Homes in ZIP Code 06783

/39
$1,149,000
- 3 Beds
- 2.5 Baths
- 4,012 Sq Ft
24 Roxbury Rd, Woodbury, CT 06798

Tucked away in the picturesque hills of Litchfield County, right on the desirable Woodbury/Roxbury line, this stunning Colonial-Contemporary residence offers an unparalleled blend of privacy, natural beauty, and modern comfort on nearly 10 acres of pristine land. Surrounded by mature trees, vibrant plantings, and lush greenery, the property is enhanced by the gentle sounds of Transylvania Brook

Shaylene Neumann

Houlihan Lawrence

(475) 265-6372

24 Roxbury Rd, Woodbury, CT 06798
/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
- Land
- 25.01 Acres
- $12,795 per Acre
- 747 Days On Market
0 Wellers Bridge Rd, Roxbury, CT 06783

Affordable housing opportunity for interested donor. Approved building lot with a complete survey which includes wetland delineation and recommended building site. This 25.01-acre wooded oasis in Roxbury, located just half a mile from scenic Route 67, offers a tranquil and private retreat in the heart of historic Roxbury. With 250 feet of road frontage on Wellers Bridge Rd, this property is a

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

/40
$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
/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
$2,501,000 Sold Nov 21, 2025
- 8,091 Sq Ft
- $309/SF
- 88 Days On Market
- 5 Beds
- 6 Baths
- Built 2005
Unlisted Address

Exquisite Country Estate in Roxbury Nestled on 42 private acres in the heart of Roxbury, this spectacular shingle-style architectural masterpiece offers an unparalleled blend of sophistication and serene country living. From the moment you meander down the picturesque drive, you'll know you have arrived at your forever home. Designed for both grand entertaining and intimate daily life, the home's

Kathryn Clair William Pitt Sotheby's Int'l

Unlisted Address

Not Listed For Sale
00 Chalybes Rd W, Roxbury, CT 06783

00 Chalybes Rd W, Roxbury, CT 06783

/39
$2,572,500
- 3 Beds
- 2.5 Baths
- 2,559 Sq Ft
277 Painter Hill Rd, Roxbury, CT 06783

This beautifully renovated 1911 colonial blends timeless charm with modern comfort in one of Roxbury's most desirable locations. The main residence offers luxury living with 2-3 bedrooms, a media room, gourmet kitchen, formal dining room, and a screened porch. The newly built guest house includes 2 bedrooms and a spacious game room/cabana with fireplace. Enjoy Summer entertaining on the covered

Stacey Matthews W. Raveis Lifestyles Realty

277 Painter Hill 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

Now available from January 2026. 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 including a wine

Melinda Dubow Klemm Real Estate Inc

10 Sentry Hill Rd, Roxbury, CT 06783
$912,500 Sold Nov 19, 2025
- 2,982 Sq Ft
- $306/SF
- 141 Days On Market
- 4 Beds
- 3 Baths
- Built 1851
11 Hodge Rd, Roxbury, CT 06783

This Circa 1851 Historic house known as 'Mine and Quarry House "in Roxbury, Ct ' Historic and Architectural resource survey is highly significant as the only surviving antique of the mining and quarrying industries. It boarders on 100's of acres of the Roxbury Land trust and enjoys valley views of the Shepaug River. Over time it became a really charming home in a very private and pretty setting

Karen Casey William Pitt Sotheby's Int'l

11 Hodge Rd, Roxbury, CT 06783

Est $1,485,659 Not Listed For Sale
- 3 Beds
18 Brandy Wine Crossing, Roxbury, CT 06783

18 Brandy Wine Crossing, Roxbury, CT 06783

/37
$1,795,000
- 4 Beds
- 5 Baths
- 6,169 Sq Ft
31 Hickory Ln, Roxbury, CT 06783

Beautiful property in highly desirable Roxbury neighborhood. Traditional colonial with double story portico set back from quiet lane in park like setting with mature trees and gardens, huge pool, fruit trees, plenty of space for animals, stable, paddock. Detached garage in addition to under house garage with plenty of possibilities for guest house, studio, office. Large woodshed and enclosed

