Woodbury, CT Homes

• 

  Est $855,386 Not Listed For Sale

  92 Tuttle Rd, Woodbury, CT 06798

  • 4 Beds
  • 3.5 Baths
  • 4,104 Sq Ft
  • Built 2005

  92 Tuttle Rd, Woodbury, CT 06798

  Last Sold Summary

  • 13% Above List Price
  • $184/SF
  • 85 Days On Market

  • Last Sold Price $755,000
  • Mar 06, 2025

  Last Listing Agent Dennis Oliveira JDS Realty Group Inc.
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  /32

  $599,900

  • 3 Beds
  • 2 Baths
  • 1,470 Sq Ft

  2 Judd Hill Rd, Woodbury, CT 06798

  Charm and modern comfort come together in this beautifully renovated 3-bedroom, 2-bath home set on nearly an acre along a quiet country road in Woodbury. Thoughtfully updated and move-in ready, this inviting home blends classic New England character with practical improvements throughout, including a fully insulated attic and insulated walls added by the current owner for enhanced comfort and

  Tim Drakeley Drakeley Real Estate, Inc.

  2 Judd Hill Rd, Woodbury, CT 06798
• 

  $585,000 Sold Aug 27, 2025

  18 Grey Fox Trail, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 1,873 Sq Ft
  • Built 1974

  Last Sold Summary

  • 10% Below List Price
  • $312/SF
  • 49 Days On Market

  Current Estimated Value $622,157

  Last Listing Agent Joseph Lorino Klemm Real Estate Inc

  18 Grey Fox Trail, Woodbury, CT 06798
• 

  Est $831,601 Not Listed For Sale

  40 Stonefield Rd, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 3,179 Sq Ft
  • Built 2006

  40 Stonefield Rd, Woodbury, CT 06798

  Last Sold Summary

  • 8% Below List Price
  • $283/SF
  • 51 Days On Market

  • Last Sold Price $900,000
  • Jul 12, 2024

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

  

  /2

  $1,495,000

  • 5 Beds
  • 4.5 Baths
  • 4,884 Sq Ft

  30 Hollow Rd, Woodbury, CT 06798

  Step through the doors of history and into one of Connecticut's most treasured colonial residences. Built in 1760 and proudly listed on the National Register of Historic Places, the Jabez Bacon House is a rare masterpiece of 18th-century American architecture that has endured with remarkable grace for over 260 years. This distinguished home has also been recognized for its exceptional

  Lisa Titcomb William Pitt Sotheby's Int'l

  30 Hollow Rd, Woodbury, CT 06798
• 

  $250,000 Sold Aug 29, 2025

  97 Westwood Rd, Woodbury, CT 06798

  • 2 Beds
  • 1 Bath
  • 1,264 Sq Ft
  • Built 1850

  Last Sold Summary

  • 11% Below List Price
  • $198/SF
  • 13 Days On Market

  Current Estimated Value $278,629

  Last Listing Agent Amy Vayan BHGRE Gaetano Marra Homes

  97 Westwood Rd, Woodbury, CT 06798
• 

  Est $341,915 Not Listed For Sale

  11 Boxwood Ct, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 2,388 Sq Ft
  • Built 1974

  11 Boxwood Ct, Woodbury, CT 06798

  Last Sold Summary

  • 17% Above List Price
  • $122/SF
  • 14 Days On Market

  • Last Sold Price $291,000
  • Jan 05, 2024

  Last Listing Agent Camron Cottam RE/MAX
• 

  

  /40

  $499,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 2,102 Sq Ft

  14 Meadow Crest Dr, Woodbury, CT 06798

  Opportunity knocks! Your chance to reside in an exclusive cul-de-sac area of north Woodbury! Homes on this street rarely come on the market. Situated on almost 4.5 acres and within a short drive of Woodbury and Watertown centers, including prestigious, private Taft School, this three bedroom, 1.5 bath colonial awaits its new owners! Exterior features include a chicken coop, above ground pool,

  Katherine Parlato Drakeley Real Estate, Inc.

