Woodbury, CT Homes

• 

  $500,000

  Sold Mar 09, 2026

  9 Hill View Ln, Woodbury, CT 06798

  • 2 Beds
  • 2.5 Baths
  • 3,362 Sq Ft
  • Built 2004

  Last Sold Summary

  • 7% Below List Price
  • $149/SF
  • 75 Days On Market

  Current Estimated Value $550,970

  Last Listing Agent Christina Zainc BHGRE Gaetano Marra Homes

  9 Hill View Ln, Woodbury, CT 06798
• 

  Est $864,560

  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

  • 85 Days On Market

  Last Listing Agent Dennis Oliveira JDS Realty Group Inc.
• 

  

  

  /30

  $1,100,000

  • 4 Beds
  • 4 Baths
  • 4,491 Sq Ft

  16 Gate Post Ln, Woodbury, CT 06798

  Spacious Colonial in desirable Carriage Hills offers approximately 5,700 square feet of living space, including a walk-out lower level that is well suited for an in-law suite or au pair quarters. The main level features wood floors, formal living and dining rooms, an eat-in kitchen, a bedroom, a full bath, and a family room with a fireplace that opens to an oversized deck. Upstairs, you'll find

  Sindy Butkus Klemm Real Estate Inc

  16 Gate Post Ln, Woodbury, CT 06798
• 

  $400,000

  Sold Jan 12, 2026

  70 Mountain Rd, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 2,240 Sq Ft
  • Built 1961

  Last Sold Summary

  • 9% Below List Price
  • $179/SF
  • 57 Days On Market

  Current Estimated Value $450,184

  Last Listing Agent Donna J. Matula William Raveis Real Estate

  70 Mountain Rd, Woodbury, CT 06798
• 

  Est $908,738

  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

  • 51 Days On Market

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

  

  /40

  $769,900

  $30K PRICE DROP Under Contract

  • 4 Beds
  • 2.5 Baths
  • 3,223 Sq Ft

  62 Heritage Dr, Woodbury, CT 06798

  Beautifully renovated 4-bedroom, 2.5-bath ranch set on a spacious corner lot in one of Woodbury's most desirable locations. Just two streets from Woodbury's nationally recognized Main Street, this home offers the perfect combination of modern updates, comfortable living, and exceptional outdoor entertaining. The complete interior renovation began in 2023 and has recently been completed, creating

  Jonathan Pinto Pinto Real Estate Group LLC

  62 Heritage Dr, Woodbury, CT 06798
• 

  $640,000

  Sold Nov 20, 2025

  32 Plumb Brook Rd, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 2,252 Sq Ft
  • Built 1979

  Last Sold Summary

  • 3% Below List Price
  • $284/SF
  • 54 Days On Market

  Current Estimated Value $668,768

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

  32 Plumb Brook Rd, Woodbury, CT 06798
• 

  Est $221,989

  Not Listed For Sale

  74 Washington Rd Unit 4, Woodbury, CT 06798

  • 2 Beds
  • 1.5 Baths
  • 960 Sq Ft
  • Built 1969

  74 Washington Rd Unit 4, Woodbury, CT 06798

  Last Sold Summary

  • 9 Days On Market

  Last Listing Agent Jack Gregory Sette Real Estate LLC
• 

  

  /28

  $765,000

  New Construction $20K PRICE INCREASE

  • 3 Beds
  • 2.5 Baths
  • 2,060 Sq Ft

  86 Quail Run Rd, Woodbury, CT 06798

  QUAIL RUN On the cul de sac - 4 NEW HOMES ALL ON FLAT LOTS! They might be what you have been looking for - SMALLER & SMARTER new homes with PRICES TO MATCH. Beautiful 1 acre+ lots on shared common drives surrounded by 12 ACRES OF PRIVATE OPEN SPACE. This is QUINTESSENTIAL WOODBURY - Quiet, woodsy, and BEAUTIFUL! Construction has begun with completion possible in early October. #86 is a 3 BR, 2.5

  Scott Volpe Coldwell Banker Realty

  86 Quail Run Rd, Woodbury, CT 06798
• 

  $35,000

  Sold Nov 20, 2025

  0 Main St N Unit 24119173, Woodbury, CT 06798

  • Land
  • 3.6 Acres
  • $9,722 per Acre

  Last Sold Summary

  • 46% Below List Price
  • 57 Days On Market

  Last Listing Agent Jeff Boucher Drakeley Real Estate, Inc.

