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 refrigerator & a 136 bottle wine fridge. Plus built-in professional expresso machine. All Wolf appliance suite including a 6 burner gas cooktop, double ovens and microwave. The sun-filled breakfast nook flows effortlessly into the comfortable, inviting family room, where a striking marble fireplace and expansive bay window frame picturesque views of the property and distant hills. A set of sliders open to a large lawn-level deck for summer enjoyment. The second floor is highlighted by an extraordinary primary suite designed as a private retreat. Luxurious space features a fireplace, elegant sitting room, spa-inspired bathroom with soaking tub, his & hers walk in closets. Three additional bedrooms with en-suite bathrooms and a large bonus room complete upstairs. Dramatically transformed and enhanced to include all new hardwood radiant floors. The spacious flat, fully fenced yard hosts a beautiful Gunite, heated, salt water pool and beautiful distant views. Extraordinary - Must See.
Classic early-1900s colonial in the heart of Woodbury with 3 bedrooms, 2 full baths, and over 1,900 square feet of living space. The home offers a comfortable mix of older-home character and practical updates, with hardwood floors, good natural light, and a layout that works well for everyday living. The updated kitchen features white cabinetry, granite counters, stainless steel appliances, recessed lighting, and a breakfast bar area. It has a clean, bright feel with plenty of cabinet and counter space. The living room offers a warm, traditional setting with hardwood floors, a brick fireplace, and large windows overlooking the property. Outside, the home sits back from the road with a large paved driveway and a detached 2-car garage. The garage provides great storage, parking, and separate workspace potential. Additional features include a full basement, newer well, and a whole-house generator. This is a solid Woodbury home with historic charm, useful updates, and a convenient location close to town, shops, restaurants, and area amenities.
Welcome to this spacious three-bedroom, two and a half bath townhouse located in the desirable Woodlake Community. The living room and dining areas offer an open-concept floor plan, making it perfect for both everyday living and entertaining guests. Sliding glass doors from the dining room lead to a private deck, which looks out upon a wooded area that offers serene views. The primary bedroom includes its own en-suite bath, while a second full bathroom serves the additional two bedrooms. In addition to the main floor living space, this unit has a partially finished basement and clean laundry space. With a newer HVAC system you can enjoy comfort throughout the year. This townhouse presents a wonderful opportunity for those seeking ample space, comfort and a peaceful setting. Residents of Woodlake. benefit from scenic walking trails and a serene natural environment. The community is conveniently located just minutes from the historic downtown Woodbury and I-84, making it easy to access shopping, dining and parks. Discover the convenience of living the Woodlake lifestyle and schedule your private showing today. Owner installing front screen door prior to closing.
Tucked away on 4.99 serene wooded acres in picturesque Woodbury, this solidly built Cape Cod offers privacy, charm, and endless potential. Surrounded by mature trees and peaceful natural beauty, the property provides a true country setting with room to create gardens, walking trails, or space for animals and hobby farm interests. Inside, the home features 3 bedrooms, 1.5 baths, beautiful hardwood floors, and a warm, inviting layout filled with timeless character. Whether you envision restoring its classic charm or creating your own private retreat, this property offers a rare opportunity to own nearly five acres in one of Litchfield County's most sought-after towns.
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 and a newly installed septic system. Other upgrades include a freshly paved driveway, new interior and exterior paint, a brand-new front walkway, and a fireplace with updated stonework and a new floating mantel. The home also features a spacious, unfinished basement with a newly updated half-bath, offering incredible potential for future expansion. Outside, an expansive yard provides plenty of room to relax, play or entertain. Turnkey and thoughtfully updated - this is one you won't want to miss!
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 designed for both intimacy and entertaining. A cozy sitting room and a dedicated office/library-complete with a classic fireplace-offer quiet retreats. For larger gatherings, the front-to-back living room, with windows on three sides, is bathed in natural light. At the heart of the home is the remodeled kitchen, which opens to the dining room centered around the original refurbished center core fireplace. Upstairs, four bedrooms await. The primary bedroom offers a new ensuite bath detailed with custom tile. The three additional bedrooms share a fully renovated bathroom with a soaking tub/shower combo. Thoughtfully curated, professionally designed interior furniture and fixtures are available upon request. The property has benefited from extensive renovations that include new bathrooms and kitchen, floor refinishing, a new well, upgraded septic, and more; a substantial list is available upon request.