Philippa Malkin W. Raveis Lifestyles Realty

31 Hickory Ln, Roxbury, CT 06783
/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
$1,195,000 Sold Nov 07, 2025
- 2,793 Sq Ft
- $428/SF
- 40 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2005
158 Painter Hill Rd, Roxbury, CT 06783

Great value, excellent location! Painter Hill is one of Roxbury's most scenic country roads. Close to Toplands Farm with beautiful pastoral views, a short drive to Maple Bank Farm for local produce, and just steps to a quiet dirt road for long walks. This charming Cape, built by the reputable local builder/owner in 2005, has 3 BR, 2.5 baths, a free-form Gunite pool and amazing outdoor living

Bonnie Garguilo William Pitt Sotheby's Int'l

158 Painter Hill Rd, Roxbury, CT 06783

Est $175,025 Not Listed For Sale
- 5 Beds
268 Southbury Rd, Roxbury, CT 06783

268 Southbury Rd, Roxbury, CT 06783

/40
$1,675,000
- 4 Beds
- 2.5 Baths
- 6,395 Sq Ft
99 Carriage Ln, Roxbury, CT 06783

Welcome to this beautifully maintained 4-bedroom, 2.5-bath home, nestled in a serene and peaceful location-perfect for those seeking comfort and tranquility. Step inside to a spacious open-concept living and dining area, ideal for hosting gatherings and entertaining with ease. The modern kitchen features state-of-the-art appliances, ample counter space, and generous storage-making it a dream for

Debra Tricarico Houlihan Lawrence

99 Carriage Ln, Roxbury, CT 06783
/37
$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
$1,400,000 Sold Nov 06, 2025
- 4,721 Sq Ft
- $297/SF
- 64 Days On Market
- 4 Beds
- 5.5 Baths
- Built 1976
30 Hickory Ln, Roxbury, CT 06783

This stunning property has undergone an extensive, down-to-the-studs renovation, creating a home that feels brand new. The redesigned layout features a spacious, open-concept great room, complemented by an elegant living room/sunroom with a striking stone fireplace that walks out to the back deck. The chef's kitchen is a showstopper, designed to impress even the most discerning culinary

Stacey Matthews W. Raveis Lifestyles Realty

30 Hickory Ln, Roxbury, CT 06783

Est $1,245,589 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

/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
/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
$499,000 Sold Nov 05, 2025
- Land
- 6.81 Acres
- $73,275 per Acre
- 33 Days On Market
Lot 2 Chalybes Rd W, Roxbury, CT 06783

This 6.81 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. A partial driveway is already in place, saving you time and money as you begin the building process. Enjoy the best

Kathryn Clair William Pitt Sotheby's Int'l

Lot 2 Chalybes Rd W, Roxbury, CT 06783

Est $672,368 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,696 Sq Ft
29 Apple Ridge, Roxbury, CT 06783

29 Apple Ridge, Roxbury, CT 06783

/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
/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
$407,500 Sold Oct 29, 2025
- Land
- 6.79 Acres
- $60,015 per Acre
- 227 Days On Market
238 North St, Roxbury, CT 06783

DRIVEWAY NOW UNDER Construction! Engineering APPROVED-Permit on File. Rarely available Lot in Roxbury! Magical 6.79 acre lot featuring a majestic stream and spring house, un-touched historic stone walls, gently sloping tree-covered hills and an abundance of pine trees, oaks and maples as your canvas. This masterpiece lot is perfect to build your dream home and to connect with what is important in

Jill Sloane Brown Harris Stevens

238 North St, Roxbury, CT 06783

Est $1,440,682 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

/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
/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 for $15,000/mo for April and May, 2026 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.

