Roxbury, CT Homes

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  /39

  $875,000 Open Mon 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 2,489 Sq Ft

  47 South St, Roxbury, CT 06783

  A colonial antique home on a level scenic lot in sought-after Litchfield County. As you enter through the front door, you're welcomed by an original staircase & hickory wood floors. The living room features an exposed wood beam, a fireplace & hickory flooring. A formal dining room with classic pine floors & french doors that lead to a 4 season room. The 4 season room features a wood-burning

  

  Michelle Alvord

  Berkshire Hathaway NE Prop.

  (860) 390-4127

  47 South St, Roxbury, CT 06783
• Explore Roxbury

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  /14

  $2,500 total monthly price

  • 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
• 

  $320,000 Sold Nov 25, 2025

  0 Wellers Bridge Rd, Roxbury, CT 06783

  • Land
  • 25.01 Acres
  • $12,795 per Acre

  Last Sold Summary

  • 42% Below List Price
  • 747 Days On Market

  Last Listing Agent David Hughes Century 21 AllPoints Realty

  0 Wellers Bridge Rd, Roxbury, CT 06783
• 

  Est $2,552,447 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 3,500 Sq Ft

  130 Tophet Rd, Roxbury, CT 06783

  130 Tophet Rd, Roxbury, CT 06783
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  /40

  $2,295,000 Pending

  • 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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  /29

  $35,000 total monthly price

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

  34 Old Roxbury Rd, Roxbury, CT 06783

  Available @ $35K for August 6-Sept 7, 2026. Also avail $15,000/mo for school year 2026/2027. Gunite Heated Pool being installed in April 2026 and will be ready for August tenant. 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

  Stacey Matthews W. Raveis Lifestyles Realty

  34 Old Roxbury Rd, Roxbury, CT 06783
• 

  $1,800,000 Sold Mar 26, 2025

  108 Davenport Rd, Roxbury, CT 06783

  • 4 Beds
  • 5.5 Baths
  • 5,100 Sq Ft
  • Built 1851

  Last Sold Summary

  • 3% Below List Price
  • $353/SF
  • 63 Days On Market

  Last Listing Agent Richard Pomerantz William Pitt Sotheby's Int'l

  108 Davenport Rd, Roxbury, CT 06783
• 

  Est $1,591,819 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,233 Sq Ft

  52 Welton Rd, Roxbury, CT 06783

  52 Welton Rd, Roxbury, CT 06783
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  /38

  $1,795,000

  • 5 Beds
  • 6 Baths
  • 5,447 Sq Ft

  233 Southbury Rd, Roxbury, CT 06783

  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

  Kathryn Clair William Pitt Sotheby's Int'l

  233 Southbury Rd, Roxbury, CT 06783
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  /40

  $9,000 total monthly price

  • 3 Beds
  • 2 Baths
  • 2,568 Sq Ft
  • House for Rent

  7 Lower County Rd, Roxbury, CT 06783

  Escape to the country and spend your Spring & Summer in Connecticut's spectacular Litchfield County! Spend your mornings sipping coffee and viewing the sunrise from the front porch, and evenings with sunsets on the back deck. This centrally located, hilltop, 3 bedroom, 2 & 1/2 bath home is bright & open - soaring ceilings and open floor-plan brings everyone together. Main level primary suite has

  Christopher Haggerty Around Town Real Estate LLC

  7 Lower County Rd, Roxbury, CT 06783
• 

  $1,966,500 Sold Dec 22, 2025

  32 Grassy Hill Rd, Roxbury, CT 06783

  • 4 Beds
  • 5 Baths
  • 4,728 Sq Ft
  • Built 2002

  Last Sold Summary

  • 21% Below List Price
  • $416/SF
  • 256 Days On Market

  Last Listing Agent Rick Distel Compass Connecticut, LLC

  32 Grassy Hill Rd, Roxbury, CT 06783
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  Not Listed For Sale

  00 Phaeton Dr, Roxbury, CT 06783

  00 Phaeton Dr, Roxbury, CT 06783
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  /40

  $2,475,000

  • 4 Beds
  • 4.5 Baths
  • 4,874 Sq Ft

  1030 Washington Woodbury Rd, Roxbury, CT 06783

  Good Hope Estate. Transport yourself to this stunning European-style home with all the bells and whistles! The well thought out 4 bedroom, 4.5 bath home with seasonal views sits on 18 acres of privacy and nature! The eat-in kitchen is a chef's dream complete with Sub-Zero, Dacor range, granite countertops and double farm sink. Plus a separate pantry to go with it. Adjacent is a cozy area with

