1,385

Homes in ZIP Code 06783

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  • 33 Sentry Hill Rd, Roxbury, CT 06783
    33 Sentry Hill Rd, Roxbury, CT 06783
    33 Sentry Hill Rd, Roxbury, CT 06783
    /27

    $1,475,000

    • 4 Beds
    • 3.5 Baths
    • 2,716 Sq Ft

    33 Sentry Hill Rd, Roxbury, CT 06783

    Mint/Move-in Condition! Private c. 2002 Colonial Clapboard 4+ bedroom home on a scenic dirt road along the Shepaug River and just down the road from Land Trust with trails. Heated Gunite Pool surrounded by endless summer hydrangea and 3 acres of level lawn bordered by the Moosehorn Brook. Magnificent design, 4 wood-burning fireplaces, beautiful wide-board softwood floors, over-sized living room,

    Peter Klemm Klemm Real Estate Inc

    33 Sentry Hill Rd, Roxbury, CT 06783
  • 27 Wakelee Rd, Roxbury, CT 06783

    $1,837,500 Sold Sep 16, 2025

    • 2,640 Sq Ft
    • $696/SF
    • 357 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1815

    27 Wakelee Rd, Roxbury, CT 06783

    Many new renovations in this stunning antique home on a quiet country road. All flat usable land with gorgeous bank barn, gunite pool, Spectacular mature trees, and pond. Town has house listed as 5 bedrooms. The primary bedroom with walk in closet is on the main level. Upstairs is more efficiently used as 2 suites each with walk in closets or offices. Alternately, one of the larger bedrooms could

    Stacey Matthews W. Raveis Lifestyles Realty

    27 Wakelee Rd, Roxbury, CT 06783
  • 97 Chalybes Rd W, Roxbury, CT 06783
    97 Chalybes Rd W, Roxbury, CT 06783
    97 Chalybes Rd W, 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
  • 322 North St, Roxbury, CT 06783

    $500,000 Sold Sep 05, 2025

    • 1,397 Sq Ft
    • $358/SF
    • 84 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1977

    322 North St, Roxbury, CT 06783

    An artists custom retreat can now be your blank slate. 5.48 acres, straddles the towns of Roxbury (3.36 acres) and Washington (2.12 acres) Best of both worlds! Tucked back into the lightly treed lot bounded by old stonewalls, this unique home offers vaulted ceilings, hardwood flooring on both levels, bright sunroom off the kitchen, dining room or den on main level. Cozy woodstove in LR. The

    Mary Ann Bennett Drakeley Real Estate, Inc.

    322 North St, Roxbury, CT 06783
  • 67 Transylvania Rd, Roxbury, CT 06783
    67 Transylvania Rd, Roxbury, CT 06783
    67 Transylvania Rd, Roxbury, CT 06783
    /40

    $919,000

    • 4 Beds
    • 4 Baths
    • 3,624 Sq Ft

    67 Transylvania Rd, Roxbury, CT 06783

    This place is a real gem! It needs some updates, but the structure is solid, and the property is beyond compare. It's set on over three gorgeous acres with beautiful stone walls and a private usable yard that's perfect for a pool. Extensive stonework is present on side steps, patios, and rear gardens, complemented by a stone breezeway connecting the 3-car garage to a side entry hall. The driveway

    Cathy Masi Flagpole Realty Inc

    67 Transylvania Rd, Roxbury, CT 06783
  • 18 Mallory Rd, Roxbury, CT 06783

    $2,575,000 Sold Aug 29, 2025

    • 3,384 Sq Ft
    • $761/SF
    • 53 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1750

    18 Mallory Rd, Roxbury, CT 06783

    Idyllic Period Colonial with Pool Set Along Tranquil Town Road. This c1750 Colonial Has been Tastefully Updated & Expanded. 3 Bedrooms, 3.5 Baths. Central AC. Striking Gunite Pool Set Privately & Surrounded by Lush Landscape & Stone Terracing. Beautifully Proportioned Public Rooms Include: Living Room with Fireplace; Formal Dining Room; Library with Fireplace; Large Eat-in Kitchen with Fireplace

    Graham Klemm Klemm Real Estate Inc

    18 Mallory Rd, Roxbury, CT 06783
  • 67 Squire Rd, Roxbury, CT 06783
    67 Squire Rd, Roxbury, CT 06783
    67 Squire Rd, 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
  • 67 Botsford Hill Rd, Roxbury, CT 06783

    $1,800,000 Sold Aug 28, 2025

    • 4,800 Sq Ft
    • $375/SF
    • 116 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1988

    67 Botsford Hill Rd, Roxbury, CT 06783

    Discover the appeal of this Swedish inspired shingle-style beauty with light and modern finishes throughout. It's nestled into 41+ ultra-private acres on a picturesque country road. Enter the front door into the two-story foyer which flows into the vaulted ceiling living room with lots of glass, adobe fireplace and easy access to the tucked away library with floor to ceiling bookshelves. The

    Maria Taylor Klemm Real Estate Inc

    67 Botsford Hill Rd, Roxbury, CT 06783
  • 24 Hickory Ln, Roxbury, CT 06783
    24 Hickory Ln, Roxbury, CT 06783
    24 Hickory Ln, Roxbury, CT 06783
    /40

