Woodbury, CT Homes

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  $824,900

  • 4 Beds
  • 3.5 Baths
  • 3,726 Sq Ft

  181 Railtree Hill Rd, Woodbury, CT 06798

  Beautifully constructed and perched atop a scenic 3+ acre lot, this stately gambrel colonial is just a 5-minute drive from charming downtown Woodbury. Offering 4 to 5 bedrooms, this home features everything one would expect in almost 3400 square feet of living space; a formal dining room, a large front-to-back living room with a fireplace and hardwood floors, and a spacious eat-in kitchen with a

  

  Tim Drakeley

  Drakeley Real Estate, Inc.

  (475) 473-8503

  181 Railtree Hill Rd, Woodbury, CT 06798
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  /12

  $2,200 per month

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

  100 Main St N Unit B, Woodbury, CT 06798

  Charming In-Town Apartment in a Classic Vintage Home Nestled in the heart of Woodbury, this delightful second-floor apartment offers both comfort and character, just moments from all the town's shops, restaurants, and amenities. Set within a beautifully maintained vintage home, the residence features wideboard hardwood floors throughout and a cozy living room complete with a wood-burning

  

  Tim Drakeley

  Drakeley Real Estate, Inc.

  (203) 442-9453

  100 Main St N Unit B, Woodbury, CT 06798
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  $128,500 Sold Jul 23, 2025

  • 546 Sq Ft
  • $235/SF
  • 19 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1965

  16 Pilgrim Trail Unit F2, Woodbury, CT 06798

  Litchfield County Condo - 1st floor unit, set in park like setting. Enjoy all Woodbury has to offer - outstanding restaurants, antiquing, hiking trails, garden shops and more. Close to several nationally recognized private schools. Easy access to highways for commuters. If complex loses power, there is a propane generator to run water systems to units. Highest & Best by Sunday, 5/18/25, 3 pm

  Karen Rigopulos BHGRE Bannon & Hebert

  16 Pilgrim Trail Unit F2, Woodbury, CT 06798
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  Est $154,802 Not Listed For Sale

  24 Meadow Crest Dr, Woodbury, CT 06798

  24 Meadow Crest Dr, Woodbury, CT 06798
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  /35

  $625,000

  • 4 Beds
  • 2.5 Baths
  • 2,256 Sq Ft

  31 McVeigh Rd, Woodbury, CT 06798

  Privately nestled on 1.70 acres in the desirable Quassapaug neighborhood, this beautiful Colonial offers the perfect combination of peace, practicality, & modern style, all while providing both privacy and convenience. Inside, the home has been upgraded for year-round energy efficiency, featuring new blown-in insulation, new baseboard heaters, & updated thermostats. For added warmth in the colder

  

  Jennifer Bundock

  Coldwell Banker Realty

  (203) 457-6837

  31 McVeigh Rd, Woodbury, CT 06798
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  /35

  $1,599 - $1,899 per month

  Woodbury Knoll

  Studio-2 Beds

  302 Tuttle Rd, Woodbury, CT 06798

  Discover our premier apartment community, Woodbury Knoll, in Woodbury, CT, near New Haven. This vibrant community in the Waterbury neighborhood is close to high end restaurants and boutique local stores. All of our apartments are pet-friendly and the perfect home for professionals, students, families, seniors, and everyone in between. Take a closer look at everything we have in store for

  302 Tuttle Rd, Woodbury, CT 06798
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  $521,000 Sold Jul 23, 2025

  • 2,715 Sq Ft
  • $192/SF
  • 59 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1969

  258 Good Hill Rd, Woodbury, CT 06798

  Nestled on over four private acres just minutes from downtown Woodbury, this expansive Cape Cod-style home offers a blend of classic charm and exceptional amenities. This four-bedroom residence features a first-floor primary suite, striking beamed ceilings, and three fireplaces, creating an inviting and warm atmosphere. The thoughtfully designed eat-in kitchen opens to an enclosed porch,

  Chip Parrish Keller Williams Realty

  258 Good Hill Rd, Woodbury, CT 06798
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  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 546 Sq Ft

  10 Pilgrim Trail Unit D8 Bldg 31, Woodbury, CT 06798

  10 Pilgrim Trail Unit D8 Bldg 31, Woodbury, CT 06798
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  $269,900 Under Contract

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

  1 Summit Ct Unit 1, Woodbury, CT 06798

  Step into this charming end-unit townhouse in the inviting Woodlake Community. It boasts 2 bedrooms and 2 full bathrooms with an open floor plan tailored to your needs. Enjoy a convenient spot near I-84 for an easy commute and close to local shops and restaurants offering farm-to-table delights. The community welcomes you with scenic walking paths and a serene lake for swimming and kayaking.

