4,956

Woodbury, CT Homes

Section Image
    • 60 Main St S, Woodbury, CT 06798

      Est $677,834

      Not Listed For Sale

      60 Main St S, Woodbury, CT 06798

      • 4 Beds
      • 2 Baths
      • 3,068 Sq Ft
      • Built 1829
      60 Main St S, Woodbury, CT 06798

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Joyce Drakeley Drakeley Real Estate, Inc.

  • 439 Washington Rd, Woodbury, CT 06798
    439 Washington Rd, Woodbury, CT 06798
    439 Washington Rd, Woodbury, CT 06798
    /32

    $289,000

    $61K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,920 Sq Ft

    439 Washington Rd, Woodbury, CT 06798

    Investors and Contractors take notice! This versatile office space located on close to 10 acres of rural Woodbury land is ripe with opportunity. The 1,920 sqft office can potentially be converted into a single family residential ranch overlooking the babbling Sprain Brook below. Across the brook, with road frontage and access off of Hoop Pole Hill Rd, lies the majority of the acreage with a dry,

    Matthew Amatruda Drakeley Real Estate, Inc.

    439 Washington Rd, Woodbury, CT 06798
  • 2 Judd Hill Rd, Woodbury, CT 06798

    $575,000

    Sold Jul 02, 2026

    2 Judd Hill Rd, Woodbury, CT 06798

    • 3 Beds
    • 2 Baths
    • 1,470 Sq Ft
    • Built 1958

    Last Sold Summary

    • 4% Below List Price
    • $391/SF
    • 48 Days On Market

    Current Estimated Value $564,532

    Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

    2 Judd Hill Rd, Woodbury, CT 06798
    • 39 Painter Hill Rd, Woodbury, CT 06798

      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

  • 18 South St, Woodbury, CT 06798
    18 South St, Woodbury, CT 06798
    18 South St, Woodbury, CT 06798
    /30

    $495,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,880 Sq Ft

    18 South St, Woodbury, CT 06798

    Sited privately on 2.7 scenic acres in Woodbury's desirable Cardinal Hill neighborhood, this classic four-bedroom Colonial offers a perfect blend of quiet country living and everyday functionality. As part of a low-fee, self-managed neighborhood association, residents enjoy a wonderful sense of privacy and peace of mind. The main level features a traditional flow, including a formal living room

    Christian Jensen William Pitt Sotheby's Int'l

    18 South St, Woodbury, CT 06798
  • 4 Deer Hill Ct Unit 4, 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
    • 194 Washington Rd, Woodbury, CT 06798

      Est $776,308

      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

  • 31 Mountain Rd, Woodbury, CT 06798
    31 Mountain Rd, Woodbury, CT 06798
    31 Mountain Rd, Woodbury, CT 06798
    /33

    $679,900

    $70K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,838 Sq Ft

    31 Mountain Rd, Woodbury, CT 06798

    Charming and full of character, this beautifully maintained three-bedroom Cape offers the perfect blend of comfort, warmth, and convenience in the heart of Woodbury. Set on a picturesque property with mature perennial gardens and a fenced-in yard, the home feels peaceful and private while being just a two-minute walk from downtown shops, restaurants, the library, schools, community center, and

    Joyce Drakeley Drakeley Real Estate, Inc.

    31 Mountain Rd, Woodbury, CT 06798
  • 148 Flanders 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 $813,143

    Last Listing Agent Ron Nettleton William Raveis Real Estate

    148 Flanders Rd, Woodbury, CT 06798
    • 82 Bear Run, Woodbury, CT 06798

      Est $814,524

      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.

  • 110 Brushy Hill Rd, Woodbury, CT 06798
    110 Brushy Hill Rd, Woodbury, CT 06798
    110 Brushy Hill Rd, Woodbury, CT 06798
    /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
  • 34 Hollow 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 $780,531

    Last Listing Agent Lorraine Consiglio BHGRE Gaetano Marra Homes

    34 Hollow Rd, Woodbury, CT 06798
    • 42 Cedar Grove, Woodbury, CT 06798

      Est $525,962

      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

  • 229 Bacon Pond Rd Unit 312, Woodbury, CT 06798
    229 Bacon Pond Rd Unit 312, Woodbury, CT 06798
    229 Bacon Pond Rd Unit 312, Woodbury, CT 06798
    /23

    $219,900

    • 2 Beds
    • 1 Bath
    • 913 Sq Ft

    229 Bacon Pond Rd Unit 312, Woodbury, CT 06798

    Welcome to 229 Bacon Pond Rd Unit 312 - located in the Town In Country complex, this 2 bed/1 bath unit has been remodeled from top to bottom featuring a brand new kitchen, new flooring, and central air. Inside you'll find an open floor plan perfect for entertaining - the kitchen has been completely redesigned featuring new cabinets, quartz countertops, and stainless steel appliances. The modern

    Joe Rohinsky Coldwell Banker Realty

    229 Bacon Pond Rd Unit 312, Woodbury, CT 06798
  • 14 Meadow Crest Dr, 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 $506,344

    Last Listing Agent Katherine Parlato Drakeley Real Estate, Inc.

