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$1,600,000
2 Beds ⋅ 3 Baths ⋅ 24065004 MLS
Offered on 34+/- acres subject to lot line revision. Abuts 100's of acres of conserved land. Long private driveway past pond to architect designed contemporary farmhouse with barn and workshop. Great room with privacy sliders allowing kitchen to be closed off if desired. Hidden media wall, views over lawn and stonewalls, modern wood stove in living room. Fabulous screen porch looking towards pond. Main floor primary suite with modern wood stove. Upstairs contains office/media room and second bedroom and bath. 1 bay attached garage and 2 bay barn for car storage with insulated workshop and loft above. Beautiful forests of mixed woods, ferns, stonewalls. Lovely large lawn area for possible pool. Complete privacy for enjoying nature and hiking. House equipped with generator. Property is gated with full security package - appointments required to visit. Acreage and taxes to be adjusted post lot line revision. Much of land currently in PA490 for temporary tax abatement.

130 Flag Swamp Rd, Roxbury
$1,560,000
2 Beds ⋅ 3 Baths ⋅ 24045245 MLS
Pristine and private Modern Farmhouse with magnificent design, vaulted ceilings, 2 fireplaces, over-sized living room, dining room for 10, chef's kitchen, 3 bedrooms. Beautifully sited heated pool surrounded by endless summer hydrangea and 8 +/- acres of lawns, pond, and fields. Ideal for walking, jogging and biking. Perfect location, minutes from the centers of Roxbury and Washington.

35 Painter Ridge Rd, Roxbury
$1,500,000
4 Beds ⋅ 4 Baths ⋅ 170626647 MLS
Taking to heart the famous quote “Simplicity is the ultimate sophistication” by Leonardo de Vinci, the current owners designed this brick saltbox to perfection. Much thought went into the high quality new and reclaimed materials used. The exterior is historically correct handmade Waterstruck brick with Lifespan Solid Select pressure treated trim from New Zealand, a 5/8” pressure treated cedar shingle roof and handmade copper lighting. The thick granite rectangular blocks that make up the rear patio came from the exterior of a 19th century prison. Other handmade details include the front entry with antique bullseye glass transom and custom staircase including the balusters. The detached two garages/barns were built by Country Carpenters Post and Beam Buildings and both have split systems. The interior is elegant and charming. The kitchen is highlighted by the handmade Cherry and Butternut wood cabinetry, custom handmade brick wood-fired pizza oven and Bertazonni appliances. The formal living room w/fireplace has gorgeous crown molding which is also found in the comfortable study. The primary bedroom upstairs has a full bath and two walk-in closets. The additional two upper-level bedrooms share a hall bath and the laundry is hidden behind a pocket door. Exactly where needed, the windows in the lower level make the space light and bright. On this floor is the fourth bedroom, full bath, family room and storage rooms. Adjacent to land trust on quiet country road.

52 Welton Rd, Roxbury
$1,500,000
4 Beds ⋅ 4 Baths ⋅ 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
$1,490,000
3 Beds ⋅ 4 Baths ⋅ 24043403 MLS
Price Adjustment! Providing wonderful countryside views, this graceful & charming Cape Cod style house has privacy & seclusion, yet it's close to the town center. The Great Room has a vaulted ceiling & a beautiful wood-burning fireplace, an abundance of windows & French doors leading to an expanded deck to take in the views. The remodeled, light-filled, gourmet kitchen includes 2 Sub-Zero freezer drawers, a Viking fridge, gas stove & breakfast bar. A 2nd fireplace is in the Family Room which has a wet bar with ice maker. The 1st floor Primary Suite addition has a private balcony, huge walk-in closet with built-ins, a Loft & a Sitting Room. A full spa-like Bath with separate soaking tub, walk-in tile shower, double sinks & a Toto toilet completes the Primary Suite. Included on the main floor is a large walk-in pantry & 2 half-baths, one with laundry area. Wide-board hardwood floors throughout. The upstairs has 2 Bedrooms (one is being used as an art studio), an Office Nook & a full Bath. A walkout lower level has a Rec Room with fireplace, 3-car garage & utility area. The property includes a 3-story Barn with the main level being used as a workshop & the upper level, with separate entrance, is an efficiency apartment adding another full bath & bedroom to the property & is perfect for guests. The compact Kitchen includes stainless refrigerator, stove & dishwasher. This unique property, located on one of Roxbury's well-maintained unpaved roads, is waiting for you to enjo

