Woodbury, CT Homes

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  $599,900

  $75K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,972 Sq Ft

  348 Hoop Pole Hill Rd, Woodbury, CT 06798

  Exceptional opportunity to renovate and create your dream country estate on 12.69 private acres in the heart of Woodbury. Privately sited along a quiet country road with seasonal long views, this 2,972 sq. ft. contemporary offers an outstanding combination of acreage, privacy, and potential rarely found at this price point. Designed for comfortable living, the home features a dramatic sunken

  

  Rebecca Doh

  W. Raveis Lifestyles Realty

  348 Hoop Pole Hill Rd, Woodbury, CT 06798
• Explore Woodbury

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  /35

  Starting at $1,739

  Total Monthly Price

  • 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 Woodbury, CT apartments you'll discover a lifestyle that's vibrant yet peaceful, perfectly balanced, and endlessly welcoming.

  Woodbury Knoll

  302 Tuttle Rd, Woodbury, CT 06798
• 

  $1,700,000

  Sold Jan 20, 2026

  225 Old Sherman Hill Rd, Woodbury, CT 06798

  • 4 Beds
  • 4.5 Baths
  • 4,517 Sq Ft
  • Built 1969

  Last Sold Summary

  • 19% Below List Price
  • $376/SF
  • 345 Days On Market

  Current Estimated Value $1,718,711

  Last Listing Agent Maria Taylor Klemm Real Estate Inc

  225 Old Sherman Hill Rd, Woodbury, CT 06798
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  Est $133,749

  Not Listed For Sale

  14 Arrowhead Way Unit 6, Woodbury, CT 06798

  • 1 Bed
  • 1 Bath
  • 546 Sq Ft
  • Built 1965

  14 Arrowhead Way Unit 6, Woodbury, CT 06798

  Last Sold Summary

  • 91 Days On Market

  Last Listing Agent Jeff Boucher Drakeley Real Estate, Inc.
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  /40

  $875,000

  Open Sun 12PM - 2PM Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 2,480 Sq Ft

  2 Pomperaug Rd, Woodbury, CT 06798

  Welcome to history, charm, and an incredible location-the best of both worlds! Tucked along a quiet side road, this lovingly cared-for antique offers a peaceful, private setting with a picturesque waterfall nearby for a relaxing stroll, yet you can walk to an amazing collection of local favorites-inc. 9 fine restaurants, 4 diners, a brewery and a pub w/ live entertainment, and a French bakery. No

  

  Pam Famiglietti

  William Raveis Real Estate

  2 Pomperaug Rd, Woodbury, CT 06798
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  $1,800 Per Month

  • 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
• 

  $650,000

  Sold May 28, 2026

  13 Park Ln, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 2,264 Sq Ft
  • Built 1955

  Last Sold Summary

  • $287/SF
  • 0 Days On Market

  Current Estimated Value $633,789

  Last Listing Agent Michael Wright RE/MAX Right Choice

  13 Park Ln, Woodbury, CT 06798
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  Est $283,210

  Not Listed For Sale

  48 Clubhouse Dr, Woodbury, CT 06798

  • 2 Beds
  • 2.5 Baths
  • 1,316 Sq Ft
  • Built 1972

  48 Clubhouse Dr, Woodbury, CT 06798

  Last Sold Summary

  • 40 Days On Market

  Last Listing Agent Taylor O'Keefe Drakeley Real Estate, Inc.
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  $420,000

  • 4 Beds
  • 1.5 Baths
  • 1,590 Sq Ft

  34 Pilgrim Trail, Woodbury, CT 06798

  Welcome to 34 Pilgrim Trail, a home thoughtfully cared for and enjoyed for 25.5 years. This peaceful Woodbury property features granite kitchen countertops, a tiled backsplash, stainless-steel appliances, and a ceramic kitchen floor. Solid pine doors throughout the home add warmth and character. The upstairs bathroom has been beautifully updated, including the tub and a solid-rock vanity

  Karen Gilmore Redfin Corporation

  34 Pilgrim Trail, Woodbury, CT 06798
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  /27

  $2,300 Per Month

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

  113 Lighthouse Rd Unit 115, Woodbury, CT 06798

  This adorable home was built in 2017 and it has very efficient heating and air conditioning. There is a split system for heat and air. The landlord maintains the lawn and snow blowing. It includes all high end appliances including washer and dryer. Enjoy the several decks overlooking the beautiful grounds and privacy. The landlord would accept a one year lease but prefers a two year lease.This

  Joyce Drakeley Drakeley Real Estate, Inc.

