Homes in ZIP Code 06798

• 

  

  

  /34

  $559,900 Pending

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

  18 Woodbury Hill, Woodbury, CT 06798

  Experience the charm of Woodbury's most desirable condominium community at 18 Woodbury Hill. This beautifully updated Putnam's Loft model offers an open and inviting floor plan perfect for both everyday living and entertaining. The main level features a spacious living room with oak floors, vaulted ceiling, fireplace, and abundant natural light, flowing seamlessly into the dining room. The

  

  Tim Drakeley

  Drakeley Real Estate, Inc.

  (475) 335-8066

  18 Woodbury Hill, Woodbury, CT 06798
• 

  

  

  /31

  $3,750 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,968 Sq Ft
  • House for Rent

  33 Washington Ave, Woodbury, CT 06798

  AVAILABLE FOR $3,950/MONTH. Stunning over-sized Cape on serene, park-like grounds adjacent to a nature preserve. Fully furnished, this inviting 2 bedroom home has been lovingly renovated with a great eye for detail. Quiet street centrally located in historic Woodbury. Newly finished hardwood oak flooring throughout. Two full bathrooms. The large living room with fireplace also includes a bright

  

  Rebecca Doh

  W. Raveis Lifestyles Realty

  (203) 872-6274

  33 Washington Ave, Woodbury, CT 06798
• 

  $640,000 Sold Nov 20, 2025

  • 2,252 Sq Ft
  • $284/SF
  • 54 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1979

  32 Plumb Brook Rd, Woodbury, CT 06798

  Falling water...Step away from the day and step on the property and take a deep breath. Instantly feel the weight of the worlds worries fade away. Commune with nature in this sanctuary property. From the front entry views direct to the back lush greenery, beautiful rock outcroppings and every window in between you can feel natures touch. Magnificent gardens and respite areas to sit and reflect or

  Mary Ann Bennett Drakeley Real Estate, Inc.

  32 Plumb Brook Rd, Woodbury, CT 06798
• 

  Not Listed For Sale

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

  23 Upper Commons Unit 23, Woodbury, CT 06798

  23 Upper Commons Unit 23, Woodbury, CT 06798
• 

  

  

  /40

  $899,900

  • 4 Beds
  • 2.5 Baths
  • 3,700 Sq Ft

  337 Main St S, Woodbury, CT 06798

  A Real Classic! Beautifully renovated with many original features. Located in the Historic District in the heart of Woodbury. Stroll along Main Street to parks, excellent restaurants, house of worship, conveniences and antique shops. Home is just lovely with exposed beams, wide board hardwood floors, 4 fireplaces, outside on the patio, primary bedroom, dining room and living room. One fireplace

  

  Marian Van Egas

  Berkshire Hathaway NE Prop.

  (475) 255-3184

  337 Main St S, Woodbury, CT 06798
• 

  

  /35

  $1,550 - $1,899 per month plus fees

  Woodbury Knoll

  Studio - 2 Beds

  302 Tuttle Rd, Woodbury, CT 06798

  Welcome to Woodbury Knoll Apartments, where modern comfort meets tranquil, lakeside living. Life unfolds at a different pace here mornings are inspired by natures quiet beauty, and evenings unwind in serene surroundings. In our Woodbury, CT apartments, you'll discover a lifestyle thats vibrant yet peaceful, perfectly balanced, and endlessly welcoming.

  302 Tuttle Rd, Woodbury, CT 06798
• 

  $35,000 Sold Nov 20, 2025

  • Land
  • 3.6 Acres
  • $9,722 per Acre

  • 57 Days On Market

  0 Main St N Unit 24119173, Woodbury, CT 06798

  Unknown access at this time for an interior lot on Woodbury / Watertown Town Line. No current access. Possible building lot. Some information has been located from Town offices. Watertown / Woodbury town line runs in from of the East side of this property. An old "wood road" is indicated on neighboring property deeds. Buyer and Agent to do due diligence. Information already obtained available in

  Jeff Boucher Drakeley Real Estate, Inc.

  0 Main St N Unit 24119173, Woodbury, CT 06798
• 

  Est $701,446 Not Listed For Sale

  • 3 Beds
  • 6 Baths
  • 8,747 Sq Ft

  785 Washington Rd, Woodbury, CT 06798

  785 Washington Rd, Woodbury, CT 06798
• 

  /2

  $399,900

  • Land
  • 56.29 Acres
  • $7,104 per Acre

  0 Main St N Unit 24072824, Woodbury, CT 06798

  56 acres in the heart of Woodbury. The perfect spot for a compound or subdivide and create an open space subdivision or a few large parcels. Potential for terrific views over the Nonnewaug Valley. Located a few minutes from downtown and 5 minutes from Nonnewaug High School. Build your dream house and enjoy the views!

