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$1,395,000

Steeped in 18th-century charm, this rare 1747 Saltbox estate seamlessly marries historic integrity with modern luxury. Tucked away on a peaceful country lane, the main home boasts original wide-plank wood floors, dual fireplaces, twin staircases, authentic built-ins, and freshly renovated baths. At its heart is the kitchen featuring Viking appliances and granite counters that open to garden views. Step through the screened stone-and-timber breezeway to a newly expanded patio and custom firepit crafted directly from native fieldstone, all beneath a classic wood-shingle and copper roof. The surrounding grounds function as a true New England compound. A separate two-bedroom carriage house offers built-in guest quarters with a covered porch and an oversized 2.5-car garage. Nearby, a newer two-story 40'x28' barn provides flexible space for a creative studio, vehicle storage, or livestock, complemented by two additional storage sheds. Recent improvements include, but are not limited to, a new cedar-shingle roof with copper downspouts (2025), new A/C, fresh interior paint throughout (2026), and refinished flooring. It is an unmistakable rural sanctuary with abundant room for hosting friends and extended family.

3 Beds ⋅ 3 Baths ⋅ 24192284 MLS

Steeped in 18th-century charm, this rare 1747 Saltbox estate seamlessly marries historic integrity with modern luxury. Tucked away on a peaceful country lane, the main home boasts original wide-plank wood floors, dual fireplaces, twin staircases, authentic built-ins, and freshly renovated baths. At its heart is the kitchen featuring Viking appliances and granite counters that open to garden views. Step through the screened stone-and-timber breezeway to a newly expanded patio and custom firepit crafted directly from native fieldstone, all beneath a classic wood-shingle and copper roof. The surrounding grounds function as a true New England compound. A separate two-bedroom carriage house offers built-in guest quarters with a covered porch and an oversized 2.5-car garage. Nearby, a newer two-story 40'x28' barn provides flexible space for a creative studio, vehicle storage, or livestock, complemented by two additional storage sheds. Recent improvements include, but are not limited to, a new cedar-shingle roof with copper downspouts (2025), new A/C, fresh interior paint throughout (2026), and refinished flooring. It is an unmistakable rural sanctuary with abundant room for hosting friends and extended family.

509 Weekeepeemee Rd, Woodbury

$1,000,000

An exceptional opportunity to own 76.9 acres in one of Woodbury's most desirable locations. This unique offering includes two contiguous parcels to be sold together, consisting of 14.9-acre parcel (MLS# 24192651) and this adjoining 62-acre parcel Featuring a charming 3-bedroom home, the property offers a rare combination of rolling meadows, mature woodlands, and open fields, creating endless possibilities for the next owner. Whether you're seeking a private country estate, equestrian property, family compound, recreational retreat, hunting property, or a prime development opportunity, this expansive acreage provides the flexibility to bring your vision to life. Surrounded by the natural beauty of Woodbury while offering convenient access to local amenities, this is a truly remarkable opportunity to invest in one of Litchfield County's most sought-after communities. A rare offering where privacy, scenic landscapes, and future potential come together.

24192209 MLS

An exceptional opportunity to own 76.9 acres in one of Woodbury's most desirable locations. This unique offering includes two contiguous parcels to be sold together, consisting of 14.9-acre parcel (MLS# 24192651) and this adjoining 62-acre parcel Featuring a charming 3-bedroom home, the property offers a rare combination of rolling meadows, mature woodlands, and open fields, creating endless possibilities for the next owner. Whether you're seeking a private country estate, equestrian property, family compound, recreational retreat, hunting property, or a prime development opportunity, this expansive acreage provides the flexibility to bring your vision to life. Surrounded by the natural beauty of Woodbury while offering convenient access to local amenities, this is a truly remarkable opportunity to invest in one of Litchfield County's most sought-after communities. A rare offering where privacy, scenic landscapes, and future potential come together.

245 Hoop Pole Hill Rd, Woodbury

$1,100,000

Spacious Colonial in desirable Carriage Hills offers approximately 5,700 square feet of living space, including a walk-out lower level that is well suited for an in-law suite or au pair quarters. The main level features wood floors, formal living and dining rooms, an eat-in kitchen, a bedroom, a full bath, and a family room with a fireplace that opens to an oversized deck. Upstairs, you'll find three bedrooms, a full bath, and a spacious primary suite with a spa-like bath and loft area. The walk-out lower level includes three finished rooms plus a full bath, offering flexible space for guests, extended living, recreation, or work-from-home needs. The private backyard is surrounded by trees and accented with perennial gardens. NEW Roof June 2026. Located in Woodbury-one of Connecticut's most beloved small towns-the home is close to charming shops, antique stores, coffee shops, and restaurants, all just about 90 minutes from New York City.

