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A masterclass in privacy and scale. A newly constructed stone-lined & gated driveway ascends through 57+ acres of pristine Litchfield County landscape to a magnificent hilltop sanctuary. This estate-quality offering, spanning two separate parcels, is defined by its dramatic sweeping views and an extraordinary sense of quietude. Enveloped by the protected forests of the Roxbury Land Trust, the terrain is a symphony of nature: a shimmering pond, a meandering stream, and ancient mature trees. This is a rare opportunity to cultivate a legacy estate just moments from the refined charm of Roxbury and Washington, and a mere 90 minutes from Manhattan. Improvements Include: 3 wells; irrigation system; driveway & underground power. The ultimate canvas for a life well-lived.

CLOSED Status ⋅ 24176550 MLS

A masterclass in privacy and scale. A newly constructed stone-lined & gated driveway ascends through 57+ acres of pristine Litchfield County landscape to a magnificent hilltop sanctuary. This estate-quality offering, spanning two separate parcels, is defined by its dramatic sweeping views and an extraordinary sense of quietude. Enveloped by the protected forests of the Roxbury Land Trust, the terrain is a symphony of nature: a shimmering pond, a meandering stream, and ancient mature trees. This is a rare opportunity to cultivate a legacy estate just moments from the refined charm of Roxbury and Washington, and a mere 90 minutes from Manhattan. Improvements Include: 3 wells; irrigation system; driveway & underground power. The ultimate canvas for a life well-lived.

20 Painter Hill Rd, Roxbury

$3,340,000

Privately Sited on a Hill in the Midst of 31+ acres, this Elegantly Renovated 5,000+ sq ft Colonial Offers Panoramic Sunset Views and Exceptional Privacy. Graciously Proportioned Rooms Populate the Main Level & Include: a Vaulted-Ceiling Living Room with Fireplace, Paneled Library, Inviting Family Room, and a Spacious Eat-in Kitchen with Top-tier Appliances. The Refined Primary Suite Features a Fireplace, ModernLuxury Bath, and Dressing Room. A Separate 1-Bedroom Guest Suite Adds Versatility. Outdoors, Discover A Heated Gunite Pool Surrounded by Mature Award-Winning Gardens. Large Stone Terraces & a Meandering Garden Path Add a Texture to this Layered Property. 3-Car Over-sized Attached Garage. Only Minutes from Roxbury, Washington Depot, and Historic Woodbury CT. First Time on the Market in Over 35 Years

5 Beds ⋅ 6 Baths ⋅ CLOSED Status ⋅ 24088086 MLS

Privately Sited on a Hill in the Midst of 31+ acres, this Elegantly Renovated 5,000+ sq ft Colonial Offers Panoramic Sunset Views and Exceptional Privacy. Graciously Proportioned Rooms Populate the Main Level & Include: a Vaulted-Ceiling Living Room with Fireplace, Paneled Library, Inviting Family Room, and a Spacious Eat-in Kitchen with Top-tier Appliances. The Refined Primary Suite Features a Fireplace, ModernLuxury Bath, and Dressing Room. A Separate 1-Bedroom Guest Suite Adds Versatility. Outdoors, Discover A Heated Gunite Pool Surrounded by Mature Award-Winning Gardens. Large Stone Terraces & a Meandering Garden Path Add a Texture to this Layered Property. 3-Car Over-sized Attached Garage. Only Minutes from Roxbury, Washington Depot, and Historic Woodbury CT. First Time on the Market in Over 35 Years

8 Bayberry Hl, Roxbury

$2,700,000

Tranquility awaits down this long paved driveway in Northern Roxbury. Complete privacy with spectacular gardens, pond and orchard surrounded by dramatic rocky outcroppings. This stone and stucco home features large eat-in kitchen, formal dining and living rooms, and a spacious media room. The main floor primary suite includes a fireplace, office space, and large walk in closet. There is an addl guest room on the main level, perfect for nursery or in-laws.3 bedrooms/2 baths on the second level. Lower level game room has full bath and can be used as a 6th bedroom. Gunite heated pool with stone terraces incorporates room for relaxing and dining pool side. 3 car garage has unfinished space above which could be finished to an apartment or studio. Multi zone stereo system. Just 5 minutes to Washington with chic shops, farmer's market and

5 Beds ⋅ 6 Baths ⋅ CLOSED Status ⋅ 24093019 MLS

Tranquility awaits down this long paved driveway in Northern Roxbury. Complete privacy with spectacular gardens, pond and orchard surrounded by dramatic rocky outcroppings. This stone and stucco home features large eat-in kitchen, formal dining and living rooms, and a spacious media room. The main floor primary suite includes a fireplace, office space, and large walk in closet. There is an addl guest room on the main level, perfect for nursery or in-laws.3 bedrooms/2 baths on the second level. Lower level game room has full bath and can be used as a 6th bedroom. Gunite heated pool with stone terraces incorporates room for relaxing and dining pool side. 3 car garage has unfinished space above which could be finished to an apartment or studio. Multi zone stereo system. Just 5 minutes to Washington with chic shops, farmer's market and

Roxbury

$2,547,500

This beautifully renovated 1911 colonial blends timeless charm with modern comfort in one of Roxbury's most desirable locations. The main residence offers luxury living with 2-3 bedrooms, a media room, gourmet kitchen, formal dining room, and a screened porch. The newly built guest house includes 2 bedrooms and a spacious game room/cabana with fireplace. Enjoy Summer entertaining on the covered porch with outdoor fireplace overlooking the heated gunite saltwater pool, scenic views, and expansive level lawn. The property features a two-car garage and borders a major estates and conserved land, ensuring privacy and beauty in an exceptional setting. Just minutes to the Mayflower Inn/Spa and chic shopping/dining in Washington and Woodbury.

3 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24138574 MLS

This beautifully renovated 1911 colonial blends timeless charm with modern comfort in one of Roxbury's most desirable locations. The main residence offers luxury living with 2-3 bedrooms, a media room, gourmet kitchen, formal dining room, and a screened porch. The newly built guest house includes 2 bedrooms and a spacious game room/cabana with fireplace. Enjoy Summer entertaining on the covered porch with outdoor fireplace overlooking the heated gunite saltwater pool, scenic views, and expansive level lawn. The property features a two-car garage and borders a major estates and conserved land, ensuring privacy and beauty in an exceptional setting. Just minutes to the Mayflower Inn/Spa and chic shopping/dining in Washington and Woodbury.

