Woodbury, CT Homes

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  $559,900 Pending

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

  18 Woodbury Hill, Woodbury, CT 06798

  Experience the charm of Woodbury's most desirable condominium community at 18 Woodbury Hill. This beautifully updated Putnam's Loft model offers an open and inviting floor plan perfect for both everyday living and entertaining. The main level features a spacious living room with oak floors, vaulted ceiling, fireplace, and abundant natural light, flowing seamlessly into the dining room. The

  

  Tim Drakeley

  Drakeley Real Estate, Inc.

  (475) 335-8066

  18 Woodbury Hill, Woodbury, CT 06798
• Explore Woodbury

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  /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

  

  Rebecca Doh

  W. Raveis Lifestyles Realty

  (203) 872-6274

  33 Washington Ave, Woodbury, CT 06798
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  $897,000 Sold Jun 27, 2025

  332 Good Hill Rd, Woodbury, CT 06798

  • 3 Beds
  • 3 Baths
  • 2,894 Sq Ft
  • Built 2015

  Last Sold Summary

  • 12% Above List Price
  • $310/SF
  • 27 Days On Market

  Current Estimated Value $878,573

  Last Listing Agent Rebecca Doh W. Raveis Lifestyles Realty

  332 Good Hill Rd, Woodbury, CT 06798
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  Est $448,949 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,058 Sq Ft

  9 Orenaug Ave, Woodbury, CT 06798

  9 Orenaug Ave, Woodbury, CT 06798
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  $539,000

  • 2 Beds
  • 2.5 Baths
  • 3,362 Sq Ft

  9 Hill View Ln, Woodbury, CT 06798

  Charming Dutch Colonial located in the desirable South Brook community in Woodbury, walking distance from the bustling shops and restaurants. This home is part of a small enclave of 21 single, detached residences. Features include a new wood roof, hardwood floors throughout, and a private backyard with patio. The first floor offers a formal dining room, an eat-in kitchen with ample cabinet and

  

  Mary Ann Hebert

  BHGRE Gaetano Marra Homes

  (475) 264-5720

  9 Hill View Ln, Woodbury, CT 06798
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  $1,550 - $1,899 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 Woodbury, CT apartments, you'll discover a lifestyle thats vibrant yet peaceful, perfectly balanced, and endlessly welcoming.

  302 Tuttle Rd, Woodbury, CT 06798
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  $375,000 Sold Feb 14, 2025

  22 Clubhouse Dr Unit 22, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 1,888 Sq Ft
  • Built 1972

  Last Sold Summary

  • 12% Below List Price
  • $199/SF
  • 154 Days On Market

  Current Estimated Value $389,330

  Last Listing Agent Sindy Butkus Klemm Real Estate Inc

  22 Clubhouse Dr Unit 22, Woodbury, CT 06798
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  Est $469,481 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,577 Sq Ft

  24 Woodbury Hill, Woodbury, CT 06798

  24 Woodbury Hill, Woodbury, CT 06798
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  $899,900

  • 4 Beds
  • 2.5 Baths
  • 3,700 Sq Ft

  337 Main St S, Woodbury, CT 06798

  A Real Classic! Beautifully renovated with many original features. Located in the Historic District in the heart of Woodbury. Stroll along Main Street to parks, excellent restaurants, house of worship, conveniences and antique shops. Home is just lovely with exposed beams, wide board hardwood floors, 4 fireplaces, outside on the patio, primary bedroom, dining room and living room. One fireplace

  

  Marian Van Egas

  Berkshire Hathaway NE Prop.

  (475) 255-3184

  337 Main St S, Woodbury, CT 06798
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  /7

  $1,595 total monthly price

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

  15 Pilgrim Trail Unit 6, Woodbury, CT 06798

  Newly renovated 1 bedroom, 1 bathroom unit in a quiet, park-like complex. Heating, trash, hot water, snow removal, and ground maintenance are included. Move-in ready. Coin-operated laundry on-site. Close to restaurants and shopping. Sorry, no pets or smoking per HOA rules.

  Jacqueline Ruppert Berkshire Hathaway NE Prop.

