Homes in ZIP Code 06798

• 

  

  

  /40

  $684,000

  Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,874 Sq Ft

  74 Middle Quarter Rd, Woodbury, CT 06798

  Welcome to 74 Middle Quarter Rd-minutes from downtown, a charming antique colonial home that has been truly loved and thoughtfully maintained, offering the perfect blend of character, space, and everyday comfort. From the moment you step inside, you'll feel the warmth of the main level, featuring a farmhouse-style kitchen with an eat-in area and a cozy wood-burning stove-the kind of space where

  Jennifer Kelley Compass Connecticut, LLC

  74 Middle Quarter Rd, Woodbury, CT 06798
• Selling your home? Sell it faster and for more with a Homes.com Boost.

  Learn More
• 

  

  

  /10

  $1,900 Per Month

  • 2 Beds
  • 1 Bath
  • 6,097 Sq Ft
  • House for Rent

  107 Main St N, Woodbury, CT 06798

  2 BEDROOM - BRAND NEW REMODEL - NEW kITCHEN - BATH TOP TO BOTTOM CENTRAL AIR- WASHER & DRYER INCLUDED AND OFF STREET PARKING

  Pat Civitella Civitella Real Estate LLC

  107 Main St N, 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 $127,709

  Last Listing Agent Jeff Boucher Drakeley Real Estate, Inc.

  14 Arrowhead Way Unit 6, Woodbury, CT 06798
• 

  Est $857,491

  Not Listed For Sale

  60 Stone Pit Rd, Woodbury, CT 06798

  • 4 Beds
  • 5 Baths
  • 3,583 Sq Ft
  • Built 1999

  60 Stone Pit Rd, Woodbury, CT 06798

  Last Sold Summary

  • 11% Above List Price
  • $216/SF
  • 35 Days On Market

  • Last Sold Price $775,000
  • Jul 12, 2024

  Last Listing Agent Sharon McGuire William Pitt
• 

  

  

  /39

  $895,000

  • 4 Beds
  • 2.5 Baths
  • 2,283 Sq Ft

  253 Bacon Pond Rd, Woodbury, CT 06798

  Welcome to Bacon Pond House. A seamless blend of 19th-century soul and 21st-century luxury. Situated on over 3 acres, this antique Colonial has been thoughtfully revived to honor its heritage while offering every modern convenience. The interior, lovingly brought back to life, features wide-plank flooring and exposed hand-hewn beams that anchor the home's historic character. The rooms are

  Christian Jensen William Pitt Sotheby's Int'l

  253 Bacon Pond Rd, Woodbury, CT 06798
• 

  

  /40

  $7,500 Per Month

  • 4 Beds
  • 2.5 Baths
  • 3,159 Sq Ft
  • House for Rent

  260 White Deer Rocks Rd, Woodbury, CT 06798

  There is no better place to spend your time in Litchfield County than the town of Woodbury. Honored as "Connecticut's most charming town" you have access to award-winning dining (indoor & outdoor), local farms & CSA's, natural food stores, spa's, vineyards & breweries, antique shops, golf courses, bike trails, lakes & hiking - all minutes away from this centrally located property. This home's

  Michael Caporizzo William Pitt Sotheby's Int'l

  260 White Deer Rocks Rd, 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 $498,885

  Last Listing Agent Michael Calabro Coldwell Banker Calabro

  67 Flanders Rd, Woodbury, CT 06798
• 

  Est $571,746

  Not Listed For Sale

  325 Cowles Rd, Woodbury, CT 06798

  • 3 Beds
  • 2 Baths
  • 2,190 Sq Ft
  • Built 1947

  325 Cowles Rd, Woodbury, CT 06798

  Last Sold Summary

  • 29% Above List Price
  • $202/SF
  • 142 Days On Market

  • Last Sold Price $442,500
  • Oct 04, 2024

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

  

  /39

  $849,900

  Under Contract

  • 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.