    14 Meadow Crest Dr, Woodbury, CT 06798
    • 19 Woodbury Place, Woodbury, CT 06798

      Est $302,839

      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

  • 133 Painter Hill Rd, Woodbury, CT 06798
    133 Painter Hill Rd, Woodbury, CT 06798
    133 Painter Hill Rd, Woodbury, CT 06798
    /6

    $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
  • 4 Hazel Plain Rd, 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 $387,100

    Last Listing Agent Gary Smith eXp Realty

    4 Hazel Plain Rd, Woodbury, CT 06798
    • 394 Washington Rd, Woodbury, CT 06798

      Est $631,781

      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

  • 8 Curtiss Meadows, Woodbury, CT 06798
    8 Curtiss Meadows, Woodbury, CT 06798
    8 Curtiss Meadows, Woodbury, CT 06798
    /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
  • 14 Tamarack Ln, 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 $261,155

    Last Listing Agent Gina Jacobs Gina Jacobs Real Estate

    14 Tamarack Ln, Woodbury, CT 06798
    • 203 Carmel Hill Rd, Woodbury, CT 06798

      Est $462,353

      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

  • 11 Pleasant St, Woodbury, CT 06798
    11 Pleasant St, Woodbury, CT 06798
    11 Pleasant St, Woodbury, CT 06798
    /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
  • 557 Upper Grassy Hill Rd, 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 $885,863

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

    557 Upper Grassy Hill Rd, Woodbury, CT 06798
    • 165 Grassy Hill Rd, Woodbury, CT 06798

      Est $796,005

      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.

  • 229 Bacon Pond Rd Unit 452, Woodbury, CT 06798
    229 Bacon Pond Rd Unit 452, Woodbury, CT 06798
    229 Bacon Pond Rd Unit 452, Woodbury, CT 06798
    /17

    $179,900

    Under Contract
    • 2 Beds
    • 1 Bath
    • 913 Sq Ft

    229 Bacon Pond Rd Unit 452, Woodbury, CT 06798

    Welcome to Town & Country, a sought-after condominium community conveniently located just minutes from the heart of Woodbury. This 2-bedroom, 1-bath lower-level ranch-style unit offers comfortable one-level living with an open layout and abundant natural light. Laminate flooring runs throughout the living areas and bedrooms, while the kitchen and bathroom feature durable tile flooring. The

    Tim Drakeley Drakeley Real Estate, Inc.

    229 Bacon Pond Rd Unit 452, Woodbury, CT 06798
  • 43 Woodbury Hill, 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 $437,801

    Last Listing Agent Joyce Drakeley Drakeley Real Estate, Inc.

    43 Woodbury Hill, Woodbury, CT 06798
    • 258 Washington Rd, Woodbury, CT 06798

      Est $830,530

      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 Lahoud William Pitt Sotheby's Int'l

  • 55 Good Hill Rd, Woodbury, CT 06798
    55 Good Hill Rd, Woodbury, CT 06798
    55 Good Hill Rd, Woodbury, CT 06798
    /40

    $1,995,000

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

    55 Good Hill Rd, Woodbury, CT 06798

    Step into History with Modern Comfort 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 with today's modern conveniences. Inside, the open floor plan creates a warm and inviting flow, with three cozy sitting rooms

    Stacey Matthews W. Raveis Lifestyles Realty

    55 Good Hill Rd, Woodbury, CT 06798
  • 207 Grassy 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 $592,376

    Last Listing Agent Laura Brodie Coldwell Banker Realty

    207 Grassy Hill Rd, Woodbury, CT 06798
    • 229 Bacon Pond Rd Unit 214, Woodbury, CT 06798

      Est $174,933

      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

  • 74 Woodbury Hill, Woodbury, CT 06798

    $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 $492,425

    Last Listing Agent Claudine McHugh Klemm Real Estate Inc

    74 Woodbury Hill, Woodbury, CT 06798
    • 24 Woodbury Hill, Woodbury, CT 06798

      Est $485,715

      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

  • 223 Tuttle Rd, Woodbury, CT 06798

    $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 $437,288

    Last Listing Agent Rhya Szymansky Drakeley Real Estate, Inc.

    223 Tuttle Rd, Woodbury, CT 06798
    • 3 Deer Hill Ct, Woodbury, CT 06798

      Est $299,459

      Not Listed For Sale

      3 Deer Hill Ct, Woodbury, CT 06798

      • 2 Beds
      • 2 Baths
      • 1,861 Sq Ft
      • Built 1979
      3 Deer Hill Ct, Woodbury, CT 06798

      Last Sold Summary

      • 39 Days On Market

      Last Listing Agent Alexander Marti Showcase Realty, Inc.

  • 14 Heather Ct Unit 14, Woodbury, CT 06798

    $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 $276,731

    Last Listing Agent Christopher Gueniat Northwest CT Realty

    14 Heather Ct Unit 14, Woodbury, CT 06798
    • 188 Scuppo Rd, Woodbury, CT 06798

      Est $638,172

      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.

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

    $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
    • 74 Washington Rd Unit 11, Woodbury, CT 06798

      Est $204,792

      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

  • 48 Clubhouse Dr, Woodbury, CT 06798

    $270,000

    Sold Sep 19, 2025

    48 Clubhouse Dr, Woodbury, CT 06798

    • 2 Beds
    • 2.5 Baths
    • 1,316 Sq Ft
    • Built 1972

    Last Sold Summary

    • 4% Below List Price
    • $205/SF
    • 40 Days On Market

    Current Estimated Value $276,775

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

    48 Clubhouse Dr, Woodbury, CT 06798

Showing Results 201 - 240, Page 6 of 18

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