Roxbury, CT Homes

$1,400,000 Sold Aug 22, 2025
- 3,389 Sq Ft
- $413/SF
- 60 Days On Market
- 2 Beds
- 2.5 Baths
- Built 1985
88 Hemlock Rd, Roxbury, CT 06783

Exquisite Barn House with Heated Pool. Set Along a Very Low Traveled Unpaved Town Road, This is a Very Chic & Sophisticated Retreat. Wonderful Public Rooms Include: Large Living Room with Vaulted Ceiling, Fireplace & Antique Beams; A Library which Envelopes you with an Antique Board Ceiling, Fireplace & French Doors; Formal Dining Room & A Timeless Eat-in Kitchen which Speaks to Family Room that

Graham Klemm Klemm Real Estate Inc

88 Hemlock Rd, Roxbury, CT 06783

Est $2,459,899 Not Listed For Sale
- 4 Beds
- 5 Baths
- 4,559 Sq Ft
98 Bacon Rd, Roxbury, CT 06783

98 Bacon Rd, Roxbury, CT 06783

/29
$1,784,000 New Construction
- 5 Beds
- 3.5 Baths
- 3,096 Sq Ft
2 Pickett Rd, Roxbury, CT 06783

NEW CONSTRUCTION. WELCOME TO YOUR DREAM HOME! This stunning new construction colonial farmhouse boasts modern elegance and top-of-the-line finishes throughout. Featuring 5 spacious bedrooms and 3.5 luxurious bathrooms, this home offers ample space for comfortable living. The open concept living area is perfect for entertaining, with a gourmet kitchen that includes high-end stainless-steel

Michael Lissack The Virtual Realty Group

2 Pickett Rd, Roxbury, CT 06783
$917,500 Sold Aug 21, 2025
- 3,004 Sq Ft
- $305/SF
- 82 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1999
88 Mallory Rd, Roxbury, CT 06783

Welcome to wonderful! Enjoy privacy & seclusion on a gorgeous rural road in southern Roxbury. This custom-built, well-designed home is now offered to new stewards by the original owner, ready for year-round country living or a weekend retreat! The expansive property features the 4.5-acre home site plus excess of 8.99 acres for a variety of options...inground pool site, paddocks, animal structures

Melissa Karaffa William Raveis Real Estate

88 Mallory Rd, Roxbury, CT 06783

Est $588,570 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,551 Sq Ft
121 Wellers Bridge Rd, Roxbury, CT 06783

121 Wellers Bridge Rd, Roxbury, CT 06783

/40
$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
$1,825,000 Sold Aug 07, 2025
- 3,450 Sq Ft
- $529/SF
- 319 Days On Market
- 3 Beds
- 3.5 Baths
- Built 1792
44 South St, Roxbury, CT 06783

PETITE ESTATE:South St in the heart of Roxbury, FoxCroft is a classic 1792 Colonial farmhouse on a generous parcel of land. The property includes a heated pool, guest house, studio, 3 car garage with hayloft, and a pond, as well as remnants of its history: an old ice house and a well house. Inside, original fireplaces anchor each of the main rooms, including a large central fireplace with a bread

Lenore Mallett William Pitt Sotheby's Int'l

44 South St, Roxbury, CT 06783

Est $1,219,881 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 3,440 Sq Ft
12 Old Roxbury Rd, Roxbury, CT 06783

12 Old Roxbury Rd, Roxbury, CT 06783

/40
$1,495,000 Pending
- 4 Beds
- 5.5 Baths
- 4,721 Sq Ft
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
$1,378,000 Sold Jul 08, 2025
- 3,481 Sq Ft
- $396/SF
- 44 Days On Market
- 4 Beds
- 4 Baths
- Built 1985
22 Highmeadow Ln, Roxbury, CT 06783

Radiant in Roxbury: A Beautifully Renovated Country Cape Nestled in one of Southern Litchfield County's most sought-after towns, this light-filled home offers an inviting blend of modern amenities and country charm. Two primary suites (one on the main level and one upstairs), two additional bedrooms, home office/guest room, and two full baths on each floor. There's So Much To Love... open kitchen

William Bolls Compass Connecticut, LLC

22 Highmeadow Ln, Roxbury, CT 06783

Est $969,064 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,301 Sq Ft
28 Garnet Rd, Roxbury, CT 06783

28 Garnet Rd, Roxbury, CT 06783

/33
$1,549,000 Under Contract
- 4 Beds
- 3.5 Baths
- 2,437 Sq Ft
253 Tophet Rd, Roxbury, CT 06783

Quintessential CT Mini- Estate of 2 Homes! Top restoration of 3-Bedroom/2.5 bath Victorian plus a Guest House with giant stunning, heated, saltwater pool, 2nd small spa pool and wonderful stone terraces and open lawns. Historic Pool House Rental Income: $50,000-$100,000 per year. Perfect for generational living as both the Main House and the Pool House have their own pools, driveways and garages.