Charm and modern comfort come together in this beautifully renovated 3-bedroom, 2-bath home set on nearly an acre along a quiet country road in Woodbury. Thoughtfully updated and move-in ready, this inviting home blends classic New England character with practical improvements throughout, including a fully insulated attic and insulated walls added by the current owner for enhanced comfort and efficiency. The main level features a warm living room with fireplace, a spacious first-floor bedroom, and a full bath, offering flexibility for guests or convenient one-level living. The newly updated kitchen opens to the dining area and leads directly to a brand-new deck overlooking a private, level backyard with distant pond and mountain views. The yard has been cleared and extends to a peaceful meadow that backs to a wooded preserve, creating a serene and private setting. A recent expansion added an oversized two-car garage, extra deep with high ceilings and potential for a loft, workshop, or additional storage. The full basement offers tall ceilings, ample storage, and rear exterior access to the leveled backyard. Adjacent to the basement door is an additional versatile room, ideal for outdoor storage, tools, hobbies, or a creative workspace.
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 true sense of retreat just minutes from Woodbury and Southbury town centers, commuting routes, and everyday amenities. Offering 3,865 sq. ft. of finished living space on the main two levels, plus an additional 550 sq. ft. recreation room in the walkout lower level, this spacious home provides plenty of room to live, work, and entertain. The first floor features a gourmet kitchen with granite countertops and a large center island perfect for gathering, a spacious great room with cathedral ceiling, formal living and dining rooms, and a cozy den with fireplace. Upstairs, an open foyer/sitting area leads to a comfortable primary suite and three generously sized bedrooms. The exterior is beautifully maintained and includes a privacy fence, rear patio, and three-car garage. Recent improvements add even more value, including a new HVAC and central air conditioning system installed in March 2026, along with solar panels added by the owners to help curb rising energy costs. The two fireplaces give wonderful comfort and warmth.
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 area facing French doors opening to a welcoming living room w/hardwood, vaulted ceilings & brick fireplace. The family room/study pulls in the strength of hardwoods, tray ceiling & plenty of natural lighting. The main level bedroom/office & guest bathroom complete this central level. Continuing the journey upstairs & you will be greeted by spectacular views from the transom window aloft the staircase. The path to the primary bedroom suite introduces a tray ceiling, large walk-in closet & full bath w/whirlpool tub, shower stall & skylight. The three additional bedrooms are generous in size while the laundry room, common full bath w/double sink vanity & tub/shower concludes this upper level. The main level full in-law is a desirable focal point showcasing a separate entry, remodeled eat-in kitchen, living room w/vaulted ceiling, gas fireplace, large bedroom, remodeled full bath, laundry closet & staircase to garage w/private basement. Exterior features two new A/C condenser units, custom retaining walls, large deck & three car garage. This sought-after home exceeds all expectations!
Rarely is a ranch style available at Woodbury Hill as there are only 7 in total, This one is almost self standing-neighbor's one car garage is adjacent to this two car garage. There is an additional 640 sq.ft. in the heated lower level with a laundry room, closets, half bath and a separate work area and all with sliders to the yard. The beamed living/dining room is cathedral in the living room section with a two story window and lovely fireplace. A nice sunny den is nearby and down the hallway is the MBR with a slider to the wrap around deck. There are two full baths on the main floor. The large kitchen also has a slider to the oversized deck that shows beautiful views of the grounds. Keep in mind that Woodbury Hill is in walking distance to the center of Woodury which includes the library, stores, post office, parks, community center for exercise classes and lectures. Take advantage of the outdoor pool, tennis court and gatherings at the gazebo. Enjoy the award winning restaurants, golf courses, nature centers, community theater, art galleries and antique shops. Remember you are only minutes from major routes and 1 1/2 hours to NYC by car and 1/2 hour to the train. This lovingly cared for home is easy to show and well worth it. Woodbury was listed as No.3 in the 10 places to live in Connecticut according to Travel and Leisure as seen in the May issue of Ct. Magazine.
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, 2.5 BA FARMHOUSE STYLE SPLIT LEVEL with large front porch, oversized 2 car garage, CATHEDRAL LIVING ROOM and finished lower level with laundry room and half bath.
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 BR, 2.5 BA Cape with FULL FRONT PORCH, 2 car attached garage and OPEN BUT LIVABLE floor plan. LL set up for future finishing.
