13

Newest Homes for Rent in Roxbury, CT

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  • /5

    $1,925

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 1,000 Sq Ft
    • House for Rent

    24 Loomba Dr, Roxbury, CT 06783

    Basement level of beautiful single family home on private property with pond and near a river.

    24 Loomba Dr, Roxbury, CT 06783
  • /29

    $35,000 Per Month

    • 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
  • /40

    $7,500 Per Month

    • 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 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 it's own

    Christopher Haggerty Compass Connecticut, LLC

    7 Lower County Rd, 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 Mid July 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
  • /28

    $6,000 Per Month

    • 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
  • /28

    $16,500 Per Month

    • 4 Beds
    • 2.5 Baths
    • 3,089 Sq Ft
    • House for Rent

    5 North St, Roxbury, CT 06783

    NEW PRICE Summer 2026: July and/or August at $16,500 per month. 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 and a Wonderful

    Melinda Dubow Klemm Real Estate Inc

    5 North St, 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 Sept 2026 - May 2027 @ $15,000/mo and $35,000 for August 2026. Enjoy Modern Luxury in Connecticut's Countryside. New Gunite heated pool being installed April 2026. This 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

    Stacey Matthews W. Raveis Lifestyles Realty

    34 Old Roxbury Rd, Roxbury, CT 06783
  • /38

    $15,000 Per Month

    • 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
  • /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
  • /25

    $26,900 Per Month

    • 4 Beds
    • 2.5 Baths
    • 1,782 Sq Ft
    • House for Rent

    23 Painter Hill Rd, Roxbury, CT 06783

    Pristine hilltop art filled home with views and only a short walk to Maple Bank Farm Stand, Toplands Farm and historic Roxbury Center. Wood burning fireplace, vaulted master bedroom with balcony and private bath. Dine or relax on the flagstone terrace. Ping pong, trampoline, croquet, badminton, gas BBQ, fire pit, bikes and board games. SUMMER June - August $18,900/month; OFF-SEASON September -

    Peter Klemm Klemm Real Estate Inc

    23 Painter Hill Rd, Roxbury, CT 06783
  • /33

    $24,900 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,080 Sq Ft
    • House for Rent

    Unlisted Address

    Meander down the most scenic of Roxbury dirt roads to reach "Tunnel Road 4-BR" tucked between the Shepaug River, historic wood Judd's Bridge and Farm and 1000 acres of Steep Rock land trust with endless hiking trails. Pristine renovated private country home with year round 8'x 16' spa pool, wood burning fireplace and open floor plan. Dine or relax on the granite terrace or covered front porch.

    Peter Klemm Klemm Real Estate Inc

    Unlisted Address
  • /22

    $30,900 Per Month

    • 3 Beds
    • 3.5 Baths
    • 4,251 Sq Ft
    • House for Rent

    45 Moosehorn Rd, Roxbury, CT 06783

    Perfect 6BR 3.5 Bath home with heated pool and child's play gym on a scenic country dirt road that leads into a land preserve along the Shepaug River - perfect for walking, jogging, biking. The most desirable rural historic location within 2 hours of NYC - Roxbury and Washington CT. Home to actors, writers, artists and the owners of luxury estate vacation homes. Many world class restaurants, inns

    Peter Klemm Klemm Real Estate Inc

    45 Moosehorn Rd, Roxbury, CT 06783
  • /29

    $30,900 Per Month

    • 6 Beds
    • 3.5 Baths
    • 2,716 Sq Ft
    • House for Rent

    33 Sentry Hill Rd, Roxbury, CT 06783

    Mint 6 bedroom colonial reproduction on scenic dirt road. Walk, jog, bike into land preserve. Heated pool, outdoor play set, bbq, 3 acre lawn, 4 wood-burning fireplaces. SUMMER:June - August $30,900/month. Memorial - Labor Day $74,900.OFF-SEASON: September - May $13,900/month If over 3 months, subtract $1,000 per month and no tax is due. ANNUAL:$169,000. Inquire about other/shorter rental terms.

    Peter Klemm Klemm Real Estate Inc

    33 Sentry Hill Rd, Roxbury, CT 06783

Frequently Asked Questions

How much does it cost to rent a home in Roxbury, CT?
The median rent for a home in Roxbury, CT is $15,000 per month, though prices vary by neighborhood, size, and property type. As of May 2026, single-family homes tend to be the most affordable option.
How much do you need to make to afford rent in Roxbury, CT?
To comfortably afford the median rent in Roxbury, CT, a household needs to earn roughly $600,000 per year. This is based on the common guideline that households should spend no more than 30% of gross income on housing. Most landlords require monthly household income of at least 3x the monthly rent, and with a median rent of $15,000 per month in Roxbury, CT, renters typically need to show $45,000 per month in gross income to qualify. Actual affordability will vary depending on household debts, other living expenses, and overall budget.
Is it more affordable to rent or buy in Roxbury, CT?
In Roxbury, CT, the price-to-rent ratio is 7.8, which generally favors renting. This ratio divides the median home price by the annual median rent: below 15 typically favors buying, 15 to 20 is balanced, and above 20 typically favors renting. Your finances, how long you plan to stay, and costs like mortgage rates, taxes, and maintenance all factor into the decision.
What neighborhoods in Roxbury, CT are best for renting a home?
The best neighborhood for renting in Roxbury, CT depends on your priorities: commute, walkability, budget, and lifestyle all play a role. Popular areas for renting a home include Bunker Hill, West End District, Village of Waterbury and North End District, each with its own character and price range.

Rental Home Trends in Roxbury, CT

Rental Home Trends

Number of Homes for Rent
13
Median Rent
$15,000
Median Single Family Home Rent
$15,000
How to Rent a Home