  0 Main St N Unit 24119173, Woodbury, CT 06798
• 

  Est $346,133

  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

  • 14 Days On Market

  Last Listing Agent Camron Cottam RE/MAX RISE
• 

  

  /40

  $825,000

  • 6 Beds
  • 3.5 Baths
  • 5,815 Sq Ft

  24 Scuppo Rd, Woodbury, CT 06798

  Impressive and spacious 5,815 sq. ft. well maintained residence with BRAND NEW ROOF (installed 1/15/26) offering exceptional one-level living with 6 bedrooms, 4 full bathrooms, and an oversized heated 3-car garage. A welcoming 12' x 9' slate-floor foyer introduces the home and leads to generously proportioned living spaces designed for both everyday comfort and entertaining. The oversized formal

  David Hughes Century 21 AllPoints Realty

  24 Scuppo Rd, Woodbury, CT 06798
• 

  $189,200

  Sold Jul 13, 2026

  229 Bacon Pond Rd Unit 451, Woodbury, CT 06798

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

  Last Sold Summary

  • 3% Above List Price
  • $207/SF
  • 40 Days On Market

  Current Estimated Value $185,914

  Last Listing Agent Susan Pelletier Berkshire Hathaway NE Prop.

  229 Bacon Pond Rd Unit 451, Woodbury, CT 06798
• 

  Est $961,435

  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

  • 168 Days On Market

  Last Listing Agent Tim Mohl HomeSmart Homes and Estates
• 

  /2

  $1,395,000

  $100K PRICE DROP

  • 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
• 

  $199,000

  Sold Sep 24, 2026

  229 Bacon Pond Rd Unit 351, Woodbury, CT 06798

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

  Last Sold Summary

  • 2% Above List Price
  • $218/SF
  • 34 Days On Market

  Current Estimated Value $189,078

  Last Listing Agent Katherine Parlato Drakeley Real Estate, Inc.

  229 Bacon Pond Rd Unit 351, Woodbury, CT 06798
• 

  Est $453,587

  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

  • 44 Days On Market

  Last Listing Agent David Aurigemma Regency Real Estate, LLC
• 

  

  /40

  $2,995,000

  • 4 Beds
  • 6 Baths
  • 5,316 Sq Ft

  920 Main St S, Woodbury, CT 06798

  Warren's Landing on the Pomperaug is an extraordinary estate where historic character is centered around a beautifully preserved 1890 Greek Revival residence. The home offers four bedrooms, timeless architectural details, spacious rooms, 4 fireplaces and custom built-ins. The impressive six-barn complex provides exceptional flexibility, featuring a retail shop, extensive equipment storage, a

  Maria Taylor Klemm Real Estate Inc

  920 Main St S, Woodbury, CT 06798
• 

  $145,000

  Sold Jun 04, 2026

  229 Bacon Pond Rd Unit 453, Woodbury, CT 06798

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

  Last Sold Summary

  • $159/SF
  • 33 Days On Market

  Current Estimated Value $146,075

  Last Listing Agent Deborah Snopkowski Coldwell Banker Realty

  229 Bacon Pond Rd Unit 453, Woodbury, CT 06798
• 

  Est $185,173

  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

  • 142 Days On Market

  Last Listing Agent Joe Dimyan Tower Realty Corp
• 

  

  /20

  $749,900

  $25K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,708 Sq Ft

  28 School St, Woodbury, CT 06798

  The Orton-Martin Homestead. One of Woodbury's oldest homes has been updated for today's lifestyle. History surrounds you with wide board flooring, library built-ins, two fireplaces and 1850 barn. This four -bedroom home offers spacious rooms, three finished levels and hidden delights. Enjoy picnics under the mature trees on your own fenced-in level yard. Sidewalks take you everywhere on Main St

  Sindy Butkus Klemm Real Estate Inc

  28 School St, 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 $504,122

  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

  • 32 Days On Market

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

  

  /15

  $990,000

  New Construction 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.

