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$3,995,000

A breathtaking country estate nestled in the picturesque town of Roxbury, Connecticut, boasts a guest cottage and an in-ground Gunite pool. Encompassing 8.03 acres, the property is surrounded by Jack's Brook and a land trust on two sides, providing a serene and secluded environment. The primary residence, meticulously updated, features exquisitely proportioned rooms. It comprises five bedrooms and five full bathrooms and one powder room. A grand living room, complete with a two-story fireplace and windows on three sides, opens to two decks overlooking the rear yard. The spacious formal dining room, equipped with a gas fireplace and soft indirect lighting, is ideal for hosting formal gatherings. The chef's-eat-in kitchen, generously furnished with ample cabinetry, marble countertops, connects to a large deck and a granite patio, facilitating seamless outdoor dining. The primary level's main suite features French doors to the gardens, a luxurious bath, two walk-in closets, and a private sitting room. Three additional ensuite bedrooms complete the main level. The lower level offers a media room, a game room, a bunk room with built-in beds, a spa bath, and a laundry facility. A separate guest cottage provides a cozy retreat with two bedrooms, two bathrooms, a vaulted great room, a kitchenette, a fireplace, and a wrap-around deck. A must see!

5 Beds ⋅ 6 Baths ⋅ 24177581 MLS

A breathtaking country estate nestled in the picturesque town of Roxbury, Connecticut, boasts a guest cottage and an in-ground Gunite pool. Encompassing 8.03 acres, the property is surrounded by Jack's Brook and a land trust on two sides, providing a serene and secluded environment. The primary residence, meticulously updated, features exquisitely proportioned rooms. It comprises five bedrooms and five full bathrooms and one powder room. A grand living room, complete with a two-story fireplace and windows on three sides, opens to two decks overlooking the rear yard. The spacious formal dining room, equipped with a gas fireplace and soft indirect lighting, is ideal for hosting formal gatherings. The chef's-eat-in kitchen, generously furnished with ample cabinetry, marble countertops, connects to a large deck and a granite patio, facilitating seamless outdoor dining. The primary level's main suite features French doors to the gardens, a luxurious bath, two walk-in closets, and a private sitting room. Three additional ensuite bedrooms complete the main level. The lower level offers a media room, a game room, a bunk room with built-in beds, a spa bath, and a laundry facility. A separate guest cottage provides a cozy retreat with two bedrooms, two bathrooms, a vaulted great room, a kitchenette, a fireplace, and a wrap-around deck. A must see!

47 Squire Rd, Roxbury

$3,950,000

Uber chic shingle-style in A+ location offering magnificent long distant views overlooking the famed Alexander Calder estate. Formal parking courtyard leads to the gracious double height entrance foyer. Mesmerizing views from almost every room. Grand Living Room with high coffered ceilings, gas fireplace, wood paneling & French door to balconies. Library with built-in bookcases. Powder room. First floor primary bedroom suite with Waterworks bathroom, soaking tub, two walk-in closets, balcony & home Office. Intimate Dining Room with large picture window. Eat-in country Kitchen with beamed ceiling and large picture window. Family Room with fireplace & wet bar. Screened porch with bluestone floor & electric stove. Laundry Room. 3 guest bedrooms en suite on the 2nd floor. Recreation Room over the 3-car attached garage. Walk-out lower level includes a gym, wine cellar, full bath & second laundry. Gracious long driveway affording total privacy amidst park-like grounds with beautiful perennial gardens, swimming pool, fire pit, mature plantings & forever views. Hardwood floors & high ceilings throughout. Lutron lighting. Central AC. Backup generator.

4 Beds ⋅ 7 Baths ⋅ 24192621 MLS

Uber chic shingle-style in A+ location offering magnificent long distant views overlooking the famed Alexander Calder estate. Formal parking courtyard leads to the gracious double height entrance foyer. Mesmerizing views from almost every room. Grand Living Room with high coffered ceilings, gas fireplace, wood paneling & French door to balconies. Library with built-in bookcases. Powder room. First floor primary bedroom suite with Waterworks bathroom, soaking tub, two walk-in closets, balcony & home Office. Intimate Dining Room with large picture window. Eat-in country Kitchen with beamed ceiling and large picture window. Family Room with fireplace & wet bar. Screened porch with bluestone floor & electric stove. Laundry Room. 3 guest bedrooms en suite on the 2nd floor. Recreation Room over the 3-car attached garage. Walk-out lower level includes a gym, wine cellar, full bath & second laundry. Gracious long driveway affording total privacy amidst park-like grounds with beautiful perennial gardens, swimming pool, fire pit, mature plantings & forever views. Hardwood floors & high ceilings throughout. Lutron lighting. Central AC. Backup generator.