277 Painter Hill Rd, Roxbury

$2,501,000

Exquisite Country Estate in Roxbury Nestled on 42 private acres in the heart of Roxbury, this spectacular shingle-style architectural masterpiece offers an unparalleled blend of sophistication and serene country living. From the moment you meander down the picturesque drive, you'll know you have arrived at your forever home. Designed for both grand entertaining and intimate daily life, the home's beautiful open spaces are bathed in natural light. Every detail has been meticulously crafted to create an atmosphere of refined elegance and comfort. This residence features five spacious bedrooms, six luxurious baths, and four fireplaces, each adding a touch of warmth and classic charm. Outdoor living is elevated to an art form here. The award-winning infinity pool and spa appear to spill into the professionally designed landscape, which seamlessly blends with the natural wooded surroundings, ensuring complete privacy. A grand stone terrace with a fireplace and a sprawling covered porch provide the perfect settings for memorable outdoor gatherings, dining, and relaxation. This estate truly offers the best of both worlds-it feels a world away from the hustle and bustle yet is conveniently located close to everything. The property consists of three separate parcels and benefits from low Roxbury taxes, adding to its appeal. This is more than just a home; it's a lifestyle. We invite you to plan extra time for your private showing to fully appreciate the except

5 Beds ⋅ 6 Baths ⋅ CLOSED Status ⋅ 24122044 MLS

Exquisite Country Estate in Roxbury Nestled on 42 private acres in the heart of Roxbury, this spectacular shingle-style architectural masterpiece offers an unparalleled blend of sophistication and serene country living. From the moment you meander down the picturesque drive, you'll know you have arrived at your forever home. Designed for both grand entertaining and intimate daily life, the home's beautiful open spaces are bathed in natural light. Every detail has been meticulously crafted to create an atmosphere of refined elegance and comfort. This residence features five spacious bedrooms, six luxurious baths, and four fireplaces, each adding a touch of warmth and classic charm. Outdoor living is elevated to an art form here. The award-winning infinity pool and spa appear to spill into the professionally designed landscape, which seamlessly blends with the natural wooded surroundings, ensuring complete privacy. A grand stone terrace with a fireplace and a sprawling covered porch provide the perfect settings for memorable outdoor gatherings, dining, and relaxation. This estate truly offers the best of both worlds-it feels a world away from the hustle and bustle yet is conveniently located close to everything. The property consists of three separate parcels and benefits from low Roxbury taxes, adding to its appeal. This is more than just a home; it's a lifestyle. We invite you to plan extra time for your private showing to fully appreciate the except

Roxbury

$2,300,000

Roxbury Shingle-Style Gem with Sparkling Pool! This grand residence sits off one of Litchfield County's most treasured and bucolic roads amidst boldfaced names - past and present - and backing up to a 60-acre parcel of Roxbury Land Trust. Prepare to be "wowed" by the sun-flooded double height living room, gorgeous eat-in-kitchen, formal dining room, four-season sunroom, wood-paneled library/den, and well-executed rec room. Four oversized bedrooms with ensuite baths, including primary suite options on both the main floor and upstairs. A large outdoor deck which spills onto a native stone terrace with grill and pizza oven; perfect for entertaining friends and family. Partially finished basement with gym and tons of storage. Pristine 20x40 gunite pool and spa added in 2022. Cagenio-wired smart home with mega-speed internet, Wifi covering the interior and exterior patio and pool areas, whole house generator. Many "hidden money" upgrades inside and out, including roof in 2021 (w/ 50-yr transferable warranty), five zone HVAC system with all units replaced 2021-2024, pool and spa in 2022, whole-house generator, mini-splits in the sunroom and gym area, and a comprehensive automation system. In the heart of Litchfield County, convenient to Lake Waramaug, fine dining, farmers markets, town tennis courts and thousands of acres of land trust to explore. 90 minutes to NYC but a world away.

4 Beds ⋅ 5 Baths ⋅ CLOSED Status ⋅ 24167123 MLS

Roxbury Shingle-Style Gem with Sparkling Pool! This grand residence sits off one of Litchfield County's most treasured and bucolic roads amidst boldfaced names - past and present - and backing up to a 60-acre parcel of Roxbury Land Trust. Prepare to be "wowed" by the sun-flooded double height living room, gorgeous eat-in-kitchen, formal dining room, four-season sunroom, wood-paneled library/den, and well-executed rec room. Four oversized bedrooms with ensuite baths, including primary suite options on both the main floor and upstairs. A large outdoor deck which spills onto a native stone terrace with grill and pizza oven; perfect for entertaining friends and family. Partially finished basement with gym and tons of storage. Pristine 20x40 gunite pool and spa added in 2022. Cagenio-wired smart home with mega-speed internet, Wifi covering the interior and exterior patio and pool areas, whole house generator. Many "hidden money" upgrades inside and out, including roof in 2021 (w/ 50-yr transferable warranty), five zone HVAC system with all units replaced 2021-2024, pool and spa in 2022, whole-house generator, mini-splits in the sunroom and gym area, and a comprehensive automation system. In the heart of Litchfield County, convenient to Lake Waramaug, fine dining, farmers markets, town tennis courts and thousands of acres of land trust to explore. 90 minutes to NYC but a world away.

77 Tophet Rd, Roxbury

$1,966,500

Roxbury dream home with forever views. Tucked away down a gracious drive off a bucolic town road this quintessential Georgian welcomes you home and envelopes you in calm and comfort. Arrival at the motor court provides the first glimpse of a western view that stretches from Roxbury as far as the eye can see, giving an immediate sense of place. The home, unabashedly radiant in its sunny yellow color, was purchased by the current owner in 2021 and underwent an exquisite glow-up by a noted local designer who transformed the residence into something formal, yet intimate; a place that feels so right with rooms that serve purpose. The masterfully appointed chef's kitchen will delight with abundant prep space, oversized range, and a refrigeration wall with dedicated cooling, freezer and wine storage. A sun-filled gathering space is adjacent as well as an informal dining area. A butler's pantry connects the kitchen and the formal dining room. The formal LR is across the foyer, a serene space with one of the home's 3 fireplaces. A den and a media lounge complete the main floor. Upstairs, the primary suite has been reimagined into a luxury space with dressing room and a spa bath. 2 guest BRs and a full bath complete this level. Above the 2 car garage is a guest apartment with living area/gym, BR and BA. Immaculate grounds with mature gardens and multiple outdoor dining spaces. Ready for new memories, this is a gem of a home within a dream of a town.

4 Beds ⋅ 5 Baths ⋅ CLOSED Status ⋅ 24085777 MLS

Roxbury dream home with forever views. Tucked away down a gracious drive off a bucolic town road this quintessential Georgian welcomes you home and envelopes you in calm and comfort. Arrival at the motor court provides the first glimpse of a western view that stretches from Roxbury as far as the eye can see, giving an immediate sense of place. The home, unabashedly radiant in its sunny yellow color, was purchased by the current owner in 2021 and underwent an exquisite glow-up by a noted local designer who transformed the residence into something formal, yet intimate; a place that feels so right with rooms that serve purpose. The masterfully appointed chef's kitchen will delight with abundant prep space, oversized range, and a refrigeration wall with dedicated cooling, freezer and wine storage. A sun-filled gathering space is adjacent as well as an informal dining area. A butler's pantry connects the kitchen and the formal dining room. The formal LR is across the foyer, a serene space with one of the home's 3 fireplaces. A den and a media lounge complete the main floor. Upstairs, the primary suite has been reimagined into a luxury space with dressing room and a spa bath. 2 guest BRs and a full bath complete this level. Above the 2 car garage is a guest apartment with living area/gym, BR and BA. Immaculate grounds with mature gardens and multiple outdoor dining spaces. Ready for new memories, this is a gem of a home within a dream of a town.

32 Grassy Hill Rd, Roxbury

$1,925,000

Located along one of Roxbury's most coveted stretches, this property is nestled among an 800+ acre greenbelt of farmland and conserved land with plentiful hiking trails. The open floor plan is designed with 9 foot+ ceilings, detailed millwork and oversized windows which infuse the interiors with natural light. The main level features a show stopping kitchen open to the dinning and media rooms. There is also a formal living room with wrap around deck which takes in the views. Interiors are newly updated with designer wallpapers, custom window treatments, and luxury lighting. The second floor hosts 3 generously sized en-suite bedrooms which surround a central gathering space with built-in desks. The attic level is fully finished with a full bath for 4th bedroom, game room, gym, home office and/or studio. The salt water heated pool and spa take in the rolling ridge line views across a vast tract of protected land. Newly cleared lawns with fire pit. Excellent mechanical systems, including a 27K generator and Buderus furnace. Peaceful and private, yet just 10 minutes to Washington or Woodbury for farm stands, organic groceries, restaurants and boutiques. 1.5 hours from NYC and 30 minutes to the train station.

