Woodbury, CT Homes

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  /40

  $675,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,073 Sq Ft

  43 Mill Rd, Woodbury, CT 06798

  Experience the ease of single-level living in this lovingly maintained residence. Nestled on a private lot bordering acres of open space, this home is a study in thoughtful design and architectural detail. The interior is defined by a sense of scale and light, featuring hardwood floors, elegant tray ceilings, and custom crown moldings. At the heart of the home, the spacious living room is

  Christian Jensen William Pitt Sotheby's Int'l

  43 Mill Rd, Woodbury, CT 06798
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• 

  

  

  /18

  $1,600 total monthly price

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

  4 Weekeepeemee Rd, Woodbury, CT 06798

  Freshly painted, new counter tops, new appliances - including the one unit washer / dryer, new tub/shower enclosure. Ready for immediate occupancy. Bright, sunny unit - pics show last bit of painting and clean up is being completed, but it's ready to show. One large bedroom, and one bedroom is small, perfect for home office, child, or a large walk in closet!! Living room and bedrooms have

  Mary Ann Bennett Drakeley Real Estate, Inc.

  4 Weekeepeemee Rd, Woodbury, CT 06798
• 

  $125,000 Sold Sep 16, 2025

  14 Arrowhead Way Unit 6, Woodbury, CT 06798

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

  Last Sold Summary

  • 4% Below List Price
  • $229/SF
  • 91 Days On Market

  Current Estimated Value $126,396

  Last Listing Agent Jeff Boucher Drakeley Real Estate, Inc.

  14 Arrowhead Way Unit 6, Woodbury, CT 06798
• 

  Est $868,595 Not Listed For Sale

  60 Stone Pit Rd, Woodbury, CT 06798

  • 4 Beds
  • 5 Baths
  • 3,583 Sq Ft
  • Built 1999

  60 Stone Pit Rd, Woodbury, CT 06798

  Last Sold Summary

  • 12% Above List Price
  • $216/SF
  • 35 Days On Market

  Last Sold Price $775,000

  Last Listing Agent Sharon McGuire William Pitt
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  /40

  $350,000

  • 3 Beds
  • 2.5 Baths
  • 1,640 Sq Ft

  24 Woods Way Unit 122A, Woodbury, CT 06798

  An updated condo w/modern overtones for you! Comfort and updated style greet you in this spacious, airy, end unit! 3 Spacious Bedrooms and 2.5 oversized bathrooms for your living enjoyment. The Condo has been tastefully renovated and professionally cleaned for your move-in-day! The Homestead floor plan provides a Galley Kitchen with a "great-room application". This is a lovely space to utilize as

  Terry Lee Adams Adams & Adams Real Estate

  24 Woods Way Unit 122A, Woodbury, CT 06798
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  /30

  $2,000 total monthly price

  • 2 Beds
  • 1 Bath
  • 913 Sq Ft
  • Condo for Rent

  229 Bacon Pond Rd Unit 229 Bacon Pond Rd APT 232, Woodbury, CT 06798

  Gorgeous 2-bedroom 1-bath condo. Luxury vinyl plank flooring. Private patio. 2 designated parking spaces. Swimming Pool. Beautiful country setting. Close to town. No smoking. No pets. Rent includes water and condo fees. Renter pays electric and utilities. 2 months' deposit and 1st month's rent due at signing.

  229 Bacon Pond Rd Unit 229 Bacon Pond Rd APT 232, Woodbury, CT 06798
• 

  $449,900 Sold Aug 08, 2025

  67 Flanders Rd, Woodbury, CT 06798

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

  Last Sold Summary

  • $163/SF
  • 25 Days On Market

  Current Estimated Value $476,886

  Last Listing Agent Michael Calabro Coldwell Banker Calabro

  67 Flanders Rd, Woodbury, CT 06798
• 

  Est $537,073 Not Listed For Sale

  325 Cowles Rd, Woodbury, CT 06798

  • 3 Beds
  • 2 Baths
  • 2,190 Sq Ft
  • Built 1947

  325 Cowles Rd, Woodbury, CT 06798

  Last Sold Summary

  • 21% Above List Price
  • $202/SF
  • 142 Days On Market

  Last Sold Price $442,500

  Last Listing Agent Mary Ann Bennett Drakeley Real Estate, Inc.
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  /16