Roxbury
$1,465,000
3 Beds ⋅ 3 Baths ⋅ 24108014 MLS
Welcome to this enchanting Roxbury home that feels like a private oasis. This stunning property sits on over 7 acres and features a heated saltwater pool, a chef's kitchen with an open concept that overlooks the great room with vault ceilings, and radiant heated floors that leads to the patio, gardens, and pool. A custom built heated 2 story post and beam barn that offers a 3-car garage was built in 2008 and also has a car lift that will be staying with the property. The wood beams throughout the home adds an extra touch of charm as you walk through. The primary bedroom features beautiful views and includes master en-suite with soaking tub. Two additional generously sized bedrooms are on the upper floor. Whether you're looking to enjoying long weekends away from the city or looking to make this a home year-round the tranquil feeling will make the world fade away.

19 Good Hill Ter, Roxbury
$1,450,000
4 Beds ⋅ 3 Baths ⋅ 170569984 MLS
Discover the Allure of this Private Modern, Nestled on 41+ Acres, Accessible by a Long Driveway. This Impeccably Designed Residence is Currently Owned by the Renowned Swedish Designer, Lars Bolander. Step Outside to the Heated Gunite Pool, Surrounded by Large Stone Terrace. A Small Pond Adds a Touch of Natural Beauty to the Expansive Grounds. The Heart of the Home is a Welcoming Country Kitchen with a Fireplace & Seating Area, Where Culinary Delights Unfold. There is a Graciously Proportioned Living Room with Fireplace & Vaulted Ceiling. A Main Level Primary Bedroom Suite is Tucked Quietly Away from Public Spaces. The wonderful Library Provides a Perfect Retreat for Literary Enthusiasts, While the Formal Dining Room Sets the Stage for Elegant Dinners. Equestrian Enthusiasts will Appreciate the 3-Stall Horse Barn, Leading to a Fenced Paddock. Practical Features Include Central AC & a 3-car Garage with Spacious Storage area. An Excellent Value.

67 Botsford Hill Rd, Roxbury
$1,425,000
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
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
$1,400,000
4 Beds ⋅ 3 Baths ⋅ 24036142 MLS
Privately sited with western views and sunset! Now with 4 bedrooms in the main house and a 1500 ft Guest house with two bedrooms and 2 baths. A long driveway winds you into this idyllic retreat with western views and sunsets, nestled minutes from town. This stunning Cape Cod Farmhouse thoughtfully constructed has been expanded to include two additional bedrooms in the Main House. An additional 780 ft of Lower Level walk out unfinished space boasting high ceilings is ready to finish as well. It is a harmonious blend of modern comfort and classic charm. The open floor plan invites effortless flow, while French doors beckon you to the expansive deck where western sunsets paint the sky. Inside, discover the allure of a gourmet kitchen with central island, perfect for culinary adventures and casual gatherings. Beyond the main house, a charming 1500 two-bedroom guest house adds versatility and privacy. The oversized two-car garage completes this exceptional property, providing ample space for your vehicles and storage. Enjoy open-concept living that seamlessly flows to a grand deck, where you can unwind while taking in breathtaking western sunsets over the neighboring horse pasture!

21 Hemlock Rd, Roxbury
$1,400,000
2 Beds ⋅ 3 Baths ⋅ 24099959 MLS
Exquisite Barn House with Heated Pool. Set Along a Very Low Traveled Unpaved Town Road, This is a Very Chic & Sophisticated Retreat. Wonderful Public Rooms Include: Large Living Room with Vaulted Ceiling, Fireplace & Antique Beams; A Library which Envelopes you with an Antique Board Ceiling, Fireplace & French Doors; Formal Dining Room & A Timeless Eat-in Kitchen which Speaks to Family Room that Has a Fireplace & French Doors. A Primary Bedroom Contains a Sitting Area, Full Bath & Deck Overlooking Manicured Grounds. A Second Bedroom Suite Completes the Offering.

