Roxbury, CT Homes

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  /40

  $1,735,000

  • 4 Beds
  • 2.5 Baths
  • 6,395 Sq Ft

  99 Carriage Ln, Roxbury, CT 06783

  Welcome to this beautifully maintained 4-bedroom, 2.5-bath home, nestled in a serene and peaceful location-perfect for those seeking comfort and tranquility. Step inside to a spacious open-concept living and dining area, ideal for hosting gatherings and entertaining with ease. The modern kitchen features state-of-the-art appliances, ample counter space, and generous storage-making it a dream for

  Debra Tricarico Houlihan Lawrence

  99 Carriage Ln, Roxbury, CT 06783
• 

  

  

  /14

  $2,500 per month

  • 1 Bed
  • 1 Bath
  • 875 Sq Ft
  • Apartment for Rent

  160 North St, Roxbury, CT 06783

  FURNISHED RENTAL AVAILABLE SEPT 2, 2025- MAY 2026 @ $2,500/MONTH. Spacious one bedroom apartment above garage on large, private estate. Clean, updated and comfortable. Bright living room with built ins and mini bar. Dining room and kitchen. Stackable washer/dryer in unit. Excellent credit, references and application required. Electricity included. Oil heat paid for by tenant.

  

  Rebecca Doh

  W. Raveis Lifestyles Realty

  (860) 750-8200

  160 North St, Roxbury, CT 06783
• 

  

  

  /38

  $1,695,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 3,302 Sq Ft

  78 Garnet Rd, Roxbury, CT 06783

  A split rail fence along the meandering drive leads you to this beautiful and sophisticated farmhouse on 15.29 acres of peaceful countryside. Storybook wrap-around porch, new Gunite heated saltwater pool, separate guest apartment, enormous barn, apple trees, perennial gardens and pond are highlights. The pristine house has recessed wood paneling and floors, window seats, built-ins and crown

  Maria Taylor Klemm Real Estate Inc

  78 Garnet Rd, Roxbury, CT 06783
• 

  Not Listed For Sale

  00 Phaeton Dr, Roxbury, CT 06783

  00 Phaeton Dr, Roxbury, CT 06783
• 

  

  

  /33

  $1,680,000

  • 3 Beds
  • 2.5 Baths
  • 2,440 Sq Ft

  85 Good Hill Rd, Roxbury, CT 06783

  At the end of a long, winding private driveway, this exceptional Roxbury estate offers total seclusion & tranquility-surrounded entirely by protected land trust. Just 2 miles from Roxbury Center and a scenic 2-hr drive from NYC, this rare property is the perfect country escape or full-time residence. The main home is in impeccable, move-in condition, featuring dramatic vaulted ceilings in both

  Pat Lahoud William Pitt Sotheby's Int'l

  85 Good Hill Rd, Roxbury, CT 06783
• 

  

  /31

  $25,000 per month

  • 3 Beds
  • 3.5 Baths
  • 2,762 Sq Ft
  • House for Rent

  24 Old Roxbury Rd, Roxbury, CT 06783

  Available SUMMER 2026 at 75,000 total. Also, school year 2025/2026 at $15,000/mo. Perched high on a scenic Roxbury hillside, this brand 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

  Stacey Matthews W. Raveis Lifestyles Realty

  24 Old Roxbury Rd, Roxbury, CT 06783
• 

  $1,378,000 Sold Jul 08, 2025

  • 3,481 Sq Ft
  • $396/SF
  • 44 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1985

  22 Highmeadow Ln, Roxbury, CT 06783

  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

  William Bolls Compass Connecticut, LLC

  22 Highmeadow Ln, Roxbury, CT 06783
• 

  Est $1,338,000 Not Listed For Sale

  • 3 Beds

  18 Brandy Wine Crossing, Roxbury, CT 06783

  18 Brandy Wine Crossing, Roxbury, CT 06783
• 

  

  /35

  $2,195,000

  • 5 Beds
  • 6 Baths
  • 5,113 Sq Ft

  88 Rucum Rd, Roxbury, CT 06783

  Located in picturesque Roxbury, CT-nestled in southern Litchfield County and under two hours from New York City-this exquisite barn-style residence offers the perfect blend of rustic charm and modern luxury. Set on 8 sprawling acres, the property features an expansive lawn, beautifully curated specimen plantings, and a sparkling pool with integrated spa-ideal for both relaxation and entertaining.