4 Beds ⋅ 6 Baths ⋅ CLOSED Status ⋅ 24093575 MLS

Located along one of Roxbury's most coveted stretches, this property is nestled among an 800+ acre greenbelt of farmland and conserved land with plentiful hiking trails. The open floor plan is designed with 9 foot+ ceilings, detailed millwork and oversized windows which infuse the interiors with natural light. The main level features a show stopping kitchen open to the dinning and media rooms. There is also a formal living room with wrap around deck which takes in the views. Interiors are newly updated with designer wallpapers, custom window treatments, and luxury lighting. The second floor hosts 3 generously sized en-suite bedrooms which surround a central gathering space with built-in desks. The attic level is fully finished with a full bath for 4th bedroom, game room, gym, home office and/or studio. The salt water heated pool and spa take in the rolling ridge line views across a vast tract of protected land. Newly cleared lawns with fire pit. Excellent mechanical systems, including a 27K generator and Buderus furnace. Peaceful and private, yet just 10 minutes to Washington or Woodbury for farm stands, organic groceries, restaurants and boutiques. 1.5 hours from NYC and 30 minutes to the train station.

143 Tophet Rd, Roxbury

$1,795,000

Perfect Country Home! Located close to town on a quiet country road. Built is 2018, the new owners have done extensive Landscaping. A privacy fence was installed on the front of the property with evergreens planted on both sides of the fence . There is a small apple orchard planted on the property. Extensive stonework and plantings have been done around the house and an in ground pool with pebble tech finish was installed with fencing in the rear yard for the pool and pets. The house was originally built by a Master Craftsman with the finest materials.The gourmet kitchen is where everyone lives. There is a center island and field stone fireplace. Thermador appliances include a 6 burner cook top as well as wall oven, built in microwave, a warming drawer, dishwasher and refrigerator. The open floor plan allows you to set up the living room/dining room in a variety of ways. There is a lovely sunroom with a vaulted ceiling off the kitchen. There is a mudroom coming in from the garage with a half bath. The ceilings are 9' on the first floor. The upper level includes a lovely Primary Suite with walk in closets, a luxurious primary bath with 2 sinks, a walk in shower and a soaking tub. There are 3 additional bedrooms on the upper level with one en-suite and the other two sharing a hall bath. The house sits up high with mountain views. The land is gently sloping with a level area with plenty of room to play. Only 90 minutes to NYC!

4 Beds ⋅ 4 Baths ⋅ CLOSED Status ⋅ 24170163 MLS

Perfect Country Home! Located close to town on a quiet country road. Built is 2018, the new owners have done extensive Landscaping. A privacy fence was installed on the front of the property with evergreens planted on both sides of the fence . There is a small apple orchard planted on the property. Extensive stonework and plantings have been done around the house and an in ground pool with pebble tech finish was installed with fencing in the rear yard for the pool and pets. The house was originally built by a Master Craftsman with the finest materials.The gourmet kitchen is where everyone lives. There is a center island and field stone fireplace. Thermador appliances include a 6 burner cook top as well as wall oven, built in microwave, a warming drawer, dishwasher and refrigerator. The open floor plan allows you to set up the living room/dining room in a variety of ways. There is a lovely sunroom with a vaulted ceiling off the kitchen. There is a mudroom coming in from the garage with a half bath. The ceilings are 9' on the first floor. The upper level includes a lovely Primary Suite with walk in closets, a luxurious primary bath with 2 sinks, a walk in shower and a soaking tub. There are 3 additional bedrooms on the upper level with one en-suite and the other two sharing a hall bath. The house sits up high with mountain views. The land is gently sloping with a level area with plenty of room to play. Only 90 minutes to NYC!

18 Ranney Hill Rd, Roxbury

$1,764,000

Your turnkey country escape is waiting in Roxbury - a modern shinglestyle home on 4+ manicured acres with a resortlevel pool, just far enough from the city to exhale, yet close enough to make spontaneous weekend getaways a reality. From the moment you arrive, this summer ready property feels like a private club: stone walls, curated landscaping, quiet woods, and outdoor spaces designed for long summer days and late night gatherings. The gunite pool is the centerpiece - sparkling, secluded, and ready the moment you are. Inside, sunlight pours through picture windows into an open layout built for effortless entertaining. Custom oak details, a dramatic fieldstone fireplace, and a chef's kitchen with high-end appliances and stone counters set the stage for everything from cozy winter weekends to lively holiday hosting. With 4 ensuite bedrooms, the home adapts beautifully to guests and long family weekends. The first floor ensuite offers effortless hospitality, while the second floor luxury primary suite- complete with 11 foot ceilings and a marble spa bath - provides a calm, spa-level retreat. A steel-and-glass office alcove and a bonus room above the garage with interior access, offer the perfect flex space for a studio, gym, or potential guest suite. The finished lower level and walkout access adds even more room to unwind. Fully renovated since 2021 including new HVAC, generator, and more - means no projects, no delays to start enjoying the Litchfield Lifestyle.

4 Beds ⋅ 5 Baths ⋅ CLOSED Status ⋅ 24176141 MLS

Your turnkey country escape is waiting in Roxbury - a modern shinglestyle home on 4+ manicured acres with a resortlevel pool, just far enough from the city to exhale, yet close enough to make spontaneous weekend getaways a reality. From the moment you arrive, this summer ready property feels like a private club: stone walls, curated landscaping, quiet woods, and outdoor spaces designed for long summer days and late night gatherings. The gunite pool is the centerpiece - sparkling, secluded, and ready the moment you are. Inside, sunlight pours through picture windows into an open layout built for effortless entertaining. Custom oak details, a dramatic fieldstone fireplace, and a chef's kitchen with high-end appliances and stone counters set the stage for everything from cozy winter weekends to lively holiday hosting. With 4 ensuite bedrooms, the home adapts beautifully to guests and long family weekends. The first floor ensuite offers effortless hospitality, while the second floor luxury primary suite- complete with 11 foot ceilings and a marble spa bath - provides a calm, spa-level retreat. A steel-and-glass office alcove and a bonus room above the garage with interior access, offer the perfect flex space for a studio, gym, or potential guest suite. The finished lower level and walkout access adds even more room to unwind. Fully renovated since 2021 including new HVAC, generator, and more - means no projects, no delays to start enjoying the Litchfield Lifestyle.

176 Apple Ln, Roxbury

$1,600,000

This special home is located in one of Roxbury's most desirable neighborhoods on a quiet dead end road. A long, winding & very private driveway leads up to the commanding double-story porticoed entrance. The traditional colonial layout includes a central chef's kitchen which rests between the formal living, media & dining rooms. The main floor is completed by an office, 2 half baths, and a 2-room bedroom suite - perfect for guests, in-laws, or live-in help. This wing could easily be converted to a main floor primary if desired. Upstairs hosts the current primary bedroom w/ frpl & updated bath, as well as 2 addl bedrooms w/ a shared hallway bath. The updated, eat-in kitchen walks out to an airy screened porch w/ ample space to accommodate both lounging & dining. It is lightly shaded by mature trees and overlooks fieldstone terraces, established gardens & fruit trees. This property offers a uniquely flat and expansive lawn in a truly 'park-like' setting. The previous owner was a master gardener who meticulously cultivated specimen Rhododendrons throughout the lightly wooded surrounds. The mature plantings combine w/ native Mountain Laurel to create a spectacular display in early Summer. The exterior is completed by a 22 x 45 salt water, Gunite pool w/ integrated 6 x 8 Jacuzzi. It is 10' deep & boasts a diving board, retractable cover, & automated chemistry system allowing for hassle free ownership.