  Judith Auchincloss Klemm Real Estate Inc

  1030 Washington Woodbury Rd, Roxbury, CT 06783
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  /8

  $2,200 total monthly price

  • 1 Bed
  • 1 Bath
  • 900 Sq Ft
  • House for Rent

  10 (LOWER) Sentry Hill Rd, Roxbury, CT 06783

  Available May 2026: $2,200 plus utilities per month. 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 1 bedroom/1 bath apartment, is located beneath the main house and may be rented with the main house(Upstairs 3-bedroom) or completely

  Melinda Dubow Klemm Real Estate Inc

  10 (LOWER) Sentry Hill Rd, Roxbury, CT 06783
• 

  $499,000 Sold Nov 05, 2025

  Lot 2 Chalybes Rd W, Roxbury, CT 06783

  • Land
  • 6.81 Acres
  • $73,275 per Acre

  Last Sold Summary

  • 33 Days On Market

  Last Listing Agent Kathryn Clair William Pitt Sotheby's Int'l

  Lot 2 Chalybes Rd W, Roxbury, CT 06783
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  Not Listed For Sale

  00 Chalybes Rd W, Roxbury, CT 06783

  00 Chalybes Rd W, Roxbury, CT 06783
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  /37

  $1,795,000

  • 4 Beds
  • 5 Baths
  • 6,169 Sq Ft

  31 Hickory Ln, Roxbury, CT 06783

  This special home is located in one of Roxbury's most desirable neighborhoods on a quiet dead end road. A long, winding & very private driveway leads up to the commanding double-story porticoed entrance. The traditional colonial layout includes a central chef's kitchen which rests between the formal living, media & dining rooms. The main floor is completed by an office, 2 half baths, and a 2-room

  Philippa Malkin W. Raveis Lifestyles Realty

  31 Hickory Ln, Roxbury, CT 06783
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  /28

  $6,000 total monthly price

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

  10 Sentry Hill Rd, Roxbury, CT 06783

  Whole House Now available from May 2026 at $6,000. 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 4-bedroom, 3 bath home rests on five acres with a gentle stream running through it. State of the art chef's kitchen with all new appliances

  Melinda Dubow Klemm Real Estate Inc

  10 Sentry Hill Rd, Roxbury, CT 06783
• 

  $1,200,000 Sold Oct 17, 2025

  53 Transylvania Rd, Roxbury, CT 06783

  • 3 Beds
  • 2.5 Baths
  • 3,920 Sq Ft
  • Built 2000

  Last Sold Summary

  • 20% Below List Price
  • $306/SF
  • 150 Days On Market

  Current Estimated Value $1,227,288

  Last Listing Agent Pels Matthews W. Raveis Lifestyles Realty

  53 Transylvania Rd, Roxbury, CT 06783
• 

  Est $1,737,211 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,928 Sq Ft

  60 Good Hill Rd, Roxbury, CT 06783

  60 Good Hill Rd, Roxbury, CT 06783
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  /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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  /28

  $20,000 total monthly price

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

  5 North St, Roxbury, CT 06783

  Summer 2026: July and/or 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

  Melinda Dubow Klemm Real Estate Inc

  5 North St, Roxbury, CT 06783
• 

  $1,050,000 Sold Oct 15, 2025

  19 Spargo Rd, Roxbury, CT 06783

  • 3 Beds
  • 2.5 Baths
  • 1,571 Sq Ft
  • Built 1966

  Last Sold Summary

  • 16% Below List Price
  • $668/SF
  • 147 Days On Market

  Current Estimated Value $1,017,903

  Last Listing Agent Pels Matthews W. Raveis Lifestyles Realty

  19 Spargo Rd, Roxbury, CT 06783
• 

  Est $173,692 Not Listed For Sale

  • 5 Beds

  268 Southbury Rd, Roxbury, CT 06783

  268 Southbury Rd, Roxbury, CT 06783
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  /38

  $1,599,000

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

  99 Carriage Ln, Roxbury, CT 06783

  Looking to escape the hectic pace of city life? Welcome to this peaceful, beautifully renovated 4-bedroom home, originally built in 2005, offering the perfect blend of comfort and tranquility. Featuring 2.5 baths and a spacious open-concept living and dining area, this home is ideal for hosting gatherings and entertaining with ease. The modern kitchen is a dream for any home chef, complete with

