Woodbury, CT Homes

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  $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.

  (203) 871-0905

  99 Plumb Brook Rd, Woodbury, CT 06798
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  $1,800 total monthly price

  • 1 Bed
  • 1 Bath
  • 2,728 Sq Ft
  • House for Rent

  65 Hard Hill Rd, Woodbury, CT 06798

  Very nice, furnished one-bedroom in-law apartment for rent. The spacious kitchen opens to a bright, sunny living room. The apartment also features a large bathroom and a separate laundry room.Enjoy a lovely backyard with patio access. No smoking and no pets, please. The landlord takes care of exterior maintenance and all utilities, including heat, hot water, electricity, central air, garbage

  

  Marian Van Egas

  Berkshire Hathaway NE Prop.

  (475) 275-6685

  65 Hard Hill Rd, Woodbury, CT 06798
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  $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 $1,678,377

  Last Listing Agent Maria Taylor Klemm Real Estate Inc

  225 Old Sherman Hill Rd, Woodbury, CT 06798
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  Est $209,083 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

  • 5% Above List Price
  • $219/SF
  • 22 Days On Market

  Last Sold Price $200,000

  Last Listing Agent Nickie O'Toole Nickie Otoole Realty LLC
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  $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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  $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
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  $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 $476,992

  Last Listing Agent Nancy Langrock William Raveis Real Estate

  145 Cat Swamp Rd, Woodbury, CT 06798
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  Est $287,669 Not Listed For Sale

  1 Racoon Ridge Rd, Woodbury, CT 06798

  • 2 Beds
  • 2 Baths
  • 1,182 Sq Ft
  • Built 1980

  1 Racoon Ridge Rd, Woodbury, CT 06798

  Last Sold Summary

  • 2% Above List Price
  • $239/SF
  • 58 Days On Market

  Last Sold Price $282,000

  Last Listing Agent Mary Ann Hebert BHGRE Gaetano Marra Homes
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  $874,900

  • 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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  $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
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  $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 $445,518

  Last Listing Agent Katherine Parlato Drakeley Real Estate, Inc.

  163 Washington Rd, Woodbury, CT 06798
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  Est $227,958 Not Listed For Sale

  74 Washington Rd Unit 14, Woodbury, CT 06798

  • 2 Beds
  • 1.5 Baths
  • 960 Sq Ft
  • Built 1969

  74 Washington Rd Unit 14, Woodbury, CT 06798

  Last Sold Summary

  • 4% Above List Price
  • $229/SF
  • 31 Days On Market

  Last Sold Price $220,000

  Last Listing Agent Carole Sansone William Raveis Real Estate
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  $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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  $1,599 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
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  $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 $444,837

  Last Listing Agent Michael Ferris eXp Realty

  158 Hazel Plain Rd, Woodbury, CT 06798
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  Est $1,146,367 Not Listed For Sale

  6 Owl Ridge Rd, Woodbury, CT 06798

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

  6 Owl Ridge Rd, Woodbury, CT 06798

  Last Sold Summary

  • 9% Above List Price
  • $217/SF
  • 165 Days On Market

  Last Sold Price $1,050,000

  Last Listing Agent Christian Jensen William Pitt
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  $475,000 Coming Soon

  • 3 Beds
  • 1 Bath
  • 1,836 Sq Ft

  242 Bacon Pond Rd, Woodbury, CT 06798

  Charming antique home in the heart of Woodbury with a separate legal 700 sq. ft. apartment over the detached 2-car garage, offering excellent rental income potential. Full of vintage character, this special property features wide board antique flooring, original details, built-ins, and three fireplaces, including one in the cozy eat-in kitchen. Set on a gorgeous long, treed in-town lot, the

  

  Tim Drakeley

  Drakeley Real Estate, Inc.