88 Hemlock Rd, Roxbury
$1,400,000
4 Beds ⋅ 6 Baths ⋅ 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
$1,400,000
4 Beds ⋅ 3 Baths ⋅ 170565855 MLS
Sunny, spacious 4-bedroom contemporary colonial estate on 10 private acres with long driveway near the village of Roxbury. Bright airy rooms with open floor plan. Dramatic double-story Great Room with wood burning fireplace and French doors to a flagstone patio with pergola. Eat-in cook’s Kitchen with French doors to stone patio. Family Room with built-in bookshelves & French doors to private stone patio. Luxurious Primary Suite. Also, upstairs a private Sitting Room/bedroom shares a jack-and-jill bath with a stylish bedroom. Additional first floor ensuite bedroom. Separate 3-car garage with unfinished space above. Inground swimming pool with cabana. Elegant professional landscaping.

60 Good Hill Rd, Roxbury
$1,378,000
4 Beds ⋅ 4 Baths ⋅ 24087170 MLS
Radiant in Roxbury: A Beautifully Renovated Country Cape Nestled in one of Southern Litchfield County's most sought-after towns, this light-filled home offers an inviting blend of modern amenities and country charm. Two primary suites (one on the main level and one upstairs), two additional bedrooms, home office/guest room, and two full baths on each floor. There's So Much To Love... open kitchen with quartz countertops & bar seating, lots of counter space, induction oven, and beautiful sunrise views. Sprawling main floor primary suite features a luxurious spa-like bathroom with heated floors, soaring double-height ceiling, mezzanine-level library/office/sitting area, and custom his-and-hers closets. Two more generous bedrooms upstairs, two full baths (one en suite), ample closet and storage space including walk-in unfinished attic access. Great floor plan: Open-concept living and dining areas are perfect for entertaining, a sunny four-season sunroom, and an additional downstairs home office (or 5th bedroom). Your backyard retreat awaits, with rectangular gunite pool and beautiful rolling lawns. Enjoy lunch on the rear deck shaded by an electric awning, or head to nearby hiking trails across 3,600 acres of conservation land. All this and a new whole-house generator, attached two-car garage, and massive basement. Proximity to shopping in Woodbury and Brookfield, and less than two hours from NYC, making this an ideal weekend home or full time home base. Low taxes, abunda

22 Highmeadow Ln, Roxbury
$1,350,000
4 Beds ⋅ 3 Baths ⋅ 170625554 MLS
Mint condition and light filled, this open concept Cape Cod with oversized windows and wraparound porch is set in a magical location with nearby Roxbury Land Trust and Battle Swamp Preserve hiking trails. This stunning 4 bedroom home offers the best in privacy and quiet with a bluestone terrace for great entertaining, professionally designed perennial gardens, fenced raised vegetable gardens, firepit, garden shed, pergola fenced backyard entry and a long estate level pea stone driveway. A new 14 x 22 post and beam studio or workshop has been added for hobby or perhaps party space. The first floor open concept plan offers living room with fireplace, a large dining room with high ceilings which reaches into the kitchen/family room with vaulted beamed ceiling and then leads out to the back terrace. The second floor is complete with primary suite, bath with large clawfoot tub, step in shower, double pedestal sinks, two walk in closets and large picture windows to overlook the sumptuous grounds, along with three additional bedrooms and a full bath. Take a hike into nearby Roxbury Land Trust, or Battle Swamp Preserve and continue on to Steep rock preserve. It is the perfect weekend or full time home with its' great comfortable flow and soothing feel. Additionally, the grounds are complete with a small pond water garden, towering pines, garden shed with pergola entry, and fruit trees. Just five minutes from both Roxbury and Washington Center!