  

  Tim Drakeley

  Drakeley Real Estate, Inc.

  (475) 255-2991

  0 Main St N Unit 24072824, Woodbury, CT 06798
• 

  

  /24

  $2,100 total monthly price

  • 2 Beds
  • 1 Bath
  • 2,841 Sq Ft
  • House for Rent

  141 Washington Rd Unit 2, Woodbury, CT 06798

  Beautifully Renovated 2-Bedroom Apartment in Woodbury, CT Welcome to your newly renovated 2-bedroom, 1-bath apartment located in the heart of Woodbury. This top floor, bright and inviting apartment blends modern updates with charming character details, including exposed wood beams and warm, wood-style flooring throughout. The brand-new kitchen features crisp white shaker cabinets, quartz

  Dean Giatas Fiorelli Realty, LLC

  141 Washington Rd Unit 2, Woodbury, CT 06798
• 

  $490,000 Sold Nov 20, 2025

  • 2,216 Sq Ft
  • $221/SF
  • 27 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1948

  15 Lynns Corner Rd, Woodbury, CT 06798

  Set along a private driveway and conveniently located near the town centers of Woodbury, Bethlehem, and Watertown, this contemporary-style Cape blends charm, character, and modern updates throughout. The open-concept kitchen and living room feature granite countertops, stainless steel appliances, and a slider leading to a spacious deck overlooking a lush yard and babbling brook - perfect for

  Taylor O'Keefe Drakeley Real Estate, Inc.

  15 Lynns Corner Rd, Woodbury, CT 06798
• 

  Not Listed For Sale

  0 Mill Rd, Woodbury, CT 06798

  0 Mill Rd, Woodbury, CT 06798
• 

  

  /40

  $769,900 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 3,196 Sq Ft

  118 Good Hill Rd, Woodbury, CT 06798

  Beautifully Spacious Colonial in the Heart of Woodbury. This inviting in-town colonial offers the perfect balance of charm and convenience-just 5 minutes from town parks, top-rated Woodbury schools, shopping, and restaurants. Freshly refinished hardwood floors bring a warm glow throughout the home's 3,200 sq. ft. of well-crafted living space. The main level features a sun-filled kitchen and great

  

  Tim Drakeley

  Drakeley Real Estate, Inc.

  (203) 350-7018

  118 Good Hill Rd, Woodbury, CT 06798
• 

  

  /20

  $4,950 per month plus fees

  • 4 Beds
  • 4.5 Baths
  • 7,112 Sq Ft
  • House for Rent

  259 Main St S, Woodbury, CT 06798

  Property Id: 1500786Located on Main Street South in the heart of Woodbury, in the Litchfield Hills this main house offers 4 BR, 4.5 baths and features original architectural elements, ample living space and beautiful outdoor space. The main living area has a half bath, EIK with island, SS appliances and door to side deck for outdoor eating and grilling + private courtyard, professionally

  259 Main St S, Woodbury, CT 06798
• 

  $600,000 Sold Nov 20, 2025

  • 2,032 Sq Ft
  • $295/SF
  • 60 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1968

  36 Heritage Dr, Woodbury, CT 06798

  Wonderful, spacious 3 bedroom 2.5 bath ranch on an open, level 1.3 acre lot. Sited on a quiet street that is still convenient to town, the home sits well back from the road and also offers a large private backyard. From the foyer one is greeted by an L shaped living and dining area with lots of large windows and an abundance of natural light. The eat-in kitchen features wood cabinets, plenty of

  Justin Bette Joseph Bette REALTORS Inc

  36 Heritage Dr, Woodbury, CT 06798
• 

  Est $1,473,409 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 5,694 Sq Ft

  17 Gate Post Ln, Woodbury, CT 06798

  17 Gate Post Ln, Woodbury, CT 06798
• 

  

  /38

  $539,000 Open Sun 11AM - 1PM

  • 2 Beds
  • 2.5 Baths
  • 3,362 Sq Ft

  9 Hill View Ln, Woodbury, CT 06798

  Charming Dutch Colonial located in the desirable South Brook community in Woodbury, walking distance from the bustling shops and restaurants. This home is part of a small enclave of 21 single, detached residences. Features include a new wood roof, hardwood floors throughout, and a private backyard with patio. The first floor offers a formal dining room, an eat-in kitchen with ample cabinet and

  

  Mary Ann Hebert

  BHGRE Gaetano Marra Homes

  (475) 264-5720

  9 Hill View Ln, Woodbury, CT 06798
• 

  

