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Woodbury, CT Homes for Rent

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    Starting at $1,674

    Total Monthly Price

    • Studio - 2 Beds

    302 Tuttle Rd, Woodbury, CT 06798

    Welcome to Woodbury Knoll Apartments, where modern comfort meets tranquil, lakeside living. Life unfolds at a different pace here — mornings are inspired by nature's quiet beauty, and evenings unwind in serene surroundings. In our apartments in Woodbury, CT, you'll discover a lifestyle that's vibrant yet peaceful, perfectly balanced, and endlessly welcoming.

    Woodbury Knoll

    302 Tuttle Rd, Woodbury, CT 06798
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    $1,850 Plus Fees

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    259 Main St S Unit 2, Woodbury, CT 06798

    Property Id: 2072920 Light and bright 2 Story 1 Bedroom Condo available for occupancy. This unit comes with a spacious and open first floor lay out, kitchen with extra cabinet space and more. The second floor has a full bathroom and spacious Bedroom with ample closet space. This condo is located on Woodbury most desirable areas and will not last long so don't wait schedule a tour today!

    259 Main St S Unit 2, Woodbury, CT 06798
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    $1,800

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • Condo for Rent

    31 Pilgrim Trail Unit 31-5 PILGRIM TRAIL, Woodbury, CT 06798

    Impeccable large 2nd floor end unit, bright, cheerful and safe location with beautiful views. Freshly painted and professionally cleaned with new carpeting throughout. Rent includes heat, hot water and appliances. Tenant pays electric, cable/internet, renters insurance. Trash and recycling services and all grounds maintenance also included. New mini blinds throughout. Neighborhood is quiet and

    31 Pilgrim Trail Unit 31-5 PILGRIM TRAIL, Woodbury, CT 06798
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    $30,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 3,282 Sq Ft
    • House for Rent

    28 Leavenworth Rd, Woodbury, CT 06798

    STUNNING RENTAL with POOL and TENNIS COURT (with lights). Enjoy summer(offered for July and/or August) at this resort-style escape with newly renovated interior and incredible entertaining space indoors and out. Extraordinary cook's kitchen with breakfast nook opens into an expansive sun-filled room overlooking lawns, tennis court and pool. Updated bedrooms and bathrooms provide a comfortable and

    Diana Bisselle William Pitt Sotheby's Int'l

    28 Leavenworth Rd, Woodbury, CT 06798
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    $1,600 Per Month

    • 2 Beds
    • 1 Bath
    • 728 Sq Ft
    • House for Rent

    48 White Oak Rd Unit B, Woodbury, CT 06798

    Come see this conveniently located and quiet 2 bedroom apartment in the heart of Woodbury! Off of the main road, it is within walking distance to shops and restaurants, yet situated on a serene and private lot on a dead-end street. With a well-designed floor plan, this apartment blends functionality with comfort. At an affordable price, don't hesitate to take the opportunity to rent in one of

    Matthew Amatruda Drakeley Real Estate, Inc.

    48 White Oak Rd Unit B, Woodbury, CT 06798
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    $2,995 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,440 Sq Ft
    • House for Rent

    650 Main St N, Woodbury, CT 06798

    Now available for rent! This well-maintained 3-bedroom home features a spacious eat-in kitchen, 1&1/2 baths, and a comfortable layout ideal for everyday living. Under house two car garage provides ample parking and additional storage. Conveniently located and ready for immediate occupancy, this home offers the space and comfort you've been looking for. Schedule your showing today!1 first month's

    Heather Wilson The Washington Agency

    650 Main St N, Woodbury, CT 06798
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    $4,800 Per Month

    • 4 Beds
    • 4.5 Baths
    • 3,200 Sq Ft
    • House for Rent

    259 Main St S, Woodbury, CT 06798

    Expansive main house with frontage on quintessential historic Main Street. RESIDENTIAL or COMMERCIAL space! Walk the sidewalks to the antique shops, parks, & restaurants. Enjoy the wineries and farm markets. Have a front row seat for the summer parades and the Christmas Eve luminaries that adorn Main Street. Deep lot with ample parking in the rear of the house. All four bedrooms have en-suite

    Gina Jacobs Gina Jacobs Real Estate

    259 Main St S, Woodbury, CT 06798
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    $2,100 Per Month

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • House for Rent

    300 Railtree Rd, Woodbury, CT 06798

    1-2 BR one bath completely renovated. Laundry in unit, private off street parking. Plowing and lawn maitenance included tenant shovels walk way. Credit check required no smoking or pets

    Doug Rose Scalzo Real Estate

    300 Railtree Rd, Woodbury, CT 06798
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    $2,650 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,550 Sq Ft
    • Townhouse for Rent

    190 Saw Pit Hill Rd, Woodbury, CT 06798

    Three Bedrooms one full and one half baths in a spacious duplex. Recently painted, updated kitchen and new carpet. Full unfinished basement for extra storage. Landlord requires good credit and employment history. pets considered. year lease and security deposit required

    Sindy Butkus Klemm Real Estate Inc

    190 Saw Pit Hill Rd, Woodbury, CT 06798
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    $1,800 Per Month

    • 2 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • House for Rent

    4-5 Weekeepeemee Rd Unit 5, Woodbury, CT 06798

    Apartment 5 is a large, bright, natural light filled apartment. Second floor with front and back private porches. Living room is very spacious with built ins. Kitchen has granite counters and two pantries. Hard wood flooring. Brand new appliances in laundry room. Freshly painted - Ready for immediate occupancy. This is a second floor unit. Rear yard is recently cleared and seeded for all tenants

    Mary Ann Bennett Drakeley Real Estate, Inc.