4 Beds ⋅ 5 Baths ⋅ CLOSED Status ⋅ 24133274 MLS

This special home is located in one of Roxbury's most desirable neighborhoods on a quiet dead end road. A long, winding & very private driveway leads up to the commanding double-story porticoed entrance. The traditional colonial layout includes a central chef's kitchen which rests between the formal living, media & dining rooms. The main floor is completed by an office, 2 half baths, and a 2-room bedroom suite - perfect for guests, in-laws, or live-in help. This wing could easily be converted to a main floor primary if desired. Upstairs hosts the current primary bedroom w/ frpl & updated bath, as well as 2 addl bedrooms w/ a shared hallway bath. The updated, eat-in kitchen walks out to an airy screened porch w/ ample space to accommodate both lounging & dining. It is lightly shaded by mature trees and overlooks fieldstone terraces, established gardens & fruit trees. This property offers a uniquely flat and expansive lawn in a truly 'park-like' setting. The previous owner was a master gardener who meticulously cultivated specimen Rhododendrons throughout the lightly wooded surrounds. The mature plantings combine w/ native Mountain Laurel to create a spectacular display in early Summer. The exterior is completed by a 22 x 45 salt water, Gunite pool w/ integrated 6 x 8 Jacuzzi. It is 10' deep & boasts a diving board, retractable cover, & automated chemistry system allowing for hassle free ownership.

31 Hickory Ln, Roxbury

$1,525,000

This 4 bedroom main house with 2 bedroom guest house provides a peaceful retreat just minutes from town and 1.5 hours from NYC. The cape style main house is privately sited to capture breathtaking western views and sunsets. It features a light-filled open floor plan designed for effortless everyday living and entertaining. French doors open to an expansive deck where sweeping western vistas create the perfect backdrop for relaxing or hosting while overlooking the frolicking horses at the neighboring property. At the heart of the home is a stylish kitchen with a generous center island, ideal for both casual gatherings and inspired culinary creations. The great room incorporates a dining area and seating area with fireplace. The main floor is completed by the primary bedroom with ensuite bath and the 2nd bedroom which is conveniently located adjacent to the primary and could be used as additional closet or office space. Upstairs, 2 bedrooms share a hall bath. An additional 800+/- square feet of walk-out lower-level space has high ceilings and is plumbed for a full bath. It offers potential to create a play room, home gym, media room, or in law suite. The under-house two-car garage offers space for vehicles and/or storage. Complementing the main residence is a 1,400-square-foot ranch style guest house featuring two bedrooms and two full baths on one level, perfect for guests, income, or in-laws.

4 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24194995 MLS

This 4 bedroom main house with 2 bedroom guest house provides a peaceful retreat just minutes from town and 1.5 hours from NYC. The cape style main house is privately sited to capture breathtaking western views and sunsets. It features a light-filled open floor plan designed for effortless everyday living and entertaining. French doors open to an expansive deck where sweeping western vistas create the perfect backdrop for relaxing or hosting while overlooking the frolicking horses at the neighboring property. At the heart of the home is a stylish kitchen with a generous center island, ideal for both casual gatherings and inspired culinary creations. The great room incorporates a dining area and seating area with fireplace. The main floor is completed by the primary bedroom with ensuite bath and the 2nd bedroom which is conveniently located adjacent to the primary and could be used as additional closet or office space. Upstairs, 2 bedrooms share a hall bath. An additional 800+/- square feet of walk-out lower-level space has high ceilings and is plumbed for a full bath. It offers potential to create a play room, home gym, media room, or in law suite. The under-house two-car garage offers space for vehicles and/or storage. Complementing the main residence is a 1,400-square-foot ranch style guest house featuring two bedrooms and two full baths on one level, perfect for guests, income, or in-laws.

21 Hemlock Rd, Roxbury

$1,500,000

Quintessential CT Mini- Estate of 2 Homes! Top restoration of 3-Bedroom/2.5 bath Victorian plus a Guest House with giant stunning, heated, saltwater pool, 2nd small spa pool and wonderful stone terraces and open lawns. Historic Pool House Rental Income: $50,000-$100,000 per year. Perfect for generational living as both the Main House and the Pool House have their own pools, driveways and garages. Main house with large wood-burning fireplace and original antique wood floors throughout. Plus a New Vaulted, Open and Airy Pool House with chef's kitchen, bedroom, full bath, finished lower level offering a second full bath and more living space. Charming, covered BBQ Deck overlooking pool and 2-car garage below. Best scenic road for walking or bike riding by historic farms and homes owned by numerous artists, authors, actors and other private luminaries. Mature plantings include beautiful hedges, blue hydrangea, specimen trees -- enough flowers to keep vases full. Barn. Special. Must see!

4 Beds ⋅ 4 Baths ⋅ CLOSED Status ⋅ 24085914 MLS

Quintessential CT Mini- Estate of 2 Homes! Top restoration of 3-Bedroom/2.5 bath Victorian plus a Guest House with giant stunning, heated, saltwater pool, 2nd small spa pool and wonderful stone terraces and open lawns. Historic Pool House Rental Income: $50,000-$100,000 per year. Perfect for generational living as both the Main House and the Pool House have their own pools, driveways and garages. Main house with large wood-burning fireplace and original antique wood floors throughout. Plus a New Vaulted, Open and Airy Pool House with chef's kitchen, bedroom, full bath, finished lower level offering a second full bath and more living space. Charming, covered BBQ Deck overlooking pool and 2-car garage below. Best scenic road for walking or bike riding by historic farms and homes owned by numerous artists, authors, actors and other private luminaries. Mature plantings include beautiful hedges, blue hydrangea, specimen trees -- enough flowers to keep vases full. Barn. Special. Must see!

253 Tophet Rd, Roxbury

$1,425,000

This cross gabled farmhouse was built in 2006 by its artisan craftsman owner, expanding upon the original foundation of a dwelling previously occupied by the caretaker of Arthur Miller's residence. The home was designed to leverage distant views east that stretch across thousands of acres of forested land to ridgelines in the towns of Woodbury and Bethlehem. The owner harvested and milled trees found locally to construct the flooring, stairs, cabinetry, interior doors and most of the finish moldings, creating exceptional detail and character rarely found at this price point. No less impressive is the handsome and considerable stonemasonry he crafted, surrounding the house and connecting its points of entry to exterior living spaces. All three bedrooms have windows facing the long views with both the primary suite and open kitchen/dining space featuring french doors to the outdoor stone terrace extending toward the panoramic scenery. Magnificent living room with granite framed wood burning fireplace and a flat screen TV cabinet above the mantle that is flanked by built-in bookshelves. Large main level den/office and dedicated pantry with sink, wine fridge and game freezer. Second floor office could also be used for overflow guests. Savor the secret lifestyle sauce located in Roxbury's coveted southeast hill country that has drawn luminaries past and present, including Miller, Monroe, Widmark, Matthau, Calder, McCourt, Hoffman, Rayburn, Reed, Bushnell, Leoni & Ecklund.