7 Wakelee Rd, Roxbury
$1,325,000
4 Beds ⋅ 4 Baths ⋅ 24035471 MLS
Welcome to this inviting must see country contemporary Tudor style home on beautiful 3.5 acre corner lot in Roxbury. This is country living at its best, as your full time home or weekend escape for every season. Professional landscaped grounds surround this impressive home which is truly a highlight of North Street. The gracious entry foyer gives you an immediate sense of the best of everything throughout. A beautiful dining room w/hardwood floors welcomes you. To the right, a step down sunlit room serves as a den, flex space, or music room. For the chef there is a custom kitchen w/beautiful cabinetry and radiant floor. The massive sunlit living room w/8 windows & wood burning fireplace are indeed highlights of the first floor. Coffered ceilings & hardwood floors make this room truly special. A unique round library w/15 ft ceilings & custom bookcases is something unique to this property. A custom designed staircase leads up to the large bedrooms. A primary bedroom suite offers a renovated bath & custom closet and storage room. French doors lead to a large fenced in swimming pool & expansive grounds are appointed w/exquisite specimens trees. A stone wall surrounds most of the property. There is a ground floor apt w/its own separate bathroom & entrance. This must see home has been well cared for by two designers who have made it a showplace you will want to visit. Great proximity to Washington, Woodbury & New Milford for shopping & dining options. Some light fixtures

235 North St, Roxbury
$1,300,000
4 Beds ⋅ 3 Baths ⋅ 24017145 MLS
Revolutionary war General, Ephraim Hinman, built this lovely house in 1784. Listed on the NR of Historic Places, this two-story home, 3,666 square foot home with 9-foot ceilings throughout, three bedrooms, two full baths and one-half bath. There is a library with built-ins, living and dining rooms, sitting area, sunroom, study (or 4th bedroom) and all contain original or restored (1930s) dentil & moldings. There are four working fireplaces, and the center hall is covered in early 20th century hand-painted chinoiserie wallpaper. The kitchen is vast, with a custom soapstone sink, Liebherr refrigerator, and a CornuFe stove, and includes a light-filled sitting area & mudroom. Recent improvements include restored scullery kitchen with under-floor radiant heat, cedar shake roof w/40 yr. warranty, new furnace, water filtration and softener system, French drains outside house perimeter and in basement, and a (local) granite patio. The exterior has recently been painted. The garage has room for two cars and more, with loft space. The yard has dry stone walls, wildflowers, a meadow, a large, fenced vegetable garden area, and a bocci court, which is surrounded by heirloom apple trees. Mature plantings and trees provide the necessary shade and greenery for keeping the house cool all summer. Litchfield County has an abundance of outdoor activities, lovely boutiques, antique shops, and dine in farm to table restaurants. Welcome to Litchfield Hills!

1 Church St, Roxbury
$1,300,000
3 Beds ⋅ 4 Baths ⋅ 24025151 MLS
Welcome to the epitome of modern elegance in this pristine contemporary retreat, set on 6 lush, landscaped acres, complete with a charming guest house. Nestled in the heart of an idyllic country retreat, this property represents a unique blend of luxury and tranquility. The 2024 renovation, masterfully executed by the acclaimed European firm Voce Di Design Studio, has elevated both the main house and the guest house to new heights of sophistication.Designed for modern living, the open floor plan creates a seamless flow between spaces. The main house features a first-floor Primary Suite with a luxurious spa-like en-suite bathroom.The sunken living room, featuring a cozy fireplace, is perfect for intimate gatherings.A visually captivating spiral staircase leads to two exquisite bedrooms.A chef's dream, the gourmet kitchen is equipped with top-of-the-line appliances, coffee/ bar station and elegant finishes. Floor-to-ceiling windows and sliding doors frame spectacular views of the verdant surroundings, enhancing the indoor-outdoor living experience.The outdoor space features three expansive decks, seamlessly connecting different parts of the home for easy access and effortless entertaining.

