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Moosehorn Rd in Roxbury was voted one of the most scenic Roads in town. Must see! Well-appointed and maintained, first time on the market, original owner, charming 1,456 sqft ranch, 3 bathrooms and 2 bedrooms, kitchen, dining, living room with fireplace, C/A, central vacuum, Generac generator connected. Walkout finished basement with entrance from garage is an in-law apartment with kitchen gas stove and full bath. The main house water comes from two sources a well and from a spring fed well. Detached barn offering heat and A/C with 950 sqfr four car garage and 600sqft attic; A two-car garage in the back with 600 sqft and 500sqft attic; many possibilities shop, studio/ in-law appt or garage/storage income. Your own Spring in your own property; close to Westchester, Fairfield and NYC. Great hiking, restaurants, and art abound within minutes. "As is Condition" See attached list of all recent maintenance service and repairs.

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24210827 MLS

Moosehorn Rd in Roxbury was voted one of the most scenic Roads in town. Must see! Well-appointed and maintained, first time on the market, original owner, charming 1,456 sqft ranch, 3 bathrooms and 2 bedrooms, kitchen, dining, living room with fireplace, C/A, central vacuum, Generac generator connected. Walkout finished basement with entrance from garage is an in-law apartment with kitchen gas stove and full bath. The main house water comes from two sources a well and from a spring fed well. Detached barn offering heat and A/C with 950 sqfr four car garage and 600sqft attic; A two-car garage in the back with 600 sqft and 500sqft attic; many possibilities shop, studio/ in-law appt or garage/storage income. Your own Spring in your own property; close to Westchester, Fairfield and NYC. Great hiking, restaurants, and art abound within minutes. "As is Condition" See attached list of all recent maintenance service and repairs.

2 Moosehorn Rd, Roxbury

$950,000

* A beautiful 3-bedroom historic farmhouse * A separate 2-bedroom guest house * A pristine 6.71-acre building lot Move in and enjoy lush, pastoral Roxbury right away in the charming and immaculate 3-bedroom, c. 1817 main house, and host family and guests in the separate 2-bedroom guest house. The adjacent 6.71-acre parcel at the rear lets you protect your views and privacy forever. You can also build the 4-bedroom estate of your dreams on this approved building lot, with its own driveway and road access. Or use the mostly flat lot as an orchard or garden, or hold the separate parcel as an investment to sell in the future. The lot abuts preserved land. Located in southern Roxbury, just 90 minutes from New York City, the main residence exudes rustic character, with original hand-hewn beams, wide-plank oak floors, a wood-burning fireplace, and classic plaster walls. A brand-new standing-seam metal roof carries a lifetime guarantee. At the heart of the house is a spacious eat-in kitchen. On one side are a formal dining room and a library, and on the other is a sunlit double living room wrapped in windows. The 658-square-foot guest house overlooks a spring-fed pond and Little Jacks Brook. It has a generous living room, two bedrooms, and a full bath, and it runs on its own well and septic system. The grounds are serene and beautifully landscaped, with a cantilevered "waterfront" sun deck, mature trees, lush gardens, and a gently rolling lawn.

5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24209875 MLS

* A beautiful 3-bedroom historic farmhouse * A separate 2-bedroom guest house * A pristine 6.71-acre building lot Move in and enjoy lush, pastoral Roxbury right away in the charming and immaculate 3-bedroom, c. 1817 main house, and host family and guests in the separate 2-bedroom guest house. The adjacent 6.71-acre parcel at the rear lets you protect your views and privacy forever. You can also build the 4-bedroom estate of your dreams on this approved building lot, with its own driveway and road access. Or use the mostly flat lot as an orchard or garden, or hold the separate parcel as an investment to sell in the future. The lot abuts preserved land. Located in southern Roxbury, just 90 minutes from New York City, the main residence exudes rustic character, with original hand-hewn beams, wide-plank oak floors, a wood-burning fireplace, and classic plaster walls. A brand-new standing-seam metal roof carries a lifetime guarantee. At the heart of the house is a spacious eat-in kitchen. On one side are a formal dining room and a library, and on the other is a sunlit double living room wrapped in windows. The 658-square-foot guest house overlooks a spring-fed pond and Little Jacks Brook. It has a generous living room, two bedrooms, and a full bath, and it runs on its own well and septic system. The grounds are serene and beautifully landscaped, with a cantilevered "waterfront" sun deck, mature trees, lush gardens, and a gently rolling lawn.

