Roxbury, CT Homes

• 

  

  

  /39

  $875,000

  • 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

• 

  

  

  /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 $586,306 Not Listed For Sale

  34 Spargo Rd, Roxbury, CT 06783

  • 2 Beds
  • 2 Baths
  • 2,321 Sq Ft
  • Built 1930

  34 Spargo Rd, Roxbury, CT 06783

  Last Sold Summary

  • 8% Above List Price
  • $235/SF
  • 12 Days On Market

  Last Sold Price $545,000

  Last Listing Agent Karan Garewal Winwin Realty
• 

  

  

  /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
• 

  

  /37

  $25,000 total monthly price

  • 3 Beds
  • 3.5 Baths
  • 2,400 Sq Ft
  • 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

  Kathryn Clair William Pitt Sotheby's Int'l

  76 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 $2,421,443

  Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty

  143 Tophet Rd, Roxbury, CT 06783
• 

  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

  Last Listing Agent WAYNE PISKURA Klemm Real Estate Inc
• 

  

  /49

  $1,600,000

  • 4 Beds
  • 4.5 Baths
  • 6,444 Sq Ft

  380 Southbury Rd, Roxbury, CT 06783

  Imagine turning onto a quiet country road in beautiful Roxbury, Connecticut, passing classic stone walls and mature trees before arriving at a private drive that gently curves you home. Set back on nearly seven acres of peaceful countryside, 380 Southbury Road offers a rare blend of privacy, elegance, and timeless New England charm. From the moment you step through the arched front entry, the

  Nancy Young BHHS Hudson Valley Properties

  380 Southbury Rd, Roxbury, CT 06783
• 

  

  /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
• 

  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

  Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty
• 

  

  /40

  $2,395,000

  • 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
• 

  

  /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

  Current Estimated Value $2,028,578

  Last Listing Agent Rick Distel Compass Connecticut, LLC

  32 Grassy Hill Rd, Roxbury, CT 06783
• 

  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

  Last Listing Agent Jay McGorty McGorty Real Estate Services
• 

  

  /37

  $1,695,000 Open Sat 11AM - 1PM

  • 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
• 

  

  /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
• 

  Est $1,846,067 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

  • 12% Above List Price
  • $335/SF
  • 49 Days On Market

  Last Sold Price $1,650,000

  Last Listing Agent Maria Taylor Klemm Real Estate Inc
• 

  

  /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
• 

  

  /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 $1,217,917

  Last Listing Agent Pels Matthews W. Raveis Lifestyles Realty

  53 Transylvania Rd, Roxbury, CT 06783
• 

  Est $172,393 Not Listed For Sale

  268 Southbury Rd, Roxbury, CT 06783

  • 5 Beds
  • Built 1950

  268 Southbury Rd, Roxbury, CT 06783

  Last Sold Summary

  • 24% Above List Price
  • $38/SF
  • 319 Days On Market

  Last Sold Price $139,000

  Last Listing Agent Rhya Szymansky Drakeley Real Estate, Inc.
• 

  

  /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
• 

  

  /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 $1,050,220

  Last Listing Agent Pels Matthews W. Raveis Lifestyles Realty

  19 Spargo 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

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

  

  /32

  $2,295,000

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

  176 Apple Ln, Roxbury, CT 06783

  Stunning modern shingle-style Colonial on over 4 manicured acres + gunnite pool in the heart of Roxbury - absolutely turnkey. No expense spared in this architect designed home blending elegant style with top-tier systems. Sun-filled open floor plan with custom oak accents, soaring ceilings, fieldstone fireplace, and picture windows that bring the outdoors in. Chef's kitchen with high-end

  Kathryn Bassett William Pitt Sotheby's Int'l

  176 Apple Ln, Roxbury, CT 06783
• 

  

  /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

  Current Estimated Value $1,216,057

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

  158 Painter Hill Rd, Roxbury, CT 06783
• 

  Est $1,268,278 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

  • 21% Above List Price
  • $690/SF
  • 90 Days On Market

  Last Sold Price $1,050,000

  Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty
• 

  

  /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 Lahoud William Pitt Sotheby's Int'l

  85 Good Hill Rd, Roxbury, CT 06783
• 

  

  /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 $1,564,854

  Last Listing Agent Donna J. Matula William Raveis Real Estate

  Unlisted Address
• 

  Est $655,842 Not Listed For Sale

  29 Apple Ridge, Roxbury, CT 06783

  • 3 Beds
  • 1 Bath
  • 1,696 Sq Ft
  • Built 1985

  29 Apple Ridge, Roxbury, CT 06783

  Last Sold Summary

  • 24% Above List Price
  • $313/SF
  • 17 Days On Market

  Last Sold Price $530,500

  Last Listing Agent Tom Slekis Berkshire Hathaway Home Services
• 

  

  /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
• 

  

  /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 $1,378,286 Not Listed For Sale

  310 North St, Roxbury, CT 06783

  • 4 Beds
  • 3.5 Baths
  • 3,360 Sq Ft
  • Built 1998

  310 North St, Roxbury, CT 06783

  Last Sold Summary

  • 10% Above List Price
  • $372/SF
  • 14 Days On Market

  Last Sold Price $1,250,000

  Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty

Showing Results 1 - 40, Page 1 of 18