Homes in ZIP Code 06783

/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
/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

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

/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 $2,381,886

Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty

143 Tophet Rd, Roxbury, CT 06783

Est $989,409 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
- 18% Above List Price
- $211/SF
- 221 Days On Market
Last Sold Price $840,000

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

/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
/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

21 Hemlock Rd, Roxbury, CT 06783
- 4 Beds
- 3 Baths
- 2,984 Sq Ft
- Built 2020
21 Hemlock Rd, Roxbury, CT 06783

Last Sold Summary
- $469/SF
- 191 Days On Market
Last Sold Price $1,400,000

Last Listing Agent Kathryn Clair William Pitt

/37
$1,745,000
- 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
/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 $2,171,333

Last Listing Agent Rick Distel Compass Connecticut, LLC

32 Grassy Hill Rd, Roxbury, CT 06783

Not Listed For Sale

Lot Davenport Rd, Roxbury, CT 06783
Lot Davenport Rd, Roxbury, CT 06783

Last Sold Summary
- 40 Days On Market
Last Sold Price $135,000

Last Listing Agent Kathryn Clair William Pitt

/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
/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

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

/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
$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 $1,259,595

Last Listing Agent Pels Matthews W. Raveis Lifestyles Realty

53 Transylvania 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

/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
/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 $1,021,037

Last Listing Agent Pels Matthews W. Raveis Lifestyles Realty

19 Spargo Rd, Roxbury, CT 06783

Est $1,780,140 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
- 8% Above List Price
- $335/SF
- 49 Days On Market
Last Sold Price $1,650,000

Last Listing Agent Maria Taylor Klemm Real Estate Inc

/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
/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 $1,203,806

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

158 Painter Hill Rd, Roxbury, CT 06783

Est $172,676 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.

/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
/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 $1,401,963

Last Listing Agent Donna J. Matula William Raveis Real Estate

Unlisted Address

Est $1,239,571 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

Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty

/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
/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 $708,002 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
- 33% Above List Price
- $313/SF
- 17 Days On Market
Last Sold Price $530,500

Last Listing Agent Tom Slekis Berkshire Hathaway Home Services

Showing Results 1 - 40, Page 1 of 18

Connecticut Litchfield County Roxbury 06783

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