Homes in ZIP Code 06798

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  /4

  $179,900 Pending

  • Land
  • 3.63 Acres
  • $49,559 per Acre

  0 Minortown Rd, Woodbury, CT 06798

  Build your dream home on this 3.63-acre parcel on scenic Minortown Road in Woodbury, where the standout feature is a wide-open meadow with room to farm. Backing up to acres of protected open space, the setting feels expansive, private, and quintessentially rural-yet you're still just minutes from town amenities, shopping, and dining. With generous acreage for gardens, animals, and outdoor living

  

  Tim Drakeley

  Drakeley Real Estate, Inc.

  (475) 447-1880

  0 Minortown Rd, Woodbury, CT 06798
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  /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
• 

  $897,000 Sold Jun 27, 2025

  332 Good Hill Rd, Woodbury, CT 06798

  • 3 Beds
  • 3 Baths
  • 2,894 Sq Ft
  • Built 2015

  Last Sold Summary

  • 12% Above List Price
  • $310/SF
  • 27 Days On Market

  Current Estimated Value $900,350

  Last Listing Agent Rebecca Doh W. Raveis Lifestyles Realty

  332 Good Hill Rd, Woodbury, CT 06798
• 

  Est $909,807 Not Listed For Sale

  62 Whittlesey Rd, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 3,205 Sq Ft
  • Built 2002

  62 Whittlesey Rd, Woodbury, CT 06798

  Last Sold Summary

  • 7% Above List Price
  • $265/SF
  • 34 Days On Market

  Last Sold Price $850,000

  Last Listing Agent Brianna Carvalho Compass Connecticut, LLC
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  /39

  $849,900

  • 4 Beds
  • 2.5 Baths
  • 3,330 Sq Ft

  99 Plumb Brook Rd, Woodbury, CT 06798

  Tucked away in a private and peaceful setting, this beautifully appointed Colonial offers an exceptional blend of comfort, style and functionality. Hardwood floors and custom millwork are showcased throughout, creating a warm and refined atmosphere. A dramatic two-story foyer welcomes you and is flanked by a first-floor office with transom-topped French doors for privacy. Opposite, a double

  

  Tim Drakeley

  Drakeley Real Estate, Inc.

  (203) 871-0905

  99 Plumb Brook Rd, Woodbury, CT 06798
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  /26

  $4,000 total monthly price

  • 3 Beds
  • 3 Baths
  • 2,320 Sq Ft
  • House for Rent

  220 Upper Grassy Hill Rd, Woodbury, CT 06798

  Recently renovated single-family home on the Woodbury/Roxbury town line. Completely rebuilt from the studs up, this three-bedroom ranch features brand-new electrical, HVAC, spray-foam insulation, trim, drywall, hardwood floors, plus a new kitchen and three new baths. Rare opportunity to rent a truly "like-new" home available immediately. Enjoy a spacious main level with three bedrooms, a living

  

  Tim Drakeley

  Drakeley Real Estate, Inc.

  (475) 281-3909

  220 Upper Grassy Hill Rd, Woodbury, CT 06798
• 

  $1,700,000 Sold Jan 20, 2026

  225 Old Sherman Hill Rd, Woodbury, CT 06798

  • 4 Beds
  • 4.5 Baths
  • 4,517 Sq Ft
  • Built 1969

  Last Sold Summary

  • 19% Below List Price
  • $376/SF
  • 345 Days On Market

  Current Estimated Value $1,780,404

  Last Listing Agent Maria Taylor Klemm Real Estate Inc

  225 Old Sherman Hill Rd, Woodbury, CT 06798
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  Not Listed For Sale

  229 Bacon Pond Rd Unit 142, Woodbury, CT 06798

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

  229 Bacon Pond Rd Unit 142, Woodbury, CT 06798

  Last Sold Summary

  • 2% Above List Price
  • $196/SF
  • 60 Days On Market

  Last Sold Price $179,000

  Last Listing Agent Anthony Rivera Pro Property Management, LLC
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  /26

  $999,900

  • 3 Beds
  • 2.5 Baths
  • 2,042 Sq Ft

  27 Middle Quarter Rd, Woodbury, CT 06798

  Discover the charm of this beautiful antique home in the heart of Woodbury! Nestled on the serene Middle Quarter Road, this vintage gem is being restored by the current owner and is just a 2-minute stroll from coffee shops, top-notch restaurants, and the historic Main Street. The home will be meticulously updated from the ground up, featuring wide board antique flooring, a stunning great room

  

  Tim Drakeley

  Drakeley Real Estate, Inc.