  113 Lighthouse Rd Unit 115, Woodbury, CT 06798
• 

  $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

  Current Estimated Value $504,708

  Last Listing Agent Nancy Langrock William Raveis Real Estate

  145 Cat Swamp Rd, Woodbury, CT 06798
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  Not Listed For Sale

  29 Woods Way, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 2,450 Sq Ft
  • Built 1980

  29 Woods Way, Woodbury, CT 06798

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent Derek Greene Derek Greene
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  $329,900

  • 3 Beds
  • 2 Baths
  • 1,210 Sq Ft

  22 Woodbury Place Unit 22B, Woodbury, CT 06798

  Move right into this beautifully updated 3-bedroom, 2-bath townhouse offering style, comfort, and low-maintenance living. Gleaming hardwood floors flow throughout the home, complemented by vaulted ceilings, a skylight providing abundant natural light. The updated galley kitchen features tasteful tile backsplash and efficient design, opening to a spacious living and dining area highlighted by a

  Adam Roy BHGRE Gaetano Marra Homes

  22 Woodbury Place Unit 22B, Woodbury, CT 06798
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  /12

  $2,100 Per Month

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

  300 Railtree Hill Rd Unit B, Woodbury, CT 06798

  Turnkey and move-in ready! This fully remodeled upper-level unit at 300 B Railtree Hill Rd offers a fresh, modern living space with thoughtful updates throughout. The unit features a beautifully updated kitchen, renovated bathroom, and new mini-split heating and cooling units for year-round comfort. An additional office provides a convenient space for working from home, studying, or a

  Kayla O'Grady William Raveis Real Estate

  300 Railtree Hill Rd Unit B, Woodbury, CT 06798
• 

  $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

  Current Estimated Value $480,049

  Last Listing Agent Michael Ferris eXp Realty

  158 Hazel Plain Rd, Woodbury, CT 06798
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  Not Listed For Sale

  31 Woods Way Unit 31, Woodbury, CT 06798

  • 2 Beds
  • 2 Baths
  • 1,582 Sq Ft
  • Built 1980

  31 Woods Way Unit 31, Woodbury, CT 06798

  Last Sold Summary

  • 213 Days On Market

  Last Listing Agent Eli Carneiro William Raveis Real Estate
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  $1,395,000

  • 3 Beds
  • 2.5 Baths
  • 2,346 Sq Ft

  509 Weekeepeemee Rd, Woodbury, CT 06798

  Steeped in 18th-century charm, this rare 1747 Saltbox estate seamlessly marries historic integrity with modern luxury. Tucked away on a peaceful country lane, the main home boasts original wide-plank wood floors, dual fireplaces, twin staircases, authentic built-ins, and freshly renovated baths. At its heart is the kitchen featuring Viking appliances and granite counters that open to garden

  Carla Mascaro William Pitt Sotheby's Int'l

  509 Weekeepeemee Rd, Woodbury, CT 06798
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  /12

  $2,100 Per Month

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

  300 Railtree Hill Rd Unit A, Woodbury, CT 06798

  Freshly updated and move-in ready! This inviting main-level unit at 300 A Railtree Hill Rd features one bedroom and one full bathroom, plus a spacious living room, comfortable dining area, and thoughtful storage throughout. The updated kitchen and bathroom feel fresh and modern, while new mini-split units with heat pump technology provide efficient heating and cooling year-round. Multiple closets

  Kayla O'Grady William Raveis Real Estate

  300 Railtree Hill Rd Unit A, Woodbury, CT 06798
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  $390,000

  Sold Mar 31, 2026

  142 Washington Rd, Woodbury, CT 06798

  • 2 Beds
  • 1 Bath
  • 1,340 Sq Ft
  • Built 1955

  Last Sold Summary

  • 3% Above List Price
  • $291/SF
  • 44 Days On Market

  Current Estimated Value $388,414

  Last Listing Agent Mary Ann Bennett Drakeley Real Estate, Inc.

  142 Washington Rd, Woodbury, CT 06798
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  Est $726,961

  Not Listed For Sale

  785 Washington Rd, Woodbury, CT 06798

  • 3 Beds
  • 6 Baths
  • 8,747 Sq Ft
  • Built 1982

  785 Washington Rd, Woodbury, CT 06798

  Last Sold Summary

  • 371 Days On Market

  Last Listing Agent Jeff Boucher Drakeley Real Estate, Inc.
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  /40

  $990,000

  Coming Soon

  • 6 Beds
  • 3.5 Baths
  • 3,842 Sq Ft

  92 Quail Run Rd, Woodbury, CT 06798

  A private retreat with Million dollar views! Nestled at the end of a peaceful cul-de-sac, this 3800+ Colonial offers a rare combination of privacy, space, and breathtaking views. Set against a backdrop of rolling hills, with gorgeous sunsets - where every season brings a beautiful new view. Step inside and you'll be greeted by expansive LR/Great RM featuring soaring cathedral ceilings, freshly

  Martha Chouinard Showcase Realty, Inc.

