25

Woodbury, CT Homes for Sale with Acreage

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  • /37

    $1,800,000

    Open House 5/31
    • 3 Beds
    • 3 Baths
    • 2,072 Sq Ft

    76 Cowles Rd, Woodbury, CT 06798

    Rare opportunity to own a spectacular 40-acre estate designed for exceptional horse care, training, and country living-while also offering the flexibility to create a private escape tucked away from it all. This remarkable property features a 150' x 80' indoor riding arena with excellent lighting and three overhead doors, along with an immaculate 9-stall barn complete with concrete floors and

    Agent Photo

    Pam Famiglietti

    William Raveis Real Estate

    (475) 252-8273

    76 Cowles Rd, Woodbury, CT 06798
  • /39

    $874,900

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

    339 Main St S, Woodbury, CT 06798

    One of Woodbury's last remaining homes built in the late 1600s. This charming residence offers a unique blend of historic character and modern convenience, ideally situated for those who appreciate easy access to local shops, parks, and restaurants. The interior of the home boasts a rich history with exposed wooden beams, 4 fireplaces, and classic hardwood floors, creating an inviting and warm

    Agent Photo

    Marian Van Egas

    Berkshire Hathaway NE Prop.

    (475) 405-2250

    339 Main St S, Woodbury, CT 06798
  • /40

    $799,900

    • 5 Beds
    • 3.5 Baths
    • 3,607 Sq Ft

    17 Carriage Ln, Woodbury, CT 06798

    Center Hall Colonial with Full In-Law! This majestic brick facing home flaunts its location atop a private lot overlooking sprawling scenic views. Main level features a two-story foyer, formal dining room w/hardwoods & pocket doors leading to a high-end kitchen w/stainless steel appliances including a gas stove. The kitchen delivers with granite tops, upscale cabinetry, breakfast bar, & eat-in

    Agent Photo

    Shane Kropo

    RE/MAX RISE

    (203) 717-5671

    17 Carriage Ln, 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

    $895,000

    Open Sat 10AM - 12PM
    • 4 Beds
    • 2.5 Baths
    • 2,283 Sq Ft

    253 Bacon Pond Rd, Woodbury, CT 06798

    Welcome to Bacon Pond House. A seamless blend of 19th-century soul and 21st-century luxury. Situated on over 3 acres, this antique Colonial has been thoughtfully revived to honor its heritage while offering every modern convenience. The interior, lovingly brought back to life, features wide-plank flooring and exposed hand-hewn beams that anchor the home's historic character. The rooms are

    Christian Jensen William Pitt Sotheby's Int'l

    253 Bacon Pond Rd, Woodbury, CT 06798
  • /2

    $1,069,900

    Coming Soon
    • 4 Beds
    • 3.5 Baths
    • 4,776 Sq Ft

    61 Silver Brook Ln, Woodbury, CT 06798

    Exceptional Colonial in one of Woodbury's finest developments, beautifully set among similar distinguished homes at the end of Silver Brook Lane. Thoughtfully updated over the past five years with high-quality materials and careful attention to detail, this 4,000+ square foot residence offers an ideal blend of elegance, comfort, and modern convenience. The heart of the home is the stunning

    Tim Drakeley Drakeley Real Estate, Inc.

    61 Silver Brook Ln, Woodbury, CT 06798
  • /40

    $895,000

    • 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
  • /26

    $999,900

    $100K PRICE DROP
    • 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

    Tim Drakeley Drakeley Real Estate, Inc.

    27 Middle Quarter Rd, Woodbury, CT 06798
  • /40

    $949,900

    Open Sun 2PM - 4PM
    • 4 Beds
    • 5 Baths
    • 3,865 Sq Ft

    8 Curtiss Meadows, Woodbury, CT 06798

    Beautiful Colonial set on a private 3+ acre lot in sought-after Curtiss Meadows, ideally located on the southern end of Woodbury abutting the Southbury line. Set back from the cul-de-sac entryway, this well-cared-for home offers a wonderful blend of privacy, comfort, convenience, and thoughtful updates. The level, light-filled driveway provides easy access, while the peaceful setting creates a

    Joyce Drakeley Drakeley Real Estate, Inc.

    8 Curtiss Meadows, Woodbury, CT 06798
  • /34

    $1,675,000

    $250K PRICE DROP
    • 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

    $1,899,000

    • 4 Beds
    • 4.5 Baths
    • 5,216 Sq Ft

    48 Coach Light Dr, Woodbury, CT 06798

    Gloriously Peaceful, Private, Magnificent views...This exceptional residence among similar spectacular homes welcomes you with a dramatic two-story entry - designed for both refined entertaining and comfortable living. The heart of the home is a beautifully appointed chef's kitchen featuring porcelain countertops with waterfall island and slab backsplash. New Sub-Zero appliances: 48inch Sub-Zero

    Becky Hood William Pitt Sotheby's Int'l

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

    $799,000

    • 4 Beds
    • 3 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
  • /17

    $579,000

    $16K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,144 Sq Ft

    437 Middle Road Turnpike, Woodbury, CT 06798

    Completely renovated and move-in ready, this single-floor ranch offers effortless living with modern updates throughout. The brand-new kitchen is absolutely stunning and opens to the dining and living area, making the space perfect for both everyday comfort and entertaining. Enjoy peace of mind with all-new bathrooms, windows, lighting fixtures, a newly installed septic system and a brand new

    Erin Loucks BHGRE Gaetano Marra Homes

    437 Middle Road Turnpike, Woodbury, CT 06798
  • /34

    $540,000

    Open Sun 11AM - 1PM $9K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 2,292 Sq Ft

