4,978

Woodbury, CT Homes

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  • 3 Inwood Ln, Woodbury, CT 06798
    3 Inwood Ln, Woodbury, CT 06798
    3 Inwood Ln, Woodbury, CT 06798
    /40

    $799,900 Pending

    • 4 Beds
    • 4 Baths
    • 3,330 Sq Ft

    3 Inwood Ln, Woodbury, CT 06798

    Set on a quiet cul-de-sac and bordering open space, this beautifully maintained 4BR, 4BTH colonial blends charm w/modern comfort & functionality. Step into the grand foyer flanked by a sunken living room with fireplace and private home office. At the heart of the home is the updated eat-in kitchen, featuring abundant white cabinetry, marble countertops, a butcher block center island, and

    Elizabeth Newnham William Pitt Sotheby's Int'l

    3 Inwood Ln, Woodbury, CT 06798
  • 7 Orenaug Ave, Woodbury, CT 06798

    $515,000 Sold Jun 30, 2025

    • 1,918 Sq Ft
    • $269/SF
    • 44 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1820

    7 Orenaug Ave, Woodbury, CT 06798

    New to market.....Lovely, classic antique colonial just off Main Street in center of town Woodbury. Home has been updated, expanded and well maintained over the years. Spacious family room off kitchen and primary bedroom/bath reflect today's lifestyle. Beautiful and private backyard. Easy walk to everything Woodbury offers.

    Lisa Titcomb William Pitt Sotheby's Int'l

    7 Orenaug Ave, Woodbury, CT 06798
  • 29 Woods Way, Woodbury, CT 06798
    29 Woods Way, Woodbury, CT 06798
    29 Woods Way, Woodbury, CT 06798
    /32

    $274,999

    • 3 Beds
    • 2.5 Baths
    • 2,450 Sq Ft

    29 Woods Way, Woodbury, CT 06798

    Spacious 3-bedroom, 2.5-bath end unit with 1,640 sq ft of interior space, ready for your personal touch. This 1980-built home features all hardwood floors, crown molding, central heat and air, and marble kitchen countertops. While the property needs cosmetic updates, it offers strong potential to add value. The finished basement provides clean, usable storage space. Great opportunity for buyers

    Derek Greene Derek Greene

    29 Woods Way, Woodbury, CT 06798
  • 332 Good Hill Rd, Woodbury, CT 06798

    $897,000 Sold Jun 27, 2025

    • 2,894 Sq Ft
    • $310/SF
    • 27 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 2015

    332 Good Hill Rd, Woodbury, CT 06798

    Stunning reproduction of a mid-1700s New England Center-Chimney Cape, masterfully built in 2015 and set on 3.3+/- acres. This 3-bed, 3-bath home blends timeless craftsmanship-12-over-12 windows, wide plank circle-sawn floors, custom trim and paneling-with modern luxuries including smart home tech, soapstone counters, and a showpiece kitchen hearth. Enjoy nearly 2,900 sq ft of living space,

    Rebecca Doh W. Raveis Lifestyles Realty

    332 Good Hill Rd, Woodbury, CT 06798
  • 35 Coach Light Dr, Woodbury, CT 06798
    35 Coach Light Dr, Woodbury, CT 06798
    35 Coach Light Dr, 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
  • 98 Old Town Farm Rd, Woodbury, CT 06798

    $499,000 Sold Jun 16, 2025

    • 1,648 Sq Ft
    • $303/SF
    • 3 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1972

    98 Old Town Farm Rd, Woodbury, CT 06798

    Discover this inviting ranch style, one level living home featuring three bedrooms and two and a half baths, beautifully situated on a scenic lot. A separate front entrance leads into a convenient mudroom that also serves as the laundry area and access to the garage.The spacious living and dining room boasts a charming brick fireplace with a wood stove, perfect for cozy gatherings. The remodeled

    Jeff Boucher Drakeley Real Estate, Inc.

    98 Old Town Farm Rd, Woodbury, CT 06798
  • 1 Alder Ct Unit 1, Woodbury, CT 06798
    1 Alder Ct Unit 1, Woodbury, CT 06798
    1 Alder Ct Unit 1, Woodbury, CT 06798
    /38

    $300,000

    • 2 Beds
    • 2.5 Baths
    • 1,365 Sq Ft

    1 Alder Ct Unit 1, Woodbury, CT 06798

    Welcome to the Woodlake Community! Experience pride of ownership in this beautifully maintained and thoughtfully updated townhouse, ideally located in the highly desirable Woodlake condominium complex in Woodbury. This bright and spacious home welcomes you with a warm and inviting open-concept living and dining area-perfect for relaxing or entertaining. A rare, approved pellet stove insert adds

    Camilo Ramirez Higgins Group Real Estate

    1 Alder Ct Unit 1, Woodbury, CT 06798
  • 1 Woods Way Unit 118E, Woodbury, CT 06798

    $290,000 Sold Jun 13, 2025

    • 1,773 Sq Ft
    • $164/SF
    • 16 Days On Market
    • 2 Beds
    • 3 Baths
    • Built 1980