50 Southbury Rd, Roxbury

$998,000

Set on a picturesque, park-like property in desirable southern Roxbury, this beautiful 4-bedroom, 2.5-bath Colonial blends timeless charm, thoughtful updates, and inviting indoor-outdoor living. A dramatic two-story foyer opens to a formal dining room, spacious living room with custom built-in bookshelves, and impressive family room with a floor-to-ceiling fireplace and custom built-ins. The well-appointed kitchen features granite countertops, center island, Sub-Zero refrigerator, and French doors leading to an expansive deck and terrace-ideal for entertaining. Beautifully landscaped grounds create a private retreat with an in-ground pool, with double fencing, mature gardens, and lush plantings.Hundreds of thousand spend on improvements like new kitchen, expanded driveway/asphalt and charming stone steps and walkway. The home is partially furnished, with new furniture included. A professionally built chicken coop adds a touch of homestead living, perfect for raising chickens and enjoying fresh eggs. Also whole house Generac generator. Peaceful and private yet just 90 minutes from NYC, this exceptional Roxbury property offers space, comfort, and a lifestyle to enjoy.

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24196812 MLS

Set on a picturesque, park-like property in desirable southern Roxbury, this beautiful 4-bedroom, 2.5-bath Colonial blends timeless charm, thoughtful updates, and inviting indoor-outdoor living. A dramatic two-story foyer opens to a formal dining room, spacious living room with custom built-in bookshelves, and impressive family room with a floor-to-ceiling fireplace and custom built-ins. The well-appointed kitchen features granite countertops, center island, Sub-Zero refrigerator, and French doors leading to an expansive deck and terrace-ideal for entertaining. Beautifully landscaped grounds create a private retreat with an in-ground pool, with double fencing, mature gardens, and lush plantings.Hundreds of thousand spend on improvements like new kitchen, expanded driveway/asphalt and charming stone steps and walkway. The home is partially furnished, with new furniture included. A professionally built chicken coop adds a touch of homestead living, perfect for raising chickens and enjoying fresh eggs. Also whole house Generac generator. Peaceful and private yet just 90 minutes from NYC, this exceptional Roxbury property offers space, comfort, and a lifestyle to enjoy.

336 South St, Roxbury

$998,000

Tucked away on a highly sought-after country road, this charming Colonial has been lovingly maintained by its original owners and offers privacy, lovely grounds, and exceptionally low taxes. Distinctive character begins with its graceful rounded-front porch and continues throughout this exceptionally well-built home, where timeless craftsmanship meets enduring charm. A welcoming foyer features a distinctive staircase to the upper level and opens to the living and dining rooms on the left, while a cozy den flows into the bright eat-in kitchen on the right. The laundry and half bath are conveniently located just off the kitchen. Beautiful hardwood floors, two fireplaces, and French doors leading to private patios create inviting spaces for everyday living and entertaining. Upstairs, the spacious primary suite offers walk-in closets and a well-appointed bath with Jacuzzi and large separate shower. Two additional bedrooms feature generous closets, complemented by a large linen closet. This well loved home is on a beautiful lot, at an approx. 1000 ft elevation, has mature landscaped grounds, private patios and a cute garden shed creating a peaceful country retreat. There is an approx 1,100 sq ft basement with tall ceilings offering a great expansion opportunity, or excellent for storage. Roxbury is a quintessential New England community with very low taxes and home to well-regarded schools. It is also known for its natural beauty, historic character, and strong sense of community.