  15 Pilgrim Trail Unit 6, Woodbury, CT 06798
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  $480,000 Sold Nov 04, 2025

  145 Cat Swamp Rd, Woodbury, CT 06798

  • 3 Beds
  • 1.5 Baths
  • 1,792 Sq Ft
  • Built 1961

  Last Sold Summary

  • 4% Above List Price
  • $268/SF
  • 51 Days On Market

  Last Listing Agent Nancy Langrock William Raveis Real Estate

  145 Cat Swamp Rd, Woodbury, CT 06798
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  Est $581,949 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,120 Sq Ft

  340 Minortown Rd, Woodbury, CT 06798

  340 Minortown Rd, Woodbury, CT 06798
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  /15

  $990,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,300 Sq Ft

  523 Main St N, Woodbury, CT 06798

  To be built Modern style home with gorgeous southern views and privacy from your neighbors. Enjoy the wall of glass overlooking a bluestone patio, and beautiful views above Main Street North! Just a few minutes from Woodbury's town center, this home provides an open floor with a kitchen/great room, a cathedral ceiling, and a floor-to-ceiling masonry fireplace. The first floor includes a primary

  

  Tim Drakeley

  Drakeley Real Estate, Inc.

  (475) 284-8768

  523 Main St N, Woodbury, CT 06798
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  /10

  $1,850 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. This condo is located on Woodbury most desirable areas and will not last long so dont wait schedule a tour

  259 Main St S Unit 4, Woodbury, CT 06798
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  $430,000 Sold Apr 04, 2025

  163 Washington Rd, Woodbury, CT 06798

  • 4 Beds
  • 3 Baths
  • 2,521 Sq Ft
  • Built 1836

  Last Sold Summary

  • 5% Below List Price
  • $171/SF
  • 162 Days On Market

  Current Estimated Value $443,569

  Last Listing Agent Katherine Parlato Drakeley Real Estate, Inc.

  163 Washington Rd, Woodbury, CT 06798
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  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,150 Sq Ft

  126 Sherman Hill Rd Unit A14, Woodbury, CT 06798

  126 Sherman Hill Rd Unit A14, Woodbury, CT 06798
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  /25

  $299,990

  • 2 Beds
  • 2 Baths
  • 1,182 Sq Ft

  4 Fox Run Unit 4, Woodbury, CT 06798

  Welcome to this beautifully refreshed townhome in the highly desirable Woodlake Condominium Complex in Woodbury. Freshly painted throughout and filled with natural light, the main level features hardwood floors, a spacious living and dining area with a cozy fireplace, and a sliding door that opens to a private deck overlooking peaceful wooded surroundings. The updated kitchen includes granite

  Henrik K Kjaer Keller Williams Realty

  4 Fox Run Unit 4, Woodbury, CT 06798
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  /9

  $2,200 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Apartment for Rent

  64 White Deer Rocks Rd Unit 5E, Woodbury, CT 06798

  Fully renovated apartment. Move-in ready, 2 bedrooms and 1 bath. Heat, hot water, trash and electricity are included in the rent.... Close to shopping. Requirement: no evictions in the last 6 months, good credit, Background check, 2 months security deposit. pets are allowed. $50 per pets. no smoking inside the house. Renter insurance is required.

  Naima Mazouzi Eagle Eye Realty PLLC

  64 White Deer Rocks Rd Unit 5E, Woodbury, CT 06798
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  $424,950 Sold Oct 23, 2025

  158 Hazel Plain Rd, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 2,085 Sq Ft
  • Built 1974

  Last Sold Summary

  • $204/SF
  • 32 Days On Market

  Last Listing Agent Michael Ferris eXp Realty

  158 Hazel Plain Rd, Woodbury, CT 06798
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  Est $496,090 Not Listed For Sale

  49 Terrell Rd, Woodbury, CT 06798

  49 Terrell Rd, Woodbury, CT 06798
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  $1,100,000

  • 4 Beds
  • 2.5 Baths
  • 3,545 Sq Ft

  45 N Gate Rd, Woodbury, CT 06798

  Welcome to Woodbury, a quintessential New England town. This house is located in a very desirable neighborhood, just north of the town center. An inviting covered front porch will greet you. This leads to a 2 story foyer and an open floor plan opens up in front of you! To the left is a formal LR/Den. (cozy up with a good book) To the right is formal Dining Room with a trey ceiling, seats 8-10

  Jeff Colt Showcase Realty, Inc.

