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$347,500

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 & 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!plan your tour soo

3 Beds ⋅ 3 Baths ⋅ 24156207 MLS ⋅ Woodlake BLDG.

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 & 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!plan your tour soo

2 S Mdws Unit 2, Woodbury

$400,000

Rare Main Street commercial property available in Woodbury, CT. The land and the building upon it are being sold in "as is, where is" condition. Neither the probate court system, the attorney, or the broker have any knowledge as to any deficiencies on the property or if they even exist Located in the OS 60 zone, interested parties should consult with the planning and zoning to verify their proposed use is allowed. Final sale is contingent on Probate Court approval.

24155988 MLS

Rare Main Street commercial property available in Woodbury, CT. The land and the building upon it are being sold in "as is, where is" condition. Neither the probate court system, the attorney, or the broker have any knowledge as to any deficiencies on the property or if they even exist Located in the OS 60 zone, interested parties should consult with the planning and zoning to verify their proposed use is allowed. Final sale is contingent on Probate Court approval.

1545 Main St N, Woodbury

$179,900

Discover your own private sanctuary on this enchanting ~4-acre parcel of pristine land perched along scenic Carmel Hill Road in historic Woodbury, CT. Nestled in the heart of Litchfield County's rolling countryside, this remarkable property captivates with mesmerizing views of a sparkling waterfall and the gentle flow of a serene river-nature's own symphony right at your doorstep. Imagine awakening to the soothing sounds of cascading water and birdsong, with sunlight dancing across the wooded landscape and open vistas. Perfectly positioned for tranquility yet convenience, the lot offers easy access to the charming town centers of both Woodbury and neighboring Bethlehem-minutes from boutique shops, acclaimed restaurants, antique treasures, and community events. This is more than land; it's a canvas for your dream home, family compound, or legacy retreat, surrounded by the timeless beauty of Connecticut's countryside. Sale is conditional upon successful subdivision approval, which is underway with the Town of Woodbury (site plan attached, tet hole results available upon request, lot for sale is Lot #2 on site plan). A rare opportunity to secure a slice of paradise with extraordinary natural features and endless potential-don't miss this gem! Property sale will be contingent upon subdivision approval. Site plan available.

24150303 MLS

Discover your own private sanctuary on this enchanting ~4-acre parcel of pristine land perched along scenic Carmel Hill Road in historic Woodbury, CT. Nestled in the heart of Litchfield County's rolling countryside, this remarkable property captivates with mesmerizing views of a sparkling waterfall and the gentle flow of a serene river-nature's own symphony right at your doorstep. Imagine awakening to the soothing sounds of cascading water and birdsong, with sunlight dancing across the wooded landscape and open vistas. Perfectly positioned for tranquility yet convenience, the lot offers easy access to the charming town centers of both Woodbury and neighboring Bethlehem-minutes from boutique shops, acclaimed restaurants, antique treasures, and community events. This is more than land; it's a canvas for your dream home, family compound, or legacy retreat, surrounded by the timeless beauty of Connecticut's countryside. Sale is conditional upon successful subdivision approval, which is underway with the Town of Woodbury (site plan attached, tet hole results available upon request, lot for sale is Lot #2 on site plan). A rare opportunity to secure a slice of paradise with extraordinary natural features and endless potential-don't miss this gem! Property sale will be contingent upon subdivision approval. Site plan available.

Carmel Hill Rd, Woodbury

$999,900

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 with a cathedral ceiling and fireplace, and formal living and dining rooms, each with its own fireplace. Upstairs, the primary suite boasts a vaulted ceiling with exposed beams, accompanied by two additional bedrooms and a walk-up attic. This will be a brand new house when complete; new mechanicals, new insulation, new wiring, new plumbing, new kitchen and baths - a new home with the charm of old. The exterior could be equally impressive, offering two post-and-beam barns, and a beautifully landscaped level lot. The Middle Quarter zoning adds extra versatility, allowing you to run a business from home and even expand the living space into the barns. This is truly one of the best locations in Woodbury!

3 Beds ⋅ 3 Baths ⋅ 24146826 MLS

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 with a cathedral ceiling and fireplace, and formal living and dining rooms, each with its own fireplace. Upstairs, the primary suite boasts a vaulted ceiling with exposed beams, accompanied by two additional bedrooms and a walk-up attic. This will be a brand new house when complete; new mechanicals, new insulation, new wiring, new plumbing, new kitchen and baths - a new home with the charm of old. The exterior could be equally impressive, offering two post-and-beam barns, and a beautifully landscaped level lot. The Middle Quarter zoning adds extra versatility, allowing you to run a business from home and even expand the living space into the barns. This is truly one of the best locations in Woodbury!

