1,388

Roxbury, CT Homes

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  • /40

    $1,495,000

    • 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
  • /14

    $2,500 per month

    • 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.

    Agent Photo

    Rebecca Doh

    W. Raveis Lifestyles Realty

    (860) 750-8200

    160 North St, 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
  • /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
  • /8

    $2,200 per month

    • 1 Bed
    • 1 Bath
    • 900 Sq Ft
    • House for Rent

    10 (LOWER) Sentry Hill Rd, Roxbury, CT 06783

    Available January, 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

    Melinda Dubow Klemm Real Estate Inc

    10 (LOWER) Sentry Hill Rd, 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
  • /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

    $6,000 per month

    • 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
  • 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
  • /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
  • /21

    $4,200 per month

    • 4 Beds
    • 2.5 Baths
    • 2,336 Sq Ft
    • House for Rent

    38 W Mountain Ln, Roxbury, CT 06783

    Located on a quiet private road in Roxbury, this open concept, four bedroom home is awaiting its new tenants. Get in before the end of the summer and beginning of the school year, nothing to do but move in! With recently refinished floors and new appliances, this neat and clean home offers three bathrooms, plenty of privacy, large basement for storage and detached two car garage. Good credit a

    Katherine Parlato Drakeley Real Estate, Inc.

    38 W Mountain Ln, 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
  • /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
  • /40

    $25,000 per month

    • 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
  • 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
  • /22

    $1,975,000

    • 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
  • /37

    $6,500 per month

    • 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
  • 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
  • /21

    $1,625,000

    • 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
  • /28

    $20,000 per month

    • 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
  • 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
  • /27

    $1,525,000

    • 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
  • /25

    $7,000 per month

    • 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
  • 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
  • /33

    $1,575,000

    • 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
  • /27

    $15,000 per month

    • 4 Beds
    • 6 Baths
    • 3,996 Sq Ft
    • House for Rent

    34 Old Roxbury Rd, Roxbury, CT 06783

    Available for $15,000/mo for 2025/26 school year 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
  • 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
  • /39

    $2,150,000

    • 4 Beds
    • 5 Baths
    • 4,728 Sq Ft

    32 Grassy Hill Rd, Roxbury, CT 06783

    Roxbury dream home with forever views. Tucked away down a gracious drive off a bucolic town road this quintessential Georgian welcomes you home and envelopes you in calm and comfort. Arrival at the motor court provides the first glimpse of a western view that stretches from Roxbury as far as the eye can see, giving an immediate sense of place. The home, unabashedly radiant in its sunny yellow

    Rick Distel Compass Connecticut, LLC

    32 Grassy Hill Rd, Roxbury, CT 06783
  • /17

    $7,500 per month

    • 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
  • 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

Showing Results 1 - 40, Page 1 of 18

Home Trends in Roxbury, CT

Housing Trends

Median Sale Price
$1,300,000
Median Single Family Sale Price
$1,400,000
Median Townhouse Sale Price
$950,000
Average Price Per Sq Ft
$515
Number of Homes for Sale
28
Last 12 months Home Sales
51
Months of Supply
6.60
Median List Price
$1,624,500
Median Change From 1st List Price
9%
Median Home Sale Price YoY Change
5%
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