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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.

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 ⋅ 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

$3,150,000

PRIVATE. GATED. EXTRAORDINARY. A Litchfield Hills estate with room for everyone-and everything. Set behind a private gated drive on more than 20 secluded acres, 11 Raven Rock Road is a rare Litchfield Hills compound offering privacy, scale and resort-style amenities in one exceptional setting. The elegant shingle-style main residence spans 7,063 square feet with four bedrooms, multiple fireplaces and beautifully refreshed interiors. But this is much more than a house. It is an estate designed for living, entertaining and gathering. A heated Gunite pool and private tennis court create a year-round country retreat, while a three-bay garage with a one-bedroom caretaker apartment and a separate two-bedroom guest apartment provide exceptional flexibility for family, guests and staff. Surrounded by the natural beauty of Roxbury and the Litchfield Hills, the property delivers the rare combination of complete privacy and proximity to the villages, restaurants, cultural attractions and outdoor pursuits that define this coveted corner of Connecticut.

4 Beds ⋅ 6 Baths ⋅ 24207145 MLS

PRIVATE. GATED. EXTRAORDINARY. A Litchfield Hills estate with room for everyone-and everything. Set behind a private gated drive on more than 20 secluded acres, 11 Raven Rock Road is a rare Litchfield Hills compound offering privacy, scale and resort-style amenities in one exceptional setting. The elegant shingle-style main residence spans 7,063 square feet with four bedrooms, multiple fireplaces and beautifully refreshed interiors. But this is much more than a house. It is an estate designed for living, entertaining and gathering. A heated Gunite pool and private tennis court create a year-round country retreat, while a three-bay garage with a one-bedroom caretaker apartment and a separate two-bedroom guest apartment provide exceptional flexibility for family, guests and staff. Surrounded by the natural beauty of Roxbury and the Litchfield Hills, the property delivers the rare combination of complete privacy and proximity to the villages, restaurants, cultural attractions and outdoor pursuits that define this coveted corner of Connecticut.

11 Ravenrock Rd, 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 ⋅ 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

$1,795,000

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 ⋅ 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 ⋅ 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 ⋅ 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 ⋅ 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

$1,425,000

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 ⋅ 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 ⋅ 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

$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 ⋅ 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 ⋅ 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

$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 ⋅ 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

$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 ⋅ 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 ⋅ 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 ⋅ 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

$606,000

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

3 Beds ⋅ 3 Baths ⋅ 24197990 MLS

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

90 Mallory Rd, Roxbury

$597,000

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

2 Beds ⋅ 2 Baths ⋅ 24182244 MLS

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

188 Bacon Rd, Roxbury

$583,000

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

2 Beds ⋅ 2 Baths ⋅ 24177292 MLS

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

94 Judds Bridge Rd, Roxbury

$455,000

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

3 Beds ⋅ 2 Baths ⋅ 24166843 MLS

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

137 Davenport Rd, Roxbury

$450,000

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

24168082 MLS

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

Lot 7 & Lot 8 & Dr, Roxbury

$235,000

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

24093092 MLS

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

Booth Road, Roxbury

$215,000

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

24169970 MLS

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

307 North St, Roxbury

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