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If privacy in the Litchfield Hills is your aspiration, this is the place for you! Gated entrance to this rustic Country Cape w/ covered porch set back off the road. Property abuts land locked acreage & Roxbury Land Trust surrounds much of the neighborhood. The current & ONLY owner constructed this quality built home with lasting craftsmanship. To say it has good bones is an understatement. 4th bedroom is in the lower level but upper level loft could be transformed to another bedroom or office. Expansive kitchen w/ angled island leads to the open 2 story "Vermont style" great room w/ floor to ceiling fieldstone fireplace. The detached garage has an upper level workshop w/ electricity & accommodations for a coal or wood stove. Perfect space for a separate workshop or artist's studio. Another unique feature is the lower level panic room & a huge vault for your valuables, guns, or collectibles. The property provides ample room for additional outbuildings, a main house addition, & a swimming pool. Property will be sold as-is but with a median sales price in Roxbury of $1.4 million, there is only room to go up! Roxbury is a blend of historic charm, environmental stewardship, & community warmth that attracts creatives, academics, & even a celebrity or 2! FREE HOME INSPECTION to the buyer. Seller is relocating & MOTIVATED! Price reflects the projects to be tasked: flooring thru most of the house, some int/ext trim, boiler & roof (fully functioning but older). Best price in town!

4 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24117052 MLS

If privacy in the Litchfield Hills is your aspiration, this is the place for you! Gated entrance to this rustic Country Cape w/ covered porch set back off the road. Property abuts land locked acreage & Roxbury Land Trust surrounds much of the neighborhood. The current & ONLY owner constructed this quality built home with lasting craftsmanship. To say it has good bones is an understatement. 4th bedroom is in the lower level but upper level loft could be transformed to another bedroom or office. Expansive kitchen w/ angled island leads to the open 2 story "Vermont style" great room w/ floor to ceiling fieldstone fireplace. The detached garage has an upper level workshop w/ electricity & accommodations for a coal or wood stove. Perfect space for a separate workshop or artist's studio. Another unique feature is the lower level panic room & a huge vault for your valuables, guns, or collectibles. The property provides ample room for additional outbuildings, a main house addition, & a swimming pool. Property will be sold as-is but with a median sales price in Roxbury of $1.4 million, there is only room to go up! Roxbury is a blend of historic charm, environmental stewardship, & community warmth that attracts creatives, academics, & even a celebrity or 2! FREE HOME INSPECTION to the buyer. Seller is relocating & MOTIVATED! Price reflects the projects to be tasked: flooring thru most of the house, some int/ext trim, boiler & roof (fully functioning but older). Best price in town!

55 Mallory Rd, Roxbury

$610,000

Sunsets beyond compare await you at the end of the curved driveway, up to your secluded 6.89-acre lot. This home needs updates, however is a tremendous opportunity to live in Roxbury CT, with 3,476 Sq feet, 11 rooms, 4 bedrooms on upper level, boasting hardwood flooring & large closets. Primary suite has large walk-in shower stall & two walk-in closets. Many possibilities with the two large finished rooms over the garage - Au pair setup or in-home office with separate entrance and back staircase from the attached garage. 4 fireplaces, large eat in kitchen, dining & living room, plus family room and separate den with fire place off the garage. Relax, enjoy the privacy and curl up with a book on the exterior front bluestone patio with fireplace. Propane, forced air furnace, plus electric baseboards. There is no basement as the home is built on a slab, however there is a large unfinished walk-up attic. TLC is needed to bring this home back to its original sparkle, and is priced accordingly. DO NOT STEP ONTO THE PROPERTY WITHOUT AN APPOINTMENT. Camera in use inside and out