  14 Meadow Crest Dr, Woodbury, CT 06798
• 

  $300,000 Sold Sep 11, 2025

  1 Alder Ct Unit 1, Woodbury, CT 06798

  • 2 Beds
  • 2.5 Baths
  • 1,365 Sq Ft
  • Built 1974

  Last Sold Summary

  • $220/SF
  • 54 Days On Market

  Current Estimated Value $297,883

  Last Listing Agent Camilo Ramirez Higgins Group Real Estate

  1 Alder Ct Unit 1, Woodbury, CT 06798
• 

  Est $938,816 Not Listed For Sale

  20 Birchwood Ln, Woodbury, CT 06798

  • 4 Beds
  • 3.5 Baths
  • 3,693 Sq Ft
  • Built 2004

  20 Birchwood Ln, Woodbury, CT 06798

  Last Sold Summary

  • 10% Above List Price
  • $230/SF
  • 168 Days On Market

  • Last Sold Price $850,000
  • Oct 31, 2024

  Last Listing Agent Tim Mohl HomeSmart Homes and Estates
• 

  

  /9

  $325,000

  • 3 Beds
  • 1 Bath
  • 1,089 Sq Ft

  54 Mountain Rd, Woodbury, CT 06798

  Welcome to the Historic town of Woodbury! Don't miss the opportunity to own this beautiful and well maintained home which offers a functional layout and abundant natural light. Features include spacious living areas, a well-appointed kitchen, comfortable bedrooms and a private outdoor space ideal for relaxing or entertaining. Conveniently located near schools, shopping, and major routes. A

  Genesis Hernandez BHGRE Shore & Country

  54 Mountain Rd, Woodbury, CT 06798
• 

  $250,000 Sold Apr 14, 2026

  5 Upper Commons, Woodbury, CT 06798

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

  Last Sold Summary

  • 6% Below List Price
  • $212/SF
  • 102 Days On Market

  Last Listing Agent Rafael Monegro Coldwell Banker Realty

  5 Upper Commons, Woodbury, CT 06798
• 

  Est $385,463 Not Listed For Sale

  354 Quassapaug Rd, Woodbury, CT 06798

  • 3 Beds
  • 1.5 Baths
  • 1,452 Sq Ft
  • Built 1966

  354 Quassapaug Rd, Woodbury, CT 06798

  Last Sold Summary

  • 3% Above List Price
  • $258/SF
  • 53 Days On Market

  • Last Sold Price $375,000
  • Jun 21, 2023

  Last Listing Agent Lisa Pompeo William Pitt
• 

  

  /20

  $245,000 Under Contract

  • 2 Beds
  • 2.5 Baths
  • 1,983 Sq Ft

  14 Tamarack Ln, Woodbury, CT 06798

  Opportunity awaits in this end unit tucked away in the Woodlake Complex. While in need of some work & new paint colors, there are some nice improvements already in place such as newer windows, wood & tile flooring, & kitchen cabinets. This unit has both a deck & patio overlooking the treed rear yard. Both are accessible from rear sliders. The lower level is finished & has a half bath within the

  Gina Jacobs Gina Jacobs Real Estate

  14 Tamarack Ln, Woodbury, CT 06798
• 

  $1,050,000 Sold Jun 06, 2025

  17 Transylvania Rd, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 3,928 Sq Ft
  • Built 2008

  Last Sold Summary

  • $267/SF
  • 34 Days On Market

  Current Estimated Value $1,078,102

  Last Listing Agent Michael Hvizdo Coldwell Banker Realty

  17 Transylvania Rd, Woodbury, CT 06798
• 

  Est $441,979 Not Listed For Sale

  18 Lake Rd, Woodbury, CT 06798

  • 4 Beds
  • 3 Baths
  • 2,028 Sq Ft
  • Built 1956

  18 Lake Rd, Woodbury, CT 06798

  Last Sold Summary

  • 5% Above List Price
  • $207/SF
  • 44 Days On Market

  • Last Sold Price $420,000
  • Aug 14, 2024

  Last Listing Agent David Aurigemma Regency Real Estate, LLC
• 

  