Stacey Matthews W. Raveis Lifestyles Realty

34 Old Roxbury Rd, Roxbury, CT 06783
$1,650,000 Sold Oct 23, 2025
- 3,302 Sq Ft
- $500/SF
- 23 Days On Market
- 3 Beds
- 3.5 Baths
- Built 1991
78 Garnet Rd, Roxbury, CT 06783

Looking for a calming and peaceful property? You'll find total peace and quiet on this 15.29 acre impeccably maintained property bordering Roxbury Land Trust land. With a beautiful wrap around porch to take in views of the beautiful fruit trees, mature gardens, pond and level grounds this farmhouse is perfect inside and out. The heated and cooled large barn is a perfect flex space for an art

Andrew Murphy E.J. Murphy Realty

78 Garnet Rd, 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

/22
$1,949,000
- 4 Beds
- 3.5 Baths
- 4,517 Sq Ft
45 Moosehorn Rd, Roxbury, CT 06783

Pristine 4+ bedroom large (4,517 sq. ft.) private home on a scenic dirt road - perfect for walking, jogging and biking surrounded by Moosehorn Land Preserve and country estates. Magnificent design incorporating picturesque country views, over-sized living room, dining room for 12+, chef's kitchen, vaulted ceilings, hardwood floors and two gas fireplaces. Heated pool surrounded by endless summer

Peter Klemm Klemm Real Estate Inc

45 Moosehorn Rd, 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
$1,200,000 Sold Oct 17, 2025
- 3,920 Sq Ft
- $306/SF
- 150 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2000
53 Transylvania Rd, Roxbury, CT 06783

Fantastic Colonial in Roxbury down long private drive featuring low maintenance salt water spa pooL. The house is surrounded by nature, with multiple entertaining spaces and gardens. Amazing bird life is a natural symphony while relaxing outdoors. The home has a lovely gracious layout all with detailed millwork and a vaulted great room with almost floor to ceiling windows on three sides creating

Pels Matthews W. Raveis Lifestyles Realty

53 Transylvania Rd, Roxbury, CT 06783

Est $1,833,115 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

/21
$1,575,000
- 3 Beds
- 4 Baths
- 2,396 Sq Ft
247 Painter Hill Rd, Roxbury, CT 06783

Pristine St. Barth-Style bungalow with two-car garage. Single-level living surrounded by Roxbury's best historic estate neighborhood, farms and homes of artists, actors and writers. Magnificent open floor plan with 2-3 bedrooms on main floor, 2 fireplaces, new eat-in kitchen, vaulted living room, den and screened porch and another bedroom in finished lower level. Dine or relax on the flagstone

Peter Klemm Klemm Real Estate Inc

247 Painter Hill Rd, Roxbury, CT 06783
/13
$10,900 total monthly price
- 1 Bed
- 2 Baths
- 900 Sq Ft
- House for Rent
253 Tophet Rd, Roxbury, CT 06783

Large Vaulted Pool House. King BR + BA,Trundle BR/BA - King Bed or 2 Twins. Chef's Kitchen. Covered BBQ. Deck Overlooking Pool.Garage. SUMMER June - August $24,900/month Memorial - Labor Day $59,000; OFF-SEASON September - May $10,900/month. If over 3 months, deduct $1,000 per month and no tax is due. ANNUAL $129,000. Possible to rent with Main House with its own plunge pool. See listing for 253

Peter Klemm Klemm Real Estate Inc

253 Tophet Rd, Roxbury, CT 06783
$1,050,000 Sold Oct 15, 2025
- 1,571 Sq Ft
- $668/SF
- 147 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1966
19 Spargo Rd, Roxbury, CT 06783

Step into timeless style and serene privacy with this beautifully maintained 1966 mid-century modern home. Set on almost 5 acres of lush, private land, this 3-bedroom, 2.5-bath residence blends classic design with modern upgrades. The just-renovated bathrooms feature high-end, spa-like finishes, while the expansive deck provides the perfect setting for outdoor entertaining or peaceful relaxation.

Pels Matthews W. Raveis Lifestyles Realty

19 Spargo Rd, Roxbury, CT 06783

Est $805,133 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

Connecticut Litchfield County Roxbury 06783

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