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$998,000

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

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24204225 MLS

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

16 Jonathan Dr, Roxbury

$3,495,000

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

4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24201025 MLS

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

35 Schoolhouse Rd, Roxbury

$575,000

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 ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24197990 MLS

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

90 Mallory Rd, Roxbury

$589,990

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

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24197040 MLS

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

21 Carriage Ln, Roxbury

$1,195,000

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

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24192986 MLS

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

22 E Woods Rd, Roxbury

$1,269,000

Completely remodeled 3 bedroom, 2.5 bath open concept home, with two fireplaces (one with wood burning insert), kitchen with stainless appliances, granite counters and large island. Property is private - boarders 18 acre land trust and farm land. Gunite pool (propane heater) with pavilion and fire pit for entertaining. Hot tub off main bedroom patio. Property features stone walls, steps and patios. Generac whole home generator. Detached oversized garage with game room (potential in-law set up). Great home for entertaining.

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24192683 MLS

Completely remodeled 3 bedroom, 2.5 bath open concept home, with two fireplaces (one with wood burning insert), kitchen with stainless appliances, granite counters and large island. Property is private - boarders 18 acre land trust and farm land. Gunite pool (propane heater) with pavilion and fire pit for entertaining. Hot tub off main bedroom patio. Property features stone walls, steps and patios. Generac whole home generator. Detached oversized garage with game room (potential in-law set up). Great home for entertaining.

85 Good Hill Rd, Roxbury

$1,795,000

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

5 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24189301 MLS

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

233 Southbury Rd, Roxbury

$850,000

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

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24180161 MLS

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

47 South St, Roxbury

$575,000

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

2 Beds ⋅ 2 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24182244 MLS

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

188 Bacon Rd, Roxbury

$725,000

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 ⋅ ACTIVE 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

$950,000

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 ⋅ ACTIVE UNDER CONTRACT 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

$1,469,000

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

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24163570 MLS

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

33 Sentry Hill Rd, Roxbury

$1,495,000

Nestled on nearly seven private acres along a quiet country road in picturesque Roxbury, this exceptional residence offers a seamless blend of elegance, comfort, and classic New England charm. Set back from the road with a gently curving drive, the home welcomes you with a dramatic two-story foyer and grand staircase, complemented by hardwood floors, detailed millwork, crown molding, tray ceilings, and abundant natural light throughout. The gourmet kitchen features custom cherry cabinetry, granite countertops, stainless steel appliances, and a butler's pantry, opening to a warm hearth room with a fieldstone fireplace. A sunken family room with a brick fireplace and French doors leads to a stone patio, creating an ideal flow for indoor-outdoor living. The upper level offers a spacious primary suite, three additional bedrooms, three full baths, and a versatile rooms suitable for a home office, lounge, or playroom. The walk-out lower level with 9-foot ceilings provides approximately 1,950square feet of additional living space, including a recreation area, full bar, exercise room, bedroom, full bath, and flexible space for entertaining or extended living. The grounds offer a peaceful retreat with woodland trails, a stream, fire pit, outbuildings, and a two-story pool house. Additional features include a chicken coop and utility structure, enhancing the property's country lifestyle appeal. Conveniently located near local amenities while offering privacy and tranquility.

4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24162311 MLS

Nestled on nearly seven private acres along a quiet country road in picturesque Roxbury, this exceptional residence offers a seamless blend of elegance, comfort, and classic New England charm. Set back from the road with a gently curving drive, the home welcomes you with a dramatic two-story foyer and grand staircase, complemented by hardwood floors, detailed millwork, crown molding, tray ceilings, and abundant natural light throughout. The gourmet kitchen features custom cherry cabinetry, granite countertops, stainless steel appliances, and a butler's pantry, opening to a warm hearth room with a fieldstone fireplace. A sunken family room with a brick fireplace and French doors leads to a stone patio, creating an ideal flow for indoor-outdoor living. The upper level offers a spacious primary suite, three additional bedrooms, three full baths, and a versatile rooms suitable for a home office, lounge, or playroom. The walk-out lower level with 9-foot ceilings provides approximately 1,950square feet of additional living space, including a recreation area, full bar, exercise room, bedroom, full bath, and flexible space for entertaining or extended living. The grounds offer a peaceful retreat with woodland trails, a stream, fire pit, outbuildings, and a two-story pool house. Additional features include a chicken coop and utility structure, enhancing the property's country lifestyle appeal. Conveniently located near local amenities while offering privacy and tranquility.