  /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
• 

  $490,000 Sold Nov 20, 2025

  15 Lynns Corner Rd, Woodbury, CT 06798

  • 4 Beds
  • 3 Baths
  • 2,216 Sq Ft
  • Built 1948

  Last Sold Summary

  • $221/SF
  • 27 Days On Market

  Current Estimated Value $510,800

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

  15 Lynns Corner Rd, Woodbury, CT 06798
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  Est $177,778 Not Listed For Sale

  229 Bacon Pond Rd Unit 233, Woodbury, CT 06798

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

  229 Bacon Pond Rd Unit 233, Woodbury, CT 06798

  Last Sold Summary

  • 3% Below List Price
  • $200/SF
  • 142 Days On Market

  • Last Sold Price $182,500
  • Apr 02, 2025

  Last Listing Agent Joe Dimyan Tower Realty Corp
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  /32

  $539,000

  • 2 Beds
  • 2 Baths
  • 1,986 Sq Ft

  43 Woodbury Hill, Woodbury, CT 06798

  Rarely is a ranch style available at Woodbury Hill as there are only 7 in total, This one is almost self standing-neighbor's one car garage is adjacent to this two car garage. There is an additional 640 sq.ft. in the heated lower level with a laundry room, closets, half bath and a separate work area and all with sliders to the yard. The beamed living/dining room is cathedral in the living room

  Joyce Drakeley Drakeley Real Estate, Inc.

  43 Woodbury Hill, Woodbury, CT 06798
• 

  $415,000 Sold Jun 04, 2025

  23 Woodbury Hill, Woodbury, CT 06798

  • 2 Beds
  • 2.5 Baths
  • 1,796 Sq Ft
  • Built 1985

  Last Sold Summary

  • 8% Below List Price
  • $231/SF
  • 55 Days On Market

  Current Estimated Value $451,831

  Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

  23 Woodbury Hill, Woodbury, CT 06798
• 

  Est $481,096 Not Listed For Sale

  38 Woodbury Hill, Woodbury, CT 06798

  • 2 Beds
  • 2.5 Baths
  • 1,796 Sq Ft
  • Built 1985

  38 Woodbury Hill, Woodbury, CT 06798

  Last Sold Summary

  • 3% Above List Price
  • $261/SF
  • 32 Days On Market

  • Last Sold Price $468,500
  • Nov 07, 2024

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

  

  /17

  $149,900 Under Contract

  • 2 Beds
  • 1 Bath
  • 913 Sq Ft

  229 Bacon Pond Rd Unit 312, Woodbury, CT 06798

  Waiting for your personal touch! This Town In Country lower level unit features a Living Room/Dining Room combo with Fireplace and slider leading to your own private Patio, Fully applianced Kitchen, 2 spacious Bedrooms, and Full Bath. Unit freshly painted with new carpet. Convenient to complex's in-ground pool and laundry. Minutes to Woodbury's town center with its shopping, top restaurants, &

  Ron Nettleton William Raveis Real Estate

  229 Bacon Pond Rd Unit 312, Woodbury, CT 06798
• 

  $970,000 Sold Dec 09, 2025

  25 Curtiss Meadows, Woodbury, CT 06798

  • 4 Beds
  • 3.5 Baths
  • 3,113 Sq Ft
  • Built 2005

  Last Sold Summary

  • 1% Below List Price
  • $312/SF
  • 132 Days On Market

  Last Listing Agent Ralph Harvey ListWithFreedom.com

  25 Curtiss Meadows, Woodbury, CT 06798
• 

  Est $469,571 Not Listed For Sale

  236 Quassuk Rd, Woodbury, CT 06798

  • 3 Beds
  • 2 Baths
  • 1,606 Sq Ft
  • Built 1840

  236 Quassuk Rd, Woodbury, CT 06798

  Last Sold Summary

  • 7% Above List Price
  • $274/SF
  • 62 Days On Market

  • Last Sold Price $440,000
  • Dec 24, 2024

  Last Listing Agent Kathryn Bassett William Pitt
• 

  