    $1,155,000

    • 4 Beds
    • 2.5 Baths
    • 3,340 Sq Ft

    24 Hickory Ln, Roxbury, CT 06783

    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 inviting interior centers around a dramatic two-story

    Sidney Nazario Coldwell Banker Realty

    24 Hickory Ln, Roxbury, CT 06783
  • 19 Good Hill Terrace, Roxbury, CT 06783

    $1,465,000 Sold Aug 22, 2025

    • 3,022 Sq Ft
    • $485/SF
    • 41 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1986

    19 Good Hill Terrace, Roxbury, CT 06783

    Welcome to this enchanting Roxbury home that feels like a private oasis. This stunning property sits on over 7 acres and features a heated saltwater pool, a chef's kitchen with an open concept that overlooks the great room with vault ceilings, and radiant heated floors that leads to the patio, gardens, and pool. A custom built heated 2 story post and beam barn that offers a 3-car garage was built

    Tanya Uhelsky RE/MAX RISE

    19 Good Hill Terrace, Roxbury, CT 06783
  • 38 W Mountain Ln, Roxbury, CT 06783
    38 W Mountain Ln, Roxbury, CT 06783
    38 W Mountain Ln, 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
  • 88 Hemlock Rd, Roxbury, CT 06783

    $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
  • 96 Squire Rd, Roxbury, CT 06783
    96 Squire Rd, Roxbury, CT 06783
    96 Squire Rd, 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
  • 88 Mallory 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
  • 69 Moosehorn Rd, Roxbury, CT 06783
    69 Moosehorn Rd, Roxbury, CT 06783
    69 Moosehorn Rd, 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
  • 44 South St, 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
  • 4 Judge Rd, Roxbury, CT 06783
    4 Judge Rd, Roxbury, CT 06783
    4 Judge 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
  • 22 Highmeadow 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
  • 336 South St, Roxbury, CT 06783
    336 South St, Roxbury, CT 06783
    336 South St, Roxbury, CT 06783
    /39

    $995,000

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

    336 South St, Roxbury, CT 06783

    Quintessential Roxbury retreat, an updated classic 4-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
  • 79 Wellers Bridge 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
  • 55 Mallory Rd, Roxbury, CT 06783
    55 Mallory Rd, Roxbury, CT 06783
    55 Mallory Rd, 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 place for you! Pass through the gated entrance to this rustic Country Cape w/ covered front porch set back 500 ft 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 good

    Gina Jacobs Gina Jacobs Real Estate

    55 Mallory Rd, Roxbury, CT 06783
  • 235 North St, 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
  • 179 South St, Roxbury, CT 06783
    179 South St, Roxbury, CT 06783
    179 South St, Roxbury, CT 06783
    /25

    $1,275,000

    • 3 Beds
    • 2 Baths
    • 1,772 Sq Ft

    179 South St, Roxbury, CT 06783

    Own a Piece of Roxbury History! One of Roxbury's three oldest homes, this site has been cherished by seven generations of the Squire family. The existing antique home, while requiring reconstruction, has the potential to be reimagined as a charming guest house, preserving a tangible link to the past. Set on 12.7-acres this property and boasts breathtaking eastern views and the unique opportunity

    Kathryn Clair William Pitt Sotheby's Int'l

    179 South St, Roxbury, CT 06783
  • 257 Southbury Rd, 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
  • 31 Holmes Rd, Roxbury, CT 06783
    31 Holmes Rd, Roxbury, CT 06783
    31 Holmes Rd, Roxbury, CT 06783
    /10

    $450,000

    • Land
    • 8.21 Acres
    • $54,811 per Acre

    31 Holmes Rd, Roxbury, CT 06783

    Peaceful 8.2-acre parcel located on a scenic, quiet road in Roxbury. Enveloped by mature hardwood forest with pockets of dappled sunlight and native fern understory, this magical setting offers both beauty and privacy. Set near the tri-town border of Roxbury, Washington, and Woodbury, the location offers easy access to all the amenities and charm of each town, including farmers markets, hiking

    Kathryn Bassett William Pitt Sotheby's Int'l

    31 Holmes Rd, Roxbury, CT 06783
  • Unlisted Address

    $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
  • 50 Southbury Rd, Roxbury, CT 06783
    50 Southbury Rd, Roxbury, CT 06783
    50 Southbury Rd, Roxbury, CT 06783
    /31

    $950,000

    • 5 Beds
    • 3 Baths
    • 2,000 Sq Ft

    50 Southbury Rd, Roxbury, CT 06783

    Cottage, Guest House & Buildable Lot Exceptional estate opportunity in pastoral Southern Roxbury, just 90 minutes from New York City. Set on 8.71 acres, the property features a historic c.1817 three-bedroom antique cape-featured in Elle Decor-a charming two-bedroom guest house, and a separate 6.71-acre buildable lot with potential for a spacious custom home at the end of a long, private driveway.

    Jeff Phillips William Pitt Sotheby's Int'l

    50 Southbury Rd, Roxbury, CT 06783

Showing Results 41 - 80, Page 2 of 18

Connecticut Litchfield County Roxbury 06783

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