Woodbury, CT Homes

• 

  

  

  /21

  $479,900

  $19K PRICE DROP Pending

  • 3 Beds
  • 2.5 Baths
  • 2,016 Sq Ft

  34 Transylvania Rd, Woodbury, CT 06798

  Price Improvement for this Charming Country Retreat- A perfect alternative to Condo Living! Nestled on a serene 3 acre lot with picturesque stream, this property offers the tranquility of country living while maintaining easy access to nearby amenities. One level living- enjoy the convenience of the primary bedroom with spacious walk-in closet on the same level as the open floor plan

  Betsy Rosa Berkshire Hathaway NE Prop.

  34 Transylvania 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 $420,626

  Not Listed For Sale

  40 Pilgrim Trail, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 2,544 Sq Ft
  • Built 1966

  40 Pilgrim Trail, Woodbury, CT 06798

  Last Sold Summary

  • 85 Days On Market
• 

  

  

  /33

  $849,000

  • 3 Beds
  • 2 Baths
  • 2,448 Sq Ft

  92 Minortown Rd, Woodbury, CT 06798

  Live Stress-Free in This Income-Producing Equestrian Retreat! Enjoy the best of country living while generating income from your property. Rental revenue from a separate 1 BR apartment and 4 of the 10 horse stalls offers a rare opportunity to offset ownership costs! Situated on 5.76 level acres of open pasture and riding space, this equestrian property is ideal for horse enthusiasts, trainers, or

  Jill Sloane Brown Harris Stevens

  92 Minortown Rd, 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 $573,803

  Last Listing Agent Matt Rose Keller Williams Realty

  81 Park Rd, Woodbury, CT 06798
• 

  Est $359,276

  Not Listed For Sale

  274 Minortown Rd, Woodbury, CT 06798

  • 2 Beds
  • 2 Baths
  • 914 Sq Ft
  • Built 1989

  274 Minortown Rd, Woodbury, CT 06798

  Last Sold Summary

  • 0 Days On Market
• 

  

  /40

  $699,900

  • 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 with quintessential wrap-around front porch, ideally situated on a desirable cul-de-sac just minutes from the charming town centers of Woodbury and Roxbury. Step inside to a gracious foyer flanked by a formal dining room and a versatile living room/den, ideal for a home office, library, or sitting room. The heart

  Stephanie Chapman BHGRE Gaetano Marra Homes

  15 Saxony Ln, Woodbury, CT 06798
• 

  $302,500

  Sold Jul 09, 2025

  8 Highpoint Ct, Woodbury, CT 06798

  • 2 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Built 1979

  Last Sold Summary

  • 2% Below List Price
  • $208/SF
  • 33 Days On Market

  Current Estimated Value $305,541

  Last Listing Agent Tom Greto William Raveis Real Estate

  8 Highpoint Ct, Woodbury, CT 06798
• 

  Est $463,535

  Not Listed For Sale

  99 Flanders Rd, Woodbury, CT 06798

  • 3 Beds
  • 3 Baths
  • 2,664 Sq Ft
  • Built 1956

  99 Flanders Rd, Woodbury, CT 06798

  Last Sold Summary

  • 337 Days On Market
• 

  

  /27

  $645,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,081 Sq Ft

  94 Quail Run Rd, Woodbury, CT 06798

  QUAIL RUN On the cul de sac - 4 NEW HOMES 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 on 2 homes with anticipated completion in August. #94 is a 3 BR,

  Scott Volpe Coldwell Banker Realty

  94 Quail Run Rd, Woodbury, CT 06798
• 

  $539,000

  Sold Jul 18, 2025

  54 Barnhill Rd, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 1,675 Sq Ft
  • Built 1985

  Last Sold Summary

  • 2% Above List Price
  • $322/SF
  • 3 Days On Market

  Current Estimated Value $551,470

  Last Listing Agent Joseph Racanelli William Raveis Real Estate

  54 Barnhill Rd, Woodbury, CT 06798
• 

  Est $289,491

  Not Listed For Sale

  49 Clubhouse Dr, Woodbury, CT 06798

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

  49 Clubhouse Dr, Woodbury, CT 06798

  Last Sold Summary

  • 24 Days On Market
• 

  