294 North St, Roxbury
$1,300,000
4 Beds ⋅ 5 Baths ⋅ 170574896 MLS
This newly-built 3600 SF Connecticut farmhouse is ready for move in. With the character of an old house but with all the modern efficiencies and open layout of new construction, this house is built to make life in the country as enjoyable and low-maintenance as possible. Traditional-style design elements such as built-in cabinetry, wainscoting, paneling, exposed wood beams, hand-built closets, and a custom kitchen make this house feel as though it belongs to a different era. The setting on a level 3-acre lot is wooded on the perimeter with the area surrounding the house cleared to allow sun to pour through the many windows. Stone walls line a bluestone patio accessible from the kitchen. A second patio area is accessible from the partially finished basement. The back yard is nearly level and has an approved pool site. The first floor with 10-foot ceilings and exposed beams includes a large mudroom, custom kitchen, an eating area with many windows, a family room with wood burning brick fireplace, a home office, and half-bath. The second floor with 9-foot ceilings has 4 bedrooms, 3 full baths, a loft with built in desk ,and a laundry room. The partially finished basement, with added ceiling height and large expanses of glass, has the same finishes as the upper floors, making it a true extension of the main house. This space includes a great room and a half bath. This house comes with a 1-year builder's warranty.

92 Hemlock Rd, Roxbury
$1,275,000
4 Beds ⋅ 3 Baths ⋅ 24029734 MLS
Welcome to Hollywood Hills meets Roxbury! This exceptional 4-bedroom, 3-bath home sits on 2.1 acres and features a vast studio perfect for artists, Pilates, yoga, or entertaining! The light-filled home boasts a gourmet eat-in kitchen with custom cabinetry, imported Spanish floor tiles, and top-of-the-line appliances, including a Subzero refrigerator, Wolf range/grill, Wolf wall oven, and Bosch dishwasher. French doors open to a sprawling deck offering breathtaking views. The living room features two sets of French doors leading to the deck, a fireplace designed by Connecticut artist, Elizabeth McDonald, and custom bookcases. The main level includes a primary bedroom with an ensuite bath featuring a soaking tub, a second bedroom, an office, and a guest bath. The lower level offers two more bedrooms, a windowed bath with a rain shower, a sauna, a laundry room, and a large rec room with easy access to a gunite infinity pool and beautifully landscaped gardens featuring local fieldstone and quarry-mined slabs comingled with perennials. Additional highlights include a detached 2-car garage, new HVAC installed in 2020, a Generac generator, laundry shoot and a DuraSlate roof. Located in the center of Roxbury, walking distance to the Roxbury Market, bank, post office, tennis courts, library, hiking trails and town park. This home seamlessly blends modern amenities with classic charm, offering both privacy and convenience.

36 Chalybes Rd, Roxbury
$1,250,000
4 Beds ⋅ 3 Baths ⋅ 170625630 MLS
Wonderful opportunity to own a 4-bedroom main house plus a 1-bedroom guest barn in the rural historic New England town of Roxbury, CT, which is known for its long-time connection to many notable artists, writers and celebrities seeking privacy and quiet. Located on 5 peaceful acres on one of the most coveted and idyllic country roads amidst farms, nature preserves and large estates, this property has pastoral views, beautiful mature plantings, ancient trees and stonewalls. The main house is bright and airy with a large eat-in country kitchen, formal dining room, spacious living room with a wood-burning fireplace, sunroom, cozy paneled den and a family room/studio with vaulted ceiling, beams and full bath over the 2-car attached garage. Upstairs, the en suite primary bedroom has a walk-in closet and three other bedrooms share a hall bath. Great opportunity in top location. Only 65 miles to NYC.

214 Tophet Rd, Roxbury
$1,250,000
4 Beds ⋅ 4 Baths ⋅ 170591518 MLS
This antique reproduction embraces the cherished and charming ideals of cozy country home. Most will enter through the mud room with abundant storage and head into the kitchen with built-ins, office nook, central island and a breakfast table which fronts a fireplace. The living room with an addl fireplace opens to a comfy media nook with built-ins and lounging sofa. There is also a formal dining room which opens to the kitchen and the front foyer. Upstairs, there are 3 bedrooms with 2 baths. The lower levels hosts a full suite with bedroom, sitting area, full bath, the 4th fireplace, and walks out to the bluestone terrace. This lower level is perfect for an in law suite, 4th guest room, and/or studio/playroom. Gorgeous hardwood floors throughout, exposed hand hewn beams, paneled walls, cedar shingle roof. Stone patios overlook a babbling brook and fern covered woodlands. Mature trees and shrubs afford wonderful privacy. The stone walls seems to go on for miles. Truly a magical property. Furniture avail separately.