  Pels Matthews W. Raveis Lifestyles Realty

  88 Rucum Rd, Roxbury, CT 06783
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  /37

  $6,500 per month

  • 4 Beds
  • 4 Baths
  • 4,000 Sq Ft
  • House for Rent

  28 Old Ln, Roxbury, CT 06783

  Tucked into the hills of Roxbury, this 4,000 sq ft Mid-Century Modern home is a private architectural retreat surrounded by wildflower clearings, forest, and dramatic granite outcroppings. The property exudes rustic country charm, favoring natural beauty over manicured formality. Inside, cathedral ceilings with numerous skylights create an airy, light-filled space that blurs the line between

  Robert Barker Houlihan Lawrence WD

  28 Old Ln, Roxbury, CT 06783
• 

  $615,000 Sold Jun 30, 2025

  • 2,769 Sq Ft
  • $222/SF
  • 12 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1957

  79 Wellers Bridge Rd, Roxbury, CT 06783

  Welcome to this beautifully updated 3 bed, 2 full bath ranch home nestled on 5.9 peaceful acres in the charming and bucolic Roxbury, CT. This light filled home offers the perfect blend of modern updates and classic comfort in a peaceful country setting.The completely updated kitchen features stainless steel appliances, granite countertops and lovely cabinetry. The spacious living room is warm and

  Amy Jeanfaivre Family Realty Group, LLC

  79 Wellers Bridge Rd, Roxbury, CT 06783
• 

  Est $444,735 Not Listed For Sale

  • 1 Bed
  • 1.5 Baths
  • 832 Sq Ft

  87 Rucum Rd, Roxbury, CT 06783

  87 Rucum Rd, Roxbury, CT 06783
• 

  

  /40

  $2,395,000

  • 4 Beds
  • 5.5 Baths
  • 5,848 Sq Ft

  143 Tophet Rd, Roxbury, CT 06783

  Located along one of Roxbury's most coveted stretches, this property is nestled among an 800+ acre greenbelt of farmland and conserved land with plentiful hiking trails. The open floor plan is designed with 9 foot+ ceilings, detailed millwork and oversized windows which infuse the interiors with natural light. The main level features a show stopping kitchen open to the dinning and media rooms.

  Stacey Matthews W. Raveis Lifestyles Realty

  143 Tophet Rd, Roxbury, CT 06783
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  /28

  $20,000 per month

  • 4 Beds
  • 2.5 Baths
  • 3,089 Sq Ft
  • House for Rent

  5 North St, Roxbury, CT 06783

  Summer 2025: August at $20,000 per month. Inquire for alternate dates. Quintessential Litchfield County Retreat with Fabulous Gunite Pool in the Heart of the Town of Roxbury on 4 +/- pastoral acres. 4 bedroom and 2 and 1/2 bath charming Colonial with Great Room/Family Room with vaulted ceilings, Eat-in Country Kitchen, Formal Living Room with wood-burning fireplace, Formal Dining Room and a

  Melinda Dubow Klemm Real Estate Inc

  5 North St, Roxbury, CT 06783
• 

  $1,325,000 Sold Jun 18, 2025

  • 3,379 Sq Ft
  • $392/SF
  • 295 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1980

  235 North St, Roxbury, CT 06783

  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

  Pels Matthews W. Raveis Lifestyles Realty

  235 North St, Roxbury, CT 06783
• 

  Est $165,047 Not Listed For Sale

  • 5 Beds

  268 Southbury Rd, Roxbury, CT 06783

  268 Southbury Rd, Roxbury, CT 06783
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  /29

  $1,995,000

  • 4 Beds
  • 2.5 Baths
  • 4,800 Sq Ft

  67 Botsford Hill Rd, Roxbury, CT 06783

  Discover the appeal of this Swedish inspired shingle-style beauty with light and modern finishes throughout. It's nestled into 41+ ultra-private acres on a picturesque country road. Enter the front door into the two-story foyer which flows into the vaulted ceiling living room with lots of glass, adobe fireplace and easy access to the tucked away library with floor to ceiling bookshelves. The