  $849,000 Open Sat 12PM - 2PM

  • 3 Beds
  • 4 Baths
  • 3,082 Sq Ft

  148 Flanders Rd, Woodbury, CT 06798

  Country Living Abounds with this unique custom built one of a kind Cape nestled on 5 secluded acres. This home features an open floor plan with post and beam construction, beamed ceilings, oak floors, Plaster Walls, fully applianced Kitchen with breakfast bar, a spacious Family Room with brick fireplace, built-ins, & slider leading to back deck. The Living Room with fireplace is adjacent to a

  Ron Nettleton William Raveis Real Estate

  148 Flanders Rd, Woodbury, CT 06798
• 

  

  /11

  $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
• 

  $522,500 Sold Feb 18, 2026

  667 Upper Grassy Hill Rd, Woodbury, CT 06798

  • 4 Beds
  • 2 Baths
  • 1,987 Sq Ft
  • Built 1973

  Last Sold Summary

  • 5% Below List Price
  • $263/SF
  • 75 Days On Market

  Current Estimated Value $556,664

  Last Listing Agent Rhya Szymansky Drakeley Real Estate, Inc.

  667 Upper Grassy Hill Rd, Woodbury, CT 06798
• 

  Est $241,544 Not Listed For Sale

  76 Washington Rd Unit 40, Woodbury, CT 06798

  • 2 Beds
  • 1.5 Baths
  • 1,430 Sq Ft
  • Built 1988

  76 Washington Rd Unit 40, Woodbury, CT 06798

  Last Sold Summary

  • 2% Below List Price
  • $172/SF
  • 22 Days On Market

  Last Sold Price $245,500

  Last Listing Agent Colleen Pickwick eXp Realty
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  /21

  $339,999

  • 2 Beds
  • 2 Baths
  • 2,118 Sq Ft

  8 Tamarack Ln Unit 8, Woodbury, CT 06798

  3 bedrooms on 2 levels in this spacious end-unit condo offering 2118 ft of comfort, style, and a peaceful setting. Although listed as a 2-bedroom, the expansive heated and cooled lower level features additional rooms, one currently used as a bedroom with a closet, a large family room, plus a storage room, and a laundry room! Many options for a home office or gym. On the main level, the updated

  Jennifer Mayo William Raveis Real Estate

  8 Tamarack Ln Unit 8, Woodbury, CT 06798
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  $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
• 

  $128,500 Sold Jul 23, 2025

  16 Pilgrim Trail Unit F2, Woodbury, CT 06798

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

  Last Sold Summary

  • $235/SF
  • 19 Days On Market

  Current Estimated Value $128,697

  Last Listing Agent Karen Rigopulos BHGRE Gaetano Marra Homes

  16 Pilgrim Trail Unit F2, Woodbury, CT 06798
• 

  Est $909,807 Not Listed For Sale

  62 Whittlesey Rd, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 3,205 Sq Ft
  • Built 2002

  62 Whittlesey Rd, Woodbury, CT 06798

  Last Sold Summary

  • 7% Above List Price
  • $265/SF
  • 34 Days On Market

  Last Sold Price $850,000

  Last Listing Agent Brianna Carvalho Compass Connecticut, LLC
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  /26

  $925,000 Pending

  • 4 Beds
  • 5.5 Baths
  • 5,114 Sq Ft

  35 Coach Light Dr, Woodbury, CT 06798

  This exceptional residence welcomes you with a dramatic two-story entry and is designed for both refined entertaining and comfortable everyday living, just minutes from town. There is a formal living and dining room with rich hardwood flooring, creating a sophisticated setting for gatherings. The heart of the home is a beautifully appointed chef's kitchen featuring granite countertops, a

  Maria Taylor Klemm Real Estate Inc

  35 Coach Light Dr, Woodbury, CT 06798
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  /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
• 

  $628,500 Sold Apr 28, 2025

  49 Jacks Bridge Rd, Woodbury, CT 06798

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft
  • Built 1987

  Last Sold Summary

  • 10% Below List Price
  • $624/SF
  • 228 Days On Market

  Last Listing Agent Christine Green Ardor Real Estate

  49 Jacks Bridge Rd, Woodbury, CT 06798
• 

  Not Listed For Sale

  267 Good Hill Rd, Woodbury, CT 06798

  • 3 Beds
  • 4 Baths
  • 3,349 Sq Ft
  • Built 1790

  267 Good Hill Rd, Woodbury, CT 06798

  Last Sold Summary

  • $366/SF
  • 54 Days On Market

  Last Sold Price $1,225,000

  Last Listing Agent Maris LeBlanc William Pitt
• 

  