  /23

  $4,450 total monthly price

  • 4 Beds
  • 2.5 Baths
  • 3,345 Sq Ft
  • House for Rent

  35 Highpoint Rd, Woodbury, CT 06798

  Elegant Colonial in a Premier Location Experience timeless sophistication in this meticulously maintained Center Hall Colonial, ideally situated just minutes from I-84. This residence offers 4 expansive bedrooms, 2.5 designer baths, and multiple living spaces, including two gracious family rooms and a sun-drenched four-season room. Refined details abound-gleaming hardwood floors, three stately

  William Voight Coldwell Banker Realty

  35 Highpoint Rd, Woodbury, CT 06798
• 

  $110,000 Sold Nov 19, 2025

  • Land
  • 2.1 Acres
  • $52,381 per Acre

  • 231 Days On Market

  0 Main St N Unit 24072843, Woodbury, CT 06798

  Residential lot of record on Main Street North, Woodbury. A private lot with the potential for distant views over the cornfields in the Nonnewaug Valley. An ideal location within a few minutes to Woodbury's historic downtown and 5 to 10 minutes to Bethlehem and Watertown town centers.

  Tim Drakeley Drakeley Real Estate, Inc.

  0 Main St N Unit 24072843, Woodbury, CT 06798
• 

  Est $519,772 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
• 

  

  /39

  $1,149,000

  • 3 Beds
  • 2.5 Baths
  • 4,012 Sq Ft

  24 Roxbury Rd, Woodbury, CT 06798

  Tucked away in the picturesque hills of Litchfield County, right on the desirable Woodbury/Roxbury line, this stunning Colonial-Contemporary residence offers an unparalleled blend of privacy, natural beauty, and modern comfort on nearly 10 acres of pristine land. Surrounded by mature trees, vibrant plantings, and lush greenery, the property is enhanced by the gentle sounds of Transylvania Brook

  

  Shaylene Neumann

  Houlihan Lawrence

  (475) 265-6372

  24 Roxbury Rd, Woodbury, CT 06798
• 

  

  /43

  $1,850 total monthly price

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • Condo for Rent

  31 Pilgrim Trail Unit 31-5 PILGRIM TRAIL, Woodbury, CT 06798

  Impeccable large 2nd floor end unit, bright, cheerful and safe location with beautiful views. Freshly painted and professionally cleaned with new carpeting throughout. Rent includes heat, hot water and appliances. Tenant pays electric, cable/internet, renters insurance. Trash and recycling services and all grounds maintenance also included. New mini blinds throughout. Neighborhood is quiet and

  31 Pilgrim Trail Unit 31-5 PILGRIM TRAIL, Woodbury, CT 06798
• 

  $420,000 Sold Nov 19, 2025

  • 1,328 Sq Ft
  • $316/SF
  • 14 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1956

  223 Tuttle Rd, Woodbury, CT 06798

  Looking for peace, privacy and small-town charm? Welcome to this delightful two-bedroom, one-bathroom Ranch tucked away in the quiet town of Woodbury. Step into a beautifully tiled breezeway- a cozy spot to relax with a book or enjoy your morning coffee. Just off the breezeway, sliding glass doors open to a brick patio, ideal for entertaining or simply enjoying the outdoors. Inside, the living

  Rhya Szymansky Drakeley Real Estate, Inc.

  223 Tuttle Rd, Woodbury, CT 06798
• 

  Est $865,013 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
• 

  

  /15

  $990,000 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.

  (475) 284-8768

  523 Main St N, Woodbury, CT 06798
• 

  

  /15

  $1,700 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
• 

  $490,000 Sold Nov 18, 2025

  • 1,874 Sq Ft
  • $261/SF
  • 28 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1986

  17 Old Flanders Rd, Woodbury, CT 06798

  Welcome to this beautifully situated saltbox colonial reproduction home that perfectly blends privacy and a cul-de-sac neighborhood setting. Step into the inviting cathedral foyer flooded by natural light from the two skylights above. The first floor features rustic wide board pine floors that complement the stone fireplace in the living room for a classic New England feel. The sunny kitchen has

  Stephanie Chapman Scalzo Real Estate

  17 Old Flanders Rd, Woodbury, CT 06798
• 

  Est $501,797 Not Listed For Sale

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

  325 Cowles Rd, Woodbury, CT 06798

  325 Cowles Rd, Woodbury, CT 06798
• 

  

  /40

  $1,100,000

  • 4 Beds
  • 2.5 Baths
  • 3,545 Sq Ft

  45 N Gate Rd, Woodbury, CT 06798

  Welcome to Woodbury, a quintessential New England town. This house is located in a very desirable neighborhood, just north of the town center. An inviting covered front porch will greet you. This leads to a 2 story foyer and an open floor plan opens up in front of you! To the left is a formal LR/Den. (cozy up with a good book) To the right is formal Dining Room with a trey ceiling, seats 8-10

  Jeff Colt Showcase Realty, Inc.