  Debra Tricarico Houlihan Lawrence

  99 Carriage Ln, Roxbury, CT 06783
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  /25

  $7,000 total monthly price

  • 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
• 

  $1,195,000 Sold Nov 07, 2025

  158 Painter Hill Rd, Roxbury, CT 06783

  • 3 Beds
  • 2.5 Baths
  • 2,793 Sq Ft
  • Built 2005

  Last Sold Summary

  • $428/SF
  • 40 Days On Market

  Last Listing Agent Bonnie Garguilo William Pitt Sotheby's Int'l

  158 Painter Hill Rd, Roxbury, CT 06783
• 

  Est $1,208,501 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,522 Sq Ft

  82 Squire Rd, Roxbury, CT 06783

  82 Squire Rd, Roxbury, CT 06783
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  /33

  $1,630,000

  • 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
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  /38

  $15,000 total monthly price

  • 3 Beds
  • 3.5 Baths
  • 2,862 Sq Ft
  • House for Rent

  24 Old Roxbury Rd, Roxbury, CT 06783

  Available March 2-May 31, 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

  Stacey Matthews W. Raveis Lifestyles Realty

  24 Old Roxbury Rd, Roxbury, CT 06783
• 

  $1,490,000 Sold May 22, 2025

  Unlisted Address

  • 3 Beds
  • 4 Baths
  • 3,337 Sq Ft
  • Built 1998

  Last Sold Summary

  • 15% Below List Price
  • $447/SF
  • 204 Days On Market

  Current Estimated Value $1,590,027

  Last Listing Agent Donna J. Matula William Raveis Real Estate

  Unlisted Address
• 

  Est $728,586 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,696 Sq Ft

  29 Apple Ridge, Roxbury, CT 06783

  29 Apple Ridge, Roxbury, CT 06783
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  /11

  $599,000

  • Land
  • 16 Acres
  • $37,438 per Acre

  Lot 4 Chalybes Rd W, Roxbury, CT 06783

  Prime Roxbury Location. Nestled off a picturesque classic country lane, flanked by distinguished residences and just minutes from the vibrant heart of Roxbury Center, awaits an exceptional opportunity. This approved building parcel is primed for complete development, offering a level to gently sloping terrain within a private and serene setting. Imagine crafting your ideal retreat amidst the

  Kathryn Clair William Pitt Sotheby's Int'l

  Lot 4 Chalybes Rd W, Roxbury, CT 06783
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  /17

  $7,500 total monthly price

  • 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
• 

  $1,670,000 Sold Jul 29, 2025

  78 Garnet Rd, Roxbury, CT 06783

  • 3 Beds
  • 3.5 Baths
  • 3,302 Sq Ft
  • Built 1991

  Last Sold Summary

  • 1% Below List Price
  • $506/SF
  • 39 Days On Market

  Last Listing Agent Maria Taylor Klemm Real Estate Inc

  78 Garnet Rd, Roxbury, CT 06783
• 

  Est $1,343,948 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
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  /22

  $399,000

  • Land
  • 4.01 Acres
  • $99,501 per Acre

  Lot 1 Chalybes Rd W, Roxbury, CT 06783

  This 4.01 acre approved building lot offers the perfect blend of tranquility and convenience, making it an exceptional opportunity to create your custom dream home. Tucked away on a quiet road, this property features beautiful, light woods that provide a serene and private setting. Enjoy the best of Roxbury's natural beauty and recreational amenities, with the lot located just minutes from the

  Kathryn Clair William Pitt Sotheby's Int'l

  Lot 1 Chalybes Rd W, Roxbury, CT 06783
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  /25

  $12,900 total monthly price

  • 4 Beds
  • 2.5 Baths
  • 1,782 Sq Ft
  • House for Rent

  23 Painter Hill Rd, Roxbury, CT 06783

  Pristine hilltop art filled home with views and only a short walk to Maple Bank Farm Stand, Toplands Farm and historic Roxbury Center. Wood burning fireplace, vaulted master bedroom with balcony and private bath. Dine or relax on the flagstone terrace. Ping pong, trampoline, croquet, badminton, gas BBQ, fire pit, bikes and board games. SUMMER June - August $18,900/month; OFF-SEASON September -

  Peter Klemm Klemm Real Estate Inc

  23 Painter Hill Rd, Roxbury, CT 06783
• 

  $407,500 Sold Oct 29, 2025

  238 North St, Roxbury, CT 06783

  • Land
  • 6.79 Acres
  • $60,015 per Acre

  Last Sold Summary

  • 15% Below List Price
  • 227 Days On Market

  Last Listing Agent Jill Sloane Brown Harris Stevens

  238 North St, Roxbury, CT 06783
• 

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,816 Sq Ft

  6 Painter Hill Rd, Roxbury, CT 06783

  6 Painter Hill Rd, Roxbury, CT 06783

Showing Results 1 - 40, Page 1 of 18