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Woodbury, CT Homes for Sale with Acreage

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  • /35

    $625,000 Open Sat 12PM - 4PM

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

    31 McVeigh Rd, Woodbury, CT 06798

    Privately nestled on 1.70 acres in the desirable Quassapaug neighborhood, this beautiful Colonial offers the perfect combination of peace, practicality, & modern style, all while providing both privacy and convenience. Inside, the home has been upgraded for year-round energy efficiency, featuring new blown-in insulation, new baseboard heaters, & updated thermostats. For added warmth in the colder

    Agent Photo

    Jennifer Bundock

    Coldwell Banker Realty

    (203) 457-6837

    31 McVeigh Rd, Woodbury, CT 06798
  • /37

    $824,900

    • 4 Beds
    • 3.5 Baths
    • 3,726 Sq Ft

    181 Railtree Hill Rd, Woodbury, CT 06798

    Beautifully constructed and perched atop a scenic 3+ acre lot, this stately gambrel colonial is just a 5-minute drive from charming downtown Woodbury. Offering 4 to 5 bedrooms, this home features everything one would expect in almost 3400 square feet of living space; a formal dining room, a large front-to-back living room with a fireplace and hardwood floors, and a spacious eat-in kitchen with a

    Agent Photo

    Tim Drakeley

    Drakeley Real Estate, Inc.

    (475) 473-8503

    181 Railtree 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.

    Agent Photo

    Tim Drakeley

    Drakeley Real Estate, Inc.

    (475) 447-1659

    0 Main St N Unit 24072843, 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 beautiful antique home in the heart of Woodbury! Nestled on the serene Middle Quarter Road, this vintage gem in need of restoration 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 with a cathedral

    Agent Photo

    Tim Drakeley

    Drakeley Real Estate, Inc.

    (475) 291-4564

    27 Middle Quarter Rd, 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!

    Agent Photo

    Tim Drakeley

    Drakeley Real Estate, Inc.

    (475) 255-2991

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

    $414,900 Coming Soon

    • 2 Beds
    • 1 Bath
    • 1,134 Sq Ft

    27 Scratchville Rd, Woodbury, CT 06798

    This charming home has just been refreshed with recent updates, including a brand new full bathroom, reworked floor plan, fresh paint, and thoughtful touches throughout to enhance functionality and flow. It features a newer roof, beautiful cedar shingles, a generator, two separate storage sheds, and an attached 24x11 workshop. A separate barn/garage and privacy fencing add even more appeal, while

    Agent Photo

    Tim Drakeley

    Drakeley Real Estate, Inc.

    (203) 941-4457

    27 Scratchville 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

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    Marian Van Egas

    Berkshire Hathaway NE Prop.

    (475) 255-3184

    337 Main St S, 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

    Agent Photo

    Tim Drakeley

    Drakeley Real Estate, Inc.

    (475) 284-8768

    523 Main St N, Woodbury, CT 06798
  • /37

    $974,000 Open Sun 1PM - 3PM

    • 5 Beds
    • 3 Baths
    • 3,450 Sq Ft

    364 Hoop Pole Hill Rd, Woodbury, CT 06798

    Private 3-Acre Retreat! Tucked away on a peaceful and private 3-acre lot, this beautifully maintained 5-bedroom, 3-bath home offers the perfect blend of luxury, space, and functionality-with over 3,450 sq ft of living space designed for comfort and entertaining.The main level features a flexible layout with either a first-floor primary suite and office or two spacious bedrooms, offering options

    Kary Apanovitch Coldwell Banker Realty

    364 Hoop Pole Hill Rd, Woodbury, CT 06798
  • /27

    $1,125,000

    • 4 Beds
    • 5.5 Baths
    • 4,214 Sq Ft

    35 Coach Light Dr, Woodbury, CT 06798

    Lovely well maintained colonial just minutes to town. The dramatic double height entry invites you into the main living area which opens to the stunning luxury kitchen and sunny breakfast nook. The living room boasts a stone fireplace flanked by a picture window for enjoying sunset views. The main floor is completed by an addl den/media room and a formal dining room. Upstairs the primary suite

    Stacey Matthews W. Raveis Lifestyles Realty

    35 Coach Light Dr, Woodbury, CT 06798
  • /40

    $949,900

    • 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
  • /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

    $875,000

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

    84 Hurds Hill Rd, Woodbury, CT 06798

    Welcome to Woodbury! Rebuilt in 1991, 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

