Woodbury, CT Homes

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  /40

  $875,000

  Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,394 Sq Ft

  385 Middle Road Turnpike, Woodbury, CT 06798

  Set on 3.29 picturesque acres bordering conservation land, this beautifully maintained and thoughtfully remodeled country Cape is filled with character, custom craftsmanship and modern amenities. The estate-like grounds and versatile floor plan offer privacy, comfort and functionality, including options for multigenerational living. At the heart of the home, the custom country kitchen features

  Elizabeth Newnham William Pitt Sotheby's Int'l

  385 Middle Road Turnpike, Woodbury, CT 06798
• 

  $290,000

  Sold Jun 15, 2026

  4 Deer Hill Ct Unit 4, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 1,467 Sq Ft
  • Built 1980

  Last Sold Summary

  • 3% Below List Price
  • $198/SF
  • 26 Days On Market

  Last Listing Agent Allysa DeRosa Mapleridge Realty

  4 Deer Hill Ct Unit 4, Woodbury, CT 06798
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  Not Listed For Sale

  39 Painter Hill Rd, Woodbury, CT 06798

  • 4 Beds
  • 3 Baths
  • 2,418 Sq Ft
  • Built 1810

  39 Painter Hill Rd, Woodbury, CT 06798

  Last Sold Summary

  • 62 Days On Market

  Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty
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  /24

  $1,200,000

  • 4 Beds
  • 5 Baths
  • 3,968 Sq Ft

  90 Sage Rd, Woodbury, CT 06798

  Fabulous Center Hall Colonial......Don't be one of those people who drive by and sum it up. This home was built in "The Era". The era I'm speaking of is truly the way homes used to be built. It's the way life used to be lived. It was elegant yet simple. It was colorful but not garish. In all honesty it's a home that knows the correctness of living life. The floor plan will tell you that. The

  Sindy Butkus Klemm Real Estate Inc

  90 Sage Rd, Woodbury, CT 06798
• 

  $810,000

  Sold Apr 28, 2026

  148 Flanders Rd, Woodbury, CT 06798

  • 3 Beds
  • 4 Baths
  • 3,082 Sq Ft
  • Built 1987

  Last Sold Summary

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

  Current Estimated Value $801,534

  Last Listing Agent Ron Nettleton William Raveis Real Estate

  148 Flanders Rd, Woodbury, CT 06798
• 

  Est $765,522

  Not Listed For Sale

  194 Washington Rd, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 3,182 Sq Ft
  • Built 1836

  194 Washington Rd, Woodbury, CT 06798

  Last Sold Summary

  • 78 Days On Market

  Last Listing Agent Kevin Hickey William Pitt Sotheby's Int'l
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  /15

  $499,999

  • 3 Beds
  • 2.5 Baths
  • 2,100 Sq Ft

  110 Brushy Hill Rd, Woodbury, CT 06798

  Experience the charm of this classic Cape Cod style property, featuring 3 bedrooms and 2 cozy fireplaces that invite warm gatherings on 1 acre of land perfect for outdoor enjoyment. This country eclectic home blends timeless architecture with modern comfort, offering a serene retreat that captures the essence of country living. Whether you're relaxing by the fire or exploring the great outdoors,

  Jacqueline Voegeli Manzi Real Estate

  110 Brushy Hill Rd, Woodbury, CT 06798
• 

  $765,000

  Sold Sep 29, 2025

  34 Hollow Rd, Woodbury, CT 06798

  • 3 Beds
  • 3 Baths
  • 1,675 Sq Ft
  • Built 1750

  Last Sold Summary

  • 4% Below List Price
  • $457/SF
  • 103 Days On Market

  Current Estimated Value $759,164

  Last Listing Agent Lorraine Consiglio BHGRE Gaetano Marra Homes

  34 Hollow Rd, Woodbury, CT 06798
• 

  Est $832,809

  Not Listed For Sale

  82 Bear Run, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 3,158 Sq Ft
  • Built 1998

  82 Bear Run, Woodbury, CT 06798

  Last Sold Summary

  • 53 Days On Market

  Last Listing Agent Katherine Parlato Drakeley Real Estate, Inc.
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  /35

  $925,000

  Open Sun 10AM - 12PM

  • 4 Beds
  • 2.5 Baths
  • 2,568 Sq Ft

  69 Nonnewaug Rd, Woodbury, CT 06798

  A Place Where Home Feels Like A Getaway Welcome to 69 Nonnewaug Road, where peaceful country living meets the charm of Woodbury! Set on approximately 9.47 acres, this 3-bedroom, 3-bath home offers an incredible combination of space, privacy, and outdoor living. Surrounded by beautiful natural scenery, the expansive property provides plenty of room to spread out, explore, garden, entertain, or