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24204225 MLS

Tucked away on a highly sought-after country road, this charming Colonial has been lovingly maintained by its original owners and offers privacy, lovely grounds, and exceptionally low taxes. Distinctive character begins with its graceful rounded-front porch and continues throughout this exceptionally well-built home, where timeless craftsmanship meets enduring charm. A welcoming foyer features a distinctive staircase to the upper level and opens to the living and dining rooms on the left, while a cozy den flows into the bright eat-in kitchen on the right. The laundry and half bath are conveniently located just off the kitchen. Beautiful hardwood floors, two fireplaces, and French doors leading to private patios create inviting spaces for everyday living and entertaining. Upstairs, the spacious primary suite offers walk-in closets and a well-appointed bath with Jacuzzi and large separate shower. Two additional bedrooms feature generous closets, complemented by a large linen closet. This well loved home is on a beautiful lot, at an approx. 1000 ft elevation, has mature landscaped grounds, private patios and a cute garden shed creating a peaceful country retreat. There is an approx 1,100 sq ft basement with tall ceilings offering a great expansion opportunity, or excellent for storage. Roxbury is a quintessential New England community with very low taxes and home to well-regarded schools. It is also known for its natural beauty, historic character, and strong sense of community.

16 Jonathan Dr, Roxbury

$585,000

A former artist retreat is waiting for you! This Ranch/Rambler style home boasts an open concept with vaulted ceilings. Enjoy all the privacy that Roxbury and the Litchfield Hills offers, yet have convenient access to major highways. The home offers 3 bedrooms and 3 full baths. There is opportunity to convert the lower level into a in-law space should you desire. The outdoor space is primed for your entertaining desires or if you prefer, curl up to a book or a cocktail on the patio, deck or porch. Opportunity is knocking...call for an appointment.

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24197040 MLS

A former artist retreat is waiting for you! This Ranch/Rambler style home boasts an open concept with vaulted ceilings. Enjoy all the privacy that Roxbury and the Litchfield Hills offers, yet have convenient access to major highways. The home offers 3 bedrooms and 3 full baths. There is opportunity to convert the lower level into a in-law space should you desire. The outdoor space is primed for your entertaining desires or if you prefer, curl up to a book or a cocktail on the patio, deck or porch. Opportunity is knocking...call for an appointment.

21 Carriage Ln, Roxbury

$1,195,000

*Completely reimagined from top to bottom, 22 E. Woods Rd. offers the rare combination of virtually new, low-maintenance living, nearly 7 acres of beautiful privacy and exceptional value. WITH JUST $7,395 in annual property taxes, the monthly cost to own and operate this home can be a fraction of what you'll find in many surrounding towns. Inside, gleaming hardwood floors, abundant natural light and an inviting open floor plan create a warm, comfortable atmosphere. The stunning custom kitchen features crisp white and natural-tone cabinetry, granite countertops and high-end stainless-steel appliances, flowing seamlessly into the living spaces anchored by a charming fireplace. The spacious primary suite offers a spa-like bath with soaking tub and oversized tiled shower, walk-in closet and separate flex space perfect for an office, nursery or dressing room. Three additional bedrooms share a brand-new full bath, while a bonus room over the garage-with its own staircase-offers even more flexibility. Outside, front and rear patios provide wonderful spaces for relaxing or entertaining while nearly 7 acres offer privacy and room to enjoy the outdoors. Freshly painted inside and out, with a new roof and driveway, this home is truly move-in ready and designed for worry-free living. Nearly a complete renovation, incredibly private, low taxes and a remarkably low cost of ownership-this is a rare opportunity to enjoy a nearly new home with the space and privacy you've been looking for!