  Maria Taylor Klemm Real Estate Inc

  67 Botsford Hill Rd, Roxbury, CT 06783
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  /25

  $7,000 per month

  • 3 Beds
  • 3.5 Baths
  • 3,236 Sq Ft
  • House for Rent

  116 Wellers Bridge Rd, Roxbury, CT 06783

  Mid-Century single-level in a convenient Roxbury location. Cool mad-men vibe with floor to ceiling windows, exposed beams, vaulted ceilings, stone and wood floors, and wood paneling. Throughout the house the many windows pour natural light in and give fabulous views over the private and manicured grounds. The home has multiple versatile rooms giving a choice of layout to fit your needs. The

  Claudine McHugh Klemm Real Estate Inc

  116 Wellers Bridge Rd, Roxbury, CT 06783
• 

  $1,875,000 Sold Jun 04, 2025

  • 3,086 Sq Ft
  • $608/SF
  • 75 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1989

  257 Southbury Rd, Roxbury, CT 06783

  Wonderfully private and updated Roxbury compound with a three bedroom, three bath Mediterranean mid-century vibe main house offering the convenience of one level living. Secluded and dramatic 10 acre property with park-like grounds that flow from the primary residence and gardens down to the saltwater pool with expansive stone terrace and newly renovated guest house. Generously sized, the guest

  Maria Taylor Klemm Real Estate Inc

  257 Southbury Rd, Roxbury, CT 06783
• 

  Est $622,145 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,696 Sq Ft

  29 Apple Ridge, Roxbury, CT 06783

  29 Apple Ridge, Roxbury, CT 06783
• 

  

  /22

  $1,995,000

  • 4 Beds
  • 3.5 Baths
  • 4,517 Sq Ft

  45 Moosehorn Rd, Roxbury, CT 06783

  Pristine 4+ bedroom large (4,517 sq. ft.) private home on a scenic dirt road - perfect for walking, jogging and biking surrounded by Moosehorn Land Preserve and country estates. Magnificent design incorporating picturesque country views, over-sized living room, dining room for 12+, chef's kitchen, vaulted ceilings, hardwood floors and two gas fireplaces. Heated pool surrounded by endless summer

  Peter Klemm Klemm Real Estate Inc

  45 Moosehorn Rd, Roxbury, CT 06783
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  /27

  $15,000 per month

  • 4 Beds
  • 6 Baths
  • 3,996 Sq Ft
  • House for Rent

  34 Old Roxbury Rd, Roxbury, CT 06783

  Available for $15,000/mo for 2025/26 school year and $75,000 for Summer 2026. Enjoy Modern Luxury in Connecticut's Countryside. The meticulously renovated 4-bedroom residence seamlessly blends the original mid century architecture with contemporary sophistication. Enter on the main level with 2 bedrooms and 2 full baths, sauna, foyer, powder room and media room with large screen tv and bar.

  Stacey Matthews W. Raveis Lifestyles Realty

  34 Old Roxbury Rd, Roxbury, CT 06783
• 

  $1,490,000 Sold May 22, 2025

  • 3,337 Sq Ft
  • $447/SF
  • 204 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 1998

  Unlisted Address

  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

  Donna J. Matula William Raveis Real Estate

  Unlisted Address
• 

  Est $1,333,989 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,360 Sq Ft

  310 North St, Roxbury, CT 06783

  310 North St, Roxbury, CT 06783
• 

  

  /21

  $1,649,000

  • 3 Beds
  • 4 Baths
  • 2,396 Sq Ft

  247 Painter Hill Rd, Roxbury, CT 06783

  Pristine St. Barth-Style bungalow with two-car garage. Single-level living surrounded by Roxbury's best historic estate neighborhood, farms and homes of artists, actors and writers. Magnificent open floor plan with 2-3 bedrooms on main floor, 2 fireplaces, new eat-in kitchen, vaulted living room, den and screened porch and another bedroom in finished lower level. Dine or relax on the flagstone

