Woodbury, CT Homes

• 

  

  

  /40

  $310,000 Open Sun 1PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 1,888 Sq Ft

  4 Heather Ct Unit 4, Woodbury, CT 06798

  Move-in ready and impeccably maintained, this desirable townhome is located in the Woodlake Condominium Complex in Woodbury. The open-concept living and dining area features gleaming hardwood floors, a board-and-batten accent wall, fireplace, abundant natural light, and newer 8' slider leading to a private deck overlooking wooded views. The spacious eat-in kitchen offers ample counter space,

  Jenn Lailer BHGRE Gaetano Marra Homes

  4 Heather Ct Unit 4, Woodbury, CT 06798
• Selling your home? Sell it faster and for more with a Homes.com Boost.

  Learn More
• 

  

  

  /15

  $1,650 total monthly price

  • 1 Bed
  • 1 Bath
  • 500 Sq Ft
  • House for Rent

  199 Hoop Pole Hill Rd, Woodbury, CT 06798

  Garden apartment - complete with private firepit and picnic table. Tend to your own gardens until your hearts content! (not required - just a privilege if you choose). Freshly deep cleaned and painted and ready for new occupants. One very large bedroom with bow window and book shelves, has been used in the past as combined LR and BR space, it's that big! Eat in kitchen leaves plenty of room for a

  Mary Ann Bennett Drakeley Real Estate, Inc.

  199 Hoop Pole Hill Rd, Woodbury, CT 06798
• 

  $1,050,000 Sold Mar 21, 2025

  6 Owl Ridge Rd, Woodbury, CT 06798

  • 4 Beds
  • 5 Baths
  • 4,832 Sq Ft
  • Built 1999

  Last Sold Summary

  • 25% Below List Price
  • $217/SF
  • 165 Days On Market

  Current Estimated Value $1,110,637

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

  6 Owl Ridge Rd, Woodbury, CT 06798
• 

  Est $514,874 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,847 Sq Ft

  990 Washington Rd, Woodbury, CT 06798

  990 Washington Rd, Woodbury, CT 06798
• 

  

  

  /22

  $550,000

  • 4 Beds
  • 2 Baths
  • 1,987 Sq Ft

  667 Upper Grassy Hill Rd, Woodbury, CT 06798

  Discover this meticulously maintained Cape-style home set on 3.4 private acres in Woodbury. The property offers exceptional curb appeal, featuring a paved circular driveway and a classic stone wall that sets a welcoming tone. Inside, a beautiful slate tile foyer opens to hardwood floors and a comfortable, well-designed layout that creates an inviting atmosphere. The main level includes a

  Rhya Szymansky Drakeley Real Estate, Inc.

  667 Upper Grassy Hill Rd, Woodbury, CT 06798
• 

  

  /17

  $2,499 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,315 Sq Ft
  • House for Rent

  25 Elephant Rock Rd Unit 2, Woodbury, CT 06798

  Welcome home to this sunny 3 bedroom 2 bath duplex on a lovely culdesac and close to all! Enjoy cozy winters by the fireplace and warm summers on the private patio and backyard surrounded by beautiful trees and shrubs. Convenient parking right outside your door and hook ups for a washer and dryer in the kitchen. Pets will be considered. Short term rental considered.

  Donna Gladstein ERA Insite Realty Services

  25 Elephant Rock Rd Unit 2, Woodbury, CT 06798
• 

  $595,000 Sold Nov 03, 2025

  90 Railtree Hill Rd, Woodbury, CT 06798

  • 3 Beds
  • 2 Baths
  • 2,772 Sq Ft
  • Built 1983

  Last Sold Summary

  • 6% Above List Price
  • $215/SF
  • 28 Days On Market

  Last Listing Agent Matthew Amatruda Drakeley Real Estate, Inc.

  90 Railtree Hill Rd, Woodbury, CT 06798
• 

  Est $886,338 Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 3,583 Sq Ft

  60 Stone Pit Rd, Woodbury, CT 06798

  60 Stone Pit Rd, Woodbury, CT 06798
• 

  

  /31

  $409,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,510 Sq Ft

  298 Railtree Hill Rd, Woodbury, CT 06798

  Don't miss this exceptional opportunity in Woodbury offering three separate living spaces, perfect for investors or owner-occupants. The main house includes 3 bedrooms and 2 full baths. A second building features two additional units: a 1 bed/1 bath apartment on the lower level and a 2 bed/1 bath unit upstairs. Each unit is separately metered for electric allowing for independent utility use. The