  45 N Gate 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
• 

  $500,000 Sold Nov 17, 2025

  • 2,064 Sq Ft
  • $242/SF
  • 77 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1900

  12 Spring St, Woodbury, CT 06798

  Step into this well-cared-for 3 bedroom, 2 bath Victorian offering just over 2,000 sq. ft. of comfortable living space. Filled with natural light and character, this home blends historic charm with thoughtful updates, including a mix of original and newer engineered hardwood floors, and two generously sized, updated baths. Original architectural details add warmth and personality, while newer

  Rhya Szymansky Drakeley Real Estate, Inc.

  12 Spring St, Woodbury, CT 06798
• 

  Est $260,696 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
• 

  

  /20

  $775,000

  • 4 Beds
  • 4 Baths
  • 2,980 Sq Ft

  432 Quassapaug Rd, Woodbury, CT 06798

  Welcome to Eastfield Farms Etates. This Colonial features an open floor plan for comfortable everyday living an entertaining alike. The large foyer flows to both the formal living room with french doors and formal dining room. Both with crown molding and accent lighting. Just down the hall step into the spacious kitchen with center island, granite counter tops stainless appliances. The dining

  Ray Manzi Manzi Real Estate

  432 Quassapaug Rd, Woodbury, CT 06798
• 

  

  /30

  $4,500 total monthly price

  • 3 Beds
  • 2.5 Baths
  • 2,100 Sq Ft
  • House for Rent

  124 Old Sherman Hill Rd, Woodbury, CT 06798

  Welcome to this charming three-bedroom, two-and-a-half-bath ranch, set on nearly 3 beautifully landscaped acres that offer both privacy and curb appeal. The home features a spacious two-car detached garage and a welcoming interior designed for comfortable living. A large eat-in kitchen with granite counters, stainless steel appliances, and abundant natural light serves as the heart of the home,

  Dave Fairty Regency Real Estate, LLC

  124 Old Sherman Hill Rd, Woodbury, CT 06798
• 

  $1,225,000 Sold Nov 16, 2025

  • 4,682 Sq Ft
  • $262/SF
  • 44 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 2006

  68 Whittlesey Rd, Woodbury, CT 06798

  This magnificent Woodbury colonial, adjacent to 42 acres of open space, offers an unparalleled blend of elegance and tranquility. Surrounded by hiking trails, park like grounds and a serene brook. A light filled interior with soaring nine foot ceilings, graceful arches and an open flowing floor plan. The wraparound mahogany deck invites you to relax and take in the peace and quiet. The back

  Michael Caporizzo William Pitt Sotheby's Int'l

  68 Whittlesey 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
• 

  

  /40

  $799,000

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

  92 Minortown Rd, Woodbury, CT 06798

  Charming Gentleman's Farm on 5.76 Acres. Welcome to this beautifully maintained gentleman's farm, perfectly set on 5.76 level acres of open pasture and riding space. Ideal for horse enthusiasts, the property features four barns with a total of 10 stalls, two wash stalls, and a 20x60 meter riding arena with quality stone dust and sand footing. The grounds offer a wonderful mix of functionality and

  Heather Crabtree Coldwell Banker Realty

  92 Minortown Rd, Woodbury, CT 06798
• 

  

  /33

  $3,500 total monthly price

  • 4 Beds
  • 3 Baths
  • 3,063 Sq Ft
  • House for Rent

  510 Good Hill Rd, Woodbury, CT 06798

  Rare opportunity to lease this c.1848 Farmhouse, set just steps from the Roxbury/Woodbury town line and overlooking the Roxbury Land Trust. Annual lease for unfurnished 10-room home offering timeless charm, sweeping views from every angle, and modern comfort. Inside, enjoy 4 bedrooms, 3 full baths, laundry on the main floor, wood burning stove and 1 fireplace. The home features a symmetrical

  Robert Pendilla W. Raveis Lifestyles Realty

  510 Good Hill Rd, Woodbury, CT 06798
• 

  $775,000 Sold Nov 13, 2025

  • 2,600 Sq Ft
  • $298/SF
  • 103 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2024

  6 Strong Field Rd, Woodbury, CT 06798

  Experience elevated New England living at 6 Strong Field Road, an exceptional 2024 custom-built Cape Cod residence set on a private, manicured 1-acre lot in one of Woodbury's most desirable enclaves. Designed for discerning buyers, this 4-bedroom, 2.5-bath masterpiece blends architectural sophistication with everyday comfort. Inside, you're welcomed by an airy open-concept floor plan, enhanced by

  Mary Ann Bennett Drakeley Real Estate, Inc.

  6 Strong Field Rd, Woodbury, CT 06798
• 

  Est $404,912 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

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