  /31

  $895,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 3,776 Sq Ft

  52 Steeple View Ln, Woodbury, CT 06798

  Nestled within an established enclave of Woodbury-a quintessential New England town-this 2001 four-bedroom Colonial offers a refined blend of understated, classic architecture, and modern comfort. Ideally located just five minutes from Main Street, the home is privately sited at the end of a quiet cul-de-sac, bordered by tranquil woodlands. The interior showcases richly layered trim details,

  Beverly Mosch William Pitt Sotheby's Int'l

  52 Steeple View Ln, Woodbury, CT 06798
• 

  $370,000 Sold Dec 29, 2025

  298 Railtree Hill Rd, Woodbury, CT 06798

  • 3 Beds
  • 2 Baths
  • 1,510 Sq Ft
  • Built 1967

  Last Sold Summary

  • 10% Below List Price
  • $245/SF
  • 95 Days On Market

  Current Estimated Value $382,512

  Last Listing Agent Shawna Mucherino Coldwell Banker Realty

  298 Railtree Hill Rd, Woodbury, CT 06798
• 

  Est $183,536 Not Listed For Sale

  229 Bacon Pond Rd Unit 142, Woodbury, CT 06798

  • 2 Beds
  • 1 Bath
  • 913 Sq Ft
  • Built 1971

  229 Bacon Pond Rd Unit 142, Woodbury, CT 06798

  Last Sold Summary

  • 3% Above List Price
  • $196/SF
  • 60 Days On Market

  Last Sold Price $179,000

  Last Listing Agent Anthony Rivera Pro Property Management, LLC
• 

  

  /40

  $699,000

  • 3 Beds
  • 3.5 Baths
  • 3,210 Sq Ft

  58 Good Hill Rd, Woodbury, CT 06798

  Located in picturesque Woodbury, voted Most Charming Town in CT by Reader's Digest in 2018, 2020 and 2024 and featured by Travel + Leisure among the 10 Best Places to Live. This stately circa 1845 home blends historic character with comfortable living. Set along scenic Good Hill Road and surrounded by lush, established gardens, featuring a black bottom gunite pool, private terrace, welcoming

  Christina Zainc BHGRE Gaetano Marra Homes

  58 Good Hill Rd, Woodbury, CT 06798
• 

  $439,900 Sold Sep 02, 2025

  22 Lake Rd, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 2,008 Sq Ft
  • Built 1956

  Last Sold Summary

  • $219/SF
  • 46 Days On Market

  Current Estimated Value $437,614

  Last Listing Agent Matt Rose Keller Williams Realty

  22 Lake Rd, Woodbury, CT 06798
• 

  Est $402,388 Not Listed For Sale

  87 Minortown Rd, Woodbury, CT 06798

  • 3 Beds
  • 1.5 Baths
  • 1,615 Sq Ft
  • Built 1965

  87 Minortown Rd, Woodbury, CT 06798

  Last Sold Summary

  • 18% Below List Price
  • $303/SF
  • 91 Days On Market

  Last Sold Price $490,000

  Last Listing Agent Rhonda Stokes Drakeley Real Estate, Inc.
• 

  

  /27

  $304,900

  • 2 Beds
  • 3.5 Baths
  • 1,762 Sq Ft

  13 Clubhouse Dr Unit 13, Woodbury, CT 06798

  Welcome to this well-maintained 3-level condo in the desirable Woodlake community. This spacious unit offers 2 bedrooms, 3 full baths and 1 half bath, plenty of natural light, and a large private deck off the main living area. The kitchen features stainless steel appliances, with washer and dryer conveniently located on the upper level. A fully finished walkout lower level with a full bathroom

  Lance Camby Robert C White & Company LLC

  13 Clubhouse Dr Unit 13, Woodbury, CT 06798
• 

  $850,000 Sold Oct 29, 2025

  84 Hurds Hill Rd, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 3,736 Sq Ft
  • Built 1966

  Last Sold Summary

  • 4% Below List Price
  • $228/SF
  • 135 Days On Market

  Current Estimated Value $868,685

  Last Listing Agent Michael Vartolone William Raveis Real Estate

  84 Hurds Hill Rd, Woodbury, CT 06798
• 

  Not Listed For Sale

  126 Sherman Hill Rd Unit B8, Woodbury, CT 06798

  • 2 Beds
  • 1.5 Baths
  • 1,150 Sq Ft
  • Built 1964

  126 Sherman Hill Rd Unit B8, Woodbury, CT 06798

  Last Sold Summary

  • $168/SF
  • 54 Days On Market

  Last Sold Price $193,000

  Last Listing Agent Sindy Butkus Klemm Real Estate Inc
• 

  