380 Southbury Rd, Roxbury

$985,000

Own a Piece of Roxbury History! One of Roxbury's three oldest homes, this site has been cherished by seven generations of the Squire family. The existing antique home, while requiring reconstruction, has the potential to be reimagined as a charming guest house, preserving a tangible link to the past. Set on 12.7-acres this property and boasts breathtaking eastern views and the unique opportunity to create a stunning estate on land steeped in local heritage. A partially intact stone foundation (approximately 1500 sq ft) provides a solid base for this endeavor. Imagine building your dream home atop the hill, capitalizing on the panoramic vistas. A beautifully renovated barn, listed as historic landmark, adds further character and value. The property abuts Land Trust for hiking, ensuring privacy and natural beauty. Infrastructure is in place with a completed A-2 survey, installed driveway, and approved septic plans (3-bedroom for the antique home and 8-bedroom for a main residence). Electrical conduit is also installed to the proposed homesite. This land has subdivision potential and is ready for you to create a legacy of your own. **Note: Home is uninhabitable at this time. A full rebuild and renovation is required.

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24159885 MLS

Own a Piece of Roxbury History! One of Roxbury's three oldest homes, this site has been cherished by seven generations of the Squire family. The existing antique home, while requiring reconstruction, has the potential to be reimagined as a charming guest house, preserving a tangible link to the past. Set on 12.7-acres this property and boasts breathtaking eastern views and the unique opportunity to create a stunning estate on land steeped in local heritage. A partially intact stone foundation (approximately 1500 sq ft) provides a solid base for this endeavor. Imagine building your dream home atop the hill, capitalizing on the panoramic vistas. A beautifully renovated barn, listed as historic landmark, adds further character and value. The property abuts Land Trust for hiking, ensuring privacy and natural beauty. Infrastructure is in place with a completed A-2 survey, installed driveway, and approved septic plans (3-bedroom for the antique home and 8-bedroom for a main residence). Electrical conduit is also installed to the proposed homesite. This land has subdivision potential and is ready for you to create a legacy of your own. **Note: Home is uninhabitable at this time. A full rebuild and renovation is required.

179 South St, Roxbury

$15,000

Available Oct 1, 2026 @ $15,000/mo. Perched high on a scenic Roxbury hillside, this new 3-bedroom home represents true luxury living. The architecture seamlessly integrates nature and light with huge walls of windows with retractable screens. The 2 embedded James Turrell light sculptures transform the living experience into an ever-changing meditation on color and space. The open floor plan maximizes the intimate spaces and enables easy entertaining. A gourmet kitchen serves as both functional workspace and visual centerpiece with custom cabinetry, countertops, and integrated professional-grade appliances. The great room hosts dining for 12, spacious seating area and uber chic floating fireplace. The main floor is completed by the 3rd bedroom (Queen Bed) with its own private bath and a powder room. Upstairs features 2 primary bedrooms (both Queen Beds) with spa-inspired bathrooms (one with soaking tub and one with shower) overlooking private woodland views. The upstairs landing host an office nook. Luxury fixtures and designer furnishings throughout. Brand new Gunite heated pool is fully fenced. 7 person free standing Jacuzzi is available for year round use. This property offers an unparalleled rental opportunity in a coveted location. Just 10 mins to village centers of Washington & Woodbury with farmer's markets, organic provisions, chic shops and cultural events. Also avail Summer 2027 at $25,000/mo.