4 Beds ⋅ 4 Baths ⋅ 24192457 MLS

Spacious Colonial in desirable Carriage Hills offers approximately 5,700 square feet of living space, including a walk-out lower level that is well suited for an in-law suite or au pair quarters. The main level features wood floors, formal living and dining rooms, an eat-in kitchen, a bedroom, a full bath, and a family room with a fireplace that opens to an oversized deck. Upstairs, you'll find three bedrooms, a full bath, and a spacious primary suite with a spa-like bath and loft area. The walk-out lower level includes three finished rooms plus a full bath, offering flexible space for guests, extended living, recreation, or work-from-home needs. The private backyard is surrounded by trees and accented with perennial gardens. NEW Roof June 2026. Located in Woodbury-one of Connecticut's most beloved small towns-the home is close to charming shops, antique stores, coffee shops, and restaurants, all just about 90 minutes from New York City.

16 Gate Post Ln, Woodbury

$1,795,000

Just 2 hours from New York City, this exceptional lakefront retreat offers a rare blend of privacy, natural beauty & turnkey luxury. Tucked at the end of West Lake Rd and bordered by the protected woodlands of Flanders Nature Center Preserve, the property enjoys sweeping, unobstructed views across pristine Lake Quassapaug to historic Tranquillity Farm, designed by McKim, Mead & White. Lake Quassapaug is a private lake with no public access & a 10-mph speed limit, creating an ideal setting for boating, fishing, swimming & year-round recreation. Private beach & dock provide direct water access, while the renovated lakeside cabana offers flexible space for a home office, fitness studio or retreat. Outdoor KIT, BBQ area & multiple patios, including a waterfront terrace, are perfect for entertaining. Renovated in 2020, the home features a beautifully appointed gourmet KIT with premium finishes & seamless flow to inviting living spaces. One of only a select few lakefront homes in Woodbury, it benefits from the town's favorable tax structure while being minutes to historic Main St, acclaimed restaurants & antique shops. Town of Woodbury recognizes 112 West Lake Road and a few other neighboring properties as condominium units. All other homes on the Lake are in Middlebury CT. Rare opportunity to own a fully renovated waterfront home with exceptional privacy, spectacular views & an unparalleled lake lifestyle.

2 Beds ⋅ 2 Baths ⋅ 24185479 MLS ⋅ Woodlake BLDG.

Just 2 hours from New York City, this exceptional lakefront retreat offers a rare blend of privacy, natural beauty & turnkey luxury. Tucked at the end of West Lake Rd and bordered by the protected woodlands of Flanders Nature Center Preserve, the property enjoys sweeping, unobstructed views across pristine Lake Quassapaug to historic Tranquillity Farm, designed by McKim, Mead & White. Lake Quassapaug is a private lake with no public access & a 10-mph speed limit, creating an ideal setting for boating, fishing, swimming & year-round recreation. Private beach & dock provide direct water access, while the renovated lakeside cabana offers flexible space for a home office, fitness studio or retreat. Outdoor KIT, BBQ area & multiple patios, including a waterfront terrace, are perfect for entertaining. Renovated in 2020, the home features a beautifully appointed gourmet KIT with premium finishes & seamless flow to inviting living spaces. One of only a select few lakefront homes in Woodbury, it benefits from the town's favorable tax structure while being minutes to historic Main St, acclaimed restaurants & antique shops. Town of Woodbury recognizes 112 West Lake Road and a few other neighboring properties as condominium units. All other homes on the Lake are in Middlebury CT. Rare opportunity to own a fully renovated waterfront home with exceptional privacy, spectacular views & an unparalleled lake lifestyle.

112 W Lake Rd Unit 112, Woodbury

$1,790,000

It's rare to find a vintage estate tucked away from a main road, but this one sits at the end of a private lane, opening to 6.3 enchanting acres framed by stone walls, manicured gardens, and a charming vintage home. The property includes a large custom two-story pole barn, inground pool, detached three-bay garage, and an adorable potting shed. The great room flows into a kitchen with handmade cabinetry, butler's pantry, soapstone counters, and a Vulcan stove, all centered around a brick fireplace flanked by double French doors leading to a shady brick patio. Off the kitchen, a spacious screened porch surrounded with stone walls, offers a peaceful spot to enjoy the seasons. The formal living room, currently an office, boasts a light-filled five-window bay, while two front entry rooms serve as a den and library. The primary suite, in its own wing above the great room, features a private living room, full bath, sleeping area, and views of Perkins Ponds. Three additional bedrooms, accessed via a second staircase, are bright, charming, and surprisingly well-appointed with closets. The impressive barn offers tandem bays for vehicles, a heated workshop, and two upper rooms perfect for future studio spaces. Relax by the pool, take in the flowers, and enjoy the chorus of birds.

4 Beds ⋅ 3 Baths ⋅ 24184948 MLS

It's rare to find a vintage estate tucked away from a main road, but this one sits at the end of a private lane, opening to 6.3 enchanting acres framed by stone walls, manicured gardens, and a charming vintage home. The property includes a large custom two-story pole barn, inground pool, detached three-bay garage, and an adorable potting shed. The great room flows into a kitchen with handmade cabinetry, butler's pantry, soapstone counters, and a Vulcan stove, all centered around a brick fireplace flanked by double French doors leading to a shady brick patio. Off the kitchen, a spacious screened porch surrounded with stone walls, offers a peaceful spot to enjoy the seasons. The formal living room, currently an office, boasts a light-filled five-window bay, while two front entry rooms serve as a den and library. The primary suite, in its own wing above the great room, features a private living room, full bath, sleeping area, and views of Perkins Ponds. Three additional bedrooms, accessed via a second staircase, are bright, charming, and surprisingly well-appointed with closets. The impressive barn offers tandem bays for vehicles, a heated workshop, and two upper rooms perfect for future studio spaces. Relax by the pool, take in the flowers, and enjoy the chorus of birds.