  99 Plumb Brook Rd, Woodbury, CT 06798
• 

  

  /25

  $2,150 Per Month

  • 2 Beds
  • 1.5 Baths
  • 960 Sq Ft
  • Townhouse for Rent

  74 Washington Rd Unit 16, Woodbury, CT 06798

  Gracious townhome just completely reborn! Excellent quality renovations throughout! Bright and open living flow. Great for entertaining. The sun-splashed living room is cheerful. The broad picture window views the lovely landscape and lawn. The new high-end kitchen boasts soft-close doors with very ample cabinet and counter space. There is a convenient first floor laundry. Dining area views

  Joel Matson Coldwell Banker Realty

  74 Washington Rd Unit 16, Woodbury, CT 06798
• 

  $310,000

  Sold Apr 13, 2026

  4 Heather Ct Unit 4, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 1,888 Sq Ft
  • Built 1974

  Last Sold Summary

  • $164/SF
  • 82 Days On Market

  Last Listing Agent Jenn Lailer BHGRE Gaetano Marra Homes

  4 Heather Ct Unit 4, Woodbury, CT 06798
• 

  Est $242,391

  Not Listed For Sale

  76 Washington Rd Unit 40, Woodbury, CT 06798

  • 2 Beds
  • 1.5 Baths
  • 1,430 Sq Ft
  • Built 1988

  76 Washington Rd Unit 40, Woodbury, CT 06798

  Last Sold Summary

  • 1% Below List Price
  • $172/SF
  • 22 Days On Market

  • Last Sold Price $245,500
  • May 17, 2024

  Last Listing Agent Colleen Pickwick eXp Realty
• 

  

  /24

  $745,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,060 Sq Ft

  86 Quail Run Rd, Woodbury, CT 06798

  QUAIL RUN On the cul de sac - 4 NEW HOMES ALL 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. #86 is a 3

  Scott Volpe Coldwell Banker Realty

  86 Quail Run Rd, Woodbury, CT 06798
• 

  $522,500

  Sold Feb 18, 2026

  667 Upper Grassy Hill Rd, Woodbury, CT 06798

  • 4 Beds
  • 2 Baths
  • 1,987 Sq Ft
  • Built 1973

  Last Sold Summary

  • 5% Below List Price
  • $263/SF
  • 75 Days On Market

  Current Estimated Value $536,308

  Last Listing Agent Rhya Szymansky Drakeley Real Estate, Inc.

  667 Upper Grassy Hill Rd, Woodbury, CT 06798
• 

  Est $841,091

  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

  • 1% Below List Price
  • $265/SF
  • 34 Days On Market

  • Last Sold Price $850,000
  • Feb 21, 2025

  Last Listing Agent Brianna Carvalho Compass Connecticut, LLC
• 

  

  /35

  $299,000

  Under Contract

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

  6 Highpoint Ct Unit 6, Woodbury, CT 06798

  ** Multiple offer situation, offers deadline extended to May 9, 5pm**. Privately situated within the complex, this beautifully updated home offers a rare blend of comfort and nature. It abuts hundreds of acres of protected forest, providing exceptional privacy along with the soothing sounds of songbirds, visits from hummingbirds, and abundant wildlife. Located in highly sought-after Woodbury,

  Patricia Huegi Kiwi Homes

  6 Highpoint Ct Unit 6, 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 $129,877

  Last Listing Agent Karen Rigopulos West View Properties, LLC

  16 Pilgrim Trail Unit F2, Woodbury, CT 06798
• 

  Not Listed For Sale

  267 Good Hill Rd, Woodbury, CT 06798

  • 3 Beds
  • 4 Baths
  • 3,349 Sq Ft
  • Built 1790

  267 Good Hill Rd, Woodbury, CT 06798

  Last Sold Summary

  • $366/SF
  • 54 Days On Market

  • Last Sold Price $1,225,000
  • Oct 02, 2024

  Last Listing Agent Maris LeBlanc William Pitt
• 

  