  Jessica Fedorich Stone Crest Realty LLC

  69 Nonnewaug Rd, Woodbury, CT 06798
• 

  $500,000

  Sold Jun 29, 2026

  14 Meadow Crest Dr, Woodbury, CT 06798

  • 3 Beds
  • 1.5 Baths
  • 2,102 Sq Ft
  • Built 1979

  Last Sold Summary

  • 5% Below List Price
  • $238/SF
  • 108 Days On Market

  Current Estimated Value $516,974

  Last Listing Agent Katherine Parlato Drakeley Real Estate, Inc.

  14 Meadow Crest Dr, Woodbury, CT 06798
• 

  Est $546,504

  Not Listed For Sale

  42 Cedar Grove, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 2,680 Sq Ft
  • Built 1953

  42 Cedar Grove, Woodbury, CT 06798

  Last Sold Summary

  • 38 Days On Market

  Last Listing Agent Justin Bette Century 21 Bette Real Estate
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  /22

  $209,900

  • 2 Beds
  • 1 Bath
  • 913 Sq Ft

  229 Bacon Pond Rd Unit 313, Woodbury, CT 06798

  Move right into this beautifully renovated upper end unit in Woodbury's desirable in-town Town & Country condominium complex. Tastefully updated throughout, this light-filled unit features an open floor plan with a completely renovated kitchen flowing into the living room with fireplace and built-ins. Updates include new windows, luxury vinyl plank flooring, interior doors, lighting, switches,

  Joyce Drakeley Drakeley Real Estate, Inc.

  229 Bacon Pond Rd Unit 313, Woodbury, CT 06798
• 

  $370,000

  Sold Nov 18, 2025

  4 Hazel Plain Rd, Woodbury, CT 06798

  • 3 Beds
  • 1 Bath
  • 1,075 Sq Ft
  • Built 1949

  Last Sold Summary

  • 8% Above List Price
  • $344/SF
  • 6 Days On Market

  Current Estimated Value $384,207

  Last Listing Agent Gary Smith eXp Realty

  4 Hazel Plain Rd, Woodbury, CT 06798
• 

  Est $295,618

  Not Listed For Sale

  19 Woodbury Place, Woodbury, CT 06798

  • 2 Beds
  • 2 Baths
  • 1,016 Sq Ft
  • Built 1979

  19 Woodbury Place, Woodbury, CT 06798

  Last Sold Summary

  • 49 Days On Market

  Last Listing Agent Mary Adzima Coldwell Banker Realty
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  /8

  $395,000

  • Land
  • 2.53 Acres
  • $156,126 per Acre

  133 Painter Hill Rd, Woodbury, CT 06798

  Nestled along one of Woodbury's finest country roads, this exceptional 2.53-acre parcel offers a rare masterclass in privacy and natural beauty. Located just moments from the Roxbury town line, the gently rolling landscape is framed by mature trees and directly abuts the Arthur Miller Preserve and the Frank and Ellen McCort protected Land Trust. Positioned just two homes away from the historic

  Judith Auchincloss Klemm Real Estate Inc

  133 Painter Hill Rd, Woodbury, CT 06798
• 

  $261,000

  Sold May 21, 2026

  14 Tamarack Ln, Woodbury, CT 06798

  • 2 Beds
  • 2.5 Baths
  • 1,983 Sq Ft
  • Built 1974

  Last Sold Summary

  • 1% Above List Price
  • $132/SF
  • 99 Days On Market

  Current Estimated Value $259,623

  Last Listing Agent Gina Jacobs Gina Jacobs Real Estate

  14 Tamarack Ln, Woodbury, CT 06798
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  Est $633,565

  Not Listed For Sale

  394 Washington Rd, Woodbury, CT 06798

  • 4 Beds
  • 3 Baths
  • 2,280 Sq Ft
  • Built 2000

  394 Washington Rd, Woodbury, CT 06798

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Wilson Lamas Regency Real Estate, LLC
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  /40

  $874,900

  $75K PRICE DROP Pending

  • 4 Beds
  • 5 Baths
  • 3,865 Sq Ft

  8 Curtiss Meadows, Woodbury, CT 06798

  Beautiful Colonial set on a private 3+ acre lot in sought-after Curtiss Meadows, ideally located on the southern end of Woodbury abutting the Southbury line. Set back from the cul-de-sac entryway, this well-cared-for home offers a wonderful blend of privacy, comfort, convenience, and thoughtful updates. The level, light-filled driveway provides easy access, while the peaceful setting creates a

  Joyce Drakeley Drakeley Real Estate, Inc.