  /25

  $289,900 Under Contract

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

  14 Heather Ct Unit 14, Woodbury, CT 06798

  Welcome to this beautifully maintained ranch-style condo nestled in the peaceful charm of Woodbury, CT. Officially listed as a 2-bedroom home, this property offers exceptional flexibility with a mostly finished lower level featuring a spacious third bedroom-perfect for guests, a home office, or additional living space. The main level boasts a generously sized living room centered around a cozy

  Christopher Gueniat Northwest CT Realty

  14 Heather Ct Unit 14, Woodbury, CT 06798
• 

  $350,000 Sold Dec 18, 2025

  0 Main St N Unit 24072824, Woodbury, CT 06798

  • Land
  • 56.29 Acres
  • $6,218 per Acre

  Last Sold Summary

  • 12% Below List Price
  • 316 Days On Market

  Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

  0 Main St N Unit 24072824, Woodbury, CT 06798
• 

  Est $658,255 Not Listed For Sale

  167 Hazel Plain Rd, Woodbury, CT 06798

  • 4 Beds
  • 3.5 Baths
  • 2,922 Sq Ft
  • Built 1977

  167 Hazel Plain Rd, Woodbury, CT 06798

  Last Sold Summary

  • 20% Above List Price
  • $188/SF
  • 13 Days On Market

  • Last Sold Price $550,000
  • Aug 07, 2023

  Last Listing Agent Kerri Dimitratos William Raveis Real Estate
• 

  

  /40

  $255,000 Under Contract

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

  9 Highpoint Ct Unit 116E, Woodbury, CT 06798

  New price point! Come take a look at this lovely home! A perfect 1st or 2nd. home. Included: one car garage, plus one assigned parking space, a deck and patio for grilling. Notice the wooded privacy in the back. Inside a convenient kitchen, a breakfast nook (Or computer area etc.) There is a large living/dining room combo. The Fireplace is sealed shut for safety. However, w/permits, you can

  Terry Lee Adams Adams & Adams Real Estate

  9 Highpoint Ct Unit 116E, Woodbury, CT 06798
• 

  $200,000 Sold Jan 22, 2026

  12 Edgehill Ct, Woodbury, CT 06798

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

  Last Sold Summary

  • 7% Below List Price
  • $169/SF
  • 38 Days On Market

  Current Estimated Value $217,022

  Last Listing Agent Jacki Hornish W. Raveis Lifestyles Realty

  12 Edgehill Ct, Woodbury, CT 06798
• 

  Est $425,202 Not Listed For Sale

  61 Sherman Heights Rd, Woodbury, CT 06798

  • 2 Beds
  • 1 Bath
  • 924 Sq Ft
  • Built 1943

  61 Sherman Heights Rd, Woodbury, CT 06798

  Last Sold Summary

  • 12% Above List Price
  • $410/SF
  • 103 Days On Market

  • Last Sold Price $379,000
  • Oct 27, 2023

  Last Listing Agent Taylor O'Keefe Drakeley Real Estate, Inc.
• 

  

  /26

  $999,900

  • 3 Beds
  • 2.5 Baths
  • 2,042 Sq Ft

  27 Middle Quarter Rd, Woodbury, CT 06798

  Discover the charm of this beautiful antique home in the heart of Woodbury! Nestled on the serene Middle Quarter Road, this vintage gem is being restored by the current owner and is just a 2-minute stroll from coffee shops, top-notch restaurants, and the historic Main Street. The home will be meticulously updated from the ground up, featuring wide board antique flooring, a stunning great room

  Tim Drakeley Drakeley Real Estate, Inc.