    1 Woods Way Unit 118E, Woodbury, CT 06798

    Country Living at its finest in award winning Woodbury CT. Recently voted The Best Small Town in CT by The Boston Globe and Readers Digest! This home has been remodeled and is in immaculate Move-in-Ready condition. The Fireplace has a pellet stove for cozy winter warmth. The Living room/dining area offer inviting wood toned floors. The deck is accessed via the LR slider. There is a lovely stretch

    Terry Lee Adams Adams & Adams Real Estate

    1 Woods Way Unit 118E, Woodbury, CT 06798
  • 557 Upper Grassy Hill Rd, Woodbury, CT 06798
    557 Upper Grassy Hill Rd, Woodbury, CT 06798
    557 Upper Grassy Hill Rd, Woodbury, CT 06798
    /40

    $999,000

    • 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
  • 17 Transylvania Rd, Woodbury, CT 06798

    $1,050,000 Sold Jun 06, 2025

    • 3,928 Sq Ft
    • $267/SF
    • 34 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2008

    17 Transylvania Rd, Woodbury, CT 06798

    A stunning 4-bedroom, 2.5-bathroom colonial nestled on a private 2-acre lot, set back along a winding newly decorative stone driveway in an estate-like setting. This beautifully designed home boasts an open floor plan with high ceilings-9+ feet in most rooms and soaring to 10.5 feet in the living room-refined finishes, and luxurious upgrades throughout. The gourmet kitchen features granite

    Michael Hvizdo Coldwell Banker Realty

    17 Transylvania Rd, Woodbury, CT 06798
  • 34 Hollow Rd, Woodbury, CT 06798
    34 Hollow Rd, Woodbury, CT 06798
    34 Hollow Rd, Woodbury, CT 06798
    /27

    $765,000

    • 3 Beds
    • 3 Baths
    • 1,675 Sq Ft

    34 Hollow Rd, Woodbury, CT 06798

    Welcome to one of the most charming communities in Connecticut. This darling of an antique home sits in the heart of Woodbury, CT. It is a Dutch colonial dating to circa 1700, bought in 1750 by a well-respected, wealthy local merchant/ financier, Jabez Bacon. The building became the town's first general store, known as the Red Store. After Bacon's death, the property served as a school and later

    Lorraine Consiglio Coldwell Banker Realty

    34 Hollow Rd, Woodbury, CT 06798
  • 23 Woodbury Hill, Woodbury, CT 06798

    $415,000 Sold Jun 04, 2025

    • 1,796 Sq Ft
    • $231/SF
    • 55 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1985

    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
  • 45 N Gate Rd, Woodbury, CT 06798
    45 N Gate Rd, Woodbury, CT 06798
    45 N Gate 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
  • 229 Bacon Pond Rd Unit 132, Woodbury, CT 06798

    $184,000 Sold May 28, 2025

    • 913 Sq Ft
    • $202/SF
    • 56 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1971

    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
  • 38 Barnhill Rd, Woodbury, CT 06798
    38 Barnhill Rd, Woodbury, CT 06798
    38 Barnhill Rd, Woodbury, CT 06798
    /23

    $729,900 Open Sun 11AM - 1PM

    • 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
  • 22 Woods Way Unit 22, Woodbury, CT 06798

    $280,000 Sold May 28, 2025

    • 1,482 Sq Ft
    • $189/SF
    • 69 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1980

    22 Woods Way Unit 22, Woodbury, CT 06798

    Beautiful townhouses in the wonderful Woodlake complex. This unit is wonderfully updated and impeccably maintained. The well appointed kitchen is light & bright with corian countertops & stainless appliances. The living room is warm & inviting featuring cozy pellet stove, accent beams and slider to a private deck. Laundry & a lovely half bath on the main floor as well. Upstairs there are two good

    Joan Junga CB Country to Coast Realty

    22 Woods Way Unit 22, Woodbury, CT 06798
  • 133 Hoop Pole Hill Rd, Woodbury, CT 06798
    133 Hoop Pole Hill Rd, Woodbury, CT 06798
    133 Hoop Pole Hill Rd, Woodbury, CT 06798
    /35

    $779,995 Pending

    • 4 Beds
    • 3.5 Baths
    • 2,994 Sq Ft

    133 Hoop Pole Hill Rd, Woodbury, CT 06798

    A short 2.5 hour drive to New York City! 133 Hoop Pole Hill Rd. offers refined country living in this exceptional 4-bedroom, 3.5-bath home set on a peaceful 3.32-acre wooded lot. Surrounded by nature, this well built home blends timeless charm with modern convenience. Step inside to find a bright and inviting foyer, beautiful hardwood floors throughout, and a layout made for everyday living. The

    William Glanville Glanville Real Estate

    133 Hoop Pole Hill Rd, Woodbury, CT 06798
  • 447 Transylvania Rd, Woodbury, CT 06798

    $875,000 Sold May 22, 2025

    • 3,978 Sq Ft
    • $220/SF
    • 149 Days On Market
    • 5 Beds
    • 4 Baths
    • Built 2004

