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Woodbury, CT Homes for Rent

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  • /10

    $1,800 total monthly price

    • 1 Bed
    • 1 Bath
    • 2,728 Sq Ft
    • House for Rent

    65 Hard Hill Rd, Woodbury, CT 06798

    Very nice, furnished one-bedroom in-law apartment for rent. The spacious kitchen opens to a bright, sunny living room. The apartment also features a large bathroom and a separate laundry room.Enjoy a lovely backyard with patio access. No smoking and no pets, please. The landlord takes care of exterior maintenance and all utilities, including heat, hot water, electricity, central air, garbage

    Agent Photo

    Marian Van Egas

    Berkshire Hathaway NE Prop.

    (475) 275-6685

    65 Hard Hill Rd, Woodbury, CT 06798
  • /26

    $4,000 total monthly price

    • 3 Beds
    • 3 Baths
    • 2,320 Sq Ft
    • House for Rent

    220 Upper Grassy Hill Rd, Woodbury, CT 06798

    Recently renovated single-family home on the Woodbury/Roxbury town line. Completely rebuilt from the studs up, this three-bedroom ranch features brand-new electrical, HVAC, spray-foam insulation, trim, drywall, hardwood floors, plus a new kitchen and three new baths. Rare opportunity to rent a truly "like-new" home available immediately. Enjoy a spacious main level with three bedrooms, a living

    Agent Photo

    Tim Drakeley

    Drakeley Real Estate, Inc.

    (475) 281-3909

    220 Upper Grassy Hill Rd, Woodbury, CT 06798
  • /31

    $3,750 total monthly price

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

    33 Washington Ave, Woodbury, CT 06798

    AVAILABLE FOR $3,950/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 a bright

    Agent Photo

    Rebecca Doh

    W. Raveis Lifestyles Realty

    (203) 872-6274

    33 Washington Ave, Woodbury, CT 06798
  • /35

    $1,599 per month plus fees

    Woodbury Knoll

    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 natures quiet beauty, and evenings unwind in serene surroundings. In our apartments in Woodbury, CT, you'll discover a lifestyle thats vibrant yet peaceful, perfectly balanced, and endlessly welcoming.

    302 Tuttle Rd, Woodbury, CT 06798
  • /25

    $3,200 total monthly price

    • 2 Beds
    • 2 Baths
    • 1,290 Sq Ft
    • House for Rent

    36 Washington Ave, Woodbury, CT 06798

    Charming 2BR,2BA Home, located on a private 1/2 acre lot is available in the Heart of Woodbury, and just 90 minutes away from the hustle and bustle of NYC. This home offers almost 1300 sf of living space featuring a modern, updated kitchen, a cozy living room with FP, a large dining area perfect for entertaining, 2 generous bedrooms and 2 full, updated bathrooms. In addition, there is LL Bonus

    Sharon Rinaldi Showcase Realty, Inc.

    36 Washington Ave, Woodbury, CT 06798
  • /10

    $1,650 per month plus fees

    • 1 Bed
    • 1 Bath
    • 1,000 Sq Ft
    • Condo for Rent

    259 Main St S Unit 4, Woodbury, CT 06798

    Property Id: 2072922Light and bright 2 Story 1 Bedroom Condo available for immediate 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. Ample off street parking and spacious yard. This condo is located on the Woodbury antique trail, one most

    259 Main St S Unit 4, Woodbury, CT 06798
  • /14

    $1,425 total monthly price

    • 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
  • /18

    $4,750 per month 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

    259 Main St S, Woodbury, CT 06798
  • /10

    $1,900 total monthly price

    • 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
  • /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
  • /17

    $2,200 total monthly price

    • 2 Beds
    • 1 Bath
    • 1,350 Sq Ft
    • House for Rent

    533 Weekeepeemee Rd, Woodbury, CT 06798

    First floor two bedroom, eat in kitchen, shower bath, laundry. IMMACULATE and immediate occupancy for the right fit. Owners were just awarded the 2025 Town of Woodbury Historic Preservation Award. Eleazer Crane House - circa 1800 on 1.3 acres in rural Woodbury. Sun filled spacious apartment. Looking for that quiet tenant to be compatible with the upstairs tenants for a cohesive living experience.

    Mary Ann Bennett Drakeley Real Estate, Inc.

    533 Weekeepeemee Rd, Woodbury, CT 06798
  • /12

    $1,750 total monthly price

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

    47A Quassuk Rd, Woodbury, CT 06798

    Country cottage near the heart of Woodbury. Freshly painted, updated fixtures & flooring, newer mini split for heat & A/C, newer windows, & well insulated for super efficiency. Serene & private grounds with a rear patio overlooking the landscape & a large pond. Owners reside in the main house & will plow & maintain the lawn. Tenant to remove the snow on his/her walkway to entry. Tenant

    Gina Jacobs Gina Jacobs Real Estate

    47A Quassuk Rd, Woodbury, CT 06798
  • /37

    $30,000 total monthly price

    • 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
  • /17

    $2,499 total monthly price

    • 3 Beds
    • 2 Baths
    • 1,315 Sq Ft
    • House for Rent

    25 Elephant Rock Rd Unit 2, Woodbury, CT 06798

    Welcome home to this sunny 3 bedroom 2 bath duplex on a lovely culdesac and close to all! Enjoy cozy winters by the fireplace and warm summers on the private patio and backyard surrounded by beautiful trees and shrubs. Convenient parking right outside your door and hook ups for a washer and dryer in the kitchen. Pets will be considered. Short term rental considered.

    Donna Gladstein ERA Insite Realty Services

    25 Elephant Rock Rd Unit 2, 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

What are the most popular neighborhoods in Woodbury, CT for renters?
The most popular neighborhoods in Woodbury, CT for renters are Bunker Hill, West End District, South End District, Village of Waterbury and North End District.
What are the most popular zip codes in Woodbury, CT for renters?
The most popular zip codes in Woodbury, CT for renters include 06798, 06783, 06762, 06795 and 06488.
How to Rent a Home