310 North St, Roxbury
$1,240,000
4 Beds ⋅ 4 Baths ⋅ 170582275 MLS
This house has been thoroughly renovated from top to bottom and is now equivalent to a new house. New siding, roof, windows, kitchen, baths and flooring. The layout has been opened to feature a great room expanse centered around a fireplace with custom fitted screen. The sitting area walks out to the spacious back yard (which is fenced) and the inground Gunite pool. The primary bedroom suite is on the main level and boasts a vaulted ceiling, loft area, large bath and closets. The main level also features a formal living room, a sun room, and a potential 5th bedroom (with full bath). Upstairs is the original primary bedroom (before the main floor suite was added) along with 2 additional bedrooms, all have spacious closets. The lower level is unfinished, but it is large and has high enough ceilings to create more living space (play room/media room?) It also houses the 2 car garage and has plenty of storage/workshop space. All of the mechanicals are also new. Take advantage of top rated school system with easy proximity to Washington, Southbury, Woodbury and New Milford.

22 Highmeadow Ln, Roxbury
$1,240,000
2 Beds ⋅ 3 Baths ⋅ 170610995 MLS
Magically enchanting, nestled, literally, into a private Roxbury hillside, this unique "bermed earth shelter home" of stone, stucco and slate overlooks nearly 8 acres of professionally landscaped grounds, a gunite pool, stone patios, seasonal views and an active year round stream. The approach over the bridge, along a gentle sloping winding driveway opens to a lush, intimate setting of mature grounds graced with an extraordinary, architectural creation that blends the building into the landscape more harmoniously than a conventional home, with the earth providing soundproofing. The architect, Louis O. Roberts, designed a structure less susceptible to the impact of extreme outdoor air temperatures with energy efficient passive solar. Earth-sheltered houses also require less outside maintenance. Additional features include a newer septic system, central air and two stone fireplaces, a lower level, walkout studio space with conversion opportunities for more bedrooms and a bath. This is a rare opportunity to own a property of special provenance in a highly coveted estate area of Roxbury. The price reflects need for skylight replacement.

76 Davenport Rd, Roxbury
$1,225,000
4 Beds ⋅ 3 Baths ⋅ 24015875 MLS
In the late 18th century Phineas Smith built the house and office where he laid out plans for the Oxford Turnpike now Southbury Road. This finely preserved home has four working fireplaces and beautiful historic details. Barn has been sensitively converted into modern studio and is currently a successful Architecture office and Antique Shop. Barn/office/studio is 3436 s.f. with heat and a/c, has 2 half baths and Pantry. Both house and barn with featured in Architectural Digest. Super visibility combined with exquisite grounds and lovely pond. Live the genteel country life and stroll to your office, surrounded by nature. Enjoy the benefits of easy living, ideal location - an exquisite property at the crossroads- convenient to all points in the heart of Roxbury! Litchfield County has a bounty of wonderful outdoor activities including hiking trails, boating, fishing, swimming, wineries, and skiing. A natural food market is less than 15 minutes away and many local farm markets and farm stands. Relax and enjoy the lovely boutiques, antique shops, and dine in farm to table restaurants. Welcome to Litchfield Hills!