  /40

  $749,000 Under Contract

  • 3 Beds
  • 3.5 Baths
  • 3,749 Sq Ft

  19 Hillview Ln, Woodbury, CT 06798

  Nestled within the exclusive South Brook community, 19 Hill View Lane offers timeless New England charm paired with exceptional craftsmanship. This beautifully appointed 3 bedroom, 3.5 bath cape colonial is rich in architectural detail, featuring refined millwork, quality finishes, and a thoughtful layout designed for both everyday living and elegant entertaining. The main living spaces flow

  Nicole Fiorelli Fiorelli Realty, LLC

  19 Hillview Ln, Woodbury, CT 06798
• 

  $1,075,000 Sold Aug 21, 2025

  5 Blueberry Ln, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 3,874 Sq Ft
  • Built 2006

  Last Sold Summary

  • 8% Above List Price
  • $277/SF
  • 36 Days On Market

  Current Estimated Value $1,101,881

  Last Listing Agent John Donato Jr Showcase Realty, Inc.

  5 Blueberry Ln, Woodbury, CT 06798
• 

  Est $593,098 Not Listed For Sale

  80 Flanders Rd, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 2,165 Sq Ft
  • Built 1950

  80 Flanders Rd, Woodbury, CT 06798

  Last Sold Summary

  • 18% Below List Price
  • $333/SF
  • 3 Days On Market

  Last Sold Price $720,000

  Last Listing Agent Sandra Kerr Berkshire Hathaway Home Services
• 

  

  /24

  $379,900 Under Contract

  • 2 Beds
  • 1 Bath
  • 1,340 Sq Ft

  142 Washington Rd, Woodbury, CT 06798

  Tucked back and hidden away, yet just a short walk into town, the elementary and middle schools, public tennis and pickle ball courts. Sidewalks run thru the town to meander into all boutiques, antiques, and restaurants. Very charming, solid ranch, hardwood flooring, large kitchen w travertine and subway tiling, dining room with french doors out to the oversized deck, living room with fireplace

  Mary Ann Bennett Drakeley Real Estate, Inc.

  142 Washington Rd, Woodbury, CT 06798
• 

  $290,000 Sold May 09, 2025

  44 Woods Way Unit 44, Woodbury, CT 06798

  • 2 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Built 1979

  Last Sold Summary

  • $199/SF
  • 4 Days On Market

  Last Listing Agent Kristie Perry William Pitt Sotheby's Int'l

  44 Woods Way Unit 44, Woodbury, CT 06798
• 

  Est $501,675 Not Listed For Sale

  54 Barbara Ln, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 2,901 Sq Ft
  • Built 1959

  54 Barbara Ln, Woodbury, CT 06798

  Last Sold Summary

  • 7% Above List Price
  • $162/SF
  • 36 Days On Market

  Last Sold Price $470,000

  Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.
• 

  

  /34

  $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
• 

  $499,000 Sold Jun 16, 2025

  98 Old Town Farm Rd, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 1,648 Sq Ft
  • Built 1972

  Last Sold Summary

  • 1% Above List Price
  • $303/SF
  • 3 Days On Market

  Current Estimated Value $505,865

  Last Listing Agent Jeff Boucher Drakeley Real Estate, Inc.

  98 Old Town Farm Rd, Woodbury, CT 06798
• 

  Est $283,325 Not Listed For Sale

  28 Fox Run, Woodbury, CT 06798

  • 2 Beds
  • 2 Baths
  • 1,182 Sq Ft
  • Built 1980

  28 Fox Run, Woodbury, CT 06798

  Last Sold Summary

  • 5% Above List Price
  • $228/SF
  • 55 Days On Market

  Last Sold Price $270,000

  Last Listing Agent Wendy Brazauskas Coldwell Banker Realty
• 

  /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
• 

  $483,000 Sold Aug 06, 2025

  3 Lynns Corner Rd, Woodbury, CT 06798

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

  Last Sold Summary

  • 9% Below List Price
  • $201/SF
  • 67 Days On Market

  Current Estimated Value $505,710

  Last Listing Agent Rhya Szymansky Drakeley Real Estate, Inc.

  3 Lynns Corner Rd, Woodbury, CT 06798

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