29

Woodbury, CT Homes for Sale

Section Image Section Image
  • /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
  • /40

    $890,000

    • 4 Beds
    • 2.5 Baths
    • 3,736 Sq Ft

    84 Hurds Hill Rd, Woodbury, CT 06798

    Welcome to Woodbury! This stunning 3,736 sq ft single-family estate sits gracefully on over 11 acres, offering the perfect blend of refined luxury and serene countryside living. Step inside to discover a spacious, light-filled interior designed for both grand entertaining and comfortable everyday living. With four generously sized bedrooms, multiple living areas, and fine architectural details

    Michael Vartolone William Raveis Real Estate

    84 Hurds Hill Rd, Woodbury, CT 06798
  • /38

    $774,900

    • 6 Beds
    • 3 Baths
    • 4,245 Sq Ft

    94 Old Town Farm Rd, Woodbury, CT 06798

    This charming colonial style barn conversion, originally built in the early 1900s, offers 6 beds, 3 full baths, and spans 4,245 square feet on a picturesque 1.59 acre lot. Rich in character, the home showcases original architectural details including a hand carved front door, exposed wood beams, wide plank floors, cabin style latches, and more. The spacious wraparound kitchen with a center island

    Dylan Longmuir eXp Realty

    94 Old Town Farm Rd, Woodbury, CT 06798
  • /40

    $1,275,000

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

    373 Transylvania Rd, Woodbury, CT 06798

    Custom-built. This unique home is made for entertaining. 4000 ft.2 home with 3 bedroom suites each containing its own full bath. 5 Bathrooms. 3 Fireplaces. Chef's kitchen with granite counters, double ovens, bow window w/bench seat & walk out to deck. Formal dining room has tray ceiling. Great room with fireplace and full bar. Den/library has fireplace. Bright piano room/sunroom/office also walks

    Beatriz Conroy William Raveis Real Estate

    373 Transylvania Rd, Woodbury, CT 06798
  • /40

    $875,000

    • 4 Beds
    • 2.5 Baths
    • 2,519 Sq Ft

    77 Northgate Rd, Woodbury, CT 06798

    Nestled in one of Woodbury's most sought-after enclaves, 77 North Gate Rd epitomizes refined living. This meticulously updated 4-bedroom, 2.5-bathroom residence spans approximately 2,519 square feet, offering a harmonious blend of modern sophistication and timeless charm. Constructed in 2016, the home's contemporary design is complemented by high-end finishes and an open-concept layout that

    Jason Arcuri eXp Realty

    77 Northgate Rd, Woodbury, CT 06798
  • /39

    $950,000

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

    148 Flanders Rd, Woodbury, CT 06798

    Come home to a unique 3082 sqft, one of a kind custom built Barn home all set on 5 secluded acres. Featuring an open floor plan, 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 spacious Dining Room area & slider leading to

    Ron Nettleton William Raveis Real Estate

    148 Flanders Rd, Woodbury, CT 06798
  • /30

    $1,075,000

    • 4 Beds
    • 4 Baths
    • 5,781 Sq Ft

    16 Gate Post Ln, Woodbury, CT 06798

    LIMITED TIME OFFERED AT THIS PRICE!! ACT NOW!!! This elegant Colonial in Carriage Hills features approximately 5700 sqft of living space, including a walk-out lower level suitable for an in-law suite. The main level has wood floors, formal living and dining rooms, an eat-in kitchen, bedroom, a full bath, and a family room with a fireplace leading to an oversized deck. Upstairs, there are three

    Sindy Butkus Klemm Real Estate Inc

    16 Gate Post Ln, Woodbury, CT 06798
  • /15

    $990,000 New Construction

    • 3 Beds
    • 2 Baths
    • 2,300 Sq Ft

    523 Main St N, Woodbury, CT 06798

    To be built Modern style home with gorgeous southern views and privacy from your neighbors. Enjoy the wall of glass overlooking a bluestone patio, and beautiful views above Main Street North! Just a few minutes from Woodbury's town center, this home provides an open floor with a kitchen/great room, a cathedral ceiling, and a floor-to-ceiling masonry fireplace. The first floor includes a primary

    Tim Drakeley Drakeley Real Estate, Inc.