  Shawna Mucherino Coldwell Banker Realty

  298 Railtree Hill Rd, Woodbury, CT 06798
• 

  

  /23

  $2,400 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft
  • Townhouse for Rent

  14 Quassuk Rd Unit 14, Woodbury, CT 06798

  The Charm of an 1840's Farmhouse with the Convenience of Condo Living. This Townhouse Features: Beautiful Wide Plank Hardwood Floors, Exposed Beams, Kitchen with Stainless Steel Appliances. Primary Bedroom has Brick Fireplace, Cedar Closets and Spacious 3rd Level Loft area (makes for a perfect Office Space, meditation room, etc). Tenant has access to Pool, Tennis Courts and Pickle Ball Courts.

  Joanne Cisek William Raveis Real Estate

  14 Quassuk Rd Unit 14, Woodbury, CT 06798
• 

  $840,000 Sold May 02, 2025

  11 Saxony Ln, Woodbury, CT 06798

  • 3 Beds
  • 4 Baths
  • 3,124 Sq Ft
  • Built 2019

  Last Sold Summary

  • 7% Below List Price
  • $269/SF
  • 84 Days On Market

  Current Estimated Value $855,189

  Last Listing Agent Chris Carey Carey & Guarrera Real Estate

  11 Saxony Ln, Woodbury, CT 06798
• 

  Est $522,433 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,190 Sq Ft

  325 Cowles Rd, Woodbury, CT 06798

  325 Cowles Rd, Woodbury, CT 06798
• 

  

  /7

  $315,000 Pending

  • 5 Beds
  • 2 Baths
  • 2,760 Sq Ft

  2 Linden Rd, Woodbury, CT 06798

  Calling All Investors! Opportunity knocks with this spacious corner lot duplex offering great potential in a sought-after location. One unit features 2 bedrooms, while the other boasts 3 bedrooms - each with a living room, dining room, and kitchen. Both units have the convenience of in-unit laundry, located in a bonus room. The home sits on a level lot, and each has its own septic system and

  Danielle Rownin Keller Williams Realty

  2 Linden Rd, Woodbury, CT 06798
• 

  

  /21

  $3,000 total monthly price

  • 1 Bed
  • 1 Bath
  • 1,312 Sq Ft
  • House for Rent

  235 White Deer Rocks Rd Unit Guest House, Woodbury, CT 06798

  This completely remodeled guest cottage offers the perfect retreat for weekend getaways or full-time living. The home comes fully furnished with couch, dining table, and king-size bed, while the kitchen features brand-new appliances and a conveniently located washer/dryer upstairs. The heart of the home is the great room living area with large center island-ideal for working from home or

  Christian Jensen William Pitt Sotheby's Int'l

  235 White Deer Rocks Rd Unit Guest House, Woodbury, CT 06798
• 

  $125,000 Sold Sep 16, 2025

  14 Arrowhead Way Unit 6, Woodbury, CT 06798

  • 1 Bed
  • 1 Bath
  • 546 Sq Ft
  • Built 1965

  Last Sold Summary

  • 4% Below List Price
  • $229/SF
  • 91 Days On Market

  Current Estimated Value $152,590

  Last Listing Agent Jeff Boucher Drakeley Real Estate, Inc.

  14 Arrowhead Way Unit 6, Woodbury, CT 06798
• 

  Est $255,883 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,430 Sq Ft

  76 Washington Rd Unit 40, Woodbury, CT 06798

  76 Washington Rd Unit 40, Woodbury, CT 06798
• 

  

  /13

  $675,000 Under Contract

  • Land
  • 23 Acres
  • $29,348 per Acre

  0 Cowles Rd, Woodbury, CT 06798

  Presenting a rare opportunity to acquire a 23-acre parcel that has been held within a family for generations. This expansive property, fronting on a tranquil county road, offers a serene and private setting for your future endeavors. The property is a picturesque combination of woodlands, offering an idyllic setting for those seeking privacy and connection to nature. With approximately 800 feet

  John Sniffen William Pitt Sotheby's Int'l

  0 Cowles Rd, Woodbury, CT 06798
• 

  

  /34

  $6,500 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,197 Sq Ft
  • House for Rent

  112 W Lake Rd Unit D4, Woodbury, CT 06798

  Available Immediately: Direct Waterfront property located on the west shore of Lake Quassapaug providing a tranquil setting to get away from the hustle and bustle of daily living. Nature surrounds you. Spotted nearby is the resident eagle, fox, turkey, and deer. Just a few hundred yards up the road is Flander's Nature Center, perfect for scenic hikes. Visit the new Tranquility Vineyard & Winery