  /30

  $425,000

  Under Contract

  • 3 Beds
  • 1 Bath
  • 1,364 Sq Ft

  104 Hard Hill Rd, Woodbury, CT 06798

  Nestled along a country road on a cul-de-sac, this charming home offers the perfect blend of warmth, comfort, and convenience. A welcoming entry greets you with soaring ceilings, wood floors, and a propane stove that adds both character and cozy ambiance. The spacious country kitchen is designed for gathering, featuring vaulted ceilings, a large center island, stainless steel appliances, and an

  Nancy Langrock William Raveis Real Estate

  104 Hard Hill Rd, Woodbury, CT 06798
• 

  $600,000

  Sold Nov 20, 2025

  36 Heritage Dr, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 2,032 Sq Ft
  • Built 1968

  Last Sold Summary

  • 5% Below List Price
  • $295/SF
  • 60 Days On Market

  Current Estimated Value $604,179

  Last Listing Agent Justin Bette Century 21 Bette Real Estate

  36 Heritage Dr, Woodbury, CT 06798
• 

  Est $456,127

  Not Listed For Sale

  50 Washington Rd, Woodbury, CT 06798

  • 3 Beds
  • 1.5 Baths
  • 1,550 Sq Ft
  • Built 1895

  50 Washington Rd, Woodbury, CT 06798

  Last Sold Summary

  • 62 Days On Market
• 

  

  /20

  $650,000

  • 3 Beds
  • 3.5 Baths
  • 2,479 Sq Ft

  30 Park Rd, Woodbury, CT 06798

  Charming in-town Gambrel Colonial with views of Orenaug Pond, located just up the road from the South Green. Surrounded by historic landmarks such as King Solomon's Lodge, the Hurd House, the Glebe House, and other notable properties, this home offers three bedrooms, three full baths, and one half bath. It also features a remodeled kitchen with stainless appliances that opens to a family room

  Sindy Butkus Klemm Real Estate Inc

  30 Park Rd, Woodbury, CT 06798
• 

  $1,225,000

  Sold Nov 16, 2025

  68 Whittlesey Rd, Woodbury, CT 06798

  • 4 Beds
  • 4 Baths
  • 4,682 Sq Ft
  • Built 2006

  Last Sold Summary

  • 4% Above List Price
  • $262/SF
  • 44 Days On Market

  Current Estimated Value $1,233,182

  Last Listing Agent Michael Caporizzo William Pitt Sotheby's Int'l

  68 Whittlesey Rd, Woodbury, CT 06798
• 

  Est $174,150

  Not Listed For Sale

  229 Bacon Pond Rd Unit 241, Woodbury, CT 06798

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

  229 Bacon Pond Rd Unit 241, Woodbury, CT 06798

  Last Sold Summary

  • 34 Days On Market
• 

  /2

  $400,000

  • Land
  • 22,215 Sq Ft
  • $784,314 per Acre

  1545 Main St N, Woodbury, CT 06798

  Rare Main Street commercial property available in Woodbury, CT. The land and the building upon it are being sold in "as is, where is" condition. Neither the probate court system, the attorney, or the broker have any knowledge as to any deficiencies on the property or if they even exist Located in the OS 60 zone, interested parties should consult with the planning and zoning to verify their

  Mario Longobucco Coldwell Banker Commercial NRT

  1545 Main St N, Woodbury, CT 06798
• 

  $300,000

  Sold Dec 30, 2025

  9 Heather Ct Unit 9, Woodbury, CT 06798

  • 2 Beds
  • 2.5 Baths
  • 1,723 Sq Ft
  • Built 1979

  Last Sold Summary

  • 2% Above List Price
  • $174/SF
  • 33 Days On Market

  Current Estimated Value $297,944

  Last Listing Agent Ann Micacci Berkshire Hathaway NE Prop.

  9 Heather Ct Unit 9, Woodbury, CT 06798
• 

  Est $691,529

  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
• 

  

  /40

  $699,000

  Pending

  • 3 Beds
  • 3.5 Baths
  • 3,210 Sq Ft

  58 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. This stately circa 1845 home blends historic character with comfortable living. Set along scenic Good Hill Road and surrounded by lush, established gardens, featuring a black bottom gunite pool, private terrace, welcoming