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

    $895,000 Open Sat 11AM - 1PM

    • 4 Beds
    • 3.5 Baths
    • 3,320 Sq Ft

    LOT#8 Wolf Hill Rd, Watertown, CT 06795

    The feel of country living-just minutes from all of life's conveniences! This stunning new construction offers the perfect blend of luxury and functionality through thoughtful design. Featuring a first-floor master bedroom suite with a spa-like soaking tub, and a second-floor master suite with vaulted ceilings, this home is ideal for multi-generational living or growing families. Step inside to

    Ken Demirs Regency Real Estate, LLC

    LOT#8 Wolf Hill Rd, Watertown, CT 06795
  • /28

    $777,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,550 Sq Ft

    LOT#9 Wolf Hill Rd, Watertown, CT 06795

    This Beautiful Farmhouse Colonial is the last home to be built in the sought-after Wolf Hill subdivision. Nestled on a peaceful cul-de-sac, this seven-room, four-bedroom home features an open floor plan with approximately 2,500 sq ft of living space. The first floor features a luxurious master bedroom suite with a walk-in closet and a full bath. The large eat-in kitchen, complete with an island,

    Ken Demirs Regency Real Estate, LLC

    LOT#9 Wolf Hill Rd, Watertown, CT 06795
  • /36

    $699,000

    • 4 Beds
    • 2.5 Baths
    • 2,506 Sq Ft

    329 Weekeepeemee Rd, Woodbury, CT 06798

    Welcome to your North Woodbury bucolic retreat! Escape from it all, nestled along the banks of the Weekeepeemee River with southern views and sunsets falling over the open fields, Heron fishing only yards from your Adirondack chair and Eagles perched on the nearby trees. Yes, this is Home. This 1780 Colonial has been well cared for, for many decades. The first floor offers a large updated

    Tom Slekis Berkshire Hathaway NE Prop.

    329 Weekeepeemee Rd, Woodbury, CT 06798
  • /7

    $129,900

    • 1 Bed
    • 1 Bath
    • 546 Sq Ft

    16 Pilgrim Trail Unit 3, Woodbury, CT 06798

    First floor 1 bedroom unit in very good condition. Newer cabinets with granite countertops and hardwood floors. Heat, hot water, trash, snow removal, and grounds maintenance included. Occupied by long term tenant on month to month lease.

    Carlo Bettini Weichert REALTORS Briotti Group

    16 Pilgrim Trail Unit 3, Woodbury, CT 06798
  • /40

    $1,950,000

    • 5 Beds
    • 6 Baths
    • 7,413 Sq Ft

    39 Quanopaug Trail, Woodbury, CT 06798

    Exceptionally constructed contemporary set on almost 9 acres with a beautiful view of distant hilltops. Both the house and the outdoor spaces are truly impressive, perfect for entertaining and nature lovers. With over 7,500 sq ft, the home is spacious with exposed beams, an abundance of windows and many updates & upgrades. The public rooms are open and airy encompassing the kitchen, dining and

    Maria Taylor Klemm Real Estate Inc

    39 Quanopaug Trail, Woodbury, CT 06798
  • /13

    $184,000

    • 2 Beds
    • 1 Bath
    • 913 Sq Ft

    229 Bacon Pond Rd Unit 132, Woodbury, CT 06798

    Ready for immediate occupancy in Woodbury's Town in Country community is this freshly painted two bedroom, one bath condominium with new laminate floors throughout, a new oven/range, microwave and dishwasher. Sliders in the living room lead to a patio with a sun-lit, open view. A great opportunity to live in one of Connecticut's favorite towns.

    Tom Greto William Raveis Real Estate

    229 Bacon Pond Rd Unit 132, Woodbury, CT 06798
  • /13

    $675,000

    • Land
    • 23 Acres
    • $29,348 per Acre

    0 Cowles Rd, Woodbury, CT 06798

    Presenting a rare opportunity to acquire a 23-acre parcel that has been held within a family for generations. This expansive property, fronting on a tranquil county road, offers a serene and private setting for your future endeavors. The property is a picturesque combination of woodlands, offering an idyllic setting for those seeking privacy and connection to nature. With approximately 800 feet

    John Sniffen William Pitt Sotheby's Int'l

    0 Cowles Rd, Woodbury, CT 06798
  • /9

    $439,900

    • 2 Beds
    • 2.5 Baths
    • 1,796 Sq Ft

    23 Woodbury Hill, Woodbury, CT 06798

    Perhaps the most desirable condominium complex in Woodbury, Woodbury Hill offers a quiet, beautiful, rural location, yet is close to shopping and accessible to major routes. This Putnam's Loft offers a spacious, open entertaining area with living room open to dining room with oak flooring, fireplace and lots of light. The updated kitchen provides access to the deck overlooking rear property. With