  8 Curtiss Meadows, Woodbury, CT 06798
• 

  $885,000

  Sold Jul 30, 2026

  557 Upper Grassy Hill Rd, Woodbury, CT 06798

  • 4 Beds
  • 3.5 Baths
  • 3,784 Sq Ft
  • Built 1999

  Last Sold Summary

  • 1% Below List Price
  • $234/SF
  • 117 Days On Market

  Current Estimated Value $883,541

  Last Listing Agent Susan Corleto William Pitt Sotheby's Int'l

  557 Upper Grassy Hill Rd, Woodbury, CT 06798
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  Est $480,560

  Not Listed For Sale

  203 Carmel Hill Rd, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 2,190 Sq Ft
  • Built 1940

  203 Carmel Hill Rd, Woodbury, CT 06798

  Last Sold Summary

  • 48 Days On Market

  Last Listing Agent Cezary Jusinski RE/MAX RISE
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  /40

  $959,000

  • 4 Beds
  • 2.5 Baths
  • 2,926 Sq Ft

  11 Pleasant St, Woodbury, CT 06798

  Timeless Elegance & Immaculate Detail. Welcome to The Naramore House, a piece of living history. Lovingly preserved since 1898, this pristine colonial home seamlessly blends grand historic character with immaculate, turnkey maintenance. A classic wraparound front porch invites you through a charming dutch door into a formal, stately foyer featuring high ceilings and original pocket doors. The

  Carla Mascaro William Pitt Sotheby's Int'l

  11 Pleasant St, Woodbury, CT 06798
• 

  $430,000

  Sold Jun 22, 2026

  43 Woodbury Hill, Woodbury, CT 06798

  • 2 Beds
  • 2 Baths
  • 1,986 Sq Ft
  • Built 1985

  Last Sold Summary

  • 28% Below List Price
  • $217/SF
  • 54 Days On Market

  Current Estimated Value $425,822

  Last Listing Agent Joyce Drakeley Drakeley Real Estate, Inc.

  43 Woodbury Hill, Woodbury, CT 06798
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  Est $829,251

  Not Listed For Sale

  165 Grassy Hill Rd, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 3,478 Sq Ft
  • Built 1999

  165 Grassy Hill Rd, Woodbury, CT 06798

  Last Sold Summary

  • 81 Days On Market

  Last Listing Agent Jeff Boucher Drakeley Real Estate, Inc.
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  /40

  $1,790,000

  $205K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 3,324 Sq Ft

  55 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. Experience the undeniable charm of this circa 1685 residence-one of the oldest continuously inhabited homes in the county. Thoughtfully restored and beautifully updated, this remarkable property blends centuries of character

  Stacey Matthews W. Raveis Lifestyles Realty

  55 Good Hill Rd, Woodbury, CT 06798
• 

  $650,000

  Sold Aug 03, 2026

  207 Grassy Hill Rd, Woodbury, CT 06798

  • 3 Beds
  • 2 Baths
  • 1,844 Sq Ft
  • Built 1993

  Last Sold Summary

  • 9% Above List Price
  • $352/SF
  • 53 Days On Market

  Current Estimated Value $588,832

  Last Listing Agent Laura Brodie Coldwell Banker Realty

  207 Grassy Hill Rd, Woodbury, CT 06798
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  Est $762,971

  Not Listed For Sale

  258 Washington Rd, Woodbury, CT 06798

  • 3 Beds
  • 3 Baths
  • 1,628 Sq Ft
  • Built 1850

  258 Washington Rd, Woodbury, CT 06798

  Last Sold Summary

  • 260 Days On Market

  Last Listing Agent Pat Lahoud William Pitt Sotheby's Int'l
• 

  $489,000

  Sold Apr 30, 2026

  74 Woodbury Hill, Woodbury, CT 06798

  • 2 Beds
  • 2.5 Baths
  • 2,463 Sq Ft
  • Built 1985

  Last Sold Summary

  • $199/SF
  • 15 Days On Market

  Current Estimated Value $491,851

  Last Listing Agent Claudine McHugh Klemm Real Estate Inc

  74 Woodbury Hill, Woodbury, CT 06798
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  Est $181,011

  Not Listed For Sale

  229 Bacon Pond Rd Unit 214, Woodbury, CT 06798

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

  229 Bacon Pond Rd Unit 214, Woodbury, CT 06798

  Last Sold Summary

  • 43 Days On Market

  Last Listing Agent Cindy Sevell Coldwell Banker Realty
• 

  $420,000

  Sold Nov 19, 2025

  223 Tuttle Rd, Woodbury, CT 06798

  • 2 Beds
  • 1 Bath
  • 1,328 Sq Ft
  • Built 1956

  Last Sold Summary

  • 6% Below List Price
  • $316/SF
  • 14 Days On Market

  Current Estimated Value $436,039

  Last Listing Agent Rhya Szymansky Drakeley Real Estate, Inc.