3 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24171072 MLS

This cross gabled farmhouse was built in 2006 by its artisan craftsman owner, expanding upon the original foundation of a dwelling previously occupied by the caretaker of Arthur Miller's residence. The home was designed to leverage distant views east that stretch across thousands of acres of forested land to ridgelines in the towns of Woodbury and Bethlehem. The owner harvested and milled trees found locally to construct the flooring, stairs, cabinetry, interior doors and most of the finish moldings, creating exceptional detail and character rarely found at this price point. No less impressive is the handsome and considerable stonemasonry he crafted, surrounding the house and connecting its points of entry to exterior living spaces. All three bedrooms have windows facing the long views with both the primary suite and open kitchen/dining space featuring french doors to the outdoor stone terrace extending toward the panoramic scenery. Magnificent living room with granite framed wood burning fireplace and a flat screen TV cabinet above the mantle that is flanked by built-in bookshelves. Large main level den/office and dedicated pantry with sink, wine fridge and game freezer. Second floor office could also be used for overflow guests. Savor the secret lifestyle sauce located in Roxbury's coveted southeast hill country that has drawn luminaries past and present, including Miller, Monroe, Widmark, Matthau, Calder, McCourt, Hoffman, Rayburn, Reed, Bushnell, Leoni & Ecklund.

56 Goldmine Rd, Roxbury

$1,400,000

Situated in Roxbury near the Washington border, this quintessential 1960's four bedroom Cape Cod with heated pool, serves as a private sanctuary, harmonizing classic New England architecture with modern refinements. The exterior is characterized by a handsome cedar wood shingle roof and landscape defined by mature trees, rock outcroppings, and vibrant perennial gardens. Outdoor living is central to the property's allure, featuring an inground pool, sprawling 19 x 22 raised deck and screened porch providing a serene, airy environment for three-season relaxation - a natural extension of the interior living space. The heart of the home is the kitchen, a chef's delight featuring high-end Sub-Zero refrigeration and finishes that overlook the lush grounds. The interior is defined by freshly painted walls and gleaming hardwood floors that lead to a coveted primary suite conveniently located on the main level. With a total of two full and two half baths, the home is thoughtfully configured for both privacy and guest convenience. Additional versatility is found in the finished lower level, which currently hosts a private gym and a spacious recreation room complete with its own half bath. This level provides the flexible space necessary for contemporary living, whether used for fitness, media, or a home office.

4 Beds ⋅ 4 Baths ⋅ CLOSED Status ⋅ 24163465 MLS

Situated in Roxbury near the Washington border, this quintessential 1960's four bedroom Cape Cod with heated pool, serves as a private sanctuary, harmonizing classic New England architecture with modern refinements. The exterior is characterized by a handsome cedar wood shingle roof and landscape defined by mature trees, rock outcroppings, and vibrant perennial gardens. Outdoor living is central to the property's allure, featuring an inground pool, sprawling 19 x 22 raised deck and screened porch providing a serene, airy environment for three-season relaxation - a natural extension of the interior living space. The heart of the home is the kitchen, a chef's delight featuring high-end Sub-Zero refrigeration and finishes that overlook the lush grounds. The interior is defined by freshly painted walls and gleaming hardwood floors that lead to a coveted primary suite conveniently located on the main level. With a total of two full and two half baths, the home is thoughtfully configured for both privacy and guest convenience. Additional versatility is found in the finished lower level, which currently hosts a private gym and a spacious recreation room complete with its own half bath. This level provides the flexible space necessary for contemporary living, whether used for fitness, media, or a home office.

315 North St, Roxbury

$1,400,000

This stunning property has undergone an extensive, down-to-the-studs renovation, creating a home that feels brand new. The redesigned layout features a spacious, open-concept great room, complemented by an elegant living room/sunroom with a striking stone fireplace that walks out to the back deck. The chef's kitchen is a showstopper, designed to impress even the most discerning culinary enthusiasts. The main level is home to a luxurious primary suite with a walk-in closet, offering a private retreat. Upstairs, two generously sized bedrooms each come with their own en-suite baths for convenience and comfort. The fully finished lower level offers versatile living space, including a fourth bedroom with its own en-suite bath, a game/media room, a kitchenette, and an addl spa-inspired bathroom for use from the pool. This level could easily serve as a private in-law suite. The beautifully finished barn adds even more appeal, featuring a three-car garage and a studio space above, perfect for creative projects, exercise room or as a private office. Studio is an additional 561+/- sq feet.

4 Beds ⋅ 6 Baths ⋅ CLOSED Status ⋅ 24110540 MLS

This stunning property has undergone an extensive, down-to-the-studs renovation, creating a home that feels brand new. The redesigned layout features a spacious, open-concept great room, complemented by an elegant living room/sunroom with a striking stone fireplace that walks out to the back deck. The chef's kitchen is a showstopper, designed to impress even the most discerning culinary enthusiasts. The main level is home to a luxurious primary suite with a walk-in closet, offering a private retreat. Upstairs, two generously sized bedrooms each come with their own en-suite baths for convenience and comfort. The fully finished lower level offers versatile living space, including a fourth bedroom with its own en-suite bath, a game/media room, a kitchenette, and an addl spa-inspired bathroom for use from the pool. This level could easily serve as a private in-law suite. The beautifully finished barn adds even more appeal, featuring a three-car garage and a studio space above, perfect for creative projects, exercise room or as a private office. Studio is an additional 561+/- sq feet.

30 Hickory Ln, Roxbury

$1,195,000

Great value, excellent location! Painter Hill is one of Roxbury's most scenic country roads. Close to Toplands Farm with beautiful pastoral views, a short drive to Maple Bank Farm for local produce, and just steps to a quiet dirt road for long walks. This charming Cape, built by the reputable local builder/owner in 2005, has 3 BR, 2.5 baths, a free-form Gunite pool and amazing outdoor living spaces. A covered front porch opens to the public living spaces. The main floor features a light-filled Great Room with a shiplap cathedral ceiling. The bookcases, bar and gas fireplace mantle are crafted from antique chestnut, and French doors open to a deck and patio. The dining room has a wood burning fireplace. An eat-in kitchen has a center island, granite counters, double ovens, refrigerator/freezer and a 4 burner gas cooktop. The primary bedroom suite is on the main level featuring built-in cabinets, a full bath and walk-in closet. There are two guest bedrooms and one full bath on the second floor. The lower level has one finished room and washer dryer. There is ample basement storage and access to a spacious two-car garage.

3 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24120750 MLS

Great value, excellent location! Painter Hill is one of Roxbury's most scenic country roads. Close to Toplands Farm with beautiful pastoral views, a short drive to Maple Bank Farm for local produce, and just steps to a quiet dirt road for long walks. This charming Cape, built by the reputable local builder/owner in 2005, has 3 BR, 2.5 baths, a free-form Gunite pool and amazing outdoor living spaces. A covered front porch opens to the public living spaces. The main floor features a light-filled Great Room with a shiplap cathedral ceiling. The bookcases, bar and gas fireplace mantle are crafted from antique chestnut, and French doors open to a deck and patio. The dining room has a wood burning fireplace. An eat-in kitchen has a center island, granite counters, double ovens, refrigerator/freezer and a 4 burner gas cooktop. The primary bedroom suite is on the main level featuring built-in cabinets, a full bath and walk-in closet. There are two guest bedrooms and one full bath on the second floor. The lower level has one finished room and washer dryer. There is ample basement storage and access to a spacious two-car garage.