    Donna Bannon BHGRE Bannon & Hebert

    23 Woodbury Hill, Woodbury, CT 06798
  • /40

    $525,000 Open Sun 1PM - 3PM

    • 6 Beds
    • 7 Baths
    • 9,296 Sq Ft

    59 Hillside Rd, Woodbury, CT 06798

    Auction Opportunity. Please review FAQ and Property Information Package included in the additional documents on MLS (you may have to request these directly from your agent or the auction company). Asking Price is Opening Bid only. Final price will be determined by competitive bidding. All bidding online, opening April 23 at 4pm and ending April 30 at 4pm. Bidding website available upon request. ~

    Samantha Kelley Tranzon Auction Properties

    59 Hillside Rd, Woodbury, CT 06798
  • /32

    $349,900

    • 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
  • /37

    $1,675,000

    • 4 Beds
    • 3 Baths
    • 2,418 Sq Ft

    39 Painter Hill Rd, Woodbury, CT 06798

    Stunning Renovated Antique Home with Scenic Views & Luxurious Amenities, Discover the perfect blend of historic charm and modern luxury in this totally renovated antique home, and Barn set on 9.44 picturesque acres bordering 20 acres of Land Trust. This home offers 4 bedrooms, 3 full baths, and exquisite craftsmanship throughout. Step inside to find new wide plank floors, recessed lighting,

    Julie Tsai William Raveis Real Estate

    39 Painter Hill Rd, Woodbury, CT 06798
  • /14

    $324,500

    • 4 Beds
    • 1 Bath
    • 1,505 Sq Ft

    9 White Deer Rocks Rd, Woodbury, CT 06798

    Nestled in lovely Woodbury and in a gorgeous neighborhood, a spacious colonial that requires a little TLC to bring it back to life. A contractor's dream. No Access - Please do not disturb occupant or walk on the property. There are no previews allowed. Please do not disturb occupant. Drive by preview only. Please do not park in driveway nor walk the property. Seller has never occupied the

    Jaida Li Keller Williams Realty

    9 White Deer Rocks Rd, Woodbury, CT 06798
  • /38

    $2,100,000

    • 4 Beds
    • 4.5 Baths
    • 4,517 Sq Ft

    225 Old Sherman Hill Rd, Woodbury, CT 06798

    A long winding drive leads you to Four Winds Farm. Perched on the hill, this remarkable 33.98-acre property includes a 4,500 sq ft, 11 room, 4 bedrooms, 4.1 bath residence as well as a home for your horses. The contemporary house has many updates throughout, cathedral ceilings, tall windows, multiple sliders to exterior entertainment areas and spacious deck. There is central air, a security

    Maria Taylor Klemm Real Estate Inc

    225 Old Sherman Hill Rd, Woodbury, CT 06798
  • /6

    $119,900

    • Land
    • 2.10 Acres
    • $57,095 per Acre

    0 Main St N Unit 24072843, Woodbury, CT 06798

    Residential lot of record on Main Street North, Woodbury. A private lot with the potential for distant views over the cornfields in the Nonnewaug Valley. An ideal location within a few minutes to Woodbury's historic downtown and 5 to 10 minutes to Bethlehem and Watertown town centers.

    Tim Drakeley Drakeley Real Estate, Inc.

    0 Main St N Unit 24072843, Woodbury, CT 06798
  • /7

    $339,500

    • 3 Beds
    • 1 Bath
    • 1,080 Sq Ft

    54 Mountain Rd, Woodbury, CT 06798

    House is half finished. Seller has completed much of downstairs including kitchen and living area but still a work in progress. Downstairs is all open with a loft upstairs. Great value and beautiful surroundings sits on half an acre. Worth a look ! There are no disclosures and will not go FHA Woodbury is a beautiful town, make this house your own...

    Gayle Forster Century 21 AllPoints Realty

    54 Mountain Rd, Woodbury, CT 06798
  • /26

    $699,900

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

    27 Middle Quarter Rd, Woodbury, CT 06798

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

    Tim Drakeley Drakeley Real Estate, Inc.