Peter Klemm Klemm Real Estate Inc

253 Tophet Rd, Roxbury, CT 06783
$615,000 Sold Jun 30, 2025
- 2,769 Sq Ft
- $222/SF
- 12 Days On Market
- 3 Beds
- 2 Baths
- Built 1957
79 Wellers Bridge Rd, Roxbury, CT 06783

Welcome to this beautifully updated 3 bed, 2 full bath ranch home nestled on 5.9 peaceful acres in the charming and bucolic Roxbury, CT. This light filled home offers the perfect blend of modern updates and classic comfort in a peaceful country setting.The completely updated kitchen features stainless steel appliances, granite countertops and lovely cabinetry. The spacious living room is warm and

Amy Jeanfaivre Family Realty Group, LLC

79 Wellers Bridge Rd, Roxbury, CT 06783

Est $1,523,862 Not Listed For Sale
- 6 Beds
- 6 Baths
- 5,439 Sq Ft
101 South St, Roxbury, CT 06783

101 South St, Roxbury, CT 06783

/40
$3,975,000
- 5 Beds
- 4 Baths
- 4,371 Sq Ft
67 Squire Rd, Roxbury, CT 06783

67 Squire Road blends striking modern architecture with timeless New England character on nearly 11 private acres in Roxbury. Thoughtfully designed and beautifully executed, this contemporary retreat offers 4,371 sq ft of light-filled living space with 5 bedrooms and 3 spa-quality baths. Radiant-heated white oak floors and walls of glass frame the surrounding landscape, bringing nature into the

Omar Cruz Compass Connecticut, LLC

67 Squire Rd, Roxbury, CT 06783
$1,325,000 Sold Jun 18, 2025
- 3,379 Sq Ft
- $392/SF
- 295 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1980
235 North St, Roxbury, CT 06783

Welcome to this inviting must see country contemporary Tudor style home on beautiful 3.5 acre corner lot in Roxbury. This is country living at its best, as your full time home or weekend escape for every season. Professional landscaped grounds surround this impressive home which is truly a highlight of North Street. The gracious entry foyer gives you an immediate sense of the best of everything

Pels Matthews W. Raveis Lifestyles Realty

235 North St, Roxbury, CT 06783

Est $800,204 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,290 Sq Ft
154 Transylvania Rd, Roxbury, CT 06783

154 Transylvania Rd, Roxbury, CT 06783

/31
$1,155,000
- 4 Beds
- 2.5 Baths
- 3,340 Sq Ft
24 Hickory Ln, Roxbury, CT 06783

Stunning Post & Beam Home with Extensive Upgrades. This beautifully updated Post & Beam residence offers exceptional craftsmanship and modern amenities throughout. Over the past five years, the home has received numerous enhancements, including a new roof, remodeled kitchen with tile flooring, all-new Pella windows and doors, asphalt driveway, 5-zone LP boiler, central A/C unit, and more. The

Sidney Nazario Coldwell Banker Realty

24 Hickory Ln, Roxbury, CT 06783
$1,875,000 Sold Jun 04, 2025
- 3,086 Sq Ft
- $608/SF
- 75 Days On Market
- 3 Beds
- 3 Baths
- Built 1989
257 Southbury Rd, Roxbury, CT 06783

Wonderfully private and updated Roxbury compound with a three bedroom, three bath Mediterranean mid-century vibe main house offering the convenience of one level living. Secluded and dramatic 10 acre property with park-like grounds that flow from the primary residence and gardens down to the saltwater pool with expansive stone terrace and newly renovated guest house. Generously sized, the guest

Maria Taylor Klemm Real Estate Inc

257 Southbury Rd, Roxbury, CT 06783

Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 3,016 Sq Ft
3 Southbury Rd, Roxbury, CT 06783

3 Southbury Rd, Roxbury, CT 06783

/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
$1,490,000 Sold May 22, 2025
- 3,337 Sq Ft
- $447/SF
- 204 Days On Market
- 3 Beds
- 4 Baths
- Built 1998
Unlisted Address

Price Adjustment! Providing wonderful countryside views, this graceful & charming Cape Cod style house has privacy & seclusion, yet it's close to the town center. The Great Room has a vaulted ceiling & a beautiful wood-burning fireplace, an abundance of windows & French doors leading to an expanded deck to take in the views. The remodeled, light-filled, gourmet kitchen includes 2 Sub-Zero freezer

