Roxbury, CT Homes

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  /27

  $1,750,000

  • 2 Beds
  • 2.5 Baths
  • 3,389 Sq Ft

  88 Hemlock Rd, Roxbury, CT 06783

  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

  Graham Klemm Klemm Real Estate Inc

  88 Hemlock Rd, Roxbury, CT 06783
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  /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
• 

  $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
• 

  Not Listed For Sale

  00 Phaeton Dr, Roxbury, CT 06783

  00 Phaeton Dr, Roxbury, CT 06783
• 

  

  

  /35

  $1,495,000

  • 3 Beds
  • 2.5 Baths
  • 3,920 Sq Ft

  53 Transylvania Rd, Roxbury, CT 06783

  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

  Pels Matthews W. Raveis Lifestyles Realty

  53 Transylvania 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
• 

  $1,490,000 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 $1,358,883 Not Listed For Sale

  • 3 Beds

  18 Brandy Wine Crossing, Roxbury, CT 06783

  18 Brandy Wine Crossing, 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
• 

  

  /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
• 

  $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 $116,608 Not Listed For Sale

  • 3 Beds

  177 E Flag Swamp Rd, Roxbury, CT 06783

  177 E Flag Swamp Rd, Roxbury, CT 06783
• 

  

  /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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  /27

  $15,000 per month

  • 3 Beds
  • 5 Baths
  • 3,888 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
• 

  $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 $504,284 Not Listed For Sale

  • 1 Bed
  • 1.5 Baths
  • 832 Sq Ft

  87 Rucum Rd, Roxbury, CT 06783

  87 Rucum Rd, 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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  /32

  $10,000 per month

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

  24 Old Roxbury Rd, Roxbury, CT 06783

  Available June and August 2025 at $25,000 ea. Also school year 2025/2026 at $10,000/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 inbedded screens. The two 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
• 

  $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 $162,398 Not Listed For Sale

  • 5 Beds

  268 Southbury Rd, Roxbury, CT 06783

  268 Southbury Rd, Roxbury, CT 06783
• 

  

  /21

  $1,675,000

  • 2 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, 2 fireplaces, new eat-in kitchen, vaulted living room, den and screened porch. Dine or relax on the flagstone terrace next to the heated gunite pool. Mature gardens with

  Peter Klemm Klemm Real Estate Inc

  247 Painter Hill Rd, Roxbury, CT 06783
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  /37

  $25,000 per month

  • 4 Beds
  • 3.5 Baths
  • 2,200 Sq Ft
  • House for Rent

  76 North St, Roxbury, CT 06783

  Available Month of August at $25k. Spend a perfect summer month in this Gorgeous Connecticut Antique "Edson Bradley Estate," beautifully updated 3 bedroom antique home, with an additional 1 bedroom guest apartment in the nearby renovated barn, a gunite pool with views west, apple orchard and a lovely park-like setting. The 3 bedroom home main house offers open kitchen to Conservatory for great

  Kathryn Clair William Pitt Sotheby's Int'l

  76 North St, 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 $648,246 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,696 Sq Ft

  29 Apple Ridge, Roxbury, CT 06783

  29 Apple Ridge, 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
• 

  

  /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
• 

  $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
• 

  Est $1,399,680 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
• 

  

  /34

  $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
• 

  

  /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
• 

  $1,725,000 Sold Apr 25, 2025

  • 4,112 Sq Ft
  • $420/SF
  • 186 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2011

  381 South St, Roxbury, CT 06783

  Meander over a small bridge and through tall pines to reach this distinctive 4 bedroom home on 6 very private acres. A gracious wood paneled central foyer directs you into the living room, dining room, or through to a thoughtfully designed great room. The kitchen features a wrap-around island with bar stools, high-end appliances walk-in pantry/laundry. It also opens to the breakfast nook and

  Stacey Matthews W. Raveis Lifestyles Realty

  381 South St, Roxbury, CT 06783
• 

  Est $805,971 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
• 

  

  /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
• 

  $1,275,000 Sold Apr 21, 2025

  • 4,572 Sq Ft
  • $279/SF
  • 256 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1969

  36 Chalybes Rd, Roxbury, CT 06783

  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

  Jill Sloane Brown Harris Stevens

  36 Chalybes Rd, Roxbury, CT 06783
• 

  Est $1,731,666 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

  $1,995,000

  • 4 Beds
  • 2.5 Baths
  • 2,640 Sq Ft

  27 Wakelee Rd, Roxbury, CT 06783

  Many new renovations in this stunning antique home on a quiet country road. All flat usable land with gorgeous bank barn, gunite pool, Spectacular mature trees, and pond. Town has house listed as 5 bedrooms. The primary bedroom with walk in closet is on the main level. Upstairs is more efficiently used as 2 suites each with walk in closets or offices. Alternately, one of the larger bedrooms could

  Stacey Matthews W. Raveis Lifestyles Realty

  27 Wakelee Rd, Roxbury, CT 06783
• 

  $1,600,000 Sold Apr 11, 2025

  • 3,123 Sq Ft
  • $512/SF
  • 103 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 2000

  130 E Flag Swamp Rd, Roxbury, CT 06783

  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

  Pels Matthews W. Raveis Lifestyles Realty

  130 E Flag Swamp Rd, Roxbury, CT 06783
• 

  Est $2,174,783 Not Listed For Sale

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

  98 Bacon Rd, Roxbury, CT 06783

  98 Bacon Rd, Roxbury, CT 06783
• 

  

  /40

  $1,495,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,379 Sq Ft

  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
• 

  $840,000 Sold Apr 03, 2025

  • 1,720 Sq Ft
  • $488/SF
  • 146 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1966

  201 Painter Hill Rd, Roxbury, CT 06783

  Painter Hill Cottage, a delightful 3BDR, 2 Bath cottage with heated, Gunite pool. Here is an opportunity to take this home to the next level on one of the most desirable roads in Roxbury. It provides a light and bright interior with an easy-living, one-level floor plan. A new deck is under construction and will be completed on or before 12/30/24. Enjoy the morning sunrise and beautiful light

  Diana Bisselle William Pitt Sotheby's Int'l

  201 Painter Hill Rd, Roxbury, CT 06783

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