  223 Tuttle Rd, Woodbury, CT 06798
• 

  Est $489,586

  Not Listed For Sale

  24 Woodbury Hill, Woodbury, CT 06798

  • 2 Beds
  • 2.5 Baths
  • 1,577 Sq Ft
  • Built 1985

  24 Woodbury Hill, Woodbury, CT 06798

  Last Sold Summary

  • 55 Days On Market

  Last Listing Agent Sindy Butkus Klemm Real Estate Inc
• 

  $284,900

  Sold Jul 14, 2026

  14 Heather Ct Unit 14, Woodbury, CT 06798

  • 2 Beds
  • 2 Baths
  • 1,138 Sq Ft
  • Built 1973

  Last Sold Summary

  • 2% Below List Price
  • $250/SF
  • 80 Days On Market

  Current Estimated Value $275,801

  Last Listing Agent Christopher Gueniat Northwest CT Realty

  14 Heather Ct Unit 14, Woodbury, CT 06798
• 

  Est $638,488

  Not Listed For Sale

  188 Scuppo Rd, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 2,285 Sq Ft
  • Built 1999

  188 Scuppo Rd, Woodbury, CT 06798

  Last Sold Summary

  • 98 Days On Market

  Last Listing Agent Valerie King Keller Williams Realty Prtnrs.
• 

  $245,000

  Sold Jul 17, 2026

  9 Highpoint Ct Unit 116E, Woodbury, CT 06798

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

  Last Sold Summary

  • 11% Below List Price
  • $207/SF
  • 160 Days On Market

  Last Listing Agent Terry Lee Adams Adams & Adams Real Estate

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

  Est $223,285

  Not Listed For Sale

  74 Washington Rd Unit 11, Woodbury, CT 06798

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

  74 Washington Rd Unit 11, Woodbury, CT 06798

  Last Sold Summary

  • 56 Days On Market

  Last Listing Agent Gina Jacobs Gina Jacobs Real Estate
• 

  $415,000

  Sold Oct 31, 2025

  60 Pomperaug Rd, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 1,668 Sq Ft
  • Built 1850

  Last Sold Summary

  • 10% Below List Price
  • $249/SF
  • 128 Days On Market

  Current Estimated Value $431,755

  Last Listing Agent Terry Lee Adams Adams & Adams Real Estate

  60 Pomperaug Rd, Woodbury, CT 06798
• 

  Est $657,385

  Not Listed For Sale

  29 Curtiss Rd, Woodbury, CT 06798

  • 4 Beds
  • 3 Baths
  • 3,045 Sq Ft
  • Built 1800

  29 Curtiss Rd, Woodbury, CT 06798

  Last Sold Summary

  • 97 Days On Market

  Last Listing Agent Rebecca Doh W. Raveis Lifestyles Realty
• 

  $575,000

  Sold Sep 15, 2026

  206 Minortown Rd, Woodbury, CT 06798

  • 3 Beds
  • 3 Baths
  • 1,692 Sq Ft
  • Built 1951

  Last Sold Summary

  • $340/SF
  • 54 Days On Market

  Current Estimated Value $565,295

  Last Listing Agent Katherine Parlato Drakeley Real Estate, Inc.

  206 Minortown Rd, Woodbury, CT 06798
• 

  Est $245,529

  Not Listed For Sale

  6 Deer Hill Ct, Woodbury, CT 06798

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

  6 Deer Hill Ct, Woodbury, CT 06798

  Last Sold Summary

  • 42 Days On Market

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

  $765,000

  Sold Dec 22, 2025

  393 Middle Road Turnpike, Woodbury, CT 06798

  • 4 Beds
  • 4 Baths
  • 3,280 Sq Ft
  • Built 1783

  Last Sold Summary

  • 15% Below List Price
  • $233/SF
  • 96 Days On Market

  Current Estimated Value $795,261

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

  393 Middle Road Turnpike, Woodbury, CT 06798

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