RECENTLY REFURBISHED and move-in-ready! Notice the tile entry. The Kitchen has new S.S. appliances. The Kitchen layout is "chef-friendly" w/plenty of cabinet storage. The first floor includes the convenience of laundry and a 1/2 Bath. Hardwood floors in the living room adds to the inviting ambiance. There is a fireplace: it can easily become working with the insert of a Pellet or Wood-burning stove insert. The Woodlake Office will guide you w/the easy permit process. New carpet upstairs. The Primary Bedroom is ensuite and offers plenty of closet space. The lower level is a spacious "clean" canvas; finish to suit your needs... perhaps a media room, home office, work out room, storage etc. Please see Prop. Disclosures RE: Fee structure. With HOA, WTD & Town of Woodbury. Note with new budgets pending: the stated fees may change July 1st, 2026. Woodbury is a quintessential Town: Recently voted the Best Small Town In CT: by the Boston Globe and Readers Digest. Main Street is picturesque with period homes and two village greens. Activities at Hollow Park, Flanders Nature Center, Antique and boutique browsing, The CT wine trail, The Glebe House Museum, learning and performing arts centers, not to be missed; fabulous restaurants to suit everyones palate. You will enjoy living the vacation at home, "Woodlake Life Style". A gem of a community with on-site management to ensure needs are promptly addressed. Watch for the summer of 2026 reopening of the Clubhouse Community Center.
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 preservation and character, having been featured in Early American Life magazine and Historic Homes magazine-an honor that speaks to its authenticity and enduring appeal. This stately five bedroom home showcases original architectural details that collectors and history enthusiasts dream about. Seven fireplaces anchor the home's character across its generous 4,800+ square feet. Five beautifully paneled rooms reveal the craftsmanship of a bygone era, while antique wide-board flooring runs throughout, whispering stories of centuries past beneath every footstep.
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, original hardwood floors, LED lighting, bow windows, a walk-in closet and ceiling fan-adjacent to a versatile three season porch. The formal dining room has a cozy brick fireplace with a wood stove. The updated kitchen features modern cabinetry and countertops, a center island, engineered flooring, under-cabinet lighting, and brand-new appliances. A conveniently located laundry room is situated just steps away. All three bedrooms showcase beautiful hardwood flooring, including the Primary Bedroom offering a walk-in closet, an additional closet and private half bath. The home has seen numerous updates, including a newly renovated full bathroom.
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 atmosphere. Outside, a private patio with an open fireplace provides an ideal setting for relaxation or entertaining, surrounded by lush perennial gardens. Adding to the property's versatility is a separate guest house. This additional structure is perfect for an artist's studio, offering a quiet and inspiring space for creative pursuits, or it can serve as a professional office, providing a dedicated work environment. Woodbury is known for its historical properties, with some homes dating back to the late 17th century. Main Street offers a charming experience with its antique shops, local restaurants, and vibrant Memorial Day parades. Woodbury is known for its picturesque downtown area, featuring beautiful streets and historic houses. As a gateway to the Litchfield Hills, the area provides access to a wider region known for its natural beauty and diverse attractions. Litchfield Hills are home to numerous wineries, forming part of Connecticut's Wine Trail,where you can enjoy tastings and scenic vineyards. The region also boasts farm-to-table restaurants that highlight local produce.
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 tranquility, providing ample room for turnout, training, and leisure. The main residence is a warm and inviting three-bedroom, two-bath ranch showcasing country charm with modern updates. Enjoy vaulted ceilings, two fireplaces, and woodstoves that create a cozy ambiance throughout. An attached one-bedroom in-law or apartment offers an open-concept living area-perfect for guests, extended family, or rental income potential. Outdoors, relax in your private backyard with space for entertaining, plus a thriving vegetable garden to complete the rural lifestyle. A rare opportunity to own a true horse lover's retreat where comfort meets countryside elegance.
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 an exclusive 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 mats, stall windows, mounted hay racks, a hay chute, three cross-tie areas, and convenient hay storage with a conveyor system. Additional equestrian amenities include an outdoor wash stall, a 200' x 150' outdoor riding arena with stadium jumps, cross-country jumps woven throughout the property, and a 130' x 65' dressage arena. Five paddocks, 13 outdoor stalls, and ample room for expansion make this an exceptional setup for horse enthusiasts, trainers, or boarding operations. Thoughtfully sited to capture breathtaking views, the custom-built home overlooks the picturesque grounds from a stunning 90-foot wraparound deck. Inside, the cathedral-ceiling great room with a cozy wood stove flows into the kitchen, dining area, and bright sunroom, with French doors opening to the expansive deck for seamless indoor-outdoor living. The main level includes a bedroom and full bath, while the second-floor primary suite offers a walk-in closet and spa-like bath featuring a clawfoot soaking tub.
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 routes, this home offers a perfect blend of comfort, convenience, and low-maintenance living.