40 Ruffin Rd, Woodbury

$2,995,000

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 two-car garage, pool cabana and pool equipment building. A newly constructed temperature controlled 3,800-square-foot post-and-beam barn with a half bath and laundry room at the rear of the property further expand the property's possibilities. There are also an equipment/horse barn and riverside cabin. Outdoor living is equally remarkable with a stunning new in-ground gunite pool surrounded by lush landscaping. Designed for both relaxation and entertaining, the grounds include a custom "summer kitchen" with a European-style outdoor pizza oven, gas grill, and screened dining pavilion-perfect for hosting gatherings or enjoying quiet evenings. The 18.3-acre setting includes mature trees, open meadows, scenic walking trails, and frontage along the protected Pomperaug River, creating a private and picturesque retreat. Rich in history yet thoughtfully updated, this rare estate offers an exceptional combination of beauty, functionality, and enduring charm. A comprehensive list of recent improvements is available upon request. Buyer must do due diligence with the town for possible uses.

4 Beds ⋅ 6 Baths ⋅ 24163576 MLS

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 two-car garage, pool cabana and pool equipment building. A newly constructed temperature controlled 3,800-square-foot post-and-beam barn with a half bath and laundry room at the rear of the property further expand the property's possibilities. There are also an equipment/horse barn and riverside cabin. Outdoor living is equally remarkable with a stunning new in-ground gunite pool surrounded by lush landscaping. Designed for both relaxation and entertaining, the grounds include a custom "summer kitchen" with a European-style outdoor pizza oven, gas grill, and screened dining pavilion-perfect for hosting gatherings or enjoying quiet evenings. The 18.3-acre setting includes mature trees, open meadows, scenic walking trails, and frontage along the protected Pomperaug River, creating a private and picturesque retreat. Rich in history yet thoughtfully updated, this rare estate offers an exceptional combination of beauty, functionality, and enduring charm. A comprehensive list of recent improvements is available upon request. Buyer must do due diligence with the town for possible uses.

920 Main St S, Woodbury

$1,150,000

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 mile of frontage along Flanders Road, classic stone walls, pristine streams, established culvert crossings, and abundant wildlife define the landscape, while private trails invite walking, hiking, and outdoor recreation. Just 90 minutes from New York City and 10 minutes from Woodbury's shops and historic antique trail, East Meadowbrook Farm offers a peaceful country sanctuary with limitless potential for a premium estate, hobby farm, or family compound.

24177403 MLS

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 mile of frontage along Flanders Road, classic stone walls, pristine streams, established culvert crossings, and abundant wildlife define the landscape, while private trails invite walking, hiking, and outdoor recreation. Just 90 minutes from New York City and 10 minutes from Woodbury's shops and historic antique trail, East Meadowbrook Farm offers a peaceful country sanctuary with limitless potential for a premium estate, hobby farm, or family compound.

Flanders Road, Woodbury

$1,495,000

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.

5 Beds ⋅ 5 Baths ⋅ 24168618 MLS

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.

30 Hollow, Woodbury

$1,350,000

Prime commercial opportunity on Main Street South in Woodbury, adjacent to the well-known 1754 House restaurant. Formerly the longtime home of Agway/Green Acres, this versatile property features a spacious retail layout with a large open display floor, multiple additional rooms, and on-site restrooms. The site also includes a sizable parking area and covered outdoor display space, making it well suited for a wide range of commercial uses. With excellent visibility, strong traffic exposure, and a sought-after location, this property offers exceptional potential. Set on 7 acres, the parcel provides ample room for storage, additional outbuildings, or future expansion. It also presents a rare opportunity for mixed-use development, with possibilities for both commercial and residential use. All mapping and soil testing have already been completed, adding further value for future planning and development.

1 Baths ⋅ 24161266 MLS

Prime commercial opportunity on Main Street South in Woodbury, adjacent to the well-known 1754 House restaurant. Formerly the longtime home of Agway/Green Acres, this versatile property features a spacious retail layout with a large open display floor, multiple additional rooms, and on-site restrooms. The site also includes a sizable parking area and covered outdoor display space, making it well suited for a wide range of commercial uses. With excellent visibility, strong traffic exposure, and a sought-after location, this property offers exceptional potential. Set on 7 acres, the parcel provides ample room for storage, additional outbuildings, or future expansion. It also presents a rare opportunity for mixed-use development, with possibilities for both commercial and residential use. All mapping and soil testing have already been completed, adding further value for future planning and development.

524 Main St S, 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