158 Painter Hill Rd, Roxbury

$995,000

Discover this charming 4-bedroom Colonial with 1 additional bedroom is attached in-law apt on the southern side of Roxbury, offering an idyllic escape with seamless access to NYC. This privately situated home rests in a serene meadow, gracefully bordered by Pierce Brook. The main residence features a comfortable layout with a living room and fireplace that flows into the dining area and kitchen. Upstairs, you'll find four spacious bedrooms and two full bathrooms. A bright slate floored sunroom overlooks the inviting heated salt pool, perfect for relaxation and entertaining. Adding to its unique appeal is an attached 1-bedroom in law/guest house with propane heating and cooling, providing flexible space for visitors or extended family. The property boasts level land and lush grounds, including a expansive pasture area, all set against the picturesque backdrop of Pierce Brook. This Roxbury gem combines tranquility with convenience, making it an ideal retreat.

5 Beds ⋅ 5 Baths ⋅ CLOSED Status ⋅ 24097497 MLS

Discover this charming 4-bedroom Colonial with 1 additional bedroom is attached in-law apt on the southern side of Roxbury, offering an idyllic escape with seamless access to NYC. This privately situated home rests in a serene meadow, gracefully bordered by Pierce Brook. The main residence features a comfortable layout with a living room and fireplace that flows into the dining area and kitchen. Upstairs, you'll find four spacious bedrooms and two full bathrooms. A bright slate floored sunroom overlooks the inviting heated salt pool, perfect for relaxation and entertaining. Adding to its unique appeal is an attached 1-bedroom in law/guest house with propane heating and cooling, providing flexible space for visitors or extended family. The property boasts level land and lush grounds, including a expansive pasture area, all set against the picturesque backdrop of Pierce Brook. This Roxbury gem combines tranquility with convenience, making it an ideal retreat.

286 South St, Roxbury

$960,000

Discover modern serenity in this private contemporary retreat nestled on 3.44 private acres. The ascending driveway assures a sense of quiet and seclusion, leading you to a home bathed in natural light from a soaring two-story wall of south-facing windows, this home perfectly blends architectural drama with a peaceful woodland backdrop. The exterior features an expansive, brand new composite deck with its sleek cable railing system--perfect for al fresco dining or quiet mornings. Inside, the light filled, open-concept main level is anchored by 5 1/4" hardwood oak flooring and a dramatic granite gas burning fireplace. A full wall of custom built in's create style and ample storage. The kitchen is designed for functionality with its central island, quartz countertops and new Fulgar Milano induction range and a new LG refrigerator. Retreat to the main-level primary on-suite, which offers its own private deck access via French patio doors. Upstairs, a glass railed loft provides additional flexible space. The fully tiled walk out lower level includes a full bath offering excellent potential for an in law apartment, guest suite or private home office with a 2nd laundry hook up area in the garage. Meticulously maintained and newly painted throughout, this sanctuary is equipped with radiant heat, central air, a main level laundry and a newer water softening system.

3 Beds ⋅ 4 Baths ⋅ CLOSED Status ⋅ 24157035 MLS

Discover modern serenity in this private contemporary retreat nestled on 3.44 private acres. The ascending driveway assures a sense of quiet and seclusion, leading you to a home bathed in natural light from a soaring two-story wall of south-facing windows, this home perfectly blends architectural drama with a peaceful woodland backdrop. The exterior features an expansive, brand new composite deck with its sleek cable railing system--perfect for al fresco dining or quiet mornings. Inside, the light filled, open-concept main level is anchored by 5 1/4" hardwood oak flooring and a dramatic granite gas burning fireplace. A full wall of custom built in's create style and ample storage. The kitchen is designed for functionality with its central island, quartz countertops and new Fulgar Milano induction range and a new LG refrigerator. Retreat to the main-level primary on-suite, which offers its own private deck access via French patio doors. Upstairs, a glass railed loft provides additional flexible space. The fully tiled walk out lower level includes a full bath offering excellent potential for an in law apartment, guest suite or private home office with a 2nd laundry hook up area in the garage. Meticulously maintained and newly painted throughout, this sanctuary is equipped with radiant heat, central air, a main level laundry and a newer water softening system.

28 Garnet Rd, Roxbury

$959,000

Privacy and space galore at this renovated Colonial, which is ready for its next residents. 4 bedrooms and 3 1/2 baths, PLUS 2 additional rooms on the 3rd floor, offering office/rec/studio space, or additional bedroom space. NEW bathrooms. NEW carpet. NEW interior paint. Refinished oak floors. Refreshed kitchen. Exterior has been power washed, and the garage doors have been refurbished. Huge basement for storage. Beautiful yard in which to enjoy each season. Bask in the quiet life that beautiful Roxbury offers, with the convenience of shopping and dining in nearby Southbury, New Milford, and Woodbury.

4 Beds ⋅ 4 Baths ⋅ CLOSED Status ⋅ 24163402 MLS

Privacy and space galore at this renovated Colonial, which is ready for its next residents. 4 bedrooms and 3 1/2 baths, PLUS 2 additional rooms on the 3rd floor, offering office/rec/studio space, or additional bedroom space. NEW bathrooms. NEW carpet. NEW interior paint. Refinished oak floors. Refreshed kitchen. Exterior has been power washed, and the garage doors have been refurbished. Huge basement for storage. Beautiful yard in which to enjoy each season. Bask in the quiet life that beautiful Roxbury offers, with the convenience of shopping and dining in nearby Southbury, New Milford, and Woodbury.

34 Bacon Rd, Roxbury

$912,500

This Circa 1851 Historic house known as 'Mine and Quarry House "in Roxbury, Ct ' Historic and Architectural resource survey is highly significant as the only surviving antique of the mining and quarrying industries. It boarders on 100's of acres of the Roxbury Land trust and enjoys valley views of the Shepaug River. Over time it became a really charming home in a very private and pretty setting on 6 acres at the end of a dirt road that runs along the river and pond.The approach is simply magical and this is only one of two homes on the road. Truly Light filled with 4 bedrooms and 3 full baths, features include a front to back living room with fireplace and a sweet kitchen with sitting area and a wood burning stove. There is a small library room in between. Access to the stunning property is from a glassed side porch that easily flows from the center of the first floor and formal dining room. There is also a large rear deck for sun baths, or dining as it has access from the kitchen and Living room, so perfect for entertaining. This property is a complete sanctuary with an in ground pool just off the deck along with an out door shower and mature beautiful landscaping a 30 year passion of one of the owners. There is a newer 2 car garage that hides the pool equipment and has etc storage. This is an enchanting property with enviable seclusion but is only minutes to farmers markets, great restaurants, a general store, and central to everything Litchfield County is know for.

4 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24082077 MLS

This Circa 1851 Historic house known as 'Mine and Quarry House "in Roxbury, Ct ' Historic and Architectural resource survey is highly significant as the only surviving antique of the mining and quarrying industries. It boarders on 100's of acres of the Roxbury Land trust and enjoys valley views of the Shepaug River. Over time it became a really charming home in a very private and pretty setting on 6 acres at the end of a dirt road that runs along the river and pond.The approach is simply magical and this is only one of two homes on the road. Truly Light filled with 4 bedrooms and 3 full baths, features include a front to back living room with fireplace and a sweet kitchen with sitting area and a wood burning stove. There is a small library room in between. Access to the stunning property is from a glassed side porch that easily flows from the center of the first floor and formal dining room. There is also a large rear deck for sun baths, or dining as it has access from the kitchen and Living room, so perfect for entertaining. This property is a complete sanctuary with an in ground pool just off the deck along with an out door shower and mature beautiful landscaping a 30 year passion of one of the owners. There is a newer 2 car garage that hides the pool equipment and has etc storage. This is an enchanting property with enviable seclusion but is only minutes to farmers markets, great restaurants, a general store, and central to everything Litchfield County is know for.

