Homes in ZIP Code 06783

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  /40

  $1,075,000

  • 4 Beds
  • 2.5 Baths
  • 2,556 Sq Ft

  336 South St, Roxbury, CT 06783

  Beautiful 4 bedroom, 2.5-bath Colonial set on a picturesque, park-like property in desirable southern Roxbury. A dramatic two-story foyer welcomes you into a thoughtfully designed layout featuring a formal dining room, a spacious living room with custom built-in bookshelves, and an impressive family room highlighted by a floor-to-ceiling fireplace and custom built-ins. The kitchen is

  Karen Gilmore Redfin Corporation

  336 South St, 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
• 

  $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 $1,799,166 Not Listed For Sale

  381 South St, Roxbury, CT 06783

  • 4 Beds
  • 4.5 Baths
  • 4,112 Sq Ft
  • Built 2011

  381 South St, Roxbury, CT 06783

  Last Sold Summary

  • 4% Above List Price
  • $420/SF
  • 186 Days On Market

  • Last Sold Price $1,725,000
  • Apr 25, 2025

  Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty
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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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  /28

  $16,500 Per Month

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

  5 North St, Roxbury, CT 06783

  NEW PRICE Summer 2026: July and/or August at $16,500 per month. 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 Wonderful

  Melinda Dubow Klemm Real Estate Inc

  5 North St, Roxbury, CT 06783
• 

  $1,925,000 Sold Feb 17, 2026

  143 Tophet Rd, Roxbury, CT 06783

  • 4 Beds
  • 5.5 Baths
  • 5,848 Sq Ft
  • Built 2005

  Last Sold Summary

  • 26% Below List Price
  • $329/SF
  • 259 Days On Market

  Current Estimated Value $2,218,446

  Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty

  143 Tophet Rd, Roxbury, CT 06783
• 

  Est $2,874,309 Not Listed For Sale

  42 Berry Rd, Roxbury, CT 06783

  • 4 Beds
  • 5.5 Baths
  • 3,043 Sq Ft
  • Built 2018

  42 Berry Rd, Roxbury, CT 06783

  Last Sold Summary

  • 1% Above List Price
  • $939/SF
  • 15 Days On Market

  • Last Sold Price $2,858,000
  • May 02, 2025

  Last Listing Agent Graham Klemm Klemm Real Estate Inc
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  /40

  $1,375,000

  • 3 Beds
  • 2.5 Baths
  • 2,620 Sq Ft

  56 Gold Mine Rd, Roxbury, CT 06783

  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

  Fred Bond William Pitt Sotheby's Int'l

  56 Gold Mine Rd, Roxbury, CT 06783
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  /37

  $25,000

  Total Monthly Price

  • 3 Beds
  • 4 Baths
  • House for Rent

  76 North St, Roxbury, CT 06783

  Available Month of August through Labor Day 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 suite 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

  76 North St, 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

  Current Estimated Value $2,028,578

  Last Listing Agent Rick Distel Compass Connecticut, LLC

  32 Grassy Hill Rd, Roxbury, CT 06783
• 

  Est $701,576 Not Listed For Sale

  396 Southbury Rd, Roxbury, CT 06783

  • 3 Beds
  • 2 Baths
  • 2,382 Sq Ft
  • Built 1943

  396 Southbury Rd, Roxbury, CT 06783

  Last Sold Summary

  • 9% Above List Price
  • $271/SF
  • 62 Days On Market

  • Last Sold Price $645,000
  • Apr 25, 2025

  Last Listing Agent Mirella D'Antonio William Raveis Real Estate
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  /40

  $2,095,000

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

  1030 Washington Woodbury Rd, Roxbury, CT 06783

  NEW PRICE - Privately set on 18.62 acres, this substantial Roxbury country estate offers scale, privacy, and the relaxed elegance that defines Litchfield County living. Designed for both comfortable daily living and effortless entertaining, the home opens to expansive grounds, a pool, and a setting defined by natural beauty and understated presence. With generously proportioned rooms and a strong