4 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24147606 MLS

Sunsets beyond compare await you at the end of the curved driveway, up to your secluded 6.89-acre lot. This home needs updates, however is a tremendous opportunity to live in Roxbury CT, with 3,476 Sq feet, 11 rooms, 4 bedrooms on upper level, boasting hardwood flooring & large closets. Primary suite has large walk-in shower stall & two walk-in closets. Many possibilities with the two large finished rooms over the garage - Au pair setup or in-home office with separate entrance and back staircase from the attached garage. 4 fireplaces, large eat in kitchen, dining & living room, plus family room and separate den with fire place off the garage. Relax, enjoy the privacy and curl up with a book on the exterior front bluestone patio with fireplace. Propane, forced air furnace, plus electric baseboards. There is no basement as the home is built on a slab, however there is a large unfinished walk-up attic. TLC is needed to bring this home back to its original sparkle, and is priced accordingly. DO NOT STEP ONTO THE PROPERTY WITHOUT AN APPOINTMENT. Camera in use inside and out

22 E Woods Rd, Roxbury

$606,000

Diamond in the rough! This solid and expansive home is waiting for its new life, with you as the steward. It has 3 good sized bedrooms, a bonus room off the primary (which is ensuite), a large partially finished lower level, perfect for a game room, gym, man or woman cave, an open floor plan from the kitchen to the family room, a multi-level deck, an oversized 2 car garage and a large, beautiful yard lined by beautiful stone walls with perennial beds, all located in the highly desirable town of Roxbury, where the average sale price is well north of $1M. 90 minutes to Manhattan, this is southern Litchfield County, so you get the beauty and cultural life found locally, with proximity to Westchester, Fairfield and NYC. Great hiking, restaurants and art abounds within minutes. This is an as-is sale, with the price reflecting the condition of the property. There will be no seller concessions for inspection issues.

3 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24197990 MLS

Diamond in the rough! This solid and expansive home is waiting for its new life, with you as the steward. It has 3 good sized bedrooms, a bonus room off the primary (which is ensuite), a large partially finished lower level, perfect for a game room, gym, man or woman cave, an open floor plan from the kitchen to the family room, a multi-level deck, an oversized 2 car garage and a large, beautiful yard lined by beautiful stone walls with perennial beds, all located in the highly desirable town of Roxbury, where the average sale price is well north of $1M. 90 minutes to Manhattan, this is southern Litchfield County, so you get the beauty and cultural life found locally, with proximity to Westchester, Fairfield and NYC. Great hiking, restaurants and art abounds within minutes. This is an as-is sale, with the price reflecting the condition of the property. There will be no seller concessions for inspection issues.

90 Mallory Rd, Roxbury

$597,000

Best Litchfield County Opportunity! Escape to your own peaceful country retreat with the perfect blend of comfort, character, and privacy on nearly 5 acres of wooded wonderland. Less than 2 hours from NYC, this home has lots of character and a flexible layout with 2 bedrooms, 2 full bathrooms plus an upper level guest room/office/rec room. Main floor layout with separate spaces set up well for relaxing or entertaining, and a kitchen with plenty of prep and storage space. Expansive wrap-around deck outside - the perfect spot for morning coffee, al fresco dining, or simply unwinding and unplugging while enjoying the sights and sounds of your private pond and surrounding woods. Nature lovers will appreciate the serene setting that offers privacy and tranquility. Hikers and bikers will gravitate to nearby trails on the Roxbury Land Trust. The town of Roxbury has long been sought-after as a convenient country getaway providing small-town Connecticut living but so close to Westchester and the city. Very convenient to shopping in nearby towns of Woodbury and Southbury.

2 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 24182244 MLS

Best Litchfield County Opportunity! Escape to your own peaceful country retreat with the perfect blend of comfort, character, and privacy on nearly 5 acres of wooded wonderland. Less than 2 hours from NYC, this home has lots of character and a flexible layout with 2 bedrooms, 2 full bathrooms plus an upper level guest room/office/rec room. Main floor layout with separate spaces set up well for relaxing or entertaining, and a kitchen with plenty of prep and storage space. Expansive wrap-around deck outside - the perfect spot for morning coffee, al fresco dining, or simply unwinding and unplugging while enjoying the sights and sounds of your private pond and surrounding woods. Nature lovers will appreciate the serene setting that offers privacy and tranquility. Hikers and bikers will gravitate to nearby trails on the Roxbury Land Trust. The town of Roxbury has long been sought-after as a convenient country getaway providing small-town Connecticut living but so close to Westchester and the city. Very convenient to shopping in nearby towns of Woodbury and Southbury.