11 Hodge Rd, Roxbury

$895,000

This place is a real gem! It needs some updates, but the structure is solid, and the property is beyond compare. It's set on over three gorgeous acres with beautiful stone walls and a private usable yard that's perfect for a pool. Extensive stonework is present on side steps, patios, and rear gardens, complemented by a stone breezeway connecting the 3-car garage to a side entry hall. The driveway is FLAT with ample parking. Inside, the kitchen and bathrooms need renovation, but everything works. An open foyer leads to a high-ceilinged living room with a Palladian window and fireplace, flowing into a dining area separated by columns for entertaining ease. The walls have been freshly painted white, and you might want to replace the bedroom carpeting or add more hardwood. The living and dining rooms have gleaming hardwood floors, and there are solid wood doors and 6-inch outer walls. The exceptional and large windows let in tons of natural light. The main floor includes a private primary bedroom with a windowed bay, elevated ceilings, a large bath with tub and separate shower, and huge walk-in closet. A four-zone heating system includes radiant floor heat in the primary bath. Upstairs has three more bedrooms, a hall full bath, and easy-access attic storage. It's all here, just waiting to become your dream home. Plus, it's in Southern Roxbury, close to shopping and highways, with low taxes and excellent schools. Enjoy this delightful small town!

4 Beds ⋅ 4 Baths ⋅ CLOSED Status ⋅ 24141041 MLS

This place is a real gem! It needs some updates, but the structure is solid, and the property is beyond compare. It's set on over three gorgeous acres with beautiful stone walls and a private usable yard that's perfect for a pool. Extensive stonework is present on side steps, patios, and rear gardens, complemented by a stone breezeway connecting the 3-car garage to a side entry hall. The driveway is FLAT with ample parking. Inside, the kitchen and bathrooms need renovation, but everything works. An open foyer leads to a high-ceilinged living room with a Palladian window and fireplace, flowing into a dining area separated by columns for entertaining ease. The walls have been freshly painted white, and you might want to replace the bedroom carpeting or add more hardwood. The living and dining rooms have gleaming hardwood floors, and there are solid wood doors and 6-inch outer walls. The exceptional and large windows let in tons of natural light. The main floor includes a private primary bedroom with a windowed bay, elevated ceilings, a large bath with tub and separate shower, and huge walk-in closet. A four-zone heating system includes radiant floor heat in the primary bath. Upstairs has three more bedrooms, a hall full bath, and easy-access attic storage. It's all here, just waiting to become your dream home. Plus, it's in Southern Roxbury, close to shopping and highways, with low taxes and excellent schools. Enjoy this delightful small town!

67 Transylvania Rd, Roxbury

$850,000

Light-filled, modern living on a private nearly 2+ acre corner lot - with room to grow. Set on a beautifully positioned corner parcel, this fully renovated home is defined by natural light and flexibility. Expansive windows and vaulted ceilings create a bright, open feel throughout the main living spaces, bringing in sunlight from multiple exposures and connecting the home to its surrounding landscape. Completely transformed with high-end finishes and energy-efficient upgrades, the home offers the ultimate floor plan, featuring two first-floor ensuite options and close proximity to Roxbury Market, town tennis courts and Hurlburt Park. The finished lower level adds another layer of versatility, with walk-out access A rare combination of move-in-ready ease and long-term optionality, all set on a private and peaceful setting.

3 Beds ⋅ 4 Baths ⋅ CLOSED Status ⋅ 24158237 MLS

Light-filled, modern living on a private nearly 2+ acre corner lot - with room to grow. Set on a beautifully positioned corner parcel, this fully renovated home is defined by natural light and flexibility. Expansive windows and vaulted ceilings create a bright, open feel throughout the main living spaces, bringing in sunlight from multiple exposures and connecting the home to its surrounding landscape. Completely transformed with high-end finishes and energy-efficient upgrades, the home offers the ultimate floor plan, featuring two first-floor ensuite options and close proximity to Roxbury Market, town tennis courts and Hurlburt Park. The finished lower level adds another layer of versatility, with walk-out access A rare combination of move-in-ready ease and long-term optionality, all set on a private and peaceful setting.

45 Chalybes Rd, Roxbury

$817,000

Large parcel of raw land offering a unique opportunity. This 66 acre parcel fronts two well connected roads, ensuring ease of access and flexibility in planning. With some clearing it offers easterly views of the rolling landscape and morning sunrises, making the parcel perfect for a large estate or residential compound. Roxbury is in southern Litchfield County with a population of less than 3,000 people, it is the epitome of a small New England town. Only 65 miles to New York City, this land's unique features and untapped potential await your vision.

CLOSED Status ⋅ 24103219 MLS

Large parcel of raw land offering a unique opportunity. This 66 acre parcel fronts two well connected roads, ensuring ease of access and flexibility in planning. With some clearing it offers easterly views of the rolling landscape and morning sunrises, making the parcel perfect for a large estate or residential compound. Roxbury is in southern Litchfield County with a population of less than 3,000 people, it is the epitome of a small New England town. Only 65 miles to New York City, this land's unique features and untapped potential await your vision.

Good Hill Road, Roxbury

$808,000

Welcome to the Truman Judson Historical Property. 2 homes on 11.36 private hillside acres overlooking the Shepaug River. House 1 is a beautifully restored 1,449 sq ft converted barn offering 1 bedroom, 1.5 baths, living room plus a large den. Rich in character, it features stone accent walls, exposed beams, custom built-ins, a brick wood-burning fireplace and an eat-in kitchen with island, new appliances and porcelain wood-look floors. Oversized windows and doors flood the home with natural light. The 2nd floor offers vaulted ceilings, a light filled front room with 3 sides of windows, a large den, walk in closets, laundry & a renovate primary bath w/radiant heated stone floors. Outdoor living is exceptional with lower BBQ/dining area, fenced yd, expansive upper stone terrace w/outdoor bar, 3 sided stone fireplace, hot tub, stone retaining walls & French doors. House 2 has been gutted to the studs & is ready for renovation. Updates to house 1 since 2020 include A/C, kitchen, baths, electrical, plumbing, roof, insulation, windows & driveway. A true Litchfield County retreat. An oasis where you can hike your own mountain, cook pizzas in your outdoor wood-fired oven, gather around your triple sided stone fireplace, soak in the hot tub & enjoy breathtaking star-filled skies. The stone home is move-in ready and sold AS-Is. Engineering complete with approved well & septic sites offering potential subdivision. Approx 79 Miles to NYC. A truly magical setting.

1 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 24149133 MLS

Welcome to the Truman Judson Historical Property. 2 homes on 11.36 private hillside acres overlooking the Shepaug River. House 1 is a beautifully restored 1,449 sq ft converted barn offering 1 bedroom, 1.5 baths, living room plus a large den. Rich in character, it features stone accent walls, exposed beams, custom built-ins, a brick wood-burning fireplace and an eat-in kitchen with island, new appliances and porcelain wood-look floors. Oversized windows and doors flood the home with natural light. The 2nd floor offers vaulted ceilings, a light filled front room with 3 sides of windows, a large den, walk in closets, laundry & a renovate primary bath w/radiant heated stone floors. Outdoor living is exceptional with lower BBQ/dining area, fenced yd, expansive upper stone terrace w/outdoor bar, 3 sided stone fireplace, hot tub, stone retaining walls & French doors. House 2 has been gutted to the studs & is ready for renovation. Updates to house 1 since 2020 include A/C, kitchen, baths, electrical, plumbing, roof, insulation, windows & driveway. A true Litchfield County retreat. An oasis where you can hike your own mountain, cook pizzas in your outdoor wood-fired oven, gather around your triple sided stone fireplace, soak in the hot tub & enjoy breathtaking star-filled skies. The stone home is move-in ready and sold AS-Is. Engineering complete with approved well & septic sites offering potential subdivision. Approx 79 Miles to NYC. A truly magical setting.