  Judith Auchincloss Klemm Real Estate Inc

  1030 Washington Woodbury Rd, Roxbury, CT 06783
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  /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
• 

  $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 Phaeton Dr, Roxbury, CT 06783

  00 Phaeton Dr, Roxbury, CT 06783

  Last Sold Summary

  • 223 Days On Market

  • Last Sold Price $115,000
  • Jun 13, 2023

  Last Listing Agent WAYNE PISKURA Klemm Real Estate Inc
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  /37

  $1,685,000

  • 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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  /33

  $24,900 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,080 Sq Ft
  • House for Rent

  Unlisted Address

  Meander down the most scenic of Roxbury dirt roads to reach "Tunnel Road 4-BR" tucked between the Shepaug River, historic wood Judd's Bridge and Farm and 1000 acres of Steep Rock land trust with endless hiking trails. Pristine renovated private country home with year round 8'x 16' spa pool, wood burning fireplace and open floor plan. Dine or relax on the granite terrace or covered front porch.

  Peter Klemm Klemm Real Estate Inc

  Unlisted Address
• 

  $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 $1,223,078

  Last Listing Agent Pels Matthews W. Raveis Lifestyles Realty

  53 Transylvania 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

  Last Sold Summary

  • 439 Days On Market

  • Last Sold Price $537,500
  • Oct 30, 2024

  Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty
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  /35

  $2,045,000

  • 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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  /40

  $9,000 Per Month

  • 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 Compass Connecticut, LLC

  7 Lower County Rd, 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 $1,063,305

  Last Listing Agent Pels Matthews W. Raveis Lifestyles Realty

  19 Spargo Rd, Roxbury, CT 06783
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  Not Listed For Sale

  0 Hemlock Rd, Roxbury, CT 06783

  0 Hemlock Rd, Roxbury, CT 06783

  Last Sold Summary

  • 173 Days On Market

  • Last Sold Price $299,000
  • Feb 20, 2025

  Last Listing Agent Jay McGorty McGorty Real Estate Services
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  /38

  $1,495,000

  • 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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  /27

  $15,000 Per Month

  • 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 $35,000 for August 2026. Enjoy Modern Luxury in Connecticut's Countryside. New Gunite heated pool being installed April 2026. This 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

  Stacey Matthews W. Raveis Lifestyles Realty

  34 Old Roxbury 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

  Current Estimated Value $1,245,548

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

  158 Painter Hill Rd, Roxbury, CT 06783
• 

  Est $1,723,597 Not Listed For Sale

  60 Good Hill Rd, Roxbury, CT 06783

  • 4 Beds
  • 3.5 Baths
  • 4,928 Sq Ft
  • Built 1996

  60 Good Hill Rd, Roxbury, CT 06783

  Last Sold Summary

  • 4% Above List Price
  • $335/SF
  • 49 Days On Market

  • Last Sold Price $1,650,000
  • Jan 16, 2025

  Last Listing Agent Maria Taylor Klemm Real Estate Inc
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  /40

  $1,550,000

  • 4 Beds
  • 4.5 Baths
  • 6,052 Sq Ft

  380 Southbury Rd, Roxbury, CT 06783

  Nestled on nearly seven private acres along a quiet country road in picturesque Roxbury, this exceptional residence offers a seamless blend of elegance, comfort, and classic New England charm. Set back from the road with a gently curving drive, the home welcomes you with a dramatic two-story foyer and grand staircase, complemented by hardwood floors, detailed millwork, crown molding, tray

  ROSEANN BLANTON Berkshire Hathaway NE Prop.