  Peter Klemm Klemm Real Estate Inc

  247 Painter Hill Rd, Roxbury, CT 06783
• 

  

  /22

  $4,000 per month

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft
  • House for Rent

  10 Sentry Hill Rd, Roxbury, CT 06783

  Upper three-bedroom, 2 bath now available from September 30, 2025. Featured in CTC & G January 2024 Issue! Striking Modern Renovation of Artist's home in private, much sought after location in the rural Litchfield Hills. On a quiet country road, surrounded by woodlands, this 3-bedroom, 2 bath home rests on five acres with a gentle stream running through it. State of the art chef's kitchen with

  Melinda Dubow Klemm Real Estate Inc

  10 Sentry Hill Rd, Roxbury, CT 06783
• 

  $749,900 Sold May 19, 2025

  • 2,265 Sq Ft
  • $331/SF
  • 74 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2006

  8 Old Ln, Roxbury, CT 06783

  Welcome to your dream home! This charming Roxbury Colonial offers the perfect blend of comfort, space, and endless possibilities for your lifestyle. Whether you're relaxing on the inviting front porch or hosting friends in one of the many entertaining areas, you'll find a warm and welcoming atmosphere throughout. The open floor plan creates an ideal space for family and friends to gather, with a

  Brandy Granata Coldwell Banker Realty

  8 Old Ln, Roxbury, CT 06783
• 

  Est $742,110 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,834 Sq Ft

  77 Squire Rd, Roxbury, CT 06783

  77 Squire Rd, Roxbury, CT 06783
• 

  

  /27

  $1,549,000

  • 4 Beds
  • 3.5 Baths
  • 2,716 Sq Ft

  33 Sentry Hill Rd, Roxbury, CT 06783

  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,

  Peter Klemm Klemm Real Estate Inc

  33 Sentry Hill Rd, Roxbury, CT 06783
• 

  

  /17

  $7,500 per month

  • 4 Beds
  • 2.5 Baths
  • 3,026 Sq Ft
  • House for Rent

  18 Bear Burrow Rd, Roxbury, CT 06783

  Charming barn-style home on 15.27 acres off quiet country road. Four bedrooms and two and one half baths. Open floor plan. Exposed timber. Double sided stone fireplace. French doors to rear patio. In ground pool and barrel sauna. The perfect summer retreat in the beautiful town of Roxbury. Available short term between September to May for $7,500 per month. Contact agent for availability. Just 90

  Maria Taylor Klemm Real Estate Inc

  18 Bear Burrow Rd, Roxbury, CT 06783
• 

  $795,000 Sold May 16, 2025

  • 2,931 Sq Ft
  • $271/SF
  • 322 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1998

  13 Evergreen Dr, Roxbury, CT 06783

  BEST Value with a Pool in Litchfield County! Stylish Private Modern with Infinity Edge Heated Pool. This Hip Modern Home Has an Open Floor-plan & Airy Feel. 3 Bedrooms, 3 Updated Baths. Inviting Eat-in Kitchen Speaks to Large Family Room with Fireplace & Vaulted Ceiling. Wonderful Formal Living Room with Modern Fireplace & Vaulted Ceiling. Generous Primary Bedroom Commands the Upper Level

  Graham Klemm Klemm Real Estate Inc

  13 Evergreen Dr, Roxbury, CT 06783
• 

  Est $1,700,471 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 4,693 Sq Ft

  49 Garnet Rd, Roxbury, CT 06783

  49 Garnet Rd, Roxbury, CT 06783
• 

  

  /33

  $1,649,000

  • 4 Beds
  • 3.5 Baths
  • 2,437 Sq Ft

  253 Tophet Rd, Roxbury, CT 06783

  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.