  Sindy Butkus Klemm Real Estate Inc

  112 W Lake Rd Unit D4, Woodbury, CT 06798
• 

  $449,900 Sold Aug 08, 2025

  67 Flanders Rd, Woodbury, CT 06798

  • 4 Beds
  • 4 Baths
  • 2,764 Sq Ft
  • Built 1972

  Last Sold Summary

  • $163/SF
  • 25 Days On Market

  Current Estimated Value $464,885

  Last Listing Agent Michael Calabro Coldwell Banker Calabro

  67 Flanders Rd, Woodbury, CT 06798
• 

  Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 3,349 Sq Ft

  267 Good Hill Rd, Woodbury, CT 06798

  267 Good Hill Rd, Woodbury, CT 06798
• 

  

  /35

  $439,000 Under Contract

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

  70 Mountain Rd, Woodbury, CT 06798

  Come with a vision! This home is ready for someone to make it their own. Several key updates have already been completed, including a new roof (2018), furnace (2022), hot water heater (2023) and water holding tank (22-23). (The front patio was done in 2021). A convenient half bath has been added to the first floor, and the primary bedroom now features a full ensuite bath with jetted tub. The

  Donna J. Matula William Raveis Real Estate

  70 Mountain Rd, Woodbury, CT 06798
• 

  $128,500 Sold Jul 23, 2025

  16 Pilgrim Trail Unit F2, Woodbury, CT 06798

  • 1 Bed
  • 1 Bath
  • 546 Sq Ft
  • Built 1965

  Last Sold Summary

  • $235/SF
  • 19 Days On Market

  Current Estimated Value $129,037

  Last Listing Agent Karen Rigopulos BHGRE Gaetano Marra Homes

  16 Pilgrim Trail Unit F2, Woodbury, CT 06798
• 

  Est $394,541 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,615 Sq Ft

  87 Minortown Rd, Woodbury, CT 06798

  87 Minortown Rd, Woodbury, CT 06798
• 

  

  /27

  $265,000

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

  5 Upper Commons, Woodbury, CT 06798

  Welcome to 5 Upper Commons, a well-maintained 2-bedroom farmhouse-style townhouse set in a quiet, wooded community with walking trails. This home offers three finished levels and a comfortable, functional layout. The main level features an open living and dining area and a practical kitchen with good cabinet space. Central air provides year-round comfort. Upstairs, both bedrooms include walk-in

  Rafael Monegro Coldwell Banker Realty

  5 Upper Commons, Woodbury, CT 06798
• 

  $628,500 Sold Apr 28, 2025

  49 Jacks Bridge Rd, Woodbury, CT 06798

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft
  • Built 1987

  Last Sold Summary

  • 10% Below List Price
  • $624/SF
  • 228 Days On Market

  Last Listing Agent Christine Green Ardor Real Estate

  49 Jacks Bridge Rd, Woodbury, CT 06798
• 

  Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,150 Sq Ft

  126 Sherman Hill Rd Unit B8, Woodbury, CT 06798

  126 Sherman Hill Rd Unit B8, Woodbury, CT 06798
• 

  

  /26

  $215,000 Under Contract

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

  12 Edgehill Ct, Woodbury, CT 06798

  Welcome to Woodlake. Light filled end unit with deck looking out toward woodland views. Two bedrooms and baths on upper level. Spacious lower level with room for media/gym/office. Also included are laundry/ storage/ mechanicals. Convenient to the fabulous shops and restaurants in Woodbury and surrounding towns. BTW, Kitchen and baths have been professional cleaned. Unit needs new flooring on all

  Jacki Hornish W. Raveis Lifestyles Realty

  12 Edgehill Ct, Woodbury, CT 06798
• 

  $439,900 Sold Sep 02, 2025

  22 Lake Rd, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 2,008 Sq Ft
  • Built 1956

  Last Sold Summary

  • $219/SF
  • 46 Days On Market

  Current Estimated Value $437,356

  Last Listing Agent Matt Rose Keller Williams Realty

  22 Lake Rd, Woodbury, CT 06798
• 

  Est $533,365 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,165 Sq Ft

  80 Flanders Rd, Woodbury, CT 06798

  80 Flanders Rd, Woodbury, CT 06798
• 

  

  /34

  $294,900 Under Contract

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

  9 Heather Ct Unit 9, Woodbury, CT 06798

  Welcome to this light-filled 2-bedroom, 2.5-bath townhouse-style end unit in the desirable Woodlake community of Woodbury, the antique capital of CT. Sunlight pours into the main level, where the updated kitchen features quartz counters, stainless steel appliances, and excellent cabinet space. The kitchen flows seamlessly into the dining area, making everyday living and entertaining easy and

  Ann Micacci Berkshire Hathaway NE Prop.