  /15

  $775,000

  Coming Soon

  • 4 Beds
  • 3.5 Baths
  • 2,708 Sq Ft

  28 School St, Woodbury, CT 06798

  The Orton-Martin Homestead. One of Woodbury's oldest homes has been updated for today's lifestyle. History surrounds you with wide board flooring, library built-ins, two fireplaces and 1850 barn. This four -bedroom home offers spacious rooms, three finished levels and hidden delights. Enjoy picnics under the mature trees on your own fenced-in level yard. Sidewalks take you everywhere on Main St

  Sindy Butkus Klemm Real Estate Inc

  28 School St, Woodbury, CT 06798
• 

  $370,000

  Sold Dec 29, 2025

  298 Railtree Hill Rd, Woodbury, CT 06798

  • 3 Beds
  • 2 Baths
  • 1,510 Sq Ft
  • Built 1967

  Last Sold Summary

  • 10% Below List Price
  • $245/SF
  • 95 Days On Market

  Last Listing Agent Shawna Mucherino Coldwell Banker Realty

  298 Railtree Hill Rd, Woodbury, CT 06798
• 

  Est $179,588

  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

  • $196/SF
  • 60 Days On Market

  • Last Sold Price $179,000
  • Feb 28, 2025

  Last Listing Agent Anthony Rivera Pro Property Management, LLC
• 

  

  /15

  $990,000

  New Construction 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.

  523 Main St N, 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 $434,895

  Last Listing Agent Matt Rose Keller Williams Realty

  22 Lake Rd, Woodbury, CT 06798
• 

  Est $453,662

  Not Listed For Sale

  87 Minortown Rd, Woodbury, CT 06798

  • 3 Beds
  • 1.5 Baths
  • 1,615 Sq Ft
  • Built 1965

  87 Minortown Rd, Woodbury, CT 06798

  Last Sold Summary

  • 7% Below List Price
  • $303/SF
  • 91 Days On Market

  • Last Sold Price $490,000
  • Sep 30, 2024

  Last Listing Agent Rhonda Stokes Drakeley Real Estate, Inc.
• 

  

  /24

  $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
• 

  $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

  Current Estimated Value $873,354

  Last Listing Agent Michael Vartolone William Raveis Real Estate

  84 Hurds Hill Rd, Woodbury, CT 06798
• 

  Not Listed For Sale

  126 Sherman Hill Rd Unit B8, Woodbury, CT 06798

  • 2 Beds
  • 1.5 Baths
  • 1,150 Sq Ft
  • Built 1964

  126 Sherman Hill Rd Unit B8, Woodbury, CT 06798

  Last Sold Summary

  • $168/SF
  • 54 Days On Market

  • Last Sold Price $193,000
  • Aug 15, 2023

  Last Listing Agent Sindy Butkus Klemm Real Estate Inc
• 

  

  /40

  $699,000

  • 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
• 

  $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 $1,097,747

  Last Listing Agent John Donato Jr Showcase Realty, Inc.

  5 Blueberry Ln, Woodbury, CT 06798
• 

  Est $561,308

  Not Listed For Sale

  80 Flanders Rd, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 2,165 Sq Ft
  • Built 1950

  80 Flanders Rd, Woodbury, CT 06798

  Last Sold Summary

  • 22% Below List Price
  • $333/SF
  • 3 Days On Market

  • Last Sold Price $720,000
  • May 19, 2023

  Last Listing Agent Sandra Kerr Berkshire Hathaway Home Services
• 

  

  /24

  $284,500

  Open Sat 11AM - 1:30PM

  • 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
• 

  $705,000

  Sold Apr 07, 2026

  43 Mill Rd, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 2,073 Sq Ft
  • Built 2009

  Last Sold Summary

  • 4% Above List Price
  • $340/SF
  • 27 Days On Market

  Current Estimated Value $672,315

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

  43 Mill Rd, Woodbury, CT 06798
• 

  Est $496,878

  Not Listed For Sale

  54 Barbara Ln, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 2,901 Sq Ft
  • Built 1959

  54 Barbara Ln, Woodbury, CT 06798

  Last Sold Summary

  • 6% Above List Price
  • $162/SF
  • 36 Days On Market

  • Last Sold Price $470,000
  • Jan 08, 2025

  Last Listing Agent Tim Drakeley Drakeley Real Estate, Inc.
• 

  