178 Baker Rd, Roxbury

$754,500

Step into a world of charm and timeless elegance in Roxbury, CT. This bucolic estate spans 5.18 acres and offers a blend of historic charm and rustic sophistication. Explore the six-bedroom main house, complete with five bathrooms and five fireplaces, wood beams and stunning wide plank flooring bring warmth and style. This tranquil home embodies classic Connecticut living with its antique patina and captivating features. The estate also includes a charming two-bedroom guest cottage, perfect for hosting guests or extended family in a romantic setting. Invest in a lifestyle that blends history, luxury, and country living. Your dream home awaits.

6 Beds ⋅ 5 Baths ⋅ CLOSED Status ⋅ 24034675 MLS

Step into a world of charm and timeless elegance in Roxbury, CT. This bucolic estate spans 5.18 acres and offers a blend of historic charm and rustic sophistication. Explore the six-bedroom main house, complete with five bathrooms and five fireplaces, wood beams and stunning wide plank flooring bring warmth and style. This tranquil home embodies classic Connecticut living with its antique patina and captivating features. The estate also includes a charming two-bedroom guest cottage, perfect for hosting guests or extended family in a romantic setting. Invest in a lifestyle that blends history, luxury, and country living. Your dream home awaits.

118 Chalybes Rd W, Roxbury

$725,000

Nestled within one of Roxbury, Connecticut's most quiet and picturesque enclaves, this charming 3-bedroom, 2-bath Cape Cod home offers a rare opportunity to cultivate your dream country retreat. Built in the 1970s, this residence presents a wonderful canvas for those seeking to personalize and update a home within a highly sought-after area, celebrated for its exquisite properties and serene landscapes. The idyllic surroundings include a tranquil stream which meanders down through the property, while established mature plantings burst with color and life, providing a private oasis for relaxation and enjoyment. Imagine alfresco dining on the inviting stone terrace, or pursuing your gardening passions in the dedicated garden shed. This home is ready for its next chapter, offering a foundation of classic Cape Cod charm awaiting modern touches. It's an exceptional chance to invest in a lifestyle of peace and natural beauty, surrounded by the distinguished homes that define this desirable corner of rural Connecticut. *Town tax records - 3 bedrooms, health file has 2.

3 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 24147507 MLS

Nestled within one of Roxbury, Connecticut's most quiet and picturesque enclaves, this charming 3-bedroom, 2-bath Cape Cod home offers a rare opportunity to cultivate your dream country retreat. Built in the 1970s, this residence presents a wonderful canvas for those seeking to personalize and update a home within a highly sought-after area, celebrated for its exquisite properties and serene landscapes. The idyllic surroundings include a tranquil stream which meanders down through the property, while established mature plantings burst with color and life, providing a private oasis for relaxation and enjoyment. Imagine alfresco dining on the inviting stone terrace, or pursuing your gardening passions in the dedicated garden shed. This home is ready for its next chapter, offering a foundation of classic Cape Cod charm awaiting modern touches. It's an exceptional chance to invest in a lifestyle of peace and natural beauty, surrounded by the distinguished homes that define this desirable corner of rural Connecticut. *Town tax records - 3 bedrooms, health file has 2.

242 Tophet Rd, Roxbury

$710,000

Tucked away on a long private road, this light and bright Roxbury retreat combines timeless character with modern comfort. The home features three spacious bedrooms and two and a half baths, thoughtfully designed for both everyday living and effortless entertaining. Soaring ceilings with exposed beams and abundant skylights fill the interior with natural light, highlighting the warmth of beautiful wood floors throughout. The open floor plan creates a sense of airiness and flow, while large windows bring the surrounding nature indoors. Whether you're relaxing in the peaceful primary bedroom or gathering in the inviting living area, every space feels serene and connected to the outdoors. The lower level offers 9'+ ceilings, windows and a walk-out. A rare opportunity to enjoy quiet country living just minutes from the heart of Roxbury - the perfect blend of rustic charm and contemporary style.

3 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24132367 MLS

Tucked away on a long private road, this light and bright Roxbury retreat combines timeless character with modern comfort. The home features three spacious bedrooms and two and a half baths, thoughtfully designed for both everyday living and effortless entertaining. Soaring ceilings with exposed beams and abundant skylights fill the interior with natural light, highlighting the warmth of beautiful wood floors throughout. The open floor plan creates a sense of airiness and flow, while large windows bring the surrounding nature indoors. Whether you're relaxing in the peaceful primary bedroom or gathering in the inviting living area, every space feels serene and connected to the outdoors. The lower level offers 9'+ ceilings, windows and a walk-out. A rare opportunity to enjoy quiet country living just minutes from the heart of Roxbury - the perfect blend of rustic charm and contemporary style.

38 W Mountain Ln, Roxbury

$695,000

This handsome 1820's Colonial, set behind large shade trees on 1.33 acres just off the Green, is an easy walk to the Library, Booth School, Apple Lane Park, Churches, Tennis courts, and a morning cuppa at the Roxbury Market. Major renovation in 2018 included New HVAC, New wiring, Rebuilt Porch and more. New Well installed dedicated to this property replaced shared source. Interior makeover included fine Kitchen with gas range and quartz counters, formal Dining room or Library, Powder Room, and front-to-back Living Room leading to full-width covered porch overlooking the lawn, wonderful for entertaining. The Main floor shines with wide-board oak floors, thermal windows and traditional trim. Greet the morning sun in the second floor primary Bedroom with ensuite bath and walk-in closet. Two other bedrooms and hall bath also share this floor. Stairs lead up to the third floor and two more finished rooms. Level lawn behind the house extends back to a large barn with water, electric and a poured concrete floor for garage or many other creative uses. There's so much here in this inviting antique Roxbury home that lives like new!

3 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24175557 MLS

This handsome 1820's Colonial, set behind large shade trees on 1.33 acres just off the Green, is an easy walk to the Library, Booth School, Apple Lane Park, Churches, Tennis courts, and a morning cuppa at the Roxbury Market. Major renovation in 2018 included New HVAC, New wiring, Rebuilt Porch and more. New Well installed dedicated to this property replaced shared source. Interior makeover included fine Kitchen with gas range and quartz counters, formal Dining room or Library, Powder Room, and front-to-back Living Room leading to full-width covered porch overlooking the lawn, wonderful for entertaining. The Main floor shines with wide-board oak floors, thermal windows and traditional trim. Greet the morning sun in the second floor primary Bedroom with ensuite bath and walk-in closet. Two other bedrooms and hall bath also share this floor. Stairs lead up to the third floor and two more finished rooms. Level lawn behind the house extends back to a large barn with water, electric and a poured concrete floor for garage or many other creative uses. There's so much here in this inviting antique Roxbury home that lives like new!

20 Wellers Bridge Rd, Roxbury

$615,000

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

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