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Roxbury, CT Homes for Rent

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  • 5 North St, Roxbury, CT 06783
    5 North St, Roxbury, CT 06783
    5 North St, Roxbury, CT 06783
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    $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
  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /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
  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /29

    $8,500 Per Month

    • 3 Beds
    • 3.5 Baths
    • 3,389 Sq Ft
    • House for Rent

    Unlisted Address

    Oct-May Rental. Newly Renovated & Exquisitely Appointed Barn House. Set Along a Very Low Traveled Unpaved Town Road, This is a Very Chic & Sophisticated 3Bedroom, 3.5 Bath Retreat Including: A Main Level Primary Bedroom with Fireplace & New Full Bath. Wonderful Public Rooms Include: Large Living Room with Vaulted Ceiling, Fireplace & Antique Beams; Formal Dining Room & A Timeless Eat-in Kitchen

    Graham Klemm Klemm Real Estate Inc

    Unlisted Address
  • 10 (UPPER) Sentry Hill Rd, Roxbury, CT 06783
    10 (UPPER) Sentry Hill Rd, Roxbury, CT 06783
    10 (UPPER) Sentry Hill Rd, Roxbury, CT 06783
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    $3,450 Per Month

    • 3 Beds
    • 2 Baths
    • 1,260 Sq Ft
    • House for Rent

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

    Upper 3-bedroom, 2-bath now available from 8/1/26 @ $4,500 for August, 9/'26 Academic/Annual @ $3,500. 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 3-bedroom, 2 bath home rests on five acres with a gentle stream running through it.

    Melinda Dubow Klemm Real Estate Inc

    10 (UPPER) Sentry Hill Rd, Roxbury, CT 06783
  • 24 Old Roxbury Rd, Roxbury, CT 06783
    24 Old Roxbury Rd, Roxbury, CT 06783
    24 Old Roxbury Rd, Roxbury, CT 06783
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    $15,000 Per Month

    • 3 Beds
    • 3.5 Baths
    • 2,862 Sq Ft
    • House for Rent

    24 Old Roxbury Rd, Roxbury, CT 06783

    Available Oct 1, 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 plan

    Stacey Matthews W. Raveis Lifestyles Realty

    24 Old Roxbury Rd, Roxbury, CT 06783
  • 45 Moosehorn Rd, Roxbury, CT 06783
    45 Moosehorn Rd, Roxbury, CT 06783
    45 Moosehorn Rd, Roxbury, CT 06783
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    $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
  • 23 Painter Hill Rd, Roxbury, CT 06783
    23 Painter Hill Rd, Roxbury, CT 06783
    23 Painter Hill Rd, Roxbury, CT 06783
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    $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 Sentry Hill Rd, Roxbury, CT 06783
    33 Sentry Hill Rd, Roxbury, CT 06783
    33 Sentry Hill 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
Connecticut Litchfield County

Homes for Rent in Roxbury, CT

Why Live in Roxbury

Roxbury, CT, located in the Litchfield Hills just east of Bridgeport, offers a rural lifestyle with nearby urban amenities. Spanning 27 square miles with a population of over 2,000, Roxbury is known for its quiet, undeveloped landscape. Residents enjoy outdoor attractions like Hurlburt Park, which hosts the annual Roxbury Pickin’ and Fiddlin’ Contest, and River Road Preserve, ideal for hiking and fly-fishing. History enthusiasts can explore Mine Hill Preserve, featuring remnants of a 19th-century iron-making complex and extensive hiking trails. Adjacent to Mine Hill is the Kelsey Museum and Sculpture Garden, showcasing works by Sterett-Gittings Kelsey, and the Mine Hill Distillery, where visitors can sample locally distilled spirits. Homes in Roxbury range from raised ranch-style houses to historic Colonial homes, often situated on large lots with mature trees. The town is served by Regional School District Number 12, with highly rated Booth Free School and Shepaug Valley School, along with the nearby Kent School. While Roxbury lacks extensive commercial activity, residents can visit the Roxbury Market & Deli for groceries and meals, or travel 20 miles to Waterbury for more shopping options. For a broader shopping experience, New York City is accessible by train from Danbury, less than 20 miles south.

Learn more about living in Roxbury

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 $20,700 per month, though prices vary by neighborhood, size, and property type. As of July 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 $828,000 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 $20,700 per month in Roxbury, CT, renters typically need to show $62,100 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 5.9, 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 West End District, Village of Waterbury, South End District and North End District, each with its own character and price range.

Rental Trends in Roxbury, CT

There are currently 8 homes available for rent in Roxbury, CT. The median rent is $20,700 per month, with single-family homes renting at $16,500.

Rental Home Trends

Number of Homes for Rent
8
Median Rent
$20,700
Median Single Family Home Rent
$16,500
How to Rent a Home

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