plain Rd, Woodbury, CT 06798

    Welcome to Sweet River Cottage, a charming riverside retreat offering the perfect blend of comfort, character, and natural beauty. This inviting 2-3 bedroom, 2 full bath home sits just steps from the water's edge, providing peaceful views and the soothing sound of the river year-round. Inside, you'll find a warm and welcoming eat-in kitchen, ideal for casual meals or gathering with friends. Enjoy

    Wendy Brazauskas Coldwell Banker Realty

    10 Hazel Plain Rd, Woodbury, CT 06798
  • /19

    $499,000

    • 3 Beds
    • 2 Baths
    • 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

    $749,000

    • 3 Beds
    • 3.5 Baths
    • 3,749 Sq Ft

    19 Hillview Ln, Woodbury, CT 06798

    Nestled within the exclusive South Brook community, 19 Hill View Lane offers timeless New England charm paired with exceptional craftsmanship. This beautifully appointed 3 bedroom, 3.5 bath cape colonial is rich in architectural detail, featuring refined millwork, quality finishes, and a thoughtful layout designed for both everyday living and elegant entertaining. The main living spaces flow

    Nicole Fiorelli Fiorelli Realty, LLC

    19 Hillview Ln, Woodbury, CT 06798
  • /36

    $850,000 Open House 1/25

    • 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

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 $554,915.
How many homes have sold over the last 12 months in Woodbury, CT?
145 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, 06762, 06751 and 06795.
How much do you need to make to afford a house in Woodbury?
The median home price in Woodbury is $492,450. If you put a 20% down payment of $98,500 and had a 30-year fixed mortgage with an interest rate of 6.16%, your estimated principal and interest payment would be $2,400 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $103K 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
$456,000
Median Single Family Sale Price
$629,000
Median Townhouse Sale Price
$340,000
Median 2 Bedroom Sale Price
$182,500
Median 1 Bedroom Sale Price
$120,000
Average Price Per Sq Ft
$266
Number of Homes for Sale
26
Last 12 months Home Sales
145
Months of Supply
2.20
Median List Price
$492,450
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
-5%
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