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24192986 MLS

*Completely reimagined from top to bottom, 22 E. Woods Rd. offers the rare combination of virtually new, low-maintenance living, nearly 7 acres of beautiful privacy and exceptional value. WITH JUST $7,395 in annual property taxes, the monthly cost to own and operate this home can be a fraction of what you'll find in many surrounding towns. Inside, gleaming hardwood floors, abundant natural light and an inviting open floor plan create a warm, comfortable atmosphere. The stunning custom kitchen features crisp white and natural-tone cabinetry, granite countertops and high-end stainless-steel appliances, flowing seamlessly into the living spaces anchored by a charming fireplace. The spacious primary suite offers a spa-like bath with soaking tub and oversized tiled shower, walk-in closet and separate flex space perfect for an office, nursery or dressing room. Three additional bedrooms share a brand-new full bath, while a bonus room over the garage-with its own staircase-offers even more flexibility. Outside, front and rear patios provide wonderful spaces for relaxing or entertaining while nearly 7 acres offer privacy and room to enjoy the outdoors. Freshly painted inside and out, with a new roof and driveway, this home is truly move-in ready and designed for worry-free living. Nearly a complete renovation, incredibly private, low taxes and a remarkably low cost of ownership-this is a rare opportunity to enjoy a nearly new home with the space and privacy you've been looking for!

22 E Woods Rd, Roxbury

$785,000

Own a piece of history with the distinguished Philo N. Hodge House, a remarkable antique home built in 1833 and proudly added to the National Register of Historic Places in 2024. Rich in character and historic charm, this unique property offers an opportunity to become the next steward of a truly special home. Bring your imagination and vision to this treasured historic property and make it your own. A welcoming foyer greets you upon entry and leads to a spacious formal living room featuring a classic fireplace. The sunroom is complete with a wood-burning stove. Upstairs, you'll find three bedrooms, including one pass-through bedroom that offers flexibility for a nursery, office, sitting room, or guest space. A full bath serves the second floor. The home's unique feature may be the finished walk-up attic, complete with a working sink and endless possibilities as an artist's studio, creative workspace, hobby room, or private retreat. Recent improvements include a professionally installed Connecticut Basement Systems waterproofing system, featuring a new sump pump and dehumidifiers to help maintain a clean, dry basement year-round. Filled with memories, history, and timeless architectural details, the Philo N. Hodge House is ready for its next chapter. Buyers are encouraged to conduct their own due diligence with the Town of Roxbury regarding any regulations, permits, approvals, historic preservation considerations, or future improvements to the property.

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24180161 MLS

Own a piece of history with the distinguished Philo N. Hodge House, a remarkable antique home built in 1833 and proudly added to the National Register of Historic Places in 2024. Rich in character and historic charm, this unique property offers an opportunity to become the next steward of a truly special home. Bring your imagination and vision to this treasured historic property and make it your own. A welcoming foyer greets you upon entry and leads to a spacious formal living room featuring a classic fireplace. The sunroom is complete with a wood-burning stove. Upstairs, you'll find three bedrooms, including one pass-through bedroom that offers flexibility for a nursery, office, sitting room, or guest space. A full bath serves the second floor. The home's unique feature may be the finished walk-up attic, complete with a working sink and endless possibilities as an artist's studio, creative workspace, hobby room, or private retreat. Recent improvements include a professionally installed Connecticut Basement Systems waterproofing system, featuring a new sump pump and dehumidifiers to help maintain a clean, dry basement year-round. Filled with memories, history, and timeless architectural details, the Philo N. Hodge House is ready for its next chapter. Buyers are encouraged to conduct their own due diligence with the Town of Roxbury regarding any regulations, permits, approvals, historic preservation considerations, or future improvements to the property.

47 South St, Roxbury

$969,000

Mint Hilltop Home with Views and only a short walk to Maple Bank Farm Stand, Toplands Farm and historic Roxbury Center. New Anderson Luxe White Oak Windows. Wood-Burning Fireplace, Vaulted Primary Bedroom with Balcony and Private Bath. Dine or relax on the Flagstone Terrace. Must See!

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24167690 MLS

Mint Hilltop Home with Views and only a short walk to Maple Bank Farm Stand, Toplands Farm and historic Roxbury Center. New Anderson Luxe White Oak Windows. Wood-Burning Fireplace, Vaulted Primary Bedroom with Balcony and Private Bath. Dine or relax on the Flagstone Terrace. Must See!

