Woodbury, CT Homes for Sale

Welcome to this light-filled and beautifully maintained townhome in the highly sought-after Woodlake community in Woodbury. Spanning three levels, this inviting home offers a rare blend of space, comfort, and seasonal views of Wood Lake. The main level features a spacious living and dining area anchored by a striking floor-to-ceiling fireplace, enhanced with a wood-burning insert (2021). Sliding

Henrik K Kjaer Keller Williams Realty

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.

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

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 48' Sub-Zero refrigerator & a

Becky Hood William Pitt Sotheby's Int'l

Welcome to this well-maintained condo offering comfortable living in a desirable Woodbury location. This inviting unit features a bright and open layout with spacious living areas, an updated kitchen, and generously sized bedrooms. Enjoy the ample storage and a private outdoor space perfect for relaxing or entertaining. Nestled in a quiet, well-kept complex close to local shops, dining, and major

Stephen Mele Houlihan Lawrence

New Price-Point on this lovely upscale residence! Don't miss the opportunity for a vacation at home "Woodlake Life Style" Each room is thoughtfully purposed and decorated with classy features.A spacious "open" concept kitchen includes "Corian" countertops. Cherry toned flooring adds a warm welcome to the first floor, as does the working fireplace. The 1st., floor powder room is oversized &

Terry Lee Adams Adams & Adams Real Estate

The finest condo complex in one of Litchfield Counties most charming towns! Woodbury Hill is a lovely community of townhouse style homes in a very attractive setting and features a saltwater pool and tennis/pickleball courts. #17 has seen many upgrades over the past dozen years including new windows, renovated kitchen and baths, upgraded heat pump HVAC and water heater, as well as recent paint

Justin Bette Century 21 Bette Real Estate

At Woodlake, you're not just buying a home, you're buying a lifestyle. From being FHA Approved condos, to water views at every balcony, trail walks to boat rides to fountains and everything in between, Woodlake truly offers the peaceful, serene setting that we all dream of. This 3 bedroom, 2.5 bath freshly painted end unit has endless possibilities. Need a main level bedroom or office? One can be

Macey Mazzella RE/MAX RISE

Everything has already been done for you. Just move in, unpack, and enjoy the ease of single-floor living in this beautifully renovated ranch with endless potential below. Completely renovated and truly move-in ready, this home offers effortless living with every major updated already completed. From the brand-new HVAC system and newly installed septic to new windows, lighting, interior and

Erin Loucks BHGRE Gaetano Marra Homes

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

A Lovely Renovated End Unit with year round Rhododendron - greenery privacy at the deck. The summer blooms are spectacular! This condo is close to the Woodlake Community Garden, for those wishing to grow your own veggies! Inside you will notice a renovated kitchen with granite countertops, tiled flooring, ceiling fan and stainless steel appliances. The living room and dining room with the

Terry Lee Adams Adams & Adams Real Estate

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

Would you like to live in beautiful Woodbury Connecticut. Please submit Highest & Best offer by Monday 6/15 5 PM. Set on 1.95 acres of peaceful, private grounds, this beautifully updated 3-bedroom, 2.1-bath home sits gracefully on a gentle rise at the top of the driveway, partially framed by classic white post and rail fencing that enhances its New England charm. The entire home-interior,

MaryAnne Betso Coldwell Banker Realty

Nestled on 1.53 acres and set back from the road, this charming Cape Cod style home offers the perfect blend of comfort, character and New England charm. The interior features 2 bedrooms and a full bath on the main and upper level. An inviting Living Room showcases a fireplace with an energy efficient woodburning insert, creating a warm and cozy gathering space. The dining area provides access to

Roberta Allen William Raveis Real Estate

Built in 1854, this 5.91 acre property offers an incredible value impossible to replicate today for the price. The property includes an Italianate stone home with an approx 675 sq foot retail/office room with a separate entrance at the driveway, a 28' x 53' post and beam barn with a full walkout lower level, a large pond, stone walls, incredible perennial garden surround, and a 21' x 45'

Amy Lapierre Coldwell Banker Realty

Nestled in the desirable Woodlake community, this townhouse at 4 Woods Way offers the perfect blend of comfort, convenience, and cozy living. The inviting layout features a bright and spacious living area with hardwood floors, a brick wood burning fireplace, open-concept dining, and easy access to a private deck-perfect for relaxing or entertaining. The kitchen offers generous cabinet storage and

Jenn Lailer BHGRE Gaetano Marra Homes

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

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

Warren's Landing on the Pomperaug is an extraordinary estate where historic character is centered around a beautifully preserved 1890 Greek Revival residence. The home offers four bedrooms, timeless architectural details, spacious rooms, 4 fireplaces and custom built-ins. The impressive six-barn complex provides exceptional flexibility, featuring a retail shop, extensive equipment storage, a

Maria Taylor Klemm Real Estate Inc

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

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

Welcome to Upper Grassy Hill Living!

Susan Corleto William Pitt Sotheby's Int'l

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.

Escape to your own private retreat in the heart of Woodbury. Nestled on over 6 picturesque acres, this charming property offers the perfect blend of privacy, natural beauty, and country living. Surrounded by mature trees and serene landscapes, the home provides a peaceful getaway while remaining conveniently close to local amenities. The residence itself is full of character and has been well

Nicholas Burrus Roundtree Realty LLC

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. Renovated kitchen with all new countertops and Italian farmhouse sink, floors, Pantry, refreshed cabinets. All newer

Beatriz Conroy William Raveis Real Estate

Nestled in the well-established Sherman Hill neighborhood, this five-bedroom home offers a generous footprint to put your personal touches on. Boasting wood flooring and newer windows throughout, the main level features a fluid layout designed for effortless living: a spacious living room, formal dining room, an eat-in kitchen, a cozy family room with a fireplace, a private home office, and a

Christian Jensen William Pitt Sotheby's Int'l

Exceptionally private, Putnam Loft model in the sought after Woodbury Hill! This unit is located in a secluded part of the community with woods behind and only sounds of the nearby babbling brook. This well-cared for unit features hardwood floors throughout, vaulted ceilings, floor to ceiling gas fireplace, a large dining room and remodeled kitchen. The primary bedroom suite is on the main level

Katherine Parlato Drakeley Real Estate, Inc.

Welcome home to this beautifully maintained 4-bedroom, 2.5-bath center hall colonial with quintessential wrap-around front porch, ideally situated on a desirable cul-de-sac just minutes from the charming town centers of Woodbury and Roxbury. Step inside to a gracious foyer flanked by a formal dining room and a versatile living room/den, ideal for a home office, library, or sitting room. The heart

Stephanie Chapman BHGRE Gaetano Marra Homes

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

Charming in-town Gambrel Colonial with views of Orenaug Pond, located just up the road from the South Green. Surrounded by historic landmarks such as King Solomon's Lodge, the Hurd House, the Glebe House, and other notable properties, this home offers three bedrooms, three full baths, and one half bath. It also features a remodeled kitchen with stainless appliances that opens to a family room

Sindy Butkus Klemm Real Estate Inc

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

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.

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

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.

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