  27 Middle Quarter Rd, Woodbury, CT 06798
• 

  $295,000 Sold May 15, 2025

  3 Woodbury Place Unit 3, Woodbury, CT 06798

  • 2 Beds
  • 1.5 Baths
  • 1,025 Sq Ft
  • Built 1979

  Last Sold Summary

  • 3% Below List Price
  • $288/SF
  • 29 Days On Market

  Current Estimated Value $302,082

  Last Listing Agent Katherine Parlato Drakeley Real Estate, Inc.

  3 Woodbury Place Unit 3, Woodbury, CT 06798
• 

  Est $1,781,486 Not Listed For Sale

  49 Owl Ridge Rd, Woodbury, CT 06798

  • 4 Beds
  • 5 Baths
  • 8,000 Sq Ft
  • Built 2006

  49 Owl Ridge Rd, Woodbury, CT 06798

  Last Sold Summary

  • 7% Above List Price
  • $208/SF
  • 135 Days On Market

  • Last Sold Price $1,660,000
  • Oct 17, 2023

  Last Listing Agent Christian Jensen William Pitt
• 

  

  /30

  $585,000 Under Contract

  • 1 Bed
  • 2 Baths
  • 1,564 Sq Ft

  123 Cross Brook Rd, Woodbury, CT 06798

  Offered for the first time, this custom-built Cape was carefully designed with a vision for both comfortable living and future expansion. Currently configured for easy one-level living, the home features a spacious, well-built layout with hardwood floors and generously proportioned rooms throughout. Upstairs, a blank canvas awaits-ready to become additional bedrooms, a full bath, and expanded

  Jeff Boucher Drakeley Real Estate, Inc.

  123 Cross Brook Rd, Woodbury, CT 06798
• 

  $110,000 Sold Nov 19, 2025

  0 Main St N Unit 24072843, Woodbury, CT 06798

  • Land
  • 2.1 Acres
  • $52,381 per Acre

  Last Sold Summary

  • 8% Below List Price
  • 231 Days On Market

  Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

  0 Main St N Unit 24072843, Woodbury, CT 06798
• 

  Est $177,606 Not Listed For Sale

  229 Bacon Pond Rd Unit 254, Woodbury, CT 06798

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

  229 Bacon Pond Rd Unit 254, Woodbury, CT 06798

  Last Sold Summary

  • 15% Above List Price
  • $170/SF
  • 6 Days On Market

  • Last Sold Price $155,000
  • Oct 26, 2023

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

  

  /39

  $419,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,716 Sq Ft

  40 Church St, Woodbury, CT 06798

  Highest and Best by 04/07 at 5:00pm. Beautiful 3-bedroom, 2-bath home located in the heart of Woodbury. Currently the only raised ranch on the market, this property offers a wonderful opportunity in a highly desirable area. The home features a level yard, perfect for outdoor enjoyment, along with a fully finished basement complete with a full bath-ideal for entertaining or providing comfortable

  Juliana Suzio RE/MAX RISE

  40 Church St, Woodbury, CT 06798
• 

  $568,000 Sold Sep 08, 2025

  81 Park Rd, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 2,144 Sq Ft
  • Built 1965

  Last Sold Summary

  • 1% Below List Price
  • $265/SF
  • 94 Days On Market

  Current Estimated Value $582,826

  Last Listing Agent Matt Rose Keller Williams Realty

  81 Park Rd, Woodbury, CT 06798
• 

  Not Listed For Sale

  203 Sprain Brook Rd, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 2,077 Sq Ft
  • Built 1862

  203 Sprain Brook Rd, Woodbury, CT 06798

  Last Sold Summary

  • $583/SF
  • 15 Days On Market

  • Last Sold Price $1,210,000
  • Oct 21, 2024

  Last Listing Agent Maria Taylor Klemm Real Estate Inc

Showing Results 121 - 160, Page 4 of 18