    447 Transylvania Rd, Woodbury, CT 06798

    Nestled at the intersection of Route 72 and Route 167 in Woodbury, this exceptional home is the perfect blend of modern amenities and unparalleled convenience. Located in close proximity to both the Center of Woodbury and the Southbury Green you'll be moments away from a diverse selection of shops and restaurants. Enjoy the close by natural beauty of Wood Lake, local parks, walking trails, and

    Casey French Litchfield County Real Estate

    447 Transylvania Rd, Woodbury, CT 06798
  • 59 Davids Hill Rd, Woodbury, CT 06798
    59 Davids Hill Rd, Woodbury, CT 06798
    59 Davids Hill Rd, Woodbury, CT 06798
    /30

    $759,900 Pending

    • 4 Beds
    • 2.5 Baths
    • 2,475 Sq Ft

    59 Davids Hill Rd, Woodbury, CT 06798

    This pristine and much-loved shingle-style residence is located at the end of a quiet cul-de-sac in the charming town of Woodbury, known as the "Antiques Capital of CT." With four bedrooms and two and a half baths, the home is nicely sized and has room for expansion. Current owners have invested over 100k in upgrades and remodeling giving it the feel of a new build. Charming details throughout

    Maria Taylor Klemm Real Estate Inc

    59 Davids Hill Rd, Woodbury, CT 06798
  • 59 Hillside Rd, Woodbury, CT 06798

    $1,720,000 Sold May 21, 2025

    • 9,296 Sq Ft
    • $185/SF
    • 31 Days On Market
    • 6 Beds
    • 7 Baths
    • Built 2006

    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
  • 101 Railtree Hill Rd, Woodbury, CT 06798
    101 Railtree Hill Rd, Woodbury, CT 06798
    101 Railtree Hill Rd, Woodbury, CT 06798
    /31

    $750,000 Pending

    • 4 Beds
    • 2.5 Baths
    • 3,341 Sq Ft

    101 Railtree Hill Rd, Woodbury, CT 06798

    This beautiful, well maintained, light and bright Colonial sits on a lot of just over 2 acres, complete with perennial gardens, stone walls stairs and pathways and bucolic views. Freshly painted inside and out, this home features a stunningly updated kitchen with walk in pantry and stainless steel appliances. The family room boasts vaulted ceilings, lots of space and a fireplace. The Primary

    Ellen Vincent William Raveis Real Estate

    101 Railtree Hill Rd, Woodbury, CT 06798
  • 229 Bacon Pond Rd Unit 411, Woodbury, CT 06798

    $160,000 Sold May 20, 2025

    • 913 Sq Ft
    • $175/SF
    • 36 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1971

    229 Bacon Pond Rd Unit 411, Woodbury, CT 06798

    Town In Country lower end unit in a great location within the complex. This unit features new mechanicals and appliances with 2 bedrooms, full bath and fireplace. Bright and sunny living space with a private patio out back overlooking the woods and rear yard. Convenient location to the pool and laundry, minutes from town, shopping and restaurants. Don't miss out.

    Jeff Boucher Drakeley Real Estate, Inc.

    229 Bacon Pond Rd Unit 411, Woodbury, CT 06798
  • 173 Railtree Hill Rd, Woodbury, CT 06798
    173 Railtree Hill Rd, Woodbury, CT 06798
    173 Railtree Hill 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
  • 16 Pilgrim Trail Unit 3, Woodbury, CT 06798

    $120,000 Sold May 19, 2025

    • 546 Sq Ft
    • $220/SF
    • 18 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1965

    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
  • 298 Railtree Hill Rd, Woodbury, CT 06798
    298 Railtree Hill Rd, Woodbury, CT 06798
    298 Railtree Hill Rd, Woodbury, CT 06798
    /31

    $409,000

    • 3 Beds
    • 2 Baths
    • 1,510 Sq Ft

    298 Railtree Hill Rd, Woodbury, CT 06798

    Don't miss this exceptional opportunity in Woodbury offering three separate living spaces, perfect for investors or owner-occupants. The main house includes 3 bedrooms and 2 full baths. A second building features two additional units: a 1 bed/1 bath apartment on the lower level and a 2 bed/1 bath unit upstairs. Each unit is separately metered for electric allowing for independent utility use. The

    Shawna Mucherino Coldwell Banker Realty

    298 Railtree Hill Rd, Woodbury, CT 06798
  • 3 Woodbury Place Unit 3, Woodbury, CT 06798

    $295,000 Sold May 15, 2025

    • 1,025 Sq Ft
    • $288/SF
    • 29 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1979

    3 Woodbury Place Unit 3, Woodbury, CT 06798

    Rare opportunity to own a Woodbury Place condo! Quaint community just minutes from all major conveniences, local restaurants, area schools, and major highway I-84. This end unit features wood burning stove to offset heating costs, and higher efficiency heat pump. The first floor includes dining area with slider to stone patio and galley kitchen offering quartz countertops, built-in pantry, and

    Katherine Parlato Drakeley Real Estate, Inc.

    3 Woodbury Place Unit 3, Woodbury, CT 06798

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