  (203) 457-8490

  27 Middle Quarter Rd, Woodbury, CT 06798
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  /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
• 

  $480,000 Sold Nov 04, 2025

  145 Cat Swamp Rd, Woodbury, CT 06798

  • 3 Beds
  • 1.5 Baths
  • 1,792 Sq Ft
  • Built 1961

  Last Sold Summary

  • 4% Above List Price
  • $268/SF
  • 51 Days On Market

  Current Estimated Value $484,620

  Last Listing Agent Nancy Langrock William Raveis Real Estate

  145 Cat Swamp Rd, Woodbury, CT 06798
• 

  Est $831,687 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

  • 85% Above List Price
  • $142/SF
  • 53 Days On Market

  Last Sold Price $450,000

  Last Listing Agent Katherine Parlato Drakeley Real Estate, Inc.
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  /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
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  /17

  $2,200 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,350 Sq Ft
  • House for Rent

  533 Weekeepeemee Rd, Woodbury, CT 06798

  First floor two bedroom, eat in kitchen, shower bath, laundry. IMMACULATE and immediate occupancy for the right fit. Owners were just awarded the 2025 Town of Woodbury Historic Preservation Award. Eleazer Crane House - circa 1800 on 1.3 acres in rural Woodbury. Sun filled spacious apartment. Looking for that quiet tenant to be compatible with the upstairs tenants for a cohesive living experience.

  Mary Ann Bennett Drakeley Real Estate, Inc.

  533 Weekeepeemee Rd, Woodbury, CT 06798
• 

  $430,000 Sold Apr 04, 2025

  163 Washington Rd, Woodbury, CT 06798

  • 4 Beds
  • 3 Baths
  • 2,521 Sq Ft
  • Built 1836

  Last Sold Summary

  • 5% Below List Price
  • $171/SF
  • 162 Days On Market

  Current Estimated Value $449,727

  Last Listing Agent Katherine Parlato Drakeley Real Estate, Inc.

  163 Washington Rd, Woodbury, CT 06798
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  Est $199,760 Not Listed For Sale

  229 Bacon Pond Rd Unit 311, Woodbury, CT 06798

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

  229 Bacon Pond Rd Unit 311, Woodbury, CT 06798

  Last Sold Summary

  • 2% Above List Price
  • $214/SF
  • 16 Days On Market

  Last Sold Price $195,000

  Last Listing Agent John Calabrese Better Living Realty, LLC
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  /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
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  /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
• 

  $424,950 Sold Oct 23, 2025

  158 Hazel Plain Rd, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 2,085 Sq Ft
  • Built 1974

  Last Sold Summary

  • $204/SF
  • 32 Days On Market

  Current Estimated Value $437,456

  Last Listing Agent Michael Ferris eXp Realty

  158 Hazel Plain Rd, Woodbury, CT 06798
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  Not Listed For Sale

  16 Pilgrim Trail Unit 6, Woodbury, CT 06798

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

  16 Pilgrim Trail Unit 6, Woodbury, CT 06798

  Last Sold Summary

  • $190/SF
  • 86 Days On Market

  Last Sold Price $104,000

  Last Listing Agent Rebecca Koladis Berkshire Hathaway Home Services
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  /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
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  /18

  $2,300 total monthly price

  • 2 Beds
  • 1.5 Baths
  • 1,000 Sq Ft
  • Apartment for Rent

  7 Washington Rd, Woodbury, CT 06798

  Enjoy the charm of Woodbury in this beautifully renovated 2-bedroom rental. The main level features living room combo with kitchen -granite center island, half bath and separate laundry area. Upper level offers two bedrooms with full bath. Step outside to a spacious backyard with a fire pit, perfect relaxing and quiet evenings. Take a stroll along historic Main Street and/or visit the array of

