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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
  • /18

    $3,995 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,277 Sq Ft
    • Townhouse for Rent

    10 Dogwood Ct Unit 10, Middlebury, CT 06762

    Welcome to this beautiful Ridgewood unit offering comfortable, easy living in a desirable setting. The main level features a modern kitchen, spacious primary suite, convenient laundry, and an inviting living area that opens to a private rear deck overlooking peaceful wooded surroundings. Upstairs, you'll find two additional bedrooms with a bright loft space between them-perfect for a home office,

    Stephanie Chapman BHGRE Gaetano Marra Homes

    10 Dogwood Ct Unit 10, 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 $3,697 per month, though prices vary by neighborhood, size, and property type. As of September 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 $147,880 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 $3,697 per month in Middlebury, CT, renters typically need to show $11,091 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 12.7, 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
2
Median Rent
$3,697
Median Single Family Home Rent
$2,200
Median Townhouse Rent
$3,950
Median Condo Rent
$3,850
How to Rent a Home