27 Middle Quarter Rd, Woodbury

$1,575,000

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 patio, new heating system, a powerful 20KW whole house generator and four energy efficient mini-splits ensuring year-round comfort. Enjoy the beautifully landscaped gardens, several tranquil ponds, a babbling brook and perennial flower beds. This spacious home boasts three bedrooms and three full baths, a well-appointed kitchen, office space, a full basement and both attached and detached garages. Relax on the screened porch overlooking the ponds and bring your four-legged friends-this property is ready for you to move right in. Come enjoy the charming little town of Woodbury, only 90 minutes to NYC

3 Beds ⋅ 3 Baths ⋅ 24139312 MLS

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 patio, new heating system, a powerful 20KW whole house generator and four energy efficient mini-splits ensuring year-round comfort. Enjoy the beautifully landscaped gardens, several tranquil ponds, a babbling brook and perennial flower beds. This spacious home boasts three bedrooms and three full baths, a well-appointed kitchen, office space, a full basement and both attached and detached garages. Relax on the screened porch overlooking the ponds and bring your four-legged friends-this property is ready for you to move right in. Come enjoy the charming little town of Woodbury, only 90 minutes to NYC

819 Main St N, Woodbury

$1,995,000

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 surrounding the impressive central hearth. The chef's kitchen features a large center island, breakfast bar, and sweeping views of the expansive lawn-perfect for both everyday living and entertaining. Original details abound, including hand-hewn beams, wide king's board flooring, and the historic cooking fireplace that anchors the heart of the home. Recent upgrades include a new HVAC system with humidification and numerous other enhancements (see attachments for the full list). A new mahogany deck overlooks the level backyard, leading toward a picturesque bridge, sparkling pool, and inviting cabana. Two barns sit near the parking area-one offering garage space and the other ready for your imagination: ideal for a future guest house, studio, or recreation room, this barn has new propane heat, water and electric service. This extraordinary home offers the rare opportunity to own a piece of history-beautifully updated for modern living.

4 Beds ⋅ 5 Baths ⋅ 24136657 MLS

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 surrounding the impressive central hearth. The chef's kitchen features a large center island, breakfast bar, and sweeping views of the expansive lawn-perfect for both everyday living and entertaining. Original details abound, including hand-hewn beams, wide king's board flooring, and the historic cooking fireplace that anchors the heart of the home. Recent upgrades include a new HVAC system with humidification and numerous other enhancements (see attachments for the full list). A new mahogany deck overlooks the level backyard, leading toward a picturesque bridge, sparkling pool, and inviting cabana. Two barns sit near the parking area-one offering garage space and the other ready for your imagination: ideal for a future guest house, studio, or recreation room, this barn has new propane heat, water and electric service. This extraordinary home offers the rare opportunity to own a piece of history-beautifully updated for modern living.

55 Good Hill Rd, Woodbury

$289,000

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, level, potential building lot. Convert office to residential, build across river and rent out office or use office and workshop yourself. There are 2, 7ft' garage doors leading to basement/workshop. The potential uses for this property are many!

2 Beds ⋅ 2 Baths ⋅ 24078648 MLS

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, level, potential building lot. Convert office to residential, build across river and rent out office or use office and workshop yourself. There are 2, 7ft' garage doors leading to basement/workshop. The potential uses for this property are many!

439 Washington Rd, Woodbury

$675,000

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 of road frontage, the property provides ample access and visibility, ideal for a potential for a private residence or nature-inspired retreat. Enriching the value of this land, the Flanders Nature Center/ Land Trust encompasses the northern boundary with about 200 acres and the southern edge with about 28 acres, ensuring the preservation of the natural surroundings and offering a legacy of conservation. This adjacency to protected lands promises enduring tranquility and a haven for local flora and fauna. Conveniently located just minutes from the vibrant Woodbury Center, future owners will enjoy the blend of seclusion with the convenience of nearby amenities, including boutique shopping, fine dining, and cultural experiences. Create something truly special in the heart of Litchfield County.

24084159 MLS

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 of road frontage, the property provides ample access and visibility, ideal for a potential for a private residence or nature-inspired retreat. Enriching the value of this land, the Flanders Nature Center/ Land Trust encompasses the northern boundary with about 200 acres and the southern edge with about 28 acres, ensuring the preservation of the natural surroundings and offering a legacy of conservation. This adjacency to protected lands promises enduring tranquility and a haven for local flora and fauna. Conveniently located just minutes from the vibrant Woodbury Center, future owners will enjoy the blend of seclusion with the convenience of nearby amenities, including boutique shopping, fine dining, and cultural experiences. Create something truly special in the heart of Litchfield County.

Cowles Rd, Woodbury

$990,000

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 suite and two other bedrooms while the upper level offers an office and a loft, both with a cathedral ceiling and views to the outside.

3 Beds ⋅ 2 Baths ⋅ 24086595 MLS

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 suite and two other bedrooms while the upper level offers an office and a loft, both with a cathedral ceiling and views to the outside.

523 Main St N, Woodbury