Donna J. Matula William Raveis Real Estate

Unlisted Address

Est $1,439,524 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 3,656 Sq Ft
12 Church St, Roxbury, CT 06783

12 Church St, Roxbury, CT 06783

/40
$1,399,000
- 4 Beds
- 3.5 Baths
- 3,077 Sq Ft
96 Squire Rd, Roxbury, CT 06783

A distinguished equestrian estate of rare beauty, this property unites timeless New England architecture with the serenity of country living. Approached by a gated, tree-lined drive, the residence evokes an air of grace and permanence, set amidst sweeping pastures and centuries-old trees. The main residence exudes historic character and refinement, where wide-plank floors, hand-hewn beams, and

Nikki Defrancesco Coldwell Banker Realty

96 Squire Rd, Roxbury, CT 06783
$749,900 Sold May 19, 2025
- 2,265 Sq Ft
- $331/SF
- 74 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2006
8 Old Ln, Roxbury, CT 06783

Welcome to your dream home! This charming Roxbury Colonial offers the perfect blend of comfort, space, and endless possibilities for your lifestyle. Whether you're relaxing on the inviting front porch or hosting friends in one of the many entertaining areas, you'll find a warm and welcoming atmosphere throughout. The open floor plan creates an ideal space for family and friends to gather, with a

Brandy Granata Coldwell Banker Realty

8 Old Ln, Roxbury, CT 06783

Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 3,087 Sq Ft
294 North St, Roxbury, CT 06783

294 North St, Roxbury, CT 06783

/13
$549,000
- Land
- 24.84 Acres
- $22,101 per Acre
69 Moosehorn Rd, Roxbury, CT 06783

Build your dream on this designated "Scenic Road" abutting spectacular land trust trails. The lot consists of 24.8+/- acres, with a 9+/- acre building envelop. The building site is to be accessed from a future driveway running at the South border, along the Land Trust access point. The lightly wooded property rises to an 820-foot elevation and is resplendent with mature trees, ferns, moss and

Stacey Matthews W. Raveis Lifestyles Realty

69 Moosehorn Rd, Roxbury, CT 06783
$795,000 Sold May 16, 2025
- 2,931 Sq Ft
- $271/SF
- 322 Days On Market
- 3 Beds
- 3 Baths
- Built 1998
13 Evergreen Dr, Roxbury, CT 06783

BEST Value with a Pool in Litchfield County! Stylish Private Modern with Infinity Edge Heated Pool. This Hip Modern Home Has an Open Floor-plan & Airy Feel. 3 Bedrooms, 3 Updated Baths. Inviting Eat-in Kitchen Speaks to Large Family Room with Fireplace & Vaulted Ceiling. Wonderful Formal Living Room with Modern Fireplace & Vaulted Ceiling. Generous Primary Bedroom Commands the Upper Level

Graham Klemm Klemm Real Estate Inc

13 Evergreen Dr, Roxbury, CT 06783

Not Listed For Sale
- 3 Beds
- 3 Baths
- 3,091 Sq Ft
277 Southbury Rd, Roxbury, CT 06783

277 Southbury Rd, Roxbury, CT 06783

/40
$3,650,000
- 4 Beds
- 4.5 Baths
- 5,072 Sq Ft
35 Schoolhouse Rd, Roxbury, CT 06783

Subtle Sophistication in A++ Roxbury Locale. Perfectly sited in an estate area of Roxbury on a quiet country road, this renovated country cottage exudes understated elegance & modern comfort. Main house offers one-level living & turn-key perfection, w/chic kitchen featuring custom cabinetry, stainless steel appliances, it flows seamlessly into the dining room. Dramatic great room

Pels Matthews W. Raveis Lifestyles Realty

35 Schoolhouse Rd, Roxbury, CT 06783
$940,000 Sold May 07, 2025
- 3,088 Sq Ft
- $304/SF
- 195 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1999
80 Transylvania Rd, Roxbury, CT 06783

Modern Farmhouse Oasis on 4 Acres in Peaceful Roxbury. A winding drive leads you to the home, where elegant stone steps guide you to a covered porch, surrounded by a lush perennial garden. Inside, the sophisticated living room features French doors, grasscloth wall-covering, and crown molding. This seamlessly connects to a formal dining room with tray ceiling and a bay window. The heart of the

Kathryn Bassett William Pitt Sotheby's Int'l

80 Transylvania Rd, Roxbury, CT 06783

Est $1,445,359 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 4,040 Sq Ft
167 Tophet Rd, Roxbury, CT 06783