    49 Scuppo Rd, Woodbury, CT 06798

    Discover this beautifully updated ranch-style home ideally situated on over an acre of level, private land. Offering 2292 square feet of comfortable one-level living space, this 3-bedroom, 1.5 bath home combines timeless character with modern upgrades-perfect for those seeking space, tranquility, and convenience. Inside you'll find a bright and expansive living room with cathedral ceilings,

    Joseph Conforti West View Properties, LLC

    49 Scuppo Rd, Woodbury, CT 06798
  • /24

    $745,000

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,060 Sq Ft

    86 Quail Run Rd, Woodbury, CT 06798

    QUAIL RUN On the cul de sac - 4 NEW HOMES ALL ON FLAT LOTS! They might be what you have been looking for - SMALLER & SMARTER new homes with PRICES TO MATCH. Beautiful 1 acre+ lots on shared common drives surrounded by 12 ACRES OF PRIVATE OPEN SPACE. This is QUINTESSENTIAL WOODBURY - Quiet, woodsy, and BEAUTIFUL! Construction has begun on 2 homes with anticipated completion in August. #86 is a 3

    Scott Volpe Coldwell Banker Realty

    86 Quail Run Rd, Woodbury, CT 06798
  • /2

    $1,495,000

    • 5 Beds
    • 4.5 Baths
    • 4,884 Sq Ft

    30 Hollow Rd, Woodbury, CT 06798

    Step through the doors of history and into one of Connecticut's most treasured colonial residences. Built in 1760 and proudly listed on the National Register of Historic Places, the Jabez Bacon House is a rare masterpiece of 18th-century American architecture that has endured with remarkable grace for over 260 years. This distinguished home has also been recognized for its exceptional

    Lisa Titcomb William Pitt Sotheby's Int'l

    30 Hollow Rd, Woodbury, CT 06798
  • /15

    $775,000

    Coming Soon
    • 4 Beds
    • 3.5 Baths
    • 2,708 Sq Ft

    28 School St, Woodbury, CT 06798

    The Orton-Martin Homestead. One of Woodbury's oldest homes has been updated for today's lifestyle. History surrounds you with wide board flooring, library built-ins, two fireplaces and 1850 barn. This four -bedroom home offers spacious rooms, three finished levels and hidden delights. Enjoy picnics under the mature trees on your own fenced-in level yard. Sidewalks take you everywhere on Main St

    Sindy Butkus Klemm Real Estate Inc

    28 School St, Woodbury, CT 06798
  • /2

    $1,150,000

    • Land
    • 42.6 Acres
    • $26,995 per Acre

    0 Flanders Rd, Woodbury, CT 06798

    East Meadowbrook Farm presents a rare opportunity to own a legacy New England property offered for the first time since 1918. Encompassing 42 acres, including 15 rolling, sun-drenched acres of open fields, this former dairy and Christmas tree farm is bordered by 250 acres of protected Flanders Nature Center conservation land, creating an extraordinary sense of privacy and permanence. A quarter

    Tim Drakeley Drakeley Real Estate, Inc.

    0 Flanders Rd, Woodbury, CT 06798
  • /39

    $649,900

    • 3 Beds
    • 2 Baths
    • 1,900 Sq Ft

    Unlisted Address

    Fantastic Potential in this home. Three bedroom Cape Cod sitting on 5.50 acre lot with a giant barn that has great potential living space to convert into an in-laws set up, office, studio space or music studio to fit your lifestyle. Home freshly painted interior and exterior. New updated kitchen and bathrooms. All newer energy star appliances. Walk out into your large screened in porch to enjoy

    Beatriz Conroy William Raveis Real Estate

    Unlisted Address
  • /17

    $479,900

    Open Sat 10AM - 12PM $19K PRICE DROP
    • 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
  • /27

    $645,000

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,081 Sq Ft

    94 Quail Run Rd, Woodbury, CT 06798

    QUAIL RUN On the cul de sac - 4 NEW HOMES ON FLAT LOTS! They might be what you have been looking for - SMALLER & SMARTER new homes with PRICES TO MATCH. Beautiful 1 acre+ lots on shared common drives surrounded by 12 ACRES OF PRIVATE OPEN SPACE. This is QUINTESSENTIAL WOODBURY - Quiet, woodsy and BEAUTIFUL! Construction has begun on 2 homes with anticipated completion in August. #94 is a 3 BR,

    Scott Volpe Coldwell Banker Realty

    94 Quail Run Rd, Woodbury, CT 06798
  • /40

    $699,000

    • 3 Beds
    • 3.5 Baths
    • 3,210 Sq Ft

    58 Good Hill Rd, Woodbury, CT 06798

    Located in picturesque Woodbury, voted Most Charming Town in CT by Reader's Digest in 2018, 2020 and 2024 and featured by Travel + Leisure among the 10 Best Places to Live. This stately circa 1845 home blends historic character with comfortable living. Set along scenic Good Hill Road and surrounded by lush, established gardens, featuring a black bottom gunite pool, private terrace, welcoming

    Christina Zainc BHGRE Gaetano Marra Homes

    58 Good Hill Rd, Woodbury, CT 06798
  • /32

    $314,900

    $35K PRICE DROP
    • 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
  • /15

    $499,999

    • 3 Beds
    • 2.5 Baths
    • 2,100 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

    $1,850,000

    $145K PRICE DROP
    • 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

Home Trends in Woodbury, CT

Housing Trends

Median Sale Price
$490,000
Median Single Family Sale Price
$597,500
Median Townhouse Sale Price
$325,000
Median 2 Bedroom Sale Price
$184,000
Median 1 Bedroom Sale Price
$128,500
Average Price Per Sq Ft
$284
Number of Homes for Sale
36
Last 12 months Home Sales
118
Months of Supply
3.70
Median List Price
$517,500
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
5%
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