Step back in time as you enter this enchanting 1846 cottage, where history and modern comfort blend seamlessly. Wide-board wood floors and exposed hand-hewn beams welcome you the moment you arrive, guiding you through rooms filled with character and warmth. The open-concept kitchen features a stainless steel gas stove and dishwasher, charming display cabinets, a farmhouse sink, and a delightful chalkboard refrigerator-perfect for leaving notes or sharing daily inspiration. A classic Dutch door adds timeless style. Just beyond, the cozy living area offers a wood-burning fireplace, built-ins, and a beautiful wood entry door with transom windows-an ideal spot to gather, relax, or enjoy a quiet evening by the fire. A convenient half bath with laundry completes the main level. Upstairs, the primary bedroom suite is a true sanctuary with its own fireplace, built-ins, and inviting sitting area. Two additional bedrooms offer large windows that fill the rooms with natural light, and a full bath completes the second floor. Outside, enjoy a two-car garage with an upstairs pool house or studio-perfect for hobbies, guests, or extra storage. Spend sunny days splashing in the inground pool, surrounded by the peaceful charm of this historic property. Located in the heart of Woodbury, Connecticut, you're just five minutes from local restaurants, boutique shops, and the famous Antiques Trail. Enjoy a gourmet bakery, grocery stores, and countless attractions right around the corner-
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, this property promises a welcoming and tranquil lifestyle.
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 doors lead to a private deck with peaceful wooded surroundings and seasonal lake views. The kitchen is appointed with granite countertops, stainless steel appliances, and direct access to a patio finished with stone pavers - ideal for outdoor dining and entertainment. Upstairs, the primary suite offers ample closet space, a full bath, and a Romeo balcony with seasonal lake views. A second bedroom and additional full bath provide flexibility for guests or a home office. A convenient laundry closet with brand new, never-used washer and dryer adds to the ease of everyday living. Additional insulation (2021) enhances energy efficiency, and generous storage is found throughout. The finished, walk-out lower level adds approximately 600 square feet of versatile living space, ideal for a family room, gym, or office. Additional highlights include two assigned outside parking spaces. Residents of Woodlake enjoy scenic walking trails and a tranquil natural setting, just minutes from historic downtown Woodbury and I-84.
Spring-Ahead & Welcome Home...to an upscale residence w/3 levels of quiet elegance. Enjoy the vacation at home..."Woodlake Life Style". Each room is thoughtfully purposed and decorated with a classy style. 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 & updated. Upstairs, the primary bedroom bath is thoughtfully renovated: notice the addition of the "closet system". You will also note the convenient feature of the laundry - in close proximity to the primary bedroom. The Lower Level is finished and provides ample storage. The garage is partitioned from the other garage units. You will love exploring Woodbury and all it has to offer. Recently voted CT's Best Small Town by The Boston Globe and Reader's Digest. There are Restaurants galore, many featuring farm to table cuisine. Woodbury is home to two Main Street Greens & lovely period homes. Woodbury is part of CT's Antique and wine trail. Shop Boutiques & Garden Ctrs. Hollow Park, Flanders Nature Ctr., Learning & Performing Art Centers, The Glebe House Museum & hiking trails, are just a few suggestions that make Woodbury Special. Close to private schools. The Commute east or west on I-84 is easy! Its time to plan your 2026 move! 2025 New Heat Pump and Attic "Blown-in" insulation, keeps this residence toasty warm. Stay tuned for info on Woodlake's Community Room Reopening!
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 front porch, and charming potting shed, creating a peaceful retreat. Inside, a sun-filled front-to-back living room offers elegant moldings, custom built-ins, and a wood-burning fireplace. The adjacent study, with built-in bookcases and a second wood-burning fireplace, provides an ideal home office or quiet sitting room. The warm and functional kitchen includes solid wood, custom cabinetry, a brand-new Thor stove, and a breakfast nook. A versatile side room, with full bath, offers flexibility for a pantry, office, or first-floor bedroom. The dining room, just beyond the wet bar, overlooks the terrace and is perfect for gatherings. Upstairs are three spacious bedrooms and two full baths, including a primary bedroom with fireplace, wall of closets and private en-suite. Cedar-lined closets are found throughout. A classic two-story barn provides three-car parking plus ample storage or hobby space and an area to lounge by the pool. Central air and a whole-house generator complete this idyllic country retreat. Good Hill leads directly to Main St. and Hollow Park, road construction ends in May
Woodbury is located in Connecticut. Woodbury, Connecticut has a population of 9,762. Woodbury is less family-centric than the surrounding county with 23.2% of the households containing married families with children. The county average for households married with children is 26.17%.
The median household income in Woodbury, Connecticut is $104,081. The median household income for the surrounding county is $84,797 compared to the national median of $69,021. The median age of people living in Woodbury is 54.7 years.
The average high temperature in July is 84.1 degrees, with an average low temperature in January of 15.8 degrees. The average rainfall is approximately 49.3 inches per year, with 40.2 inches of snow per year.
