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Middlebury, CT Homes for Rent

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  • /32

    $3,400 Per Month

    • 4 Beds
    • 2 Baths
    • 2,245 Sq Ft
    • House for Rent

    111 North St, Middlebury, CT 06762

    A beautiful rental in Middlebury, CT history. Located near "The Green" on desired North Street, This Charming Greek Revival home has so many upgrades! Sitting on private acres, this home boasts 10 spacious rooms, 4 bedrooms,LR with fireplace, DR with Fireplace,Eat In Kitchen with an island, library/office with built ins and 2 sitting rooms. The two full baths have claw tubs and have been fully

    Agent Photo

    Bonnie Wilson

    Berkshire Hathaway NE Prop.

    111 North St, Middlebury, CT 06762
  • /14

    $2,800 Per Month

    • 4 Beds
    • 2 Baths
    • 1,766 Sq Ft
    • House for Rent

    443 Benson Rd, Middlebury, CT 06762

    Come view this spacious, modern four bedroom 2 full bathroom single family home for rent! This home features a fresh looking kitchen with all white appliances and plenty of white cabinetry for all your storage needs! Enjoy the experience of living on a home set back from the street and enjoy the sights of nature looking out over the extensive yard from your very own deck! Book an appointment

    Levi Judqin Brass Moon Realty

    443 Benson Rd, Middlebury, CT 06762
  • /33

    $17,000 Per Month

    • 5 Beds
    • 7 Baths
    • 6,600 Sq Ft
    • House for Rent

    372 Tucker Hill Rd, Middlebury, CT 06762

    5 bedrooms 4,3 baths cape house set on 3.5 acres.

    Naima Mazouzi Eagle Eye Realty PLLC

    372 Tucker Hill Rd, Middlebury, CT 06762
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    $3,700 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,874 Sq Ft
    • House for Rent

    405 Washington Dr, Middlebury, CT 06762

    Incredible spacious and bright custom colonial home with 3 levels of comfortable living. This charming home features a large welcoming foyer, with a formal living room and formal dining room. Living room opens up to a large open family room with gas fireplace, French doors that lead to a balcony. Eat in Kitchen with bay window with magnificent views boasts hardwood, Cherry cabinets, granite

    Gina Farra Keller Williams Realty

    405 Washington Dr, Middlebury, CT 06762

Why Live in Middlebury

Middlebury, Connecticut, is a picturesque New England town located in New Haven County, known for its scenic beauty and tight-knit community. With a population of 7,500, Middlebury offers a blend of rural charm and urban accessibility, being a short drive from New Haven. The town is surrounded by lush forests, state parks, rolling hills, and lakes, with nearly 2,000 acres of conserved land, making it a haven for outdoor activities. Residents enjoy local attractions such as Meadowview Park, Quassapaug Lake, and the Middlebury Greenway, as well as nearby state forests like Naugatuck, Mattatuck, and Paugussett, which offer extensive trails and recreational opportunities. Middlebury's educational system is highly regarded, with Pomperaug Regional School District No. 15 and Westover School providing top-notch education. The town's largest employers include Timex Group, Quassy Amusement Park, Waterbury Hospital, and Danbury Hospital. Middlebury maintains a low crime rate compared to the national average, contributing to its appeal for families and retirees. The housing market features classic New England homes, historic colonials, Cape Cods, and lakeside retreats, with properties often including antique barns and garden areas. Local businesses thrive in Middlebury, with popular spots like Willie’s Wood Smoked BBQ, The Local Gourmet, Vyne Restaurant, and Pies & Pub. The town's biggest entertainment draw is Quassy Amusement Park, one of the nation's oldest amusement parks. Middlebury is well-connected via Interstates 8 and 84, State Routes 63 and 64, and is close to Tweed New Haven Airport and Windsor Locks International Airport. Despite recent development proposals, the community remains committed to preserving its small-town charm.

Frequently Asked Questions

How much does it cost to rent a home in Middlebury, CT?
The median rent for a home in Middlebury, CT is $3,550 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 while condos and townhouses are currently more expensive.
How much do you need to make to afford rent in Middlebury, CT?
To comfortably afford the median rent in Middlebury, CT, a household needs to earn roughly $142,000 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 $3,550 per month in Middlebury, CT, renters typically need to show $10,650 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 Middlebury, CT?
In Middlebury, CT, the price-to-rent ratio is 13.1, 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 Middlebury, CT are best for renting a home?
The best neighborhood for renting in Middlebury, CT depends on your priorities: commute, walkability, budget, and lifestyle all play a role. Popular areas for renting a home include West End District, Bunker Hill, South End District, Village of Waterbury and North End District, each with its own character and price range.

Rental Home Trends

Number of Homes for Rent
4
Median Rent
$3,550
Median Single Family Home Rent
$2,200
Median Townhouse Rent
$3,950
Median Condo Rent
$2,875
How to Rent a Home