  

  Tim Drakeley

  Drakeley Real Estate, Inc.

  (203) 496-8395

  1 Summit Ct Unit 1, Woodbury, CT 06798
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  /12

  $2,200 per month

  • 2 Beds
  • 1.5 Baths
  • 1,050 Sq Ft
  • House for Rent

  226 Main St N Unit 2, Woodbury, CT 06798

  Beautifully renovated 2 bedroom apartment. Granite and new appliances in the spacious eat-in kitchen. The living room leads to the private and cozy bluestone patio. 2nd floor full bath has a frameless shower enclosure and is flanked by both bedrooms with hardwood floors. Close to highways, shopping and restaurants. Broker related/owner.

  Frances Mirabilio Town & Country Realty and Design, LLC

  226 Main St N Unit 2, Woodbury, CT 06798
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  $290,000 Sold Jul 22, 2025

  • 1,532 Sq Ft
  • $189/SF
  • 47 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1980

  2 Edgehill Ct, Woodbury, CT 06798

  Recently Remodeled Move-in Ready in this quiet Woodlake community. 2 Bedroom, 2 Bathroom Condo w/ beautiful landscaped grounds in front yard, New luxury vinyl plank flooring on first floor, new interior paint throughout, updated appliances including WiFi equipped Range, new cabinetry hardware and countertops in Kitchen w/ smart led under cabinet lighting , new light fixtures, both bathrooms

  Christina Moulthrop Showcase Realty, Inc.

  2 Edgehill Ct, Woodbury, CT 06798
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  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
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  /5

  $179,900

  • 2 Beds
  • 1 Bath
  • 913 Sq Ft

  229 Bacon Pond Rd Unit 322, Woodbury, CT 06798

  Prime location for affordable living in Woodbury CT! Charming, updated 2-bedroom, 1-bath condo with an open-concept layout. The dining area features sliding doors to a patio, flooding the space with natural light. The living room boasts built-in bookcases flanking a cozy fireplace. Relax on the patio with views of the community's in-ground pool. The Town and Country complex is just 2 minute ride

  

  Tim Drakeley

  Drakeley Real Estate, Inc.

  (475) 335-8422

  229 Bacon Pond Rd Unit 322, Woodbury, CT 06798
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  $4,850 per month

  • 4 Beds
  • 2.5 Baths
  • 2,906 Sq Ft
  • House for Rent

  581 Flanders Rd, Woodbury, CT 06798

  Annual Furnished Rental Available September of a classic New England charmer, with 8 acres, an in-ground pool and pond in Woodbury. Circa 1765, this inviting home offers the perfect blend of historic warmth and modern comfort, sitting on a picturesque lot minutes from town. Spacious and sun-filled layout featuring 3 or 4 bedrooms, 2.5 baths, hardwood floors, and a bright, open eat-in kitchen with

  William Bolls Compass Connecticut, LLC

  581 Flanders Rd, Woodbury, CT 06798
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  $214,000 Sold Jul 18, 2025

  • 1,182 Sq Ft
  • $181/SF
  • 42 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1980

  6 Deer Hill Ct, Woodbury, CT 06798

  Nestled in with only woods in your back yard and hidden on the back side of a bank of garages, this end unit offers privacy you don't find in many condos. Short walk from garage by a pretty perennial garden. This is the least expensive two-bedroom unit in Woodlake at the moment. Country house style with the exposed natural beams and columns, nook off kitchen (many have closed in for a half bath

  Mary Ann Bennett Drakeley Real Estate, Inc.

  6 Deer Hill Ct, Woodbury, CT 06798
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  Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,895 Sq Ft

  13 Tamarack Ln Unit 13, Woodbury, CT 06798

  13 Tamarack Ln Unit 13, Woodbury, CT 06798
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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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  /40

  $4,950 per month

  • 4 Beds
  • 4.5 Baths
  • 3,000 Sq Ft
  • House for Rent

  259 Main St S, Woodbury, CT 06798

  Located on Main Street South in the heart of Woodbury, in the Litchfield Hills, this versatile property offers the perfect opportunity for a retail antique showroom or traditional living. The main house features 4 bedrooms, 4.5 baths, and boasts original architectural elements, generous living space, and beautifully maintained outdoor areas. The main living area includes a half bath, an eat-in