297 Painter Hill Rd, Roxbury

$3,600,000

Quintessential Litchfield County Estate on 41+/- acres. Restored 1850's Colonial. Set in private, park-like grounds, overlooking spring-fed pond & meadows w/ views and mature trees. 5-bedrooms, 4.5 bathrooms, eat-in kitchen w/ fp, great room w/ fp and dining room with French doors, family room w/ fp, sunroom with wet bar, library, office, media room, recreational room, porch, 3-car garage, gunite pool, pool house, 4-stall horse barn, tennis court. Riding ring, fenced pastures, wooded trails for hiking etc. Perennial gardens. Property abuts conservation land. Complete privacy. Rare opportunity. Property has only been on the market twice before in past 100 years.

5 Beds ⋅ 5 Baths ⋅ 24183686 MLS

Quintessential Litchfield County Estate on 41+/- acres. Restored 1850's Colonial. Set in private, park-like grounds, overlooking spring-fed pond & meadows w/ views and mature trees. 5-bedrooms, 4.5 bathrooms, eat-in kitchen w/ fp, great room w/ fp and dining room with French doors, family room w/ fp, sunroom with wet bar, library, office, media room, recreational room, porch, 3-car garage, gunite pool, pool house, 4-stall horse barn, tennis court. Riding ring, fenced pastures, wooded trails for hiking etc. Perennial gardens. Property abuts conservation land. Complete privacy. Rare opportunity. Property has only been on the market twice before in past 100 years.

268 South St, Roxbury

$3,495,000

Subtle Sophistication in A++ Roxbury Locale. Perfectly sited in an estate area of Roxbury on a quiet country road, this renovated country cottage exudes understated elegance & modern comfort. Main house offers one-level living & turn-key perfection, w/chic kitchen featuring custom cabinetry, stainless steel appliances, it flows seamlessly into the dining room. Dramatic great room w/floor-to-ceiling glass & fireplace anchors the living spaces, opening directly to large deck for effortless outdoor entertaining & picturesque views of the grounds. There are 4 ensuite bdrms, incl a stunning 1st-flr primary suite w/sitting room, gas fireplace, 2 fully built-out walk-in closets, & French doors leading to a private terrace with outdoor fireplace. Cozy library/den with built-ins and a versatile lower-level bonus space are ideal for an art studio or private home office. Add'l highlights incl a steam shower, smart-home features, radiant heat w/hydro-air backup, 2 washers & dryers. Dramatic post-and-beam guest house w/ vaulted ceiling, balcony, & full kitchen sits above a 2 car garage and prep kitchen, offering a private retreat complete w/its own washer/dryer. The grounds are exceptional-mature trees, stone walls, a pond, sweeping lawns, and lush gardens surrounding a heated gunite pool. Expansive porches and terraces provide seamless indoor-outdoor living, ensuring total privacy. Minutes from The Mayflower Inn, town center and close to acres of Roxbury Land Trust. 90 min to NYC.

4 Beds ⋅ 5 Baths ⋅ 24201025 MLS

Subtle Sophistication in A++ Roxbury Locale. Perfectly sited in an estate area of Roxbury on a quiet country road, this renovated country cottage exudes understated elegance & modern comfort. Main house offers one-level living & turn-key perfection, w/chic kitchen featuring custom cabinetry, stainless steel appliances, it flows seamlessly into the dining room. Dramatic great room w/floor-to-ceiling glass & fireplace anchors the living spaces, opening directly to large deck for effortless outdoor entertaining & picturesque views of the grounds. There are 4 ensuite bdrms, incl a stunning 1st-flr primary suite w/sitting room, gas fireplace, 2 fully built-out walk-in closets, & French doors leading to a private terrace with outdoor fireplace. Cozy library/den with built-ins and a versatile lower-level bonus space are ideal for an art studio or private home office. Add'l highlights incl a steam shower, smart-home features, radiant heat w/hydro-air backup, 2 washers & dryers. Dramatic post-and-beam guest house w/ vaulted ceiling, balcony, & full kitchen sits above a 2 car garage and prep kitchen, offering a private retreat complete w/its own washer/dryer. The grounds are exceptional-mature trees, stone walls, a pond, sweeping lawns, and lush gardens surrounding a heated gunite pool. Expansive porches and terraces provide seamless indoor-outdoor living, ensuring total privacy. Minutes from The Mayflower Inn, town center and close to acres of Roxbury Land Trust. 90 min to NYC.