    Michael Vartolone William Raveis Real Estate

    84 Hurds Hill 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

    $850,000

    • 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
  • /22

    $520,000

    • 4 Beds
    • 3.5 Baths
    • 3,350 Sq Ft

    173 Railtree Hill Rd, Woodbury, CT 06798

    This well-appointed Colonial offers four spacious bedrooms and is set on a secluded lot for added privacy. The front-to-back living room features built-in shelving and a classic fireplace. A sunlit main-level family room includes a raised-hearth fireplace and expansive windows. The primary suite offers French doors leading to a covered porch overlooking the private backyard-ideal for quiet

    Lawrence Madow Calcagni Real Estate

    173 Railtree Hill Rd, Woodbury, CT 06798
  • /35

    $650,000

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

    105 Minortown Rd, Woodbury, CT 06798

    Looking for space? Need a workshop? Collect cars? Need room for the in-laws? 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

    Sindy Butkus Klemm Real Estate Inc

    105 Minortown Rd, Woodbury, CT 06798
  • /40

    $2,495,000

    • 4 Beds
    • 3.5 Baths
    • 6,459 Sq Ft

    562 Upper Grassy Hill Rd, Woodbury, CT 06798

    Shingle style home with horse barn, paddocks & riding arena, set on over 9 acres with a gorgeous westerly view of Roxbury's bucolic rolling hills! This property is an equestrian's dream. Horse barn w 5 stalls w waterers. 2nd level in barn loft for additional space. 6 horse paddocks w waterers & electric fence. Perfectly set riding arena w views. Built in 2013, no expense was spared on the

    John Donato Jr Showcase Realty, Inc.

    562 Upper Grassy Hill Rd, Woodbury, CT 06798
  • /40

    $649,900

    • 3 Beds
    • 2.5 Baths
    • 2,124 Sq Ft

    130 Grassy Hill Rd, Woodbury, CT 06798

    Majestically perched on 2+ private acres, this beautifully maintained three-bedroom Colonial offers seasonal panoramic views of rolling hills and treetops, providing a picturesque year-round backdrop while being close to town. Thoughtfully updated with modern finishes, this home blends comfort and style with ease. Step into the inviting Great Room, where soaring ceilings with exposed beams,

    Wendy Brazauskas Coldwell Banker Realty

    130 Grassy Hill Rd, Woodbury, CT 06798
  • /40

    $559,900

    • 4 Beds
    • 2.5 Baths
    • 2,555 Sq Ft

    467 Weekeepeemee Rd, Woodbury, CT 06798

    Experience the true essence of country living in this classic Saltbox Colonial, perfectly situated on 2.5 acres of peaceful, wooded land in picturesque Woodbury. Surrounded by nature's beauty, this home offers a tranquil retreat. Inside, gleaming HW floors flow throughout a timeless layout designed for comfortable living and relaxed entertaining. The spacious eat-in kitchen features a welcoming

    Tammy Powling Coldwell Banker Realty

    467 Weekeepeemee Rd, Woodbury, CT 06798
  • /39

    $585,000

    • 4 Beds
    • 3 Baths
    • 2,861 Sq Ft

    212 Main St N, Woodbury, CT 06798

    Charming antique home in the heart of Woodbury! Set on a spacious, cleared lot, this beautifully maintained property offers a perfect mix of historic character and modern updates. The kitchen features quartz countertops, stainless steel appliances, and ample cabinetry. With three full baths and a large primary suite with walk-in closet and private bath, comfort and convenience abound. Enjoy the

    Heather Crabtree Coldwell Banker Realty

    212 Main St N, Woodbury, CT 06798
  • /23

    $729,900

    • 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

    $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

    $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
  • /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

    $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
  • /37

    $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 Colonial 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

    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

    Need space! 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 or for your au pair . 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 bedrooms, a full

    Sindy Butkus Klemm Real Estate Inc

    16 Gate Post Ln, 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. New survey added to docs. Acreage at 25.228. 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 25.228 acres. AVAILABLE IN ATT. DOCS: 1) New survey. Dated: 2) Revised lot line survey. 3) Perked results. 4)

    John Gould W. Raveis Lifestyles Realty

    00-1055 Main St N, Woodbury, CT 06798

Home Trends in Woodbury, CT

Housing Trends

Median Sale Price
$735,000
Median Single Family Sale Price
$839,000
Median Townhouse Sale Price
$265,000
Median 2 Bedroom Sale Price
$254,500
Median 1 Bedroom Sale Price
$128,500
Average Price Per Sq Ft
$247
Number of Homes for Sale
3
Last 12 months Home Sales
56
Months of Supply
0.60
Median List Price
$839,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
194%
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