  523 Main St N, Woodbury, CT 06798
• 

  $426,500

  Sold Jun 23, 2026

  360 Old Sherman Hill Rd, Woodbury, CT 06798

  • 3 Beds
  • 1 Bath
  • 1,296 Sq Ft
  • Built 1966

  Last Sold Summary

  • 5% Below List Price
  • $329/SF
  • 41 Days On Market

  Current Estimated Value $428,979

  Last Listing Agent Levi Judqin Brass Moon Realty

  360 Old Sherman Hill Rd, Woodbury, CT 06798
• 

  Est $470,495

  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

  • 62 Days On Market

  Last Listing Agent Kathryn Bassett William Pitt Sotheby's Int'l
• 

  

  /33

  $299,000

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,467 Sq Ft

  8 Woods Way Unit 8, Woodbury, CT 06798

  PRETTY AND SO PRIVATE!! Enjoy nature right from your back door in this spacious, freshly painted 3-bedroom home! Imagine relaxing with a cup of coffee on your private deck. Kitchen is nicely updated with large pantry, stainless appliances, dining area and ceiling fan. The living room features a warming fireplace with Pellet Stove for an economical heat source. and the dining room boasts sliders

  Marian Van Egas Berkshire Hathaway NE Prop.

  8 Woods Way Unit 8, 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 $513,007

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

  15 Lynns Corner Rd, Woodbury, CT 06798
• 

  Est $396,087

  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

  • 103 Days On Market

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

  

  /34

  $589,000

  • 3 Beds
  • 2.5 Baths
  • 3,282 Sq Ft

  323 Upper Grassy Hill Rd, Woodbury, CT 06798

  Welcome home! The details of this home are what make it unique. From the gigantic hydrangeas to the appetizing peach and pear trees, this home will continue to exceed expectations. Inside is remodeled and immaculate with the great elasticity that so many lack. The finely scaled rooms are so versatile, the home really allows you to figure out what works for you. For instance, the dining room,

  Gabby Addison Keller Williams Realty

  323 Upper Grassy Hill Rd, 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 $1,900,552

  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

  • 135 Days On Market

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

  

  /26

  $999,900

  $100K PRICE DROP Under Contract

  • 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
• 

  $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
• 

  

  /25

  Est $238,275

  Not Listed For Sale

  74 Washington Rd Unit 16, Woodbury, CT 06798

  • 2 Beds
  • 1.5 Baths
  • 960 Sq Ft
  • Built 1969

  74 Washington Rd Unit 16, Woodbury, CT 06798

  Last Sold Summary

  Last Listing Agent Cal Massaro Coldwell Banker Realty
• 

  

  /40

  $699,900

  Under Contract

  • 4 Beds
  • 2.5 Baths
  • 3,017 Sq Ft

  15 Saxony Ln, Woodbury, CT 06798

  Welcome home to this beautifully maintained 4-bedroom, 2.5-bath center hall colonial, ideally situated on a desirable cul-de-sac just minutes from the charming town centers of Woodbury and Roxbury. With its quintessential wrap-around front porch and classic New England character, this home offers timeless appeal in a wonderful setting. A gracious foyer welcomes you with a formal dining room and

  Stephanie Chapman BHGRE Gaetano Marra Homes

  15 Saxony Ln, 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 $217,706

  Last Listing Agent Jacki Hornish W. Raveis Lifestyles Realty

  12 Edgehill Ct, Woodbury, CT 06798
• 

  Est $181,572

  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

  • 6 Days On Market

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

  

  /39

  $289,000

  • 2 Beds
  • 2 Baths
  • 1,112 Sq Ft

  5 Alder Ct Unit 84A, Woodbury, CT 06798

  Woodlake has 7 Ranch Style Units with either a carport or garage; making #5 Alder Court is a rare-find-end unit! The walk from the parking area is level to an inviting Court-yard and onto this lovely ranch style home. You will notice the natural private surroundings. Once inside, beautiful wood floors greet you. Beautiful windows provide natural sunlight. The LR has a cathedral ceiling. The

  Terry Lee Adams Adams & Adams Real Estate

  5 Alder Ct Unit 84A, 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

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