35 Schoolhouse Rd, Roxbury

$2,000,000

If You are looking for land with views to build your dream home, this is it. This is truly an "Estate Property". The 27 acres is cleared and open. There are several building sites at the top with 180 degree views. The land slopes gently down with a brook and 2 small ponds at the bottom. There is a fairly large barn and a smaller shop on the property in need of repairs. They are being sold AS IS! Bring your plans and build in a most beautiful part of the world in a sought after Connecticut town. Litchfield County is rural and beautiful. Enjoy farmers markets and country fairs. Visit any number of great restaurants in the area. There are many art shows, antique shops and boutiques to visit. As for outdoor activities, there are thousands of acres of land trust and hiking trails in Roxbury and surrounding towns. The Shepard River offers great fishing. There are ski areas close by as well as lakes for boating, fishing and swimming. Located under 2 hours from NYC! Taxes are based on 490 farming designation.

24170752 MLS

If You are looking for land with views to build your dream home, this is it. This is truly an "Estate Property". The 27 acres is cleared and open. There are several building sites at the top with 180 degree views. The land slopes gently down with a brook and 2 small ponds at the bottom. There is a fairly large barn and a smaller shop on the property in need of repairs. They are being sold AS IS! Bring your plans and build in a most beautiful part of the world in a sought after Connecticut town. Litchfield County is rural and beautiful. Enjoy farmers markets and country fairs. Visit any number of great restaurants in the area. There are many art shows, antique shops and boutiques to visit. As for outdoor activities, there are thousands of acres of land trust and hiking trails in Roxbury and surrounding towns. The Shepard River offers great fishing. There are ski areas close by as well as lakes for boating, fishing and swimming. Located under 2 hours from NYC! Taxes are based on 490 farming designation.

55 Ranney Hill Rd, Roxbury

$1,795,000

Perched above the tranquil waters of Jacks Brook in southern Roxbury, this Modern Mountain Tudor offers refined open-concept living with exceptional accessibility to New York City, just five minutes from Roxbury Center. Set on a private, level site, the property enjoys protected brookside land that preserves the natural landscape and uninterrupted views that define the home's character. A grand circular driveway introduces the residence, where sweeping lawns and striking architecture create a powerful sense of arrival, privacy, and seclusion. Inside, light-filled interiors showcase soaring ceilings and oversized windows that capture serene vistas from nearly every room, blending contemporary sophistication with warmth and comfort. The remodeled kitchen serves as the heart of the home, seamlessly combining modern design with functional luxury as it flows into the main living areas. With five generously proportioned bedrooms and six bathrooms, the thoughtfully scaled floor plan accommodates both grand entertaining and intimate everyday living. The lower level features a versatile in-law suite complete with a full kitchen, private bedroom, bathroom, living room, separate entrance, and direct access to the grounds, along with an additional great room or family room that opens to the expansive lawn, offering a seamless indoor-outdoor connection ideal for guests or multigenerational living.

5 Beds ⋅ 6 Baths ⋅ 24189301 MLS

Perched above the tranquil waters of Jacks Brook in southern Roxbury, this Modern Mountain Tudor offers refined open-concept living with exceptional accessibility to New York City, just five minutes from Roxbury Center. Set on a private, level site, the property enjoys protected brookside land that preserves the natural landscape and uninterrupted views that define the home's character. A grand circular driveway introduces the residence, where sweeping lawns and striking architecture create a powerful sense of arrival, privacy, and seclusion. Inside, light-filled interiors showcase soaring ceilings and oversized windows that capture serene vistas from nearly every room, blending contemporary sophistication with warmth and comfort. The remodeled kitchen serves as the heart of the home, seamlessly combining modern design with functional luxury as it flows into the main living areas. With five generously proportioned bedrooms and six bathrooms, the thoughtfully scaled floor plan accommodates both grand entertaining and intimate everyday living. The lower level features a versatile in-law suite complete with a full kitchen, private bedroom, bathroom, living room, separate entrance, and direct access to the grounds, along with an additional great room or family room that opens to the expansive lawn, offering a seamless indoor-outdoor connection ideal for guests or multigenerational living.