  92 Quail Run Rd, Woodbury, CT 06798
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  /17

  $2,750 Per Month

  • 3 Beds
  • 1.5 Baths
  • 1,440 Sq Ft
  • House for Rent

  650 Main St N, Woodbury, CT 06798

  Now available for rent! This well-maintained 3-bedroom home features a spacious eat-in kitchen, 1&1/2 baths, and a comfortable layout ideal for everyday living. Under house two car garage provides ample parking and additional storage. Conveniently located and ready for immediate occupancy, this home offers the space and comfort you've been looking for. Schedule your showing today!1 first month's

  Heather Wilson The Washington Agency

  650 Main St N, Woodbury, CT 06798
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  $435,000

  Sold Sep 15, 2026

  9 Spring St, Woodbury, CT 06798

  • 3 Beds
  • 1.5 Baths
  • 1,332 Sq Ft
  • Built 1890

  Last Sold Summary

  • 9% Above List Price
  • $327/SF
  • 15 Days On Market

  Current Estimated Value $394,085

  Last Listing Agent Claudine McHugh Klemm Real Estate Inc

  9 Spring St, Woodbury, CT 06798
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  Est $129,350

  Not Listed For Sale

  16 Pilgrim Trail Unit F2, Woodbury, CT 06798

  • 1 Bed
  • 1 Bath
  • 546 Sq Ft
  • Built 1965

  16 Pilgrim Trail Unit F2, Woodbury, CT 06798

  Last Sold Summary

  • 19 Days On Market

  Last Listing Agent Karen Rigopulos West View Properties, LLC
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  /40

  $675,000

  $24K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,081 Sq Ft

  61 Minortown Rd, Woodbury, CT 06798

  Some homes make their impression at the front door. This one begins long before it. Set nearly out of sight on almost three acres, the home is approached by a long driveway that opens to a circular drive and generous garage parking, a gracious arrival that feels worlds away. Inside, the floor plan delivers more than expected: a sunlit living room, formal dining room, updated white kitchen with

  Mustafa Muaremi Coldwell Banker Realty

  61 Minortown Rd, Woodbury, CT 06798
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  /35

  $4,800 Per Month

  • 4 Beds
  • 4.5 Baths
  • 3,200 Sq Ft
  • House for Rent

  259 Main St S, Woodbury, CT 06798

  Expansive main house with frontage on quintessential historic Main Street. RESIDENTIAL or COMMERCIAL space! Walk the sidewalks to the antique shops, parks, & restaurants. Enjoy the wineries and farm markets. Have a front row seat for the summer parades and the Christmas Eve luminaries that adorn Main Street. Deep lot with ample parking in the rear of the house. All four bedrooms have en-suite

  Gina Jacobs Gina Jacobs Real Estate

  259 Main St S, Woodbury, CT 06798
• 

  $1,500,000

  Sold Jul 15, 2026

  76 Cowles Rd, Woodbury, CT 06798

  • 3 Beds
  • 3 Baths
  • 2,072 Sq Ft
  • Built 2001

  Last Sold Summary

  • 17% Below List Price
  • $724/SF
  • 89 Days On Market

  Current Estimated Value $1,388,667

  Last Listing Agent Pam Famiglietti William Raveis Real Estate

  76 Cowles Rd, Woodbury, CT 06798
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  Not Listed For Sale

  0 Mill Rd, Woodbury, CT 06798

  0 Mill Rd, Woodbury, CT 06798

  Last Sold Summary

  • 54 Days On Market

  Last Listing Agent Jason Arcuri eXp Realty
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  /38

  $289,900

  Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,247 Sq Ft

  6 Upper Commons, Woodbury, CT 06798

  Welcome to sought-after Woodlake Estates! A peaceful, resort-like community surrounded by nature and recreational amenities. This spacious Townhouse-style end unit offers 9 rooms, 3+ bedrooms, 2.5 baths, a finished basement, and a detached 1-car garage. The main level features a generous sized living room with sliders leading to your private deck, kitchen with separate dining area, convenient

  Vasco Silva Great Estates, CT

  6 Upper Commons, Woodbury, CT 06798
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  /12

  $2,000 Per Month

  • 2 Beds
  • 1.5 Baths
  • 1,500 Sq Ft
  • Townhouse for Rent

  13 Pleasant St Unit 15, Woodbury, CT 06798

  Spacious two bedroom half duplex located up the street from Canfield Pharmacy.It's antique character features a light filled living room wit wood floors.eatin kitchen and dining toom. half bath on main level as laundry hookups. two bedrooms up and the full bath. Walk up attic for plenty of storage. Tenant must have FICO over 650 with good employment history. Year lease, NO PETS and NO SMOKERS!

