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Woodbury, CT Homes for Rent

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  • /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

    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

    302 Tuttle Rd, Woodbury, CT 06798
  • /43

    $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
  • /61

    $1,500

    Total Monthly Price

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

    14 Arrowhead Way Unit 3, Woodbury, CT 06798

    Heat and hot water are included with this immaculate first floor condo. Freshly painted and professionally cleaned, this unit is bright and cheerful offering spectacular views. In a small complex on a dead end road with beautifully landscaped grounds. Also included are: fridge, stove/oven, lockable basement storage, snow removal and year round grounds maintenance, trash and recycling services,

    14 Arrowhead Way Unit 3, 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 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
  • /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
  • /16

    $1,400 Per Month

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

    4-2 Weekeepeemee Rd Unit 2, Woodbury, CT 06798

    Available immediately. First floor one bed apartment. Front to back filled with natural. Very good size kitchen w granite and breakfast bar, dining room area with half wall bookshelf delineation to Living room with picture window. One bedroom and walk in closet off set in hallway. Hardwood flooring - clean, charming and ready for new tenant. This building was renovated approx 10 years ago w all

    Mary Ann Bennett Drakeley Real Estate, Inc.

    4-2 Weekeepeemee Rd Unit 2, Woodbury, CT 06798
  • /7

    $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
  • /12

    $2,750 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
  • /22

    $1,900 Per Month

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

    4 Weekeepeemee Rd, 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. 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

    Mary Ann Bennett Drakeley Real Estate, Inc.

    4 Weekeepeemee Rd, Woodbury, CT 06798
  • /9

    $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
  • /37

    $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

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 $2,150 per month, though prices vary by neighborhood, size, and property type. As of July 2026, condos tend to be the most affordable option while single-family homes and townhouses 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 $86,000 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 $2,150 per month in Woodbury, CT, renters typically need to show $6,450 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 19.0, 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

Number of Homes for Rent
12
Median Rent
$2,150
Median Single Family Home Rent
$2,200
Median Townhouse Rent
$2,250
Median Condo Rent
$1,848
How to Rent a Home