3 Southbury Rd, Roxbury
$1,200,000
3 Beds ⋅ 3 Baths ⋅ 24095086 MLS
Fantastic Colonial in Roxbury down long private drive featuring low maintenance salt water spa pooL. The house is surrounded by nature, with multiple entertaining spaces and gardens. Amazing bird life is a natural symphony while relaxing outdoors. The home has a lovely gracious layout all with detailed millwork and a vaulted great room with almost floor to ceiling windows on three sides creating a conservatory feel. A scented rose garden courtyard is off the great room. It flows directly off the kitchen which has a lovely breakfast area. The adjoining room is currently being used as a billiard room but could be a den, playroom or used in many different ways. Formal dining room and sitting room/library with gas fireplace are off the front hall. Second floor has 3 bedrooms including a primary suite with oversized marble bathroom, balcony deck (great for star gazing) and dressing room. There is a hall bath, laundry and bonus room currently being used as a gym. This room could be a 4th bedroom with the possibility of an en-suite bathroom. The attached 2 and half car garage leads to a newly renovated mudroom area. The lower level is partially finished and has additional potential. Pool with spa and cabana is surrounded by granite patio and coping, evergreens, shrubs, perennials and roses that provide summer long color and fragrance. Recent upgrades include automatic generator. Don't miss this opportunity!

53 Transylvania Rd, Roxbury
$1,200,000
3 Beds ⋅ 3 Baths ⋅ 24019637 MLS
One of Roxbury's finest saltbox replica. Built in 1981 with great care, quality and attention to detail. This property is pristine, bursting with charm and move-in ready. The house is set back on a 5.12 acres level lot with stones walls, boxwoods and espaliers. It is professionally landscaped with apple trees and a spring pond. Downstairs boasts an open kitchen enhanced with a wood stove and sliding doors giving access to the stone terrace. The adjacent family room feel cozy with its wooden beams and fireplace, another fireplace warms the living room. The formal dining room and powder room round out the downstairs. Front and back staircases give access to the second floor. There are 3 bedrooms and 2 baths with beautiful views. In addition a large, sunny bonus room which can be an office/gym is also on the second floor. Attached 2-car garage, a generator and a walk out basement. The attic is finished with a cedar closet. The property offers privacy, comfort and charm. It is a must see!

219 Good Hill Rd, Roxbury
$1,195,000
3 Beds ⋅ 3 Baths ⋅ 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
$1,150,000
3 Beds ⋅ 3 Baths ⋅ 170617668 MLS
This Roxbury, CT property epitomizes a distinctive and adaptable living space, catering to diverse needs such as multi-generational living, guest hosting, income generation, or serving as an Air B&B. Nestled in Litchfield County, CT, within the Town of Roxbury, the 4.6-acre property exudes a secluded, park-like ambiance and comprises two distinct dwellings on a unified deeded property: the main residence and a carriage house with a private office. The main residence boasts over 3,000 sq ft of living space, featuring 3 bedrooms, 3 full baths, 2 primary suites, one of which spans over 600 sq ft on a dedicated level, and an array of modern amenities including a newly installed kitchen in 2021. The carriage house, set in a wooded environment, offers over 1,000 sq ft of open floor plan living, complete with a fully equipped kitchen, dining and living areas, 2 bedrooms, full bath and a private deck. A private executive office adds a unique touch, providing nearly 400 sq ft of workspace with a half bath, autonomous utilities and private access. With additional features like central air, automatic generators, immediate occupancy, and the potential for a pool and tennis court, this property excels in accommodating various living arrangements while ensuring privacy and charm.

277-279 Southbury Rd, Roxbury
$1,150,000
3 Beds ⋅ 3 Baths ⋅ 170604450 MLS
Journey down a quiet country road to a private all inclusive retreat. Charming main house features sunroom with vaulted ceilings, beams and French doors to screened porch, terrace, deck and pond. Main floor has wood floors, beams, fireplaces in dining room and living room. Relax in cozy reading nook with bookshelves. Upstairs to primary bedroom suite with fireplace. 2 more bedrooms that share a full bath. Finished 3rd floor has potential as overflow guest space, office, gym with plenty of storage space. Newly finished studio apartment over spacious 3 car garage. Deck looks over Scott gunite pool. Tennis court needs rehab. Mechanicals and systems, pool and septic are serviced and up to date. Property is surrounded by woodlands, professional landscaping on 18.5+/- acres. Conveniently located close to Roxbury's gourmet market and amenities of Woodbury and Washington Depot.

25 Holmes Rd, Roxbury

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