    4-5 Weekeepeemee Rd Unit 5, Woodbury, CT 06798
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    $2,000 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,500 Sq Ft
    • Townhouse for Rent

    13 Pleasant St Unit 15, Woodbury, CT 06798

    Spacious two bedroom half duplex located up the street from Canfield Pharmacy.It's antique character features a light filled living room wit wood floors.eatin kitchen and dining toom. half bath on main level as laundry hookups. two bedrooms up and the full bath. Walk up attic for plenty of storage. Tenant must have FICO over 650 with good employment history. Year lease, NO PETS and NO SMOKERS!

    Sindy Butkus Klemm Real Estate Inc

    13 Pleasant St Unit 15, Woodbury, CT 06798
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    $3,250 Per Month

    • 2 Beds
    • 2 Baths
    • 2,408 Sq Ft
    • House for Rent

    47 Terrell Rd, Woodbury, CT 06798

    Welcome home to this beautifully updated single-family rental nestled on 14 private acres, offering the perfect blend of comfort, space, and tranquility. This 2-bedroom, 2-bath home features a new spacious bonus room which leads to the brand-new oversized deck overlooking the surrounding natural beauty. The newly finished walk-out lower level will be great for additional flexible living space or

    Wendy Brazauskas Coldwell Banker Realty

    47 Terrell Rd, Woodbury, CT 06798
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    $1,450 Per Month

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

    35 Mill Rd, Woodbury, CT 06798

    Nestled in a peaceful residential setting with a scenic brook and bridge entry, this cozy ranch-style home offers the perfect blend of rural charm, natural beauty and convenient access to everyday conveniences. Freshly painted with refinished floors, this inviting home features comfortable living space, a kitchen with dining area, one bedroom, home office and a full bathroom with a freestanding

    Lisa McDonald The Brokerage of New England

    35 Mill Rd, Woodbury, CT 06798
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    $7,500 Per Month

    • 4 Beds
    • 2.5 Baths
    • 3,159 Sq Ft
    • House for Rent

    260 White Deer Rocks Rd, Woodbury, CT 06798

    There is no better place to spend your time in Litchfield County than the town of Woodbury. Honored as "Connecticut's most charming town" you have access to award-winning dining (indoor & outdoor), local farms & CSA's, natural food stores, spa's, vineyards & breweries, antique shops, golf courses, bike trails, lakes & hiking - all minutes away from this centrally located property. This home's

    Michael Caporizzo William Pitt Sotheby's Int'l

    260 White Deer Rocks Rd, Woodbury, CT 06798
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    $2,800 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,916 Sq Ft
    • Townhouse for Rent

    54 Clubhouse Dr Unit 54, Woodbury, CT 06798

    Bright, well-maintained 3-level townhome in Woodbury's Woodlake community with seasonal views of Wood Lake. The main level features an open living/dining area with a floor-to-ceiling fireplace (wood-burning insert, 2021) and a private deck. The kitchen has granite counters, stainless appliances, and opens to a paver patio. Upstairs: a primary suite with full bath and lake-view balcony, plus a

    Henrik K Kjaer Keller Williams Realty

    54 Clubhouse Dr Unit 54, Woodbury, CT 06798

Why Live in Woodbury

Woodbury, CT, established in 1673, is renowned as the "Antiques Capital of Connecticut," with over 50 antiques dealers offering a range of items from trinkets to 18th-century furniture. The town's historic charm is complemented by modern amenities, including a variety of dining options such as the 1754 House and Woodbury Brewing Co., which also serves as a nightlife hub with live music and events. Outdoor enthusiasts can explore Orenaug Park, featuring a fire tower with panoramic views of the Pomperaug River Valley, and Hollow Park, which hosts community events like the annual Fire Department Carnival. The Flanders Nature Center & Land Trust provides educational programs and extensive trails across 2,100 acres. Woodbury's residential areas showcase a mix of historic saltbox-style Colonials and Cape Cods alongside contemporary homes, often situated on multi-acre lots. The town is served by Regional School District 14, with schools earning solid ratings, and the highly-rated Kent School nearby. Community events are frequent, with holiday gatherings at Hollow Park and literary events at the Woodbury Library. The town's proximity to Route 6 ensures convenient commuting, while maintaining a somewhat rural atmosphere.

Frequently Asked Questions

How much does it cost to rent a home in Woodbury, CT?
The median rent for a home in Woodbury, CT is $2,450 per month, though prices vary by neighborhood, size, and property type. As of August 2026, condos tend to be the most affordable option while townhouses and single-family homes are currently more expensive.
How much do you need to make to afford rent in Woodbury, CT?
To comfortably afford the median rent in Woodbury, CT, a household needs to earn roughly $98,000 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 $2,450 per month in Woodbury, CT, renters typically need to show $7,350 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 Woodbury, CT?
In Woodbury, CT, the price-to-rent ratio is 16.8, 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 Woodbury, CT are best for renting a home?
The best neighborhood for renting in Woodbury, 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, South End District and Waterville, each with its own character and price range.

Rental Home Trends

Number of Homes for Rent
15
Median Rent
$2,450
Median Single Family Home Rent
$2,450
Median Townhouse Rent
$2,050
Median Condo Rent
$1,895
How to Rent a Home