  9 Heather Ct Unit 9, Woodbury, CT 06798
• 

  $205,000 Sold Feb 14, 2025

  126 Sherman Hill Rd Unit B9, Woodbury, CT 06798

  • 2 Beds
  • 1 Bath
  • 1,150 Sq Ft
  • Built 1964

  Last Sold Summary

  • 24% Below List Price
  • $178/SF
  • 56 Days On Market

  Last Listing Agent Jose Taverner All Connecticut Realty

  126 Sherman Hill Rd Unit B9, Woodbury, CT 06798
• 

  Est $295,654 Not Listed For Sale

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

  28 Fox Run, Woodbury, CT 06798

  28 Fox Run, Woodbury, CT 06798
• 

  

  /39

  $649,000 Under Contract

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

  94 Old Town Farm Rd, Woodbury, CT 06798

  Built in 1900 as a barn and converted to a home in 1990, the architecture fuses countryside charm and mid-century design - two contrasting genres married to create an interesting and unique experience. The home is entered via an offset entry that opens into an all-seasons sunken sunroom overlooking the expansive backyard. You flow directly into the eat-in kitchen, which is outfitted with maple

  Michael Caporizzo William Pitt Sotheby's Int'l

  94 Old Town Farm Rd, Woodbury, CT 06798
• 

  $390,000 Sold Dec 31, 2024

  20 Scuppo Rd, Woodbury, CT 06798

  • 3 Beds
  • 1 Bath
  • 1,160 Sq Ft
  • Built 1960

  Last Sold Summary

  • 4% Below List Price
  • $336/SF
  • 8 Days On Market

  Current Estimated Value $404,012

  Last Listing Agent David Hughes Century 21 AllPoints Realty

  20 Scuppo Rd, Woodbury, CT 06798
• 

  Est $889,187 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,447 Sq Ft

  18 River View Ln, Woodbury, CT 06798

  18 River View Ln, Woodbury, CT 06798
• 

  

  /21

  $355,000

  • 2 Beds
  • 2 Baths
  • 2,118 Sq Ft

  8 Tamarack Ln Unit 8, Woodbury, CT 06798

  Unique opportunity! This spacious end-unit condo offers 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 kitchen

  Jennifer Mayo William Raveis Real Estate

  8 Tamarack Ln Unit 8, Woodbury, CT 06798
• 

  $850,000 Sold Oct 29, 2025

  84 Hurds Hill Rd, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 3,736 Sq Ft
  • Built 1966

  Last Sold Summary

  • 4% Below List Price
  • $228/SF
  • 135 Days On Market

  Last Listing Agent Michael Vartolone William Raveis Real Estate

  84 Hurds Hill Rd, Woodbury, CT 06798
• 

  Est $966,689 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,468 Sq Ft

  41 Curtiss Meadows, Woodbury, CT 06798

  41 Curtiss Meadows, Woodbury, CT 06798
• 

  

  /40

  $1,275,000

  • 3 Beds
  • 5 Baths
  • 4,059 Sq Ft

  373 Transylvania Rd, Woodbury, CT 06798

  This unique allergy free home is made for entertaining. 4000 ft. home with 3 bedroom suites each containing its own full bath. Total of 5 Bathrooms. 3 Fireplaces. Chef's kitchen with granite counters, double ovens, center island, bow window w/bench seat & walk out to solid mahogany wood deck. Formal dining room has tray ceiling. Living room with fireplace and full bar. Bright piano

  Beatriz Conroy William Raveis Real Estate

  373 Transylvania Rd, Woodbury, CT 06798
• 

  $1,075,000 Sold Aug 21, 2025

  5 Blueberry Ln, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 3,874 Sq Ft
  • Built 2006

  Last Sold Summary

  • 8% Above List Price
  • $277/SF
  • 36 Days On Market

  Current Estimated Value $1,056,032

  Last Listing Agent John Donato Jr Showcase Realty, Inc.

  5 Blueberry Ln, Woodbury, CT 06798

Showing Results 41 - 80, Page 2 of 18