23

Woodbury, CT Homes for Rent

Section Image Section Image
  • /31

    $3,750 Per Month

    • 2 Beds
    • 2 Baths
    • 1,968 Sq Ft
    • House for Rent

    33 Washington Ave, Woodbury, CT 06798

    AVAILABLE SEPT 2026 FOR $3,750/MONTH. Stunning over-sized Cape on serene, park-like grounds adjacent to a nature preserve. Fully furnished, this inviting 2 bedroom home has been lovingly renovated with a great eye for detail. Quiet street centrally located in historic Woodbury. Newly finished hardwood oak flooring throughout. Two full bathrooms. The large living room with fireplace also includes

    Agent Photo

    Rebecca Doh

    W. Raveis Lifestyles Realty

    (203) 872-6274

    33 Washington Ave, Woodbury, CT 06798
  • /35

    Starting at $1,599 Plus Fees

    • 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

    (860) 590-8441

    302 Tuttle Rd, Woodbury, CT 06798
  • /20

    $4,750 Plus Fees

    • 4 Beds
    • 4.5 Baths
    • 7,112 Sq Ft
    • House for Rent

    259 Main St S, Woodbury, CT 06798

    Property Id: 1500786Located on Main Street South in the heart of Woodbury, in the Litchfield Hills this main house offers 4 BR, 4.5 baths and features original architectural elements, ample living space and beautiful outdoor space. The main living area has a half bath, EIK with island, SS appliances and door to side deck for outdoor eating and grilling + private courtyard, professionally

    (475) 313-1724

    259 Main St S, Woodbury, CT 06798
  • /43

    $1,600

    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
  • /37

    $30,000 Per Month

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

    28 Leavenworth Rd, Woodbury, CT 06798

    STUNNING MEMORIAL DAY - LABOR DAY RENTAL with POOL and TENNIS COURT (with lights). Enjoy a month or all summer 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

    Diana Bisselle William Pitt Sotheby's Int'l

    28 Leavenworth Rd, Woodbury, CT 06798
  • /13

    $1,600 Per Month

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

    34 Arrowhead Way Unit A1, Woodbury, CT 06798

    Well-maintained first-floor end unit featuring a bright living room with beautiful built-in bookshelves, a cozy galley kitchen, and a spacious bedroom. Rent includes heat, hot water, and electricity for added convenience. Located in the Quassuk Heights community, this home offers easy living with plenty of parking, on-site laundry, lower-level storage, and easy walkways from parking to unit.

    Tim Drakeley Drakeley Real Estate, Inc.

    34 Arrowhead Way Unit A1, Woodbury, CT 06798
  • /9

    $2,200 Per Month

    • 2 Beds
    • 1 Bath
    • 1,080 Sq Ft
    • House for Rent

    17 Pleasant St, Woodbury, CT 06798

    This darling little cottage style cape is in the center of Woodbury's Historic District. Recently painted inside and out, new roof, No smokers, no pets. Good credit a must!(700 FICO) Year lease. Landlord maintains lawn care and snow removal. Tenant pays all utilities!

    Sindy Butkus Klemm Real Estate Inc

    17 Pleasant St, Woodbury, CT 06798
  • /22

    $2,000 Per Month

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

    4 Weekeepeemee Rd, Woodbury, CT 06798

    Large bright, natural light filled apartment. Second floor with front and back private porches. Living room is very spacious with built ins. Hard wood flooring. Freshly painted - Ready for immediate occupancy. This is a second floor unit. Rear yard is recently cleared and seeded for all tenants to enjoy. Square footage is approximate. Preference is no pets, but will discuss on case by case basis.

    Mary Ann Bennett Drakeley Real Estate, Inc.

    4 Weekeepeemee Rd, Woodbury, CT 06798
  • /14

    $1,400 Per Month

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

    16 Pilgrim Trail Unit F8, Woodbury, CT 06798

    Cozy one-bedroom end unit on the second floor featuring hardwood floors and plenty of natural light. Coin-operated laundry available in the complex. Heat and hot water are included. No pets, no smoking. Available May 1st. Credit check required. Convenient one-level living in a quiet Woodbury community, just minutes from Woodbury center, shopping, and restaurants.

    David Landau RE/MAX Right Choice

    16 Pilgrim Trail Unit F8, Woodbury, CT 06798
  • /10

    $2,000 Per Month

    • 2 Beds
    • 1 Bath
    • 6,097 Sq Ft
    • House for Rent

    107 Main St N, Woodbury, CT 06798

    2 BEDROOM - BRAND NEW REMODEL - NEW kITCHEN - BATH TOP TO BOTTOM CENTRAL AIR- WASHER & DRYER INCLUDED AND OFF STREET PARKING

    Pat Civitella Civitella Real Estate LLC

    107 Main St N, Woodbury, CT 06798
  • /40

    $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
  • /25

    $2,150 Per Month

    • 2 Beds
    • 1.5 Baths
    • 960 Sq Ft
    • Townhouse for Rent

    74 Washington Rd Unit 16, Woodbury, CT 06798

    Gracious townhome just completely reborn! Excellent quality renovations throughout! Bright and open living flow. Great for entertaining. The sun-splashed living room is cheerful. The broad picture window views the lovely landscape and lawn. The new high-end kitchen boasts soft-close doors with very ample cabinet and counter space. There is a convenient first floor laundry. Dining area views

    Joel Matson Coldwell Banker Realty

    74 Washington Rd Unit 16, 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 $2,100 per month, though prices vary by neighborhood, size, and property type. As of May 2026, townhouses tend to be the most affordable option while condos 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 $84,000 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 $2,100 per month in Woodbury, CT, renters typically need to show $6,300 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 19.4, 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, South End District, Village of Waterbury and North End District, each with its own character and price range.

Rental Home Trends in Woodbury, CT

Rental Home Trends

Number of Homes for Rent
12
Median Rent
$2,100
Median Single Family Home Rent
$2,200
Median Townhouse Rent
$2,100
Median Condo Rent
$2,100
How to Rent a Home