167 Tophet Rd, Roxbury, CT 06783

/40
$3,200,000
- 3 Beds
- 2 Baths
- 1,974 Sq Ft
4 Judge Rd, Roxbury, CT 06783

Complete Equestrian Facility with Cape Cod Style Home. An ideal property for horse enthusiasts, trainers, or those seeking a turn-key boarding operation. This thoughtfully designed equestrian facility offers 16 matted stalls, a spacious indoor riding arena, and an elevated viewing area with a kitchen-perfect for hosting clinics, lessons, or simply watching rides in comfort. The barn also includes

Heather Crabtree Coldwell Banker Realty

4 Judge Rd, Roxbury, CT 06783
$2,858,000 Sold May 02, 2025
- 3,043 Sq Ft
- $939/SF
- 15 Days On Market
- 4 Beds
- 5.5 Baths
- Built 2018
42 Berry Rd, Roxbury, CT 06783

Impeccable 4 Bedroom, 5.5 Bath Colonial with Heated Pool. Set Privately Along Quaint Dead-End Town Rd. Jaw-Dropping Kitchen/Great Room with Vaulted Ceiling & Fireplace. Main Level Primary Suite with Luxurious Full Bath. Exquisite Living Room with Beamed Ceiling & Gas Fireplace. Heated Gunite Pool Steps from Finished Lower Level with Wet Bar, 2 Full Baths, Gym & Bedroom. 2 en-Suite Upper Bedrooms

Graham Klemm Klemm Real Estate Inc

42 Berry Rd, Roxbury, CT 06783

Not Listed For Sale
- 4 Beds
- 6 Baths
- 5,808 Sq Ft
19 Golden Harvest Rd, Roxbury, CT 06783

19 Golden Harvest Rd, Roxbury, CT 06783

/39
$995,000
- 3 Beds
- 2.5 Baths
- 2,556 Sq Ft
336 South St, Roxbury, CT 06783

Quintessential Roxbury retreat, an updated classic 3-bedroom Colonial with open floor plan and separate office, nestled on over 4.5 picturesque park-like acres. This property offers the perfect blend of tranquil country living with the convenience of a great commuting location, just 90 minutes to NYC. Step inside to discover a home that has been freshly painted both inside and out, exuding a

Kathryn Clair William Pitt Sotheby's Int'l

336 South St, Roxbury, CT 06783
$645,000 Sold Apr 25, 2025
- 2,382 Sq Ft
- $271/SF
- 62 Days On Market
- 3 Beds
- 2 Baths
- Built 1943
396 Southbury Rd, Roxbury, CT 06783

Welcome home to 396 Southbury Rd in charming Roxbury CT in desirable Litchfield Hills. In off-winter months, one will adore the lush green landscaped grounds on these 4 tranquil acres. Nature's beauty at its best, lovely pond, a place of peace & solace, a treasure to call Home Sweet Home. Where rustic Country design meets distinctive Swiss Chalet styling - complete w/window flower boxes! This is

Mirella D'Antonio William Raveis Real Estate

396 Southbury Rd, Roxbury, CT 06783

Est $1,884,170 Not Listed For Sale
- 3 Beds
- 2 Baths
- 3,050 Sq Ft
36 Clover Knolls, Roxbury, CT 06783

36 Clover Knolls, Roxbury, CT 06783

/34
$739,000
- 4 Beds
- 3 Baths
- 2,682 Sq Ft
55 Mallory Rd, Roxbury, CT 06783

If privacy in the Litchfield Hills is your aspiration, this is the residence for you! Pass through the gated entrance to this rustic Country Cape with covered front porch set back 500 feet off the road. Property abuts land locked acreage & Roxbury Land Trust surrounds much of the neighborhood. The current & ONLY owner constructed this quality built home with lasting craftsmanship. To say it has

Gina Jacobs Gina Jacobs Real Estate

55 Mallory Rd, Roxbury, CT 06783
$1,725,000 Sold Apr 25, 2025
- 4,112 Sq Ft
- $420/SF
- 186 Days On Market
- 4 Beds
- 4.5 Baths
- Built 2011
381 South St, Roxbury, CT 06783

Meander over a small bridge and through tall pines to reach this distinctive 4 bedroom home on 6 very private acres. A gracious wood paneled central foyer directs you into the living room, dining room, or through to a thoughtfully designed great room. The kitchen features a wrap-around island with bar stools, high-end appliances walk-in pantry/laundry. It also opens to the breakfast nook and

Stacey Matthews W. Raveis Lifestyles Realty

381 South St, Roxbury, CT 06783

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