188 Bacon Rd, Roxbury

$583,000

Compelling opportunity nestled in the heart of Roxbury's coveted Battleswamp and Mine Hill Preserve area. This remarkable 8.9 acre property features approximately four acres of open meadows, dramatic stone outcroppings, sweeping lawns, woodland privacy and natural beauty. Extensive road frontage- over 800ft along the most peaceful pristine roads- enjoy walking paths, bike rides. This setting provides a canvas for a country retreat, thoughtful renovation, expansion, or a distinctive country compound. Equally rare is its accessibility-peacefully away, yet just minutes to Washington Depot, Woodbury, and convenient routes to Fairfield County, making it an ideal gateway Litchfield County and beyond.

2 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 24177292 MLS

Compelling opportunity nestled in the heart of Roxbury's coveted Battleswamp and Mine Hill Preserve area. This remarkable 8.9 acre property features approximately four acres of open meadows, dramatic stone outcroppings, sweeping lawns, woodland privacy and natural beauty. Extensive road frontage- over 800ft along the most peaceful pristine roads- enjoy walking paths, bike rides. This setting provides a canvas for a country retreat, thoughtful renovation, expansion, or a distinctive country compound. Equally rare is its accessibility-peacefully away, yet just minutes to Washington Depot, Woodbury, and convenient routes to Fairfield County, making it an ideal gateway Litchfield County and beyond.

94 Judds Bridge Rd, Roxbury

$455,000

INCREDIBLE OPPORTUNITY TO OWN IN THE PAINTER HILL RD AREA OF ROXBURY! This 1,600 sq ft, 3-bedroom, 2-bathroom Ranch home with a 2-car garage sits on a sun-filled, gently sloping lot with tremendous potential for the new Homeowner. The home features a new roof, furnace, water heater and bilco doors giving you a solid foundation to make it your own. The septic was last pumped September 2025, and annual taxes are just $3,851. Bring your vision and remodel it yourself, or take advantage of our RARE option to have Design Builders & Remodeling Inc. handle ALL the renovations for you - see MLS # 24174231 for details. Either way, you'll be planting roots in Roxbury, one of the most sought-after towns in the Litchfield Hills - known for its low taxes, natural beauty, and year-round outdoor activities.

3 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 24166843 MLS

INCREDIBLE OPPORTUNITY TO OWN IN THE PAINTER HILL RD AREA OF ROXBURY! This 1,600 sq ft, 3-bedroom, 2-bathroom Ranch home with a 2-car garage sits on a sun-filled, gently sloping lot with tremendous potential for the new Homeowner. The home features a new roof, furnace, water heater and bilco doors giving you a solid foundation to make it your own. The septic was last pumped September 2025, and annual taxes are just $3,851. Bring your vision and remodel it yourself, or take advantage of our RARE option to have Design Builders & Remodeling Inc. handle ALL the renovations for you - see MLS # 24174231 for details. Either way, you'll be planting roots in Roxbury, one of the most sought-after towns in the Litchfield Hills - known for its low taxes, natural beauty, and year-round outdoor activities.

137 Davenport Rd, Roxbury

$450,000

Welcome to Willow Brook Drive! If your dream has been to build your new home in what feels like a Monet painting, this property will make your dream a reality. Here is your chance to have two prime lots of land, together making 20+ acres of endless possibility! With year-round beautiful meadows and enchanting woods, you can have the best of both worlds. Originally cattle pasture, the vast fields offer easy building sites and 360 views of nature. If seclusion in the forest is more up your alley, this plentiful land will accommodate for that too. Let your imagination run wild. These approved building lots are ready to develop! Multiple flat & cleared building sites. Underground power and utilities, running up Willow Brook Dr. Feasibility map available upon request with original percolation/soil data.

