Litchfield, CT Homes

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  $799,000

  • 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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  Explore Woodbury

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  /12

  $2,000 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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  $449,900 Sold Aug 08, 2025

  • 2,764 Sq Ft
  • $163/SF
  • 25 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1972

  67 Flanders Rd, Woodbury, CT 06798

  Recently updated Colonial offering 7 rooms, 4 bedrooms, 2 full bathrooms, and 2 half bathrooms with pond views and frontage. The living room includes a fireplace, and the finished walk-out lower level provides added living space with new luxury vinyl plank flooring. Updates include a repointed chimney, refinished hardwood floors, new roof, two new lower-level patio doors, and two new overhead

  Michael Calabro Coldwell Banker Calabro

  67 Flanders Rd, 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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  $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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  $805,000 Sold Aug 07, 2025

  • 2,475 Sq Ft
  • $325/SF
  • 16 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1979

  59 Davids Hill Rd, Woodbury, CT 06798

  This pristine and much-loved shingle-style residence is located at the end of a quiet cul-de-sac in the charming town of Woodbury, known as the "Antiques Capital of CT." With four bedrooms and two and a half baths, the home is nicely sized and has room for expansion. Current owners have invested over 100k in upgrades and remodeling giving it the feel of a new build. Charming details throughout

  Maria Taylor Klemm Real Estate Inc

  59 Davids Hill Rd, 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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  $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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  /35

  $7,000 per month

  • 2 Beds
  • 2 Baths
  • 1,197 Sq Ft
  • House for Rent

  112 W Lake Rd Unit D4, Woodbury, CT 06798

  This property is an ideal retreat for nature enthusiasts and outdoor lovers. Located on the west shore of the lake, it provides a tranquil setting to enjoy the lazy days of summer. You may even spot the resident eagles flying over head! Activities such as canoeing, kayaking, fishing, and swimming are readily available. The lake is speed restricted and stocked with bass and trout, offering

  Sindy Butkus Klemm Real Estate Inc

  112 W Lake Rd Unit D4, Woodbury, CT 06798
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  $483,000 Sold Aug 06, 2025

  • 2,400 Sq Ft
  • $201/SF
  • 67 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1948

  3 Lynns Corner Rd, Woodbury, CT 06798

  Welcome to this beautifully remodeled colonial, nestled in the charming town of Woodbury, CT! Offering 2,400 square feet of thoughtfully updated living space, this home features large front-facing picture windows that flood the interior with natural light. Sleek vinyl flooring runs throughout, providing a durable, low-maintenance finish that complements the home's modern appeal. Step into the

  Rhya Szymansky Drakeley Real Estate, Inc.

  3 Lynns Corner 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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  /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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  $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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  $740,000 Sold Aug 01, 2025

  • 3,341 Sq Ft
  • $221/SF
  • 19 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1987

  101 Railtree Hill Rd, Woodbury, CT 06798

  This beautiful, well maintained, light and bright Colonial sits on a lot of just over 2 acres, complete with perennial gardens, stone walls stairs and pathways and bucolic views. Freshly painted inside and out, this home features a stunningly updated kitchen with walk in pantry and stainless steel appliances. The family room boasts vaulted ceilings, lots of space and a fireplace. The Primary

  Ellen Vincent William Raveis Real Estate

  101 Railtree 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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  /6

  $119,900 Under Contract

  • 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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  /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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  $765,000 Sold Jul 29, 2025

  • 3,330 Sq Ft
  • $230/SF
  • 58 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1986

  3 Inwood Ln, Woodbury, CT 06798

  Set on a quiet cul-de-sac and bordering open space, this beautifully maintained 4BR, 4BTH colonial blends charm w/modern comfort & functionality. Step into the grand foyer flanked by a sunken living room with fireplace and private home office. At the heart of the home is the updated eat-in kitchen, featuring abundant white cabinetry, marble countertops, a butcher block center island, and

  Elizabeth Newnham William Pitt Sotheby's Int'l

  3 Inwood Ln, 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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  /26

  $414,900

  • 2 Beds
  • 1 Bath
  • 1,134 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 heated workshop. Don't be fooled by the square feet. There is additional living

  

  Tim Drakeley

  Drakeley Real Estate, Inc.

  (203) 941-4457

  27 Scratchville Rd, 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 Gaetano Marra Homes

  16 Pilgrim Trail Unit F2, 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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  /16

  $174,900

  • 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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  $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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  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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  /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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  $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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  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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  /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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  $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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  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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  /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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  $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 $1,261,939 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,325 Sq Ft

  452 Middle Road Turnpike, Woodbury, CT 06798

  452 Middle Road Turnpike, Woodbury, CT 06798
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  /14

  $269,900 Pending

  • 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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  $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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  Est $499,532 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft

  71 Mill Rd, Woodbury, CT 06798

  71 Mill Rd, Woodbury, CT 06798
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  /15

  $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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  $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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