  Peter Klemm Klemm Real Estate Inc

  253 Tophet Rd, Roxbury, CT 06783
• 

  $940,000 Sold May 07, 2025

  • 3,088 Sq Ft
  • $304/SF
  • 195 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1999

  80 Transylvania Rd, Roxbury, CT 06783

  Modern Farmhouse Oasis on 4 Acres in Peaceful Roxbury. A winding drive leads you to the home, where elegant stone steps guide you to a covered porch, surrounded by a lush perennial garden. Inside, the sophisticated living room features French doors, grasscloth wall-covering, and crown molding. This seamlessly connects to a formal dining room with tray ceiling and a bay window. The heart of the

  Kathryn Bassett William Pitt Sotheby's Int'l

  80 Transylvania Rd, Roxbury, CT 06783
• 

  Est $2,213,759 Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 4,559 Sq Ft

  98 Bacon Rd, Roxbury, CT 06783

  98 Bacon Rd, Roxbury, CT 06783
• 

  

  /39

  $2,395,000

  • 4 Beds
  • 5 Baths
  • 4,728 Sq Ft

  32 Grassy Hill Rd, Roxbury, CT 06783

  Roxbury dream home with forever views. Tucked away down a gracious drive off a bucolic town road this quintessential Georgian welcomes you home and envelopes you in calm and comfort. Arrival at the motor court provides the first glimpse of a western view that stretches from Roxbury as far as the eye can see, giving an immediate sense of place. The home, unabashedly radiant in its sunny yellow

  Rick Distel Compass Connecticut, LLC

  32 Grassy Hill Rd, Roxbury, CT 06783
• 

  $2,858,000 Sold May 02, 2025

  • 3,043 Sq Ft
  • $939/SF
  • 15 Days On Market

  • 4 Beds
  • 5.5 Baths
  • Built 2018

  42 Berry Rd, Roxbury, CT 06783

  Impeccable 4 Bedroom, 5.5 Bath Colonial with Heated Pool. Set Privately Along Quaint Dead-End Town Rd. Jaw-Dropping Kitchen/Great Room with Vaulted Ceiling & Fireplace. Main Level Primary Suite with Luxurious Full Bath. Exquisite Living Room with Beamed Ceiling & Gas Fireplace. Heated Gunite Pool Steps from Finished Lower Level with Wet Bar, 2 Full Baths, Gym & Bedroom. 2 en-Suite Upper Bedrooms

  Graham Klemm Klemm Real Estate Inc

  42 Berry Rd, Roxbury, CT 06783
• 

  Est $570,865 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,551 Sq Ft

  121 Wellers Bridge Rd, Roxbury, CT 06783

  121 Wellers Bridge Rd, Roxbury, CT 06783
• 

  

  /26

  $1,784,000 New Construction

  • 5 Beds
  • 3.5 Baths
  • 3,220 Sq Ft

  2 Pickett Rd, Roxbury, CT 06783

  NEW CONSTRUCTION. WELCOME TO YOUR DREAM HOME! This stunning new construction colonial farmhouse boasts modern elegance and top-of-the-line finishes throughout. Featuring 5 spacious bedrooms and 3.5 luxurious bathrooms, this home offers ample space for comfortable living. The open concept living area is perfect for entertaining, with a gourmet kitchen that includes high-end stainless-steel

  Michael Lissack The Virtual Realty Group

  2 Pickett Rd, Roxbury, CT 06783
• 

  $645,000 Sold Apr 25, 2025

  • 2,382 Sq Ft
  • $271/SF
  • 62 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1943

  396 Southbury Rd, Roxbury, CT 06783

  Welcome home to 396 Southbury Rd in charming Roxbury CT in desirable Litchfield Hills. In off-winter months, one will adore the lush green landscaped grounds on these 4 tranquil acres. Nature's beauty at its best, lovely pond, a place of peace & solace, a treasure to call Home Sweet Home. Where rustic Country design meets distinctive Swiss Chalet styling - complete w/window flower boxes! This is

  Mirella D'Antonio William Raveis Real Estate

  396 Southbury Rd, Roxbury, CT 06783

Showing Results 1 - 40, Page 1 of 18