  Frances Mirabilio Town & Country Realty and Design, LLC

  7 Washington Rd, Woodbury, CT 06798
• 

  $660,000 Sold Feb 05, 2026

  38 Barnhill Rd, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 2,835 Sq Ft
  • Built 1986

  Last Sold Summary

  • 5% Below List Price
  • $233/SF
  • 134 Days On Market

  Current Estimated Value $686,628

  Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

  38 Barnhill Rd, Woodbury, CT 06798
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  Est $1,294,067 Not Listed For Sale

  362 Transylvania Rd, Woodbury, CT 06798

  • 2 Beds
  • 4.5 Baths
  • 6,334 Sq Ft
  • Built 1920

  362 Transylvania Rd, Woodbury, CT 06798

  Last Sold Summary

  • 12% Above List Price
  • $182/SF
  • 60 Days On Market

  Last Sold Price $1,155,000

  Last Listing Agent Justin Bette Century 21 Bette Real Estate
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  /25

  $279,990

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

  4 Fox Run Unit 4, Woodbury, CT 06798

  Welcome to this beautifully refreshed townhome in the highly desirable Woodlake Condominium Complex in Woodbury. Freshly painted throughout and filled with natural light, the main level features hardwood floors, a spacious living and dining area with a cozy fireplace, and a sliding door that opens to a private deck overlooking peaceful wooded surroundings. The updated kitchen includes granite

  Henrik K Kjaer Keller Williams Realty

  4 Fox Run Unit 4, Woodbury, CT 06798
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  /43

  $1,600 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
• 

  $350,000 Sold Aug 08, 2025

  306 Upper Grassy Hill Rd, Woodbury, CT 06798

  • 3 Beds
  • 2 Baths
  • 1,936 Sq Ft
  • Built 1964

  Last Sold Summary

  • $181/SF
  • 6 Days On Market

  Current Estimated Value $384,830

  Last Listing Agent Shawna Mucherino Coldwell Banker Realty

  306 Upper Grassy Hill Rd, Woodbury, CT 06798
• 

  Est $400,761 Not Listed For Sale

  550 Grassy Hill Rd, Woodbury, CT 06798

  • 3 Beds
  • 1 Bath
  • 1,332 Sq Ft
  • Built 1939

  550 Grassy Hill Rd, Woodbury, CT 06798

  Last Sold Summary

  • 7% Above List Price
  • $282/SF
  • 162 Days On Market

  Last Sold Price $375,000

  Last Listing Agent Dee Ceylan Coldwell Banker Realty
• 

  

  /40

  $649,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,264 Sq Ft

  13 Park Ln, Woodbury, CT 06798

  Set on a picturesque lot with mature landscaping and gorgeous outdoor spaces, this beautifully maintained home offers a flexible layout designed for both entertaining and everyday living. The front entry opens to a bright and inviting living room with built-ins and gas fireplace. The kitchen blends style and function with granite countertops, stainless appliances, and a natural flow into the

  Michael Wright RE/MAX Right Choice

  13 Park Ln, Woodbury, CT 06798
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  /18

  $1,600 total monthly price

  • 2 Beds
  • 1 Bath
  • 600 Sq Ft
  • House for Rent

  4 Weekeepeemee Rd, Woodbury, CT 06798

  Freshly painted, new counter tops, new appliances - including the one unit washer / dryer, new tub/shower enclosure. Ready for immediate occupancy. Bright, sunny unit - pics show last bit of painting and clean up is being completed, but it's ready to show. One large bedroom, and one bedroom is small, perfect for home office, child, or a large walk in closet!! Living room and bedrooms have

  Mary Ann Bennett Drakeley Real Estate, Inc.

  4 Weekeepeemee Rd, Woodbury, CT 06798
• 

  $465,000 Sold Sep 23, 2025

  9 Nettleton Hollow Rd, Bethlehem, CT 06751

  • 3 Beds
  • 2.5 Baths
  • 2,034 Sq Ft
  • Built 1978

  Last Sold Summary

  • 3% Below List Price
  • $229/SF
  • 73 Days On Market

  Current Estimated Value $464,827

  Last Listing Agent Matthew Egan Regency Real Estate, LLC

  9 Nettleton Hollow Rd, Bethlehem, CT 06751
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  Est $562,884 Not Listed For Sale

