Roxbury, CT Homes

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  $875,000

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

  47 South St, Roxbury, CT 06783

  Step back in time w/ this 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

  

  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
• 

  $865,000 Sold Dec 23, 2024

  68 Carriage Ln, Roxbury, CT 06783

  • 5 Beds
  • 4.5 Baths
  • 4,102 Sq Ft
  • Built 2004

  Last Sold Summary

  • 13% Below List Price
  • $211/SF
  • 129 Days On Market

  Current Estimated Value $960,434

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

  68 Carriage Ln, Roxbury, CT 06783
• 

  Est $605,219 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,501 Sq Ft

  44 Baker Rd, Roxbury, CT 06783

  44 Baker Rd, Roxbury, CT 06783
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  /25

  $849,000

  • 3 Beds
  • 2 Baths
  • 1,862 Sq Ft

  242 Tophet Rd, Roxbury, CT 06783

  Nestled within one of Roxbury, Connecticut's most quiet and picturesque enclaves, this charming 3-bedroom, 2-bath Cape Cod home offers a rare opportunity to cultivate your dream country retreat. Built in the 1970s, this residence presents a wonderful canvas for those seeking to personalize and update a home within a highly sought-after area, celebrated for its exquisite properties and serene

  Kathryn Clair William Pitt Sotheby's Int'l

  242 Tophet Rd, Roxbury, CT 06783
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  /10

  $1,800 total monthly price

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • Apartment for Rent

  346 Southbury Rd, Roxbury, CT 06783

  Handsome upper level apartment located above garage on beautiful property near main house. Great condition. Nice kitchen and bath with full laundry. Heat, AC, electricity included.

  Lisa Titcomb William Pitt Sotheby's Int'l

  346 Southbury Rd, 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
• 

  Not Listed For Sale

  00 Phaeton Dr, Roxbury, CT 06783

  00 Phaeton Dr, Roxbury, CT 06783
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  /40

  $2,295,000

  • 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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  /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
• 

  $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
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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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  /39

  $2,150,000 Pending

  • 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
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  $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
• 

  $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
• 

  Est $175,096 Not Listed For Sale

  • 5 Beds

  268 Southbury Rd, Roxbury, CT 06783

  268 Southbury Rd, Roxbury, CT 06783
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  $2,480,000 New Construction

  • 4 Beds
  • 4 Baths
  • 4,266 Sq Ft

  97 Chalybes Rd W, Roxbury, CT 06783

  TO BE BUILT - A New Classic by Connecticut Residential. A rare opportunity to bring your dream home to life in scenic Roxbury, CT-this timeless Farm House Colonial-inspired residence is thoughtfully designed for both elegance and ease. Sited on a private 4-acre parcel, the proposed 4,266 sq ft home offers antique wooden timbers, refined architectural details, enduring craftsmanship, and a layout

  Christopher Haggerty Around Town Real Estate LLC

  97 Chalybes Rd W, Roxbury, CT 06783
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  /39

  $25,000 total monthly price

  • 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
• 

  $1,200,000 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

  Last Listing Agent Pels Matthews W. Raveis Lifestyles Realty

  53 Transylvania Rd, Roxbury, CT 06783
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  Est $1,251,230 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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  /13

  $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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  $5,500 total monthly price

  • 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
• 

  $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

  Last Listing Agent Pels Matthews W. Raveis Lifestyles Realty

  19 Spargo Rd, Roxbury, CT 06783
• 

  Est $617,084 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

  $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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  /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
• 

  $1,195,000 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 $1,364,747 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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  /26

  $795,000

  • 3 Beds
  • 2.5 Baths
  • 2,336 Sq Ft

  38 W Mountain Ln, Roxbury, CT 06783

  Tucked away on a long private road, this light and bright Roxbury retreat combines timeless character with modern comfort. The home features three spacious bedrooms and two and a half baths, thoughtfully designed for both everyday living and effortless entertaining. Soaring ceilings with exposed beams and abundant skylights fill the interior with natural light, highlighting the warmth of

  Maria Taylor Klemm Real Estate Inc

  38 W Mountain 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
• 

  $1,490,000 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 $1,655,903

  Last Listing Agent Donna J. Matula William Raveis Real Estate

  Unlisted Address
• 

  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
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  /33

  $699,900

  • 4 Beds
  • 2 Baths
  • 2,008 Sq Ft

  216 Baker Rd, Roxbury, CT 06783

  Step back in time with this historic 1800s Colonial that retains its original character and charm while offering modern amenities, including an updated kitchen and bathrooms. The home features four bedrooms upstairs with wood floors, including a primary bedroom with an attached room currently used as an office. The main level with a den, living room with fireplace, dining room, and a

  David Landau RE/MAX Right Choice

  216 Baker Rd, Roxbury, CT 06783
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  /27

  $15,000 total monthly price

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

  34 Old Roxbury Rd, Roxbury, CT 06783

  Available Sept 2026 - May 2027 @ $15,000/mo 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. Upstairs

  Stacey Matthews W. Raveis Lifestyles Realty

  34 Old Roxbury 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 $1,836,307 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
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  /35

  $3,995,000

  • 5 Beds
  • 6 Baths
  • 5,940 Sq Ft

  8 Bayberry Hill, Roxbury, CT 06783

  Privately Sited on a Hill in the Midst of 31+ acres, this Elegantly Renovated 5,000+ sq ft Colonial Offers Panoramic Sunset Views and Exceptional Privacy. Graciously Proportioned Rooms Populate the Main Level & Include: a Vaulted-Ceiling Living Room with Fireplace, Paneled Library, Inviting Family Room, and a Spacious Eat-in Kitchen with Top-tier Appliances. The Refined Primary Suite Features a

  Graham Klemm Klemm Real Estate Inc

  8 Bayberry Hill, 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
• 

  $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
• 

  Est $789,001 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,249 Sq Ft

  112 Southbury Rd, Roxbury, CT 06783

  112 Southbury Rd, Roxbury, CT 06783

Showing Results 1 - 40, Page 1 of 18