  Michael Baldwin Oxford Realty

  259 Main St S, Woodbury, CT 06798
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  $539,000 Sold Jul 18, 2025

  • 1,675 Sq Ft
  • $322/SF
  • 3 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1985

  54 Barnhill Rd, Woodbury, CT 06798

  This Extraordinary Custom Design and Engineered One - Level Modern/ Contemporary 3 Bedroom, 2.5 Bath is a Masterpiece of Tranquility. A Prominent Design Feature is the Vaulted Ceilings exposing the Natural Wood Beams and Steel with 9 Skylights Illuminating Bright Natural Light in every room. The Beautiful Open Floor allows for a Stunning Great Room encompassing a new Kitchen with Quartz

  Joseph Racanelli William Raveis Real Estate

  54 Barnhill Rd, Woodbury, CT 06798
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  Est $639,670 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,015 Sq Ft

  305 Main St S, Woodbury, CT 06798

  305 Main St S, Woodbury, CT 06798
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  /6

  $119,900

  • Land
  • 2.10 Acres
  • $57,095 per Acre

  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.

  (475) 447-1659

  0 Main St N Unit 24072843, Woodbury, CT 06798
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  $1,400,000 Sold Jul 17, 2025

  • 2,418 Sq Ft
  • $579/SF
  • 62 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1810

  39 Painter Hill Rd, Woodbury, CT 06798

  Stunning Renovated Antique Home w/ Scenic Views & Luxurious Amenities. 4 beds, 3 full baths w/ exquisite craftsmanship throughout. As you enter the WOW factor takes hold as you look through floor to ceiling windows over a spectacular rushing brook. Inside, find wide plank floors, recessed lighting, skylights, & a wood-burning fireplace which create a warm and inviting ambiance. The high-end

  Stacey Matthews W. Raveis Lifestyles Realty

  39 Painter Hill Rd, Woodbury, CT 06798
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  Not Listed For Sale

  0 Mill Rd, Woodbury, CT 06798

  0 Mill Rd, Woodbury, CT 06798
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  /26

  $699,900

  • 3 Beds
  • 3 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 in need of restoration is just a 2-minute stroll from coffee shops, top-notch restaurants, and the historic Main Street. The home could be meticulously updated from the ground up, featuring wide board antique flooring, a stunning great room with a cathedral

  

  Tim Drakeley

  Drakeley Real Estate, Inc.

  (475) 291-4564

  27 Middle Quarter Rd, Woodbury, CT 06798
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  $130,000 Sold Jul 16, 2025

  • 546 Sq Ft
  • $238/SF
  • 43 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1965

  14 Arrowhead Way Unit 1, Woodbury, CT 06798

  Excellent location in Quassuk Heights. This 1st floor, light and bright end unit is one of only 4 in the entire complex with direct interior access to the Laundry facility. A well maintained unit that is move in ready. Updates to kitchen and bath with stall shower. Close proximity to parking and mail. Updated A/C. Walk to town for shopping, restaurants and parks. Don't miss out on this great

  Jeff Boucher Drakeley Real Estate, Inc.

  14 Arrowhead Way Unit 1, Woodbury, CT 06798
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  Est $1,381,714 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,050 Sq Ft

  8 Stone Hollow Rd, Woodbury, CT 06798

  8 Stone Hollow Rd, Woodbury, CT 06798
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  /2

  $399,900

  • Land
  • 56 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
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  $302,500 Sold Jul 09, 2025

  • 1,456 Sq Ft
  • $208/SF
  • 33 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1979

  8 Highpoint Ct, Woodbury, CT 06798

  This extensively renovated (2022) Cornerhouse model condominium offers immediate occupancy and a desirable private setting with a level approach. The updated open-concept floor plan features a redesigned kitchen that seamlessly integrates with the family room, providing an ideal layout for both daily living and entertaining. The kitchen is appointed with quartz countertops, stainless steel

  Tom Greto William Raveis Real Estate

  8 Highpoint Ct, Woodbury, CT 06798
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  Est $1,370,495 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
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  /29

  $343,317 Pre-Foreclosure

  • 3 Beds
  • 1 Bath
  • 1,075 Sq Ft

  4 Hazel Plain Rd, Woodbury, CT 06798

  If you dream of finding an Oasis within an Oasis (Woodbury often ranks in the Top 10 of CT towns annually), then look no further! This home is it! Nestled on the banks of the Sprain Brook, this unique property provides pretty views of the water and the sweet sound of the babbling brook as you relax on either the front or the back decks. The home has a large two-car detached garage with an

