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Woodbury, CT Homes for Sale with Pool

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  • /24

    $289,000

    $30K PRICE DROP
    • 2 Beds
    • 3 Baths
    • 1,059 Sq Ft

    3 Tamarack Ln Unit 3, Woodbury, CT 06798

    Welcome to this well-maintained condo offering comfortable living in a desirable Woodbury location. This inviting unit features a bright and open layout with spacious living areas, an updated kitchen, and generously sized bedrooms. Enjoy the ample storage and a private outdoor space perfect for relaxing or entertaining. Nestled in a quiet, well-kept complex close to local shops, dining, and major

    Stephen Mele Houlihan Lawrence

    3 Tamarack Ln Unit 3, Woodbury, CT 06798
  • /27

    $545,000

    • 2 Beds
    • 2.5 Baths
    • 1,673 Sq Ft

    17 Woodbury Hill Unit 17, Woodbury, CT 06798

    The finest condo complex in one of Litchfield Counties most charming towns! Woodbury Hill is a lovely community of townhouse style homes in a very attractive setting and features a saltwater pool and tennis/pickleball courts. #17 has seen many upgrades over the past dozen years including new windows, renovated kitchen and baths, upgraded heat pump HVAC and water heater, as well as recent paint

    Justin Bette Century 21 Bette Real Estate

    17 Woodbury Hill Unit 17, Woodbury, CT 06798
  • /21

    $459,000

    $16K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,032 Sq Ft

    241 Hoop Pole Hill Rd, Woodbury, CT 06798

    Nestled in the highly desirable town of Woodbury, this charming Cape offers just over 2,000 square feet of comfortable living space with endless potential. The home features 3 bedrooms, 2.5 bathrooms, and beautiful hardwood floors throughout. A dedicated home office with custom built-in shelving provides the perfect space for working from home or studying. The inviting living room includes a cozy

    Rhya Szymansky Drakeley Real Estate, Inc.

    241 Hoop Pole Hill Rd, Woodbury, CT 06798
  • /40

    $1,900,000

    • 4 Beds
    • 2.5 Baths
    • 2,732 Sq Ft

    40 Ruffin Rd, Woodbury, CT 06798

    It's rare to find a vintage estate tucked away from a main road, but this one sits at the end of a private lane, opening to 6.3 enchanting acres framed by stone walls, manicured gardens, and a charming vintage home. The property includes a large custom two-story pole barn, inground pool, detached three-bay garage, and an adorable potting shed. The great room flows into a kitchen with handmade

    Mary Ann Bennett Drakeley Real Estate, Inc.

    40 Ruffin Rd, Woodbury, CT 06798
  • /40

    $799,900

    • 4 Beds
    • 2.5 Baths
    • 3,223 Sq Ft

    62 Heritage Dr, Woodbury, CT 06798

    Beautifully renovated 4-bedroom, 2.5-bath ranch set on a spacious corner lot in one of Woodbury's most desirable locations. Just two streets from Woodbury's nationally recognized Main Street, this home offers the perfect combination of modern updates, comfortable living, and exceptional outdoor entertaining. The complete interior renovation began in 2023 and has recently been completed, creating

    Jonathan Pinto Pinto Real Estate Group LLC

    62 Heritage Dr, Woodbury, CT 06798
  • /40

    $2,995,000

    • 4 Beds
    • 6 Baths
    • 5,316 Sq Ft

    920 Main St S, Woodbury, CT 06798

    Warren's Landing on the Pomperaug is an extraordinary estate where historic character is centered around a beautifully preserved 1890 Greek Revival residence. The home offers four bedrooms, timeless architectural details, spacious rooms, 4 fireplaces and custom built-ins. The impressive six-barn complex provides exceptional flexibility, featuring a retail shop, extensive equipment storage, a

    Maria Taylor Klemm Real Estate Inc

    920 Main St S, Woodbury, CT 06798
  • /22

    $325,000

    $53K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 2,118 Sq Ft

    8 Tamarack Ln Unit 8, Woodbury, CT 06798

    Spacious end-unit condo offering over 2,100 sq. ft. of comfortable living space in desirable Woodbury! While officially a 2-bedroom, the finished heated and cooled lower level includes additional rooms currently used as a bedroom, family room, office, gym, and storage space-providing exceptional flexibility for today's lifestyle. The updated kitchen, beautiful hardwood floors, and cozy pellet

    Jennifer Mayo William Raveis Real Estate

    8 Tamarack Ln Unit 8, Woodbury, CT 06798
  • /40

    $895,000

    • 4 Beds
    • 3.5 Baths
    • 3,784 Sq Ft

    557 Upper Grassy Hill Rd, Woodbury, CT 06798

    Welcome to Upper Grassy Hill Living!

    Susan Corleto William Pitt Sotheby's Int'l

    557 Upper Grassy Hill Rd, Woodbury, CT 06798
  • /40

    $519,000

    • 2 Beds
    • 2.5 Baths
    • 1,796 Sq Ft

    63 Woodbury Hill Unit 63, Woodbury, CT 06798

    Exceptionally private, Putnam Loft model in the sought after Woodbury Hill! This unit is located in a secluded part of the community with woods behind and only sounds of the nearby babbling brook. This well-cared for unit features hardwood floors throughout, vaulted ceilings, floor to ceiling gas fireplace, a large dining room and remodeled kitchen. The primary bedroom suite is on the main level

    Katherine Parlato Drakeley Real Estate, Inc.

    63 Woodbury Hill Unit 63, Woodbury, CT 06798
  • /33

    $849,000

    • 3 Beds
    • 2 Baths
    • 2,448 Sq Ft

    92 Minortown Rd, Woodbury, CT 06798

    Live Stress-Free in This Income-Producing Equestrian Retreat! Enjoy the best of country living while generating income from your property. Rental revenue from a separate 1 BR apartment and 4 of the 10 horse stalls offers a rare opportunity to offset ownership costs! Situated on 5.76 level acres of open pasture and riding space, this equestrian property is ideal for horse enthusiasts, trainers, or

    Jill Sloane Brown Harris Stevens

    92 Minortown Rd, Woodbury, CT 06798
  • /40

    $1,995,000

    • 4 Beds
    • 4.5 Baths
    • 3,324 Sq Ft

    55 Good Hill Rd, Woodbury, CT 06798

    Step into History with Modern Comfort Experience the undeniable charm of this circa 1685 residence-one of the oldest continuously inhabited homes in the county. Thoughtfully restored and beautifully updated, this remarkable property blends centuries of character with today's modern conveniences. Inside, the open floor plan creates a warm and inviting flow, with three cozy sitting rooms

    Stacey Matthews W. Raveis Lifestyles Realty

    55 Good Hill Rd, Woodbury, CT 06798

Home Price Trends

Median Sale Price
$489,500
Median Single Family Sale Price
$597,500
Median Townhouse Sale Price
$325,000
Median 2 Bedroom Sale Price
$288,995
Median 1 Bedroom Sale Price
$129,250
Average Price Per Sq Ft
$286
Number of Homes for Sale
36
Last 12 months Home Sales
128
Months of Supply
3.40
Median List Price
$527,450
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
7%
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