233 Southbury Rd, Roxbury

$1,469,000

Mint/Move-in Condition! Private c. 2002 Colonial Clapboard 4+ bedroom home on a scenic dirt road along the Shepaug River and just down the road from Land Trust with trails. Heated Gunite Pool surrounded by endless summer hydrangea and 3 acres of level lawn bordered by the Moosehorn Brook. Magnificent design, 4 wood-burning fireplaces, beautiful wide-board softwood floors, over-sized living room, spacious dining room and chef's kitchen with striking polished hardwood center island. Upstairs, Primary En Suite Bedroom with lovely clawfoot tub, double sinks, large separate shower and spacious dressing room. Two more bedrooms share a charming hall bath. Finished lower level currently outfitted as a family room with French doors to a serene patio leading out to the pool, another en suite bedroom and two more finished flexible spaces. (Makes the total finished sq feet: 3676!)The perfect peaceful location, minutes from the centers of Roxbury and Washington. Must see!

4 Beds ⋅ 4 Baths ⋅ 24163570 MLS

Mint/Move-in Condition! Private c. 2002 Colonial Clapboard 4+ bedroom home on a scenic dirt road along the Shepaug River and just down the road from Land Trust with trails. Heated Gunite Pool surrounded by endless summer hydrangea and 3 acres of level lawn bordered by the Moosehorn Brook. Magnificent design, 4 wood-burning fireplaces, beautiful wide-board softwood floors, over-sized living room, spacious dining room and chef's kitchen with striking polished hardwood center island. Upstairs, Primary En Suite Bedroom with lovely clawfoot tub, double sinks, large separate shower and spacious dressing room. Two more bedrooms share a charming hall bath. Finished lower level currently outfitted as a family room with French doors to a serene patio leading out to the pool, another en suite bedroom and two more finished flexible spaces. (Makes the total finished sq feet: 3676!)The perfect peaceful location, minutes from the centers of Roxbury and Washington. Must see!

33 Sentry Hill Rd, Roxbury

$725,000

Cottage & Guest House Located in pastoral Southern Roxbury, just 90 minutes from New York City. Set on 2 acres, the property features a historic c.1817 three-bedroom antique cape-featured in Elle Decor-a charming two-bedroom guest house. The main residence exudes rustic character, with original hand-hewn beams, wide-plank oak floors, a wood-burning fireplace, and classic plaster walls and it has a brand new steel standing seam roof. At its heart is a spacious eat-in kitchen, flanked by a formal dining room and library on one side, and a sunlit living room wrapped in windows on the other. The 658 square-foot guest house overlooks the spring-fed pond and includes a generous living room, two bedrooms, and a full bath-serviced by its own septic. The grounds are serene and beautifully landscaped, with a cantilevered "waterfront" sun deck, mature trees, lush gardens, and gently rolling lawn. This charming home blends history, potential, and natural beauty in one of Litchfield County's most coveted locations., Additional acreage available- separate 6.71-acre buildable lot with potential for a spacious custom home at the end of a long, private driveway. Total square footage is combined main house and guest house.

5 Beds ⋅ 3 Baths ⋅ 24178189 MLS

Cottage & Guest House Located in pastoral Southern Roxbury, just 90 minutes from New York City. Set on 2 acres, the property features a historic c.1817 three-bedroom antique cape-featured in Elle Decor-a charming two-bedroom guest house. The main residence exudes rustic character, with original hand-hewn beams, wide-plank oak floors, a wood-burning fireplace, and classic plaster walls and it has a brand new steel standing seam roof. At its heart is a spacious eat-in kitchen, flanked by a formal dining room and library on one side, and a sunlit living room wrapped in windows on the other. The 658 square-foot guest house overlooks the spring-fed pond and includes a generous living room, two bedrooms, and a full bath-serviced by its own septic. The grounds are serene and beautifully landscaped, with a cantilevered "waterfront" sun deck, mature trees, lush gardens, and gently rolling lawn. This charming home blends history, potential, and natural beauty in one of Litchfield County's most coveted locations., Additional acreage available- separate 6.71-acre buildable lot with potential for a spacious custom home at the end of a long, private driveway. Total square footage is combined main house and guest house.

50 Southbury Rd, Roxbury

$575,000

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 ⋅ 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

$425,000

Rare in the Litchfield Hills-a flat, lightly wooded 6.71-acre buildable lot with a stream and stone walls. Perc'd for a spacious 4 bedroom custom home, and potential for a long private driveway. Perc's are 20 years old may have to be redone based on your plan.

24178195 MLS

Rare in the Litchfield Hills-a flat, lightly wooded 6.71-acre buildable lot with a stream and stone walls. Perc'd for a spacious 4 bedroom custom home, and potential for a long private driveway. Perc's are 20 years old may have to be redone based on your plan.

Southbury Road, Roxbury

Dave Jones Realty llc

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