  

  Gary Smith

  eXp Realty

  (203) 463-5946

  4 Hazel Plain Rd, Woodbury, CT 06798
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  $545,000 Sold Jul 07, 2025

  • 3,149 Sq Ft
  • $173/SF
  • 30 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1977

  259 Old Town Farm Rd, Woodbury, CT 06798

  Enjoy small town living in Woodbury, CT! Come home to this 3 Bedroom, 3 Bath Cape which features an open floor plan with Hardwood Floors throughout (less Kitchen). This well maintained home offers: a spacious Living Room with hardwood floors & ceiling fan, a fully applianced (Sub-Zero, Miele) granite Kitchen with "Bird Watching" Bay Window, built-ins and slider to the back Deck, a Dining Room

  Ron Nettleton William Raveis Real Estate

  259 Old Town Farm Rd, Woodbury, CT 06798
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  Est $748,172 Not Listed For Sale

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

  107 Stagecoach Rd, Woodbury, CT 06798

  107 Stagecoach Rd, Woodbury, CT 06798
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  /2

  $414,900 Coming Soon

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft

  27 Scratchville Rd, Woodbury, CT 06798

  This charming home has just been refreshed with recent updates, including a brand new full bathroom, reworked floor plan, fresh paint, and thoughtful touches throughout to enhance functionality and flow. It features a newer roof, beautiful cedar shingles, a generator, two separate storage sheds, and an attached 24x11 workshop. A separate barn/garage and privacy fencing add even more appeal, while

  

  Tim Drakeley

  Drakeley Real Estate, Inc.

  (203) 941-4457

  27 Scratchville Rd, Woodbury, CT 06798
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  $700,000 Sold Jul 02, 2025

  • 2,614 Sq Ft
  • $268/SF
  • 47 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1998

  16 Fairgrounds Rd, Woodbury, CT 06798

  Nestled in a sought-after neighborhood, this charming Colonial home welcomes you w/ its classic wrap-around porch, mature plantings, & timeless curb appeal. Inside, you'll find a formal living room w/wood-burning fireplace, formal dining room, powder room & laundry area, & bright kitchen w/ granite countertops, stainless steel appliances, breakfast bar w/ backyard views, & cozy dining nook.

  Taylor O'Keefe Drakeley Real Estate, Inc.

  16 Fairgrounds Rd, Woodbury, CT 06798
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  Est $818,911 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
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  /2

  $119,900 Under Contract

  • Land
  • 0.81 Acre
  • $148,025 per Acre

  Lot 64 Highpoint Rd, Woodbury, CT 06798

  Looking for a modest size lot to build your dream home? This lot in bucolic Woodbury sits near the top of Hurds Hill in an area of lovely homes. The lot is a level rectangle with 150 feet of street frontage. Interesting opportunity!

  

  Justin Bette

  Joseph Bette REALTORS Inc

  (203) 590-9397

  Lot 64 Highpoint Rd, Woodbury, CT 06798
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  $385,000 Sold Jul 02, 2025

  • 1,693 Sq Ft
  • $227/SF
  • 26 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1964

  59 Arrowhead Way, Woodbury, CT 06798

  Discover the potential in this generously sized split level 5-bedroom, 2-full-bath home nestled in charming Woodbury, CT. Situated on just over an acre, this property offers ample space inside and out, perfect for growing families and those who love to entertain. While the home is in need of updating, it offers a lifetime roof under warranty on both the home and pool house. A major investment

  Shawna Mucherino Coldwell Banker Realty

  59 Arrowhead Way, Woodbury, CT 06798
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  Est $997,176 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,726 Sq Ft

  181 Joshua Hill Rd, Woodbury, CT 06798

  181 Joshua Hill Rd, Woodbury, CT 06798
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  $990,000 New Construction

  • 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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  $165,000 Sold Jul 01, 2025

  • 913 Sq Ft
  • $181/SF
  • 18 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1971

  229 Bacon Pond Rd Unit 144, Woodbury, CT 06798

  Welcome to 229 Bacon Pond Road, Unit 144, a spacious 2-bedroom, 1-bath condo nestled in the highly desirable Woodberry neighborhood. This unit offers great potential for buyers eager to add their personal touch and create a truly special home. Though it may benefit from some updating, it provides a solid foundation with a comfortable layout and ample natural light. The open living space is

  Reza Abbassi New Door Realty

  229 Bacon Pond Rd Unit 144, Woodbury, CT 06798

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