CLOSED Status ⋅ 24168082 MLS

Welcome to Willow Brook Drive! If your dream has been to build your new home in what feels like a Monet painting, this property will make your dream a reality. Here is your chance to have two prime lots of land, together making 20+ acres of endless possibility! With year-round beautiful meadows and enchanting woods, you can have the best of both worlds. Originally cattle pasture, the vast fields offer easy building sites and 360 views of nature. If seclusion in the forest is more up your alley, this plentiful land will accommodate for that too. Let your imagination run wild. These approved building lots are ready to develop! Multiple flat & cleared building sites. Underground power and utilities, running up Willow Brook Dr. Feasibility map available upon request with original percolation/soil data.

Lot 7 & Lot 8 & Dr, Roxbury

$320,000

Affordable housing opportunity for interested donor. Approved building lot with a complete survey which includes wetland delineation and recommended building site. This 25.01-acre wooded oasis in Roxbury, located just half a mile from scenic Route 67, offers a tranquil and private retreat in the heart of historic Roxbury. With 250 feet of road frontage on Wellers Bridge Rd, this property is a prime opportunity for those looking to build a family compound or estate. Situated between the charming towns of Washington and Woodbury, you'll enjoy easy access to great shopping, dining, a brewery, and more. Roxbury is renowned for its historic charm and natural beauty, making it the perfect backdrop for your dream property. The land is currently designated as forest, which is reflected in its low taxes and assessed value. Essential preliminary work has already been completed, including a survey with perk and pit tests conducted on 10/20/2016, wetland delineation 2024 added to the survey 2025 recorded with the Town. If you're seeking a serene natural haven, this property is a must-see. The land features a combination of wooded areas, partially bordered by charming stone walls, offering the perfect canvas for your private estate. Explore the attached documents for more details and start envisioning the possibilities this exceptional property holds. Ther survey map is included in the listing documents.

CLOSED Status ⋅ 170604882 MLS

Affordable housing opportunity for interested donor. Approved building lot with a complete survey which includes wetland delineation and recommended building site. This 25.01-acre wooded oasis in Roxbury, located just half a mile from scenic Route 67, offers a tranquil and private retreat in the heart of historic Roxbury. With 250 feet of road frontage on Wellers Bridge Rd, this property is a prime opportunity for those looking to build a family compound or estate. Situated between the charming towns of Washington and Woodbury, you'll enjoy easy access to great shopping, dining, a brewery, and more. Roxbury is renowned for its historic charm and natural beauty, making it the perfect backdrop for your dream property. The land is currently designated as forest, which is reflected in its low taxes and assessed value. Essential preliminary work has already been completed, including a survey with perk and pit tests conducted on 10/20/2016, wetland delineation 2024 added to the survey 2025 recorded with the Town. If you're seeking a serene natural haven, this property is a must-see. The land features a combination of wooded areas, partially bordered by charming stone walls, offering the perfect canvas for your private estate. Explore the attached documents for more details and start envisioning the possibilities this exceptional property holds. Ther survey map is included in the listing documents.

Wellers Bridge Rd, Roxbury

$235,000

Get away to the Country! Such a peaceful location to build your dream home. Lightly traveled road. All of nature loves the location, so will you!

CLOSED Status ⋅ 24093092 MLS

Get away to the Country! Such a peaceful location to build your dream home. Lightly traveled road. All of nature loves the location, so will you!

Booth Road, Roxbury

$215,000

Approved Building lot with DOT approval for the driveway. Driveway has been roughed in and leads to the building site set back well from the road. Beautiful outcroppings, mature hardwoods, antique stone walls all set in a private rolling terrain. Survey, perc test and soil survey are available. Peaceful wooded lot to build your weekend or forever home! Close to Washington and Roxbury centers makes this the perfect place to call home.90 minutes to NYC.

CLOSED Status ⋅ 24169970 MLS

Approved Building lot with DOT approval for the driveway. Driveway has been roughed in and leads to the building site set back well from the road. Beautiful outcroppings, mature hardwoods, antique stone walls all set in a private rolling terrain. Survey, perc test and soil survey are available. Peaceful wooded lot to build your weekend or forever home! Close to Washington and Roxbury centers makes this the perfect place to call home.90 minutes to NYC.

307 North St, Roxbury

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