Woodbury, CT Homes

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  /26

  $649,900

  $25K 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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  /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

  

  Rebecca Doh

  W. Raveis Lifestyles Realty

  33 Washington Ave, 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
• 

  Est $787,975

  Not Listed For Sale

  101 Railtree Hill Rd, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 3,341 Sq Ft
  • Built 1987

  101 Railtree Hill Rd, Woodbury, CT 06798

  Last Sold Summary

  • 19 Days On Market

  Last Listing Agent Ellen Vincent William Raveis Real Estate
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  /40

  $774,900

  $25K PRICE DROP Pending

  • 5 Beds
  • 3.5 Baths
  • 3,607 Sq Ft

  17 Carriage Ln, Woodbury, CT 06798

  Center Hall Colonial with Full In-Law! This majestic brick facing home flaunts its location atop a private lot overlooking sprawling scenic views. Main level features a two-story foyer, formal dining room w/hardwoods & pocket doors leading to a high-end kitchen w/stainless steel appliances including a gas stove. The kitchen delivers with granite tops, upscale cabinetry, breakfast bar, & eat-in

  

  Shane Kropo

  RE/MAX RISE

  17 Carriage Ln, Woodbury, CT 06798
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  /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
• 

  $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 $635,781

  Last Listing Agent Michael Wright RE/MAX Right Choice

  13 Park Ln, Woodbury, CT 06798
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  Est $517,355

  Not Listed For Sale

  67 Flanders Rd, Woodbury, CT 06798

  • 4 Beds
  • 4 Baths
  • 2,764 Sq Ft
  • Built 1972

  67 Flanders Rd, Woodbury, CT 06798

  Last Sold Summary

  • 25 Days On Market

  Last Listing Agent Michael Calabro Coldwell Banker Calabro
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  /33

  $494,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 1,704 Sq Ft

  38 Mountain Rd, Woodbury, CT 06798

  Welcome to 38 Mountain Road, a perfect blend of functional living space and privacy while still offering a close proximity to town. Upon entering you are greeted with a warm and welcoming living room. This space flows into the dining room which is right next to the remodeled kitchen making dinner hosting a breeze! The kitchen offers a view of your private back yard from the window and beautiful

  

  Tami Hoxhallari

  Lotus Realty Group, LLC.

  38 Mountain Rd, Woodbury, CT 06798
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  /10

  $1,850 Plus Fees

  • 1 Bed
  • 1 Bath
  • Condo for Rent

  259 Main St S Unit 2, Woodbury, CT 06798

  Property Id: 2072920 Light and bright 2 Story 1 Bedroom Condo available for 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 don't wait schedule a tour today!

  259 Main St S Unit 2, 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 $493,100

  Last Listing Agent Nancy Langrock William Raveis Real Estate

  145 Cat Swamp Rd, Woodbury, CT 06798
• 

  Est $393,874

  Not Listed For Sale

  306 Upper Grassy Hill Rd, Woodbury, CT 06798

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

  306 Upper Grassy Hill Rd, Woodbury, CT 06798

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Shawna Mucherino Coldwell Banker Realty
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  /39

  $849,500

  $25K PRICE DROP

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

  339 Main St S, Woodbury, CT 06798

  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, parks, and restaurants. The interior of the home boasts a rich history with exposed wooden beams, 4 fireplaces, and classic hardwood floors, creating an inviting and warm

  

  Marian Van Egas

  Berkshire Hathaway NE Prop.

  339 Main St S, Woodbury, CT 06798
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  /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
• 

  $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 $484,504

  Last Listing Agent Michael Ferris eXp Realty

  158 Hazel Plain Rd, Woodbury, CT 06798
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  Est $838,644

  Not Listed For Sale

  59 Davids Hill Rd, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 2,475 Sq Ft
  • Built 1979

  59 Davids Hill Rd, Woodbury, CT 06798

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent Maria Taylor Klemm Real Estate Inc
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  /20