3 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24081154 MLS

Available Oct 1, 2026 @ $15,000/mo. Perched high on a scenic Roxbury hillside, this new 3-bedroom home represents true luxury living. The architecture seamlessly integrates nature and light with huge walls of windows with retractable screens. The 2 embedded James Turrell light sculptures transform the living experience into an ever-changing meditation on color and space. The open floor plan maximizes the intimate spaces and enables easy entertaining. A gourmet kitchen serves as both functional workspace and visual centerpiece with custom cabinetry, countertops, and integrated professional-grade appliances. The great room hosts dining for 12, spacious seating area and uber chic floating fireplace. The main floor is completed by the 3rd bedroom (Queen Bed) with its own private bath and a powder room. Upstairs features 2 primary bedrooms (both Queen Beds) with spa-inspired bathrooms (one with soaking tub and one with shower) overlooking private woodland views. The upstairs landing host an office nook. Luxury fixtures and designer furnishings throughout. Brand new Gunite heated pool is fully fenced. 7 person free standing Jacuzzi is available for year round use. This property offers an unparalleled rental opportunity in a coveted location. Just 10 mins to village centers of Washington & Woodbury with farmer's markets, organic provisions, chic shops and cultural events. Also avail Summer 2027 at $25,000/mo.

24 Old Roxbury Rd, Roxbury

$30,900

Mint 6 bedroom colonial reproduction on scenic dirt road. Walk, jog, bike into land preserve. Heated pool, outdoor play set, bbq, 3 acre lawn, 4 wood-burning fireplaces. SUMMER:June - August $30,900/month. Memorial - Labor Day $74,900.OFF-SEASON: September - May $13,900/month If over 3 months, subtract $1,000 per month and no tax is due. ANNUAL:$169,000. Inquire about other/shorter rental terms.

6 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 170305994 MLS

Mint 6 bedroom colonial reproduction on scenic dirt road. Walk, jog, bike into land preserve. Heated pool, outdoor play set, bbq, 3 acre lawn, 4 wood-burning fireplaces. SUMMER:June - August $30,900/month. Memorial - Labor Day $74,900.OFF-SEASON: September - May $13,900/month If over 3 months, subtract $1,000 per month and no tax is due. ANNUAL:$169,000. Inquire about other/shorter rental terms.

33 Sentry Hill Rd, Roxbury

$30,900

Perfect 6BR 3.5 Bath home with heated pool and child's play gym on a scenic country dirt road that leads into a land preserve along the Shepaug River - perfect for walking, jogging, biking. The most desirable rural historic location within 2 hours of NYC - Roxbury and Washington CT. Home to actors, writers, artists and the owners of luxury estate vacation homes. Many world class restaurants, inns and spas. Skiing, Lake Waramaug Beaches, BBQ, farm stands and fairs, antiquing, and numerous recreational activities.SUMMER June - August $30,900/month; Memorial - Labor Day $74,900; OFF-SEASON September - May $13,900/month. If over 3 months, deduct $1,000 per month and no tax is due. ANNUAL $169,000. Inquire about other/shorter rental terms.

3 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 170306004 MLS

Perfect 6BR 3.5 Bath home with heated pool and child's play gym on a scenic country dirt road that leads into a land preserve along the Shepaug River - perfect for walking, jogging, biking. The most desirable rural historic location within 2 hours of NYC - Roxbury and Washington CT. Home to actors, writers, artists and the owners of luxury estate vacation homes. Many world class restaurants, inns and spas. Skiing, Lake Waramaug Beaches, BBQ, farm stands and fairs, antiquing, and numerous recreational activities.SUMMER June - August $30,900/month; Memorial - Labor Day $74,900; OFF-SEASON September - May $13,900/month. If over 3 months, deduct $1,000 per month and no tax is due. ANNUAL $169,000. Inquire about other/shorter rental terms.

45 Moosehorn Rd, Roxbury