Woodbury, CT Homes

• 

  Est $174,509

  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
• 

  

  

  /40

  $2,995,000

  Open Sat 12PM - 2PM

  • 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
• 

  $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 $649,316

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

  32 Plumb Brook Rd, Woodbury, CT 06798
• 

  Est $464,319

  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
• 

  

  

  /20

  $775,000

  • 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
• 

  $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 $459,689

  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
• 

  

  /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
• 

  $700,000

  Sold Jul 02, 2025

  16 Fairgrounds Rd, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 2,614 Sq Ft
  • Built 1998

  Last Sold Summary

  • 1% Above List Price
  • $268/SF
  • 47 Days On Market

  Current Estimated Value $720,279

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

  16 Fairgrounds Rd, Woodbury, CT 06798
• 

  Est $659,124

  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

  • 13 Days On Market
• 

  

  /24

  $325,000

  $53K PRICE DROP

  • 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
• 

  $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 $601,670

  Last Listing Agent Joseph Lorino Klemm Real Estate Inc

  18 Grey Fox Trail, Woodbury, CT 06798
• 

  Est $397,942

  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
• 

  

  /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
• 

  $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 $269,105

  Last Listing Agent Amy Vayan BHGRE Gaetano Marra Homes

  97 Westwood Rd, Woodbury, CT 06798
• 

  Est $1,781,344

  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
• 

  

  /39

  $599,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,844 Sq Ft

  207 Grassy Hill Rd, Woodbury, CT 06798

  Nestled on a picturesque 2+ acre park-like setting, this beautifully maintained 3-bedroom, 2-bath home offers the perfect blend of comfort, space, and natural beauty-with the ease of one-level living. Designed with both style and functionality in mind, the sun-filled open layout is enhanced by vaulted ceilings, skylights, and elegant bay windows, creating a bright and airy atmosphere throughout.

  Laura Brodie Coldwell Banker Realty

  207 Grassy Hill Rd, 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 $170,636

  Last Listing Agent Deborah Snopkowski Coldwell Banker Realty

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

  

  /25

  Est $259,019

  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
• 

  

  /25

  $284,900

  $5K PRICE DROP 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
• 

  $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 $300,790

  Last Listing Agent Camilo Ramirez Higgins Group Real Estate

  1 Alder Ct Unit 1, Woodbury, CT 06798
• 

  Est $173,940

  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
• 

  

  /40

  $255,000

  $20K PRICE DROP 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
• 

  $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
• 

  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

  • 15 Days On Market
• 

  

  /26

  $999,900

  $100K PRICE DROP

  • 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
• 

  $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 $400,766

  Last Listing Agent Levi Judqin Brass Moon Realty

  360 Old Sherman Hill Rd, Woodbury, CT 06798
• 

  Est $480,441

  Not Listed For Sale

  24 Joshua Hill Rd, Woodbury, CT 06798

  • 3 Beds
  • 3 Baths
  • 2,072 Sq Ft
  • Built 1997

  24 Joshua Hill Rd, Woodbury, CT 06798

  Last Sold Summary

  • 128 Days On Market
• 

  /2

  $1,150,000

  • Land
  • 42.6 Acres
  • $26,995 per Acre

  0 Flanders Rd, Woodbury, CT 06798

  East Meadowbrook Farm presents a rare opportunity to own a legacy New England property offered for the first time since 1918. Encompassing 42 acres, including 15 rolling, sun-drenched acres of open fields, this former dairy and Christmas tree farm is bordered by 250 acres of protected Flanders Nature Center conservation land, creating an extraordinary sense of privacy and permanence. A quarter

  Tim Drakeley Drakeley Real Estate, Inc.

  0 Flanders 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 $508,317

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

  15 Lynns Corner Rd, Woodbury, CT 06798
• 

  Est $426,074

  Not Listed For Sale

  9 Orenaug Ave, Woodbury, CT 06798

  • 3 Beds
  • 1.5 Baths
  • 2,058 Sq Ft
  • Built 1912

  9 Orenaug Ave, Woodbury, CT 06798

  Last Sold Summary

  • 233 Days On Market
• 

  

  /39

  $649,900

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft

  16 Cross Brook Rd, Woodbury, CT 06798

  Fantastic Potential in this home. Three bedroom Cape Cod sitting on 5.50 acre lot with a giant barn that has great potential living space to convert into an in-laws set up, office, studio space or music studio to fit your lifestyle. Home freshly painted interior and exterior. Renovated kitchen with all new countertops and Italian farmhouse sink, floors, Pantry, refreshed cabinets. All newer

  Beatriz Conroy William Raveis Real Estate

  16 Cross Brook 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 $1,176,809

  Not Listed For Sale

  45 Birchwood Ln, Woodbury, CT 06798

  • 5 Beds
  • 5.5 Baths
  • 5,956 Sq Ft
  • Built 2004

  45 Birchwood Ln, Woodbury, CT 06798

  Last Sold Summary

  • 15 Days On Market
• 

  

  /40

  $565,000

  Open Sat 11AM - 1PM

  • 5 Beds
  • 3 Baths
  • 4,130 Sq Ft

  33 Hurds Hill Rd, Woodbury, CT 06798

  Nestled in the well-established Sherman Hill neighborhood, this five-bedroom home offers a generous footprint to put your personal touches on. Boasting wood flooring and newer windows throughout, the main level features a fluid layout designed for effortless living: a spacious living room, formal dining room, an eat-in kitchen, a cozy family room with a fireplace, a private home office, and a

  Christian Jensen William Pitt Sotheby's Int'l

  33 Hurds Hill 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
• 

  Est $188,905

  Not Listed For Sale

  229 Bacon Pond Rd Unit 443, Woodbury, CT 06798

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

  229 Bacon Pond Rd Unit 443, Woodbury, CT 06798

  Last Sold Summary

  • 8 Days On Market
• 

  

  /40

  $519,000

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

  63 Woodbury Hill Unit 63, Woodbury, CT 06798

  Exceptionally private, Putnam Loft model in the sought after Woodbury Hill! This unit is located in a secluded part of the community with woods behind and only sounds of the nearby babbling brook. This well-cared for unit features hardwood floors throughout, vaulted ceilings, floor to ceiling gas fireplace, a large dining room and remodeled kitchen. The primary bedroom suite is on the main level

  Katherine Parlato Drakeley Real Estate, Inc.

  63 Woodbury Hill Unit 63, 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 $218,717

  Last Listing Agent Jacki Hornish W. Raveis Lifestyles Realty

  12 Edgehill Ct, Woodbury, CT 06798
• 

  Est $621,475

  Not Listed For Sale

  97 Hard Hill Rd, Woodbury, CT 06798

  • 4 Beds
  • 2 Baths
  • 3,022 Sq Ft
  • Built 1981

  97 Hard Hill Rd, Woodbury, CT 06798

  Last Sold Summary

  • 91 Days On Market

Showing Results 121 - 160, Page 4 of 18