  (475) 882-8908

  242 Bacon Pond Rd, Woodbury, CT 06798
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  $1,900 total monthly price

  • 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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  $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 $674,068

  Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

  38 Barnhill Rd, Woodbury, CT 06798
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  Est $278,574 Not Listed For Sale

  29 Fox Run, Woodbury, CT 06798

  • 2 Beds
  • 2 Baths
  • 1,182 Sq Ft
  • Built 1980

  29 Fox Run, Woodbury, CT 06798

  Last Sold Summary

  • 5% Above List Price
  • $224/SF
  • 131 Days On Market

  Last Sold Price $265,000

  Last Listing Agent Wendy Brazauskas Coldwell Banker Realty
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  $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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  $1,750 per month plus fees

  • 1 Bed
  • 1 Bath
  • 1,000 Sq Ft
  • Condo for Rent

  259 Main St S Unit 4, Woodbury, CT 06798

  Property Id: 2072922Light and bright 2 Story 1 Bedroom Condo available for immediate occupancy. This unit comes with a spacious and open first floor lay out, kitchen with extra cabinet space and more. The second floor has a full bathroom and spacious Bedroom with ample closet space. This condo is located on Woodbury most desirable areas and will not last long so dont wait schedule a tour

  259 Main St S Unit 4, Woodbury, CT 06798
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  $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 $388,943

  Last Listing Agent Shawna Mucherino Coldwell Banker Realty

  306 Upper Grassy Hill Rd, Woodbury, CT 06798
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  Not Listed For Sale

  33 Woods Way Unit 33, Woodbury, CT 06798

  • 2 Beds
  • 2 Baths
  • 1,726 Sq Ft
  • Built 1979

  33 Woods Way Unit 33, Woodbury, CT 06798

  Last Sold Summary

  • $174/SF
  • 13 Days On Market

  Last Sold Price $300,000

  Last Listing Agent Todd Rogers Todd & Company Realtors
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  $279,990 Under Contract

  • 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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  $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
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  $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 $801,283

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

  3 Inwood Ln, Woodbury, CT 06798
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  Est $705,045 Not Listed For Sale

  785 Washington Rd, Woodbury, CT 06798

  • 3 Beds
  • 6 Baths
  • 8,747 Sq Ft
  • Built 1982

  785 Washington Rd, Woodbury, CT 06798

  Last Sold Summary

  • 4% Above List Price
  • $77/SF
  • 371 Days On Market

  Last Sold Price $675,000

  Last Listing Agent Jeff Boucher Drakeley Real Estate, Inc.
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  $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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  $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
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  $291,000 Sold Apr 11, 2025

  17 Tamarack Ln Unit 17, Woodbury, CT 06798

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Built 1974

  Last Sold Summary

  • 4% Above List Price
  • $224/SF
  • 22 Days On Market

  Last Listing Agent Sharisse Steiner William Raveis Real Estate

  17 Tamarack Ln Unit 17, Woodbury, CT 06798
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  Not Listed For Sale

  0 Mill Rd, Woodbury, CT 06798

  0 Mill Rd, Woodbury, CT 06798

  Last Sold Summary

  • $0/SF
  • 54 Days On Market

  Last Sold Price $55,000

  Last Listing Agent Jason Arcuri eXp Realty
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  $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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  $2,100 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
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  $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

  Current Estimated Value $593,266

  Last Listing Agent Matthew Amatruda Drakeley Real Estate, Inc.

  90 Railtree Hill Rd, Woodbury, CT 06798
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  Est $1,392,076 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

  • 11% Above List Price
  • $220/SF
  • 48 Days On Market

  Last Sold Price $1,250,000

  Last Listing Agent Russell Antonacci Realtyworx, LLC
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  $310,000 Pending

  • 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
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  $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
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  $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 $873,606

  Last Listing Agent Chris Carey Carey & Guarrera Real Estate

  11 Saxony Ln, Woodbury, CT 06798
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  Est $510,889 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

  Last Listing Agent Pam Famiglietti William Raveis Real Estate

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