  45 N Gate Rd, Woodbury, CT 06798
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  /20

  $4,950 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
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  $350,000 Sold Aug 08, 2025

  306 Upper Grassy Hill Rd, Woodbury, CT 06798

  • 3 Beds
  • 2 Baths
  • 1,936 Sq Ft
  • Built 1964

  Last Sold Summary

  • $181/SF
  • 6 Days On Market

  Current Estimated Value $367,416

  Last Listing Agent Shawna Mucherino Coldwell Banker Realty

  306 Upper Grassy Hill Rd, Woodbury, CT 06798
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  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,138 Sq Ft

  14 Wintergreen Ct Unit 77A, Woodbury, CT 06798

  14 Wintergreen Ct Unit 77A, Woodbury, CT 06798
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  $1,998,000 Under Contract

  • 4 Beds
  • 4.5 Baths
  • 4,517 Sq Ft

  225 Old Sherman Hill Rd, Woodbury, CT 06798

  Discover refined country living in this remarkable Woodbury estate set on 33.98 private acres in sought-after Litchfield County. The 4,517 sq ft residence features 4 bedrooms, 4.1 baths, and bright, open interiors designed to capture serene views of distant hills. A spacious deck overlooks the sparkling saltwater gunite pool, creating an ideal setting for relaxation or entertaining. Equestrians

  Maria Taylor Klemm Real Estate Inc

  225 Old Sherman Hill Rd, Woodbury, CT 06798
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  /19

  $2,200 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,182 Sq Ft
  • Townhouse for Rent

  7 Woods Way Unit 7, Woodbury, CT 06798

  Two-Bedroom townhome for rent in Woodlake, close to town and schools. This updated, light-filled unit offers an open main floor with a large living/dining area, hardwood floors, a half bath, and a small office/mudroom space. Sliders lead to a private back patio. The lower level is partially finished and great for extra storage or bonus space. Upstairs you'll find two oversized bedrooms with

  Taylor O'Keefe Drakeley Real Estate, Inc.

  7 Woods Way Unit 7, Woodbury, CT 06798
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  $445,000 Sold Mar 03, 2025

  397 Railtree Hill Rd, Woodbury, CT 06798

  • 3 Beds
  • 2 Baths
  • 1,444 Sq Ft
  • Built 1978

  Last Sold Summary

  • 1% Below List Price
  • $308/SF
  • 41 Days On Market

  Current Estimated Value $465,686

  Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

  397 Railtree Hill Rd, Woodbury, CT 06798
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  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,182 Sq Ft

  23 Upper Commons Unit 23, Woodbury, CT 06798

  23 Upper Commons Unit 23, Woodbury, CT 06798
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  /23

  $675,000

  • 3 Beds
  • 2.5 Baths
  • 2,835 Sq Ft

  38 Barnhill Rd, Woodbury, CT 06798

  If you are looking for peace and tranquility, you will find it here in this expansive cape. Located on a quiet country road, it provides the privacy and tranquility as well as great spaces for a variety of lifestyles. For preparing great meals, this oversized kitchen is just the place. Enjoy friends and family as you prepare & dine. Spill over into the 25' x 22' family room with custom

  Donna Bannon BHGRE Gaetano Marra Homes

  38 Barnhill Rd, Woodbury, CT 06798
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  $1,850 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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  $765,000 Sold Jul 29, 2025