23 Painter Hill Rd, Roxbury

$925,000

Tucked away at the end of a quiet cul-de-sac in one of Roxbury's most desirable neighborhoods, this beautifully updated 4-bed, 3.5-bath Post & Beam Colonial offers a rare combination of privacy, character & flexibility. Exposed white oak beams, soaring 27ft ceilings, and 3 fireplaces create a warm architectural presence throughout the home, while thoughtful updates provide modern comfort and convenience. An active solar energy system helps offset utility costs and enhances long-term efficiency. Set on 3+ private acres, the property enjoys an exceptional natural backdrop with extensive undeveloped acreage beyond the rear property line, creating privacy and peaceful woodland views. Mature landscaping, a spacious deck, and a serene setting make the outdoor spaces ideal for entertaining or quiet enjoyment. The flexible floor plan includes a private in-law, studio, or home office space, ideal for today's evolving lifestyle needs. Beyond the 3,340 sq. ft. of above-grade living space, the home offers an expansive full lower level providing approximately 1,700 sq. ft. of dry bonus space ideal for storage, recreation, workshop, fitness, or future customization. An enormous walkable attic spanning nearly the entire 2nd floor footprint provides exceptional add'l storage rarely found in homes of this era.

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24164547 MLS

Tucked away at the end of a quiet cul-de-sac in one of Roxbury's most desirable neighborhoods, this beautifully updated 4-bed, 3.5-bath Post & Beam Colonial offers a rare combination of privacy, character & flexibility. Exposed white oak beams, soaring 27ft ceilings, and 3 fireplaces create a warm architectural presence throughout the home, while thoughtful updates provide modern comfort and convenience. An active solar energy system helps offset utility costs and enhances long-term efficiency. Set on 3+ private acres, the property enjoys an exceptional natural backdrop with extensive undeveloped acreage beyond the rear property line, creating privacy and peaceful woodland views. Mature landscaping, a spacious deck, and a serene setting make the outdoor spaces ideal for entertaining or quiet enjoyment. The flexible floor plan includes a private in-law, studio, or home office space, ideal for today's evolving lifestyle needs. Beyond the 3,340 sq. ft. of above-grade living space, the home offers an expansive full lower level providing approximately 1,700 sq. ft. of dry bonus space ideal for storage, recreation, workshop, fitness, or future customization. An enormous walkable attic spanning nearly the entire 2nd floor footprint provides exceptional add'l storage rarely found in homes of this era.

24 Hickory Ln, Roxbury

$969,000

MUST SEE! New Nantucket white cedar shingle siding, window trim, new interior doors and hardware and heated, year-round Spa Pool -- all on the best rural Roxbury scenic dirt road with walking area along the Shepaug River and nearby historic farmhouses and land preserve. All minutes to The Mayflower. Pristine renovated private country home with 3 bedrooms/2.5 baths and an ample home office. Open floorplan Living/Eat-in Kitchen/Family Room with wood burning fireplace and sliders to a year-round, heated pool and patio. Dine or relax on the granite terrace or covered front porch surrounded by mature woods and amazing rock outcroppings. Attached 2-car garage. Mint Condition! Move Right In!

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24163273 MLS

MUST SEE! New Nantucket white cedar shingle siding, window trim, new interior doors and hardware and heated, year-round Spa Pool -- all on the best rural Roxbury scenic dirt road with walking area along the Shepaug River and nearby historic farmhouses and land preserve. All minutes to The Mayflower. Pristine renovated private country home with 3 bedrooms/2.5 baths and an ample home office. Open floorplan Living/Eat-in Kitchen/Family Room with wood burning fireplace and sliders to a year-round, heated pool and patio. Dine or relax on the granite terrace or covered front porch surrounded by mature woods and amazing rock outcroppings. Attached 2-car garage. Mint Condition! Move Right In!

18 Tunnel Rd, Roxbury