Woodbury, CT Homes

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  /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
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  /22

  $2,000 Per Month

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • House for Rent

  4 Weekeepeemee Rd, Woodbury, CT 06798

  Large bright, natural light filled apartment. Second floor with front and back private porches. Living room is very spacious with built ins. Hard wood flooring. Freshly painted - Ready for immediate occupancy. This is a second floor unit. Rear yard is recently cleared and seeded for all tenants to enjoy. Square footage is approximate. Preference is no pets, but will discuss on case by case basis.

  Mary Ann Bennett Drakeley Real Estate, Inc.

  4 Weekeepeemee 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 $966,944 Not Listed For Sale

  17 Birchwood Ln, Woodbury, CT 06798

  • 3 Beds
  • 3 Baths
  • 3,283 Sq Ft
  • Built 2008

  17 Birchwood Ln, Woodbury, CT 06798

  Last Sold Summary

  • 7% Above List Price
  • $276/SF
  • 80 Days On Market

  • Last Sold Price $905,000
  • Mar 28, 2025

  Last Listing Agent Christian Jensen William Pitt
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  /12

  $895,000 Coming Soon

  • 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
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  /14

  $1,400 Per Month

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

  16 Pilgrim Trail Unit F8, Woodbury, CT 06798

  Cozy one-bedroom end unit on the second floor featuring hardwood floors and plenty of natural light. Coin-operated laundry available in the complex. Heat and hot water are included. No pets, no smoking. Available May 1st. Credit check required. Convenient one-level living in a quiet Woodbury community, just minutes from Woodbury center, shopping, and restaurants.

  David Landau RE/MAX Right Choice

  16 Pilgrim Trail Unit F8, 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
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  Est $1,301,030 Not Listed For Sale

  17 Gate Post Ln, Woodbury, CT 06798

  • 4 Beds
  • 4.5 Baths
  • 5,694 Sq Ft
  • Built 1998

  17 Gate Post Ln, Woodbury, CT 06798

  Last Sold Summary

  • 4% Above List Price
  • $220/SF
  • 48 Days On Market

  • Last Sold Price $1,250,000
  • Oct 25, 2023

  Last Listing Agent Russell Antonacci Realtyworx, LLC
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  /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
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  /17

  $2,200 Per Month

  • 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
• 

  $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
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  Est $511,952 Not Listed For Sale

  990 Washington Rd, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 1,847 Sq Ft
  • Built 2006

  990 Washington Rd, Woodbury, CT 06798

  Last Sold Summary

  • 16% Above List Price
  • $238/SF
  • 85 Days On Market

  • Last Sold Price $440,000
  • Sep 13, 2024

  Last Listing Agent Pam Famiglietti William Raveis Real Estate
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  /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
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  /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
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  $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 $132,126

  Last Listing Agent Karen Rigopulos West View Properties, LLC

  16 Pilgrim Trail Unit F2, Woodbury, CT 06798
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  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
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  /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
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  $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
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  $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
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  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.
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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.

  523 Main St N, Woodbury, CT 06798
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  /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
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  $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 $442,790

  Last Listing Agent Matt Rose Keller Williams Realty

  22 Lake Rd, Woodbury, CT 06798
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  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
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  /24

  $325,000

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

  8 Tamarack Ln Unit 8, Woodbury, CT 06798

  3 bedrooms on 2 levels in this spacious end-unit condo offering 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

  Jennifer Mayo William Raveis Real Estate

  8 Tamarack Ln Unit 8, Woodbury, CT 06798
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  $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 $888,329

  Last Listing Agent Michael Vartolone William Raveis Real Estate

  84 Hurds Hill Rd, Woodbury, CT 06798
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  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
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  /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
• 

  $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
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  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
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  /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
• 

  $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 $670,703

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

  43 Mill Rd, Woodbury, CT 06798
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  Est $181,114 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

  • 1% Above List Price
  • $196/SF
  • 60 Days On Market

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

  Last Listing Agent Anthony Rivera Pro Property Management, LLC
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  /38

  $289,900

  • 2 Beds
  • 2 Baths
  • 1,457 Sq Ft

  9 Upper Commons Unit 9, Woodbury, CT 06798

  Welcome to 9 Upper Commons, Woodbury - Tucked away in a quiet, well-maintained community surrounded by mature trees and walking trails, this inviting 2-bedroom townhouse offers three levels for a comfortable, functional lifestyle. The main level features a spacious open-concept floor plan, ideal for everyday living or entertaining. Sliding doors off the dining area leads to your private

  Athan Zeno William Raveis Real Estate

  9 Upper Commons Unit 9, 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 $516,026

  Last Listing Agent Jeff Boucher Drakeley Real Estate, Inc.

  98 Old Town Farm Rd, Woodbury, CT 06798
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  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.
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  /29

  $293,000 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
• 

  $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 $536,209

  Last Listing Agent Rhya Szymansky Drakeley Real Estate, Inc.

  3 Lynns Corner Rd, Woodbury, CT 06798
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  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
• 

  

  /27

  $304,900 Pending

  • 2 Beds
  • 3.5 Baths
  • 1,762 Sq Ft

  13 Clubhouse Dr Unit 13, Woodbury, CT 06798

  Welcome to this well-maintained 3-level condo in the desirable Woodlake community. This spacious unit offers 2 bedrooms, 3 full baths and 1 half bath, plenty of natural light, and a large private deck off the main living area. The kitchen features stainless steel appliances, with washer and dryer conveniently located on the upper level. A fully finished walkout lower level with a full bathroom

  Lance Camby Robert C White & Company LLC

  13 Clubhouse Dr Unit 13, Woodbury, CT 06798

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