  380 Southbury Rd, Roxbury, CT 06783
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  /8

  $2,200 Per Month

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

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

  Available Mid July 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

  Melinda Dubow Klemm Real Estate Inc

  10 (LOWER) Sentry Hill 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 $1,426,853

  Last Listing Agent Donna J. Matula William Raveis Real Estate

  Unlisted Address
• 

  Est $1,698,765 Not Listed For Sale

  130 E Flag Swamp Rd, Roxbury, CT 06783

  • 2 Beds
  • 2.5 Baths
  • 3,123 Sq Ft
  • Built 2000

  130 E Flag Swamp Rd, Roxbury, CT 06783

  Last Sold Summary

  • 6% Above List Price
  • $512/SF
  • 103 Days On Market

  • Last Sold Price $1,600,000
  • Apr 11, 2025

  Last Listing Agent Pels Matthews W. Raveis Lifestyles Realty
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  /31

  $1,995,000

  • 4 Beds
  • 4.5 Baths
  • 3,566 Sq Ft

  176 Apple Ln, Roxbury, CT 06783

  Your turnkey country escape is waiting in Roxbury - a modern shinglestyle home on 4+ manicured acres with a resortlevel pool, just far enough from the city to exhale, yet close enough to make spontaneous weekend getaways a reality. From the moment you arrive, this summer ready property feels like a private club: stone walls, curated landscaping, quiet woods, and outdoor spaces designed for long

  Kathryn Bassett William Pitt Sotheby's Int'l

  176 Apple Ln, Roxbury, CT 06783
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  /38

  $15,000 Per Month

  • 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
• 

  $1,670,000 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

  Current Estimated Value $1,669,479

  Last Listing Agent Maria Taylor Klemm Real Estate Inc

  78 Garnet Rd, Roxbury, CT 06783
• 

  Est $812,228 Not Listed For Sale

  208 E Flag Swamp Rd, Roxbury, CT 06783

  • 4 Beds
  • 3.5 Baths
  • 3,974 Sq Ft
  • Built 1986

  208 E Flag Swamp Rd, Roxbury, CT 06783

  Last Sold Summary

  • 3% Below List Price
  • $211/SF
  • 221 Days On Market

  • Last Sold Price $840,000
  • Feb 19, 2025

  Last Listing Agent Mary Ann Bennett Drakeley Real Estate, Inc.
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  /40

  $2,895,000

  • 4 Beds
  • 4.5 Baths
  • 4,570 Sq Ft

  220 Painter Hill Rd, Roxbury, CT 06783

  Perched atop Painter Hill-Roxbury's highest elevation and one of its most coveted addresses-this newly renovated residence offers breathtaking, year-round Sunrise and Sunset views. Spanning over 4,500 sq ft, featuring 4-5 bedrooms and is thoughtfully designed for both comfort and entertaining, complete with a three-story elevator & dedicated game/media room. The chef's kitchen is a showpiece,

  Stacey Matthews W. Raveis Lifestyles Realty

  220 Painter Hill Rd, Roxbury, CT 06783
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  /22

  $30,900 Per Month

  • 3 Beds
  • 3.5 Baths
  • 4,251 Sq Ft
  • House for Rent

  45 Moosehorn Rd, Roxbury, CT 06783

  Perfect 6BR 3.5 Bath home with heated pool and child's play gym on a scenic country dirt road that leads into a land preserve along the Shepaug River - perfect for walking, jogging, biking. The most desirable rural historic location within 2 hours of NYC - Roxbury and Washington CT. Home to actors, writers, artists and the owners of luxury estate vacation homes. Many world class restaurants, inns

  Peter Klemm Klemm Real Estate Inc

  45 Moosehorn 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 $1,236,072 Not Listed For Sale

  82 Squire Rd, Roxbury, CT 06783

  • 3 Beds
  • 2.5 Baths
  • 1,522 Sq Ft
  • Built 1880

  82 Squire Rd, Roxbury, CT 06783

  Last Sold Summary

  • 18% Above List Price
  • $690/SF
  • 90 Days On Market

  • Last Sold Price $1,050,000
  • Oct 25, 2024

  Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty

Showing Results 1 - 40, Page 1 of 18