    27 Middle Quarter Rd, Woodbury, CT 06798
  • /6

    $195,000

    • Land
    • 9 Acres
    • $21,036 per Acre

    14 Roxbury Rd, Woodbury, CT 06798

    In The Hills of Lichfield County! Fantastic Opportunity to Build Your Dream Home w/ Lots of Privacy on this Wooded 9.27 Acres of Nature & Tranquility. Enjoy the Sounds of Transylvania Brook that Flows through this Property. Located in The Overbrook Subdivision of Woodbury. Woodbury named " Most Charming Small Town" by Reader's Digest! Near Roxbury Line and Scenic Route 67 and only 90 Minutes to

    Debbie Kranidis Preston Gray Real Estate

    14 Roxbury Rd, Woodbury, CT 06798
  • /11

    $400,000

    • Land
    • 25 Acres
    • $15,804 per Acre

    00-1055 Main St N, Woodbury, CT 06798

    VIEWS: Wonderful views for a home site or farm. Possible two points of entrance. Buyer is responsible for due diligence and approvals. The property runs behind 1053 Main Street North and is contiguous to 867 Main Street North. Approximately 25.31 acres. AVAILABLE IN ATT. DOCS: Dated: 1) Revised lot line survey. 2) Perked results. 3) Soil tests. 4) Elevations

    John Gould W. Raveis Lifestyles Realty

    00-1055 Main St N, Woodbury, CT 06798
  • /2

    $399,900

    • Land
    • 56 Acres
    • $7,104 per Acre

    0 Main St N Unit 24072824, Woodbury, CT 06798

    56 acres in the heart of Woodbury. The perfect spot for a compound or subdivide and create an open space subdivision or a few large parcels. Potential for terrific views over the Nonnewaug Valley. Located a few minutes from downtown and 5 minutes from Nonnewaug High School. Build your dream house and enjoy the views!

    Tim Drakeley Drakeley Real Estate, Inc.

    0 Main St N Unit 24072824, Woodbury, CT 06798
  • /2

    $729,900 Coming Soon

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

    38 Barnhill Rd, Woodbury, CT 06798

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

    Donna Bannon BHGRE Bannon & Hebert

    38 Barnhill Rd, Woodbury, CT 06798
  • /40

    $569,900

    • 2 Beds
    • 2.5 Baths
    • 2,593 Sq Ft

    112 Periwinkle Dr Unit 112, Middlebury, CT 06762

    Welcome to Benson Woods - an exclusive community of 78 single-family homes designed for active adults. This beautifully maintained home boasts an open floor plan, featuring a great room with a cozy fireplace and soaring cathedral ceilings. The eat-in kitchen is a chef's delight, complete with a spacious island, dining area, white shaker-style cabinets, granite countertops, and a stylish tile

    Mary Ann Hebert BHGRE Bannon & Hebert

    112 Periwinkle Dr Unit 112, Middlebury, CT 06762

About Woodbury

Fittingly for a town founded more than 100 years before the birth of the United States, Woodbury is known as the “Antiques Capital of Connecticut.” But while the town, established in 1673, may be old in a chronological sense, it also has a vibrant present. With its assortment of restaurants, shopping and outdoor amenities – not to mention its proximity to Route 6 – Woodbury has plenty of modern conveniences to make clear the fact that the town is more than just a destination for those seeking vintage items. "Woodbury has a lot going for it," sa ...

Frequently Asked Questions

What is the average home price in Woodbury, CT?
Homes for sale in Woodbury, CT have an average home price of $579,547.
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 06488, 06010, 06776, 06810 and 06511.
How much do you need to make to afford a house in Woodbury?
The median home price in Woodbury is $494,500. If you put a 20% down payment of $98,900 and had a 30-year fixed mortgage with an interest rate of 6.83%, your estimated principal and interest payment would be $2,590 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $111K a year to afford the median home price in Woodbury.
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 Pomperaug Regional High School, Shepaug Valley School and Long Meadow Elementary School. Browse all the schools in Woodbury, CT to learn more.

Home Trends in Woodbury, CT

Home Trends

Median Price (12 Mo)
$445,000
Median Single Family Price
$650,000
Median Townhouse Price
$330,000
Median 2 Bedroom Price
$190,000
Median 1 Bedroom Price
$114,500
Average Price Per Sq Ft
$254
Number of Homes for Sale
20
Last 12 months Home Sales
145
Months of Supply
1.70
Median List Price
$494,500
Median Discount From 1st List Price
3%
Median Home Sale Price YoY Change
12%
How to Buy a Home How to Finance a Home How to Sell a Home