  Sindy Butkus Klemm Real Estate Inc

  13 Pleasant St Unit 15, Woodbury, CT 06798
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  $660,000

  Sold Feb 05, 2026

  38 Barnhill Rd, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 2,835 Sq Ft
  • Built 1986

  Last Sold Summary

  • 5% Below List Price
  • $233/SF
  • 134 Days On Market

  Current Estimated Value $681,591

  Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

  38 Barnhill Rd, Woodbury, CT 06798
• 

  Est $963,381

  Not Listed For Sale

  17 Birchwood Ln, Woodbury, CT 06798

  • 3 Beds
  • 3 Baths
  • 3,283 Sq Ft
  • Built 2008

  17 Birchwood Ln, Woodbury, CT 06798

  Last Sold Summary

  • 80 Days On Market

  Last Listing Agent Christian Jensen William Pitt Sotheby's Int'l
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  /40

  $699,900

  $175K PRICE DROP Under Contract

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

  339 Main St S, Woodbury, CT 06798

  Watch the parade from your front yard, walk to school, walk to the excellent restaurants in town, walk to the library and to the local park and market! Fabulous location! One of Woodbury's last remaining homes built in the late 1600s. This charming residence offers a unique blend of historic character and modern convenience, ideally situated for those who appreciate easy access to local shops,

  Marian Van Egas Berkshire Hathaway NE Prop.

  339 Main St S, Woodbury, CT 06798
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  /15

  $1,450 Per Month

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

  35 Mill Rd, Woodbury, CT 06798

  Nestled in a peaceful residential setting with a scenic brook and bridge entry, this cozy ranch-style home offers the perfect blend of rural charm, natural beauty and convenient access to everyday conveniences. Freshly painted with refinished floors, this inviting home features comfortable living space, a kitchen with dining area, one bedroom, home office and a full bathroom with a freestanding

  Lisa McDonald The Brokerage of New England

  35 Mill Rd, Woodbury, CT 06798
• 

  $288,990

  Sold Sep 02, 2026

  54 Clubhouse Dr Unit 54, Woodbury, CT 06798

  • 2 Beds
  • 2.5 Baths
  • 1,916 Sq Ft
  • Built 1972

  Last Sold Summary

  • 7% Below List Price
  • $151/SF
  • 150 Days On Market

  Last Listing Agent Henrik K Kjaer Keller Williams Realty

  54 Clubhouse Dr Unit 54, Woodbury, CT 06798
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  Est $1,458,211

  Not Listed For Sale

  17 Gate Post Ln, Woodbury, CT 06798

  • 4 Beds
  • 4.5 Baths
  • 5,694 Sq Ft
  • Built 1998

  17 Gate Post Ln, Woodbury, CT 06798

  Last Sold Summary

  • 48 Days On Market

  Last Listing Agent Russell Antonacci Realtyworx, LLC
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  /32

  $549,900

  Pending

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

  25 Woodbury Hill, Woodbury, CT 06798

  Beautifully renovated and move-in ready, this stand-alone unit in the charming Woodbury Hill condominium community offers a bright, open floor plan and the convenience of first-floor living. Hardwood floors run throughout, while the expanded living room features a cathedral ceiling and dramatic floor-to-ceiling brick fireplace. The completely renovated kitchen opens to the dining room, creating

  Tim Drakeley Drakeley Real Estate, Inc.

  25 Woodbury Hill, Woodbury, CT 06798
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  /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
• 

  $750,000

  Sold Jun 15, 2026

  54 Bear Run, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 2,849 Sq Ft
  • Built 1998

  Last Sold Summary

  • 7% Above List Price
  • $263/SF
  • 46 Days On Market

  Current Estimated Value $732,207

  Last Listing Agent Becky Hood William Pitt Sotheby's Int'l

  54 Bear Run, Woodbury, CT 06798
• 

  Est $517,835

  Not Listed For Sale

  990 Washington Rd, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 1,847 Sq Ft
  • Built 2006

  990 Washington Rd, Woodbury, CT 06798

  Last Sold Summary

  • 85 Days On Market

  Last Listing Agent Pam Famiglietti William Raveis Real Estate

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