  Christina Zainc BHGRE Gaetano Marra Homes

  58 Good Hill Rd, Woodbury, CT 06798
• 

  $130,000

  Sold Oct 01, 2025

  Lot 64 Highpoint Rd, Woodbury, CT 06798

  • Land
  • 35,283 Sq Ft
  • $160,494 per Acre

  Last Sold Summary

  • 8% Above List Price
  • 88 Days On Market

  Last Listing Agent Justin Bette Century 21 Bette Real Estate

  Lot 64 Highpoint Rd, Woodbury, CT 06798
• 

  Est $738,280

  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
• 

  

  /38

  $267,500

  $5K PRICE DROP Under Contract

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

  23 Lower Commons Unit 23, Woodbury, CT 06798

  Note New Price-point! REFURBISHED, fresh paint, move in ready W/tile entry. The Kitchen has new S.S. appliances, loads of cabinet storage, spacious workspace for the chef! The first floor includes the convenience of laundry and a 1/2 Bath. Hardwood floors in the living room adds to the inviting ambiance. There is a fireplace: it can easily become working with the insert of a Pellet or

  Terry Lee Adams Adams & Adams Real Estate

  23 Lower Commons Unit 23, Woodbury, CT 06798
• 

  $775,000

  Sold Nov 13, 2025

  6 Strong Field Rd, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 2,600 Sq Ft
  • Built 2024

  Last Sold Summary

  • 8% Below List Price
  • $298/SF
  • 103 Days On Market

  Current Estimated Value $781,855

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

  6 Strong Field Rd, Woodbury, CT 06798
• 

  Est $777,589

  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
• 

  

  /25

  $284,500

  Under Contract

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

  7 Highpoint Ct Unit 7, Woodbury, CT 06798

  Welcome to this spacious three-bedroom, two and a half bath townhouse located in the desirable Woodlake Community. The living room and dining areas offer an open-concept floor plan, making it perfect for both everyday living and entertaining guests. Sliding glass doors from the dining room lead to a private deck, which looks out upon a wooded area that offers serene views. The primary bedroom

  Karen Dibble-flaherty Keller Williams Realty

  7 Highpoint Ct Unit 7, Woodbury, CT 06798
• 

  $592,750

  Sold Feb 05, 2026

  94 Old Town Farm Rd, Woodbury, CT 06798

  • 6 Beds
  • 3 Baths
  • 4,245 Sq Ft
  • Built 1900

  Last Sold Summary

  • 21% Below List Price
  • $140/SF
  • 175 Days On Market

  Current Estimated Value $602,130

  Last Listing Agent Michael Caporizzo William Pitt Sotheby's Int'l

  94 Old Town Farm Rd, Woodbury, CT 06798
• 

  Est $526,750

  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
• 

  

  /36

  $450,000

  Under Contract

  • 3 Beds
  • 3 Baths
  • 1,210 Sq Ft

  89 Lighthouse Rd, Woodbury, CT 06798

  ** Multiple offers highest and best 5/17 5pm**Tucked away on 4.99 serene wooded acres in picturesque Woodbury, this solidly built Cape Cod offers privacy, charm, and endless potential. Surrounded by mature trees and peaceful natural beauty, the property provides a true country setting with room to create gardens, walking trails, or space for animals and hobby farm interests. Inside, the home

  Heather Crabtree RE/MAX RISE

  89 Lighthouse Rd, 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
• 

  Est $280,377

  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
• 

  

  /33

  $389,900

  Pending

  • 3 Beds
  • 2 Baths
  • 1,578 Sq Ft

  134 Old Sherman Hill Rd, Woodbury, CT 06798

  Welcome home to this charming 3-bedroom, 2-bath ranch, perfectly situated on a lovely lot. This home offers comfortable one-level living with a bright and inviting floor plan designed for everyday living and entertaining. The spacious living areas flow seamlessly into the kitchen and dining space, while three generously sized bedrooms provide ample room for family, guests, or a home office. Enjoy

  Tracey Fiasconaro Berkshire Hathaway NE Prop.

  134 Old Sherman Hill 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 $832,630

  Last Listing Agent Ron Nettleton William Raveis Real Estate

  148 Flanders Rd, Woodbury, CT 06798
• 

  Est $612,267

  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
• 

  

  /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
• 

  $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 $769,985

  Last Listing Agent Lorraine Consiglio BHGRE Gaetano Marra Homes

  34 Hollow Rd, Woodbury, CT 06798
• 

  Est $441,013

  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
• 

  

  /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

Showing Results 161 - 200, Page 5 of 18