  3 Inwood Ln, Woodbury, CT 06798

  • 4 Beds
  • 4 Baths
  • 3,330 Sq Ft
  • Built 1986

  Last Sold Summary

  • 13% Below List Price
  • $230/SF
  • 58 Days On Market

  Current Estimated Value $784,091

  Last Listing Agent Elizabeth Newnham William Pitt Sotheby's Int'l

  3 Inwood Ln, Woodbury, CT 06798
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  Est $690,301 Not Listed For Sale

  • 3 Beds
  • 6 Baths
  • 8,747 Sq Ft

  785 Washington Rd, Woodbury, CT 06798

  785 Washington Rd, Woodbury, CT 06798
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  $1,925,000

  • 3 Beds
  • 3 Baths
  • 2,992 Sq Ft

  819 Main St N, Woodbury, CT 06798

  Open Meadow Farm, a beautifully maintained property offering a blend of rural charm and modern conveniences. Set on 9.88 picturesque acres, this property features three fenced fields, ideal for horses or other livestock and a two-story barn equipped with four stalls, a tack room, gravel storage area and a gleaming concrete main floor. Recent updates include a paved driveway with turnaround, back

  Sindy Butkus Klemm Real Estate Inc

  819 Main St N, Woodbury, CT 06798
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  $2,100 total monthly price

  • 2 Beds
  • 1 Bath
  • 2,841 Sq Ft
  • House for Rent

  141 Washington Rd Unit 2, Woodbury, CT 06798

  Beautifully Renovated 2-Bedroom Apartment in Woodbury, CT Welcome to your newly renovated 2-bedroom, 1-bath apartment located in the heart of Woodbury. This top floor, bright and inviting apartment blends modern updates with charming character details, including exposed wood beams and warm, wood-style flooring throughout. The brand-new kitchen features crisp white shaker cabinets, quartz

  Dean Giatas Fiorelli Realty, LLC

  141 Washington Rd Unit 2, Woodbury, CT 06798
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  $265,000 Sold Jan 24, 2025

  1 Hickory Ln Unit 1, Woodbury, CT 06798

  • 2 Beds
  • 2.5 Baths
  • 1,895 Sq Ft
  • Built 1974

  Last Sold Summary

  • $140/SF
  • 48 Days On Market

  Current Estimated Value $284,048

  Last Listing Agent Stephen Kocis Roost Realty

  1 Hickory Ln Unit 1, Woodbury, CT 06798
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  Not Listed For Sale

  0 Mill Rd, Woodbury, CT 06798

  0 Mill Rd, Woodbury, CT 06798
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  $584,900

  • 4 Beds
  • 2.5 Baths
  • 2,256 Sq Ft

  31 McVeigh Rd, Woodbury, CT 06798

  Welcome home to 31 McVeigh Rd! Privately set on 1.70 acres in the Quassapaug neighborhood, this home blends comfort, efficiency, and convenience. The living room offers a wood-burning fireplace, while a 2019 high-efficiency wood stove in the family room adds warmth and helps lower heating costs. The main level features connected yet distinct spaces-living room, family room, dining area, and a

  Jennifer Bundock Coldwell Banker Realty

  31 McVeigh Rd, Woodbury, CT 06798
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  /27

  $4,300 per month

  • 4 Beds
  • 2.5 Baths
  • 3,345 Sq Ft
  • House for Rent

  Unlisted Address

  Elegant Colonial in a Premier Location Experience timeless sophistication in this meticulously maintained Center Hall Colonial, ideally situated just minutes from I-84. This residence offers 4 expansive bedrooms, 2.5 designer baths, and multiple living spaces, including two gracious family rooms and a sun-drenched four-season room. Refined details abound-gleaming hardwood floors, three stately

  William Voight Great Estates, CT

  Unlisted Address
• 

  $291,000 Sold Apr 11, 2025

  17 Tamarack Ln Unit 17, Woodbury, CT 06798

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Built 1974

  Last Sold Summary

  • 4% Above List Price
  • $224/SF
  • 22 Days On Market

  Last Listing Agent Sharisse Steiner William Raveis Real Estate

  17 Tamarack Ln Unit 17, Woodbury, CT 06798
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  Est $1,347,805 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 5,694 Sq Ft

  17 Gate Post Ln, Woodbury, CT 06798

  17 Gate Post Ln, Woodbury, CT 06798

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