  58 Railtree Hill Rd, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 1,900 Sq Ft
  • Built 1949

  58 Railtree Hill Rd, Woodbury, CT 06798

  Last Sold Summary

  • 13% Above List Price
  • $263/SF
  • 82 Days On Market

  Last Sold Price $500,000

  Last Listing Agent William Piccirillo BHGRE Gaetano Marra Homes
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  /40

  $675,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,073 Sq Ft

  43 Mill Rd, Woodbury, CT 06798

  Experience the ease of single-level living in this lovingly maintained residence. Nestled on a private lot bordering acres of open space, this home is a study in thoughtful design and architectural detail. The interior is defined by a sense of scale and light, featuring hardwood floors, elegant tray ceilings, and custom crown moldings. At the heart of the home, the spacious living room is

  Christian Jensen William Pitt Sotheby's Int'l

  43 Mill Rd, Woodbury, CT 06798
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  /30

  $2,000 total monthly price

  • 2 Beds
  • 1 Bath
  • 913 Sq Ft
  • Condo for Rent

  229 Bacon Pond Rd Unit 229 Bacon Pond Rd APT 232, Woodbury, CT 06798

  Gorgeous 2-bedroom 1-bath condo. Luxury vinyl plank flooring. Private patio. 2 designated parking spaces. Swimming Pool. Beautiful country setting. Close to town. No smoking. No pets. Rent includes water and condo fees. Renter pays electric and utilities. 2 months' deposit and 1st month's rent due at signing.

  229 Bacon Pond Rd Unit 229 Bacon Pond Rd APT 232, Woodbury, CT 06798
• 

  $445,000 Sold Mar 03, 2025

  397 Railtree Hill Rd, Woodbury, CT 06798

  • 3 Beds
  • 2 Baths
  • 1,444 Sq Ft
  • Built 1978

  Last Sold Summary

  • 1% Below List Price
  • $308/SF
  • 41 Days On Market

  Current Estimated Value $469,935

  Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.

  397 Railtree Hill Rd, Woodbury, CT 06798
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  Not Listed For Sale

  49 Woods Way, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 2,045 Sq Ft
  • Built 1980

  49 Woods Way, Woodbury, CT 06798

  Last Sold Summary

  • $153/SF
  • 90 Days On Market

  Last Sold Price $312,000

  Last Listing Agent Cathy Masi Flagpole Realty Inc
• 

  

  /31

  $895,000 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 3,776 Sq Ft

  52 Steeple View Ln, Woodbury, CT 06798

  Nestled within an established enclave of Woodbury-a quintessential New England town-this 2001 four-bedroom Colonial offers a refined blend of understated, classic architecture, and modern comfort. Ideally located just five minutes from Main Street, the home is privately sited at the end of a quiet cul-de-sac, bordered by tranquil woodlands. The interior showcases richly layered trim details,

  Beverly Mosch William Pitt Sotheby's Int'l

  52 Steeple View Ln, Woodbury, CT 06798
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  /11

  $1,750 total monthly price

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

  47A Quassuk Rd, Woodbury, CT 06798

  Well maintained cottage near the heart of Woodbury. Freshly painted, updated fixtures & flooring, newer mini split for heat & A/C, newer windows, & well insulated for super efficiency. Serene & private grounds with a rear patio overlooking the landscape & a large pond. Owners reside in the main house & will plow & maintain the lawn. Tenant to remove the snow on his/her walkway to entry. Tenant

  Gina Jacobs Gina Jacobs Real Estate

  47A Quassuk Rd, Woodbury, CT 06798
• 

  $765,000 Sold Jul 29, 2025

  3 Inwood Ln, Woodbury, CT 06798

  • 4 Beds
  • 4 Baths
  • 3,330 Sq Ft
  • Built 1986

  Last Sold Summary

  • 13% Below List Price
  • $230/SF
  • 58 Days On Market

  Current Estimated Value $803,474

  Last Listing Agent Elizabeth Newnham William Pitt Sotheby's Int'l

  3 Inwood Ln, Woodbury, CT 06798
• 

  Not Listed For Sale

  126 Sherman Hill Rd Unit B9, Woodbury, CT 06798

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

  126 Sherman Hill Rd Unit B9, Woodbury, CT 06798

  Last Sold Summary

  • $178/SF
  • 56 Days On Market

  Last Sold Price $205,000

  Last Listing Agent Jose Taverner All Connecticut Realty

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