  /29

  $293,000

  $22K PRICE DROP Under Contract

  • 2 Beds
  • 2 Baths
  • 1,542 Sq Ft

  24 Fox Run, Woodbury, CT 06798

  Motivated seller!! Price drop 22k! Don't cry over high mortgage rates!! This unit offers an assumable 2.99% mortgage for those who qualify. Lowers your monthly payments substantially!! This renovated 2-bedroom, 2-bath townhouse with over 1,500 square feet has so much to offer. Don't wait! This end unit features white kitchen cabinets and stainless appliances, gleaming hardwood floors, semi

  Sindy Butkus Klemm Real Estate Inc

  24 Fox Run, Woodbury, CT 06798
• 

  $499,000

  Sold Jun 16, 2025

  98 Old Town Farm Rd, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 1,648 Sq Ft
  • Built 1972

  Last Sold Summary

  • 1% Above List Price
  • $303/SF
  • 3 Days On Market

  Current Estimated Value $501,002

  Last Listing Agent Jeff Boucher Drakeley Real Estate, Inc.

  98 Old Town Farm Rd, Woodbury, CT 06798
• 

  

  /40

  Est $200,018

  Not Listed For Sale

  229 Bacon Pond Rd Unit 352, Woodbury, CT 06798

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

  229 Bacon Pond Rd Unit 352, Woodbury, CT 06798

  Last Sold Summary

  • $219/SF

  • Last Sold Price $200,000

  Last Listing Agent Cheryl Vitale Berkshire Hathaway Home Services
• 

  

  /40

  $749,000

  Under Contract

  • 3 Beds
  • 3.5 Baths
  • 3,749 Sq Ft

  19 Hillview Ln, Woodbury, CT 06798

  Nestled within the exclusive South Brook community, 19 Hill View Lane offers timeless New England charm paired with exceptional craftsmanship. This beautifully appointed 3 bedroom, 3.5 bath cape colonial is rich in architectural detail, featuring refined millwork, quality finishes, and a thoughtful layout designed for both everyday living and elegant entertaining. The main living spaces flow

  Nicole Fiorelli Fiorelli Realty, LLC

  19 Hillview Ln, Woodbury, CT 06798
• 

  $483,000

  Sold Aug 06, 2025

  3 Lynns Corner Rd, Woodbury, CT 06798

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft
  • Built 1948

  Last Sold Summary

  • 9% Below List Price
  • $201/SF
  • 67 Days On Market

  Current Estimated Value $511,884

  Last Listing Agent Rhya Szymansky Drakeley Real Estate, Inc.

  3 Lynns Corner Rd, Woodbury, CT 06798
• 

  Est $348,122

  Not Listed For Sale

  51 Joshua Hill Rd, Woodbury, CT 06798

  • 3 Beds
  • 1.5 Baths
  • 1,508 Sq Ft
  • Built 1960

  51 Joshua Hill Rd, Woodbury, CT 06798

  Last Sold Summary

  • 17% Above List Price
  • $197/SF
  • 10 Days On Market

  • Last Sold Price $297,500
  • Apr 30, 2025

  Last Listing Agent Sarah Perrotti Regency Real Estate, LLC
• 

  

  /34

  $1,675,000

  $250K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,992 Sq Ft

  819 Main St N, Woodbury, CT 06798

  Open Meadow Farm, a beautifully maintained property offering a blend of rural charm and modern conveniences. Set on 9.88 picturesque acres, this property features three fenced fields, ideal for horses or other livestock and a two-story barn equipped with four stalls, a tack room, gravel storage area and a gleaming concrete main floor. Recent updates include a paved driveway with turnaround, back

  Sindy Butkus Klemm Real Estate Inc

  819 Main St N, Woodbury, CT 06798

Showing Results 41 - 80, Page 2 of 18