  $288,990

  $21K PRICE DROP Under Contract

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

  54 Clubhouse Dr Unit 54, Woodbury, CT 06798

  Welcome to this light-filled and beautifully maintained townhome in the highly sought-after Woodlake community in Woodbury. Spanning three levels, this inviting home offers a rare blend of space, comfort, and seasonal views of Wood Lake. The main level features a spacious living and dining area anchored by a striking floor-to-ceiling fireplace, enhanced with a wood-burning insert (2021). Sliding

  Henrik K Kjaer Keller Williams Realty

  54 Clubhouse Dr Unit 54, Woodbury, CT 06798
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  $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
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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 $383,788

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

  142 Washington Rd, Woodbury, CT 06798
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  Est $520,571

  Not Listed For Sale

  3 Lynns Corner Rd, Woodbury, CT 06798

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft
  • Built 1948

  3 Lynns Corner Rd, Woodbury, CT 06798

  Last Sold Summary

  • 67 Days On Market

  Last Listing Agent Rhya Szymansky Drakeley Real Estate, Inc.
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  /33

  $329,900

  Under Contract

  • 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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  /15

  $1,600 Per Month

  • 2 Beds
  • 1 Bath
  • 728 Sq Ft
  • House for Rent

  48 White Oak Rd Unit B, Woodbury, CT 06798

  Come see this conveniently located and quiet 2 bedroom apartment in the heart of Woodbury! Off of the main road, it is within walking distance to shops and restaurants, yet situated on a serene and private lot on a dead-end street. With a well-designed floor plan, this apartment blends functionality with comfort. At an affordable price, don't hesitate to take the opportunity to rent in one of

  Matthew Amatruda Drakeley Real Estate, Inc.

  48 White Oak Rd Unit B, 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 $1,366,781

  Last Listing Agent Pam Famiglietti William Raveis Real Estate

  76 Cowles 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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  /35

  $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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  /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
• 

  $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 $681,038

  Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

  38 Barnhill Rd, Woodbury, CT 06798
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  Est $707,108

  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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  /19

  $398,000

  Pending

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

  9 Spring St, Woodbury, CT 06798

  Warm and welcoming, this vintage home with a classic rocking chair front porch is ideally located within walking distance of Woodbury's town center. Beautifully maintained, it blends timeless character with thoughtful updates throughout. A gracious foyer with hardwood floors and a wall of closets provides exceptional storage. The living room features hardwood floors, built-in shelving, and an

  Claudine McHugh Klemm Real Estate Inc

  9 Spring St, Woodbury, CT 06798
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  /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
• 

  $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 $732,968

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

  54 Bear Run, Woodbury, CT 06798
• 

  Est $131,905

  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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  /36

  $1,575,000

  $350K PRICE DROP

  • 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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  /16

  $2,995 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
• 

  $1,400,000

  Sold Jul 16, 2026

  48 Coach Light Dr, Woodbury, CT 06798

  • 4 Beds
  • 4.5 Baths
  • 5,216 Sq Ft
  • Built 2001

  Last Sold Summary

  • 26% Below List Price
  • $268/SF
  • 40 Days On Market

  Current Estimated Value $1,563,618

  Last Listing Agent Nan Jane Keough William Pitt Sotheby's Int'l

  48 Coach Light Dr, 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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  /2

  $179,900

  Under Contract

  • Land
  • 4 Acres
  • $44,975 per Acre

  0 Carmel Hill Rd, Woodbury, CT 06798

  Discover your own private sanctuary on this enchanting ~4-acre parcel of pristine land perched along scenic Carmel Hill Road in historic Woodbury, CT. Nestled in the heart of Litchfield County's rolling countryside, this remarkable property captivates with mesmerizing views of a sparkling waterfall and the gentle flow of a serene river-nature's own symphony right at your doorstep. Imagine

  Melissa Gordon Coldwell Banker Realty

  0 Carmel Hill 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
• 

  $530,000

  Sold May 01, 2026

  31 McVeigh Rd, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 2,256 Sq Ft
  • Built 1987

  Last Sold Summary

  • 12% Below List Price
  • $235/SF
  • 211 Days On Market

  Current Estimated Value $539,906

  Last Listing Agent Jennifer Bundock Coldwell Banker Realty

  31 McVeigh Rd, Woodbury, CT 06798
• 

  Est $944,434

  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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